DE202013011967U1 - Compositions for dyeing and straightening hair - Google Patents

Abstract

Hair straightening composition having a pH of 4 or less, comprising: - 0.1 to 40% by weight of glyoxylic acid and / or a hydrate thereof and / or a salt thereof; and 0.1 to 20% by weight of an amino-modified silicone; each based on the total weight of the composition.

Description

Field of the invention

The present invention relates to compositions for use in a process for dyeing and semi-permanent hair straightening in two steps.

Background of the invention

One known method for straightening curly or frizzy hair involves the use of a straightening iron. The high temperature of the iron leads to a break in the hydrogen bonds in the keratin of the hair, causing a temporary smoothing. The hydrogen bonds are re-formed by the action of moisture, so that the hair returns to its original shape over time due to the humidity, and the smoothness effect after washing the hair disappears.

The shape of the hair is largely determined by the disulfide bonds linking two cysteine units of the hair keratin. To effect more permanent shaping of the hair, known methods include cleavage of the disulfide bonds by the action of a sulfide or thio group-containing reducing agent. After the hair has been formed into the desired shape, new disulfide bonds are formed by the use of an oxidizing agent such as hydrogen peroxide, thereby fixing the shape of the hair. However, the use of such agents can damage the hair.

As an example of this type of hair styling treatment is on GB 1 416 564 Which describes reducing compositions comprising thioglycolates or thiolactates as reducing agents, as well as fixing compositions comprising hydrogen peroxide as the oxidizing agent. The reducing compositions may further comprise a salt of an acid such as glyoxylic acid as a buffering agent.

As an alternative to the two-step reduction and oxidation process described above, the disulfide bridges can also be cleaved by the action of an alkaline agent such as sodium hydroxide at a pH of about 11 or higher. Under these conditions, the disulfide (or cystine) moiety undergoes a disproportionation reaction to eliminate sulfur, and is cleaved into an alpha-beta-unsaturated dehydro-alanine moiety and a cysteine moiety. After the hair has been formed into the desired shape, the dehydro-alanine units and the cysteine units form thioether bonds and combine to form lanthionine, stabilizing the smoothed state of the hair. Since the disulfide or cystine units are converted to lanthionine units, this type of hair straightening process using an alkaline agent is also called lanthionization.

Both the two-step reduction / oxidation process and the lanthionization process are based on cleavage of the disulfide bonds and the formation of new bonds among the hair proteins, resulting in an irreversible change in the shape of the hair. That is, these methods can cause a permanent smoothing, wherein the treated part of the hair retains its shape, and the smoothing effect only disappears due to hair growth.

Recently, it has been found that carboxylic acids having a carbonyl group adjacent to the carboxy group, such as glyoxylic acid, known as buffering agents in cosmetic compositions, may have a semi-permanent smoothing effect when used in combination with mechanical smoothing agents. In this context, semi-permanent means that the hair retains its smooth appearance over several wash cycles. This contrasts with permanent smoothing in which the shape of the hair is irreversibly modified, as in the disulphide bond-based cleavage processes described above, and in contrast to the transient smoothening achieved with a straightening iron which disappears by the action of moisture ,

In this regard describes WO 2011/104282 a semi-permanent hair straightening method comprising applying a composition comprising an α-keto acid to the hair, keeping the composition in contact with the hair for 15 to 120 minutes, drying the hair and straightening the hair with a straightening iron at a temperature of 200 ± 50 ° C included.

Further describes WO 2012/010351 a treatment for semi-permanent smoothing of curly, frizzy or wavy hair by applying a solution of glyoxylic acid in combination with mechanical smoothing using a flat iron at a temperature of 200 ± 30 ° C. It is said that the hair retains its shape after treatment for at least six consecutive washes.

Hair dyeing methods and agents can be classified according to the type of dye and the permanence of the color on the hair. Depending on the permanence of the color, hair dyes are typically classified as "permanent", "demi-permanent", "semi-permanent" or "temporary". Permanent and demi-permanent dyes are typically formed by oxidation dyes, while direct dyes are used for semi-permanent or temporary dyeing.

Oxidative dyes are formed from low molecular weight intermediates known as "precursors" or "couplers" (couplers). These molecules are small enough to penetrate the hair. The precursors are usually aromatic para compounds such as 1,4-diaminobenzene and are used alone or in combination with aromatic meta compounds such as 1,3-diaminobenzene as a coupler. By the action of an oxidizing agent such as hydrogen peroxide under alkaline conditions, the precursor is oxidized and reacts with the coupler to form the dye molecule.

Typically, the oxidative dyeing composition comprises ammonia as the alkaline agent to cause swelling of the hair, thereby enhancing the penetration of the precursor and the coupler into the hair. The effect of the oxidizing agent couples the intermediates inside the hair. Since the size of the dye molecule thus formed is larger than the size of the intermediates, the dye molecule remains trapped inside the hair, so that a permanent coloration can be achieved.

In the case of direct dyes, the actual dye molecule is applied to the hair and adheres, for example due to electrostatic interactions on the hair surface. In contrast to the oxidation dye intermediates, penetration of the direct dyes into the hair is relatively weak due to the larger molecular size. As a result, direct dyes can be washed out, so that the coloration is only temporary.

Some direct dyes, especially nitro dyes, may adhere more to the hair and may penetrate deeper into the hair surface to a degree. Dyeing compositions containing these dyes are less easily washed out and therefore termed semi-permanent.

However, the combination of these hair dyeing and smoothing processes has not yet been described in the prior art.

Summary of the invention

The present invention relates to a hair straightening composition having a pH of 4 or less, comprising:
0.1 to 40% by weight of glyoxylic acid and / or a hydrate thereof and / or a salt thereof; and
0.1 to 20% by weight of an amino-modified silicone;
each based on the total weight of the composition.

Furthermore, the invention relates to the use of the composition for straightening hair using a flat iron, which has a temperature in the range of 130 to 250 ° C, preferably 180 ± 50 ° C.

