# US 7,612,130 B2 · Composition of polyester, aromatic epoxy compound and epoxy-functional polyolefin and/or copolyester > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,612,130 B2 - Document ID: US7612130B2 - Status: Granted - Kind: B2 - Application number: 11/581,247 - Filed: 2006-10-16 - Published: 2008-04-17 - Granted: 2009-11-03 - Earliest claimed: 2006-10-16 - Assignees: Sabic Innovative Plastics IP B.V. - Inventors: Sung Dug Kim - Web page: https://patentgrep.com/patent/US7612130B2 ## CPC - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) - C08K 3/40: Glass - C08L 23/02: not modified by chemical after-treatment - C08L 23/0884: Epoxide-containing esters - C08L 67/025: {containing polyether sequences} - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A composition contains a polyester; an aromatic epoxy compound, in an amount sufficient to provide 5 to 300 milliequivalents of epoxy per kilogram of polyester; and 0.5 to 6 weight percent, based on the weight of the polyester, and an ethylene-glycidyl methacrylate containing copolymer; and/or a copolyester copolymer, wherein the copolyester comprises, based on the weight of the copolyester, 15 to 95 weight percent of polyester units derived from the reaction of a C6-C24 aromatic dicarboxylic acid or a chemical equivalent thereof with a C2-C6 aliphatic diol, and 5 to 85 weight percent of polyester units derived from the reaction of a C6-C24 aromatic dicarboxylic acid or a chemical equivalent thereof with a poly(alkylene oxide) glycol having a molecular weight of 400-6,000 and a carbon to oxygen ratio of 2.0-4.3. The compositions have excellent hydrolytic resistance, and are suitable for making automotive and electronic parts. ## Claims ### Claim 1 A composition, comprising: a polyester; an aromatic epoxy compound, in an amount sufficient to provide 5 to 300 milliequivalents of epoxy per kilogram of polyester; and from 0.5 to 6 weight percent, based on the weight of the polyester, an epoxy-functional polyolefin; and a copolyester copolymer, wherein the copolyester comprises, based on the weight of the copolyester, 15 to 95 weight percent of polyester units derived from the reaction of a C6-C24 aromatic dicarboxylic acid or a chemical equivalent thereof with a C2-C6 aliphatic diol, and 5 to 85 weight percent of polyester units derived from the reaction of a C6-C24 aromatic dicarboxylic acid or a chemical equivalent thereof with a poly(alkylene oxide) glycol having a molecular weight of 400 to 6,000 and a carbon to oxygen ratio from 2.0 to 4.3. ### Claim 2 (depends on 1) The composition of claim 1, wherein an article comprising the composition has an initial tensile stress at break, and wherein the article retains 8000 or more of the initial tensile stress at break after aging at 110° C. at 1075 mmHg (0.143 Mpa) for 48 hours at 100% relative humidity, wherein the tensile stress at break is measured in accordance with ASTM D638. ### Claim 3 (depends on 1) The composition of claim 1, wherein an article comprising the composition has an initial tensile stress at break, and wherein the article retains 70% or more of the initial tensile stress at break after aging at 110° C. at 1075 mmHg (0.143 Mpa) for five days at 100% relative humidity, wherein the tensile stress at break is measured in accordance with ASTM D638. ### Claim 4 (depends on 1) The composition of claim 1, wherein an article comprising the composition has an initial tensile strength, and wherein the article retains more of the initial tensile strength after aging at 110° C. at 1075 mmHg (0.143 Mpa) for 120 hours at 100% relative humidity relative to a composition without the aromatic epoxy compound and epoxy-functional polyolefin and/or copolyester, wherein the tensile strength is measured in accordance with ASTM D638. ### Claim 5 (depends on 1) The composition of claim 1, wherein the polyester is poly(ethylene terephthalate), poly(1,4-butylene terephthalate), poly(ethylene naphthalate), poly(butylene naphthalate), (polytrimethylene terephthalate), poly(1,4-cyclohexylenedimethylene 1,4-cyclohexanedicarboxylate), poly(1,4-cyclohexylenedimethylene terephthalate) poly(cyclohexylenedimethylene-co-ethylene terephthalate), or a combination comprising at least one of the foregoing polyesters. ### Claim 6 (depends on 5) The composition of claim 5, wherein the polyester is poly(butylene terephthalate), poly(ethylene terephthalate), a combination of poly(ethylene naphthalate) and poly(butylene naphthalate), or poly(trimethylene terephthalate). ### Claim 7 (depends on 5) The composition of claim 5, wherein the polyester is poly(butylene terephthalate). ### Claim 8 (depends on 1) The composition of claim 1, wherein the aromatic epoxy compound has an epoxy equivalent weight of 100 to 3,000. ### Claim 9 (depends on 1) The composition of claim 1, wherein the aromatic epoxy compound is of the formula wherein Ra′ and Rb′ are each independently halogen or C1-C12 alkyl, Xa is a substituted or unsubstituted C1-C18 alkylidene bridging group or a substituted or unsubstituted C3-C18 cycloalkylidene bridging group, n is 1 to 6, and r and s are each independently 0 to 4. ### Claim 10 (depends on 1) The composition of claim 1, wherein the aromatic epoxy compound is of the formula wherein Xa is a substituted or unsubstituted C1-18 alkylidene bridging group or a substituted or unsubstituted C3-18 cycloalkylidene bridging group, n is 1 to 6, and x and y are each independently 0 to 4. ### Claim 11 (depends on 1) The composition of claim 1, wherein the epoxy-functional polyolefin copolymer comprises units derived from glycidyl (meth)acrylate. ### Claim 12 (depends on 1) The composition of claim 1, wherein the epoxy-functional polyolefin