WO2013076148A2 - Compositions d'hygiène corporelle à diffusion de parfum améliorée par le biais de sels d'ammonium quaternaires de polyhydroxy - Google Patents

Compositions d'hygiène corporelle à diffusion de parfum améliorée par le biais de sels d'ammonium quaternaires de polyhydroxy Download PDF

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Publication number
WO2013076148A2
WO2013076148A2 PCT/EP2012/073250 EP2012073250W WO2013076148A2 WO 2013076148 A2 WO2013076148 A2 WO 2013076148A2 EP 2012073250 W EP2012073250 W EP 2012073250W WO 2013076148 A2 WO2013076148 A2 WO 2013076148A2
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Prior art keywords
acetate
alpha
fragrance
methyl
beta
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Ceased
Application number
PCT/EP2012/073250
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English (en)
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WO2013076148A3 (fr
Inventor
Bijan Harichian
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.)
Hindustan Unilever Ltd
Unilever NV
Conopco Inc
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Hindustan Unilever Ltd
Unilever NV
Conopco Inc
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Application filed by Hindustan Unilever Ltd, Unilever NV, Conopco Inc filed Critical Hindustan Unilever Ltd
Publication of WO2013076148A2 publication Critical patent/WO2013076148A2/fr
Publication of WO2013076148A3 publication Critical patent/WO2013076148A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/30—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
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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

