# US 5,683,850 A · Diazo heat-sensitive recording material comprising hydroxy coumarin as a coupler > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,683,850 A - Document ID: US5683850A - Status: Granted - Kind: A - Application number: 08/753,886 - Filed: 1996-12-02 - Granted: 1997-11-04 - Earliest claimed: 1995-12-05 - Assignees: Fuji Photo Film Co., Ltd. - Inventors: Tetunori Matushita; Hiroshi Sato; Sadao Ishige; Kimiatsu Nomura; Mitsuyuki Tsurumi - Web page: https://patentgrep.com/patent/US5683850A ## CPC - G03C 1/54: Diazonium salts or diazo anhydrides - G03C 1/58: Coupling substances therefor - G03C 1/002: {containing microcapsules (with photopolymerisable compositions G03F7/002)} - G03C 1/52: Compositions containing diazo compounds as photosensitive substances (G03C1/64 takes precedence) - 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 diazo heat-sensitive recording material having excellent raw stock storability and image storage characteristics, which comprises a support having thereon a recording layer comprising a diazo compound, a coupling component and an organic base. The diazo compound is a 4-disubstituted amino-2-alkoxybenzenediazonium salt and the coupling component is a compound represented by the following general formula: ##STR1## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, a sulfamoyl group, a halogen atom, a cyano group or a nitro group. ## Claims ### Claim 1 A diazo heat-sensitive recording material comprising a support having thereon a recording layer comprising a diazo compound, a coupling component and an organic base, wherein said diazo compound is a diazonium salt represented by the following general formula (I) and said coupling component is a compound represented by the following general formula (II): ##STR8## wherein R.sub.1, R.sub.2 and R.sub.3 each represents an alkyl group, an aralkyl group or an aryl group; R.sub.2 and R.sub.3 may form a ring together with the nitrogen atom in formula (I) adjacent to R.sub.2 and R.sub.3 ; and X represents an acid anion, ##STR9## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, a sulfamoyl group, a halogen atom, a cyano group or a nitro group; and R.sub.4 and R.sub.5, R.sub.5 and R.sub.6, or R.sub.6 and R.sub.7 may be combined with each other to form a ring. ### Claim 2 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein said recording layer further comprises microcapsules, and said diazo compound is encapsulated in said microcapsules. ### Claim 3 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein the total number of carbon atoms in R.sub.1, R.sub.2 and R.sub.3 of formula (I) is 12 or more. ### Claim 4 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein the alkyl, aralkyl, or aryl groups represented by R.sub.1, R.sub.2 and R.sub.3 are substituted or unsubstituted. ### Claim 5 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein said diazonium salt represented by formula (I) is represented by the following general formula (III): ##STR10## wherein R.sub.8 represents an alkyl group, an aralkyl group or an aryl group; L.sub.1 and L.sub.2 each represents an alkylene group; A.sub.1 and A.sub.2 each represents an alkyl group, an aralkyl group, an aryl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, an alkylsulfonyl group, an arylsulfonyl group, a sulfamoyl group, a halogen atom or a cyano group; L.sub.1 and L.sub.2, and A.sub.1 and A.sub.2 may each be the same or different; and X represents an acid anion. ### Claim 6 (depends on 5) The diazo heat-sensitive recording material as claimed in claim 5, wherein at least one of A.sub.1 and A.sub.2 is an alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group or a cyano group. ### Claim 7 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein the total number of carbon atoms in R.sub.4, R.sub.5, R.sub.6 and R.sub.7 in formula (II) is 12 or more. ### Claim 8 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein the compound represented by formula (II) is represented by general formula (IV): ##STR11## wherein R.sub.9 represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, a sulfamoyl group or a halogen atom; R.sub.10, R.sub.11 and R.sub.12 each represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group or a sulfamoyl group; Y represents an oxygen atom or a sulfur atom; and l+m is an integer of 1 to 4 with the proviso that m is an integer of 1 or more and n represents an integer of 1 to 10. ### Claim 9 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein the diazo compound has a melting point of from 30.degree. to 200.degree. C. ### Claim 10 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein said recording layer contains the diazo compound in an amount of from 0.02 g/m.sup.2 to 3 g/m.sup.2. ### Claim 11 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1, wherein said recording layer contains the compound represented by formula (II) in an amount of from 0.1 to 30 parts by weight per one part by weight of the diazo compound. ### Claim 12 (depends on 2) The diazo heat-sensitive recording material as claimed in claim 2, wherein said recording layer further comprises an organic base, and said compound represented by formula (II) and said organic base are arranged outside the microcapsules. ### Claim 13 (depends on 1) The diazo heat-sensitive recording material as claimed in claim 1 comprising at least two recording layers, wherein each of said recording layers contains a diazonium salt represented by formula (I) having a maximum absorption wavelength different from that of the diazonium salt contained in the other recording layers.