WO1994010971A1 - Composition cosmetique renfermant des esters d'acide succinique - Google Patents

Composition cosmetique renfermant des esters d'acide succinique Download PDF

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Publication number
WO1994010971A1
WO1994010971A1 PCT/EP1993/003095 EP9303095W WO9410971A1 WO 1994010971 A1 WO1994010971 A1 WO 1994010971A1 EP 9303095 W EP9303095 W EP 9303095W WO 9410971 A1 WO9410971 A1 WO 9410971A1
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WO
WIPO (PCT)
Prior art keywords
composition according
succinic acid
alkyl
acid derivative
oil
Prior art date
Application number
PCT/EP1993/003095
Other languages
English (en)
Inventor
Anthony Vincent Rawlings
Brian Rossall
Original Assignee
Unilever Plc
Unilever Nv
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 Unilever Plc, Unilever Nv filed Critical Unilever Plc
Priority to AU54640/94A priority Critical patent/AU5464094A/en
Publication of WO1994010971A1 publication Critical patent/WO1994010971A1/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
    • A61K8/30—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
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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
    • A61Q19/007—Preparations for dry skin
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • Cosmetic composition containing sucdnlc add esters Cosmetic composition containing sucdnlc add esters.
  • the invention relates to a novel cosmetic composition for topical application to skin, hair or nails comprising a novel succinic acid derivatives having a lipid-like structure, and a co ⁇ metically acceptable vehicle.
  • Ceramides present within the intercellular lipid lamellae of the stratum corneum play an important role in the production and maintenance of the water permeability barrier of the skin. Ceramides, or substances closely related to them, have been widely disclosed as components of skin care compositions.
  • Unilever NV in EP 0 097 059 disclosed the vital role played by ⁇ -linoleoyl ceramides in the water barrier of the skin and described the synthesis and application for skin care of such ⁇ -substituted ceramides.
  • Kao Corporation in GB 2 178 312 and GB 2 213 723, disclose the use of natural ceramides extracted from skin in topical products, and in EP 0 227 994, they disclose synthetic analogues of ceramides.
  • alkyl and alkenyl acid monoester alkoxylates which are easily synthesised, also have an action analogous to that of the natural and synthetic ceramides.
  • composition suitable for topical application. to skin, hair or nails comprising:
  • R 1 represents an alkyl, alkenyl, mono- or dihydroxyalkyl or hydroxyalkenyl group having from 6-22 carbon atoms;
  • R 2 and R 3 individually represent H or an alkyl or alkenyl group having from 12 to 22 carbon atoms; providing that when R 2 is H, R 3 is an alkyl or alkenyl group and when R 3 is H, R 2 is an alkyl or alkenyl group;
  • R 4 represents hydrogen, an alkyl, alkenyl, mono- or dihydroxyalkyl or hydroxyalkenyl group having from 6 to 22 carbon atoms or the group (2):
  • n is an integer of from 2 to 3
  • x and y are average degrees of alkoxylation, namely x is from 0 to 20 and y is from 1 to 20;
  • the group R 4 preferably represents H, while the group R 1 preferably represents an alkyl group having from 16 to 22 carbon atoms and most preferably from 20 to 22 carbon atoms.
  • n and m are preferably 2 and (x+y) is preferably from 1 to 20.
  • lipid components are those having the structures (3) to (7) :
  • the composition according to the invention may contain more than one succinic acid derivative having the structure (1) .
  • a particularly preferred example of such a composition is one comprising structure (3) and structure (5) .
  • the succinic acid derivatives of the invention are manufactured by methods of preparative chemistry that are of themselves known, starting from the known alkenylsuccinic anhydrides that can be obtained by ene- addition of maleic anhydride to olefins.
  • the succinic anhydride of structure (8) the monoester or the alkoxylate can be hydrogenated to saturate the double bonds that are present.
  • Suitable alcohols of the formula R OH are, for example, fatty alcohols with 6-22 carbon atoms, preferably, for example, stearyl, arachidyl, behenyl, oleyl, linoleyl and erucyl alcohol.
