# US 5,708,109 A · Pressure sensitive adhesives with good oily surface adhesion > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,708,109 A - Document ID: US5708109A - Status: Granted - Kind: A - Application number: 08/796,393 - Filed: 1997-02-06 - Granted: 1998-01-13 - Earliest claimed: 1993-11-10 - Assignees: Minnesota Mining and Manufacturing Company - Inventors: Greggory S. Bennett; Christopher A. Haak - Web page: https://patentgrep.com/patent/US5708109A ## CPC - F16F 9/306: {of the constrained layer type, i.e. comprising one or more constrained viscoelastic layers} - C08F 220/1808: {C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate} - C08F 220/1811: {C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate} - C08F 220/1812: {C12-(meth)acrylate, e.g. lauryl (meth)acrylate} - C08L 33/08: Homopolymers or copolymers of acrylic acid esters - 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 9/02: Electrically-conducting adhesives - C09J 133/08: Homopolymers or copolymers of acrylic acid esters - C08L 2666/02: Organic macromolecular compounds, natural resins, waxes or and bituminous materials - C09J 2301/302: the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C - C09J 2301/416: use of irradiation - H05K 3/323: {by applying an anisotropic conductive adhesive layer over an array of pads} - F16F: SPRINGS; SHOCK-ABSORBERS; MEANS FOR DAMPING VIBRATION - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) - H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS ## Abstract A pressure sensitive adhesive that includes the polymerization product of: (a) 25-97 parts by weight of an acrylic acid ester of a monohydric alcohol whose homopolymer has a T.sub.g less than 0.degree. C.; (b) 3-75 parts by weight of a non-polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of no greater than 10.50 and a T.sub.g greater than 15.degree. C.; and (c) 0-5 parts by weight of a polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of greater than 10.50 and a T.sub.g greater than 15.degree. C. The relative amounts of the acrylic acid ester, the non-polar ethylenically unsaturated monomer, and the polar ethylenically unsaturated monomer are chosen such that the 90.degree. peel adhesion of the pressure sensitive adhesive to a surface provided with 1.5.+-.0.25 mg/in.sup.2 oil is greater than zero after a 10 second dwell at room temperature as measured according to Test Procedure B. ## Claims ### Claim 1 A fastener comprising a hook and loop fastener provided with a pressure sensitive adhesive composition, said pressure sensitive adhesive composition consisting essentially of a pressure sensitive adhesive polymer consisting of the reaction product of: (a) 25-97 parts by weight of an acrylic acid ester of a monohydric alcohol whose homopolymer has a Tg less than 0.degree. C.; (b) 3-75 parts by weight of a non-polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of no greater than 10.50 and a Tg greater than 15.degree. C.; and (c) 0-5 parts by weight of a polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of greater than 10.50 and a Tg greater than 15.degree. C., the relative amounts of said acrylic acid ester, said non-polar ethylenically unsaturated monomer, and said polar ethylenically unsaturated monomer being chosen such that 90.degree. peel adhesion of said reaction product to a surface provided with 1.5.+-.0.25 mg/in.sup.2 oil is greater than zero after a 10 second dwell at room temperature as measured according to Test Procedure B, with the proviso that the composition contains essentially no emulsifier. ### Claim 2 (depends on 1) The fastener of claim 1, wherein the relative amounts of said acrylic acid ester, said non-polar ethylenically unsaturated monomer, and said polar ethylenically unsaturated monomer being chosen such that the shear strength of said reaction product at both room temperature and at 70.degree. C. is greater than 50 minutes as measured according to Test Procedure C. ### Claim 3 (depends on 1) The fastener of claim 1, wherein the 1 radian/second tan delta maximum glass transition temperature of said reaction product is between -45.degree. C. and 15.degree. C., inclusive. ### Claim 4 (depends on 1) The fastener of claim 1, wherein said pressure sensitive adhesive comprises the reaction product of said acrylic acid ester, said non-polar ethylenically unsaturated monomer, and 0 parts by weight of said polar ethylenically unsaturated monomer. ### Claim 5 (depends on 1) The fastener of claim 1, wherein said non-polar ethylenically unsaturated monomer is a monomer other than a methacrylate monomer. ### Claim 6 (depends on 1) The fastener of claim 1, wherein said non-polar ethylenically unsaturated monomer is isobornyl acrylate. ### Claim 7 (depends on 1) The fastener of claim 1, wherein said pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, isobornyl acrylate, and acrylic acid. ### Claim 8 (depends on 1) The fastener of claim 1, wherein said pressure sensitive adhesive comprises the reaction product of isooctyl acrylate and isobornyl