WO1996010388A1 - Preparations cosmetiques et/ou pharmaceutiques - Google Patents

Preparations cosmetiques et/ou pharmaceutiques Download PDF

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Publication number
WO1996010388A1
WO1996010388A1 PCT/EP1995/003794 EP9503794W WO9610388A1 WO 1996010388 A1 WO1996010388 A1 WO 1996010388A1 EP 9503794 W EP9503794 W EP 9503794W WO 9610388 A1 WO9610388 A1 WO 9610388A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
weight
ether
acidates
fatty
Prior art date
Application number
PCT/EP1995/003794
Other languages
German (de)
English (en)
Inventor
Rolf Wachter
Andreas Sander
Holger Tesmann
Edith Von Kries
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1996010388A1 publication Critical patent/WO1996010388A1/fr

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Classifications

    • 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
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
    • 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

Definitions

  • the invention relates to cosmetic and / or pharmaceutical preparations with improved skin cosmetic compatibility, containing esterification products of vegetable protein hydrolysates and optionally further anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants and a process for the preparation of the esterification products.
  • Protein hydrolysates are degradation products of animal or vegetable proteins, for example collagen, elastin or keratin and preferably almond and potato protein and in particular wheat and soy protein, which are cleaved by acidic, alkaline and / or enzymatic hydrolysis.
  • protein hydrolyzates in the absence of a hydrophobic residue, are not surfactants in the classical sense, they are widely used for the formulation of surface-active agents because of their dispersing properties. Overviews of the production and use of protein hydrolyzates are, for example, by G. Schuster and A. Domsch in Soap oils Fette Wachsen, 108, 177 (1982) and Cosm.Toil. 9, 63 (1984), by HW Steisslinger in Parf.Kosm. 72., 556 (1991) and F.Au ⁇ rich et al. in Tens.Surf.De. 23, 389 (1992).
  • the object of the invention was therefore to provide new cosmetic and / or pharmaceutical agents based on protein breakdown products, the performance and dermatological properties of which are significantly improved.
  • the invention relates to cosmetic and / or pharmaceutical preparations containing
  • the invention further relates to a process for the preparation of esterification products of vegetable protein hydrolyzates, in which a solution of hydrogen chloride gas in a lower alcohol having 1 to 4 carbon atoms, preferably ethanol, is first prepared, and the preferably solid, anhydrous vegetable protein hydrolysates. If desired, the unreacted alcohol can remain in the product and then serves as a preservative detergents or by distillation.
  • the degree of esterification can essentially be set via the reaction time and is in the range from 5 to 90, preferably 25 to 75% of theory.
  • the invention includes the knowledge that it can be advantageous for a number of applications not to strive for complete esterification, but rather partially esterified products, for example with a degree of esterification in the range from 40 to 60 and in particular 45 to Use 55% of theory.
  • the esterification products are not individual discrete compounds, but rather complex homologues which differ in their degree of oligomerization and esterification.
  • esterification products of the vegetable protein hydrolyzates can be used individually. However, mixtures with other surfactants are preferably used.
  • anionic surfactants are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, o-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerin ether sulfates, hydroxymixed ether sulfates, monoglyme ether sulfates, monoglyme ether sulfates , Mono- and dialkyl sulfosuccinates.
  • the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • 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, alk (en) yl oligoglycosides, in particular fatty acid n-protein hydrolysates, especially fatty acid-N-alkylglucose products Soy or wheat base) polyol fatty acid esters, sugar esters, sorbitan esters and polysorbates. 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, aminopropionates, amino glycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example J.Falbe (ed.), “Surf c nts in Consumer Products”, Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.), “Catalysts, surfactants and mineral oil additives”, Thie e Verlag, Stuttgart, 1978, pp. 123-217.
  • esterification products of the vegetable protein hydrolyzates and the further surfactants can be used in a weight ratio of 1:99 to 99: 1, preferably 10:90 to 75:25 and in particular 40:60 to 60:40.
  • the preparations according to the invention are notable for improved foaming power, high substantivity and dermatological compatibility and, in particular, good solubility in water and alcohol, even at low temperatures.
  • suitable preparations are skin and hair care products such as hair shampoos, hair treatments, hair rinses, hair lotions, hair dye and hair waving agents, foam baths, moisturizing and moisturizing creams, sunscreens, ointments, hand lotions and predominantly alcoholic systems such as e.g. After shaves, pre shaves, skin and hair tonics, hair sprays, deodorant sprays and the like.
  • Skin care products such as creams, lotions and the like, generally have - in addition to the surfactants already mentioned - a content of oil bodies, emulsifiers, fats and waxes, stabilizers and superfatting agents, thickeners, biogenic agents, film formers, preservatives, dyes and fragrances.
