WO2000067716A1 - Compositions cosmetiques renfermant des oligosaccharides cycliques et un parfum - Google Patents

Compositions cosmetiques renfermant des oligosaccharides cycliques et un parfum Download PDF

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Publication number
WO2000067716A1
WO2000067716A1 PCT/US1999/009907 US9909907W WO0067716A1 WO 2000067716 A1 WO2000067716 A1 WO 2000067716A1 US 9909907 W US9909907 W US 9909907W WO 0067716 A1 WO0067716 A1 WO 0067716A1
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WO
WIPO (PCT)
Prior art keywords
fragrance
cyclic oligosaccharide
composition according
present
compositions
Prior art date
Application number
PCT/US1999/009907
Other languages
English (en)
Inventor
Lynette Holland
George Rizzi
Peter Malton
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to PCT/US1999/009907 priority Critical patent/WO2000067716A1/fr
Priority to AU38851/99A priority patent/AU3885199A/en
Priority to EP00926513A priority patent/EP1176942A1/fr
Priority to AU45032/00A priority patent/AU4503200A/en
Priority to PCT/US2000/012415 priority patent/WO2000067718A1/fr
Publication of WO2000067716A1 publication Critical patent/WO2000067716A1/fr

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Classifications

    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/738—Cyclodextrins
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • the present invention relates to cosmetic compositions and in particular to long- lasting fragrance compositions.
  • compositions that they comprise a fragrance.
  • a fragrance can mask unpleasant odours or can improve consumer acceptance of a composition through delivering a pleasant smell.
  • the sole purpose of some compositions is the application of a pleasant odour to the skin, hair or other suitable substrate.
  • the fragrant effect of these compositions is transitory and the fragrance quickly becomes imperceptible.
  • the fragrance may be formulated in such a way as to include a higher proportion of fragrance materials with a low volatility. This means the fragrance persists for longer. However, using less volatile materials restricts the fragrance character that can be achieved. It has also been suggested that it may be possible to utilise cyclic oligosaccharides, and in particular cyclodextrins.
  • JP-A-50/63126 discloses perfume and cyclodextrin complexes for use in bath preparations
  • JP-A-7/241333 discloses a long-lasting, room deodorising composition containing a fragrance and cyclodextrin.
  • compositions comprising greater than about 0.2%, by weight, fragrance and cyclic oligosaccharide having an average degree of substitution of at least about 1.6 provide an initial burst of fragrance and improved fragrance longevity.
  • the stability profile of the complexes formed between the fragrance and the cyclic oligosaccharide of the present invention is such that a perceptible amount of fragrance is released over a sufficiently long time to satisfy the consumers desire for long lasting fragrance.
  • cosmetic compositions comprising:
  • compositions of the present invention provide a long-lasting fragrance while at the same time having a 'burst' of fragrance on application.
  • the present invention relates to compositions comprising two essential elements, greater than 0.2% fragrance and cyclic oligosaccharide having an average degree of substitution of at least about 1.6. These two elements will be described in more detail below.
  • fragrance material comprises greater than about 0.2%, by weight, fragrance material.
  • fragrance material is used to indicate any odouriferous material. Any fragrance material suitable for use in cosmetic compositions may be used herein but the fragrance will most often be liquid at ambient temperatures. Preferably, the fragrance material will be present at a level of from about 0.25% to about 40%, more preferably from about 0.5% to about 30%, even more preferably from about 2.5% to about 25%, even more preferably still from about 8% to about 15%, by weight, of total composition.
  • chemicals are known for fragrance uses, including materials such as aldehydes, ketones and esters.
  • fragrances More commonly, naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are known for use as fragrances.
  • the fragrance materials useful herein include pro-fragrances such as acetal pro-fragrances, ketal pro- fragrances, ester pro-fragrances, hyrdolyzable inorganic-organic pro-fragrances and mixtures thereof.
  • the fragrance material may be released from the pro- fragrances in a number of ways. For example, the fragrance may be released as a result of simple hydrolysis, or by a shift in an equilibrium reaction, or by a pH- change, or by enzymatic release.
