Synthesis and Application of Dihydroxyalkylamino Groups Modified Polysiloxane

Synthesis and Application of Dihydroxyalkylamino Groups Modified Polysiloxane | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Synthesis and Application of Dihydroxyalkylamino Groups Modified Polysiloxane Weijie Yan, Yunhe Lai, Yuxia Zhang, Hong Dong, Yanjiang Song, and 2 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6962058/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 15 Dec, 2025 Read the published version in Silicon → Version 1 posted 7 You are reading this latest preprint version Abstract Several single- and double-dihydroxyalkylamino groups terminated polysiloxanes with different molecular weights were prepared by a four-step synthesis method using diethanolamine, allyl bromide, and hydrogen-containing silicone oil. The emulsified dihydroxyalkylamino group-modified polysiloxane lotion was used as a softener in fabric finishing. Compared to fabric treated with the commercial amino silicone oil softener, fabric treated with them can improve the hydrophilicity from hydrophobic to hydrophilic, and the tertiary amine structure can resist yellowing defects of the amino silicone oil with the whiteness difference value in line with the normal yellowing value change range. It will not affect the color brightness of the fabric. Fabric treated with such modified polydimethylsiloxane will increase softness rating greater than 4.0. Meanwhile, its improved anti-static ability was indicated by fabric resistance lowered from 10 13 to 10 12 Ω, and fracture strength was enhanced from 211.2 N to more than 400 N. Dihydroxyalkylmino groups Group-modified polydimethylsiloxane Softener Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 1. Introduction The main chain of polydimethylsiloxane with methyl organic groups is very flexible, with the energy required to rotate around Si-O bonds close to zero, which makes the polydimethylsiloxane chains rotate freely to angles of 360°. Due to the rotational freedom of Si-O-Si bonds and the low interaction energy between methyl groups on silicon atoms, organosiloxane has the advantages of low surface tension, electrical properties, softness, and thermal oxidation stability. These characteristics make organosiloxane an excellent fabric finishing agent that provides good stress resilience and softness for fabrics [1,2]. In order to impart a fabric with a good feel and appearance, anti-fouling, anti-static, and other properties [3–6], chemicals are widely applied to provide a finish and broaden the application range [7–27]. Since amino-modified silicone softener has little effect on fabric strength and does not significantly affect the color fastness of dyed fabrics, meanwhile it endows fabrics with good washability and a “super soft” treatment effect, Amino silicone oil is a fundamental component used explicititly as a soft finishing agent for textiles. Despite being known as the “king of softeners”, it still has the drawbacks of poor hydrophilicity and susceptibility to yellowing when used as an organic silicon softener. To obtain a better comprehensive effect of an organic silicon finishing agent, multi-functional modified polysiloxane can be prepared, and other functional groups can be introduced on the basis of amino-modified organosilicon to improve the deficiency of amino silicone oil [28–30]. Compared with other functional group modifications, aminoalkyl groups are commonly used to modify the main chain of polysiloxane chemically. According to the reasons for amino yellowing, converting primary amino groups into sterically hindered secondary or tertiary amino groups is an effective method to improve resistance to yellowing. Modified silicone oil with secondary and tertiary amino groups shows little yellowing phenomenon. Diethanolamine (DEA) and allyl bromide were used to obtain hydroxyl-protected N, N-bis[2-(trimethylsiloxy)ethyl]allyl amine (TMSEAA). Then it reacts with hydrogen-containing silicone oil of α-trimethylsilyl-ω-dimethylsilylpolydimethylsiloxane or α, ω-dimethylsilylpolydimethyl-siloxane (PDMS-H) via hydrosilylation to produce a single or double N. N-disubstituted amino terminated polydimethylsiloxane of α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane or α,ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane (TMSEAP-PDMS). Then, N, N-dihydroxyethylamino propyl polydimethylsiloxanes (TMSEAP-PDMS) were obtained after hydroxyl deprotection. Emulsified N, N-dihydroxyalkylamino groups terminated polysiloxanes as a softener can improve the hydrophilicity and yellowing resistance of fabrics in fabric finishing applications. 2. Experimental section 2.1 Raw materials Single-ended hydrogen-containing polysiloxane (purity greater than 97%) and double-ended hydrogen-containing silicone oil (Mn: 1000 ~ 5000 g/mol) were purchased from Shanghai Guangrui Biotechnology Co., Ltd. Toluene, industrial grade, was obtained from HangzhouShuanglin Chemical Co., Ltd. Allyl bromide, 98%, was obtained from Beijing Bailingwei Technology Co., Ltd.; Diethanolamine, 98%, was from Shanghai Lingfeng Chemical Reagent Co., Ltd. Karstedt’s catalyst, industrial grade, were obtained from Jiaxing United Chemical Co., Ltd. And deionized water is self-made in the laboratory. Ammonia value test Follow the national standard “Determination of Ammonia Value in Chemical Reagents” (GB/T 6730.35–2007). 2.2 Experimental Instruments The relative molecular weights of polymers were determined by a PL-GPC50 gel-permeation chromatograph from Varian (USA) with the standard polydimethylsiloxanes from American Polymer Standards Corp. 1 H NMR spectra of the polymers were recorded on an AVANCE AV 400MHz Nuclear Magnetic Resonance instrument (Bruker, Germany), During the test, approximately 10 mg of the liquid sample was dissolved in approximately 0.6 mL of internal standard-free deuterated chloroform (CDCl 3 ), and the relaxation time D 1 was set to 5 s. Surface morphologies of polymer-treated fabrics were inspected using a ZEISS Sigma500 Scanning Electron Microscope (Germany), and the properties of polymer-treated fabrics were tested using a VPM-1A-600 pneumatic paddle and a PT-1A needle plate tenter (Japan Qianjing Dyeing Machinery Co., Ltd.). Water contact angles of polymer-treated fabrics were measured using a Kruss DSA30 water-contact angle measuring instrument (Kruss GmbH, Germany). 2.3 Synthesis of Single-ended Dihydroxyalkylamino Modified Polysiloxane The preparation of single-ended dihydroxyalkylamino-modified polysiloxane using diethanolamine (DEA) as raw material includes four steps. The corresponding chemical equation is shown in Scheme 1 . According to the scheme shown, the four-step synthesis includes Step 1: the reflux reaction of diethanolamine and hexamethyldisilazane to obtain bis[2-(trimethylsiloxy)ethyl]amine (TMSEA). Step 2: Add allyl bromide dropwise to TMSEA and continue the reaction to obtain N, N-bis[2-(trimethylsiloxy)ethyl]allyl amine (TMSEAA). Step 3: TMSEAA was reacted with single-ended hydrogenated silicone oil (PDMS-H) via hydrosilylation to obtain α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl] aminopropyl-polydimethylsiloxane (TMSEAP-PDMS). In step 4, the hydroxyl groups of TMSEAP-PDMS were deprotected from trimethylsilyl groups to obtain single-ended dihydroxyamine modified polysiloxane (DEAP-PDMS). 2.3.1 Preparation of TMSEA Diethanolamine (158.0 g, 1.5 mol) was put into a 1000 mL three-necked flask equipped with a condenser, thermometer, and constant pressure dropping funnel, hexamethyldisilazane (314.0 g, 1.95 mol) was added dropwise under stirring and refluxing at 100 ℃ in 225 minutes, then raise the temperature at a rate of 10 ℃/h to 140 ℃, turn off the heating after constant stirring and refluxing for 30 hours. TMSEA, a product with hydroxyl groups protected by trimethylsilyl groups, was obtained as a transparent liquid by vacuum distillation at 140 ℃/-100 kPa. Yield 93%, and a GC purity of 99.9%. 1 H-NMR(CDCl 3 ) (ppm) is consistent with the reported data [31]: δ0.11(SiC H 3 ), δ1.98(N H ), δ2.73(-NC H 2 ), δ3.69(OC H 2 ). 2.3.2 Preparation of TMSEAA 8 g of TMSEA was added to a three-necked flask and cooled to 5 ℃; 25.4 g of allyl bromide was added dropwise. When the yellow color of the solution was observed to be more pronounced, remove the ice bath and let the temperature gradually rise, and then the flak was placed into an oil bath with a temperature set to 40 ℃. A NaOH solution with a mass fraction of 20% was added slowly to provide the system with a weakly alkaline state and facilitated the reaction to proceed in the positive direction. Terminated the reaction 2 hours later than dropwise addition of allyl bromide finished, to do extraction with CH 2 Cl 2 , followed by fractional distillation of the oil phase to remove the solvent and the low boiling substances from the system, then the residue was further purified by vacuum distillation to get N, N-bis[2-(trimethyl siloxy)ethyl]allylamine (TMSEAA) with a yield of 51.2%, GC-MS purity of 99%. 1 H-NMR(CDCl 3 ) (ppm) data is consistent with reported before [31]: δ0.12(SiC H 3 ), δ2.60(OCH 2 C H 2 N), δ3.03(CH 2 = CHC H 2 N), δ3.67(OC H 2 CH 2 N), δ5.19(C H 2 = CHCH 2 N) And δ5.86(CH 2 = C H CH 2 N). 2.3.3 Preparation of TMSEAP-PDMS 15 mL of dry toluene (content of H 2 O is about 200ppm), 1.09g (3.76 × 10-3mol) of TMSEAA, and 0.38g of 1wt% Pt in Karstedt catalyst were put to a 100mL three necked flask with N 2 protection. After the mixture was stirred and activated at 70 ℃ for 30 minutes, 15.5g of single-ended hydrogen-containing silicone oil (PDMS-H) was uniformly added by an injection pump with an injection time of 1.5 hours. Continued the reaction at 70 ℃ for 10 hours and then cooled to room temperature. The system was left open to inactivate the catalyst, and the product was subjected to vacuum distillation to remove low boiling materials, resulting in the addition product α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane with a yield of 82.0%. A series of single-ended dihydroxyalkyl-modified amino polysiloxanes with hydroxyl groups protected by TMS (trimethylsilyl) groups were prepared by reacting PDMS-H with different molecular weights. 2.3.4 Preparation of DEAP-PDMS The target product, single-ended dihydroxyalkyl-modified amino polysiloxane (DEAP-PDMS), was obtained by deprotection of trimethylsilyl-protected single-ended dihydroxyalkyl-modified amino polysiloxane TMSEAP-PDMS. For example, using a single-ended hydrogen-containing silicone oil with a relative molecular weight Mn of about 1000 g/mol as the raw material, the conversion rate of the raw material is greater than 90%, but the conversion rate decreases as the molecular weight increases. To 14.5 g of TMSEAP-PDMS (Mn ≈ 5000 g/mol), 0.1 g (1.67 × 10 − 3 mol) of acetic acid and 4.6 g of methanol were added to a 100mL three-necked flask. The mixture was stirred and raised to 65 ℃ for 6 hours. The low boiling point was removed by vacuum distillation to obtain the target product single terminal dihydroxyalkyl-modified amino polysiloxane of α-methyl-ω-N, N-dihydroxyethylaminopropyl polydimethylsiloxane, with a yield of 64% (Table 1 , OH-5). A series of single-ended dihydroxyalkyl-modified amino polydimethylsiloxane samples with a relative molecular weight of approximately 1000 ~ 5000 g/mol are shown in Table 1 . 2.3.5 Preparation of Polydimethylsiloxane Modified with Double Terminal Dihydroxyamine Groups TMSEAA reacted with double-terminal hydrogen-containing silicone oils will obtain double-terminal dihydroxyalkyl modified amino polydimethylsiloxane. Structural formula of α, ω-N, N-dihydroxyethylaminopropyl polydimethylsiloxane is shown in Scheme 2 , with the repeat unit numbers from 10 to 65. 2.4 Preparation the lotion of dihydroxyalkyl modified amino polysiloxane The dihydroxyalkyl-modified amino polysiloxane can be successfully emulsified by a mixed emulsifier of polyoxyethylene ether AE0-6 and AEO-9 in a 1:1 mass ratio. When the dosage of the emulsifier is 6% and 1wt% of acetic acid used as a catalyst were applied to transfer a certain amount of dihydroxyalkyl-modified amino polysiloxane into lotion, a small amount of water can achieve phase transition. When the total mass fraction of water reaches 73%, it will change from "water in oil (W/O)" to "oil in water (O/W)" and become a lotion after passing the phase inversion point. When the lotion was tested at 2000 r/min in the homogenizer, no phenomenon of demulsification occurred. After phase inversion, dilute 6 g lotion with 200 g water to obtain a stable O/W lotion. Furthermore, the diluted lotion was used as a fabric softener to test the fabric finishing performance. 