  • Alkane diols and alkane triols with 6-22 carbon atoms such as, for example, ricinolyl alcohol, 9- hydroxystearyl alcohol and 9, 10-dihydroxystearyl alcohol are also suitable.
  • the alkoxylation of the monoester is preferably carried out in the presence of basic catalysts such as, for example, LiOH, NaOH, KOH, NaOCH 3 , KOCH 3 and other known catalysts for reacting ethylene oxide or propylene oxide with reactive hydroxyl groups. It is preferable to work at temperatures of 100-200°C, a slightly higher than atmospheric pressure of 1-10 bar and with an excess of ethylene or propylene oxide.
  • basic catalysts such as, for example, LiOH, NaOH, KOH, NaOCH 3 , KOCH 3 and other known catalysts for reacting ethylene oxide or propylene oxide with reactive hydroxyl groups. It is preferable to work at temperatures of 100-200°C, a slightly higher than atmospheric pressure of 1-10 bar and with an excess of ethylene or propylene oxide.
  • alkylene oxide is also introduced into the ester bond of the monoester; this results in the attachment of the alkoxy groups designated x in structure (1) .
  • R 4 H
  • the monoester can also be converted into the alkali metal or alkaline earth metal salt and the latter then alkoxylated in an inert solvent.
  • composition according to the invention also comprises a cosmetically acceptable aqueous or non-aqueous vehicle to act as a dilutant, dispersant or carrier for the succinic acid derivative in the composition, so as to facilitate its distribution when the composition is applied to the skin, hair and/or nails.
  • a cosmetically acceptable aqueous or non-aqueous vehicle to act as a dilutant, dispersant or carrier for the succinic acid derivative in the composition, so as to facilitate its distribution when the composition is applied to the skin, hair and/or nails.
  • Vehicles other than water can include liquid or solid emollients, solvents, humectants, thickeners and powders. Examples of each of these types of vehicle, which can be used singly or as mixtures of one or more vehicles, are as follows:
  • Emollients such as stearyl alcohol, glyceryl monoricinoleate, glyceryl onostearate, mink oil, cetyl alcohol, isoproopyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, volatile or non-volatile silicone oils such as dimethylpolysiloxane, di-n-butyl sebacate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, lanolin, cocoa butter, corn oil, cotton seed oil, tallow, lard, olive oil,
  • Propellants such as air, propane, butane, isobutane, dimethyl ether, carbon dioxide, nitrous oxide;
  • Solvents such as ethyl alcohol, methylene chloride, i ⁇ opropanol, acetone, squalane, ⁇ qualene, ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, polyethylene glycol, dimethyl sulphoxide, dimethyl formamide, butylene glycol, tetrahydrofuran;
  • Powders such as chalk, talc, fullers earth, kaolin, starch, gums, particularly xanthum gum, colloidal silica sodium polyacrylate, tetra alkyl and/or trialkyl aryl ammonium smectites, chemically modified magnesium aluminium silicate, organically modified montmorillonite clay, hydrated aluminium silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethyl cellulose, ethylene glycol monostearate.
  • colloidal silica sodium polyacrylate tetra alkyl and/or trialkyl aryl ammonium smectites
  • chemically modified magnesium aluminium silicate organically modified montmorillonite clay
  • hydrated aluminium silicate fumed silica
  • carboxyvinyl polymer sodium carboxymethyl cellulose, ethylene glycol monostearate.
  • the cosmetically acceptable vehicle will usually form from 10 to 99.9%, preferably from 50 to 99% by weight of the emulsion, and can, in the absence of other cosmetic adjuncts, form the balance of the composition.
  • composition according to the invention can be aqueous or non-aqueous
  • a particularly convenient form is an emulsion, in which case an oil or oily material will normally be present, together with an emulsifier to provide a water-in-oil emulsion, an oil-in-water emulsion, or a complex emulsion, depending largely on the average hydrophillic-lyophilic balance (HLB) of the emulsifier employed.
