CA1151548A - Pressure-sensitive adhesive containing iodine - Google Patents

Pressure-sensitive adhesive containing iodine

Info

Publication number
CA1151548A
CA1151548A CA000354628A CA354628A CA1151548A CA 1151548 A CA1151548 A CA 1151548A CA 000354628 A CA000354628 A CA 000354628A CA 354628 A CA354628 A CA 354628A CA 1151548 A CA1151548 A CA 1151548A
Authority
CA
Canada
Prior art keywords
iodine
sensitive adhesive
pressure
adhesive
composition
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.)
Expired
Application number
CA000354628A
Other languages
French (fr)
Inventor
Paul D. Rosso
Michael Y. Moss
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22041975&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1151548(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Application granted granted Critical
Publication of CA1151548A publication Critical patent/CA1151548A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/12—Iodine, e.g. iodophors; Compounds thereof
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F2013/00361—Plasters
    • A61F2013/00655—Plasters adhesive
    • A61F2013/0071—Plasters adhesive containing active agent
    • 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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/106—Halogens or compounds thereof, e.g. iodine, chlorite
    • 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

Abstract

Abstract A process for making a stable chemical complex of iodine, an iodide ion and a dermatologically acceptable room temperature tacky pressure-sensitive adhesive which is substantially free of acidic components. The resulting composition exhibits broad-spectrum antimicrobial activity when placed in contact with mammalian skin and is useful in or on tapes, drapes, and other medical devices.

Description

A PRESSURE-SENSITIVE ~DHESIVE
CONTAINING IODINE

This invention relates to a process for making dermatologically acceptable pressure-sensitive adhesive containing iodine. An aspect of this invention relates to the ability of the resulting composition to exhibit anti-septic broad-spectrum antimil~robial activity in a controlled and sustained manner.
Numerous pathogens are present on the human skin. In a hospital environment it is generally desired that the growth of disease-producing microorganisms be inhibited and preferably that these microorganisms be destroyed so as to control patient infection and encourage wound healing. As a result, the application to the skin surface of topical bactericidally active agents has become a standard part of the aseptic hospital technique.
One often used antimicrobial agent is iodine but because of its inherent chemical and physical limitations, its use as an antiseptic broad-spectrum antimicrobial has been limited. Elemental iodine has a high vapor pressure which causes great loss in germicidal potency as the iodine content volatilizes from antiseptic preparations containing iodine as the antimicrobial agent. Moreover, iodine is generally not occluded with bandages because of potential for corrosive destruction of skin.
In order to preserve the antimicrobial activity of iodine and at the same time reduce the corrosive properties and vapor pressure, complexes of polyvinyl-pyrrolidone and iodine have been formed. An example of the synthesis of one such polyvinylpyrrolidone-iodine complex (PVP-I) is disclosed in U.S. Patent 4,128,633.
The topical applications of broad-spectrum antimicrobials have been in the form of preoperative skin preps, surgical scrub tissues, e.g. U.S. Patent 4,045,364, washes, wound cleaners r lotions and ointments. In some instances such a delivery is effective for the particular ,. ,~.

:

5~8 purpose for a limited period of time. Microorganisms that may have survived the initial application of the antimicrobial agent act as a seed -to cause -the pathogen population in some instances to rise to their initial levels. Contin-uous application of an antimicrobial agent to the site is a means of inhibiting the increase in population.
While numerous other biologically active agen-ts have been incorporated into adhesive layers on a substrate to provide a continuous application to the body of the agent, there has been no successful incorporation of a broad-spectrum antimicrobial into an adhesive layer which has been characterized by stability and unaltered activity of the broad-spectrum antimicrobial. Examples of various other agents that have been incorporated into adhesives are United States Patent 2,137,169 where phenol, thymol, menthol, e-tc. are added to a starch adhesive; United States Patent 3,249,109 where benzocaine was added to a tacky gelatin; United States Patent 3,632,740 where a corticosteroid is added to an adhesive; United States Patent 3,734,097 where a microencapsulated anti-neoplastic agent is added to an adhesive; United States Patent 4,073,291 where Tretinoin is added to an adhesive; United States Patent 3,769,071 where 5-fluorouracil is incorporated into an adhesive; and United States Patent 3,896,789 where retinoic acid is incorporated into a pressure sensitive tape.
Previous attempts at incorporating broad-spectrum antimicrobials into adhesives have~been frustrated by reduced biological activity, and uncontrollable release which causes skin irritation in some patients.
The term broad-spectrum is used herein to mean that the antimicrobial exhibits activity against more than one type of microorganism, i.e. both gram positive and gram negative bacteria and would very likely also have activity against fungi and viruses (Reference: Federal Register, Vol. 39, No. 179).
The present invention provides a process for making a composition which exhibits controlled and sustained antiseptic broad-spectrum antimicrobial 9~-~ --2--.~

activity when placed in contact with the skin comprising forming a solution of an iodide, a solvent and iodine, and reacting said solution with a dermato-logically acceptable pressure-sensitive adhesive.
The present invention may be generally described as a process for the formation of a chemical and storage .. ~
- 2a -: .
;, ' .
- : :

5~8 stable composition which when placed in contact with the skin uniformly and controllably releases the broad-spectrum antimicrobial agent iodine. This release occurs with substantially unalterecl broad-spectrum antimicrobial activity even after being subjected to irradiation sterilization. This antiseptic antimicrobial activity is accomplished by the present invention with essentially no skin irritation.
The resulting composition of the process of the present invention is a stable chemical complex oE iodine, an iodide ion and a dermatologically acceptable normally room temperature tacky pressure sensitive adhesive (PSA).
By "stable" it is meant that a composition coating of 11 grains per 24 sq. in. which is attached to a polyethylene sheet can be exposed to a temperature of 120F and a relative humidity of 9~ for two (2) weeks or to a dose of
2.5 megarads of gamma irradiation without substantial alteration of the physical appearance or of the chemical activity, as tested by the starch test and microbiological activity as tested by Zone Inhibition Assay.
The Zone Inhibition Assay test is performed as follows: An assay bacterium Bacillus subtilis is grown in rotary shake culture (200 rpm) for approxiamtely 6 hours at 37C. The growth medium, L-broth, consist of the following ingredients dissolved in 1 L of distilled water and adjusted to pH 7.0: tryptone 10 g, yeast extract 5 g, sodium chloride 10 g, glucose 1 g. This culture is diluted in sterile L-broth to 50% T @ 660 mu, further diluted 1:10, and inoculated at a ratio of 1:100 into molten soybean-casein digest agar medium (Inolex) maintained at 45-50C. Assay plates are prepared by first pipesetting a 5 ml base layer of soybean-casein digest agar medium (TSA), allowing this to harden at room temperature in disposable petri dishes, and then overlaying with 5 ml of seeded TSA. These preparations are used the same day.

, .

