CN107974837B - 一种含季铵盐聚氨酯改性有机硅共聚物及其制备方法 - Google Patents
一种含季铵盐聚氨酯改性有机硅共聚物及其制备方法 Download PDFInfo
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Abstract
本发明提供了一种含季铵盐聚氨酯改性有机硅共聚物及其制备方法,将端环氧基的聚硅氧烷与含三级胺基团的化合物反应,得到含季铵化结构的硅油,然后加入二异氰酸酯和含与异氰酸酯反应活性基团的聚醚进行逐步聚合反应,得到含季铵盐聚氨酯改性有机硅共聚物。本发明的含季铵盐聚氨酯改性有机硅共聚物,相比原有技术中聚醚改性聚硅氧烷,由于主链中含有季铵化结构,不仅大大提高共聚物的亲水性,而且可以赋予织物柔软、吸湿抗静电及抗菌等功能,可有效改善现有氨基硅类整理,最重要的是无需外加比如硫酸二甲酯等剧毒的季铵化试剂,即可获得含季铵化结构的聚氨酯改性有机硅共聚物,工艺较为简单,操作条件易于控制。
Description
技术领域
本发明属于纺织品整理剂的领域,具体涉及一种含季铵盐聚氨酯改性有机硅共聚物及其制备方法。
背景技术
聚二甲基硅氧烷是一种性能非常优越的织物柔软剂,由于其良好的分子柔顺性和丰富的甲基含量,可以使得在纤维表面形成甲基覆盖层,从而降低纤维之间的动静摩擦系数,达到很好的柔软效果。但由于它没有牢固的与纤维形成结合力,只是通过数量有限的范德华力和氢键与纤维结合,同时,由于分子内没有可交联的基团所以无法单独在纤维表面成膜,牢度较差。为了解决这些问题,人们开发出了许多改良的有机硅产品,其中以氨基硅油为代表,由于氨基的存在,在弱酸性条件下,氨基可以阳离子化,产生可以与纤维上负电荷基团形成静电引力结合的较为牢固的键合,牢度由于普通硅油,并且由于这种静电引力的作用,使得有更多的甲基可以外部,故此类产品有超级柔软的效果,是目前市场上柔软性能最好的有机硅产品。但是氨基硅也有它的缺点,由于氨基中的氮原子电子云密度较高,所以容易与吸收光电子发生光化学反应,从而产生所谓的黄变现象,并且氨基硅油还有不易乳化,容易破乳在织物上形成油斑等亲水性差的缺点。目前比较先进的产品是三元共聚有机硅,即通过嵌段共聚在有机硅产品中嵌入亲水性好的氨基聚醚链段,利用氨基的隐性阳离子特性和聚醚的亲水性解决上述问题。但是其合成的工序比较复杂,关键的原料依赖进口,特别是在硅氢和烯丙基缩水甘油醚加成过程中不能100%转化,导致市场上的嵌段硅油质量不稳定,成本高,同时可选择的端氨基聚醚种类有限,对于分子量较大的端氨基聚醚需要的溶剂大,导致应用过程中无法体现出氨基硅油的效果。
聚氨酯改性有机硅,能够结合聚氨酯和有机硅的优点,克服了单一品种的高分子物的缺点,在保留有机硅柔软剂良好柔软性的同时具有聚氨酯的优异性能。专利CN20160826047.2公开了一种手感优异的有机硅-聚氨酯共聚物织物柔软剂的制备方法。虽然保留了氨基硅油的柔软性,回弹性,而且具有一定的亲水性,鲜艳度和白度,但是其爽滑和亲水性仍满足不了市场的需求。
发明内容
本发明的目的在于提供一种含季铵盐聚氨酯改性有机硅共聚物的制备方法,从而进一步提高聚氨酯改性有机硅共聚物的亲水与爽滑性能。
本发明的再一目的在于提供上述制备方法所得的含季铵盐聚氨酯改性有机硅共聚物。
本发明的目的通过下述技术方案实现:
首先,将端环氧基的聚硅氧烷与含三级胺基团的化合物反应,然后加入二异氰酸酯,聚醚多元醇或者聚醚胺进行逐步聚合反应,得到含季铵盐聚氨酯改性有机硅共聚物。
所述的含季铵盐聚氨酯改性有机硅共聚物的制备方法,具体步骤如下:
1)在装有搅拌器,温度计,回流冷凝管以及氮气吹入管的四口反应装置中加入100份端环氧基的聚硅氧烷,再加入含三级胺化合物和中和剂混合物,于60-100℃搅拌反应3-8小时,得到含季铵盐的聚硅氧烷;
其中,
步骤(1)中,所述的端环氧基的聚硅氧烷具有如下式(Ⅰ)所示结构通式:
其中,式(Ⅰ)中,n为25~400的自然数;