  • HLB hydrophillic-lyophilic balance
  • composition according to the invention can optionally comprise one or more oils or other materials having the properties of an oil.
  • oils examples include mineral oil and vegetable oils, and oil materials, such as those already proposed herein as emollients.
  • oils or oily materials include silicone oils, both volatile and non-volatile, such as polydimethyl siloxanes.
  • the oil or oily material when present for the purposes for forming an emulsion, will normally form up to 90%, preferably from 10 to 80% by volume of the composition.
  • composition according to the invention can also optionally comprise one or more emulsifiers the choice of which will normally determine whether a water-in-oil or and oil-in-water emulsion is formed.
  • the chosen emulsifier or emulsifiers should normally have an average HLB value of from 1 to 6.
  • a chosen emulsifier or emulsifiers should have an average HLB value of >6.
  • Suitable emulsifiers are set below in Table 1 in which the chemical name of the emulsifiers is given together with an example of a trade name as commercially available, and the average HLB value.
  • Sorbitan trioleate Arlacel 85 1.8 Sorbitan tristearate Span 65 2.1 Glycerol monoleate Aldo MD 2.7 Glycerol monostearate Atmul 84S 2.8 Glycerol monolaurate Aldo MC 3.3 Sorbitan sesquioleate Arlacel 83 3.7 Sorbitan monooleate Arlacel 80 4.3 Sorbitan monostearate Arlacel 60 4.7 Poloxyethylene (2) stearyl ether Brij 72 4.9 Poloxyethylene sorbitol beeswax derivative G-1702 5 PEG 200 dilaurate Emerest 2622 6.3 Sorbitan monopalmitate Arlacel 40 6.7 Polyoxyethylene (3.5) nonyl phenol Emulgen 903 7.8 PEG 200 monostearate Tegester PEG
  • Polyoxyethylene (9.3) octyl phenol Triton X-100 13.0 Polyoxyethylene (4) sorbitan monolaurate Tween 21 13.3 PEG 600 monooleate Emerest 2660 13.7 PEG 1000 dilaurate Kessco 13.9 Polyoxyethylene sorbitol lanolin derivative G-1441 14.0 Polyoxyethylene (12) lauryl ether Ethosperse LA-12 14.4
  • the amount of emulsifier or mixtures thereof, to be incorporated in the composition of the invention, when appropriate is from 1 to 50%, preferably from 2 to 20% and most preferably from 2 to 10% by weight of the composition.
  • composition of the invention can be anhydrous, it can also comprise water, usually up to 98%, preferably from 5 to 80% by volume.
  • composition of the invention can also optionally comprise a high molecular weight silicone surfactant which can also act as an emulsifier, in place of or in addition to the optional emulsifier(s) already mentioned.
  • a high molecular weight silicone surfactant which can also act as an emulsifier, in place of or in addition to the optional emulsifier(s) already mentioned.
  • the silicone surfactant is a high molecular weight polymer of dimethyl polysiloxane with polyoxyethylene and/or polyoxypropylene side chains having a molecular weight of from 10,000 to 50,000 and having the structure:
  • R 13 and R 14 are each chosen from -H , C 18 alkyl and - [ CH 2 CH 2 0 ] t [ CH 2 CHO ] u H
  • t has a value of from 9 to 115
  • u has a value of from 0 to 50
  • v has a value of from 133 to 673
  • w has a value of from 25 to 0.25.
  • the dimethyl polysiloxane polymer is one in which:
  • t has a value of from 10 to 114 u has a value of from 0 to 49 v has a value of from 388 to 402 w has a value of from 15 to 0.75
  • groups R 13 and R being lauryl, and the other having a molecular weight of from 1000 to 5000.
  • a particularly preferred dimethyl polysiloxane polymer is one in which: t has the value 14 u has the value 13 v has the value 249 w has the value 1.25
  • the dimethyl polysiloxane polymer is conveniently provided as a dispersion in a volatile siloxane, the dispersion comprising, for example, from 1 to 20% by volume of the polymer and from 80 to 99% by volume of the volatile siloxane.
