Hexaarylbiimidazole-heterocyclic compound compositions

Claim 2

The composition of claim 2 wherein the hexaarylbiimidazole is a 2,2'', 4,4'', 5,5''-hexaphenylbiimidazole in which the phenyl groups can contain substituents which do not interfere with the photodissociation of the hexaarylbiimidazole and which have Hammett sigma values in the -0.5 to 0.8 range; and wherein the heterocyclic compound is represented by the formula wherein X and Y are each individually selected from C-H, C-CH3, C-CH2CH3, or N, and wherein Ar1 is phenyl, biphenylyl or naphthyl, any one of which may be substituted with lower alkyl, lower aralkyl or lower alkylaralkyl.

Claim 3

The composition of claim 3 wherein the phenyl groups of the 2,2'', 4,4'', 5,5''-hexaphenylbiimidazole can contain substituents selected from lower alkyl, lower alkoxy, chloro, fluoro, bromo and benzo; and wherein in the formula of the heterocyclic compound the group where R is hydrogen or alkyl of one or two carbon atoms, and wherein Ar1 is phenyl, biphenylyl or naphthyl.

Claim 4

The composition of claim 4 wherein the 2 and 2'' phenyl groups of the hexaarylbiimidazole each contain an ortho substituent selected from lower alkyl, lower alkoxy, chloro, fluoro or bromo and wherein the 4,4'', 5, and 5'' phenyl groups of the hexaarylbiimidazole are either unsubstituted or contain up to three lower alkoxy groups each; and wherein the heterocyclic compound is selected from 2,5-diphenylfuran, 2, 5-diphenyloxazole, 2-phenyl-5-(alpha-naphthyl)oxazole, 1,4-bis(2-(5, -phenyloxazoyl))benzene, 2-phenyl-5-(alpha-naphthyl)oxadiazole, 2,5-di(alpha-naphthyl)oxadiazole or 2-phenyl-5-(4-biphenylyl)oxadiazole.

Claim 5

The composition of claim 5 wherein the hexaarylbiimidazole is selected from 2,2''-bis(o-chlorophenyl)-4,4'', 5,5''-tetraphenylbiimidazole or 2,2''-bis-(o-chlorophenyl)4,4'', 5,5''-(m-methoxyphenyl)biimidazole, and wherein the heterocyclic compound is 2,5-diphenylfuran.

Claim 6

The composition of claim 2 containing, additionally, (C) a leuco dye that is oxidizable to dye by triarylimidazolyl radicals.

Claim 7

The composition of claim 3 containing, additionally, (C) a leuco dye that is oxidizable to dye by triarylimidazolyl radicals which is selected from aminotriarylmethanes, aminoxanthanes, aminothioxanthenes, amino-9,10-dihydroacridines, aminophenoxazines, aminophenothiazines, aminodihydrophenazines, aminodiphenylmethanes, leuco indamines, aminohydrocinnamic acids, hydrazines, leuco indigoid dyes, amino-2,3-dihydroanthraquinones, tetrahalo-p,p''-biphenols, 2(p-hydroxyphenyl)-4,5-diphenylimidazoles, or phenethylanilines.

Claim 8

The composition of claim 4 containing, additionally, (C) a strong acid salt of an aminotriarylmethane leuco dye wherein at leasT two of the aryl groups are phenyl groups having (a) an R1R2N-substituent in the position para to the bond to the methane carbon wherein R1 and R2 are each selected from the class consisting of hydrogen, C1 to C10 alkyl, 2-hydroxyethyl, 2-cyanoethyl, benzyl or phenyl, and (b) a group ortho to the bond to the methane carbon atom which is selected from lower alkyl, lower alkoxy, fluorine, chlorine, bromine, or butadienylene which when joined to the phenyl group forms a naphthalene ring; and the third aryl group, when different from the first two, is selected from thienyl, furyl, oxazylyl, pyridyl, thiazolyl, indolyl, indolinyl, benzoxazolyl, quinolyl, benzothiazolyl, phenyl, naphthyl, or such aforelisted groups substituted with lower alkyl, lower alkoxyl, methylenedioxy, fluoro, chloro, bromo, amino, lower alkylamino, lower dialkylamino, lower alkylthio, hydroxy, carboxy, carbonamido, lower carbalkoxy, lower alkylsulfonyl, lower alkylsulfonamido, C6 to C10 arylsulfonamido, nitro or benzylthio.