步骤(1)中,所述的含三级胺化合物具有如下(II)所示结构通式:
其中,式(II)中,m为1~20的自然数;R1为烷基链,碳数为1~3;R2为CH3-,或-NH2,或-OH;R3为烷基链或者支化烷基链,碳数为1~20,用量为环氧硅油摩尔数的50-110%。
步骤(1)中,所述的中和剂选自甲酸、醋酸、丙酸、月桂酸中的一种,为三级胺化合物摩尔数的90%-110%。
2)在上述中的季铵盐聚硅氧烷中加入1-50份二异氰酸酯、30-100份溶剂,在25-80℃搅拌反应1-6小时,用二正丁胺法分析残留NCO含量,然后加入10-50份聚醚二元醇或者聚醚胺以及催化剂,在65-100℃保持反应5-12小时,得到含季铵盐聚氨酯改性有机硅共聚物;
其中,
步骤(2)中,所述的二异氰酸酯选自异弗尔酮二异氰酸酯(IPDI)、己二异氰酸酯(HDI)、二甲苯甲烷二异氰酸酯(MDI)、亚苯二甲基二异氰酸酯(XDI)或甲苯二异氰酸酯(TDI)中的一种或者或者不少于两种的组合;
步骤(2)中,所述的溶剂为丙酮、甲丁酮、丁酮、乙二醇二甲醚、二乙二醇二甲醚、乙二醇二丁醚、二乙二醇二丁醚、丙二醇二甲醚、二丙二醇二甲醚中的一种;
步骤(2)中,所述的催化剂为有机锡催化剂、有机锌催化剂和有机铋催化剂中的一种,其中优选的有机锡催化剂为二丁基锡二月桂酸酯,用量为季铵盐聚硅氧烷、二异氰酸酯和聚醚总质量的0.1-0.5%;
步骤(2)中,所述的聚醚多元醇为聚乙二醇、聚丙二醇或者两者共聚以及聚四氢呋喃醚二醇中的一种或者不少于两种的组合,分子量为300-6000;
步骤(2)中,所述的聚醚胺为伯胺封端的聚醚,具有如下(III)所示结构通式:
其中,式(III)中,x+y+z为1~70的自然数。
一种含季铵盐聚氨酯改性有机硅共聚物,根据上述制备方法所制得。
本发明与现有技术相比,具有如下优点和效果:
(1)本发明的含季铵盐聚氨酯改性有机硅共聚物的制备方法,工艺较为简单,操作条件易于控制,最重要的是无需外加比如硫酸二甲酯等剧毒的季铵化试剂,即可获得含季铵化结构的聚氨酯改性有机硅共聚物。
(2)本发明的聚氨酯改性有机硅共聚物主链中含有季铵化结构,不仅大大提高共聚物的亲水性,而且可以赋予织物柔软、吸湿抗静电及抗菌等功能,可有效改善现有氨基硅类整理。
附图说明
图1为实施例1中含季铵化结构的聚氨酯改性有机硅共聚物的红外谱图;
具体实施方式
下面结合实施例及附图对本发明作进一步详细的描述,但本发明的实施方式不限于此。
实施例1
将100g端环氧硅油(分子量12000,m≈159)加入到装有温度计和回流冷凝管的四口烧瓶中,在搅拌条件下,加入1.2g N,N-二甲基乙胺和醋酸1g,于90℃搅拌反应5小时,得到含季铵盐的聚硅氧烷;接着,加入异佛尔酮二异氰酸酯3.5g,溶剂丙酮30g,在50℃搅拌反应1小时,用二正丁胺法分析残留NCO含量,等达到计算值后,再加入30g聚醚二元醇PEG-PPG2000(分子量2000,EO/PO=),催化剂二丁基锡二月桂酸酯0.1g,65℃搅拌反应5小时,得到含季铵盐聚氨酯改性有机硅共聚物。
从附图1中可以看出,800cm-1和1261cm-1出现的吸收峰应属于硅油结构中Si-O-Si和Si-C的特征吸收峰。在2280-2240cm-1范围内没有出现的NCO特征吸收峰,表明制备的共聚物中无游离的CNO存在。在1530cm-1出现的峰应是CO-NH中N-H基团的变形振动吸收峰,在1698cm-1出现的峰应是CO-NH中C=O基团的伸缩振动峰,以上两点为氨基甲酸酯基的特征振动峰,表明所测物质含聚氨酯结构,另外从吸收峰强度来看,其含量相对较低,与实验投料比例是相一致的。1097cm-1和1032cm-1出现的2个峰应是聚醚中C-O-C的不对称伸缩震动吸收峰,说明该共聚物中存在聚醚成分。
实施例2
