# US 2006/0234155 A1 · Radiation-sensitive compositions comprising oxazole derivatives and imageable elements based thereon > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2006/0234155 A1 - Document ID: US20060234155A1 - Status: Published application - Kind: A1 - Application number: 10/544,758 - Filed: 2004-02-20 - Published: 2006-10-19 - Earliest claimed: 2003-02-21 - Assignees: Eastman Kodak Company - Inventors: Harald Baumann; Udo Dwars; Detlef Pietsch; Michael Flugel - Web page: https://patentgrep.com/patent/US20060234155A1 ## CPC - G03F 7/029: Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur - G03F 7/031: Organic compounds not covered by group G03F7/029 - 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) ## Abstract Radiation-sensitive element comprising: (a) one or more types of monomers each comprising at least one ethylenically unsaturated group accessible to a free-radical polymerization, (b) at least one sensitizer, (c) at least one coinitiator capable of forming free radicals together with the sensitizer (b) and selected from the following classes of compounds: metallocenes; 1,3,5-triazine derivatives with one to three CX3 groups, wherein X represents chlorine or bromine; peroxides; hexaarylbiimidazoles; oxime ethers; oxime esters; N-aryl glycines and derivatives thereof; thiol compounds; N-aryl, S-aryl and O-aryl polycarboxylic acids with at least 2 carboxyl groups of which at least one is bonded to the N, S or O atom of the aryl unit; alkyltriarylborates; benzoin ethers; benzoin esters; trihalogenomethylarylsulfones; amines; N,N-dialkylaminobenzoic acid esters; aromatic sulfonyl halides; trihalogenomethylsulfones; imides; diazosulfonates; 9,10-dihydroanthracene derivatives; a-hydroxy and a-amino acetophenones; and (d) optionally one or more components selected from alkali-soluble binders, colorants, exposure indicators, plasticizers, chain transfer agents, leuco dyes, surfactants, inorganic fillers and thermopolymerization inhibitors characterized in that the at least one sensitizer is an oxazole derivative of the formula (I), wherein each R1, R2 and R3 is independently selected from a halogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, which may also be fused, an optionally substituted aralkyl group, a group —NR4R5 and a group —OR6, wherein R4 and R5 are independently selected from a hydrogen atom, an alkyl, aryl or ralkyl group, R6 is an alkyl, aryl or aralkyl group or a hydrogen atom and k, m and n are independently 0 or an integer from 1 to 5. ## Claims ### Claim 1 Radiation-sensitive composition comprising (a) one or more types of monomers and/or oligomers and/or polymers, each comprising at least one ethylenically unsaturated group accessible to a free-radical polymerization, (b) at least one sensitizer, (c) at least one coinitiator capable of forming free radicals together with the sensitizer (b) and selected from the following classes of compounds: metallocenes; 1,3,5-triazine derivatives with one to three CX3 groups, wherein X represents chlorine or bromine; peroxides; hexaarylbiimidazoles; oxime ethers; oxime esters; N-aryl glycines and derivatives thereof; thiol compounds; N-aryl, S-aryl and O-aryl polycarboxylic acids with at least 2 carboxyl groups of which at least one is bonded to the N, S or O atom of the aryl unit; alkyltriarylborates; benzoin ethers; benzoin esters; trihalogenomethylarylsulfones; amines; N,N-dialkylaminobenzoic acid esters; aromatic sulfonyl halides; trihalogenomethylsulfones; imides; diazosulfonates; 9,10-dihydro-anthracene derivatives; α-hydroxy and α-amino acetophenones; and (d) optionally one or more components selected from alkali-soluble binders, colorants, exposure indicators, plasticizers, chain transfer agents, leuco dyes, surfactants, inorganic fillers and thermopolymerization inhibitors, characterized in that the at least one sensitizer is an oxazole derivative of the formula (I) wherein each R1, R2 and R3 is independently selected from a halogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, which may also be fused, an optionally substituted aralkyl group, a group —NR4R5 and a group —OR6, wherein R4 and R5 are independently selected from a hydrogen atom, an alkyl, aryl or aralkyl group, R6 is an alkyl, aryl or aralkyl group or a hydrogen atom and k, m and n are independently 0 or an integer from 1 to 5. ### Claim 2 (depends on 1) Radiation-sensitive composition according to claim 1, wherein an oxazole derivative of formula (I) in used as a sensitizer and k, m