CN113817122A - 一种含硅链的耐低温柔性聚氨酯光敏预聚体及其制备方法 - Google Patents
一种含硅链的耐低温柔性聚氨酯光敏预聚体及其制备方法 Download PDFInfo
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Abstract
本发明提供了一种含硅链的耐低温柔性聚氨酯光敏预聚体及其制备方法。本发明将羟基硅油、二元醇与二异氰酸酯在一定条件下反应,得到含硅链及‑NCO基团封端的聚氨酯预聚体,再与含羟基、C=C的丙烯酸单体在一定温度下反应,得到所需的含硅链的耐低温柔性聚氨酯光敏预聚体。本发明提供的含硅链的耐低温柔性聚氨酯光敏预聚体保留了C=C的光敏性,硅链具有耐低温性能;可以用于柔性光敏树脂的制备、耐低温聚氨酯树脂的生产、胶黏剂的合成等,而且具有生产效率高、污染小、节省能源等优点。
Description
技术领域
本发明涉及聚氨酯光敏预聚体技术领域,特别涉及一种含硅链的耐低温柔性聚氨酯光敏预聚体及其制备方法。
背景技术
聚氨酯丙烯酸酯(PUA)的分子中含有丙烯酸官能团和氨基甲酸酯键,固化后的胶黏剂具有聚氨酯的高耐磨性、粘附力、高剥离强度以及聚丙烯酸酯卓越的光学性能和耐候性。但市面上具有光敏性的柔性耐低温聚氨酯丙烯酸酯相对较少,且价格昂贵。但聚氨酯丙烯酸酯能广泛地应用于聚氨酯胶粘剂、3D打印、涂料、弹性体、泡沫和纤维等诸多领域。因此,开发出一种新型的具有光敏性且高柔性耐低温的聚氨酯预聚体极具现实意义。
有机硅材料主链是由Si—O—Si链节构成的,侧链则通过硅原子与其他有机基团相连接。这种特殊的分子结构使其具有耐候性、耐高低温、耐老化、电绝缘、低表面活性、耐腐蚀等特性。紫外光固化通常在常温下数妙或数十秒即可固化,得到硬化干燥的涂膜。且紫外光固化技术具有效率高、环保、能耗低、操作简单、可行性强等特点。将紫外光固化技术应用到有机硅材料中,不仅可以有效地结合两者的优点,还可以拓宽光固化技术应用的领域。
但大多数有机硅材料与其他树脂相溶性较差。如何将聚氨酯和有机硅材料的优异性能结合起来成了研究的热点。如孙芳等人通过在有机硅链段上接入聚氨酯链段合成了具有优异感光性和较好混溶性的光敏有机硅预聚体。J.Y.Cheng等人以聚醚封端的有机硅共聚物、聚丙二醇(Mn=2000g/mol)、甲苯二异氰酸酯(TDI)为反应原料合成了一系列可进行光固化的多官能团聚氨酯丙烯酸酯预聚物。将预聚物进行光固化,所得固化薄膜具备良好的热稳定性。但是对于含硅链的聚氨酯树脂的柔性、耐低温性都没有相关的研究报道。
因此,积极开展含硅链的耐低温柔性聚氨酯光敏预聚体的研究具有重要的理论意义和应用价值。
发明内容
针对现有技术的情况和不足,本发明的目的在于提供一种含硅链的耐低温柔性聚氨酯光敏预聚体及其制备方法。本发明提供的含硅链的耐低温柔性聚氨酯光敏预聚体带有光敏基团C=C、较好的柔韧性以及优良的耐低温性能。
为了实现上述目的,本发明采用的技术方案为:
一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,包括以下步骤:
(1)在装有二元醇的圆底烧瓶中,加入计量的二异氰酸酯,在氮气保护及50~120℃条件下反应0.1~5.0h,再加入计量的羟基硅油,在氮气保护及50~120℃条件下反应0.1~5.0h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与含羟基、C=C的丙烯酸单体在氮气保护及40~120℃条件下反应0.1~5.0h,即得所述的含硅链耐低温柔性聚氨酯光敏预聚体。
具体反应式为:
优选的,所述的二元醇为聚己内酯二醇、聚己二酸乙二醇酯、聚四氢呋喃二醇、聚己二酸乙二醇丙二醇酯等中的一种或几种。
优选的,所述的二异氰酸酯为对苯二异氰酸酯、甲苯二异氰酸酯、异佛尔酮二异氰酸酯、六亚甲基二异氰酸酯等中的一种或几种。
优选的,所述的羟基硅油为分子量为450、500、1000、1800、2000、10000、20000的羟基硅油中的一种或几种。
优选的,按摩尔比,所述的二元醇与二异氰酸酯的比例为1:0.9~1:5;二异氰酸酯与羟基硅油比例为1:0.1~1:3.0;二异氰酸酯与带有羟基、C=C的丙烯酸单体的比例为1:1~1:2。
与现有技术相比,本发明取得的有益效果是:
