CN110615861A - 一种氯醋树脂基的二苯甲酮大分子光引发剂及其制备方法 - Google Patents
一种氯醋树脂基的二苯甲酮大分子光引发剂及其制备方法 Download PDFInfo
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- CN110615861A CN110615861A CN201910802077.3A CN201910802077A CN110615861A CN 110615861 A CN110615861 A CN 110615861A CN 201910802077 A CN201910802077 A CN 201910802077A CN 110615861 A CN110615861 A CN 110615861A
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- vinyl chloride
- ethyl acetate
- benzophenone
- photoinitiator
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- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 title description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 138
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- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
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- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
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Abstract
本发明涉及一种氯醋树脂基的二苯甲酮大分子光引发剂及其制备方法,其制备方法是以N‑甲基二乙醇胺、二异氰酸酯合成异氰酸根封端的含有氨基甲酸酯结构的中间物PU‑1,将PU‑1依次与羟基三元氯醋树脂、对羟基二苯甲酮反应得到目标产物PV‑PU。本发明制得的这种大分子光引发剂,其结构通式如(I),因在同一分子链上同时含有二苯甲酮和叔胺结构,可提高光敏分解产生活性物种效率,又由于其同时含有氯醋、聚氨酯结构,不仅增加与引发体系的相容性,大大降低光引发剂的表面迁移,同时对颜料有优异的展色性,对底材的附着力俱佳,可作为氯醋树脂特种功能材料使用,在UV光固化、木器漆、PVC基材、油墨印刷等领域可以有广泛应用。
Description
技术领域
本发明涉及一种氯醋树脂基的二苯甲酮大分子光引发剂及其制备方法。
背景技术
紫外光固化技术是涂料、粘合剂和油墨发展过程中的一个代表性的起步,是20世纪60年代问世的新型绿色技术,是利用光(紫外光或可见光)为能源,引发具有化学反应活性的液态物质快速转变为固态的过程。与传统的溶液成型相比,紫外光固化技术被归纳为具有“5E”特点:高效(Efficient)、适应性广(Enabling)、经济(Economical)、节能(Energysav-ing)和环境友好(Environmental friendly)。光固化体系通常包括活性单体、预聚物和光引发剂。在紫外辐射下,通过光引发剂的光解反应产生活性种引发单体和预聚物的聚合。随着科学技术的不断发展及对环保的日益重视,光固化技术迅猛发展,目前该技术已经广泛应用于涂料、油墨、胶粘剂、生物材料、纳米材料等领域。
在光固化体系的技术进步过程中,新型光敏引发剂体系的研究与开发始终占据着十分重要的位置。在自由基光聚合中,二苯甲酮衍生物是使用得最为广泛的光引发剂。中国发明专利(公开号:CN 107163206A)公开了一种高分子二苯甲酮类化合物的制备及其在抗光污染中的应用,利用二苯甲酮与过量的碱金属钠生成二苯甲酮二钠引发剂,在催化剂的作用下与甲苯-2,4-二异氰酸酯反应,再与4,4’-二羟基二苯甲酮反应制备高分子二苯甲酮类化合物。
近年来,由光引发剂和共引发剂胺组成的夺氢型光引发体系受到广泛关注。但随着科学技术的发展,人们对光引发剂提出了更高的要求,包括具有良好的光引发性能,与体系相容性好,迁移率低、毒性小,环境兼容性好,存储稳定性高。因此,亟需开发稳定、低毒、高效环保且与固化体系具有良好相容性的光引发体系。另外,光引发剂大分子化,将具有很多优点,例如:(1)气味低,挥发度低;(2)抗迁移性好,毒性小,环境兼容性更好;(3)树脂的相容性好;(4)减少黄变等。
氯醋树脂开发始于20世纪20年代末,一般具有对颜料的高分散性,优异的成膜性和溶剂释放性、柔韧性、高耐磨性、耐化学性、阻燃性、良好溶解性和工艺性以及广泛的可调配性。因此,氯醋树脂为配置工业涂料、油墨的优选粘接树脂。特别是在UV应用领域的木器涂料、PVC软包装油墨等行业有越来越广泛的应用。
发明内容
针对上述传统小分子光引发性能光引发效率不高,与体系相容性差,表面迁移率高的问题。本发明提供了一种氯醋树脂基二苯甲酮大分子光引发剂及其制备方法。
本法所制备的氯醋树脂基的二苯甲酮大分子光引发剂,在同一分子链上同时含有二苯甲酮和叔胺结构,故可提高光敏分解产生活性物种效率,光引发效率较高,由于其同时含有氯醋、聚氨酯结构,增加了与引发体系的相容性,光引发剂的大分子结构还大大降低了光引发剂的表面迁移。
本发明的技术方案是:
本发明从分子结构设计出发,通过分子设计生成二异氰酸酯封端的聚氨酯分子结构,并与含羟基的氯醋树脂和对羟基苯甲酮反应,合成出聚氨酯分子链两端连接有叔胺结构的氯醋树脂基苯甲酮大分子光引发剂。
本发明制备的大分子光引发剂,该光引发剂的化学结构式如下:
其中,R1-OH为羟基或羟烷基结构。
本发明提供一种氯醋树脂基的二苯甲酮大分子光引发剂及其制备方法,包含以下步骤(以下均以官能团摩尔分数表示,反应全程通氮气保护):
