CN110337454B - 水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐 - Google Patents
水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐 Download PDFInfo
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- CN110337454B CN110337454B CN201880014240.3A CN201880014240A CN110337454B CN 110337454 B CN110337454 B CN 110337454B CN 201880014240 A CN201880014240 A CN 201880014240A CN 110337454 B CN110337454 B CN 110337454B
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- 150000003732 xanthenes Chemical class 0.000 description 1
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- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- OEERILNPOAIBKF-UHFFFAOYSA-J zirconium(4+);tetraformate Chemical compound [Zr+4].[O-]C=O.[O-]C=O.[O-]C=O.[O-]C=O OEERILNPOAIBKF-UHFFFAOYSA-J 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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Abstract
提供:保存稳定性优异、能适应于宽范围的光源、能形成高精细的图案的水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐。含有:下述通式(I)(式中,X1表示碳原子数6~15的芳基,X2表示碳原子数1~8的直链的烷基等,Am+表示碱金属离子等,m表示1~3的数。)所示的酰基次膦酸盐(A)、具有下述通式(II)(式中,R1表示氢原子等,Z1表示氧原子等,R2表示氢原子等,Z2表示碳原子数1~6的亚烷基,n表示0~30的数,*是指结合键,具有多个通式(II)所示的基团的情况下,多个存在的R1、X1、X2、n任选分别相同或不同。)所示的基团的化合物(B)。
Description
技术领域
本发明涉及水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐,详细而言,涉及保存稳定性优异、能适应于宽范围的光源、能形成高精细的图案的水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐。
背景技术
水溶性组合物用于涂料、墨、粘接剂、光学薄膜等各种用途。关注到水溶性组合物的水溶性引发剂,专利文献1中,提出了一种水溶性墨水组合物,其含有:微粒、具有烯属不饱和基的聚合性化合物、具有甜菜碱结构的光聚合引发剂及水;专利文献2中,提出了一种经时稳定性、固化灵敏度及液位置精度良好的墨水组合物,其含有:作为水溶性引发剂的具有吗啉结构的α-氨基苯乙酮以及作为水溶性化合物的具有丙烯酰胺结构的化合物;专利文献3中,提出一种对于牙质、特别是象牙质的粘接性优异的牙科用粘接性组合物,其含有:丙烯酸酯系单体及作为光聚合引发剂的水溶性的酰基氧化膦化合物。
现有技术文献
专利文献
专利文献1:国际公开2014/050551号
专利文献2:日本特开2012-007070号公报
专利文献3:日本特开2000-159621号公报
发明内容
发明要解决的问题
水溶性组合物要求保存稳定性优异、能适应于宽范围的光源、能形成高精细的图案的水溶性组合物。在这种状况下,对于专利文献1~3中提出的那种水溶性组合物,未必以市场要求的高水平来兼具这些特性,故要求水溶性组合物的进一步改良为现状。
因此,本发明的目的在于,提供:保存稳定性优异、能适应于宽范围的光源、能形成高精细的图案的水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐。
用于解决问题的方案
本发明人等为了解决上述课题,进行了深入研究,结果发现:使用含有具有特定结构的酰基次膦酸盐、环氧烷改性(甲基)丙烯酸酯化合物或(甲基)丙烯酰胺化合物的水溶性组合物,可以解决上述课题,至此完成本发明。
即,本发明的水溶性组合物的特征在于,含有:下述通式(I)所示的酰基次膦酸盐(A),和具有下述通式(II)所示的基团的化合物(B),
(式中,X1表示碳原子数6~15的芳基,
X1所示的基团中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基所取代,
X2表示碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、或碳原子数6~15的芳基,
X2所示的碳原子数6~15的芳基中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基、卤素原子、硝基、氰基、羟基、氨基、羧基、甲基丙烯酰基、丙烯酰基、环氧基、乙烯基、乙烯基醚基、巯基、异氰酸酯基或含杂环基所取代,
X2所示的基团中的亚甲基任选被氧原子或硫原子所取代,
Am+表示碱金属离子、碱土金属离子或N+HY1Y2Y3,
Y1、Y2及Y3分别独立地表示氢原子、羟基、碳原子数1~6的烷基、碳原子数1~6的烯基、碳原子数6~15的芳基或碳原子数7~13的芳烷基,
Y1、Y2及Y3所示的基团中的氢原子任选被羟基所取代,
Y1、Y2及Y3所示的基团中的亚甲基任选被氧原子、硫原子、羰基或-N+H-所取代,
Y1和Y2、Y1和Y3及Y2和Y3中任一者以上任选键合形成环,
m表示1~3的数。)
(式中,R1表示氢原子或甲基,
Z1表示氧原子或-NR2-,
R2表示氢原子或碳原子数1~20的烃基,
Z2表示碳原子数1~6的亚烷基,
n表示0~30的数,
*是指结合键,
具有多个通式(II)所示的基团的情况下,多个存在的R1、Z1、Z2、n任选分别相同或不同。)
本发明的水溶性组合物中,前述通式(I)中的X1优选为2,4,6-三甲基苯基。另外,本发明的水溶性组合物中,前述通式(I)中的X2优选为苯基、且Am+为N+HY1Y2Y3。进而,本发明的水溶性组合物中,前述通式(I)中的Am+优选为N+HY1Y2Y3、且Y1、Y2及Y3中任一者以上的氢原子被羟基所取代。进而另外,本发明的水溶性组合物中,前述通式(II)中的Z1优选为-NR2-。进而另外,本发明的水溶性组合物中,进而优选含有着色剂(C)。
另外,本发明的固化物的制造方法的特征在于,使本发明的水溶性组合物利用光照射或加热而固化。
进而,本发明的固化物的特征在于,由本发明的水溶性组合物得到。
进而,本发明的酰基次膦酸盐的特征在于,其为下述通式(I)所示的酰基次膦酸盐。
(式中,X1表示碳原子数6~15的芳基,
X1所示的基团中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基所取代,
X2表示碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、或碳原子数6~15的芳基,
X2所示的碳原子数6~15的芳基中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基、卤素原子、硝基、氰基、羟基、氨基、羧基、甲基丙烯酰基、丙烯酰基、环氧基、乙烯基、乙烯基醚基、巯基、异氰酸酯基或含杂环基所取代,
X2所示的基团中的亚甲基任选被氧原子或硫原子所取代,
Am+表示碱金属离子、碱土金属离子或N+HY1Y2Y3,
Y1、Y2及Y3分别独立地表示氢原子、羟基、碳原子数1~6的烷基、碳原子数1~6的烯基、碳原子数6~15的芳基或碳原子数7~13的芳烷基,
Y1、Y2及Y3所示的基团中的氢原子任选被羟基所取代,
Y1、Y2及Y3所示的基团中的亚甲基任选被氧原子、硫原子、羰基或-N+H-所取代,
Y1和Y2、Y1和Y3及Y2和Y3中任一者以上任选键合形成环,
m表示1~3的数。)
其中,所述通式(I)中的X2为苯基,Am+为N+HY1Y2Y3,且
Y1和Y2、Y1和Y3及Y2和Y3中任一者以上任选键合而形成环。
本发明的酰基次膦酸盐优选的是前述通式(I)中的Am+为N+HY1Y2Y3、且Y1、Y2及Y3中任一者以上的氢原子被羟基所取代。
发明的效果
根据本发明,可提供:保存稳定性优异、能适应于宽范围的光源、能形成高精细的图案的水溶性组合物、其固化物的制造方法及其固化物、以及酰基次膦酸盐。本发明的水溶性组合物在对应于高压汞灯、超高压汞灯、无极灯及LED光源等的各种波长的光中能够制作高精细的图案。另外,保存稳定性优异,因此可适合用于涂料、墨、粘接剂、光学薄膜等各种用途。另外,本发明的酰基次膦酸盐适合用于本发明的水溶性组合物。
具体实施方式
以下,对本发明的水溶性组合物进行说明。本发明的水溶性组合物含有下述通式(I)所示的酰基次膦酸盐(A)和具有下述通式(II)所示的基团的化合物(B)。本发明的水溶性组合物的保存稳定性优异、以单液存在、可对应于各种波长的光源,因此可简便制作固化物。以下,对各成分依次进行说明。
<酰基次膦酸盐(A)>
本发明的水溶性组合物的酰基次膦酸盐(A)是指本发明的酰基次膦酸盐,可以具有下述通式(I)所示的基团,没有特别限定。
此处,通式(I)中,X1表示碳原子数6~15的芳基,X1所示的基团中的氢原子可以被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基所取代。
