Claims
- 1. A method for bonding a fibrous substrate surface to a second substrate surface comprising:
(a) providing a catalyst at the fibrous substrate surface; (b) contacting the catalyst on the fibrous substrate surface with a metathesizable material so that the metathesizable material undergoes a metathesis reaction; and (c) contacting the fibrous substrate surface with a second substrate surface.
- 2. A method according to claim 1 wherein the fibrous substrate comprises polyester, nylon or polyamide.
- 3. A method according to claim 2 wherein the second substrate surface comprises an elastomeric substrate.
- 4. A method according to claim 3 wherein the elastomeric substrate is selected from the group consisting of natural rubber, polychloroprene, polybutadiene, polyisoprene, styrene-butadiene copolymer rubber, acrylonitrile-butadiene copolymer rubber, ethylene-propylene copolymer rubber, ethylene-propylene-diene terpolymer rubber, butyl rubber, brominated butyl rubber, alkylated chlorosulfonated polyethylene rubber, hydrogenated nitrile rubber, poly(n-butyl acrylate), thermoplastic elastomer and mixtures thereof.
- 5. A method according to claim 3 wherein the elastomeric substrate is natural rubber or ethylene-propylene-diene terpolymer rubber.
- 6. A method according to claim 1 wherein step (a) comprises soaking the fibrous substrate in a catalyst solution and step (b) comprises dipping the catalyst-soaked fibrous substrate into a metathesizable material and allowing polymerization.
- 7. A method according to claim 1 wherein step (c) comprises placing the fibrous substrate between two layers of second substrate surface in a mold and curing the second substrate surface with heat and pressure.
- 8. A method according to claim 1 wherein the catalyst is dissolved or mixed into a liquid carrier fluid.
- 9. A method according to claim 1 wherein the catalyst is included as a component of the first fibrous substrate.
- 10. A method according to claim 1 wherein the catalyst is selected from at least one of a rhenium compound, ruthenium compound, osmium compound, molybdenum compound, tungsten compound, titanium compound, niobium compound, iridium compound and MgCl2.
- 11. A method according to claim 10 wherein the catalyst has a structure represented by
- 12. A method according to claim 11 wherein X is Cl, Br, I, F, CN, SCN, N3, O-alkyl or O-aryl; L is a heterocyclic ring or Q(R2)a wherein Q is P, As, Sb or N; R2 is H, cycloalkyl, alkyl, aryl, alkoxy, arylate, amino, alkylamino, arylamino, amido or a heterocyclic ring; and a is 1, 2 or 3; M is Ru; and R2 is H, phenyl, —CH═C(phenyl)2, —CH═C(CH3)2 or —C(CH3)2(phenyl).
- 13. A method according to claim 10 wherein the catalyst is a phosphine-substituted, an imidazolylidene-substituted, or a dihydroimidazolylidene-substituted ruthenium carbene.
- 14. A method according to claim 13 wherein the catalyst is
- 15. A method according to claim 1 wherein the catalyst is stable in the presence of moisture and oxygen and can initiate polymerization of the metathesizable material upon contact at room temperature.
- 16. A method according to claim 1 wherein the metathesizable material is selected from ethene, α-alkene, acyclic alkene, acyclic diene, acetylene, cyclic alkene, cyclic polyene and mixtures thereof.
- 17. A method according to claim 16 wherein the metathesizable material comprises a cycloolefin.
- 18. A method according to claim 17 wherein the metathesizable material is a monomer or oligomer selected from norbornene, cycloalkene, cycloalkadiene, cycloalkatriene, cycloalkatetraene, aromatic-containing cycloolefin and mixtures thereof.
- 19. A method according to claim 18 wherein the metathesizable material has a structure represented by
- 20. A method according to claim 17 wherein the metathesizable material comprises ethylidenenorbornene monomer or oligomer, dicyclopentadiene or bicyclo[2.2. 1 ]hept-5-en-2-yl-trichlorosilane.
- 21. A method for bonding a fibrous substrate to an elastomeric substrate comprising:
(a) applying a catalyst on the fibrous substrate; (b) contacting the catalyst on the fibrous substrate with a metathesizable material so that the metathesizable material undergoes a metathesis reaction; (c) contacting the fibrous substrate with the elastomeric substrate to form a composite material; and (d) curing said composite material.
- 22. A method according to claim 21 wherein the catalyst has a structure represented by
- 23. A method according to claim 22 wherein X is Cl, Br, I, F, CN, SCN, N3, O-alkyl or O-aryl; L is a heterocyclic ring or Q(R2)a wherein Q is P, As, Sb or N; R2 is H, cycloalkyl, alkyl, aryl, alkoxy, arylate, amino, alkylamio, arylamino, amido or a heterocyclic ring; and a is 1, 2 or 3; M is Ru; and R1 is H, phenyl, —CH═C(phenyl)2, —CH═C(CH3)2 or —C(CH3)2(phenyl).
