WO1996003971A1 - Preparations efficaces contre l'odeur des pieds, a teneur en esters oligoglyceriniques d'acides gras - Google Patents

Preparations efficaces contre l'odeur des pieds, a teneur en esters oligoglyceriniques d'acides gras Download PDF

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Publication number
WO1996003971A1
WO1996003971A1 PCT/EP1995/002766 EP9502766W WO9603971A1 WO 1996003971 A1 WO1996003971 A1 WO 1996003971A1 EP 9502766 W EP9502766 W EP 9502766W WO 9603971 A1 WO9603971 A1 WO 9603971A1
Authority
WO
WIPO (PCT)
Prior art keywords
monocarboxylic acid
acid esters
triglycerol
esters
diglycerol
Prior art date
Application number
PCT/EP1995/002766
Other languages
German (de)
English (en)
Inventor
Manfred Klier
Bernd Traupe
Florian Wolf
Original Assignee
Beiersdorf Ag
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 Beiersdorf Ag filed Critical Beiersdorf Ag
Priority to JP8506124A priority Critical patent/JPH10503498A/ja
Priority to EP95926882A priority patent/EP0772433A1/fr
Publication of WO1996003971A1 publication Critical patent/WO1996003971A1/fr

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Classifications

    • 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
    • A61Q17/005—Antimicrobial 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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