另外,通式(I)中,X2表示碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、或碳原子数6~15的芳基。
X2所示的碳原子数6~15的芳基中的氢原子可以被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基、卤素原子、硝基、氰基、羟基、氨基、羧基、甲基丙烯酰基、丙烯酰基、环氧基、乙烯基、乙烯基醚基、巯基、异氰酸酯基或含杂环基所取代,X2所示的基团中的亚甲基可以被氧原子或硫原子所取代。
另外,Am+表示碱金属离子、碱土金属离子或N+HY1Y2Y3,Y1、Y2及Y3分别独立地表示碳原子数1~6的烷基、碳原子数1~6的烯基、碳原子数6~15的芳基或碳原子数7~13的芳烷基。另外,Y1、Y2及Y3所示的基团中的氢原子可以被羟基所取代,Y1、Y2及Y3所示的基团中的亚甲基可以被氧原子、硫原子、羰基、或-N+H-所取代,Y1和Y2、Y1和Y3及Y2和Y3中任一者以上可以键合而形成环。另外,m表示1~3的数。
作为通式(I)中的X1、X2及Y1~Y3所示的碳原子数6~15的芳基,例如可列举出:苯基、三甲基苯基、甲苯基、二甲苯基、2,4,6-三甲基苯基、萘基及蒽基等。
作为取代通式(I)中的X1及X2所示的基团中的氢原子的基团,可列举出碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基及碳原子数3~8的具有支链的卤代烷氧基。作为卤素原子,可列举出氟原子、氯原子、溴原子、碘原子等。
作为上述碳原子数1~8的直链的烷基,例如可列举出:甲基、乙基、丙基、丁基、戊基、己基、庚基及辛基等。
作为上述碳原子数3~8的具有支链的烷基,例如可列举出:异丙基、丁基、异丁基、仲丁基、叔丁基、异戊基、叔戊基、异辛基、2-乙基己基及叔辛基等。
作为上述碳原子数1~8的直链的卤代烷基,为表示上述碳原子数1~8的直链的烷基的氢原子1个以上被卤素原子所取代者。
作为上述碳原子数3~8的具有支链的卤代烷基,为表示上述碳原子数3~8的直链的烷基的氢原子1个以上被卤素原子所取代者。
作为上述碳原子数1~8的直链的烷氧基,例如可列举出:甲氧基、乙氧基、正丙氧基、正丁氧基、叔丁氧基、正戊氧基、正己氧基及正辛氧基等。
作为上述碳原子数3~8的具有支链的烷氧基,例如可列举出:异丙氧基、异丁氧基、环丁氧基、叔丁氧基、异戊氧基、新戊氧基及异辛氧基等。
作为上述碳原子数1~8的直链的卤代烷氧基,为表示上述碳原子数1~8的直链的烷氧基的氢原子1个以上被卤素原子所取代者。
作为上述碳原子数3~8的具有支链的卤代烷氧基,为表示上述碳原子数3~8的直链的烷氧基的氢原子1个以上被卤素原子所取代者。
通式(I)中的X2所示的碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、及碳原子数6~15的芳基与取代上述通式(I)中的X1及X2所示的基团中的氢原子的基团所示例的相同。
作为通式(I)中的Y1~Y3所示的碳原子数1~6的烷基,可列举出甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、叔戊基及己基等。
作为通式(I)中的Y1~Y3所示的碳原子数1~6的烯基,例如可列举出:乙烯基、乙烯、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基及5-己烯基等。
作为通式(I)中的Y1~Y3所示的碳原子数7~13的芳烷基,意味着烷基的氢原子被芳基所取代的具有7~13的碳原子的基团。例如,可列举出苄基、α-甲基苄基、α,α-二甲基苄基、苯乙基及萘基丙基等。
本发明的水溶性组合物中,通式(I)中的X1为苯基、甲苯基、二甲苯基、2,4,6-三甲基苯基及萘基的化合物时,稳定性、吸收波长及水中的溶解性优异,故优选。其中,上述通式(I)中的X1为2,4,6-三甲基苯基的酰基次膦酸盐时,水溶性组合物的灵敏度高,故优选。
本发明的水溶性组合物中,上述通式(I)中的X2为苯基、甲苯基、二甲苯基、2,4,6-三甲基苯基及萘基的化合物时,稳定性、吸收波长及水中的溶解性优异故优选。其中,上述通式(I)中的X2为苯基时,灵敏度高,故优选。
本发明的水溶性组合物中,上述通式(I)中的X2为苯基且Am+为N+HY1Y2Y3的酰基次膦酸盐时,水中的溶解性高、水溶性组合物的灵敏度高,故优选。作为N+HY1Y2Y3的优选者,列举下述化合物No.A1~A41。其中,本发明的水溶性组合物不受以下化合物任何限制。
上述通式(I)中,X2为苯基、Am+为N+HY1Y2Y3、且Y1和Y2、Y1和Y3及Y2和Y3中任一者以上进行键合而形成环的酰基次膦酸盐时,水中的溶解性高、水溶性组合物的灵敏度高,故特别优选。
作为Y1和Y2、Y1和Y3及Y2和Y3中任一者以上进行键合而形成环的N+HY1Y2Y3的优选者,列举上述化合物No.A1~A15。
上述N+HY1Y2Y3中Y1~Y3的氢原子为被1个以上羟基所取代的酰基次膦酸盐(A)时,与水的相容性高,故优选。
酰基次膦酸盐(A)的含量相对于酰基次膦酸盐(A)及化合物(B)的总计100质量份为0.05~50质量份,优选0.1~35质量份。酰基次膦酸盐(A)的含量处于该范围时,在高压汞灯、超高压汞灯、无极灯及LED光源之类的宽范围的光源下可得到固化性良好的水溶性组合物,由该水溶性组合物可得到具有高精细的图案的固化物,故优选。
<化合物(B)>
本发明的水溶性组合物的化合物(B)只要具有下述通式(II)所示的基团即可,没有特别限定。
此处,通式(II)中,R1表示氢原子或甲基,Z1表示氧原子或-NR2-,R2表示氢原子或碳原子数1~20的烃基,Z2表示碳原子数1~6的亚烷基,n表示0~30的数,*是指结合键。具有多个通式(II)所示的基团的情况下,多个存在的R1、X1、X2、n任选分别相同或不同。
通式(II)中的R2所示的碳原子数1~20的烃基没有特别限定,优选的是碳原子数1~20的烷基、碳原子数2~20的烯基、碳原子数3~20的环烷基、碳原子数4~20的环烷基烷基、碳原子数6~20的芳基及碳原子数7~20的芳烷基等。由于水溶性组合物的灵敏度良好,故更优选碳原子数1~10的烷基、碳原子数2~10的烯基、碳原子数3~10的环烷基、碳原子数4~10的环烷基烷基、碳原子数6~10的芳基及碳原子数7~10的芳烷基等。
作为碳原子数1~20的烷基,例如可列举出:甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、叔戊基、己基、庚基、辛基、异辛基、2-乙基己基、叔辛基、壬基、异壬基、癸基、异癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基及二十烷基等,作为上述碳原子数1~10的烷基,例如可列举出:甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、叔戊基、己基、庚基、辛基、异辛基、2-乙基己基、叔辛基、壬基、异壬基、癸基及异癸基等。
作为碳原子数2~20的烯基,例如可列举出:乙烯基、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基、5-己烯基、2-庚烯基、3-庚烯基、4-庚烯基、3-辛烯基、3-壬烯基、4-癸烯基、3-十一烯基、4-十二烯基、3-环己烯基、2,5-环己二烯基-1-甲基及4,8,12-十四烷三烯基烯丙基等,作为上述碳原子数2~10的烯基,例如可列举出:乙烯基、2-丙烯基、3-丁烯基、2-丁烯基、4-戊烯基、3-戊烯基、2-己烯基、3-己烯基、5-己烯基、2-庚烯基、3-庚烯基、4-庚烯基、3-辛烯基、3-壬烯基及4-癸烯基等。
碳原子数3~20的环烷基是指,具有3~20的碳原子的饱和单环式或饱和多环式烷基的含义。例如可列举出:环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、金刚烷基、十氢萘基、八氢并环戊二烯基、双环[1.1.1]戊烷基及十四氢蒽基等,作为上述碳原子数3~10的环烷基,例如可列举出:环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、金刚烷基、十氢萘基、八氢并环戊二烯基及双环[1.1.1]戊烷基等。
碳原子数4~20的环烷基烷基是指,烷基的氢原子被环烷基所取代的具有4~20的碳原子的基团的含义。例如可列举出:环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环庚基甲基、环辛基甲基、环壬基甲基、环癸基甲基、2-环丁基乙基、2-环戊基乙基、2-环己基乙基、2-环庚基乙基、2-环辛基乙基、2-环壬基乙基、2-环癸基乙基、3-环丁基丙基、3-环戊基丙基、3-环己基丙基、3-环庚基丙基、3-环辛基丙基、3-环壬基丙基、3-环癸基丙基、4-环丁基丁基、4-环戊基丁基、4-环己基丁基、4-环庚基丁基、4-环辛基丁基、4-环壬基丁基、4-环癸基丁基、3-3-金刚烷基丙基及十氢萘基丙基等,作为碳原子数4~10的环烷基烷基,例如可列举出:环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环庚基甲基、环辛基甲基、环壬基甲基、2-环丁基乙基、2-环戊基乙基、2-环己基乙基、2-环庚基乙基、2-环辛基乙基、3-环丁基丙基、3-环戊基丙基、3-环己基丙基、3-环庚基丙基、4-环丁基丁基、4-环戊基丁基及4-环己基丁基等。
作为碳原子数6~20的芳基,例如可列举出:苯基、甲苯基、二甲苯基、乙基苯基、萘基、蒽基、菲基等、或被上述烷基、上述烯基、羧基、卤素原子等的1个以上取代的苯基、联苯基、萘基、蒽基等,例如可列举出:4-氯苯基、4-羧基苯基、4-乙烯基苯基、4-甲基苯基、2,4,6-三甲基苯基等,作为上述碳原子数6~10的芳基,例如可列举出:苯基、甲苯基、二甲苯基、乙基苯基及萘基等、或被上述烷基、上述烯基、羧基、卤素原子等的1个以上取代的苯基、联苯基、萘基、蒽基等,例如可列举出:4-氯苯基、4-羧基苯基、4-乙烯基苯基、4-甲基苯基、2,4,6-三甲基苯基等。
