CN108728011A - 一种新型粘接促进剂及其制备方法 - Google Patents
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Abstract
本发明涉及一种新型粘接促进剂的制备方法，包括：三烯丙基异氰脲酸酯、贵金属催化剂和溶剂加入反应釜中，升温搅拌后，向其中缓慢滴加三烷氧基硅烷、端氢基硅油和溶剂的混合液，滴加完毕之后，保温反应，降温至60℃，向其中滴加烯丙基缩水甘油醚和溶剂的混合液，保温反应后，过滤，旋蒸除去溶剂及低沸物，即得到目标产物粘接促进剂。由上述方法合成的粘接促进剂，同时含有烷氧基、环氧基以及六元环异氰脲酸酯三种极性基团，可大大促进有机硅胶黏剂对不同基材的粘接性能；与有机硅体系具有良好的相容性，尤其适用于光学应用的有机硅胶(如LED硅胶)体系，对其具有良好的相容性和粘接促进作用。
Description
技术领域
本发明涉及一种新型粘接促进剂及其制备方法，属于有机合成领域。
技术背景
有机硅体系由于可形成耐候性、耐热性优异的固化物，又可通过配方调整满足各种不同硬度、弹性的需求，正被越来越多的领域所应用。但是因为有机硅极性小，在应用于各种领域的过程中难免会遇到基材粘接不良的问题，因而需要引入有效的粘接促进剂，改善其对不同基材的粘接性能。
甲基有机硅以及苯基有机硅因为其优异的耐热性以及耐候性，近年来已经取代环氧封装胶基本主导了LED封装领域，尤其是对光色要求较高的LED领域，如车灯、显示屏背光源等。在这样的光学领域应用的有机硅体系中引入粘接促进剂，常常会面临相容性不良，导致胶水不透明影响出光的情况，或者相容性较好，极性又不足，粘结促进效果不理想的情况发生。本发明提供一种新型粘接促进剂及其制备方法，与有机硅体系具有良好的相容性，同时又可显著提高有机硅体系与不同基材的粘接性能。
发明内容
本发明所要解决的技术问题是提供一种新型粘接促进剂及其制备方法，该粘接促进剂与有机硅体系具有良好的相容性，同时又可显著提高有机硅体系与不同基材的粘接性能。
本发明所述的一种新型粘接促进剂，其结构式如下：
式中，R1和R2彼此独立地代表未取代或取代的一价烃基。作为一价烃基，优选碳原子数1～10、特别优选1～6的基团，具体可列举：甲基、乙基、丙基、异丙基等低级烷基，环己基等环烷基，苯基、甲苯基、二甲苯基等芳基，苄基等芳烷基，乙烯基、丙烯基等含稀键的烷烃基，或上述基团的部分或全部氢原子被卤原子、氰基等取代得到的基团、例如氯甲基、氰乙基等。
式中，n为0或正整数。且n是使该粘接促进剂在25℃下的粘度为10～20,000mPa·s的数值。上述n为0～10,000的正整数或0，优选为0～2000的整数，更优选为0～500的整数。
式中，R3为甲基、乙基、丙基、异丙基或丁基等低级烷基。
本发明所述的一种新型粘接促进剂的制备方法，其特征在于，合成路径如下：
将一定量的三烯丙基异氰脲酸酯、贵金属催化剂和溶剂①加入反应釜中，升温至30～60℃，混合搅拌0.5～1h后，向其中缓慢滴加三烷氧基硅烷、端氢基硅油和溶剂②的混合液，滴加完毕之后，保温反应0.5～1h，随后升温至60～100℃，保温反应1～6h。反应完毕后，降温至60℃，向其中滴加烯丙基缩水甘油醚和溶剂③的混合液，保温反应0.5～1h，随后升温至60～100℃，保温反应1～6h。反应结束之后，过滤，旋蒸除去溶剂及低沸物，即得到目标产物粘接促进剂。
