+

WO1993002717A1 - Produits adhesifs - Google Patents

Produits adhesifs Download PDF

Info

Publication number
WO1993002717A1
WO1993002717A1 PCT/GB1992/001481 GB9201481W WO9302717A1 WO 1993002717 A1 WO1993002717 A1 WO 1993002717A1 GB 9201481 W GB9201481 W GB 9201481W WO 9302717 A1 WO9302717 A1 WO 9302717A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive
product according
medicament
dressing
layer
Prior art date
Application number
PCT/GB1992/001481
Other languages
English (en)
Inventor
Mark Christopher Richardson
Original Assignee
Smith & Nephew Plc
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 Smith & Nephew Plc filed Critical Smith & Nephew Plc
Publication of WO1993002717A1 publication Critical patent/WO1993002717A1/fr

Links

Classifications

    • 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
    • A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
    • 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
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/202—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with halogen atoms, e.g. triclosan, povidone-iodine
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
    • A61L2300/206—Biguanides, e.g. chlorohexidine
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents

Definitions

  • the present invention relates to adhesive products suitable for application to the human body and to processes for their preparation. More particularly the invention relates to adhesive products containing releasable medicaments.
  • Adhesive products suitable for application to the human body such as adhesive coated wound dressings often comprise a medicament, for example an anti-microbial agent, within the adhesive coating thereof to assist the wound healing process.
  • a medicament for example an anti-microbial agent
  • the present invention provides an adhesive product suitable for application to the body which product comprises a support layer having on one side thereof a layer of ' an emulsion adhesive comprising residues of a copolymerisable emulsifier and wherein said adhesive coating contains a medicament.
  • Suitable medicaments for use in the invention include medicaments for topical use such as antimicrobial agents.
  • Favoured antimicrobial agents are water soluble.
  • antimicrobial agents can include iodine compounds such as povidone iodine, triclosan and chlorhexidine and its derivatives.
  • Apt water soluble antimicrobial agents for use in the invention are chlorhexidine gluconate and acetate.
  • the amount of medicament in the adhesive coating of the adhesive product of the invention can suitably be from 0.1 to 10% by wt, desirably 0.1 to 5% by wt and can preferably be 0.15 to 2% by wt of the adhesive coating.
  • the adhesive used in the invention are typically water based adhesives and will normally and preferably be a pressure sensitive adhesive.
  • the pressure sensitive adhesive will be an emulsion adhesive polymer containing residues of a vinyl monomer.
  • Preferred adhesives for use in the invention are acrylic pressure sensitive adhesives.
  • the copolymerisable emulsifier used in the invention therefore will normally be a surfactant containing a terminally unsaturated vinyl monomeric portion which can copolymerise with vinyl monomers such as acrylic monomers to form a pressure sensitive adhesive which is preferably an acrylic pressure sensitive adhesive.
  • a pressure sensitive adhesive is desirably an acrylate or methacrylate based adhesive.
  • the copolymerisable emulsifier can be an anionic, cationic or non-ionic emulsifier.
  • Favoured copolymerisable e ulsifiers will contain an anionic group such as a sulphonate.
  • Favoured adhesive products of the invention are those in which the emulsion adhesive polymer comprises residues of acrylic monomers containing 80 to 98.5% by weight of residues of alkyl esters of acrylic or methacrylic acid in which the alkyl group contains from 3 to 12 carbon atoms, from 0.1 to 20% by weight of residues of onoesters of methacrylic acid and 0.1 to 5% by weight of residues of a compound of the formula (I): CH, C - C - 0 - ( " CH 2 ) 3 s ( o 2 ) - OM
  • R is a C ⁇ o - C ⁇ 4 alkyl radical and M is hydrogen, ammonia or an alkali metal.
  • Emulsion adhesive polymers of this type are in European Patent Application No. 0194881.
  • the alkyl radical in formula (I) may contain 12 carbon atoms and M can be sodium, that is the compound of formula (I) may be sodium ono-lauryl itaconoxy propane sulphonate.
  • the emulsion adhesive polymer used in the invention can suitably comprise residues of one or more, for example two, alkyl esters of acrylic acid in which alkyl group contains 3 to 12 carbon atoms.
  • Favoured alkyl esters of acrylic acid are those in which the alkyl group has 4 to 9 carbon atoms, such as n-butyl acrylate 2-ethylhexyl acrylate and other octyl acrylates.
  • Preferred alkyl acrylates are n-butyl acrylate and 2-ethylhexyl acrylate.
  • the emulsion adhesive polymer used in the adhesive can comprise residues of one or more, for example two, monoesters of methacrylic acid.
  • Suitable monoesters of methacrylic acid can be selected from a group consisting of a lower alkyl, hydroxylated or alkoxylated esters for example methyl methacrylate, n-buty methacrylate hydroxyethylmethacrylate and ethoxyethylmethacrylate.
  • Preferred monoesters include hydroxyethyl methacrylate, methyl methacrylate and n-butyl methacrylate.
  • the emulsion adhesive polymers for use in the invention can comprise 36 to 50% by weight of n-butyl acrylate residues, 39 to 59% by weight of 2-ethyl hexyl acrylate residues, 1 to 15% by weight of lower alkyl methacrylate residues, 0.3 to 5% by weight of hydroxyethyl methacrylate residues and 0.1 to 5% by weight of residues of a compound of formula (I).
  • Lower alkyl when used herein means an alkyl radical containing from 1 to 6 carbon atoms.
