CN106365974B - 新的羟基酮类光引发剂及其制备和应用 - Google Patents
新的羟基酮类光引发剂及其制备和应用 Download PDFInfo
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- CN106365974B CN106365974B CN201610743345.5A CN201610743345A CN106365974B CN 106365974 B CN106365974 B CN 106365974B CN 201610743345 A CN201610743345 A CN 201610743345A CN 106365974 B CN106365974 B CN 106365974B
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Abstract
本发明公开一种如通式Ⅰ所示新的羟基酮类光引发剂及其制备和应用,该光引发剂不仅在高活性、低气味、低迁移、耐黄变等方面性能优异。本发明提出的新的α‑羟基酮类光引发剂,具有如通式Ⅰ:
Description
技术领域
本发明涉及一种新的羟基酮类化合物,它们的制备方法,以及该类化合物作为烯属不饱和化合物体系的光聚合物引发剂。
背景技术
α-羟基酮类光引发剂中目前最常用的是Darocur 1173和Irgacure 184,Darocur1173和Irgacure 184在各类光固化清漆中是主引发剂,具有热稳定性优良,使用方便,活性高,耐黄变性好,价格较低等优点,但缺点是光解过程中会产生包括苯甲醛、丙酮和环己酮在内的一系列挥发性有害有机化合物,有不良气味,同时由于分子量小,有易挥发和易迁移倾向,由此造成的环境和健康污染已经成为本领域日益引起关注的问题。
已经有相当多的专利文献报道新的α-羟基酮类光引发剂,致力于解决这些问题,例如,目前常见的代用品是Irgacure 2959(US4861916)和Esacure KIP150(Di Battista,New optimized oligomeric alpha hydroxyl acetophenone photoinitiator. Rad Tech Asia Conf. Proc.1991:398-403), Irgacure 2959由于对位引入羟乙氧基,较好地解决了Darocur 1173挥发性大及光解产物中苯甲醛气味大的问题,但因为Irgacure 2959价格较高,另外其溶解性较差,实际应用较少。Esacure KIP150是一个不迁移、低气味和耐黄变的大分子光引发剂,有较好的溶解性,但其光引发速率只有Darocur 1173的1/4,另外EsacureKIP150是室温下发粘的固体,也存在操作上的问题。
汽巴公司(CN1249009)开发出了光引发剂Irgacure 127,Irgacure 127 是以二苯甲烷为芳基的双官能团的α-羟基酮类光引发剂,是一种很好的Darocur 1173代用品,由于分子量大,所以自身气味及光解产物气味较低。但Irgacure 127本身不易结晶析出,有水或溶解存在下才能结晶析出,而且价格较高,应用上受到一定限制。蓝宝迪(CN1832912)通过二苯醚作为芳基,得到了双官能团的光引发剂 1,价格低廉,光引发效率高,但是存在易黄变和溶剂差的问题。叶正培等(CN102504504)使用二苯醚或二苯硫醚作为芳基,得到了类似的大分子光引发剂 2,但同样存在易黄变的问题;同时以 N-乙基咔唑作为芳基,通过同样的方法得到新的双官能团α-羟基酮类光引发剂 3,其吸收波长比Darocur 1173 高,摩尔吸收系数高,使得光引发效率大大提高,但价格较高。
深圳有为公司(CN102060684)也对α-羟基酮类光引发剂做了较多的研究,开发出多种α-
