P
USRE34675EExpiredUtilityPatentIndex 93

Coupling agent compositions

Assignee: DOW CORNINGPriority: Jun 30, 1986Filed: May 1, 1992Granted: Jul 26, 1994
Est. expiryJun 30, 2006(expired)· nominal 20-yr term from priority
Inventors:PLUEDDEMANN EDWIN P
C08K 5/5419C03C 25/40C03C 17/30Y10S528/901C09D 4/00
93
PatentIndex Score
23
Cited by
13
References
56
Claims

Abstract

Coupling agent and primer compositions comprising a conventional silane coupling agent (1), and a disilyl crosslinker compound (II) of the general formula (RO).sub.3 SiR'Si(OR).sub.3 where RO denotes a hydrolyzable group, R' denotes a divalent organic radical, and the weight ratio of (I) to (II) is between 1:99 and 99:1 inclusive.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A .[.comprising.]. .Iadd.coupling agent and primer .Iaddend..Iadd.mixture consisting essentially of: .Iaddend. (I) a silane coupling agent; .[.and.].   (II) a disilyl crosslinker compound represented by the general formula   (RO).sub.3 SiR'Si(OR).sub.3       wherein RO denotes an alkoxy radical having 1 to 8 carbon atoms, R' is selected from alkylene groups having 1 to 9 carbon atoms, ##STR5## in which x and y are 1 to 5.[...]. .Iadd., .Iaddend. ##STR6## in which x and y are between 0 and 3 inclusive, or ##STR7## in which s, t, u, and v are 1 to 3 inclusive and wherein the weight ratio of (I) : (II) is between 1:99 and 99:1 inclusive.Iadd.; and   a solvent mutually compatible with said coupling agent (I) and said disilyl crossliner compound (II), whereby said mixture is effective as both a coupling agent and a primer. .Iaddend.   
     
     
       2. The composition of claim 1 wherein the R' radical of the disilyl crosslinker compound is an alkylene radical with 1 to 8 carbon atoms. 
     
     
       3. The composition of claim 2 wherein the R' radical of the disilyl crosslinker compound is a methylene radical. 
     
     
       4. The composition of claim 2 wherein the R' radical of the disilyl crosslinker compound is an ethylene radical. 
     
     
       5. The composition of claim 2 wherein the R' radical of the disilyl crosslinker compound is a propylene radical. 
     
     
       6. The composition of claim 2 wherein the R' radical of the disilyl crosslinker compound is a hexylene radical. 
     
     
       7. The composition of claim 1 wherein said divalent organic radical, R', of said disilyl crosslinker compound is represented by the formula   --(CH.sub.2).sub.x OOCCH═(CHCOO(CH.sub.2).sub.y --     where x and y have values of 1 to 5.   
     
     
       8. The composition of claim 7 wherein the R' radical of said disilyl crosslinker compound is .[.--(CH 2 ) 3  OOCCH═CHCOO(CH 2 ) 3  --.]. .Iadd.--(CH 2 ) 3  OOCCH═CHCOO(CH 2 ) 3  --. .[.and wherein the composition further comprises a solvent mutually compatible with said coupling agent (I) and said disilyl crosslinker compound (II)..]. 
     
     
       9. The composition of claim 1 wherein the divalent organic radical of said disilyl crosslinker compound is of the general formula ##STR8## where the value of x and y is between 0 and 3 inclusive, the two alkylene radicals are positioned either meta or para on the benzene ring, .[.and wherein the composition further comprises a solvent mutually compatible with said coupling agent (I) and said disilyl crosslinker compound (II).].. 
     
     
       10. The composition of claim 9 wherein the value of x and y is zero. 
     
     
       11. The composition of claim 1 wherein the R' radical of the disilyl crosslinker compound is represented by the general formula ##STR9## where s, t, u, and v have values between 1 and 3 inclusive.Iadd..[., and and wherein the composition further comprises a solvent mutually compatible with said coupling agent (I) and said disilyl crosslinker compound (II).]..Iaddend.. 
     