- 24. A method according to claim 21 wherein the catalyst is a phosphine-substituted, an imidazolylidene-substituted, or a dihydroimidazolylidene-substituted ruthenium carbene.
- 25. A method according to claim 24 wherein the catalyst is
- 26. A method according to claim 21 wherein the metathesizable material comprises a cycloolefin.
- 27. A method according to claim 26 wherein the metathesizable material is a monomer or oligomer selected from norbornene, cycloalkene, cycloalkadiene, cycloalkatriene, cycloalkatetraene, aromatic-containing cycloolefin and mixtures thereof.
- 28. A method according to claim 27 wherein the metathesizable material comprises a norbornene having a structure represented by
- 29. A method according to claim 26 wherein the metathesizable material comprises ethylidenenorbornene monomer or oligomer, dicyclopentadiene or bicyclo [2.2.1 ]hept-5-en-2-yl-trichlorosilane.
- 30. A method according to claim 21 wherein the fibrous substrate is polyester, nylon or polyamide.
- 31. A method according to claim 30 wherein the second substrate surface is selected from the group consisting of natural rubber, polychloroprene, polybutadiene, polyisoprene, styrene-butadiene copolymer rubber, acrylonitrile-butadiene copolymer rubber, ethylene-propylene copolymer rubber, ethylene-propylene-diene terpolymer rubber, butyl rubber, brominated butyl rubber, alkylated chlorosulfonated polyethylene rubber, hydrogenated nitrile rubber, silicone rubber, fluorosilicone rubber, poly(n-butyl acrylate), thermoplastic elastomer and mixtures thereof.
- 32. A method according to claim 31 wherein the elastomeric substrate is natural rubber or ethylene-propylene-diene terpolymer rubber.
- 33. A method according to claim 21 wherein steps (a) and (b) take place at room temperature.
- 34. A manufactured article produced by the method of claim 1.
- 35. A manufactured article comprising a fibrous substrate sandwiched between and bonded to a second substrate surface and a third substrate and an adhesive layer interposed between the fibrous substrate and the second substrate and the third substrate wherein the second and third substrate comprise a rubber material and the adhesive layer comprises a metathesis polymer. comprises a metathesis polymer.
- 36. A manufactured article according to claim 35 wherein the metathesis polymer is produced from a norbornene monomer having a structure represented by
- 37. A manufactured article according to claim 35 wherein the metathesis polymer is produced from a norbornene monomer comprising ethylidenenorbornene, dicyclopentadiene or bicyclo[2.2. 1 ]hept-5-en-2-yl-trichlorosilane.
- 38. A method for providing a coating on a fibrous substrate comprising:
(a) providing a catalyst on the fibrous substrate; and (b) contacting the catalyst on the fibrous substrate with a material that undergoes a metathesis reaction to form a coating on the fibrous substrate.
- 39. A method according to claim 38 wherein the catalyst is included as a component of the fibrous substrate.
- 40. A method according to claim 38 wherein the catalyst is selected from at least one of a rhenium compound, ruthenium compound, osmium compound, molybdenum compound, tungsten compound, titanium compound, niobium compound, iridium compound and MgCl2.
- 41. A method according to claim 40 wherein the catalyst has a structure represented by
- 42. A method according to claim 41 wherein X is Cl, Br, I, F, CN, SCN, N3, O-alkyl or O-aryl; L is a heterocyclic ring or Q(R2)a wherein Q is P, As, Sb or N; R2 is H, cycloalkyl, alkyl, aryl, alkoxy, arylate, amino, alkylamino, arylamino, amido or a heterocyclic ring; and a is 1, 2 or 3; M is Ru; and R1 is H, phenyl, —CH═C(phenyl)2, —CH═C(CH3)2 or —C(CH3)2phenyl).
- 43. A method according to claim 40 wherein the catalyst is a phosphine-substituted, an imidazolylidene-substituted, or a dihydroimidazolylidene-substituted ruthenium carbene.
- 44. A method according to claim 43 wherein the catalyst is
- 45. A method according to claim 38 wherein the metathesizable material is selected from ethene, α-alkene, acyclic alkene, acyclic diene, acetylene, cyclic alkene, cyclic polyene and mixtures thereof.
- 46. A method according to claim 45 wherein the metathesizable material is a monomer or oligomer selected from norbornene, cycloalkene, cycloalkadiene, cycloalkatriene, cycloalkatetraene, aromatic-containing cycloolefin and mixtures thereof.
- 47. A method according to claim 38 wherein the metathesizable material comprises ethylidenenorbornene, dicyclopentadiene or bicyclo[2.2. 1]hept-5-en-2yl-trichlorosilane.
- 48. A method according to claim 38 wherein the fibrous substrate is fiberglass, polyester, polyamide or cotton.
Parent Case Info
[0001] This application is continuation-in-part of U.S. Ser. No. 09/209,706, filed Dec. 11, 1998.
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
09209709 |
Dec 1998 |
US |
Child |
09772157 |
Jan 2001 |
US |