In particular, this use can be carried out in combination with a dyeing composition comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidising agent, for dyeing the hair before smoothing.

• (a) Aufbringen der Färbezusammensetzung auf das Haar,
• (b) Belassen der Zusammensetzung auf dem Haar für 5 bis 45 Minuten, Abspülen der Zusammensetzung und optional Waschen des Haars mit Shampoo,
• (c) optionales Trocknen des Haars,
• (d) Auftragen der Glättungszusammensetzung auf das Haar,
• (e) Belassen der Zusammensetzung auf dem Haar für 1 bis 120 Minuten,
• (f) optionales Spülen des Haars mit Wasser,
• (g) Trocknen des Haars,
• (h) Behandeln des Haars mit einem Eisen, das eine Oberflächentemperatur von 130–250°C, vorzugsweise 180 ± 50°C aufweist, und
• (i) optionales Spülen des Haars und Trocknen des Haars,

worin die Schritte (d) bis (i) direkt nach den Schritten (a) bis (c) durchgeführt werden.This coloring and smoothing is done by the following steps, which are performed in this order:

• (a) applying the coloring composition to the hair,
• (b) leaving the composition on the hair for 5 to 45 minutes, rinsing off the composition and optionally washing the hair with shampoo,
• (c) optional drying of the hair,
• (d) applying the smoothing composition to the hair,
• (e) leaving the composition on the hair for 1 to 120 minutes,
• (f) optionally rinsing the hair with water,
• (g) drying the hair,
• (h) treating the hair with an iron having a surface temperature of 130-250 ° C, preferably 180 ± 50 ° C, and
• (i) optionally rinsing the hair and drying the hair,

wherein steps (d) to (i) are performed directly after steps (a) to (c).

In this context, "immediately after" means that the time interval between the completion of steps (a) to (c) and the start of steps (d) to (i) is not more than two to three hours, preferably not more than one Hour, more preferably not more than 30 minutes.

The described method achieves a semi-permanent smoothing of the hair. Generally, hair straightening can be divided into two main categories. The first is permanent smoothing, where the shape of the hair is irreversibly altered, either by a two-step reduction and oxidation process, or alternatively by treating the hair with a strongly alkaline composition having pHs of 11.0 or above.

The second is semi-permanent straightening in which the hair is relatively reversibly smoothed and returns to its original shape after a certain number of washing cycles. The present invention relates to semi-permanent smoothing, and does not include cleavage of disulfide bonds by sulfur-based or alkali reducing agents.

The coloring composition and / or the smoothing composition may suitably contain other ingredients such as surfactants and / or conditioning components defined below, and may suitably be in the form of a solution, emulsion, cream, paste and mousse.

Detailed description of the invention

Conventionally, hair dyeing and smoothing treatment is performed in two separate sessions, which is time consuming and uneconomical for consumers. Hair coloring, especially under alkaline conditions, usually causes hair damage, resulting in poor color stability.

In addition, it is also known that conventional hair straightening methods damage the hair, for example, by the action of the disulfide-cleaving agents and / or by the means for forming new disulfide bonds. Accordingly, the combination of conventional hair straightening immediately after hair dyeing was likely to result in severe hair damage, resulting in a hazy appearance and diminished color stability since the dye can be washed out by the cracks and fractures formed.

In other words, if a conventional hair straightening treatment is performed immediately after a dyeing treatment, the colors are quickly washed out of the hair, so that the dyed hair loses its attractive appearance in terms of glossiness and vividness of the colors relatively quickly.

The present invention solves this problem by using a dyeing and a smoothing composition which achieves dyeing and smoothing of the hair in two steps in direct succession.

For this purpose, the invention employs a first composition (coloring composition) comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent, and a second composition (smoothing composition) comprising glyoxylic acid. The hair is treated sequentially with these compositions so that the smoothing treatment is performed immediately after the staining treatment.

By the term "immediately after", it is meant that the time interval between the two treatments is not more than two or three hours, preferably not more than one hour, more preferably not more than 30 minutes.

It has surprisingly been found by the inventors of the present invention that dyeing and smoothing processes carried out in direct succession (for example at the same salon visit) result in less hair damage, better color and smoothing stability compared to two separate sessions, so that the hair after using the present Invention, retains its newly achieved cosmetic properties for a longer period of time, that is, longer lasting staining and smoothing effects are obtained.

1. The dyeing composition

The coloring composition used in the present invention contains at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidizing agent. The at least one hair dye is generally at least one direct dye, at least one oxidation dye or a combination thereof. That is, the coloring composition may be a direct dyeing composition or an oxidation dyeing composition. For example, the oxidation dye compositions described in U.S. Pat EP 2 407 149 described or the compositions described in EP 2 329 809 described and comprising a combination of an oxidation dye and a direct dye can be used.

The coloring composition may suitably comprise further ingredients such as surfactants and / or conditioning components as defined below, and may suitably be in the form of a solution, emulsion, cream, paste or mousse.

direct dye

The coloring composition may comprise a direct dye. According to the invention, there are no restrictions on the nature of the direct dye, and any direct dye suitable for hair dyeing can be used.

Examples of the direct dye include an anionic dye, a nitro dye, a disperse dye and a cationic dye, and mixtures thereof.

Nonlimiting examples of the cationic dye are Basic Blue 6, Basic Blue 7, Basic Blue 9, Basic Blue 26, Basic Blue 41, Basic Blue 99, Basic Brown 4, Basic Brown 16, Basic Brown 17, Natural Brown 7, Basic Green 1 Basic Orange 31, Basic Red 2, Basic Red 12, Basic Red 22, Basic Red 51, Basic Red 76, Basic Violet 1, Basic Violet 2, Basic Violet 3, Basic Violet 10, Basic Violet 14, Basic Yellow 57 and Basic Yellow 87 and mixtures thereof. Particularly preferred are Basic Red 51, Basic Orange 31, Basic Yellow 87 and mixtures thereof.

