CN110396163B - 含氨基甲酸酯结构的水***联剂及其制备方法和应用 - Google Patents
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Abstract
本发明公开了一种含氨基甲酸酯结构的水***联剂及其制备方法和应用,制备方法,包括如下步骤:将聚乙二醇和溶剂混合,然后加入含三个异氰酸酯基团的化合物,反应,再加入催化剂和弱反应活性氢化合物,在相同温度下反应,然后从反应产物中收集所述的含氨基甲酸酯结构的水***联剂,可用于水性聚氨酯涂层的制备,本发明与水性聚氨酯有较好的亲和性,并更容易与聚氨酯树脂形成稳定的氢键结构,能进一步提升产品的物理强度和耐化学品性能。
Description
技术领域
本发明涉及一种水***联剂及其制备方法,具体涉及一种含氨基甲酸酯结构的水***联剂及其制备方法。
背景技术
近年来,水性聚氨酯大量用于涂层制备、皮革表面处理、纺织品的功能处理及水性超细纤维合成的浸渍等等诸多领域中。而在这些应用领域中,若加入合适的交联剂则可以改善产品的耐热、耐水及耐溶剂性能。而如何实现交联剂在水中稳定均匀分散,则是交联剂能否应用于水性聚氨酯体系的关键,也是一个难点。
发明内容
本发明的目的在于提供一种含氨基甲酸酯结构的水***联剂及其制备方法和应用,以克服现有产品的不足。
本发明所述的含氨基甲酸酯结构的水***联剂,制备方法包括如下步骤:
将聚乙二醇和溶剂混合,然后加入含三个异氰酸酯基团的化合物,在50~100℃下进行反应0.5~6小时,再加入催化剂和弱反应活性氢化合物(俗称封闭剂),在相同温度下反应0.5~2小时,然后从反应产物中收集所述的含氨基甲酸酯结构的水***联剂。
各组份的摩尔比为:
聚乙二醇:含三个异氰酸酯基团的化合物=1:2~1:1,当聚乙二醇的摩尔用量超过含三个异氰酸酯基团的化合物的摩尔量时,制备的化合物无法用作交联剂。
所述的封闭剂含三个异氰酸酯基团的化合物=2:1~1:1;
所述的催化剂用量为聚乙二醇、含三个异氰酸酯基团的化合物和封闭剂的总质量的0.1%~10%;
所述的溶剂用量为聚乙二醇、含三个异氰酸酯基团的化合物和封闭剂总质量的5%~500%,优选的为10%~100%;
所述的聚乙二醇是一类由乙二醇或二甘醇为起始剂,由环氧乙烷聚合而成的聚醚二醇;其平均分子量为190-8500,参考文献《聚氨酯原料及助剂手册》第121页表2-78,优选的分子量范围是570~2200;
所述的含三个异氰酸酯基团的化合物为TDI三聚体(CAS编号:
26603-40-7)、TDI-TMP加成物(CAS编号:9017-09-8)、HDI三聚体(CAS编号:3779-63-3)、HDI缩二脲(CAS编号:4035-89-6)、HDI-TMP加成物(CAS编号:50886-64-1)、IPDI三聚体(CAS编号:67873-91-0)中的一种或多种。
所述的封闭剂选自乙酰乙酸乙酯(CAS编号:141-97-9)、乙酰丙酮(CAS编号:123-54-6)、丙二酸二乙酯(CAS编号:105-53-3)、丙酮肟(CAS编号:127-06-0)、甲乙酮肟(CAS编号:96-29-7)、亚硫酸氢钠(CAS编号:7631-90-5)中的一种或多种;
所述的催化剂为二丁基锡二月桂酸酯(CAS编号:77-58-7)、辛酸亚锡(CAS编号:301-10-0)、二乙酸二丁锡(CAS编号:1067-33-0)辛酸锌(CAS编号:136-53-8)、异辛酸铋(CAS编号:67874-71-9)、钛酸四丁酯(CAS编号:5593-70-4)、钛酸四异丙酯(CAS编号:546-68-9)中的一种或多种;