2.5 Application of Dihydroxyalkyl Amino Modified Polysiloxane Lotion 2.5.1 Application method of lotion Since amino silicone oil is a fundamental component used explicitly as a textile softening agent, with the best adsorption, compatibility, and emulsifying properties, it is suitable for various textile softening treatments. Amino silicone oil can be easily emulsified into stable and transparent micro-emulsion by appropriate surfactant. It can be used alone or combined with other organic silicon or organic softeners to form special softening finishing agents. As literature reports [32–34], Since there are primary and secondary amino groups present in the structure of commercially available amino silicone oil, the yellowing mechanism is caused by the oxidation and decomposition of amino groups to form azo and oxidized azo chromophores, resulting in yellowing of the fabric. Among the side chain amino groups, the dual amine type of amino silicone oil showed the most severe yellowing, followed by the primary amino group. The modified silicone oil with secondary and tertiary amine groups showed little yellowing phenomenon. The lotion made by adding an emulsifier to the amino silicone oil is often used as a fabric treatment agent to improve the softness, crease resistance, elasticity, and tear resistance significantly. The application testing method is as follows. Cut the woven fabric into an A 4 paper size and conduct tests on its whiteness, hydrophilicity, antistatic performance, and softness after soaking, shaping, and moisture regain. The fabric processing and testing methods are: (1) Dipping: Soak the woven fabric in lotion for about 10 s and then pass through the rolling car. The wet woven fabric is preliminarily shaped by a rolling mill through a process of immersion and rolling; (2) Molding: The fabric that has been rolled is taken out and passed through a molding machine at 160 ℃ for a total of 60 seconds at a speed of 4 m/min. The fabric that has been taken out and passed through the molding machine is then allowed to regain moisture for 1 hour; (3) Whiteness test: After moisture is regained, the fabric is placed on a colorimeter for whiteness testing. The fabric is folded into four layers and tested four times, with an automatic average reading of the four values; (4) Hydrophilicity test: Fix the moisture fabric sample on the stretch cloth ring, use a dropper with a rubber head to drop a water droplet at a height of 1 cm from the fabric surface, and start timing. When the water droplet decreases to a non-reflective watermark, stop timing. Hydrophilicity can also be expressed by the water contact angle of the fabric after the immersion rolling process treatment. Under the same soaking and rolling process, the length of water absorption time of the measuring sample cloth indicates poorer water absorption; (5) Antistatic performance test: Use a resistance electrostatic tester. Preheat the instrument before testing, cut the woven fabric that has been dipped and rolled into 45 mm × 45 mm, and place it in an environment with a humidity of 29.6% RH and a temperature of 20.2 ℃ for 5 hours before testing; (6) Softness testing: Indicators such as softness and hand feel are subjective evaluation indicators, mainly obtained through the tester's tactile sensation to obtain evaluation results; (7) Tear strength shall be tested using a drop hammer fabric tear tester in accordance with GB/T 3917.1 standard. The sliding friction force is tested according to the GB/T 3925 − 2009 standard using a friction coefficient tester. The fracture strength is tested according to ASTM D638 standard using a universal material testing machine. 3. Results and Discussion 3.1 Preparation of dihydroxyamine modified polydimethylsiloxane by hydrosilylation Single-ended hydrogen-containing silicone oil (PDMS-H) was used as the key component to undergo hydrosilylation with N, N-bis[2-(trimethylsiloxy)ethyl]allyl-amine (TMSEAA) under the action of Karlstedt catalyst, resulting in TMS protected hydroxylalkylamino polysiloxane of α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl] aminopropylpolydimethylsiloxane (TMSEAP-PDMS). Then, under acidic conditions, the TMS group was removed to obtain the target single-ended dihydroxyalkyl-modified amino polysiloxane material of α-methyl-ω-N, N-dihydroxyethylamino-propylpolydimethylsiloxane (DEAP-PDMS). Using single-ended hydrogen-containing silicone oil with a relative molecular weight of approximately 1000–5000 g∙mol − 1 , the data for different molecular weights of α-methyl-ω-N, N-dihydroxyethylaminopropyl polydimethylsiloxane are shown in Table 1. Among them, OH-1 ~ OH-5 represents the sample numbers of α-methyl-ω-N, N-dihydroxyethylaminopropyl-polydimethylsiloxane with different molecular weights. Mn/g∙mol − 1 refers to the relative number of the average molecular weight of the sample obtained through GPC testing. η 25 /cP is the viscosity value of the testing sample at 25 ℃. n D 25 is the refractive index of the testing sample at 25 ℃. Av b /mmol∙g − 1 is the ammonia value obtained by titration. The trend of product yield shows that the higher the molecular weight of DEAP-PDMS, the more difficult it is to synthesize. Figure 1 displays an α-methyl-ω-N, N-dihydroxyethylaminopropyl-polydimethylsiloxane with a molecular weight of M NMR = 1425 g/mol determined by 1 H NMR spectrum. Its GPC curve shows typical distribution characteristics of a homolog polymer. Together with data of IR(cm − 1 ): 3500(w, υO-H), 2918, 2874(s, υC-H), 1086(v, υSi-O-Si), 1255(m, υSi-CH 3 ), 798(s, υSi-CH 3 ). 1 H-NMR(CDCl 3 ) (ppm): δ0.07(SiCH 3 ), δ0.52(SiCH 2 ), δ1.71(SiCH 2 CH 2 CH 2 N), δ2.87(CH 2 OH), δ2.96(SiCH 2 CH 2 CH 2 N), δ3.09(NCH 2 CH 2 O), δ3.91(OCH 2 CH 2 N). Table 1 Data of single-ended dihydroxyalkyl modified amino polysiloxane with different molecular weights Sample a M n/g∙mol − 1 η 25 /cP n D 25 Av b /mmol·g − 1 Yield% OH-1 1000 111.5 1.4147 1.57 90% OH-2 1500 142.6 1.4146 0.64 88% OH-3 2500 204.3 1.4045 0.52 75% OH-4 4000 207.5 1.4125 0.25 72% OH-5 5000 245.0 1.4041 0.18 64% Note: a. Type of single-ended dihydroxyalkyl modified amino polysiloxane; b. the monomer containing C = C bond. Precursor of single-ended dihydroxyalkyl-modified amino polysiloxane is α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropylpolydimethylsiloxane (TMSEAP-PDMS). It was prepared by the hydrosilylation of α, ω-di(trimethylsiloxyethyl)allyl amine (TMSEAA) with single terminal hydrogen containing silicone oil (PDMS-H) with a Karstedt catalyst. The literature said [35] that when the silicon hydride addition catalyst is a Speier catalyst, one NH 3 molecule can cause poisoning of 0.1 Pt atoms; at the same time, NH 3 generates NH 4 Cl in the presence of water, which can cause chlorine loss in the catalyst and reduce the number of acidic centers on the catalyst surface, leading to a mismatch between the metal and acidic functions of the catalyst and a decrease in catalyst activity [36]. Therefore, the amount of catalyst used should consider the amount of N-containing raw materials to resist catalyst poisoning when the Speier catalyst is used. During the experiment, it was found that using a Karstedt catalyst and adding Pt in an amount of 0.5% mol of TMSEAA can resist catalyst poisoning. In addition, another amount of Pt used in the hydrosilylation reaction, about 10 to 40 ppm (relative to the total amount of TMSEAA and PDMS-H raw materials), can achieve the hydrosilylation reaction between TMSEAA and PDMS-H. Taking PDMS-H with a relative molecular weight of about 1000 g/mol as an example, the comparison of the 1 H NMR spectra of the reaction raw materials and products (Fig. 2) shows that the conversion rate of double bonds is close to 100%, and the yield is greater than 90%. The characteristic peaks of double bond (δ 5.19ppm, δ 5.86ppm) in TMSEAA and PDMS-H’s Si-H (δ 4.75ppm) disappear, and generating the characteristic peak of -SiCH 2 - (δ 0.5ppm). 1 H-NMR(CDCl 3 ) (ppm) of the product: δ0.07(SiCH 3 ), δ0.60(SiCH 2 ), δ1.46(SiCH 2 CH 2 ), δ2.54(SiCH 2 CH 2 CH 2 N), δ2.65(NHCH 2 CH 2 O), δ3.62(NHCH 2 CH 2 O). The absorption peaks are consistent with the target product. TMSEAP-PDMS with relative molecular weights of approximately 1000, 1500, 2500, 4000, and 5000 g/mol were prepared using single-ended hydrogen-containing silicone oil (PDMS-H) with different numbers of chain links. Using a Karstedt catalyst, double-terminal dihydroxyalkyl-modified amino polysiloxane samples with a relative molecular weight of approximately 1000 to 5000 g/mol were obtained. The data for different molecular weights of double-terminal dihydroxyalkyl-modified amino polysiloxane samples are shown in Table 2. The 1 H NMR spectrum (Mn ≈ 1000 g/mol) clearly shows the characteristic peak of silicon hydrogen addition -SiCH 2 - near δ 0.5ppm in Fig. 3. Table 2 Data of double-ended dihydroxyalkyl modified amino polysiloxane with different molecular weights Sample M n/g∙mol − 1 η 25 /cP n D 25 Av b /mmol·g − 1 Yield% D OH -1 2000 63.0 1.4547 0.41 1.3 D OH -2 3000 52.0 1.4146 0.46 1.6 D OH -3 4000 51.0 1.4045 0.42 2.1 D OH -1 ~ D OH -3 represents the sample numbers of α, ω-N, N-dihydroxyethylaminopropyl-polydimethylsiloxane with different molecular weights. Mn /g∙mol − 1 refers to the relative number average molecular weight of the sample obtained through GPC testing; η 25 /cP is the viscosity value of the testing sample at 25 ℃; n D 25 is the refractive index of the testing sample at 25 ℃; Av b /mmol∙g − 1 is the ammonia value obtained by titration, and b is the monomer containing a C = C bond. 3.2 Emulsification of Dihydroxyalkylamino Modified Polydimethylsiloxane The emulsification of dihydroxyalkylamino-modified polydimethylsiloxane is affected by the molecular weight of the polysiloxane. The phase transition emulsification process from "water in oil (W/O)" to "oil in water (O/W)" is shown in Fig. 4a. The polydimethylsiloxane, with a relative molecular weight of less than 1000 g/mol has poor adhesion with the fabric surface, which affects the washability of the fabric. Then, the exploration of the emulsification for polydimethylsiloxane with a relative molecular weight of more than 1000 g/mol was conducted. The lotion successfully emulsified shows nothing on the wall in Fig. 4b, and demulsification occurs even when the test is conducted at 2000 r/min in a homogenizer. The viscosity of polydimethylsiloxane with a relative molecular weight of about 5000 g/mol is too high to fulfill the phase inversion, which makes it difficult to obtain homogeneous lotion, and there is an evident wall hanging phenomenon observed in Fig. 4c. The experimental results confirm that the relative molecular weight of the single-ended dihydroxyalkylamino modified polysiloxane is less than 5000 g/mol, and the relative molecular weight of the double-ended dihydroxyalkylamino-modified polysiloxane less than 4000 g/mol can be successfully emulsified by a mixed emulsifier. The cloth with dihydroxyalkylamino-modified polysiloxane lotion evenly coated on the surface can be obtained for performance testing. 3.3 Application of N, N-dihydroxyethylaminopropyl polydimethylsiloxane lotion with different molecular weights The hydrophilicity, softness, antistatic ability, anti-breaking ability, and whiteness of woven fabrics before and after lotion treatment were investigated by using the lotion of Single-ended or double-terminal dihydroxyalkylamino groups modified polydimethylsiloxane as fabric softeners. The test results of α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane lotion with different molecular weights after treatment of woven fabrics present in Table 3 and Table 4. Table 3 Application Test of Single-ended Dihydroxyalkylamino Polysiloxane lotion Sample M n/ g∙mol − 1 Static water absorption time /s Softness rating Fabric resistance /Ω Whiteness difference coefficient of friction breaking strength /N Fabric - > 180 2.0 3.6×10 13 - 0.649 211.20 OH-1 1000 11 3.2 2.6×10 12 4.0 0.148 383.7 OH-2 1500 20 3.3 2.2×10 12 4.0 0.146 332.2 OH-3 2500 22 3.5 2.3×10 12 5.0 0.242 532.1 OH-4 4000 32 4.1 3.6×10 12 6.6 0.252 478.1 OH-5 5000 29 4.2 3.1×10 12 5.3 0.123 433.7 The fabric is a machine woven raw fabric without any treatment, and OH-1 to OH-5 are single-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine. Table 4 Application Test of double-ended Dihydroxyalkylamino Polysiloxane lotion Sample M n/ g∙mol − 1 Static water absorption time /s Softness rating Fabric resistance /Ω Whiteness difference coefficient of friction breaking strength /N Fabric - > 180 2.0 3.6×10 13 - 0.649 211.2 D OH -1 2000 15 2.7 1.9×10 13 5.39 0.345 412.8 D OH -2 3000 25 4.0 1.9×10 12 4.28 0.279 383.8 D OH -3 4000 20 3.6 2.1×10 12 7.12 0.269 446.1 The fabric is a machine woven raw fabric without any treatment, and D OH -1 to D OH -3 are double-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine. 3.3.1 Hydrophilicity Test data shows that the static water absorption time of the woven raw fabric is greater than 180 seconds, which means that water droplets on the fabric surface do not wet for a long time, and after 180 seconds, non-reflective watermarks are basically formed at the dripping point of the fabric. The water absorption time of the woven fabric treated with single-ended dihydroxyalkylamino polysiloxane lotion is significantly reduced, the static water