CN109306027B - 一种双官能光引发剂及其应用 - Google Patents
一种双官能光引发剂及其应用 Download PDFInfo
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- CN109306027B CN109306027B CN201710627524.7A CN201710627524A CN109306027B CN 109306027 B CN109306027 B CN 109306027B CN 201710627524 A CN201710627524 A CN 201710627524A CN 109306027 B CN109306027 B CN 109306027B
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供一种具有双官能团的光引发剂，其特点在于同时具有了裂解型光引发剂和夺氢型光引发剂的活性基团。其结构如式(Ⅰ)所示，其中X为CH2或(CH2CH2O)n(n为1～8的整数)；R1、R2、R3、R4、R5取自H、C1～C12烷基、C1～C12烷氧基、卤素原子，或除R3是苯基外，R1、R2、R4、R5均为H。本发明的化合物适用于作为烯属不饱和化合物或该类化合物的混合物的光聚合引发剂。式(Ⅰ)化合物可单独使用或与其他光引发剂，胺促进剂，增敏剂、添加剂等混合使用。
Description
应用领域
本发明提供一类同时具有了裂解型和夺氢型光引发剂活性基团的新型双官能光引发剂。该类化合物适用于作为烯属不饱和化合物或该类化合物的混合物的光聚合引发剂。
背景技术
目前，二苯甲酮类光引发剂、苯甲酰甲酸酯类、α-羟基酮类光引发剂是UV固化清漆中广泛而大量使用的商业光引发剂种类，因为它表面固化良好、不易泛黄、溶解性良好。例如4-甲基二苯甲酮(MBP)、苯甲酰甲酸甲酯(MBF)、2-甲基-2-羟基-1-苯基-1-丙酮(Irgacure1173)，但这些小分子量光引发剂的不足之处是固化后的固化膜气味较大，而且易从固化膜中迁移污染接触物。
单官能的α-羟基酮类化合物如Irgacure 1173、Irgacure 184是Ciba公司较早披露(EP0003002)和上市的品种，在此基础上又推出了活性更好的诸如Irgacure 127之类的双官能度的α-羟基酮类化合物(CN1582267、CN101812142)。
在专利申请书CN103709036A中公布了两种结构如式A、式B所示的以裂解型苯甲酰甲酸酯类化合物和α-羟基酮类化合物复合到一起得到的双官能团的光引发剂。
在专利申请书CN104736513A中也公布了类似结构的双官能团的光引发剂，如式C所示。
其中R8为式D或者式E。
以上这些双官能光引发剂尽管克服了小分子光引发剂的气味大，迁移率高的缺点，但由于它们都属于裂解型光引发剂，在光固化过程中裂解的活性自由基很容易被氧猝灭形成氧阻聚，导致其表面固化慢，直接表现就是固化膜粘手，尤其在较薄的涂膜固化时表现尤为明显。
本发明提供一种同时具有苯甲酰甲酸酯类化合物和二苯甲酮类化合物的双官能光引发剂。其特点在于同时具有了裂解型光引发剂和夺氢型光引发剂的活性基团。这类化合物具有良好的光固化活性，优异的表面抗氧阻聚和耐黄变的性能，同时能克服原有小分子光引发剂挥发性、迁移性、气味大的缺点，在光固化油墨和涂料的配方，尤其是在光固化上光油和清漆配方中具有良好的应用前景。
