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WO2003014274A1 - Produit de nettoyage antimicrobien - Google Patents

Produit de nettoyage antimicrobien Download PDF

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Publication number
WO2003014274A1
WO2003014274A1 PCT/EP2002/006755 EP0206755W WO03014274A1 WO 2003014274 A1 WO2003014274 A1 WO 2003014274A1 EP 0206755 W EP0206755 W EP 0206755W WO 03014274 A1 WO03014274 A1 WO 03014274A1
Authority
WO
WIPO (PCT)
Prior art keywords
antimicrobial
cleaning
ester
acrylic acid
chloride
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.)
Ceased
Application number
PCT/EP2002/006755
Other languages
German (de)
English (en)
Inventor
Peter Ottersbach
Friedrich Sosna
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.)
Creavis Gesellschaft fuer Technologie und Innovation mbH
Original Assignee
Creavis Gesellschaft fuer Technologie und Innovation mbH
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 Creavis Gesellschaft fuer Technologie und Innovation mbH filed Critical Creavis Gesellschaft fuer Technologie und Innovation mbH
Publication of WO2003014274A1 publication Critical patent/WO2003014274A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers

Definitions

  • the invention relates to cleaning agents and disinfectants which contain antimicrobial polymers.
  • Mucus layers often form, which cause microbial populations to rise extremely, which have a lasting impact on the quality of water, beverages and food, and which can even spoil the goods and damage the health of consumers.
  • Bacteria must be kept away from all areas of life where hygiene is important. This affects textiles for direct body contact, especially for the genital area and for nursing and elderly care. In addition, bacteria must be kept away from furniture and device surfaces in care stations, in particular in the area of intensive care and the care of small children, in hospitals, in particular in rooms for medical interventions and in isolation stations for critical infections and in toilets.
  • substances are sought that have an efficient microbicidal effect over a longer period of time, are as little or not toxic to higher organisms, are not released into the air and can be used as easily as conventional cleaning agents or disinfectants ,
  • Antimicrobial polymers are e.g. B. from European patent applications 0 862 858 and patent applications DE 100 24 270, DE 100 22 406, PCT / EP00 / 06501, DE 100 14 726, DE 100 08 177, PCT / EP00 / 06812, PCT / EP00 / 06487 , PCT / EP00 / 06506, PCT / EP00 / 02813, PCT / EP00 / 02819, PCT / EP00 / 02818, PCT / EP00 / 02780, PCT / EP00 / 02781, PCT / EP00 / 02783, PCT / EP00 / 02782, PCT / EP00 / 02799, PCT / EP00 / 02798, PCT / EP00 / 00545, PCT / EP00 / 00544.
  • These polymers do not contain any low molecular weight components; the antimicrobial properties are due to the contact of bacteria with the surface.
  • the task was therefore to find a cleaning agent and disinfectant, the effect of which lasts for a long period of time like low molecular weight compounds and at the same time is not fixed to a surface. It has been found that microbicidal cleaning and disinfectants based on antimicrobial polymers can be produced, which combine excellent microbicidal effects with good toxicological behavior towards higher organisms.
  • the present invention therefore relates to cleaning agents and disinfectants containing 0.01-70% by weight of at least one antimicrobial polymer.
  • the cleaning and disinfecting agents according to the invention can therefore also other microbicidal agents such.
  • the antimicrobial polymers the other, generally toxicologically questionable microbicides can be reduced in their use concentration without worsening the antimicrobial effect of the cleaning agents and disinfectants. In individual cases, the addition of further microbicidal substances can even be dispensed with entirely.
  • ingredients of the cleaning and disinfecting agents according to the invention include peroxygen and chlorine compounds (toilet cleaners), alcohols and phenols, disinfectants such as trichlosan (5-chloro-2- (2,4-dichlorophenoxy) phenol, terpenes such as geraniol and D- Limonene, biguanides and quaternary ammonium compounds such as benzalkonium chloride or didecyldimonium chloride.
  • peroxygen and chlorine compounds toilet cleaners
  • alcohols and phenols disinfectants
  • trichlosan (5-chloro-2- (2,4-dichlorophenoxy) phenol
  • terpenes such as geraniol and D- Limonene
  • biguanides and quaternary ammonium compounds such as benzalkonium chloride or didecyldimonium chloride.