Definitions

  • the invention concerns personal care compositions which upon application to a human body surface quickly release fragrance components thereby improving aesthetics of these compositions.
  • fragrance Perhaps the most significant aesthetic of a personal care product for a consumer is fragrance. It is also important to rapidly deliver the scent.
  • a personal care composition which includes: (i) from 0.0001 to 5% of a fragrance to impart a pleasant scent onto a human body to which the composition is applied;
  • a scent boosting agent which is a polyhydroxy quaternary ammonium salt of structure (I):
  • a burst of fragrance from a personal care composition can be quickly released when the composition is deposited upon a human body part. More particularly, we have found that polyhydroxy quaternary ammonium salts function as scent boosting agent. These agents allow rapid volatilization of fragrance components during application of the personal care composition to skin or hair.
  • personal care composition is meant any product applied to a human body for improving appearance, cleansing, odor control or general aesthetics.
  • Nonlimiting examples of personal care compositions include leave-on skin lotions and creams, shampoos,
  • X " is selected from the group consisting of chloride, bromide, hydroxyl, sulphate, phosphate, methosulphate, carboxyl, citrate and tartrate.
  • Amounts of the polyhydroxy quaternary ammonium salts may range from 0.01 to 20%, and preferably, from 0.1 to 15%, and more preferably, from 0.5 to 10%, optimally from 1 to 8% by weight of the composition.
  • Most preferred as the polyhydroxy quaternary ammonium salt is bis(dihydroxypropyl)dimethylammonium chloride.
  • fragment is defined as a mixture of odoriferous components, optionally mixed with a suitable solvent diluent or carrier, which is employed to impart a desired odor. Fragrance components and mixtures thereof may be obtained from natural products such as essential oils, absolutes, resinoids, resins and concretes, as well as synthetic products such as hydrocarbons, alcohols, aldehydes, ketones, ethers, carboxylic acids, esters, acetals, ketals, nitriles and the like, including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds.
  • Suitable characteristics of fragrances can include at least one of the following, in any combination: (1 ) liquid or semi-liquid after mixing with the other components; (2) pleasant and/or clean odor when mixed with other components, e.g., one or more of lavender, violet, rose, jasmin, pine, woody, floral, fruity, lemon, lime, apple, peach, raspberry, strawberry, banana, plum, apricot, vanilla, pear, eucalyptus, aromatic, aldehydic, tutti frutti, oriental, sweet, amber, Paola, Muguet, Citron (lime) ella, and the like; (3) specific gravity (20/20) in the range of 0.600-1 .300, preferably 0.800-1.100, each preferably varying 0.001 -0.05, more preferably 0.008-0.020; (4) refractive index (20°C) of 1.300-1 .800, preferably 1.400-1.600, each preferably varying 0.001 -0.05, more preferably 0.008-0.020; (5) sapon
  • Typical fragrance components which may be employed for the present invention can be selected from one or more of:
  • fragrances include but are not limited to: Camphor
  • Suitable solvents, diluents or carriers for perfumes as mentioned above are for example: ethanol, isopropanol, diethylene glycol monoethyl ether, dipropyl glycol, triethyl citrate and the like.
  • Particularly preferred fragrance components of the present invention are cyclic and acyclic terpenes and terpenoids. These materials are based upon isoprene repeating units.
  • Examples include alpha and beta pinene, myrcene, geranyl alcohol and acetate, camphene, dl-limonene, alpha and beta phellandrene, tricyclene, terpinolene, allocimmane, geraniol, nerol, linanool, dihydrolinanool, citral, ionone, methyl ionone, citronellol, citronellal, alpha terpineol, beta terpineol, alpha fenchol, borneol, isoborneol, camphor, terpinen-1 -ol, terpin- 4-ol, dihydroterpineol, methyl chavicol, anethole, 1 ,4 and 1 ,8 cineole, geranyl nitrile, isobornyl acetate, linalyl acetate, caryophyllene, alpha cedrene, gu
  • Amounts of the fragrance may range from 0.0001 to 5%, usually from 0.001 to 2.5%, more usually from 0.1 to 1 .5% by weight of the composition.
  • Compositions of this invention may also include a cosmetically acceptable carrier. Amounts of the carrier may range from 1 to 99.9%, preferably from 70 to 95%, optimally from 80 to 90% by weight of the composition.
  • the useful carriers are water, emollients, fatty acids, fatty alcohols, humectants, thickeners and combinations thereof.
  • the carrier may be aqueous, anhydrous or an emulsion.
  • the compositions are aqueous, especially water and oil emulsions of the W/O or O/W or triplex W/O/W variety. Water when present may be in amounts ranging from 5 to 95%, preferably from 20 to 70%, optimally from 35 to 60% by weight.
  • Emollient materials may serve as cosmetically acceptable carriers. These may be in the form of silicone oils, synthetic esters and hydrocarbons. Amounts of the emollients may range anywhere from 0.1 to 95%, preferably between 1 and 50% by weight of the composition.
  • Silicone oils may be divided into the volatile and nonvolatile variety.
  • volatile refers to those materials which have a measurable vapor pressure at ambient temperature.
  • Volatile silicone oils are preferably chosen from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
  • Nonvolatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers.
