WO1996004899A1 - Antimicrobial flexible material having barrier properties - Google Patents

Antimicrobial flexible material having barrier properties Download PDF

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Publication number
WO1996004899A1
WO1996004899A1 PCT/US1994/008924 US9408924W WO9604899A1 WO 1996004899 A1 WO1996004899 A1 WO 1996004899A1 US 9408924 W US9408924 W US 9408924W WO 9604899 A1 WO9604899 A1 WO 9604899A1
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Prior art keywords
composition
weight
amount
mixture
compound
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PCT/US1994/008924
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French (fr)
Inventor
Victor Staats
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International Laboratory Technology Corp.
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Publication date
Priority to US08/086,022 priority Critical patent/US5336305A/en
Priority claimed from US08/086,022 external-priority patent/US5336305A/en
Application filed by International Laboratory Technology Corp. filed Critical International Laboratory Technology Corp.
Priority to PCT/US1994/008924 priority patent/WO1996004899A1/en
Publication of WO1996004899A1 publication Critical patent/WO1996004899A1/en

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D129/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
    • C09D129/10—Homopolymers or copolymers of unsaturated ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides

Definitions

  • the present invention relates to an antimicrobial barrier and more particularly to a moisture activated antimicrobial composition which can be applied to textiles used in the medical industry.
  • the present invention provides a novel composition which can be applied to any flexible material and in particular to woven or nonwoven textiles either during or after manufacture to provide an antimicrobial barrier against a broad spectrum of potential pathogens.
  • the novel composition is moisture activated such that once applied to the fabric or material it remains inert until it comes into contact with bodily secretions, water or other liquid.
  • a hydrophilic polymeric component of the composition breaks down and precipitates upon contact with moisture, thus activating the composition.
  • the composition once activated, continues to afford protection for up to 12 hours.
  • the active antimicrobial component of the composition consists of a mixture of a quaternary ammonium compound and nonoxynol 9.
  • a further object lies in the provision of an antimicrobial composition which is moisture activated .
  • the present invention is directed to a moisture activated coating composition for substrates of flexible materials and in a preferred embodiment for application to disposable medical gowns , garments , and face masks .
  • a functional substance which is biologically active against a broad spectrum of viruses , bacteria, fungii, and other pathogenic species .
  • a large number of biologically active substances are available which retard bacterial , microbial , or fungal growth. It is contemplated that any of these commonly known biologically active substances could be utilized, however, in the preferred embodiment, the functional substance is comprised of a quaternary ammonium compound, nonoxynol 9, or a mixture of a quaternary ammonium compound and nonoxynol 9.
  • the preferred quaternary ammonium compound is a blend of Myristalkonium chloride and Quaternium 14 shown by the general formula:
  • R ia 60% C14, 30% C16 and R is 68% C12, 32% C14 5% C12, 5% C18 n-alkyl dimethyl benzyl n-alkyl dimethyl ethyl- ammonium chloride benzyl ammonium chloride
  • Nonoxynol 9 is an ethoxylated nonyl phenol containing 9 moles of ethylene oxide and serves both as a nonoinic surfactant and an antimicrobial agent. Although both nonoxynol 9 and the blend of Myristalkonium chloride and Quaternium 14 can function alone, a synergistic effect is achieved when they are used in combination, producing substantially greater activity against pathogens than either substance alone.
  • the nonoxynol 9 enables the coating composition to be spread evenly over the entire surface of the substrate or garment, thus achieving and maintaining a uniform antimicrobial effectiveness throughout.
  • Nonoxynol 9 is preferably present in the amount of 1%-10% by weight and the quaternary ammonium compound blend in the amount of 0.021-0.06% by weight.