本发明通过二元醇与二异氰酸酯、羟基硅油、丙烯酸单体易反应形成异含硅链的耐低温柔性聚氨酯光敏预聚体,具有反应速度快、生产效率高、污染小、操作便捷、降低成本等优点。同时所得的含硅链的耐低温柔性聚氨酯光敏预聚体保留了C=C的光敏性,硅链具有耐低温性能,还具有高柔性、高反应活性、优良的耐低温性能等特点,可以用于耐低温柔性光敏树脂的制备、涂层材料及胶黏剂等的使用、耐低温柔性聚氨酯的合成等。
附图说明
图1是本发明制备的含硅链的耐低温柔性聚氨酯光敏预聚体涉及的反应示意图。
图2是本发明制备的含硅链的耐低温柔性聚氨酯光敏预聚体涉及的红外谱图。
图3是本发明制备的含硅链的耐低温柔性聚氨酯光敏预聚体涉及的核磁谱图。
具体实施方式
实施例1
(1)在装有60g聚己内酯二醇的圆底烧瓶中,加入9.6g对苯二异氰酸酯,在氮气保护及100℃条件下反应2h,再加入15.29g羟基硅油(2000分子量),在氮气保护及80℃条件下反应1h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与7.8g甲基丙稀酸羟乙酯在氮气保护及80℃条件下反应1h,即得含硅链耐低温柔性聚氨酯光敏预聚体1。
将所得的含硅链耐低温柔性聚氨酯光敏预聚体进行红外谱图表征,结果如图2所示:1000-1130cm-1处为Si-O-Si的不对称伸缩振动特征吸收峰;1640cm-1处为C=C伸缩振动特征吸收峰;1720cm-1处为C=O伸缩振动特征吸收峰;2270cm-1处无明显的-NCO特征吸收峰;2960cm-1处为CH3伸缩振动特征吸收峰。综上,说明含硅链耐低温柔性聚氨酯光敏预聚体合成成功。
将所得的含硅链耐低温柔性聚氨酯光敏预聚体进行核磁谱图表征,结果如图3所示。0.00~0.07ppm处为与硅相连甲基上H的特征峰,说明Si-O链已接枝上。化学位移7.90~8.00ppm处为-CO-NH-上的H特征峰,说明HEMA与多余的-NCO基本反应完全,生成-CO-NH-。综上,说明含硅链耐低温柔性聚氨酯光敏预聚体合成成功。
实施例2
(1)在装有60g聚己内酯二醇的圆底烧瓶中,加入10.45g甲苯二异氰酸酯,在氮气保护及85℃条件下反应3h,再加入6.375g羟基硅油(500分子量),在氮气保护及80℃条件下反应2h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与7.8g甲基丙稀酸羟乙酯在氮气保护及80℃条件下反应2h,即得含硅链耐低温柔性聚氨酯光敏预聚体2。
实施例3
(1)在装有50g聚四氢呋喃二醇酯的圆底烧瓶中,加入16.67g异佛尔酮二异氰酸酯,在氮气保护及70℃条件下反应3h,再加入10g羟基硅油(450分子量),在氮气保护及60℃条件下反应2h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与5.4g甲基丙稀酸羟丙酯在氮气保护及60℃条件下反应2.5h,即得含硅链耐低温柔性聚氨酯光敏预聚体3。
实施例4
(1)在装有50g聚己二酸乙二醇酯的圆底烧瓶中,加入6g对苯二异氰酸酯,在氮气保护及110℃条件下反应1.5h,再加入15.92g羟基硅油(2000分子量),在氮气保护及90℃条件下反应2h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与4.88g甲基丙稀酸羟乙酯在氮气保护及80℃条件下反应1.5h,即得含硅链耐低温柔性聚氨酯光敏预聚体4。
实施例5
(1)在装有50g聚己二酸乙二醇酯的圆底烧瓶中,加入8.71g甲苯二异氰酸酯,在氮气保护及85℃条件下反应2h,再加入12.75g羟基硅油(2000分子量),在氮气保护及90℃条件下反应2h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与5.4g甲基丙稀酸羟丙酯在氮气保护及80℃条件下反应1h,即得含硅链耐低温柔性聚氨酯光敏预聚体5。
实施例6
(1)在装有50g聚己二酸乙二醇丙二醇酯的圆底烧瓶中,加入8.41g六亚甲基二异氰酸酯,在氮气保护及95℃条件下反应3.5h,再加入18.89g羟基硅油(1800分子量),在氮气保护及95℃条件下反应4h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与5.86g甲基丙稀酸羟乙酯在氮气保护及80℃条件下反应1h,即得含硅链耐低温柔性聚氨酯光敏预聚体6。
实施例7