  • the essentially nonvolatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from 5 x 10 "6 to 0.1 m 2 /s at 25°C.
  • the preferred nonvolatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from 1 x 10 "5 to 4 x 10 "4 m 2 /s at 25°C.
  • Another class of nonvolatile silicones are emulsifying and non-emulsifying silicone elastomers.
  • DimethiconeA inyl Dimethicone Crosspolymer available as Dow Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18.
  • Silicone waxes such as Silwax WS-L (Dimethicone Copolyol Laurate) may also be useful.
  • ester emollients are:
  • Alkyl esters of saturated fatty acids having 10 to 24 carbon atoms examples thereof include behenyl neopentanoate, isononyl isonanonoate, isopropyl myristate and octyl stearate.
  • Ether-esters such as fatty acid esters of ethoxylated saturated fatty alcohols.
  • Polyhydric alcohol esters Ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl mono-stearate, 1 ,3-butylene glycol monostearate, 1 ,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters. Particularly useful are pentaerythrito
  • Wax esters such as beeswax, spermaceti wax and tribehenin wax.
  • Sugar ester of fatty acids such as sucrose polybehenate and sucrose
  • Hydrocarbons which are suitable cosmetically acceptable carriers include petrolatum, mineral oil, C11-C13 isoparaffins, and especially isohexadecane, available commercially as Permethyl 101 A from Presperse Inc.
  • Fatty acids having from 10 to 30 carbon atoms may also be suitable as cosmetically acceptable carriers. Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, oleic, hydroxystearic and behenic acids.
  • Fatty alcohols having from 10 to 30 carbon atoms are another useful category of cosmetically acceptable carrier. Illustrative of this category are stearyl alcohol, lauryl alcohol, myristyl alcohol and cetyl alcohol.
  • Humectants of the polyhydric alcohol-type can be employed as cosmetically acceptable carriers.
  • Typical polyhydric alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol,
  • humectant may range anywhere from 0.5 to 50%, preferably between 1 and 15% by weight of the composition.
  • Thickeners can be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention.
  • Typical thickeners include crosslinked acrylates (e.g.
  • Carbopol 982® hydrophobically-modified acrylates (e.g. Carbopol 1382®), cellulosic derivatives and natural gums.
  • useful cellulosic derivatives are sodium
  • Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and combinations of these gums.
  • Inorganics may also be utilized as thickeners, particularly clays such as bentonites and hectorites, fumed silicas, and silicates such as magnesium aluminum silicate (Veegum®). Amounts of the thickener may range from 0.0001 to 10%, usually from 0.001 to 1 %, optimally from 0.01 to 0.5% by weight of the composition.
  • Personal care compositions of the present invention may be in any form. These forms may include lotions, creams, roll-on formulations, sticks, mousses, aerosol and non-aerosol sprays and fabric (e.g. nonwoven textile)-applied formulations.
  • Surfactants may also be present in compositions of the present invention. Total concentration of the surfactant when present may range from 0.1 to 40%, preferably from 1 to 20%, optimally from 1 to 5% by weight of the composition.
  • the surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteric actives.
  • nonionic surfactants are those with a Ci 0 -C 2 o fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C 2 -Ci 0 alkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono- and di-fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- C 8 -C 2 o fatty acids; and polyoxyethylene sorbitan as well as combinations thereof.
  • Alkyl polyglycosides and saccharide fatty amides are also suitable nonionic surfactants.
  • Preferred anionic surfactants include soap, alkyl ether sulfates and sulfonates, alkyl sulfates 5 and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuccinates, C 8 -C 2 o acyl
  • Sunscreen actives may also be included in compositions of the present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinnamate (available as Parsol MCX®), Avobenzene (available as Parsol 1789®), octylsalicylate (available as Dermablock OS®),
  • Inorganic sunscreen actives may be employed such as microfine titanium dioxide, zinc oxide, polyethylene and various other polymers.
  • microfine is meant particles of average size ranging from 10 to 200 nm, preferably from 20 to 100 nm. Amounts of the sunscreen agents when present may generally range from 0.1 to
  • composition 15 30%, preferably from 2 to 20%, optimally from 4 to 10% by weight of the composition.
  • Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms.
  • Suitable traditional preservatives for compositions of this invention are alkyl esters of para-hydroxybenzoic acid.
  • Other preservatives which have more recently come into use include hydantoin derivatives,
  • propionate salts and a variety of quaternary ammonium compounds.
  • Cosmetic chemists are familiar with appropriate preservatives and routinely choose them to satisfy the preservative challenge test and to provide product stability.
  • Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol. The preservatives should be selected having regard for the use of the
  • Preservatives are preferably employed in amounts ranging from 0.01 % to 2% by weight of the composition.
  • compositions of the present invention may include vitamins.