  • the coating composition additionally contains a hydrophobic, waterproofing agent.
  • the hydrophobic agent is preferably a polymer derived from vinylpyrrolidone and a long chain alpha olefin represented by the general formula:
  • R is alkyl or hydrogen
  • the hydrophobic agent is a PVP/eicosene copolymer (polyvinylpyrrolidone and eicosene) and is present 0.5%-6% by weight.
  • a hydrophilic film forming compound which is highly moisture sensitive and breaks down upon contact with water is further included in the coating composition.
  • the film forming compound provides an adhesive type barrier between the functional substance and the environment, thus rendering the composition inert.
  • the hydrophilic film forming compound breaks down and precipitates, thereby allowing the functional substance to migrate to the outer surface of the substrate to effectively eliminate any pathogens present in the fluid or proximate to such.
  • the functional substance continues to inhibit microbial growth at the surface of the substrate or garment for up to 12 hours, thus affording protection to the wearer of the garment or any person or patient in close contact with the wearer.
  • R is ethyl, isopropyl, or n-butyl Most particularly the ethyl ester of PVM/MA copolymer is selected with a molecular weight between 110,000-150,000 and present from 0.5%-6% by weight. These compounds are preferred due to their exceedingly high water sensitivity upon neutralization.
  • an organic solvent Due to the general water insolubility of the hydrophilic film forming compound, the inclusion of 2-8% by weight of an organic solvent is contemplated with anhydrous ethanol SD 40 being preferred.
  • the organic solvent also functions as a drying agent.
  • Anhydrous ethanol SD 40 and most other commonly utilized organic solvents exhibit relatively high flammability characteristics, therefore requiring that a stabilizer that effectively eliminates the flammable nature of the mixture be included. While the use of various stabilizers of the prior art may be acceptable to reduce fla mability, 1-10% by weight of 1,3 butylene glycol is a preferred species. 1,3 butylene glycol not only effectively stabilizes the ethanol or other solvent, but further aids in dispersion.
  • the coating composition may also include additional materials such as aloe, present in the range of 1-5% by weight, to provide comfort to the skin and decrease the likelihood of skin irritation.
  • additional materials such as aloe, present in the range of 1-5% by weight, to provide comfort to the skin and decrease the likelihood of skin irritation.
  • the formation of the coating composition includes the use of three separate mixing tanks.
  • a first mixing tank approximately 1/3 of the total volume of the stabilizer (butylene glycol) is heated to 160 degrees F while stirring slowly.
  • the hydrophobic waterproof polymeric compound (PVP/eicosene) is then added and the resultant mixture is stirred until dissolved. This mixture is then cooled to 100 degrees F.
  • a second mixing tank a second 1/3 portion of the butylene glycol is mixed with the functional substance (nonoxynol 9 and the quaternary ammonium compound).
  • the hydrophilic film forming compound (PVM/MA) is then dissolved in the solvent (ethanol) in a third tank.
  • the last 1/3 portion of the butylene glycol is then added to the third tank along with aloe and water to bring the mixture to the desired concentration.
  • the mixture in the second tank is slowly added to the first tank under constant stirring and agitation.
  • the mixture from the third tank is then introduced very slowly to the first tank, mixing until a homogeneous mixture is achieved.
  • the manner of application of the resultant composition to the flexible material or garment may be varied and could include such methods as spraying, dipping, painting, or adding to the final rinse cycle during a machine washing operation.
  • the composition will coat the material or fabric and in some instances impregnate the fiber structure of the material.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A moisture activated, antimicrobial composition is provided which can be applied to any flexible material and in particular to woven or nonwoven textiles and disposable medical garments and masks. This composition, in a preferred embodiment, contains a quaternary ammonium compound/nonoxynol 9 complex as the pathogenic growth inhibitor.