(a)将单体4-4.5份二异氰酸酯、2份催化剂溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌2-4h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.5-1.7份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,滴完后继续磁力搅拌0.5h后,继续使用恒压滴液漏斗滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌12-24h后,红外检测-NCO基团消失即停止反应,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物PV-PU。
本发明的大分子光引发剂的反应式如下:
本发明中所述的二异氰酸酯与N-甲基二乙醇胺的摩尔比为:4-4.5:2,羟基三元氯醋树脂与对羟基二苯甲酮的摩尔比为1:1.5-1.7。
本发明中所述的催化剂为异辛酸锌,辛酸亚锡,二月桂酸二丁基锡,马来酸二甲基锡中的任一种。
本发明中所述的二异氰酸酯是4,4’-二苯基甲烷二异氰酸酯(MDI)、甲苯-2,4-二异氰酸酯(TDI)、六亚甲基二异氰酸酯(HDI)、异佛尔酮二异氰酸酯(IPDI)中的任意一种。
所述PU-1与对羟基二苯甲酮的摩尔比为1:1。
本发明的有益效果是:
本发明所制备的氯醋树脂基的二苯甲酮大分子光引发剂具备以下优点:(1)在同一分子链上同时含有二苯甲酮和叔胺结构,具有较高的光引发效率;(2)同时含有氯醋树脂和聚氨酯结构,增加了与引发体系的相容性;(3)光引发剂分子结构上引入的氯醋树脂基具有丰富的-OH,引入的叔胺结构具有较多的-NH-都能和水分子形成氢键结构,增加光引发剂在水中的溶解性;(4)光引发剂分子结构上引入氯醋树脂基可以改善水性光固化涂料的柔韧性;(5)光引发剂大分子化大大降低了光引发剂的表面迁移;(6)分子结构可设计性强;(7)对PVC等基材有较好的附着力;(8)对颜料拥有优异的展色性。
具体实施方式
现结合以下实施例对本发明作进一步详细的描述。但应理解,以下实施例仅是对本发明实施方式的举例说明,而非是对本发明范围的限定。
实施例1
(a)将单体4.5份MDI、2份异辛酸锡溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌4h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.7份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,PU-1与对羟基二苯甲酮的摩尔比为1:1,滴完后继续磁力搅拌0.5h后,使用恒压滴液漏斗将继续滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌24h后,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物(PV-PU-1)。
实施例2
(a)将单体4份TDI、2份辛酸亚锡溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌2h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.5份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,PU-1与对羟基二苯甲酮的摩尔比为1:1,滴完后继续磁力搅拌0.5h后,使用恒压滴液漏斗将继续滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌12h后,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物(PV-PU-2)。
实施例3
(a)将单体4.5份HDI、2份二月桂酸二丁基锡溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌3h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.6份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,PU-1与对羟基二苯甲酮的摩尔比为1:1,滴完后继续磁力搅拌0.5h后,使用恒压滴液漏斗将继续滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌20h后,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物(PV-PU-3)。
实施例4
(a)将单体4.2份IPDI、2份马来酸二甲基锡溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌4h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.7份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,PU-1与对羟基二苯甲酮的摩尔比为1:1,滴完后继续磁力搅拌0.5h后,使用恒压滴液漏斗将继续滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌16h后,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物(PV-PU-4)。
实施例5
(a)将单体4.5份TDI、2份二月桂酸二丁基锡溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌2h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.7份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,PU-1与对羟基二苯甲酮的摩尔比为1:1,滴完后继续磁力搅拌0.5h后,使用恒压滴液漏斗将继续滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌18h后,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物(PV-PU-5)。
实施例6
