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EP0858320A1 - Preparations cosmetiques - Google Patents

Preparations cosmetiques

Info

Publication number
EP0858320A1
EP0858320A1 EP96934806A EP96934806A EP0858320A1 EP 0858320 A1 EP0858320 A1 EP 0858320A1 EP 96934806 A EP96934806 A EP 96934806A EP 96934806 A EP96934806 A EP 96934806A EP 0858320 A1 EP0858320 A1 EP 0858320A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
preparations
fatty acid
sulfosuccinates
surfactants
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Withdrawn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
EP96934806A
Other languages
German (de)
English (en)
Inventor
Catherine Le Hen Ferrenbach
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.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0858320A1 publication Critical patent/EP0858320A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/02—Alkyl sulfonates or sulfuric acid ester salts derived from monohydric alcohols
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61Q19/10—Washing or bathing 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
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

Definitions

  • the invention relates to cosmetic agents containing selected sulfosuccinates and their use in the manufacture of cosmetic agents.
  • Sulfosuccinates are anionic surfactants which, in addition to outstanding technical properties, also have a particularly high level of ecotoxicological compatibility. For these reasons, sulfosuccinates are widely used today for producing hand dishwashing detergents and, in particular, cosmetic products for which foaming power and skin tolerance are two decisive parameters. Nevertheless, there is a constant need in the market for products with further improved properties and, in particular, increased dermatological compatibility, in order to be able to satisfy customers who are particularly easily prone to skin and mucous membrane irritations.
  • the object of the invention was to provide new cosmetic compositions based on sulfosuccinates, which are characterized by significantly improved dermatological compatibility with at least consistently good foaming power.
  • the invention relates to cosmetic compositions containing sulfosuccinates of the formula (I),
  • R represents a behenyl radical
  • R represents R or Mg and m and n independently of one another represent 0 or numbers from 1 to 10.
  • sulfosuccinate magnesium salts based on behenyl alcohols or behenyl alcohol ethoxylates not only have a particularly strong foaming power, but at the same time also have a very high tolerance to the mucous membrane. These two properties make the products interesting for use in a variety of cosmetic products.
  • Sulfosuccinates which are also referred to as sulfosuccinic acid esters, are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry.
  • maleic acid but preferably maleic anhydride
  • the first step with optionally ethoxylated primary alcohols.
  • the mono / diester ratio can be adjusted by varying the amount of alcohol and the temperature.
  • bisulfite is added, which is usually carried out in the solvent methanol. More recent reviews of the manufacture and use of sulfosuccinates are, for example, from T. Schoenberg in Cosm. Toil. 104, 105 (1989), J.A.
  • Typical examples are sulfosuccinic acid mono- and / or dibehenyl esters in the form of their magnesium salts; the behenyl alcohol can be etherified with an average of 1 to 10 and preferably 1 to 5 moles of ethylene oxide, both conventional and preferably have a narrow homolog distribution.
  • Examples include di-n-behenyl sulfosuccinate and monobehenyl + 3EO sulfosuccinate in the form of their magnesium salts.
  • the preparations according to the invention can contain further anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants.
  • anionic surfactants are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, hydroxymixed ether sulfates, amine sulfide ether, mono sulfide ether fatty acid, monoglyl glyceride fatty acids, mono sulfide ether sulfate, monoglyl glyceride, fatty acid (mono sulfide ether), mono sulfide ether fatty acid, mono sulfide ether, mono sulfide ether, mono sulfide ether fatty acid, mono
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, alkyl oligoglucosides, fatty acid N-alkylglucamides, protein hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, sugar hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, especially vegetable hydrolysates, Sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, amino propionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, see relevant reviews for example J.Falbe (ed.), “Surfactants in Consumer Products”, Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), “Catalysts, Surfactants and Mineral Oil Additives”, Thieme Verlag, Stuttgart, 1978, pp. 123-217.
  • the preparations according to the invention are distinguished by a high foaming power and a particularly advantageous tolerance to the mucous membrane.
  • Another object of the invention therefore relates to the use of the sulfosuccinates mentioned at the outset for the production of cosmetic preparations, in which they can be present in amounts of 1 to 50, preferably 5 to 35% by weight, based on the composition.
  • the solids content of these compositions is likewise usually 5 to 55% by weight and preferably 15 to 35% by weight.
  • the preparations can contain, as further auxiliaries and additives, emulsifiers, superfatting agents, thickeners, cation polymers, silicone compounds, biogenic active substances, film formers, preservatives, colorants and fragrances contain.
  • the proportion of the sulfosuccinates in the cosmetic compositions can be 1 to 55, preferably 5 to 35% by weight, based on the preparations.
  • Nonionic, ampholytic and / or zwitterionic surface-active compounds which are distinguished by a lipophilic, preferably linear alkyl or alkenyl group and at least one hydrophilic group can be used as emulsifiers or co-emulsifiers.
  • This hydrophilic group can be both an ionogenic and a nonionic group.
  • Non-ionic emulsifiers contain as a hydrophilic group z.
  • Preferred agents are those which contain nonionic surfactants from at least one of the following groups as OAV emulsifiers: (al) addition products of 2 to 30 mol of ethylene oxide and / or 0 to 5 mol of propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms , on fatty acids with 12 to 22 C atoms and on alkylphenols with 8 to 15 C atoms in the alkyl group; (a2) C 12 / i 8 fatty acid monoesters and diesters of addition products of 1 to 30 mol ethylene oxide onto glycerol; (a3) glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products; (a4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogues and (a5) addition products of 15 to
  • adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C ⁇ 2 / i 8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • Cg / ⁇ 8 - alkyl mono- and oligoglycosides their preparation and their use as surface-active substances are, for example, from US 3,839,318, US 3,707,535, US 3,547,828, DE-OS 19 43 689, DE-OS 20 36 472 and DE-Al 30 01 064 and EP-A 0 077 167 are known. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyldimethylammonium glycinate, and 2-alkylyl 1- 3-carboxy-1-methyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a Cg / 18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 / lg -acyl sarcosine.
  • Possible W / O emulsifiers are: (b1) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil; (b2) partial esters based on linear, branched, unsaturated or saturated C 12-2 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol) and polyglucosides (eg cellulose); (b3) trialkyl phosphates; (b4) wool wax alcohols; (b5) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives; (b6) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 11 65574 and (b7) polyalkylene glycols.
  • Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as, for example, fatty alcohol alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as table salt and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L, Grünau GmbH), polyethyleneimine, cationic silicone polymers such as e.g.
  • Amidomethicone or Dow Corning, Dow Corning Co./US copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Cartaretine®, Sandoz / CH), polyamino polyamides such as e.g. described in FR-A 22 52 840 and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese / US, quaternized ammonium salt polymers such as Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol / US.
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine and / or alkyl modified silicone compounds.
  • Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. This - 8th -
  • Dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the foaming power was determined according to the Ross Miles Test (DIN 53 902, Part II) at a temperature of 20 ° C and a water hardness of 16 ° d.
  • the amount of surfactants used was 1 g of active substance / 1.
  • the dermatological tolerance was assessed on the chorionallantoic membrane of the incubated chicken egg (HET-CAM), which represents a model for the tolerance of a substance to the eye mucosa.
  • the cytotoxicity was determined relative to a comparative product of the trade.
  • the example formulations 1 to 4 are according to the invention, the example formulations VI to V4 are used for comparison.
  • the composition of the formulations and cytotoxicity and foam levels are summarized in Table 1 (percentages as% by weight).
  • Texapon® SB3 Laureth-3 Sulfosuccinate Sodium Salt
  • Plantaren® APG 1200 dodecyl polyglucose
  • Gluadin® WQ Wheat Hydrolyzed Proteins

