WO2012084533A1

WO2012084533A1 - Method for shaping keratin-containing fibers

Info

Publication number: WO2012084533A1
Application number: PCT/EP2011/072207
Authority: WO
Inventors: Thorsten Knappe; Helga Flodrop Van; Anna Henschel; Rolf Bayersdörfer; Georg KNÜBEL; Wibke Gross
Original assignee: Henkel Ag & Co. Kgaa
Priority date: 2010-12-23
Filing date: 2011-12-08
Publication date: 2012-06-28
Also published as: DE102010064054A1

Abstract

(C₃ to C₄) ketoses, in particular 1,3-dihydroxyacetone, are suitable for shaping keratin-containing fibers, in particular human hair. When using a shaping process supported by heat, particularly good and long-lasting hold can be achieved.

Description

"Process for reshaping keratin-containing fibers"

The invention relates to the technical field of reshaping keratin-containing fibers, in particular human hair. The invention relates to the use of at least one (C ₃ to C ₄ ) - Ketose for reshaping keratinhaltiger fibers, especially human hair, and a corresponding forming process and usable therein means for forming.

As keratin-containing fibers, in principle all animal hair, e.g. Wool, horsehair, angora hair, furs, feathers and products made therefrom or textiles. However, the invention is preferably used in the context of a hair shaping, in particular the smoothing of curly human hair and wigs made therefrom.

A permanent deformation keratinhaltiger fibers is usually carried out so as to mechanically deform the fiber and determines the deformation by suitable means. Before and / or after this deformation, the fiber is treated with a keratin-reducing preparation. After a rinsing operation, the fiber is then treated with an oxidizing agent preparation in the so-called fixing step, rinsed and freed from the forming aids (e.g., winders, papillots) after or during the fusing step. When, as a keratin reducing component, a mercaptan, e.g. Ammonium thioglycolate is used, this part of the disulfide bridges of the keratin molecule cleaves to -SH groups, so that there is a softening of keratin fibers. In the later oxidative fixation again disulfide bridges are knotted in the hair keratin, so that the Keratingefüge is fixed in the predetermined deformation. Alternatively, it is known to use sulfite instead of the mercaptans for hair styling. By bisulfite solutions and / or sulfite solutions and / or disulfite solutions disulfide bridges of keratin in a sulfitolysis according to the equation

R - S - S - R + HSO ₃ ⁽⁾ ►R - SH + R - S - S0 ₃ ⁽⁾ , thus softening the keratin fiber. Hydrogen sulfite, sulfite or disulfite containing reducing agents do not have the strong odor of the mercaptan-containing agents. The cleavage can be reversed as described above in a fixing step using an oxidizing agent to form new disulfide bridges.

The permanent smoothing of keratin-containing fibers is achieved analogously by the use of keratin-reducing and -oxidierenden compositions. In a similar process, the frizzy hair is either wound on large diameter winders, usually more than 15 mm, or the hair is combed smooth under the action of the keratin reducing composition. Instead of the winder, it is also possible to put the fiber on Smoothing out the smoothing board. Smoothing boards are usually rectangular boards, for example made of plastic. Preferably, the fiber is wetted with the keratin-reducing preparation.

Another way of hair straightening is smoothing with a hot iron. However, the structure of the keratin-containing fiber changes upon heat treatment of the hair during smoothing (see R. McMullen et al., J. Cosmet., Sci., 1998, 49, 223-244). This change in fiber structure should be counteracted by appropriate measures.

In general, the known forming methods, especially in the case of smoothing, have the disadvantage that the keratin-containing fiber is charged electrostatically. In addition, the deformation result of the known methods in terms of the degree of deformation and the uniformity of the deformation is in need of improvement. When an improvement in the degree of deformation is achieved, this is usually accompanied by an increased damage to the keratin-containing fiber.

The object of the invention is therefore to provide a shaping method for keratin-containing fibers, in particular for human hair, which provides a very good and lasting deformation result, which cares for the fiber and protects the structure of the fiber.

Surprisingly, it has been found that the object is achieved by the use of at least one (C ₃ to C ₄ ) -ketose in the context of a reshaping keratin-containing fibers. The keratin fibers are not visibly changed in color.

A first subject of the invention is therefore the use of at least one (C ₃ to C ₄ ) ketose for the transformation of keratin-containing fibers, in particular human hair.

The (C ₃ to C ₄ ) -ketoses according to the invention obey the formula (I)

R-CH-C-CH ₂ OH (I)

I II

OH O wherein R represents a hydrogen atom or a hydroxymethyl group.

The (C ₃ to C ₄ ) -ketoses according to the invention are thus selected from at least one compound of the group which is formed

1, 3-dihydroxyacetone,

D-erythrulose

• L-erythrulose

(|. ₂ )

The use of 1, 3-dihydroxyacetone is particularly preferred according to the invention.

It is inventively preferred if the transformation keratinhaltiger fibers, especially human hair, with the supply of heat in the context of a heat-assisted transformation keratinhaltiger fibers. Thus, it is again particularly preferred at least one (C ₃ to C ₄ ) -Ketose for heat-assisted forming keratinhaltiger fibers, especially human hair, at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, especially preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C). Here, the use of 1, 3-dihydroxyacetone as said ketosis is again preferred. As a heat source is preferably a hot air blower (for example, in the embodiment as a hair dryer, hood or curling iron), a flat iron or a corrugated iron.