and n are independently selected from 0 and 1. ### Claim 3 (depends on 1) Radiation-sensitive composition according to claim 1, wherein the stabilizer is a 1,3-oxazole of the formula (I) wherein at least one of the groups R1, R2 and R3 represents a group —NR4R5. ### Claim 4 (depends on 1) Radiation-sensitive composition according to claim 1, wherein the coinitiator (c) is selected from metallocenes, triarylimidazolyl dimers and mixtures thereof. ### Claim 5 (depends on 1) Radiation-sensitive composition according to claim 1, additionally comprising one or more onium salts. ### Claim 6 (depends on 1) Radiation-sensitive element comprising (a) an optionally pretreated substrate and (b) a radiation-sensitive coating consisting of a composition as defined in claim 1 applied on the substrate. ### Claim 7 (depends on 6) Radiation-sensitive element according to claim 6, wherein the substrate is an aluminum foil or plate. ### Claim 8 (depends on 7) Radiation-sensitive element according to claim 7, wherein prior to coating, the aluminum plate or foil is subjected to at least one treatment selected from graining, anodizing and hydrophilizing. ### Claim 9 (depends on 6) Radiation-sensitive element according to claim 6, wherein the element furthermore comprises an oxygen-impermeable overcoat. ### Claim 10 (depends on 6) Process for imaging a radiation-sensitive element comprising (a) providing a radiation-sensitive element as defined in claim 6; (b) image-wise irradiation of the element with UV radiation of >300 nm; (c) optionally heating of the irradiated element; (d) removing the non-irradiated areas of the coating by means of an aqueous alkaline developer; (e) optionally heating the developed element and/or subjecting it to overall exposure. ### Claim 11 (depends on 10) Process according to claim 10, wherein the image-wise irradiation is carried out with UV radiation of a wavelength in the range of 350 to 450 nm. ### Claim 12 (depends on 10) Imaged element obtainable according to the process of claim 10. ### Claim 13 (depends on 12) Imaged element according to claim 12, wherein the element is a lithographic printing form. ### Claim 14 Process for producing a radiation-sensitive element comprising (a) providing an optionally pretreated substrate, (b) providing a radiation-sensitive composition comprising (i) one or more types of monomers and/or oligomers and/or polymers, each comprising at least one ethylenically unsaturated group accessible to a free-radical polymerization, (ii) at least one sensitizer, (iii) at least one coinitiator capable of forming free radicals together with the sensitizer (b) and selected from the following classes of compounds: metallocenes; 1,3,5-triazine derivatives with one to three CX3 groups, wherein X represents chlorine or bromine; peroxides; hexaarylbiimidazoles; oxime ethers; oxime esters; N-aryl glycines and derivatives thereof; thiol compounds; N-aryl, S-aryl and O-aryl polycarboxylic acids with at least 2 carboxyl groups of which at least one is bonded to the N, S or O atom of the aryl unit; alkyltriarylborates; benzoin ethers; benzoin esters; trihalogenomethylarylsulfones; amines; N,N-dialkylaminobenzoic acid esters; aromatic sulfonyl halides; trihalogenomethylsulfones; imides; diazosulfonates; 9,10-dihydroanthracene derivatives; α-hydroxy and a-amino acetophenones; and (iv) optionally one or more components selected from alkali-soluble binders, colorants, exposure indicators, plasticizers, chain transfer agents, leuco dyes, surfactants, inorganic fillers and thermopolymerization inhibitors, (v) at least one solvent, characterized in that the sensitizer is an oxazole derivative of the formula (I) wherein each R1, R2 and R3 is independently selected from a halogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, which may also be fused, an optionally substituted aralkyl group, a group —NR4R5 and a group —OR6, wherein R4 and R5 are independently selected from a hydrogen atom, an alkyl, aryl or aralkyl group, R6 is an alkyl, aryl or aralkyl group or a hydrogen atom and k, m and n are independently 0 or an integer from 1 to 5; c) applying the radiation-sensitive composition provided in step (b) onto the substrate provided in step (a); d) drying. ### Claim 15 (depends on 14) Process according to claim 14, wherein the substrate provided in step (a) is an aluminum substrate that has been subjected to at least one treatment selected from graining, anodizing and application of a hydrophilizing layer. ### Claim 16 (canceled)