     
       12. The composition of claim 2 wherein the silane coupling agent is an aminofunctional silane coupling agent chosen from the group consisting of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,(aminoethylaminomethyl) phenyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyl tris(2-ethylhexoxy) silane, 3-aminopropyltrimethoxysilane, trimethoxysilylpropyldiethylenetriamine, 3-aminopropyltrimethoxysilane, aminopropyltriethoxysilane, bis(2-hydroxyethyl)-3-aminopropyltrimethoxysilane, and 4-aminobutyltriethoxysilane. 
     
     
       13. The composition of claim 12 wherein the silane coupling agent is N-(2-aminoethyl)-3-aminopropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       14. The composition of claim 2 wherein the silane coupling agent is a methacrylic functional couplingagent chosen from the group consisting of 3-methacryloxypropyltrimethoxysilane, and 2-methacryloxyethyldimethyl[3-trimethoxysilylpropyl]ammonium chloride. 
     
     
       15. The composition of claim 14 wherein the silane coupling agent is 3-methacryloxypropyl-trimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       16. The composition of claim 2 wherein the silane coupling agent is a epoxy functional coupling agent chosen from the group consisting of 3-glycidoxypropyltrimethoxysilane, and beta (3,4 epoxycyclohexyl) ethyltrimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       17. The composition of claim 2 wherein the silane coupling agent is a vinyl functional coupling agent chosen from the group consisting of 3[2(vinyl benzylamino) ethylamino]propyltrimethoxysilane, triacetoxyvinylsilane, tris-(2-methoxyethoxy)vinylsilane, vinyltrimethoxysilane, and vinyl tris(t-butylperoxy)silane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       18. The composition of claim 2 wherein the silane coupling agent is a halo-organic radical functional coupling agent chosen from the group consisting of 3-chloropropyltrimethoxysilane, and 3-chloropropyltriethoxysilane, 1-trimethoxysilyl-2-(p,m-chloromethyl)phenyl-ethane, and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent. 
     
     
       19. The composition of claim 18 where the haloorganic radical is 3-chloropropyltrimethoxysilane. 
     
     
       20. The composition of claim 2 wherein the silane coupling agent is a mercapto functional coupling agent chosen from the group consisting of mercaptopropyltrimethoxysilane, mercaptopropyltriethoxysilane, 3-mercaptopropylmethyltrimethoxysilane, and 3-mercaptopropylmethyidimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       21. The composition of claim 3 wherein the silane coupling agent is an aminofunctional silane coupling agent chosen from the group consisting of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,(aminoethylaminomethyl) phenyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyl tris(2-ethylhexoxy) silane, 3-aminopropyltrimethoxysilane, trimethoxysilylpropyldiethylenetriamine, 3-aminopropyltrimethoxysilane, aminopropyltriethoxysilane, Bis(2-hydroxyethyl)-3-aminopropyltrimethoxysilane, and 4-aminobutyltriethoxysilane. 
     
     
       22. The composition of claim 21 wherein the silane coupling agent is N-(2-aminoethyl)-3-aminopropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       23. The composition of claim 3 wherein the silane coupling agent is a methacrylic functional coupling agent chosen from the group consisting of 3-methacryloxypropyltrimethoxysilane, and 2-methacryloxyethyldimethyl[3-trimethoxysilylpropyl]ammonium chloride. 
     
     
       24. The composition of claim 23 wherein the silane coupling agent is 3-methacryloxypropyl-trimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       25. The composition of claim 3 wherein the silane coupling agent is a epoxy functional coupling agent chosen from the group consisting of 3-glycidoxypropyltrimethoxysilane, and beta (3,4 epoxycyclohexyl) ethyltrimethoxysilane.Iadd..[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.]..Iaddend.. 
     
