Organosilicon Functional Boron Amine Catalyst Complexes and Curable Compositions Made Therefrom

• US 20080050552A1
• Filed: 12/13/2005
• Published: 02/28/2008
• Est. Priority Date: 01/04/2005
• Status: Active Grant

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Ahn, Dongchan, Mustafa, Mohamed, Olney, Patricia
• Granted Patent: US 7,928,174 B2
• Time in Patent Office: Days
• US Class Current: 428/98
• CPC Class Codes: C08F 4/00 Polymerisation catalysts
• CPC Class Codes: Y10T 428/24 Structurally defined web or sheet [e.g., overall dimension, etc.]
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer
• CPC Class Codes: Y10T 428/2878 including addition polymer from unsaturated monomer
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers

Abstract

Organosilicon functional boron amine catalyst complexes have an organosilicon functional organoborane portion of the complex that contains at least one silicon atom. The complexes can be used as components in curable compositions containing (i) a free radical polymerizable monomer, oligomer or polymer; (ii) the organosilicon functional boron amine catalyst complex; and (iii) an amine reactive compound having amine reactive groups. The curable compositions may contain a component capable of generating a gas, as well as various other optional ingredients. These curable compositions can be used as rubbers, tapes, adhesives, protective coatings, thin films, thermoplastic monolithic molded parts, thermosetting monolithic molded parts, sealants, foams, gaskets, seals, o-rings, pressure sensitive adhesives, die attachment adhesives, lid sealants, encapsulants, potting compounds, conformal coatings, and electronic components. The compositions can also be used in composite articles of manufacture in which substrates are coated or bonded together with the composition and cured, such as in connectors, diving masks, or other integrally bonded parts.

Claims

1. An organosilicon functional boron amine catalyst complex comprising a complex having an organosilicon functional organoborane portion containing at least one silicon atom, the silicon atom being present in the organosilicon functional organoborane portion of the complex as a silicon atom containing group, a siloxane oligomer containing group, or as a siloxane polymer containing group.

2. An organosilicon functional boron amine catalyst complex according to claim 1 in which the complex comprises a compound having the formula:

wherein B represents boron;

R6, R7, and R8 are groups independently selected from the group consisting of hydrogen;

a cycloalkyl group;

a linear or branched alkyl group having 1-12 carbon atoms on the backbone;

an alkylaryl group;

an organosilane group;

an organosiloxane group;

an alkylene group capable of functioning as a covalent bridge to a boron atom;

a divalent organosiloxane group capable of functioning as a covalent bridge to a boron atom; and

halogen substituted homologues thereof;

with the provisos that at least one of the R6, R7, or R8 groups contains one or more silicon atoms, and the silicon-containing group is covalently bonded to boron;

R9, R10, and R11 are a group that yields an amine compound or a polyamine compound capable of complexing boron; and

wherein two or more of the R6, R7, or R8 groups, and two or more of the R9, R10, or R11 groups, are such that they can combine to form heterocyclic structures, provided the sum of the number of atoms from the two combining groups does not exceed 11.

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

(ii) an organosilicon functional boron amine catalyst complex having an organosilicon functional organoborane portion containing at least one silicon atom, the silicon atom being present in the organosilicon functional organoborane portion of the complex as a silicon atom containing group, a siloxane oligomer containing group, or as a siloxane polymer containing group; and

optionally, (iii) an amine reactive compound having amine reactive groups.

4. A composition according to claim 3 wherein the free radical polymerizable monomer, oligomer, or polymer (i) is an organic compound (a);

a mixture of mono-functional or multi-functional organic compounds (b);

an organosilicon monomer, oligomer, or polymer (c);

a mixture of mono-functional or multi-functional organosilanes (d);

a mixture of mono-functional or multi-functional organopolysiloxanes (e);

or a mixture of (a)-(e);

in which (a)-(e) are unsaturated and capable of undergoing free radical polymerization.

5. A composition according to claim 3 in which the complex comprises a compound having the formula:

wherein B represents boron;

R6, R7, and R8 are groups independently selected from the group consisting of hydrogen;

a cycloalkyl group;

a linear or branched alkyl group having 1-12 carbon atoms on the backbone;

an alkylaryl group;

an organosilane group;

an organosiloxane group;

an alkylene group capable of functioning as a covalent bridge to a boron atom;

a divalent organosiloxane group capable of functioning as a covalent bridge to a boron atom; and

halogen substituted homologues thereof;

with the provisos that at least one of the R6, R7, or R8 groups contains one or more silicon atoms, and the silicon-containing group is covalently bonded to boron;

R9, R10, and R11 are a group that yields an amine compound or a polyamine compound capable of complexing boron; and

wherein two or more of the R6, R7, or R8 groups, and two or more of the R9, R10, or R11 groups, are such that they can combine to form heterocyclic structures, provided the sum of the number of atoms from the two combining groups does not exceed 11.

6. A composition according to claim 5 in which the complex is attached to solid particles.

7. A composition according to claim 3 wherein the amine reactive compound having amine reactive groups (iii) 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.

8. A composition according to claim 7 wherein the amine reactive groups are borne by an organosilane, an organopolysiloxane, an organotitanate, or an organozirconate.

9. A composition according to claim 7 wherein the amine reactive compound (iii) is attached to solid particles.

10. A composition according to claim 3 further comprising a component capable of generating a gas (iv) when mixed with a compound bearing active hydrogen and a catalyst, the component capable of generating a gas 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 3 wherein the organosilicon functional boron amine catalyst complex (ii) is packaged separately from the amine reactive compound (iii).

12. A composition according to claim 3 wherein the free radical polymerizable monomer, oligomer or polymer (i), the organosilicon functional boron amine catalyst complex (ii), and the amine reactive compound (iii) are packaged together in one part in a substantially oxygen free environment.

13. A composite article of manufacture comprising a substrate coated with the composition according to claim 3.

14. A composite article of manufacture according to claim 13 wherein the composition on the substrate is cured.

15. A composite article of manufacture comprising two or more substrates coated with the composition according to claim 3, and the composition is disposed between the substrates as a bond line of a fixed or a varying thickness.

16. A composite article of manufacture according to claim 15 wherein the composition disposed between the substrates is cured.

17. An article of manufacture comprising a rubber, tape, adhesive, protective coating, thin film, electronic component, photonic component, acoustic dampening components, thermoplastic monolithic molded part, thermosetting monolithic molded part, sealant, foam, gasket, seal, o-ring, connector, or pressure sensitive adhesive wherein a component thereof is the cured product of the composition according to claim 3.

18. An article of manufacture according to claim 17 in which the cured product of the composition has properties ranging from a compliant gel to a rigid resin.

19. An article of manufacture according to claim 18 in which the cured product is a self-adherent silicone elastomer or a self-adherent silicone gel.

20. An article of manufacture according to claim 19 in which the cured product is a die attachment adhesive, a lid sealant, an encapsulant, a potting compound, a conformal coating, or an electronic component bonded to a flexible or rigid substrate.

21. A method of curing the composition according to claim 3 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.

22. A method according to claim 21 wherein the amine reactive compound is a compound capable of generating amine reactive groups when exposed to ultraviolet radiation.

23. A method according to claim 21 wherein the composition further comprises a photosensitizing compound.