碳原子数7~20的芳烷基是指,烷基的氢原子被芳基所取代的具有7~30的碳原子的基团的含义。例如可列举出:苄基、α-甲基苄基、α,α-二甲基苄基、苯基乙基及萘基丙基等,上述碳原子数7~20的芳烷基是指,烷基的氢原子被芳基所取代的具有7~20的碳原子的基团的含义。例如可列举出:苄基、α-甲基苄基、α,α-二甲基苄基及苯基乙基等。
作为通式(II)中的Z2所示的碳原子数1~6的亚烷基,例如可列举出:亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基等直链状的亚烷基以及异亚丙基和异亚丁基等支链状的亚烷基等。
作为化合物(B),例如优选可使用环氧烷改性(甲基)丙烯酸酯化合物及(甲基)丙烯酰胺化合物。
上述环氧烷改性(甲基)丙烯酸酯化合物是指,环氧烷改性丙烯酸酯化合物或环氧烷改性甲基丙烯酸酯化合物的含义。
上述(甲基)丙烯酰胺化合物是指,丙烯酰胺化合物或甲基丙烯酰胺化合物的含义。
上述环氧烷改性丙烯酸酯化合物是指,通式(II)中,R1为氢原子、Z1为氧原子、n为1~30的化合物,上述环氧烷改性甲基丙烯酸酯化合物是指,通式(II)中,R1为甲基、Z1为氧原子、n为1~30的化合物。
作为上述环氧烷改性丙烯酸酯化合物,例如可列举出:二环氧乙烷改性新戊二醇二丙烯酸酯、二环氧丙烷改性新戊二醇二丙烯酸酯、二环氧乙烷改性1,6-己二醇二丙烯酸酯、二环氧丙烷改性1,6-己二醇二丙烯酸酯等,作为上述环氧烷改性甲基丙烯酸酯化合物,例如可列举出:二环氧乙烷改性新戊二醇二甲基丙烯酸酯、二环氧丙烷改性新戊二醇二甲基丙烯酸酯、二环氧乙烷改性1,6-己二醇二甲基丙烯酸酯、二环氧丙烷改性1,6-己二醇二甲基丙烯酸酯等。
作为上述环氧烷改性丙烯酸酯化合物及上述环氧烷改性甲基丙烯酸酯化合物,也可优选使用市售品,例如可列举出:NK ESTER A-600、A-GLY-20E、NK EKONOMA A-PG5054E(以上,新中村化学工业制)等。
上述环氧烷改性丙烯酸酯化合物及上述环氧烷改性甲基丙烯酸酯化合物中,上述通式(II)中的X2为亚乙基或亚丙基时,水溶性优异,故优选,亚乙基时,水溶性特别优异,故优选。
上述环氧烷改性丙烯酸酯化合物及上述环氧烷改性甲基丙烯酸酯化合物具有1个通式(II)所示的基团时,水溶性优异,n为6以上时,特别优选。上述环氧烷改性丙烯酸酯化合物及环氧烷改性甲基丙烯酸酯化合物具有多个通式(II)所示的基团时,水溶性优异,多个存在的n的总计为10以上时,特别优选。
上述丙烯酰胺化合物是指,上述通式(II)中,R1为氢原子、Z1为-NR2-、n为0的化合物,上述甲基丙烯酰胺化合物是指,上述通式(II)中,R1为甲基、Z1为-NR2-、n为0的化合物。
作为上述丙烯酰胺化合物,可列举出羟基丙烯酰胺、N-甲基丙烯酰胺、N-乙基丙烯酰胺、N-异丙基丙烯酰胺、N-丁基丙烯酰胺、二丙酮丙烯酰胺、N,N-二甲基丙烯酰胺、N,N-二乙基丙烯酰胺、N,N-二丙基丙烯酰胺、丙烯酰基吗啉、N-正丁氧基甲基丙烯酰胺、N-异丁氧基甲基丙烯酰胺、N-甲氧基甲基丙烯酰胺等,作为上述甲基丙烯酰胺化合物,可列举出:羟基甲基丙烯酰胺、N-甲基甲基丙烯酰胺、N-乙基甲基丙烯酰胺、N-异丙基甲基丙烯酰胺、N-丁基甲基丙烯酰胺、二丙酮甲基丙烯酰胺、N,N-二甲基甲基丙烯酰胺、N,N-二乙基甲基丙烯酰胺、N,N-二丙基甲基丙烯酰胺、甲基丙烯酰基吗啉、N-正丁氧基甲基甲基丙烯酰胺、N-异丁氧基甲基甲基丙烯酰胺、N-甲氧基甲基甲基丙烯酰胺等。
作为上述丙烯酰胺化合物及上述甲基丙烯酰胺化合物,也可优选使用市售品,例如可列举出:FFM-2、FFM-3、FFM-4及FFM-5、(Fujifilm公司制)。
化合物(B)的含量相对于酰基次膦酸盐(A)及化合物(B)的总计100质量份为70~99.5质量份,优选90~99.5质量份,化合物(B)的含量处于该范围时,在宽范围的光源(LED)下可得到固化性良好的水溶性组合物,由该水溶性组合物可得到具有高精细的图案的固化物,故优选。
<溶剂>
本发明的水溶性组合物可以含有水作为溶剂,可以与有机溶剂组合使用,但作为溶剂仅为水的单液时,环境低负荷及涂布于有机材料上时不会侵蚀有机材料,故优选。
作为上述有机溶剂,可列举出:通过与水组合使用而能溶解或分散上述各成分(酰基次膦酸盐(A)及化合物(B))等的溶剂,例如甲乙酮、甲基戊酮、二乙酮、丙酮、甲基异丙酮、甲基异丁酮、环己酮和2-庚酮等酮类;乙基醚、二氧杂环己烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷和二丙二醇二甲醚等醚系溶剂;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸环己酯、乳酸乙酯、琥珀酸二甲酯和酯醇等酯系溶剂;乙二醇单甲醚和乙二醇单乙醚等溶纤剂系溶剂;甲醇、乙醇、异丙醇或正丙醇、异丁醇或正丁醇和戊醇等醇系溶剂;乙二醇单甲基乙酸酯、乙二醇单乙基乙酸酯、丙二醇-1-单甲醚(PGM)、丙二醇-1-单甲醚-2-乙酸酯(PGMEA)、二丙二醇单甲醚乙酸酯、3-甲氧基丁基乙酸酯和乙氧基乙基丙酸酯等醚酯系溶剂;苯、甲苯和二甲苯等芳香族系溶剂;己烷、庚烷、辛烷和环己烷等脂肪族烃系溶剂;松节油、D-柠檬烯和蒎烯等萜烯系烃油;矿物油精、Swasol#310(以上,COSMOMATSUYAMA OIL Co.,Ltd.制);和Solvesso#100(以上、Exxon化学制);等石蜡系溶剂;四氯化碳、氯仿、三氯乙烯、二氯甲烷和1,2-二氯乙烷等卤代脂肪族烃系溶剂;氯苯等卤代芳香族烃系溶剂;卡必醇系溶剂、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜和水等,由于与水的相容性良好,故优选醇系溶剂。
本发明的水溶性组合物中,使用上述溶剂时,其使用量没有特别限定,相对于水溶性组合物总量优选成为70~95质量%。溶剂的含量为上述范围时,操作性(固化性组合物的粘度、润湿性)及液体稳定性(不伴有组合物所含成分的析出、沉降)优异的固化性组合物以及能够适宜地控制固化物的厚度,故优选。
<其他>
本发明的水溶性组合物中,根据需要也可添加具有光敏基团及羟基的水溶性聚合物、聚乙烯醇改性水溶性聚合物、交联剂、不具有光敏基团及下述通式(VI)所示的部分结构的水溶性聚合物、有机酸、偶联剂、敏化剂、表面活性剂、碱性化合物、着色剂、自由基引发剂(除酰基次膦酸盐(A)以外)、水溶性防腐剂及导电性物质等。
作为上述具有光敏基团及羟基的水溶性聚合物的优选者,从固化物的耐热性、耐水性及耐湿热性高的方面出发,可列举出具有下述通式(IIIα)~(IIIε)作为结构单元的化合物,其中,具有(IIIδ)及(IIIε)作为结构单元的化合物即使在使用LED光源(365nm)的情况下,也可得到固化性优异的水溶性组合物以及耐热性、耐水性及耐湿热性优异的固化物,故更优选。
此处,Y4、Y5及Y6分别独立地表示直接键合或2价的连接基团,Q1、Q2及Q3分别独立地表示光敏基团,*是指结合键。
此处,通式(IIIδ)、(IIIε)中,Anq-表示q价的阴离子,q表示1或2,p表示将电荷保持为中性的系数,*是指结合键。
作为通式(IIIα)、(IIIβ)及(IIIγ)中的Y4、Y5及Y6所示的2价的连接基团,没有特别限定,例如可优选列举亚甲基、亚乙基、三亚甲基、亚丙基、亚丁基等碳原子数1~10的亚烷基、亚苯基、亚萘基等碳原子数6~30的亚芳基、杂环连接基团、-CH=CH-、-O-、-S-、-C(=O)-、-CO-、-NR-、-CONR-、-OC-、-SO-、-SO2-和将它们组合2种以上而成的连接基团。此处,R分别独立地表示氢原子、烷基、芳基、或杂环基。
作为通式(IIIα)、(IIIβ)及(IIIγ)中的Q1、Q2及Q3所示的光敏基团,例如可列举出:肉桂基、肉桂酰基、亚肉桂基、亚肉桂基乙酰基、查尔酮基、香豆素基、异香豆素基、2,5-二甲氧基二苯乙烯基、马来酰亚胺基、α-苯基马来酰亚胺基、2-吡喃酮基、叠氮基、胸腺嘧啶基、醌基、尿嘧啶基、嘧啶基、1-甲基-4-[(E)-2-苯乙烯基]吡啶鎓基(stilbazoliumgroup)、1-[2-苯乙烯基]吡啶鎓基(styryl pyridinium group)、苯乙烯基喹啉鎓基、环氧基、氧杂环丁烷基、乙烯基醚基、烯丙基醚基、丙烯酰基、甲基丙烯酰基、丙烯酰胺基、甲基丙烯酰胺基、乙烯基、烯丙基、苯乙烯基等,这些当中,从可得到感光性高、液体稳定性(不伴有增稠、凝胶化、析出等)高的水溶性组合物的方面出发,可优选使用1-甲基-4-[(E)-2-苯乙烯基]吡啶鎓基、肉桂酰基、丙烯酰基、甲基丙烯酰基、丙烯酰胺基或甲基丙烯酰胺基。
上述光敏基团之中,由于1-甲基-4-[(E)-2-苯乙烯基]吡啶鎓基在水中的溶解性高,另外在365nm附近具有吸收带,因此可以得到在LED光源(365nm)等波长较长的光源下也表现出光敏性的水溶性组合物。由该水溶性组合物可以得到耐热性、耐水性和耐湿热性优异且高精细的图案的固化物,因此可以特别优选地使用。
作为优选的具有光敏基团及羟基的水溶性聚合物的具体例,可列举出下述通式(IV)及下述通式(V)所示的水溶性感光聚合物。
此处,式(IV)中,Y4及Q1与上述通式(IIIα)相同,Y6及Q3与上述通式(IIIγ)相同,a、b、c及d为0~5000为止的数,a及d不会同时为0,100<a+b+c+d<5000,*是指结合键。
此处,式(V)中,a、b、c及d与通式(IV)相同,a及d不会同时为0,100<a+b+c+d<5000,*是指结合键。
通过本发明的水溶性组合物得到的固化物的耐热性及密合性良好,因此通式(IV)及(V)中a、b、c及d(摩尔比)的优选值为a:b:c:d=0.1~4:5~30:5~70:0.1~4,重均分子量为1.5万~500万、优选为10万~100万。
通式(V)所示的聚合物可以通过在pH 1~4的条件下使具有光敏基团的醛与丁二醇/聚乙烯醇共聚物进行缩醛化反应而得到。另外,还可以通过使用市售品来制造,例如,可以通过在pH 1~4的条件下使具有光敏基团的醛与日本合成化学株式会社制的G聚合物(丁二醇乙烯醇共聚物)OKS-1081、OKS-1083、OKS-1109进行缩醛化反应而得到。