     
       26. The composition of claim 3 wherein the silane coupling agent is a vinyl functional coupling agent chosen from the group consisting of 3[2(vinyl benzylamino) ethylamino]propyltrimethoxysilane, triacetoxyvinylsilane, tris-(2-methoxyethoxy)vinylsilane, vinyltrimethoxysilane, and vinyl tris(t-butylperoxy)silane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       27. The composition of claim 3 wherein the silane coupling agent is a halo-organic radical functional coupling agent chosen from the group consisting of 3-chloropropyltrimethoxysilane, and 3-chloropropyltriethoxysilane, 1-trimethoxysilyl-2-(p,m-chloromethyl)phenyl-ethane. 
     
     
       28. The composition of claim 27 where the haloorganic radical is 3-chloropropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       29. The composition of claim 3 wherein the silane coupling agent is a mercapto functional coupling agent chosen from the group consisting of mercaptopropyltrimethoxysilane, mercaptopropyltriethoxysilane, 3-mercaptopropylmethyltrimethoxysilane, and 3-mercaptopropylmethyldimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       30. The composition of claim 4 wherein the silane coupling agent is an aminofunctional silane coupling agent chosen from the group consisting of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,(aminoethylaminomethyl) phenyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyl tris(2-ethylhexoxy) silane, 3-aminopropyltrimethoxysilane, trimethoxysilylpropyldiethylenetriamine, 3-aminopropyltrimethoxysilane, aminopropyltriethoxysilane, Bis(2-hydroxyethyl)-3-aminopropyltrimethoxysilane, and 4-aminobutyltriethoxysilane. 
     
     
       31. The composition of claim 30 wherein the silane coupling agent is N-(2-aminoethyl)-3-aminopropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       32. The composition of claim 4 wherein the silane coupling agent is a methacrylic functional coupling agent chosen from the group consisting of 3-methacryloxypropyltrimethoxysilane, and 2-methacryloxyethyldimethyl[3-trimethoxysilylpropyl]ammonium chloride. 
     
     
       33. The composition of claim 32 wherein the silane coupling agent is 3-methacryloxypropyl-trimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       34. The composition of claim 4 wherein the silane coupling agent is a epoxy functional coupling agent chosen from the group consisting of 3-glycidoxypropyltrimethoxysilane, and beta (3,4 epoxycyclohexyl) ethyltrimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       35. The composition of claim 4 wherein the silane coupling agent is a vinyl functional coupling agent chosen from the group consisting of 3[2(vinyl benzylamino) ethylamino]propyltrimethoxysilane, triacetoxyvinylsilane, tris-(2-methoxyethoxy)vinylsilane, vinyltrimethoxysilane, and vinyl tris(t-butylperoxy)silane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       36. The composition of claim 4 wherein the silane coupling agent is a halo-organic radical functional coupling agent chosen from the group consisting of 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 1-trimethoxysilyl-2-(p,m-chloromethyl)pbenylethane. 
     
     
       37. The composition of claim 36 where the haloorganic radical is 3-chloropropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       38. The composition of claim 4 wherein the silane coupling agent is a mercapto functional coupling agent chosen from the group consisting of 3-mercaptopropylmethyltrimethoxysilane, and 3-mercaptopropylmethyldimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       39. The composition of claim 10 wherein the silane coupling agent is an aminofunctional silane coupling agent chosen from the group consisting of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,(aminoethylaminomethyl) phenyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyl tris(2-ethylhexoxy) silane, 3-aminopropyltrimethoxysilane, trimethoxysilylpropyldiethylenetriamine, 3-aminopropyltrimethoxysilane, aminopropyltriethoxysilane, Bis(2-hydroxyethyl)-3-aminopropyltrimethoxysilane, and 4-aminobutyltriethoxysilane. 
     
     
       40. The composition of claim 39 wherein the silane coupling agent is N-(2-aminoethyl)-3-aminopropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       41. The composition of claim 10 wherein the silane coupling agent is a methacrylic functional coupling agent chosen from the group consisting of 3-methacryloxypropyltrimethoxysilane, and 2-methacryloxyethyldimethyl[3-tri-methoxysilylpropyl]ammonium chloride. 
     