  • Emulsion adhesive polymers of this type can comprise 39 to 45% by weight of n-butyl acrylate residues, 47 to 49.5% by weight of 2-ethylhexyl acrylate residues, 5 to 10% by weight of lower alkyl methacrylate residues, 0.8 to 3% by weight of hydroxyethyl methacrylate residues and 0.1 to 1% by weight of residues of a compound of formula (I).
  • An example of an adhesive polymer for use in the invention comprises 44.5% by weight of n-butyl acrylate residues, 49.5% by weight of 2-ethylhexyl acrylate residues, 5% by weight of n-butyl methacrylate residues, 1% by weight of hydroxyethyl methacrylate residues and 0.2% by weight of sodium mono-lauryl itaconoxypropane sulphate.
  • the coating of emulsion adhesive of the adhesive product of the invention can suitably have a weight per unit area of 10 to 75g/m 2 ., desirably of 15 to 65g/m 2 and can preferably have a weight per unit area of 20 to 40g/m 2 for example 30g/m 2 .
  • Adhesive product of the invention can favourably be a surgical or medical adhesive dressing.
  • the support layer therefore can suitably be a backing layer of a dressing of the invention, such back layers can be any of conformable backing layers used on conventional adhesive dressings, such backing layers can include woven and non-woven and knitted fabrics, flexible nets and flexible polymer films, including microporous films.
  • Preferred backing layers are moisture vapour transmitting films and in particular elastomeric moisture vapour transmitting films.
  • Favoured elastomeric moisture vapour transmitting films include those formed from polyether polyurethane, polyester polyurethane, hydrophilic polyurethane and polyester-polyether copolymers.
  • Suitable polyether polyurethanes are described in United States Patent No. 2899411. Suitable polyester polyurethanes are described in United States Patent No. 2871218. Apt polyester and polyether polyurethanes are known Estane (Trade Mark) available from B.F. Goodrich and in particular grades 5701, 5702, 5803, 5714F and 580201.
  • Hytral 4056 An apt polyester-polyether copolymer is known as Hytral 4056 available from Dupont. Suitable hydrophil ⁇ c polyurethane films for use in the inventions are disclosed in European Patent No. 91800.
  • the thickness of the films used for the backing layer can suitably be 9 to 80 ⁇ m, more suitable 15 to 50 ⁇ m and can preferably be 210 to 40 / um for example
  • Moisture vapour permeable dressings of the invention can suitably have a moisture vapour transmission rate of at least 300g/m 2 /24h, more suitably at least 500g/m 2 /24h and preferably at least 700g/m 2 /24h at 37°C at 100% to 10% relative humidity difference.
  • the moisture vapour permeable dressings of the invention suitably have a moisture vapour transmission (indicated) rate of at least 1200 gm/m 2 /24h when in contact with water.
  • a suitable method of determining the upright moisture vapour transmission rate of the dressing of this invention is as follows. Discs of material under test are clamped over Payne Permeability Cups (flanged metal cups) using sealing- rings and screw clamps. The exposed surface area of the test sample may be conveniently 10cm . Each cup contains approximately 10ml of distilled water. After weighing the cups are placed in a fan assisted'electric oven maintained at 37 ⁇ l ⁇ C. The relative humidity within the oven is maintained at 10% by placing 1 KG of anhydrous 3-8 mesh calcium chloride on the floor of the oven. The cups are removed after 24 hours, allowed to cool for 20 minutes and re-weighed. The MVTR of the test material is calculated from the weight loss expressed in units of grams of weight per square metre per 24 hours.
  • a suitable method of determining the inverted moisture vapour transmission rate of the dressing of this invention is as follows. The method described above is employed except that the Payne Cups are inverted in the oven so that the water within the cups is in contact with the test material and in this case with the adhesive.
  • the adhesive product of the invention preferably have a relea ⁇ able protector on the adhesive surface thereof.
  • the protector used may be any of the flexible release materials conventionally used to protect the adhesive surface of dressings. Suitable protectors include those made from plastics films such polyethylene, polypropylene or unplasticised polyvinyl chloride films, paper sheets and coated paper sheets which have been treated with a release agent such as a silicone resin.
  • Adhesive products in accordance with the invention can have a handle which is preferably removable attached to one or each of the opposing edge margins of the product material such as release coated paper or plastics film.
  • the handles can be attached either directly to the adhesive at opposed margins of the dressing indirectly by means of strips of adhesive tape which are preferably tearable to render the handles removable.
  • Suitable dressings with removable handles of the type are disclosed in United Kingdom Patent Application No. 2157955.
  • the handles can be adhered in a position in which they lie on top of the backing layer or preferably in a position where they lie alongside the backing layer.
  • the adhesive product can suitably be an adhesive surgical or medical dressing such as an adhesive wound dressing including a bandage, a first aid dressing, a burns dressing, a ulcer dressing, an IV or catheter dressing or a surgical incise drape.
  • an adhesive surgical or medical dressing such as an adhesive wound dressing including a bandage, a first aid dressing, a burns dressing, a ulcer dressing, an IV or catheter dressing or a surgical incise drape.
  • Such dressings can be in the form of a sheet, tape or roll.
  • the dressings of the invention are sterile within a bacteria-proof package.
  • the adhesive dressings of the invention have an advantage over conventional adhesive dressing in that in use on a exuding wound the adhesive surface of the dressing can provide immediate and sustained delivery of a medicament such as an antimicrobial agent to the wound. Such dressings therefore may be effective in protecting wounds against pathogenic organisms.
