# US 2014/0154506 A1 · Pressure sensitive adhesives prepared from maleated vegetable oils and expoxidized vegetable oils > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0154506 A1 - Document ID: US20140154506A1 - Status: Published application - Kind: A1 - Application number: 14/098,148 - Filed: 2013-12-05 - Published: 2014-06-05 - Earliest claimed: 2012-12-05 - Assignees: Avery Dennison Corporation - Applicants: Avery Dennison Corporation - Inventors: Charles R. WILLIAMS; Qiang LUO; Mark GOWER - Web page: https://patentgrep.com/patent/US20140154506A1 ## CPC - C09J 191/00: Adhesives based on oils, fats or waxes; Adhesives based on derivatives thereof - C09J 7/38: Pressure-sensitive adhesives [PSA] - C09J 163/00: Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins - C09J 2463/00: Presence of epoxy resin - C09J 2491/00: Presence of oils, fats or waxes - Y10T 428/2852: Adhesive compositions - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract A method that includes reacting an epoxidized naturally-occurring oil or fat with a triacid to form a pressure sensitive adhesive or a pressure sensitive adhesive precursor is disclosed. The present invention also includes methods for preparing a triacid and for preparing a pressure sensitive adhesive label or tape. ## Claims ### Claim 1 A method comprising: combining one or more epoxidized naturally-occurring oils or fats with at least one triacid to form a reaction mixture, and applying heat to the reaction mixture to form pressure sensitive adhesive. ### Claim 2 (depends on 1) The method of claim 1 wherein the naturally occurring oil or fat is selected from one or more of soybean oil, palm oil, olive oil, corn oil, canola oil, linseed oil, rapeseed oil, castor oil, coconut oil, cottonseed oil, palm kernel oil, rice bran oil, safflower oil, sesame oil, sunflower oil, tall oil, lard, tallow, fish oil and fats or oils from algae. ### Claim 3 (depends on 1) The method of claim 1, further comprising adding a catalyst to the reaction mixture, wherein the catalyst comprises a compound selected from the group consisting of amines, imidazoles, phenols, and metal complexes. ### Claim 4 (depends on 3) The method of claim 3 wherein the catalysts are selected from the group consisting of dimethyl benzyl amine, triethylamine, triethanolamine, 2-ethyl-4-methylimidazole, 2,4,6-tris(dimethylaminomethyl)phenol, and chromium acetylacetonate. ### Claim 5 (depends on 3) The method of claim 3 wherein the reaction mixture comprises a weight ratio of triacids to epoxidized naturally-occurring oils and fats in the range of about 1:1 to about 5.5:1. ### Claim 6 (depends on 5) The method of claim 5 wherein the reaction mixture comprises a weight ratio of triacids to epoxidized naturally-occurring oils and fats in the range of about 3.5:1 to about 5.0:1. ### Claim 7 (depends on 5) The method of claim 5 wherein the reaction mixture comprises a weight ratio of triacids to epoxidized naturally-occurring oils and fats of about 4.5:1. ### Claim 8 (depends on 1) The method of claim 1 wherein the reaction mixture is heated at a temperature in the range of about 60° C. to about 120° C. ### Claim 9 (depends on 8) The method of claim 8 wherein the reaction mixture is heated between about 30 and about 60 minutes. ### Claim 10 (depends on 1) The method claim 1 further comprising forming the triacid by the steps comprising: mixing a naturally-occurring oil or fat having at least three hydroxyl groups with an anhydride to form an acid formation mixture, and heating the acid formation mixture to form a triacid. ### Claim 11 (depends on 10) The method of claim 10 wherein the acid formation mixture is prepared by mixing a molar ratio of triacid to naturally-occurring oil in the range of about 2.5:1 to about 3:1. ### Claim 12 (depends on 11) The method of claim 11 wherein the acid formation mixture is heated at a temperature between room temperature and about 200° C. from about 2 to about 72 hours. ### Claim 13 (depends on 11) The method of claim 11 wherein the triacid has a functionality of about 2.0 to about 3.0. ### Claim 14 (depends on 11) The method of claims 11 wherein the triacid is castor oil triacid. ### Claim 15 (depends on 11) The method of claim 11 wherein the naturally-occurring oil or fat having at least three hydroxyl groups is castor oil and the anhydride is maleic anhydride. ### Claim 16 (depends on 11) The method of claim 11 wherein the pressure sensitive adhesive has a biocontent between about 20 wt % and about 100 wt %. ### Claim 17 (depends on 1) The method of claim 1 further comprising adding at least one enhancer selected from crosslinkers, catalyst, co-initiators, tackifiers, UV absorber, enhancer, and sensitizers to the reaction mixture. ### Claim 18 (depends on 17) The method of claim 17 wherein the enhancer is selected from one or more of methyltriethoxysilane, tetraethyl orthosilicate, 1,4-cyclohexanedimethanol diglycidyl ether, pentaerythritol, tetra(ethylene glycol dimethyl ether), acetophenone, benzophenone, and anthracene. ### Claim 19 (depends on 1) The method of claim 1 wherein the method further comprises the step of applying the pressure sensitive adhesive to a facestock. ### Claim 20 A pressure sensitive adhesive label or tape, comprising: a facestock comprising an upper face and a lower face; and one or more layers of adhesive disposed on the lower face of the facestock; wherein at least a portion of one layer of the adhesive comprises a compound made by reacting one or more epoxidized naturally-occurring oils or fats with at least one triacid. ### Claim 21 A method for forming a triacid, wherein the method comprises mixing a naturally-occurring oil or fat having at least three hydroxyl groups with an anhydride to form an acid formation mixture, and heating the acid formation mixture to form a triacid. ### Claim 22 (depends on 21) The method of claim 21 wherein the acid formation mixture is prepared by mixing triacid and naturally-occurring oil at a molar ratio of about 2.5:1 to about 3:1. ### Claim 23 (depends on 22) The method of claim 22 wherein the acid formation mixture is heated at a temperature between room temperature and about 200° C. from about 2 to about 72 hours. ### Claim 24 (depends on 23) The method of claim 23 wherein the triacid has a functionality of about 2.0 to about 3.0. ### Claim 25 (depends on 24) The method of claim 24 wherein the triacid is castor oil triacid. ### Claim 26 (depends on 24) The method of claim 24 wherein the castor oil triacid is prepared by reacting a mixture of castor oil and an anhydride. ### Claim 27 (depends on 26) The method of claim 26 wherein the anhydride is maleic anhydride.