~51~8 Coated polyethylene films (prepared in the manner taught in the Example below) are tested in the same way regardless of the antimicrobial incorporated into the adhesive layer. Ten o mm discs are cut from an evenly coated area (i.e. no visible flaws) with a heavy duty paper punch (Master Products, Series 25). The paper backing is removed from the coated disc with the aid of forceps and microspatula. The coated disc is then placed adhesive-side down on the seeded-agar surface, 4 per plate.
Iodine reference discs are then prepared. A
solution containing 10 percent iodine is prepared by dissolving 1 g of iodine and 1 g of sodium iodide in 10 percent aqueous acetone using a 10 ml volumetric flask.
This stock solution, freshly prepared and the same solvent is used to prepare 0.~5, 0.5, 0.75 and 1.0 percent iodine solutions. From these dilutions, 10 uI aliquots are applied to 6 mm polyester fabric discs placed on the seeded agar surface to provide discs containing 25, 50, 75 and 100 ug iodine each. IThe polyester fabric should be leached overnight in solvent to remove inherent antibacterial activity prior to punching ) Each reference disc is covered with a 1 inch square of 2-ml polyethylene to prevent vaporization prior to diffusion through the underlying agar.
The coated discs and reference disc assay plates are incubated overnight at room temperature. Zones of inhibition around the discs were measured to the nearest 0.5 mm with the aid of a binocular stereoscopic microscope. In the case of iodine antimicrobials, the coated discs are also removed to examine plates for areas of growth inhibition under the discs.
Assay results for reference antimicrobials using the preceding methods demonstrate that the diameter of the zone of inhibition measured in mm is linearly proportional to LOGlo concentration for each agent over the range examined. The release of antimicrobial from the adhesive S41~

of the present invention can be estimated by graphic interpolation oE the inhibition values.
The starch test is performed as follows: An dicator solution is prepared by dissolving 62.5 g of .i " ~`~ qd~ ~
~ Iodine Titration Indicator (Eastern Chemical, Division of Guardian Chemical Corp., Hauppauge, N~) is dissolved in 250 ml of distilled water with stirring. A
drop of the Paragon Indicator solution from then is placed on the adhesive surface. Formation of blue coloration in the drop indicates availability of iodine.
The process for forming the composition of the present invention involves forming a pressure sensitive adhesive and mixing into it an antimicrobial treating solution comprising iodine, an iodide, and a solvent. The resulting composition preferably contains N-vinyl-pyrrolidone (NVP) in the backbone of the pressure-sensitive adhesive which serves to complex iodine. It is believed that complexation provides stability while maintaining an appropriate equilibrium to provide sustained release of iodine.
The composition which is the resulting chemical complex of the aforementioned process is stable, non-irritating, non-sensitizing, non-toxic and non-trauma-tizing to skin or other tissues. Although it is generally recognized that an acid medium renders many broad-spectrum antimicrobial agents more stable, i.e.
PVP-I, it has been found that a pressure sensitive adhesive having a significant acidic content causes a negative alteration in the stability of iodine in the present system. Therefore it is desirable that the normally room temperature tacky pressure-sensitive adhesive monomers which is to act as the base of the present composition be substantially free of acidic components. By "substantially free of acidic components"
it is meant that the pressure-sensitive adhesive monomers be substantially free of substituent groups which exhibit acid functionality, e.g., acrylic acid~ etc. Examples of ~ f~fJ,cfe M,3~k s~

adhesive monomer which can be utilized in the preparation present antimicrobial composition PSA include acrylics and vinyl/acrylics. The formulation of these adhesives are well known in the art, e.g. U.S. Patents RE 24906, 2,973,286, 3,307,544, 3,728,148, etc. It will be appreciated by one skilled in the art that the aforestated adhesive types might also include various chemical modifiers so as to enable them to have the utility dictated by the situation, e.y. tackifiers, crosslinkers, stabili2ers, initiators etc. The preferred pressure sensitive adhesive for use in this invention is a copolymer comprised of N-vinylpyrrolidone (NVP) and isooctyl acrylate (IOA).
It is believed that the iodine release is controlled by the copolymerization of low levels of the NVP into the adhesive backbone. The iodine release from the adhesive matrix is a function of the level of NVP
copolymerized into the adhesive backbone. For a given iodine content, the higher the NVP level, the lower the antimicrobial activity~ For this invention, the useful NVP comonomer level is less than 30% (preferentially 5-10%) of the total adhesive solids. At higher ~VP
levels, skin adhesion and antimicrobial activity are - reduced.
An antimicrobial solution is used to incorporate iodine into the pressure sensitive adhesive. This solution contains iodine, inorganic iodide (e.g., potassium iodide) and a suitable solvent compatible with the adhesive. A solution recommended for use with the 5-10% NVP copolymer adhesive above would have a ~.5:1 to 4:1 molar ratio of iodide:iodine dissolved in denatured ethanol (preferred solution, 2:1 molar ratio of iodide:iodine). For example, a solution utilizing sodium iodide would have a formulation of 1-20 wt.% iodine, 1.2-24 wt.~; sodium iodide and 97.8-56 wt.% ethanol.
Although the mechanism of complexation of iodine into the aclhesive matrix of this invention is not 15~8 completely understood, it is believed to have some analogy to the complexation of iodine with polyvinylpyrrolidone.
The following is one possible representation of the complex of the present invention:
5 / IOR ~ ~ ~ C=~ ~ OR ~ ¦ ~ C=o~
C=OI N ~ ~1 C=o~
~CH2-CH-~L - -CH2-CH---/ CH2-CH-~ CH2-CH~

where m, n, o and p are integers.

The composition of the process of the present invention may be either attached directly onto a flexible backing substrate or ~ormed onto a release liner for later use. The backing may be any material known for use in medical application with the preferred material being polyethylene film. The solvents are then evaporated by means known to the art whereby an adhesive film is formed which is useable in or on tapes, drapes and other medical 15 devices.
The invention is further illustrated by the following non-limiting example:
A solution polymer adhesive of composition isooctyl acrylate/N-vinylpyrrolidone/ -methacryloxypropyl trimethoxysilane (94.95/5/0.05) is prepared by polymeriza-tion in ethyl acetate/heptane/ethanol (48/47/5) (Conditions: nitrogen atmosphere, azobisisobutyronitrile initiator, 6 hours at 53C; Properties: total solids =
45%, intrinsic viscosity = 0.8).
25 The following formulation is prepared:
adhesive from above 500 g.
a solution containing 20 wt.% iodine/24 wt.%
sodium iodide in denatured ethanol 11 g.
additional denatured ethanol 78 g.
30 a 10 wt.% solution of p-toluenesulfonic acid (p-TSA) in denatured ethanol (0.1 wt.%
p-TSA on adhesive solids) 2.3 g.

5~8 The formulation is stirred at room temperature with a spatula to yield a uniform solution of 1 wt.% iodine/1.2 wt.% sodium iodide on adhesive solids. This solution is coated onto a silicone release liner and dried (10 min., 175F) to form a homogeneous, iodine-colored adhesive film of coating weight equal to 11 grains/24 sq. in. The adhesive film is laminated to a backing of a corona and quatarnary amine antistat treated polyethylene to form a construction containing the antimicrobial iodine. This construction exhibited an activity when applied in vivo on seeded human skin of a four ~4) log reduction of Staph~lococcus aureus and Pseudomonas aeruginosa after one hour. The construction exhibited satisfactory adhesion and stability after sterilization by irradiation.