  • Dressings of the invention which comprise an adhesive containing chlorhexidine gluconate have been found to have a high activity against Staphylococus Aureus.
  • the dressings of the present invention may be employed, with advantage, as surgical incise drapes. Immediate release of the medicament such as chlorhexidine gluconate, provides rapid skin disinfection due to the bactericidal effect of the medicament. Sustained release provides a bacteristatic environment.
  • the medicament such as chlorhexidine gluconate
  • the dressings of the present invention can be used as IV dressings to protect, for example, catheter implants.
  • the invention provides a process for forming the adhesive product of the invention which comprises coating an aqueous solution of a medicament onto the exposed adhesive surface of an adhesive product which comprises a support layer having on one side thereof a coating of emulsion adhesive comprising residues of a copolymerisable emulsifier.
  • the materials used in the process of the invention can be the same as those used in the adhesive product of the invention.
  • Suitable adhesive products and methods of preparation for use in the process of the invention include those disclosed in the aforementioned European Patent Application No. 0194881.
  • the aqueous solution used in the process of the invention can be obtained by dissolving the medicament in water or a mixture of water and an water mixible organic solvent such as ethyl alcohol or isopropyl alcohol.
  • Favoured solutions for use in the process comprise an aqueous solution of chlorhexidine salts such as the acetate or gluconate in suitable amounts in water or water - alcohol mixture.
  • the alcohol may be isopropyl alcohol at a weight ratio of for example, 30 : 70 to 50 : 50.
  • the concentration of medicament in the aqueous solution can be adapted to the coated process and the weight per unit area desired.
  • the adhesive may be applied either as a continuous or discontinuous coating.
  • dressings of high moisture vapour permeability eg greater than 1400 and preferably greater than 3000 pattern spread adhesives may be employed.
  • the aqueous solution of medicament can be coated on the exposed adhesive surface of the adhesive product by any suitable conventional coating method including spraying, doctor blade coating and roller methods such as a gravure roller printing method which is preferred.
  • the medicament solution may be dried, for example by air drying or gentle heating.
  • coating solutions containing 2 to 30% by weight of chlorhexidine gluconate can be coated by a gravure roller printing method and will provide dry coatings having desired antimicrobial activity. Coating weights may be as high as 0.4 gm/m . However, coating weights (dry) of chlorhexidine gluconate as low as 0.040 g/m 2 have been found effective, and typically may be about 0.15 gm/m 2 .
  • a acrylic adhesive emulsion containing residues of ethylhexyl acrylate (49.5% by wt) n-butyl acrylate (44.5% by wt, n-butyl methacrylate (5% by wt) hydroxy ethyl methacrylate (1% by wt) and sodium mono-lauryl itaconoxy propane sulphonate (0.2%) was prepared in the same manner as Example 1 of European Patent Application No. 0194881.
  • the acrylic adhesive emulsion prepared above was thickened by addition of Prima ASE60 neutralised with ammoniam hydroxide and an antioxidant MONO & WSC (0.6% BY WT) added to the emulsion.
  • the emulsion was then coated onto a silicone
  • release coated paper by means of a blade over flat bed coating head and dried in an oven at 110° and 5°C to give a dry adhesive coating weight per unit area of 30g/m 2 .
  • the adhesive coating was then transferred to a polyether polyurethane (Estane 5712) film (30/m ) by laminating under pressure the film and the adhesive coated release paper by pressing the layers between the nip of two pressure rollers.
  • Adhesive dressings of the invention were prepared by coating the exposed adhesive surface of adhesive coated dressing samples prepared above with aqueous solutions containing different concentrations of chlorhexidine gluconate in water or water/isopropanol mixture by means of a gravure roller coating technique and allowed to air dry.
  • Example 1 to 4 has satisfactory adhesive properties.
  • An adhesive dressing control was prepared by coating the exposed adhesive surface of a adhesive coated dressing sample prepared above with water in same manner as the adhesive dressings of Examples 1 to
  • Adhesive dressing samples of Example 1 to 5 and the Control were then subjected to a test to determine the antimicrobial activity of the exposed adhesive surface of these dressings.
  • the test was carried out by the following procedure.
  • a number of 2.5 centimeter square samples were cut from the test dressings. Individual samples were placed in a petri dish. The samples were each inoculated with the test bacteria Staphylococus aureus. The adhesive surface of each sample was inoculated with about 10 5 bacteria, and the sample covered with a one 2.5cm glass square. The antibacterial activity of the chlorhexidine gluconate was inhibited after 0, 10 and 30 minutes, respectively by applying to the innoculum a Triptone-soya broth containing 3% by weight of lecothin and 2% by weight of a surfactant (Tween 80). The samples are cultured for 48 hours in an agar culture medium, and the surviving bacteria counted.
  • results are reported as a log decrease in bacteria from the ⁇ O" time to test time.
  • a 3 log reduction is desirable.
  • a 3 log reduction equals a 99.9% kill of the bacteria originally present in the sample.
  • the adhesive coating weight on the polyethylene terephthlete film was 30 gs and the chlorhexidine coating weight (dry) was 0.3 gs .
  • the chlorhexidine coating solution also contained a pink dye (Carmine).

