# US 4,399,210 A · Photosensitive compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,399,210 A - Document ID: US4399210A - Status: Granted - Kind: A - Application number: 06/364,274 - Filed: 1982-04-01 - Granted: 1983-08-16 - Earliest claimed: 1981-04-01 - Assignees: Fuji Photo Film Co., Ltd. - Inventors: Teruo Nagano; Akira Nagashima - Web page: https://patentgrep.com/patent/US4399210A ## CPC - G03F 7/105: having substances, e.g. indicators, for forming visible images - G03C 7/02: Direct bleach-out processes; Materials therefor; Preparing or processing such materials - G03F 7/022: Quinonediazides (G03F7/075 takes precedence) - G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) - G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G) ## Abstract A photosensitive composition containing at least one o-naphthoquinonediazide compound represented by the following general formula (I): ##STR1## wherein A represents a divalent aliphatic residue, a divalent substituted aliphatic residue, a divalent aromatic residue or a divalent substituted aromatic residue, and a discoloring agent which changes its color tone upon the interaction with a photodecomposition product of the o-naphthoquinonediazide compound. The photosensitive composition directly provides visible contrast between exposed portions and unexposed portions upon light exposure without development and is particularly useful for making lithographic printing plates, letterpress printing plates, IC circuits, photomasks, etc. ## Claims ### Claim 1 A photosensitive composition containing at least one o-naphthoquinonediazide compound represented by the following general formula (I) ##STR5## wherein A represents a divalent aliphatic residue, a divalent substituted aliphatic residue, a divalent aromatic residue or a divalent substituted aromatic residue, and a discoloring agent which changes its color tone upon the interaction with a photodecomposition product of the o-naphthoquinonediazide compound. ### Claim 2 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the divalent aliphatic residue represented by A is a straight chain, branched chain and/or cyclic residue containing a saturated bond and/or unsaturated bond. ### Claim 3 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the divalent aliphatic residue represented by A contains 2 to 20 carbon atoms. ### Claim 4 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the divalent substituted aliphatic residue represented by A is a divalent aliphatic residue substituted with an aryl group, a divalent aliphatic residue in which an ether bond is formed or a divalent aliphatic residue substituted with a halogen atom. ### Claim 5 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the divalent aromatic residue represented by A is an arylene group or an aromatic heterocyclic residue. ### Claim 6 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the divalent aromatic residue represented by A is a monocyclic group or a dicyclic group. ### Claim 7 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the divalent substituted aromatic residue represented by A is a divalent aromatic residue substituted with a lower alkyl group, a halogen atom, a nitro group or an acetamino group. ### Claim 8 (depends on 1) The photosensitive composition as claimed in claim 1, wherein A represents a phenylene group substituted with an alkyl group, a phenylene group substituted with a halogen atom or a phenylene group. ### Claim 9 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the discoloring agent is inherently colorless but is colored upon reaction with the photodecomposition product of the compound represented by the general formula (I). ### Claim 10 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the discoloring agent is originally colored but is discolored or decolored upon reaction with the photodecomposition product of the compound represented by the general formula (I). ### Claim 11 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the discoloring agent is a primary aromatic amine, a secondary aromatic amine or a leuco dye. ### Claim 12 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the discoloring agent is a diphenylmethane series dye, a triphenylmethane series dye, a thiazine series dye, an oxazine series dye, a xanthene series dye, an anthraquinone series dye, an iminonaphthoquinone series dye or an azomethine series dye. ### Claim 13 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the compound represented by the general formula (I) is present in an amount of 0.01 to 100 parts by weight per 1 part by weight of the discoloring agent. ### Claim 14 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the composition additionally containing a photosensitive resist forming material. ### Claim 15 (depends on 14) The photosensitive composition as claimed in claim 14, wherein the photosensitive resist forming material is a diazo resin or an o-quinonediazide compound. ### Claim 16 (depends on 14) The photosensitive composition as claimed in claim 14, wherein the photosensitive resist forming material is a condensate of a p-diazodiphenylamine and paraformaldehyde. ### Claim 17 (depends on 14) The photosensitive composition as claimed in claim 14, wherein the photosensitive resist forming material is an o-naphthoquinonediazide compound. ### Claim 18 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the composition additionally containing a diazo resin and a binder polymer containing a hydroxy group, an amino group, a carboxylic acid group, an amido group, a sulfonamido group, an active methylene group, a thioalcohol group or an epoxy group. ### Claim 19 (depends on 18) The photosensitive composition as claimed in claim 18, wherein the binder polymer is present in an amount of 40 to 95% by weight of the photosensitive composition. ### Claim 20 (depends on 1) The photosensitive composition as claimed in claim 1, wherein the composition additionally containing an o-naphthoquinonediazide compound and an alkali-soluble resin. ### Claim 21 (depends on 20) The photosensitive composition as claimed in claim 20, wherein the alkali-soluble resin is present in an amount of 50 to 85% by weight of the photosensitive composition. ### Claim 22 (depends on 14) The photosensitive composition as claimed in claim 14, wherein the combined amount of the discoloring agent and the compound represented by the general formula (I) is 0.1 to 150 parts by weight per 100 parts by weight of the photosensitive resist forming material. ### Claim 23 A photosensitive element, comprising: a support; and a photosensitive layer on the support wherein the layer is comprised of an o-naphthoquinonediazide compound represented by the following general formula (I) ##STR6## wherein A represents a divalent aliphatic residue, a divalent substituted aliphatic residue, a divalent aromatic residue or a divalent substituted aromatic residue, and a discoloring agent which changes its color tone upon the interaction with a photodecomposition product of the o-naphthoquinonediazide compound.