Description

Description ANTIMICROBIAL FLEXIBLE MATERIAL HAVING BARRIER PROPERTIES
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to an antimicrobial barrier and more particularly to a moisture activated antimicrobial composition which can be applied to textiles used in the medical industry.
Summary of the Invention
The present invention provides a novel composition which can be applied to any flexible material and in particular to woven or nonwoven textiles either during or after manufacture to provide an antimicrobial barrier against a broad spectrum of potential pathogens. In accordance with this invention, the novel composition is moisture activated such that once applied to the fabric or material it remains inert until it comes into contact with bodily secretions, water or other liquid. A hydrophilic polymeric component of the composition breaks down and precipitates upon contact with moisture, thus activating the composition. The composition, once activated, continues to afford protection for up to 12 hours. The active antimicrobial component of the composition consists of a mixture of a quaternary ammonium compound and nonoxynol 9.
It is therefore an important object of the present invention to provide a convenient and effective means for protecting patients and medical personnel against infection.
It is a further object of the present invention to provide an antimicrobial composition which can be applied to any flexible material including but not limited to disposable medical garments and face masks , paper products , or any woven or nonwoven textile.
A further object lies in the provision of an antimicrobial composition which is moisture activated .
It is yet a further object of the present invention to provide a composition wherein the active antimicrobial component consists of nonoxynol 9 and a quaternary ammonium compound.
These and other objects will become readily apparent from the detailed description which follows .
Detailed Description of the Preferred Embodiment
The present invention is directed to a moisture activated coating composition for substrates of flexible materials and in a preferred embodiment for application to disposable medical gowns , garments , and face masks . Incorporated into and throughout the composition is a functional substance which is biologically active against a broad spectrum of viruses , bacteria, fungii, and other pathogenic species . A large number of biologically active substances are available which retard bacterial , microbial , or fungal growth. It is contemplated that any of these commonly known biologically active substances could be utilized, however, in the preferred embodiment, the functional substance is comprised of a quaternary ammonium compound, nonoxynol 9, or a mixture of a quaternary ammonium compound and nonoxynol 9. The preferred quaternary ammonium compound is a blend of Myristalkonium chloride and Quaternium 14 shown by the general formula:
Figure imgf000005_0001
R ia 60% C14, 30% C16 and R is 68% C12, 32% C14 5% C12, 5% C18 n-alkyl dimethyl benzyl n-alkyl dimethyl ethyl- ammonium chloride benzyl ammonium chloride
Nonoxynol 9 is an ethoxylated nonyl phenol containing 9 moles of ethylene oxide and serves both as a nonoinic surfactant and an antimicrobial agent. Although both nonoxynol 9 and the blend of Myristalkonium chloride and Quaternium 14 can function alone, a synergistic effect is achieved when they are used in combination, producing substantially greater activity against pathogens than either substance alone. The nonoxynol 9 enables the coating composition to be spread evenly over the entire surface of the substrate or garment, thus achieving and maintaining a uniform antimicrobial effectiveness throughout. Nonoxynol 9 is preferably present in the amount of 1%-10% by weight and the quaternary ammonium compound blend in the amount of 0.021-0.06% by weight.
The coating composition additionally contains a hydrophobic, waterproofing agent. The hydrophobic agent is preferably a polymer derived from vinylpyrrolidone and a long chain alpha olefin represented by the general formula:
Figure imgf000006_0001
wherein R is alkyl or hydrogen
In the preferred embodiment, the hydrophobic agent is a PVP/eicosene copolymer (polyvinylpyrrolidone and eicosene) and is present 0.5%-6% by weight.
A hydrophilic film forming compound which is highly moisture sensitive and breaks down upon contact with water is further included in the coating composition. The film forming compound provides an adhesive type barrier between the functional substance and the environment, thus rendering the composition inert. Upon contact with blood or other bodily secretion, water, or any moisture or fluid in general, the hydrophilic film forming compound breaks down and precipitates, thereby allowing the functional substance to migrate to the outer surface of the substrate to effectively eliminate any pathogens present in the fluid or proximate to such. Once the film forming compound breaks down, the functional substance continues to inhibit microbial growth at the surface of the substrate or garment for up to 12 hours, thus affording protection to the wearer of the garment or any person or patient in close contact with the wearer.
Although many hydrophilic film forming agents are contemplated, preferred species include alkyl monesters or poly (methyl vinyl ether/maleic acid), represented by the following formula:
Figure imgf000007_0001
R is ethyl, isopropyl, or n-butyl Most particularly the ethyl ester of PVM/MA copolymer is selected with a molecular weight between 110,000-150,000 and present from 0.5%-6% by weight. These compounds are preferred due to their exceedingly high water sensitivity upon neutralization.
Due to the general water insolubility of the hydrophilic film forming compound, the inclusion of 2-8% by weight of an organic solvent is contemplated with anhydrous ethanol SD 40 being preferred. The organic solvent also functions as a drying agent. Anhydrous ethanol SD 40 and most other commonly utilized organic solvents exhibit relatively high flammability characteristics, therefore requiring that a stabilizer that effectively eliminates the flammable nature of the mixture be included. While the use of various stabilizers of the prior art may be acceptable to reduce fla mability, 1-10% by weight of 1,3 butylene glycol is a preferred species. 1,3 butylene glycol not only effectively stabilizes the ethanol or other solvent, but further aids in dispersion.
The coating composition may also include additional materials such as aloe, present in the range of 1-5% by weight, to provide comfort to the skin and decrease the likelihood of skin irritation.
The formation of the coating composition includes the use of three separate mixing tanks. In a first mixing tank, approximately 1/3 of the total volume of the stabilizer (butylene glycol) is heated to 160 degrees F while stirring slowly. The hydrophobic waterproof polymeric compound (PVP/eicosene) is then added and the resultant mixture is stirred until dissolved. This mixture is then cooled to 100 degrees F. In a second mixing tank, a second 1/3 portion of the butylene glycol is mixed with the functional substance (nonoxynol 9 and the quaternary ammonium compound). The hydrophilic film forming compound (PVM/MA) is then dissolved in the solvent (ethanol) in a third tank. The last 1/3 portion of the butylene glycol is then added to the third tank along with aloe and water to bring the mixture to the desired concentration. The mixture in the second tank is slowly added to the first tank under constant stirring and agitation. The mixture from the third tank is then introduced very slowly to the first tank, mixing until a homogeneous mixture is achieved.
The manner of application of the resultant composition to the flexible material or garment may be varied and could include such methods as spraying, dipping, painting, or adding to the final rinse cycle during a machine washing operation. The composition will coat the material or fabric and in some instances impregnate the fiber structure of the material.
Having described the invention in detail and by reference to the preferred embodiment thereof, it will be apparent that modifications and variations are possible without departing from the appended claims.

