WO2001027162A2 - Adhesif par pression contenant un copolymere greffe pelable faiblement volatil et non corrosif - Google Patents

Adhesif par pression contenant un copolymere greffe pelable faiblement volatil et non corrosif Download PDF

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Publication number
WO2001027162A2
WO2001027162A2 PCT/US2000/026245 US0026245W WO0127162A2 WO 2001027162 A2 WO2001027162 A2 WO 2001027162A2 US 0026245 W US0026245 W US 0026245W WO 0127162 A2 WO0127162 A2 WO 0127162A2
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Prior art keywords
copolymer
alkyl
moiety
monomer
macromer
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PCT/US2000/026245
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English (en)
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WO2001027162A3 (fr
Inventor
Michael J. Zajaczkowski
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Adhesives Research, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Adhesives Research, Inc. filed Critical Adhesives Research, Inc.
Priority to AU78325/00A priority Critical patent/AU7832500A/en
Publication of WO2001027162A2 publication Critical patent/WO2001027162A2/fr
Publication of WO2001027162A3 publication Critical patent/WO2001027162A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials

Definitions

  • the present invention is directed to a crosslinked, non- corrosive, low volatiles-containing removable graft copolymer pressure sensitive adhesive.
  • Polymeric compositions are known which are comprised of backbone polymers having grafted thereto pendant polymeric moieties.
  • the type of backbone polymer and graft polymeric moiety employed varies depending upon the desired characteristics of the end product. See, for example, U.S. Patent Nos. 3,786,116 3,832,423; 3,842,146; 3,862,077; 3,879,494; 3,928,255; 3,989,768 4,085,168; 4,551,388; 4,554,324; 4,656,213; 4,693,776; 4,732,808 4,871 ,812; 5,352,516; 5,703,169; and 5,703,170. These patents disclose various types of such polymers which may or may not exhibit pressure sensitive adhesive properties.
  • compositions comprised of a backbone polymer such as an acrylic or methacrylic backbone polymer having attached thereto a graft polymer comprised of apolymerizable macromolecular monomer such as styrene or alpha-methyl styrene.
  • a backbone polymer such as an acrylic or methacrylic backbone polymer having attached thereto a graft polymer comprised of apolymerizable macromolecular monomer such as styrene or alpha-methyl styrene.
  • 5,352,516 may be made from an acrylic ester and a polar acrylic monomer.
  • the polar acrylic monomer can be one or a mixture of acrylic acid, acrylamide, acrylonitrile, itaconic acid, etc.
  • the acrylic ester can be any aliphatic ester of acrylic acid.
  • Such monomers are typically polymerized free radically by solution, suspension or emulsion polymerization.
  • the acrylate portion of the copolymer is generally present in a generally high concentration and renders the polymer tacky.
  • the polar monomer increases the ability of the adhesive to bond to a surface.
  • a crosslinked, non-conosive, low volatiles-containing strippable graft copolymer pressure sensitive adhesive comprised of a backbone polymer having a polymeric moiety grafted thereto, said graft copolymer comprising the crosslinked reaction product of:
  • the present invention is a crosslinked graft colymer pressure sensitive adhesive comprised of a backbone polymer having a polymeric moiety grafted thereto.
  • the graft copolymer comprises the crosslinked reaction product of at least one A monomer (as defined), optionally at least one B monomer, at least one polymeric graft moiety C having a T g greater than 20 °C, and at least one polymeric graft moiety D containing repeat hydrophilic units.
  • the graft copolymer includes at least one A monomer consisting of a monomeric (meth)acrylic acid ester of a non-tertiary alcohol where the alcohol portion has from 4 to 12 carbon atoms.
  • Exemplary A monomers include but are not limited to esters of acrylic acid or methacrylic acid with non-tertiary alcohols such as 1 - butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-l-butanol, 1- methyl-1-pentanol, 2-methyl- 1-pentanol, 3 -methyl- 1-pentanol, 2- ethyl-1 -butanol, 3,5,5-trimethyl-l-hexanol, 3-heptanol, 2-octanol, 1- decanol, 1-dodecanol, etc.
  • one or more polymerizable B monomers may be incorporated in the copolymer which B monomer(s) is copolymerizable with the A monomer.