Nonlimiting examples of the anionic dye are Acid Black 1, Acid Blue 1, Acid Blue 3, Food Blue 5, Acid Blue 7, Acid Blue 9, Acid Blue 74, Acid Orange 3, Acid Orange 6, Acid Orange 7, Acid Orange 10 Acid red 1, acid red 14, acid red 18, acid red 27, acid red 50, acid red 52, acid red 73, acid red 87, acid red 88, acid red 92, acid red 155, acid red 180, acid Violet 9, Acid Violet 43, Acid Violet 43, Acid Yellow 1, Acid Yellow 23, Acid Yellow 3, Food Yellow No. 8, D & C Brown No. 1, D & C Green no. 5, D & C Green no. 8, D & C Orange No. 4, D & C Orange No. 10, D & C Orange No. 11, D & C Red No. 21, D & C Red no. 27, D & C Red no. 33, D & C Violet 2, D & C Yellow no. 7, D & C Yellow No. 8, D & C Yellow No. 10, FD & C Red 2, FD & C Red 40, FD & C Red no. 4, FD & C Yellow No. 6, FD & C Blue 1, Food Black 1, Food Black 2, Disperse Black 9 and Disperse Violet 1 and their alkali metal salts such as the sodium or potassium salt, and mixtures thereof.

Among these are the preferred anionic dyes Acid Red 52, Acid Violet 2, Acid Red 33, Acid Orange 4, Acid Red 27 and Acid Yellow 10 and their salts. Even more preferred anionic dyes are Acid Red 52, Acid Violet 2, Acid Red 33, Acid Orange 4 and Acid Yellow 10 and their salts and mixtures thereof.

Non-limiting examples of the nitro dye are HC Blue No. 2, HC Blue No. 4, HC Blue No. 5, HC Blue No. 6, HC Blue No. 7, HC Blue No. 8, HC Blue No. 9, HC Blue No. 10, HC Blue No. 11, HC Blue No. 12, HC Blue No. 13, HC Brown No. 1, HC Brown No. 2, HC Green No. 1, HC Orange No. 1, HC Orange No. 2, HC Orange No. 3, HC Orange No. 5, HC Red BN, HC Red No. 1, HC Red No. 3, HC Red No. 7, HC Red No. 8, HC Red No. 9, HC Red No. 10, HC Red No. 11, HC Red No. 13, HC Red No. 54, HC Red No. 14, HC Violet BS, HC Violet No. 1, HC Violet No. 2, HC Yellow No. 2, HC Yellow No. 4, HC Yellow No. 5, HC Yellow No. 6, HC Yellow No. 7, HC Yellow No. 8, HC Yellow No. 9, HC Yellow No. 10, HC Yellow No. 11, HC Yellow No. 12, HC Yellow No. 13, HC Yellow No. 14, HC Yellow No. 15, 2-amino-6-chloro-4-nitrophenol, picric acid, 1,2-diamino-4-nitrobenzene, 1,4-diamino-2-nitrobenzene, 3-nitro-4-aminophenol, 1-hydroxy-2- amino-3-nitrobenzene and 2-hydroxyethyl picric acid and mixtures thereof.

The coloring composition may suitably comprise only a direct dye or a combination of direct dyes. In this regard, direct dyes of different ionic character may also be included in the same composition.

The total amount of the direct dye in the composition is in the range of 0.001 to 10% by weight, preferably 0.01 to 7.5% by weight, more preferably 0.05 to 5% by weight, based on the total weight of the coloring composition ,

If the dyeing composition comprises only direct dyes, an oxidizing agent is not required to dye the hair. If lightening of hair color is desired, an oxidizing agent may be included in the composition.

oxidation dye

If the dyeing composition comprises an oxidation dye, it is typically of the two-component type wherein the first component comprises the oxidation dye intermediates (precursors and couplers) and an alkalizing agent, while the second component comprises an oxidizing agent such as hydrogen peroxide. The two components are typically stored separately and combined before application to the hair.

In the present invention, there are no particular restrictions on the oxidation dye intermediates, and known precursors and couplers normally used in a hair dyeing product can be suitably used.

Non-limiting examples of the precursor include para-phenylenediamine, toluene-2,5-diamine, 2-chloro-para-phenylenediamine, N-methoxyethyl-para-phenylenediamine, N, N-bis (2-hydroxyethyl) -para-phenylenediamine, 2- (2-hydroxyethyl) para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 4,4'-diaminodiphenylamine, 1,3-bis (N- (2-hydroxyethyl) -N- (4-aminophenyl) amino) -2-propanol, PEG-3,2,2'-para-phenylenediamine, para-aminophenol, para-methylaminophenol, 3-methyl-4-aminophenol, 2-aminomethyl-4-aminophenol, 2- (2-hydroxyethylaminomethyl ) -4-aminophenol, ortho-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 2-amino-5-acetamidophenol, 3,4-diaminobenzoic acid, 5-aminosalicylic acid, 2,4,5, 6-tetraaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4,5-diamino-1-hydroxyethylpyrazole, and salts of these substances and mixtures thereof ,

Non-limiting examples of the coupler include meta-phenylenediamine, 2,4-diaminophenoxyethanol, 2-amino-4- (2-hydroxyethylamino) anisole, 2,4-diamino-5-methylphenol, 2,4-diamino-5- (2-amino) hydroxyethoxy) toluene, 2,4-dimethoxy-1,3-diaminobenzene, 2,6-bis (2-hydroxyethylamino) toluene, 2,4-diamino-5-fluorotoluene, 1,3-bis (2,4-diaminophenoxy) propane, meta-aminophenol, 2-methyl-5-aminophenol, 2-methyl-5- (2-hydroxyethylamino) phenol, 2,4-dichloro-3-aminophenol, 2-chloro-3-amino-6-methylphenol, 2 Methyl 4-chloro-5-aminophenol, N-cyclopentyl-meta-aminophenol, 2-methyl-4-methoxy-5- (2-hydroxyethylamino) phenol, 2-methyl-4-fluoro-5-aminophenol, resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 1-naphthol, 1,5-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 2-isopropyl-5-methylphenol, 4-hydroxyindole, 5-hydroxyindole, 6-hydroxyindole, 7-hydroxyindole, 6-hydroxybenzomorpholine, 3,4-methylenedioxyphenol, 2-bromo-4,5-methylenedioxyphenol, 3,4-methylenedioxyaniline, 1- (2-hydroxyethyl) amino-3,4-methylenediox ybenzene, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dimethoxy-3,5-diaminopyridine, 2,3-diamino-o-methoxypyridine, 2-methylamino-3-amino-6-methoxypyridine, 2- Amino-3-hydroxypyridine, 2,6-diaminopyridine, and salts of these substances and mixtures thereof.

