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

Patent metadata

Field	Value
Publication number	US-10189867-B2
Application number	US-201715443476-A
Country	US
Kind code	B2
Filing date	Feb 27, 2017
Priority date	Aug 29, 2014
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

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.

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.

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.

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.

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

• C08L83/06

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

• C08J3/28

  Treatment by wave energy or particle radiation · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title

• C09J133/14

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

• C07F7/1804 Primary

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