Definitions

  • Anti-odor preparations containing oligoglycerol esters of fatty acids containing oligoglycerol esters of fatty acids
  • the present invention relates to active substances and preparations containing active substances which are effective against foot odor.
  • mycobacteria, streptococci, staphylococci and propionibacteria are mainly found on healthy human skin.
  • Coryneform bacteria also occurring on the skin have recently been made responsible for the development of unpleasant body odor through the decomposition of apocrine sweat.
  • the typical cheese-like smell of sweaty feet is caused by Brevibacterium spec.
  • Brevibacteria are also coryneform bacteria. They are facultative anaerobic, gram-positive, cylindrical bacteria. The fact that Brevibacterium spec. The "cheesy" smell caused is no coincidence, as some cheeses, especially when ripening Soft cheese, Brevibacteria play a role (e.g. Brevibacterium linens).
  • Foot odor is usually combated with conventional deodorants or antiperspirants, analogous to the armpit smell, or simply with water and soap.
  • astringents primarily aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate).
  • aluminum salts such as aluminum hydroxychloride (aluminum chlorohydrate).
  • the substances used for this depending on their dosage, have a drastic effect on the heat balance of the foot region and should only be used in exceptional cases.
  • the bacterial flora on the skin can be reduced.
  • only the odor-causing microorganisms should be effectively reduced. In practice, however, it has been found that the entire microflora of the skin can be impaired.
  • the sweat flow itself is not affected by this, in the ideal case only the microbial decomposition of the sweat is temporarily stopped.
  • foot odor can also be covered by fragrances, a method that least meets the aesthetic needs of the consumer, since the mixture of foot odor and perfume smells rather unpleasant.
  • most cosmetics are perfumed, even if they contain antimicrobial1 substances. Perfuming can also serve to increase the consumer acceptance of a cosmetic product or to give a product a certain flair.
  • oligoglycerides of branched and / or unbranched saturated and / or unsaturated monocarboxylic acids with 8 - 14 carbon atoms for the prophylaxis or control of the foot odor caused by the decomposition of human foot sweat by Brevibacteria.
  • the 01 iogoglycerides according to the invention penetrate into the skin of the foot and selectively combat the Brevibacteria responsible for the foot odor.
  • fatty acid esters of glycerol have certain antimicrobial effects.
  • glycerol fatty acid esters in deodorising cosmetics.
  • the only fatty acid ester that was really considered to be practical is the glycerol onolaurate.
  • JP-OS Sho-48/019940 describes Taiyo Kagaku Kogyo Co. Ltd. a cosmetic with antiseptic properties is known which is characterized by a content of caprylic acid monoglyceride.
  • EP-OS 530 861 describes topical antimicrobial pharmaceutical combinations comprising, in addition to glycerol monocaprylate and glycerol monocaprinate, a mixture of saturated fatty acids.
  • the 01 igoglycerides are preferably selected from the group of the di- and triglycerides, the di- and triglycerol units of the monocarboxylic acid esters according to the invention being linear, unbranched molecules, ie via the respective OH groups in 1- or 3- Etherified "monoglycerol molecules" are present.
  • a small proportion of cyclic di- or triglycerol units and glycerol molecules etherified via the OH groups in the 2-position can be tolerated. However, it is advantageous to keep such impurities as low as possible.
  • the monocarboxylic acid esters of diglycerol according to the invention are preferably monocarboxylic acid onoesters and are preferred characterized by the following structure (substitution positions indicated):
  • R ' is a hydrocarbon radical, advantageously a branched or unbranched alkyl or alkenyl radical of 7 to 13 carbon atoms.
  • the monocarboxylic acid esters of triglycerol according to the invention are preferably monocarboxylic acid onoesters and are preferably characterized by the following structure (substitution positions indicated):
  • R " is a hydrocarbon radical, advantageously a branched or unbranched alkyl or alkenyl radical, alkyl radical of 7 to 13 carbon atoms.
  • esters of diglycerol are preferred to those of triglycerol.
  • TML Triglycerol onolaurate
  • TMS Triglycerol Monomyristate
  • Diglycerol monocaprinate has proven to be the preferred monocarboxylic acid ester according to the invention.
  • the monofatty acid esters of diglycerol according to the invention are preferably in the 1-position, the monofatty acid esters of triglycerol according to the invention are preferably esterified in the 2'-position.
  • the 2-position is a center of asymmetry.
  • the 2S and 2R configurations are active and equally advantageous according to the invention.
  • an additional portion of di- or triglycerol esterified in other places is used, as is a portion of the various diesters of di- or triglycerol.
  • Those monocarboxylic acid esters which can be obtained by a process as described in DE-OS 38 18 293 are particularly advantageous.
  • the diglycerol esters which are distinguished by two, and the triglycerol esters, which are distinguished by three centers of asymmetry, are effective according to the invention in all their configurations.
  • the diglycerol esters have four, the triglycerol esters eight stereoisomers.
  • the 2-, the 2 'and the 2 "-positions are asymmetry centers.
  • mixtures of one or more monocarboxylic acid esters of diglycerol with one or more monocarboxylic acid esters of triglycerol are used.
  • one or more monocarboxylic acid esters of diglycerol and / or one or more monocarboxylic acid esters of triglycerol are used in combination with other active ingredients (substitute active ingredients), auxiliaries, blends and / or Additives used.
  • the blends and / or replacement active ingredients are then advantageously present in a concentration of up to 50 parts by weight, preferably up to 35 parts by weight, based on the 100 parts by weight of the total amount resulting from the monocarboxylic acid ester or the monocarboxylic acid esters of diglycerol and / or triglycerol and these substitute active ingredients and / or blends.
  • one or more monocarboxylic acid esters of diglycerol and / or one or more monocarboxylic acid esters of triglycerol are used in combination with other substances which inhibit the growth of Brevibacteria or kill Brevibacteria.
  • one or more monocarboxylic acid esters of diglycerol and / or one or more monocarboxylic acid esters of triglycerol are used in combination with monocarboxylic acid esters of glycerol (ie the "monoglycerol").
  • monocarboxylic acid esters of glycerol take on the role of blending agents and / or substitute active ingredients and are preferably used in a concentration of up to 50 parts by weight, preferably up to 35 parts by weight, based on 100 parts by weight of the total amount. which is composed of the monocarboxylic acid ester or the monocarboxylic acid esters of diglycerol and / or triglycerol and these monocarboxylic acid esters of glycerol.
  • the cosmetic preparations according to the invention against foot odor are particularly advantageously characterized in that the mono- or oligoglycerol esters according to the invention are present in concentrations of 0.05-10.00% by weight, preferably 0.1-5.0 % By weight are present, in each case based on the total weight of the preparations.
  • the preparations according to the invention which are effective against impure skin can be in the form of liquid compositions which can be applied by means of brushes or scrapers or roll-on devices, as pens and in the form of W / O or O / W water which can be applied from normal bottles and containers.
  • Emulsions e.g. Creams or lotions.
  • skin-caring fat or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetyl stearyl alcohol and 2-0ctyldodecanol can be used as customary carriers for the preparation of the preparations according to the invention against impure skin in addition to water, ethanol and isopropanol, glycerol and propylene glycol usual proportions are used as well as slime-forming substances and thickeners, for example Hydroxyethyl or hydroxypropyl cellulose, polyacrylic acid, polyvinylpyrrole idone, but also in small quantities also cyclic silicone oils (polydimethylsiloxanes) and liquid polymethylphenylsiloxanes of low viscosity.
  • emulsifiers for the preparation of the preparations according to the invention effective against foot odor which should advantageously be applied to the feet as liquid preparations, advantageously by means of a cotton ball, and which are present in the preparations in small amounts, for example 2 to 5 weights. %, based on the total composition, can be used as non-ionic types, such as polyoxyethylene fatty alcohol ethers, for example cetylstearyl alcohol polyethyleneglycol ether with 12 or 20 added ethylene oxide units per molecule, cetylstearyl alcohol and sorbitan esters and sorbitan esters.
  • Etiylene oxide compounds e.g. sorbitan monostearate and polyoxyethylene sorbitan onostearate
  • long-chain, high molecular weight waxy polyglycol ethers have been found to be suitable.
  • BHT butylated hydroxytoluene
  • the pH of the preparations according to the invention is advantageously adjusted in the weakly acidic to neutral range, preferably from 4.0 to 7.0, particularly preferably from 5.0 to 6.5.
  • the amounts of carrier substances to be used can easily be determined by a person skilled in the art by simply trying them out.
  • the preparations according to the invention are prepared in the customary manner, apart from special preparations which are noted separately in the examples, mostly by simply mixing with stirring, if appropriate with gentle heating. It offers no difficulties.
  • fat phase and water phase e.g. prepared separately, optionally with heating and then emulsified.
  • the finished pump spray can then be filled into pump atomizers.
  • 1,3-butylene glycol 2.00 hydroxyethyl cellulose 0.50 e.g. Tylose 4000, Hoechst
  • the ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.
  • the constituents mentioned under (a) are processed to a homogeneous solution, then slowly filled up with the water phase (b).
  • the finished pump spray can then be filled into pump atomizers.
  • 1,3-butylene glycol 2.00 hydroxyethyl cellulose 0.50 e.g. Tylose 4000, Hoechst
  • the ingredients are melted at approx. 75 ° C, mixed well and poured into suitable molds.