The concentration of the dye precursors and couplers is in the range of 0.001 to 10% by weight, preferably 0.01 to 7.5% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the coloring composition ,

The oxidation coloring composition further comprises an alkalizing agent. Suitable non-limiting examples of the alkalizing agent include ammonia and a salt thereof; Alkanolamine such as monoethanolamine, isopropanolamine, 2-amino-2-methylpropanol and 2-aminobutanol and a salt thereof; Alkanediamine such as 1,3-propanediamine and a salt thereof; and carbonate such as guanidine carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate and mixtures thereof. The concentration of the alkalizing agent is in the range of 0.1 to 15% by weight, preferably 0.5 to 10% by weight, more preferably 1 to 7.5% by weight, based on the total weight of the coloring composition.

In the oxidation dye composition, the component comprising the oxidizing agent is stored separately and mixed with the dye component before application to the hair. Suitable non-limiting examples of the oxidizing agent include hydrogen peroxide, urea peroxide, melamine peroxide and sodium bromate. Among these oxidizing agents, hydrogen peroxide is preferred.

The concentration of the at least one oxidizing agent, preferably hydrogen peroxide, is in the range of 1 to 20% by weight, preferably 1 to 15% by weight, more preferably 1 to 12% by weight and even more preferably 2 to 9% by weight. %, based on the total weight of the dyeing composition.

When stored separately, the pH of the component comprising the oxidizing agent is preferably 2 to 6, more preferably 2.5 to 4. The pH can be adjusted by means of suitable buffering agents. After mixing the dye component with the oxidation component, the pH of the dyeing composition is typically in the range of 6 to 11, preferably 6.5 to 10.5, and more preferably 6.8 to 10, measured at room temperature (25 ° C).

The oxidation dye composition may further comprise at least one direct dye. The direct dyes mentioned above are all suitable for this purpose.

2. The smoothing composition

The smoothing composition has a pH of 4 or less and comprises:
0.1 to 40% by weight of glyoxylic acid and / or a hydrate thereof and / or a salt thereof; and
0.1 to 20% by weight of an amino-modified silicone;
each based on the total weight of the composition.

Glyoxylic acid (H-CO-COOH) is almost quantitatively present in aqueous solution as a hydrate (HC (OH) ₂ -COOH). In addition, the hydrate can also condense to form dimers.

It is also possible to use a salt of glyoxylic acid. As examples, there may be mentioned alkali metal salts such as the sodium or potassium salt and alkaline earth metal salts such as the magnesium salt or the calcium salt.

The concentration of the glyoxylic acid and / or the hydrate thereof and / or the salts thereof is in the range of 0.1 to 40% by weight, preferably 0.5 to 30% by weight, more preferably 1 to 25% by weight and even more preferably 2.5 to 20% by weight, based on the total weight of the smoothing composition.

The pH of the smoothing composition is lower than or equal to 4, preferably in the range of 0.5 to 3, more preferably 1 to 2.5, as measured directly and at room temperature (25 ° C). The pH of the compositions can be adjusted using known alkaline solutions, preferably with sodium hydroxide solution.

As discussed above, conventional hair styling / smoothing techniques are based on the disulfide bond rearrangement and involve cleavage of the disulfide bonds by either use of a sulfur based or alkaline reducing agent, followed by hair styling and new bond formation (that is, by action) an oxidizing agent formed disulfide bonds or thioether bonds). In contrast to these permanent smoothing methods, the present invention does not exploit cleavage of the disulfide bonds and fixation of the bonds in the new form. Therefore, the smoothing composition of the present invention does not require the presence of sulfur-based reducing agents. However, up to 2% by weight, calculated on the total composition, of sulfur-based reducing agents do not interfere with the smoothing performance of the compositions. Therefore, the smoothing composition has less than 2% by weight of sulfur-based reducing agents, and is preferably free of sulfur-based reducing agents.

The smoothing composition may suitably comprise other ingredients such as surfactants and / or conditioning components as defined below, and may suitably be in the form of a solution, emulsion, cream, paste and mousse.

3. Surfactant

The coloring composition and the smoothing composition may comprise a surfactant. As the surfactant, any of a cationic surfactant, a nonionic surfactant, an amphoteric surfactant and an anionic surfactant may be used. It is also possible to use two or more kinds of surfactants in combination.

The cationic surfactant is preferably a mono-long chain alkyl quaternary ammonium salt having a C ₈ -C ₂₄ alkyl radical and three C ₁ -C ₄ alkyl radicals.

