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WO2000068369A1 - Technique permettant d'empecher ou de minimiser la biodegradation d'une substance - Google Patents

Technique permettant d'empecher ou de minimiser la biodegradation d'une substance Download PDF

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Publication number
WO2000068369A1
WO2000068369A1 PCT/US2000/008881 US0008881W WO0068369A1 WO 2000068369 A1 WO2000068369 A1 WO 2000068369A1 US 0008881 W US0008881 W US 0008881W WO 0068369 A1 WO0068369 A1 WO 0068369A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
odoriferous
replaced
substance
product obtained
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/US2000/008881
Other languages
English (en)
Inventor
Gilbert Levin
Roy Pinchot
Yongming Lu
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.)
Dominari Holdings Inc
Original Assignee
Biospherics Inc
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
Priority claimed from US09/305,739 external-priority patent/US6585964B1/en
Application filed by Biospherics Inc filed Critical Biospherics Inc
Priority to EP00920094A priority Critical patent/EP1173558A4/fr
Priority to JP2000616336A priority patent/JP2003519246A/ja
Priority to AU40684/00A priority patent/AU4068400A/en
Priority to CA002372612A priority patent/CA2372612A1/fr
Publication of WO2000068369A1 publication Critical patent/WO2000068369A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • 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
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier 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
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70—Biological properties of the composition as a whole