  • the dispersion consists of a 10% by volume of the polymer dispersed in the volatile siloxane.
  • Examples of the volatile siloxanes in which the polysiloxane polymer can be dispersed include polydimethyl siloxane (pentamer and/or hexa er) .
  • a particularly preferred silicone surfactant is cyclomethicone and dimethicone copolyol, such as DC 3225C Formulation Aid available from DOW CORNING.
  • Another is laurylmethicone copolyol, such as DC Q2—5200, also available from Dow Corning.
  • the amount of silicone surfactant, when present in the composition will normally be up to 25%, preferably from 0.5 to 15% by weight of the emulsion.
  • adjuncts examples include preservatives, such as para-hydroxy benzoate esters; antioxidants, such as -tocopherol, humectants, such as glycerol, sorbitol, 2-pyrrolidone-5- carboxylate, dibutylphthalate, gelatin, polyethylene, glycol, preferably PEG 200-600; buffers, such as lactic acid together with a base such as triethanolamine or sodium hydroxide; surfactants, such as glycerol ethers; waxes, such as beeswax, ozokerite wax, paraffin wax, plant extracts, such as Aloe vera, cornflower, witch hazel, elderflower, cucumber; thickeners; activity enhancers; colourants; perfumes; and sunscreen materials such as ultrafine titanium dioxide and organic sunscreens such as p-aminobenzoic acid and esters thereof, ethylhexyl p- methoxycinnamate, 2-ethoxyethy
  • preservatives such
  • the succinic acid derivative is combined with conventional ceramides, pseudoceramides, polyol fatty acid polyesters, sterols, particularly cholesterol, galactosyldiacyl glycerols, phospholipid ⁇ , alkyl polyglucoside ⁇ , glycosphingolipids, fatty acids and esters thereof and mixtures thereof and other ingredients well known to those skilled in the art to produce a liposomal dispersion.
  • a further preferred composition may also contain in combination with the succinic acid derivative and optional additional ingredients disclosed above, an organic acid component chosen from hydroxy carboxylic acids, keto carboxylic acids, esters thereof and mixtures thereof.
  • Cosmetic adjuncts can form the balance of the composition.
  • Use of the Composition can form the balance of the composition.
  • the composition according to the invention is intended primarily as a product for topical application to human skin, especially a ⁇ an agent for reducing the permeability of water through the ⁇ kin, particularly for treating dry, ageing or damaged ⁇ kin, in order to reduce moisture loss, increase stratum corneum flexibility and generally to enhance the quality of skin.
  • the composition may further be used to improve skin desquamation and a ⁇ an agent to influenence epidermal differentiation.
  • the composition can also be applied to hair and nails.
  • a ⁇ mall quantity of the composition for example from 0.2 to 5 ml, is applied to exposed areas of the skin, from a suitable container or applicator and, if necessary, it is then spread over and/or rubbed into the skin using the hand or fingers or a suitable device.
  • the topical skin, hair or nail treatment composition of the invention can be formulated as a lotion having a viscosity of from 4,000 to 10,000 mPas, a fluid cream having a viscosity of from 10,000 to 20,000 mPas or a cream having a visco ⁇ ity of from 20,000 to 100,000 mPa ⁇ , or above.
  • Alternative product forms include liquids, microemulsion ⁇ , mousse ⁇ and gels.
  • the composition can be packaged in a suitable container to suit its visco ⁇ ity and intended u ⁇ e by the con ⁇ umer.
  • a lotion or fluid cream, or the alternative product forms can be packaged in a bottle or a roll-ball applicator or a propellant-driven aerosol device or a container fitted with a pump suitable for finger operation.
  • the composition When the composition is a cream, it can simply be stored in a non-deformable bottle or squeeze container, such as a tube or a lidded jar.
  • the invention accordingly also provides a closed container containing a cosmetically acceptable composition as herein defined.