copolymer is a terpolymer comprising units derived from ethylene, glycidyl methacrylate, and methyl acrylate. ### Claim 13 (depends on 1) The composition of claim 1, wherein the C2-C6 aliphatic diol of the copolyester copolymer is butanediol and the poly(alkylene oxide) glycol is poly(tetramethylene oxide) glycol having a molecular weight of 600-2,000. ### Claim 14 (depends on 1) The composition of claim 1, further comprising a catalyst, wherein the catalyst is a hydroxide, hydride, amide, carbonate, borate, phosphate, C2-18 enolate, C2-36 dicarboxylate, or C2-36 carboxylate of a metal; a Lewis acid catalyst; a tetraalkyl ammonium hydroxide or acetate; a C1-36 tetraalkyl phosphonium hydroxide or acetate; an alkali or alkaline earth metal salt of a negatively charged polymer; or a combination comprising at least one of the foregoing catalysts. ### Claim 15 (depends on 11) The composition of claim 11, wherein the catalyst is sodium stearate, sodium carbonate, sodium acetate, sodium bicarbonate, sodium benzoate, sodium caproate, potassium oleate, a boron compound, or a mixture comprising at least one of the foregoing salts. ### Claim 16 (depends on 1) The composition of claim 1, further comprising an antioxidant, a particulate filler, a reinforcing filler, a colorant, a mold release agent, a nucleating agent, a UV light stabilizer, a heat stabilizer, a lubricant, or a combination comprising at least one of the foregoing additives. ### Claim 17 (depends on 13) The composition of claim 13, further comprising 5 to 50 weight percent of reinforcing filler, based on the total weight of the composition. ### Claim 18 (depends on 17) The composition of claim 17 wherein reinforcing filler comprises short glass fibers and/or long glass fibers. ### Claim 19 (depends on 1) The composition of claim 1, further comprising 0.1 to 30 weight percent of an acrylic impact modifier, based on the total weight of the composition. ### Claim 20 (depends on 19) The composition of claim 19, wherein the acrylic impact modifier comprises a multi-phase composite interpolymer comprising 25 to 95 weight percent of a first acrylic electrometric phase polymerized from a monomer system comprising 75 to 99.8% by weight C1 to C14 alkyl acrylate, 0.1 to 5% by weight crosslinking member, 0.1 to 5% by weight graftlinking monomer, said crosslinking monomer being a polyethylenically unsaturated monomer having a plurality of addition polymerizable reactive groups and 75 to 5 weight percent of a final, rigid thermoplastic acrylic or methacrylic phase polymerized in the presence of said elastomer. ### Claim 21 (depends on 1) The composition of claim 1 further comprising a polycarbonate, polyamide, polyolefin, polyphenylene ether, polyphenylene sulfide, or polyetherimide. ### Claim 22 (depends on 1) The composition of claim 1, wherein the composition further comprises a flame retarding component. ### Claim 23 (depends on 1) An article comprising the composition of claim 1. ### Claim 24 (depends on 23) The article of claim 23, in the form of a component of an automotive part. ### Claim 25 (depends on 1) A method of forming an article, comprising shaping, extruding, or molding the composition of claim 1 to form the article. ### Claim 26 (depends on 1) A method of forming a composition, comprising blending the components of the composition of claim 1. ### Claim 27 A composition, comprising: (a) a polyester component selected from the group consisting of poly(ethylene terephthalate), poly(1,4-butylene terephthalate), poly(ethylene naphthalate), poly(butylene naphthalate), (polytrimethylene terephthalate), poly(1,4-cyclohexylenedimethylene 1,4-cyclohexanedicarboxylate), poly(1,4-cyclohexylenedimethylene terephthalate) poly(cyclohexylenedimethylene-co-ethylene terephthalate), and combinations thereof; (b) a glass filler; (c) a aromatic epoxy compound is of the formula wherein Xa is a substituted or unsubstituted C1-18 alkylidene bridging group or a substituted or unsubstituted C3-18 cycloalkylidene bridging group, n is 1 to 6, and x and y are each independently 0 to 4, in an amount sufficient to provide 5 to 300 milliequivalents of epoxy per kilogram of polyester; an alkali metal salt of a C8-C36 carboxylic acid catalyst; and 0.5 to 6 weight percent, based on the weight of the polyester, of both of (d) an ethylene-methyl acrylate-glycidyl methacrylate terpolymer and a copolyester copolymer wherein the copolyester comprises, based on the weight of the copolyester, (e) 15 to 95 weight percent of polyester units derived from the reaction of terephthalic acid or chemical equivalent thereof with butanediol, and (f) 5 to 85 weight percent of polyester units derived from the reaction of a terephthalic acid and poly(tetramethylene oxide) glycol having a molecular weight of 600-2,000. ### Claim 28 A composition, comprising: a polybutylene terephthalate polyester; a glass filler; an aromatic epoxy compound is of the formula wherein Xa is isopropylidene, n is 1 to 6, and x and y are each independently 0 to 2, in an amount sufficient to provide 5 to 300 milliequivalents of epoxy per kilogram of polyester; an alkali metal salt of a C8-C36 carboxylic acid catalyst; and 0.5 to 6 weight percent, based on the weight of the polyester, of both of an ethylene-methyl acrylate-glycidyl methacrylate terpolymer and a copolyester copolymer wherein the copolyester comprises, based on the weight of the copolyester, 15 to 95 weight percent of polyester units derived from the reaction of terephthalic acid or chemical equivalent thereof with butanediol, and 5 to 85 weight percent of polyester units derived from the reaction of a terephthalic acid and poly(tetramethylene oxide) glycol having a molecular weight of 600-2,000.