Organosilicon modified photoinitiator and a photo-curable adhesive composition comprising the same

Patent metadata

Field	Value
Publication number	US-2017166594-A1
Application number	US-201715443476-A
Country	US
Kind code	A1
Filing date	Feb 27, 2017
Priority date	Aug 29, 2014
Publication date	Jun 15, 2017
Grant date	—

Abstract

The present document discloses an organosilicon modified photoinitiator represented by the general formula (I):

wherein,
R 1 and R 2 are each independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, aryl C 1 -C 3 alkyl; one of R 3 , R 4 , R 5 , R 6 , and R 7 is SIL1-X, and the others are each independently selected from the group consisting of hydrogen, C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, aryl C 1 -C 3 alkyl, and halogen; X is a direct bond or C 1 -C 12 alkylene; and SIL1 and SIL2 are each independently represented by the formula —SiR 8 R 9 R 10 or (R′SiO 3/2 ) a (R″ 2 SiO 2/2 ) b (R′″ 3 SiO 1/2 ) c , wherein R 8 , R 9 and R 10 are each independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, aryl, and aryl C 1 -C 3 alkyl, R′, R″ and R′″ each independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, and phenyl C 1 -C 3 alkyl, and a, b, and c are numbers that satisfy a≧0, b≧0, c>0, the ratio of a to c is from 0 to 100, and the ratio of b to c is from 0 to 10.

First claim

What is claimed is:

1 . An organosilicon modified photoinitiator represented by the general formula (I):

wherein,
R 1 and R 2 are each independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, aryl C 1 -C 3 alkyl;
one of R 3 , R 4 , R 5 , R 6 , and R 7 is SIL1-X, and the others are each independently selected from the group consisting of hydrogen, C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, aryl C 1 -C 3 alkyl, and halogen;
X is a direct bond or C 1 -C 12 alkylene; and
SIL1 and SIL2 are each independently represented by the formula —SiR 8 R 9 R 10 or (R′SiO 3/2 ) a (R″ 2 SiO 2/2 ) b (R′″ 3 SiO 1/2 ) c , wherein
R 8 , R 9 and R 10 are each independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, aryl, and aryl C 1 -C 3 alkyl,
R′, R″ and R′″ each independently selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 8 alkenyl, C 5 -C 8 cycloalkyl, and phenyl C 1 -C 3 alkyl, and
a, b, and c are numbers that satisfy a≧0, b≧0, c>0, the ratio of a to c is from 0 to 100, and the ratio of b to c is from 0 to 10.

2 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are C 1 -C 4 alkyl, preferably methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl or tert-butyl, especially methyl.

3 . The organosilicon modified photoinitiator according to claim 1 , wherein R 5 represents SIL1-X—, and R 3 , R 4 , R 6 , and R 7 are each independently selected from the group consisting of hydrogen, C 1 -C 4 alkyl and phenyl C 1 -C 3 alkyl, preferably from hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, hexyl, or octyl, especially hydrogen.

4 . The organosilicon modified photoinitiator according to claim 1 , wherein SIL1 and/or SIL2 is represented by the formula —SiR 8 R 9 R 10 where R 8 , R 9 and R 10 are each independently selected from the group consisting of C 1 -C 4 alkyl, phenyl, and phenyl C 1 -C 3 alkyl, preferably from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, phenyl, benzyl, and phenylethyl.

5 . The organosilicon modified photoinitiator according to claim 4 , wherein SIL1 and/or SIL2 is selected from the group consisting of trimethylsilyl, dimethylphenylsilyl, dimethylphenylethylsilyl and tri-n-propylsilyl.

6 . The organosilicon modified photoinitiator according to claim 1 , wherein SIL1 and/or SIL2 is represented by the formula (R′SiO 3/2 ) a (R″ 2 SiO 2/2 ) b (R′″ 3 SiO 1/2 ) c , wherein R′, R″ and R′″ are methyl, a=0, b=1, c=2, and SIL1 and/or SIL2 corresponds to 1,1,1,3,5,5,5-heptamethyltrisiloxane.

7 . The organosilicon modified photoinitiator according to claim 1 , wherein SIL1 and/or SIL2 is represented by the formula (R′SiO 3/2 ) a (R″ 2 SiO 2/2 ) b (R′″ 3 SiO 1/2 ) c , wherein R′, R″ and R′″ are methyl, a=0, b=1, c=3, and SIL1 and/or SIL2 corresponds to 1,1,1,3,5,5,5,7,7,7-nonamethyltetrasiloxyl.

8 . The organosilicon modified photoinitiator according to claim 1 , wherein X is a direct bond or C 1 -C 3 alkylene, preferably a direct bond, methylene, ethylene or n-propylene.

9 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is trimethylsilyl and X is a direct bond, R 3 , R 4 , R 6 and R 7 are hydrogen, and SIL2 is 1,1,1,3,5,5,5-heptamethyltrisiloxyl.

10 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is 1,1,1,3,5,5,5-heptamethyltrisiloxyl and X is ethylene, R 3 , R 4 , R 6 and R 7 are hydrogen, and SIL2 is 1,1,1,3,5, 5,5-heptamethyltrisiloxyl.

11 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is 1,1,1,3,5,5,5-heptamethyltrisiloxyl and X is n-propylene, R 3 , R 4 , R 6 and R 7 are hydrogen, X is n-propyl, and SIL2 is 1,1,1,3,5,5,5-heptamethyltrisiloxyl.

12 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is 1,1,1,5,5,5,7,7,7-nonamethyltetrasiloxyl and X is ethylene, R 3 , R 4 , R 6 and R 7 are hydrogen, and SIL2 is 1,1,1,5,5,5,7,7,7-nonamethyltetrasiloxyl.

13 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is dimethylphenylsilane and X is ethylene, R 3 , R 4 , R 6 and R 7 are hydrogen, and SIL2 is dimethylphenylsilane.

14 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is dimethylbenzylsilane and X is ethylene, R 3 , R 4 , R 6 and R 7 are hydrogen, and SIL2 is dimethylbenzylsilane.

15 . The organosilicon modified photoinitiator according to claim 1 , wherein R 1 and R 2 are methyl, R 5 is SIL1-X—, in which SIL1 is tri-n-propylsilane and X is ethylene, R 3 , R 4 , R 6 and R 7 are hydrogen, and SIL2 is tri-n-propylsilane.

16 . A photo-curable composition comprising the organosilicon modified photoinitiator according to claim 1 .

17 . The photo-curable composition according to claim 16 , wherein the amount of the organosilicon modified photoinitiator is 0.5% to 5% by weight, based on the total amount of the composition.

18 . A substrate having a surface which is coated on the surface with a photo-curable composition according to claim 17 .

19 . Cured reaction products of the photo-curable composition according to claim 17 .

20 . An organosilicon modified photoinitiator, selected from the group consisting of:

and the combination thereof.

Assignees

• Henkel Ag & Co Kgaa
• Henkel IP & Holding GmbH

Inventors

• Wu Hao
• Li Zhiming
• Li Jinyou
• Zhang Yong
• Zhang Xingang
• Lu Zhixiang
• Lu Zheng

Classifications

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C08J2333/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C08F120/68

  Esters · CPC title