聚乙烯醇改性水溶性聚合物是指,在结构中不具有上述光敏基团、且具有下述通式(VI)所示的结构单元的水溶性聚合物,通过与后述的交联剂组合添加,从而可提高所得到的固化物的耐热性。
此处,通式(VI)中,*是指结合键。
聚乙烯醇改性水溶性聚合物作为主链与现有公知的聚乙烯醇是同样的,可列举出:通常被称为Poval的使乙烯醇聚合而成的聚乙烯醇、部分皂化聚乙烯醇、完全皂化聚乙烯醇、或乙酸乙烯酯与具有共聚性的单体的共聚物的皂化物等。需要说明的是,构成聚乙烯醇改性水溶性聚合物的聚乙烯醇可以是将乙烯醇作为必须单体的均聚物,还可以是共聚物。
作为聚乙烯醇改性水溶性聚合物的制造方法,没有特别限定,例如可以列举出如下方法:使聚乙烯醇与双烯酮反应的方法、使聚乙烯醇与乙酰乙酸酯反应而进行酯交换的方法、对乙酸乙烯酯与乙酰乙酸乙烯酯的共聚物进行皂化的方法等。其中,从制造工序简化且可以得到品质良好的具有乙酰乙酸酯基的聚乙烯醇方面考虑,优选利用使聚乙烯醇与双烯酮反应的方法来制造。
作为与乙酸乙烯酯具有共聚性的单体,例如可列举出:马来酸、马来酸酐、富马酸、巴豆酸、衣康酸、丙烯酸、甲基丙烯酸等不饱和羧酸及其酯类;乙烯、丙烯等α-烯烃;烯丙基磺酸、甲基烯丙基磺酸、烯丙基磺酸钠、甲基烯丙基磺酸钠、磺酸钠、磺酸钠单烷基马来酸酯、二磺酸钠烷基马来酸酯、N-羟甲基丙烯酰胺、丙烯酰胺烷基磺酸碱金属盐、N-乙烯基吡咯烷酮、N-乙烯基吡咯烷酮衍生物等,这些单体优选为全部结构单元的10摩尔%以下、特别优选为5摩尔%。过多时有水溶性降低的担心。
本发明的水溶性组合物中,通过添加基于凝胶渗透色谱仪(GPC)的聚苯乙烯换算重均分子量(Mw)为10000~200000、皂化度(水解率)为85~100的聚乙烯醇改性水溶性聚合物和后述的交联剂,所得到的固化物的耐水性提高、膜的耐久性提高,因此优选,皂化度为95~100的聚乙烯醇改性水溶性聚合物的耐水性进而提高,因此更优选。
作为聚乙烯醇改性水溶性聚合物,若使用具有下述通式(VII)所示的结构单元的化合物时,由本发明的水溶性组合物得到的固化物的耐热性、耐水性及耐湿热性特别优异,故更优选。
通式(VII)所示的结构单元的含量通常为0.1~20摩尔%,进而优选0.2~15摩尔%、特别优选0.3~10摩尔%时,从固化物的耐水性、交联速度、水溶性、水溶液的稳定性的观点出发,优选。
作为聚乙烯醇改性水溶性聚合物,也可以使用市售品,例如可列举出:GOHSENX Z-100、Z-200、Z-220、Z-300及Z-410(日本合成化学工业株式会社制)等。
上述交联剂只要能使聚乙烯醇改性水溶性聚合物交联就可以没有限制地使用。作为交联剂,例如可列举出:现有公知的有机系交联剂、具有螯合剂的金属螯合物、锆化合物和钛化合物。
作为有机系交联剂,可以从作为交联剂常用的交联剂中任意选择地使用,例如可以列举出:二叠氮化合物、具有羟基或烷氧基的氨基树脂、聚乙烯亚胺、三聚氰胺树脂、脲树脂、胍胺树脂、甘脲-甲醛树脂、琥珀酰胺-甲醛树脂、亚乙基脲-甲醛树脂等。它们可以使用使三聚氰胺、脲、胍胺、甘脲、琥珀酰胺、亚乙基脲在沸水中与福尔马林反应而羟甲基化、或使其进一步与低级醇反应而烷氧基化的物质。
作为螯合剂,可列举出:羟基羧酸或其盐、乙醛酸或其盐、氨基醇、氨基羧酸、丙氨酸、精氨酸、亮氨酸、异亮氨酸、二羟基丙基甘氨酸、乙二胺四乙酸、二亚乙基三胺五乙酸、次氮基三乙酸、β-二酮、二甲基乙二醛肟、柠檬酸、酒石酸、马来酸、聚酰肼、磷酸酯等,它们可以使用一种或组合使用两种以上。
在使用相对于1个金属原子具有通过共价键、氢键等能够以2齿或2齿以上的多齿进行配位的螯合剂的金属螯合物的情况下,交联反应速度被适度地调节,故优选。作为螯合型配位体,具体而言可列举出羟基羧酸或其盐、氨基醇、β-二酮等。
作为锆化合物,可列举出:氧氯化锆、羟基氯化锆、四氯化锆、溴化锆等卤化锆;硫酸锆、碱性硫酸锆、硝酸氧锆、二乙酸基氧化锆、碳酸氧锆等无机酸的锆盐;甲酸锆、乙酸锆、丙酸锆、辛酸锆、硬脂酸锆、乳酸锆、硝酸锆、碳酸锆、辛酸锆、柠檬酸锆、磷酸锆等有机酸的锆盐;碳酸锆铵、硫酸锆钠、乙酸锆铵、碳酸锆铵、碳酸锆钾、草酸锆钠、柠檬酸锆钠、柠檬酸锆铵、乳酸锆铵等锆配盐,此外还有将一种或两种以上的螯合剂作为配位体的锆螯合物。其中,优选水溶性锆、更优选氧卤化锆、二乙酸基氧化锆、硫酸锆和硝酸氧锆。
作为锆螯合物,例如可列举出:四乙酰丙酮锆、单乙酰丙酮锆、氧卤化锆、硝酸氧锆、乳酸锆铵、硫酸锆和二乙酸基氧化锆、双乙酰丙酮锆、单乙基乙酰乙酸锆、乙酸锆等。
锆化合物中,四乙酰丙酮锆、单乙酰丙酮锆、氧卤化锆、硝酸氧锆、乳酸锆铵、硫酸锆和二乙酸基氧化锆等由于稳定性、水溶性、反应性高而优选。它们可以使用一种或两种以上的混合物。
作为锆化合物,可以使用市售品,例如可列举出:氧氯化锆、Zircosol ZC-2、Zircosol ZN、Zircosol HA、Zircosol AC-7、Zircosol ZK-10、Zircosol ZN、Zircosol ZA-10、Zircosol ZA-20、辛酸锆、碳酸锆(以上,第一稀元素化学工业株式会社制)、ORGATIXZA-45、ORGATIX ZA-65、ORGATIX ZB-126、ORGATIX ZC-126、ORGATIX ZC-150、ORGATIX ZC-200、ORGATIX ZC-300、ORGATIX ZC-320、ORGATIX ZC-540、ORGATIX ZC-580、ORGATIX ZC-700、ZC-300(以上,Matsumoto Fine Chemical Co.,Ltd.制)等。
作为钛化合物,可列举出:四甲基钛酸酯、四乙基钛酸酯、四正丙基钛酸酯、四异丙基钛酸酯、四正丁基钛酸酯、四异丁基钛酸酯、四叔丁基钛酸酯、四辛基钛酸酯、四(2-乙基己基)钛酸酯、四甲基钛酸酯等烷氧基钛;钛丁基二聚体、钛丁基四聚体等通过烷氧基钛的水解反应而得到的低聚物、聚合物和它们的衍生物;乙酰丙酮钛、甘醇酸辛酯钛、四乙酰丙酮钛、乙酰乙酸乙酯钛、三乙醇铝酸钛、草酸钛等钛螯合物;多羟基硬脂酸钛等钛酰化物;四氯化钛、乳酸钛、三乙醇胺钛、二(三乙醇胺)钛酸二异丙酯等,它们可以使用一种或组合使用两种以上。
作为钛化合物,可以使用市售品,例如可列举出:ORGATIX TA-8、ORGATIX TA-10、ORGATIX TA-12、ORGATIX TC-100、ORGATIX TC-120、ORGATIX TC-300、ORGATIX TC-310、ORGATIX TC-315、ORGATIX TC-335、ORGATIX TC-401、ORGATIX TC-800、ORGATIX WS-700(以上,Matsumoto Fine Chemical Co.,Ltd.制)TITA BOND T-100、TITA BOND T-120、TITABOND T-120A、TITA BOND T-150、TITA BOND T-160、TITA BOND T-180E、TITA BOND T-185E、(以上,日本曹达制)等。
由于通过本发明的水溶性组合物而得到的固化物的耐湿热性良好,因此在上述交联剂中也特别优选锆化合物或钛化合物。
添加交联剂和聚乙烯醇改性水溶性聚合物的情况下,交联剂的添加量相对于聚乙烯醇改性水溶性聚合物的100质量份为0.01~5质量份时,没有析出、增稠等变化、水溶性组合物稳定,故优选。
本发明的水溶性组合物中包含源自交联剂的金属成分,但金属含量在除了水溶性组合物的溶剂之外的成分中,优选0.01~3质量%、更优选0.01~1质量%。
作为不具有上述光敏基团及上述通式(VI)所示的结构单元的水溶性聚合物,可列举出:氧化淀粉、经醚化/酯化/接枝化的改性淀粉、明胶/干酪素/羧甲基纤维素等纤维素衍生物;聚乙烯吡咯烷酮、水溶性聚酯树脂、丙烯酸2-羟基丙酯聚合物/丙烯酸4-羟基丁酯聚合物等水溶性聚丙烯酸酯树脂、水溶性聚碳酸酯树脂、水溶性聚乙酸乙烯酯树脂、水溶性苯乙烯丙烯酸酯树脂、水溶性乙烯基甲苯丙烯酸酯树脂、水溶性聚氨基甲酸酯树脂、聚乙烯基酰胺/聚丙烯酰胺、改性丙烯酰胺等水溶性聚酰胺树脂;水溶性尿素树脂、水溶性聚己内酯树脂、水溶性聚苯乙烯树脂、水溶性聚氯乙烯树脂、水溶性聚丙烯酸酯树脂、水溶性聚丙烯腈树脂等水溶性树脂和苯乙烯-丁二烯共聚物、丙烯酸酯共聚物、乙烯-乙酸乙烯酯共聚物等。
作为上述有机酸,只要是具有羧基的弱酸性的化合物就可以没有限制地使用,例如可列举出:乙酸、柠檬酸、苹果酸、乙醇酸、乳酸、碳酸、甲酸、草酸、丙酸、辛酸(octylicacid)、癸酸(caprylic acid)、葡萄糖醛酸、硬脂酸、苯甲酸、扁桃酸等。这些当中,优选乳酸、乙酸、柠檬酸、乙醇酸或苹果酸。
作为上述偶联剂,可以使用:二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、甲基乙基二甲氧基硅烷、甲基乙基二乙氧基硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷、乙基三甲氧基硅烷、乙基三甲氧基硅烷等烷基官能性烷氧基硅烷;乙烯基三氯硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、烯丙基三甲氧基硅烷等烯基官能性烷氧基硅烷;3-甲基丙烯酰氧基丙基三乙氧基硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-甲基丙烯酰氧基丙基甲基二乙氧基硅烷、3-甲基丙烯酰氧基丙基甲基二甲氧基硅烷、2-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-缩水甘油醚氧丙基三甲氧基硅烷、γ-缩水甘油醚氧丙基甲基二乙氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷等环氧官能性烷氧基硅烷;N-β(氨基乙基)-γ-氨基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、N-苯基-γ-氨基丙基三甲氧基硅烷等氨基官能性烷氧基硅烷和γ-巯基丙基三甲氧基硅烷等巯基官能性烷氧基硅烷等。