ausgewählt, worin R₈ eine gesättigte oder ungesättigte, verzweigte oder gerade Alkylkette mit 8 bis 22 C-Atomen oder R₁₂-CO-NH-(CH₂)n- worin R₁₂ eine gesättigte oder ungesättigte, verzweigte oder gerade Alkylkette mit 7 bis 21 C-Atomen und n eine ganze Zahl von 1 bis 4 ist, oder R₁₂-CO-O-(CH₂)n- worin R₁₂ eine gesättigte oder ungesättigte, verzweigte oder gerade Alkylkette mit 7 bis 21 C-Atomen und n eine ganze Zahl von 1 bis 4 ist, ist, und R₉, R₁₀ und R₁₁ unabhängig voneinander eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen, eine Hydroxyalkylkette mit 1 bis 4 Kohlenstoffatomen oder eine Ethoxy- oder Propoxygruppe mit einer Anzahl von Ethoxy- oder Propoxygruppen, die im Bereich von 1 bis 4 variiert, sind, und X Chlorid, Bromid, Methosulfat oder Ethosulfat ist.Preferably, at least one monoalkyl quaternary ammonium surfactant is selected from the compounds having the general formula

wherein R _{8 is} a saturated or unsaturated, branched or straight alkyl chain having 8 to 22 carbon atoms or R ₁₂ -CO-NH- (CH ₂ ) n- wherein R _{12 is} a saturated or unsaturated, branched or straight alkyl chain having 7 to 21 C atoms and n is an integer from 1 to 4, or R ₁₂ -CO-O- (CH ₂ ) n- wherein R _{12 is} a saturated or unsaturated, branched or straight alkyl chain of 7 to 21 carbon atoms and n is an integer of 1 to 4, and R ₉ , R ₁₀ and R _{11 are} independently an alkyl group having 1 to 4 carbon atoms , a hydroxyalkyl chain having 1 to 4 carbon atoms or an ethoxy or propoxy group having a number of ethoxy or propoxy groups varying in the range of 1 to 4, and X is chloride, bromide, methosulfate or ethosulfate.

Suitable cationic surfactants are, for example, long-chain quaternary ammonium compounds which can be used singly or in admixture with one another, such as cetyltrimethylammonium chloride, myristyltrimethylammonium chloride, behentrimonium chloride, trimethylcetylammonium bromide, stearyltrimethylammonium chloride, stearyltrimonium chloride and stearylamidopropyltrimonium chloride.

Examples of the nonionic surfactant include polyoxy C ₁ -C ₄ alkylene C ₈ -C ₂₄ alkyl ethers, polyoxy C ₁ -C ₄ alkylene C ₈ -C ₂₄ alkylene alkenyl ethers, higher ^{( C} 12 ^{-C 24) -} Fettsäuresaccharoseester, polyglycerol-C ₈ -C ₂₄ fatty acid esters, höheres- (C ₁₂ -C ₂₄₎ fatty acid mono- or diethanolamide, polyoxyethylene hardened castor oil, polyoxyethylene C ₈ -C ₂₄ fatty acid esters, polyoxyethylene C ₈ -C ₂₄ fatty acid esters, C ₈ -C ₂₄ -Alkylsaccharidtensid, C ₈ -C ₂₄ -Alkylaminoxid and C ₈ -C ₂₄ ^- Alkylamidoaminoxid.

Examples of the amphoteric surfactant include an imidazoline-based surfactant, a carbobetaine-based surfactant, an amidobetaine-based surfactant, a sulfobetaine-based surfactant, a hydroxysulfobetaine-based surfactant, and an amidosulfobetaine-based surfactant.

Examples of the anionic surfactant include alkylbenzenesulfonate, alkyl or alkenyl ether sulfate, alkyl or alkenyl sulfate, olefin sulfonate, alkanesulfonate, saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylate, α-sulfofatty acid salts, N-acylamino acid type surfactants, phosphoric mono or diester type surfactants, and sulfosuccinate one. Examples of the alkyl ether sulfate include polyoxyethylene alkyl ether sulfate. Examples of the counter ion for the anionic groups of these surfactants include an alkali metal ion such as sodium ion or potassium ion, an alkaline earth metal ion such as calcium ion or magnesium ion; an ammonium ion and an alkanolamine having 1 to 3 alkanol groups each having 2 or 3 carbon atoms (for example, monoethanolamine, diethanolamine, triethanolamine or triisopropanolamine).

The surfactant may be used singly or in combination of two or more kinds. When a surfactant is added to the dyeing composition and / or the smoothing composition, its content is usually 0.05 to 10% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the dyeing composition and the smoothing composition, respectively ,

4. conditioning component

The coloring composition and the smoothing composition may optionally comprise a conditioning component suitable for application to the hair. The conditioning component is an oil or polymer that adheres to the hair and improves the feel and manageability.

When the conditioning component is used, its total amount is preferably 0.01 to 30% by weight, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight, based on the total weight the dyeing composition or the smoothing composition.

Examples of the conditioning component generally include silicones, higher alcohols, and organic conditioning oils (such as hydrocarbon oil, polyolefin, and fatty acid esters). The composition may comprise one kind of conditioning component or two or more in combination.

silicones

In order to improve the feeling of use, the coloring composition and / or the smoothing composition preferably contains a silicone. Examples of the silicone include dimethylpolysiloxane and modified silicone (for example, amino-modified silicone, fluorine-modified silicone, alcohol-modified silicone, polyether-modified silicone, epoxy-modified silicone or alkyl-modified silicone), but dimethylpolysiloxane, polyether-modified silicone and amino-modified silicone are preferred.

The dimethylpolysiloxane may be any cyclic or non-cyclic dimethylsiloxane polymer, and examples thereof include SH200 series, BY22-019, BY22-020, BY11-026, B22-029, BY22-034, BY22-050A, BY22-055 , BY22-060, BY22-083, FZ-4188 (all from Dow Coming Toray Co., Ltd.), KF-9008, KM-900 series, MK-15H and MK-88 (all from Shin-Etsu Chemical Co ., Ltd.).