所述的溶剂为丙二醇甲醚醋酸酯、醋酸乙酯、醋酸丁酯、丙酮、甲乙酮、环己酮、四氢呋喃、二氧六环或二甲基甲酰胺中的一种或多种。
采用上述方法获得的含氨基甲酸酯结构的水***联剂,可用于水性聚氨酯涂层的制备,应用方法如下:
将本发明水***联剂加入到水性聚氨酯涂层浆料中,混合均匀,然后和水性聚氨酯浆料一起制备成涂层,即可得到具有优良耐热性、耐水解性及耐溶剂性的涂层。
本发明的有益效果:
本发明的含氨基甲酸酯结构的水***联剂,不需要额外添加乳化剂即可以实现均匀的分散在水中;通过对游离的异氰酸酯基团与弱反应活性氢化合物进行封闭反应,一方面保护了异氰酸酯基团不与水进行反应,达到了稳定分散在水中的目的,另一方面只要加入一定的温度又可实现异氰酸酯基团与其它活性基团进行反应,达到交联的作用。
本发明的含氨基甲酸酯结构的水***联剂,至少有三个异氰酸酯基团可以通过加热解封,然后参与交联反应,具有卓越的交联效果,可以使水性聚氨酯涂层形成致密的网状结构,得到的涂层具有优良的耐热性、耐水解性及耐溶剂性。
本发明的含氨基甲酸酯结构的水***联剂因其含有氨基甲酸酯结构,与水性聚氨酯有较好的亲和性,并更容易与聚氨酯树脂形成稳定的氢键结构,能进一步提升产品的物理强度和耐化学品性能。
具体实施方式
下面用实施例来进一步说明本发明,但本发明并不受其限制。
实施例1
将平均分子量为190的聚乙二醇190g(1摩尔)和79.27g丙二醇甲醚醋酸酯溶剂(5%重量)搅拌混合,然后加入TDI三聚体1046.96g(2摩尔),在50℃下进行反应6小时,再加入158.54g二丁基锡二月桂酸酯催化剂(10%)和封闭剂甲乙酮肟348.48g(4摩尔),在相同温度下反应0.5小时,将溶剂蒸干,即可得到所述的一种含氨基甲酸酯结构的水***联剂。将此水***联剂分散于水中,采用离心机以3000r/min的速度离心沉降15min,无沉淀,说明该水***联剂在25℃温度下可以稳定存放6个月以上。检测方法:采用离心机以3000r/min离心沉降15min,视其有无沉降进行判断是否可以稳定贮存6个月。(参考资料《水性聚氨酯材料》许戈辉(化学工业出版社2007年2月第一版)第176页第⑥点贮存稳定性)
将本实施例制备的水***联剂5份加入到100份水性聚氨酯树脂JF-PDY-851MY(浙江华峰合成树脂有限公司,公开出售的产品)中,制备得到涂层:
其耐热性如下:在105℃下,测试504小时,按DIN EN 20105-A02-1994进行评级涂层变色为4级(5级最好,1级最差)。
耐水解性如下:90℃,95%-100%(相对湿度)条件下,测试840hrs,涂层表面无异常
耐溶剂性如下:涂层按DIN EN ISO 11640:2013方法,用99%酒精测试100次,然后用DIN EN 20105-A02-1994进行评级,表面变色等级为4级。
实施例2
将平均分子量为8500的聚乙二醇8500g(1摩尔)和46357.25g二甲基甲酰胺(500%)搅拌混合,然后加入IPDI三聚体666.85g(1摩尔),在100℃下进行反应0.5小时,再加入9.27g异辛酸铋催化剂(0.1%)和亚硫酸氢钠封闭剂104.06g(1摩尔),在相同温度下反应2小时,将溶剂蒸干,即可得到所述的一种含氨基甲酸酯结构的水***联剂。将此水***联剂分散于水中,采用离心机以3000r/min的速度离心沉降15min,无沉淀,说明该水***联剂在25℃温度下可以稳定存放6个月以上。检测方法:采用离心机以3000r/min离心沉降15min,视其有无沉降进行判断是否可以稳定贮存6个月。