Claims

Claims
1. An antimicrobial composition for application to a substrate comprising: a quaternary ammonium compound in an amount of between .02% to .06% by weight of said composition, an ethoxylated nonyl phenol containing 9 moles of ethylene oxide in an amount of between 1% to 10% by weight of said composition,
1,3 butylene glycol in an amount of between 1% to 10% by weight of said composition, a hydrophobic waterproof polymeric compound in an amount of between .5% to 6% by weight of said composition, a hydrophilic film forming compound in an amount of between .5% to 6% by weight of said composition, an organic solvent including anhydrous ethanol in an amount of between 2% to 8% by weight of said composition, aloe in an amount of between 1% to 5% by weight of said composition, and water in an amount of between 55% to 90% by weight of said composition.
2. The antimicrobial composition as set forth in claim 1 wherein said hydrophobic waterproof polymeric compound is a copolymer of polyvinylpyrrolidone and eicosene.
3. The antimicrobial composition as set forth in claim 1 wherein said hydrophilic film forming compound is a copolymer of monoethyl ester of poly(methyl vinyl ether) and maleic acid.
4. The antimicrobial composition as set forth in claim 1 wherein said quaternary ammonium compound is a blend of n-alkyl dimethyl benzyl ammonium chloride and n-alkyl dimethyl ethylbenzyl ammonium chloride.
5. A method of producing an antimicrobial composition for application to a substrate including: a quaternary ammonium compound in an amount of between .02% to .06% by weight of said composition, ethoxylated nonyl phenol containing 9 moles of ethylene oxide in an amount of between 1% to 10% by weight of said composition, 1,3 butylene glycol in an amount of between 1% to 10% by weight of said composition, a hydrophobic waterproof polymeric compound in an amount of between .5% to 6% by weight of said composition, a hydrophilic film forming compound in an amount of between .5% to 6% by weight of said composition, an organic solvent including anhydrous ethanol in an amount of between 1% to 5% by weight of said composition, aloe in an amount of between 1% to 5% by weight of said composition, and water in an amount of between 55% to 90% by weight of said composition, said method comprising the steps of: a) heating 1/3 of a total volume of the 1,3 butylene glycol to 160 degrees F stirring continuously, b) adding and mixing the hydrophobic waterproof polymeric compound with the 1,3 butylene glycol in a first mixing tank to form a first mixture; c) cooling said first mixture to 100 degrees F; d) mixing 1/3 of the total volume of the 1,3 butylene glycol with the quaternary ammonium compound and the nonoxynol 9 in a second mixing tank to form a second mixture; e) mixing and dissolving the hydrophilic film forming compound in the anhydrous ethanol in a third mixing tank; f) adding one third of the total volume of the 1,3 butylene glycol to the third mixing tank; g) adding the water and the aloe to the third mixing tank while stirring continuously to form a third mixture; h) gradually combining said first mixture with said second mixture in said first mixing tank; and i) gradually adding and mixing said third mixture to said first mixing tank, stirring until a homogeneous mixture is achieved.
6. An antimicrobial composition for application to a substrate comprising: a quaternary ammonium compound in an amount of between .02% to .06% by weight of said composition, an ethoxylated nonyl phenol containing 9 moles of ethylene oxide in an amount of between 1% to 10% by weight of said composition,
1,3 butylene glycol in an amount of between 1% to 10% by weight of said composition, a hydrophobic waterproof polymeric compound in an amount of between .5% to 6% by weight of said composition, a hydrophilic film forming compound in an amount of between .5% to 6% by weight of said composition, an organic solvent including anhydrous ethanol in an amount of between 2% to 8% by weight of said composition, and water in an amount of between 55% to 90% by weight of said composition.
PCT/US1994/008924 1993-07-06 1994-08-06 Antimicrobial flexible material having barrier properties WO1996004899A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US08/086,022 US5336305A (en) 1993-07-06 1993-07-06 Flexible material having barrier properties
PCT/US1994/008924 WO1996004899A1 (en) 1993-07-06 1994-08-06 Antimicrobial flexible material having barrier properties

