CN110872372B - 含三嗪环的六官能团丙烯酸聚氨酯及其制备方法和应用 - Google Patents
含三嗪环的六官能团丙烯酸聚氨酯及其制备方法和应用 Download PDFInfo
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Abstract
本发明的目的是为了提高异氰脲酸酯的热稳定和与丙烯酸酯的相容性,提供了一种含三嗪环的六官能团丙烯酸聚氨酯及其制备方法和应用,属于有机合成技术领域。本发明的产品首先由异氰尿酸三缩水甘油酯与丙烯酸反应,得到的产物在与异氰酸酯反应,得到的产物再与羟基丙烯酸酯,既得到产品。本发明的产品与各种丙烯酸单体、丙烯酸环氧树脂、丙烯酸聚氨酯任意比例完全溶解,并具有优异热稳定性,成膜机械性能优良,韧性好,硬度高;该制备方法简单,收率高,适合工业生产。
Description
技术领域
本发明属于有机合成技术领域,特别涉及一种含三嗪环的六官能团丙烯酸聚氨酯及其制备方法和应用。
背景技术
异氰脲酸酯是异氰酸酯三聚反应生成的碳氮六节环结构。该异氰脲酸酯环具有良好的热稳定性、阻燃性和耐化学品性。尤其适合于制备耐高温、高强的玻璃钢产品;也可用于橡胶、电缆行业,做高度饱和橡胶的硫化促进剂,提高硫化效果;也可用于做聚烯辐照交联的光敏剂,降低辐照量。
有研究者用丙烯酸改性异氰尿酸缩水甘油酯得到丙烯酸三环氧丙基异氰尿酸酯。该预聚体具有良好热稳定性,但与其他的丙烯酸酯相容性差,无法用于紫外光固化涂料。
发明内容
本发明的目的是为了提高异氰脲酸酯的热稳定和与丙烯酸酯的相容性,提供了一种含三嗪环的六官能团丙烯酸聚氨酯及其制备方法和应用。本发明的产品与各种丙烯酸单体、丙烯酸环氧树脂、丙烯酸聚氨酯任意比例完全溶解,并具有优异热稳定性,成膜机械性能优良,韧性好,硬度高;该制备方法简单,收率高,适合工业生产。
本发明的技术方案之一为,一种含三嗪环的六官能团丙烯酸聚氨酯,其化学结构式(I)如下:
其中,R=2,4位取代的甲苯基,2,6位取代的甲苯基,-(CH2)6-或1,3位取代的3,5,5-三甲基环己烷基;
R’=-(CH2)2-,-(CH2)3-,或-(CH2)4-。
本发明的技术方案之二为,上述含三嗪环的六官能团丙烯酸聚氨酯的制备方法,包括如下步骤:
1)将异氰尿酸三缩水甘油酯与丙烯酸投入反应容器中,同时加入催化剂1和阻聚剂,开启搅拌,搅拌速度为60~110转/分钟,加热升温至85~90℃反应0.5~1小时,再升温至95~100℃,反应0.5~1小时,接着升温至110~115℃继续反应,当反应液中酸值低于5mgKOH/g、环氧值低于0.02当量/100g,反应结束;
本步骤的反应方程式(1)如下:
2)将步骤1)的产物降温至55~60℃,加入异氰酸酯和催化剂2,控制温度在60~70℃之间,保温反应至反应液中异氰酸根反应掉47~50%时,反应结束;
本步骤的反应方程式(2)如下:
3)向步骤2)的产物中投入羟基丙烯酸酯,在55~60℃下反应至反应液中的异氰酸根质量分数低于0.2%,反应终止,出料。
本步骤的反应方程式(3)如下:
进一步的,上述制备方法中,所述异氰尿酸三缩水甘油酯∶丙烯酸∶异氰酸酯∶羟基丙烯酸酯的摩尔比=1∶2.98~3.05∶2.98~3.05∶3.10~3.25;
较好的,所述异氰尿酸三缩水甘油酯∶丙烯酸∶异氰酸酯∶羟基丙烯酸酯的摩尔比=1∶3.03∶3.03∶3.2;