  • These compounds can optionally be added in a concentration of 0.1-10% by weight.
  • the antimicrobial polymers can be added in the course of the manufacturing process of the cleaning agents and disinfectants or afterwards.
  • the cleaners according to the invention can be used as sanitary surface cleaners in the food industry, in hospitals or in milk and agriculture, as an algicide for swimming pools, fountains or cooling towers.
  • the antimicrobial cleaning agents and disinfectants produced in this way can be used like conventional cleaning agents and disinfectants.
  • Spraying on surfaces to be disinfected is just as feasible as application by sponges or direct pouring, as well as by brushes or analogous application methods, in retarded form, e.g. in storage containers that are hung directly into a toilet and continuously dispense product.
  • the addition of other substances, e.g. Fragrances generally do not change the antimicrobial properties of the products according to the invention and are therefore easily possible in individual cases.
  • the special properties of the antimicrobial polymers generally lead to the formation of thin films on the treated surfaces during use. These films have an antimicrobial effect over a longer period of time and only need to be removed mechanically, e.g. by water-related erosion, can be renewed or replaced.
  • antimicrobial cleaning agents and disinfectants that combine the required application properties for the tasks as well as the biochemical inhibitory effect on microbial growth in an almost ideal way. Since the antimicrobial polymer does not release any low-molecular components into the environment and thus into ambient air or wastewater, such systems can be used without any problems, without the toxicologically questionable transfer of biocides from the product.
  • Nitrogen- and phosphorus-functionalized monomers are preferably used for the production of the antimicrobial polymers.
  • these polymers are produced from at least one of the following monomers:
  • 2-tert-butylaminoethyl methacrylic acid 2-diethylaminoethyl methacrylic acid, 2-diethylaminomethyl methacrylate, 2-tert-butylaminoethyl acrylate, 3- acrylic acid dimethylaminopropyl ester, acrylic acid 2-diethylaminoethyl ester, acrylic acid 2-dimethylaminoethyl ester, dimethylaminopropyl methacrylamide, diethylamino propyl methacrylamide, acrylic acid 3-dimethylaminopropylamide, 2-methacryloyloxyethyltrimethylammonium methosulfate, methacrylic acid 2-diethylaminoethyl ester
  • Methacryloyloxyethyltrimethylammonium chloride 3-methacryloylaminopropyltrimethylammonium chloride, 2-methacryloyloxyethyltrimethylammonium chloride, 2-
  • acrylates or methacrylates e.g. B. acrylic acid, tert-butyl methacrylate or methyl methacrylate, styrene or its derivatives, vinyl chloride, vinyl ether, acrylamides, acrylonitriles, olefins (ethylene, propylene, butylene, isobutylene), AUylENSen, vinyl ketones, vinyl acetic acid, vinyl acetate or vinyl esters, especially z.
  • methacrylic acid methyl ester methacrylic acid ethyl ester, methacrylic acid butyl ester, methacrylic acid tert-butyl ester, acrylic acid methyl ester,
  • Acrylic acid ethyl ester acrylic acid butyl ester and / or acrylic acid tert-butyl ester.
  • the proportion of antimicrobial polymers in the cleaning agents and disinfectants can be 0.01 to 70% by weight, preferably 0.1 to 40% by weight, particularly preferably 0.1 to 20% by weight.
  • the addition of an antimicrobial aqueous emulsion or dispersion prepared on the basis of an antimicrobial polymer also offers itself.
  • the cleaning agents and disinfectants according to the invention can be liquid (e.g. aqueous solution), solid (e.g. urine scale) or pasty.
  • ingredients include e.g. B. surfactants, water, alcohols, scouring powder or antistatic agents.
  • Example 2 5 g of the product from Example 1 are dissolved in 100 mL ethanol and placed in a commercially available spray bottle, as described e.g. also used for bathroom and toilet cleaners.
  • a commercially available ceramic tile as is widely used in the sanitary field, is cut into pieces of 2 by 3 cm and then sprayed with the spray bottle with part of the contents of the bottle in such a way that the surfaces of the tile pieces are covered. After 5 seconds, the tiles treated in this way are rinsed with 50 mL water each, which simulates the effect of flushing the toilet.
  • a 2 x 3 cm piece of a treated tile fragment from example la is placed on the bottom of a beaker, which contains 10 ml of a test seed suspension from Pseudomonas contains aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs has dropped from 10 to 10 germs per mL.
