# US 2014/0194575 A1 · Crosslinkable bioplasticizers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0194575 A1 - Document ID: US20140194575A1 - Status: Published application - Kind: A1 - Application number: 14/234,396 - Filed: 2012-07-25 - Published: 2014-07-10 - Earliest claimed: 2011-07-27 - Assignees: PolyOne Corporation - Inventors: Roger W. Avakian; Ling Hu - Web page: https://patentgrep.com/patent/US20140194575A1 ## CPC - C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers - C08G 59/027: {obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer} - C08G 59/42: Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof - C08J 3/18: Plasticising macromolecular compounds (plasticisers C08K) - C08K 5/1539: Cyclic anhydrides - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08L 67/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) - C08J 2327/16: Homopolymers or copolymers of vinylidene fluoride - C08J 2367/04: Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2367/06 takes precedence) - C08K 5/0016: {Plasticisers} - C08K 5/092: Polycarboxylic acids - C08L 91/00: Compositions of oils, fats or waxes; Compositions of derivatives thereof - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A crosslinkable bioplasticizer is disclosed, a mixture of an epoxy-functional bio-derived plasticizer and an aromatic dianhydride. When heated, the mixture crosslinks, which can be accelerated by the addition of a Lewis Acid metal catalyst. The crosslinked bioplasticizer can be melt compounded into a thermoplastic resin or can be formed in situ in the thermoplastic resin. The crosslinking of the bioplasticizer can reduce blooming of the bioplasticizer to the surface of a plastic article made by extrusion, molding, calendering, or thermoforming techniques. ## Claims ### Claim 1 A crosslinkable bioplasticizer mixture, comprising: (a) an epoxy-functional bio-derived plasticizer and (b) an effective amount of an aromatic dianhydride, wherein when heated, the mixture crosslinks to form a crosslinked bioplasticizer. ### Claim 2 (depends on 1) The mixture of claim 1, wherein the mixture further comprises a Lewis Acid metal catalyst, and wherein when heated in the presence of the catalyst, the mixture crosslinks to form a crosslinked bioplasticizer more rapidly than the mixture crosslinks without the presence of the catalyst. ### Claim 3 (depends on 1) The mixture of claim 1, wherein the epoxy-functional bio-derived plasticizer comprises a fatty acid product derived from a vegetable oil having at least 80% by weight of unsaturated fatty acids, wherein said unsaturated fatty acids are substantially fully esterified with a monool or a polyol, and said esterified unsaturated fatty acids have been substantially fully epoxidized. ### Claim 4 (depends on 1) The mixture of claim 1, wherein the epoxy-functional bio-derived plasticizer comprises one or more monoesters or one or more multiesters of epoxidized vegetable oils or combinations thereof. ### Claim 5 (depends on 1) The mixture of claim 1, wherein the epoxy-functional bio-derived plasticizer is an epoxy-functional fatty acid ester obtained from a vegetable oil selected from the group consisting of soybean oil, canola oil, corn oil, linseed oil, rapeseed oil, safflower oil, sunflower oil, tall oil, tung oil, and mixtures and derivatives thereof. ### Claim 6 (depends on 1) The mixture of claim 1, wherein the epoxy-functional bio-derived plasticizer is an epoxidized fatty acid ester of an unsaturated fatty acid selected from the group consisting of oleic, linolenic, and linoleic acids, and combinations thereof. ### Claim 7 (depends on 1) The mixture of claim 1, wherein the epoxy-functional bio-derived plasticizer is an epoxidized soyate selected from the group consisting of epoxidized pentaerythritol tetrasoyate; epoxidized propylene glycol disoyate; epoxidized ethylene glycol disoyate; epoxidized methyl soyate; epoxidized sucrose octasoyate; the epoxidized product of soybean oil interesterified with linseed oil; and combinations thereof. ### Claim 8 (depends on 1) The mixture of claim 1, wherein the aromatic anhydride is pyromellitic dianhydride present in an amount from about 1 to about 50 parts per one hundred parts of the epoxy-functional bio-derived plasticizer. ### Claim 9 (depends on 1) The mixture of claim 1, wherein the aromatic anhydride is pyromellitic dianhydride. ### Claim 10 (depends on 1) The mixture of claim 1, wherein the catalyst is butyl tin tris(2-ethyl hexanoate). ### Claim 11 (canceled) ### Claim 12 (depends on 1) A thermoplastic compound comprising (a) a thermoplastic resin and (b) the crosslinkable bioplasticizer of claim 1. ### Claim 13 (depends on 12) The compound of claim 12, wherein the thermoplastic resin is selected from the group consisting of polyvinyl chloride, polylactic acid, and poly(meth)acrylate. ### Claim 14 (depends on 1) A method of making a crosslinked bioplasticizer of claim 1, comprising the steps of: (a) mixing the aromatic dianhydride and the epoxy-functional bio-derived plasticizer in a heated environment and optionally, (b) introducing an effective amount of Lewis Acid metal catalyst, wherein the aromatic dianhydride and the epoxy-functional bioplasticizer react to form the crosslinked bioplasticizer. ### Claim 15 (canceled) ### Claim 16 (depends on 14) The method of claim 14, wherein the heated environment of step (a) is between 150° C. and 160° C.