  • Illustrative vitamins are Vitamin A (retinol), Vitamin B 2 , Vitamin B 3 (niacinamide), Vitamin B 6 , Vitamin C, Vitamin E and Biotin. 30 Derivatives of the vitamins may also be employed. For instance, Vitamin C derivatives
  • Vitamin E examples include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate and ascorbyl glycoside.
  • Derivatives of Vitamin E include tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed.
  • a particularly suitable Vitamin B 6 derivative is Pyridoxine Palmitate.
  • Flavanoids may also be useful, particularly glucosyl hesperidin, rutin, and soy isoflavones (including genistein, daidzein, equol, and their glucosyl derivatives) and mixtures thereof.
  • Total amount of vitamins or flavonoids when present may range from 0.0001 to 10%, preferably from 0.01 % to 1 %, optimally from 0.1 to 0.5% by weight of the composition.
  • Another type of useful substance can be that of an enzyme such as oxidases, proteases, lipases and combinations. Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from the Brooks Company, USA.
  • Skin lightening compounds may be included in the compositions of the invention.
  • Illustrative substances are placental extract, lactic acid, niacinamide, arbutin, kojic acid, ferulic acid, resorcinol and derivatives including 4-substituted resorcinols and combinations thereof.
  • Amounts of these agents may range from 0.1 to 10%, preferably from 0.5 to 2% by weight of the composition.
  • Desquamation promoters may be present.
  • Illustrative are the alpha-hydroxycarboxylic acids and beta-hydroxycarboxylic acids.
  • the term "acid” is meant to include not only the free acid but also salts and Ci-C 30 alkyl or aryl esters thereof and lactones generated from removal of water to form cyclic or linear lactone structures.
  • Representative acids are glycolic, lactic and malic acids.
  • Salicylic acid is representative of the beta-hydroxycarboxylic acids. Amounts of these materials when present may range from 0.01 to 15% by weight of the composition.
  • compositions of this invention may optionally be included in compositions of this invention.
  • Illustrative are pomegranate, white birch (Betula Alba), green tea, chamomile, licorice and extract combinations thereof.
  • the extracts may either be water soluble or water-insoluble carried in a solvent which respectively is hydrophilic or hydrophobic. Water and ethanol are the preferred extract solvents.
  • compositions of the present invention may also be utilized for many compositions of the present invention but may also be excluded. Amounts of these materials may range from 0.000001 to 10%, preferably from 0.0001 to 1 % by weight of the composition. Colorants, opacifiers and abrasives may also be included in compositions of the present invention. Each of these substances may range from 0.05 to 5%, preferably between 0.1 and 3% by weight of the composition.
  • compositions of the present invention can also be, optionally, incorporated into a water insoluble substrate for application to the skin such as in the form of a treated wipe.
  • a representative personal care composition of the present invention in the form of a cosmetic lotion is outlined under Table I.
  • Natrosol® 250HHR ethyl cellulose 0.50
  • a water-in-oil topical liquid make-up foundation according to invention is described in Table II below.
  • a disposable, single use personal care towelette product is described according to the present invention.
  • a 70/30 polyester/rayon non-woven towelette is prepared with a weight of 1 .8 grams and dimensions of 15 cm by 20 cm.
  • Onto this towelette is impregnated a composition with a terpenoid type fragrance, and bis(dihydroxypropyl)dimethylammonium chloride as outlined in
  • Vitamin E Acetate 0.001
  • a toilet bar illustrative of the present invention is outlined under Table IV.
  • a shampoo composition useful in the context of the present invention is described in Table V below.
  • This Example illustrates an antiperspirant/deodorant formula according to the present invention.
  • This Example illustrates a series of skin lotions formulated for purposes of the present invention.
  • Samples were prepared by mixing 10% of scent boosting agent (Bis(dihydroxypropyl)dimethylammonium chloride) in water along with 0.05% commercially available oils like Deep Moisture perfume oil.
  • scent boosting agent Bis(dihydroxypropyl)dimethylammonium chloride
  • This oil is a mixture of many components including but not limited to limonene, dihydromyrcenol, gamma terpinene, benzyl acetate, linalool, pinene, isomethyl ionone and others.
  • GC gas chromatography
  • SPME solid phase microextraction
  • fragrance/water mixture One gram of fragrance/boosting agent/water mixture was prepared in 20 ml GC headspace sampling vials sealed with caps having septums (from Gerstel, Inc.).
  • the GC column was a HP-5MS column from Agilent (inner diameter 0.25 mm, length 30 m, stationary phase thickness 0.25um).
  • the GC conditions were as follows: Injector in splitless
  • camphor 76-22-2 1 1.15
  • dodecanal 112-54-9 1 1.53 octalactone 104-50-7 1 2.05
  • amyl cinnamic aldehyde 122-40-7 1 2.30
  • Example 9 The experiments in Example 9 were conducted in a manner similar to the one described in Example 8 except the following: Fragrance oil concentration was 0.01 % in water with 10% boosting agent as compared to 0.01 % fragrance oil in water with no boosting agent.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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  • Epidemiology (AREA)
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Abstract

