Composition having improved adherence with an addition-curable material and composite article incorporating the composition

• US 7,858,197 B2
• Filed: 01/21/2005
• Issued: 12/28/2010
• Est. Priority Date: 01/22/2004
• Status: Expired due to Fees

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Shepard, Nick Evan, Warakomski, John Matthew, Nichols, Kevin Louis, Ahn, Dongchan, Fowler, Harold Christian
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LOEWE, ROBERT S
• Application Number:
  US10/585,844
• Publication Number:
  US 20080177000A1
• Time in Patent Office: 2,167 Days
• Field of Search: 525/102
• US Class Current: 428/447
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 23/10 Homopolymers or copolymers of propene
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 2666/34 Oxygen-containing compounds, including ammonium and metal salts
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 69/00 Compositions of polycarbonates; Compositions of derivatives of polycarbonates
• 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 83/04 Polysiloxanes
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

A composition and composite article have improved adherence with an addition-curable material. The composition and therefore the composite article, which includes at least one substrate formed from the composition, include a resin and an additive that is incorporated into the resin. The resin is organic and polymeric and free of ethylenically unsaturated and silicon hydride functional groups. The additive is selected from the group of a fluorine-substituted organopolysiloxane, an amino-functional organopolysiloxane, an unsaturated carboxylic acid or carboxylic acid salt, and combinations thereof. Further, the additive includes a hydrosilylation reactive group present at a surface of the substrate for reaction with the addition-curable material. This improves adherence of the substrate with the addition-curable material. The substrate and the addition-curable material bond together to make the composition article.

Claims

1. A composition having improved adherence with an addition-curable material, said composition comprising:

a resin component that is organic and polymeric and free of ethylenically unsaturated and silicon hydride functional groups; and

an additive incorporated into said resin component and comprising a fluorine-substituted organopolysiloxane, wherein said additive comprises a hydrosilylation reactive group for reaction with the addition-curable material and wherein said fluorine-substituted organopolysiloxane is copolymerized with an organic block selected from the group of polyamide blocks, polyester blocks, polyolefin blocks, fluorine-substituted organic polymer blocks, polyurea blocks, poly(phenylene ether) blocks, syndiotactic polystyrene blocks, and combinations thereof.

2. A composition as set forth in claim 1 wherein said hydrosilylation reactive group of said additive comprises an ethylenically unsaturated functional group for reaction with the addition-curable material.

3. A composition as set forth in claim 1 wherein said fluorine-substituted organopolysiloxane comprises a copolymer of organosiloxanes.

4. A composition as set forth in claim 1 wherein said fluorine-substituted organopolysiloxane includes fluorinated hydrocarbon groups selected from the group of 3,3,3-trifluoropropyl;

6,6,6,5,5,4,4,3,3-nonafluorohexyl; and

combinations thereof.

5. A composition as set forth in claim 1 wherein said fluorine-substituted organopolysiloxane comprises dimethylvinylsiloxy-terminated methyl 3,3,3-trifluoropropyl siloxane.

6. A composition as set forth in claim 1 wherein said hydrosilylation reactive group of said additive comprises a silicon hydride functional group for reaction with the addition-curable material.

7. A composition as set forth in claim 6 wherein said fluorine-substituted organopolysiloxane comprises a fluorine-substituted organohydrogenpolysiloxane.

8. A composition as set forth in claim 7 wherein said fluorine-substituted organohydrogenpolysiloxane comprises a copolymer of organohydrogenpolysiloxanes and organopolysiloxanes.

9. A composition as set forth in claim 7 wherein said fluorine-substituted organohydrogenpolysiloxane includes fluorinated hydrocarbon groups selected from the group of 3,3,3-trifluoropropyl;

6,6,6,5,5,4,4,3,3-nonafluorohexyl; and

combinations thereof.

10. A composition as set forth in claim 7 wherein said fluorine-substituted organohydrogenpolysiloxane comprises trimethylsiloxy-terminated poly (methylhydrogensiloxane/methyl-6,6,6,5,5,4,4,3,3-nonafluorohexylsiloxane).

11. A composition as set forth in claim 1 further comprising a compatibilizing agent for compatibilizing said resin component and said additive, wherein said compatibilizing agent comprises an organic segment compounded with said additive.

12. A composition as set forth in claim 1 further comprising a catalyst selected from the group of hydrosilylation catalysts, activators for free radical initiators, and combinations thereof.

13. A composition as set forth in claim 1 wherein said additive is present in an amount of from 0.001 to 30 parts by weight based on 100 parts by weight of said resin component.

14. A composition as set forth in claim 1 wherein said resin component is further defined as a polymer derived from a monomer or monomers selected from the group of styrene, substituted styrenes, diamines, diacids, lactams, diols, olefin, substituted olefin, dienes, diisocyanate, epoxide, phenol, substituted phenols, ketones, substituted ketones, aldehydes, substituted aldehydes, acrylates, methacrylates, acrylic acid, fumaric acid, maleic acid, maleic anhydride, carbon dioxide, and combinations thereof.

