Compositions of silylated polymer and aminosilane adhesion promoters

• US 6,310,170 B1
• Filed: 08/17/1999
• Issued: 10/30/2001
• Est. Priority Date: 08/17/1999
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: Ck Witco Corporation (Lanxess AG)
• Inventors: Lehmann, Patrice, Johnston, Robert R.
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): Zimmer, Marc S.
• Application Number:
  US09/376,123
• Time in Patent Office: 805 Days
• Field of Search: 556/413, 528/18, 528/34, 528/901, 528/38, 526/279
• US Class Current: 528/38
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C09J 175/04 Polyurethanes
• CPC Class Codes: C09K 2200/0239 Oxides, hydroxides, carbonates
• CPC Class Codes: C09K 2200/0247 Silica
• CPC Class Codes: C09K 2200/0441 Carboxylic acids, salts, anhydrides or esters thereof
• CPC Class Codes: C09K 3/1021 Polyurethanes or derivatives thereof
• CPC Class Codes: Y10S 528/901 Room temperature curable silicon-containing polymer

Abstract

Compositions comprising a silylated polymer and an adhesion promoter, the silylated polymer having an inorganic or organic backbone and at least two groups thereon selected from alkoxysilyl, aryloxysilyl, alkyloximinosilyl and silanol groups and the adhesion promoter being a silane adhesion promoter of the formula:

R¹ is a branched or cyclic alkylene group, an arylene group or an alkarylene group, any of which may be optionally interrupted by one or more ether oxygen atoms or a (poly)sulfide bridge, provided that R¹ has at least 4 carbon atoms; R² is an alkyl, aryl or alkaryl radical having 1 to 6 carbons; R³ is a C₁ to C₆ alkoxy group or a C₃ to C₅ ketoximato group; R⁴ is hydrogen, a hydrocarbon group, which may optionally be substituted, or a group which will thermally deblock to form an amine group containing the nitrogen atom to which it is attached; and z is 0 or 1.

Claims

1. A composition comprising:

a) a silylated polymer selected from the group consisting of silylated acrylics, silylated polyurethanes, silylated polyethers, silylated polyesters, silylated polyolefins and mixtures thereof, said silylated polymer having terminal or pendant hydrolyzable alkoxysilyl, aryloxysilyl or alkyloximinosilyl groups thereon; and

b) a silane adhesion promoter of the formula;

where R¹ is a branched or cyclic alkylene group, an arylene group or an alkarylene group, any of which may be optionally interrupted by one or more ether oxygen atoms or a (poly)sulfide bridge, provided that R¹ has at least 4 carbon atoms;

R² is an alkyl, aryl or alkaryl radical having 1 to 6 carbons;

R³ is a C₃ to C₆ alkoxy group or a C₁ to C₅ ketoximato group;

R⁴ is hydrogen, a hydrocarbon group, which may optionally be substituted, or a group which will thermally deblock to form an amine group containing the nitrogen atom to which it is attached; and

z is 0 or 1.

2. A composition as in claim 1 wherein R¹ is selected from the group consisting of 1,3-butylene;

1,2-butylene;

2,2-dimethyl-1,3-propylene;

3-methylbutylene;

3,3-dimethylbutylene;

2-ethylhexylene;

1,4-diethylenephenylene;

3-phenyl-1,3-propylene;

1,4-cyclohexylene;

1,4-diethylenecyclohexylene;

1,2-phenylene;

1,3-phenylene;

1,4-phenylene;

2-methyl-1,4-phenylene;

groups of the formula;

3. A composition as in claim 1 wherein R¹ is a branched alkylene group of 4-8 carbon atoms.

4. A composition as in claim 1 wherein R² is methyl, ethyl, propyl, isopropyl, butyl, hexyl, phenyl, cyclohexyl, or tolyl.

5. A composition as in claim 1 wherein R³ is methoxy, ethoxy, isopropoxy, n-propoxy, phenoxy, 2-phenylethoxy, dimethylketoximo, methyl ethyl ketoximo or diethylketoximo.

6. A composition as in claim 1 wherein R⁴ is hydrogen, methyl, ethyl, 2-hydroxyethyl, 2-aminoethyl, propyl, 3-hydroxypropyl, 3-aminopropyl, butyl, cyclohexyl, phenyl, methylphenyl, 2-cyanoethyl, isopropoxyethyl, R²—

C(═

O)—

or R²O—

C(═

O)—

).

7. A composition as in claim 1 wherein R¹ is a branched alkylene group, R³ is methoxy, R⁴ is H, methyl or ethyl, and either R² is a methyl group or z is 0.

8. A composition as in claim 1 further comprising a silane condensation cure catalyst.

9. A composition as in claim 1 wherein said silylated polymer has an organic backbone.

10. A composition as in claim 1 wherein the silylated polyurethane is a reaction product of an isocyanate terminated prepolymer and a silane of the formula

11. A composition as in claim 1 wherein the silylated polyurethane is a reaction product of a prepolymer terminated with an active hydrogen group and a silane of the formula:

12. A composition as in claim 1 wherein the adhesion promoter is selected from the group consisting of 4-amino-3,3-dimethylbutyltrimethoxysilane, 4-amino-3,3-dimethylbutyldimethoxymethylsilane, N-methyl-4-amino-3,3-dimethylbutyltrimethoxysilane, aminoisopropoxyethyltrimethoxysilane, aminoisopropoxypropyltrimethoxysilane, 4-amino-3,3-dimethylbutyltriethoxysilane, 4-amino-3,3-dimethylbutyldiethoxymethylsilane, N-methyl-4-amino-3,3-dimethylbutyltriethoxysilane, aminoisopropoxyethyltriethoxysilane, and mixtures thereof.

13. A composition as in claim 1 further comprising at least one of a silane condensation cure catalyst, a crosslinker, a filler, a plasticizer, a thixotrope, an antioxidant, a UV stabilizer, and a dehydrating agent.

14. A composition as in claim 1 wherein said silylated polymer has a polyorganosiloxane backbone.

15. A composition as in claim 1 wherein said silylated polymer has a plurality of alkoxysilyl groups thereon.

17. A composition as in claim 1 wherein R⁴ is hydrogen or a hydrocarbon group, which may be optionally substituted.

18. A composition as in claim 1 wherein R⁴ is a group which will thermally deblock to form an amine group containing the nitrogen atom to which it is attached.

16. A composition prepared by mixing a silylated polymer and an adhesion promoter, the silylated polymer being selected from the group consisting of silylated acrylics, silylated polyurethanes, silylated polyethers, silylated polyesters, silylated polyolefins and mixtures thereof and having at least two groups thereon selected from alkoxysilyl, aryloxysilyl, alkyloximinosilyl and silanol groups and the adhesion promoter being a silane adhesion promoter of the formula:

wherein;

R¹ is a branched or cyclic alkylene group, an arylene group or an alkarylene group, any of which may be optionally interrupted by one or more ether oxygen atoms or a (poly)sulfide bridge, provided that R¹ has at least 4 carbon atoms;

R² is an alkyl, aryl or alkaryl radical having 1 to 6 carbons;

R³ is a C₁ to C₆ alkoxy group or a C₃ to C₅ ketoximato group;

R₄ is hydrogen, a hydrocarbon group, which may optionally be substituted, or a group which will thermally deblock to form an amine group containing the nitrogen atom to which it is attached; and

z is 0 or 1.