L'invention concerne un produit d'hygiène corporelle qui contient un parfum, un sel d'ammonium quaternaire de polyhydroxy et un véhicule cosmétiquement acceptable. Le sel d'ammonium quaternaire de polyhydroxy agit comme système renforçateur de parfum en améliorant la volatilisation des composants de parfum lors de la première application de la composition d'hygiène corporelle sur la peau.
PCT/EP2012/073250 2011-11-22 2012-11-21 Compositions d'hygiène corporelle à diffusion de parfum améliorée par le biais de sels d'ammonium quaternaires de polyhydroxy Ceased WO2013076148A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161562481P 2011-11-22 2011-11-22
US61/562,481 2011-11-22

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WO2013076148A2 true WO2013076148A2 (fr) 2013-05-30
WO2013076148A3 WO2013076148A3 (fr) 2013-12-19

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5135747A (en) 1991-05-17 1992-08-04 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Deodorant/antiperspirant products with fragrance and encapsulated odor counteractant
US5833999A (en) 1994-10-20 1998-11-10 The Proctor & Gamble Company Personal treatment compositions and /or cosmetic compositions containing enduring perfume
US5849310A (en) 1994-10-20 1998-12-15 The Procter & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
US6086903A (en) 1996-02-26 2000-07-11 The Proctor & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
US6100233A (en) 1996-08-19 2000-08-08 The Procter & Gamble Company Odor control compositions comprising β-ketoester pro-fragrances

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2504053C3 (de) * 1975-01-31 1978-04-27 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt N-23-Dihydroxypropyl-N-2'-hydroxyalkyl-amine sowie deren Säureadditionsbzw, quaternäre Ammoniumsalze, Verfahren zu deren Herstellung und ihre Verwendung als Antistatika für Kunststoffe
DE19517048C1 (de) * 1995-05-10 1996-10-02 Henkel Kgaa Verwendung von quartären Aminoglycerinverbindungen
US6869977B1 (en) * 2004-04-09 2005-03-22 Colonial Chemical Inc. Skin moisturization compound
US7659233B2 (en) * 2004-10-25 2010-02-09 Conopco, Inc. Personal care compositions with silicones and dihydroxypropyl trialkyl ammonium salts
CN101296684B (zh) * 2005-08-25 2012-10-10 高露洁-棕榄公司 保湿组合物
US7794741B2 (en) * 2007-05-30 2010-09-14 Conopco, Inc. Enhanced delivery of certain fragrance components from personal care compositions
JP5898214B2 (ja) * 2010-09-30 2016-04-06 ダウ グローバル テクノロジーズ エルエルシー ４級アンモニウムポリヒドロキシ化合物とパーソナルケア組成物におけるその使用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5135747A (en) 1991-05-17 1992-08-04 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Deodorant/antiperspirant products with fragrance and encapsulated odor counteractant
US5833999A (en) 1994-10-20 1998-11-10 The Proctor & Gamble Company Personal treatment compositions and /or cosmetic compositions containing enduring perfume
US5849310A (en) 1994-10-20 1998-12-15 The Procter & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
US6086903A (en) 1996-02-26 2000-07-11 The Proctor & Gamble Company Personal treatment compositions and/or cosmetic compositions containing enduring perfume
US6100233A (en) 1996-08-19 2000-08-08 The Procter & Gamble Company Odor control compositions comprising β-ketoester pro-fragrances

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