# US 5,350,814 A · Unsaturated polyester-epoxy resin network composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,350,814 A - Document ID: US5350814A - Status: Granted - Kind: A - Application number: 08/103,611 - Filed: 1993-08-06 - Granted: 1994-09-27 - Earliest claimed: 1992-04-27 - Assignees: GenCorp Inc. - Inventors: Frederick J. McGarry; Ramnath Subramaniam - Web page: https://patentgrep.com/patent/US5350814A ## CPC - C08L 63/10: Epoxy resins modified by unsaturated compounds - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08L 67/06: Unsaturated polyesters - Y10S 525/942: Polymer derived from nitrile, conjugated diene and aromatic co-monomers - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract A unsaturated polyester resin composition is described that contains an epoxy resin reacted with an amine-terminated flexible polymer while dissolved in the unsaturated polyester resin and its ethylenically unsaturated crosslinking monomer. A compatible system results from the reaction which has a controllable modulus based on the amount of flexible polymer included in the resin. The resin is generally transparent if unfilled and has a higher calculated fracture energy than similar unsaturated polyester resin without modification. The unsaturated polyester resin can be filled with particulate filler or reinforced with fibrous fillers. ## Claims ### Claim 1 A reaction product of a mixture comprising: a) an unsaturated polyester resin, b) one or more ethylenically unsaturated monomers, c) an epoxy resin having 2 or more epoxy groups per molecule, d) an amine-terminated flexible polymer, said polymer having a tg of 0.degree. C. or less and from about 1.7 to about 3 primary or secondary amine groups per polymer, and e) a catalyst component for amine-epoxy reactions, and f) a free radical initiator; wherein said epoxy resin, said amine-terminated flexible polymer, and said catalyst component for amine-epoxy reactions are reacted in the presence of said one or more ethylenically unsaturated monomers and said unsaturated polyester resin to form a composition having a single Tg value by dynamic mechanical analysis when cured. ### Claim 2 (depends on 1) A reaction product as set forth in claim 1, wherein said unsaturated polyester and said ethylenically unsaturated monomers are present in combination from about 30 to about 80 parts by weight; wherein said unsaturated polyester is a 500 to 10,000 molecular weight reaction product of diols having from 2 to 12 carbon atoms with dicarboxylic acids or their anhydrides having from 3 to 12 carbon atoms, wherein said epoxy resin is present from about 10 to about 23 parts by weight; wherein said amine-terminated flexible polymer is present from about 1 to about 47 parts by weight; wherein a catalyst component is present from about 0.1 to about 15 parts by weight; wherein all parts by weight are based on 100 parts by weight of combined components of said composition of epoxy resin, unsaturated polyester resin, ethylenically unsaturated monomers, and amine-terminated flexible polymer. ### Claim 3 (depends on 2) A reaction product as set forth n claim 2, wherein said amine-terminated flexible polymer is present from about 1 to about 23 parts by weight. ### Claim 4 (depends on 3) A reaction product as set forth in claim 3, wherein said amine-terminated flexible polymer is present from about 6 to 23 parts by weight. ### Claim 5 (depends on 3) A reaction product as set forth in claim 3, used as a molding compound with fibers wherein said fibers are present from 5 to 85 percent by weight in the reaction product. ### Claim 6 (depends on 2) A reaction product as set forth in claim 2, wherein said polyester and said ethylenically unsaturated monomers are present in combination from about 40 to about 80 parts by weight; wherein said epoxy resin is present from about 13 to about 20 parts by weight; wherein said amine-terminated flexible polymer is present from about 1 to about 23 parts by weight; wherein said catalyst component is present from about 0.2 to about 10 parts by weight; wherein all parts by weight are based on 100 parts by weight of said composition of epoxy resin, unsaturated polyester resin, ethylenically unsaturated monomers, and amine-terminated flexible polymer; wherein said ethylenically unsaturated monomers is styrene; and wherein said polymer is used to make structural components. ### Claim 7 (depends on 6) A reaction product as set forth in claim 6, wherein said epoxy resin is polyglycidyl ether of bisphenol A, epoxy phenol novolak, or triglycidyl isocyanurate. ### Claim 8 (depends on 2) A reaction product as set forth in claim 2, wherein said amine-terminated flexible polymer is an anime-terminated butadiene-acrylonitrile copolymer. ### Claim 9 (depends on 8) A reaction product as set forth in claim 8, wherein the epoxy resin is a polyglycidly ether of bisphenol A. ### Claim 10 (depends on 9) A reaction product as set forth in claim 9, wherein the amine-terminated butadiene acrylonitrile copolymer is made by reacting a carboxyl or ester-terminated butadiene-acryonitrile copolymer with a heterocyclic amine species having at least two primary and/or secondary amine groups. ### Claim 11 (depends on 5) A reaction product as set forth in claim 5, wherein the amine-terminated flexible polymer is an amine-terminated butadiene-acrylonitrile copolymer. ### Claim 12 (depends on 11) A reaction product as set forth in claim 11, wherein said epoxy resin is a polyglycidyl ether of bisphenol A and/or epoxy phenol novolak. ### Claim 13 (depends on 12) A reaction product as set forth in claim 12, wherein the amine-terminated flexible polymer is made by reacting a carboxyl or ester-terminated butadiene-acrylonirile copolymer with a heterocyclic amine species having at least two primary and/or secondary amine groups. ### Claim 14 (depends on 2) A cured thermoset plastic material formed from a reaction product as set forth in claim 2, wherein the cured composition from an unsaturated polyester resin, ethylenically unsaturated monomers, epxoy resin, and amine-terminated flexible polymer has only one broad Tg in dynamic mechanical analyses. ### Claim 15 (depends on 6) A cured thermoset plastic material formed from a reaction product as set forth in claim 6, wherein the cured composition from an unsaturated polyester resin, ethylenically unsaturated monomers, epoxy resin, and amine-terminated flexible polymer has a single Tg in dynamic mechanical analyses. ### Claim 16 (depends on 5) A cured thermoset plastic material formed from a reaction product as set forth in claim 5, wherein the cured composition from an unsaturated polyester resin, ethylenically unsaturated monomers, epoxy resin, and amine-terminated flexible polymer has a single Tg in dynamic mechanical analyses. ### Claim 17 A process for making a themoset unsaturated polyester composition comprising mixing one or more unsaturated polyester resins, one or more ethylenically unsaturated monomers, and a free radical initiator; wherein the improvement comprises reacting an amine-terminated flexible polymer having a Tg of 0.degree. C. or less and having from 1.7 to about 3 primary or secondary amine groups per molecule with an epoxy resin having 2 or more epoxy groups per molecule in the presence of said one or more unsaturated polyester resins and said one or more ethylenically unsaturated monomers forming a modified polymer network that upon curing has a single Tg and flexibility greater than that of similar networks without the flexible polymer. ### Claim 18 (depends on 17) A process according to claim 17, wherein said amine-terminated flexible polymer is a butadiene-acrylonitrile copolymer and wherein said composition is reinforced with fibers. ### Claim 19 (depends on 18) A process according to claim 18, wherein the epoxy resin comprises a polyglycidyl ether of bisphenol A.