上述敏化剂在通过光照射而固化时能扩大可适应光的波长范围的化合物,作为敏化剂,例如优选日本特开2005-307199中记载的噻吨酮类、日本特开2012-7071中记载的噻吨酮类、WO2014/050551中记载的二苯甲酮类、噻吨酮类、硫代色满酮类、联咪唑类等。
作为上述以外的敏化剂,例如可列举出:α-氨基苯乙酮类、α-羟基苯乙酮类、苄基缩酮类二苯甲酮、3-羟基二苯甲酮、4-羟基二苯甲酮、4,4-二羟基二苯甲酮、2-甲基二苯甲酮、3-甲基二苯甲酮、4-甲基二苯甲酮、2,5-二甲基二苯甲酮、3,4-二甲基二苯甲酮、4-甲氧基二苯甲酮、4,4-二甲氧基二苯甲酮、3,3-二甲基-4-甲氧基二苯甲酮、4-苯基二苯甲酮等二苯甲酮类、苯乙酮、4-甲氧基苯乙酮、2,4-二甲氧基苯乙酮、2,5-二甲氧基苯乙酮、2,6-二甲氧基苯乙酮、4,4-二甲氧基苯乙酮、4-乙氧基苯乙酮、二乙氧基苯乙酮、2,2-二乙氧基苯乙酮、2-乙氧基-2-苯基苯乙酮、4-苯基苯乙酮等苯乙酮类、蒽醌、羟基蒽醌、1-硝基蒽醌、氨基蒽醌、2-氯蒽醌、2-甲基蒽醌、2-乙基蒽醌、蒽醌磺酸、1,2-苯并蒽醌、1,4-羟基蒽醌(醌茜)等蒽醌类、蒽、1,2-苯并蒽、9-氰基蒽、9,10-二氰基蒽、2-乙基-9,10-二甲氧基蒽、9,10-双(苯基乙基)蒽等蒽类、2,3-二氯-6-二氰基-对苯醌、2,3-二甲氧基-5-甲基-1,4-苯醌、甲氧基苯醌、2,5-二氯-对苯醌、2,6-二甲基-1,4-苯醌、9,10-菲醌、樟脑醌、2,3-二氯-1,4-萘醌、呫吨酮等醌类;噻吨酮、2-甲基噻吨酮、2,4-二甲基噻吨酮、异丙基噻吨酮、2,4-二乙基噻吨酮、2,4-异丙基噻吨酮等噻烷类;二苯并环庚酮、二苯并环庚烯、二苯并环庚醇、二苯并环庚烷等环庚烷类、2-甲氧基萘、苯偶姻异丙基醚、4-苯甲酰基联苯、邻苯甲酰基苯甲酸、邻苯甲酰基苯甲酸甲酯、4-苯甲酰基-4-甲基-二苯基硫醚、苯偶酰、苯偶姻甲醚等芳香族化合物;以及作为色素系敏化性物质的香豆素系、噻嗪系、吖嗪系、吖啶系、呫吨系化合物等,其中,特别是从在水中的稳定性高(不易受到水解)的观点出发,优选二苯甲酮类、噻吨酮类、硫代色满酮类、联咪唑类、α-氨基苯乙酮类、α-羟基苯乙酮类、苄基缩酮类。
作为上述表面活性剂,可以使用:全氟烷基磷酸酯、全氟烷基羧酸盐等氟表面活性剂;高级脂肪酸碱金属盐、烷基磺酸盐、烷基硫酸盐等阴离子系表面活性剂;高级胺卤酸盐、季铵盐等阳离子系表面活性剂;聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨醇酐脂肪酸酯、脂肪酸单甘油酯等非离子表面活性剂;两性表面活性剂;有机硅系表面活性剂等表面活性剂,还可以组合使用它们。
作为上述碱性化合物,例如可列举出:氨、氢氧化钠、氢氧化钾、三乙胺、三乙醇胺、二乙醇胺、单乙醇胺、三异丙醇胺、二异丙醇胺、单异丙醇胺、N,N-二甲基乙醇胺、乙烯亚胺、吡咯烷、哌啶、聚乙烯亚胺等,它们可以使用一种或组合使用两种以上,有时出于pH调节等的目的而添加碱性化合物。
作为上述着色剂,可以使用颜料和染料。作为颜料和染料,可以分别使用无机着色材料或有机着色材料,可以单独使用它们或混合2种以上来使用。此处,颜料是指不溶于后述溶剂的着色剂,无机或有机着色材料中还包括不溶于溶剂的材料、或使无机或有机染料色淀化而成的材料。
作为上述颜料,可列举出:通过熔炉法(furnace)、槽法(channel)或热裂法(thermal)而得到的炭黑或乙炔黑、科琴黑或灯黑等炭黑;用环氧树脂调节或覆盖上述炭黑而成的物质;预先在溶剂中将上述炭黑用树脂进行了分散处理、并用20~200mg/g树脂覆盖而成的物质;对上述炭黑进行酸性或碱性表面处理而成的物质;平均粒径为8nm以上且DBP吸油量为90ml/100g以下的炭黑、由在950℃下的挥发成分中的CO和CO2计算出的总氧量是每100m2表面积9mg以上的炭黑、石墨化炭黑、石墨、活性炭、碳纤维、碳纳米管、碳微线圈、碳纳米角、碳气凝胶、富勒烯、苯胺黑、颜料黑7、钛黑等所代表的黑色颜料,氧化铬绿、米洛丽蓝、钴绿、钴蓝、锰系、亚铁氰化物、磷酸盐群青、普鲁士蓝、佛青、天蓝、铬绿、翡翠绿、硫酸铅、黄色铅、锌黄、三氧化二铁(红色氧化铁(III))、镉红、合成铁黑、棕土、色淀颜料等有机或无机颜料,从遮光性高的方面出发,优选使用黑色颜料,作为黑色颜料进一步优选使用炭黑。
作为上述颜料,可以使用市售品,例如可列举出:MICROPIGMO WMYW-5、MICROPIGMOWMRD-5、MICROPIGMO WMBN-5、MICROPIGMO WMGN-5、MICROPIGMO WMBK-5、MICROPIGMO WMBE-5、MICROPIGMO WMVT-5、MICROPIGMO WMWE-1、BONJET BLACK CW-1(以上,Orient ChemicalIndustries Co.,Ltd.制)颜料红1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、254、228、240及254;颜料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65及71;颜料黄1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180及185;颜料绿7、10、36及58;颜料蓝15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62及64;颜料紫1、19、23、27、29、30、32、37、40及50等。
作为上述染料,例如可列举出:亚硝基化合物、硝基化合物、偶氮化合物、重氮化合物、呫吨化合物、喹啉化合物、蒽醌化合物、香豆素化合物、花青化合物、酞菁化合物、异吲哚啉酮化合物、异吲哚满化合物、喹吖啶酮化合物、蒽嵌蒽醌化合物、芘酮化合物、二萘嵌苯化合物、二酮吡咯并吡咯化合物、硫靛化合物、二噁嗪化合物、三苯基甲烷化合物、喹酞酮化合物、萘四羧酸、偶氮染料、花青染料的金属络合物等。
作为上述染料,可以适时地使用水溶性染料及油溶性染料。
作为上述染料,可以使用市售品,例如可列举出:WATER YELLOW 1、WATER YELLOW2、WATER YELLOW 6C、WATER YELLOW 6CL、WATER ORANGE 18、WATER ORANGE 25、WATER RED1、WATER RED 2S、WATER RED 3、WATER RED 9、WATER RED 27、WATER PINK 2S、WATER BROWN16、WATER GREEN 8、WATER BLUE 3、WATER BLUE 9、WATER BLUE 105S、WATER BLUE 106、WATER BLUE 117-L、WATER VIOLET 7、WATER BLACK 31、WATER BLACK 191-L、WATER BLACK256-L、WATER BLACK R-455、WATER BLACK R-510、BONJET YELLOW 161-L、BONJET MAGENTAXXX、BONJET CYAN XXX、BONJET BLACK 891-L、VALIFAST YELLOW 1101、VALIFAST YELLOW3150、VALIFAST RED 1308、VALIFAST RED 2320、VALIFAST PINK 1364、VALIFAST PINK2310N、VALIFAST VIOLET 1701、VALIFAST BLACK 1815、VALIFAST BLACK 1807、VALIFASTBLACK 3804、VALIFAST BLACK 3810、VALIFAST BLACK 3820、VALIFAST BLACK 3830、VALIFAST BLACK 3840、VALIFAST BLACK 3866、VALIFAST BLACK 3870、VALIFAST ORANGE2210、VALIFAST BROWN3402、VALIFAST BLUE 1613及VALIFAST BLUE 1605(以上,OrientChemical Industries Co.,Ltd.制)Acid Green 1、Acid Green 3、Acid Green 5、AcidGreen9、Acid Green 27、Acid Green 50、Acid Green A、Alizarin Cyanin Green F、BasicGreen 1、Basic Green 5、Bromocresol Green、Bromocresol Green Sodium Salt、ErioGreen B、Fast Green FCF、Fiter Blue Green Sodium Salt、Indocyanine Green、JanusGreen B、Leuco Malachite Green、Malachite Green,Oxalate、Methyl Green、PalatineChrome Green、Quinizarin Green SS、Acid Red 1、Acid Red 9、Acid Red 13、Acid Red18、Acid Red 26、Acid Red 27、Acid Red 52、Acid Red 87、Acid Red 88、Acid Red 91、Acid Red 92、Acid Red 94、Acid Red112、Acid Red 114、Acid Red 151、Acid Red 289、Alizarin、Allura Red AC、Astrazon Red 6B、Azo Rubine、Basic Red 5、Benzopurpurine4B、Bordezux Red、Chlorantine Fast Red 5B、Chromotrope 2B、Chromotrope 2R、CongoRed、Cresol Red、Crezol Red Sodium Salt、Crocein Scarlet 3B、Direct Fast Red 3B、Direct Red 80、Direct Scarlet B、Eriochrome Red