Claims
- 1. A photopolymerizable composition comprising:
- (a) an organic material which is cationically polymerizable; and
- (b) about 0.5 to 30 parts by weight, per 100 parts by weight of said organic material, of an aromatic iodonium complex salt photoinitiator of the formula ##STR9## wherein Ar.sup.1 and Ar.sup.2 are aromatic groups having 4 to 20 carbon atoms and are selected from the group consisting of phenyl, thienyl, furanyl, and pyrazolyl groups; Z is selected from the group consisting of an oxygen atom; a sulfur atom; ##STR10## where R is hydrogen, lower alkyl or acyl; a carbon-to-carbon bond; or ##STR11## where R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms, and an alkenyl radical having 2 to 4 carbon atoms; and n is zero or 1; and X.sup.- is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.
- 2. A photopolymerizable composition in accordance with claim 1, wherein said organic material has an epoxy functionality of at least 1.
- 3. A photopolymerizable composition in accordance with claim 2, wherein said organic material is selected from the group consisting of epichlorohydrins, alkylene oxides, alkenyl oxides, glycidyl esters, glycidyl ethers, epoxy novolaks, copolymers of acrylic acid esters of glycidol and copolymerizable vinyl compounds, and polyurethane polyepoxides.
- 4. A photopolymerizable composition in accordance with claim 1, wherein said Ar.sup.1 and Ar.sup.2 are selected from the group consisting of phenyl and substituted phenyl groups.
- 5. A photopolymerizable composition in accordance with claim 1, wherein said Ar.sup.1 and Ar.sup.2 groups are selected from the group consisting of thienyl and substituted thienyl groups.
- 6. A photopolymerizable composition in accordance with claim 4, wherein n is zero.
- 7. A photopolymerizable composition in accordance with claim 4, wherein n is 1 and Z is a carbon-to-carbon bond.
- 8. A photopolymerizable composition in accordance with claim 5, wherein n is zero.
- 9. A photopolymerizable composition in accordance with claim 4, wherein Ar.sup.1 and Ar.sup.2 are alkylphenyl groups.
- 10. A photopolymerizable composition in accordance with claim 1, wherein said halogen-containing complex anion is selected from the group consisting of tetrafluoroborate, hexafluorophosphate, and hexafluoroantimonate.
- 11. A photopolymerizable composition in accordance with claim 1, wherein said photoinitiator is present in an amount of about 1 to 7 parts by weight per 100 parts by weight of said organic compound.
- 12. A photopolymerizable composition in accordance with claim 1 further containing about 0.01 to 1 part by weight of sensitizing dye per part by weight of photoinitiator.
- 13. A photopolymerizable composition in accordance with claim 1, wherein said organic material contains a vinyl ether group.
- 14. A photopolymerizable composition in accordance with claim 1, wherein said organic material contains an oxetane group.
- 15. A photopolymerizable composition in accordance with claim 1, wherein said organic material is a lactone.
- 16. A process for obtaining a cured coating comprising:
- (a) supplying a thin layer of the composition of claim 1 to a substrate, and
- (b) exposing said layer to actinic radiation or electron beam irradiation.
- 17. A substrate bearing a thin layer of the composition of claim 1 which has been cured in situ.
- 18. A photopolymerizable composition comprising:
- (a) an organic compound having an epoxy functionality of at least 1; and
- (b) about 0.5 to 30 parts by weight, per 100 parts by weight of said organic compound, of an aromatic iodonium complex salt photoinitiator of the formula ##STR12## wherein Ar.sup.1 and Ar.sup.2 are aromatic groups having 4 to 20 carbon atoms and are selected from the group consisting of phenyl, thienyl, and furanyl groups; Z is an oxygen atom, a carbon-to-carbon bond, or ##STR13## where R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms, and an alkenyl radical having 2 to 4 carbon atoms, and n is zero or 1; and X.sup.- is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.
- 19. A photopolymerizable composition in accordance with claim 18, wherein said organic material is selected from the group consisting of epichlorohydrins, alkylene oxides, alkenyl oxides, glycidyl esters, glycidyl ethers, epoxy novolaks, copolymers of acrylic acid esters of glycidol and copolymerizable vinyl compounds, and polyurethane polyepoxides.
- 20. A photopolymerizable composition in accordance with claim 18, wherein said organic material comprises a copolymer of acrylic acid esters of glycidol and copolymerizable vinyl compounds.
- 21. A photopolymerizable composition in accordance with claim 18, wherein said organic material contains one or more cyclohexene oxide groups.
- 22. A photopolymerizable composition in accordance with claim 21, wherein said organic material comprises epoxycyclohexanecarboxylate.
- 23. A photopolymerizable composition in accordance with claim 18, wherein said organic material comprises glycidyl ether of the formula ##STR14## where R is alkyl or aryl and n is an integer of 1 to 6.
- 24. A photopolymerizable composition in accordance with claim 18, wherein said Ar.sup.1 and Ar.sup.2 are selected from the group consisting of phenyl and substituted phenyl groups.
- 25. A photopolymerizable composition in accordance with claim 18, wherein said Ar.sup.1 and Ar.sup.2 groups are selected from the group consisting of thienyl and substituted thienyl groups.
- 26. A photopolymerizable composition in accordance with claim 24, wherein n is zero.
- 27. A photopolymerizable composition in accordance with claim 24, wherein n is 1 and Z is a carbon-to-carbon bond.
