# US 8,148,471 B2 · Acrylic pressure-sensitive adhesives with aziridinyl-epoxy crosslinking system > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,148,471 B2 - Document ID: US8148471B2 - Status: Granted - Kind: B2 - Application number: 12/939,205 - Filed: 2010-11-04 - Published: 2011-05-26 - Granted: 2012-04-03 - Earliest claimed: 2009-11-23 - Assignees: 3M Innovative Properties Company - Inventors: Maureen A. Kavanagh; Larry R. Krepski; Kelly S. Anderson; Peiwang Zhu; Belma Erdogan-Haug; Babu N. Gaddam - Web page: https://patentgrep.com/patent/US8148471B2 ## CPC - C08F 2/48: by ultraviolet or visible light - C08F 220/1808: {C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate} - C09J 133/08: Homopolymers or copolymers of acrylic acid esters - C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators} - C08K 5/1515: Three-membered rings - C08K 5/3412: having one nitrogen atom in the ring - 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) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A pre-adhesive composition is described comprising an acid-functional (meth)acrylate copolymer and a crosslinking system comprising an aziridine crosslinking agent and epoxy-functional (meth)acryloyl monomer, which when crosslinked, provides a pressure-sensitive adhesive and pressure-sensitive adhesive articles. ## Claims ### Claim 1 A crosslinkable composition comprising: a) a first component acid-functional acrylic copolymer comprising: i. 85 to 99 parts by weight of an (meth)acrylic acid ester of non-tertiary alcohol; ii. 1 to 15 parts by weight of an acid functional monomer; iii. 0 to 10 parts by weight of a second, non-acid functional, polar monomer; iv. 0 to 5 parts vinyl monomer; and b) a second component epoxy-functional (meth)acryloyl monomer; and c) a third component aziridine crosslinking agent of the formula: wherein R1 is H or C1-C4 alkyl; z is 0, 1 or 2 R2 is a H or C1-C4 alkyl; R3 is a (hetero)hydrocarbyl group: X1 is —O— or —NR1—; Z is —H or a water-solubilizing group. ### Claim 2 (depends on 1) The crosslinkable composition of claim 1, wherein R3 is a hydrocarbyl group and X1 is —O—. ### Claim 3 (depends on 1) The crosslinkable composition of claim 1, wherein Z is a water-solubilizing group. ### Claim 4 (depends on 3) The crosslinkable composition of claim 3 wherein said water-solubilizing group is a cationic, anionic, zwitterionic or nonionic water solubilizing group. ### Claim 5 (depends on 3) The crosslinkable composition of claim 3 wherein Z is Z1, where Z1 is an ionic water solubilizing groups selected from ammonium groups, phosphonium groups, sulfonium groups, carboxylates, sulfonates, phosphates, phosphonates or phosphinate groups. ### Claim 6 (depends on 3) The crosslinkable composition of claim 3 wherein Z is Z2, where Z2 is a poly(oxyalkylene) group. ### Claim 7 (depends on 2) The crosslinkable composition of claim 2 wherein Z is a hydroxyl group. ### Claim 8 (depends on 1) The crosslinkable composition of claim 1 wherein said epoxy-functional (meth)acrylate monomer is of the formula: wherein R2 is a H or C1-C4 alkyl; X1 is —O— or —NR1—; and R5 is an epoxy-containing hydrocarbyl group. ### Claim 9 (depends on 1) The crosslinkable composition of claim 1 comprising 0.005 to 5.0 parts by weight of an aziridine crosslinking agent, relative to 100 parts by weight of said first component acid-functional acrylic copolymer. ### Claim 10 (depends on 1) The crosslinkable composition of claim 1 wherein the epoxy-functional (meth)acrylate monomer is used in amounts up to a stoichiometric equivalent of said aziridine crosslinking agent. ### Claim 11 (depends on 1) The crosslinkable composition of claim 1 wherein the epoxy-functional (meth)acrylate monomer is used in amounts 0.005 to 5.0 parts by weight relative to 100 parts by weight of said first component acid-functional acrylic copolymer. ### Claim 12 (depends on 1) The crosslinkable composition of claim 1 wherein said epoxy-functional (meth)acrylate monomer is of the formula: wherein R7 is a (hetero)hydrocarbyl group; R2 is H or C1-C4 alkyl; X1 is —NR1— or —O—, wherein R1 is an H or C1-C4 alkyl. ### Claim 13 (depends on 1) The crosslinkable composition of claim 1 comprising 0.005 to 5.0 parts by weight of the aziridine crosslinking agent, relative to 100 parts of the copolymer. ### Claim 14 (depends on 1) The crosslinkable composition of claim 1 wherein said copolymer comprises 1 to 5 parts by weight of acrylic acid and 1 to 5 parts by weight of a polar monomer. ### Claim 15 (depends on 1) The crosslinkable composition of claim 1 wherein Z is a water-solubilizing groups and said composition is an aqueous emulsion. ### Claim 16 (depends on 1) The crosslinkable composition of claim 1 comprising an emulsion comprising: (a) 30 to about 70 weight percent, based on the total weight of the emulsion, of the crosslinkable composition of claim 1, and (b) 30 to 70 weight percent of an aqueous phase comprising a surfactant, based on the total weight of the emulsion. ### Claim 17 (depends on 16) The emulsion of claim 16 wherein said composition has a pH of ≧4. ### Claim 18 (depends on 1) The crosslinkable composition of claim 1 comprising a syrup polymer comprising: a) a first component acid-functional acrylic copolymer comprising: i. 85 to 99 parts by weight of an (meth)acrylic acid ester of non-tertiary alcohol; ii. 1 to 15 parts by weight of an acid functional monomer; iii. 0 to 10 parts by weight of a second, non-acid functional, polar monomer; iv. 0 to 5 parts vinyl monomer; b) a second component comprising at least one free-radically polymerizable solvent monomer, c) a third component epoxy-functional (meth)acryloyl monomer; and d) a fourth component aziridine crosslinking agent of the formula: wherein R1 is H or C1-C4 alkyl; z is 0, 1 or 2 R2 is a H or C1-C4 alkyl; R3 is a (hetero)hydrocarbyl group: X1 is —O— or —NR1—; Z is —H or a water-solubilizing group.