羟基酮类大分子光引发剂,如间位取代的双官能团的α-羟基酮类光引发剂 4,由于间位取代的Darocur 1173 比对位溶解度更好,一般为液体,使用方便,有较好的应用前景,但由于取代基对芳环的定位效应从而影响付克反应的产物,间位取代的这类α-羟基酮类化合物不太容易制备。另外,他们以联苯、萘及苯酚为芳基(CN101812142、CN101921184),得到了双官能团的α-羟基酮类光引发剂 5,以联苯为芳基(CN101724099)合成了Irgacure184 类似物 6。
这些文献反映出该领域的一个强有力的发展趋势是研究新一代环保和健康型产品,特别是要竭力减轻或消除上述传统市售光引发剂在实际应用时所体现出来的缺陷,包括光解碎片导致致癌性化合物苯和芳烃污染、VOCs释放、散发不良气味以及耐黄变、低迁移等。然而从现实应用的角度考量,新一代光引发剂替代产品的研发不仅要致力于解决上述挑战性问题,提供综合性能优化的新化合物,同时必须尽可能使这些新化合物在经济成本上也要具有相当的竞争力。
发明内容
本发明的目的是提供一种性能优异的α-羟基酮类光引发剂、其制备方法、以及以该类化合物为有效成分的含烯属不饱和化合物的自由基光聚合引发剂的应用。该光引发剂不仅在活性高、性能更好、易制备、成本低、低迁移、耐黄变等方面性能优异。
本发明提出的新的α-羟基酮类光引发剂,其具有如通式Ⅰ:
Ⅰ
其中,
X选自CH、P、P=O、N;
R1、R2、R3、R4、R5、R6可以相同也可以不同,独立选自H、C1-C20的直链或支链烷基,或R1和R2、R3和R4、R5或R6链接起来形成C3-C8环烷基;
C1-C20的直链或支链烷基可以是甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、异戊基、新戊基、己基、庚基、辛基、、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基等。
C3-C8环烷基优选环己基、环戊基、甲基或乙基取代环己基、环丁基。
本发明还涉及上述通式Ⅰ的新的α-羟基酮类光引发剂的制备方法。
当X选自CH、P、N时,新的α-羟基酮类光引发剂的制备方法包括以下步骤:
1)以式II化合物和至少一种A、B、C酰氯为原料,在三氯化铝、三氯化铁或氯化锌的
存在下对苯基进行酰基化;
2)对式III酰基化产物的羰基α-H进行卤代;
3)对式IV卤代产物进行水解反应,得到式I化合物;
当X选自P=O时,上述通式Ⅰ的新的α-羟基酮类光引发剂的制备方法,包括以下步骤:
1)以式II化合物为原料,在三氯化铝、三氯化铁或氯化锌的存在下对苯基进行酰基化;
2)对式III酰基化产物的羰基α-H进行卤代,优选氯气作为卤化试剂;
3)对式IV卤代产物进行水解反应;
4)在双氧水、过氧叔丁醇、过氧乙酸、对氯过氧苯甲酸或过氧苯甲酸存在下对式V化合物进行氧化,得到式I化合物;
步骤2)所述的卤代反应所用卤化试剂选自氯气、溴素,优选氯气作为卤化试剂。
。
上述制备方法中,使用的原料均是现有技术中的已知化合物,可商业购得或者通过已知的合成方法制备而成。该制备方法简单,制备过程中不产生污染性废弃物,且产品纯度高,收率好,适用于工业化批量生产。
本发明还涉及上述通式Ⅰ所示的新的α-羟基酮类光引发剂在光固化组合物包括:
a)至少一种烯属不饱和可光聚合化合物和
b)作为光引发剂的至少一种通式Ⅰ的化合物。
含烯属不饱和双键化合物可以含有一个或多个双键。它们可以是低分子量的(单体)或相对高分子量的(低聚物)。包含双键的单体实例为烷基或羟基烷基丙烯酸酯或甲基丙烯酸酯,例如,甲基、乙基、丁基、2-乙基己基-或2-羟基乙基丙烯酸酯,异冰片基丙烯酸酯,或者甲基丙烯酸甲基或乙基酯;硅氧烷丙烯酸酯;丙烯酰胺,甲基丙烯酰胺,N-取代的(甲基)丙烯酰胺;乙烯基酯如乙酸乙烯酯,乙烯基醚如异丁基乙烯醚,苯乙烯,烷基-和卤代苯乙烯,N-乙烯基吡咯烷酮,乙烯基氯或1,1-二氯乙烯。
含两个或多个双键的单体如乙二醇、丙二醇、新戊基乙二醇,1,6-己二醇和双酚A的二丙烯酸酯,4,4’-双(2-丙烯酰氧基乙氧基)二苯基丙烷,三羟甲基丙烷三丙烯酸酯,季戊四醇三丙烯酸酯或四丙烯酸酯,乙烯基丙烯酸酯,二乙烯基苯,二乙烯基琥珀酸酯,邻苯二甲酸二烯丙基酯,磷酸三烯丙基酯,异氰尿酸三烯丙基酯和异氰尿酸三(2-丙烯酰乙基)酯。
