WO2023228090A1 - Adhésifs sensibles à la pression à base d'acrylate comprenant de l'huile hydrophobe - Google Patents

Adhésifs sensibles à la pression à base d'acrylate comprenant de l'huile hydrophobe Download PDF

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Publication number
WO2023228090A1
WO2023228090A1 PCT/IB2023/055308 IB2023055308W WO2023228090A1 WO 2023228090 A1 WO2023228090 A1 WO 2023228090A1 IB 2023055308 W IB2023055308 W IB 2023055308W WO 2023228090 A1 WO2023228090 A1 WO 2023228090A1
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Prior art keywords
radiation
sensitive adhesive
pressure sensitive
adhesive precursor
crosslinkable pressure
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PCT/IB2023/055308
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English (en)
Inventor
Patrick D. Hyde
Christopher R. Johnson
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3M Innovative Properties Company
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Publication of WO2023228090A1 publication Critical patent/WO2023228090A1/fr

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    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate

Definitions

  • the present disclosure relates generally to the field of adhesives, more specifically to the field of radiation crosslinked pressure sensitive adhesives which contain an acrylic ester copolymer and a hydrophobic oil.
  • Adhesives are used in a variety of marking, holding, protecting, sealing, and masking applications.
  • Adhesive tapes generally comprise a backing, or substrate, and an adhesive.
  • One type of adhesive, a pressure sensitive adhesive is particularly preferred for many applications.
  • Pressure sensitive adhesives (“PSAs”) are well known persons having ordinary skill in the relevant arts to possess certain properties at room temperature, including: (1) aggressive and permanent tack, (2) adherence with no more than finger pressure, (3) sufficient ability to hold onto an adherend, and (4) sufficient cohesive strength.
  • the present disclosure provides radiation-crosslinkable, pressure-sensitive adhesive precursor including 50 wt.% to 90 wt.% of an acrylic ester copolymer, the acrylic ester copolymer comprising a C4 to C16 acrylic monomer, and 10 wt.% to 50 wt.% of a hydrophobic oil.
  • the pressuresensitive adhesive precursor mixture may be cross-linked using electron beam radiation to provide an adhesive composition having a corrected gel content greater than 50%, clean removal from stainless steel, and instant wet-out to both smooth and structured surfaces with controlled adhesion and with low adhesion build.
  • articles including these adhesives are provided herein.
  • PSAs pressure-sensitive adhesives
  • synthetic rubbers e.g., styrene/butadiene copolymers (“SBR”) and styrene/isoprene/styrene (“SIS”) block copolymers
  • various (meth)acrylate e.g., acrylate and methacrylate copolymers
  • silicones e.g., silicones, silicones, and silicones.
  • Silicone gels are softer than silicone PSAs and have characteristics such as, for example, low lift, low residue, “gentle” to “aggressive” skin bonding adjustable through formulation changes, low-temperature bonding performance, masking and roughsurface tape applications, and bonding to oily surfaces.
  • acrylic PSAs tend to form strong aggressive bonds to skin and smooth surfaces such as stainless steel.
  • Acrylic PSAs are used in medical stick-to-skin tapes but require a balance of cohesive strength, removal without stripping skin, and enough compliance to stay bonded to skin over 24 hours without edge lifting.
  • Acrylic PSAs are not typically modified with high levels of hydrophobic oil due to inherent immiscibility and lack of cohesive strength.
  • the addition of the hydrophobic oil in combination with electron beam cross-linking provides a gel which is softer compared to traditional acrylates, reduces the long-term adhesion build, and facilitates the need for less aggressive removal force.
  • Adhesive composition and performance are also dependent upon the intended use of the adhesive. Some uses require a gentle tape, whereas other uses require an aggressive tape. If an adhesive is adhered to a sensitive area of the body, commonly a “gentle” tape is used. However, if it is critical that the adhesive remain adhered for an extended period of time or if the adhesive is adhered to an area which is very mobile, a more aggressive tape is used.
  • the term “gentle” adhesive generally refers to an adhesive for which the adhesion does not substantially build over time.
  • the term “aggressive” adhesive refers to an adhesive which has a substantial resistance to lifting or peeling.
