# US 5,710,193 A · Photopolymerisable components of radiation sensitive compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,710,193 A - Document ID: US5710193A - Status: Granted - Kind: A - Application number: 08/646,808 - Filed: 1996-05-21 - Granted: 1998-01-20 - Earliest claimed: 1992-01-21 - Assignees: DuPont (U.K.) Limited - Inventors: John Robert Wade; Michael John Pratt; Jianrong Ren - Web page: https://patentgrep.com/patent/US5710193A ## CPC - G03F 7/031: Organic compounds not covered by group G03F7/029 - C07C 271/24: with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring - C07C 271/28: to a carbon atom of a non-condensed six-membered aromatic ring - C08G 18/329: {containing aromatic groups} - C08G 18/8158: {with unsaturated compounds having only one group containing active hydrogen} - G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) - Y10S 522/904: Monomer or polymer contains initiating group - Y10S 522/905: Benzophenone group - 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) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract Colorants, polymeric binder resins, photoinitiators, photosensitizers, color-change agents, anti-halation agents, stabilizers, and other active hydrogen-containing components of radiation sensitive compositions for lithographic printing plate production and the like are reacted with a polyethylenically unsaturated monoisocyanate compound of the formula ##STR1## wherein Y is the residue of a monohydroxyl compound of formula YOH and Y contains at least two ethylenically unsaturated double bonds. In this way the components are bonded to the image on exposure. ## Claims ### Claim 1 A process for producing a polyunsaturated compound which comprises (a) forming a mono isocyanate compound having the formula ##STR9## by reacting a compound YOH with a polyisocyanate OCN--Z--(NCO).sub.n where n is 1 or 2; Z represents the residue of a polyisocyanate OCN--Z--(NCO).sub.n, and Y is the residue of a monohydroxyl compound of the formula YOH where Y contains at least two ethylenically unsaturated double bonds in a reaction medium in which said compound YOH and said polyisocyanate are miscible and said mono isocyanate compound is immiscible; (b) recovering said mono isocyanate compound from said reaction medium, and reacting a compound of the formula .COPYRGT.-(XH).sub.r with said mono isocyanate compound wherein .COPYRGT. represents the residue of an active hydrogen containing compound of the formula .COPYRGT.-(XH).sub.r where XH is a hydroxyl group, a mercapto group or a primary or secondary amino group; and r is an integer ranging from 1 to 10 for a simple molecule and from 1 to 10,000 for a polymeric macromolecule. ### Claim 2 (depends on 1) The process of claim 1 wherein said compound .COPYRGT.-(XH).sub.r is an organic colorant or a chromophore functioning as a shading dye or colour-change dye, an anti-halation reagent, a photosensitizer, an organic azide photoactive material, a photoinitiator, a polymeric binder resin, or an isocyanate blocking agent. ### Claim 3 (depends on 2) The process of claim 2 wherein said polymeric binder resin is a poly(vinyl acetal), a styrene-allyl alcohol copolymer, an acrylic co- or terpolymer containing hydroxy alkyl methacrylate, a novolak resin or a poly(vinyl phenol). ### Claim 4 (depends on 1) The process of claim 1 wherein said ethylenically unsaturated compound YOH has the formula: ##STR10## where: (i) a is 2 or 3; b, c, and e are 0 or 1; R' is hydrogen or alkyl; (ii) D has the structure: ##STR11## (iii) E has the structure: ##STR12## (iv) B is a single bond, --CH.sub.2 --, or ##STR13## and (v) x is 1 to 3, and R.sup.2 through R.sup.6 are independently H or CH.sub.3. ### Claim 5 A polyunsaturated compound having the general formula: ##STR14## where .COPYRGT. represents the residue of an active hydrogen containing compound of the formula .COPYRGT.-(XH).sub.r where XH is a hydroxyl group, a mercapto group or a primary or secondary amino group; and r is an integer ranging from 1 to 10 for a simple molecule and from 1 to 10,000 for a polymeric macromolecule, Z represents the residue of a polyisocyanate OCN--Z--(NCO).sub.n, where n is 1 or 2; ##STR15## is provided by a pure polyethylenically unsaturated monoisocyanate of the formula ##STR16## and Y is the residue of a monohydroxy compound of formula YOH where Y contains at least two ethylenically unsaturated double bonds, with the proviso that said active hydrogen containing compound is an organic colorant or a chromophore functioning as a shading dye or colour-change dye, an anti-halation reagent, a photosensitizer, an organic azide photoactive material, a photoinitiator, a polymeric binder resin, or an isocyanate blocking agent. ### Claim 6 (depends on 5) The compound of claim 5 wherein said compound .COPYRGT.-(XH).sub.r is an organic anti-halation reagent or a photosensitizer which is a monazo, methine or polycyclic derivative. ### Claim 7 (depends on 5) The compound of claim 5 wherein said polymeric binder resin is a poly(vinyl acetal), a styrene-allyl alcohol copolymer, an acrylic co- or terpolymer containing hydroxy alkyl methacrylate, a novolak resin or a poly(vinyl phenol). ### Claim 8 (depends on 5) The compound of claim 5 wherein said isocyanate blocking agent is an oxime, phenol or caprolactam.