absorption time is 11 to 32 s, and the static water absorption time of the woven fabric treated with double-ended dihydroxyalkylamino polysiloxane lotion is 15 to 30 s. Figure 5 shows the water contact angle test of the woven fabric before and after treatment. the water contact angle of the original fabric (left) is 98.37 °, and the water contact angle of the woven fabrics treated by single-ended and double-ended dihydroxyalkylamino polysiloxane lotions is 0 ° (right). In contrast, the water contact angles of the commercial amino silicone oils are about 126.69° and 141.16° [37]. The poor hydrophilicity of amino silicone oil softener is due to the strong polarity of the amino group, with the oxygen in the polysiloxane structure, which form strong directional adsorption and good orientation to the fiber surface, resulting in hydrophobic polymer segments. However, both single-ended and double-ended dihydroxyalkylamino polydimethylsiloxane exhibit good hydrophilicity as a whole. Like amino silicone oil, the self-condensation of dihydroxyalkylamino-modified polysiloxane forms a thin film on fabrics. The hydrophilic and hydrophobic structures and properties of the film on the fiber surface can be explained in Fig. 6. Hydrophilicity is attributed to the outward extension of the hydrophilic end of hydroxyl groups in the single-ended dihydroxyalkylamino polydimethylsiloxane, which has high polarity and is prone to hydrogen bonding with water molecules. Moreover, hydrogen bond allows amino softeners modified with dihydroxyalkyl groups to improve the hydrophilic properties of woven fabrics significantly. Double-ended dihydroxyalkyl amino polydimethylsiloxane with similar molecular weight has a higher hydrophilic functional group content and shorter static water absorption time than single-ended dihydroxyalkylamino polydimethylsiloxane, which is consistent with the structural characteristics of fiber surface films. The static water absorption time of modified polydimethylsiloxane shows an increasing trend with the increase of molecular weight, which is also consistent with the structural feature that siloxane chains are hydrophobic chains, and the longer the chain is, the worse the water absorption is. 3.3.2 Softness rating A softener is a chemical substance that can adsorb on the surface of fibers, reduce the dynamic and static friction coefficients of fibers, and weaken the frictional resistance between fibers and the human body. Softness is an important indicator for measuring fabric finishing agents, and fabrics with softness can provide a comfortable sensation to the human body. The softness of the woven fabric treated with the lotion of mono-terminal dihydroxy alkylamino polysiloxane differs in relative molecular weight. The softness of the fabric treated by the lotion of mono-terminal dihydroxy alkylamino polysiloxane reaches a rate of 3.2–4.2, which is somewhat higher than 2.0 of the original fabric and usually rates higher with the increase of the molecular weight (Table 3). The higher softness rating is owing to the low surface tension of polysiloxane chains on fabrics. which will be oriented and arranged on the fabric surface, giving fibers flexibility. In addition, amino polysiloxane will undergo self-condensation on the fabric, forming a thin film, ultimately making the fiber surface smoother [38]. The state of the fiber surface can be observed by scanning electron microscope. The original woven fabric's rough and uneven surface (Fig. 7a) before fiber finishing has changed significantly after being treated with the lotion of mono-terminal dihydroxy alkylamino polydimethylsiloxane. The finished woven fabric fibers are covered with film-forming substances, and the cracks in the fibers are also filled, resulting in varying degrees of improvement in surface smoothness (7b) [37, 39]. The main component of the film-forming material on the fiber surface is polysiloxane, which has low surface tension of its chain links and is oriented and arranged on the fabric surface [2], giving the fiber softness. The amino group also undergoes self-condensation on the fabric to form a good organic silicon film and to fill the cracks in the fiber, ultimately making the fiber surface smoother [39]. The significant decrease in the friction coefficient on the surface of the fabric also indicates that the single-ended dihydroxy alkylamino-modified polysiloxane film can effectively reduce the frictional resistance between fibers, and the softness of the treated woven fabric is improved [40]. 3.3.3 Whiteness Whiteness is an important indicator for measuring fabric softeners, and low whiteness or high whiteness difference value may affect the brightness of fabric color. The amino group in the structure of dihydroxy alkylamino-modified polysiloxane is in the form of a tertiary amine group, and it was said that the tertiary amine-modified silicone oil has almost no yellowing phenomenon, which is beneficial for improving the yellowing phenomenon of amino silicone oil. The whiteness value of the woven fabric treated with dihydroxyalkylamino polysiloxane lotion has little change from that of the original fabric, which is in line with the normal yellowing value change range. Table 5 displays the whiteness value of the fabric before and after coped with lotion. The fabric treated with single-ended dihydroxyalkylamino polysiloxane with relative molecular weights of 1000 and 1500 g/mol has decreased a minimal value by 4.0, and the whiteness of the fabric treated with double-ended dihydroxyalkylamino polysiloxane with relative molecular weights of 4000 g/mol has decreased by a maximal value by 7.12. The difference in whiteness is caused by the organosilicon film formed on the surface of the fabric fiber, and most of the value difference is less than 6.0. It shows that lotion with a relative molecular weight of less than 4000 g/mol of single- or double-ended dihydroxy alkylamino polydimethylsiloxane will not affect the color brightness of the fabric. Table 5 Whiteness test data of single-ended and double-ended dihydroxyalkyl amino polysiloxane Sample M n/ g∙mol − 1 Whiteness value (Fabric) Whiteness value (Sample) Whiteness difference OH-1 1000 139.09 135.09 4.00 OH-2 1500 142.12 138.12 4.00 OH-3 2500 142.14 137.12 5.02 OH-4 4000 142.97 136.40 6.57 OH-5 5000 142.52 137.20 5.32 D OH -1 2000 142.14 136.75 5.39 D OH -2 3000 140.71 136.43 4.28 D OH -3 4000 141.80 134.68 7.12 The fabric is a machine woven raw fabric without any treatment; OH-1 to OH-5 are single-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine; and D OH -1 to D OH -3 are double-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine. 3.3.4 Antistatic performance Static electricity is a common physical phenomenon, and when static charges accumulate to a certain point, the static electricity generated by clothing may cause discomfort to the human body and may affect daily life and work. The antistatic performance of a fabric refers to its ability to reduce or prevent the accumulation of static electricity. Fabrics with high antistatic performance can quickly release static electricity, reducing the inconvenience and potential harm caused by static electricity. The resistance of a fabric is an important indicator for measuring its antistatic performance. Low-resistance fabrics can more effectively conduct charges, reduce the accumulation of static electricity, and thus improve anti-static performance. Since the resistance of the original fabric is 3.6 × 10 13 Ω, and the resistance of the woven fabric treated with single- or double-ended dihydroxyalkylamino polysiloxane lotion decreases effectively (Fig. 8). that is, the antistatic performance of the woven fabric treated with single- and double-ended dihydroxyalkylamino polysiloxane is higher than that of the woven original fabric with lower resistance to 10 12 Ω. Because hydroxyl hydrophilic groups exist in the structure of modified polydimethylsiloxane with dihydroxyalkylamino groups, the mechanism of action of antistatic agents mainly relies on the hydrophilic end to absorb water from the external environment, forming a conductive layer that can accelerates to release the charges [41], so that compared to untreated raw fabric, the introduction of hydrophilic groups make the anti-static performance improve. Among them, the resistance of single-ended modified amino silicone oil with a molar mass of about 1500 g/mol and double-ended modified amino silicone oil with a molar mass of about 3000 g/mol decreased the most, and there was a trend of decreasing anti-static performance with increasing molecular weight. The relationship between the fabric resistance and molecular weight is consistent with the fact that hydrophilic groups play a role in anti-static properties. Dihydroxyalkylamine groups are hydrophilic groups, so compared to the original fabric, the silicon oxide chains with increased molecular weight are hydrophobic chains. Suggesting that the relationship between single- and double-end dihydroxy alkylamino polydimethylsiloxane will decrease in antistatic performance with increased molecular weight, resulting in the best antistatic effect of dihydroxy alkylamino modified polysiloxane with each hydrophilic functional group matching the relative molecular weight of about 750 g/mol is achieved. Suggesting that the relationship between single- and double-end dihydroxyalkylamino polydimethylsiloxane will decrease in antistatic performance with increased molecular weight, resulting in the best anti-static effect of dihydroxyalkylamino modified polysiloxane with each hydrophilic functional group matching relative molecular weight of about 750 g/mol is achieved. The fabric is a machine woven raw fabric without any treatment; OH-1 to OH-5 are fabric treated by single-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine; and D OH -1 to D OH -3 are double-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine. 3.3.5 Mechanical Properties - Fracture Strength The breaking strength of a fabric is related to its strength, which refers to the maximum force that the fabric can withstand when stretched by external forces until it breaks. It is an important indicator for measuring the mechanical properties of a fabric and is closely related to its durability. Qualified softeners should not have adverse effects on the mechanical properties of the fabric. Figures 9a and 9b indicate that the breaking strength of the original cloth is 211.2 N, and the breaking strength of the cloth treated with the single-ended dihydroxyalkylamino polysiloxane lotion is increased to 300 ~ 500 N. Among them, the breaking strength of the cloth treated with the single-ended dihydroxy alkylamino polysiloxane lotion with a relative molecular weight of about 2500 g/mol is the highest. Moreover, the breaking strength of the cloth treated with the double-ended dihydroxyalkylamino polysiloxane lotion is more than 400 N. The data is consistent with the speculated film-forming structure state of the modified dihydroxyalkylamino polysiloxane on the fabric surface. Overall, the film formation of polysiloxane on the fiber surface can increase the toughness and fracture strength of fabrics, and the thickness of polysiloxane film formation is related to the molecular weight. The polarity of the amino group in the single-ended dihydroxyalkyl amino polysiloxane structure is high, and the interaction force with the fabric is strong. However, the dihydroxyalkyl group extends outward, and the binding effect with the fabric is small. The thickness of the film formed by polysiloxane with a relative molecular weight of around 2500 g/mol has the most substantial resistance to external forces. 4 Conclusion Single-ended dihydroxyalylamino modified polysiloxane with a relative molecular weight in the range of 1000–5000 g/mol and double-ended dihydroxyalkylamino modified polysiloxane with a relative molecular weight in the range of 2000–4000 g/ mol were prepared from diethanolamine, allyl bromide, and hydrogen-containing silicone oil, which can be uniformly emulsified by a complex emulsifier by fatty alcohol polyoxyethylene ether AE0-6 and AEO-9 in a 1:1 mass ratio. Then, it can be used as a fabric softener to treat woven fabrics and display some characterization to make them better softer than commercial amino silicone oil. Hydrophilicity and yellowing resistance are improved. Some fabric treated with dihydroxyalkylamino polysiloxane lotion not only show higher softness rate and hydrophilicity than that of the original woven fabric but also improve the antistatic ability and fracture strength of the fabric, and the tertiary amine structure does not affect the brightness of the fabric. The use of dihydroxyalkylamino-modified silicone oil has significantly improved performance when applied to softeners. Declarations Credit authorship contribution statement Weijie Yan & Yunhe Lai : Investigation; Software; Data Curation; Writing Original Draft; Yuxia Zhang : Methodology, Investigation of partial experimental data; Hong Dong : conceptualization; Table design and inspection; Yanjiang Song : Software, Writing - Review & Editing; Chuan Wu : Supervision, Conceptualization, Writing - Review & Editing. Zhirong Qu : Supervision, Validation; Funding Acquisition; Conceptualization; Writing - Review & Editing; Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. Acknowledgment Funding The authors would like to thank the Plan Project of Zhejiang Provincial Natural Science Foundation (LGG21B040002) for its financial supporting of this work. References B. Wahle, J. Falkowski, Rev. Prog. Color. Relat. Top. 2002, 32, 118. P. Habereder, A. Bereck, Rev. Prog. Color. Relat. Top. 2002, 32, 125. M.