Definitions

  • This invention relates to the extension of the useful lifetimes of biodegradable products by substituting lesser biodegradable ingredients having the same required functional characteristics such as odor.
  • the practice of the invention relates to identifying such lesser biodegradable substances and substituting them, in existing or planned products, for those substances more subject to degradation.
  • One aspect of this invention relates to a method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer (or enantiomer, or optical stereoisomer) . More particularly, this aspect of the invention relates to a process for rendering a fragrant substance, or surface, either bearing microorganisms or subject to deliberate or accidental contamination with microorganisms, odoriferous, e.g., fragrant, for an extended period of time .
  • fragrance industry has grown to its present enormous size.
  • Commercially sold fragrances are based on natural products and synthetic ones . The latter have become of increasing importance as the science of chemistry has become more inventive. Natural fragrances have also been synthesized. However, many of the most pleasant, or otherwise desired odors are highly transient, requiring frequent re-applications, or disappearing after periods shorter than desired for the intended uses.
  • Fragrant or odoriferous preparations generally consist of two functional components : the odor-producing compound or material, and a vehicle which serves as a carrier for the fragrant molecules .
  • Such vehicles have served their purpose when the fragrance has been adequately disseminated.
  • These vehicles are generally short-chain organic compounds which then evaporate quite quickly. This leaves the generally longer-chain fragrant molecules in situ in the desired locations from which they, in turn, volatilize, although somewhat more slowly. The sustained volatilization of these fragrant molecules achieves the desired effect by contacting the olfactories of the target persons or animals in the affected area.
  • a method for preventing or minimizing biodegradation of a substance which normally contains a biodegradable compound comprises replacing the biodegradable compound with a corresponding lesser biodegradable compound providing the same desired functionality .
  • a method for preventing or minimizing biodegradation of a substance which normally contains a naturally occurring optical isomer comprises replacing the naturally occurring optical isomer with the corresponding unnatural optical isomer.
  • substances include fragrances, substances which contain fragrances, and nonfragrant substances which contain optical isomer (s), such as body lotions, soaps, deodorants, and dyes and paints.
  • a process for prolonging emanation of odor(s) from a substance or surface containing one or more odoriferous optically isomeric compounds and which substance or surface also contains or becomes contaminated with microorganisms comprises selecting (an) unnatural optical isomer (s) of the compound (s) to prevent or delay biodegradation of the odoriferous compound (s).
  • a functional substance or compound may retain the desired function for an extended period of time by substituting its non-naturally occurring optical stereoisomer, or an uncommon isomer or lesser biodegradable substance possessing the same functionality.
  • the resulting substance will remain functional for a longer period of time than if the more naturally occurring form or the naturally occurring uncommon form or substance had been applied. This is because the non-naturally occurring form or the naturally occurring uncommon form or substance is non-biodegradable, or is of greatly reduced biodegradability since the microbial enzymes necessary to the biodegradation process can cope only with the more commonly occurring form or substance .
  • Some of the organic molecules synthesized for fragrance purposes, and some of the natural fragrance molecules which can be synthesized have structures which contain carbon atoms bonded to four different atomic groups.
  • the four atomic groups can assume one of two opposite configurations about their central carbon atom. For the purpose of chemical reactions, these configurations behave identically.
  • amino acids and carbohydrates are important examples of chirality, the occurrence of optical stereoisomers of the same molecule, and serve to illustrate the point. Virtually all amino acids in nature are of the optically stereoisomeric form designated "left handed", while natural carbohydrates occur almost exclusively in the optically stereoisomeric form called "right handed".
  • optical isomers displayed by biological entities are because virtually all biological reactions are conducted through the participation of enzymes . From the time life originated, its first enzymes have consistently passed on their optical isomeric specificity to all life forms evolved down through the eons. Enzymes, being templates which position molecules for specific reactions, do distinguish between optical isomers of the same molecule. Not being able to fit physically to the other optical isomer of the reactive molecular species, an enzyme cannot induce the reaction with the unnatural optical isomer.
  • carboxypeptidase which catalyzes the hydrolysis of carbobenzoxyglycyl-L-phenalalanine, has no measurable action on carbobenzoxyglycyl-D-phenalalanine .
  • stereochemical specificity involve an absolute discrimination between enantiomorphs . " (General Biochemistry, Fruton and Simmonds, eds, 3rd printing, p. 277, John Wiley & Sons, Inc., NY, 1960) .
  • a number of fragrant or odoriferous compounds are natural optical isomers . It would be expected that the unnatural enantiomers of these compounds would not trigger the sense of smell, because their molecules would not fit the protein (enzyme) receptor encountered.
  • odoriferous compounds used in the practice of the fragrance-prolonging aspect of this invention may be used in perfumes, eau de colognes, powders, mouth washes, dentifrices, confections, deodorants for personal and area uses, douches, hair applications, simulated odors for various products (such as leather odors for plastic upholstery) , tobacco products, insect and animal repellants and attractants, and the wide variety of other products and uses for fragrances, masking odors, artificial odors, or other scents including those used in foodstuffs, beverages and the like.
  • the naturally-occurring optical isomer of menthol (1R, 2S, 5R) - (-) is used as a fragrance in a variety of products, such as perfumes, gums, and cigarettes.
  • Both the natural and the unnatural (IS, 2R, 5S) - (+) optical isomer of menthol were obtained in 99% purity.
  • a 0.001M solution of each enantiomer was prepared in reagent grade acetone. The solutions were allowed to equilibrate at room temperature for approximately one hour. Twenty drops of each solution were pipetted into separate glass Petri dishes. All glassware was clean. The acetone was then allowed to evaporate at room temperature . Human subjects then smelled the two Petri dishes separately and recorded any sensations.
  • the subjects had been instructed to determine the presence of odor in the Petri dishes, and, if odor emanated from each, to determine whether the odors were the same or different.
  • the test was performed twice on each of six human subjects, three female and three male. Each subject was given freshly prepared Petri dish servings to smell, and each immediately recorded his or her impressions without communicating with the other subjects.
  • Objectionable odors may be absorbed by a variety of chemicals . Such chemicals may be added to an odoriferous material, or sprayed onto surfaces.
  • This example relates to the use of zinc glutamate as an odor absorber.
  • Zinc glutamate is normally used in the form of zinc salt of L- glutamic acid for this purpose.
  • this form of the compound is readily biodegraded by microorganisms that are generally abundant in the treatment area.
  • the zinc salt of D- glutamic acid is substituted for the normal form, with the result that the odor-absorbing material, and, hence, odor removal function, lasts considerably longer than when the natural form of zinc glutamate is used.
  • D-gluconic acid and D-lactic acid are natural products, which are readily biodegradable.
  • the use of their unnatural optical isomers, the zinc salt of L-gluconic acid and the sodium aluminum salt of L-lactic acid, instead of the natural products will result in the odor absorbing material lasting considerably longer.
  • D-glucitol i.e., sorbitol
  • D-mannitol the naturally occurring sugar alcohol
  • humectants water-attracting/binding
  • emollient ingredients in many cosmetic products, for example, in body lotions and sunblock.
  • a moisturizing lotion in which D-glucitol is provided as a humectant and emollient, is applied to the skin daily or twice daily, especially by persons with dry skin. The lotion is spread over the skin, where it comes into contact with the coating of microorganisms normally covering the skin.
  • L-mannitol is used instead of D-mannitol based on the same concept, and producing the same result .
  • Deodorants operate by absorbing odors, reducing perspiration at the skin surface or masking malodors with other odors.
  • Popular underarm deodorants consist of hard gels in the forms of sticks or bars which are applied under the arm where they leave a film of their material .
  • a paramount feature of such deodorants is the length of time the application retains its effectiveness.
  • the underarm harbors many microorganisms which biodegrade the organic ingredients of the deodorant, thereby significantly reducing the lifetime of the product .
  • a widely used stick applicator deodorant/antiperspirant contains cobalt acetylmethionate as its principal active ingredient.
  • Methionine is optically active. This example of the invention substitutes the unnatural optical isomer of methionine (D-methionine) for the natural isomer (L-methionine) , thereby extending the lifetime of this key ingredient, and hence the effectiveness of the product.
  • Menthyl anthranilate is frequently used as the active ingredient in sunblock lotions applied to the body to prevent excessive sunburn by absorbing the ultraviolet rays of the sun.
  • This compound is prepared from menthol by its esterification with anthranilic acid.
  • the enantomeric form of the menthol used is carried into the product.
  • the naturally occurring enantiomer of menthol (1-menthol) is used, or, in the case of synthetic menthol, the racemic mixture (1- and d-menthol in equal quantities) produced by the synthesis is used.
  • L-menthyl anthranilate, made from 1-menthol, is biodegradable.
  • d-menthol unnatural enantiomer of menthol
  • the d-menthyl anthranilate provides the sunblock lotion with a longer useful lifetime than does the normally used 1- or dl-menthyl anthranilate.
  • This example illustrates the broad application of this invention beyond the concept of using a lesser biodegradable isomer of a compound.
  • a completely different compound but with the same functionality and with lesser biodegradability, is substituted for the normally used compound.
  • a widely used stick deodorant has aluminum zirconium tetrachlorohydrex glycine as its active ingredient.
  • This compound is biodegradable.
  • glycine is not optically active, there is no enantiomeric, lesser biodegradable form of that amino acid to substitute for it.
  • the function of the glycine is to neutralize the active ingredient in order to prevent or reduce its irritability to the skin of the user.
  • alanine Another amino acid, in this case alanine, will serve the same function if used in place of glycine.
  • Alanine does have optical isomers L-alanine and D-alanine.
  • the lesser biodegradable enantiomer of alanine (D-alanine) is used to make aluminum zirconium tetrachlorohydrex alanine.
  • This compound provides the deodorant product with the same functionality as did the aluminum zirconium tetrachlorohydrex glycine, but being less biodegradable, provides longer useful life for the product.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Confectionery (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