Applications Claiming Priority (2)

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US08/086,022 US5336305A (en) 1993-07-06 1993-07-06 Flexible material having barrier properties
PCT/US1994/008924 WO1996004899A1 (en) 1993-07-06 1994-08-06 Antimicrobial flexible material having barrier properties

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101665659A (en) * 2008-09-04 2010-03-10 罗门哈斯公司 Microbiocidal coatings
EP2173175A1 (en) * 2007-03-07 2010-04-14 Thomas L. Higgins Organosilane -nonionic-water stable quaternary ammonium compositions and methods
AU2015224383B2 (en) * 2008-09-04 2016-11-03 Rohm And Haas Company Microbiocidal coatings

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4810489A (en) * 1986-12-04 1989-03-07 Bristol-Myers Company High oil phase pharmaceutical vehicles and sunscreen compositions having waterproof sun protection factors
US5154920A (en) * 1985-03-13 1992-10-13 Ecolab Inc. Disinfectant polymeric coatings for hard surfaces

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5154920A (en) * 1985-03-13 1992-10-13 Ecolab Inc. Disinfectant polymeric coatings for hard surfaces
US4810489A (en) * 1986-12-04 1989-03-07 Bristol-Myers Company High oil phase pharmaceutical vehicles and sunscreen compositions having waterproof sun protection factors

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 111, issued 20 October 1989, MURRAY et al., "High Oil Phase Pharmaceutical Vehicles and Sunscreens Containing PVP-Long-Chain Olefin Copolymers", page 382, Abstract 140215j; & US,A,4 810 489 (07 March 1989). *
CHEMICAL ABSTRACTS, Volume 116, issued 12 September 1992, KLEBANOFF, "Effects of the Spermicidal Agent Nonoxynol-9 on Vaginal Microbial Flora", page 469, Abstract No. 124748h; & J. INFECT. DIS., Vol. 165(1), 19-25. *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2173175A1 (en) * 2007-03-07 2010-04-14 Thomas L. Higgins Organosilane -nonionic-water stable quaternary ammonium compositions and methods
EP2173175A4 (en) * 2007-03-07 2013-05-29 Thomas L Higgins Organosilane -nonionic-water stable quaternary ammonium compositions and methods
CN101665659A (en) * 2008-09-04 2010-03-10 罗门哈斯公司 Microbiocidal coatings
EP2161311A1 (en) * 2008-09-04 2010-03-10 Rohm and Haas Company Microbiocidal coatings
US8007834B2 (en) 2008-09-04 2011-08-30 Rohm And Haas Company Microbiocidal coatings
CN101665659B (en) * 2008-09-04 2012-12-05 罗门哈斯公司 Microbiocidal coatings
TWI399171B (en) * 2008-09-04 2013-06-21 Rohm & Haas Microbiocidal coatings
AU2015224383B2 (en) * 2008-09-04 2016-11-03 Rohm And Haas Company Microbiocidal coatings

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