  • a 2 x 3 cm piece of a treated tile fragment from Example 1a is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, no Staphylococcus aureus germs can be detected.
  • a 2 x 3 cm piece of a treated tile fragment from example la is treated with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be found on any of the treated tile pieces.
  • the treated tile fragments from example la are rinsed a total of 20 times with 50 ml of water every 30 minutes in order to simulate the effect of a toilet flush that is in use.
  • Example lg A 2 x 3 cm piece of a treated tile fragment from example le is placed on the bottom of a beaker containing 10 ml of a test germ suspension of Staphylococcus aureus. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the
  • Germ count decreased from 10 to 10 germs per mL.
  • Example li A 2 x 3 cm piece of a treated steel fragment from example li is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 3 germs per mL.
  • a 2 x 3 cm piece of a treated steel fragment from example li is placed on the bottom of a beaker containing 10 ml of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours.
  • a 2 x 3 cm piece of a treated steel fragment from example li is also included
  • Example 2 40 ml of dimethylaminopropyl methacrylamide (Aldrich) and 200 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.4 g of azobisisobutyronitrile dissolved in 20 ml of ethanol are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 6 hours. After this time, the solvent is removed from the reaction mixture by distillation and dried for 24 hours at 50 ° C in a vacuum. The product is then dissolved in 200 ml of acetone, after which the solvent is removed from the reaction mixture by distillation and dried in vacuo at 50 ° C. for 24 hours. The reaction product is then ground up finely.
  • Example 2 5 g of the product from Example 2 are dissolved in 100 mL ethanol and placed in a commercially available spray bottle, as described e.g. also used for bathroom and toilet cleaners.
  • a commercially available ceramic tile as is widely used in the sanitary field, is cut into pieces of 2 by 3 cm and then sprayed with the spray bottle with part of the contents of the bottle in such a way that the surfaces of the tile pieces are covered. After 5 seconds, the tiles treated in this way are rinsed with 50 mL water each, which simulates the effect of flushing the toilet.
  • Example 2b A 2 x 3 cm piece of a treated tile fragment from Example 2a is placed on the bottom of a beaker containing 10 mL of a test seed suspension of Pseudomonas aeruginosa. The system prepared in this way will now run for 4 hours shaken. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 4 germs per mL.
  • a 2 x 3 cm piece of a treated tile fragment from Example 2a is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, no Staphylococcus aureus germs can be detected.
  • a 2 x 3 cm piece of a treated tile fragment from Example 2a is treated with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be found on any of the treated tile pieces.
  • the treated tile fragments from Example 2a are rinsed a total of 20 times with 50 mL water every 30 minutes in order to simulate the effect of a toilet flush that is in use.
  • a 2 x 3 cm piece of a treated tile fragment from Example 2e is placed on the bottom of a beaker containing 10 mL of a test seed suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 4 germs per mL.
  • Example 2g A 2 x 3 cm piece of a treated tile fragment from Example 2e is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 4 germs per mL.
  • Example 2h A 2 x 3 cm piece of a treated tile fragment from example 2e is blended with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be found on any of the treated tile pieces.
  • Example 3 5 g of the product from Example 3 are dissolved in 100 mL ethanol and placed in a commercially available spray bottle, as described e.g. also used for bathroom and toilet cleaners.
  • a commercially available ceramic tile as is widely used in the sanitary field, is cut into pieces of 2 by 3 cm and then sprayed with the spray bottle with part of the contents of the bottle in such a way that the surfaces of the tile pieces are covered. After 5 seconds, the tiles treated in this way are rinsed with 50 mL water each, which simulates the effect of flushing the toilet.