Landscapes

  • Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Un produit adhésif apte à être appliqué au corps, par exemple un pansement, comprend une couche support, tel qu'une couche support conformable présentant sur l'un de ses côtés une couche d'une matière adhésive à émulsion comportant des restes d'un émulsifiant copolymérisable, ladite couche adhésive contenant un médicament. Les médicaments qui se prêtent à une utilisation topique comprennent les agents antimicrobiens tels que la polyvidone iodée, le triclosan et la chorhexidine et ses dérivés.
PCT/GB1992/001481 1991-08-09 1992-08-10 Produits adhesifs WO1993002717A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919117256A GB9117256D0 (en) 1991-08-09 1991-08-09 Adhesive products
GB9117256.9 1991-08-09

Publications (1)

Publication Number Publication Date
WO1993002717A1 true WO1993002717A1 (fr) 1993-02-18

Family

ID=10699772

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1992/001481 WO1993002717A1 (fr) 1991-08-09 1992-08-10 Produits adhesifs

Country Status (4)

Country Link
AU (1) AU2397092A (fr)
GB (1) GB9117256D0 (fr)
WO (1) WO1993002717A1 (fr)
ZA (1) ZA925975B (fr)

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994026258A1 (fr) * 1993-05-13 1994-11-24 Unilever N.V. Compositions orales contenant du triclosan, destinees au traitement des ulceres aphteux
WO1996014094A1 (fr) * 1994-11-04 1996-05-17 Minnesota Mining And Manufacturing Company Pansement pour peaux sensibles a permeabilite a l'humidite amelioree
WO1996030429A1 (fr) * 1995-03-30 1996-10-03 Smith & Nephew Plc Agents tensio-actifs, adhesifs et pansements formes a partir de ceux-ci
WO1997032613A1 (fr) * 1996-03-07 1997-09-12 Leatherite Pty Limited Ameliorations apportees a la gestion des soins des blessures
US5772640A (en) * 1996-01-05 1998-06-30 The Trustees Of Columbia University Of The City Of New York Triclosan-containing medical devices
AU700866B2 (en) * 1996-03-07 1999-01-14 Leatherite Pty. Limited Improvements in wound care management
WO1999038929A1 (fr) * 1998-01-30 1999-08-05 Coloplast A/S Article ayant une surface presentant des proprietes adhesives
US5979450A (en) * 1997-05-16 1999-11-09 3M Innovative Properties Company Surgical incise drape
US6224579B1 (en) 1999-03-31 2001-05-01 The Trustees Of Columbia University In The City Of New York Triclosan and silver compound containing medical devices
EP1508601A1 (fr) * 2003-08-21 2005-02-23 Closure Medical Corporation Compositions cyanoacryliques contenant un agent antimicrobien
US7329412B2 (en) 2000-12-22 2008-02-12 The Trustees Of Columbia University In The City Of New York Antimicrobial medical devices containing chlorhexidine free base and salt
US7456331B2 (en) * 2002-05-24 2008-11-25 Corium International, Inc. Composition for cushions, wounds dressings and other skin-contacting products
WO2010080936A2 (fr) 2009-01-07 2010-07-15 Entrotech, Inc. Stratifiés antimicrobiens contenant de la chlorhexidine
EP2386615A1 (fr) * 2010-04-26 2011-11-16 Nitto Denko Corporation Feuille adhésive sensible à la pression
USRE44145E1 (en) 2000-07-07 2013-04-09 A.V. Topchiev Institute Of Petrochemical Synthesis Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties
CN103381130A (zh) * 2012-05-03 2013-11-06 3M创新有限公司 抗菌型输液胶贴
WO2013167671A2 (fr) 2012-05-08 2013-11-14 Nolax Ag Procédé de production d'une composition de polyuréthane à deux composants comprenant un ou plusieurs additifs solubles dans des solvants polaires
WO2014003844A1 (fr) * 2012-06-29 2014-01-03 University Of South Florida Compositions de polyacrylate biocompatible et leurs procédés d'utilisation
US8840918B2 (en) 2001-05-01 2014-09-23 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions for tooth whitening
US8932624B2 (en) 2007-06-20 2015-01-13 The Trustees Of Columbia University In The City Of New York Bio-film resistant surfaces
US9084723B2 (en) 2001-05-01 2015-07-21 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions with an erodible backing member
US9089481B2 (en) 2001-05-01 2015-07-28 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions demonstrating phase separation on contact with aqueous media
US9127140B2 (en) 2001-05-01 2015-09-08 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Water-absorbent adhesive compositions and associated methods of manufacture and use
US9144552B2 (en) 2004-01-30 2015-09-29 A.V. Topchiev Institute Of Petrochemical Synthesis, Russian Academy Of Sciences Rapidly dissolving film for delivery of an active agent
US9242021B2 (en) 2004-08-05 2016-01-26 Corium International, Inc. Adhesive composition
US9259504B2 (en) 2001-05-01 2016-02-16 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Non-electrically conductive hydrogel composition
US9346981B2 (en) 2011-01-21 2016-05-24 Avery Dennison Corporation Chlorhexidine gluconate containing solvent adhesive
US9497975B2 (en) 2011-12-06 2016-11-22 The Trustees Of Columbia University In The City Of New York Broad spectrum natural preservative composition
US9511040B2 (en) 2007-06-20 2016-12-06 The Trustees Of Columbia University In The City Of New York Skin and surface disinfectant compositions containing botanicals
US9610253B2 (en) 2009-01-14 2017-04-04 Corium International, Inc. Transdermal administration of tamsulosin
US9687429B2 (en) 2007-06-20 2017-06-27 The Trustees Of Columbia University In The City Of New York Antimicrobial compositions containing low concentrations of botanicals
US9968101B2 (en) 2011-11-03 2018-05-15 The Trustees Of Columbia University In The City Of New York Botanical antimicrobial compositions
US9970303B2 (en) 2014-05-13 2018-05-15 Entrotech, Inc. Erosion protection sleeve
US9981069B2 (en) 2007-06-20 2018-05-29 The Trustees Of Columbia University In The City Of New York Bio-film resistant surfaces
US10456498B2 (en) 2013-02-07 2019-10-29 Avery Dennison Corporation Antimicrobial adhesives having improved properties
US10806144B2 (en) 2011-11-03 2020-10-20 The Trustees Of Columbia University In The City Of New York Composition with sustained antimicrobial activity
US11039615B2 (en) 2014-04-18 2021-06-22 Entrotech Life Sciences, Inc. Methods of processing chlorhexidine-containing polymerizable compositions and antimicrobial articles formed thereby
US11058793B2 (en) 2011-05-16 2021-07-13 Avery Dennison Corporation Adhesive containing microparticles
US11213432B2 (en) 2013-03-15 2022-01-04 Avery Dennison Corporation Transparent cover dressing application system and inclusion of label strip
US11337940B2 (en) 2014-06-05 2022-05-24 Avery Dennison Corporation Articles with active agent concentrated at the substrate contacting surface and related methods

