# US 9,434,814 B2 · Unsaturated polyester resin compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,434,814 B2 - Document ID: US9434814B2 - Status: Granted - Kind: B2 - Application number: 14/155,811 - Filed: 2014-01-15 - Published: 2014-05-08 - Granted: 2016-09-06 - Earliest claimed: 2006-07-06 - Assignees: Dsm IP Assets B.V. - Applicants: Dsm IP Assets B.V. - Inventors: Johan Franz Gradus Antonius Jansen; Ronald Ivo Kraeger - Web page: https://patentgrep.com/patent/US9434814B2 ## CPC - C08G 63/91: Polymers modified by chemical after-treatment - C08F 283/01: on to unsaturated polyesters {(C08F283/004 takes precedence)} - C08K 5/098: Metal salts of carboxylic acids - C08K 5/14: Peroxides - C08K 5/17: Amines; Quaternary ammonium compounds - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract The present invention relates to a two-component composition comprising a first component and a second component, wherein the first component being a pre-accelerated resin composition comprising an unsaturated polyester resin or vinyl ester resin and a copper2+ compound, at least one N-containing organic base selected from an amine compound and/or an ammonium salt; and wherein copper is present in an amount of at least 50 ppm (relative to the primary resin system), wherein the resin composition contains less than 0.01 mmol cobalt per kg primary resin system, the resin composition has an acid value in the range of from 0.001-300 mg KOH/g of resin composition, the molecular weight of the resin containing reactive unsaturations is in the range of from 500 to 200,000 g/mole and wherein the second component comprises a peroxide compound. ## Claims ### Claim 1 A two-component composition comprising a first component and a second component, wherein the first component is a pre-accelerated resin composition having an acid value in the range of from 0.001-300 mg KOH/g of resin composition, the resin composition comprising (i) an unsaturated polyester resin having a molecular weight in a range of 500 to 200,000 g/mole, (ii) an accelerator consisting essentially of a copper2+ compound in an amount of least 50 ppm, based on the primary resin system, and (iii) at least one N-containing organic base selected from an amine compound and/or an ammonium salt; wherein the amine compound has the following formula: and the ammonium salt has the following formula: R1R2R3N+H whereby R1, R2 and R3 each individually may represent hydrogen (H), C1-C20 alkyl, C5-C20 cycloalkyl or C7-C20 alkylaryl, that each optionally may contain one or more hetero-atoms and/or substituents and a ring may be present between R1 and R2, R2 and R3 and/or R1 and R3, which may contain heteroatoms, wherein the second component comprises a peroxide compound, and wherein the two-component composition contains less than 0.01 mmol cobalt per kg primary resin system, and wherein a molar ratio between the copper and basic functionality of the base is from 40:1 to 1:125. ### Claim 2 (depends on 1) The two-component composition according to claim 1, wherein the copper2+ compound is a copper carboxylate or a copper acetoacetate. ### Claim 3 (depends on 1) The two-component composition according to claim 1, wherein the copper2+ compound is present in an amount of at least 100 ppm relative to the primary resin system. ### Claim 4 (depends on 1) The two-component composition according to claim 1, wherein R1, R2 and R3 arehydrogen. ### Claim 5 (depends on 1) The two-component composition according to claim 1, wherein R1, R2 and R3 each individually may represent a C1-C20 alkyl. ### Claim 6 (depends on 1) The two-component composition according to claim 1, wherein at least one of R1, R2 and R3 is an alkyl-O—R4 group, whereby R4 is hydrogen, a C1-C20 alkyl group or a ring is present between R4 and at least one of the other R groups. ### Claim 7 (depends on 6) The two-component composition according to claim 6, wherein the-O—R4 group is in the β-position with respect to the nitrogen atom. ### Claim 8 (depends on 1) The two-component composition according to claim 1, wherein the amount of the N-containing organic base is from 0.05 to 5% by weight, calculated on the total weight of the primary resin system. ### Claim 9 (depends on 1) The two-component composition according to claim 1, wherein the resin composition further comprises a radical inhibitor. ### Claim 10 (depends on 1) Cured structural parts obtained by curing a two-component composition according to claim 1. ### Claim 11 (depends on 1) A process which comprises radically curing a two-component composition according to claim 1 in the absence of cobalt. ### Claim 12 (depends on 11) The process according to claim 11, wherein the peroxide compound is at least one selected from the group consisting of hydroperoxides, perethers and perketones. ### Claim 13 (depends on 12) The process according to claim 12, wherein the peroxide compound is methylethylketone peroxide. ### Claim 14 (depends on 9) The two-component composition according to claim 9, wherein the radical inhibitor is at least one selected from the group consisting of phenolic compounds, stable radicals, catechols and phenothiazines. ### Claim 15 (depends on 1) The two-component composition according to claim 1, wherein the accelerator consists of the copper2+ compound. ### Claim 16 (depends on 15) previously presented) The two-component coposition according to claim 15, wherein the the copper2+ compound is a copper carboxylate or a copper acetoacetate. ### Claim 17 (depends on 16) The two-component composition according to claim 16, wherein the resin composition consists of (i) the unsaturated polyester resin, (ii) the copper2+ compound, (iii) the at least one N-containing organic base, (iv) and optionally a radical inhibitor. ### Claim 18 (depends on 17) The two-component composition according to claim 17, wherein the N-containing organic base is at least one selected from the group consisting of ammonia, triethylamine, dimethylbenzylamine, ethanol amine, N-methyl ethanolamine, N,N-dimethyl ethanol amine, N,N-diethyl ethanol amine, N,N-dibutyl ethanol amine, 1-amino-2-propanol, choline chloride, morpholine, N-methyl morpholine, ethylene diamine and tetramethyl ethylene diamine. ### Claim 19 A two-component composition comprising first and second components and less than 0.01 mmol cobalt per kg primary resin system, wherein (1) the first component is a resin composition having an acid value in the range of from 0.001-300 mg KOH/g of resin composition, the resin composition comprising; (i) an unsaturated polyester resin having a molecular weight in a range of 500 to 200,000 g/mole, (ii) an amount of least 50 ppm, based on the primary resin system, of an accelerator consisting of a copper2+ compound selected from the group consisting of a copper carboxylate and a copper acetoacetate, and (iii) at least one N-containing organic base selected from the group consisting of ammonia, triethylamine, dimethylbenzylamine, ethanol amine, N-methyl ethanolamine, N,N-dimethyl ethanol amine, N,N-diethyl ethanol amine, N,N-dibutyl ethanol amine, 1-amino-2-propanol, choline chloride, morpholine, N-methyl morpholine, ethylene diamine and tetramethyl ethylene diamine, and wherein (2) the second component comprises a peroxide.