Very particular preference is given to at least one (C ₃ to C ₄ ) -ketose (in particular 1, 3-dihydroxyacetone) in the context of a heat-assisted smoothing of keratin-containing fibers, in particular human hair, at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, more preferably 150 ° C to 250 ° C, more preferably 120 ° C to 220 ° C).

In the context of the use according to the invention, it has proven to be favorable to incorporate the (C ₃ to C ₄ ) -ketose into a cosmetic carrier and to use the resulting cosmetic agent for shaping. It turned out to be preferable if the cosmetic agent, based on the total weight of the agent, at least 1, 0 wt .-%, again preferred at least 10.0 wt .-%, more preferably at least 15.0 wt .-%, particularly preferably at least 20.0 wt .-%, most preferably at least 25.0 wt .-%, at least one (C ₃ to C ₄ ) -ketose (especially 1, 3-dihydroxyacetone).

A second aspect of the invention is a cosmetic composition comprising, in a cosmetically acceptable carrier, based on the total weight of the composition, at least 1.0% by weight of a (C ₃ to C ₄ ) -ketose.

It is preferred according to the invention if the agent according to the invention contains the (C ₃ to C ₄ ) -ketoses (in particular 1, 3-dihydroxyacetone) in an amount of at least 10.0% by weight, more preferably of at least 15.0% by weight. %, more preferably at least 20.0 wt .-%, most preferably at least 25.0 wt .-%, each based on the total weight of the composition contains.

With regard to the (C ₃ to C ₄ ) -ketoses and their preferred embodiments, what is said in the first subject of the invention applies mutatis mutandis.

For preparing inventive compositions of the embodiment with 1, 3-dihydroxyacetone as (C ^ to C ₆ ) -Ketose, it is conceivable, the 1, 3-dihydroxyacetone as a monomer and / or in its dimeric form as 2,5-dihydroxy-2, 5-dihydroxymethyl-1, 4-dioxane to use the cosmetic agent.

The agents according to the invention contain the ingredients or active ingredients in a cosmetically acceptable carrier. Preferred cosmetically acceptable carriers are aqueous, alcoholic or aqueous-alcoholic media. Aqueous alcoholic media preferably contain at least 10% by weight of water, in particular at least 30% by weight of water, in each case based on the total agent.

As alcohols, in particular the lower alcohols having 1 to 4 carbon atoms (especially (C 1 to C ₄ ) monohydroxyalkanes) commonly used for cosmetic purposes, such as, for example, ethanol and isopropanol, may be contained. It is inventively preferred at least one (C ^ to C ₄ ) monohydroxyalkane in the inventive compositions in particular in an amount of 1 to 50 wt .-% in particular from 5 to 30 wt .-% use.

The cosmetically acceptable carrier of the agent according to the invention very particularly preferably contains at least 10% by weight of water and 0 to 50% by weight of at least one (C 1 -C ₄ ) -monohydroxyalkane (in particular at least 30% by weight of water and optionally 5%) to 30 wt .-% of at least one (C ^ to C ₄ ) monohydroxyalkane), each based on the total weight of the composition according to the invention. As additional co-solvents, organic solvents or a mixture of solvents having a boiling point below 400 ° C. may be present in an amount of from 0.1 to 15% by weight, preferably from 1 to 10% by weight, based on the total agent according to the invention. Particularly suitable as additional co-solvents are unbranched or branched hydrocarbons such as pentane, hexane, isopentane and cyclic hydrocarbons such as cyclopentane and cyclohexane. Further, particularly preferred water-soluble solvents are glycerol, ethylene glycol and 1, 2-propylene glycol in an amount of up to 30 wt .-% based on the total agent.

It is preferred according to the invention if the agent, based on the total weight of the composition, contains less than 0.5% by weight (in particular less than 0.1% by weight) of sulfur-containing keratin-reducing compounds. The agents according to the invention are particularly preferably free from sulfur-containing, keratin-reducing compounds. Keratin reducing compounds are capable of reductively cleaving keratin fiber disulfide groups to form thiol groups.

In one embodiment of the invention, it is preferred that the agent according to the invention additionally contains at least one setting polymer selected from at least one compound from the group consisting of strengthening nonionic polymers, setting anionic polymers, setting amphoteric polymers and setting cationic polymers.

According to the invention, polymers are understood as meaning compounds which are made up of a large number of molecules in which one or more types of atoms or atomic groups (so-called constitutive units, basic units or repeating units) are repeatedly arranged next to one another and which has a molecular weight of at least 10,000 g / mol have. The polymers are obtained by polyreaction, the latter being synthetic (i.e., synthetic) or natural.

Firming polymers contribute to the maintenance and / or build-up of the hair volume and hair fullness of the overall hairstyle. These polymers are at the same time also film-forming polymers and therefore generally typical substances for shaping hair treatment agents such as hair fixatives, hair foams, hair waxes, hair sprays. The film formation can be quite selective and connect only a few fibers.

In addition, the agent according to the invention preferably contains at least one consolidating cationic polymer.

The additional strengthening cationic polymers have at least one structural unit containing at least one permanently cationized nitrogen atom. Under permanent cationization Nitrogen atoms are to be understood as meaning those nitrogen atoms which carry a positive charge and thereby form a quaternary ammonium compound. Quaternary ammonium compounds are usually prepared by reacting tertiary amines with alkylating agents such as methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide. Depending on the tertiary amine used, the following groups are known in particular: alkylammonium compounds, alkenylammonium compounds, imidazolinium compounds and pyridinium compounds. Preferred agents in the context of this embodiment comprise the setting cationic polymers in an amount of from 0.1 to 20.0% by weight, more preferably from 0.2 to 10.0% by weight, most preferably from 0.5 wt .-% to 5.0 wt .-%, each based on the weight of the composition.