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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)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation d'oligoglycérides d'acides monocarboxyliques de 8 à 14 atomes de carbone saturés et/ou insaturés, ramifiés et/ou non ramifiés, en prophylaxie ou pour lutter contre l'odeur des pieds occasionnée par la décomposition, par des bactéries Brevi, de la sueur humaine du pied.
PCT/EP1995/002766 1994-07-30 1995-07-14 Preparations efficaces contre l'odeur des pieds, a teneur en esters oligoglyceriniques d'acides gras WO1996003971A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP8506124A JPH10503498A (ja) 1994-07-30 1995-07-14 脂肪酸のオリゴ−グリセロールエステルを含有する、足の悪臭に対して活性な調製物
EP95926882A EP0772433A1 (fr) 1994-07-30 1995-07-14 Preparations efficaces contre l'odeur des pieds, a teneur en esters oligoglyceriniques d'acides gras

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944427075 DE4427075A1 (de) 1994-07-30 1994-07-30 Gegen Fußgeruch wirksame Zubereitungen mit einem Gehalt an Oligoglycerinestern von Fettsäuren
DEP4427075.5 1994-07-30

Publications (1)

Publication Number Publication Date
WO1996003971A1 true WO1996003971A1 (fr) 1996-02-15

Family

ID=6524560

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002766 WO1996003971A1 (fr) 1994-07-30 1995-07-14 Preparations efficaces contre l'odeur des pieds, a teneur en esters oligoglyceriniques d'acides gras

Country Status (4)

Country Link
EP (1) EP0772433A1 (fr)
JP (1) JPH10503498A (fr)
DE (1) DE4427075A1 (fr)
WO (1) WO1996003971A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007039086A1 (fr) * 2005-09-19 2007-04-12 Basf Aktiengesellschaft Micro-organismes inhibiteurs de la formation de la mauvaise odeur des pieds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9814656D0 (en) * 1998-07-07 1998-09-02 Quest Int Method of reducing or preventing malodour

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0433132A1 (fr) * 1989-12-13 1991-06-19 L'oreal Composition cosmétique pour application topique contenant des huiles essentielles
DE4237081A1 (de) * 1992-11-03 1994-05-05 Beiersdorf Ag Desodorierende kosmetische Zubereitungen mit einem Gehalt an Di- oder Triglycerinestern
DE4309372A1 (de) * 1993-03-23 1994-09-29 Beiersdorf Ag Desodorierende Wirkstoffkombinationen auf der Basis von Wollwachssäuren und Partialglyceriden

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0433132A1 (fr) * 1989-12-13 1991-06-19 L'oreal Composition cosmétique pour application topique contenant des huiles essentielles
DE4237081A1 (de) * 1992-11-03 1994-05-05 Beiersdorf Ag Desodorierende kosmetische Zubereitungen mit einem Gehalt an Di- oder Triglycerinestern
WO1994009753A1 (fr) * 1992-11-03 1994-05-11 Beiersdorf Ag Preparations cosmetiques deodorantes contenant des esters di- ou triglyceriques
DE4309372A1 (de) * 1993-03-23 1994-09-29 Beiersdorf Ag Desodorierende Wirkstoffkombinationen auf der Basis von Wollwachssäuren und Partialglyceriden

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007039086A1 (fr) * 2005-09-19 2007-04-12 Basf Aktiengesellschaft Micro-organismes inhibiteurs de la formation de la mauvaise odeur des pieds
JP2009508478A (ja) * 2005-09-19 2009-03-05 ビーエーエスエフ ソシエタス・ヨーロピア 足臭の形成を阻害する微生物

Also Published As

Publication number Publication date
DE4427075A1 (de) 1996-02-01
JPH10503498A (ja) 1998-03-31
EP0772433A1 (fr) 1997-05-14

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