WO1996014824A1 - Hair-regenerating preparations - Google Patents

Abstract

Described are preparations containing an active-substance complex made from a cationic derivative of panthenol and a carbohydrate, such preparations having a significant regenerative effect on split hairs. This action can be increased by the addition of non-ionic or anionic polymers.

Description

 "Hair Regenerating Preparations"

The invention relates to hair cosmetic preparations which contain a special hair-regenerating active ingredient combination.

The human hair is treated in many different ways with hair cosmetic preparations. This includes, for example, cleaning the hair with shampoos and shower preparations and bleaching, dyeing and shaping hair with waving agents, tinting agents and styling preparations. As a result of almost all hair treatments, the hair structure can be undesirably impaired. These impairments can be seen, among other things. in poor wet and dry combability, an increased electrostatic charge, increased brittleness and, in more serious cases, in split, i.e. split hair. This not only worsens the external appearance of the hairstyle, but in particular the hair split should also be counteracted on account of the health of the hair.

A known way to alleviate these abuses is to subject the hair to a post-treatment with appropriate active ingredients, mostly cationic surfactants, which may be combined with other substances.

However, this approach cannot be satisfied on a number of points.

It is known, for example, that cationic surfactants are only suitable for the treatment of non-greasy hair; However, their use with rapidly regreasing hair is problematic, since they put additional strain on the hair and strengthen the natural regreasing of the hair.

It is also unsatisfactory that the treatment with cationic surfactants usually takes place in a separate step, usually a rinse. must follow, since these cationic surfactants often cannot be incorporated into preparations with anionic surfactants such as shampoos.

Alternatively, the path was followed to add special, hair-regenerating active ingredients to the hair, in particular to combat hair splitting. According to German Offenlegungsschrift 37 11 841, the combinations of panthenol with a mono- or disaccharide are distinguished by a strong, hair-regenerating effect, even if they remain on the hair only for a short time.

Finally, it is known from PCT publication WO 92/13829 that quaternized panthenol derivatives are distinguished by an increased substantivity on the hair and, inter alia, counteract the hair splitting caused by combing.

It has now surprisingly been found that the regeneration of split hair can be achieved to a very large extent if the split hair is treated with preparations which contain certain carbohydrates in addition to a quaternized panthenol derivative.

The invention thus relates to preparations for the treatment of keratin fibers, in particular human hair, characterized in that they contain an active ingredient combination consisting of (A) a cationically derivatized panthenol and (B) a carbohydrate selected from monosaccharides, oligosaccharides, On and uronic acids (sugar acids), sugar alcohols, glycosides and quaternized monosaccharides.

Preferred cationically derivatized panthenols (A) are compounds of the formula (I)

in which R, R and R2 independently of one another for an alkyl group with 1-24 carbon atoms or an alkenyl group with 8-24 carbon atoms, 3 for an alkylene group with 1-18 carbon atoms, Y for an OH group or for hydrogen and X for a monovalent one , organic or inorganic anion.

Preferred compounds of the formula (I) are those in which R represents an alkyl or alkenyl group having 8-24 carbon atoms. Such alkyl or alkenyl groups are, for example, lauryl, myristyl, cetyl, stearyl and oleyl groups. R ¹ and R ² are preferably alkyl groups with 1-4 carbon atoms, especially methyl groups. R3 is preferably a shorter alkylene group with 1-4 carbon atoms, in particular a methylene group. Y, due to the production process, preferably represents a hydroxyl group, X represents a halide ion, in particular chloride.

Information regarding the production of these panthenol derivatives can be found in the mentioned publication WO 92/13829, to which reference is expressly made here. A corresponding product is sold by the Tri-K company under the name PANTHEQUAT ^R.

The cationically derivatized panthenols are preferably present in the preparations according to the invention in an amount of 0.05 to 10% by weight, in particular 0.05 to 5% by weight, based on the preparation as a whole.

According to the invention, both monosaccharides and oligosaccharides, such as cane sugar, milk sugar and raffinose, can be used as carbohydrates (B). The use of monosaccharides is preferred. Among the monosaccharides, those compounds are preferred which contain 5 or 6 carbon atoms. Suitable pentoses and hexoses are, for example, ribose, arabinose, xylos, lyxose, allose, old rose, glucose, mannose, gulose, idose, galactose, talose and fructose. Arabinose, glucose, galactose and fructose are preferred carbohydrates; Glucose is especially preferred.

Derivatives of these pentoses and hexoses, such as the corresponding on- and uronic acids (sugar acids), sugar alcohols and glycosides, can also be used according to the invention. Preferred sugar acids are gluconic acid, glucuronic acid, sugar acid, mannosugar acid and mucic acid. Preferred sugar alcohols are sorbitol, mannitol and dulcite. Preferred glycosides are the methyl glucosides.