  • Medical adhesives are generally used in wound dressings, surgical drapes, bandages, and tapes. These items are commonly constmcted of a backing coated with an adhesive. A liner may or may not be used to protect the adhesive. The performance of the adhesive is in part dependent upon the occlusivity of the backing. Backings are generally categorized by their porosity into either nonocclusive or occlusive backings. When nonocclusive backings are used to prepare bandages or the like for medical applications the resulting bandage typically does not adhere well to skin over extended time periods. Though not wishing to be bound to a particular theory, this probably occurs because the bandages cannot release water vapor which leads to retention of moisture and in turn causes the adhesive to lift from the skin.
  • Conformability and cohesiveness are two inversely related properties which are each important to consider when preparing or selecting adhesives for medical applications. It is typically desirable for a medical adhesive to conform to the terrain of the skin to which it is adhered as this may enhance comfort to the wearer and may also ensure a higher initial adhesion to the skin because the adhesive is able to flow into the skin's topography. However, if an adhesive is too conformable it may lack the cohesiveness necessary to remove the dressing from skin with the adhesive intact. If an adhesive lacks cohesive strength the adhesive on a bandage may split upon an attempt to remove the bandage leaving some adhesive residue adhered to the skin and some adhesive removed along with the bandage backing; this characteristic is unacceptable to most medical professionals and patients.
  • the present disclosure provides tacky, hydrophobic oil-gel acrylic ester pressure-sensitive adhesives (“PSAs”) that are softer than typical acrylic PSAs through the addition of hydrophobic oil.
  • PSAs hydrophobic oil-gel acrylic ester pressure- sensitive adhesives
  • the addition of hydrophobic oil results in adhesives that may be useful for bonding to smooth surfaces, rough surfaces, and skin surfaces.
  • These PSAs may have characteristics, such as, for example, high oil loading (/.e.,10 to 50 wt.%), high corrected gel content (i.e., greater than 50 wt.%), no oily residue, and instant wet-out as a consequence of having a low glass transition temperature (“T g ”) at 1Hz frequency e.g., where -60°C ⁇ T g ⁇ -20°C.
  • radiation-crosslinkable pressure-sensitive adhesive precursors comprising 40 wt.% to 90 wt.%, optionally 40 wt.% to 80 wt.%, optionally 50 wt.% to 90 wt.%, optionally 50 wt.% to 80 wt.% of an acrylic ester copolymer and 10 wt.% to 50 wt.%, optionally 20 wt.% to 40 wt.% of a hydrophobic oil.
  • Acrylic ester copolymer useful in embodiments of the present disclosure are known in the art and are described, for example, in U.S. Pat. No. 9,102,774 (Clapper et al.), U.S. RE 24,906 (Ulrich) and U.S. Pat. No. 5,804,610 (Hamer et. al.).
  • Such acrylic acid ester copolymers may be prepared by methods known to those of ordinary skill in the relevant arts from C4 to C16 acrylic monomers.
  • the C4 to C16 acrylic monomer comprises 10 wt.% to 100 wt.%, optionally 20 wt.% to 80 wt.%, optionally 30 wt.% to 70 wt.% of a CIO to C16 acrylic monomer.
  • CIO to C16 acrylic monomers useful in embodiments of the present disclosure include those selected from the group consisting of primary (“1°”) acrylic monomers, secondary (“2°”) acrylic monomers, and combinations thereof.
  • CIO to C 16 acrylic monomers may include, but are not limited to decyl acrylate, isononyl acrylate, dododecyl acrylate, 2-propylheptyl acrylate, isodecyl acrylate, tridecyl acrylate, 2-decylacrylate, 2-dodecylacrylate, 2-tetradecylacrylate, and combinations thereof.
  • the C4 to C16 acrylic monomer comprises 10 wt.% to 100 wt.%, optionally 20 wt.% to 80 wt.%, optionally 30 wt.% to 50 wt.% of a C4 to C8 acrylic monomer.
  • C4 to C8 acrylic monomers may include, but are not limited to, butyl acrylate, hexyl acrylate, octyl acrylate, 2-ethylhexylacrylate, 2-octyl acrylate, iso-octylacrylate, and combinations thereof.
