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US4247618A Expired / Lapsed US ⏱️ 0.0 years remaining

Photoimaging systems with cyclic hydrazides

Assignee: EIDP Inc
•
Filing: 1979-05-11
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Granted: 1981-01-27
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Expires: 1999-05-11
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Abstract

Abstract A photosensitive system comprising in intimate admixture (1) a dye in its leuco form, (2) a photooxidant taken from the group of hexaarylbiimidazole compounds, benzophenone, para-aminophenyl ketones, polynuclear quinones and thioxanthenones, and mixtures thereof and in the presence of the admixture is a 5-member-heterocyclic phenylhydrazide compound. The cyclic phenylhydrazide can be present in the admixture, or a dry coating of the admixture, after imagewise exposure, is treated with a solution of the heterocyclic compound. The system is useful in formation of colored images.

Inventors

  • 👤 Rolf Dessauer
  • 👤 Raymond A. Firmani

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 22:29
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/72; G03C1/73; G03C1/732

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 256 words
A photosensitive system comprising in intimate admixture (1) at least one dye in the leuco form having one to two removable hydrogens, the removal of which forms a differently colored compound; with the proviso that when the leuco form has only one removable hydrogen and the resultant dye is cationic, there is also present a mineral acid, organic acid or acid-supplying compound which forms a salt with the leuco form of the dye, and (2) at least one photooxidant compound taken from the group of 2,4,5-triarylbiimidazolyl dimer consisting of two lophine radicals bound together by a single covalent bond, benzophenone, a para-aminophenyl ketone, a polynuclear quinone, a thioxanthenone, and mixtures thereof, the improvement being that in the presence of said admixture is at least one cyclic phenylhydrazide compound of the formula: ##STR15## wherein X may be either H 2 C< or O═C< with the proviso that when X is H 2 C<, Y is ##STR16## and when X is O═C<, Y is ##STR17## R 1 and R 2 are the same or different and are hydrogen atoms, alkyl of 1 to 4 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms in the ortho, meta or para positions, alkoxy of 1 to 4 carbon atoms in the ortho, meta or para positions, chloro, fluoro or bromo in the meta or para positions, sulfo in the para position, substituted alkyl, aralkoxy, and aryloxy; and R 4 is hydrogen and alkyl of 1 to 4 carbon atoms.
Claim 2
Dependent Claim 256 words
A photosensitive system comprising in intimate admixture (1) at least one dye in the leuco form having one to two removable hydrogens, the removal of which forms a differently colored compound; with the proviso that when the leuco form has only one removable hydrogen and the resultant dye is cationic, there is also present a mineral acid, organic acid or acid-supplying compound which forms a salt with the leuco form of the dye, and (2) at least one photooxidant compound taken from the group of 2,4,5-triarylbiimidazolyl dimer consisting of two lophine radicals bound together by a single covalent bond, benzophenone, a para-aminophenyl ketone, a polynuclear quinone, a thioxanthenone, and mixtures thereof, the improvement being that in the presence of said admixture is at least one cyclic phenylhydrazide compound of the formula: ##STR15## wherein X may be either H 2 C< or O═C< with the proviso that when X is H 2 C<, Y is ##STR16## and when X is O═C<, Y is ##STR17## R 1 and R 2 are the same or different and are hydrogen atoms, alkyl of 1 to 4 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms in the ortho, meta or para positions, alkoxy of 1 to 4 carbon atoms in the ortho, meta or para positions, chloro, fluoro or bromo in the meta or para positions, sulfo in the para position, substituted alkyl, aralkoxy, and aryloxy; and R 4 is hydrogen and alkyl of 1 to 4 carbon atoms.
Claim 3
Dependent Claim 29 words
A photosensitive system according to claim 1 wherein in the presence of the admixture is up to 10 mole percent of the cyclic phenylhydrazide based on the photooxidant compound.
Claim 4
Dependent Claim 26 words
A photosensitive system according to claim 2 wherein the photooxidant is a 2,4,5-triarylbiimidazolyl dimer consisting of two lophone radicals bound together by a single covalent bond.
Claim 5
Dependent Claim 19 words
A photosensitive system according to claim 2 wherein the photooxidant is the combination of benzophenone and a para-aminophenyl ketone.
Claim 6
Dependent Claim 14 words
A photosensitive system according to claim 2 wherein the photooxidant is a polynuclear quinone.
Claim 7
Dependent Claim 13 words
A photosensitive system according to claim 2 wherein the photooxidant is a thioxanthenone.
Claim 8
Dependent Claim 13 words
A photosensitive system according to claim 2 wherein the cyclic phenylhydrazide is 1-phenylpyrazolidine-3-one.
Claim 9
Dependent Claim 13 words
A photosensitive system according to claim 2 wherein the cyclic phenylhydrazide is 1-phenyl-4-methyl-pyrazolidine-3-one.
Claim 10
Dependent Claim 13 words
A photosensitive system according to claim 2 wherein the cyclic phenylhydrazide is 1-phenyl-4,4-dimethyl-pyrazolidine-3-one.
Claim 11
Dependent Claim 13 words
A photosensitive system according to claim 2 wherein the cyclic phenylhydrazide is 3-methyl-1-(p-sulfophenyl)-2-pyrazoline-5-one.
Claim 12
Dependent Claim 13 words
A photosensitive system according to claim 2 wherein the cyclic phenylhydrazide is 3-methyl-1-phenyl-2-pyrazoline-5-one.
Claim 13
Dependent Claim 14 words
A photosensitive system according to claim 3 wherein the leuco dye is an aminotriarylmethane.
Claim 14
Dependent Claim 13 words
A photosensitive system according to claim 12 wherein the 2,4,5-triarylbiimidazolyl dimer is bis(o-chlorophenyl)tetraphenylbiimidazole.
Claim 15
Dependent Claim 13 words
A photosensitive system according to claim 12 wherein the 2,4,5-triarylbiimidazolyl dimer is 2,2'-bis(o-chlorophenyl)4,4',5,5'tetrakis-(m-methoxyphenyl)biimidazole.
Claim 16
Dependent Claim 16 words
A photosensitive system according to claim 13 or claim 14 wherein the cyclic phenylhydrazide is 1-phenyl-pyrazolidine-3-one.
Claim 17
Dependent Claim 14 words
A photosensitive system according to claim 4 wherein the leuco dye is an aminotriarylmethane.
Claim 18
Dependent Claim 13 words
A photosensitive system according to claim 16 wherein the 2,4,5-triarylbiimidazolyl dimer is bis(o-chlorophenyl)tetraphenylbiimidazole.
Claim 19
Dependent Claim 13 words
A photosensitive system according to claim 16 wherein the 2,4,5-triarylbiimidazolyl dimer is 2,2'-bis(o-chlorophenyl)4,4',5,5'-tetrakis-(m-methoxyphenyl)biimidazole.
Claim 20
Dependent Claim 16 words
A photosensitive system according to claim 17 or claim 18 wherein the cyclic phenylhydrozide is 1-phenyl-pyrazolidine-3-one.

References Cited (Backward Citations)

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US2728115A Cited
US3445234A Cited
US3585038A Cited
US3552973A Cited
US3753395A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-01-27 1984-07-28 1985-01-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-01-27 1988-07-28 1989-01-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-01-27 1992-07-28 1993-01-27 $7700.00 Window Closed / Lapsed

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