  • the fragrances herein can be relatively simple in their compositions, comprising a single chemical, or can comprise highly sophisticated complex mixtures of natural and synthetic chemical components, all chosen to provide any desired odour.
  • the present compositions are particularly good at improving the longevity of the more volatile fragrance materials which commonly give 'fresh', 'floral', 'fruity' 'green' and/or 'citrus' notes.
  • the fragrance materials of the present invention will have boiling points (BP) of about 500°C or lower, more preferably about 400°C or lower, even more preferably about 350°C or lower.
  • BP boiling points
  • the ClogP value of the fragrance materials useful herein is preferably greater than about 0.1 , more preferably greater than about 0.5, even more preferably greater than about 1.0, even more preferably still greater than about 1.2.
  • ClogP means the logarithm to the base 10 of the octanol/water partition coefficient. This can be readily calculated from a program called "CLOGP" which is available from Daylight Chemical Information Systems Inc., Irvine CA, USA. Octanol/water partition coefficients are described in more detail in US-A-5,578,563.
  • fragrances useful herein include, but are not limited to, animal fragrances such as musk oil, civet, castoreum, ambergris, plant fragrances such as nutmeg extract, cardomon extract, ginger extract, cinnamon extract, patchouli oil, geranium oil, orange oil, mandarin oil, orange flower extract, cedarwood, vetyver, lavandin, ylang extract, tuberose extract, sandalwood oil, bergamot oil, rosemary oil, spearmint oil, peppermint oil, lemon oil, lavender oil, citronella oil, chamomille oil, clove oil, sage oil, neroli oil, labdanum oil, eucalyptus oil, verbena oil, mimosa extract, narcissus extract, carrot seed extract, jasmine extract, olibanum extract, rose
  • fragrance materials include, but are not limited to, chemical substances such as acetophenone, adoxal, aldehyde C-12, aldehyde C-14, aldehyde C-18, allyl caprylate, ambroxan, amyl acetate, dimethylindane derivatives, ⁇ -amylcinnamic aldehyde, anethole, anisaldehyde, benzaldehyde, benzyl acetate, benzyl alcohol and ester derivatives, benzyl propionate, benzyl salicylate, borneol, butyl acetate, camphor, carbitol, cinnamaldehyde, cinnamyl acetate, cinnamyl alcohol, cis-3-hexanol and ester derivatives, cis-3-hexenyl methyl carbonate, citral, citronnellol and ester derivatives, cumin aldehyde,
  • a second essential element of the compositions of the present invention is that they comprise a cyclic oligosaccharide having one or more unsubstituted alkyl substituents.
  • cyclic oligosaccharide means a cyclic structure comprising six or more saccharide units.
  • Preferred for use herein are cyclic oligosaccharides having six, seven or eight saccharide units and mixtures thereof, more preferably seven saccharide units. It is common in the art to abbreviate six, seven and eight membered cyclic oligosaccharides to ⁇ , ⁇ and ⁇ respectively.
  • compositions of the present invention preferably comprise from about 0.001% to about 40%, more preferably from about 0.1 % to about 25%, even more preferably from about 1% to about 20%, especially from about 2% to about 15%, by weight, of cyclic oligosaccharide.
  • the cyclic oligosaccharide of the present invention may comprise any suitable saccharide or mixtures of saccharides.
  • suitable saccharides include, but are not limited to, glucose, fructose, mannose, galactose, maltose and mixtures thereof.
  • preferred for use herein are cyclic oligosaccharides of glucose. Therefore, the preferred cyclic oligosaccharides for use herein are ⁇ -cyclodextrins.
  • the cyclic oligosaccharide for use herein may be substituted by any suitable substituent.
  • suitable substituents include, but are not limited to, alkyl groups, hydroxyalkyl groups, aryl groups, maltosyl groups, allyl groups, benzyl groups, alkanoyl groups and mixtures thereof.
  • the substituent is selected from alkyl groups, hydroxyalkyl groups and mixtures thereof. More preferably, the substituent is selected from alkyl groups and mixtures thereof.
  • Preferred alkyl substituents are selected from C C 8 alkyl groups and mixtures thereof, more preferred alkyl substituents are selected from alkyl groups and mixtures thereof, even more preferred alkyl substituents are selected from C r C 4 alkyl groups and mixtures thereof.
  • Especially preferred alkyl substituents are ethyl and methyl, more especially methyl.
