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US4298678A Expired / Lapsed US ⏱️ 0.0 years remaining

Photosensitive compositions and elements containing substituted hydroxylamine

Assignee: EIDP Inc
•
Filing: 1980-08-14
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Granted: 1981-11-03
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Expires: 2000-08-14
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Abstract

Abstract A photosensitive composition comprising a photooxidant, leuco dye and a substituted hydroxylamine compound of the formula R 1 R 2 NOH wherein R 1 and R 2 , e.g., are alkyl, cyclic alkyl, aryl, aralkyl, alkaryl and R 1 and R 2 taken together form a heterocyclic ring of 5 to 7 carbon atoms. Optionally monomers and polymeric binders can be present. The compositions are useful for photoimaging and in solvent and aqueous developable resist-forming films.

Inventors

  • 👤 Mark R. McKeever

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 20:10
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/105; G03C; G03C1/00; G03C1/72; G03C1/73; G03C1/732

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 165 words
A photosensitive composition comprising an admixture of (A) a photooxidant compound, (B) a leuco dye that is oxidizable to dye by the photooxidant, and (C) a hydroxylamine compound of the formula R 1 R 2 NOH, and acid salts thereof, wherein each of R 1 and R 2 can be hydrogen with the proviso that both cannot be hydrogen, a linear or branched-chain alkyl group of 2 to 14 carbon atoms, a cyclic alkyl group of 5 to 14 carbon atoms, an aryl group of 6 to 10 carbon atoms, an aralkyl group wherein the aryl moiety is of 6 to 10 carbon atoms and the alkyl moiety is of 1 to 14 carbon atoms, and an alkaryl group wherein the aryl moiety is of 6 to 10 carbon atoms and the alkyl moiety is of 1 to 9 carbon atoms, and R 1 and R 2 when taken together may with the nitrogen atom form a heterocyclic ring of 5 to 7 carbon atoms.
Claim 2
Dependent Claim 165 words
A photosensitive composition comprising an admixture of (A) a photooxidant compound, (B) a leuco dye that is oxidizable to dye by the photooxidant, and (C) a hydroxylamine compound of the formula R 1 R 2 NOH, and acid salts thereof, wherein each of R 1 and R 2 can be hydrogen with the proviso that both cannot be hydrogen, a linear or branched-chain alkyl group of 2 to 14 carbon atoms, a cyclic alkyl group of 5 to 14 carbon atoms, an aryl group of 6 to 10 carbon atoms, an aralkyl group wherein the aryl moiety is of 6 to 10 carbon atoms and the alkyl moiety is of 1 to 14 carbon atoms, and an alkaryl group wherein the aryl moiety is of 6 to 10 carbon atoms and the alkyl moiety is of 1 to 9 carbon atoms, and R 1 and R 2 when taken together may with the nitrogen atom form a heterocyclic ring of 5 to 7 carbon atoms.
Claim 3
Dependent Claim 23 words
A photosensitive composition according to claim 1 wherein (D) at least one addition polymerizable ethylenically unsaturated monomeric compound is present in the admixture.
Claim 4
Dependent Claim 22 words
A photosensitive composition according to claim 1 or claim 2 wherein (E) at least one polymeric binder is present in the admixture.
Claim 5
Dependent Claim 21 words
A photosensitive composition according to claim 1 wherein an additional NOH group is attached to R 1 or R 2 .
Claim 6
Dependent Claim 22 words
A photosensitive composition according to claim 1 wherein the photooxidant compound is a 2,4,5-triphenylimidazolyl dimer where the phenyl groups may be substituted.
Claim 7
Dependent Claim 13 words
A photosensitive composition according to claim 5 wherein the 2,4,5-triphenylimidazolyl dimer is 2,2'-bis-(o-chlorophenyl)-4,4,5,5'-tetraphenylbiimidazole.
Claim 8
Dependent Claim 15 words
A photosensitive composition according to claim 1 wherein the photooxidant compound is a ketone compound.
Claim 9
Dependent Claim 14 words
A photosensitive composition according to claim 7 wherein the ketone compound is Michler's ketone.
Claim 10
Dependent Claim 21 words
A photosensitive composition according to claim 2 wherein the monomeric compound is trimethylolpropane triacrylate, triethyleneglycoldimethacrylate or a combination of both compounds.
Claim 11
Dependent Claim 22 words
A photosensitive composition according to claim 3 wherein the polymeric binder is a combination of styrene/maleic anhydride copolymer and styrene/acrylic acid copolymer.
Claim 12
Dependent Claim 34 words
A photosensitive composition according to claim 1 wherein the hydroxylamine compound is of the formula R 1 R 2 NOH wherein R 1 and R 2 are alkyls of 2 to 14 carbon atoms.
Claim 13
Dependent Claim 13 words
A photosensitive composition according to claim 11 wherein the hydroxylamine compound is N,N-diethylhydroxylamine.
Claim 14
Dependent Claim 68 words
A photosensitive composition according to claim 1 wherein the leuco dye has 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.
Claim 15
Dependent Claim 71 words
A photosensitive composition according to claim 13 wherein the leuco dye is the salt of an acid in leuco form of a triphenylmethane dye having, in at least two of the phenyl rings positioned para to the methane carbon atom, a substituent selected from the group consisting of amino, and C 1 to C 4 dialkyl amino groups, the acid being a mineral acid, an organic acid, or a acid-supplying compound.
Claim 16
Dependent Claim 18 words
A photosensitive element which comprises a support bearing a layer of a photosensitive composition according to claim 3.
Claim 17
Dependent Claim 14 words
A photosensitive element according to claim 15 wherein the support is a film support.

References Cited (Backward Citations)

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US3479185A 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) 1984-11-02 1985-05-04 1985-11-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-11-02 1989-05-04 1989-11-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-11-02 1993-05-04 1993-11-03 $7700.00 Window Closed / Lapsed

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