将本实施例制备的水***联剂5份加入到100份水性聚氨酯树脂JF-PDY-851MY中,制备得到涂层:
其耐热性如下:在105℃下,测试504小时,按DIN EN 20105-A02-1994进行评级涂层变色为4级。
耐水解性如下:90℃,95%-100%(相对湿度)条件下,测试840hrs,涂层表面无异常
耐溶剂性如下:涂层按DIN EN ISO 11640:2013方法,用99%酒精测试100次,然后用DIN EN 20105-A02-1994进行评级,表面变色等级为4级。
实施例3
将平均分子量为2200的聚乙二醇2200g(1摩尔)和3207.15g丙酮(100%)搅拌混合,然后加入HDI三聚体756.87g(1.5摩尔),在80℃下进行反应1.2小时,再加入32.07g钛酸四异丙酯(1%)和乙酰丙酮封闭剂250.28g(2.5摩尔),在相同温度下反应1.5小时,将溶剂蒸干,即可得到所述的一种含氨基甲酸酯结构的水***联剂。将此水***联剂分散于水中,采用离心机以3000r/min的速度离心沉降15min,无沉淀,说明该水***联剂在25℃温度下可以稳定存放6个月以上。检测方法:采用离心机以3000r/min离心沉降15min,视其有无沉降进行判断是否可以稳定贮存6个月。
将本实施例制备的水***联剂5份加入到100份水性聚氨酯树脂JF-PDY-851MY中,制备得到涂层:
其耐热性如下:在105℃下,测试504小时,按DIN EN 20105-A02-1994进行评级涂层变色为4.5级。
耐水解性如下:90℃,95%-100%(相对湿度)条件下,测试840hrs,涂层表面无异常。
耐溶剂性如下:涂层按DIN EN ISO 11640:2013方法,用99%酒精测试100次,然后用DIN EN 20105-A02-1994进行评级,表面变色等级为4.5级。
实施例4
将平均分子量为570的聚乙二醇570g(1摩尔)和135.09g醋酸乙酯(10%)搅拌混合,然后加入HDI缩二脲574.31g(1.2摩尔),在70℃下进行反应1.4小时,再加入67.55g钛酸四丁酯(5%)和乙酰乙酸乙酯封闭剂206.61g(1.6摩尔),在相同温度下反应1.8小时,将溶剂蒸干,即可得到所述的一种含氨基甲酸酯结构的水***联剂。将此水***联剂分散于水中,采用离心机以3000r/min的速度离心沉降15min,无沉淀,说明该水***联剂在25℃温度下可以稳定存放6个月以上。检测方法:采用离心机以3000r/min离心沉降15min,视其有无沉降进行判断是否可以稳定贮存6个月。
将本实施例制备的水***联剂5份加入到100份水性聚氨酯树脂JF-PDY-851MY,制备得到涂层:
其耐热性如下:在105℃下,测试504小时,按DIN EN 20105-A02-1994进行评级涂层变色为4级。
耐水解性如下:90℃,95%-100%(相对湿度)条件下,测试840hrs,涂层表面无异常。
耐溶剂性如下:涂层按DIN EN ISO 11640:2013方法,用99%酒精测试100次,然后用DIN EN 20105-A02-1994进行评级,表面变色等级为4.5级。
实施例5