The polyether-modified silicone may be any silicone having a polyoxyalkylene group, and the group constituting the polyoxyalkylene group may be an oxyethylene group or oxypropylene group. More specific examples include KF-6015, KF-945A, KF-6005, KF-6009, KF-6013, KF-6019, KF-6029, KF-6017, KF-6043, KF-353A, KF-354A, KF-355A (all from Shin-Etsu Chemical Co., Ltd.), FZ-2404, SS-2805, FZ-2411, FZ-2412, SH3771M, SH3772M, SH3773M, SH3775M, SH3749, SS-280X series, BY22-008M , BY11-030 and BY25-337 (all from Dow Corning Toray Co., Ltd.).

worin R' eine Hydroxylgruppe, ein Wasserstoffatom oder R^x darstellt; R^x eine substituierte oder unsubstituierte einwertige Kohlenwasserstoffgruppe mit 1 bis 20 Kohlenstoffatomen darstellt; D R^x, R''-(NHCH₂CH₂)_mNH₂, OR^x oder eine Hydroxylgruppe darstellt; R'' eine zweiwertige Kohlenwasserstoffgruppe mit 1 bis 8 Kohlenstoffatomen darstellt; m eine Zahl von 0 bis 3 darstellt; p und q Zahlen darstellen, deren Summe im Zahlenmittelwert gleich oder größer als 10 und kleiner als 20.000 ist, vorzugsweise gleich oder größer als 20 und weniger als 3.000, stärker bevorzugt gleich oder größer als 30 und weniger als 1.000, und noch stärker bevorzugt gleich oder größer als 40 und weniger als 800.The amino-modified silicone may be any silicone having an amino group or an ammonium group, and examples thereof include an amino-modified silicone oil in which all or part of the terminal hydroxyl groups are capped with a methyl group or the like, and an amodimethicone not the capped ends, a. A preferred example of the amino-modified silicone may be a compound of the following formula.

wherein R 'represents a hydroxyl group, a hydrogen atom or R ^x ; R ^{x represents} a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms; DR ^x , R "- (NHCH ₂ CH ₂ ) _m NH ₂ , OR ^x or a hydroxyl group; R '' represents a divalent hydrocarbon group having 1 to 8 carbon atoms; m represents a number from 0 to 3; p and q represent numbers whose sum-number average is equal to or greater than 10 and less than 20,000, preferably equal to or greater than 20 and less than 3,000, more preferably equal to or greater than 30 and less than 1,000, and even more preferably equal to or greater than 40 and less than 800.

Specific examples of suitable commercially available amino modified silicone products include amine-modified silicone oils SF8452C, SS-3551 (all from Dow Corning Toray Co., Ltd.), KF-8004, KF-867S, and KF-8015 (all of which are incorporated herein by reference). Etsu Chemical Co., Ltd.); and amodimethicone emulsions such as SM8704C, SM8904, BY22-079, FZ-4671 and FZ-4672 (all from Dow Corning Toray Co., Ltd.).

The total content of these silicones in the composition according to the invention is usually from 0.1 to 20% by weight, preferably from 0.2 to 10% by weight and more preferably from 0.5 to 5% by weight, based on the total weight of the dyeing composition or the smoothing composition.

oil component

To improve the feeling of use, the coloring composition and / or the smoothing composition may also include an organic conditioning oil. The organic conditioning oil suitably used as the conditioning component is preferably a low viscosity water-insoluble liquid, and is selected from hydrocarbon oil having at least 10 carbon atoms, polyolefin, a fatty acid ester, a fatty acid amide, a polyalkylene glycol, and mixtures thereof. The viscosity of such organic conditioning oil, measured at 40 ° C, is preferably 1 to 200 mPa · s, more preferably 1 to 100 mPa · s and even more preferably 2 to 50 mPa · s. To determine the viscosity, a capillary viscometer can be used.

Examples of the hydrocarbon oil include a cyclic hydrocarbon, a linear aliphatic hydrocarbon (saturated or unsaturated) and a branched aliphatic hydrocarbon (saturated or unsaturated), and polymers or mixtures thereof are also included. The linear hydrocarbon oil preferably has 12 to 19 carbon atoms. The branched hydrocarbon oil includes hydrocarbon polymers and preferably has more than 19 carbon atoms.

The polyolefin is a liquid polyolefin, more preferably a liquid poly-α-olefin, and even more preferably a hydrogenated liquid poly-α-olefin. The polyolefin used herein is prepared by polymerizing an olefin monomer having 4 to 14 carbon atoms, and preferably 6 to 12 carbon atoms.

The fatty acid ester may preferably be a fatty acid ester having at least 10 carbon atoms. Examples of such a fatty acid ester include esters having a fatty acid-derived hydrocarbon chain and an alcohol (for example, monoesters, polyhydric alcohol esters or di- and tricarboxylic acid esters). The hydrocarbon group of these fatty acid esters may contain another compatible functional group such as an amide group or an alkoxy group as a substituent, or the hydrocarbon group may be covalently bonded to these functional groups. Specifically, an alkyl and alkenyl ester of a fatty acid having a fatty acid chain of 10 to 22 carbon atoms may be a carboxylic acid ester of an aliphatic alcohol having an aliphatic chain derived from an alkyl and / or alkenyl alcohol having 10 to 22 carbon atoms, and a mixture thereof be suitably used. Specific examples of these preferred fatty acid esters include isopropyl isostearate, hexyl laurate, isohexyl laurate, isohexyl palmitate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, dihexadecyl adipate, lauryl lactate, myristyl lactate, cetyl lactate, oleyl stearate, oleyl oleate, oleyl myristate, lauryl acetate, cetyl propionate and dioleyl adipate.

Other suitable oil components are natural oils such as paraffin oil and natural triglycerides.

Suitable natural triglycerides are argan oil, shea butter oil, shea butter oil, olive oil, almond oil, avocado oil, castor oil, coconut oil, palm oil, sesame oil, peanut oil, sunflower oil, peach kernel oil, wheat germ oil, macadamia nut oil, macadamia oil, evening primrose oil, jojoba oil, castor oil, soybean oil, lanolin, passiflora oil, black cumin oil ( black cumin oil), borage oil, grape seed oil, hempseed oil, kukui nut oil and rosehip oil.

The organic conditioning oil may be used in combination of two or more kinds, and the total concentration is typically in the range of 0.1 to 20% by weight, preferably 0.2 to 10% by weight, more preferably 0.5 to 5 Wt .-% based on the total weight of the dyeing composition or the smoothing composition.

alcohols

From the viewpoint of improving the touch feeling and the stability, the hair dyeing composition and / or the smoothing composition may also contain a higher alcohol having 8 or more carbon atoms. Usually, the higher alcohol has 8 to 22 carbon atoms, and preferably 16 to 22 carbon atoms. Specific examples thereof include cetyl alcohol, stearyl alcohol, behenyl alcohol and mixtures thereof.