Quaternized carbohydrates can also be used according to the invention as component (B). The commercial product GlucquatR100 (according to the CTFA nomenclature a lauryl methyl gluceth-10 hydroxypropyl dimonium chloride) is a preferred quaternized carbohydrate.

Since the carbohydrates used are usually obtained from natural raw materials such as starch, the carbohydrates generally have the configurations corresponding to these raw materials (e.g. D-glucose, D-fructose and D-galactose).

The carbohydrates are preferably present in the preparations according to the invention in an amount of 0.1 to 10% by weight, in particular 0.1 to 5% by weight, based on the total preparation.

Furthermore, it was found that certain polymer classes, the representatives of which themselves have no or in combination with panthenol derivatives no increased hair-regenerating properties, increase the hair-regenerating effect in the agents according to the invention in a synergistic manner.

These polymer classes are nonionic and anionic polymers.

Suitable nonionic polymers are, for example: Polyvinylpyrrolidones, such as those sold under the name Luviskol ^R (BASF). Polyvinylpyrrolidones are preferred nonionic polymers in the context of the invention.

Vinyl pyrrolidone / vinyl ester copolymers, such as those sold under the trademark Luviskol ^R (BASF). Lüviskol ^R VA 64 and Luviskol VA 73, each vinylpyrrolidone / vinyl acetate copolymers, are also preferred nonionic polymers.

Cellulose ethers, such as hydroxypropyl cellulose, hydroxyethyl cellulose and methyl hydroxypropyl cellulose, as are sold, for example, under the trademark Culminal ^R and Benecel ^R (AQUALON).

shellac

Examples of anionic polymers suitable according to the invention are:

Polyacrylic and polymethacrylic acids, their salts, their copolymers with acrylic acid and methacrylic acid esters and amides and their derivatives which are obtained by crosslinking with polyfunctional agents. Compounds of this type are, for example, under the names Carbopol ^R 934, Carbopol ^R 934P, Carbopol ^R 940 (Carbopol EDT 2001), Carbopol 941 (Carbopol ^R EDT 2050), Carbopol ^R 950, Carbopol ^R 980, Carbopol ^R 981, Carbopol ^R EDT 2020 and Hostacerin ^R PN 73 available.

Copolymers of acrylic acid and / or methacrylic acid or their esters with Cιo-30-alkyl acrylates, such as those sold under the name Pemulen ^R.

Polyoxycarboxylic acids, such as polyketo- and polyaldehydocarboxylic acids and their salts, such as, for example, P0C ^R HS 5060 and P0C ^R AS5060.

Polymers and copolymers of crotonic acid with esters and amides of acrylic and methacrylic acid, such as vinyl acetate-crotonic acid and vinyl acetate-vinyl propionate-crotonic acid copolymers. Such connections are under the brand names Resyn ^R (NATIONAL STARCH), Luviset ^R (BASF) and Gafset ^R (GAF) in retail; the products Luviset ^R CA-66 and Luviset ^R CAP can be particularly preferred.

Vinyl pyrrolidone / vinyl acrylate copolymers, available, for example, under the trademark Luviflex ^R (BASF). A preferred polymer is the vinyl pyrrolid / acrylate terpolymers available under the name Luviflex ^R VBM-35 (BASF).

Acrylic acid / ethyl acrylate / N-tert-butyl acrylamide terpolymers, which are sold, for example, under the name Ultrahold ^R strong (BASF), and methacrylic acid / ethyl acrylate / t-butyl acrylate terpolymer, which are sold under the name Luvimer ^R 100P (BASF) become.

These nonionic or anionic polymers are preferably used in an amount of 0.01 to 5% by weight, in particular 0.1 to 2% by weight, based on the preparation as a whole.

The preparations according to the invention can furthermore contain surfactants, in particular nonionic surfactants. Non-ionic surfactants contain z. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group. Such connections are, for example

Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 carbon atoms, with fatty acids with 12 to 22 carbon atoms and with alkylphenols with 8 to 15 carbon atoms in the alkyl group,

Cι ₂ -C ₂ 2- ^{fatty acid} mono - ^and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol,

Addition products of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil. Methyl glucose difatty acid esters etherified with oligoglycerin.

Particularly preferred nonionic surfactants are the alkyl polyglycosides of the general formula R0- (Z) _x . These connections are characterized by the following parameters. The alkyl radical R contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred. Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, compounds with an odd number of carbon atoms in the alkyl chain predominate.

The alkyl glycosides which can be used according to the invention can contain only one specific alkyl radical R. Usually, however, these compounds are produced from natural fats and oils or mineral oils. In this case, the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.

Particularly preferred are those alkyl polyglycosides in which R consists essentially of Cg and CiQ alkyl groups, essentially from C ₂ and Ci 4 alkyl groups, essentially from C 6 to C 5 alkyl groups or essentially from C ₂ to C _j ß Alkyl groups.