15. A composition as set forth in claim 1 wherein said resin component is further defined as a polymer selected from the group of polystyrenes, polyamides, polycarbonates, polyolefins, styrene acrylonitriles, acrylonitrile-butadiene-styrenes, polyesters, polyurethanes, epoxies, polyphenylene oxides, halogen-substituted organic polymers, polyphthalamides, polyphenylene sulfides, liquid crystalline polymer, polycyclohexaneterephthalates, and combinations thereof.

16. A composition as set forth in claim 1 wherein said resin component is selected from the group of atactic polystyrene, isotactic polystyrene, syndiotactic polystyrene, nylon 6, nylon 6,6, polyethylene terephthalate, polybutylene terephthalate, polyethylene, polypropylene, polytetrafluoroethylene, cyanate esters, bismaleimide triazine, and combinations thereof.

17. A composite article comprising:

at least one substrate formed from a composition having improved adherence with an addition-curable material and comprising;

a resin component that is organic and polymeric and free of ethylenically unsaturated and silicon hydride functional groups, and

an additive incorporated into said resin component and selected from the group of a fluorine-substituted organopolysiloxane, an amino-functional organopolysiloxane, an unsaturated carboxylic acid or carboxylic acid salt, and combinations thereof, wherein said additive comprises a hydrosilylation reactive group for reaction with the addition-curable material; and

said addition-curable material is disposed on said at least one substrate.

18. A composite article as set forth in claim 17 wherein said additive comprises said amino-functional organopolysiloxane.

19. A composite article as set forth in claim 18 wherein said amino-functional organopolysiloxane comprises a copolymer of organosiloxanes.

20. A composite article composition as set forth in claim 18 wherein said amino-functional organopolysiloxane is copolymerized with an organic block selected from the group of polyamide blocks, polyester blocks, polyolefin blocks, fluorine-substituted organic polymer blocks, polyurea blocks, poly(phenylene ether) blocks, syndiotactic polystyrene blocks, and combinations thereof.

21. A composite article as set forth in claim 18 wherein said amino-functional organopolysiloxane comprises an amine-terminated random copolymer of dimethylsiloxane and methylvinylsiloxane.

22. A composite article as set forth in claim 17 wherein said additive comprises said unsaturated carboxylic acid or carboxylic acid salt.

23. A composite article as set forth in claim 22 wherein said unsaturated carboxylic acid or carboxylic acid salt is copolymerized or grafted with an unsaturated organic block selected from the group of polyamide blocks, polyester blocks, polysiloxane blocks, polyolefin blocks, fluorine-substituted organic polymer blocks, polyurea blocks, poly(phenylene ether) blocks, syndiotactic polystyrene blocks, and combinations thereof.

24. A composite article as set forth in claim 22 wherein said unsaturated carboxylic acid or carboxylic acid salt is selected from the group of 10-undecenoic acid, zinc undecylenate, sodium undecylenate, magnesium undecylenate, calcium undecylenate, lithium undecylenate, potassium undecylenate, lead undecylenate, functionalized stearates having unsaturation at the first carbon atom in the chain, functionalized montanates having unsaturation at the first carbon atom in the chain, and combinations thereof.

25. A composite article as set forth in claim 17 wherein said addition-curable material comprises a hydrosilylation-curable material.

26. A composite article as set forth in claim 17 wherein said additive comprises said fluorine-substituted organopolysiloxane.

27. A composite article as set forth in claim 26 wherein said fluorine-substituted organopolysiloxane comprises a copolymer of organosiloxanes.

28. A composite article as set forth in claim 26 wherein said fluorine-substituted organopolysiloxane is copolymerized with an organic block selected from the group of polyamide blocks, polyester blocks, polyolefin blocks, fluorine-substituted organic polymer blocks, polyurea blocks, poly(phenylene ether) blocks, syndiotactic polystyrene blocks, and combinations thereof.

29. A composite article as set forth in claim 26 wherein said fluorine-substituted organopolysiloxane includes fluorinated hydrocarbon groups selected from the group of 3,3,3-trifluoropropyl;

6,6,6,5,5,4,4,3,3-nonafluorohexyl; and

combinations thereof.

30. A composite article as set forth in claim 26 wherein said fluorine-substituted organopolysiloxane comprises dimethylvinylsiloxy-terminated methyl 3,3,3-trifluoropropyl siloxane.

31. A composite article as set forth in claim 26 wherein said fluorine-substituted organopolysiloxane comprises a fluorine-substituted organohydrogenpolysiloxane.

32. A composite article as set forth in claim 31 wherein said fluorine-substituted organohydrogenpolysiloxane comprises a copolymer of organohydrogenpolysiloxanes and organopolysiloxanes.

33. A composite article as set forth in claim 31 wherein said fluorine-substituted organohydrogenpolysiloxane includes fluorinated hydrocarbon groups selected from the group of 3,3,3-trifluoropropyl;

6,6,6,5,5,4,4,3,3-nonafluorohexyl; and

combinations thereof.

34. A composite article as set forth in claim 31 wherein said fluorine-substituted organohydrogenpolysiloxane comprises trimethylsiloxy-terminated poly (methylhydrogensiloxane/methyl-6,6,6,5,5,4,4,3,3-nonafluorohexylsiloxane).