EP1003469A2 - Precurseurs de parfums - Google Patents

Precurseurs de parfums

Info

Publication number
EP1003469A2
EP1003469A2 EP97903286A EP97903286A EP1003469A2 EP 1003469 A2 EP1003469 A2 EP 1003469A2 EP 97903286 A EP97903286 A EP 97903286A EP 97903286 A EP97903286 A EP 97903286A EP 1003469 A2 EP1003469 A2 EP 1003469A2
Authority
EP
European Patent Office
Prior art keywords
acid
formula
compound
hydroxy
coor
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Withdrawn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
EP97903286A
Other languages
German (de)
English (en)
Inventor
Denise Anderson
Georg Frater
Peter Gygax
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.)
Givaudan SA
Original Assignee
Givaudan Roure International SA
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 Givaudan Roure International SA filed Critical Givaudan Roure International SA
Publication of EP1003469A2 publication Critical patent/EP1003469A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
    • 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
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation

Definitions

  • the invention relates to fragrance precursors.
  • the invention relates to the use of several classes of compounds which can act as fragrance precursors, e.g. in consumer, e.g. cosmetic products, such as deodorants and antiperspirants. These compounds are normally odourless or nearly so, but upon contacting the skin as for example, in skin care compositions or in personal care compositions, produce fragrances.
  • a principal strategy currently employed in imparting odours to consumer products is the admixing of the fragrance directly into the product. There are however, several drawbacks to this strategy.
  • the fragrance material can be too volatile, resulting in fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in loss during storage.
  • fragrances are microencapsulated or treated with cyclodextrins to form inclusion complexes to help decrease volatility and improve stability.
  • cyclodextrins can be too expensive.
  • the present invention now provides compounds (and their use), which show a low level of odour, or are even odourless, prior to application to the skin, but which release odorant molecules after application to the skin (that is, they provide a delayed release of the fragrance), in particular to the skin in the axilla.
  • the compounds under consideration are compounds of the formula
  • Rl is a radical derived from an odoriferous alcohol of the formula Rl OH, wherein
  • R 2 is one or more building blocks selected from an optionally substituted C ⁇ _30-alkyl or C2-30- alkenyl radical, a carbocyclic, aromatic or heterocyclic radical, whereby all these radicals may in addition contain one or more hetero atoms, such as O, N, S, P, and groups such as (OCH2CH2) n
  • R 3 is independently H, R 1 , R 2 , X ,
  • R 4 is R 1 or R 2 ,
  • X is H, an alkali metal ion, one equivalent of an earth alkali metal or of the Al, Zn or Fe ion, or an optionally mono-, di- or trisubstituted ammonium ion,
  • n 1 -20.
  • alcohols R ⁇ OH are primary or secondary alcohols- or phenols - such as:
  • Flavors & Fragrances * citronellol* geraniol* oct- l -en-3-ol
  • BASF * l-(2-tert-butyl-cyclohexyloxy)-2-butanol (Amber Core, Kao)* l-(4-isopropyl-cyclohexyl)-ethanol (Mugetanol, H&R)* etc.
  • 3-hydroxy-3-ethyl-dodecanoic acid myristic acid stearic acid hydroxystearic acid isostearic acid palmitic acid arachidic acid behenic acid stearoyi lactylic acid sorbic acid undecylenic acid linoleic acid linolenic acid oleic acid ricinoleic acid arachidonic acid succinic acid adipic acid sebacic acid citric acid
  • (polyoxyethylene) acids such as: deceth-7 carboxylic acid laureth-5 carboxylic acid laureth- 10 carboxylic acid isosteareth-6 carboxylic acid isosteareth- l 1 carboxylic acid trideceth-4 carboxylic acid trideceth-7 carboxylic acid trideceth- 15 carboxylic acid trideceth- 19 carboxylic acid; glycolic acid lactic acid malic acid maleic acid tartaric acid benzoic acid o-cresotic acid diphenolic acid salicyclic acid, acrylinoleic acid abietic acid dihydroabietic acid tetrahydroabietic acid glycyrrhetinic acid deoxycholic acid cyclohexanediamine tetra acetic acid biotin
  • 4-(acetylamino)-butanoic acids and ⁇ -amino acids such as: glycine alanine arginine asparagine aspartic acid glutamic acid histidine isoleucine leucine lysine proline serine threonine tyrosine phenylalanine tryptophan valine; gluconic acid glycyrrhizic acid, thiodiglycolic acid thiodipropionic acid thiosalicyclic acid phenyl thioglycolic acid dithiodiglycolic acid etc.
  • glycine alanine arginine asparagine aspartic acid glutamic acid histidine isoleucine leucine lysine proline serine threonine tyrosine phenylalanine tryptophan valine gluconic acid glycyrrhizic acid, thiodiglycolic acid thiodiprop
  • R 2 extends from C l to C30 alkyl and alkenyl, and one or more unsaturations may be present, and the respective chains may be linear or branched.
  • the carbocycles encompass in particular, optionally substituted
  • cycloalkanes cycloalkenes polycycloalkanes polycycloalkenes
  • aromatic rings encompass in particular, optionally substituted
  • heterocycles encompass in particular, optionally substituted pyridine pyrrole pyrrolidine pyrimidine furane thiophene tetrah ydrofuran quinoline furanose pyranose.
  • the radicals R 3 may be the same or different.