     
       42. The composition of claim 41 wherein the silane coupling agent is 3-methacryloxypropyl-trimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       43. The composition of claim 10 wherein the silane coupling agent is an epoxy functional coupling agent chosen from the group consisting of 3-glycidoxypropyltrimethoxysilane, and beta (3,4 epoxycyclohexyl) ethyltrimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       44. The composition of claim 10 wherein the silane coupling agent is a vinyl functional coupling agent chosen from the group consisting of 3[2(vinyl benzylamino) ethylamino]propy]trimethoxysilane, triacetoxyvinylsilane, and vinyl tris-(2-methoxyethoxy)vinylsilane, vinyltrimethoxysilane, and vinyl tris(t-butylperoxy)silane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       45. The composition of claim 10 wherein the silane coupling agent is a halo-organic radical functional coupling agent chosen from the group consisting of 3-chloropropyltrimethoxysilane, and 3-chloropropyltriethoxysilane, 1-trimethoxysilyl-2-(p,m-chloromethyl)phenyl-ethane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       46. The composition of claim 45 where the haloorganic radical is 3-chloropropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       47. The composition of claim 10 wherein the silane coupling agent is a mercapto functional coupling agent chosen from the group consisting of mercaptopropyltrimethoxysilane, mercaptopropyltriethoxysilane, 3-mercaptopropylmethyltrimethoxysilane, and 3-mercaptopropylmethyldimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       48. The composition of claim 8 wherein the silane coupling agent is an amino functional silane coupling agent chosen from the group consisting of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,(aminoethylaminomethyl) phenyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyl tris(2-ethylhexoxy) silane, 3-aminopropyltrimethoxysilane, trimethoxysilylpropyldiethylenetriamine, 3-aminopropyltrimethoxysilane, aminopropyltriethoxysilane, Bis(2-hydroxyethyl)-3-aminopropyltrimethoxysilane, and 4-aminobutyltriethoxysilane. 
     
     
       49. The composition of claim 48 wherein the silane coupling agent is N-(2-aminoethyl)-3-aminopropyltrimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       50. The composition of claim 8 wherein the silane coupling agent is a methacrylic functional coupling agent chosen from the group consisting of 3-methacryloxypropyltrimethoxysilane, and 2-methacryloxyethyldimethyl[3-trimethoxysilylpropyl]ammonium chloride. 
     
     
       51. The composition of claim 50 wherein the silane coupling agent is 3-methacryloxypropyl-trimethoxysilane.[., and the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       52. The composition of claim 8 wherein the silane coupling agent is a epoxy functional coupling agent chosen from the group consisting of 3-glycidoxypropyltrimethoxysilane, and beta (3,4 epoxycyclohexyl) ethyltrimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       53. The composition of claim 8 wherein the silane coupling agent is a vinyl functional coupling agent chosen from the group consisting of 3[2(vinyl benzylamino) ethylamino]propyltrimethoxysilane, triacetoxyvinyisilane, tris-(2-methox yethoxy)vinylsilane, vinyltrimethoxysilane, and vinyl tris(t-butylperoxy)silane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       54. The composition of claim 8 wherein the silane coupling agent is a halo-organic radical functional coupling agent chosen from the group consisting of 3-chloropropyltrimethoxysilane, and 3-chloropropyltriethoxysilane, 1-trimethoxysilyl-2-(p,m-chloromethyl)phenyl-ethane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.].. 
     
     
       55. The composition of claim 54 where the haloorganic radical is 3-chloropropyltrimethoxysilane. 
     
     
       56. The composition of claim 8 wherein the silane coupling agent is a mercapto functional coupling agent chosen from the group consisting of mercaptopropyltrimethoxysilane, mercaptopropyltriethoxysilane, 3-mercaptopropylmethyltrimethoxysilane, and 3-mercaptopropylmethyldimethoxysilane.[., and where the composition further comprises a mutual solvent for said disilyl crosslinker and coupling agent.]..

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