EP0140941A1 - Adhesif et materiau en feuille enduit d'adhesif pour la peau mouillee - Google Patents

Adhesif et materiau en feuille enduit d'adhesif pour la peau mouillee

Info

Publication number
EP0140941A1
EP0140941A1 EP84901684A EP84901684A EP0140941A1 EP 0140941 A1 EP0140941 A1 EP 0140941A1 EP 84901684 A EP84901684 A EP 84901684A EP 84901684 A EP84901684 A EP 84901684A EP 0140941 A1 EP0140941 A1 EP 0140941A1
Authority
EP
European Patent Office
Prior art keywords
monomer
adhesive
monomers
sheet material
copolymer
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP84901684A
Other languages
German (de)
English (en)
Inventor
William R. Snyder
Cheryl L. Spence
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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 Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of EP0140941A1 publication Critical patent/EP0140941A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/58—Adhesives
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Definitions

  • the present invention relates to normally tacky pressure-sensitive adhesive compositions and sheet materials coated therewith.
  • Pressure-sensitive adhesives which meet all of the requirements of industrial and domestic applications generally fall short of the requirements of an adhesive which is to be employed in a medical or surgical use involving adhesion to skin, and 5 only a select few of the commercially available pressure-sensitive adhesives are actually completely acceptable for such use.
  • An adhesive which is to be employed on skin may be expected to experience moisture found on the skin.
  • Moisture may be experienced as the result of physiological changes involving skin or underlying tissue.
  • the adhesive may experience perspiration or tissue or wound exudate which is found on skin prior to application of the adhesive bandage or the like thereto or which appears subsequently to such application.
  • Moisture may also be experienced by an adhesive as the result of cleansing of skin which may precede application of an adhesive bandage or surgical incise drape thereto, and current practice generally requires that the skin be allowed to dry thoroughly prior to such an application.
  • Moisture may further be experienced during routine cleansing of skin adjacent to the site of an adhesive bandage or the like.
  • an adhesive may experience moisture as the result of environmental changes involving, for example, condensa ⁇ tion of air-borne moisture on skin. °
  • the bond-making and bond-breaking require ⁇ ments of an adhesive which is intended for employment on dry skin are compounded by adding the requirement that the adhesive adhere suitably to moist skin, the balancing of the physical properties of the adhesive becomes much more 5 critical.
  • the adhesive while retaining the properties of suitable shear adhesion and ease of removal, must exhibit the wholly different property of suitable adhesion to moist skin. Further, in order to be useful in a variety of applications, that adhesive should retain the property of " suitable adhesion to dry skin. Such versatility requires that the adhesive exhibit a proper balance of hydrophobic and hydrophilic properties.
  • A is a hydrophobic monomeric acrylic acid ester of a non-tertiary alcohol, said alcohol having from 4 to about 14 carbon atoms;
  • B is a hydrophilic monomer which has a vinyl group copolymerizable with the A monomer and is other than acrylic acid, methacrylic acid, itaconic acid, acrylamide, methacrylamide, lower alkyl-substituted acrylamide, and N-vinyl-2-pyrrolidone, the amount by weight of B monomer being about 5 to 30% of the total weight of all monomers in the copolymer;
  • C is at least one polar monomer copolymerizible with the A and B monomers, selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, acrylamide, methacrylamide, lower alkyl-substituted acrylamide, and N-vinyl-2-pyrrolidone, the amount by weight of C monomer being about 0.5 to 30% of the total weight of all mono
  • the preferred B monomer is a hydrophilic raacromolecular monomer
  • the preferred hydrophilic macromolecular monomer has the general formula X-Y-Z, wherein
  • Preferred adhesives and adhesive-coated sheet materials of the invention further exhibit a moist-skin adhesion value of at least about 3 Newtons per 100 millimeters of width.
  • Most preferred adhesives and adhesive-coated sheet materials exhibit a moist-skin adhesion value of at least about 4 Newtons per 100 millimeters, thereby rendering them useful in what have heretobefore been particularly troublesome applications, ⁇
  • Certain of these adhesives and adhesive-coated sheet materials also exhibit an initial dry skin adhesion value of at least about 2 Newtons per 100 millimeters of width and/or an initial dry skin adhesion value after 48 hours of not more than about 8 Newtons per 100 millimeters of width.
  • the adhesive copolymer comprises a hydrophobic monomer A, a hydrophilic monomer B and a polar monomer C.
  • the A monomer is believed to contribute hydrophobicity to the copolymer, and in combination with the C monomer, provides a versatile pressure-sensitive adhesive which exhibits suitable adhesion performance on dry skin.
  • the B monomer is believed to contribute hydrophilicity to the copolymer and to plasticize the adhesive copolymer.
  • lower alkyl designates straight or branched-chain alkyl groups containing 1 to about 6 carbon atoms.
  • the preferred “lower alkyl” groups contain 1 to about 4 carbon atoms.