Claims (7)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for making a composition which exhibits controlled and sustained antiseptic broad-spectrum antimicrobial activity when placed in con-tact with the skin comprising forming a solution of an iodide, a solvent and iodine, and reacting said solution with a dermatologically acceptable pressure-sensitive adhesive.
2. A composition which exhibits antiseptic broad-spectrum antimicrobial activity when placed in contact with the skin comprising a stable chemical complex of an iodide, iodine and a dermatologically acceptable pressure-sensitive adhesive.
3. The composition of claim 2 wherein said dermatologically acceptable pressure-sensitive adhesive is substantially free of acidic components.
4. A flexible sheet material having attached thereto a composition comprising a stable chemical complex of an iodide, iodine and a dermatologically acceptable pressure-sensitive adhesive.
5. The composition of claim 2 or 4 wherein said pressure-sensitive adhesive is a copolymer comprising isooctyl arylate and N-vinyl-pyrrolidone.
6. A process in accordance with claim 1 wherein said pressure-sensitive adhesive is substantially free of acidic components.
7. A process in accordance with claim 1 or 6 wherein said pressure-sensi-tive adhesive is a copolymer comprising N-vinyl pyrrolidone and isooctyl acrylate.
CA000354628A 1979-07-31 1980-06-23 Pressure-sensitive adhesive containing iodine Expired CA1151548A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62,362 1979-07-31
US06/062,362 US4323557A (en) 1979-07-31 1979-07-31 Pressure-sensitive adhesive containing iodine

Publications (1)

Publication Number Publication Date
CA1151548A true CA1151548A (en) 1983-08-09

Family

ID=22041975

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000354628A Expired CA1151548A (en) 1979-07-31 1980-06-23 Pressure-sensitive adhesive containing iodine

Country Status (8)

Country Link
US (1) US4323557A (en)
EP (1) EP0024107B2 (en)
JP (2) JPS5622727A (en)
AU (1) AU537351B2 (en)
CA (1) CA1151548A (en)
DE (1) DE3065603D1 (en)
ES (1) ES493775A0 (en)
ZA (1) ZA804631B (en)