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0023395A1 (fr) * 1979-07-31 1981-02-04 Minnesota Mining And Manufacturing Company Adhésif sensible à la pression contenant un microbicide à large spectre
EP0024107A1 (fr) * 1979-07-31 1981-02-25 Minnesota Mining And Manufacturing Company Adhésif sensible à la pression contenant de l'iode
EP0194881A2 (fr) * 1985-03-13 1986-09-17 Smith & Nephew plc Polymères en émulsion
EP0196459A2 (fr) * 1985-02-28 1986-10-08 Surgikos, Inc. Pansement microbicide
EP0256893A2 (fr) * 1986-08-20 1988-02-24 SMITH & NEPHEW plc Pansement pour blessures, sa fabrication et son application
WO1991001706A1 (fr) * 1989-08-03 1991-02-21 Smith & Nephew Plc Pansements adhesifs
WO1991001707A1 (fr) * 1989-08-03 1991-02-21 Smith & Nephew Plc Pansements adhesifs

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0023395A1 (fr) * 1979-07-31 1981-02-04 Minnesota Mining And Manufacturing Company Adhésif sensible à la pression contenant un microbicide à large spectre
EP0024107A1 (fr) * 1979-07-31 1981-02-25 Minnesota Mining And Manufacturing Company Adhésif sensible à la pression contenant de l'iode
EP0196459A2 (fr) * 1985-02-28 1986-10-08 Surgikos, Inc. Pansement microbicide
EP0194881A2 (fr) * 1985-03-13 1986-09-17 Smith & Nephew plc Polymères en émulsion
EP0256893A2 (fr) * 1986-08-20 1988-02-24 SMITH & NEPHEW plc Pansement pour blessures, sa fabrication et son application
WO1991001706A1 (fr) * 1989-08-03 1991-02-21 Smith & Nephew Plc Pansements adhesifs
WO1991001707A1 (fr) * 1989-08-03 1991-02-21 Smith & Nephew Plc Pansements adhesifs