发明内容
本发明提供一种双官能光引发剂，其结构如式(Ⅰ)所示：
其中：X为CH2或(CH2CH2O)n(n为1～8的整数)；
R1、R2、R3、R4、R5取自H、C1～C12烷基、C1～C12烷氧基、卤素原子，或除R3是苯基外，R1、R2、R4、R5均为H。
上述的双官能光引发剂，具体结构有如式(Ⅱ)、式(Ⅲ)、式(Ⅳ)、式(Ⅴ)、式(Ⅵ)所示。
本发明还提出一种光固化组合物，其特征是含有至少一种本发明中所述的式(Ⅰ)化合物作为光引发剂和至少一种可进行自由基聚合的烯属不饱和化合物。
除上述两种组分外，光固化组合物还可以包含其他引发剂、胺促进剂，增敏剂和/或其他添加剂。
可光聚合的组合物中，式(Ⅰ)化合物的添加量为基于总组分的0.05～20％重量％，优选0.5～10％重量％。
光固化组合物可用于光固化涂料、油墨、粘合剂及3D打印中，特别适用于上光油和罩光清漆，其特征是含有至少一种式(Ⅰ)光引发剂化合物。
上述光固化组合物经光固化后得到的物品，例如上光的纸张、印刷品、木板等。
烯属不饱和化合物例如，含双键单体的实例为(甲基)丙烯酸及其盐、(甲基)丙烯酸酯(例如，烷基醋，如甲基、乙基、2-氯乙基、N-二甲氨基乙基、正丁基、异丁基、戊基、己基、环己基、2-乙基己基、辛基、异茨基[2-外冰片基]酯)、苯基、苄基及邻-、间-及对-羟基苯基酯、羟基烷基酯(例如2-羟基乙基、2-羟基丙基、4-羟基丁基、3,4-二羟基丁基或甘油[1,2,3-丙三醇]酯)、环氧基烷基酯(例如缩水甘油基、2,3-环氧基丁基、3,4-环氧基丁基、2,3-环氧基环己基、10,11-环氧基十一烷基酯)、(甲基)丙烯酰胺、N取代的(甲基)丙烯酰胺(例如N-羟甲基丙烯酰胺、N-羟甲基甲基丙烯酰胺、N-乙基丙烯酰胺、N-乙基甲基丙烯酰胺、N-己基丙烯酰胺、N-己基甲基丙烯酰胺、N-环己基丙烯酰胺、N-环己基甲基丙烯酰胺、N-羟乙基丙烯酰胺、N-苯基丙烯酰胺、N-苯基甲基丙烯酰胺、N-苄基丙烯酰胺、N-苄基甲基丙烯酰胺、N-硝基苯基丙烯酰胺、N-硝基苯基甲基丙烯酰胺、N-乙基-N-苯基丙烯酰胺、N-乙基-N-苯基甲基丙烯酰胺、N-(4-羟基苯基)丙烯酰胺及N-(4-羟基苯基)甲基丙烯酰胺、IBMAA(N-异丁氧基甲基丙烯酰胺))、(甲基)丙烯睛、不饱和酸酯(如衣康酸酯、马来酸酯、2,3-二甲基马来酸酯,2-氯马来酸酯)、不饱和酯(如马来酸酯、邻苯二甲酸酯、衣康酸酯[亚甲琥珀酸酯])、苯乙烯(如甲基苯乙烯、氯甲基苯乙烯及邻-、间-及对-羟基苯乙烯、二乙烯苯)、乙烯基醚(如异丁基乙烯基醚、乙基乙烯基醚,2-氯乙基乙烯基醚、羟乙基乙烯基醚、丙基乙烯基醚、丁基乙烯基醚、异丁基乙烯基醚、辛基乙烯基醚及苯基乙烯基醚)、乙烯及烯丙酯(如乙酸乙烯酯、丙烯酸乙烯、氯乙酸乙烯酯、丁酸乙烯酯及苯甲酸乙烯酯、琥珀酸二乙烯酯、邻苯二甲酸二烯丙酯、磷酸三烯丙酯、氯乙烯及偏二氯乙烯酯)、异氰尿酸酯(如异氰尿酸三烯丙酯及参(2-丙烯酰基乙基)异氰尿酸酯)、N-乙烯基-杂环化合物(如N-乙烯基毗咯烷酮或N取代的乙烯基毗咯烷酮,N-乙烯基己内酰胺或N取代的乙烯基己内酰胺、N-乙烯基吡啶,N-乙烯基吡啶。
包含两个或更多个双键的单体的实例为乙二醇、丙二醇、新戊二醇、1,6-己二醇或双酚A的二丙烯酸酯、及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、新戊四醇三丙烯酸酯或四丙烯酸酯、丙烯酸乙烯酯、二乙烯苯、琥珀酸二乙烯酯、邻苯二甲酸二烯丙酯、磷酸三烯丙酯、异氰尿酸三烯丙酯或异氰尿酸参(2-丙酰基)乙酯。