  • the B monomer is a non-polar monomer comprising a monomeric acrylic or methacrylic acid ester of a non-tertiary alcohol having from 1 to 3 carbon atoms, such as methyl(meth)acrylate, ethyl(meth)acrylate, n- propyl(meth)acrylate, and isopropyl(meth)acrylate.
  • Additional B monomers include vinyl acetate and aromatic monomers such as styrene.
  • a polar B monomer such as acrylic acid
  • the graft copolymer of the present invention thus contains no more than about 5 wt. % polar B monomers, based on the total weight of the reactants.
  • any polar B monomer which is present includes alcohol, amide, amine and/or acid functionalities to permit crosslinking to occur by means of such functionalities.
  • the graft polymeric moiety C has a T g greater than 20oQ
  • Graft polymeric moiety C has the formula X-Z wherein X is a group copolymerizable with monomers A and B or capable of attachment to copolymerized A and B monomers and Z is a polymeric graft moiety having a T g greater than 20°C.
  • the Z moiety is essentially unreactive under copolymerization conditions.
  • the X moiety is an unsaturated polymerizable moiety the composition of which is not critical.
  • the X moiety may be, for example, when intended to be copolymerizable with monomers A and B, simply a vinyl group of the formula CHR DR 1 - where R is hydrogen or CO OH and R 1 is hydrogen or alkyl such as methyl.
  • the X moiety may comprise an amine or alcohol moiety (such as amonohydroxyl or monoamine moiety) which permits attachment of the macromer to a suitable functionality on previously- polymerized monomers A and B.
  • the hydroxyl moiety can serve as a terminal reactive group by reaction with suitable moieties on the polymer backbone resulting from the use of monomers such as isocyanate-substituted (meth)acrylic acid, (meth)acrylic acid anhydride, etc.
  • a variety of functional groups may be employed to attach the graft Z to the polymer backbone.
  • Exemplary functional groups include but are not
  • R is a hydrogen atom or a lower alkyl group.
  • the polymeric moiety C is formed from a vinyl aromatic monomer such as styrene, alpha-methylstyrene, indene and p-tert-butylstyrene.
  • the polymeric moiety Z may also be formed from vinyl toluene, acenaphthalene, acrylonitrile and methacrylonitrile; organic isocyanates including lower alkyl, phenyl, lower alkyl phenyl andhalophenyl isocyanates; organic diisocyanates including lower alkylene, phenylene, and tolylene diisocyanates; lower alkyl and allyl acrylates and methacrylates, including methyl, t-butyl acrylates, and methacrylates; lower olefins, such as ethylene, propylene, butyl ene, isobutylene, pentene, hexene, etc.; vinyl esters of aliphatic carboxylic acids such as vinyl
  • the selection of the specific porymerizable monomer for the polymer graft is not critical, since as the above listing suggests, a wide variety of monomers (and the resulting polymeric moieties) can be used with success as a polymeric graft in the claimed composition which meet the minimum T g requirement.
  • the molecular weight of the graft polymeric moiety C is preferably sufficient to result in the formation of a "phase-separated" graft copolymer composition.
  • the molecular weight of the graft polymeric moiety will be within the range of from about 2,000 to 60,000, and will preferably range from about 2,000 to 13,000.
  • the graft polymeric moiety D also forms polymeric sidechains on the copolymer.
  • the macromer D contains repeat hydrophilic units.
  • the macromer D may be represented by the formula X-( Y) p -Z- R.
  • X is as defined above and is a moiety copolymerizable with monomers A and B or, in the alternative, capable of attachment to polymerized monomers A and B, Y is a divalent linking group, Z is a homo- or copolymeric moiety essentially unreactive at copolymerization conditions containing repeat hydrophilic units, R is a terminal group, and p is 0 or 1.
  • a preferred Y divalent linking group is -C-, or a linking group which incorporates such a moiety.
  • Additional Y linking groups which may be employed in connection with the present invention include but are not limited to the following moieties:
  • the presence of the Y linking group is optional in the event the moiety includes a functionality which enables the Z moiety to react with the X moiety.
  • the choice of a suitable X and Y moiety for use in the present invention may be readily made upon practice of the present invention. See, for example, the discussion in U.S. Patent Nos. 3,786,116; 3,832,423; 3,842,058; 3,842,059; 3,842,146; and 4,554,324, herein incorporated by reference.