  • suitable monomers for use as the A monomer include the esters of acrylic acid or methacrylic acid with non-tertiary alcohols such as 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl- 1-butanol, 1-hexanol, 2-hexanol, 2-methyl-l-pentanol, 3-methyl-l-pentanol, 2-ethyl-l-butanol, 3,5,5-trimethyl- 1-hexanol, 3-heptanol, 1-octanol, 2-octanol, isooctyl alcohol, 2-ethyl-l-hexanol, 1-decanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol and the like.
  • the preferred A monomer is the ester of acrylic acid with isooctyl alcohol.
  • hydrophilic in connection with the B monomer is meant that the B monomer has substantial affinity for water. It is preferred that the B monomer contain one and only one vinyl group copolymerizable with the A and C monomers.
  • monomer B is preferably a 0 hydrophilic macromolecular monomer containing a plurality of hydrophilic sites which impart the required hydrophilicity to the monomer.
  • the most preferred W moiety of Formula III is a poly(ethylene oxide) radical, a poly(propylene oxide) radical, or a radical of a copolymer of ethylene oxide and propylene oxide.
  • B monomers are available commer ⁇ cially.
  • commercially available B monomers which have been found to be suitable are the 2-(2-ethoxyethoxy)ethyl acrylate which is available under the trade designation "SR-256" from Sartomer Company, West Chester, PA; the methoxy poly(ethylene acrylate which is available under the trade designation “No. 8816” from Monomer-Polymer & Dajac Laboratories, Inc., Trevose, PA; the methoxy poly(ethylene oxide) methacrylates of 200 Daltons, 400 Daltons, and 1000 Daltons which are available under the trade designations "No. 16664", “No. 16665" and “No. 16666", respectively, from Polysciences, Inc., Warrington, PA; the hydroxy poly(ethylene oxide) 5 methacrylate which is available under the trade designation "No. 16712” from Polysciences, Inc., Warrington, PA.
  • Examples of suitable mono-hydroxyl-terminated poly(lower alkylene oxides) which may be used to prepare the preferred B monomers using the above-described procedure include Carbowax ® 350, Carbowax ® 550, Carbowax ® 750, Carbowax ® 2000 and Carbowax ® 5000 (i.e., the methoxy- poly(ethylene oxide) ethanols of about 350 MW, 550 MW, 750 MW, 2000 MW and 5000 MW, respectively, commercially available from Union Carbide Corp); a monoalcohol of a polytetrahydrofuran of about 16,000 MW prepared as described in connection with the preparation of Monomer "B-9" in the Examples below; ⁇ CON ® LB-285 (an n-butoxy poly(propylene oxide) propanol having about a 1000 MW, commercially available from Union Carbide Corp.); UCON ® 50-HB260 (an n-butoxy poly(ethylene oxide/propylene oxide) [50:
  • B monomers wherein R is hydrogen may be prepared by reacting an ⁇ , ⁇ -unsaturated carboxylic acid or hydroxyalkyl ester with an anhydride selected from monoepoxides, lactones or mixtures thereof as taught in U.S. Patent No. 4,126,527, incorporated herein by reference.
  • the pressure-sensitive adhesive copolymer may comprise a single type of B monomer or may comprise two or more different B monomers.
  • the C monomer is a polar monomer which is copolymerizable with the A and B monomers.
  • the C monomer is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, acrylamide, methacrylamide, lower alkyl-substituted acrylamide, and N-vinyl-2-pyrrolidone.
  • suitable lower alkyl-substituted acrylamides are methyl acrylamide, ethyl acrylamide, and t-butylacrylamide.
  • the preferred C monomers are acrylic acid and acrylamide.
  • the pressure- sensitive adhesive copolymer may comprise a single type of C monomer or may comprise two or more different C monomers.
  • the adhesive properties of the pressure-sensi ive adhesive copolymer vary depending upon the particular combination and relative amounts of the A, B and C monomers employed in preparing the copolymer.
  • the combination of types and amounts of A, B and C monomers is such that the adhesive and the adhesive-coated sheet material exhibit the indicated initial dry skin adhesion value, dry skin adhesion value after 48 hours, and moist skin adhesion value.
  • any combination of types of A, B and C monomers may be employed so long as the resulting copolymer exhibits the required adhesion values.
  • amounts the amount
  • _ OMPI B monomer is present in an amount of about 5 to 30% of the total weight of all monomers in the copolymer and the C monomer is present 'in an amount of about 0.5 to 30% of the total weight of all monomers.
  • the particular amounts of the A, B and C monomers employed depend on the nature of the A, B and C monomers selected. The amounts of the B and
  • C monomers may be varied within the above ranges so long as the resulting adhesive copolymer exhibits the indicated adhesion values.
  • the amount of A monomer employed is preferably about 50 to 95% by weight of the total weight of all monomers in the copolymer, and is most preferably about
  • B and C monomers are about 10 to 20% and about 5 to 20%, respectively, based upon the total amount of all monomers in the copolymer.
  • Copolymers containing solely A, B and C monomers of appropriate types and in appropriate amounts perform suitably in the practice of the invention.
  • the copolymers of the invention may further include minor amounts of non-essential monomers such as methylacrylate, ethylacrylate, vinylacetate and the like.