Any mono- or oligosaccharides can be used as sugar building block Z. Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used. Examples of such sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose. Preferred sugar components are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.

The alkyl polyglycosides which can be used according to the invention contain on average

1.1 to 5 sugar units. Alkyl glycosides with x values from 1.1 to 1.6 are preferred. Alkyl glycosides in which x is 1.1 to 1.4 are very particularly preferred.

The alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can be average contain up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.

The compounds with alkyl groups used as surfactants can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.

In the case of the surfactants, which are addition products of ethylene and / or propylene oxide onto fatty alcohols or derivatives of these addition products, both products with a "normal" homolog distribution and those with a restricted homolog distribution can be used. “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted using alkali metals, alkali metal hydroxides or alkali metal alcoholates. By contrast, narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.

The preparations according to the invention preferably contain surfactants in quantities of 0.2 to 20% by weight, based on the respective preparation.

The other constituents of the hair treatment compositions according to the invention depend on the type of hair treatment composition. In principle, the formulations according to the invention include all known types of hair treatment agents, such as Hair shampoos, hair rinses, hair conditioners, hair treatments, hair fixers, hair sprays, blow-dry waves, permanent waving agents and hair colorants. Hair treatments are a preferred form of the agent according to the invention.

Preferred hair treatment compositions according to the invention are generally those which remain on the hair after use. Nevertheless, it can be In particular cases, it may also be preferred to formulate the agents according to the invention in the form of rinse-off products.

Further constituents of the agents according to the invention can be, for example: anionic surfactants, such as, for example, fatty alkyl sulfates and ether sulfates and alkyl ether carboxylic acids, zwitterionic surfactants, such as betaines, ampholytic surfactants, structurants such as maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and Cephalins, as well as silicone oils, protein hydrolyzates, especially elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids as well as quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,

Solubilizers, such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, dyes,

Anti-dandruff agents such as Piroctone Olamine and zinc Omadine, other substances for adjusting the pH value,

Active ingredients such as panthenol, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, light stabilizers,

Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax, paraffins and fatty alcohols, fatty acid alkanolamides,

Complexing agents such as EDTA, NTA and phosphonic acids,

Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and also primary, secondary and tertiary phosphates, opacifiers such as latex,

Pearlescent agents such as ethylene glycol mono- and distearate, blowing agents such as propane-butane mixtures, N ₂ 0, dimethyl ether, C0 ₂ and air and antioxidants, direct dyes, so-called coupler and developer components as oxidation dye precursors,

Reducing agents such as Thioglycolic acid and its derivatives, thiolactic acid, cysteamine, thio malic acid and α-mercaptoethanesulfonic acid,

Oxidation agents such as hydrogen peroxide, potassium bromate and sodium bromate.

The invention also relates to the use of the compositions according to the invention for the treatment of keratin fibers, in particular hair.

The invention also relates to a method for treating hair, in which a preparation according to the invention is applied to the hair and remains there.

Finally, the invention also relates to a method for treating hair, in which a preparation according to the invention is applied to the hair and rinsed out again after an exposure time (1 to 40 minutes).

The following examples are intended to explain the invention in more detail.

Example: anti-split effect

20 split hairs were immersed in a 12.5% sodium lauryl ether sulfate solution for 5 minutes and rinsed with lukewarm water. The hair was then held in the sample preparations for 5 minutes and dried in a forced-air drying cabinet at 60 ° C. for 30 minutes. This procedure was repeated 5 times and the hair was then examined at room temperature (65% relative atmospheric humidity). The compositions of the sample preparations and the split rates after 5 treatments are shown in Table 1.

Table 1: [all amounts in% by weight]

VI V2 V3 V4 Bl B2

components

Panthequat ^R 1 1.0 - - 1.0 1.0 1.0

Glucose - 0.3 - - 0.3 0.3

Luviskol ^R K 30 ² - - 0.1 0.1 - 0.1

Ethanol 7.0 7.0 7.0 7.0 7.0 7.0

Water - ad 100 -

Split rate [%] 55 100 100 60 30 5

¹ cationic panthenol derivative (45% active ingredient; CTFA name: panthenyl hydroxypropylsteardimonium chloride) (TRI-K Industries)

² polyvinylpyrrolidone (95% active substance, remainder water) (BASF). II. Examples of use

The amounts in the following examples are% by weight.