将100g端环氧硅油(分子量15000,m≈)加入到装有温度计和回流冷凝管的四口烧瓶中,在搅拌条件下,加入1.0g N,N-二甲基乙醇胺和丙二酸1.2g,于100℃搅拌反应3小时,得到含季铵盐的聚硅氧烷;接着,加入甲基苯基二异氰酸酯4.6g,溶剂乙酸丙酯80g,在50℃搅拌反应2小时,用二正丁胺法分析残留NCO含量,等达到计算值后,再加入10g羟基聚醚胺PEG400(分子量400,a=9,b=0),催化剂二丁基锡二月桂酸酯0.1g,80℃搅拌反应8小时,得到含季铵盐聚氨酯改性有机硅共聚物。
实施例3
将100g端环氧硅油(分子量30000,m≈)加入到装有温度计和回流冷凝管的四口烧瓶中,在搅拌条件下,加入1g N,N-二甲基乙二胺和月桂酸2g,于100℃搅拌反应8小时,得到含季铵盐的聚硅氧烷;接着,加入六己基二异氰酸酯2.4g,溶剂二丙二醇二甲醚100g,在25℃搅拌反应3小时,用二正丁胺法分析残留NCO含量,等达到计算值后,再加入20g羟基聚醚PEG-PPG100(分子量1000,a=12,b=8),催化剂二丁基锡二月桂酸酯0.5g,100℃搅拌反应12小时,得到含季铵盐聚氨酯改性有机硅共聚物。
实施例4
将100g端环氧硅油(分子量2000,m≈)加入到装有温度计和回流冷凝管的四口烧瓶中,在搅拌条件下,加入8g N,N-二乙基乙二胺和醋酸6g,于60℃搅拌反应5小时,得到含季铵盐的聚硅氧烷;接着,加入二苯基甲烷二异氰酸酯50g,溶剂二乙二醇二丁醚30g,在25℃搅拌反应3小时,用二正丁胺法分析残留NCO含量,等达到计算值后,再加入35g聚醚胺D400(分子量400,x+z=6,y=0),80℃搅拌反应6小时,得到含季铵盐聚氨酯改性有机硅共聚物。
实施例5
将100g端环氧硅油(分子量8000,m≈)加入到装有温度计和回流冷凝管的四口烧瓶中,在搅拌条件下,加入20g N,N-二甲基十二胺和醋酸6g,于90℃搅拌反应5小时,得到含季铵盐的聚硅氧烷;接着,加入异佛尔酮二异氰酸酯10g,溶剂丙酮30g,在80℃搅拌反应6小时,用二正丁胺法分析残留NCO含量,等达到计算值后,再加入50g聚醚胺ED900(分子量900,x+z=6,y=12.5),75℃搅拌反应8小时,得到含季铵盐聚氨酯改性有机硅共聚物。
对比例
将100g端环氧硅油(分子量12000,m≈)加入到装有温度计和回流冷凝管的四口烧瓶中,加入30g ED2003和溶剂异丙醇100g,于85℃搅拌反应24小时,得到聚醚改性氨基聚硅氧烷。
应用实施例
对比标准:将以上硅油配制成20%的水溶液,比较布样为纯白色针织棉布,用量为10g/L,一浸一轧,在170℃定形烘干90秒。
评价方法:手感主要从柔软性和平滑性方面综合考察,由多名专家盲摸,5级最好,1级最差。
织物的亲水性通过以秒为单位测定一滴水完全被织物吸收的时间定义。
比较结果如下:
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (6)
1.一种含季铵盐聚氨酯改性有机硅共聚物的制备方法,其特征在于包括以下步骤:
1)在装有搅拌器,温度计,回流冷凝管以及氮气吹入管的四口反应装置中加入100份端环氧基的聚硅氧烷,再加入含三级胺化合物和中和剂混合物,于60-100℃搅拌反应3-8小时,得到含季铵盐的聚硅氧烷;
2)在步骤1)所得到的含季铵盐的聚硅氧烷中加入1-50份二异氰酸酯、30-100份溶剂,在25-80℃搅拌反应1-6小时,用二正丁胺法分析残留NCO含量,然后加入10-50份聚醚多元醇或者聚醚胺以及催化剂,在65-100℃保持反应5-12小时,得到含季铵盐聚氨酯改性有机硅共聚物;
在步骤1)中,所述的端环氧基的聚硅氧烷具有以下结构通式:
其中,n为25~400的自然数;
所述的含三级胺化合物具有以下结构通式:
在步骤2)中,所述的二异氰酸酯选自异弗尔酮二异氰酸酯(IPDI)、己二异氰酸酯(HDI)、二甲苯甲烷二异氰酸酯(MDI)、亚苯二甲基二异氰酸酯(XDI)或甲苯二异氰酸酯(TDI)中的一种或者不少于两种的组合。
