WO1997016167A1 - Cosmetic preparations - Google Patents

Abstract

The invention concerns novel cosmetic agents containing sulphosuccinates of formula (I), in which R1 stands for a behenyl group, R2 stands for R1 or Mg, and m and n, independently of each other, are 0 or numbers from 1 to 10. The preparations are characterized by a high foaming capacity and particularly good tolerance by the mucous membranes.

Description

 "Cosmetic preparations"

Field of the Invention

The invention relates to cosmetic agents containing selected sulfosuccinates and their use in the manufacture of cosmetic agents.

State of the art

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.

Accordingly, 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. Description of the invention

The invention relates to cosmetic compositions containing sulfosuccinates of the formula (I),

SO ₃ mg

I.

R ¹ (OCH ₂ CH ₂ ) _n OOC-CH-CH ₂ -COO (CH ₂ CH ₂ O) _m R ² (I)

in which 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.

Surprisingly, it has been found that 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

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. To prepare them, maleic acid, but preferably maleic anhydride, is usually used, which are esterified in the first step with optionally ethoxylated primary alcohols. At this point, the mono / diester ratio can be adjusted by varying the amount of alcohol and the temperature. In the second step, 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. Milne in R. Soc. Chem. (Ind. Appl. Surf.II) 22, 77 (1990) and W. Hreczuch et al. in J. Am. Oil. Chem. Soc. 2fi, 707 (1993).

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.

Isnside

The preparations according to the invention can contain further anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants.

Typical examples of anionic surfactants are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, α-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 sulfide ether, mono sulfide ether fatty acid, mono sulfide ether, mono sulfide ether, mono sulfide ether, mono sulfide ether, ¬ Bon acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, acyl lactylates, acyl tartrates, acyl glutamates, acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable products based on wheat) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.

Typical examples of 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 , 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.

Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts. Typical examples of 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. Synergistic effects with regard to base foam, foam resistance - even in the presence of water hardness and sebum - and mucous membrane compatibility are achieved if the behenyl sulfosuccinate magnesium salts are used with nonionic and / or amphoteric surfactants, preferably alkyl oligoglucosides, fatty acid N-alkyl glucamides, vegetable Protein hydrolyzates and / or betaines are mixed, the weight ratio being 10:90 to 90:10, preferably 25:75 to 75:25 and in particular 40:60 to 60:40. Cosmetic preparations with particularly advantageous tolerance to the eye mucosa are otherwise obtained if no further anionic surfactants are present; Mixtures of this type are therefore preferred for the production of baby shampoos, for example.

Industrial applicability

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.

Cosmetic preparations

The preparations, such as, for example, hair shampoos, hair lotions or foam baths, bar soaps (combibars and syndet bars) and hand washing pastes, 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, which are usually present as more or less dilute aqueous solutions, 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. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.

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 60 mol ethylene oxide with castor oil and / or hardened castor oil; (a6) Polyol and in particular polyglycerol esters such as polyglycerol polyricin oleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable. The 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. Cι _{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 _/ ι 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. Regarding the glycoside residue, it applies that 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. The 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. Examples of suitable 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.

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.

Examples

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).

Legend: Dibehenyl + 3-SS-Mg = Beheneth-3 Sulfosuccinate Magnesium Salt

Texapon® SB3 = Laureth-3 Sulfosuccinate Sodium Salt

Plantaren® APG 1200 = dodecyl polyglucose

Dehyton® K = Cocoamidopropyl Betaine

Gluadin® WQ = Wheat Hydrolyzed Proteins

Claims

claims 1. Cosmetic preparations containing sulfosuccinates of the formula (I) SO ₃ mg I. R ¹ (OCH ₂ CH ₂ ) _n OOC-CH-CH ₂ -COO (CH ₂ CH ₂ O) _m R ² (I) 1 2 I in which 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. 2. Preparations according to claim 1, characterized in that they contain alkyl oligoglucosides, fatty acid N-alkyl glucamides, vegetable protein hydrolyzates and / or betaines as further surfactant components. 3. Preparations according to claims 1 and 2, characterized in that they contain the sulfosuccinates of the formula (I) in amounts of 1 to 55% by weight, based on the preparations. 4. Use of sulfosuccinates according to claim 1 for the production of cosmetic preparations.