  • Hair care products such as hair shampoos, hair lotions, foam baths and the like, can contain, in addition to the surfactants already mentioned, emulsifiers, superfatting agents, thickeners, biogenic agents, film formers, preservatives, colorants and fragrances as further auxiliaries and additives.
  • Suitable oil bodies are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, lenstoffatomen preferably 8 to 10 Koh ⁇ , esters of linear C6-C20 ⁇ fatty äuren with li ⁇ -linear Cg-C20 Fet 'koholen tal, esters of branched C6-C13 - Carboxylic acids with linear cis-cig fatty alcohols, esters of linear with branched alcohols, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with dihydric alcohols and / or Guerbet alcohols, triglycerides based on Cß-Cio fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates and / or dialkyl ethers in consideration.
  • Suitable emulsifiers are both known W / 0 and 0 / W emulsifiers, such as, for example, hardened and ethoxylated castor oil, polyglycerol fatty acid esters or polyglycerol poly ricinoleates.
  • Typical examples of fats are glycerides; waxes include beeswax, paraffin wax or microwaxes. in combination with hydrophilic waxes, eg cetyl stearyl alcohol.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate can be used.
  • Substances such as 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 gu, 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 ethoxylates with a narrow homolog distribution or alkyl oligoglucosides and electrolytes such as sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gu, 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
  • 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, polyvinyl pyrrolidone, vinyl pyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives 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 those which are suitable and approved for cosmetic purposes, such as are compiled, for example, in the publication "Cosmetic Dyes” by the Dye Immission of the German Research Foundation, published by Verlag Chemie, Weinheim, 1984, pp. 81-106. These 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 and the non-aqueous proportion (“active substance content”) 20 to 80, preferably 30 to 70% by weight, based on the composition.
  • the preparation of the agents can be carried out in a manner known per se, i.e. for example by hot, cold, hot-hot / cold or PIT emulsification. This is a purely mechanical process, there is no chemical reaction.
  • the reaction mixture was then heated to 80 ° C., a further 10 kg of activated carbon and 120 kg of filter aid (Perlite ( R) P50) were added and the mixture was stirred for 30 minutes.
  • the reaction product was then filtered through a filter press and the filtrate was adjusted to a pH of 11.5 with calcium oxide. After a residence time of 30 min at 90 ° C., the solution was filtered, sodium carbonate solution was added and the calcium salts which had precipitated out were again separated off using a filter press.
  • the filtrate was concentrated in a falling stream evaporator to a content of 41% Brix and, after a storage period of 3 days, was finally filtered until bare. Production of wheat protein ethyl ester.
  • a mixture of 20 kg of ethanol and 0.55 kg of hydrogen chloride gas was prepared with stirring. After this solution had cooled to room temperature, 10 kg of powdered wheat protein hydrolyzate according to Example la) were added. The resulting suspension was stirred for 24 h, then made up to 100 kg with deionized water and adjusted to pH 4.5 with 2.7 kg of 20% strength by weight sodium hydroxide solution. The mixture was then filtered in the presence of 1 kg of filter aid (Perlite ( R ) P50). The wheat protein ethyl ester was obtained in a yield of 96 kg.
  • filter aid Perlite ( R ) P50
  • Wheat protein hydrolyzate from example (Ia) was esterified for 24 h with ethanol according to specification (Ib) and adjusted to a residual ethanol content [EtOH] of 20 to 50% by weight.
  • Aqueous solutions of these products with an active substance content [AS] of 1 or 5% by weight at a temperature (T) of 8 or 20 ° C. were then stored over a period of 24 h and the solutions visually assessed.
  • AS active substance content
  • the non-esterified starting material served as the reference substance.
  • the results are summarized in Table 1 (percentages as% by weight).
  • the foaming power of the products was examined both alone and in a mixture with other surfactants according to the Ross-Miles Test (DIN 53 902, Part 2) in water with a hardness of 16 d, at 23 ° C (1 g AS / 1). The foam height is given after 20 min.
  • test substances were assessed alone and in a mixture with surfactants using two methods.
  • the test on the chorionallantoic membrane of the incubated chicken egg represents a model for the tolerance of a substance to the mucous membrane of the eye. The cytotoxicity is determined.
  • the neutral red method is based on the determination of changes in the ability of cells to absorb the neutral red dye after exposure to the substance to be tested. The relative stimulus potential is determined.
  • A wheat protein hydrolyzate, esterified with ethanol
  • the viscosities were determined in a Brookfield RVF viscometer at 23 ° C., spindle TE (with Helipath) and 4 rpm after a storage time of 1 week.
  • the formulations are understood to be water and 0.2% by weight of preservative ad 100% by weight.
  • An explanation of the trade names can be found in Table 3.
  • Paraffin oil viscous 4.0% by weight
  • Glycerin 86% by weight and 5.0% by weight
  • Emulgade ( R ) SE 8.0% by weight
  • Paraffin oil viscous 4.0% by weight
  • Glycerin 86% by weight and 5.0% by weight
  • Paraffin oil viscous 4.0% by weight
  • Glycerin 86% by weight and 5.0% by weight
  • Emulgade (R) SE 8.0% by weight
  • Glycerin 86% by weight and 5.0% by weight
  • Cutina ( R) CBS 3.0% by weight
  • Emulgade SE Glyceryl Stearate (and) Ceteareth-20
  • Lama cream DGE 18 polyglyceryl-2 PEG-4 stearate