B、4-EthoxychrysoidineHydrochloride、Ethyl Red、Fast Red B Salt、Fast Red ITR Base、Lake Red CBA、LitholRubin BCA、Methoxy Red、Methyl Red、Methyl Red Sodium Salt、Oralith BrilliantPink R、Para Red、Phenol Red Sodium Salt、Pigment Red、Pigment Red 254、Rhodamine6G、Sudan II、Sudan III、Sudan R、2,3,5-Triphenyltetrazolium Chloride、Acid Black1、Acid Blue 1、Acid Blue 9、Acid Blue 92、Acid Blue3Sodium Salt、Acid Red 91、AzoBlue、Basic Blue 1、Basic Blue 7、Basic Blue12、Basic Blue 17、Basic Blue 24、BasicBlue 26、Briliant Blue G、Brilliant Blue R、Bromocresol Blue、Bromophenol Blue、Bromothymol Blue、Chrome Pure Blue BX、Coomassie Brilliant Blue G-250、CoomassieBrilliant Blue R-250、Direct Blue 1、Direct Blue 2、Direct Blue 14、Direct SkyBlue、Disperse Blue 14、Eriochrome Blue Black B、Eriochrome Cyanine R、EvansBlue、Filter Blue Green Sodium Salt、Indigo Carmine、Indigo、Methylene BlueHydrate、Mordant Black17、Mordant Blue 13、Mordant Blue 29、Omega Chrome BlackBlue G、Pigment Blue 15、Quinizarin Blue、Sudan Blue、Thymol Blue、Xylene CyanolFF、Acid Orange 5、Acid Orange 7、1-Amino-2-methylanthraquione、Astrazon OrangeR、Basic Orange 14、Crocein Orange G、Ethyl Orange、Methyl Orange、Mordant Orange1、α-Naphtol Orange、Oil Orange、Orange G、Permanent Orange、Pyrazolone Orange、Sudan I、Sudan II(以上,东京化成工业公司制)等。
作为上述自由基引发剂(除酰基次膦酸盐(A)以外)可以使用现有公知化合物,例如可以使用:日本特开平6-228218、日本特开2009-102455、日本特开2012-007071、WO2014/050551、日本特开平06-239910、日本特开2003-192712、日本特开2016-185929中记载的化合物,以及二苯甲酮、噻吨酮、1-氯-4-丙氧基噻吨酮、异丙基噻吨酮、二乙基噻吨酮、乙基蒽醌等夺氢型的光聚合引发剂;苯基联苯酮、1-羟基-1-苯甲酰基环己烷(α-羟基烷基苯酮)、苯偶姻、苯偶酰二甲基缩酮、1-苄基-1-二甲基氨基-1-(4’-吗啉基苯甲酰基)丙烷、2-吗啉基-2-(4’-甲基巯基)苯甲酰基丙烷、4-苯甲酰基-4’-甲基二苯基硫化物、苯偶姻丁基醚、2-羟基-2-苯甲酰基丙烷、2-羟基-2-(4’-异丙基)苯甲酰基丙烷、4-丁基苯甲酰基三氯甲烷、4-苯氧基苯甲酰基二氯甲烷、苯甲酰基甲酸甲酯、1-羟基-环己基-苯基-酮、2-羟基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羟基乙氧基)-苯基]-2-羟基-2-甲基-1-丙烷-1-酮、1,7-双(9’-吖啶基)庚烷、9-正丁基-3,6-双(2’-吗啉基异丁酰基)咔唑、2-甲基-4,6-双(三氯甲基)-均三嗪、2-苯基-4,6-双(三氯甲基)-均三嗪、2-萘基-4,6-双(三氯甲基)-均三嗪、2,2-双(2-氯苯基)-4,5,4’,5’-四苯基-1-2’-联咪唑等光分解型光聚合引发剂,从反应性方面考虑,优选光分解型光聚合引发剂。
上述光分解型光聚合引发剂之中,由于Irg2959、Irg819DW(BASF公司制)、ESACUREONE、ESACURE 1001M、ESACURE KIP 150及ESACURE DP250(Lamberti公司)等水溶性引发剂等在水中的亲和性高,故优选。
作为上述水溶性防腐剂,可以举出在水中的溶解度高、在室温下的溶解度为1%以上的物质,具体而言,可列举出:对羟基苯甲酸甲酯、苯甲酸、苯甲酸盐、水杨酸、水杨酸盐、苯氧基乙醇、水溶性阳离子抗菌剂、有机硫化合物、卤化化合物、环状有机氮化合物、低分子量醛、对羟基苯甲酸酯、丙二醇物质、异噻唑啉酮、季化物、苯甲酸酯、低分子量醇、脱氢乙酸、ACQ(铜/季铵化合物)、CUAZ(铜/唑化合物)、AAQ(季铵化合物)、亚硫酸氢钠、硫酸氢钠、硫代硫酸钠、抗坏血酸盐、苯扎氯铵、氯丁醇、硫柳汞、乙酸苯汞、硼酸苯汞、硝酸苯汞、对羟基苯甲酸酯、对羟基苯甲酸甲酯、聚乙烯醇、苄醇、异噻唑酮、三嗪、溴硝醇、噻苯唑、吡啶硫酮锌、多菌灵、吡啶氧化物硫醇钠盐和苯基乙醇等。
作为上述水溶性防腐剂,可以使用市售品,可列举出:SAN-AI BAC P、SAN-AI BAC300K、SAN-AI BAC IT-15SA、SAN-AI BAC AS-30、SAN-AI BAC T-10、SAN-AI BAC M-30、SAN-AI BAC SODIUM OMADINE(均为三爱石油株式会社制)等。
作为上述导电性物质,例如可列举出:金属、金属的氧化物、导电性碳和导电性聚合物等。
作为上述金属,例如可列举出:金、银、铜、铂、锌、铁、铅、锡、铝、钴、铟、镍、铬、钛、锑、铋、锗和镉等金属、及锡-铅合金、锡-铜合金、锡-银合金和锡-铅-银合金等由2种以上的金属构成的合金等。其中,优选镍、铜、银或金。
作为上述导电性碳,例如可列举出:科琴黑、乙炔黑、炉黑、槽法炭黑等炭黑、富勒烯、碳纳米管、碳纳米纤维、石墨烯、非晶碳、碳纤维、天然石墨、人造石墨、石墨化科琴黑和介孔碳等。
作为上述导电性聚合物,例如可列举出:聚乙炔、聚吡咯、聚(3-甲基吡咯)、聚(3-丁基吡咯)、聚(3-辛基吡咯)、聚(3-癸基吡咯)、聚(3,4-二甲基吡咯)、聚(3,4-二丁基吡咯)、聚(3-羟基吡咯)、聚(3-甲基-4-羟基吡咯)、聚(3-甲氧基吡咯)、聚(3-乙氧基吡咯)、聚(3-辛氧基吡咯)、聚(3-羧基吡咯)、聚(3-甲基-4-羧基吡咯)、聚N-甲基吡咯、聚噻吩、聚(3-甲基噻吩)、聚(3-丁基噻吩)、聚(3-辛基噻吩)、聚(3-癸基噻吩)、聚(3-十二烷基噻吩)、聚(3-甲氧基噻吩)、聚(3-乙氧基噻吩)、聚(3-辛氧基噻吩)、聚(3-羧基噻吩)、聚(3-甲基-4-羧基噻吩)、聚(3,4-乙烯二氧噻吩)、聚苯胺、聚(2-甲基苯胺)、聚(2-辛基苯胺)、聚(2-异丁基苯胺)、聚(3-异丁基苯胺)、聚(2-苯胺磺酸)、聚(3-苯胺磺酸)和在聚噻吩衍生物(PEDOT:聚(3,4)-乙烯二氧噻吩)中掺杂了聚苯乙烯磺酸(PSS)而成的物质等。
另外,在不损害本发明的效果的范围内,除了上述以外还可以根据需要添加光聚合引发剂、热聚合引发剂、光碱产生剂、产酸剂、无机填料、有机填料、消泡剂、增稠剂、流平剂、有机金属偶联剂、触变剂、碳化合物、金属微粒、金属氧化物、阻燃剂、增塑剂、光稳定剂、热稳定剂、防老剂、弹性体颗粒、链转移剂、阻聚剂、紫外线吸收剂、抗氧化剂、抗静电剂、脱模剂、流动调整剂、密合促进剂、不饱和单体、环氧化合物/氧杂环丁烷化合物/乙烯基醚等阳离子聚合性化合物等各种树脂添加物等。
接着,对本发明的固化物的制造方法进行说明。
本发明的固化物的制造方法是使本发明的水溶性组合物利用光照射或加热而固化的方法。关于使用了本发明的水溶性组合物的固化物的制造方法,以下示出优选的涂布方法、固化条件。
优选的涂布方法可利用旋涂机、棒涂机、辊涂机、帘式涂布机、各种印刷、浸渍等公知的手段涂布于玻璃、金属、纸、塑料等支撑基体上。另外,也可以暂时施于薄膜等支撑基体上之后转印到其它支撑基体上,其应用方法没有特别限制。
作为透明支撑体的材料,例如可列举出:玻璃等无机材料;二乙酰基纤维素、三乙酰基纤维素(TAC),丙酰基纤维素、丁酰基纤维素、乙酰丙酰基纤维素、硝基纤维素等纤维素酯;聚酰胺;聚碳酸酯;聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚对苯二甲酸-1,4-环己烷二甲醇酯、聚亚乙基-1,2-二苯氧基乙烷-4,4’-二羧酸酯、聚对苯二甲酸丁二醇酯等聚酯;聚苯乙烯;聚乙烯、聚丙烯、聚甲基戊烯等聚烯烃;聚甲基丙烯酸甲酯等丙烯酸类树脂;聚碳酸酯;聚砜;聚醚砜;聚醚酮;聚醚酰亚胺;聚氧乙烯、降冰片烯树脂等高分子材料。透明支撑体的透光率优选为80%以上、进一步优选为86%以上。雾度优选为2%以下、进一步优选为1%以下。折射率优选为1.45~1.70。
就优选的固化条件而言,将本发明的水溶性组合物涂布于透明支撑体上后进行光照射时,所照射的光的波长、强度及照射时间等照射条件可根据光引发剂的活性、所使用的光聚合性树脂的活性等进行适宜调整,但作为光波长,通常为了使光充分地进入至内部而优选波长峰300~500nm、更优选波长峰350~450nm、最优选波长峰360~380nm。另外,作为光强度,优选10~300mW/cm2、更优选25~100mW/cm2,照射时间优选5~500秒、更优选10~300秒。
将本发明的水溶性组合物涂布于透明支撑体上后也可以通过加热而使交联反应进行。加热是以50~200℃、优选以70~150℃进行10分钟~1小时进行的。低于50℃时有交联反应不进行的担心,高于200℃时有发生构成成分的分解、或光学薄膜的透明性降低的担心。