2.根据权利要求1所述含季铵盐聚氨酯改性有机硅共聚物的制备方法,其特征在于:在步骤2)中,所述的溶剂为丙酮、甲丁酮、丁酮、乙二醇二甲醚、二乙二醇二甲醚、乙二醇二丁醚、二乙二醇二丁醚、丙二醇二甲醚、二丙二醇二甲醚中的一种,所述的催化剂为有机锡催化剂、有机锌催化剂和有机铋催化剂中的一种。
3.根据权利要求2所述含季铵盐聚氨酯改性有机硅共聚物的制备方法,其特征在于:所述有机锡催化剂为二丁基锡二月桂酸酯,用量为季铵盐聚硅氧烷、二异氰酸酯和聚醚总质量的0.1-0.5%;所述的聚醚多元醇为聚乙二醇、聚丙二醇或者两者共聚以及聚四氢呋喃醚二醇中的一种或者不少于两种的组合,分子量为300-6000。
5.根据权利要求1所述含季铵盐聚氨酯改性有机硅共聚物的制备方法,其特征在于:在步骤1)中,所述的中和剂选自甲酸、醋酸、丙酸、月桂酸中的一种,为三级胺化合物摩尔数的90%-110%。
6.一种含季铵盐聚氨酯改性有机硅共聚物,其特征在于:根据权利要求1-4任一所述的含季铵盐聚氨酯改性有机硅共聚物制备方法所制得。
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Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102417595A (zh) * | 2011-11-20 | 2012-04-18 | 浙江精业生化有限公司 | 一种聚氨酯改性有机硅胶的制备方法 |
CN102604026A (zh) * | 2011-02-17 | 2012-07-25 | 浙江深蓝轻纺科技有限公司 | 合成革用有机硅改性聚氨酯树脂及其制备方法 |
CN102926208A (zh) * | 2012-10-16 | 2013-02-13 | 淮安凯悦科技开发有限公司 | 肤感的聚氨酯树脂人造革表面处理剂 |
CN103351461A (zh) * | 2013-06-26 | 2013-10-16 | 佛山市顺德区德美瓦克有机硅有限公司 | 一种封闭型异氰酸酯改性聚醚有机硅及其制备方法 |
CN103951809A (zh) * | 2014-04-23 | 2014-07-30 | 西安工程大学 | 一种聚氨酯改性有机硅多元共聚物织物柔软剂的制备方法 |
CN104327238A (zh) * | 2014-10-22 | 2015-02-04 | 齐鲁工业大学 | 一种有机硅阳离子水性聚氨酯的制备方法 |
CN105482074A (zh) * | 2015-09-07 | 2016-04-13 | 杭州美高华颐化工有限公司 | 一种阴离子型聚氨酯改性有机硅乳液及其制备方法 |
CN106589385A (zh) * | 2017-01-05 | 2017-04-26 | 佛山市顺德区德美瓦克有机硅有限公司 | 一种低黄变季铵型亲水氨基硅油乳液及其制备方法 |
CN106810664A (zh) * | 2016-11-23 | 2017-06-09 | 杭州乐新材料科技有限公司 | 一种聚氨酯改性有机硅树脂的制备方法 |
CN107059405A (zh) * | 2017-03-01 | 2017-08-18 | 苏州依司特新材料科技有限公司 | 一种聚氨酯改性有机硅拒水与抗菌整理剂、制备方法及应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4067844A (en) * | 1976-12-22 | 1978-01-10 | Tremco Incorporated | Urethane polymers and sealant compositions containing the same |
JP3444287B2 (ja) * | 2001-01-25 | 2003-09-08 | 荒川化学工業株式会社 | アルコキシ基含有シラン変性ポリウレタン樹脂、当該樹脂組成物およびポリウレタン樹脂−シリカハイブリッド体 |