The cationic fixing polymers can be selected according to the invention from cationic, quaternized cellulose derivatives. In general, such cationic, quaternized celluloses prove to be advantageous in the sense of the embodiment which carries more than one permanent cationic charge in a side chain.

Of these, among the cationic cellulose derivatives are those which are prepared from the reaction of hydroxyethylcellulose with a dimethyldiallylammonium reactant (in particular dimethyldiallylammonium chloride), if appropriate in the presence of further reactants.

Also suitable are those cationic setting polymers which comprise at least one structural unit of the formula (N1) and at least one structural unit of the formula (N2) and, if appropriate, at least one structural unit of the formula K1

)

wherein

R and R ⁴ independently of one another represent a hydrogen atom or a methyl group,

A and A ² are each independently a group of ethane-1, 2-diyl, propane-1, 3-diyl or

Butane-1, 4-diyl,

R ² , R ³ , R ⁵ and R ⁶ independently of one another represent a (C 1 -C ₄ ) -alkyl group,

R ⁷ is a (C ₈ to C ₃₀ ) alkyl group.

Suitable compounds are, for example, as Copolymers of diethyl sulfate quaternized dimethylaminoethyl methacrylate, with N-vinylpyrrolidone having the INCI name Polyquaternium-1 1,

Copolymers of methacryloylaminopropyllauryldimethylammonium chloride with N-vinylpyrrolidone and dimethylaminopropylmethacrylamide with the INCI name Polyquaternium-55,

Copolymers of methacryloylaminopropyllauryldimethylammonium chloride with N-vinylpyrrolidone, N-vinylcaprolactam and dimethylaminopropylmethacrylamide with the INCI name Polyquaternium-69.

In the context of this embodiment, it is again preferred according to the invention if at least one copolymer (c1) which additionally comprises a structural element of the formula (N1) in addition to at least one structural element of the formula (K2) is present as the consolidating cationic polymer

wherein

R is a (C 1 to C ₄ ) -alkyl group, in particular a methyl group.

Particular preference is given to N-methylvinylimidazole / vinylpyrrolidone copolymers which are designated according to INCI nomenclature as Polyquaternium-16 and N-methylvinylimidazole / vinylpyrrolidone copolymers, which are referred to as Polyquaternium-44 according to INCI nomenclature.

Particularly preferred polymers are also N-

Methylvinylimidazole / vinylpyrrolidone / vinylcaprolactam copolymers, which according to INCI nomenclature are referred to as Polyquarternium-46.

Finally, N-

Methylvinylimidazole / vinylpyrrolidone / vinylimidazole / methacrylamide copolymers, which according to INCI nomenclature are referred to as Polyquaternium-68.

Among the additional strengthening cationic polymers selected from the cationic polymers having at least one structural element of the above formula (K2), the following are preferred:

N-vinylpyrrolidone / 1-vinyl-3-methyl-1H-imidazolium chloride copolymers,

N-vinylpyrrolidone / 1-vinyl-3-methyl-1H-imidazolium methylsulfate copolymers,

N-vinylpyrrolidone / N-vinylcaprolactam / 1-vinyl-3-methyl-1H-imidazolium terpolymer,

- N-vinylpyrrolidone / methacylamide / N-vinylim

copolymer, and mixtures of these polymers.

The reinforcing nonionic polymers are preferably contained in the agent of this embodiment in an amount of from 0.1% to 20.0% by weight, more preferably from 0.2% to 15.0% by weight. , very particularly preferably from 0.5 wt .-% to 10.0 wt .-%, each based on the weight of the inventive composition.

The compositions according to the invention particularly preferably contain at least one chitosan as nonionic setting polymer. In addition to the chitosans as typical biopolymers come within the meaning of the invention as derivatives alkoxylated chitosans in question.

Agents preferred according to the invention are characterized in that they contain as chitosan at least one neutralization product of chitosan with at least one organic carboxylic acid. In this case, it is preferred according to the invention to select the organic carboxylic acid from lactic acid, pyrrolidonecarboxylic acid, nicotinic acid, hydroxyisobutyric acid, hydroxyisovaleric acid or mixtures of these acids.

The chitosans or their derivatives are preferred in the inventive compositions in an amount of 0.01 wt .-% to 5 wt .-%, particularly preferably from 0.05 wt .-% to 2.0 wt .-%, completely particularly preferably from 0.1% by weight to 1% by weight, based in each case on the weight of the composition according to the invention.

The strengthening nonionic polymers are preferably selected from at least one

Polymer of the group that is formed out

Homopolymers and nonionic copolymers of N-vinylpyrrolidone,

Homopolymers and nonionic copolymers of vinyl alcohol

nonionic copolymers of isobutene.