Cited By (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994026258A1 (fr) * 1993-05-13 1994-11-24 Unilever N.V. Compositions orales contenant du triclosan, destinees au traitement des ulceres aphteux
US5908693A (en) * 1994-11-04 1999-06-01 Minnesota Mining And Manufacturing Company Low trauma wound dressing with improved moisture vapor permeability
WO1996014094A1 (fr) * 1994-11-04 1996-05-17 Minnesota Mining And Manufacturing Company Pansement pour peaux sensibles a permeabilite a l'humidite amelioree
US5614310A (en) * 1994-11-04 1997-03-25 Minnesota Mining And Manufacturing Company Low trauma wound dressing with improved moisture vapor permeability
WO1996030429A1 (fr) * 1995-03-30 1996-10-03 Smith & Nephew Plc Agents tensio-actifs, adhesifs et pansements formes a partir de ceux-ci
US6706024B2 (en) 1995-06-07 2004-03-16 The Trustees Of Columbia University In The City Of New York Triclosan-containing medical devices
US6872195B2 (en) 1996-01-05 2005-03-29 The Trustees Of Columbia University In The City Of New York Chlorhexidine-containing medical devices
US5772640A (en) * 1996-01-05 1998-06-30 The Trustees Of Columbia University Of The City Of New York Triclosan-containing medical devices
US6626873B1 (en) 1996-01-05 2003-09-30 Trustees Of Columbia University Tricolosan-containing medical devices
US6083208A (en) * 1996-01-05 2000-07-04 The Trustees Of Columbia University Of The City Of New York Triclosan-containing medical devices
US6106505A (en) * 1996-01-05 2000-08-22 The Trustees Of Columbia University Of The City Of New York Triclosan-containing medical devices
AU700866B2 (en) * 1996-03-07 1999-01-14 Leatherite Pty. Limited Improvements in wound care management
WO1997032613A1 (fr) * 1996-03-07 1997-09-12 Leatherite Pty Limited Ameliorations apportees a la gestion des soins des blessures
US6700032B1 (en) 1996-03-07 2004-03-02 Leatherite Pty Limited Wound care management
CN1121877C (zh) * 1996-03-07 2003-09-24 莱瑟里特有限公司 伤口护理的改进
US6742522B1 (en) 1997-05-16 2004-06-01 3M Innovative Properties Company Surgical incise drape
US5979450A (en) * 1997-05-16 1999-11-09 3M Innovative Properties Company Surgical incise drape
US6482491B1 (en) 1998-01-30 2002-11-19 Coloplast A/S Article having a surface showing adhesive properties
WO1999038929A1 (fr) * 1998-01-30 1999-08-05 Coloplast A/S Article ayant une surface presentant des proprietes adhesives
US6224579B1 (en) 1999-03-31 2001-05-01 The Trustees Of Columbia University In The City Of New York Triclosan and silver compound containing medical devices
US6843784B2 (en) 1999-03-31 2005-01-18 The Trustees Of Columbia University In The City Of New York Triclosan and silver compound containing medical devices
USRE44145E1 (en) 2000-07-07 2013-04-09 A.V. Topchiev Institute Of Petrochemical Synthesis Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties
USRE45666E1 (en) 2000-07-07 2015-09-08 A.V. Topchiev Institute Of Petrochemical Synthesis Preparation of hydrophilic pressure sensitive adhesives having optimized adhesive properties
US7329412B2 (en) 2000-12-22 2008-02-12 The Trustees Of Columbia University In The City Of New York Antimicrobial medical devices containing chlorhexidine free base and salt
US8906401B2 (en) 2000-12-22 2014-12-09 The Trustees Of Columbia University In The City Of New York Antimicrobial medical devices containing chlorhexidine free base and salt
US7537779B2 (en) 2000-12-22 2009-05-26 The Trustees Of Columbia University In The City Of New York Antimicrobial medical devices
US8840918B2 (en) 2001-05-01 2014-09-23 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions for tooth whitening
US9089481B2 (en) 2001-05-01 2015-07-28 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions demonstrating phase separation on contact with aqueous media
US10869947B2 (en) 2001-05-01 2020-12-22 Corium, Inc. Hydrogel compositions
US10835454B2 (en) 2001-05-01 2020-11-17 Corium, Inc. Hydrogel compositions with an erodible backing member
US9532935B2 (en) 2001-05-01 2017-01-03 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions for tooth whitening
US9687428B2 (en) 2001-05-01 2017-06-27 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions for tooth whitening
US10179096B2 (en) 2001-05-01 2019-01-15 Corium International, Inc. Hydrogel compositions for tooth whitening
US9259504B2 (en) 2001-05-01 2016-02-16 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Non-electrically conductive hydrogel composition
US9127140B2 (en) 2001-05-01 2015-09-08 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Water-absorbent adhesive compositions and associated methods of manufacture and use