Cette invention concerne une technique permettant d'empêcher ou de minimiser la biodégradation d'une substance qui contient normalement un composé biodégradable. Cette technique consiste à remplacer ce composé par un composé correspondant moins biodégradable qui possède la même fonctionnalité recherchée.
PCT/US2000/008881 1999-05-06 2000-04-04 Technique permettant d'empecher ou de minimiser la biodegradation d'une substance Ceased WO2000068369A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP00920094A EP1173558A4 (fr) 1999-05-06 2000-04-04 Technique permettant d'empecher ou de minimiser la biodegradation d'une substance
JP2000616336A JP2003519246A (ja) 1999-05-06 2000-04-04 物質の生分解の防止または最小化方法
AU40684/00A AU4068400A (en) 1999-05-06 2000-04-04 Method for preventing or minimizing biodegradation of a substance
CA002372612A CA2372612A1 (fr) 1999-05-06 2000-04-04 Technique permettant d'empecher ou de minimiser la biodegradation d'une substance

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US09/305,739 1999-05-06
US09/305,739 US6585964B1 (en) 1999-05-06 1999-05-06 Method for preventing or minimizing biodegradation of a substance
US44144099A 1999-11-17 1999-11-17
US09/441,440 1999-11-17

Publications (1)

Publication Number Publication Date
WO2000068369A1 true WO2000068369A1 (fr) 2000-11-16

Family

ID=26974757

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/008881 Ceased WO2000068369A1 (fr) 1999-05-06 2000-04-04 Technique permettant d'empecher ou de minimiser la biodegradation d'une substance

Country Status (5)