The higher alcohol may be used in combination of two or more kinds, and its content is typically 0.1 to 20% by weight, preferably 0.2 to 10% by weight, more preferably 0.5 to 5% by weight. % based on the total weight of the coloring composition or the smoothing composition.

Furthermore, suitable polyols may be included in the compositions. Examples of the polyalkylene glycol include polyethylene glycol and polypropylene glycol, and a mixture of the two may be used, or a copolymer of ethylene oxide and propylene oxide may also be used.

In addition, the coloring composition may comprise other ingredients conventionally used in the field of cosmetics, such as preservatives, chelating agents, stabilizers, antioxidants, plant extracts, ultraviolet absorbers, vitamins, dyes and fragrances.

5. Hair treatment procedure

The smoothing composition of the present invention is applicable to a hair treatment process including two stages, namely, the dyeing treatment (steps (a) to (c)) and the smoothing treatment (steps (d) to (i)).

In the staining steps (steps (a) to (c)) of the method, the first composition (staining composition) is applied to the hair (step (a)) and left on the hair for 5 to 45 minutes, preferably 5 to 30 minutes, and then rinsed with water (step (b)). Optionally, the hair can be shampooed.

The application ratio of hair to the composition by weight is preferably 0.5: 2 to 2: 0.5, more preferably 0.5: 1 to 1: 0.5, even more preferably about 1: 1.

Optionally, the hair may be dried after the dyeing step to reduce the water content of the hair. For this purpose, a hair dryer can be used (step (c)).

After completion of the staining treatment (steps (a) to (c)), the hair is subjected to a smoothing treatment according to steps (d) to (i).

The smoothing treatment achieves a semi-permanent smoothing of the hair using glyoxylic acid as the active ingredient. The smoothing effect is not achieved by cleavage of the disulfide bridges by reduction or action of strong alkali. Accordingly, the use of a reducing composition or an alkaline relaxer (lanthionizing agent) is not required.

In step (d), the smoothing composition is applied to the hair. The application ratio of the hair to the composition by weight is preferably 0.5: 2 to 2: 0.5, more preferably 0.5: 1 to 1: 0.5, and even more preferably about 1: 1.

After application, the hair straightening composition is left on the hair for 1 to 120 minutes, preferably 5 to 90 minutes, more preferably 10 to 60 minutes and especially 15 to 45 minutes at a temperature in the range of 20 to 45 ° C and preferably at room temperature ( Steps)). The time that the composition is left on the hair depends on the type of hair or whether the hair is damaged or resistant.

After processing, the hair can optionally be rinsed with water. Then, the hair is dried to prevent excessive vapor formation in the subsequent step of treating the hair with the iron (steps (f) and (g)). Typically, a hair dryer is used for this purpose. It is preferred to dry the hair with continuous combing to avoid tangling of the hair.

After drying, the hair is treated with iron (step (h)). A standard straightener can be used for this purpose. In order to avoid damage to the hair, the surface temperature of the iron is 250 ° C or lower, preferably 230 ° C or lower, more preferably 200 ° C or lower. To achieve a good smoothing effect, the temperature of the iron is 130 ° C or higher, preferably 150 ° C or higher, more preferably 170 ° C or higher. The iron may preferably have a surface temperature of 180 ± 50 ° C, more preferably 170 to 200 ° C.

Furthermore, after treatment with the iron, the hair can be rinsed off with water and dried with a hair dryer (step (i)).

Examples

The following examples are intended to illustrate but not limit the invention. Example 1: Smoothing Composition % g / g 10.00 - Glyoxylic acid 1.50 - Amodimethicone 0.30 - Fragrance / Perfume qs to pH 1.5 - Sodium hydroxide on 100 - Water Direktfärbezusammensetzung % g / g 1.50 - Amodimethicone 1.40 - Hydroxyethyl cellulose 0.30 - Fragrance / Perfume 0.55 Acid Red 52 / CI 45100 0.28 - Basic red 51 0.01 - HC red 3 on 100 - Water

The hair is dyed with the direct dyeing composition and rinsed with water. Then, the smoothing composition is applied to the pre-shampooed hair in a ratio of about 1: 1, rubbed into the hair and left on the hair for about 30 minutes. Then the hair is dried with a hair dryer. For the subsequent smoothing, a flat iron with a temperature of about 200 ° C is used. Example 2: Oxidative Hair Dye Composition for Permanent Dyeing % g / g 0.25 - ammonium chloride 8.00 - ammonia 25% 0.30 - Fragrance / Perfume 0.55 P-toluenediamine 0.28 - resorcinol 0.01 - m-phenylenediamine on 100 - Water pH: 9.5

The oxidative hair dye composition is mixed with a 6% H ₂ O ₂ solution at a weight ratio of 1: 1 before application to the hair. The smoothing composition described in Example 1 is used as a smoothing composition. Example 3: Demi-permanent dyeing composition % g / g 0.25 - ammonium chloride 0.80 - monoethanolamine 0.30 - Fragrance / Perfume 0.55 P-toluenediamine 0.28 - resorcinol 0.01 - m-phenylenediamine on 100 - Water pH: 6.8

The demi-permanent staining composition is mixed with a 6% H ₂ O ₂ solution at a weight ratio of 1: 1 before application to the hair. The smoothing composition described in Example 1 is used as a smoothing composition.

The hair dyed and smoothened with the compositions of Examples 1 to 3 above showed long-lasting color and the hair was smooth for a long period of time.

test Examples

Four strands of white goat hair (1 g each) were subjected to a permanent wave treatment to obtain permed white goat hair samples.