An agent which comprises, as a consolidating nonionic polymer, at least one polymer selected from the group formed

polyvinylpyrrolidone,

Copolymers of N-vinylpyrrolidone and vinyl esters of carboxylic acids having 2 to 18 carbon atoms, in particular N-vinylpyrrolidone and vinyl acetate,

Copolymers of N-vinylpyrrolidone and N-vinylimidazole and methacrylamide,

Copolymers of N-vinylpyrrolidone and N-vinylimidazole and acrylamide,

Copolymers of N-vinylpyrrolidone with NN-DC _! to C ₄₎ alkylamino (C ₂ to C ₄₎ -alkylacrylamid, copolymers of N-vinylpyrrolidone with N, N-di _(C! to C ₄₎ alkylamino (C ₂ to C ₄₎ -alkylacrylamid, are according to the invention very particularly preferred. Further possible means according to the invention with additional nonionic setting polymer are characterized in that they comprise as nonionic setting polymer at least one copolymer containing at least one further structural unit of formula (N1) and at least one structural unit of formula (M3) and at least one structural unit of formula Contains (N3)

A particularly preferred polymer is selected from the polymers of INCI name VP / methacrylamide / vinyl imidazole copolymer.

The compositions according to the invention may also contain as consolidating polymer at least one consolidating amphoteric polymer. An example of a usable according to the invention setting amphoteric polymer is the acrylic resin commercially available as Amphomer ^®, which is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group Acrylic acid, methacrylic acid and their simple alkyl esters. The strengthening amphoteric polymers are preferably present in the water-based compositions which can be used according to the invention in amounts of from 0.01% by weight to 20% by weight, particularly preferably from 0.05 to 10% by weight, based on the total composition. Quantities of 0.1 to 5 wt .-% are very particularly preferred.

Furthermore, at least one solidifying anionic polymer can be used as setting polymers. When the composition of the invention contains a solidifying anionic polymer, it is preferably in the form of a spray, in particular an aerosol spray.

The solidifying anionic polymers are polymers which have carboxylate and / or sulfonate groups. Examples of anionic monomers from which such polymers may consist are acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid. The acidic groups may be wholly or partly present as sodium, potassium, ammonium, mono- or triethanolammonium salt. The setting anionic polymers are preferred in the composition according to the invention in an amount of 0.1 wt .-% to 20.0 wt .-%, particularly preferably from 0.2 wt .-% to 15.0 wt .-%, completely particularly preferably from 0.5 wt .-% to 10.0 wt .-%, each based on the total composition. Particularly preferred polymers of this type are selected from at least one polymer of the group formed

- Copolymers of vinyl acetate and crotonic acid.

- copolymers of vinyl propionate and crotonic acid,

- Copolymers of vinyl neodecanoate, vinyl acetate and crotonic acid.

Further particularly preferred polymers are selected from at least one polymer of the group which is formed from copolymers of acrylic acid and ethyl acrylate and N-tert-butylacrylamide.

In addition, the water-based composition which can be used according to the invention as an anionic setting polymer may contain at least one polyurethane having at least one carboxyl group (for example a copolymer of isophthalic acid, adipic acid, 1,6-hexanediol, neopentyl glycol). The setting anionic polymers are preferably contained in an amount of 0.1 wt .-% to 15 wt .-%, in particular from 0.5 wt .-% to 10 wt .-%, each based on the weight of the water-based composition ,

It has proved to be particularly preferred if the agents according to the invention additionally contain at least one cationic surfactant. Again, cationic surfactants selected from quaternary ammonium compounds, esterquats and amidoamines or mixtures thereof are preferred. Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylbenzylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83. The long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.

Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element. Preferred esterquats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines. Such products are marketed under the trade names Stepantex® ^®, ^® and Dehyquart® Armocare® ^®. The products Armocare ^® VGH-70, a N, N-bis (2-palmitoyloxyethyl) dimethylammonium chloride, as well as Dehyquart ^® F-75, Dehyquart ^® C-4046, Dehyquart ^® L80 and Dehyquart ^® AU-35 are examples of such esterquats. The alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines. An inventively particularly suitable compound from this group of substances under the name Tegoamid ^® S 18 commercial stearamidopropyl dimethylamine is.

The cationic surfactants are contained in the agents according to the invention preferably in amounts of 0.05 to 10 wt .-%, based on the total agent. Amounts of 0.1 to 5 wt .-% are particularly preferred.

It has proved to be particularly preferred if the agents according to the invention additionally comprise at least one nonionic surfactant.

Nonionic surfactants contain as hydrophilic group e.g. a polyol group, a polyalkylene glycol ether group, or a combination of polyol and polyglycol ether groups. Such compounds are, for example

- Addition products of 2 to 100 moles of ethylene oxide and / or 1 to 5 moles of propylene oxide to linear and branched fatty alcohols having 8 to 30 carbon atoms, to fatty acids having 8 to 30 carbon atoms and to alkylphenols having 8 to 15 carbon atoms in the alkyl group,

- With a methyl or (C ₂ to C ₆ ) -alkyl radical endgruppenverschlossene addition products of 2 to 50 moles of ethylene oxide and / or 1 to 5 moles of propylene oxide to linear and branched fatty alcohols having 8 to 30 carbon atoms, to fatty acids having 8 to 30 C atoms and alkylphenols having 8 to 15 C atoms in the alkyl group,

C ₂ -C ₃₀ -fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol,

Adducts of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil,

Polyol fatty acid esters, such as the commercial product Hydagen® HSP (Cognis) or Sovermol types (Cognis),

- alkoxylated triglycerides,

alkoxylated fatty acid alkyl esters of the formula (E4-I)

R CO- (OCH ₂ CHR ² ) _w OR ³ (E4-I)

in which R is CO for a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms, R ^{2 is} hydrogen or methyl, R ^{3 is} linear or branched alkyl radicals having 1 to 4 carbon atoms and w is a number from 1 to 20 .