  • the compounds I may preferably be used as sustained release odorants but also to mask or attenuate undesirable odours or to provide additional odours not initially present in consumer products, i.e. cosmetic products destined for application to human skin such as underarm deodorants or antiperspirants or other deodorants contacting the body, or in hand lotions, baby powders, baby lotions, ointments, foot products, facial cleansers, body wipes, facial make-up, colognes, after-shave lotions, shaving creams, etc.
  • the compounds I are virtually odourless under normal temperature and atmospheric conditions, i.e. about 10-50 degrees Celsius and about 20 to 100% relative humidity. However, when applied to the body, they undergo a transformation in which the fragrant alcohol is released.
  • the compounds I are not limited to any particular stereo- isomers, all possible stereoisomers, geometric isomers as well as well as racemates are thus included within the scope of formula I.
  • the compounds I upon cleavage, provide alcohols having organoleptic properties and therefore permit the development of methods useful in enhancing the odour of consumer products. These compounds may be used individually in an amount effective to enhance the characteristic odour of a material. More commonly, however, the compounds are mixed with other fragrance components in an amount sufficient to provide the desired odour characteristics.
  • the amount required to produce the desired, overall effect varies depending upon the particular compounds I chosen, the product in which it will be used, and the particular effect desired.
  • an odorant i.e. an odoriferous alcohol in an "organoleptically effective amount" is released when the deodorant is used.
  • This newly formed odorant serves to enhance the odour of the fragrance and in this way mask, e.g. the underarm odour, depending upon the selection and use levels of the compounds I.
  • the compounds I can accordingly be used in the manufacture of odorant compositions used in the preparation of cosmetic products, e.g. deodorants and antiperspirants, and as is evident from the above compilation, a broad range of known odorants or odorant mixtures can be used.
  • the known odorants or odorant mixtures set forth above can be used according to methods known to the perfumer, such as e.g. from W.A. Poucher, Perfumes, Cosmetics, Soaps, 2, 7th Edition, Chapman and Hall, London 1974.
  • the present invention relates to:
  • a fragrance precursor composition preferably a composition for application to human skin, containing an organoleptically effective amount of at least one compound of the formula I in a acceptable, preferably a cosmetically acceptable carrier.
  • a fragrance precursor containing product e.g. cosmetic product, e.g. a personal body deodorant or antiperspirant article, containing at least one compound I.
  • a method of suppressing human body malodour by means of compounds of the formula I which comprises the application, e.g. to human skin of a cosmetic product as defined above.
  • these compounds I may be obtained by reaction of the alcohol part, if necessary derivated, with the acid part, if necessary activated, of the molecule I.
  • This compound was prepared as above, but starting from 10- undecenyl bromo acetate.
  • citronellol was reacted with 3,6,9-trioxaundecanedioic acid (Hoechst) as above.
  • NMR (CDCI3) 5.03-5.13 (m, 2H), 4.12-4.26 (m, 8H), 3.14-3.29 (m, 8H), 1.90-2.09 (m, 4H), 1.68 (s,3H), 1.62 (s,3H), 1.10-1.60 (m,
  • Acetyl chloride ( 15.7 g) was added quickly under nitrogen to a solution of 20.8 g of 3-methyl-5-(2,2,3-trimethylcyclopent-3- enyl)pent-4-en-2-ol in 500 ml of cyclohexane. 20.2 g of triethylamine was added dropwise in -30 minutes with cooling, the temperature being maintained at 20° C. After an additional 2 hours stirring at room temperature, the reaction mixture was filtered and the white solid washed with 200 ml of MTBE. The filtrate was washed with 10% sodium bicarbonate solution, 0.1N hydrochloric acid and brine, dried and evaporated to dryness to give 35 g of yellow oil. Purification by distillation yielded 18 g of colourless liquid; bp: 84° C / 0.06 Torr.
  • the monosodium salt of this acid was prepared by running a THF-solution of the acid through a column charged with Amberlite IRC 86 in its sodium-form. Evaporation of the solvent gave the salt in quantitative yield.
  • the compound was prepared starting from cis-3-hexenol.
  • Examples 15 to 20 illustrate the preparation of compounds lb .
  • the mixture is heated to 50°C to maintain this temperature (the addition of the first half of the thionyl chloride is exothermic, the second half endothermic). After all the thionyl chloride has been added, the temperature is raised gradually to 80°C under reduced pressure (200 mbar) over a period of 2 hours to complete the reaction and remove the remainder of hydrogen chloride.
  • the crude product yielded 151.0 g.
  • This compound was prepared as above, but starting from triethyl methanetricarboxylate and geraniol.
  • novel compounds are compounds of the subgroup R 1 OOC-CH(COOR 1 )-COOR 1 of la.
  • R 1 is as defined above.
  • this compound was prepared from citronellol and fumaric acid.
  • Axilla bacteria cultures containing 0.1 % precursor I were incubated for 20 hours at 30°. After filtration from the cells, the presence of the parent alcohol was in each case detected by headspace-GC techniques and/or 6 panelists.
  • Triclosan (Ciba-Geigy) 1 .0 - 0.75 1 .0 Ethanol 1 00 1 00 1 00 1 00 1 00
  • Neobee 1053 (PVO International) 12.0
  • Triton X-102 (Union Carbide) 2.0