进一步的,上述制备方法中,所述催化剂1∶丙烯酸的质量比=1∶270~330;
较好的,所述催化剂1∶丙烯酸的质量比=1∶300;
进一步的,上述制备方法中,所述催化剂2∶异氰酸酯的质量比=1∶9000~11000;
较好的,所述催化剂2∶异氰酸酯的质量比=1∶10000;
进一步的,上述制备方法中,所述阻聚剂∶丙烯酸的质量比=1∶180~220;
较好的,所述阻聚剂∶丙烯酸的质量比=1∶200;
进一步的,上述制备方法中,所述催化剂1为三乙胺或者N,N-二甲基丙胺;
进一步的,上述制备方法中,所述催化剂2为二月桂酸二丁基锡;
进一步的,上述制备方法中,所述阻聚剂为对羟基苯甲醚或者二叔丁基对甲酚;
进一步的,上述制备方法中,所述异氰酸酯为甲苯二异氰酸酯,四亚甲基二异氰酸酯或异佛尔酮二异氰酸酯;
进一步的,上述制备方法中,所述羟基丙烯酸酯为丙烯酸羟乙酯,丙烯酸羟丙酯或丙烯酸羟丁酯。
本发明的技术方案之三为,上述含三嗪环的六官能团丙烯酸聚氨酯的应用,用于制备紫外光固化涂料。
与现有技术相比,本发明的优势在于:
1、本发明的产品与各种丙烯酸单体、丙烯酸环氧树脂、丙烯酸聚氨酯任意比例完全溶解。
2、本发明的制备方法简单,收率高,适合工业生产。
具体实施方式
实施例1
一种含三嗪环的六官能团丙烯酸聚氨酯的制备方法,包括如下步骤:
1)将异氰尿酸三缩水甘油酯与丙烯酸按摩尔比1∶3.03投入反应釜中,同时加入催化剂1三乙胺和阻聚剂对羟基苯甲醚,催化剂1与丙烯酸的质量比为1∶300,阻聚剂与丙烯酸的质量比为1∶200,开启搅拌,加热升温至90℃反应1小时,再升温至100℃,反应1小时,接着升温至115℃,反应至酸值低于5mg KOH/g,并且环氧值低于0.02当量/100g,反应1)结束。
2)将反应1)的产物降温至60℃,加入催化剂2二月桂酸二丁基锡和甲苯二异氰酸酯,异氰尿酸三缩水甘油酯与甲苯二异氰酸酯的投料摩尔比为1∶3.03,催化剂2与甲苯二异氰酸酯的质量比=1∶10000,控制温度在65℃保温反应至异氰酸根反应掉50%时,反应2)结束。
3)向反应2)产物中投入丙烯酸羟乙酯,异氰尿酸三缩水甘油酯与丙烯酸羟乙酯的投料摩尔比为1∶3.2,在60℃下反应,取样测异氰酸根值,当异氰酸根质量分数低于0.2%,反应终止,出料。
经检测,本实施例制得的化合物化学结构式(Ia)如下所示:
反应产物收率为100%。
本实施例的产品进行相容性测试:
该树脂与各种丙烯酸单体、丙烯酸环氧树脂、丙烯酸聚氨酯任意比例完全溶解。
本实施例的产品进行成膜性能测试:
将本方案的树脂加入4%的光敏剂,混合均匀涂在金属试片上。用2KW中压汞灯、以80m/s传送速度进行固化,得到的膜进行测试:
1、固化速度快,大于80m/s。
2、高硬度,大于4H。
3、韧性好,弯曲半径小于5mm。
4、热稳定好,200℃1小时无变化。
5、抗老化性好,加速老化时间大于1000小时。
实施例2
一种含三嗪环的六官能团丙烯酸聚氨酯的制备方法,包括如下步骤:
1)将异氰尿酸三缩水甘油酯与丙烯酸按摩尔比1∶2.98投入反应釜中,同时加入催化剂1N,N-二甲基丙胺和阻聚剂二叔丁基对甲酚,催化剂1与丙烯酸的质量比为1∶270,阻聚剂与丙烯酸的质量比为1∶180,开启搅拌,加热升温至88℃反应45min,再升温至98℃,反应45min,接着升温至113℃反应至酸值低于5mg KOH/g,并且环氧值低于0.02当量/100g,反应1)结束。