- amine oxides,

Sorbitan fatty acid esters and adducts of ethylene oxide with sorbitan fatty acid esters such as the polysorbates,

Sugar fatty acid esters and addition products of ethylene oxide with sugar fatty acid esters,

Adducts of ethylene oxide with fatty acid alkanolamides and fatty amines,

Sugar surfactants of the alkyl and alkenyl oligoglycoside type of formula (E4-II),

R ₄ Q- [G] p (E4-II) in which R ^{4 is} an alkyl or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10. They can be obtained by the relevant methods of preparative organic chemistry.

The alkylene oxide addition products of saturated linear fatty alcohols and fatty acids with in each case 2 to 100 mol of ethylene oxide per mole of fatty alcohol or fatty acid have proven to be very particularly preferred nonionic surfactants. Preparations with excellent properties are also obtained when they contain as nonionic surfactants C ₂ -C ₃₀ fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol and / or addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil ,

The agents according to the invention as surfactant very particularly preferably contain at least one addition product of from 15 to 100 mol of ethylene oxide, in particular from 15 to 50 mol of ethylene oxide, to a linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms. These are very particularly preferably ceteareth-15, ceteareth-25 or ceteareth-50.

The agents preferably have a pH of 2 to 1 1. The pH range between 2 and 8 is particularly preferred. The pH value in the context of this document refers to the pH at 25 ° C., unless stated otherwise.

The compositions of the invention may further contain the auxiliaries and additives which are usually added to conventional styling agents.

As suitable auxiliaries and additives in particular additional care substances are mentioned.

As a care material, for example, a silicone oil and / or a silicone gum can be used.

Silicone oils or silicone gums which are suitable according to the invention are in particular dialkyl and alkylaryl siloxanes, for example dimethylpolysiloxane and methylphenylpolysiloxane, and also their alkoxylated, quaternized or else anionic derivatives. Preference is given to cyclic and linear polydialkylsiloxanes, their alkoxylated and / or aminated derivatives, dihydroxypolydimethylsiloxanes and polyphenylalkylsiloxanes.

Dimethicones form the second group of silicones which may be present according to the invention. These may be both linear and branched as well as cyclic or cyclic and branched.

Dimethicone copolyols form another group of silicones that are suitable. Of course, the teaching according to the invention also encompasses the fact that the dimethiconols, dimethicones and / or dimethicone copolymers can already be present as an emulsion.

Particularly suitable silicones are amino-functional silicones, in particular the silicones, which are summarized under the INCI name Amodimethicone.

The agents contain the silicones preferably in amounts of from 0.01% by weight to 15% by weight, particularly preferably from 0.05 to 2% by weight, based on the total agent.

As a care substance of another class of compounds, the agent may contain, for example, at least one protein hydrolyzate and / or one of its derivatives.

The protein hydrolysates are present in the agents according to the invention, for example, in concentrations of from 0.01% by weight to 20% by weight, preferably from 0.05% by weight to 15% by weight and very particularly preferably in amounts of 0 , 05 wt .-% up to 5 wt .-%, each based on the total application preparation included.

As a care substance, the agent according to the invention may further comprise at least one vitamin, a provitamin, a vitamin precursor and / or one of their derivatives. Very particular preference is given to using D-panthenol as care substance, if appropriate in combination with at least one of the abovementioned silicone derivatives.

As a conditioner, the compositions according to the invention may further contain at least one plant extract.

Mono- or oligosaccharides can also be used as a care substance in the compositions according to the invention. The mono- or oligosaccharides are preferably present in the compositions according to the invention in an amount of from 0.1 to 8% by weight, particularly preferably from 1 to 5% by weight, based on the total application preparation.

The agent may further contain at least one lipid as a care substance. The agents according to the invention preferably contain the lipids in amounts of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight, based on the total application preparation.

Furthermore, oil bodies are suitable as a care substance.

The natural and synthetic cosmetic oil bodies include, for example:

- vegetable oils.

liquid paraffin oils, isoparaffin oils and synthetic hydrocarbons and di-n-alkyl ethers having a total of from 12 to 36 carbon atoms, in particular 12 to 24 carbon atoms, such as, for example, di-n-octyl ether, di-n-decyl ether, di-n- nonyl ether, di-n-undecyl ether, di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl n-decyl ether, n-decyl n-undecyl ether, n-undecyl n-dodecyl ether and n-hexyl n-undecyl ether and di-tert-butyl ether, di-iso-pentyl ether, di-3-ethyldecyl ether, tert-butyl-n-octyl ether, iso-pentyl-n-octyl ether and 2-methyl-pentyl-n-octyl ether. - Ester oils. Ester oils are to be understood as meaning the esters of C ₆ - C ₃₀ fatty acids with C ₂ - C ₃₀ fatty alcohols.