For the dyeing, a composition for an oxidative hair dye has been used which comprises the following ingredients: 0.5333% by weight - Toluene-2,5-diaminesulfate 0.2667% by weight - Resocinol 5.00% by weight - isopropyl alcohol 0.50% by weight - Sodium sulfide 0.20% by weight - ascorbic acid 8.00% by weight - ammonia 25% to 100% by weight - Water

The composition was mixed with an aqueous 6% hydrogen peroxide solution in a ratio of 1: 1 to prepare the oxidative coloring composition.

The mixed oxidative staining composition was applied to the permanent-corrugated samples at a ratio of dry hair to stain of 1: 3, evenly distributed with a brush and processed on the hair for 20 minutes at a temperature of 40 ° C. Then, the samples were rinsed with water (2 L, for 30 seconds at 37 ° C) and allowed to dry for four hours at room temperature.

Two of the four permed, colored strands served as reference samples and were not subjected to the smoothing treatment. The remaining strands were treated with an aqueous solution of 10% by weight of glyoxylic acid of pH 1.5 (adjusted with NaOH) as a smoothing composition in a ratio of dry hair to smoothing composition of 1: 1.5. The smoothing composition was uniformly spread with a comb and treated for 15 minutes at 40 ° C (5 strokes). After rinsing the hair with water (2 L, for 30 seconds at 37 ° C), the hair was allowed to dry for four hours at room temperature.

The color of the smoothed colored strands and the unsmoothed, colored reference strands were measured in terms of L a b values.

Then, each tress was dipped in 100 ml of a 5% sodium lauryl ester sulfate solution and treated in a shaking bath at 40 ° C for 30 minutes at a stirring rate of 100 min ^-1 .

After rinsing the tresses with water and drying for four hours at room temperature, the color of the tresses was measured in terms of L · a · b values. Then, the color difference (ΔE values) was determined.

For the reference strands which were not subjected to the smoothing treatment with glyoxylic acid, ΔE values of 5.2 and 8.8, respectively, were obtained. In addition, the sodium lauryl ether sulfate solution had a clearly visible color after treatment with the shaking bath.

For the stained and smoothed streaks dyed according to the invention, the ΔE values were 1.1 and 1.3, respectively, and the sodium lauryl ether sulfate solution was clear. A visual inspection also showed that the strands treated according to the invention showed a deeper coloration.

This shows that not only does the invention make it possible to perform dyeing and smoothening in the same treatment session, but also to achieve a substantial improvement in the washing fastness and durability of the coloring.

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited patent literature

• GB 1416564 [0004]
• WO 2011/104282 [0008]
• WO 2012/010351 [0009]
• EP 2407149 [0031]
• EP 2329809 [0031]

Claims (16)

Hair straightening composition having a pH of 4 or less, comprising: From 0.1 to 40% by weight of glyoxylic acid and / or a hydrate thereof and / or a salt thereof; and 0.1 to 20% by weight of an amino-modified silicone; each based on the total weight of the composition. The smoothing composition according to claim 1, wherein the amino-modified silicone is a compound of the following formula:

wherein R 'represents a hydroxyl group, a hydrogen atom or R ^x ; R ^{x represents} a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms; DR ^x , R "- (NHCH ₂ CH ₂ ) _m NH ₂ , OR ^x or a hydroxyl group; R '' represents a divalent hydrocarbon group having 1 to 8 carbon atoms; m represents a number from 0 to 3; p and q represent numbers whose sum in number average is equal to or greater than 10 and less than 20,000. A smoothing composition according to claim 1 or 2, wherein the pH is from 0.5 to 3. A smoothing composition according to any one of claims 1 to 3, wherein the content of glyoxylic acid and / or a hydrate thereof and / or a salt thereof is 2.5-20% by weight. A smoothing composition according to any one of claims 1 to 4, wherein the content of the amino-modified silicone is 0.2-10% by weight. A smoothing composition according to any one of claims 1 to 5, which further comprises at least one surfactant. A smoothing composition according to claim 6, wherein the surfactant is a cationic surfactant of the following general formula:

wherein R _{8 is} a saturated or unsaturated, branched or straight alkyl chain having 8 to 22 carbon atoms, or R _{12 is} -CO-NH- (CH ₂ ) _n - wherein R _{12 is} a saturated or unsaturated, branched or straight alkyl chain having 7 to 21 C atoms and n is an integer from 1 to 4, or R ₁₂ -CO-O- (CH ₂ ) n- wherein R _{12 is} a saturated or unsaturated, branched or straight alkyl chain of 7 to 21 carbon atoms and n is an integer of 1 to 4, and R ₉ , R ₁₀ and R _{11 are} independently an alkyl group having 1 to 4 carbon atoms , a hydroxyalkyl chain having 1 to 4 carbon atoms or an ethoxy or propoxy group having a number of ethoxy or propoxy groups varying in the range of 1 to 4, and X is chloride, bromide, methosulfate or ethosulfate. A smoothing composition according to any one of claims 1 to 7, which comprises at least one higher alcohol having 8 to 22 carbon atoms, preferably in an amount of 0.5 to 5% by weight, based on the total weight of the smoothing composition. A smoothing composition according to any one of claims 1 to 8, which is in the form of an emulsion. Use of the smoothing composition as defined in any one of claims 1 to 9 for straightening hair using a straightening iron having a temperature in the range of 130 to 250 ° C, preferably 180 ± 50 ° C. Use according to claim 10 in combination with a coloring composition comprising at least one hair dye, optionally at least one alkalizing agent and optionally at least one oxidising agent, for dyeing the hair before smoothing. Use according to claim 11, wherein the coloring composition comprises one or more direct dyes, preferably selected from anionic, cationic and nitro dyes. Use according to claim 11 or 12, wherein the coloring composition comprises oxidation dye precursors and couplers. Use according to any one of claims 11 to 13, wherein the coloring composition comprises an alkalizing agent. Use according to any one of claims 11 to 14, wherein the coloring composition comprises an oxidizing agent. Use according to any one of claims 11 to 15, wherein the oxidizing agent is hydrogen peroxide.