  • a 2 x 3 cm piece of a treated tile fragment from Example 3a is placed on the bottom of a beaker, which contains 10 mL of a test seed suspension from Pseudomonas contains aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • a 2 x 3 cm piece of a treated tile fragment from Example 3a is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, no Staphylococcus aureus germs can be detected.
  • a 2 x 3 cm piece of a treated tile fragment from Example 3a is blended with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be found on any of the treated tile pieces.
  • the treated tile fragments from Example 3a are rinsed a total of 20 times with 50 mL water every 30 minutes in order to simulate the effect of a toilet flush that is in use.
  • a 2 x 3 cm piece of a treated tile fragment from Example 3e is placed on the bottom of a beaker containing 10 mL of a test seed suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • a 2 x 3 cm piece of a treated tile fragment from Example 3e is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus contains.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • Each 2 x 3 cm piece of a treated tile fragment from Example 3e is treated with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be found on any of the treated tile pieces.
  • Example 4a 10 g of the product from Example 4 are diluted with in 40 mL water and placed in a commercially available spray bottle, as described e.g. also used for bathroom and toilet cleaners.
  • a commercially available ceramic tile as is widely used in the sanitary field, is cut into pieces of 2 by 3 cm and then sprayed with the spray bottle with part of the contents of the bottle in such a way that the surfaces of the tile pieces are covered. After 5 seconds, the tiles treated in this way are rinsed with 50 mL water each, which simulates the effect of flushing the toilet.
  • a 2 x 3 cm piece of a treated tile fragment from Example 4a is placed on the bottom of a beaker containing 10 mL of a test seed suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time 7 ⁇ the number of germs has dropped from 10 to 10 germs per mL.
  • a 2 x 3 cm piece of a treated tile fragment from example 4a is placed on the bottom of a beaker containing 10 ml of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours.
  • Example 4d A 2 x 3 cm piece of a treated tile fragment from example 4a is also included
  • the treated tile fragments from Example 4a are rinsed a total of 20 times with 50 mL water every 30 minutes in order to simulate the effect of a toilet flush that is in use.
  • a 2 x 3 cm piece of a treated tile fragment from Example 4e is placed on the bottom of a beaker containing 10 mL of a test seed suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 3 germs per mL.
  • Example 4h A 2 x 3 cm piece of a treated tile fragment from Example 4e is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • Example 4h
  • a 2 x 3 cm piece of a treated tile fragment from example 4e is blended with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be found on any of the treated tile pieces.
  • 10 g of the product from Example 4 are diluted with in 40 mL water and placed in a commercially available spray bottle, as described e.g. also used for bathroom and toilet cleaners.
  • a commercial steel sheet such as is used in the sanitary area, is cut into pieces of 2 by 3 cm and then sprayed with the spray bottle with part of the contents of the bottle in such a way that the surfaces of the steel pieces are covered. After 5 seconds, the pieces treated in this way are rinsed with 50 mL water each, which simulates the effect of flushing the toilet.
  • a 2 by 3 cm piece of a treated steel fragment from Example 4i is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs has dropped from 10 to 10 germs per mL.
  • a 2 x 3 cm piece of a treated steel fragment from Example 4i is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, no Staphylococcus aureus germs can be detected.
  • a 2 x 3 cm piece of a treated steel fragment from Example 4i is blended with Chlorella sp., Trentepohlia sp., Gloeocapsa sp. Calothrix sp. and Aspergilus niger. These samples are then placed in an incubator for 3 weeks. In contrast to moving ones, no growth can be detected on any of the treated steel fragments.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne un produit de nettoyage et de désinfection antimicrobien à base de polymères antimicrobiens.
PCT/EP2002/006755 2001-08-02 2002-06-19 Produit de nettoyage antimicrobien Ceased WO2003014274A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10137978.1 2001-08-02
DE2001137978 DE10137978A1 (de) 2001-08-02 2001-08-02 Antimikrobielle Reinigungsmittel