  • copolymer may also be desirable in some instances in the practice of the invention to increase internal strength or cohesiveness of the copolymer by crosslinking the copolymer using conventional methods (e.g., irradiation of the copolymer or reaction of a crosslinking agent with reactive functionality contained in the copolymer through inclusion of a small amount of- an appropriate monomer therein).
  • conventional methods e.g., irradiation of the copolymer or reaction of a crosslinking agent with reactive functionality contained in the copolymer through inclusion of a small amount of- an appropriate monomer therein).
  • Nitrogen is bubbled through the solution to purge air from within the bottle, and the bottle is then sealed.
  • the sealed bottle is tumbled in a heated water bath for a
  • the backing may be, for example, a conventional nonwoven fabric, woven fabric, knit, paper, or synthetic film backing.
  • Preferred backings are nonwoven fabrics, woven fabrics, knits and the like which permit transpiraton of perspiration and tissue or wound exudate therethrough.
  • the backing may be of any desired shape to provide adhesive coated sheet materials embodied as adhesive tapes, strips, wound dressings, monitoring or neuro-stimulating electrodes, drapes or the like.
  • the pressure-sensitive adhesive copolymer may be 5 applied to the backing by conventional methods. As is known to those skilled in the art, the particular method selected may depend upon the nature of the backing being employed. For example, where the backing is a nonwoven fabric, a suitable method for applying the adhesive 0 copolymer thereto involves coating a solution of the adhesive copolymer in an organic solvent onto a release liner, followed by lamination of the nonwoven fabric backing to the (semi-dry) adhesive coating.
  • each strip is removed at a 90° angle from a line formed by the spinal 5 column using a conventional adhesion tester having a 25# test line and a 1-inch clip attached to the test line.
  • the clip is attached to the edge of the strip which is farthest - from the spinal cord, the clip being attached by manually lifting about 1/2-inch of that edge of the strip and ⁇ attaching the clip thereto.-
  • This orientation permits the strip to be removed starting from the outside of the back towards the spine so that pull is with the direction of fine hair growth on the back. This is facilitated by positioning the adhesion tester opposite the side of the individual's back from which the strip is to be removed.
  • the adhesion tester is aligned with and is at the same height as the strip to be removed in order to maintain the
  • the strip is pulled over itsself in a plane parallel ( 180° ) to the back and the rate of removal is 6 inches (15.2 cm) per minute. To determine initial skin adhesion, the strip is removed within about 5 minutes of its application to the back.
  • An acceptable sheet material in accordance with the invention exhibits an average initial dry skin adhesion value of at least about 0.75 Newton per 100 millimeters of width.
  • An example of a suitable adhesion tester for use in this Test Method A comprises a conventional motor driven screw with moving carriage and a transducer. Connected to the transducer is a load cell accessory. Removal force placed on the transducer results in a signal change which is passed through a readout meter to a strip chart recorder.
  • the adhesive-coated sheet material to be tested is cut into 1x3 inch (2.5 x 7.6 cm) strips which are applied to the (dry) backs of 6 individuals in accordance with the procedures of Test Method A above. Here, each strip is removed about 48 hours after its application. The procedure used for removal of the strip is that described in of Test Method A.
  • An acceptable sheet material in accordance with the invention exhibits an average dry skin adhesion value after 48 hours of no -more than about 12 Newtons per 100 millimeters of width.
  • conditioning compartment 11 which houses the machinery that provides the proper conditions of temperature and humidity within conditioning compartment 11.
  • control instruments 13 which maintain the proper conditions of temperature and humidity within conditioning compartment 11.
  • Control instruments 13 include a recorder for recording the conditions of temperature and humidity over a period of time.
  • Moisture is introduced into conditioning compartment 11 from an electrically-heated water reservoir (not illustrated) located within compressor compartment 12.
  • Conditioning compartment 11 is fitted with door 14 which preferably comprises methylmethacrylate or other transparent material.
  • Door 14 contains two iris ports 15 and 16 which permit passage of bare arms therethrough into the constant temperature/humidity chamber.
  • Conditioning chamber 11 also includes an adhesion tester 17 mounted on the exterior of wall 18 which is located opposite door 14, one suitable adhesion tester being that discussed above in connection with Test Method A.
  • Test line 19 of adhesion tester 17 passes through channel 20 of wall 18.
  • Water drain 21 functions to remove condensate from within conditioning compartment 11.
  • a suitable commercially available constant temperature/humidity chamber which may be modified to include iris ports as described above is that available under the trade designation "TH-10" from Tenney Engineering, Inc., Union, N.J.
  • the chamber is equilibrated at approximately 100°F and 95% relative humidity.
  • the individual after moistening his or her forearm with tap water, places the forearm 22 in the chamber via iris port 15.