如上所述，贵金属催化剂为硅氢加成常用催化剂，可以是铑、铂、钯、钌及其络合物催化剂；溶剂①，溶剂②，溶剂③可以是甲苯、苯、四氢呋喃、环己酮、乙二醇二甲醚、邻苯二甲酸二甲酯、异丙醇等中的一种或几种。
溶剂①的添加量为三烯丙基异氰脲酸酯质量的0～1.5倍，且包括0；溶剂②的添加量为三烷氧基硅烷质量的0～10倍，且包括0；溶剂③的添加量为烯丙基缩水甘油醚质量的0～1.5倍，且包括0；三烷氧基硅烷与三烯丙基异氰脲酸酯的摩尔比为0.8～1.5:1；端氢基硅油的Si-H与三烯丙基异氰脲酸酯的摩尔比为1.5～2.5:1；烯丙基缩水甘油醚与端氢基硅油的Si-H的摩尔比为0.5～0.8:1；贵金属催化剂在体系内的含量为反应物总质量的2ppm～0.5‰。
由上所述的合成方法，获得的本发明所述的一种新型粘接促进剂，同时含有烷氧基、环氧基以及六元环异氰脲酸酯三种极性基团，可大大促进有机硅胶黏剂对不同基材的粘接性能。其次，该粘接促进剂中含有有机硅链段，与有机硅体系具有良好的相容性，尤其适用于光学应用的有机硅胶(如LED硅胶)体系，对其具有良好的相容性和粘接促进作用。
附图说明
图1为本发明实施例2所得产物的红外光谱图，如图1所示，1254cm-1处出峰为环氧基、1045cm-1和1127cm-1处出峰为Si-O-Si、2800～3100cm-1处出峰为分子中甲基与亚甲基的出峰、1699cm-1处出峰为六元环异氰脲酸酯中的C＝O、1447cm-1处出峰为六元环异氰脲酸酯中的C-N、2130cm-1没有明显出峰说明Si-H已基本全部参与反应。
具体实施案例
以下列举实例对本发明进行描述，所举实例只用于解释本发明，并非用于限定本发明的应用。
实施例1
将24.9g的三烯丙基异氰脲酸酯、20uL Pt含量为25％的Karstedt催化剂和30g甲苯加入反应釜中，升温至40℃，混合搅拌30min后，向其中缓慢滴加14g三甲氧基硅烷、13.4g含氢双封头和50g甲苯的混合液，滴加完毕之后，保温反应1h，随后升温至80℃，保温反应4h；反应完毕后，降温至60℃，向其中滴加11.4g烯丙基缩水甘油醚和15g甲苯的混合液，保温反应1h，随后升温至100℃，保温反应6h；反应结束之后，旋蒸除去溶剂及低沸物，即得到目标产物粘接促进剂51.2g。
实施例2
将50g的三烯丙基异氰脲酸酯、0.106g Pt-C(5％)催化剂和50g甲苯加入反应釜中，升温至50℃，混合搅拌30min后，向其中缓慢滴加25g三甲氧基硅烷、66g四甲基二苯基二氢化三硅氧烷和50g甲苯的混合液，滴加完毕之后，保温反应1h，随后升温至70℃，保温反应3h；反应完毕后，降温至60℃，向其中滴加23g烯丙基缩水甘油醚和20g甲苯的混合液，保温反应1h，随后升温至80℃，保温反应4h；反应结束之后，过滤，旋蒸除去溶剂及低沸物，即得到目标产物粘接促进剂132.7g。
实施例3
将24.9g的三烯丙基异氰脲酸酯、0.15g Ru-C(5％)催化剂和25g甲苯加入反应釜中，升温至40℃，混合搅拌30min后，向其中缓慢滴加14g三甲氧基硅烷、50g 200mPa.s的端含氢硅油和100g甲苯的混合液，滴加完毕之后，保温反应1h，随后升温至70℃，保温反应4h；反应完毕后，降温至60℃，向其中滴加10g烯丙基缩水甘油醚和15g甲苯的混合液，保温反应1h，随后升温至100℃，保温反应6h；反应结束之后，过滤，旋蒸除去溶剂及低沸物，即得到目标产物粘接促进剂90.8g。