US9084723B2 (en) 2001-05-01 2015-07-21 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences Hydrogel compositions with an erodible backing member
US7456331B2 (en) * 2002-05-24 2008-11-25 Corium International, Inc. Composition for cushions, wounds dressings and other skin-contacting products
EP1508601A1 (fr) * 2003-08-21 2005-02-23 Closure Medical Corporation Compositions cyanoacryliques contenant un agent antimicrobien
US9144552B2 (en) 2004-01-30 2015-09-29 A.V. Topchiev Institute Of Petrochemical Synthesis, Russian Academy Of Sciences Rapidly dissolving film for delivery of an active agent
US9242021B2 (en) 2004-08-05 2016-01-26 Corium International, Inc. Adhesive composition
US8932624B2 (en) 2007-06-20 2015-01-13 The Trustees Of Columbia University In The City Of New York Bio-film resistant surfaces
US9687429B2 (en) 2007-06-20 2017-06-27 The Trustees Of Columbia University In The City Of New York Antimicrobial compositions containing low concentrations of botanicals
US9981069B2 (en) 2007-06-20 2018-05-29 The Trustees Of Columbia University In The City Of New York Bio-film resistant surfaces
US9511040B2 (en) 2007-06-20 2016-12-06 The Trustees Of Columbia University In The City Of New York Skin and surface disinfectant compositions containing botanicals
US10542760B2 (en) 2007-06-20 2020-01-28 The Trustees Of Columbia University In The City Of New York Skin and surface disinfectant compositions containing botanicals
WO2010080936A2 (fr) 2009-01-07 2010-07-15 Entrotech, Inc. Stratifiés antimicrobiens contenant de la chlorhexidine
US10314935B2 (en) 2009-01-07 2019-06-11 Entrotech Life Sciences, Inc. Chlorhexidine-containing antimicrobial laminates
EP2373270A4 (fr) * 2009-01-07 2012-08-15 Entrotech Inc Stratifiés antimicrobiens contenant de la chlorhexidine
US9610253B2 (en) 2009-01-14 2017-04-04 Corium International, Inc. Transdermal administration of tamsulosin
US10238612B2 (en) 2009-01-14 2019-03-26 Corium International, Inc. Transdermal administration of tamsulosin
EP2386615A1 (fr) * 2010-04-26 2011-11-16 Nitto Denko Corporation Feuille adhésive sensible à la pression
US9764059B2 (en) 2011-01-21 2017-09-19 Avery Dennison Corporation Chlorhexidine gluconate containing solvent adhesive
US9346981B2 (en) 2011-01-21 2016-05-24 Avery Dennison Corporation Chlorhexidine gluconate containing solvent adhesive
US12036335B2 (en) 2011-05-16 2024-07-16 Avery Dennison Corporation Adhesive containing microparticles
US11707549B2 (en) 2011-05-16 2023-07-25 Avery Dennison Corporation Adhesive containing microparticles
US11058793B2 (en) 2011-05-16 2021-07-13 Avery Dennison Corporation Adhesive containing microparticles
US9968101B2 (en) 2011-11-03 2018-05-15 The Trustees Of Columbia University In The City Of New York Botanical antimicrobial compositions
US10806144B2 (en) 2011-11-03 2020-10-20 The Trustees Of Columbia University In The City Of New York Composition with sustained antimicrobial activity
US9497975B2 (en) 2011-12-06 2016-11-22 The Trustees Of Columbia University In The City Of New York Broad spectrum natural preservative composition
CN103381130A (zh) * 2012-05-03 2013-11-06 3M创新有限公司 抗菌型输液胶贴
WO2013167671A3 (fr) * 2012-05-08 2014-02-13 Nolax Ag Procédé de production d'une composition de polyuréthane à deux composants comprenant un ou plusieurs additifs solubles dans des solvants polaires
WO2013167671A2 (fr) 2012-05-08 2013-11-14 Nolax Ag Procédé de production d'une composition de polyuréthane à deux composants comprenant un ou plusieurs additifs solubles dans des solvants polaires
WO2014003844A1 (fr) * 2012-06-29 2014-01-03 University Of South Florida Compositions de polyacrylate biocompatible et leurs procédés d'utilisation
US10456498B2 (en) 2013-02-07 2019-10-29 Avery Dennison Corporation Antimicrobial adhesives having improved properties
US11318223B2 (en) 2013-02-07 2022-05-03 Avery Dennison Corporation Antimicrobial adhesives having improved properties
US11213432B2 (en) 2013-03-15 2022-01-04 Avery Dennison Corporation Transparent cover dressing application system and inclusion of label strip
US11039615B2 (en) 2014-04-18 2021-06-22 Entrotech Life Sciences, Inc. Methods of processing chlorhexidine-containing polymerizable compositions and antimicrobial articles formed thereby
US9970303B2 (en) 2014-05-13 2018-05-15 Entrotech, Inc. Erosion protection sleeve
US11337940B2 (en) 2014-06-05 2022-05-24 Avery Dennison Corporation Articles with active agent concentrated at the substrate contacting surface and related methods
US12109180B2 (en) 2014-06-05 2024-10-08 Avery Dennison Corporation Articles with active agent concentrated at the substrate contacting surface and related methods

