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US 4,394,403 AGranted
Photopolymerizable compositions
AssigneeMinnesota Mining and Manufacturing Company
InventorGeorge H. Smith
Life of this patent
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Abstract
Photopolymerizable compositions which comprise cationically polymerizable organic material and photosensitive aromatic iodonium salt of a halogen-containing complex ion are described as are coated substrates and methods for bonding materials together using such compositions.
Claims41
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.
7 more elements
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.
2 more elements
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.
9 more elements
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.
4 more elements
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.-.
6 more elements
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.-.
4 more elements
Dependencies are inferred from the claim text.