  • the alkyl substituent may be saturated or unsaturated, straight or branched chain but is preferably saturated and straight chain. As used in this paragraph, the term "mixtures thereof means two or more different alkyl groups are substituted on the same cyclic oligosaccharide.
  • the cyclic oligosaccharides of the present invention are preferably substituted only by unsubstituted alkyl substituents. Therefore, the most preferred cyclic oligosaccharides for use herein are methyl- ⁇ -cyclodextrins. Preferred methyl- ⁇ - cyclodextrins are available from Wacker-Chemie GmbH Hanns-Seidel-Platz 4, Munchen, DE under the tradename Beta W7 M1.8.
  • the cyclic oligosaccharides of the present invention have an average degree of substitution of at least about 1.6.
  • Preferred cyclic oligosaccharides for use herein have an average degree of substitution of less than about 2.8. More preferably the cyclic oligosaccharides for use herein have an average degree of substitution of from about 1.7 to about 2.0.
  • degree of substitution means the average number of substituents per saccharide unit. The average number of substituents can be determined using common Nuclear Magnetic Resonance techniques known in the art.
  • the cyclic oligosaccharides of the present invention are preferably soluble in both water and ethanol.
  • soluble means at least about 0.1g of solute dissolves in 100ml of solvent, at 25°C and 1 atm of pressure.
  • the cyclic oligosaccharides for use herein have a solubility of at least about 1g/100ml, more preferably at least about 10g/100ml, even more preferably at least about 100g/100ml, at 25°C and 1atm of pressure.
  • the weight ratio of total fragrance to cyclic oligosaccharide in the compositions of the present invention is at least about 1 :1 , more preferably at least about 1.5:1 , even more preferably at least about 2:1.
  • compositions herein can contain a variety of other optional components suitable for rendering such compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • Such conventional optional ingredients are well-known to those skilled in the art. These include any cosmetically acceptable ingredients such as those found in the CTFA International Cosmetic Ingredient Dictionary and Handbook, 7th edition, edited by Wenninger and McEwen, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, D.C., 1997).
  • cosmetically acceptable means a material (e.g., compound or composition) which is suitable for use in contact with skin, hair or other suitable substrate as defined hereinbelow.
  • compositions of the present invention will preferably comprise a cosmetically acceptable carrier.
  • Cosmetically acceptable carrier means one or more compatible solid or liquid fillers, diluents, extenders and the like, which are cosmetically acceptable as defined hereinabove.
  • compatible means that the components of the compositions of this invention are capable of being combined with the primary actives of the present invention, and with each other, in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations.
  • the type of carrier utilized in the present invention depends on the type of product desired.
  • the compositions useful in the present invention may be a wide variety of product types.
  • These include, but are not limited to, lotions, creams, gels, sticks, sprays, ointments, pastes, mousses and cosmetics (e.g., solid, semi-solid, or liquid make-up, including foundations).
  • These product types may comprise several types of carriers including, but not limited to, solutions, aerosols, emulsions (including oil-in-water or water-in-oil), gels, solids, and liposomes.
  • compositions of the present invention preferably comprise a volatile solvent or mixture of volatile solvents.
  • the solvents for use herein are preferably organic volatile solvents. If present, the volatile solvent or mixture of solvents will generally be at a level of about 5% or greater, preferably about 10% or greater, more preferably about 20% or greater, even more preferably about 50% or greater, by weight of total composition.
  • volatile refers to substances with a significant amount of vapour pressure under ambient conditions, as is understood by those in the art.
  • the volatile solvents for use herein will preferably have a vapour pressure of about 2kPa or more, more preferably about 6kPa or more, at 25°C.
  • the volatile solvents for use herein will preferably have a boiling point under one atmosphere (atm) of less than about 150°C, more preferably less than about 100°C, even more preferably less than about 90°C, even more preferably still less than about 80°C.