Families Citing this family (248)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011471B1 (en) * 1978-11-17 1983-02-09 SMITH & NEPHEW RESEARCH LIMITED Adhesive-coated sheet material incorporating anti-bacterial substances
US4323557A (en) * 1979-07-31 1982-04-06 Minnesota Mining & Manufacturing Company Pressure-sensitive adhesive containing iodine
SU1170663A1 (en) * 1983-04-14 1987-04-23 Всесоюзный научно-исследовательский и испытательный институт медицинской техники Compound for joning tissues and organs
JPS6041968A (en) * 1983-08-19 1985-03-05 日東電工株式会社 Hydrophilic drug member
EP0163653A4 (en) * 1983-11-29 1987-01-10 Avtex Fibers Inc Microbicidal materials.
US4584192A (en) * 1984-06-04 1986-04-22 Minnesota Mining & Manufacturing Company Film-forming composition containing an antimicrobial agent and methods of use
US4904247A (en) * 1984-08-31 1990-02-27 Kendall Company Pressure-sensitive hydrophilic laminate structures for use in wound dressing, transdermal and topical drug delivery
US4685455A (en) * 1984-10-16 1987-08-11 Akzo Nv Watervapor-permeable, pressure sensitive, antiseptic wound covering material
AU563054B2 (en) * 1984-10-24 1987-06-25 Sekisui Kagaku Kogyo Kabushiki Kaisha Percutaneous tape of isdn
US4643180A (en) * 1985-02-28 1987-02-17 Surgikos, Inc. Antimicrobial dressing
US4693776A (en) * 1985-05-16 1987-09-15 Minnesota Mining And Manufacturing Company Macromer reinforced pressure sensitive skin adhesive
US4732808A (en) * 1985-11-14 1988-03-22 Minnesota Mining And Manufacturing Company Macromer reinforced pressure sensitive skin adhesive sheet material
US4643181A (en) * 1986-04-04 1987-02-17 Surgikos, Inc. Antimicrobial dressing or drape material
US4788971A (en) * 1987-07-13 1988-12-06 Hill Top Research, Inc. Patch system for use on the skin
NL8702275A (en) * 1987-09-24 1989-04-17 Avery International Corp PRESSURE SENSITIVE ADHESIVE.
US4812305A (en) * 1987-11-09 1989-03-14 Vocal Rodolfo S Well medicine strip
US4931282A (en) * 1987-11-25 1990-06-05 Minnesota Mining And Manufacturing Company Pressure-sensitive medical sealant
US4985235A (en) * 1988-08-02 1991-01-15 Kligman Albert M Treatment of periodontoclasia with retinoic acid
US5071648A (en) * 1989-04-06 1991-12-10 Merocel Corporation Polymeric broad-spectrum antimicrobial materials
US4978527A (en) * 1989-04-10 1990-12-18 Minnesota Mining And Manufacturing Company Film-forming emulsion containing iodine and methods of use
MY105521A (en) * 1989-04-17 1994-10-31 Healthpoint Ltd Moisturizing vehicle for topical application of vitamin a acid.
ATE142557T1 (en) * 1989-05-11 1996-09-15 Landec Corp TEMPERATURE ACTIVATED BINDER UNITS
US5156911A (en) * 1989-05-11 1992-10-20 Landec Labs Inc. Skin-activated temperature-sensitive adhesive assemblies
US5045601A (en) * 1989-06-13 1991-09-03 Biointerface Technologies, Inc. Pressure-sensitive adhesive compositions suitable for medical uses
US5409472A (en) * 1989-08-03 1995-04-25 Smith & Nephew Plc Adhesive polymeric foam dressings
US5197493A (en) * 1989-12-14 1993-03-30 Kimberly-Clark Corporation Incise system
GB9006346D0 (en) * 1990-03-21 1990-05-16 Euro Celtique Sa Pharmaceutical composition
US5069907A (en) * 1990-03-23 1991-12-03 Phoenix Medical Technology Surgical drape having incorporated therein a broad spectrum antimicrobial agent
US5258421A (en) * 1991-03-20 1993-11-02 Hydromer, Inc. Method for making tacky, hydrophilic gel dressings
US5156601A (en) * 1991-03-20 1992-10-20 Hydromer, Inc. Tacky, hydrophilic gel dressings and products therefrom
GB9117256D0 (en) * 1991-08-09 1991-09-25 Smith & Nephew Adhesive products
US5232838A (en) * 1991-12-09 1993-08-03 Minnesota Mining And Manufacturing Company Culture media device and method of use
EP0662783B1 (en) * 1992-09-22 1997-07-23 Arda Technologies, Co. Antimicrobial composition and method of preparation
NZ248977A (en) * 1992-11-09 1995-06-27 Squibb & Sons Inc Pressure-sensitive adhesive comprising a polyurethane having excess hydroxyl functionality; medical articles comprising a layer of such adhesive
US5407368A (en) * 1992-12-15 1995-04-18 Minnesota Mining And Manufacturing Company Electrode connector
US5454739A (en) * 1992-12-15 1995-10-03 Minnesota Mining And Manufacturing Company Electrode connector
CA2157040C (en) 1993-03-22 2007-12-11 Steven B. Heinecke Windowless frame delivered dressing and method of manufacture
US6685682B1 (en) 1993-03-22 2004-02-03 3M Innovative Properties Company Carrier delivered dressing and method of manufacture
US5420197A (en) * 1994-01-13 1995-05-30 Hydromer, Inc. Gels formed by the interaction of polyvinylpyrrolidone with chitosan derivatives
WO1996019921A1 (en) * 1994-12-23 1996-07-04 Commonwealth Scientific And Industrial Research Organisation Iodine biocidal material
US5660823A (en) * 1995-10-11 1997-08-26 Isp Investments Inc. Fast drying, film forming iodine release solution
US5736228A (en) * 1995-10-25 1998-04-07 Minnesota Mining And Manufacturing Company Direct print film and method for preparing same
US5827184A (en) * 1995-12-29 1998-10-27 Minnesota Mining And Manufacturing Company Self-packaging bioelectrodes
EP0910303B1 (en) * 1996-05-16 2002-03-20 Minnesota Mining And Manufacturing Company Surgical incise drape
US5803086A (en) * 1996-05-16 1998-09-08 Minnesota Mining And Manufacturing Company Linerless surgical incise drape
US20080078413A1 (en) * 1996-06-12 2008-04-03 Padget David B Surgical drape
US20040234605A1 (en) * 1996-06-12 2004-11-25 Cox David D. Antimicrobial adhesive system
US5829442A (en) 1996-06-12 1998-11-03 Medical Concepts Development, Inc. Antimicrobial containing solventless hot melt adhesive composition
EP1249354A1 (en) 1996-06-14 2002-10-16 Minnesota Mining And Manufacturing Company Display unit and methods of displaying an image
JP2000513608A (en) * 1996-07-02 2000-10-17 ミネソタ マイニング アンド マニュファクチャリング カンパニー Packaged medical adhesive composite
USD410087S (en) 1996-07-02 1999-05-18 Dunshee Wayne K Adhesive bandage
US5976117A (en) * 1996-09-25 1999-11-02 3M Innovative Properties Company Wound dressing
DE19649237A1 (en) * 1996-11-28 1998-06-04 Bluecher Gmbh Agent with antiseptic activity, which produces iodine vapour
US5684042A (en) * 1997-01-10 1997-11-04 Medlogic Global Corporation Cyanoacrylate compositions comprising an antimicrobial agent
CA2317413A1 (en) 1997-01-10 1998-07-16 Medlogic Global Corporation Cyanoacrylate compositions comprising an antimicrobial agent
US6018092A (en) * 1997-03-04 2000-01-25 3M Innovative Properties Company Medical adhesive bandage, delivery system and method
EP0983094A1 (en) * 1997-05-06 2000-03-08 Minnesota Mining And Manufacturing Company Textured, matte-finish, low adhesion coatings
CA2288019C (en) 1997-05-16 2008-01-22 Minnesota Mining And Manufacturing Company Surgical incise drape
US6420622B1 (en) 1997-08-01 2002-07-16 3M Innovative Properties Company Medical article having fluid control film
US6007532A (en) 1997-08-29 1999-12-28 3M Innovative Properties Company Method and apparatus for detecting loss of contact of biomedical electrodes with patient skin
US6096428A (en) * 1998-04-09 2000-08-01 3M Innovative Properties Company Multi-layer compositions comprising a fluoropolymer
US6156400A (en) 1998-04-09 2000-12-05 3M Innovative Properties Company Multi-layer compositions comprising a fluoropolymer
USD409754S (en) * 1998-04-13 1999-05-11 Dunshee Wayne K Bandage