Claim 9

The composition of claim 5 containing, additionally (C) a strong acid salt of an aminotriarylmethane leuco dye having the structural formula wherein R3 and R4 are each lower alkyl or benzyl, Y and Y'' are lower alkyl and X is p-methoxyphenyl, 2-thienyl, phenyl, 1-naphthyl, 2,3-dimethoxyphenyl, 3,4-methylenedioxyphenyl, or benzylthiophenyl.

Claim 10

The composition of claim 6 which contains, additionally, a leuco dye selected from the p-toluenesulfonic acid salt of tris(p-N,N-diethylamino-o-tolyl)methane, or an equimolar mixture of the p-toluene sulfonic acid salts of bis(p-N,N-diethylamino-o-chlorophenyl) (p-chlorophenyl)methane and bis(p-N,N-diethylamino-o-tolyl)(p-isopropylthio-m-tolyl)methane.

Claim 11

The composition of claim 2 which contains, additionally, an addition-polymerizable, ethylenically unsaturated compound having at least one polymerizable ethylenic group, a photooxidizable amine and, optionally, a chain transfer agent.

Claim 12

The composition of claim 3 which contains, additionally, an addition-polymerizable, ethylenically unsaturated compound selected from terminally unsaturated carboxylic ester monomers, a photooxidizable amine, and optionally, a chain transfer agent selected from N-phenylglycine, 1,1-dimethyl-3,5-diketocyclohexane or an organic thiol.

Claim 13

The composition of claim 5 which contains additionally an addition-polymerizable, ethylenically unsaturated compound selected from terminally unsaturated carboxylic ester monomers, a photooxidizable amine selected from a strong acid salt of an aminotriarylmethane leuco dye having the structural formula wherein R3 and R4 are each lower alkyl or benzyl, Y and Y'' are lower alkyl and X is p-methoxyphenyl, 2-thienyl, phenyl, 1-naphthyl, 2,3-dimethoxyphenyl, 3,4-methylenedioxyphenyl, or benzylthiophenyl, and optionally, a chain transfer agent selected from N-phenylglycine, 1,1-dimethyl-3,5-diketocyclohexane or an organic thiol.

Claim 14

The composition of claim 11 which contains additionally, trimethylolpropane triacrylate.

Claim 15

Process of irradiating the composition of claim 2 with light having wavelengths within the range of the absorption bands of the heterocyclic compound.

Claim 16

Process for imaging which comprises irradiating the composition of claim 7 with a color-forming dosage of light having wavelengths within the range of the absorption bands of the heterocyclic compound.

Claim 17

Process for polymerization which comprises irradiating the composition of claim 12 with light having wavelengths within the range of the absorption bands of the heterocyclic compound.

Claim 18

Process for imaging and polymerization which compriSes irradiating the composition of claim 14 with light having a wavelength within the range of the absorption bands of the heterocyclic compound and an intensity sufficient to simultaneously produce a colored polymerized composition.

Claim 19

The composition of claim 1 coated on a plastic film.

Claim 20

The composition of claim 7 coated on a plastic film.

Claim 21

The composition of claim 9 coated on a plastic film.

Claim 22

The composition of claim 12 coated on a plastic film.

Claim 23

The composition of claim 14 coated on a plastic film.

Claim 24

The composition of claim 1 coated on paper.

Claim 25

The composition of claim 7 coated on paper.

Claim 26

The composition of claim 9 coated on paper.

Claim 27

The composition of claim 12 coated on paper.

Claim 28

The composition of claim 14 coated on paper.

Claim 29

A composition comprising the composition of claim 1 and an inert solvent.

Claim 30

A composition comprising the composition of claim 7 and an inert solvent.

Claim 31

A composition comprising the composition of claim 9 and an inert solvent.

Claim 32

A composition comprising the composition of claim 12 and an inert solvent.

Claim 33

A composition comprising the composition of claim 14 and an inert solvent.

Claim 34

The composition of claim 1 wherein the heterocyclic compound has an extinction coefficient of at least 15,000 in the 290-400 m Mu region of the electromagnetic spectrum.