(a)将单体4.5份IPDI、2份辛酸亚锡溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌4h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.7份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,PU-1与对羟基二苯甲酮的摩尔比为1:1,滴完后继续磁力搅拌0.5h后,使用恒压滴液漏斗将继续滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌24h后,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物(PV-PU-6)。
配方应用
将实施例1-6制备的氯醋树脂基的二苯甲酮大分子光引发剂应用于可光聚合的复合材料中。
应用实施例1
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
丙烯酸缩水甘油酯20%;
邻苯二甲酸二乙二醇二丙烯酸酯20%;
实施例1所制备的氯醋树脂基的二苯甲酮大分子光引发剂5%;
碳酸钙5%
应用实施例2
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
丙烯酸丁酯30%;
季戊四醇三丙烯酸酯10%;
实施例2所制备的氯醋树脂基的二苯甲酮大分子光引发剂5%;
碳酸钙5%
应用实施例3
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
二丙二醇二丙烯酸酯25%;
乙氧基化三羟甲基丙烷三丙烯酸酯15%;
实施例3所制备的氯醋树脂基的二苯甲酮大分子光引发剂5%;
碳酸钙5%
应用实施例4
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
丙烯酸羟丙酯10%
乙氧基化双酚A二丙烯酸酯25%;
丙氧基化甘油三丙烯酸酯5%;
实施例4所制备的氯醋树脂基的二苯甲酮大分子光引发剂5%;
碳酸钙5%。
应用实施例5
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
丙烯酸羟丙酯10%
乙氧基化双酚A二丙烯酸酯25%;
丙氧基化甘油三丙烯酸酯5%;
实施例5所制备的氯醋树脂基的二苯甲酮大分子光引发剂5%;
碳酸钙5%。
应用实施例6
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
丙烯酸羟丙酯10%
乙氧基化双酚A二丙烯酸酯25%;
丙氧基化甘油三丙烯酸酯5%;
实施例6所制备的氯醋树脂基的二苯甲酮大分子光引发剂5%;
碳酸钙5%。
应用对比例1
可光聚合的复合材料由如下组分及其百分含量组成:
环氧丙烯酸酯10%
聚氨酯丙烯酸酯25%
聚酯丙烯酸酯15%;
丙烯酸缩水甘油酯20%;
邻苯二甲酸二乙二醇二丙烯酸酯20%;
总质量为5%的PU-1与对羟基二苯甲酮和三元氯醋树脂摩尔比为1.7:1.7:1;
碳酸钙5%。
上述应用实施例1-6和应用对比例1将一种具有光活性的氯醋树脂基的二苯甲酮大分子应用于可光聚合的复合材料,具体包括如下步骤:
先将丙烯酸酯树脂与活性稀释剂搅拌混合均匀,然后在搅拌的条件下依次加入光引发剂、填料,用高速分散机高速研磨分散均匀,真空脱泡,将获得的液体复合物涂布在基材上,经烘烤去除溶剂,再经过高压紫外汞灯固化即获得聚合物复合材料。
实施例1-6和应用对比例1所制备的聚合物复合材料性能测试如表1所示。
表1
实施例1-4和应用对比例1-2所制备的聚合物复合材料附着力测试按照《GB/T9286-98》标准进行测试,硬度测试按照《GB/T 6739-1996》标准进行测试,耐水性测试按照《GB1733-(79)88漆膜耐水性测定法》标准进行测试,耐冲击强度按照《GB/T 1732-1993》标准进行测试,柔韧性按照《GB/T 1731-1993》标准进行测试。
从表1可以看出,应用实施例1-6的添加了氯醋树脂基的二苯甲酮大分子光引发剂的复合材料的各项性能优于应用对比例1。
以上述依据本发明的理想实施例为启示,通过上述的说明内容,相关工作人员完全可以在不偏离本项发明技术思想的范围内,进行多样的变更以及修改。本项发明的技术性范围并不局限于说明书上的内容,必须要根据权利要求范围来确定其技术性范围。
Claims (6)
1.一种氯醋树脂基的二苯甲酮大分子光引发剂,其化学结构式为:
其中,R1-OH为羟基或羟烷基结构。
2.一种氯醋树脂基的二苯甲酮大分子光引发剂的制备方法,其特征在于:包括如下步骤(反应全程通氮气保护):
(a)将单体4-4.5份二异氰酸酯、2份催化剂溶于40份乙酸乙酯中,2份N-甲基二乙醇胺溶于20份乙酸乙酯并加入到恒压滴液漏斗中,控制滴速4-5s/滴,室温下磁力搅拌2-4h后,红外检测羟基消失即停止反应,得到中间产物PU-1的乙酸乙酯溶液。
(b)将1.5-1.7份对羟基二苯甲酮溶于20份乙酸乙酯中并加入到恒压滴液漏斗中,控制滴速4-5s/滴,滴加到完全溶解的PU-1的乙酸乙酯溶液中,滴完后继续磁力搅拌0.5h后,继续使用恒压滴液漏斗滴加溶有1份羟基三元氯醋树脂的10份乙酸乙酯溶液,控制滴速4-5s/滴,室温下磁力搅拌12-24h后,红外检测-NCO基团消失即停止反应,然后用无水硫酸钠干燥有机层,过滤,滤液减压蒸馏除去溶剂后,真空干燥后得到目标产物PV-PU。
3.根据权利要求2所述的一种氯醋树脂基的二苯甲酮大分子光引发剂的制备方法,其特征在于:所述二异氰酸酯是MDI、TDI、HDI、IPDI中的任意一种。
4.根据权利要求2所述的一种氯醋树脂基的二苯甲酮大分子光引发剂的制备方法,其特征在于:所述的二异氰酸酯与N-甲基二乙醇胺的摩尔比为:4-4.5:2,羟基三元氯醋树脂与对羟基二苯甲酮的摩尔比为1:1.5-1.7。
5.根据权利要求2所述的一种氯醋树脂基的二苯甲酮大分子光引发剂的制备方法,其特征在于:所述催化剂为异辛酸锌,辛酸亚锡,二月桂酸二丁基锡,马来酸二甲基锡中的任意一种。
6.根据权利要求2所述的一种氯醋树脂基的二苯甲酮大分子光引发剂的制备方法,其特征在于:所述PU-1与对羟基二苯甲酮的摩尔比为1:1。
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