acrylate. ### Claim 9 (depends on 1) The fastener of claim 1, wherein said pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, lauryl acrylate, and N-octyl acrylamide. ### Claim 10 (depends on 1) The fastener of claim 1, wherein said pressure sensitive adhesive comprises the reaction product of lauryl acrylate and N-octyl acrylamide. ### Claim 11 (depends on 1) The fastener of claim 1, wherein said pressure sensitive adhesive comprises the reaction product of isodecyl acrylate and isobornyl acrylate. ### Claim 12 (depends on 1) The fastener of claim 1, wherein the pressure sensitive adhesive comprises the reaction product of lauryl acrylate and isobornyl acrylate. ### Claim 13 (depends on 1) The fastener of claim 1, wherein the pressure sensitive adhesive comprises the reaction product of lauryl acrylate, isodecyl acrylate, and isobornyl acrylate. ### Claim 14 (depends on 1) The fastener of claim 1, wherein the pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, octadecyl acrylate, and isobornyl acrylate. ### Claim 15 (depends on 1) The fastener of claim 1, wherein the pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, octadecyl acrylate, and N-octyl acrylamide. ### Claim 16 A fastener comprising a headed fastener provided with a pressure sensitive adhesive composition, said pressure sensitive adhesive composition consisting essentially of a pressure sensitive polymer consisting of the reaction product of: (a) 25-97 parts by weight of an acrylic acid ester of a monohydric alcohol whose homopolymer has a Tg less than 0.degree. C.; (b) 3-75 parts by weight of a non-polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of no greater than 10.50 and a Tg greater than 15.degree. C.; and (c) 0-5 parts by weight of a polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of greater than 10.50 and a Tg greater than 15.degree. C., the relative amounts of said acrylic acid ester, said non-polar ethylenically unsaturated monomer, and said polar ethylenically unsaturated monomer being chosen such that 90.degree. peel adhesion of said reaction product to a surface provided with 1.5.+-.0.25 mg/in.sup.2 oil is greater than zero after a 10 second dwell at room temperature as measured according to Test Procedure B, with the proviso that the composition contains essentially no emulsifier. ### Claim 17 (depends on 16) The fastener of claim 16, wherein the relative amounts of said acrylic acid ester, said non-polar ethylenically unsaturated monomer, and said polar ethylenically unsaturated monomer being chosen such that the shear strength of said reaction product at both room temperature and at 70.degree. C. is greater than 50 minutes as measured according to Test Procedure C. ### Claim 18 (depends on 16) The fastener of claim 16, wherein the 1 radian/second tan delta maximum glass transition temperature of said reaction product is between -45.degree. C. and 15.degree. C., inclusive. ### Claim 19 (depends on 16) The fastener of claim 16, wherein said pressure sensitive adhesive comprises the reaction product of said acrylic acid ester, said non-polar ethylenically unsaturated monomer, and 0 parts by weight of said polar ethylenically unsaturated monomer. ### Claim 20 (depends on 16) The fastener of claim 16, wherein said non-polar ethylenically unsaturated monomer is a monomer other than a methacrylate monomer. ### Claim 21 (depends on 16) The fastener of claim 16, wherein said non-polar ethylenically unsaturated monomer is isobornyl acrylate. ### Claim 22 (depends on 16) The fastener of claim 16, wherein said pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, isobornyl acrylate, and acrylic acid. ### Claim 23 (depends on 16) The fastener of claim 16, wherein said pressure sensitive adhesive comprises the reaction product of isooctyl acrylate and isobornyl acrylate. ### Claim 24 (depends on 16) The fastener of claim 16, wherein said pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, lauryl acrylate, and N-octyl acrylamide. ### Claim 25 (depends on 16) The fastener of claim 16, wherein said pressure sensitive adhesive comprises the reaction product of lauryl acrylate and N-octyl acrylamide. ### Claim 26 (depends on 16) The fastener of claim 16, wherein said pressure sensitive adhesive comprises the reaction product of isodecyl acrylate and isobornyl acrylate. ### Claim 27 (depends on 16) The fastener of claim 16, wherein the pressure sensitive adhesive comprises the reaction product of lauryl acrylate and isobornyl acrylate. ### Claim 28 (depends on 16) The fastener of claim 16, wherein the pressure sensitive adhesive comprises the reaction product of lauryl acrylate, isodecyl acrylate, and isobornyl acrylate. ### Claim 29 (depends on 16) The fastener of claim 16, wherein the pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, octadecyl acrylate, and isobornyl acrylate. ### Claim 30 (depends on 16) The fastener of claim 16, wherein the pressure sensitive adhesive comprises the reaction product of isooctyl acrylate, octadecyl acrylate, and N-octyl acrylamide.