Claims
- 1. A polymerisable adhesive composition for bonding a low surface energy substrate to a similar or different substrate, comprising:
a) at least one free-radically polymerisable monomer component, and b) an effective amount of an initiator system for initiating polymerisation of the free-radically polymerisable monomer, said initiator system comprising an initiator compound of the formula I: 13wherein R1 is C1-C10 alkyl,
R2, R3 and R4, which may be the same or different, are C1-C10 alkyl or C3-C10 cycloalkyl, phenyl, or phenyl-substituted C1-C10 alkyl or C3-C10 cycloalkyl, provided that any two of R1-R4 may optionally be part of a carbocyclic ring, and M+ is a metal ion, or a quaternary ammonium cation, which is a two-part composition in which the free-radically polymerisable monomer component is provided in part a and the initiator compound is provided in part b, wherein the weight ratio of part a to part b is in the range from 8:10 to 10:8.
- 2. A composition according to claim 1 wherein the initiator compound is of formula I in which M+ is a metal ion.
- 3. A composition according to claim 2 wherein the initiator compound is of formula I in which M+ is an alkali metal ion.
- 4. A composition according to claim 1 wherein the initiator compound is of the formula I in which M+ is a quaternary ammonium cation of the formula II:
- 5. A composition according to claim 1 wherein the initiator compound is of formula I in which each of R1-R4 is the same C1-C10 alkyl group.
- 6. A composition according to claim 1 wherein the initiator compound is of formula I in which each of R1-R4 is the same C2-C4 alkyl group.
- 7. A composition according to claim 3 wherein the alkali metal salt is selected from the group consisting of sodium tetraethylborate and lithium tetraethylborate.
- 8. A composition according to claim 1 wherein the initiator compound is of formula I in which three of R1-R4 are the same C1-C10 alkyl group and one of R1-R4 is phenyl or phenyl-substituted C1-C10 alkyl.
- 9. A composition according to claim 1 wherein the initiator compound is of formula I in which three of R1-R4 are the same C2-C4 alkyl group and one of R1-R4 is phenyl.
- 10. A composition according to claim 8 wherein the initiator compound is selected from the group consisting of lithium phenyl triethyl borate and sodium phenyl triethyl borate.
- 11. A composition according to claim 1 wherein the initiator compound is of the formula III:
- 12. A composition according to claim 11 wherein the initiator compound is selected from the group consisting of tetra methyl ammonium phenyl triethyl borate and tetra methyl ammonium phenyl tri-n-butyl borate.
- 13. A composition according to claim 1 which is a two-part composition in which the free-radically polymerisable monomer component is at least one (meth)acrylate monomer which is provided in both parts and the initiator compound of the formula I is provided in one part.
- 14. A two-part polymerisable adhesive composition according to claim 1 comprising:
part A) an effective amount of a polymerisation initiator comprising a compound of the formula I as defined in claim 1, and a carrier which is inert to the compound of formula I; part B) at least one (meth)acrylate monomer, optionally with a toughener, acidic monomer, filler or thickener.
- 15. A composition according to claim 1, wherein the initiator compound is of formula I in which each of R1-R4 is a C2-C6 alkyl group.
- 16. A composition according to claim 14 wherein the carrier includes at least one (meth)acrylate monomer.
- 17. A two-part polymerisable adhesive composition according to claim 1 comprising.
part A) an effective amount of a polymerisation initiator comprising a compound of the formula I as defined in claim 1, and at least one (meth)acrylate monomer, optionally with a toughener, filler or thickener, but without any compound that is reactive with the compound of the formula I to free an organoborane therefrom; and part B) at least one (meth)acrylate monomer together with a compound reactive with the compound of formula I to free an organoborane therefrom, and optionally with a toughener, filler or thickener.
- 18. A composition according to claim 17 wherein the compound in part B that is reactive with the compound of formula I is an acid or acidic monomer.
- 19. A composition accordingly to claim 17 wherein the compound of formula I is soluble in the (meth)acrylate monomer in part A.
- 20. A composition according to claim 1 wherein the initiator compound is of the formula III:
- 21. A composition according to claim 20 wherein the initiator compound is of the formula III in which:
R1-R3 are each the same C2-C4 alkyl group, R4 and R5-R8 are as defined in claim 35.
- 22. A composition according to claim 1, further comprising a polyolefin filler.
- 23. A composition according to claim 1, wherein the free-radically polymerisable monomer component comprises a (meth)acrylic monomer.
- 24. A composition according to claim 1, wherein the quantity of the initiator compound of formula I is such as to provide 0.01% to 5% by weight of boron in the total composition.
- 25. A composition according to claim 1 which includes an acidic monomer that is free-radically polymerisable.