  • the Z moiety is preferably selected from the group consisting of (but not limited to) a polyalkylene oxide radical, a polyethyloxazoline radical such as a radical of poly(2-ethyl-2- oxazoline), poly vinylpynoli done radical, polyester(meth)acrylate radical, polyvinyl caprolactam radical, polymethyl vinyl ether radical or mixtures thereof.
  • exemplary D macromers formed from such radicals include but are not limited to ethoxylated or propoxylated hydroxy(C ⁇ _ 5 )alkyl meth(acrylate), polymethylvinyl ether mono(meth)acrylate and beta-carboxyethyl acrylate.
  • the molecular weight of the macromer used in the present invention is not critical but will generally range from about 300 to about 50,000, and preferably from about 300 to 3,000.
  • the Z moiety is preferably comprised solely of one or more hydrophilic monomer radicals.
  • the Z moiety may also be a copolymer of hydrophilic and hydrophobic monomers.
  • any non-hydrophilic portion employed in the D macromer is present in an amount of 50% or less based on the weight of the macromer.
  • the macromer D is preferably represented by the formula:
  • X-Y-(0-C m H 2 n -R or X-Y-(C m H 2m -C-0) n -R wherein X and Y are as defined above and R represents a terminal group; and in which m is an integer of from 2 to 6, and n ranges up to 300.
  • macromer D may be an ethoxylated or propoxylated hydroxy(C 1 . 5 )alkyl (meth)acrylate represented by the formula:
  • CH 2 C - C - (0 - C m H 2 n - R ( ii wherein R ⁇ is hydrogen or C ⁇ 5 alkyl and R is a terminal group.
  • R ⁇ is hydrogen or C ⁇ 5 alkyl and R is a terminal group.
  • m is 2 or 3 and n is 4 to 30, and R is H, OH, C, ⁇ alkyl, or nonyl -phenol.
  • macromer D may advantageously comprise a 2- carboxy(C 1 . 5 )alkyl acrylate of the formula:
  • Rj is hydrogen or C ⁇ alkyl and R is a terminal group.
  • m is 2 or 3 and n is 4 to 30, and R is H, OH, C j . 5 alkyl or nonyl -phenol.
  • macromer D may incorporate mixtures of polyether and polyester repeat units with advantage in a variety of ratios. Such ratios are non-critical to practice of the present invention.
  • the macromer D may employ a variety of terminal groups R. While the terminal group may typically be OH or C ⁇ alkyl, it may be desirable to select a terminal group based on the functional character of the terminal group.
  • suitable terminal groups include but are not limited to (1) acid/ionic groups such as carboxyl, phosphate or sulfate groups, (2) hydrophobic groups such as lower alkyl, phenyl or substituted phenyl, and (3) hydrophilic groups such as hydroxyl or amine groups.
  • ionic end groups may be used to provide pH-dependent solubility characteristics for the copolymer.
  • Hydrophobic terminal groups may be used to reduce the water sensitivity of the copolymer.
  • copolymer of the present invention may be covalently or ionically- crosslinked in a conventional manner.
  • Ionic terminal groups may be used to provide a desired degree of crosslinking; for example, by neutralizing acid moieties with metal hydroxides.
  • High temperature performance may be enhanced by incorporating an acid functionality in conjunction with a ditertiary amine.
  • Aqueous solution viscosities may be influenced by the presence of ionic terminal groups.
  • the graft copolymer of the present invention may be crosslinked by use of a suitable internal or external crosslinking agent, the identity of which is not particularly critical to practice of the claimed invention.
  • Exemplary internal crosslinking agents are disclosed in U.S. Patent Nos. 3,714,096; 3,923,931 ; 4,454,301; 4,950,708; 5,194,486; 5,214,094; 5,420,195; and 5,563,205, each herein incorporated by reference.
  • Exemplary internal crosslinking agents include polyfunctional compounds having at least two non-conjugated carbon-to-carbon double bonds.
  • Exemplary polyfunctional compounds include but are not limited to diallyl maleate, diallyl phthlate, and multifunctional acrylates and methacrylates (such as polyethylene glycol diacrylate, hexane diol diacrylate, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate, propylene glycol diacrylate and trimethylolpropane trimethylacrylate.
  • Such crosslinking agents are disclosed in U.S. Patent Nos. 5,420,195 and 5,563,205, each herein incorporated by reference.
  • Suitable internal crosslinking agents include (1) alkyl acylamidoglycolate alkyl ethers or acrylamidoglycoamide alkyl ethers having the formulae