  • the reduction in water permeability of the skin following topical application of the composition according to the invention can be determined by in vitro measurement of the water vapour transmis ⁇ ion rate (WVTR) u ⁇ ing a water transmission cell adapted from that described by Blank I.H., J. Invest. Dermatol., [1952], 18 . , 433-440.
  • WVTR water vapour transmis ⁇ ion rate
  • Isolated porcine stratum corneum was floated on propan-2-ol contained in a glas ⁇ petri di ⁇ h. The di ⁇ h was gently agitated for 4 hours and the sample of extracted stratum corneum was then removed, floated in saline solution onto spectra mesh and air dried overnight.
  • 850 ⁇ l distilled water was placed in the centre well of the cell and a sample of pretreated stratum corneum (see above) was carefully laid over the well ensuring that it completely covered the O-ring, ⁇ uch that a watertight ⁇ eal wa ⁇ achieved. Care wa ⁇ taken to avoid wrinkle ⁇ , tears and holes in the stratum corneum sample.
  • the transmission cell was then ⁇ crewed into po ⁇ ition and allowed to equilibrate at room temperature before an initial measurement was made.
  • the cell wa ⁇ weighed after 5 minutes, then placed in an incubator at 37°C, 0% RH. Two further weight measurements were taken at suitable interval ⁇ over a period of 24 hours at the the end of which time a test or control solution was applied and two more measurements were taken during a further 21 hours. Five cells were used for each test or control treatment.
  • test material for each test, a solution of test material in chloroform/methanol (2:1 v/v) were prepared at 24 mg/ml concentration. 10 ⁇ l of this solution was applied to the previously selected propan-2-ol extracted skin as described above. The chloroform/methanol quickly evaporated. The five cells containing the skin samples were weighed after 5 minutes prior to placing in the incubator at 37°C, 0% RH. As mentioned above, two weight measurements were then taken at intervals over a period of 21 hours.
  • the WVTR was calculated for each sample (pre and post topical application) as follows:
  • the level of significance was calculated using Duncan's Multiple Range test between WVTR measurements.
  • Example 1 The invention is illustrated by the following examples.
  • Example 1 The invention is illustrated by the following examples.
  • This example illustrates a high internal phase water-in-oil emulsion in accordance with the invention.
  • a high internal phase water-in-oil emulsion having the following formulation was prepared:
  • This example illustrates an oil-in-water cream containing a succinic acide derivative of the invention.
  • This example illustrates an alcoholic lotion containing a succinic acid derivative of the invention.
  • the lotion had the following formulation:
  • This example illustrates an alcoholic lotion containing a succinic acid derivative of the invention.
  • the lotion had the following formulations:
  • composition according to the invention represents a lotion which can be used in the treatment of dry or ageing skin:
  • composition according to the invention represents a lotion which can be used in the treatment of dry or ageing skin:
  • This example illustrates non-aqueous skincare composition:
  • This example illustrates a suntan lotion
  • Succinic acid derivative having the structure (5) 0.02 Acetulan (cetyl acetate and acetylated lanolin alcohol) 4

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

Abstract

Composition destinée à une application locale sur la peau, les cheveux ou les ongles, renfermant: 1) une dose efficace d'un dérivé d'acide succinique présentant une structure de type lipidique; 2) un excipient cosmétiquement acceptable.
