EP0836469A4 - BACTERICIDAL - Google Patents

BACTERICIDAL

Info

Publication number
EP0836469A4
EP0836469A4 EP96919315A EP96919315A EP0836469A4 EP 0836469 A4 EP0836469 A4 EP 0836469A4 EP 96919315 A EP96919315 A EP 96919315A EP 96919315 A EP96919315 A EP 96919315A EP 0836469 A4 EP0836469 A4 EP 0836469A4
Authority
EP
European Patent Office
Prior art keywords
bactericidal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96919315A
Other languages
German (de)
French (fr)
Other versions
EP0836469A1 (en
Inventor
Gerard Marcel Baillely
Robin Gibson Hall
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP0836469A1 publication Critical patent/EP0836469A1/en
Publication of EP0836469A4 publication Critical patent/EP0836469A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00Preservation of foods or foodstuffs, in general
    • A23B2/70Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729Organic compounds; Microorganisms; Enzymes
    • A23B2/742Organic compounds containing oxygen
    • A23B2/754Organic compounds containing oxygen containing carboxyl groups
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00Preservation of foods or foodstuffs, in general
    • A23B2/70Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729Organic compounds; Microorganisms; Enzymes
    • A23B2/762Organic compounds containing nitrogen
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362Polycarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/51Chelating agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants

Definitions

  • the present invention relates to the use of a chelant as a a bactericidal compound as well as a bactericidal composition containing a chelant, suitable for use in deodorants, soaps, oral health care, dermatological preparations and also in food as a food preservative. More particularly, it relates to a bactericidal composition comprising a chelant as a bactericidal agent or as a co-bactericidal agent.
  • Bacteria may be found in the food or clinic environment. Bacteria strains are divided into two types: gram negative and gram positive. Gram negative bacteria types include bacteria such as Salmonella typhimurium, Bacterioides gingivalis, Actinobacillus actinomycetescomitans, Klebsiella pneumoniae, Escherichia coli and Pseudomonas aeruginosa while gram positive bacteria include bacteria such as Staphilococcus aureus, Streptococcus mutans, Listeria monocytogenes, Streptococcus agalactiae and Coryneform bacteria.
  • Gram negative bacteria types include bacteria such as Salmonella typhimurium, Bacterioides gingivalis, Actinobacillus actinomycetescomitans, Klebsiella pneumoniae, Escherichia coli and Pseudomonas aeruginosa
  • gram positive bacteria include bacteria such as Staphilococcus aureus, Strept
  • bactericides of the bacterial or chemical type To retard and/or prevent such growth, it is known in the art to use bactericides of the bacterial or chemical type. However, a problem encountered with such bactericides is that they are expensive and/or sometimes are not fully active. Not to be bound by theory, it is believed that the cations present on the cell wall of the bacteria prevent the bactericidal action. The Applicant has found that the problems of bacteria growth and reduced bactericidal activity are particularly troublesome with bactericidal agents of the chlorophenol and/or quaternary ammonium type.
  • the formulator thus faces the challenge of formulating a product which maximises the bactericidal activity, minimises the contamination and is also inexpensive.
  • WO 89/1239 discloses the use of lanthionine containing bacteriocin and a chelating agent for inhibiting Gram negative bacteria growth. More particularly disclosed are lanthionine containing bacteriocins with ethylene diamine tetraacetic acid (EDTA) for inhibiting Pseudomonas aeruginosa growth.
  • EDTA ethylene diamine tetraacetic acid
  • EP 0,639,636 discloses the use of a cationic germicide with a chelating agent and a surfactant. More particularly disclosed are cationic germicides with EDTA and a surfactant for inhibiting gram negative bacteria growth such as Escherichia coli and Pseudomonas aeruginosa.
  • the present invention relates to the use of a chelant selected from the succinic acid, glutaric acid, phosphonic acid classes or any salts thereof and mixtures thereof as a bactericidal compound. Also provided herein are bactericidal compositions containing said chelant together with or without a conventional bactericidal agent.
  • a method for reducing the bacterial growth which comprises the step of exposing said bacteria strain with a bactericidal composition according to the invention.
  • An essential component of the invention is a chelant.
  • the chelant When used as a bactericidal compound per se, the chelant will be present in amount of at least 0.05%, preferably at least 0.7% and more preferably at least 1 % by weight of the composition.
  • said chelant When used as a co-bactericide, said chelant will be present in amount from at least 0.05%, preferably at least 0.5% and more preferably at least 1 % by weight of the composition.
  • Suitable chelants for the purpose of the invention are compounds selected from succinic acid, glutaric acid, phosphonic acid classes or any salts thereof and mixtures thereof.
  • Non limiting examples of chelants of the succinic acid class include emylenediamine disuccinic acid (EDDS), 2-hydroxypropy lenediamine disuccinic acid (HPDDS) and any salts thereof and mixtures thereof.
  • EDDS emylenediamine disuccinic acid
  • HPDDS 2-hydroxypropy lenediamine disuccinic acid
  • a suitable chelant of the glutaric acid class is ethylenediamine diglutaric acid (EDDG) or salt thereof.
  • Non limiting examples of chelants of the phosphonic acid class include emylenediaminetetrakis (methylenephosphonic acid), diethylene triamine penta (methylene phosphonic acid), ethylene diamine tri (methylene phosphonic acid), hexamethylene diamine tetra (methylene phosphonic acid), ⁇ -hydroxy-2 phenyl ethyl diphosphonic acid, methylene diphosphonic acid, hydroxy 1,1-hexylidene diphosphonic acid, vinylidene 1,1 diphosphonic acid, 1,2 dihydroxyethane 1,1 diphosphonic acid and hydroxy-ethane 1,1 diphosphonic acid and any salts thereof and mixtures thereof.
  • Preferred from the above phosphonic acid species is hydroxy-ethane 1,1 diphosphonic acid. More preferably, said chelants are selected from ethylenediamine disuccinic acid, ethylenediamine diglutaric acid, 2- hydroxypropylenediamine disuccinic acid, hydroxy ethane 1,1 diphosphonic acid or any salts thereof and mixtures thereof. Especially preferred is ethylenediarnine-N,N'-disuccinic acid or the alkali metal, alkaline earth metal, ammonium, or substituted ammomum salts thereof, or mixtures thereof.
  • Preferred EDDS compounds are the free acid form and the sodium or magnesium salt or complex thereof. Examples of such preferred sodium salts of EDDS include Na2EDDS and Na ⁇ EDDS. Examples of such preferred magnesium complexes of EDDS include MgEDDS and Mg2EDDS.
  • a bactericidal composition comprising a chelant, wherein said chelant is as defined herein before.
  • the bactericidal composition of the invention may further comprise one or more conventional bactericidal agents.
  • the combination of said conventional bactericidal agent with said chelant is seen to produce a synergistic action on bacteria strain, particularly on Gram negative bacteria types and more specifically on Pseudomonas aeruginosa.
  • the said combination allows the use of a reduced amount of conventional bactericides. More specifically, the combination produces a reduction in the minimum inhibitory concentration (MIC) of the conventional bactericide used per se.