利用光刻法(以下,也称为“光刻”)制作固化物的图案时,使用以利用触针式形状测定器(ULVAC,Inc.制Dektak150)测得的膜厚为5.0~5.5μm的方式调整了条件的旋涂机,将本发明的水溶性组合物涂布于玻璃基板上,然后用90℃的热板进行10分钟预烘焙。然后,冷却至室温,借由光掩模(LINE/SPACE=50μm/50μm),使用高压汞灯,照射包含365nm的波长的光500mJ/cm2,在23℃的离子交换水中浸渍1分钟后,用气枪去除附着了的水,在140℃的烘箱内将基板干燥30分钟。优选的固化条件与上述同样。
本发明的固化物是由本发明的水溶性组合物形成的。作为本发明的水溶性组合物的具体用途,可列举出:眼镜、拍摄用透镜所代表的光学材料、涂料、各种涂覆剂、衬里剂、墨、抗蚀剂、液体抗蚀剂、粘接剂、液晶滴加方法用密封剂、图像形成材料、图案形成材料、印刷版、绝缘清漆、绝缘片、层叠板、印刷电路板、半导体装置用/封装用/液晶注入口用/有机EL用/光元件用/电绝缘用/电子部件用/分离膜用等密封剂、成型材料、二次电池的电极、分隔件、修补剂、建筑材料、板壁、玻璃纤维浸渗剂、填隙剂、半导体用/太阳能电池用等钝化膜、层间绝缘膜、保护膜、液晶显示装置的背光中使用的棱镜透镜薄片、投影电视等的屏幕中使用的菲涅尔透镜薄片、柱状透镜薄片等透镜薄片的透镜部、或使用这样的片的背灯等、液晶滤色器的保护膜、间隔物、DNA分离芯片、微反应器、纳米生物装置、硬盘用记录材料、固体拍摄元件、太阳能电池面板、发光二极管、有机发光装置、发光薄膜、荧光薄膜、MEMS元件、致动器、全息照相、等离子体装置、偏光板、偏光薄膜、微透镜等光学透镜、光学元件、光连接器、光波导、光学的造形用铸塑剂等,例如作为可用作涂覆剂的基材,可以列举出:金属、木材、橡胶、塑料、玻璃、陶瓷制品等。
将本发明的水溶性组合物用于光学薄膜时,光学薄膜可以利用常用的方法进行薄膜或片成型,在不对得到的薄膜或片进行拉伸(或取向处理)的前提下制造,还可以通过进行拉伸(或取向处理)来制造。薄膜成型时可以利用挤出成型、吹塑成型等熔融成型法(熔融制膜法),还可以利用流延成型法(流延制膜法、溶液流延法)。
使用了本发明的水溶性组合物的光学薄膜对其形状没有特别限制,通常为在透明支撑体上具有光学膜而可用于光学用途的薄膜,可以列举出:液晶显示装置等中使用的偏光板用保护薄膜、相位差薄膜、视角扩大薄膜、等离子体显示器中使用的防反射薄膜、低反射率薄膜等各种功能薄膜、此外有机EL显示器等中使用的各种功能薄膜等。
使用了本发明的水溶性组合物的光学薄膜可以用作:将光学薄膜应用于支撑体上的可写入型光盘(CD±R、DVD±R、下一代型高密度盘等)的光学记录层;各种透镜;图像显示装置用光学过滤器;滤色器、色转换过滤器所代表的各种过滤器;或有机EL发光元件、无机EL发光元件或电子纸显示体等的保护密封薄膜。
实施例
以下列举实施例等对本发明进行进一步详细地说明,但本发明不限定于这些实施例。需要说明的是,本实施例中记载的固体成分是指去除了溶剂后的成分所占的质量%。
[制造例1:苯基(2,4,6-三甲基苯甲酰基)次膦酸的合成]
在附有回流管的反应烧瓶中,加入2,4,6-三甲基苯甲酰基苯基次膦酸乙酯71.2g(225mmol)、2-丁酮(MEK)420g,在氮气气流下、以室温边搅拌边使其溶解。添加碘化钠35.4g(236mmol),直接在室温下搅拌15分钟,然后升温至65℃。以65℃继续搅拌8小时后,冷却至室温,过滤析出物,将过滤物用MEK 100g清洗。在减压下以60℃干燥,从而得到苯基(2,4,6-三甲基苯甲酰基)次膦酸钠53.8g(收率77.2%)。在附有回流管的反应烧瓶中,加入苯基(2,4,6-三甲基苯甲酰基)次膦酸钠50.0g(161mmol)、离子交换水278g,边搅拌边使其完全溶解。然后,在室温下滴加浓硫酸15.8g和离子交换水553g的混合液,直接继续搅拌2小时。过滤析出物,用水100ml清洗2次。将过滤物用60℃热风烘箱干燥,得到淡黄色晶体42.3g(收率91.2%)。
<实施例1-1:4-甲基吗啉-4-鎓=苯基(2,4,6-三甲基苯甲酰基)次膦酸盐(酰基次膦酸盐No.1)的合成>
在反应烧瓶中加入苯基(2,4,6-三甲基苯甲酰基)次膦酸3.0g(10.4mmol)、二氯甲烷15ml,在室温下边搅拌边使其完全溶解。缓慢加入4-甲基吗啉1.05g(10.4mmol),直接在室温下继续搅拌2小时。过滤不溶物后,进行脱溶剂,用己烷清洗残渣,减压干燥后,以收量3.8g(收率93.8%)得到作为淡黄色的晶体的酰基次膦酸盐No.1(下述结构)。分析结果示于〔表1〕及〔表2〕。
酰基次膦酸盐No.1
<实施例1-2:吡咯烷-1-鎓=苯基(2,4,6-三甲基苯甲酰基)次膦酸盐(酰基次膦酸盐No.2)的合成
在反应烧瓶中加入苯基(2,4,6-三甲基苯甲酰基)次膦酸1.0g(3.5mmol)、二氯甲烷5ml,在室温下边搅拌边使其完全溶解。缓慢加入吡咯烷0.25g(3.5mmol),直接在室温下继续搅拌2小时。过滤不溶物后,进行脱溶剂,用己烷清洗残渣,减压干燥后,以收量1.0g(收率80.0%)得到作为淡褐色的晶体的酰基次膦酸盐No.2(下述结构)。分析结果示于〔表1〕及〔表2〕。
酰基次膦酸盐No.2
<实施例1-3:1-苄基-4-羟基哌啶-1-鎓=(苯基(2,4,6-三甲基苯甲酰基)次膦酸盐(酰基次膦酸盐No.3)的合成>
在反应烧瓶中加入苯基(2,4,6-三甲基苯甲酰基)次膦酸1.0g(3.47mmol)、二氯甲烷5ml,在室温下边搅拌边使其完全溶解。滴加溶解于二氯甲烷3ml中的1-苄基-4-羟基哌啶0.796g(4.16mmol),直接在室温下继续搅拌3小时。对反应溶液进行脱溶剂,用己烷清洗得到的残渣,减压干燥后,以收量1.5g(收率90.4%)得到作为淡黄色的晶体的酰基次膦酸盐No.3(下述结构)。分析结果示于〔表1〕及〔表2〕。
酰基次膦酸盐No.3
<实施例1-4:N,N-双(2-羟基乙基)丁烷-1-铵=苯基(2,4,6-三甲基苯甲酰基)次膦酸盐(酰基次膦酸盐No.4)的合成>
在反应烧瓶中加入苯基(2,4,6-三甲基苯甲酰基)次膦酸5.0g(17.3mmol)、二氯甲烷50ml,在室温下边搅拌边使其完全溶解。加入N-丁基二乙醇胺2.8g(17.3mmol),直接在室温下持续搅拌5小时。对反应溶液进行脱溶剂,冷却至10℃以下而固化的残渣用己烷清洗,减压干燥后,以收量7.5g(收率97.4%)得到作为淡黄色的晶体的酰基次膦酸盐No.4(下述结构)。分析结果示于〔表1〕及〔表2〕。
酰基次膦酸盐No.4
[表1]
[表2]
[制造例2:具有光敏基团及羟基的水溶性聚合物水溶液No.1]
在加入有1000份离子交换水的反应烧瓶中,缓慢投入作为含羟基的聚合物的Nichigo G-Polymer OKS-1083(皂化度99;日本合成化学工业制)138份,搅拌1小时后,加热至90℃使其完全溶解。冷却至40℃,投入羟基2mol%份的光敏基团赋予剂的甲酰基苯乙烯基吡啶鎓和磷酸0.7份,在40℃下持续搅拌2小时。将溶液冷却至室温后,追加离子交换水使其成为固形成分15%,在室温下进而进行搅拌1小时,用5μm过滤器过滤后,加入离子交换水,调整固形成分为10质量%,得到具有光敏基团及羟基的水溶性聚合物水溶液No.1。
[制造例3:具有光敏基团及羟基的水溶性聚合物水溶液No.2]
在加入有1000份的离子交换水的反应烧瓶中,缓慢投入[表1]所示的作为含羟基的聚合物的Gohsenol GL-05(皂化度87;日本合成化学工业制)138份,搅拌1小时后,加热至90℃使其完全溶解。冷却至50℃,作为感光性赋予剂投入羟基2mol%份的N-羟甲基丙烯酰胺和对甲苯磺酸0.1份,在50℃下持续搅拌3小时。将溶液冷却至室温后,追加离子交换水,在室温下进而进行搅拌1小时,用5μm过滤器过滤后,加入离子交换水,调整固形成分为10质量%,得到具有光敏基团及羟基的水溶性聚合物水溶液No.2。
[制造例4:聚乙烯醇改性水溶性聚合物水溶液No.1]
将聚乙烯醇Gohsenol NL-05(皂化度98;日本合成化学工业制)10.0g缓慢添加到进行搅拌中的离子交换水90.0g中,直接在室温下搅拌1小时。然后,将内温由85℃调整至90℃,持续搅拌2小时。确认溶解后,冷却至室温,用1μm过滤器过滤后,加入离子交换水,调整固形成分为10质量%,得到聚乙烯醇改性水溶性聚合物水溶液No.1。
[制造例5:聚乙烯醇改性水溶性聚合物水溶液No.2]
将GOHSENX Z-200(皂化度99;日本合成化学工业制)10.0g缓慢添加到进行搅拌中的离子交换水90.0g中,直接在室温下搅拌1小时。然后,将内温由85℃调整至90℃,持续搅拌2小时。确认溶解后,冷却至室温,用1μm过滤器过滤,得到聚乙烯醇改性水溶性聚合物水溶液No.2。
[制造例6:聚吡咯烷酮水溶液No.1]
将作为聚乙烯基吡咯烷酮的K90(日本触媒制)10.0g缓慢添加到进行搅拌中的离子交换水90.0g,直接在室温下搅拌1小时。然后,将内温由85℃调整至90℃,持续搅拌2小时。确认溶解后,冷却至室温,用1μm过滤器过滤,得到聚吡咯烷酮水溶液No.1。
<实施例2-1~2-24及比较例2-1~2-8:水溶性组合物的制备>
按照[表3]~[表6]的配混,将各成分在室温搅拌1小时后,用1μm过滤器过滤,得到水溶性组合物(实施例2-1~2-24及比较例2-1~2-8)。需要说明的是,表中的配混的数值表示质量份。另外,表中的各成分的符号表示下述的成分。
A-1酰基次膦酸盐No.1[本发明的酰基次膦酸盐(A)]
A-2酰基次膦酸盐No.2[本发明的酰基次膦酸盐(A)]
A-3酰基次膦酸盐No.3[本发明的酰基次膦酸盐(A)]
A-4酰基次膦酸盐No.4[酰基次膦酸盐(A)]
A-5酰基次膦酸盐No.5[酰基次膦酸盐(A):下述中记载结构]
A-6’比较自由基引发剂No.1[下述中记载结构]
A-7’比较自由基引发剂No.2[下述中记载结构]
A-8’比较自由基引发剂No.3[下述中记载结构]
B-1NK ESTER A-GLY-20E[化合物(B)]
(环氧烷改性丙烯酸酯;新中村化学工业制)
B-2NK EKONOMA A-PG5054E[化合物(B)]
(环氧烷改性丙烯酸酯;新中村化学工业制)
