Polyorganosiloxane and a moisture and radiation curable adhesive composition comprising the same

Patent metadata

Field	Value
Publication number	US-10100155-B2
Application number	US-201715695104-A
Country	US
Kind code	B2
Filing date	Sep 5, 2017
Priority date	Mar 10, 2015
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The present invention relates to a polyorganosiloxane and a moisture and radiation curable adhesive composition comprising the same, in particular, to a polyorganosiloxane and a moisture and radiation curable adhesive composition used in a liquid optical clear adhesive (LOCA) for handheld device and display (HHDD).

First claim

What is claimed is:

1. A polyorganosiloxane represented by the structural formula (1):

wherein:
R 1 and R 4 -R 10 are each independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkoxyl, C 2 -C 20 alkenyl, C 3 -C 20 cycloalkyl, C 7 -C 22 aralkyl, and (meth)acryloxy, wherein at least one of R 1 or R 4 is a C 1 -C 20 alkoxyl,
R 2 , R 3 and R 11 -R 14 are selected from C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 3 -C 20 cycloalkyl, and C 7 -C 22 aralkyl,
a is an integer of from 0 to 1000,
b is an integer of from 0 to 1000,
l is an integer of from 0 to 1000,
m is an integer of from 2 to 1000,
n is an integer of from 1 to 1500,
A 1 and A 2 are each independently represented by the formula (2):
(R 15 ) c (R 16 ) d (R 17 ) e R 18   (2)

wherein:
R 15 is C 1 -C 20 alkylene,
R 16 is C 6 -C 21 arylene,
R 17 is C 1 -C 20 alkylene,
R 18 is (meth)acryloxy,
c is an integer of from 0 to 10,
d is an integer of from 0 to 10, and
e is an integer of from 0 to 10, wherein at least one of c or d or e is greater than 0.

2. The polyorganosiloxane according to claim 1 , wherein R 1 and R 4 -R 10 are each independently selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 alkoxyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, and C 7 -C 16 aralkyl and R 2 , R 3 and R 11 -R 14 are selected from the group consisting of C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, and C 7 -C 16 aralkyl.

3. The polyorganosiloxane according to claim 1 , wherein R 15 is C 1 -C 8 alkylene; and/or R 16 is C 6 -C 9 alkylene; and/or R 17 is C 1 -C 8 alkylene.

4. The polyorganosiloxane according to claim 1 , wherein c is an integer of from 1 to 5, d is an integer of from 1 to 5, and e is an integer of from 1 to 5.

5. The polyorganosiloxane according to claim 1 , wherein n is 430, m and a are 68, l and b are 0, A 1 and A 2 are acryloxypropyl, R 2 , R 3 , R 5 to R 14 are methyl, and R 1 and R 4 are methoxy.

6. The polyorganosiloxane according to claim 1 , wherein n, a and m are 190, l and b are 0, A 1 and A 2 are methacryloxymethyl, and R 1 to R 14 are methyl.

7. The process for producing the polyorganosiloxane according to claim 1 , comprising the steps of:
(1) end-capping a silanol-terminated polyorganosiloxane with an alkoxysilane having (meth)acryloxy to form a polyorganosiloxane;
(2) chain extending the polyorganosiloxane obtained in step (1) by reacting with a silanol-terminated polyorganosiloxane to form a product; and
(3) end-capping residual silanol groups contained in the product obtained in step (2).

8. The process according to claim 7 , wherein the silanol-terminated polyorganosiloxane in step (1) is an α,ω-hydroxyl terminated polydimethylsiloxane or an ω-hydroxyl terminated polydimethylsiloxane.

9. The process according to claim 7 , wherein the alkoxysilane having (meth)acryloxy is selected from γ-(meth)acryloxymethyltrimethoxysilane, γ-(meth)acryloxymethylmethyldimethoxysilane, γ-(meth)acryloxymethylmethyldiethoxysilane, γ-(meth)acryloxymethylethyldimethoxysilane, γ-(meth)acryloxymethyltriethoxysilane, γ-(meth)acryloxyethyltrimethoxysilane, γ-(meth)acryloxyethylmethyldimethoxysilane, γ-(meth)acryloxyethylmethyldiethoxysilane, γ-(meth)acryloxyethylethyldimethoxysilane, γ-(meth)acryloxyethyltriethoxysilane, γ-(meth)acryloxypropyltrimethoxysilane, γ-(meth)acryloxypropylmethyldimethoxysilane, γ-(meth)acryloxypropylmethyldiethoxysilane, γ-(meth)acryloxypropylethyldimethoxysilane γ-(meth)acryloxypropyltriethoxysilane, and combinations thereof.

10. The process according to claim 7 , wherein the silanol-terminated polyorganosiloxane in step (2) is an α,ω-hydroxyl terminated polydimethylsiloxane or an ω-hydroxyl terminated polydimethylsiloxane.

11. A moisture and radiation curable composition, comprising:
(a) the polyorganosiloxane according to claim 1 ,
(b) a photoinitiator,
(c) a moisture catalyst,
(d) a reactive plasticizer, and
(e) optionally, a moisture crosslinker.

12. The moisture and radiation curable composition according to claim 11 , wherein component (a) is a mixture of different polyorganosiloxanes with each polyorganosiloxane of component (a) being of formula 1.

13. The moisture and radiation curable composition according to claim 11 , wherein component (a) comprises at least one polyorganosiloxane selected from:
(i) n=430, m and a=68, l and b=0, A 1 and A 2 =acryloxypropyl, R 1 and R 4 =methoxy, and R 2 , R 3 , R 5 to R 14 =methyl;
(ii) n=430, l, m and a=68, b=0, A 1 and A 2 =acryloxypropyl, R 1 to R 3 and R 5 to R 14 =methyl, and R 4 =methoxy;
(iii) n=430, m=68, a, b and l=0, A 1 and A 2 =acryloxypropyl, R 1 =methoxy, R 2 to R 14 =methyl;
(iv) m and n=430, a=68, b and l=0, A 1 and A 2 =acryloxypropyl, R 1 and R 4 =methoxy, and R 2 , R 3 , R 5 to R 14 =methyl; and
(v) n=190, m=190, l, a and b=0, A 1 and A 2 =methacryloxymethyl, R 1 to R 3 and R 5 to R 14 methyl, and R 4 =methoxy.

14. The moisture and radiation curable composition according to claim 11 , wherein component (a) is present in an amount from 20 to 90% by weight, based on the total weight of the components.

15. The moisture and radiation curable composition according to claim 11 , wherein component (d) is present in an amount from 10 to 60% by weight, based on the total weight of the components.

16. The moisture and radiation curable composition according to claim 11 , wherein component (e) is present in an amount from 1 to 5% by weight based on the total weight of the components.

17. The moisture and radiation curable composition according to claim 11 , wherein the composition further comprises a chain extender present in an amount from 5 to 30% by weight, based on the total weight of the components.

18. A cured reaction product of the moisture and radiation curable adhesive composition according to claim 11 .

19. A substrate which is coated on at least one surface with the moisture and radiation curable adhesive composition according to claim 11 .

Assignees

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

Inventors

• Lu Zhixiang
• Li Zhiming
• Li Jinyou
• Lu Zheng
• Zhang Yong

Classifications

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08G77/44 Primary

  containing only polysiloxane sequences · CPC title

• C09J183/10

  Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09J151/08, C09J153/00) · CPC title

• C08J2383/06

  containing silicon bound to oxygen-containing groups (C08J2383/12 takes precedence) · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title