1) Leave-on hair treatment

Panthequat ^R 1.2

Glucose 0.3

Luviquat ^R FC 550 ³ 0.6

Luviskol ^R K 90 ⁴ 0.4

Ethanol 8.0

Water ad 100

Vinyl imidazolinium methochloride / vinyl pyrrolidone copolymer (50:50) (average molecular weight: approx. 80,000 daltons; 40% active substance; CTFA name: Polyquaternium-16) (BASF) polyvinyl pyrrolidone (95% active substance; CTFA name: PVP) (BASF)

2) Leave-on hair treatment

Panthequat ^R 0.6

Sucrose 0.7

Shellac 0.8

Merquat ^R 280 ⁵ 0.4

Sorbitol 0.5

Ethanol 25.0

Water ad 100

Dimethyldiallylammonium chloride-acrylic acid copolymer (approx. 40% active substance in water; CTFA name: Polyquaternium 22) (CHEMVIR0N) 3) shampoo

Texapon ^R N 28 ⁶ 48.0

Plantaren ^R 2000 UP ⁷ 10.0

Dehyton ^R κ8 8.0

Panthequat ^R 3.0

Lactose 4.0

Luviskol ^R VA 649 1.5

NaCl 0.9

Benzoic acid 0.45

Citric acid ad pH 4.7

Water to 100

Lauryl ether sulfate, sodium salt (28% active ingredient; CTFA name: Sodium Laureth Sulfate (HENKEL)

Cß-iö-fatty alcohol-l ^ -glucoside (approx. 53% active substance; CTFA name: Decyl Polyglucose) (HENKEL)

Fatty acid amide derivative with betaine structure of the formula R- C0NH (CH ₂ ) 3N ⁺ (CH3) ₂ CH ₂ C00- (approx. 30% active substance; CTFA name Cocoa idopropyl Betaine) (HENKEL)

Vinyl pyrrolidone-vinyl acetate copolymer (60:40) (CTFA name: PVP-VA copolymer) (BASF)

4) hair fixer

Carbopol ^R ETD 2001 ¹⁰ 0.65

Panthequat 2.0

Luviskol ^R K 30 2.0

Glucose 2.0

Dow Corning 345 * - * 0.4

Cremophor ^R RH 40 ¹² 0.8

Ethanol 10.0

NaOH ad pH 6.7

Water ad 100 cross-linked polyacrylic acid (CTFA name: Carbomer) (GOODRICH) decamethylcyclopentasiloxane (CTFA name: Cyclomethicone)

(DOW CORNING) castor oil, hydrogenated + 45 ethylene oxide (CTFA name: PEG-40

Hydrogenated Castor Oil) (BASF)

Claims

Claims Preparations for the treatment of keratin fibers, in particular human hair, characterized in that they consist of a combination of active substances (A) a cationically derivatized panthenol and (B) a carbohydrate selected from - monosaccharides, - oligosaccarids, - On and uronic acids (sugar acids), - sugar alcohols, - glycosides and - contain quaternized monosaccharides. Preparations according to claim 1, characterized in that the cationically derivatized panthenol (A) is a compound of formula (I),

in which R, R ^{and R2} independently of one another for an alkyl group with 1-24 carbon atoms or an alkenyl group with 8-24 carbon atoms, R ³ for an alkylene group with 1-18 carbon atoms, Y for an OH group or for hydrogen and X stands for a monovalent, organic or inorganic anion. Preparations according to Claim 2, characterized in that (A) is a compound of the formula (I) in which R is an alkyl or alkenyl group with 8-24 carbon atoms, R ¹ and R ^{2 are} methyl groups, and R ^{3 is} a Alkylene group having 1-4 carbon atoms, Y is a hydroxy group and X is a halide ion. 4. Preparations according to one of claims 1 to 3, characterized gekennzeich¬ net that the carbohydrate (B) is a mono- or disaccharide. 5. Preparations according to claim 1, characterized in that the carbohydrate (B) contains 5 or 6 carbon atoms. Preparations according to claim 5, characterized in that the carbohydrate (B) is glucose. Preparations according to one of Claims 1 to 6, characterized in that they additionally contain a nonionic or anionic polymer. 8. Preparations according to claim 7, characterized in that the polymer is non-ionic. 9. Preparations according to claim 8, characterized in that the non-ionic polymer is a homo- or copolymer of vinyl pyrrolidone. 10. Preparations according to one of claims 1 to 9, characterized gekennzeich¬ net that component (A) in an amount of 0.05 to 10 wt .-%, in particular 0.05 to 5 wt .-%, based on the total Preparation that is included. 11. Preparations according to one of claims 1 to 10, characterized gekennzeich¬ net that the component (B) in an amount of 0.1 to 10 wt .-%, in particular 0.1 to 5% by weight, based on the entire preparation, is present. 12. Preparations according to one of claims 7 to 11, characterized gekennzeich¬ net that the polymer in an amount of 0.01 to 5 wt .-%, in particular 0.1 to 2 wt .-%, based on the entire preparation , is included. 13. A method for treating hair, characterized in that a preparation according to one of claims 1 to 12 is applied to the hair and remains there. 14. A method for treating hair, characterized in that a preparation according to one of claims 1 to 12 is applied to the hair and is rinsed out again after an exposure time.