USD408541S (en) * 1998-04-13 1999-04-20 Dunshee Wayne K Bandage and bandage with carrier
US6221198B1 (en) 1998-06-09 2001-04-24 3M Innovative Properties Company Method of stabilizing films or membranes using adhesive as a reservoir
US6607799B1 (en) 1998-10-15 2003-08-19 3M Innovative Properties Company Surgical dressing with delivery system and method of manufacture
US6356779B1 (en) 1999-06-04 2002-03-12 3M Innovative Properties Company Universally functional biomedical electrode
US6232366B1 (en) 1999-06-09 2001-05-15 3M Innovative Properties Company Pressure sensitive conductive adhesive having hot-melt properties and biomedical electrodes using same
US6365169B1 (en) 1999-09-30 2002-04-02 Solomon Rosenblatt Polymeric broad spectrum antimicrobial coatings
US6579469B1 (en) 1999-10-29 2003-06-17 Closure Medical Corporation Cyanoacrylate solutions containing preservatives
US6264976B1 (en) 1999-11-29 2001-07-24 3M Innovative Properties Company Absorbent pad dressing frame delivery system
US6831205B2 (en) * 1999-11-29 2004-12-14 Clozex Medical, Llc Bandage for wound or incision closure
JP2003530489A (en) 1999-12-28 2003-10-14 キンバリー クラーク ワールドワイド インコーポレイテッド Wipes containing controlled release antimicrobial agents
CA2393542C (en) 1999-12-28 2011-08-16 Kimberly-Clark Worldwide, Inc. Use-dependent indicator system for absorbent articles
ATE396038T1 (en) 1999-12-28 2008-06-15 Kimberly Clark Co ANTIMICROBIAL WIPE WITH CONTROLLED RELEASE FOR HARD SURFACES
ATE318566T1 (en) 2000-03-10 2006-03-15 3M Innovative Properties Co MEDICAL WOUND DRESSING WITH MULTIPLE ADHESIVES AND MANUFACTURING METHODS
US6379702B1 (en) 2000-07-05 2002-04-30 Hydromer, Inc. Gels formed by the interaction of polyvinylpyrrolidone with chitosan derivatives
US6903243B1 (en) 2000-09-08 2005-06-07 3M Innovative Properties Company Multi-layer absorbent wound dressing
US6797743B2 (en) * 2000-09-27 2004-09-28 Michigan Biotechnology Institute Antimicrobial polymer
US6664309B2 (en) 2000-12-07 2003-12-16 Bostik Findley, Inc. Antimicrobial hot melt adhesive
US6531206B2 (en) * 2001-02-07 2003-03-11 3M Innovative Properties Company Microstructured surface film assembly for liquid acquisition and transport
US6709716B2 (en) 2001-04-27 2004-03-23 3M Innovative Properties Company Microemulsion compositions and methods of making and using same
JP2005503189A (en) 2001-05-04 2005-02-03 スリーエム イノベイティブ プロパティズ カンパニー Corrosion prevention in biomedical electrodes
US6731965B2 (en) 2001-06-20 2004-05-04 3M Innovative Properties Company Corrosion prevention in biomedical electrodes
US6602496B2 (en) 2001-07-05 2003-08-05 Closure Medical Corporation Adhesive treatment for tinea corporis
US6942875B2 (en) * 2001-07-05 2005-09-13 Closure Medical Corporation Adhesive treatment for skin yeast infections
US6746667B2 (en) 2001-07-05 2004-06-08 Closure Medical Corporation Adhesive treatment for tinea pedis
US6767552B2 (en) 2001-07-05 2004-07-27 Closure Medical Corporation Adhesive treatment for oral fungal infection
US6585967B2 (en) 2001-07-05 2003-07-01 Closure Medical Corporation Adhesive treatment for tinea cruris
US6902740B2 (en) * 2001-07-09 2005-06-07 3M Innovative Properties Company Pyrrolidonoethyl (meth)acrylate containing pressure sensitive adhesive compositions
US7063887B2 (en) 2002-02-04 2006-06-20 3M Innovative Properties Company Stretch releasable foams, articles including same and methods for the manufacture thereof
US20030175497A1 (en) * 2002-02-04 2003-09-18 3M Innovative Properties Company Flame retardant foams, articles including same and methods for the manufacture thereof
US6939554B2 (en) * 2002-02-05 2005-09-06 Michigan Biotechnology Institute Antimicrobial polymer
WO2003080730A1 (en) 2002-03-20 2003-10-02 Michigan Biotechnology Institute Conductive polymer-based material
US6708050B2 (en) 2002-03-28 2004-03-16 3M Innovative Properties Company Wireless electrode having activatable power cell
US7181875B2 (en) 2002-03-29 2007-02-27 3M Innovative Properties Company Stock material for trim caps
US6866928B2 (en) 2002-04-08 2005-03-15 3M Innovative Properties Company Cleanly removable tapes and methods for the manufacture thereof
US6939936B2 (en) * 2002-04-25 2005-09-06 3M Innovative Properties Company Iodine/iodide-containing hot melt coatable adhesive, methods and uses therefor
US6803090B2 (en) 2002-05-13 2004-10-12 3M Innovative Properties Company Fluid transport assemblies with flame retardant properties
US6923320B2 (en) * 2002-07-06 2005-08-02 Victor A. Grossman Bandage package and dispenser
US6951902B2 (en) * 2002-08-16 2005-10-04 Michigan Biotechnology Institute Two dimensional polymer that generates nitric oxide
US6838589B2 (en) 2003-02-19 2005-01-04 3M Innovative Properties Company Conformable wound dressing
US7229683B2 (en) * 2003-05-30 2007-06-12 3M Innovative Properties Company Thermal interface materials and method of making thermal interface materials
US7744991B2 (en) * 2003-05-30 2010-06-29 3M Innovative Properties Company Thermally conducting foam interface materials
US9278155B2 (en) * 2003-06-05 2016-03-08 3M Innovative Properties Company Adhesive compositions, articles incorporating same and methods of manufacture
US20040247654A1 (en) * 2003-06-05 2004-12-09 3M Innovative Properties Company Hydrophilic adhesives for delivery of herbal medicines
US7354446B2 (en) * 2003-07-24 2008-04-08 Clozex Medical, Llc Device for laceration or incision closure
US7414168B2 (en) * 2003-07-24 2008-08-19 Clozex Medical Llc Device for laceration or incision closure
US7838718B2 (en) * 2003-07-24 2010-11-23 Clozex Medical, Llc Device for laceration or incision closure
US8636763B2 (en) * 2003-07-24 2014-01-28 Clozex Medical, Llc Device for laceration or incision closure
US20050021081A1 (en) * 2003-07-24 2005-01-27 Clozex Medical, Llc Device for laceration or incision closure
USD495419S1 (en) 2003-08-15 2004-08-31 3M Innovative Properties Company Bandage
US7332641B2 (en) * 2003-10-10 2008-02-19 Clozex Medical Llc Interlaced compositions and methods of production
US20050106360A1 (en) 2003-11-13 2005-05-19 Johnston Raymond P. Microstructured surface building assemblies for fluid disposition
US20050130527A1 (en) * 2003-12-11 2005-06-16 3M Innovative Properties Company UV stabilized fibrous articles and method of making the same
US20050249791A1 (en) * 2004-05-07 2005-11-10 3M Innovative Properties Company Antimicrobial articles
US20060035039A1 (en) * 2004-08-12 2006-02-16 3M Innovative Properties Company Silver-releasing articles and methods of manufacture
US20060034899A1 (en) * 2004-08-12 2006-02-16 Ylitalo Caroline M Biologically-active adhesive articles and methods of manufacture
US7563941B2 (en) * 2004-09-10 2009-07-21 Clozex Medical, Llc Modular wound dressing system
US7781041B2 (en) 2004-11-19 2010-08-24 Beekley Corporation Tattoo cover and related method
US7506760B2 (en) * 2005-01-10 2009-03-24 Grossman Victor A Packaging and dispensers for adhesive backed elements
USD559985S1 (en) 2005-04-08 2008-01-15 Beekley Corporation Mammogram marker
USD590949S1 (en) * 2005-06-30 2009-04-21 Beekley Corporation Temporary tattoo cover
US20070010777A1 (en) * 2005-07-06 2007-01-11 3M Innovative Properties Company Medical tape and bandages
US20070038246A1 (en) * 2005-08-09 2007-02-15 Clozex Medical, Llc Four component wound closure device with locking strip