  • the radiation-crosslinkable pressure sensitive adhesive precursor of the present disclosure includes an acrylic ester copolymer free of insoluble gel as determined by the Corrected Gel Test. In some preferred embodiments, the radiation-crosslinkable pressure sensitive adhesive precursor of the present disclosure includes an acrylic ester copolymer free of multifunctional acrylates, such as, for example, hexanediol diacrylate, trimethylolpropane triacrylate. In some preferred embodiments, the radiation-crosslinkable pressure sensitive adhesive precursor may have a weight average molecular weight (“Mw”) of 500,000 g/mol to 1,500,000 g/mol, optionally 750,000 g/mol to 1,000,000 g/mol as determined by gel permeation chromatography (“GPC”).
  • Mw weight average molecular weight
  • Hydrophobic oils useful in embodiments of the present disclosure are typically oils having low solubility in water (i.e., ⁇ 1% wt.%).
  • hydrophobic oils commercially available include paraffinic oils such as KAYDOL USP grade oil available from Sonnebom, Inc.
  • polybutenes having terminal unsaturation such as, for example, the INDOPOL L and H series from Ineos Oligomers, League City, Texas, and hydrogenated polybutenes such as, for example, PANALANE L and H series available from Vantage Specialty Chemicals, Deerfield, Illinois.
  • Useful polybutenes generally have molecular weight range from 350-1500 gr/mol.
  • hydrophobic oils compatible with embodiments of the present disclosure produce minimal interference with the electron beam curing step.
  • Radiation-crosslinkable pressure-sensitive adhesive precursors of the present disclosure may include additional additives depending on the envisaged properties for the resulting crosslinked pressuresensitive adhesive.
  • the radiation-crosslinkable pressure-sensitive adhesive precursor may further include up to 5 wt.%, optionally up to 4 wt.%, or optionally up to 2 wt.% of a polar acrylic monomer.
  • polar acrylic monomers useful in embodiments of the present disclosure include, without limitation, acrylic acid, N,N-dimethylacrylamide, and combinations thereof.
  • the radiation-crosslinkable pressure-sensitive adhesive precursor may further including up to 10 wt.%, up to 5 wt.%, up to 4 wt.%, or up to 2 wt.% of a high T g acrylate monomer.
  • high T g acrylate monomers useful in embodiments of the present disclosure include, without limitation, isobomyl acrylate, polystyrene macromonomer, and combinations thereof.
  • the radiation-crosslinkable pressure sensitive adhesive precursor may include an additive selected from the group consisting of a photoinitiator, a chain transfer agent, an antioxidant, a tackifying resin, and combinations thereof.
  • the radiation-crosslinkable pressure-sensitive adhesive precursor may include an amount of a photo initiator in parts per hundred of the acrylic monomers (“pphm”). In some preferred embodiments the radiation-crosslinkable pressure-sensitive adhesive precursor may include up to 0.1 pphm, up to 0.5 pphm, or up to 1 pphm of the photo initiator.
  • OMNIRAD 651 now IRGACURE 651
  • 2-hydroxy-2-methyl-l-phenyl-propan-l-one commercially available as OMNIRAD 1173
  • OMNIRAD 184 1 -hydro xy-cyclohexyl-phenyl-ketone
  • the radiation-crosslinkable pressure-sensitive adhesive precursor may include an amount of a chain transfer agent in parts per hundred of the acrylic monomers (“pphm”). In some preferred embodiments the radiation-crosslinkable pressure-sensitive adhesive precursor may include up to 0.001 pphm, up to 0.005 pphm, or up to 0.01 pphm of the chain transfer agent.
  • chain transfer agents useful in embodiments of the present disclosure include, without limitation, iso-octyl thioglycolate (“IOTG”), carbon tetrabromide (“CBr4”), and combinations thereof.
  • the radiation-crosslinkable pressure-sensitive adhesive precursor may include an amount of an antioxidant in parts per hundred of the acrylic monomers (“pphm”). In some preferred embodiments the radiation-crosslinkable pressure-sensitive adhesive precursor may include up to 0.1 pphm, up to 0.2 pphm, up to 0.5 pphm, or up to 1 pphm of the antioxidant.