  • MIC minimum inhibitory concentration
  • MIC is meant the “Minimum Inhibitory Concentration”, e.g the minimum level necessary of such conventional bactericides to inhibit the bacteria growth.
  • Conventional bactericidal agents of use herein, for the purpose of the invention, will be selected from agents having their original MIC (e.g when used without the presence of a chelant of the invention) reduced by at least 50%, preferably 70% and more preferably at least 90% when in the presence of said chelant.
  • bactericidal agents selected from chlorophenol and quaternary ammonium species and mixtures thereof.
  • chlorophenol species are compounds selected from 2,4,4' trichloro-2' -hydroxydiphenyl ether available under the tradename Irgasan DP 300 from Ciba Geigy, 2,2'-dihydroxy-5,5'-dibromo-diphenyl ether and mixtures thereof.
  • Preferred among the quaternary ammonium species is cetyl trimethyl ammonium bromide.
  • these conventional bactericides are selected from 2,4,4' trichloro-2 * -hydroxydiphenyl ether (Irgasan DP 300), cetyl trimethyl ammonium bromide and mixtures thereof.
  • a most preferred conventional bactericide to be used in combination with a chelant of the invention is 2,4,4' trichloro-2' -hydroxydiphenyl ether (Irgasan DP 300).
  • Additional compounds may also be added to the composition. Such additional compounds should not be detrimental to the bactericidal composition of the invention.
  • Non limiting examples of classes of suitable additional compounds which may be of use herein include surfactants, binders and thickeners.
  • Non limiting examples of surfactants useful herein typically at levels from 1% to 95%, preferably 1% to 55% by weight, include the conventional Cn-Ci8 alkyl benzene sulfonates ("LAS") and primary, branched-chain and random C10-C20 alkyl sulfates (“AS”), the C10-C18 secondary (2,3) alkyl sulfates of the formula CH3(CH2) (CHOS ⁇ 3 ⁇ M + ) CH3 and CH3 (CH2) y (CHOS ⁇ 3 " M ) CH2CH3 where x and y - 1) are integers of at least 7, preferably at least 9, and M is a water-solubilizing cation, especially sodium, unsaturated sulfates such as oleyl sulfate, the CiQ-Cis alkyl alkoxy sulfates ("AE S”; especially EO 1-7 ethoxy sulfates), C10-C18 alkyl alkoxy carboxylates (
  • the conventional nonionic and amphoteric surfactants such as the C ⁇ 2-C ⁇ g alkyl ethoxylates ("AE"), including the so-called narrow peaked alkyl ethoxylates and C6-C12 alkyl phenol alkoxylates (especially ethoxylates and mixed ethoxy/propoxy), C ⁇ 2-Cl8 betaines and sulfobetaines ("sultaines"), C10-C18 amine oxides, and the like, can also be included in the overall compositions.
  • the C10-C18 N-alkyl polyhydroxy fatty acid amides can also be used. Typical examples include the C12- 18 N- methylglucamides. See WO 9,206,154.
  • sugar-derived surfactants include the N-alkoxy polyhydroxy fatty acid amides, such as C10-C18 N (3-methoxypropyl) glucamide.
  • the N-propyl through N-hexyl C12-C18 glucamides can be used for low sudsing.
  • C10-C20 conventional soaps may also be used. If high sudsing is desired, the branched-chain C10- Ci6 soaps may be used.
  • Suitable surfactants suitable for the purpose of the invention are the anionic alkali metal sarcosinates of formula:
  • R is a C9-C17 linear or branched alkyl or alkenyl group
  • Rl is a C1-C4 alkyl group
  • M is an alkali metal ion.
  • Preferred examples are the lauroyl, cocoyl (C12-C14), myristyl and oleyl methyl sarcosinates in the form of their sodium salts.
  • Binders and thickeners such as sodium carboxymethylcellulose, xantham gum, gum arabic may also be included, as well as synthetic polymers such as polyacrylates, copolymers of polyvinylmethylether with maleic anhydride, copolymers of maleic acid with acrylic acid, terpolymers of maleic/acrylic/vinyl alcohol and hydroxy alkyl cellulose ethers.
  • Flavours such as peppermint and spearmint oils may also be included, as well as preservatives, opacifying agents, colouring agents, pH-adjusting agents and sweetening agents.
  • compositions of the invention can be formulated in any desirable form such as powders, granulates, pastes, liquids, tablets, capsules, pills, solutions, suspensions, salves and gels.
  • compositions of the present invention may be formulated as liquid compositions.
  • Such liquid compositions typically comprise from 94% to 35% by weight, preferably from 90% to 40% by weight, most preferably from 80% to 50% by weight of a liquid carrier, e.g., water, preferably a mixture of water and organic solvent.
  • compositions of the present invention may also be in the form of gels.
  • Such compositions are typically formulated with polyalkenyl polyether having a molecular weight of from about 750,000 to about 4,000,000.
  • compositions of the invention may also be in the form of solids, such as powders, tablets, capsules, pills and granules.
  • a method for reducing the growth of a bacteria strain which comprises the step of exposing said bacteria strain to a bactericidal composition of the invention.
  • a particularly effective action is seen on gram negative bacteria and more specifically Pseudomonas aeruginosa.
  • Cultures of the test bacterium were prepared with Pseudomonas aeruginosa in nutrient broth and subcultured at 30°C daily for between three and five successive days before they were required.
  • the inocula were prepared by diluting each of the overnight broth cultures 1:100 in
  • Solutions or suspensions of the antibacterials were prepared in sterile distilled water or water/ethanol mixtures immediately before use.
  • EDDS is seen to produce an effective bactericidal action against Pseudomonas aeruginosa bacteria.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP96919315A 1995-07-05 1996-06-07 BACTERICIDAL Withdrawn EP0836469A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9513731.1A GB9513731D0 (en) 1995-07-05 1995-07-05 Bactericidal compositions
GB9513731 1995-07-05
PCT/US1996/009860 WO1997002010A1 (en) 1995-07-05 1996-06-07 Bactericidal composition