  • a 1x3 inch (2.5 x 7.6 cm) strip 23 of the adhesive-coated sheet material to be tested is introduced into the chamber via iris port 16, and is applied to the inside, flat section of the forearm at a location about midway between the elbow and the wrist with the length of the strip parallel to the length of the arm (Fig. 1).
  • the strip is secured with firm thumb pressure.
  • the medial end of the strip is connected to a 1-inch clip 24 which in turn is connected through the test line 19 to the adhesion tester 17. While the forearm is held in a horizontal position with the strip facing up (Fig. 2), the strip is removed, at a 180° peel angle, parallel to the direction of the arm at a removal rate of 6 inches (15.2 cm) per minute.
  • An acceptable sheet material in accordance with the invention exhibits an average moist skin adhesion value of at least about 2.2 Newtons -per 100 millimeters of width.
  • Test Method D The adhesion performance of the pressure- sensitive adhesives of the- invention is determined by incorporating the particular pressure-sensitive adhesive in an adhesive-coated sheet material which is then tested in accordance with Test Methods A, B and C above.
  • the adhesive-coated sheet material is prepared as follows: A solution of the pressure-sensitive adhesive in an organic solvent is coated onto a silicone-treated release paper and allowed to air-dry at ambient conditions for about one minute. To the semi-dry adhesive layer is then laminated the web that is available commercially under the trade designatibn H 916L" from Hollingsworth & Vose Co.,
  • An acrylate ester of a polyether containing an average of about 7 repeating ethoxy units was prepared as follows: To a 1000 ml round bottom flask fitted with a magnetic stirrer and a Dean Stark trap were added 144 g (0.4 m) of Carbowax ® 350 (a methoxy poly(ethylene oxide) ethanol of about 350 MW, available from Union Carbide Corp.) 36 g (0.5 m) of acrylic acid, 9.6 g of p-toluene- sulfonic acid, 0.15 g of phenothiazine, and 160 g of toluene.
  • Carbowax ® 350 a methoxy poly(ethylene oxide) ethanol of about 350 MW, available from Union Carbide Corp.
  • An acrylate ester of a polyether containing an average of about 12*repeating ethoxy units was prepared as follows. To a flask of the type described above were added
  • MONOMER "B-3" 5 An acrylate ester of a polyether containing an average of about 16 repeating ethoxy units was prepared as follows.
  • Monomer "B-3” was also prepared by following the above procedure, except that here the monomer was isolated from the solvent by rotary evaporation as described in connection with the preparation of monomer "B-2". This solid was then used to prepare certain copolymers as described in the examples which follow.
  • MONOMER "B-4" A methacrylate ester of a polyether containing an average of about 16 repeating ethoxy units was prepared as follows.
  • An acrylate ester of a polyether containing an average of about 45 repeating ethoxy units was prepared as follows. To a flask of the type described above were added
  • An acrylate ester of a polyether containing an average of about 20 repeating ethoxy/propoxy units was prepared as follows.
  • An acrylate ester of a polyether containing an average of about 222 repeating tetramethylene oxide units was prepared as follows.
  • the polytetrahydrofuran polymer-containing mixture obtained above was added to a mixture of 2.2 g (0.02987 m) of acrylic acid, 2.9 g of anhydrous ammonium carbonate and 80 g of ethanol. The mixture was stirred overnight, after which time 300 g of the hydroxy form of
  • Pressure-sensitive adhesive copolymers of the invention which comprised the indicated A, B, and C monomers in the indicated amounts (TABLE I) were prepared as follows: To a 4 ounce glass bottle were added the indicated amounts (by weight) of the indicated A, B and C monomers; an amount (by weight) of the indicated solvent blend which provided a solution which was either 40% solids by weight (Examples 29, 30 and 33) or 50% solids by weight (Examples 1-28, 31-32 and 34-45); and ⁇ ,o'-azobis- isobutyronitrile in an amount of either 0.2% by weight (Examples 1-7 and 24) or 0.3% by weight (Examples 8-23 and 25-45) based on the total weight of the A, B and C monomers and the solvent blend.' ⁇ s indicated above.
  • Monomers "B-4", “B-7”, and “B-8" were added to the other ingredients of the various reaction mixtures as solutions in toluene, thereby introducing the indicated amounts of toluene into those reaction mixtures containing those B monomers. This was also the case where indicated for Monomer "B-3".
  • the reaction medium contained only ethyl acetate and isopropanol. The bottle was purged to eliminate air therefrom by bubbling nitrogen through the solution. The bottle was then sealed, and was tumbled for 24 hours in a water bath maintained at 55°C. The solution of the respective pressure-sensitive adhesive copolymer was then coated onto a backing as described below.
  • the resulting adhesive-coated sheet materials of the invention were tested in accordance with Test Methods A, B and C above and the results observed are listed in TABLE I. All of these adhesive-coated sheet materials were suitable in terms of initial dry skin adhesion performance, dry skin adhesion performance after 48 hours, and moist skin adhesion performance, and no irritation of skin was observed. TABLE I also lists the inherent viscosity (determined as described above) for each copolymer.
  • Copolymer Composition (% by weight) (% by weight) Initial ⁇ hesion Moist Monomer Monomer Inherent Dcy Skin After Skin
  • IOA isooctylacrylate
  • t-BAM t-butylacryamide