  • primary antioxidants such as the sterically hindered phenols including IRGANOX 1076 (octadecyl-[3-(3,5-di-tert- butyl-4-hydroxyphenyl)propionate) and IRGANOX 1010 (pentaerythritol tetrakis [3- [3,5-di-tert-butyl-4- hydroxyphenyl]propionat
  • the radiation-crosslinkable pressure-sensitive adhesive precursor may further including up to 20 wt.%, up to 10 wt.%, up to 5 wt.%, or up to 1 wt.% of a tackifying resin.
  • Solid tackifying resins that may be useful in embodiments of the present disclosure typically develop tack in the adhesives including the radiation-crosslinkable pressure-sensitive adhesive precursor and have softening points (“SP”) less than 120°C.
  • C5 aliphatic hydrocarbon-derived resins such as the ESCOREZ 1000 series from ExxonMobil Chemical Co., Irving, Texas, the WINGTACK series available from Cray Valley, Exton, Pennsylvania, the PICCOTAC series available from Eastman Chemical Co., Kingsport, Pennsylvania, and the QUINTONE series available from Zeon Corp., Tokyo, Japan.
  • cycloaliphatic C9 hydrocarbon resins such as the ARKON P series (fully hydrogenated) and ARKON M series (partially hydrogenated) from Arakawa Chemical Inc., Chicago, Illinois
  • cycloaliphatic CIO hydrocarbons such as the ESCOREZ 5000 series from ExxonMobil Chemical Co.
  • hydrogenated pure monomer resins such as the REGALREZ series from Eastman Chemical Co.
  • gum rosin esters such as the FORAL series and the STAYBELITE A and E series from Pinova, Inc., Brunswick, GeoOrgia
  • tall oil rosin esters such as the SYLVATAC and SYLVALITE series from Kraton Polymers LLC, Houston, Texas, the WESTREZ 5000 series from MeadWestvaco Corp., Richmond, Virginia, and the PERMALYN series from Eastman Chemical Co.
  • polyterpenes such as the PICCOLYTE A, F, C and S series from Pinova, Inc.
  • turpentines such as S
  • liquid resins examples include, but are not limited to: alpha-pinene-derived polyterpenes such as that available under the trade name PICCOLYTE A25 Pinova, Inc.; beta-pinene-derived polyterpenes such as that available under the trade name PICCOLYTE S25 from Pinova, Inc.; hydrogenated C9-derived aliphatic resins such as that available under the trade name REGALREZ 1018 from Eastman Chemical Co., and that available under the trade name WINGTACK 10 from Cray Valley; and tall oil-based liquid rosin esters such as that available under the trade name SYLVALITE RE10L from Kraton Polymers.
  • the compatible tackifying resins can be a mixture of solid and liquid and should have minimal interference with the electron beam curing step. The presence of aromatic content may reduce electron beam curing efficiency.
  • Radiation-crosslinkable pressure-sensitive adhesive precursors of the present disclosure are readily prepared and processible via both hot melt and solvent mixing and coating processes known to those of ordinary skill in the relevant arts and are described in International Publication WO 2016/106003 (D’Haese et al.)
  • the radiation-crosslinkable pressure-sensitive adhesive precursor mixtures may be exposed to electron beam (“EB”) radiation to induce cross-linking of the radiation-crosslinkable pressuresensitive adhesive precursor and provide an adhesive composition.
  • EB doses suitable for embodiments of the present disclosure are typically 4 Megarads (“MR”) to 10 MR.
  • Adequate gel content and crosslinking have been achieved, for example, at 6 MR and 175 kilovolts (“kV”) accelerating energy for coating thicknesses ranging from 0.001” to 0.004” (0.00254 cm to 0.01016 cm).
  • the final composition preferably has a corrected gel content greater than 50%. This generally corresponds to enough crosslinking to provide clean removal (i.e., no oily residue) and no onset of flow (i.e., no G7G” cross-over temperature) from ambient temperature (e.g., 22°C) temperatures to temperatures greater than 150°C at 1 Hz frequency.
  • G’ is the storage modulus and G” is the loss modulus.
  • the corresponding tangent delta (8) ranges at 1Hz frequency from 0.4 - 0.6 at temperatures greater than 22°C to provide a pressure-sensitive adhesive that is useful for clean removal from stainless steel.