-M. Hassan, Ind. Eng. Chem. Res. 2014, 53, 10954. M.-M. Hassan, ACS Omega. 2018, 3, 17656. J.-L. Sheng, Y. Xu, J.-Y. Yu, B. Ding, ACS. Appl. Mater. Interfaces, 2017, 9, 15139. J.-L. Sheng, M. Zhang, Y. Xu, J.-Y. Yu, B. Ding, ACS. Appl. Mater. Interfaces. 2016, 8, 27218. Y.-M. Wang, D.-D. Xiao, Y. Zhong, Y.-J. Liu, L.-P. Zhang, Z.-Z Chen, X.-F. Sui, B.-J. 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Macromol. 2011, 48, 482. T.-J. Kang, M.-S. Kim, Text. Res. J. 2001, 71, 295. A.-A. Badr, J. Eng. Fibers Fabr. 2018, 13, 47. Y.-T. Yu, Q.-S. Zhang, M. Zhang, H.-F. Sun, J. Appl. Polym. Sci. 2008, 109, 2576. R.Q. Chen, TEXTILE AUXILIARIES. 2002, 19, 1. M.-S. Islam, S.-K. Lahiri, J. Nahar, M. Alomgir, IJSER, 2015, 6 1195. L.-P. Du, Z.-X. Li, D.-W. He, R.-B. Lin, TEXTILE AUXILIARIES. 2010, 27, 16. F. Wang, W.-R. Wei, W.-M. Guo, H.-P. Wang, Z.-Y Liu, China New Technologies and Products. 2012, 1, 252. H. Wang, Y.-S. Chang, H.-G. Xu, Petroleum Refinery Engineering. 2024, 54, 36. Y.-C. Cheng, Y.-X. Zhang, X. Hu, H. Dong, Z.-R. Qu, X.-Y. Cheng, T. Zhang, W. Chen, C. Wu, Phosphorus, Sulfur, and Silicon and the Related Elements. 2023, 198, 47. S. Akbaril, A. Asayesh, S. Khaliliazar, M. Razipour, N. Esmaeeli, M. Ryszard, M. Mackiewicz-Talarczyk, Handbook of Natural Fibres (2nd Edition). Volume 2: Processing and Applications. The Textile Institute Book Series. 2020, 2, 451. J.-F. Yuan, G.-B. Du, H.-X. Yang, S.-C. Liu, Y.-C. Wu, K.-L. Ni, X. Ran, W. Gao, L. Yang, J. Li, Int. J. Biol. Macromol .2022, 222, 2719. A. Adetunla, S. Afolalu, T.-C. Jen, A. Ogundana, E3S Web Conf. 2023, 391, 010012. J. Guo, X.-Y. Shen, W. Chen, Synthetic Fiber SFC. 2008, 12, 10. Schemes Schemes are available in the Supplementary Files section. Additional Declarations No competing interests reported. Supplementary Files Scheme1.png Scheme 1 Four-step reaction formula for the preparation of single ended dihydroxyamine modified polydimethylsiloxane Scheme2.png Scheme 2 Structural formula of α, ω-N, N-dihydroxyethylaminopropyl polysiloxane n:10～65 Cite Share Download PDF Status: Published Journal Publication published 15 Dec, 2025 Read the published version in Silicon → Version 1 posted Editorial decision: Revision requested 20 Oct, 2025 Reviews received at journal 03 Sep, 2025 Reviewers agreed at journal 29 Aug, 2025 Reviewers invited by journal 28 Aug, 2025 Editor assigned by journal 14 Jul, 2025 Submission checks completed at journal 14 Jul, 2025 First submitted to journal 24 Jun, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6962058","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":509439303,"identity":"3240f0e7-32c5-4d25-83fa-4a4575de0ec3","order_by":0,"name":"Weijie Yan","email":"","orcid":"","institution":"Ministry of Education, Hangzhou Normal University","correspondingAuthor":false,"prefix":"","firstName":"Weijie","middleName":"","lastName":"Yan","suffix":""},{"id":509439304,"identity":"c6eca7b9-46bc-442a-9978-0bf538218711","order_by":1,"name":"Yunhe Lai","email":"","orcid":"","institution":"Ministry of Education, Hangzhou Normal 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3","display":"","copyAsset":false,"role":"figure","size":172538,"visible":true,"origin":"","legend":"\u003cp\u003e\u003csup\u003e1\u003c/sup\u003eH-NMR spectrum of double terminal dihydroxyakylamino modified polysiloxane\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/0548c5606fcbd43b108d5a0d.png"},{"id":90573905,"identity":"9fabe85c-c4af-48b0-a384-d75953f43269","added_by":"auto","created_at":"2025-09-04 08:54:10","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":524642,"visible":true,"origin":"","legend":"\u003cp\u003eEmulsification process 4a, Homogeneouslotion state 4b and demulsification phenomenon 4c of dihydroxyalkylamino modified polysiloxane\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/07fb9152635a45e1be7b6dd1.png"},{"id":90575054,"identity":"9f02efcd-da23-47b2-8775-e3f9d04fda82","added_by":"auto","created_at":"2025-09-04 09:10:10","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":216531,"visible":true,"origin":"","legend":"\u003cp\u003eTest of water contact angle before and after treatment of woven fabric\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/22dd3848245a8e36b3760c4a.png"},{"id":90573911,"identity":"77dfa994-3acb-4291-8bf2-8fc317e82405","added_by":"auto","created_at":"2025-09-04 08:54:10","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":251358,"visible":true,"origin":"","legend":"\u003cp\u003eStructural characteristics of the thin film formed by dihydroxyalkylamino polysiloxane on fiber surface\u003c/p\u003e","description":"","filename":"6.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/6f274e2147ac4ba708278d65.png"},{"id":90573915,"identity":"bdc49e9f-2374-4d43-962c-45c126ec1250","added_by":"auto","created_at":"2025-09-04 08:54:11","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":1855798,"visible":true,"origin":"","legend":"\u003cp\u003eSEM images of original fabric (7a) and fabric treated by lotion (7b)\u003c/p\u003e","description":"","filename":"7.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/0ebe2da882d9b14a6650e9c6.png"},{"id":90574252,"identity":"58cff945-76ea-4180-a05c-06f6f6c19695","added_by":"auto","created_at":"2025-09-04 09:02:10","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":64722,"visible":true,"origin":"","legend":"\u003cp\u003eFabric resistance treated with the dihydroxyalkylamino modified polysiloxane\u003c/p\u003e","description":"","filename":"8.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/4c951da4d0635ed95ca35001.png"},{"id":90573907,"identity":"d99d9dbd-7540-4c12-a7ed-4cba58ea991b","added_by":"auto","created_at":"2025-09-04 08:54:10","extension":"png","order_by":9,"title":"Figure 9","display":"","copyAsset":false,"role":"figure","size":105097,"visible":true,"origin":"","legend":"\u003cp\u003eThe breaking strength of fabric treated by the dihydroxyalkylamino modified polysiloxane\u003c/p\u003e","description":"","filename":"9.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/72db1c224657505b974230bf.png"},{"id":98813874,"identity":"48526f1d-dc59-4e0e-8a9f-f32c828ee95f","added_by":"auto","created_at":"2025-12-22 16:06:39","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":4871551,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/9b63bc40-115c-41c1-b871-f3d31a510120.pdf"},{"id":90573900,"identity":"56a4ca63-a8b2-4220-ab06-4eb191cd5221","added_by":"auto","created_at":"2025-09-04 08:54:10","extension":"png","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":15841,"visible":true,"origin":"","legend":"\u003cp\u003eScheme 1 Four-step reaction formula for the preparation of single ended dihydroxyamine modified polydimethylsiloxane\u003c/p\u003e","description":"","filename":"Scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/7ba37552d66645d0ede8f831.png"},{"id":90574251,"identity":"9f076cf0-2a3a-42ca-b773-f1991e1a3d8c","added_by":"auto","created_at":"2025-09-04 09:02:10","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":33766,"visible":true,"origin":"","legend":"\u003cp\u003eScheme 2 Structural formula of α, ω-N, N-dihydroxyethylaminopropyl polysiloxane n:10～65\u003c/p\u003e","description":"","filename":"Scheme2.png","url":"https://assets-eu.researchsquare.com/files/rs-6962058/v1/e14a3a17ef52cdd05eeee493.png"}],"financialInterests":"No competing interests reported.","formattedTitle":"Synthesis and Application of Dihydroxyalkylamino Groups Modified Polysiloxane","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eThe main chain of polydimethylsiloxane with methyl organic groups is very flexible, with the energy required to rotate around Si-O bonds close to zero, which makes the polydimethylsiloxane chains rotate freely to angles of 360\u0026deg;. Due to the rotational freedom of Si-O-Si bonds and the low interaction energy between methyl groups on silicon atoms, organosiloxane has the advantages of low surface tension, electrical properties, softness, and thermal oxidation stability. These characteristics make organosiloxane an excellent fabric finishing agent that provides good stress\u003c/p\u003e\u003cp\u003eresilience and softness for fabrics [1,2]. In order to impart a fabric with a good feel and appearance, anti-fouling, anti-static, and other properties [3\u0026ndash;6], chemicals are widely applied to provide a finish and broaden the application range [7\u0026ndash;27]. Since amino-modified silicone softener has little effect on fabric strength and does not significantly affect the color fastness of dyed fabrics, meanwhile it endows fabrics with good washability and a \u0026ldquo;super soft\u0026rdquo; treatment effect, Amino silicone oil is a fundamental component used explicititly as a soft finishing agent for textiles. Despite being known as the \u0026ldquo;king of softeners\u0026rdquo;, it still has the drawbacks of poor hydrophilicity and susceptibility to yellowing when used as an organic silicon softener. To obtain a better comprehensive effect of an organic silicon finishing agent, multi-functional modified polysiloxane can be prepared, and other functional groups can be introduced on the basis of amino-modified organosilicon to improve the deficiency of amino silicone oil [28\u0026ndash;30]. Compared with other functional group modifications, aminoalkyl groups are commonly used to modify the main chain of polysiloxane chemically. According to the reasons for amino yellowing, converting primary amino groups into sterically hindered secondary or tertiary amino groups is an effective method to improve resistance to yellowing. Modified silicone oil with secondary and tertiary amino groups shows little yellowing phenomenon.\u003c/p\u003e\u003cp\u003eDiethanolamine (DEA) and allyl bromide were used to obtain hydroxyl-protected N, N-bis[2-(trimethylsiloxy)ethyl]allyl amine (TMSEAA). Then it reacts with hydrogen-containing silicone oil of α-trimethylsilyl-ω-dimethylsilylpolydimethylsiloxane or α, ω-dimethylsilylpolydimethyl-siloxane (PDMS-H) via hydrosilylation to produce a single or double N. N-disubstituted amino terminated polydimethylsiloxane of α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane or α,ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane (TMSEAP-PDMS). Then, N, N-dihydroxyethylamino propyl polydimethylsiloxanes (TMSEAP-PDMS) were obtained after hydroxyl deprotection. Emulsified N, N-dihydroxyalkylamino groups terminated polysiloxanes as a softener can improve the hydrophilicity and yellowing resistance of fabrics in fabric finishing applications.\u003c/p\u003e"},{"header":"2. Experimental section","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e\u003ch2\u003e2.1 Raw materials\u003c/h2\u003e\u003cp\u003eSingle-ended hydrogen-containing polysiloxane (purity greater than 97%) and double-ended hydrogen-containing silicone oil (Mn: 1000\u0026thinsp;~\u0026thinsp;5000 g/mol) were purchased from Shanghai Guangrui Biotechnology Co., Ltd. Toluene, industrial grade, was obtained from HangzhouShuanglin Chemical Co., Ltd. Allyl bromide, 98%, was obtained from Beijing Bailingwei Technology Co., Ltd.; Diethanolamine, 98%, was from Shanghai Lingfeng Chemical Reagent Co., Ltd. Karstedt\u0026rsquo;s catalyst, industrial grade, were obtained from Jiaxing United Chemical Co., Ltd. And deionized water is self-made in the laboratory.\u003c/p\u003e\u003cp\u003e\u003cstrong\u003eAmmonia value test\u003c/strong\u003e\u003cp\u003eFollow the national standard \u0026ldquo;Determination of Ammonia Value in Chemical Reagents\u0026rdquo; (GB/T 6730.35\u0026ndash;2007).\u003c/p\u003e\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec4\" class=\"Section2\"\u003e\u003ch2\u003e2.2 Experimental Instruments\u003c/h2\u003e\u003cp\u003eThe relative molecular weights of polymers were determined by a PL-GPC50 gel-permeation chromatograph from Varian (USA) with the standard polydimethylsiloxanes from American Polymer Standards Corp. \u003csup\u003e1\u003c/sup\u003eH NMR spectra of the polymers were recorded on an AVANCE AV 400MHz Nuclear Magnetic Resonance instrument (Bruker, Germany), During the test, approximately 10 mg of the liquid sample was dissolved in approximately 0.6 mL of internal standard-free deuterated chloroform (CDCl\u003csub\u003e3\u003c/sub\u003e), and the relaxation time D\u003csub\u003e1\u003c/sub\u003e was set to 5 s. Surface morphologies of polymer-treated fabrics were inspected using a ZEISS Sigma500 Scanning Electron Microscope (Germany), and the properties of polymer-treated fabrics were tested using a VPM-1A-600 pneumatic paddle and a PT-1A needle plate tenter (Japan Qianjing Dyeing Machinery Co., Ltd.). Water contact angles of polymer-treated fabrics were measured using a Kruss DSA30 water-contact angle measuring instrument (Kruss GmbH, Germany).