Country Link
EP (1) EP1173558A4 (fr)
JP (1) JP2003519246A (fr)
AU (1) AU4068400A (fr)
CA (1) CA2372612A1 (fr)
WO (1) WO2000068369A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1541122A1 (fr) * 2003-12-12 2005-06-15 L'oreal Composition cosmétique déodorante comprenant l'association du pidolate de zinc et d'un sel d'aluminium anti-transpirant
EP1541123A1 (fr) * 2003-12-12 2005-06-15 L'oreal Composition cosmétique déodorante comprenant l'association du gluconate de zinc et d'un sel d'aluminium anti-transpirant
US7326409B2 (en) 2003-12-12 2008-02-05 L'oreal S.A. Deodorant cosmetic composition comprising a combination of zinc pidolate and an antiperspirant aluminum salt
US7332154B2 (en) 2003-12-12 2008-02-19 L'oreal S.A. Deodorant cosmetic composition comprising a combination of zinc gluconate and an antiperspirant aluminum salt

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011256137A (ja) * 2010-06-09 2011-12-22 Shiseido Co Ltd アミノ酸含有組成物における防腐力低下抑制剤
JP6639767B2 (ja) * 2013-10-07 2020-02-05 小林製薬株式会社 消臭装置及び消臭方法
JP7011894B2 (ja) * 2017-02-10 2022-02-10 アサヒビール株式会社 アルコール飲料及びその製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0884045A1 (fr) * 1997-06-06 1998-12-16 Pfizer Products Inc. Formulations autobronzantes de dihydroxyacetone à stabilité améliorée et conférant une administration accrue

Family Cites Families (6)

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JPS57158724A (en) * 1981-03-26 1982-09-30 Shiseido Co Ltd Antimicrobial composition
JPH0728213A (ja) * 1993-05-14 1995-01-31 Konica Corp ハロゲン化銀カラー写真感光材料用固体処理剤
JPH092999A (ja) * 1995-06-16 1997-01-07 Taki Chem Co Ltd 乳酸アルミニウム結晶の製造方法
JP3528072B2 (ja) * 1995-10-13 2004-05-17 高砂香料工業株式会社 （４ｒ）−シス−４−メチル−２−置換テトラヒドロ−２ｈ−ピラン誘導体を含有する香料組成物及び（４ｒ）−シス−４−メチル−２−置換テトラヒドロ−２ｈ−ピラン誘導体を用いる香気改善方法
US5902572A (en) * 1997-06-23 1999-05-11 Procter & Gamble Company Anhydrous gel deodorant compositions
GB9715751D0 (en) * 1997-07-26 1997-10-01 Ciba Geigy Ag Formulations

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0884045A1 (fr) * 1997-06-06 1998-12-16 Pfizer Products Inc. Formulations autobronzantes de dihydroxyacetone à stabilité améliorée et conférant une administration accrue

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1541122A1 (fr) * 2003-12-12 2005-06-15 L'oreal Composition cosmétique déodorante comprenant l'association du pidolate de zinc et d'un sel d'aluminium anti-transpirant
EP1541123A1 (fr) * 2003-12-12 2005-06-15 L'oreal Composition cosmétique déodorante comprenant l'association du gluconate de zinc et d'un sel d'aluminium anti-transpirant
FR2863489A1 (fr) * 2003-12-12 2005-06-17 Oreal Composition cosmetique deodorante comprenant l'association du pidolate de zinc et d'un sel d'aluminium anti-tranpirante
FR2863488A1 (fr) * 2003-12-12 2005-06-17 Oreal Composition cosmetique deodorante comprenant l'association du gluconate de zinc et d'un seul sel d'aluminium anti-transpirant
US7326409B2 (en) 2003-12-12 2008-02-05 L'oreal S.A. Deodorant cosmetic composition comprising a combination of zinc pidolate and an antiperspirant aluminum salt
US7332154B2 (en) 2003-12-12 2008-02-19 L'oreal S.A. Deodorant cosmetic composition comprising a combination of zinc gluconate and an antiperspirant aluminum salt

Also Published As

Publication number Publication date
JP2003519246A (ja) 2003-06-17
EP1173558A4 (fr) 2002-07-24
CA2372612A1 (fr) 2000-11-16
AU4068400A (en) 2000-11-21
EP1173558A1 (fr) 2002-01-23

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