具有相对高分子量(低聚物)多不饱和化合物的实例为丙烯酸化的环氧树脂和聚醚、聚氨基甲酸酯;丙烯酸化或含乙烯基醚基或环氧基的聚酯。不饱和低聚物还可以是不饱和聚酯树脂,它们大多是有马来酸,邻苯二甲酸和一种或多种二醇制备的并且具有大约500-3000的分子量。另外,也可以使用乙烯醚单体和乙烯基醚低聚物,以及以马来酸酯为终端的,具有聚酯、聚氨基甲酸酯、聚醚、聚乙烯醚和环氧主链的低聚物。
烯属不饱和化合物还可以是烯属不饱和羧酸和多元醇环氧化合物的酯,和在主链或侧链基上含烯属不饱和基团的聚合物,例如不饱和聚酯,聚酰胺或聚氨基甲酸酯及其共聚物,聚丁二烯或丁二烯共聚物,聚异戊二烯和异戊二烯共聚物,在侧链上含(甲基)丙烯酸基的聚合物和共聚物,在侧链上含(甲基)丙烯酸基的聚合物和共聚物,及一种或多种该聚合物的混合物。
不饱和羧酸的例子是丙烯酸、甲基丙烯酸、丁烯酸、亚甲基丁二酸、肉桂酸和不饱和脂肪酸如亚麻酸和油酸。优选丙烯酸和甲基丙烯酸。
适宜的多元醇为芳族多元醇并尤其为脂族和环状脂族多元醇。芳族多元醇如氢醌、4,4’-二羟基二苯基、2,2-二(4-羟基苯基)丙烷,以及(线型)酚醛清漆和酚醛树脂A。脂族和环状脂族多元醇如亚烷基二醇,优选C2-12,如乙二醇、1,2-或1,3-丙二醇、1,2-、1,3-或1,4-丁二醇、戊二醇、己二醇、辛二醇、十二碳烷二醇、二甘醇、三甘醇、分子量优选为200-1500的聚乙二醇、1,3-环戊二醇、1,2-、1,3-或1,4-环己二醇、1,4-二羟甲基环己烷、甘油、季戊四醇、三羟甲基丙烷、二季戊四醇或山梨糖醇等。
本发明还涉及上述通式Ⅰ所示的新的α-羟基酮类光引发剂在光固化组合物中的应用。本发明提供的光固化组合物发生聚合的方法,包括用200-600nm范围的光源照射。非限制性地,该光引发剂可应用在光固化的纸张上光涂料、电路板用的光固化阻焊油墨、光固化标识油墨以及紫外光固化的地板涂料、塑料涂料、光导纤维涂料、光盘涂料等。尤其适用需要经受长期日晒而且耐黄变的UV-固化涂料中。
具体实施方式
以下进一步描述本发明的具体技术方案,以便于本领域技术人员进一步地理解本发明,而不构成对其权利的限制。
实施例1:化合物1的制备
1)将三苯基甲烷(48.9g,0.2mol)溶于300ml氯苯中,控制反应温度在0-10℃,加入三氯化铝(82.7g,0.62mol)搅匀后,滴加异丁酰氯(66.1,0.62mol),滴毕搅拌2h,停止反应,将反应液倒入800g与130ml浓盐酸配成的稀盐酸中,搅拌0.5h,静置分出有机相,用二氯甲烷萃取水相,合并有机相,并用200ml饱和碳酸氢钠溶液洗涤,至有机相pH值成中性,干燥,脱溶回收溶剂,得到淡黄色油状物,纯度97%,也可以不回收溶剂,有机相用无水硫酸镁干燥,直接进行下一步反应。
2)向步骤1)中性的有机相,通入氯气,LC或TLC跟踪反应,反应结束后,加入饱和碳酸氢钠溶液洗至中性,静置分出有机相,回收溶剂得黄色油状物,也可以不回收溶剂直接进行下一步反应。
3)向步骤2)所得到的有机相中加入100mL 30%的氢氧化钠溶液,加热回流反应,至反应完全,降温至室温,静置,分出有机相,回收溶剂,得浅黄色油状物90.6g,用200mL甲醇重结晶得到灰白色固体70.4g。
产物结构通过核磁共振氢谱得到确认,具体表征结果如下:1H-NMR(CDCl3,400MHz):δ 7.45(d,6H), 6.89 (d,6H), 5.48(s,1H),3.65 (s,3H), 1.46 (s,18H)。
实施例2:化合物2的制备
1)将三苯基膦(52.5g,0.2mol)溶于300ml氯苯中,控制反应温度在0-10℃,加入三氯化铝(82.7g,0.62mol)搅匀后,滴加异丁酰氯(66.1,0.62mol),滴毕搅拌反应2h,停止反应,将反应液倒入800g与130ml浓盐酸配成的稀盐酸中,搅拌0.5h,静置分出有机相,用二氯甲烷萃取水相,合并有机相,并用200ml饱和碳酸氢钠溶液洗涤,至有机相pH值成中性,干燥,脱溶回收溶剂,得到淡黄色油状物,纯度95%,也可以不回收溶剂,有机相用无水硫酸镁干燥,直接进行下一步反应。