对比实施例1
将24.9g的三烯丙基异氰脲酸酯、20uL Pt含量为25％的Karstedt催化剂和30g甲苯加入反应釜中，升温至40℃，混合搅拌30min后，向其中缓慢滴加14g三甲氧基硅烷和20g甲苯的混合液，滴加完毕之后，保温反应1h，随后升温至80℃，保温反应6h；反应结束之后，旋蒸除去溶剂及低沸物，即得到不含有机硅及环氧基团的对比实施例1的产物32.3g。
对比实施例2
将24.9g三烯丙基异氰脲酸酯和23.6g KH-560混合搅拌均匀，即得到不含有机硅链段的小分子化合物的混合液。
对比测试方法：
分别以一种苯基有机硅LED封装硅胶配方与一种甲基有机硅LED封装硅胶配方为基础，向其中添加等量上述具体实施案例，观察胶水的外观，测试胶水封装2835支架并经过回流焊后的红墨水特性。
红墨水测试方法：
灯珠浸入红墨水溶液(红墨水与乙醇1:1比例)中，将红墨水溶液煮沸一定时间之后，观察灯珠的红墨水渗入情况。
对比测试结果：
苯基有机硅LED封装硅胶体系
从苯基有机硅LED封装硅胶体系的对比测试结果可以看出：环氧基、烷氧基以及六元环异氰脲酸酯三个基团必须同时存在，且共存于一个分子当中，三个基团单纯共混在一起对粘接促进并不能起到理想的效果。
甲基有机硅LED封装硅胶体系
从甲基有机硅LED封装硅胶体系的对比测试结果不仅可以看出粘接性的差异，同时也可看出在甲基有机硅体系中，必须引入有机硅链段才能增强相容性，否则相容性不良就会产生浑浊现象，影响出光。
Claims (3)
1.一种新型粘接促进剂的制备方法，其特征在于，合成路径如下：将一定量的三烯丙基异氰脲酸酯、贵金属催化剂和溶剂①加入反应釜中，升温至30～60℃，混合搅拌0.5～1h后，向其中缓慢滴加三烷氧基硅烷、端氢基硅油和溶剂②的混合液，滴加完毕之后，保温反应0.5～1h，随后升温至60～100℃，保温反应1～6h；反应完毕后，降温至60℃，向其中滴加烯丙基缩水甘油醚和溶剂③的混合液，保温反应0.5～1h，随后升温至60～100℃，保温反应1～6h；反应结束之后，过滤，旋蒸除去溶剂及低沸物，即得到目标产物粘接促进剂；
所述新型粘接促进剂，其特征在于，其结构式如下：
其中，R1和R2为甲基、乙基、丙基、异丙基、环己基、苯基、甲苯基、二甲苯基、苄基、乙烯基、丙烯基中的一种或上述基团的部分或全部氢原子被氯甲基、氰乙基取代；n为0～10,000的正整数，R3为甲基、乙基、丙基、异丙基或丁基。
2.根据权利要求1所述的制备方法，其特征在于，溶剂①的添加量为三烯丙基异氰脲酸酯质量的0～1.5倍，且包括0；溶剂②的添加量为三烷氧基硅烷质量的0～10倍，且包括0；溶剂③的添加量为烯丙基缩水甘油醚质量的0～1.5倍，且包括0；三烷氧基硅烷与三烯丙基异氰脲酸酯的摩尔比为0.8～1.5:1；端氢基硅油的Si-H与三烯丙基异氰脲酸酯的摩尔比为1.5～2.5:1；烯丙基缩水甘油醚与端氢基硅油的Si-H的摩尔比为0.5～0.8:1；贵金属催化剂在体系内的含量为反应物总质量的2ppm～0.5‰。
3.根据权利要求1所述的制备方法，其特征在于，贵金属催化剂为铑、铂、钯、钌及其络合物催化剂；溶剂①，溶剂②，溶剂③为甲苯、苯、四氢呋喃、环己酮、乙二醇二甲醚、邻苯二甲酸二甲酯、异丙醇中的一种或几种的混合物。
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