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des précurseurs de parfums. En particulier, l'invention concerne l'utilisation de plusieurs classes de composés qui peuvent servir de précurseurs de parfums, par exemple, dans des produits de consommation tels que des produits cosmétiques, et plus précisément, des déodorants et des antitranspirants. Ces composés sont normalement sans, ou pratiquement, sans odeur, mais lors de leur contact avec la peau, comme par exemple dans les compositions de soins de beauté ou de soins personnels, ils dégagent un parfum en libérant un alcool odoriférant.
EP97903286A 1996-02-21 1997-02-14 Precurseurs de parfums Withdrawn EP1003469A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP96102568 1996-02-21
PCT/EP1997/000705 WO1997030687A2 (fr) 1996-02-21 1997-02-14 Precurseurs de parfums
EP96102568 1997-02-14

Publications (1)

Publication Number Publication Date
EP1003469A2 true EP1003469A2 (fr) 2000-05-31

Family

ID=8222492

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97903286A Withdrawn EP1003469A2 (fr) 1996-02-21 1997-02-14 Precurseurs de parfums

Country Status (3)

Country Link
EP (1) EP1003469A2 (fr)
JP (1) JP2000512663A (fr)
WO (1) WO1997030687A2 (fr)

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US5932198A (en) * 1997-12-15 1999-08-03 The Gillette Company α-amides of L-amino acids as fragrance precursors
EP0936211B1 (fr) 1998-02-13 2010-07-07 Givaudan SA Esters de l'acide arylacrylique, utilisés en tant que précurseurs de composés organoleptiques
SG93823A1 (en) 1998-02-13 2003-01-21 Givaudan Roure Int Aryl-acrylic acid esters
US6036964A (en) * 1998-03-05 2000-03-14 Colgate-Palmolive Company Personal hygiene product with enhanced fragrance delivery
EP0952142B1 (fr) * 1998-04-20 2006-10-18 Givaudan SA Composés ayant des groupes hydroxyles protégés
US6479682B1 (en) 1998-04-20 2002-11-12 Givaudan Sa Compounds having protected hydroxy groups
EP0953562A1 (fr) * 1998-04-28 1999-11-03 Givaudan Roure (International) S.A. Delta-céto-esters béta, gamma-insaturés
SG87805A1 (en) * 1998-04-28 2002-04-16 Givaudan Roure Int Beta, gamma-unsaturated delta-keto esters
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DE10013762A1 (de) * 2000-03-20 2001-10-11 Henkel Kgaa Alkoxylierte Duftalkohole, insbesondere Terpenalkohole, und ihre Verwendung in Wasch-, Spül- oder Reinigungsmitteln oder kosmetischen Zubereitungen
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DE102007037147A1 (de) 2007-08-07 2009-02-12 Henkel Ag & Co. Kgaa Duftkomposite mit verbesserter Duftfreisetzung
DE102009032244A1 (de) * 2009-07-06 2011-01-13 Beiersdorf Ag Glycyrrhetinsäure enthaltende, parfümierte kosmetische Zubereitung
FR2961208B1 (fr) * 2010-06-09 2012-11-23 Oreal Poly 2-pyrrolidones fonctionnalisees par un radical ester, acide ou amide, composition cosmetique les comprenant et leur utilisation comme agent dispersant
WO2013121407A1 (fr) * 2012-02-17 2013-08-22 Budhi Haryanto Composition d'aérosol d'élimination des mauvaises odeurs pour objets ou articles portés quotidiennement
US20160168508A1 (en) * 2013-07-29 2016-06-16 Takasago International Corporation Microcapsules
CN105431226B (zh) * 2013-07-29 2018-01-12 高砂香料工业株式会社 微囊
EP3085758B1 (fr) 2013-12-19 2018-06-06 Kao Corporation Procédé de parfumage
FR3030512B1 (fr) * 2014-12-18 2018-03-30 L'oreal Utilisation comme agent deodorant et/ou parfumant de derives esters du l-tryptophane
JP6423758B2 (ja) * 2015-06-23 2018-11-14 花王株式会社 液体芳香剤組成物
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Also Published As

Publication number Publication date
JP2000512663A (ja) 2000-09-26
WO1997030687A2 (fr) 1997-08-28
WO1997030687A3 (fr) 1997-11-27

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