2)向步骤1)中性的有机相,通入氯气,LC或TLC跟踪反应,反应结束后,加入饱和碳酸氢钠溶液洗至中性,静置分出有机相,回收溶剂得黄色油状物,也可以不回收溶剂直接进行下一步反应。
3)向步骤2)所得到的有机相中加入100mL 30%的氢氧化钠溶液,加热回流反应,至反应完全,降温至室温,静置,分出有机相,回收溶剂,得浅黄色油状物92.9g,用200mL甲醇重结晶得到灰白色固体74.0g。
产物结构通过核磁共振氢谱得到确认,具体表征结果如下:
1H-NMR(CDCl3,400MHz):δ 8.50(m,6H), 7.68 (m,6H), 3.65 (s,3H), 1.45 (s,18H);31P-NMR (CDCl3,400 MHz):δ -6.3 (s)。
实施例3:化合物3的制备
1)将三苯基膦(52.5g,0.2mol)溶于300ml氯苯中,控制反应温度在0-10℃,加入三氯化铝(82.7g,0.62mol)搅匀后,滴加异丁酰氯(66.1,0.62mol),滴毕搅拌反应2h,停止反应,将反应液倒入800g与130ml浓盐酸配成的稀盐酸中,搅拌0.5h,静置分出有机相,用二氯甲烷萃取水相,合并有机相,并用200ml饱和碳酸氢钠溶液洗涤,至有机相pH值成中性,干燥,脱溶回收溶剂,得到淡黄色油状物,纯度96%,也可以不回收溶剂,有机相用无水硫酸镁干燥,直接进行下一步反应。
2)向步骤1)中性的有机相,通入氯气,LC或TLC跟踪反应,反应结束后,加入饱和碳酸氢钠溶液洗至中性,静置分出有机相,回收溶剂得黄色油状物,也可以不回收溶剂直接进行下一步反应。
3)向步骤2)所得到的有机相中加入100mL 30%的氢氧化钠溶液,加热回流反应,至反应完全,降温至室温,静置,分出有机相。
4)向步骤3)中加入30%的双氧水,在60℃下反应3h,反应结束后,分别加入亚硫酸钠溶液和饱和碳酸氢钠溶液洗,有机相最后用无水硫酸镁干燥,回收溶剂,得浅黄色油状物92.0g,用200mL甲醇重结晶得到浅黄色固体71.8g。
产物结构通过核磁共振氢谱得到确认,具体表征结果如下:
1H-NMR(CDCl3,400MHz):δ 8.00-7.6(m,12H) , 3.65 (s,3H), 1.40 (s,18H);31P-NMR (CDCl3,400 MHz):δ 28.2 (s)。
实施例4:化合物4 的制备
1)取甲基丙二酸二乙酯(52.2g,0.3mol)和氯代十二烷(61.2g,0.3mol)加入到1000mL反应瓶中,常温下滴加102g 20%乙醇钠乙醇溶液,滴加完毕,缓慢升温至50-60℃,反应3h,继续升温回流反应2h,反应完后回收溶剂(控制蒸馏温度不高于135℃),降温后加入500mL 10%氢氧化钠溶液,回流进行水解反应,TLC或GC监测反应,反应完全后将反应液倒入500mL 10%的洗盐酸中,加入300ml二乙苯,静置分层,弃去水层,有机相进行共沸脱水,当温度升至175-180℃进行脱羧反应,无气体产生时再保温1h,低压回收或利用与水共沸回收二乙苯,冷却至室温,用甲醇重结晶,得61.8g浅黄色固体,熔点为30-32℃。
2)将步骤1)所得浅黄色固体加升温至熔融,加入60mL三氯化磷,升温至80℃反应3h,静置降温,弃去下层,上层得到2-甲基十四烷酰氯66.6g,备用。
3)将三苯基胺(49.1g,0.2mol)溶于300ml氯苯中,控制反应温度在0-10℃,加入三氯化铝(82.7g,0.62mol)搅匀后,滴加异丁酰氯(44.0,0.41mol),滴毕搅拌反应,TLC或GC监测反应,反应2h后,再滴加步骤2)制备的酰氯(49.4g,0.2mol),TLC或GC监测反应,反应完全后,将反应液倒入800g与130ml浓盐酸配成的稀盐酸中,搅拌0.5h,静置分出有机相,用二氯甲烷萃取水相,合并有机相,并用200ml饱和碳酸氢钠溶液洗涤,至有机相pH值成中性,干燥,脱溶回收溶剂,得到淡黄色油状物,纯度97%,也可以不回收溶剂,有机相用无水硫酸镁干燥,直接进行下一步反应。