Publications (1)

Publication Number Publication Date
WO2003014274A1 true WO2003014274A1 (fr) 2003-02-20

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Application Number Title Priority Date Filing Date
PCT/EP2002/006755 Ceased WO2003014274A1 (fr) 2001-08-02 2002-06-19 Produit de nettoyage antimicrobien

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DE (1) DE10137978A1 (fr)
WO (1) WO2003014274A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100513398C (zh) * 2002-12-03 2009-07-15 Axys药物公司 作为因子viia抑制剂的2-(2-羟基联苯-3-基)-1h-苯并咪唑-5-甲脒衍生物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1774951A1 (fr) * 2005-10-11 2007-04-18 Dux S.A. Composition liquide de nettoyage et de soin

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3428680A (en) * 1964-01-03 1969-02-18 Procter & Gamble Polyquaternary ammonium salts of polymerized epichlorohydrin
US4755327A (en) * 1986-11-26 1988-07-05 Sterling Drug Inc. Isotropic laundry detergents containing polymeric quaternary ammonium salts
EP0359574A2 (fr) * 1988-09-15 1990-03-21 Alcon Laboratories, Inc. Solutions aqueuses antimicrobiennes pour l'entretien des lentilles de contact
WO1990006125A1 (fr) * 1988-12-05 1990-06-14 Olin Corporation Utilisation de polymeres contenant du pyrithione comme agents antimicrobiens dans les produits cosmetiques
EP0591024A2 (fr) * 1992-09-23 1994-04-06 Centre Technique Industriel dit: INSTITUT TEXTILE DE FRANCE Polymère antiseptique
EP0602254A1 (fr) * 1992-07-06 1994-06-22 Otsuka Kagaku Kabushiki Kaisha Monomere polymerisable et son polymere; procede de production associe
GB2304286A (en) * 1995-08-18 1997-03-19 Rhone Poulenc Chemicals Biocidal hard surface treatment with sustained effect based on use of a copolymer of hydrophilic oxyethylene/oxypropylene and hydrophobic ester chain units
WO1999024543A1 (fr) * 1997-11-12 1999-05-20 Bausch & Lomb Incorporated Desinfection des lentilles de contact avec des polyquaterniums et des biguanides polymeres
WO2001051530A1 (fr) * 2000-01-14 2001-07-19 Fancl Corporation Agent antimicrobien faiblement irritant a masse moleculaire elevee
DE10024270A1 (de) * 2000-05-17 2001-11-22 Creavis Tech & Innovation Gmbh Antimikrobielle Polymere und Polymerblends aus polymeren Alkylacrylamiden

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3428680A (en) * 1964-01-03 1969-02-18 Procter & Gamble Polyquaternary ammonium salts of polymerized epichlorohydrin
US4755327A (en) * 1986-11-26 1988-07-05 Sterling Drug Inc. Isotropic laundry detergents containing polymeric quaternary ammonium salts
EP0359574A2 (fr) * 1988-09-15 1990-03-21 Alcon Laboratories, Inc. Solutions aqueuses antimicrobiennes pour l'entretien des lentilles de contact
WO1990006125A1 (fr) * 1988-12-05 1990-06-14 Olin Corporation Utilisation de polymeres contenant du pyrithione comme agents antimicrobiens dans les produits cosmetiques
EP0602254A1 (fr) * 1992-07-06 1994-06-22 Otsuka Kagaku Kabushiki Kaisha Monomere polymerisable et son polymere; procede de production associe
EP0591024A2 (fr) * 1992-09-23 1994-04-06 Centre Technique Industriel dit: INSTITUT TEXTILE DE FRANCE Polymère antiseptique
GB2304286A (en) * 1995-08-18 1997-03-19 Rhone Poulenc Chemicals Biocidal hard surface treatment with sustained effect based on use of a copolymer of hydrophilic oxyethylene/oxypropylene and hydrophobic ester chain units
WO1999024543A1 (fr) * 1997-11-12 1999-05-20 Bausch & Lomb Incorporated Desinfection des lentilles de contact avec des polyquaterniums et des biguanides polymeres
WO2001051530A1 (fr) * 2000-01-14 2001-07-19 Fancl Corporation Agent antimicrobien faiblement irritant a masse moleculaire elevee
DE10024270A1 (de) * 2000-05-17 2001-11-22 Creavis Tech & Innovation Gmbh Antimikrobielle Polymere und Polymerblends aus polymeren Alkylacrylamiden

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 200161, Derwent World Patents Index; Class A13, AN 2001-549853, XP002218311 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100513398C (zh) * 2002-12-03 2009-07-15 Axys药物公司 作为因子viia抑制剂的2-(2-羟基联苯-3-基)-1h-苯并咪唑-5-甲脒衍生物

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DE10137978A1 (de) 2003-02-13

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