Siloxanes and Silanes Cured by Organoborane Amine Complexes

• US 20070298223A1
• Filed: 12/13/2005
• Published: 12/27/2007
• Est. Priority Date: 01/04/2005
• Status: Active Grant

• Current Assignee: Dow Silicones Corporation (Dow, Inc.)
• Original Assignee: Dow, Inc.
• Inventors: Ahn, Dongchan, Olney, Patricia, Tonge, James, Shephard, Nick, Loch, Cheryl
• Granted Patent: US 7,732,543 B2
• Time in Patent Office: Days
• US Class Current: 428/172
• CPC Class Codes: C08K 5/55 Boron-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence
• CPC Class Codes: Y10T 428/24612 Composite web or sheet

Abstract

Curable compositions contain (i) a free radical polymerizable organosilicon monomer, oligomer or polymer; (ii) an organoborane amine complex; optionally (iii) an amine reactive compound having amine reactive groups; and optionally (iv) a component capable of generating a gas when mixed with a compound bearing active hydrogen and a catalyst. The curable compositions can be used as a rubber, tape, adhesive, foam, pressure sensitive adhesive, protective coating, thin film, thermoplastic monolithic molded part, thermosetting monolithic molded part, sealant, gasket, seal, or o-ring, die attachment adhesive, lid sealant, encapsulant, potting compound, or conformal coating. The compositions can also be used in composite articles of manufacture such as integrally bonded device including electrical and electronic connectors and scuba diving masks, in which substrates are coated or bonded together with the composition and cured.

Claims

1. A composition comprising (i) a free radical polymerizable organosilicon monomer, oligomer or polymer;

(ii) an organoborane amine complex; and

optionally (iii) an amine reactive compound;

the composition being free of any free radical polymerizable monomer, oligomer, or polymer, that does not contain one or more silicon atoms.

2. A composition according to claim 1 wherein the free radical polymerizable organosilicon monomer, oligomer, or polymer is (a) an organosilicon monomer, oligomer, or polymer or (b) a mixture of monofunctional or multifunctional organosilanes, or monofunctional or multifunctional organopolysiloxanes, in which (a) and (b) are unsaturated and capable of undergoing free radical polymerization.

3. A composition according to claim 1 wherein the organoborane amine complex (ii) is a complex formed between an organoborane and an amine compound, the organoborane having the formula B—

R′

₃ where R″

is a linear, branched, aliphatic, or aromatic hydrocarbon group containing 1-20 carbon atoms; and

wherein the amine compound is an organic amine compound or a silicon containing amine compound.

4. A composition according to claim 1 wherein the organoborane amine complex is attached to solid particles.

5. A composition according to claim 1 wherein the amine reactive compound is a compound having amine reactive groups and is selected from the group consisting of mineral acids, Lewis acids, carboxylic acids, carboxylic acid derivatives, carboxylic acid metal salts, isocyanates, aldehydes, epoxides, acid chlorides, and sulphonyl chlorides.

6. A composition according to claim 5 wherein the amine reactive groups are borne by an organosilane, an organopolysiloxane, an organotitanate, or an organozirconate.

7. A composition according to claim 5 wherein the amine reactive compound is attached to solid particles.

8. A composition according to claim 1 wherein the amine reactive compound is a compound

capable of generating amine reactive groups when exposed to ultraviolet radiation.

9. A composition according to claim 8 wherein the composition further comprises a photosensitizing compound.

10. A composition according to claim 1 further comprising (iv) a component capable of generating a gas when mixed with a compound bearing active hydrogen and a catalyst, the component (iv) being a silicon hydride functional compound;

the compound bearing active hydrogen being water, an alcohol, or a carboxylic acid; and

the catalyst being platinum, a platinum group metal, tin, titanium, or zirconium.

11. A composition according to claim 1 wherein the organoborane amine complex is packaged separately from the amine reactive compound.

12. A composition according to claim 1 wherein the free radical polymerizable organosilicon monomer, oligomer or polymer, the organoborane amine complex, and the amine reactive compound are packaged together in one part in a substantially oxygen free environment.

13. A composition according to claim 1 wherein the free radical polymerizable organosilicon monomer, oligomer or polymer and the organoborane amine complex are packaged together in one part.

14. A composite article of manufacture comprising a substrate coated with the composition according to claim 1.

15. A composite article of manufacture according to claim 14 wherein the composition on the substrate is cured.

16. A composite article of manufacture comprising two or more substrates coated with the composition according to claim 1, and the composition is disposed between the substrates as a bond line of a fixed or a varying thickness.

17. A composite article of manufacture according to claim 16 wherein the composition disposed between the substrates is cured.

18. A rubber, tape, adhesive, foam, pressure sensitive adhesive, protective coating, thin film, electronic component, photonic component, acoustic dampening component, thermoplastic monolithic molded part, thermosetting monolithic molded part, sealant, gasket, seal, o-ring, or connector, comprising the cured product of the composition according to claim 1.

19. A rubber, tape, adhesive, foam, pressure sensitive adhesive, protective coating, thin film, electronic component, photonic component, acoustic dampening component, thermoplastic monolithic molded part, thermosetting monolithic molded part, sealant, gasket, seal, o-ring, or connector according to claim 18, comprising a silicone rubber, silicone tape, silicone adhesive, silicone foam, silicone pressure sensitive adhesive, silicone protective coating, silicone thin film, silicone electronic component, silicone photonic component, silicone acoustic dampening component, silicone thermoplastic monolithic molded part, silicone thermosetting monolithic molded part, silicone sealant, silicone gasket, silicone seal, silicone o-ring, or silicone connector.

20. A method of curing the composition according to claim 1 comprising applying the composition to a substrate, between multiple substrates, or to a mold;

and exposing the composition to the amine reactive compound in the gas phase.

21. A method according to claim 20 wherein the amine reactive compound is a compound

capable of generating amine reactive groups when exposed to ultraviolet radiation.

22. A method according to claim 20 wherein the composition further comprises a photosensitizing compound.