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec5\" class=\"Section2\"\u003e\u003ch2\u003e2.3 Synthesis of Single-ended Dihydroxyalkylamino Modified Polysiloxane\u003c/h2\u003e\u003cp\u003eThe preparation of single-ended dihydroxyalkylamino-modified polysiloxane using diethanolamine (DEA) as raw material includes four steps. The corresponding chemical equation is shown in Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e\u003cp\u003eAccording to the scheme shown, the four-step synthesis includes Step 1: the reflux reaction of diethanolamine and hexamethyldisilazane to obtain bis[2-(trimethylsiloxy)ethyl]amine (TMSEA). Step 2: Add allyl bromide dropwise to TMSEA and continue the reaction to obtain N, N-bis[2-(trimethylsiloxy)ethyl]allyl amine (TMSEAA). Step 3: TMSEAA was reacted with single-ended hydrogenated silicone oil (PDMS-H) via hydrosilylation to obtain α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl] aminopropyl-polydimethylsiloxane (TMSEAP-PDMS). In step 4, the hydroxyl groups of TMSEAP-PDMS were deprotected from trimethylsilyl groups to obtain single-ended dihydroxyamine modified polysiloxane (DEAP-PDMS).\u003c/p\u003e\u003cdiv id=\"Sec6\" class=\"Section3\"\u003e\u003ch2\u003e2.3.1 Preparation of TMSEA\u003c/h2\u003e\u003cp\u003eDiethanolamine (158.0 g, 1.5 mol) was put into a 1000 mL three-necked flask equipped with a condenser, thermometer, and constant pressure dropping funnel, hexamethyldisilazane (314.0 g, 1.95 mol) was added dropwise under stirring and refluxing at 100 ℃ in 225 minutes, then raise the temperature at a rate of 10 ℃/h to 140 ℃, turn off the heating after constant stirring and refluxing for 30 hours. TMSEA, a product with hydroxyl groups protected by trimethylsilyl groups, was obtained as a transparent liquid by vacuum distillation at 140 ℃/-100 kPa. Yield 93%, and a GC purity of 99.9%. \u003csup\u003e1\u003c/sup\u003eH-NMR(CDCl\u003csub\u003e3\u003c/sub\u003e) (ppm) is consistent with the reported data [31]: δ0.11(SiC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e3\u003c/sub\u003e), δ1.98(N\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e), δ2.73(-NC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e2\u003c/sub\u003e), δ3.69(OC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e2\u003c/sub\u003e).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec7\" class=\"Section3\"\u003e\u003ch2\u003e2.3.2 Preparation of TMSEAA\u003c/h2\u003e\u003cp\u003e8 g of TMSEA was added to a three-necked flask and cooled to 5 ℃; 25.4 g of allyl bromide was added dropwise. When the yellow color of the solution was observed to be more pronounced, remove the ice bath and let the temperature gradually rise, and then the flak was placed into an oil bath with a temperature set to 40 ℃. A NaOH solution with a mass fraction of 20% was added slowly to provide the system with a weakly alkaline state and facilitated the reaction to proceed in the positive direction. Terminated the reaction 2 hours later than dropwise addition of allyl bromide finished, to do extraction with CH\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003e, followed by fractional distillation of the oil phase to remove the solvent and the low boiling substances from the system, then the residue was further purified by vacuum distillation to get N, N-bis[2-(trimethyl siloxy)ethyl]allylamine (TMSEAA) with a yield of 51.2%, GC-MS purity of 99%. \u003csup\u003e1\u003c/sup\u003eH-NMR(CDCl\u003csub\u003e3\u003c/sub\u003e) (ppm) data is consistent with reported before [31]: δ0.12(SiC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e3\u003c/sub\u003e), δ2.60(OCH\u003csub\u003e2\u003c/sub\u003eC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e2\u003c/sub\u003eN), δ3.03(CH\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;CHC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e2\u003c/sub\u003eN), δ3.67(OC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eN), δ5.19(C\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;CHCH\u003csub\u003e2\u003c/sub\u003eN) And δ5.86(CH\u003csub\u003e2\u003c/sub\u003e\u0026thinsp;=\u0026thinsp;C\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003eCH\u003csub\u003e2\u003c/sub\u003eN).\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec8\" class=\"Section3\"\u003e\u003ch2\u003e2.3.3 Preparation of TMSEAP-PDMS\u003c/h2\u003e\u003cp\u003e15 mL of dry toluene (content of H\u003csub\u003e2\u003c/sub\u003eO is about 200ppm), 1.09g (3.76 \u0026times; 10-3mol) of TMSEAA, and 0.38g of 1wt% Pt in Karstedt catalyst were put to a 100mL three necked flask with N\u003csub\u003e2\u003c/sub\u003e protection. After the mixture was stirred and activated at 70 ℃ for 30 minutes, 15.5g of single-ended hydrogen-containing silicone oil (PDMS-H) was uniformly added by an injection pump with an injection time of 1.5 hours. Continued the reaction at 70 ℃ for 10 hours and then cooled to room temperature. The system was left open to inactivate the catalyst, and the product was subjected to vacuum distillation to remove low boiling materials, resulting in the addition product α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane with a yield of 82.0%. A series of single-ended dihydroxyalkyl-modified amino polysiloxanes with hydroxyl groups protected by TMS (trimethylsilyl) groups were prepared by reacting PDMS-H with different molecular weights.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec9\" class=\"Section3\"\u003e\u003ch2\u003e2.3.4 Preparation of DEAP-PDMS\u003c/h2\u003e\u003cp\u003eThe target product, single-ended dihydroxyalkyl-modified amino polysiloxane (DEAP-PDMS), was obtained by deprotection of trimethylsilyl-protected single-ended dihydroxyalkyl-modified amino polysiloxane TMSEAP-PDMS. For example, using a single-ended hydrogen-containing silicone oil with a relative molecular weight \u003cem\u003eMn\u003c/em\u003e of about 1000 g/mol as the raw material, the conversion rate of the raw material is greater than 90%, but the conversion rate decreases as the molecular weight increases.\u003c/p\u003e\u003cp\u003eTo 14.5 g of TMSEAP-PDMS (Mn\u0026thinsp;\u0026asymp;\u0026thinsp;5000 g/mol), 0.1 g (1.67 \u0026times; 10\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e mol) of acetic acid and 4.6 g of methanol were added to a 100mL three-necked flask. The mixture was stirred and raised to 65 ℃ for 6 hours. The low boiling point was removed by vacuum distillation to obtain the target product single terminal dihydroxyalkyl-modified amino polysiloxane of α-methyl-ω-N, N-dihydroxyethylaminopropyl polydimethylsiloxane, with a yield of 64% (Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e, OH-5). A series of single-ended dihydroxyalkyl-modified amino polydimethylsiloxane samples with a relative molecular weight of approximately 1000\u0026thinsp;~\u0026thinsp;5000 g/mol are shown in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec10\" class=\"Section3\"\u003e\u003ch2\u003e2.3.5 Preparation of Polydimethylsiloxane Modified with Double Terminal Dihydroxyamine Groups\u003c/h2\u003e\u003cp\u003eTMSEAA reacted with double-terminal hydrogen-containing silicone oils will obtain double-terminal dihydroxyalkyl modified amino polydimethylsiloxane. Structural formula of α, ω-N, N-dihydroxyethylaminopropyl polydimethylsiloxane is shown in Scheme \u003cspan refid=\"Sch2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, with the repeat unit numbers from 10 to 65.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e\u003c/div\u003e\u003c/div\u003e\u003cdiv id=\"Sec11\" class=\"Section2\"\u003e\u003ch2\u003e2.4 Preparation the lotion of dihydroxyalkyl modified amino polysiloxane\u003c/h2\u003e\u003cp\u003eThe dihydroxyalkyl-modified amino polysiloxane can be successfully emulsified by a mixed emulsifier of polyoxyethylene ether AE0-6 and AEO-9 in a 1:1 mass ratio. When the dosage of the emulsifier is 6% and 1wt% of acetic acid used as a catalyst were applied to transfer a certain amount of dihydroxyalkyl-modified amino polysiloxane into lotion, a small amount of water can achieve phase transition. When the total mass fraction of water reaches 73%, it will change from \"water in oil (W/O)\" to \"oil in water (O/W)\" and become a lotion after passing the phase inversion point. When the lotion was tested at 2000 r/min in the homogenizer, no phenomenon of demulsification occurred. After phase inversion, dilute 6 g lotion with 200 g water to obtain a stable O/W lotion. Furthermore, the diluted lotion was used as a fabric softener to test the fabric finishing performance.\u003c/p\u003e\u003c/div\u003e\u003cdiv id=\"Sec12\" class=\"Section2\"\u003e\u003ch2\u003e2.5 Application of Dihydroxyalkyl Amino Modified Polysiloxane Lotion\u003c/h2\u003e\u003cdiv id=\"Sec13\" class=\"Section3\"\u003e\u003ch2\u003e2.5.1 Application method of lotion\u003c/h2\u003e\u003cp\u003eSince amino silicone oil is a fundamental component used explicitly as a textile softening agent, with the best adsorption, compatibility, and emulsifying properties, it is suitable for various textile softening treatments. Amino silicone oil can be easily emulsified into stable and transparent micro-emulsion by appropriate surfactant. It can be used alone or combined with other organic silicon or organic softeners to form special softening finishing agents. As literature reports [32\u0026ndash;34], Since there are primary and secondary amino groups present in the structure of commercially available amino silicone oil, the yellowing mechanism is caused by the oxidation and decomposition of amino groups to form azo and oxidized azo chromophores, resulting in yellowing of the fabric. Among the side chain amino groups, the dual amine type of amino silicone oil showed the most severe yellowing, followed by the primary amino group. The modified silicone oil with secondary and tertiary amine groups showed little yellowing phenomenon. The lotion made by adding an emulsifier to the amino silicone oil is often used as a fabric treatment agent to improve the softness, crease resistance, elasticity, and tear resistance significantly. The application testing method is as follows.\u003c/p\u003e\u003cp\u003eCut the woven fabric into an A\u003csub\u003e4\u003c/sub\u003e paper size and conduct tests on its whiteness, hydrophilicity, antistatic performance, and softness after soaking, shaping, and moisture regain. The fabric processing and testing methods are:\u003c/p\u003e\u003cp\u003e(1) Dipping: Soak the woven fabric in lotion for about 10 s and then pass through the rolling car. The wet woven fabric is preliminarily shaped by a rolling mill through a process of immersion and rolling;\u003c/p\u003e\u003cp\u003e(2) Molding: The fabric that has been rolled is taken out and passed through a molding machine at 160 ℃ for a total of 60 seconds at a speed of 4 m/min. The fabric that has been taken out and passed through the molding machine is then allowed to regain moisture for 1 hour;\u003c/p\u003e\u003cp\u003e(3) Whiteness test: After moisture is regained, the fabric is placed on a colorimeter for whiteness testing. The fabric is folded into four layers and tested four times, with an automatic average reading of the four values;\u003c/p\u003e\u003cp\u003e(4) Hydrophilicity test: Fix the moisture fabric sample on the stretch cloth ring, use a dropper with a rubber head to drop a water droplet at a height of 1 cm from the fabric surface, and start timing. When the water droplet decreases to a non-reflective watermark, stop timing. Hydrophilicity can also be expressed by the water contact angle of the fabric after the immersion rolling process treatment. Under the same soaking and rolling process, the length of water absorption time of the measuring sample cloth indicates poorer water absorption;\u003c/p\u003e\u003cp\u003e(5) Antistatic performance test: Use a resistance electrostatic tester. Preheat the instrument before testing, cut the woven fabric that has been dipped and rolled into 45 mm \u0026times; 45 mm, and place it in an environment with a humidity of 29.6% RH and a temperature of 20.2 ℃ for 5 hours before testing;\u003c/p\u003e\u003cp\u003e(6) Softness testing: Indicators such as softness and hand feel are subjective evaluation indicators, mainly obtained through the tester's tactile sensation to obtain evaluation results;\u003c/p\u003e\u003cp\u003e(7) Tear strength shall be tested using a drop hammer fabric tear tester in accordance with GB/T 3917.1 standard. The sliding friction force is tested according to the GB/T 3925\u0026thinsp;\u0026minus;\u0026thinsp;2009 standard using a friction coefficient tester. The fracture strength is tested according to ASTM D638 standard using a universal material testing machine.