- dicarboxylic acid ester,

symmetrical, unsymmetrical or cyclic esters of carbonic acid with fatty alcohols, for example described in DE-OS 197 56 454, glycerol carbonate or dicaprylyl carbonate (Cetiol® CC),

Triflic acid esters of saturated and / or unsaturated linear and / or branched fatty acids with glycerol,

- fatty acid partial glycerides, which are understood to mean monoglycerides, diglycerides and their technical mixtures. With the use of technical products production reasons may still contain small amounts of triglycerides. The partial glycerides preferably follow the formula (D4-I),

CH ₂ O (CH ₂ CH ₂ O) _m R

I

CHO (CH ₂ CH ₂ O) _n R ² (D4-I)

I

CH ₂ O (CH ₂ CH ₂ O) _q R ³

in which R, R ² and R ³ independently of one another represent hydrogen or a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18, carbon atoms, with the proviso that at least one of these groups represents an acyl radical and at least one of these groups is hydrogen. The sum (m + n + q) is 0 or numbers from 1 to 100, preferably 0 or 5 to 25. Preferably, R is an acyl radical and R ² and R ^{3 are} hydrogen and the sum (m + n + q ) is 0. Typical examples are mono- and / or diglycerides based on caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, Elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. Preferably, oleic acid monoglycerides are used.

The amount used of the natural and synthetic cosmetic oil bodies in the compositions according to the invention is usually from 0.1 to 30% by weight, based on the total application preparation, preferably from 0.1 to 20% by weight, and in particular from 0.1 to 15% by weight. %.

Although each of the aforementioned care substances alone already gives a satisfactory result, in the context of the present invention, all embodiments are also included, in which the agent contains a plurality of care substances also from different groups.

By adding a UV filter, both the agents themselves and the treated fibers can be protected from the harmful effects of UV radiation. The UV filters are usually contained in amounts of 0.01-5 wt .-%, based on the total application preparation. Amounts of 0.1-2.5 wt .-% are preferred. In a particular embodiment, the composition according to the invention also contains one or more substantive dyes.

Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols. Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, HC Red 1, HC Red 1, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 1, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds and 1, 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1, 4-bis (ß-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- (ß- hydroxyethyl) aminophenol, 2- (2'-hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) amino-4-methyl-2-nitrobenzene, 1-amino-4- (2'-hydroxyethyl ) - amino-5-chloro-2-nitrobenzene, 4-amino-3-nitrophenol, 1- (2'-ureidoethyl) amino-4-nitrobenzene, 4-amino-2-nitrod iphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, 2-hydroxy-1,4-naphthoquinone, picramic acid and its salts, 2-amino-6-chloro-4-nitrophenol, 4- Ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-1-hydroxy-4-nitrobenzene. Preference is given to using cationic substantive dyes. Particularly preferred are

(a) cationic triphenylmethane dyes such as Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14,

(b) aromatic systems substituted with a quaternary nitrogen group, such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as

(C) substantive dyes containing a heterocycle having at least one quaternary nitrogen atom, as mentioned for example in EP-A2-998 908, to which reference is explicitly made at this point in claims 6 to 1 1 are called.

The dyes which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51 are very particularly preferred cationic substantive dyes of group (c). The cationic substantive dyes sold under the trademark Arianor® are also very particularly preferred cationic substantive dyes according to the invention.

The agents according to the invention according to this embodiment preferably contain the substantive dyes in an amount of 0.001 to 20 wt .-%, based on the total agent.

It is preferred according to the invention that the agents according to the invention are free of oxidation dye precursors. Oxidation dye precursors are classified into so-called developer components and coupler components. Form the developer components under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components, the actual dyes.

The formulation of the compositions according to the invention can be carried out in all forms customary for styling agents, for example in the form of solutions which can be applied to the hair as hair lotions or pump or aerosol spray, in the form of creams, emulsions, waxes, gels or surfactant-containing foaming solutions or other preparations suitable for use on the hair.

A third object of the invention is a method for reshaping, in particular for smoothing, keratin-containing fibers, in particular human hair, in which

(i) a cosmetic agent containing, in a cosmetically acceptable carrier, at least one (C ₃ to C ₄ ) -ketose (preferably a cosmetic agent of the second subject of the invention) is applied to the fibers,

(ii) the fibers after an exposure time

- not be rinsed and

- optionally dried,

(iii) the fibers are subjected to a heat treatment,

(iv) optionally rinsing the fibers.

In a method which is preferred according to the invention, the fibers are formed with the aid of deformation aids

- deformed after, before or during step (i), and / or

- deformed during step (iii).

Deformation aids in the sense of the method according to the invention can

- e.g. Curlers or papillots in the case of a perm,

- or auxiliary for a mechanical smoothing, such as a comb or a brush, a smoothing board or a heated flat iron in case of hair straightening.

Mechanical smoothing is understood according to the invention to mean stretching of the curly fiber along its longest spatial extent.

It is preferred, in the context of a hair straightening, to smooth the fibers mechanically during the contact time from step (ii), in particular by combing or with the aid of a smoothing board.

If the shaping aids, for example winder, are attached to the fiber by means of a corrugated process for a longer period of time, it is expedient to remove these deformation aids after step (iv). In a preferred embodiment of the invention, the keratin-containing fibers are moistened prior to step (i). This can be done by spraying the fibers with a liquid, preferably water. Preferably, prior to step (i), the fibers are shampooed with a conventional shampoo, rinsed and then toweled with a towel. After completion of the terry step remains a noticeable residual moisture in the hair back.

The reaction time of step (ii) is preferably 5-150 minutes, more preferably 10-60 minutes.

