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US 4,318,766 AGranted
Process of using photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials
AssigneeMinnesota Mining and Manufacturing Company
InventorGeorge H. Smith
Life of this patent
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Abstract
Photocopolymerizable compositions are described which contain epoxides, organic material with hydroxyl functionality, and a photosensitive aromatic sulfonium or iodonium salt of a halogen-containing complex ion. Coated substrates are also described.
Claims6
A process for obtaining a cured coating comprising:
- (a) providing a photocopolymerizable composition comprising:
- (i) a first organic material having epoxide functionality greater than about 1.5;
- (ii) a second organic material having aliphatic hydroxyl functionality of at least 1;
- said material being free of other active hydrogens and being free of epoxide groups;
- and
- (iii) a complex salt photoinitiator selected from the group consisting of:
- (1) aromatic iodonium complex salts having the formula ##STR14## where 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 oxygen;
- sulfur;
- ##STR15## R-N where R is aryl or acyl;
- a carbon-to-carbon bond;
- or ##STR16## where R.sub.1 and R.sub.2 are selected from hydrogen, alkyl radicals of 1 to 4 carbons, and alkenyl radicals of 2 to 4 carbons;
- and n is zero or 1;
- and wherein X.sup.- is a halogen-containing complex anion selected from tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate;
- and (2) aromatic sulfonium complex salt having the formula ##STR17## the group consisting of aromatic groups having 4 to 20 carbon atoms and alkyl radicals having 1 to 20 carbon atoms;
- wherein at least one of R.sub.1, R.sub.2 and R.sub.3 is aromatic;
- wherein Z is selected from the group consisting of oxygen;
- sulfur;
- ##STR18## where R is aryl or acyl;
- a carbon-to-carbon bond;
- or ##STR19## where R.sub.4 and R.sub.5 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 is a halogen-containing complex anion selected from tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate;
- wherein the ratio of hydroxyl equivalents in said second organic material to epoxide equivalents in said first organic material is in the rane of 0.001/1 to 10/1;
- and wherein said photoinitiator is present in said composition in an amount of about 0.1 to 30 parts by weight per 100 parts by weight of combined first and second organic materials;
- (b) applying a thin layer of said composition to a substrate, and
- (c) exposing said layer to actinic radiation or electron beam irradiation.
24 more elements
A process for bonding a radiation-transparent substrate to a second substrate comprising:
- (a) providing a photocopolymerizable composition comprising:
- (i) a first organic material having epoxide functionality greater than about 1.5;
- (ii) a second organic material having aliphatic hydroxyl functionality of at least 1;
- said material being free of other active hydrogens and being free of epoxide groups;
- and
- (iii) a complex salt photoinitiator selected from the group consisting of:
- (1) aromatic iodonium complex salts having the formula ##STR20## where 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 oxygen;
- sulfur;
- ##STR21## where R is aryl or acyl;
- a carbon-to-carbon bond;
- or ##STR22## where R.sub.1 and R.sub.2 are selected from hydrogen, alkyl radicals of 1 to 4 carbons, and alkenyl radicals of 2 to 4 carbons;
- and n is zero or 1;
- and wherein X.sup.- is a halogen-containing complex anion selected from tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate;
- and (2) aromatic sulfonium complex salt having the formula ##STR23## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of aromatic groups having 4 to 20 carbon atoms and alkyl radicals having 1 to 20 carbon atoms;
- wherein at least one of R.sub.1, R.sub.2 and R.sub.3 is aromatic;
- wherein Z is selected from the group consisting of oxygen;
- sulfur;
- ##STR24## where R is aryl or acyl;
- a carbon-to-carbon bond;
- or ##STR25## where R.sub.4 and R.sub.5 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 is a halogen-containing complex anion selected from tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate;
- wherein the ratio of hydroxyl equivalents in said second organic material to epoxide equivalents in said first organic material is in the range of 0.001/1 to 10/1;
- and wherein said photoinitiator is present in said composition in an amount of about 0.1 to 30 parts by weight per 100 parts by weight of combined first and second organic materials;
- (b) disposing a layer of said composition between said substrates and in contact therewith;
- and
- (c) 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.
25 more elements
Dependencies are inferred from the claim text.