B-3FFM-2[化合物(B)]
(多官能丙烯酰胺化合物;Fujifilm制)
B-4丙烯酰吗啉
B-5羟基丙烯酰胺
C-1BONJET BLACK CW-1[着色剂(C)]
(改性炭黑自分散体、浓度20%;Orient化学工业公司制)
C-2MICROPIGMO WMRD-5[着色剂(C)]
(Pigment Red17树脂分散体、浓度20%;Orient化学工业公司制)
C-3MICROPIGMO WMGN-5[着色剂(C)]
(Pigment Green7树脂分散体、浓度21%;Orient化学工业公司制)
C-4MICROPIGMO WMBE-5[着色剂(C)]
(Pigment Blue15:6树脂分散体、浓度20%;Orient化学工业公司制)
D-1具有光敏基团及羟基的水溶性聚合物水溶液No.1
D-2具有光敏基团及羟基的水溶性聚合物水溶液No.2
D-3聚乙烯醇改性水溶性聚合物水溶液No.1
D-4聚乙烯醇改性水溶性聚合物水溶液No.2
D-5聚吡咯烷酮水溶液No.1
E-1MEGAFACE F-444(氟系流平剂;DIC制)
E-2ORGATIX ZC-126
(氯化锆水溶液:成分浓度30%、Zr含量11%;
Matsumoto Fine Chemical制)
E-3ORGATIX WS-700
(有机钛改性聚乙烯亚胺、成分浓度10%水溶液;
Matsumoto Fine Chemical制)
酰基次膦酸盐No.5
比较自由基引发剂No.1
比较自由基引发剂No.2
比较自由基引发剂No.3
[水溶性组合物及固化物的评价]
各水溶性组合物(实施例2-1~2-24及比较例2-1~2-8)中,依照下述顺序进行相容性、涂布性、光刻性及固化物的耐湿热性、及LED光源下的固化性的评价。结果合并示于[表3]~[表6]。
(相容性)
用目视确认各水溶性组合物(实施例2-1~2-19及比较例2-1~2-6)的状态,以以下的基准评价。
◎:透明均匀
○:微白浊
△:白浊
×:不相容、可见凝胶化或不溶物
××:在室温下放置1天以内可见析出、凝胶化或不溶物
评价为◎或○者为可优选使用,◎者为特别优选使用,评价为△者可通过处理后使用,评价为×或××者不适于使用。
(含着色剂的水溶性组合物的相容性)
用目视确认各含着色剂的水溶性组合物(实施例2-20~2-24及比较例2-7、2-8)的状态,以以下的基准评价。
○:均匀
×:不相容、可见凝胶化或不溶物
评价为○者为可优选使用,评价为×者不适于使用。
(涂布性)
通过触针式形状测定器(Ulvac制Dektak 150),使用调整条件来使膜厚成为5.0~5.5μm的旋转涂布机,将各水溶性组合物(实施例2-1~2-24及比较例2-1~2-8)涂布于玻璃基板上,然后,利用90℃的热板进行10分钟预烘焙。用目视确认此时的膜的状态,以以下的基准评价。
○:涂布膜为透明均匀
×:确认到表面有不均等不均匀的状态或析出物
评价为○者为可优选使用,评价为×者不适于使用。
(光刻性)
通过触针式形状测定器(Ulvac制Dektak 150),使用调整条件来使膜厚成为5.0~5.5μm的旋转涂布机,将各水溶性组合物(实施例2-1~2-24及比较例2-1~2-8)涂布于玻璃基板上,然后,利用90℃的热板进行10分钟预烘焙。然后,冷却至室温,借由光掩模(LINE/SPACE=50μm/50μm),使用高压汞灯,照射包含365nm的波长的光300mJ/cm2,在23℃的离子交换水中浸渍1分钟后,用气枪去除附着了的水,在140℃的烘箱内将基板干燥30分钟。用激光显微镜确认干燥后的图案,以以下的基准评价。
○:图案为50±3μm以内
△:50±10μm以内
×:超过50±10μm或无图案
评价结果为○或△者可作为图案形成剂使用,其中,○为可特别优选使用,×不适于图案形成所需的用途。
(耐湿热性)
通过触针式形状测定器(Ulvac制Dektak 150),使用调整条件来使膜厚成为5.0~5.5μm的旋转涂布机,将各水溶性组合物(实施例2-1~2-24及比较例2-1~2-8)涂布于玻璃基板上,然后,利用90℃的热板进行10分钟预烘焙。然后,冷却至室温后,使用高压汞灯照射包含365nm的波长的光500mJ/cm2,将基板在140℃的烤箱内干燥30分钟。将所得固化物在85℃、85%RH的条件下放置24小时,然后,同样地测定固化物的雾度。在耐湿性试验前后,以以下的基准评价。
〇:雾度的变化量不足1.0
△:雾度的变化量为1以上且不足3
×:雾度的变化量为3以上
××:膜的一部分为剥离或溶出
评价结果为○或△的固化物可用于要求耐湿热性的用途,耐湿热性优异的顺序为○、△。其中,为〇的固化物特别适于要求耐湿热性的用途。另一方面,为×及××的固化物无法用于要求耐湿热性的用途。
(LED光源下的固化性)
使用实施例2-13、2-15及2-16以及比较例2-4及2-5的组合物,用敷抹器涂布到玻璃基板上,进行曝光(365nmLED光源、100mJ/cm2)后,浸渍于23℃的离子交换水30秒,确认在140℃下干燥10分钟后的膜厚的变化(不浸渍于水而仅曝光、干燥的涂布膜的膜厚为15μm)。
实施例2-13、2-15及2-16的残膜率分别为93%、92%、90%,与此相对,比较例2-4为54%、比较例2-5为65%。由以上可知,本发明的水溶性组合物对于LED光源曝光也体现出优异的固化特性。
[表3]
[表4]
[表5]
[表6]
由[表3]~[表6]可知,本发明的水溶性组合物的相容性高、涂布性优异、光刻性优异、所得到的固化物的耐湿热性良好。因此,本发明的水溶性组合物可适合用于墨、图像形成材料及图案形成剂等用途,本发明的固化物可适合用于光学薄膜等用途。
Claims (9)
1.一种水溶性组合物,其特征在于,含有:
下述通式(I)所示的酰基次膦酸盐(A),和
具有下述通式(II)所示的基团的化合物(B),
式中,X1表示碳原子数6~15的芳基,
X1所示的基团中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基所取代,
X2表示碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、或碳原子数6~15的芳基,
X2所示的碳原子数6~15的芳基中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基、卤素原子、硝基、氰基、羟基、氨基、羧基、甲基丙烯酰基、丙烯酰基、环氧基、乙烯基、乙烯基醚基、巯基、异氰酸酯基或含杂环基所取代,
X2所示的基团中的亚甲基任选被氧原子或硫原子所取代,
Am+表示碱金属离子、碱土金属离子或N+HY1Y2Y3,
Y1、Y2及Y3分别独立地表示氢原子、羟基、碳原子数1~6的烷基、碳原子数1~6的烯基、碳原子数6~15的芳基或碳原子数7~13的芳烷基,
Y1、Y2及Y3所示的基团中的氢原子任选被羟基所取代,
Y1、Y2及Y3所示的基团中的亚甲基任选被氧原子、或硫原子所取代,
Y1和Y2、Y1和Y3及Y2和Y3中任一者以上任选键合形成环,
m表示1~3的数,
式中,R1表示氢原子或甲基,
Z1表示氧原子或-NR2-,
R2表示氢原子或碳原子数1~20的烃基,
Z2表示碳原子数1~6的亚烷基,
n表示0~30的数,
*是指结合键,
具有多个通式(II)所示的基团的情况下,多个存在的R1、Z1、Z2、n任选分别相同或不同,
所述通式(I)中的X2为苯基、且Am+为N+HY1Y2Y3,Y1和Y2、Y1和Y3及Y2和Y3中任一者以上键合而形成环。
2.根据权利要求1所述的水溶性组合物,其中,所述通式(I)中的X1为2,4,6-三甲基苯基。
3.根据权利要求1或2所述的水溶性组合物,其中,所述通式(I)中的Am+中的Y1、Y2及Y3中任一者以上的氢原子被羟基所取代。
4.根据权利要求1或2所述的水溶性组合物,其中,所述通式(II)中的Z1为-NR2-。
5.根据权利要求1或2所述的水溶性组合物,其进而含有着色剂(C)。
6.一种固化物的制造方法,其特征在于,使权利要求1~5中任一项所述的水溶性组合物利用光照射或加热而固化。
7.一种固化物,其特征在于,由权利要求1~5中任一项所述的水溶性组合物得到。
8.一种酰基次膦酸盐,其特征在于,其为下述通式(I)所示的酰基次膦酸盐,
式中,X1表示碳原子数6~15的芳基,
X1所示的基团中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基所取代,
X2表示碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、或碳原子数6~15的芳基,
X2所示的碳原子数6~15的芳基中的氢原子任选被碳原子数1~8的直链的烷基、碳原子数3~8的具有支链的烷基、碳原子数1~8的直链的卤代烷基、碳原子数3~8的具有支链的卤代烷基、碳原子数1~8的直链的烷氧基、碳原子数3~8的具有支链的烷氧基、碳原子数1~8的直链的卤代烷氧基、碳原子数3~8的具有支链的卤代烷氧基、卤素原子、硝基、氰基、羟基、氨基、羧基、甲基丙烯酰基、丙烯酰基、环氧基、乙烯基、乙烯基醚基、巯基、异氰酸酯基或含杂环基所取代,
X2所示的基团中的亚甲基任选被氧原子或硫原子所取代,
Am+表示碱金属离子、碱土金属离子或N+HY1Y2Y3,
Y1、Y2及Y3分别独立地表示氢原子、羟基、碳原子数1~6的烷基、碳原子数1~6的烯基、碳原子数6~15的芳基或碳原子数7~13的芳烷基,
Y1、Y2及Y3所示的基团中的氢原子任选被羟基所取代,
Y1、Y2及Y3所示的基团中的亚甲基任选被氧原子、或硫原子所取代,
Y1和Y2、Y1和Y3及Y2和Y3中任一者以上任选键合形成环,
m表示1~3的数,
其中,所述通式(I)中的X2为苯基,Am+为N+HY1Y2Y3,且
Y1和Y2、Y1和Y3及Y2和Y3中任一者以上键合而形成环。
9.根据权利要求8所述的酰基次膦酸盐,其中,所述通式(I)中的Am+为N+HY1Y2Y3、且Y1、Y2及Y3中任一者以上的氢原子被羟基所取代。
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