It is preferred according to the invention to dry the fibers in step (ii) before the heat treatment of step (iii). A dry keratin-containing fiber according to step (ii) of the method according to the invention is present when the water residues adhering to the hair have evaporated to such an extent that the hairs fall individually. Preferably, in dry keratin fiber, either the moisture content of the fiber is substantially in equilibrium with the humidity of the air, or the fiber absorbs moisture from the ambient air. Such a dry fiber is preferably obtained by drying the wet fiber with hot air using a hair dryer. The drying in step (ii) is preferably carried out if after step (ii) a heat treatment takes place in the context of a forming process, in which the surface of the keratin-containing fibers is directly with a tempered surface of a forming aid (eg flat iron or corrugated iron) during a forming step ,

In a preferred embodiment, in step (iii), the fibers are subjected to a heat treatment with simultaneous deformation of the fiber at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, more preferably 100 ° C to 250 ° C). more preferably 140 ° C to 220 ° C). Simultaneous deformation means that during the heat treatment the fiber is transformed into a mold, e.g. by mechanical smoothing or fixation of the form by Wckler or Papilloten, brought or held.

In a specific embodiment, as part of a hair straightening the fibers in step (iii) a heat treatment with mechanical smoothing of the fiber at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, particularly preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C). The heat treatment can be done with hot air. In this case, the fiber is heated during the combing exactly at the point where the mechanical smoothing takes place. Moreover, it is particularly preferred that the heat treatment in the manner of smoothing with the aid of a so-called smoothing iron with appropriately tempered plates, in particular metal or ceramic plates, takes place in which the plate is pressed onto the fiber to be smoothed and pressed onto the fiber plate is moved along the fiber. The plates may optionally be coated with heat resistant materials. Particularly preferred is the keratin-containing fiber to be smoothed between two pressed according to tempered plates and both plates simultaneously moved along the longest spatial extent of the fiber. It is again preferred that both plates are connected to each other, so that both plates can be moved uniformly along the fiber. When the heat treatment is performed on living hair, the fiber is attached to one end (hair root). The plates in this case are preferably moved evenly away from the hair root along the entire fiber. This movement causes a mechanical smoothing of the fiber. A suitable device for heat treatment, for example, the device "Ceramic Fiat-Master" (sold by: Efalock, Germany) or Schwarzkopf Professional: Model No: IP30A.

In a further embodiment, as part of a corrugation, the fibers are heat-treated under mechanical curling of the fiber in a step (iii) following step (ii) at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C , more preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C). The heat treatment can be done with a hot air blower. In this case, either the fiber is wound around a corresponding hot air curling iron and heated precisely at the point where the Krausung occurs. Or the fibers are wound on curlers as a deformation aid and heated with a hair dryer. Another possibility of heat-assisted corrugation takes place in which the fibers are wound around a rod with a correspondingly heated surface without the use of a hot-air blower and heated precisely at the point at which the curling takes place. A suitable device for heat treatment, for example, the device from Schwarzkopf Professional, Model No: CPL Type F37.

Furthermore, the fibers can be treated as part of a post-treatment at the end of the process according to the invention with a commercial conditioner.

B e i s p e e l e

All amounts are in weight percent based on the total weight of the composition unless otherwise indicated.

1 .0 Example recipe

The following cosmetic agent according to the invention was prepared by mixing the components.

Table 1 :

Raw material amount

1, 3-dihydroxyacetone 30.00

Cetyltrimethylammonium chloride 0.17

Silk protein hydrolyzate 0.03

with 3- (N-lauryl-N, N-dimethyl-ammonium) -2-hydroxypropyl-modified,

0.35

hydrolyzed wheat protein

Chitosan lactate 0.90

Polyquaternium-4 1, 40

Ethanol 15.00

Water, fully desalinated ad 100

2.0 proof of effect:

For the proof of action, the following compositions were provided. The compositions marked with E are according to the invention, the V marked are non-inventive compositions. The compositions marked S are comparative standards.

Table 2:

E1 E2 E3 E4 V1 V2 V3 S1 S2

1, 3-dihydroxyacetone 6.0 10.0 25.0 32.0 - - - - -

Vanillin - - - - 5.0 - - - -

DL-Glyceraldehyde - - - - - 3,0 - - -

4-hydroxy-2-methoxybenzaldehyde - - - - - - 6.0 - -

Ethanol - - - - 47.5 48.5 47.0 - 50.0

Water <- -ad 100> 100 50.0 2.1 Conduct hair straightening

For each formulation according to Table 2, a hair strand of "Frizzy Hair" (15 grams, 15 cm in length, bonded with epoxy resin at one end; VWR; PO # 4505423007149H) was used, as was one strand of hair with the standard formulation S1 and another with the standard formulation S2 treated accordingly.

1 . The hair strand was washed with an alkaline shampoo: (Schwarzkopf) "Global Keratin Clarifying Shampoo" (pH = 8.45), the water temperature being about 35 to 39 ° C. The hair strand became 1 gram for about 1 minute shampooed the said shampoo and then rinsed under clean water (about 1 minute).

2. The lock of hair was slightly squeezed between tissues but not completely dried.

3. In the case of knotted hair of the strand of hair, the strand was carefully unraveled with a comb of horn.

4. The strand of hair was as smooth as possible and placed straight on a watch glass and drizzled with the composition of the invention. The product was lightly rubbed in with a finger (wear gloves!). The strand of hair was well moistened.

5. The agent according to the invention acted for 1 hour.

6. Subsequently, excess product between two fingers was scraped off the lock of hair and the strand was subsequently squeezed between tissues so that it was no longer dripping wet.

7. With the hair dryer (brand: BaByliss type S25) the strand of hair was dried. Care was taken to blow dry the streak as smoothly as possible. Aid here was a comb of horn. The foehn temperature was about 80 to 120 ° C.