  • the coating compositions can be blended with compatible polymer components and/or foamed prior to EB cross-linking.
  • the radiation crosslinked pressure sensitive adhesives and radiation crosslinked pressure sensitive adhesive precursors of the present disclosure may advantageously be used to prepare a wide range of adhesive tapes and articles. Many of these tapes and articles contain backings or other substrates to support the layer of adhesive. Other adhesive tapes and articles do not contain a backing or substrate layer and therefore are free standing adhesive layers. Double-sided tapes are an example of such an adhesive article. Double-sided tapes, also called “transfer tapes”, are adhesive tapes that have adhesive on both exposed surfaces. In some transfer tapes, the exposed surfaces are simply the two surfaces of a single adhesive layer.
  • transfer tapes are multi-layer transfer tapes with at least two adhesive layers that may be the same or different, and in some instances intervening layers that may not be adhesive layers.
  • a multi-layer transfer tape may be a 3 layer construction with an adhesive layer, a film layer and another adhesive layer.
  • the film layer can provide handling and/or tear strength or other desirable properties.
  • double-sided adhesives are prepared that comprise one free standing layer of pressure sensitive adhesive. Since the double-sided adhesives are free standing, they must have sufficient handling strength to be handled without the presence of a supporting layer.
  • Adhesives of the present disclosure may be useful in the preparation of medical articles including adhesives such as, for example, surgical tapes and drapes, bandages, athletic tapes, and wound dressings.
  • the adhesives disclosed herein may be coated using solvent or hot melt methods well known in the art onto any backing suitable for medical uses including, for example, occlusive (substantially nonbreathable) and non-occlusive (breathable) backings.
  • Occlusive backings are also known as low porosity backings.
  • Nonlimiting examples of occlusive backings include films, foams, and laminates thereof.
  • Nonlimiting examples of nonocclusive backings include woven substrates, nonwoven substrates such as hydroentangled materials or melt blown webs, foams, and thermally embossed nonwoven substrates.
  • the adhesives of the present invention are amenable to continuous (knife or contact rod), discontinuous (e.g., stripe coating) or pattern coating which can provide either spatially distinct (e.g., dots, triangles or squares) or spatially thick and thin regions of the adhesive on the substrate.
  • sampled weight 50 grams of 50/50 toluene/ethyl acetate in a glass jar that was placed on a mechanical roller at room temperature for 1-2 days. The mixture was filtered through a 200-mesh screen. The screen and insoluble material were dried at 220 °F (104°C) for 1-2 hours. The weight of insoluble component was measured and referred to in the formula below as insoluble weight.
  • the corrected gel content was calculated according to the formula:
  • the second ramp of the DMA test involved ramping the temperature from 30 °C to 150 °C at a rate of 3 °C/min. Results from both ramps were combined to determine the Tan Delta value. The auto strain adjustment was enabled to ensure the material was in the Linear Viscoelastic Region (LVR) during all temperature ramps.
  • LVR Linear Viscoelastic Region
  • an acrylic ester copolymer was prepared as follows: a monomer mixture was prepared by blending acrylic monomers, IOTG, PHOTOINITIATOR, and ANTIOXIDANT A in ajar in the amounts indicated in Table 2. To this mixture was added a magnetic stir bar, and the mixture was placed on a stir plate, forming a curable composition. EVA FILM was heat sealed to form open ended receptacles each measuring 18 cm by 5 cm. Each receptacle was filled with approximately 24 grams of the curable composition. Air was forced out of the open end which was then sealed using a heat sealer (obtained under the trade designation “MIDWEST PACIFIC IMPULSE SEALER” from J. J.