在装有50g聚己二酸乙二醇丙二醇酯的圆底烧瓶中,加入9.58g甲苯二异氰酸酯,在氮气保护及75℃条件下反应4h,再加入10.63g羟基硅油(1000分子量),在氮气保护及85℃条件下反应2.5h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与6.85g甲基丙稀酸羟丙酯在氮气保护及85℃条件下反应1.5h,即得含硅链耐低温柔性聚氨酯光敏预聚体7。
实施例8
(1)在装有50g聚己内酯二醇的圆底烧瓶中,加入11.11g异佛尔酮二异氰酸酯,在氮气保护及90℃条件下反应5h,再加入11.81g羟基硅油(1800分子量),在氮气保护及80℃条件下反应2h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与4.55g甲基丙稀酸羟乙酯在氮气保护及80℃条件下反应1.5h,即得含硅链耐低温柔性聚氨酯光敏预聚体8。
实施例9
(1)在装有10g聚己内酯二醇的圆底烧瓶中,加入1.68g六亚甲基二异氰酸酯,在氮气保护及85℃条件下反应2.5h,再加入21.25g羟基硅油(10000分子量),在氮气保护及70℃条件下反应1h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与1.44g甲基丙稀酸羟丙酯在氮气保护及80℃条件下反应0.5h,即得含硅链耐低温柔性聚氨酯光敏预聚体9。
实施例10
(1)在装有20g聚己二酸乙二醇酯的圆底烧瓶中,加入4.2g六亚甲基二异氰酸酯,在氮气保护及95℃条件下反应2h,再加入85g羟基硅油(20000分子量),在氮气保护及80℃条件下反应2h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与2.6g甲基丙稀酸羟丙酯在氮气保护及80℃条件下反应1h,即得含硅链耐低温柔性聚氨酯光敏预聚体10。
Claims (7)
1.一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,其特征在于:将羟基硅油、二元醇与二异氰酸酯在一定条件下反应,得到含硅链及-NCO基团封端的聚氨酯预聚体,再与含羟基、C=C的丙烯酸单体在一定温度下反应,得到含硅链的耐低温柔性聚氨酯光敏预聚体。
2.根据权利要求1所述的一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,其特征在于:包括如下步骤:
(1)在装有二元醇的圆底烧瓶中,加入计量的二异氰酸酯,在氮气保护及50~120℃条件下反应0.1~5.0h,再加入计量的羟基硅油,在氮气保护及50~120℃条件下反应0.1~5.0h,得到含硅链及-NCO基团封端的聚氨酯预聚体;
(2)所得的含硅链及-NCO基团封端的聚氨酯预聚体再与含羟基、C=C的丙烯酸单体在氮气保护及40~120℃条件下反应0.1~5.0h,得到含硅链耐低温柔性聚氨酯光敏预聚体。
3.根据权利要求1所述的一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,其特征在于:所述的二元醇为聚己内酯二醇、聚己二酸乙二醇酯、聚四氢呋喃二醇、聚己二酸乙二醇丙二醇酯中的一种或其组合。
4.根据权利要求1所述的一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,其特征在于:所述的二异氰酸酯为对苯二异氰酸酯、甲苯二异氰酸酯、异佛尔酮二异氰酸酯、六亚甲基二异氰酸酯中的一种或其组合。
5.根据权利要求1所述的一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,其特征在于:所述的羟基硅油为分子量为450、500、1000、1800、2000、10000、20000的羟基硅油中的一种或其组合。
6.根据权利要求1所述的一种含硅链的耐低温柔性聚氨酯光敏预聚体的制备方法,其特征在于:按摩尔比,所述的二元醇与二异氰酸酯的比例为1:0.9~1:5;二异氰酸酯与羟基硅油比例为1:0.1~1:3.0;二异氰酸酯与带有羟基、C=C的丙烯酸单体的比例为1:1~1:2。
7.一种含硅链的耐低温柔性聚氨酯光敏预聚体,其特征在于:其是根据权利要求1至6之一所述的制备方法制得。
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