\u003c/p\u003e\u003c/div\u003e\u003c/div\u003e"},{"header":"3. Results and Discussion","content":"\u003cdiv id=\"Sec15\"\u003e\n \u003ch2\u003e3.1 Preparation of dihydroxyamine modified polydimethylsiloxane by hydrosilylation\u003c/h2\u003e\n \u003cp\u003eSingle-ended hydrogen-containing silicone oil (PDMS-H) was used as the key component to undergo hydrosilylation with N, N-bis[2-(trimethylsiloxy)ethyl]allyl-amine (TMSEAA) under the action of Karlstedt catalyst, resulting in TMS protected hydroxylalkylamino polysiloxane of α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl] aminopropylpolydimethylsiloxane (TMSEAP-PDMS). Then, under acidic conditions, the TMS group was removed to obtain the target single-ended dihydroxyalkyl-modified amino polysiloxane material of α-methyl-ω-N, N-dihydroxyethylamino-propylpolydimethylsiloxane (DEAP-PDMS). Using single-ended hydrogen-containing silicone oil with a relative molecular weight of approximately 1000–5000 g∙mol\u003csup\u003e− 1\u003c/sup\u003e, the data for different molecular weights of α-methyl-ω-N, N-dihydroxyethylaminopropyl polydimethylsiloxane are shown in Table 1. Among them, OH-1 ~ OH-5 represents the sample numbers of α-methyl-ω-N, N-dihydroxyethylaminopropyl-polydimethylsiloxane with different molecular weights. Mn/g∙mol\u003csup\u003e− 1\u003c/sup\u003e refers to the relative number of the average molecular weight of the sample obtained through GPC testing. η\u003csup\u003e25\u003c/sup\u003e/cP is the viscosity value of the testing sample at 25 ℃. \u003cem\u003en\u003c/em\u003e\u003csub\u003eD\u003c/sub\u003e\u003csup\u003e25\u003c/sup\u003e is the refractive index of the testing sample at 25 ℃. \u003cem\u003eAv\u003c/em\u003e\u003csup\u003eb\u003c/sup\u003e/mmol∙g\u003csup\u003e− 1\u003c/sup\u003e is the ammonia value obtained by titration. The trend of product yield shows that the higher the molecular weight of DEAP-PDMS, the more difficult it is to synthesize. Figure 1 displays an α-methyl-ω-N, N-dihydroxyethylaminopropyl-polydimethylsiloxane with a molecular weight of M\u003csub\u003eNMR\u003c/sub\u003e = 1425 g/mol determined by \u003csup\u003e1\u003c/sup\u003eH NMR spectrum. Its GPC curve shows typical distribution characteristics of a homolog polymer. Together with data of IR(cm\u003csup\u003e− 1\u003c/sup\u003e): 3500(w, υO-H), 2918, 2874(s, υC-H), 1086(v, υSi-O-Si), 1255(m, υSi-CH\u003csub\u003e3\u003c/sub\u003e), 798(s, υSi-CH\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e1\u003c/sup\u003eH-NMR(CDCl\u003csub\u003e3\u003c/sub\u003e) (ppm): δ0.07(SiCH\u003csub\u003e3\u003c/sub\u003e), δ0.52(SiCH\u003csub\u003e2\u003c/sub\u003e), δ1.71(SiCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eN), δ2.87(CH\u003csub\u003e2\u003c/sub\u003eOH), δ2.96(SiCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eN), δ3.09(NCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eO), δ3.91(OCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eN).\u003c/p\u003e\n \u003cdiv\u003e\n \u003ctable id=\"Tab1\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 1\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eData of single-ended dihydroxyalkyl modified amino polysiloxane with different molecular weights\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSample\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eM\u003c/em\u003en/g∙mol\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eη\u003c/em\u003e\u003csub\u003e25\u003c/sub\u003e/cP\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003en\u003c/em\u003e\u003csub\u003eD\u003c/sub\u003e\u003csup\u003e25\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eAv\u003c/em\u003e\u003csup\u003eb\u003c/sup\u003e/mmol·g\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield%\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e111.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4147\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.57\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e90%\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e142.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4146\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.64\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e88%\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e204.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4045\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.52\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75%\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e207.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4125\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e72%\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e245.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4041\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e64%\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003ctfoot\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"6\"\u003eNote: a. Type of single-ended dihydroxyalkyl modified amino polysiloxane; b. the monomer containing C = C bond.\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tfoot\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003ePrecursor of single-ended dihydroxyalkyl-modified amino polysiloxane is α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropylpolydimethylsiloxane (TMSEAP-PDMS). It was prepared by the hydrosilylation of α, ω-di(trimethylsiloxyethyl)allyl amine (TMSEAA) with single terminal hydrogen containing silicone oil (PDMS-H) with a Karstedt catalyst. The literature said [35] that when the silicon hydride addition catalyst is a Speier catalyst, one NH\u003csub\u003e3\u003c/sub\u003e molecule can cause poisoning of 0.1 Pt atoms; at the same time, NH\u003csub\u003e3\u003c/sub\u003e generates NH\u003csub\u003e4\u003c/sub\u003eCl in the presence of water, which can cause chlorine loss in the catalyst and reduce the number of acidic centers on the catalyst surface, leading to a mismatch between the metal and acidic functions of the catalyst and a decrease in catalyst activity [36]. Therefore, the amount of catalyst used should consider the amount of N-containing raw materials to resist catalyst poisoning when the Speier catalyst is used.\u003c/p\u003e\n \u003cp\u003eDuring the experiment, it was found that using a Karstedt catalyst and adding Pt in an amount of 0.5% mol of TMSEAA can resist catalyst poisoning. In addition, another amount of Pt used in the hydrosilylation reaction, about 10 to 40 ppm (relative to the total amount of TMSEAA and PDMS-H raw materials), can achieve the hydrosilylation reaction between TMSEAA and PDMS-H. Taking PDMS-H with a relative molecular weight of about 1000 g/mol as an example, the comparison of the \u003csup\u003e1\u003c/sup\u003eH NMR spectra of the reaction raw materials and products (Fig. 2) shows that the conversion rate of double bonds is close to 100%, and the yield is greater than 90%. The characteristic peaks of double bond (δ 5.19ppm, δ 5.86ppm) in TMSEAA and PDMS-H’s Si-H (δ 4.75ppm) disappear, and generating the characteristic peak of -SiCH\u003csub\u003e2\u003c/sub\u003e- (δ 0.5ppm). \u003csup\u003e1\u003c/sup\u003eH-NMR(CDCl\u003csub\u003e3\u003c/sub\u003e) (ppm) of the\u003c/p\u003e\n \u003cp\u003eproduct: δ0.07(SiCH\u003csub\u003e3\u003c/sub\u003e), δ0.60(SiCH\u003csub\u003e2\u003c/sub\u003e), δ1.46(SiCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003e), δ2.54(SiCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eN), δ2.65(NHCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eO), δ3.62(NHCH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e2\u003c/sub\u003eO). The absorption peaks are consistent with the target product. TMSEAP-PDMS with relative molecular weights of approximately 1000, 1500, 2500, 4000, and 5000 g/mol were prepared using single-ended hydrogen-containing silicone oil (PDMS-H) with different numbers of chain links.\u003c/p\u003e\n \u003cp\u003eUsing a Karstedt catalyst, double-terminal dihydroxyalkyl-modified amino polysiloxane samples with a relative molecular weight of approximately 1000 to 5000 g/mol were obtained. The data for different molecular weights of double-terminal dihydroxyalkyl-modified amino polysiloxane samples are shown in Table 2. The \u003csup\u003e1\u003c/sup\u003eH NMR spectrum (Mn ≈ 1000 g/mol) clearly shows the characteristic peak of silicon hydrogen addition -SiCH\u003csub\u003e2\u003c/sub\u003e- near δ 0.5ppm in Fig. 3.\u003c/p\u003e\n \u003cdiv\u003e\n \u003ctable id=\"Tab2\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 2\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eData of double-ended dihydroxyalkyl modified amino polysiloxane with different molecular weights\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSample\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eM\u003c/em\u003en/g∙mol\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eη\u003c/em\u003e\u003csub\u003e25\u003c/sub\u003e/cP\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003en\u003c/em\u003e\u003csub\u003eD\u003c/sub\u003e\u003csup\u003e25\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eAv\u003c/em\u003e\u003csup\u003eb\u003c/sup\u003e/mmol·g\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield%\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e63.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4547\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.41\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.3\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e52.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4146\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.46\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e51.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.4045\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.42\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-1 ~ D\u003csub\u003eOH\u003c/sub\u003e-3 represents the sample numbers of α, ω-N, N-dihydroxyethylaminopropyl-polydimethylsiloxane with different molecular weights. \u003cem\u003eMn\u003c/em\u003e/g∙mol\u003csup\u003e− 1\u003c/sup\u003e refers to the relative number average molecular weight of the sample obtained through GPC testing; η\u003csup\u003e25\u003c/sup\u003e/cP is the viscosity value of the testing sample at 25 ℃; n\u003csub\u003eD\u003c/sub\u003e\u003csup\u003e25\u003c/sup\u003e is the refractive index of the testing sample at 25 ℃; \u003cem\u003eAv\u003c/em\u003e\u003csup\u003eb\u003c/sup\u003e/mmol∙g\u003csup\u003e− 1\u003c/sup\u003e is the ammonia value obtained by titration, and b is the monomer containing a C = C bond.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec16\"\u003e\n \u003ch2\u003e3.2 Emulsification of Dihydroxyalkylamino Modified Polydimethylsiloxane\u003c/h2\u003e\n \u003cp\u003eThe emulsification of dihydroxyalkylamino-modified polydimethylsiloxane is affected by the molecular weight of the polysiloxane. The phase transition emulsification process from \"water in oil (W/O)\" to \"oil in water (O/W)\" is shown in Fig.\u0026nbsp;4a. The polydimethylsiloxane, with a relative molecular weight of less than 1000 g/mol has poor adhesion with the fabric surface, which affects the washability of the fabric. Then, the exploration of the emulsification for polydimethylsiloxane with a relative molecular weight of more than 1000 g/mol was conducted. The lotion successfully emulsified shows nothing on the wall in Fig.\u0026nbsp;4b, and demulsification occurs even when the test is conducted at 2000 r/min in a homogenizer. The viscosity of polydimethylsiloxane with a relative molecular weight of about 5000 g/mol is too high to fulfill the phase inversion, which makes it difficult to obtain homogeneous lotion, and there is an evident wall hanging phenomenon observed in Fig.\u0026nbsp;4c. The experimental results confirm that the relative molecular weight of the single-ended dihydroxyalkylamino modified polysiloxane is less than 5000 g/mol, and the relative molecular weight of the double-ended dihydroxyalkylamino-modified polysiloxane less than 4000 g/mol can be successfully emulsified by a mixed emulsifier. The cloth with dihydroxyalkylamino-modified polysiloxane lotion evenly coated on the surface can be obtained for performance testing.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec18\"\u003e\n \u003ch2\u003e3.3 Application of N, N-dihydroxyethylaminopropyl polydimethylsiloxane lotion with different molecular weights\u003c/h2\u003e\n \u003cp\u003eThe hydrophilicity, softness, antistatic ability, anti-breaking ability, and whiteness of woven fabrics before and after lotion treatment were investigated by using the lotion of Single-ended or double-terminal dihydroxyalkylamino groups modified polydimethylsiloxane as fabric softeners. The test results of α-methyl-ω-N, N-bis[2-(trimethylsiloxy)ethyl]aminopropyl polydimethylsiloxane lotion with different molecular weights after treatment of woven fabrics present in Table 3 and Table 4.