  • R is hydrogen or methyl
  • R 1 is C ⁇ alkyl, C 5 . 6 cycloalkyl
  • R 2 is C j _ 6 alkyl and C 5 ⁇ cycloalkyl, each of which may be optionally substituted by oxygen or nitrogen heteroatoms
  • R 3 and R 4 are hydrogen or C l 2 ⁇ alkyl or cycloaliphatic alkyls optionally substituted with nitrogen or oxygen moieties
  • alkoxides of a central atom further substituted with apolymerizable methacrylyl function, wherein the central atom is selected from the group consisting of Groups LT, Ln or IV, such as methacryloxyalkyl silanes having at least one alkoxy group.
  • crosslinking agents are disclosed in U.S. Patent Nos.4,454,301; 5,194,486; and 5,214,094, each herein incorporated by reference.
  • the crosslinking agent may be acetoacetoxyalkyl (meth)acrylate and N- methylolacrylamide.
  • CH 2 C - C - N - C - C- OCH 3
  • CH 2 C - C - N - C - OH
  • crosslinking agents may also be employed with advantage to crosslink the graft copolymer through functionalities on either the polar B monomer or on the graft polymeric moieties.
  • Such crosslinking agents include without limitation melamine resins, melamine-formaldehyde resins, aziridine compounds and diamines.
  • the A monomer is present in the graft copolymer in an amount of from 30 to 95 percent by weight
  • the optional non- polar B monomer is present in an amount of from 0 to 50 percent by weight
  • the C macromer is present in an amount of from 12 to 15 percent by weight
  • the D macromer is present in an amount of from 3 to 50 percent by weight
  • the internal crosslinking agent (if employed) is present in an amount of from 0.1 to 7 percent by weight, based on the total weight of the respective components in the graft copolymer.
  • the copolymer composition of the present invention may be prepared by any conventional polymerization technique, including (1) free radical -initiated copolymerization of components A, C and D and optionally B in the presence of a solvent and the crosslinking agent(s), or (2) attachment of the macromer grafts to a preformed crosslinked backbone polymer formed from copolymerized monomer A optionally copolymerized with monomer B via reaction with a suitable functional group on the backbone polymer subsequent to formation of same.
  • S u i t a b l e copolymerization temperatures range from about 20 °C. to about 150°C. for periods of time of from 2 to 24 hours until the desired degree of conversion occurs.
  • the solvent is removed and a tacky copolymer results having acceptable adhesive properties.
  • the adhesive of the present invention may be used in association with a variety of body members (e.g., tapes, patches, strips, labels, etc.) to provide an adhesive assembly.
  • the body member may be in the form of a backing material coated on at least one side thereof with the adhesive to provide an adhesive- backed sheet film or tape.
  • Exemplary backing materials used in the production of such a product include but are not limited to flexible and inflexible backing materials conventionally employed in the area of pressure sensitive adhesives, such as creped paper, kraft paper, fabrics (knits, non-wovens, wovens), foil and synthetic polymer films such as polyethylene, polypropylene, polyvinyl chloride, poly(ethylene terephthalate) and cellulose acetate, as well as glass, ceramics, metallized polymer films and other compatible sheet or tape materials.
  • pressure sensitive adhesives such as creped paper, kraft paper, fabrics (knits, non-wovens, wovens), foil and synthetic polymer films such as polyethylene, polypropylene, polyvinyl chloride, poly(ethylene terephthalate) and cellulose acetate, as well as glass, ceramics, metallized polymer films and other compatible sheet or tape materials.
  • the body member (e.g., in sheet form) may be coated in any conventional manner with the adhesive composition of the present invention, such as by roll coating, spray coating, extrusion coating, co-extrusion coating, hot melt coating by use of conventional coating devices.
  • the adhesive of the present invention may be applied as a solution to at least one surface of the body member and the solvent subsequently removed to leave a tacky adhesive residue on the body member.
  • the adhesive may be applied to the body member either in the form of a continuous layer or in discontinuous form.
  • a one liter baffled reactor is heated to 115 to 120 °F, and purged with nitrogen.
  • the following reaction mixture is provided:
  • VAZO 52 catalyst 1.08 grams

