Fast moisture curing and uv-moisture dual curing compositions

• US 20050267276A1
• Filed: 10/15/2003
• Published: 12/01/2005
• Est. Priority Date: 10/23/2002
• Status: Active Grant

• Current Assignee: Henkel AG & Co KGaA
• Original Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Inventors: Chu, Hsien-Kun
• Granted Patent: US 7,368,519 B2
• Time in Patent Office: Days
• US Class Current: 528/34
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/16 to hydroxyl groups
• CPC Class Codes: C08G 77/18 to alkoxy or aryloxy groups
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08K 5/0025 Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08K 5/0091 Complexes with metal-heteroatom-bonds
• CPC Class Codes: C08K 5/07 Aldehydes; Ketones
• CPC Class Codes: C08K 5/31 Guanidine; Derivatives thereof
• CPC Class Codes: C08K 5/541 containing oxygen
• CPC Class Codes: C08K 5/5425 containing at least one C=C bond
• CPC Class Codes: C08L 101/10 containing hydrolysable silane groups
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

The invention provides fast moisture and photo/moisture curing silicone ions and methods for the preparation thereof. More particularly, the compositions are prepared from silanol and silane cappers; the cappers have an α-carbon bonded to the silicon atom allowing for a favorable hypervalent silicon transition state when reacting the silane and silanol. This favorable transition state enables both a fast endcapping reaction and contributes to the fast moisture curing properties of the inventive compositions.

Claims

1. A composition comprising:

a) a compound having the structural formula;

wherein

R is a C_1-20 alkyl which may be substituted or unsubstituted or an unsaturated free radical-curing group;

R¹ is hydrogen or a C_1-6 hydrocarbon radical;

R² is a hydrolyzable group;

X is oxygen,

R³ is H or C_1-12 hydrocarbyl group; and

b) a polymer having the structure formula;

wherein A is a backbone selected from the group consisting of organic and siloxane backbones, and R^e is CH₃ or H.

2. The composition according to claim 1, wherein said curable composition is a dual cure photo/moisture curable composition.

3. The composition according to claim 2 wherein R is alkenyl, which may be substituted or unsubstituted.

4. The composition according to claim 1, wherein said curable composition is a moisture curable composition.

5. The composition according to claim 4 wherein R is a C_1-20 alkyl which may be substituted or unsubstituted.

6. The composition according to claim 4 wherein R is a methyl group.

7. The composition according to claim 1, wherein X is O.

8. The composition according to claim 1 wherein R² is an alkoxy group having the formula R⁴O—

wherein R⁴ is a C_1-2 alkyl group.

9. The composition according to claim 1 wherein R is

10. The composition according to claim 1, wherein R is CH₃, X is O, R² is OR⁴, R⁴ is a C_1-2 alkyl group R¹ is hydrogen or a C_1-6 hydrocarbyl radical.

11. The composition of claim 1, further comprising a cure system.

12. The composition of claim 11, where the cure system includes a catalyst selected from the group consisting of tetraisopropyltitanate, dibutyltin dilaurate and tetramethylguanidine.

13. The composition of claim 12 wherein the cure system further includes a photoinitiator selected from the group consisting of 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino propan-1-one, 2-benzyl-2-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone, the combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone, 2,2-dimethoxy-2-phenyl acetophenone, the combination of bis(2,6-dimethoxybenzoyl-2,4,4-trimethyl pentyl) phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and [bis (2,4,6-trimethyl benzoyl) phenyl phosphine oxide], 2-hydroxy-2-methyl-1-phenyl-1-propan-1-one, the combination of 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one, dl-camphorquinone, alkyl pyruvates, 2,2-dimethoxy-2-phenyl acetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propane, bis(2,4,6-trimethyl benzoyl) phenyl phosphine oxide, bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl) phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(n⁵-2,4-cyclopentadien-1-yl)-bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl]titanium, diethoxyacetophenone and combinations thereof.

14. The composition of claim 1 wherein A is a siloxane.

15. The composition of claim 1 wherein formula I and formula II are present in amounts such that the resulting ratio of said hydrolyzable groups of formula I to said OH groups of formula II is 1.2.

16. A curable composition comprising the reaction product of

a) a compound having the structural formula:

wherein

R is a C_1-20 alkyl which may be substituted or unsubstituted or an unsaturated free radical-curing group;

R¹ is hydrogen or a C_1-6 hydrocarbyl radical;

R² is a hydrolyzable group;

X is oxygen,

 

R³ is H or C_1-12 hydrocarbyl group; and

b) a polymer having the structure formula;

wherein A is a backbone selected from the group consisting of organic and siloxane backbones, and R^e is CH₃ or H.

17. The curable composition of claim 16 wherein said reaction product has a skin over time of about 15 minutes or less.

18. The curable composition of claim 17 wherein said skin over time is about 5 minutes or less.

19. A method of preparing a curable composition comprising the step of combining:

a) a compound having the structural formula;

wherein

R is a C_1-20 alkyl which may be substituted or unsubstituted or an unsaturated free radical-curing group;

R¹ is hydrogen or a C_1-6 hydrocarbon radical;

R² is a hydrolyzable group;

X is oxygen,

 

R³ is H or C_1-12 hydrocarbyl group; and

b) a polymer having the structure formula;

wherein A is a backbone selected from the group consisting of organic and siloxane backbones, and R^e is CH₃ or H.

20. The method of claim 19, further including the step of incorporating a curing system.