- 28. A photopolymerizable composition in accordance with claim 25, wherein n is zero.
- 29. A photopolymerizable composition in accordance with claim 24, wherein Ar.sup.1 and Ar.sup.2 are alkylphenyl groups.
- 30. A photopolymerizable composition in accordance with claim 18, wherein said halogen-containing complex anion is selected from the group consisting of tetrafluoroborate, hexafluorophosphate, and hexafluoroantimonate.
- 31. A photopolymerizable composition in accordance with claim 18, wherein said photoinitiator is present in an amount of about 1 to 7 parts by weight per 100 parts by weight of said organic compound.
- 32. A photopolymerizable composition in accordance with claim 18, further containing about 0.01 to 1 part by weight of sensitizing dye per part by weight of photoinitiator.
- 33. A photopolymerizable composition comprising an admixture of:
- (a) 80 to 100 parts by weight of a diglycidyl ether of Bisphenol A,
- (b) up to 20 parts by weight of a phenyl glycidyl ether,
- (c) up to 10 parts by weight of a solvent carrier,
- (d) up to about 1 part by weight of a sensitizing dye,
- (e) 0.5 to 20 parts by weight of an aromatic iodonium complex salt photoinitiator of the formula ##STR15## wherein Ar.sup.1 and Ar.sup.2 are aromatic groups having 4 to 20 carbon atoms and are selected from the group consisting of phenyl, thienyl, furanyl, and pyrazolyl groups; Z is selected from the group consisting of an oxygen atom; a sulfur atom; ##STR16## where R is hydrogen, lower alkyl or acyl; a carbon-to-carbon bond; or ##STR17## where R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms; and n is zero or 1; and X.sup.- is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.
- 34. A process for bonding a radiation-transparent substrate to a second substrate comprising:
- (a) disposing a layer of the composition of claim 1 between said substrates and in contact therewith; and
- (b) exposing said layer to actinic radiation or electron beam irradiation through said radiation-transparent substrate in an amount and for a time sufficient to render said layer insoluble.
- 35. An aromatic iodonium complex salt of the formula ##STR18## wherein Ar.sup.1 and Ar.sup.2 are aromatic groups having 4 to 20 carbon atoms and are selected from the group consisting of phenyl, thienyl, furanyl, and pyrazolyl groups; Z is selected from the group consisting of an oxygen atom; a sulfur atom; ##STR19## where R is hydrogen, lower alkyl or acyl; a carbon-to-carbon bond; or ##STR20## where R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms, and an alkenyl radical having 2 to 4 carbon atoms; and n is zero or 1; and wherein X.sup.- is a halogen-containing complex anion selected from the group consisting of hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate.
- 36. An aromatic iodonium complex salt in accordance with claim 35, wherein X is hexafluorophosphate.
- 37. An aromatic iodonium complex salt in accordance with claim 35, wherein X is hexafluoroantimonate.
- 38. An aromatic iodonium complex salt in accordance with claim 35, wherein X is hexafluoroarsenate.
- 39. A photopolymerizable composition in accordance with claim 1 further containing up to 50% by volume of a filler.
- 40. A photopolymerizable composition comprising:
- (a) a cationically polymerizable organic material having an oxirane ring polymerizable by ring opening and
- (b) about 0.5 to 30 parts by weight per 100 parts by weight of said organic material of a photo-decomposable aromatic iodonium salt of the formula ##STR21## wherein Ar.sup.1 and Ar.sup.2 are aromatic groups having 4 to 20 carbon atoms and are selected from the group consisting of phenyl, thienyl, furanyl, pyrazolyl, chlorophenyl, nitrophenyl, methoxyphenyl and pyridyl groups; Z is selected from the group consisting of an oxygen atom; a sulfur atom; ##STR22## where R is hydrogen, lower alkyl or acyl; a carbon-to-carbon bond; or ##STR23## where R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms, and an alkenyl radical having 2 to 4 carbon atoms; and n is zero or 1; a is 1 or 2 and X is a halogen containing complex anion selected from the group consisting of BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, and SbCl.sub.6.sup.-.
- 41. An iodonium salt of the formula ##STR24## wherein Ar.sup.1 and Ar.sup.2 are aromatic groups having 4 to 20 carbon atoms and are selected from the group consisting of phenyl, thienyl, furanyl, pyrazolyl, chlorophenyl, nitrophenyl, methoxyphenyl and pyridyl groups; Z is selected from the group consisting of an oxygen atom; a sulfur atom; ##STR25## where R is hydrogen, lower alkyl or acyl; a carbon-to-carbon bond; or ##STR26## where R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, an alkyl radical having 2 to 4 carbon atoms; and n is zero or 1; a is 1 or 2 and X is a halogen containing complex anion selected from the group consisting of PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, and SbCl.sub.6.sup.-.
Parent Case Info
This application is a continuation-in-part of my copending application Ser. No. 467,899, filed May 8, 1974, now abandoned.
US Referenced Citations (11)
Foreign Referenced Citations (2)
Number |
Date |
Country |
1071652 |
Jun 1967 |
GBX |
1111232 |
Apr 1968 |
GBX |
Non-Patent Literature Citations (2)
Entry |
Irving et al., Journal of Chemical Society (1960), pp. 2078-2081. |
Banks, Chemical Review, vol. 66, No. 3, May 25, 1966, pp. 243-263. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
467899 |
May 1974 |
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