PCT/EP1993/003095 1992-11-11 1993-11-04 Composition cosmetique renfermant des esters d'acide succinique WO1994010971A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU54640/94A AU5464094A (en) 1992-11-11 1993-11-04 Cosmetic composition containing succinic acid esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9223578.7 1992-11-11
GB9223578 1992-11-11

Publications (1)

Publication Number Publication Date
WO1994010971A1 true WO1994010971A1 (fr) 1994-05-26

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PCT/EP1993/003095 WO1994010971A1 (fr) 1992-11-11 1993-11-04 Composition cosmetique renfermant des esters d'acide succinique

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995035088A1 (fr) * 1994-06-17 1995-12-28 Henkel Kommanditgesellschaft Auf Aktien Emulsions cosmetiques et/ou pharmaceutiques d'huile dans l'eau
EP0791353A1 (fr) * 1996-02-26 1997-08-27 Shiseido Company Limited Composition absorbant les rayonnements ultraviolets
JPH11500121A (ja) * 1995-02-15 1999-01-06 ビーエーエスエフ アクチェンゲゼルシャフト アルク（エン）イルジカルボン酸ビスエステル、それらの使用、及びそれらの製造方法
WO2002002720A2 (fr) * 2000-07-03 2002-01-10 The Associated Octel Company Limited Additifs de carburant
WO2008057003A1 (fr) * 2006-11-08 2008-05-15 Tatyana Vyacheslavovna Popkova Composition de soin pour les ongles
US8314584B2 (en) 2007-05-08 2012-11-20 Robert Bosch Gmbh Motor arrangement with an electronic isolating relay module
US10617617B1 (en) 2018-12-04 2020-04-14 Momentive Performance Materials Inc. Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361097A1 (fr) * 1976-08-10 1978-03-10 Nisshin Oil Mills Ltd Produits cosmetiques pour les cheveux ou la peau
FR2374027A1 (fr) * 1976-12-20 1978-07-13 Henkel Kgaa Utilisation d'esters alcoxymethyliques d'acides carboxyliques pour l'amelioration de la structure de chevelures endommagees
JPS60136507A (ja) * 1983-12-23 1985-07-20 Kao Corp 風呂水清浄剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361097A1 (fr) * 1976-08-10 1978-03-10 Nisshin Oil Mills Ltd Produits cosmetiques pour les cheveux ou la peau
FR2374027A1 (fr) * 1976-12-20 1978-07-13 Henkel Kgaa Utilisation d'esters alcoxymethyliques d'acides carboxyliques pour l'amelioration de la structure de chevelures endommagees
JPS60136507A (ja) * 1983-12-23 1985-07-20 Kao Corp 風呂水清浄剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 104, no. 4, 27 January 1986, Columbus, Ohio, US; abstract no. 24069w, H. NISHIQUCHI: "bath preparations containing succinate derivatives" *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995035088A1 (fr) * 1994-06-17 1995-12-28 Henkel Kommanditgesellschaft Auf Aktien Emulsions cosmetiques et/ou pharmaceutiques d'huile dans l'eau
JPH11500121A (ja) * 1995-02-15 1999-01-06 ビーエーエスエフ アクチェンゲゼルシャフト アルク（エン）イルジカルボン酸ビスエステル、それらの使用、及びそれらの製造方法
EP0791353A1 (fr) * 1996-02-26 1997-08-27 Shiseido Company Limited Composition absorbant les rayonnements ultraviolets
US5849272A (en) * 1996-02-26 1998-12-15 Shiseido Co., Ltd. Ultraviolet absorbing composition
GB2381789A (en) * 2000-07-03 2003-05-14 Ass Octel Fuel additives
WO2002002720A3 (fr) * 2000-07-03 2002-10-24 Ass Octel Additifs de carburant
WO2002002720A2 (fr) * 2000-07-03 2002-01-10 The Associated Octel Company Limited Additifs de carburant
GB2381789B (en) * 2000-07-03 2004-06-30 Ass Octel Fuel additives
WO2008057003A1 (fr) * 2006-11-08 2008-05-15 Tatyana Vyacheslavovna Popkova Composition de soin pour les ongles
US8314584B2 (en) 2007-05-08 2012-11-20 Robert Bosch Gmbh Motor arrangement with an electronic isolating relay module
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair
US10617617B1 (en) 2018-12-04 2020-04-14 Momentive Performance Materials Inc. Polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
WO2020117509A1 (fr) 2018-12-04 2020-06-11 Momentive Performance Materials Inc. Composés de poly(acide carboxylique) pour le traitement de substrats fibreux à base d'acides aminés, en particulier les cheveux
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair

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