\u003c/p\u003e\n \u003cdiv\u003e\n \u003ctable id=\"Tab3\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 3\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eApplication Test of Single-ended Dihydroxyalkylamino Polysiloxane lotion\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSample\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eM\u003c/em\u003en/ g∙mol\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eStatic water absorption time /s\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSoftness rating\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eFabric resistance /Ω\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eWhiteness difference\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003ecoefficient of friction\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003ebreaking strength /N\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eFabric\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u0026gt; 180\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.6×10\u003csup\u003e13\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.649\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e211.20\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.6×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.148\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e383.7\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.2×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.146\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e332.2\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e22\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.3×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.242\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e532.1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.6×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.252\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e478.1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e29\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.1×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.123\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e433.7\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eThe fabric is a machine woven raw fabric without any treatment, and OH-1 to OH-5 are single-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine.\u003c/p\u003e\n \u003cdiv\u003e\n \u003ctable id=\"Tab4\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 4\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eApplication Test of double-ended Dihydroxyalkylamino Polysiloxane lotion\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSample\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eM\u003c/em\u003en/ g∙mol\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eStatic water absorption time /s\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSoftness rating\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eFabric resistance /Ω\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eWhiteness difference\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003ecoefficient of friction\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003ebreaking strength /N\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eFabric\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u0026gt; 180\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.6×10\u003csup\u003e13\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.649\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e211.2\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.9×10\u003csup\u003e13\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5.39\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.345\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e412.8\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1.9×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4.28\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.279\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e383.8\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2.1×10\u003csup\u003e12\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7.12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e0.269\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e446.1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eThe fabric is a machine woven raw fabric without any treatment, and D\u003csub\u003eOH\u003c/sub\u003e-1 to D\u003csub\u003eOH\u003c/sub\u003e-3 are double-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine.\u003c/p\u003e\n \u003cdiv id=\"Sec19\"\u003e\n \u003ch2\u003e3.3.1 Hydrophilicity\u003c/h2\u003e\n \u003cp\u003eTest data shows that the static water absorption time of the woven raw fabric is greater than 180 seconds, which means that water droplets on the fabric surface do not wet for a long time, and after 180 seconds, non-reflective watermarks are basically formed at the dripping point of the fabric. The water absorption time of the woven fabric treated with single-ended dihydroxyalkylamino polysiloxane lotion is significantly reduced, the static water absorption time is 11 to 32 s, and the static water absorption time of the woven fabric treated with double-ended dihydroxyalkylamino polysiloxane lotion is 15 to 30 s.\u003c/p\u003e\n \u003cp\u003eFigure 5 shows the water contact angle test of the woven fabric before and after treatment. the water contact angle of the original fabric (left) is 98.37 °, and the water contact angle of the woven fabrics treated by single-ended and double-ended dihydroxyalkylamino polysiloxane lotions is 0 ° (right). In contrast, the water contact angles of the commercial amino silicone oils are about 126.69° and 141.16° [37].\u003c/p\u003e\n \u003cp\u003eThe poor hydrophilicity of amino silicone oil softener is due to the strong polarity of the amino group, with the oxygen in the polysiloxane structure, which form strong directional adsorption and good orientation to the fiber surface, resulting in hydrophobic polymer segments. However, both single-ended and double-ended dihydroxyalkylamino polydimethylsiloxane exhibit good hydrophilicity as a whole. Like amino silicone oil, the self-condensation of dihydroxyalkylamino-modified polysiloxane forms a thin film on fabrics. The hydrophilic and hydrophobic structures and properties of the film on the fiber surface can be explained in Fig. 6. Hydrophilicity is attributed to the outward extension of the hydrophilic end of hydroxyl groups in the single-ended dihydroxyalkylamino polydimethylsiloxane, which has high polarity and is prone to hydrogen bonding with water molecules. Moreover, hydrogen bond allows amino softeners modified with dihydroxyalkyl groups to improve the hydrophilic properties of woven fabrics significantly. Double-ended dihydroxyalkyl amino polydimethylsiloxane with similar molecular weight has a higher hydrophilic functional group content and shorter static water absorption time than single-ended dihydroxyalkylamino polydimethylsiloxane, which is consistent with the structural characteristics of fiber surface films. The static water absorption time of modified polydimethylsiloxane shows an increasing trend with the increase of molecular weight, which is also consistent with the structural feature that siloxane chains are hydrophobic chains, and the longer the chain is, the worse the water absorption is.\u003c/p\u003e\n \u003c/div\u003e\n \u003cdiv id=\"Sec20\"\u003e\n \u003ch2\u003e3.3.2 Softness rating\u003c/h2\u003e\n \u003cp\u003eA softener is a chemical substance that can adsorb on the surface of fibers, reduce the dynamic and static friction coefficients of fibers, and weaken the frictional resistance between fibers and the human body. Softness is an important indicator for measuring fabric finishing agents, and fabrics with softness can provide a comfortable sensation to the human body.\u003c/p\u003e\n \u003cp\u003eThe softness of the woven fabric treated with the lotion of mono-terminal dihydroxy alkylamino polysiloxane differs in relative molecular weight. The softness of the fabric treated by the lotion of mono-terminal dihydroxy alkylamino polysiloxane reaches a rate of 3.2–4.2, which is somewhat higher than 2.0 of the original fabric and usually rates higher with the increase of the molecular weight (Table 3). The higher softness rating is owing to the low surface tension of polysiloxane chains on fabrics. which will be oriented and arranged on the fabric surface, giving fibers flexibility. In addition, amino polysiloxane will undergo self-condensation on the fabric, forming a thin film, ultimately making the fiber surface smoother [38]. The state of the fiber surface can be observed by scanning electron microscope. The original woven fabric's rough and uneven surface (Fig. 7a) before fiber finishing has changed significantly after being treated with the lotion of mono-terminal dihydroxy alkylamino polydimethylsiloxane. The finished woven fabric fibers are covered with film-forming substances, and the cracks in the fibers are also filled, resulting in varying degrees of improvement in surface smoothness (7b) [37, 39].\u003c/p\u003e\n \u003cp\u003eThe main component of the film-forming material on the fiber surface is polysiloxane, which has low surface tension of its chain links and is oriented and arranged on the fabric surface [2], giving the fiber softness. The amino group also undergoes self-condensation on the fabric to form a good organic silicon film and to fill the cracks in the fiber, ultimately making the fiber surface smoother [39]. The significant decrease in the friction coefficient on the surface of the fabric also indicates that the single-ended dihydroxy alkylamino-modified polysiloxane film can effectively reduce the frictional resistance between fibers, and the softness of the treated woven fabric is improved [40].\u003c/p\u003e\n \u003c/div\u003e\n \u003cdiv id=\"Sec21\"\u003e\n \u003ch2\u003e3.3.3 Whiteness\u003c/h2\u003e\n \u003cp\u003eWhiteness is an important indicator for measuring fabric softeners, and low whiteness or high whiteness difference value may affect the brightness of fabric color. The amino group in the structure of dihydroxy alkylamino-modified polysiloxane is in the form of a tertiary amine group, and it was said that the tertiary amine-modified silicone oil has almost no yellowing phenomenon, which is beneficial for improving the yellowing phenomenon of amino silicone oil. The whiteness value of the woven fabric treated with dihydroxyalkylamino polysiloxane lotion has little change from that of the original fabric, which is in line with the normal yellowing value change range. Table 5 displays the whiteness value of the fabric before and after coped with lotion. The fabric treated with single-ended dihydroxyalkylamino polysiloxane with relative molecular weights of 1000 and 1500 g/mol has decreased a minimal value by 4.0, and the whiteness of the fabric treated with double-ended dihydroxyalkylamino polysiloxane with relative molecular weights of 4000 g/mol has decreased by a maximal value by 7.12. The difference in whiteness is caused by the organosilicon film formed on the surface of the fabric fiber, and most of the value difference is less than 6.0. It shows that lotion with a relative molecular weight of less than 4000 g/mol of single- or double-ended dihydroxy alkylamino polydimethylsiloxane will not affect the color brightness of the fabric.\u003c/p\u003e\n \u003cdiv\u003e\n \u003ctable id=\"Tab5\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 5\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eWhiteness test data of single-ended and double-ended dihydroxyalkyl amino polysiloxane\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSample\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e\u003cem\u003eM\u003c/em\u003en/ g∙mol\u003csup\u003e− 1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eWhiteness value (Fabric)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eWhiteness value\u003c/p\u003e\n \u003cp\u003e(Sample)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eWhiteness difference\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e139.09\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e135.09\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4.00\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e1500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e142.12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e138.12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4.00\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2500\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e142.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e137.12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5.02\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e142.97\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e136.40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e6.57\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOH-5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e142.52\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e137.20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5.32\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e2000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e142.