US8105353B2 (en) 2005-08-09 2012-01-31 Clozex Medical, Llc Wound closure kit and method of using the same
US7442849B2 (en) * 2005-12-30 2008-10-28 3M Innovative Properties Company Thin film delivery system and method of manufacture
US20090186332A1 (en) * 2006-03-15 2009-07-23 Manders Ernest K Preparation and storage of stable, antimicrobially active materials
US20070243258A1 (en) * 2006-04-13 2007-10-18 3M Innovative Properties Company Method and apparatus for forming crosslinked chromonic nanoparticles
USD611156S1 (en) 2006-06-12 2010-03-02 3M Innovative Properties Company Bandage
US7858838B2 (en) * 2006-08-10 2010-12-28 3M Innovative Properties Company Conformable wound dressing
US20080200890A1 (en) * 2006-12-11 2008-08-21 3M Innovative Properties Company Antimicrobial disposable absorbent articles
US9555167B2 (en) * 2006-12-11 2017-01-31 3M Innovative Properties Company Biocompatible antimicrobial compositions
US8729121B2 (en) * 2007-06-25 2014-05-20 Adhezion Biomedical, Llc Curing accelerator and method of making
EP2211727B1 (en) 2007-11-14 2014-03-12 Adhezion Biomedical, LLC Cyanoacrylate tissue adhesives
CA2711177A1 (en) * 2007-12-31 2009-07-16 3M Innovative Properties Company Medical dressing with edge port and methods of use
US9242022B2 (en) * 2008-01-18 2016-01-26 3M Innovative Properties Company Hydrogels with tapered edge
BRPI0906549A8 (en) * 2008-04-04 2019-02-12 3M Innovative Properties Co medical bandage
US20110112492A1 (en) 2008-04-04 2011-05-12 Vivek Bharti Wound dressing with micropump
JP2011518222A (en) * 2008-04-21 2011-06-23 スリーエム イノベイティブ プロパティズ カンパニー Nitric oxide releasing composition, device and method
WO2009143249A2 (en) * 2008-05-23 2009-11-26 3M Innovative Properties Company Grounding electrode
CA2727427A1 (en) 2008-06-12 2009-12-17 3M Innovative Properties Company Melt blown fine fibers and methods of manufacture
AU2009257361A1 (en) 2008-06-12 2009-12-17 3M Innovative Properties Company Biocompatible hydrophilic compositions
US8198344B2 (en) 2008-06-20 2012-06-12 Adhezion Biomedical, Llc Method of preparing adhesive compositions for medical use: single additive as both the thickening agent and the accelerator
US8293838B2 (en) * 2008-06-20 2012-10-23 Adhezion Biomedical, Llc Stable and sterile tissue adhesive composition with a controlled high viscosity
US20110117047A1 (en) 2008-06-23 2011-05-19 Adhezion Biomedical, Llc Cyanoacrylate tissue adhesives with desirable permeability and tensile strength
US9457123B2 (en) * 2008-09-24 2016-10-04 3M Innovative Properties Company Hydrogels with release element
JP5421379B2 (en) * 2008-09-30 2014-02-19 スリーエム イノベイティブ プロパティズ カンパニー Thin film nasal dilator with delivery system
MX2011004294A (en) * 2008-10-24 2011-05-23 3M Innovative Properties Co Conformable wound dressing.
US8110718B2 (en) * 2008-10-27 2012-02-07 3M Innovative Properties Company Thin film delivery system and method of manufacture
US8609128B2 (en) 2008-10-31 2013-12-17 Adhezion Biomedical, Llc Cyanoacrylate-based liquid microbial sealant drape
US9254133B2 (en) 2008-10-31 2016-02-09 Adhezion Biomedical, Llc Sterilized liquid compositions of cyanoacrylate monomer mixtures
US8652510B2 (en) 2008-10-31 2014-02-18 Adhezion Biomedical, Llc Sterilized liquid compositions of cyanoacrylate monomer mixtures
US11278740B2 (en) 2008-11-03 2022-03-22 Berkley Corporation Temporary tattoo cover and related method
US10314935B2 (en) 2009-01-07 2019-06-11 Entrotech Life Sciences, Inc. Chlorhexidine-containing antimicrobial laminates
EP2411061B1 (en) 2009-03-27 2014-11-19 3M Innovative Properties Company Hydrophilic polypropylene melt additives
EP2414574B1 (en) 2009-03-31 2018-12-12 3M Innovative Properties Company Dimensionally stable nonwoven fibrous webs and methods of making and using the same
CN104095709B (en) 2009-06-16 2017-06-13 3M创新有限公司 Conformable Medical with self-supporting substrate
WO2011022525A1 (en) 2009-08-21 2011-02-24 3M Innovative Properties Company Methods and products for illuminating tissue
EP2467081A4 (en) 2009-08-21 2015-05-06 3M Innovative Properties Co Methods and products for reducing tissue trauma using water-absorbing stress-distributing materials
EP3143943B1 (en) 2009-08-21 2019-02-27 3M Innovative Properties Company Products for reducing tissue trauma using water-resistant stress-distributing materials
WO2011055388A2 (en) 2009-11-05 2011-05-12 Indian Institute Of Technology Wound dressing polymer matrix
CN102596560B (en) * 2009-11-09 2015-11-25 3M创新有限公司 Medical article and the method using miscible composition to be prepared
KR20120091339A (en) 2009-11-09 2012-08-17 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Medical articles and methods of making using immiscible material
BR112012014945A2 (en) 2009-12-17 2018-10-09 3M Innovative Properties Co dimensionally stable non-woven fibrous mat, meltblown thin fibers, and methods of fabrication and use thereof
CN105274733B (en) * 2009-12-17 2018-11-20 3M创新有限公司 Non-woven fibre web of dimensionally stable and production and preparation method thereof
JP2013520583A (en) 2010-02-23 2013-06-06 スリーエム イノベイティブ プロパティズ カンパニー Dimensionally stable nonwoven fibrous webs and methods for their manufacture and use
US9309019B2 (en) 2010-05-21 2016-04-12 Adhezion Biomedical, Llc Low dose gamma sterilization of liquid adhesives
TW201221714A (en) 2010-10-14 2012-06-01 3M Innovative Properties Co Dimensionally stable nonwoven fibrous webs and methods of making and using the same
CN103281997A (en) 2010-12-29 2013-09-04 3M创新有限公司 An elastic strip
EP2658492B1 (en) 2010-12-29 2023-11-22 3M Innovative Properties Company An apertured hydrogel
EP2731563B1 (en) 2011-07-12 2017-05-17 3M Innovative Properties Company A wound dressing assembly
EP2755620A4 (en) 2011-09-14 2015-06-03 3M Innovative Properties Co Positive pressure medical dressings with valve and kits containing same
US9220627B2 (en) 2011-11-30 2015-12-29 Mark Allen Fisher Abdominal elevator
KR20140101416A (en) 2011-12-13 2014-08-19 쓰리엠 이노베이티브 프로퍼티즈 컴파니 Method of making pressure-sensitive adhesive article including active agent
US20130171203A1 (en) 2011-12-16 2013-07-04 Solomon Rosenblatt Composition And Methods For Antimicrobial Articles
CN104334113A (en) 2011-12-29 2015-02-04 3M创新有限公司 Filled incise drape
US11944519B2 (en) 2012-01-18 2024-04-02 Worldwide Innovative Healthcare, Inc. Unbacked and modifiable tapes and skin dressings
WO2013162680A1 (en) 2012-04-23 2013-10-31 3M Innovative Properties Company Conforming securement articles and methods of use
BR112015001280A2 (en) 2012-07-20 2017-07-04 3M Innovative Properties Co fixing set, method for fixing a fixing set and method for fixing a device
US10342628B2 (en) 2012-09-21 2019-07-09 3M Innovative Properties Company Incision protection
JP2016504212A (en) 2012-11-20 2016-02-12 スリーエム イノベイティブ プロパティズ カンパニー Laminates and articles comprising block copolymer coatings comprising polyorganosiloxane and polyolefin
WO2014081682A1 (en) 2012-11-20 2014-05-30 3M Innovative Properties Company Block copolymer comprising polyorganosiloxane block and polyolefin block
EP2934659B1 (en) 2012-12-21 2019-03-06 3M Innovative Properties Company Adhesive assemblies and microneedle injection apparatuses comprising same
US10434284B2 (en) 2012-12-21 2019-10-08 3M Innovative Properties Company Medical dressing comprising a flap