US7348392B2 (en) * | 2002-09-09 | 2008-03-25 | Reactamine Technology, Llc | Silicone modified acrylics and epoxies |
CN101392062B (zh) * | 2008-11-04 | 2011-02-09 | 北京化工大学 | 一种碱溶性光敏有机硅预聚物及其制备方法 |
CN101914343B (zh) * | 2010-08-26 | 2012-09-26 | 合肥工业大学 | 一种有机硅氧烷改性水性聚氨酯涂料的制备方法 |
CN103450437B (zh) * | 2013-08-28 | 2015-10-28 | 桐乡市濮院毛针织技术服务中心 | 一种有机硅氧烷改性水性聚氨酯制备羊毛柔软剂的方法 |
CN105755837B (zh) * | 2016-02-29 | 2018-05-15 | 东莞市佳乾新材料科技有限公司 | 一种季铵化改性氨基硅油柔顺剂的制备方法与应用 |
CN107974837B (zh) * | 2017-12-06 | 2020-04-24 | 佛山市顺德区德美瓦克有机硅有限公司 | 一种含季铵盐聚氨酯改性有机硅共聚物及其制备方法 |
-
2017
- 2017-12-06 CN CN201711272416.9A patent/CN107974837B/zh active Active
- 2017-12-06 CN CN201910855402.2A patent/CN110527052B/zh active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102604026A (zh) * | 2011-02-17 | 2012-07-25 | 浙江深蓝轻纺科技有限公司 | 合成革用有机硅改性聚氨酯树脂及其制备方法 |
CN102417595A (zh) * | 2011-11-20 | 2012-04-18 | 浙江精业生化有限公司 | 一种聚氨酯改性有机硅胶的制备方法 |
CN102926208A (zh) * | 2012-10-16 | 2013-02-13 | 淮安凯悦科技开发有限公司 | 肤感的聚氨酯树脂人造革表面处理剂 |
CN103351461A (zh) * | 2013-06-26 | 2013-10-16 | 佛山市顺德区德美瓦克有机硅有限公司 | 一种封闭型异氰酸酯改性聚醚有机硅及其制备方法 |
CN103951809A (zh) * | 2014-04-23 | 2014-07-30 | 西安工程大学 | 一种聚氨酯改性有机硅多元共聚物织物柔软剂的制备方法 |
CN104327238A (zh) * | 2014-10-22 | 2015-02-04 | 齐鲁工业大学 | 一种有机硅阳离子水性聚氨酯的制备方法 |
CN105482074A (zh) * | 2015-09-07 | 2016-04-13 | 杭州美高华颐化工有限公司 | 一种阴离子型聚氨酯改性有机硅乳液及其制备方法 |
CN106810664A (zh) * | 2016-11-23 | 2017-06-09 | 杭州乐新材料科技有限公司 | 一种聚氨酯改性有机硅树脂的制备方法 |
CN106589385A (zh) * | 2017-01-05 | 2017-04-26 | 佛山市顺德区德美瓦克有机硅有限公司 | 一种低黄变季铵型亲水氨基硅油乳液及其制备方法 |
CN107059405A (zh) * | 2017-03-01 | 2017-08-18 | 苏州依司特新材料科技有限公司 | 一种聚氨酯改性有机硅拒水与抗菌整理剂、制备方法及应用 |
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