二丙烯酸酯，如1,6-己二醇二丙烯酸酯(HDDA)、乙二醇二丙烯酸酯、丙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、新戊二醇二丙烯酸酯,1,6-己二醇二丙烯酸酯及双酚A二丙烯酸酯、三羟甲基丙烷三丙烯酸酯、三羟甲基乙烷三丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、三羟甲基乙烷三甲基丙烯酸酯,1,4-丁二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯、四乙二醇二丙烯酸酯、新戊四醇二丙烯酸酯、新戊四醇三丙烯酸酯、新戊四醇四丙烯酸酯、新戊四醇四丙烯酸酯、二聚新戊四醇二丙烯酸酯、二聚新戊四醇三丙烯酸酯、二聚新戊四醇四丙烯酸酯、二聚新戊四醇五丙烯酸酯、二聚新戊四醇六丙烯酸酯、三聚新戊四醇八丙烯酸酯、新戊四醇二甲基丙烯酸酯、新戊四醇三甲基丙烯酸酯、二聚新戊四醇二甲基丙烯酸酯、二聚新戊四醇四甲基丙烯酸酯、三聚新戊四醇八甲基丙烯酸酯、新戊四醇二衣康酸酯、二聚新戊四醇三衣康酸酯、二聚新戊四醇五衣康酸酯、二聚新戊四醇六衣康酸酯、乙二醇二丙烯酸酯,1,3-丁二醇二丙烯酸酯,1,3-丁二醇二甲基丙烯酸酯、1,4-丁二醇二衣康酸酯、山梨糖醇三丙烯酸酯、山梨糖醇四丙烯酸酯、经新戊四醇改性的三丙烯酸酯、山梨糖醇四甲基丙烯酸酯、山梨糖醇五丙烯酸酯、山梨糖醇六丙烯酸酯、低聚酯丙烯酸酯及甲基丙烯酸酯、甘油二-及三-丙烯酸酯,1,4-环己烷二丙烯酸酯、具有200至1500分子量的聚乙二醇的双丙烯酸酯及双甲基丙烯酸酯、或其混合物。
还常常会使用烷氧基化醇的丙烯酸酯，例如乙氧基化甘油三丙烯酸酯、丙氧基化甘油三丙烯酸酯、乙氧基化三羟甲基丙烷三丙烯酸酯、丙氧基化三羟甲基丙烷三丙烯酸酯、乙氧基化新戊四醇四丙烯酸酯、丙氧基化新戊四醇三丙烯酸酯、丙氧基化新戊四醇四丙烯酸酯、乙氧基化新戊二醇二丙烯酸酯、丙氧基化新戊二醇二丙烯酸酯。
高分子量不饱和化合物(低聚物、预聚物)的实例为烯属不饱和单或多官能羧酸及多元醇的酯或聚环氧化物、及链或侧基中具有烯属不饱和基团的聚合物例如不饱和聚酯、聚酰胺及聚氨基甲酸酯及其共聚物)、醇酸树脂、聚丁二烯及丁二烯共聚物、聚异戊二烯及异戊二烯共聚物、侧链中具有(甲基)丙烯酸基团的聚合物及共聚物、以及一种或多种该聚合物的混合物。
本发明还提出一种印刷清漆，其特征是含有至少一种本发明中所述的式(Ⅰ)化合物。清漆除光引发剂外还可包含各种添加剂。其实例为意欲防止过早聚合的热抑制剂，例如2,2,6,6-四甲基-4-羟基-哌啶-1-氧基(4-羟基-TEMPO)及其衍生物(例如双(2,2,6,6-四甲基哌啶-1-氧-4-基)-癸二酸酯或多烷基-哌啶-N-氧自由基),3-芳基-苯并呋喃-2-酮及其衍生物(例如5,7-二-叔丁基-3-苯基-3H-苯并呋喃-2-酮(如例如W001/42313中所述))、氢醌、氢醌衍生物、对甲氧基苯酚、R-萘酚或空间位阻苯酚(例如2,6-二(叔丁基)-对甲酚)。为了提高黑暗贮藏稳定，可使用例如铜化合物(如环烷酸铜、硬脂酸铜或辛酸铜)、磷化合物(例如三苯基膦、三丁基膦、亚磷酸三乙酯、亚磷酸三苯酯或亚磷酸三苄酯)、季铵化合物(例如氯化四甲铵或氯化三甲基苄基铵)、或羟胺衍生物(例如N-二乙基羟基胺)。基于在聚合期间排除大气氧气在外的目的，可添加石蜡或类似的蜡状物质，其不溶于聚合物中，在开始聚合时迁移至表面且形成防止空气进来的透明表面层。