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e136.75\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5.39\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e3000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e140.71\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e136.43\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4.28\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eD\u003csub\u003eOH\u003c/sub\u003e-3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e4000\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e141.80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e134.68\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e7.12\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003eThe fabric is a machine woven raw fabric without any treatment; OH-1 to OH-5 are single-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine; and D\u003csub\u003eOH\u003c/sub\u003e-1 to D\u003csub\u003eOH\u003c/sub\u003e-3 are double-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine.\u003c/p\u003e\n \u003c/div\u003e\n \u003cdiv id=\"Sec22\"\u003e\n \u003ch2\u003e3.3.4 Antistatic performance\u003c/h2\u003e\n \u003cp\u003eStatic electricity is a common physical phenomenon, and when static charges accumulate to a certain point, the static electricity generated by clothing may cause discomfort to the human body and may affect daily life and work. The antistatic performance of a fabric refers to its ability to reduce or prevent the accumulation of static electricity. Fabrics with high antistatic performance can quickly release static electricity, reducing the inconvenience and potential harm caused by static electricity. The resistance of a fabric is an important indicator for measuring its antistatic performance. Low-resistance fabrics can more effectively conduct charges, reduce the accumulation of static electricity, and thus improve anti-static performance. Since the resistance of the original fabric is 3.6 × 10\u003csup\u003e13\u003c/sup\u003e Ω, and the resistance of the woven fabric treated with single- or double-ended dihydroxyalkylamino polysiloxane lotion decreases effectively (Fig. 8). that is, the antistatic performance of the woven fabric treated with single- and double-ended dihydroxyalkylamino polysiloxane is higher than that of the woven original fabric with lower resistance to 10\u003csup\u003e12\u003c/sup\u003e Ω. Because hydroxyl hydrophilic groups exist in the structure of modified polydimethylsiloxane with dihydroxyalkylamino groups, the mechanism of action of antistatic agents mainly relies on the hydrophilic end to absorb water from the external environment, forming a conductive layer that can accelerates to release the charges [41], so that compared to untreated raw fabric, the introduction of hydrophilic groups make the anti-static performance improve. Among them, the resistance of single-ended modified amino silicone oil with a molar mass of about 1500 g/mol and double-ended modified amino silicone oil with a molar mass of about 3000 g/mol decreased the most, and there was a trend of decreasing anti-static performance with increasing molecular weight. The relationship between the fabric resistance and molecular weight is consistent with the fact that hydrophilic groups play a role in anti-static properties. Dihydroxyalkylamine groups are hydrophilic groups, so compared to the original fabric, the silicon oxide chains with increased molecular weight are hydrophobic chains. Suggesting that the relationship between single- and double-end dihydroxy alkylamino polydimethylsiloxane will decrease in antistatic performance with increased molecular weight, resulting in the best antistatic effect of dihydroxy alkylamino modified polysiloxane with each hydrophilic functional group matching the relative molecular weight of about 750 g/mol is achieved. Suggesting that the relationship between single- and double-end dihydroxyalkylamino polydimethylsiloxane will decrease in antistatic performance with increased molecular weight, resulting in the best anti-static effect of dihydroxyalkylamino modified polysiloxane with each hydrophilic functional group matching relative molecular weight of about 750 g/mol is achieved.\u003c/p\u003e\n \u003cp\u003eThe fabric is a machine woven raw fabric without any treatment; OH-1 to OH-5 are fabric treated by single-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine; and D\u003csub\u003eOH\u003c/sub\u003e-1 to D\u003csub\u003eOH\u003c/sub\u003e-3 are double-ended dihydroxyalkylamino polydimethylsiloxane woven by the processing machine.\u003c/p\u003e\n \u003c/div\u003e\n \u003cdiv id=\"Sec23\"\u003e\n \u003ch2\u003e3.3.5 Mechanical Properties - Fracture Strength\u003c/h2\u003e\n \u003cp\u003eThe breaking strength of a fabric is related to its strength, which refers to the maximum force that the fabric can withstand when stretched by external forces until it breaks. It is an important indicator for measuring the mechanical properties of a fabric and is closely related to its durability. Qualified softeners should not have adverse effects on the mechanical properties of the fabric. Figures\u0026nbsp;9a and 9b indicate that the breaking strength of the original cloth is 211.2 N, and the breaking strength of the cloth treated with the single-ended dihydroxyalkylamino polysiloxane lotion is increased to 300 ~ 500 N. Among them, the breaking strength of the cloth treated with the single-ended dihydroxy alkylamino polysiloxane lotion with a relative molecular weight of about 2500 g/mol is the highest. Moreover, the breaking strength of the cloth treated with the double-ended dihydroxyalkylamino polysiloxane lotion is more than 400 N.\u003c/p\u003e\n \u003cp\u003eThe data is consistent with the speculated film-forming structure state of the modified dihydroxyalkylamino polysiloxane on the fabric surface. Overall, the film formation of polysiloxane on the fiber surface can increase the toughness and fracture strength of fabrics, and the thickness of polysiloxane film formation is related to the molecular weight. The polarity of the amino group in the single-ended dihydroxyalkyl amino polysiloxane structure is high, and the interaction force with the fabric is strong. However, the dihydroxyalkyl group extends outward, and the binding effect with the fabric is small. The thickness of the film formed by polysiloxane with a relative molecular weight of around 2500 g/mol has the most substantial resistance to external forces.\u003c/p\u003e\n \u003c/div\u003e\n\u003c/div\u003e"},{"header":"4 Conclusion","content":"\u003cp\u003eSingle-ended dihydroxyalylamino modified polysiloxane with a relative molecular weight in the range of 1000\u0026ndash;5000 g/mol and double-ended dihydroxyalkylamino modified polysiloxane with a relative molecular weight in the range of 2000\u0026ndash;4000 g/ mol were prepared from diethanolamine, allyl bromide, and hydrogen-containing silicone oil, which can be uniformly emulsified by a complex emulsifier by fatty alcohol polyoxyethylene ether AE0-6 and AEO-9 in a 1:1 mass ratio. Then, it can be used as a fabric softener to treat woven fabrics and display some characterization to make them better softer than commercial amino silicone oil. Hydrophilicity and yellowing resistance are improved. Some fabric treated with dihydroxyalkylamino polysiloxane lotion not only show higher softness rate and hydrophilicity than that of the original woven fabric but also improve the antistatic ability and fracture strength of the fabric, and the tertiary amine structure does not affect the brightness of the fabric. The use of dihydroxyalkylamino-modified silicone oil has significantly improved performance when applied to softeners.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eCredit authorship contribution statement\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eWeijie Yan \u0026amp; Yunhe Lai\u003c/strong\u003e: Investigation; Software; Data Curation; Writing Original Draft; \u003cstrong\u003eYuxia Zhang\u003c/strong\u003e: Methodology, Investigation of partial experimental data;\u003cstrong\u003e\u0026nbsp;Hong Dong\u003c/strong\u003e: conceptualization; Table design and inspection; \u003cstrong\u003eYanjiang Song\u003c/strong\u003e: Software, Writing - Review \u0026amp; Editing; \u003cstrong\u003eChuan Wu\u003c/strong\u003e: Supervision, Conceptualization, Writing - Review \u0026amp; Editing. \u003cstrong\u003eZhirong Qu\u003c/strong\u003e: Supervision, Validation; Funding Acquisition; Conceptualization; Writing - Review \u0026amp; Editing;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eDeclaration of competing interest\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgment\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors would like to thank the Plan Project of Zhejiang Provincial Natural Science Foundation (LGG21B040002) for its financial supporting of this work.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eB. 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Chen, Synthetic Fiber SFC. 2008, 12, 10.\u003c/li\u003e\n\u003c/ol\u003e"},{"header":"Schemes","content":"\u003cp\u003eSchemes are available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"silicon","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scon","sideBox":"Learn more about [Silicon](https://www.springer.com/journal/12633)","snPcode":"12633","submissionUrl":"https://submission.nature.com/new-submission/12633/3","title":"Silicon","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Dihydroxyalkylmino groups, Group-modified polydimethylsiloxane, Softener","lastPublishedDoi":"10.21203/rs.3.rs-6962058/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-6962058/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eSeveral single- and double-dihydroxyalkylamino groups terminated polysiloxanes with different molecular weights were prepared by a four-step synthesis method using diethanolamine, allyl bromide, and hydrogen-containing silicone oil. The emulsified dihydroxyalkylamino group-modified polysiloxane lotion was used as a softener in fabric finishing. Compared to fabric treated with the commercial amino silicone oil softener, fabric treated with them can improve the hydrophilicity from hydrophobic to hydrophilic, and the tertiary amine structure can resist yellowing defects of the amino silicone oil with the whiteness difference value in line with the normal yellowing value change range. It will not affect the color brightness of the fabric. Fabric treated with such modified polydimethylsiloxane will increase softness rating greater than 4.0. Meanwhile, its improved anti-static ability was indicated by fabric resistance lowered from 10\u003csup\u003e13\u003c/sup\u003e to 10\u003csup\u003e12\u003c/sup\u003e Ω, and fracture strength was enhanced from 211.2 N to more than 400 N.\u003c/p\u003e\u003cp\u003e\u003c/p\u003e","manuscriptTitle":"Synthesis and Application of Dihydroxyalkylamino Groups Modified Polysiloxane","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-09-04 08:54:06","doi":"10.21203/rs.3.rs-6962058/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-10-20T09:13:13+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-09-03T05:34:20+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"249349066673764636957907541196811345758","date":"2025-08-29T04:21:49+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-08-28T12:19:19+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-07-14T10:47:20+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-07-14T10:45:46+00:00","index":"","fulltext":""},{"type":"submitted","content":"Silicon","date":"2025-06-24T06:03:50+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"silicon","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scon","sideBox":"Learn more about [Silicon](https://www.springer.com/journal/12633)","snPcode":"12633","submissionUrl":"https://submission.nature.com/new-submission/12633/3","title":"Silicon","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"c797552a-1189-4d54-9182-7841f1f280c6","owner":[],"postedDate":"September 4th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-12-22T16:00:15+00:00","versionOfRecord":{"articleIdentity":"rs-6962058","link":"https://doi.org/10.1007/s12633-025-03531-0","journal":{"identity":"silicon","isVorOnly":false,"title":"Silicon"},"publishedOn":"2025-12-15 15:57:00","publishedOnDateReadable":"December 15th, 2025"},"versionCreatedAt":"2025-09-04 08:54:06","video":"","vorDoi":"10.1007/s12633-025-03531-0","vorDoiUrl":"https://doi.org/10.1007/s12633-025-03531-0","workflowStages":[]},"version":"v1","identity":"rs-6962058","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6962058","identity":"rs-6962058","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}