Publications (2)

Publication Number Publication Date
EP0836469A1 EP0836469A1 (en) 1998-04-22
EP0836469A4 true EP0836469A4 (en) 1999-09-15

Family

ID=10777188

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96919315A Withdrawn EP0836469A4 (en) 1995-07-05 1996-06-07 BACTERICIDAL

Country Status (5)

Country Link
EP (1) EP0836469A4 (en)
AU (1) AU6168496A (en)
CA (1) CA2228945C (en)
GB (1) GB9513731D0 (en)
WO (1) WO1997002010A1 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9615633D0 (en) * 1996-07-25 1996-09-04 Procter & Gamble Shampoo compositions
DE19650102A1 (en) * 1996-12-03 1998-06-04 Basf Ag Use of bis (dicarboxylic acid) diaminoalkylene derivatives as biodegradable complexing agents for alkaline earth and heavy metal ions
GB9721394D0 (en) * 1997-10-09 1997-12-10 Ass Octel Anti-microbial compound
EP0968658A1 (en) * 1998-07-02 2000-01-05 Akzo Nobel N.V. Feed additives comprising ethylene diamine disuccinic acid as a chelant
GB0024689D0 (en) 2000-10-09 2000-11-22 Unilever Plc Deodorant products
FR2818150B1 (en) * 2000-12-15 2004-04-30 Anios Lab Sarl COMPOSITION FOR THE TREATMENT OF OBJECTS FOR DISINFECT
JP4518367B2 (en) * 2002-03-25 2010-08-04 株式会社資生堂 Pore reducing agent
GB0714575D0 (en) 2007-07-26 2007-09-05 Innospec Ltd Composition
GB0714569D0 (en) 2007-07-26 2007-09-05 Innospec Ltd Composition
EP2206506A1 (en) * 2008-12-18 2010-07-14 Bracco Imaging S.p.A Probiotic formulations
US8628812B2 (en) 2008-12-30 2014-01-14 Pepsico, Inc. Preservative system for acidic beverages based on sequestrants
US8257720B2 (en) * 2009-04-20 2012-09-04 Conopco, Inc. Stabilized cationic ammonium compounds and compositions comprising the same
US8324255B2 (en) 2009-09-15 2012-12-04 Conopco, Inc. Chelator stabilized cationic ammonium compounds and compositions comprising the same
DE102017207927A1 (en) * 2017-05-10 2018-11-15 Henkel Ag & Co. Kgaa Process for reducing perspiration and / or body odor using phosphonate compounds having amine and / or hydroxyl groups

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0341662A2 (en) * 1988-05-09 1989-11-15 The B.F. Goodrich Company Tartar inhibiting oral compositions and method
WO1994000103A1 (en) * 1992-06-26 1994-01-06 The Procter & Gamble Company Anticalculus compositions
WO1995007616A1 (en) * 1993-09-14 1995-03-23 Minnesota Mining And Manufacturing Company Disinfectant composition

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8310081D0 (en) * 1983-04-14 1983-05-18 Interox Chemicals Ltd Peroxygen compounds
US5338748A (en) * 1985-01-18 1994-08-16 Cetylite Industries, Inc. Sterilant composition
DE3611522A1 (en) * 1986-04-05 1987-10-08 Henkel Kgaa DIPHOSPHONYLATED OXONITRILE, METHOD FOR THE PRODUCTION AND THEIR USE IN MICROBISTATIC COMPOSITIONS AND MICROBISTATICALLY EFFECTIVE DIPHOSPHONYLATED OXONITRILE CONTAINERS
NZ240775A (en) * 1990-11-30 1994-09-27 Solvay Interox Gmbh Substitute Solid acetyl peroxyborate compound; use for bleaching or disinfecting
US5460802A (en) * 1994-07-18 1995-10-24 Minnesota Mining And Manufacturing Company Oral disinfectant for companion animals

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0341662A2 (en) * 1988-05-09 1989-11-15 The B.F. Goodrich Company Tartar inhibiting oral compositions and method
WO1994000103A1 (en) * 1992-06-26 1994-01-06 The Procter & Gamble Company Anticalculus compositions
WO1995007616A1 (en) * 1993-09-14 1995-03-23 Minnesota Mining And Manufacturing Company Disinfectant composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9702010A1 *

Also Published As

Publication number Publication date
CA2228945A1 (en) 1997-01-23
EP0836469A1 (en) 1998-04-22
GB9513731D0 (en) 1995-09-06
WO1997002010A1 (en) 1997-01-23
AU6168496A (en) 1997-02-05
CA2228945C (en) 2001-05-01

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