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne de nouveaux agents cosmétiques qui contiennent des sulfosuccinates de la formule (I), dans laquelle R1 désigne un reste béhényle, R2 désigne R1 ou Mg, et m et n valent, indépendamment l'un de l'autre, 0 ou des nombres compris entre 1 et 10. Ces compositions se caractérisent par un haut pouvoir moussant et par une tolérance particulièrement bonne au niveau des muqueuses.
EP96934806A 1995-11-02 1996-10-24 Preparations cosmetiques Withdrawn EP0858320A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19540830 1995-11-02
DE19540830A DE19540830A1 (de) 1995-11-02 1995-11-02 Kosmetische Zubereitungen
PCT/EP1996/004617 WO1997016167A1 (fr) 1995-11-02 1996-10-24 Preparations cosmetiques

Publications (1)

Publication Number Publication Date
EP0858320A1 true EP0858320A1 (fr) 1998-08-19

Family

ID=7776438

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96934806A Withdrawn EP0858320A1 (fr) 1995-11-02 1996-10-24 Preparations cosmetiques

Country Status (3)

Country Link
EP (1) EP0858320A1 (fr)
DE (1) DE19540830A1 (fr)
WO (1) WO1997016167A1 (fr)

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5015414A (en) * 1988-09-08 1991-05-14 Kao Corporation Low-irritant detergent composition containing alkyl saccharide and sulfosuccinate surfactants
DE4007808A1 (de) * 1990-03-12 1991-09-19 Henkel Kgaa Oberflaechenaktive mischungen
DE4217673A1 (de) * 1992-05-29 1993-12-02 Huels Chemische Werke Ag Elektrolytverdickbare Tensidkombinationen
DE4301994C1 (de) * 1993-01-26 1994-08-25 Wella Ag Haar- und Körperreinigungsmittel
DE4331297A1 (de) * 1993-09-15 1995-03-16 Henkel Kgaa Stückseifen
JP3207034B2 (ja) * 1993-12-29 2001-09-10 サンスター株式会社 洗浄剤組成物
JPH07197079A (ja) * 1993-12-29 1995-08-01 Sunstar Inc 洗浄剤組成物
DE4416566A1 (de) * 1994-05-11 1995-11-16 Huels Chemische Werke Ag Wäßrige viskoelastische Tensidlösungen zur Haar- und Hautreinigung
ES2179108T3 (es) * 1994-08-10 2003-01-16 Kao Corp Composicion detergente.
DE4435387C2 (de) * 1994-10-04 1997-08-14 Henkel Kgaa Pumpfähige wäßrige Tensidkonzentrate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9716167A1 *

Also Published As

Publication number Publication date
DE19540830A1 (de) 1997-05-07
WO1997016167A1 (fr) 1997-05-09

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