2)向步骤1)中性的有机相,通入氯气,LC或TLC跟踪反应,反应结束后,加入饱和碳酸氢钠溶液洗至中性,静置分出有机相,回收溶剂得黄色油状物,也可以不回收溶剂直接进行下一步反应。
3)向步骤2)所得到的有机相中加入100mL 30%的氢氧化钠溶液,加热回流反应,至反应完全,降温至室温,静置,分出有机相,回收溶剂,得浅黄色油状物124.4g,用200mL甲醇重结晶得到灰白色固体88.2g。
产物结构通过核磁共振氢谱得到确认,具体表征结果如下:1H-NMR(CDCl3,400MHz):δ 7.72(d,6H), 6.71(d,6H), 4.05(s,3H),1.65-1.23(m,37H),0.88(t,3H)
目标化合物4~21的结构及其1H-NMR数据列于表1:
表1
实施例22:性能评价
通过配制示例光固化组合物,对本发明通式Ⅰ所示光引发剂的各项应用性能进行评价,包括储存固化速率、气味、迁移等方面。
1.光固化组合物的配制
上述组合物中,光引发剂为本发明公开的通式Ⅰ所示的羟基酮类光引发剂或作为对比的现有技术中已知的光引发剂,各组分均为质量份。
2.固化速率
使用22μm线棒涂布器在玻璃片上涂布上述组合物比较光引发剂1173、184和本发明实施例光引发剂的光引发剂性能。将涂布的样品安装在带上,在中压汞灯下输送该样品。以指甲反复压刻刮擦不产生印记为完全固化标准,确定完全固化样品的带速。
3.气味等级
按上述固化方法及固化速度,将光固化组合物完全固化。残余气味测试以5人分别独立的评价气味级别,以≥3人对气味等级评价相近或统一为标准。评估的标准以数字表示如下:
A级:感觉不到气味;
B级:非常轻微的气味;
C级:轻微的气味;
D级:明显的气味;
E级:强烈的气味;
F级:非常强烈的气味。
4.迁移性能
按上述固化方法及固化速度,将光固化组合物完全固化。固化后在固化体系中分别研磨下一定质量的粉末,称重,通过已知的配比可以算出光引发剂的质量;将粉末分别浸泡在一定体积的乙睛中一个月,然后测量上清液的紫外吸收光谱,通过已知的摩尔消光系数可算出溶液中光引发剂的浓度,从而算出有多少光引发剂迁移到溶液中。迁移出的光引发剂的质量/理论光引发剂质量=迁移率。
评价结果如表2中所示:
表2
由表2内容的结果可以看出,包含本发明通式Ⅰ所示的新的羟基酮类光引发剂的光固化组合物具有很好的光引发活性,均表现出了低气味、低迁移等特性。
综上所述,本发明公开的通式Ⅰ所示的新的羟基酮类光引发剂的应用性能优异,应用于光固化组合物可极大的提高光固化产品的性能。
Claims (4)
1.羟基酮类光引发剂,其具有如通式Ⅰ:
其中,
X选自N、CH、P、P=O;
R1、R2、R3、R4、R5、R6可以相同也可以不同,独立选自H、C1-C20的直链或支链烷基,或R1和R2、R3和R4、R5或R6链接起来形成C3-C8环烷基;
所述通式I化合物为:
2.一种权利要求1所述光引发剂的制备方法,其特征在于包括以下步骤:
当X选自CH、P、N时,权利要求1所述的α-羟基酮类光引发剂的制备方法包括以下步骤:
1)以式II化合物和至少一种A、B、C酰氯为原料,在三氯化铝、三氯化铁或氯化锌的存在下对苯基进行酰基化;
2)对式III酰基化产物的羰基α-H进行卤代;
3)对式IV卤代产物进行水解反应,得到式I化合物;
当X选自P=O时,上述通式Ⅰ的新的α-羟基酮类光引发剂的制备方法,包括以下步骤:
1)以式II化合物为原料,在三氯化铝、三氯化铁或氯化锌的存在下对苯基进行酰基化;
2)对式III酰基化产物的羰基α-H进行卤代;
3)对式IV卤代产物进行水解反应;
4)在双氧水、过氧叔丁醇、过氧乙酸、对氯过氧苯甲酸或过氧苯甲酸存在下对式V化合物进行氧化,得到式I化合物;
其中X'选自Cl或Br,X、R1、R2、R3、R4、R5、R6定义如权利要求1所述。
3.一种光固化组合物包括:
a)至少一种烯属不饱和可光聚合化合物和
b)作为光引发剂的至少一种权利要求1所述结构的化合物。
4.权利要求3所述的光固化组合物发生聚合的方法,包括用200-600nm范围的光源照射。
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