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Materials Engineering (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Adhésif sensible à la pression et matériau en feuille enduit d'adhésif sensible à la pression présentant une valeur initiale d'adhésion sur peau sèche au moins égale à 0,75 Newton par 100 millimètres de largeur, une valeur d'adhésion sur peau sèche après 48 heures ne dépassant pas environ 12 Newtons par 100 millimètres de largeur et une valeur d'adhésion sur peau mouillée au moins égale à environ 2,2 Newtons par 100 millimètres de largeur.
EP84901684A 1983-04-07 1984-04-06 Adhesif et materiau en feuille enduit d'adhesif pour la peau mouillee Withdrawn EP0140941A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48299183A 1983-04-07 1983-04-07
US482991 1995-06-07

Publications (1)

Publication Number Publication Date
EP0140941A1 true EP0140941A1 (fr) 1985-05-15

Family

ID=23918199

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84901684A Withdrawn EP0140941A1 (fr) 1983-04-07 1984-04-06 Adhesif et materiau en feuille enduit d'adhesif pour la peau mouillee

Country Status (4)

Country Link
EP (1) EP0140941A1 (fr)
JP (1) JPS60500992A (fr)
BR (1) BR8406510A (fr)
WO (1) WO1984003837A1 (fr)

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WO2008002743A1 (fr) 2006-06-27 2008-01-03 3M Innovative Properties Company Capteurs colorimétriques
EP2281860A1 (fr) 2009-08-03 2011-02-09 Morgan Adhesives Company Compositions adhésives pour une application facile et une durabilité améliorée
US10465017B2 (en) 2008-12-17 2019-11-05 3M Innovative Properties Company Bulk polymerization of silicone-containing copolymers
WO2025012822A2 (fr) 2023-07-12 2025-01-16 Solventum Intellectual Properties Company Adhésifs sensibles à la pression emballés

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US6949297B2 (en) 2001-11-02 2005-09-27 3M Innovative Properties Company Hybrid adhesives, articles, and methods
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US7449146B2 (en) 2002-09-30 2008-11-11 3M Innovative Properties Company Colorimetric sensor
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WO1984003837A1 (fr) 1984-10-11
JPS60500992A (ja) 1985-07-04
BR8406510A (pt) 1985-03-12

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