为了加速光聚合，可添加胺作为其它添加剂，特别是叔胺，例如三丁胺、三乙醇胺、对二甲氨基苯甲酸乙酯、米氏酮(Michler's ketone),N-甲基-二乙醇胺、N-二甲基乙醇胺、N-乙基吗琳,N-甲基吗琳、二氮杂双环辛烷(三乙二胺),18-二氮杂双环[5.4.0]十--7-烯(DBU),1,5-二氮杂双环「4.3.0〕壬-5-烯(DBN)。胺的作用可通过添加二苯甲酮或噻吨酮类芳族酮来强化。适于作为氧捕获剂的胺为例如EP339841中所述的N,N-二烷基苯胺或N,N-二甲基氨基苯甲酸乙酯。
具体实施方式
实施例一
2-(4-(3-甲基苯甲酰基)苯氧基)乙基乙酸酯合成
在250ml四口瓶中加入乙二醇苯醚醋酸酯31.5g，加入二氯乙烷200g，无水三氯化铝50.1g，滴加苯甲酰氯29g，-5℃反应2h，反应后水洗，减压脱溶后的到产物白色固体30g，含量97.55％。2-(4-(3-甲基苯甲酰基)苯氧基)乙醇合成
在250ml四口瓶中放入2-(4-(3-甲基苯甲酰基)苯氧基)乙基乙酸酯30g，加入甲醇50ml，加入15％氢氧化钠水溶液100g，25℃反应2h，减压脱去甲醇，加100ml二氯乙烷后水洗至中性，脱溶去掉二氯乙烷得产物淡黄色油状液体25g，含量98.55％。
2-(4-(3-甲基苯甲酰基)苯氧基)乙基苯甲酰基甲酸酯合成
100ml单口瓶中加入2-(4-(3-甲基苯甲酰基)苯氧基)乙醇2g，甲醇钠0.1g，苯甲酰甲酸甲酯6g，50℃下减压反应7h，加入50ml甲苯，水洗至中性，减压蒸馏至175℃，得黄色油状产物2.6g，含量95％。核磁氢谱确认为目标物。1H-NMR(CDCl3，300MHz，δppm)8.039-6.978(m,9H,ArH)，4.806-4.776(t,2H,CH2)，4.415-4.385(t,2H,CH2)，2.418(s,3H,CH3)实施例二
2-(4-(4-氯苯甲酰基)苯氧基)乙基乙酸酯合成
在250ml四口瓶中加入乙二醇苯醚醋酸酯30g，加入二氯乙烷200g，无水三氯化铝47g，滴加4-氯苯甲酰氯30.8g，-5℃反应2h，反应后水洗，减压脱溶后的到产物白色固体52g，含量96.29％。
2-[4-(4-氯苯甲酰基)苯氧基]乙醇合成
在250ml四口瓶中放入2-(4-(3-甲基苯甲酰基)苯氧基)乙基乙酸酯30g，加入甲醇50ml，加入15％氢氧化钠水溶液100g，25℃反应7h，减压脱去甲醇，加100ml二氯乙烷后水洗至中性，脱溶去掉二氯乙烷得产物白色固体24g，含量97.45％。
2-(4-(4-氯苯甲酰基)苯氧基)乙基苯甲酰基甲酸酯合成
100ml单口瓶中加入2-(4-(3-甲基苯甲酰基)苯氧基)乙醇2g，甲醇钠0.1g，苯甲酰甲酸甲酯1g，50℃下减压反应7h，加入50ml甲苯，水洗至中性，减压蒸馏至175℃，加甲苯5ml，乙酸乙酯5ml结晶得白色针状结晶产物1.8g，含量98.73％，熔点83.5℃～86.9℃。核磁氢谱确认为目标物。1H-NMR(CDCl3，300MHz，δppm)8.040-6.906(m,9H,ArH)，4.791-4.718(t,2H,CH2)，4.417(t,2H,CH2)