- 26. A composition according to claim 1 which includes an aziridine-functional material as a carrier for the initiator compound of formula I.
- 27. A composition according to claim 26 wherein no significant quantity of an aziridine-functional material is present in Part A of the composition.
- 28. A composition according to claim 1 wherein the weight ratio of part A to part B is about 1:1.
- 29. A method for bonding a low surface energy substrate, such as a polyolefin substrate, to a similar or different substrate, wherein the method comprises applying a composition according to claim 1 to at least one of the substrates, bringing the substrates together with the composition between them and allowing the composition to cure.
- 30. A method for bonding a low surface energy substrate to a similar or different substrate, wherein the method comprises mixing parts A and B of a two part adhesive composition according to claim 1 immediately prior to use in order to initiate polymerisation, applying the mixed adhesive composition to at least one of the substrates, bringing the substrates together and allowing the composition to cure by completion of the polymerisation initiated on mixing of the two parts A and B.
- 31. A cured adhesive composition comprising the polymerisation product of a composition according to claim 1.
- 32. A bonded article comprising two substrates bonded by the polymerisation product of a composition according to claim 1.
- 33. A bond formed between two substrates by the polymerisation product of a composition according to claim 1.
- 34. A polymerisable composition, which includes
a) at least one free-radically polymerisable monomer component, b) an effective amount of an initiator system for initiating polymerisation of the free-radically polymerisable monomer, said initiator system comprising a compound of the formula I as defined in claim 1, and c) an effective amount of a compound that is reactive with the compound of the formula I to free an organoborane from the compound of formula I and thus to initiate polymerisation of the at least one free-radically polymerisable monomer.
- 35. A system capable of initiating the polymerisation of a (meth)acrylic monomer, the system comprising.
a) a compound of the formula I as defined in claim 1; and b) an effective amount of a compound that is reactive with the compound of the formula I to free an organoborane from the compound of the formula I.
- 36. A polymerisable acrylic composition comprising:
a) a (meth)acrylate component comprising at least one (meth)acrylic monomer, b) an effective amount of a compound of the formula I as defined in claim 1; and c) an effective amount of a compound that is reactive with the compound of formula I to free an organoborane from the compound of the formula I and thus to initiate polymerisation of the at least one (meth)acrylic monomer.
- 37. A composite article comprising a first substrate and a second substrate bonded to the first substrate by an acrylic adhesive, wherein the acrylic adhesive comprises the polymerisation product of a polymerisable acrylic composition that comprised:
a) a (meth)acrylic component comprising at least one (meth)acrylic monomer, b) an effective amount of a compound of the formula I as defined in claim 1, and c) an effective amount of a compound that is reactive with the compound of the formula I to free an organoborane from the compound of the formula I and thus to initiate polymerisation of the at least one (meth)acrylic monomer.
- 38. A method of bonding a low surface energy polymer to a substrate, the method comprising the steps of:
i) providing a low surface energy polymer; ii) providing a substrate; iii) providing an adhesive composition comprising:
a) a (meth)acrylic component comprising at least one (meth)acrylic monomer; b) an effective amount of a compound of the formula I as defined in claim 1; and c) an effective amount of the compound that is reactive with the compound of the formula I to free an organoborane from the compound of the formula I and thus to initiate polymerisation of the at least one (meth)acrylic monomer; (iv) applying the adhesive composition to either the low surface energy polymer or the substrate; v) joining the low surface energy polymer and the substrate with the adhesive composition there between; and (vi) permitting the adhesive composition to cure to adhesively bond the low surface energy polymer and the substrate.
- 39. A compound of the formula I as defined in claim 1 for use as an initiator of polymerisation in an adhesive composition for bonding a low surface energy substrate.
- 40. A compound according to claim 47 wherein the compound is of formula I in which three of R1-R4 are the same C2-C4 alkyl group and one of R1-R4 is phenyl.
- 41. Tetra methyl ammonium phenyl tri-n-butyl borate.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2002/0286 |
Apr 2002 |
IE |
|
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application is related to the application entitled “Polymerisation Initiators, Polymerisable Compositions, and Uses Thereof for Bonding Low Surface Energy Substrates” filed as International application No. PCT/IE01/00133 on Oct. 23, 2001; and the application entitled “Polymerisation Initiators, Polymerisable Compositions, and Uses Thereof” filed as International application No. PCT/IE01/00134 on Oct. 23, 2001; the contents of the said International applications are incorporated herein by reference.
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
PCT/IE01/00133 |
Oct 2001 |
US |
Child |
10412331 |
Apr 2003 |
US |
Parent |
PCT/IE01/00134 |
Oct 2001 |
US |
Child |
10412331 |
Apr 2003 |
US |