Also Published As

Publication number Publication date
AU2397092A (en) 1993-03-02
ZA925975B (en) 1993-05-27
GB9117256D0 (en) 1991-09-25

Similar Documents

Publication Publication Date Title
WO1993002717A1 (fr) Produits adhesifs
US5069907A (en) Surgical drape having incorporated therein a broad spectrum antimicrobial agent
KR950003697B1 (ko) 항미생물성 드레싱 및 그의 제조방법
EP0196459B1 (fr) Pansement microbicide
US5183664A (en) Thin film adhesive dressings preparation and use
EP0123465B2 (fr) Pansement chirurgical adhésif
EP0501124B1 (fr) Composition d'adhésif sensible à la pression, perméable à la vapeur d'eau
KR101651709B1 (ko) 수용성 감압 접착제
US4323557A (en) Pressure-sensitive adhesive containing iodine
EP2410962B1 (fr) Compositions multicouches et pansements
EP3068448B1 (fr) Composition multicouche
US5648167A (en) Adhesive compositions
US20070282237A1 (en) Absorbent materials and articles
US8609128B2 (en) Cyanoacrylate-based liquid microbial sealant drape
US5717005A (en) Adhesive compositions and products
JPH0622558B2 (ja) 抗菌剤を含有する皮膜形成性組成物
CA1334643C (fr) Pansements adhesifs
WO2009098518A2 (fr) Composites hydrogels et pansements pour blessures
EP0594609B1 (fr) Compositions adhesives
WO2007113452A1 (fr) Matériaux et articles absorbants
JP3253431B2 (ja) 医療用貼付材
JPS61187867A (ja) 医療用粘着シ−トもしくはテ−プ
JPS61228868A (ja) 医療用粘着剤に用いられる樹脂およびそれを用いた医療用粘着シ−トもしくはテ−プ
JPH07275339A (ja) 創傷被覆材
EP3976121A1 (fr) Compositions adhésives

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AT AU BB BG BR CA CH CS DE DK ES FI GB HU JP KP KR LK LU MG MN MW NL NO PL RO RU SD SE US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL SE BF BJ CF CG CI CM GA GN ML MR SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA

122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载