将平均分子量为1000的聚乙二醇1000g(1摩尔)和4510.42g甲乙酮(200%)搅拌混合,然后加入HDI-TMP加成物1050.56g(1.6摩尔),在60℃下进行反应1.7小时,再加入67.66g辛酸锌(3%)和丙酮肟204.65g(2.8摩尔),在相同温度下反应0.9小时,将溶剂蒸干,即可得到所述的一种含氨基甲酸酯结构的水***联剂。将此水***联剂分散于水中,采用离心机以3000r/min的速度离心沉降15min,无沉淀,说明该水***联剂在25℃温度下可以稳定存放6个月以上。检测方法:采用离心机以3000r/min离心沉降15min,视其有无沉降进行判断是否可以稳定贮存6个月。
将本实施例制备的水***联剂5份加入到100份水性聚氨酯树脂JF-PDY-851MY,制备得到涂层:
其耐热性如下:在105℃下,测试504小时,按DIN EN 20105-A02-1994进行评级涂层变色为4级(5级最好,1级最差)。
耐水解性如下:90℃,95%-100%(相对湿度)条件下,测试840hrs,涂层表面无异常。
耐溶剂性如下:涂层按DIN EN ISO 11640:2013方法,用99%酒精测试100次,然后用DIN EN 20105-A02-1994进行评级,表面变色等级为4级。
Claims (7)
1.含氨基甲酸酯结构的水***联剂的制备方法,其特征在于,包括如下步骤:将聚乙二醇和溶剂混合,然后加入含三个异氰酸酯基团的化合物,反应,再加入催化剂和封闭剂,在相同温度下反应,然后从反应产物中收集所述的含氨基甲酸酯结构的水***联剂;
所述的含氨基甲酸酯结构的水***联剂中原料的摩尔比为:
聚乙二醇:含三个异氰酸酯基团的化合物=1:1.5~1:1.2;
封闭剂:含三个异氰酸酯基团的化合物=2:1~1:1;
所述的催化剂用量为聚乙二醇、含三个异氰酸酯基团的化合物和封闭剂的总质量的0.1%~10%;
所述的溶剂用量为聚乙二醇、含三个异氰酸酯基团的化合物和封闭剂总质量的5%~500%;
所述的聚乙二醇平均分子量为570-2200;
所述聚乙二醇与含三个异氰酸酯基团的化合物在70~100℃下进行反应0.5~1.4小时。
2.根据权利要求1所述的含氨基甲酸酯结构的水***联剂的制备方法,其特征在于,所述的含三个异氰酸酯基团的化合物为TDI三聚体、TDI-TMP加成物、HDI三聚体、HDI缩二脲、HDI-TMP加成物、IPDI三聚体中的一种或多种。
3.根据权利要求1所述的含氨基甲酸酯结构的水***联剂的制备方法,其特征在于,所述的封闭剂选自乙酰乙酸乙酯、乙酰丙酮、丙二酸二乙酯、丙酮肟、甲乙酮肟、亚硫酸氢钠中的一种或多种。
4.根据权利要求1所述的含氨基甲酸酯结构的水***联剂的制备方法,其特征在于,所述的催化剂为二丁基锡二月桂酸酯、辛酸亚锡、二乙酸二丁锡、辛酸锌、异辛酸铋、钛酸四丁酯、钛酸四异丙酯中的一种或多种;所述的溶剂为丙二醇甲醚醋酸酯、醋酸乙酯、醋酸丁酯、丙酮、甲乙酮、环己酮、四氢呋喃、二氧六环或二甲基甲酰胺中的一种或多种。
5.根据权利要求1~4任一项所述的方法制备的含氨基甲酸酯结构的水***联剂。
6.根据权利要求5所述的含氨基甲酸酯结构的水***联剂的应用,其特征在于,用于水性聚氨酯涂层的制备。
7.根据权利要求6所述的应用,其特征在于,应用方法如下:
将所述的水***联剂加入到水性聚氨酯涂层浆料中,混合均匀,然后和水性聚氨酯浆料一起制备成涂层,即得到具有优良耐热性、耐水解性及耐溶剂性的涂层。
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