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un adhésif par pression contenant un copolymère greffé pelable faiblement volatil, non corrosif et réticulé, qui comprend un squelette de polymère possédant une fraction de polymère greffé sur celui-ci. Ce copolymère réticulé comprend au moins un monomère A constitué d'ester d'acide (méth)acrylique monomère d'un alcool non tertiaire, éventuellement au moins un monomère B, au moins une fraction C de greffe polymère ayant une Tg supérieure à 20 °C, et un groupe fonctionnel D de greffe macromère contenant des unités hydrophiles répétitives.
PCT/US2000/026245 1999-10-08 2000-10-10 Adhesif par pression contenant un copolymere greffe pelable faiblement volatil et non corrosif WO2001027162A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU78325/00A AU7832500A (en) 1999-10-08 2000-10-10 Non-corrosive, low volatiles containing strippable graft copolymer pressure sensitive adhesive

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41449799A 1999-10-08 1999-10-08
US09/414,497 1999-10-08

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WO2001027162A2 true WO2001027162A2 (fr) 2001-04-19
WO2001027162A3 WO2001027162A3 (fr) 2009-09-03

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1428844A2 (fr) * 2002-12-12 2004-06-16 L'oreal Dispersions de polymères en milieu organique.
FR2848559A1 (fr) * 2002-12-12 2004-06-18 Oreal Polymere acrylique, dispersion dudit polymere stable dans un milieu organique non aqueux et non silicone et composition comprenant ladite dispersion.
WO2010033381A1 (fr) * 2008-09-16 2010-03-25 Henkel Corporation Formulation acrylique adhésive sensible à la pression et articles la renfermant
CN113549415A (zh) * 2021-08-16 2021-10-26 江苏耐斯数码科技股份有限公司 一种高固含量可剥离水性压敏胶及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6239228B1 (en) * 1997-02-21 2001-05-29 Adhesives Research, Inc. Pressure sensitive adhesive containing macromer having repeat hydrophilic moieties

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6239228B1 (en) * 1997-02-21 2001-05-29 Adhesives Research, Inc. Pressure sensitive adhesive containing macromer having repeat hydrophilic moieties

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1428844A2 (fr) * 2002-12-12 2004-06-16 L'oreal Dispersions de polymères en milieu organique.
FR2848559A1 (fr) * 2002-12-12 2004-06-18 Oreal Polymere acrylique, dispersion dudit polymere stable dans un milieu organique non aqueux et non silicone et composition comprenant ladite dispersion.
EP1428844A3 (fr) * 2002-12-12 2005-04-06 L'oreal Dispersions de polymères en milieu organique.
WO2010033381A1 (fr) * 2008-09-16 2010-03-25 Henkel Corporation Formulation acrylique adhésive sensible à la pression et articles la renfermant
US8440304B2 (en) 2008-09-16 2013-05-14 Henkel Corporation Acrylic pressure sensitive adhesive formulation and articles comprising same
CN113549415A (zh) * 2021-08-16 2021-10-26 江苏耐斯数码科技股份有限公司 一种高固含量可剥离水性压敏胶及其制备方法

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WO2001027162A3 (fr) 2009-09-03

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