  • GSM grams/meter 2
  • Samples were exposed to radiation from an electron beam source using a Model CB-300 electron beam generating apparatus (available from Energy Sciences, Inc. (Wilmington, Mass.). The uncured material was exposed to EB irradiation through the release liner. Sample compositions, EB doses after the release liner, and coating weights are presented in Table 3. Characterization of the samples following EB irradiation is presented in Table 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Précurseurs d'adhésifs sensibles à la pression réticulables par rayonnement comprenant de 50 % en poids à 90 % en poids d'un copolymère d'ester acrylique, le copolymère d'ester acrylique comprenant un monomère acrylique en C4 à C16, et de 10 % en poids à 50 % en poids d'une huile hydrophobe. Le mélange de précurseurs d'adhésifs sensibles à la pression peut être réticulé à l'aide d'un rayonnement de faisceau d'électrons pour fournir une composition adhésive ayant une teneur en gel corrigée supérieure à 50 %, un retrait propre à partir d'acier inoxydable, et une extraction instantanée à la fois vers des surfaces lisses et structurées avec une adhérence contrôlée et avec une faible formation d'adhérence. L'invention concerne également des procédés de préparation de tels précurseurs d'adhésifs sensibles à la pression réticulables par rayonnement ainsi que des adhésifs comprenant une forme réticulée du précurseur d'adhésif sensible à la pression réticulable par rayonnement et des articles comprenant ces adhésifs.
PCT/IB2023/055308 2022-05-26 2023-05-23 Adhésifs sensibles à la pression à base d'acrylate comprenant de l'huile hydrophobe WO2023228090A1 (fr)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE24906E (en) 1955-11-18 1960-12-13 Pressure-sensitive adhesive sheet material
US5804610A (en) 1994-09-09 1998-09-08 Minnesota Mining And Manufacturing Company Methods of making packaged viscoelastic compositions
US6497949B1 (en) * 2000-08-11 2002-12-24 3M Innovative Properties Company Adhesive blends comprising hydrophilic and hydrophobic pressure sensitive adhesives
US20060216523A1 (en) * 2003-08-19 2006-09-28 Shunsuke Takaki Pressure-sensitive adhesive tape and pressure-sensitive adhesive composition for medical adhesive tape
US9102774B2 (en) 2010-12-21 2015-08-11 3M Innovative Properties Company Polymers derived from secondary alkyl (meth)acrylates
EP2957303A1 (fr) * 2014-06-20 2015-12-23 Nitto Denko Corporation Composition durcissable et adhésif de la peau
WO2016106003A1 (fr) 2014-12-22 2016-06-30 3M Innovative Properties Company Adhésif sensible à la pression à base d'acrylate, à faible teneur en acide, contenant des tackifiants
US20180243463A1 (en) * 2015-08-31 2018-08-30 3M Innovative Properties Company Negative pressure wound therapy dressings comprising (meth)acrylate pressure-sensitive adhesive with enhanced adhesion to wet surfaces
US20210324243A1 (en) * 2018-06-29 2021-10-21 3M Innovative Properties Company Tapes and methods of use for masking aluminum surfaces in acid anodization

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE24906E (en) 1955-11-18 1960-12-13 Pressure-sensitive adhesive sheet material
US5804610A (en) 1994-09-09 1998-09-08 Minnesota Mining And Manufacturing Company Methods of making packaged viscoelastic compositions
US6497949B1 (en) * 2000-08-11 2002-12-24 3M Innovative Properties Company Adhesive blends comprising hydrophilic and hydrophobic pressure sensitive adhesives
US20060216523A1 (en) * 2003-08-19 2006-09-28 Shunsuke Takaki Pressure-sensitive adhesive tape and pressure-sensitive adhesive composition for medical adhesive tape
US9102774B2 (en) 2010-12-21 2015-08-11 3M Innovative Properties Company Polymers derived from secondary alkyl (meth)acrylates
EP2957303A1 (fr) * 2014-06-20 2015-12-23 Nitto Denko Corporation Composition durcissable et adhésif de la peau
WO2016106003A1 (fr) 2014-12-22 2016-06-30 3M Innovative Properties Company Adhésif sensible à la pression à base d'acrylate, à faible teneur en acide, contenant des tackifiants
US20180243463A1 (en) * 2015-08-31 2018-08-30 3M Innovative Properties Company Negative pressure wound therapy dressings comprising (meth)acrylate pressure-sensitive adhesive with enhanced adhesion to wet surfaces
US20210324243A1 (en) * 2018-06-29 2021-10-21 3M Innovative Properties Company Tapes and methods of use for masking aluminum surfaces in acid anodization

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