实施例三
4-苯甲酰基苯甲基苯甲酰甲酸酯合成
100ml单口瓶中放入14g苯甲酰甲酸甲酯，0.7g对甲苯磺酸，6g 4-苯甲酰基苯甲醇，50℃减压反应8h后，加入60ml甲苯，水洗至中性，减压旋干脱溶，加30ml二氯乙烷结晶，得产物白色固体2.2g，含量99.89％，熔点91.3～95.3℃。核磁氢谱确认为目标物。
1H-NMR(CDCl3，300MHz，δppm)8.020-7.471(m,14H,ArH),5.497(s,2H,CH2)
实施例四
2-(4-苯甲酰基)苯氧基乙基苯甲酰基甲酸酯合成
100ml单口瓶中加入2-(4-苯甲酰基苯氧基)乙醇10g，苯甲酰甲酸甲酯34g，甲醇钠0.42g，50℃减压反应8h，加入60ml甲苯，水洗至中性，150℃减压整馏，加48g甲苯结晶，得白色产物10g，含量99.56％，熔点92.0～96.8℃。核磁氢谱确认为目标物。1H-NMR(CDCl3，300MHz，δppm)8.04-6.98(m,14H,ArH)，4.80-4.78(t,2H,CH2)，4.40(t,2H,CH2)
实施例五
2-[2-(4-苯甲酰基苯氧基)乙氧基]乙基苯甲酰甲酸酯
100ml单口瓶中放入2g 2-[2-(4-苯甲酰基苯氧基)乙氧基]乙醇，6g苯甲酰甲酸甲酯，0.1g甲醇钠，50℃反应8h后加入50ml甲苯水洗至中性，减压蒸馏至170℃，的黄色液体2.6g。含量92％。核磁氢谱确认为目标物。1H-NMR(CDCl3，300MHz，δppm)8.036-6.944(m,14H,ArH)，4.607-4.576(t,2H,CH2)，4.237-4.208(t,2H,CH2),3.989-3.932(m,4H,2CH2)实施例六
按表1所示配制光固化组合物
表1
测试步骤如下：
a.按照配方表称量、配制各组样品，60℃下进行混合；
b.用线棒涂布器涂膜；
c.使用2000W高压汞灯固化；
d.观察固化样品的表干情况(指触干法)、气味、硬度和黄度；
测试方法：
a.硬度测试方法
膜的硬度由QYB摆式硬度计测定，摆幅5°，以玻璃板计数为基准，计算公式：
数值越大则硬度越高，表明其固化活性越好。
测试条件：用25um线棒涂布器在载玻片上涂膜；使用2000W高压汞灯固化，带速为8m/min。
b.指触干测试方法
涂膜固化后，用手指轻触涂膜表面，涂膜越光滑越不粘手则表面固化效果越好，也说明涂膜抗氧阻聚效果越好。
测试条件：分别用10um、25um线棒涂布器在载玻片上涂膜；使用2000W高压汞灯固化，带速为8m/min。
c.黄度测试方法
黄度指数由SC-80C全自动色差仪测定。固化膜的黄度指数由反射法测定。黄度指数值越小则涂膜透明性越好，光引发剂对涂膜的黄度影响越小。
测试条件：用25um线棒涂布器在载玻片上涂膜；使用2000W高压汞灯固化，带速为4m/min。
d.气味测试方法
将样品用线棒涂布器分别涂在PT纸上，涂布面积为1dm2，经紫外线固化机固化后，60℃恒温30min。评价其气味大小。数值越小表示气味越低。
测试条件：用25um线棒涂布器在载玻片上涂膜；使用2000W高压汞灯固化，带速为4m/min。
测试数据如表2所示：
表2
由测试数据可以得出：
本发明提供的双官能光引发剂在固化活性(硬度及表干)、气味上都要优于现有的单官能小分子光引发剂，同时与市售双官能光引发剂Omnirad 754相比在固化活性、气味及固化后黄度方面都具有相当的优势。
