# US 4,400,458 A · Diazonium salts and a diazo-type material comprising these diazonium salts > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,400,458 A - Document ID: US4400458A - Status: Granted - Kind: A - Application number: 06/302,286 - Filed: 1981-09-14 - Granted: 1983-08-23 - Earliest claimed: 1980-12-15 - Assignees: VEB Filmfabrik Wolfen - Inventors: Fred Walkow; Peter Czerney; Horst Hartmann; Jorg Marx - Web page: https://patentgrep.com/patent/US4400458A ## CPC - C07D 311/16: substituted in position 7 - G03C 1/54: Diazonium salts or diazo anhydrides - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - 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 It is the purpose and object of the present invention to make better use of the emission range of light sources and to create the diazonium salts necessary for such purpose. The diazonium salts of the present invention of the general formula ##STR1## wherein Y is ##STR2## R.sub.1, R.sub.2 are equal or different and are, alkyl having 1 to 10 carbon atoms, aryl having 6 to 10 carbon atoms in a mono or polycylic ring; R.sub.3 is hydrogen, halogen, alkyl, alkoxy, cyano; R.sub.4 is hydrogen, halogen, alkyl, alkoxy; and X.sup.e is an anion, can be employed with all known couplers and additives in diazotype materials. They have an absorption range of 480 to 550 nm. ## Claims ### Claim 1 A light-sensitive diazonium salt of the general formula ##STR7## wherein Y is ##STR8## R.sub.1, R.sub.2 are equal or different, and are alkyl having 1 to 10 carbon atoms, aryl having 6 to 10 carbon atoms in a mono or polycyclic ring; R.sub.3 is hydrogen, halogen, alkyl, alkoxy, cyano; R.sub.4 is hydrogen, halogen, alkyl, alkoxy; and x.sup..theta. is an anion. ### Claim 2 A diazo-type material, comprising a diazonium salt in the light-sensitive layer of the general formula ##STR9## wherein Y is ##STR10## R.sub.1, R.sub.2 are equal or different, and are alkyl having 1 to 10 carbon atoms, aryl having 6 to 10 carbon atoms in a mono or polycyclic ring; R.sub.3 is hydrogen, halogen, alkyl, alkoxy, cyano; R.sub.4 is hydrogen, halogen, alkyl, alkoxy; and X.sup..theta. is an anion. ### Claim 3 (depends on 1) The compound of claim 1 which is 3-(4'-diazoniumphenyl)-7-dimethylamino coumarin. ### Claim 4 (depends on 1) The compound of claim 1 which is 3-(4'-diazoniumphenyl-2',5'-dimethoxy)-7-phenylethylamino coumarin. ### Claim 5 (depends on 1) The compound of claim 1 which is 3-(4'-diazoniumphenyl)-7-di-n-butylamino coumarin. ### Claim 6 (depends on 1) The compound of claim 1 which is 3-(4'-diazoniumphenyl)-7-diethylamino coumarin. ### Claim 7 (depends on 1) The compound of claim 1 which is 3-(4'-diazoniumphenyl)-7-pyrrolidino coumarin. ### Claim 8 (depends on 1) The compound of claim 1 wherein said anion X is selected from the group consisting of tetrafluoroborate, p-chlorobenzene sulfonate, sulfate, phosphate, nitrate, chloride, zinc chloride, stannic chloride, manganese chloride, cadmium chloride. ### Claim 9 (depends on 2) The material of claim 2 wherein said diazonium salt is sensitive to light at a wavelength from 480 to 550 nm. ### Claim 10 (depends on 9) The material of claim 9 additionally comprising a coupler. ### Claim 11 (depends on 10) The material of claim 10 wherein said coupler is selected from the group consisting of 2-hydroxy-3-naphthanilides, 2,3-dihydroxynaphthalines, cyanoacetic acidamides, and mixtures thereof. ### Claim 12 (depends on 10) The material of claim 10 additionally comprising a polymeric bonding agent. ### Claim 13 (depends on 12) The material of claim 12 wherein said polymeric binding agent is selected from the group consisting of cellulose derivatives, vinyl polymers, copolymers of vinyl chloride and vinyl acetate, polystyrene, copolymers or alkylacrylates and acrylic acid, polyethylene oxides. ### Claim 14 (depends on 12) The material of claim 12 additionally comprising a component selected from the group consisting of UV-absorbers, stabilizing agents, light protective substances, developing accelerators, plasticizers. ### Claim 15 (depends on 9) The material of claim 9 wherein said anion X is selected from the group consisting of tetrafluoroborate, p-chlorobenzene, sulfonate, sulfate, phosphate, nitrate, chloride, zinc chloride, stannic chloride, manganese chloride, cadmium chloride. ### Claim 16 (depends on 15) The material of claim 15 wherein 3-(4'-diazoniumphenyl)-7-dimethylamino coumarin tetrafluoroborate, dihydroxynaphthalene, and sulfosalicyclic acid are all dispersed in a cellulose acetate solution and then deposited on a polymeric base. ### Claim 17 (depends on 15) The material of claim 15 wherein 3-(4-diazoniumphenyl)-7-dibutylamino coumarin tetrachlorozincate, and .beta.-naphthol are dissolved in a cellulose acetate solution and deposited on a polymeric carrier. ### Claim 18 (depends on 15) The material of claim 15 wherein 3-(4'-diazoniumphenyl)-7-pyrrolidino coumarin tetrachlorozincate, acetoacetanilide, and sulfosalicyclic acid are all dissolved in a cellulose acetate solution and deposited on a polymeric carrier. ### Claim 19 (depends on 15) The material of claim 15 wherein 3-(4'-diazoniumphenyl)-diethylamino coumarin tetrafluoroborate, 2-hydroxy-3-naphthalenic acid-(2'-methoxy anilide), .beta.-naphthol, acetoacetanilide, and sulfosalicyclic acid are all dissolved in a cellulose acetate solution and deposited onto a polymeric carrier material. ### Claim 20 (depends on 15) The material of claim 15 wherein 3-(4'-diazoniumphenyl)-7-diethylamino coumarin tetrachlorozincate and sulfosalicyclic acid are dissolved in a cellulose acetate solution and deposited onto a polymeric carrier. ### Claim 21 (depends on 12) The material of claim 12 wherein said coupler is present in at least about a 0.1 mole excess over said diazonium salt. ### Claim 22 (depends on 21) The material of claim 21 wherein about 20 to 40 parts by weight of said diazonium salt and coupler are present to about 100 parts by weight of said polymeric binding agent.