8. Meanwhile, the flat iron (brand: Schwarzkopf Professional, Model No: IP30A) was heated at the highest level (210 ° C) for at least 10 minutes. The temperature between the heating plates measured with a contact thermometer (brand: Qtemp 300) was 180 ° C after 10 minutes.

9. Now the dried strand of hair was smoothed with the preheated flat iron. Care was taken to the following guidance of the flat iron along the hair fiber: 3x short (1 second per hair strand), Ixlang (5 seconds per strand of hair), 3x short, I xlang.

The temperatures reached fluctuate between 146 and 181 ° C.

10. The hair strand was hung for 2 days and allowed to rest.

1 1. After this time the tress was washed under the same conditions as indicated in point 1.

12. The lock of hair was slightly squeezed between tissues but not completely dried. 13. With the hair dryer (brand: BaByliss type S25) the strand of hair was dried. Care was taken to blow dry the streak as smoothly as possible. Aid here was a comb of horn. The foehn temperature was about 80 to 120 ° C.

14. Now the strand of hair was hung on a leash for about 30 minutes.

15. Thereafter, the tress was dipped in a beaker with water until completely wetted. The water was easily expressed between the fingertips. Then the tress was hung on a leash again and allowed to air dry.

16. The smoothing result was evaluated on the air-dried tress.

2.2 Carrying out hair rush

4. The strand of hair was wound with the aid of lace paper around a plastic winder, fixed with a hair clip, placed on a watch glass and drizzled with the composition according to the invention. The strand of hair was well moistened.

5. The agent according to the invention acted for 1 hour.

6. Subsequently, the Wckler was placed with the tress on a new watch glass and dried in a warming cabinet at 45 ° C. It was then removed from the oven and allowed to cool.

7. Meanwhile, the curling iron (brand: Schwarzkopf Professional, Model No: CPL Type F37) was heated to the highest level (30) for at least 10 minutes. The temperature measured with a contact thermometer (brand: Qtemp 300) was 150 ° C. after 10 minutes.

8. Now the dried strand of hair was carefully removed from the winder and wrapped around the curling iron for 1 minute. The temperature fluctuated between 140 and 149 ° C.

9. The hair strand was placed on a clean watch glass for 2 days and allowed to rest. 10. After this time the tress was washed under the same conditions as indicated in point 1 and with the shampoo "Syoss Nutrition Oil Care".

1 1. The strand of hair was gently squeezed between 2 fingers and wound again on plastic wrappers. It took again tip paper and hair clamps to help.

12. The winder and hair strand was again dried at 45 ° C in a warming cabinet, then removed from the oven and allowed to cool.

13. The hair strand was carefully detached from the winder and allowed to rest for one hour.

14. Thereafter, the tress was immersed in a beaker of water until completely wetted. The water was easily expressed between the fingertips.

15. Then the tress was put back on a watch glass and allowed to air dry.

16. The curl result was evaluated on the air-dried tress.

2.3 Assessment of forming results

The strands formed with E1 to E4 were compared with standard S1. The strands formed with the means V1 to V3 were compared with the standard S2.

The standard of evaluation was:

+++ much better than standard

++ much better than standard

+ better than standard

0 just like standard

Table 3: Evaluation

E1 E2 E3 E4 V1 V2 V3

Rating + + ++ +++ 0 0 0

Claims

Patent claims

1 . Use of at least one (C ₃ to C ₄ ) -ketose for reshaping keratin-containing fibers, in particular human hair.

2. Use according to claim 1, characterized in that the (C ₃ to C ₄ ) -Ketose for heat-assisted forming keratin fibers, in particular human hair, at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, more preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C) is used.

3. Cosmetic agent containing in a cosmetically acceptable carrier, based on the total weight of the composition, at least 1, 0 wt .-% of a (C ₃ to C ₄ ) -Ketose.

4. Cosmetic composition according to claim 3, characterized in that the (C ₃ to C ₄ ) -Ketosen in an amount of at least 10.0 wt .-%, more preferably of at least 15.0 wt .-%, particularly preferably at least 20.0 wt .-%, most preferably at least 25.0 wt .-%, each based on the total weight of the composition, are included.

5. Cosmetic composition according to one of claims 3 or 4, characterized in that it contains as a (C ₃ to C ₄ ) -ketose 1, 3-dihydroxyacetone.

6. Cosmetic composition according to one of claims 3 to 5, characterized in that the cosmetically acceptable carrier of the agent according to the invention, based in each case on the total weight of the agent according to the invention, at least 10 wt .-% water and 0 to 50 wt .-% of at least one (C ^ to C ₄ ) monohydroxyalkane.

7. A method for reshaping, in particular for smoothing, keratin-containing fibers, in particular human hair, in which

(i) a cosmetic agent comprising, in a cosmetically acceptable carrier, at least one (C ₃ to C ₄ ) -ketose, preferably a cosmetic agent of the second subject matter to which fibers are applied,

(ii) the fibers after an exposure time

- not be rinsed,

- optionally dried,

(iii) the fibers are subjected to a heat treatment,

(iv) optionally rinsing the fibers.

8. The method according to claim 7, characterized in that in step (i) a cosmetic agent according to any one of claims 3 to 6 is applied.

9. The method according to any one of claims 7 or 8, characterized in that the fibers are dried in step (ii). Method according to one of claims 7 to 9, characterized in that in step (iii) a heat treatment with simultaneous deformation of the fiber at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, particularly preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C).