Claims (7)
1.一种双官能光引发剂，其结构如式(Ⅰ)所示：
其中：X为CH2或(CH2CH2O)n(n为1～8的整数)；
R1、R2、R3、R4、R5取自H、C1～C12烷基、C1～C12烷氧基、卤素原子，或除R3是苯基外，R1、R2、R4、R5均为H。
2.根据权利要求1所述的双官能光引发剂，具体结构有如式(Ⅱ)、式(Ⅲ)、式(Ⅳ)、式(Ⅴ)、式(Ⅵ)所示。
3.一种可UV光固化聚合的组合物，其特征是包含：
(A)至少一种可进行光聚合的烯属不饱和化合物和
(B)至少一种权利要求1所述的式(Ⅰ)化合物作为光引发剂。
4.如权利要求3的可UV光固化聚合的组合物，其除组分(B)外，还可以包含其他引发剂、胺促进剂，增敏剂，和/或其他添加剂。
5.如权利要求3的可UV光固化聚合的组合物，其组分(B)的添加量为基于总组分的0.05～20重量％。
6.一种可用于印刷上光油和罩光清漆的光固化组合物，其特征是含有至少一种权利要求1所述的式(Ⅰ)光引发剂。
7.任何包含权利要求3-5的光固化组分经固化得到的物品。
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|---|---|---|---|---|
| WO2007017348A3 (en) * | 2005-08-05 | 2007-04-05 | Lamberti Spa | Photopolymerisable systems containing radiation curable, low-extractable and low-volatile coinitiators |
| CN102020728A (zh) * | 2010-11-29 | 2011-04-20 | 长沙新宇高分子科技有限公司 | 复合型多官能团光引发剂 |
| CN102206293A (zh) * | 2010-03-29 | 2011-10-05 | 比亚迪股份有限公司 | 一种光引发剂，一种光固化涂料和模内装饰方法 |
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| WO2007017348A3 (en) * | 2005-08-05 | 2007-04-05 | Lamberti Spa | Photopolymerisable systems containing radiation curable, low-extractable and low-volatile coinitiators |
| CN102206293A (zh) * | 2010-03-29 | 2011-10-05 | 比亚迪股份有限公司 | 一种光引发剂，一种光固化涂料和模内装饰方法 |
| CN102020728A (zh) * | 2010-11-29 | 2011-04-20 | 长沙新宇高分子科技有限公司 | 复合型多官能团光引发剂 |
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| 双官能度单组分光引发剂的制备及其光引发活性研究;简凯;《影像科学与光化学》;20161130;第34卷(第6期);第505-512页 * |
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