2)将反应1)的产物降温至55℃,加入催化剂2二月桂酸二丁基锡和己二异氰酸酯,异氰尿酸三缩水甘油酯与己二异氰酸酯的投料摩尔比为1∶3.05,催化剂2与己二异氰酸酯的质量比=1∶11000,控制温度在60℃保温反应至异氰酸根反应掉47%时,反应2)结束。
3)向反应2)产物中投入丙烯酸羟丙酯,异氰尿酸三缩水甘油酯与丙烯酸羟丙酯的投料摩尔比为1∶3.1,在58℃下反应至异氰酸根质量分数低于0.2%,反应终止,出料。
经检测,本实施例制得的化合物化学结构式(Ib)如下:
反应产物收率为97.8%。
实施例3
一种含三嗪环的六官能团丙烯酸聚氨酯的制备方法,包括如下步骤:
1)将异氰尿酸三缩水甘油酯与丙烯酸按摩尔比1∶3.05投入反应釜中,同时加入催化剂1三乙胺和阻聚剂二叔丁基对甲酚,催化剂1与丙烯酸的质量比为1∶330,阻聚剂与丙烯酸的质量比为1∶220,开启搅拌,加热升温至85℃反应30min,再升温至95℃,反应30min,接着升温至110℃反应至酸值低于5mg KOH/g,并且环氧值低于0.02当量/100g,反应1)结束。
2)将反应1)的产物降温至58℃,加入催化剂2二月桂酸二丁基锡和异佛尔酮二异氰酸酯,异氰尿酸三缩水甘油酯与异佛尔酮二异氰酸酯的投料摩尔比为1∶2.98,催化剂2与异佛尔酮二异氰酸酯的质量比=1∶9000,控制温度在70℃保温反应至异氰酸根反应掉50%时,反应2)结束。
3)向反应2)产物中投入丙烯酸羟丁酯,异氰尿酸三缩水甘油酯与丙烯酸羟丁酯的投料摩尔比为1∶3.25,在55℃下反应至异氰酸根质量分数低于0.2%,反应终止,出料。
经检测,本实施例制得的化合物化学结构式(Ic)如下:
反应产物收率为99.2%。
Claims (8)
2.权利要求1所述含三嗪环的六官能团丙烯酸聚氨酯的制备方法,其特征在于,包括如下步骤:
1)将异氰尿酸三缩水甘油酯与丙烯酸投入反应容器中,同时加入催化剂1和阻聚剂,开启搅拌,加热升温至85~90℃反应0.5~1小时,再升温至95~100℃,反应0.5~1小时,接着升温至110~115℃继续反应,当反应液中酸值低于5mg KOH/g、环氧值低于0.02当量/100g,反应结束;
2)将步骤1)的产物降温至55~60℃,加入异氰酸酯和催化剂2,控制温度在60~70℃之间,保温反应至反应液中异氰酸根反应掉47~50%时,反应结束;
3)向步骤2)的产物中投入羟基丙烯酸酯,在55~60℃下反应至反应液中的异氰酸根质量分数低于0.2%,反应终止,出料。
3.根据权利要求2所述的制备方法,其特征在于,所述异氰尿酸三缩水甘油酯∶丙烯酸∶异氰酸酯∶羟基丙烯酸酯的摩尔比=1∶2.98~3.05∶2.98~3.05∶3.10~3.25。
4.根据权利要求2所述的制备方法,其特征在于,所述催化剂1∶丙烯酸的质量比=1∶270~330;所述催化剂2∶异氰酸酯的质量比=1∶9000~11000。
5.根据权利要求2所述的制备方法,其特征在于,所述阻聚剂∶丙烯酸的质量比=1∶180~220。
6.根据权利要求2所述的制备方法,其特征在于,所述催化剂1为三乙胺或者N,N-二甲基丙胺;所述催化剂2为二月桂酸二丁基锡。
7.根据权利要求2所述的制备方法,其特征在于,所述阻聚剂为对羟基苯甲醚或者二叔丁基对甲酚。
8.权利要求1所述含三嗪环的六官能团丙烯酸聚氨酯的应用,其特征在于,用于制备紫外光固化涂料。
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