Photopolymerizable compositions

Claim 2

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 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.

Claim 3

A photopolymerizable composition in accordance with claim 1, wherein said organic material has an epoxy functionality of at least 1.

Claim 4

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.

Claim 5

A photopolymerizable composition in accordance with claim 1, wherein said Ar 1 and Ar 2 are selected from the group consisting of phenyl and substituted phenyl groups.

Claim 6

A photopolymerizable composition in accordance with claim 1, wherein said Ar 1 and Ar 2 groups are selected from the group consisting of thienyl and substituted thienyl groups.

Claim 7

A photopolymerizable composition in accordance with claim 4, wherein n is zero.

Claim 8

A photopolymerizable composition in accordance with claim 4, wherein n is 1 and Z is a carbon-to-carbon bond.

Claim 9

A photopolymerizable composition in accordance with claim 5, wherein n is zero.

Claim 10

A photopolymerizable composition in accordance with claim 4, wherein Ar 1 and Ar 2 are alkylphenyl groups.

Claim 11

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.

Claim 12

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.

Claim 13

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.

Claim 14

A photopolymerizable composition in accordance with claim 1, wherein said organic material contains a vinyl ether group.

Claim 15

A photopolymerizable composition in accordance with claim 1, wherein said organic material contains an oxetane group.

Claim 16

A photopolymerizable composition in accordance with claim 1, wherein said organic material is a lactone.

Claim 17

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.

Claim 18

A substrate bearing a thin layer of the composition of claim 1 which has been cured in situ.

Claim 19

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 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.

Claim 20

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 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.

Claim 21

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.

Claim 22

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.

Claim 23

A photopolymerizable composition in accordance with claim 18, wherein said organic material contains one or more cyclohexene oxide groups.

Claim 24

A photopolymerizable composition in accordance with claim 21, wherein said organic material comprises epoxycyclohexanecarboxylate.

Claim 25

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.

Claim 26

A photopolymerizable composition in accordance with claim 18, wherein said Ar 1 and Ar 2 are selected from the group consisting of phenyl and substituted phenyl groups.

Claim 27

A photopolymerizable composition in accordance with claim 18, wherein said Ar 1 and Ar 2 groups are selected from the group consisting of thienyl and substituted thienyl groups.

Claim 28

A photopolymerizable composition in accordance with claim 24, wherein n is zero.

Claim 29

A photopolymerizable composition in accordance with claim 24, wherein n is 1 and Z is a carbon-to-carbon bond.

Claim 30

A photopolymerizable composition in accordance with claim 25, wherein n is zero.

Claim 31

A photopolymerizable composition in accordance with claim 24, wherein Ar 1 and Ar 2 are alkylphenyl groups.

Claim 32

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.

Claim 33

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.

Claim 34

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.

Claim 35

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 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.

Claim 36

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 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, and hexafluoroantimonate.

Claim 37

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.

Claim 38

An aromatic iodonium complex salt of the formula ##STR18## wherein Ar 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate.

Claim 39

An aromatic iodonium complex salt of the formula ##STR18## wherein Ar 1 and Ar 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 1 and R 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 - is a halogen-containing complex anion selected from the group consisting of hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate.

Claim 40

An aromatic iodonium complex salt in accordance with claim 35, wherein X is hexafluorophosphate.

Claim 41

An aromatic iodonium complex salt in accordance with claim 35, wherein X is hexafluoroantimonate.

Claim 42

An aromatic iodonium complex salt in accordance with claim 35, wherein X is hexafluoroarsenate.

Claim 43

A photopolymerizable composition in accordance with claim 1 further containing up to 50% by volume of a filler.

Claim 44

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 1 and Ar 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 1 and R 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 4 - , PF 6 - , AsF 6 - , SbF 6 - , and SbCl 6 - .

Claim 45

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 1 and Ar 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 1 and R 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 4 - , PF 6 - , AsF 6 - , SbF 6 - , and SbCl 6 - .

Claim 46

An iodonium salt of the formula ##STR24## wherein Ar 1 and Ar 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 1 and R 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 6 - , AsF 6 - , SbF 6 - , and SbCl 6 - .

Claim 47

An iodonium salt of the formula ##STR24## wherein Ar 1 and Ar 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 1 and R 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 6 - , AsF 6 - , SbF 6 - , and SbCl 6 - .