# US 11,306,169 B2 · Pressure sensitive adhesive compositions and methods for preparing same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,306,169 B2 - Document ID: US11306169B2 - Status: Granted - Kind: B2 - Application number: 16/057,194 - Filed: 2018-08-07 - Published: 2019-05-09 - Granted: 2022-04-19 - Earliest claimed: 2015-08-05 - Assignees: Synthomer USA LLC - Applicants: Synthomer USA LLC - Inventors: Jong S. Guo; Peter L. Shaw - Web page: https://patentgrep.com/patent/US11306169B2 ## CPC - C08F 220/1808: {C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate} - C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} - C09J 7/385: {Acrylic polymers} - C09J 133/066: {containing -OH groups} - C08F 220/1804: {C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate} - C08F 220/1811: {C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate} - C08F 2800/20: as weight or mass percentages - C09J 2301/408: additives as essential feature of the adhesive layer - C09J 2301/414: presence of a copolymer - C09J 2423/00: Presence of polyolefin - C09J 2433/00: Presence of (meth)acrylic polymer - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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) ## Abstract A pressure sensitive adhesive composition is described. The pressure sensitive adhesive composition includes a polymerization product of a monomer mixture. The monomer mixture includes the following components: (a) at least one alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylates; (b) at least one vinyl ester of a C4-C20 carboxylic acid; (c) at least one hydroxyl functional (meth)acrylate monomer, or at least one epoxy functional (meth)acrylate monomer; (d) at least one ureido substituted ethylenically unsaturated monomer; and one or more optional monomer components (e)-(g). The pressure sensitive adhesive composition provides a desirable combination of low and high temperature performance, and good adhesion to both metal and organic polymer surfaces. ## Claims ### Claim 1 A pressure sensitive adhesive composition comprising a polymerization product of a monomer mixture, the monomer mixture comprising the following components: (a) one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate, wherein the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate comprises at least one low Tg monomer that produces a homopolymer having a Tg of less than −20° C., and wherein the sum of all of the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate is more than 30 wt. %; (b) 0.1 to less than 25 wt. % of a vinyl ester of versatic acid; (c) 0.1 to 8 wt. % of at least one hydroxyl functional (meth)acrylate monomer, or 0.1 to 10 wt. % of at least one epoxy functional (meth)acrylate monomer; (d) 0.05 to 3 wt. % of least one ureido substituted ethylenically unsaturated monomer; (e) optionally 0 to 6 wt. % at least one ethylenically unsaturated carboxylic acid; [[and]] (f) optionally 0 to 20 wt. % of at least one vinyl aromatic monomer; and (g) optionally 0 to 25 wt. % of at least one ethylenically unsaturated monomer different from monomers (a) to (f), wherein the wt. % is based on the total weight of the monomer mixture. ### Claim 2 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein component (a) further comprises at least one medium Tg monomer that produces a homopolymer having a Tg of greater than or equal to −20° C. and less than or equal to 50° C. ### Claim 3 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein component (a) further comprises at least one high Tg monomer that produces a homopolymer having a Tg greater than 50° C. ### Claim 4 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein component (a) further comprises a second low Tg monomer. ### Claim 5 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the sum of all of the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate is between 70 to 92% by weight of monomers (a) to (g). ### Claim 6 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the at least one ureido substituted ethylenically unsaturated monomer of component (d) comprises at least two ureido substituted ethylenically unsaturated monomers. ### Claim 7 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate of component (a) is a C1-C18 alkyl (meth)acrylate. ### Claim 8 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein component (c) comprises the at least one hydroxyl functional (meth)acrylate monomer (c), and the at least one hydroxyl functional (meth)acrylate monomer (c) is a C1-C17 hydroxy alkyl (meth)acrylate. ### Claim 9 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein component (c) comprises the at least one epoxy functional (meth)acrylate monomer (c), and the at least one epoxy functional (meth)acrylate monomer (c) is selected from glycidyl (meth)acrylate, C1-C17 hydroxyalkyl (meth)acrylate glycidyl ether, and combinations thereof. ### Claim 10 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the at least one hydroxyl functional (meth)acrylate monomer (c) is selected from hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutylacrylate, hydroxybutyl(meth)acrylate, hydroxyhexyl acrylate, hydroxyhexyl methacrylate, hydroxyethylhexyl acrylate, hydroxyethylhexyl methacrylate, and combinations thereof. ### Claim 11 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the at least one ureido substituted ethylenically unsaturated monomer component (d) is selected from ureido substituted (meth)acrylate monomers, ureido substituted allyl monomers, and combinations thereof. ### Claim 12 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the at least one vinyl aromatic monomer (f) is selected from the group consisting of styrene, methylstyrene, tert-butylstyrene, dimethyl styrene, ethylstyrene, diisopropylstyrene, dimethylstyrene, butyl-methylstyrene, chlorostyrene, bromostyrene methyl-dichlorostyrene, dibromostyrene, vinylnaphthalene, vinyltoluene, vinylxylene, vinylpyridine, diphenylethylenes, substituted diphenylethylenes, and mixtures thereof. ### Claim 13 (depends on 1) The pressure sensitive adhesive composition of claim 1, further comprising tackifiers or polyolefin emulsions or combinations thereof. ### Claim 14 (depends on 1) The pressure sensitive adhesive composition of claim 1, wherein the at least one ethylenically unsaturated monomer component (g) is selected from the group consisting of vinyl esters of C1-C3 carboxylic acid monomers, nitriles of ethylenically unsaturated carboxylic acids, ethylenically unsaturated surfactants, and combinations thereof. ### Claim 15 A method for making a polymerization product comprising reacting a monomer mixture comprising the following components: (a) one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate, wherein the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate comprises at least one low Tg monomer that produces a homopolymer having a Tg of less than −20° C., and wherein the sum of all of the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate is more than 30 wt. %; (b) 0.1 to less than 25 wt. % of a vinyl ester of versatic acid; (c) 0.1 to 8 wt. % of at least one hydroxyl functional (meth)acrylate monomer, or 0.1 to 10 wt. % of at least one epoxy functional (meth)acrylate monomer; (d) 0.05 to 3 wt. % of least one ureido substituted ethylenically unsaturated monomer; (e) optionally 0 to 6 wt. % at least one ethylenically unsaturated carboxylic acid; (f) optionally 0 to 20 wt. % of at least one vinyl aromatic monomer; and (g) optionally 0 to 25 wt. % of at least one ethylenically unsaturated monomer different from monomers (a) to (f), wherein the wt. % is based on the total weight of the monomer mixture. ### Claim 16 (depends on 15) The method according to claim 15, further comprising subjecting the product to treatment with glycidyl alkyl compounds or diol compounds to at least partially convert structural units resulting from polymerization of the at least one ethylenically unsaturated carboxylic acid (e) into structural units which can result from polymerization of the at least one hydroxy] functional (meth)acrylate monomer (c). ### Claim 17 (depends on 15) The method according to claim 15, wherein component (a) further comprises at least one medium Tg monomer that produces a homopolymer having a Tg of greater than or equal to −20° C. and less than or equal to 50° C. ### Claim 18 (depends on 15) The method according to claim 15, wherein component (a) further comprises at least one high Tg monomer that produces a homopolymer having a Tg greater than 50° C. ### Claim 19 An article made by a process comprising reacting a monomer mixture comprising the following components: (a) one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylates, wherein the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate comprises at least one low Tg monomer that produces a homopolymer having a Tg of less than −20° C., and wherein the sum of all of the one or more alkyl ester of (meth)acrylic acid or cyclic hydrocarbon acrylate is more than 30 wt. %; (b) 0.1 to less than 25 wt. % of a vinyl ester of versatic acid; (c) 0.1 to 8 wt. % of at least one hydroxyl functional (meth)acrylate monomer, or 0.1 to 10 wt. % of at least one epoxy functional (meth)acrylate monomer; (d) 0.05 to 3 wt. % of least one ureido substituted ethylenically unsaturated monomer; (e) optionally 0 to 6 wt. % at least one ethylenically unsaturated carboxylic acid; [[and]] (f) optionally 0 to 20 wt. % of at least one vinyl aromatic monomer; and (g) optionally 0 to 25 wt. % of at least one ethylenically unsaturated monomer different from monomers (a) to (f), wherein the wt. % is based on the total weight of the monomer.