  • the volatile solvents for use herein will be relatively odourless and safe for use on human skin.
  • Suitable volatile solvents include, but are not limited to, C C 4 alcohols, volatile silicones and mixtures thereof.
  • Preferred volatile solvents are C, ⁇ alcohols and mixtures thereof. More preferred for use herein is ethanol.
  • Nonvolatile solvents While the compositions of the present invention preferably comprise a volatile solvent they may also comprise "nonvolatile" solvents. Suitable non-volatile solvents include, but are not limited to, benzyl benzoate, diethyl phtalate, isopropyl myristate, propylene glycol, dipropylene glycol and mixtures thereof.
  • compositions of the present invention may also comprise water. If present, the water will preferably comprise from about 0.1 % to about 40%, more preferably from about 1 % to about 30%, even more preferably about 5% to about 20%, by weight, of total composition.
  • alcohol denaturants such as denatonium benzoate
  • UV stabilisers such as benzophenone-2
  • antioxidants such as tocopheryl acetate
  • preservatives such as phenoxyethanol, benzyl alcohol, methyl paraben, propyl paraben
  • dyes pH adjusting agents such as lactic acid, citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate
  • deodorants and antimicrobials such as famesol and zinc phenolsulphonate
  • humectants such as glycerine
  • oils skin conditioning agents such as allantoin
  • cooling agents such as trimethyl isopropyl butanamide and menthol
  • hair conditioning ingredients such as panthenol, panthetine, pantotheine, panthenyl ethyl
  • compositions of the present invention can be used to provide a long-lasting fragrance to a suitable substrate.
  • suitable substrate means any surface to which the present composition may be applied without an unduly adverse effect.
  • suitable substrates include, but are not limited to, skin, hair and fabrics.
  • the present compositions are applied to skin or hair, especially skin.
  • the cosmetic compositions of the present invention may be used in a conventional manner for fragrancing a suitable substrate.
  • An effective amount of the composition typically from about 1 ⁇ l to about 1000 ⁇ l, preferably from about 10 ⁇ l to about 250 ⁇ l, more preferably from about 25 ⁇ l to about 100 ⁇ l, is applied to the substrate.
  • the composition may be applied by hand but is preferably applied utilising a vaporiser. Preferably, the composition is then left to dry.
  • the preferred method of treating the substrate comprises:
  • compositions of the present invention may take any form suitable for cosmetic use. These include, but are not limited to, vapour sprays, aerosols, emulsions, solid sticks, lotions and liquids. Preferably the compositions of the present invention take the form of a vapour spray.
  • Beta W7 M1.8 available from Wacker-Chemie GmbH, Hanns-Seidel-Platz 4, Munchen, DE
  • the cyclic oligosaccharide was dissolved in the ethanol at room temperature, with stirring. Then the fragrance and water were added with stirring.
  • Beta W7 M1.8 available from Wacker-Chemie GmbH, Hanns-Seidel-Platz 4, Munchen, DE
  • the cyclic oligosaccharide was dissolved in the ethanol at room temperature, with stirring. Then the fragrance was added with stirring.
  • Beta W7 M1.8 available from Wacker-Chemie GmbH, Hanns-Seidel-Platz 4, Munchen, DE
  • a propellant such as propane butane (CAP 40®) can be added to Examples VII-IX according to standard industry practice.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des compositions cosmétiques contenant a) approximativement 0,2 % en poids de parfum et b) des oligosaccharides cycliques présentant un degré moyen de substitution d'au moins 1,6. Les compositions de la présente invention fournissent un parfum durable tout en exhalant un parfum soutenu lors de l'application.
PCT/US1999/009907 1999-05-07 1999-05-07 Compositions cosmetiques renfermant des oligosaccharides cycliques et un parfum WO2000067716A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
PCT/US1999/009907 WO2000067716A1 (fr) 1999-05-07 1999-05-07 Compositions cosmetiques renfermant des oligosaccharides cycliques et un parfum
AU38851/99A AU3885199A (en) 1999-05-07 1999-05-07 Cosmetic compositions comprising cyclic oligosaccharide and fragrance
EP00926513A EP1176942A1 (fr) 1999-05-07 2000-05-05 Composition cosmetique renfermant un oligosaccharide cyclique et un parfum
AU45032/00A AU4503200A (en) 1999-05-07 2000-05-05 Cosmetic composition comprising cyclic oligosaccharide and fragrance
PCT/US2000/012415 WO2000067718A1 (fr) 1999-05-07 2000-05-05 Composition cosmetique renfermant un oligosaccharide cyclique et un parfum