CN105188623B (en) 2013-03-11 2020-09-25 3M创新有限公司 Conformable medical dressing
WO2014209620A1 (en) 2013-06-28 2014-12-31 3M Innovative Properties Company Fibrin-coated wound dressing
WO2015013093A1 (en) 2013-07-23 2015-01-29 3M Innovative Properties Company Adjustable wound dressing
WO2015020882A1 (en) 2013-08-05 2015-02-12 3M Innovative Properties Company Catheter securement device
JP2016533436A (en) 2013-10-04 2016-10-27 スリーエム イノベイティブ プロパティズ カンパニー Multicomponent fibers, nonwoven webs, and articles comprising polydiorganosiloxane polyamides
CN105873549B (en) 2013-12-31 2017-10-27 3M创新有限公司 Conformal drape covering dressing
WO2015130608A1 (en) 2014-02-25 2015-09-03 3M Innovative Properties Company Medical dressing
US10209213B2 (en) 2014-02-27 2019-02-19 3M Innovative Properties Company Flexible sensor patch and method of using the same
US9421297B2 (en) 2014-04-02 2016-08-23 Adhezion Biomedical, Llc Sterilized compositions of cyanoacrylate monomers and naphthoquinone 2,3-oxides
WO2015161302A1 (en) 2014-04-18 2015-10-22 Entrotech Life Sciences, Inc. Methods of processing chlorhexidine-containing polymerizable compositions and antimicrobial articles formed thereby
WO2015179235A1 (en) 2014-05-23 2015-11-26 3M Innovative Properties Company A discontinuous silicone adhesive article
ES2921990T3 (en) 2014-09-10 2022-09-05 Bard Inc C R Protective dressing for a medical device placed on the skin
US10286100B2 (en) 2014-10-01 2019-05-14 3M Innovative Properties Company Medical dressings comprising fluid management articles and methods of using same
US10973692B2 (en) 2014-12-19 2021-04-13 3M Innovative Properties Company Viscoelastic wound closure dressing
CA2971621A1 (en) 2014-12-19 2016-06-23 3M Innovative Properties Company Adhesive article comprising a poly(meth)acrylate-based primer layer and methods of making same
CN107106833B (en) 2014-12-22 2020-10-16 3M创新有限公司 Biomedical electrodes including discontinuous primer layers
WO2016109418A1 (en) 2014-12-30 2016-07-07 3M Innovative Properties Company Wound dressing with multiple adhesive layers
CN107427601B (en) 2015-03-27 2021-08-31 3M创新有限公司 Fibrin compositions, methods and articles for wounds
US11571490B2 (en) 2015-06-29 2023-02-07 3M Innovative Properties Company Anti-microbial articles and methods of using same
EP3337545B1 (en) 2015-08-21 2021-01-13 3M Innovative Properties Company Nasogastric tube securement systems
CN107921238A (en) 2015-08-21 2018-04-17 3M创新有限公司 Nose catheter fixed system and its application method
CN107949416A (en) 2015-08-21 2018-04-20 3M创新有限公司 Nose catheter fixed system and its application method
WO2017058628A1 (en) 2015-09-30 2017-04-06 3M Innovative Properties Company Surgical site cover comprising conformable polymeric film and methods of use
USD804678S1 (en) 2015-09-30 2017-12-05 3M Innovative Properties Company Oval surgical drape with a retraction member
USD804677S1 (en) 2015-09-30 2017-12-05 3M Innovative Properties Company Surgical drape with a retraction member
WO2017083482A1 (en) 2015-11-13 2017-05-18 3M Innovative Properties Company Anti-microbial articles and methods of using same
WO2017083166A1 (en) 2015-11-13 2017-05-18 3M Innovative Properties Company Anti-microbial articles and methods of using same
US11827754B2 (en) 2016-10-05 2023-11-28 3M Innovative Properties Company Fibrin composition comprising carrier material, method and wound articles
US10940233B2 (en) 2016-10-05 2021-03-09 3M Innovative Properties Company Fibrinogen composition, method and wound articles
US11246761B2 (en) 2016-10-07 2022-02-15 3M Innovative Properties Company Conformable wound dressing and delivery system
EP3528855A1 (en) 2016-10-19 2019-08-28 3M Innovative Properties Company Anti-microbial articles
WO2018089563A1 (en) 2016-11-11 2018-05-17 3M Innovative Properties Company Trimmable conformable wound dressing
EP3589345A1 (en) 2017-03-02 2020-01-08 3M Innovative Properties Company Endotracheal tube securement systems and methods of using same
CN110636820A (en) 2017-05-19 2019-12-31 3M创新有限公司 Medical article securement devices comprising viscoelastic polymers
US20200146892A1 (en) 2017-06-22 2020-05-14 3M Innovative Properties Company Negative pressure wound therapy article with features
US11224544B2 (en) 2017-09-29 2022-01-18 Johnson & Johnson Consumer Inc. Extensible dressings
US20190099294A1 (en) 2017-09-29 2019-04-04 Johnson & Johnson Consumer Inc. Extensible Dressings
JP7304868B2 (en) 2017-10-09 2023-07-07 スリーエム イノベイティブ プロパティズ カンパニー Fixed dressings with compatible margins
EP3703635A1 (en) 2017-10-31 2020-09-09 3M Innovative Properties Company Negative pressure wound therapy article
EP3723682A1 (en) 2017-12-14 2020-10-21 3M Innovative Properties Company Negative pressure wound therapy article with features
WO2020035811A1 (en) 2018-08-17 2020-02-20 3M Innovative Properties Company Wound dressing system
US20220017785A1 (en) 2018-12-12 2022-01-20 3M Innovative Properties Company Release inkjet printing ink articles
EP3894229A1 (en) 2018-12-12 2021-10-20 3M Innovative Properties Company Releasable article manufactured by inkjet printing of an adhesive
EP3894500A1 (en) 2018-12-12 2021-10-20 3M Innovative Properties Company Release inkjet printing ink articles
US20220112404A1 (en) 2018-12-31 2022-04-14 3M Innovative Properties Company Thermally bondable adhesive tape backing
US20220175585A1 (en) 2019-04-01 2022-06-09 3M Innovative Properties Company Conformable dressing
EP3975955B1 (en) 2019-05-28 2023-11-01 3M Innovative Properties Co. Medical dressing for securing a tubiform component of a medical device
WO2020245721A1 (en) 2019-06-05 2020-12-10 3M Innovative Properties Company Medical dressings with stiffening systems
JP2022543769A (en) 2019-08-01 2022-10-14 スリーエム イノベイティブ プロパティズ カンパニー Antibacterial device for insertion needle
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CN114466675A (en) 2019-10-29 2022-05-10 3M创新有限公司 Pipe fixing adhesive tape
CN114630876A (en) 2019-11-04 2022-06-14 3M创新有限公司 Reinforced adhesive substrate
EP4061901A1 (en) 2019-11-20 2022-09-28 3M Innovative Properties Company Medical tapes with high optical clarity when over-taped
WO2021209846A1 (en) 2020-04-13 2021-10-21 3M Innovative Properties Company Medical adhesive articles having a low effective modulus of elasticity
US20230277385A1 (en) 2020-07-16 2023-09-07 3M Innovative Properties Company Conformable medical dressing
US11241902B1 (en) 2020-09-17 2022-02-08 Temptime Corporation Environmental history monitor with positional displacement and security features
JP2023552590A (en) 2020-12-11 2023-12-18 スリーエム イノベイティブ プロパティズ カンパニー Perforated tape for medical applications
WO2022137062A1 (en) 2020-12-21 2022-06-30 3M Innovative Properties Company Dual-sided adhesive tapes with on-demand adhesion
WO2023031697A1 (en) 2021-09-01 2023-03-09 3M Innovative Properties Company Anti-virus respirator and mask
WO2023203449A1 (en) 2022-04-20 2023-10-26 3M Innovative Properties Company Stretch to fit bandage
CN115181208B (en) * 2022-06-23 2023-10-20 浙江工业大学 Medical pressure-sensitive adhesive and pressure-sensitive adhesive tape with iodine slow release function and preparation method thereof
WO2024023619A1 (en) 2022-07-28 2024-02-01 3M Innovative Properties Company Cover dressing, kit, and method of use
EP4349311A1 (en) 2022-10-05 2024-04-10 Gergonne SAS Thin film dressing with perforations and slits