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

Abstract

L'invention concerne de nouvelles préparations cosmétiques et/ou pharmaceutiques, présentant une meilleure compatibilité sur le plan dermatologique et contenant (a) des produits d'estérification d'hydrolysats de protéine végétaux, avec des alcools aliphatiques comportant 1 à 4 atomes de carbone, ainsi que, le cas échéant, (b) d'autres tensioactifs anioniques, non ioniques, cationiques et/ou amphotères ou zwitterioniques.
PCT/EP1995/003794 1994-10-04 1995-09-25 Preparations cosmetiques et/ou pharmaceutiques WO1996010388A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944435384 DE4435384C1 (de) 1994-10-04 1994-10-04 Kosmetische und/oder pharmazeutische Zubereitungen
DEP4435384.7 1994-10-04

Publications (1)

Publication Number Publication Date
WO1996010388A1 true WO1996010388A1 (fr) 1996-04-11

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PCT/EP1995/003794 WO1996010388A1 (fr) 1994-10-04 1995-09-25 Preparations cosmetiques et/ou pharmaceutiques

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WO (1) WO1996010388A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010001193A1 (de) * 2010-01-25 2011-07-28 Dahms, Gerd, 47138 Neue Tensidzusammensetzungen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1617854A1 (de) * 1965-07-23 1969-10-30 Stepan Chemical Co Alkoholloesliche Proteinderivate
FR2297033A2 (fr) * 1975-01-13 1976-08-06 Procter & Gamble Compositions proteinees pour la protection des matieres keratineuses
JPS5913705A (ja) * 1982-07-13 1984-01-24 Nisshin Oil Mills Ltd:The 化粧料の製造方法
EP0361391A2 (fr) * 1988-09-29 1990-04-04 Seiwa Kasei Co., Ltd. Composition pour onduler les cheveux
FR2688229A1 (fr) * 1992-03-09 1993-09-10 Ulice Soc Procede de synthese enzymatique d'esters alkyliques de peptides, produits ainsi obtenus et utilisation desdits produits.

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1617854A1 (de) * 1965-07-23 1969-10-30 Stepan Chemical Co Alkoholloesliche Proteinderivate
FR2297033A2 (fr) * 1975-01-13 1976-08-06 Procter & Gamble Compositions proteinees pour la protection des matieres keratineuses
FR2304669A1 (fr) * 1975-01-13 1976-10-15 Procter & Gamble Compositions detergentes moussantes et de conditionnement
JPS5913705A (ja) * 1982-07-13 1984-01-24 Nisshin Oil Mills Ltd:The 化粧料の製造方法
EP0361391A2 (fr) * 1988-09-29 1990-04-04 Seiwa Kasei Co., Ltd. Composition pour onduler les cheveux
FR2688229A1 (fr) * 1992-03-09 1993-09-10 Ulice Soc Procede de synthese enzymatique d'esters alkyliques de peptides, produits ainsi obtenus et utilisation desdits produits.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8409, Derwent World Patents Index; AN 84-053791 *

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