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1999/009907 WO2000067716A1 (fr) 1999-05-07 1999-05-07 Compositions cosmetiques renfermant des oligosaccharides cycliques et un parfum

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WO2000067716A1 true WO2000067716A1 (fr) 2000-11-16

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PCT/US1999/009907 WO2000067716A1 (fr) 1999-05-07 1999-05-07 Compositions cosmetiques renfermant des oligosaccharides cycliques et un parfum
PCT/US2000/012415 WO2000067718A1 (fr) 1999-05-07 2000-05-05 Composition cosmetique renfermant un oligosaccharide cyclique et un parfum

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AU (2) AU3885199A (fr)
WO (2) WO2000067716A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11279774B2 (en) 2019-01-03 2022-03-22 Underdog Pharmaceuticals, Inc. Cyclodextrin dimers, compositions thereof, and uses thereof

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
EP2694017B1 (fr) 2011-04-07 2019-05-22 The Procter and Gamble Company Compositions d'hygiène personnelle à dépôt accru de microcapsules de polyacrylate
EP2694016B1 (fr) 2011-04-07 2017-05-24 The Procter and Gamble Company Compositions de shampooing à dépôt accru de microcapsules de polyacrylate
JP2014510140A (ja) 2011-04-07 2014-04-24 ザ プロクター アンド ギャンブル カンパニー ポリアクリレートマイクロカプセルの付着が増大したコンディショナー組成物
MX362369B (es) 2011-05-26 2019-01-14 Procter & Gamble Composiciones que comprenden un aroma de perfume eficiente.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63192706A (ja) * 1987-02-06 1988-08-10 Kao Corp ロ−シヨン組成物
WO1996004940A1 (fr) * 1994-08-12 1996-02-22 The Procter & Gamble Company Composition reduisant l'impression de mauvaise odeur sur les surfaces inanimees
WO1996004937A1 (fr) * 1994-08-12 1996-02-22 The Procter & Gamble Company Solutions a base de cyclodextrine non complexee pour la lutte contre les odeurs des surfaces inanimees
JPH08176587A (ja) * 1994-12-27 1996-07-09 Shiseido Co Ltd 香料組成物
WO1998056342A1 (fr) * 1997-06-09 1998-12-17 The Procter & Gamble Company Compositions parfumees a une ou a deux phases pour combattre les odeurs corporelles et leur mode d'utilisation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63192706A (ja) * 1987-02-06 1988-08-10 Kao Corp ロ−シヨン組成物
WO1996004940A1 (fr) * 1994-08-12 1996-02-22 The Procter & Gamble Company Composition reduisant l'impression de mauvaise odeur sur les surfaces inanimees
WO1996004937A1 (fr) * 1994-08-12 1996-02-22 The Procter & Gamble Company Solutions a base de cyclodextrine non complexee pour la lutte contre les odeurs des surfaces inanimees
JPH08176587A (ja) * 1994-12-27 1996-07-09 Shiseido Co Ltd 香料組成物
WO1998056342A1 (fr) * 1997-06-09 1998-12-17 The Procter & Gamble Company Compositions parfumees a une ou a deux phases pour combattre les odeurs corporelles et leur mode d'utilisation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 11 29 November 1996 (1996-11-29) *
STN INTERNATIONAL. FILE CHEMICAL ABSTRACTS, AN=109:236737, XP002120592 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11279774B2 (en) 2019-01-03 2022-03-22 Underdog Pharmaceuticals, Inc. Cyclodextrin dimers, compositions thereof, and uses thereof

Also Published As

Publication number Publication date
AU3885199A (en) 2000-11-21
WO2000067718A1 (fr) 2000-11-16
AU4503200A (en) 2000-11-21
EP1176942A1 (fr) 2002-02-06

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