Family Cites Families (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE685805C (en) 1935-04-19 1939-12-23 Du Pont Adhesive mass, adhesive plaster, etc. Like. For bandage purposes
US2400389A (en) * 1942-03-26 1946-05-14 Wingfoot Corp Film containing iodine
US2427022A (en) * 1942-11-07 1947-09-09 Ward Baking Co Surgical adhesive tape
US2739922A (en) * 1952-03-13 1956-03-27 Herman A Shelanski Mixtures of polymeric n-vinyl pyrrolidone and halogens
US2752281A (en) * 1953-06-01 1956-06-26 Rohm & Haas Iodine dissolved in aqueous solutions of maleic anhydride-vinyl ether copolymers
NL91314C (en) * 1955-09-19
US2927914A (en) * 1956-06-28 1960-03-08 Gen Aniline & Film Corp Crosslinking of vinyl ether polymers with iodine
US2826528A (en) * 1957-05-20 1958-03-11 West Laboratories Inc Halide polyalkylacrylic compositions
US2951766A (en) * 1957-07-15 1960-09-06 Le Roy A White Antiseptic plastic
US3028300A (en) * 1960-09-13 1962-04-03 West Laboratories Inc Germicidal compositions and methods for preparing the same
US3307544A (en) * 1963-09-10 1967-03-07 Johnson & Johnson Surgical pressure-sensitive adhesive sheet with n-tert-butylacrylamide copolymer adhesive
US3347233A (en) * 1964-02-06 1967-10-17 Colgate Palmolive Co Occlusive medicated sheath
DE1925348U (en) 1965-08-31 1965-10-14 Karl Altenburger K G SHELF.
GB1213295A (en) 1967-04-27 1970-11-25 Boots Pure Drug Co Ltd Improvements in therapeutic compositions for topical application
US3579628A (en) * 1967-07-03 1971-05-18 Johnson & Johnson Dressing film
US3632740A (en) * 1968-06-13 1972-01-04 Johnson & Johnson Topical device for the therapeutic management of dermatological lesions with steroids
NO134790C (en) * 1968-07-09 1984-03-22 Smith & Nephew Kleber ,; PRESSURE SENSITIVE, WATERPUME-PERMEABLE PRODUCT FOR SKIN USE BY HUMANS.
FR2012584A1 (en) * 1968-07-09 1970-03-20 Smith & Nephew Surgical and other materials adhering to skin
US3535774A (en) 1968-07-09 1970-10-27 Rca Corp Method of fabricating semiconductor devices
US3734097A (en) * 1969-04-01 1973-05-22 Alza Corp Therapeutic adhesive tape
US3598123A (en) * 1969-04-01 1971-08-10 Alza Corp Bandage for administering drugs
US3907720A (en) * 1969-11-10 1975-09-23 Gaf Corp Insoluble porous polymeric iodine complexes useful as bactericides
US3577516A (en) * 1969-12-02 1971-05-04 Nat Patent Dev Corp Preparation of spray on bandage
US3728148A (en) * 1969-12-24 1973-04-17 Beiersdorf Ag Method for the production of electrical pressure sensitive insulating tapes
US3749772A (en) * 1970-12-04 1973-07-31 Univ Akron Dermal protective film
US3769071A (en) * 1971-06-04 1973-10-30 Minnesota Mining & Mfg Pressure sensitive adhesive tape comprising 5-fluorouracil
US3996934A (en) * 1971-08-09 1976-12-14 Alza Corporation Medical bandage
US3886268A (en) * 1972-05-30 1975-05-27 Synergistics Iodophor-steroid compound pharmaceutical compositions
US3898326A (en) * 1973-05-14 1975-08-05 West Laboratories Inc Polyvinylpyrrolidone-iodide compositions and polyvinylpyrrolidone-iodide-iodine complexes prepared therefrom
US3969498A (en) * 1973-09-13 1976-07-13 University Of The Pacific Dressing and method for treating a wound
DE2403225B2 (en) 1974-01-24 1979-05-17 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt Process for the production of iodophores
US3896789A (en) * 1974-06-10 1975-07-29 Riker Laboratories Inc Retinoic acid dipensing pressure sensitive dermotological tape
CH612984A5 (en) 1974-12-02 1979-08-31 Ciba Geigy Ag
DE2557607A1 (en) * 1974-12-27 1976-07-08 Hydrophilics Int Inc PRODUCTS AND PHARMACEUTICAL PREPARATIONS CONTAINING IODINE
SU578971A1 (en) 1975-04-29 1977-11-05 2-Й Московский Ордена Ленина Государственный Медицинский Институт Им. Н.И. Пирогова Wound treatment method
US4045364A (en) * 1975-11-24 1977-08-30 American Cyanamid Company Iodophor soap tissues
US4113851A (en) * 1976-04-15 1978-09-12 Leveen Harry H Microbiocidal composition and articles prepared therefrom
CA1083481A (en) * 1976-06-07 1980-08-12 Abraham Cantor Stabilized iodine tincture
US4073291A (en) * 1976-07-28 1978-02-14 Johnson & Johnson Topical device for administering tretinoin
US4147775A (en) * 1976-10-06 1979-04-03 Schwartz Stephen H Antiseptic composition
US4094967A (en) * 1976-10-22 1978-06-13 Allor Foundation Iodine-polyvinylpyrrolidone solid product and method of preparation
US4113857A (en) * 1977-05-16 1978-09-12 The Purdue Frederick Company Process for the preparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing the same
EP0011471B1 (en) * 1978-11-17 1983-02-09 SMITH & NEPHEW RESEARCH LIMITED Adhesive-coated sheet material incorporating anti-bacterial substances
US4323557A (en) * 1979-07-31 1982-04-06 Minnesota Mining & Manufacturing Company Pressure-sensitive adhesive containing iodine
US4310509A (en) * 1979-07-31 1982-01-12 Minnesota Mining And Manufacturing Company Pressure-sensitive adhesive having a broad spectrum antimicrobial therein

Also Published As

Publication number Publication date
EP0024107B1 (en) 1983-11-16
EP0024107A1 (en) 1981-02-25
DE3065603D1 (en) 1983-12-22
AU6087180A (en) 1981-02-05
ZA804631B (en) 1981-07-29
JPH0257262A (en) 1990-02-27
AU537351B2 (en) 1984-06-21
JPH0149499B2 (en) 1989-10-25
EP0024107B2 (en) 1991-01-16
ES8106655A1 (en) 1981-09-01
ES493775A0 (en) 1981-09-01
US4323557A (en) 1982-04-06
JPH0643298B2 (en) 1994-06-08
JPS5622727A (en) 1981-03-03

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