SELECTED DICARBOXYLIC ACIDS IN AGENTS THAT ARE GENTLE TO HAIR, AND METHOD FOR OXIDATIVE HAIR DYEING OR BLEACHING

Abstract

The present disclosure relates to an oxidising agent that is gentle to hair for oxidative hair dyeing or bleaching, and to a gentle method for oxidative hair dyeing or bleaching, in which keratin fibres are protected against oxidative influences.

Claims

1. An oxidative colourant or bleaching agent for keratin fibres, comprising a) at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms, selected from malic acid, D-tartaric acid, L-tartaric acid, meso-tartaric acid, racemic acid, alpha-ketoglutaric acid, beta-ketoglutaric acid, oxaloacetic acid, maleic acid, fumaric acid, and/or at least one salt of these acids, b) at least one amino acid of formula (VI) ##STR00029## in which X stands for a hydrogen atom or a monovalent or divalent cation; n stands for zero, 1, 2 or 3; R.sup.1 stands for a group which is selected from an amino group, a guanidine group, a (1H-imidazol-4-yl) group, a carboxylic acid amide group, a 1H-indol-3-yl group, a thiol group, and a methylsulfanyl group, or at least one salt of this amino acid, c) at least one alkalising agent, selected from ammonium hydroxide, monoethanolamine, sodium silicate, or mixtures hereof, d) optionally at least one oxidation dye precursor product and/or at least one substantive dye, e) water, and f) at least one peroxide compound.

2. A colourant or bleaching agent according to claim 1, wherein the at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms is selected from malic acid, D-tartaric acid, L-tartaric acid, meso-tartaric acid, racemic acid, and mixtures of these acids.

3. The colourant or bleaching agent according to claim 1, wherein the at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms, is included in a total amount of from about 0.2 to about 4% by weight calculated with respect to the undissociated dicarboxylic acid and based on the weight of the colourant or bleaching agent.

4. The treatment agent according to claim 1, wherein the at least one amino acid of formula (VI) is selected from arginine, lysine, histidine, asparagine, glutamine, cysteine, methionine, tryptophan, or mixtures hereof.

5. The treatment agent according to claim 1, wherein the at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms is included in a total amount of from about 0.05 to about 5% by weight calculated with respect to the undissociated dicarboxylic acid and based on the weight of the treatment agent.

6. The treatment agent according to claim 1, wherein at least one compound of general formula (III) is included, ##STR00030## wherein R1 stands for a hydrogen atom or for a structural element of formula (IV), ##STR00031## wherein x stands for an integer from about 1 to about 100, the group R2 in each of the structural elements of formula (IV) can bois selected in each case independently of the previous structural element of formula (IV), R2 stands for a hydrogen atom, a methyl group, an isopropyl group, a 2-methylpropyl group, a 1-methyl-propyl group, a benzyl group, a 4-hydroxybenzyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 4-aminobutyl group, a 3-carbamimidamidopropyl group, a 2-carboxyethyl group, a carboxymethyl group, a 2-carbamoylethyl group, a carbamoylmethyl group, a sulfanylmethyl group, a 2-(methylsulfanyl)ethyl group, a 1H-imidazol-4-ylmethyl group, a 1H-indol-3-ylmethyl group, or a (sulfosulfanyl)methyl group, M1 stands for the grouping OM2 or for a structural element of formula (V) ##STR00032## wherein y stands for an integer of from about 1 to about 100, the group R3 in each of the structural elements of formula (V) is selected in each case independently of the previous structural elements of formula (V), R3 stands for a hydrogen atom, a methyl group, an isopropyl group, a 2-methylpropyl group, a 1-methyl-propyl group, a benzyl group, a 4-hydroxybenzyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 4-aminobutyl group, a 3-carbamimidamidopropyl group, a 2-carboxyethyl group, a carboxymethyl group, a 2-carbamoylethyl group, a carbamoylmethyl group, a sulfanylmethyl group, a 2-(methylsulfanyl)ethyl group, a 1H-imidazol-4-ylmethyl group, a 1H-indol-3-ylmethyl group,. or a (sulfosulfanyl)methyl group, and M2 stands for a hydrogen atom, an equivalent of a monovalent or polyvalent cation or an ammonium ion (NH.sub.4).sup.+.

7. The colourant or bleaching agent according to claim 1, wherein hydrogen peroxide is included as the at least one peroxide compound.

8. The colourant or bleaching agent according to claim 1, wherein at least one polymer A is included which comprises at least ten constitutive units of formula (I), ##STR00033## in which X stands for nitrogen or oxygen, and R.sup.1 and R.sup.2, in each case independently of one another, stand for hydrogen or a C2-C10 acyl group, or R.sup.1 and R.sup.2 together with X form a five- or six-membered, saturated or unsaturated ring, which optionally comprises further heteroatoms, which are selected from N and O, and/or optionally is substituted with at least one C1-C6 alkyl group and/or is optionally substituted with at least one functional group, and P=0 when X stands for oxygen, and p=1 when X stands for nitrogen, wherein the polymer A does not contain any permanently ionic constitutive units.

9. The colourant or bleaching agent according to claim 8, wherein the at least one polymer A with at least ten constitutive units of formula (I) is selected from polymers that comprise from about 98 to about 100 mol % of constitutive units of formula (Ia) ##STR00034## and have a degree of polymerisation in the range of from about 40 to about 1000, wherein the polymer A does not contain any permanently ionic constitutive units.

10. A method for oxidative dyeing and/or lightening of keratin fibres, in which a treatment agent according to claim 1 is applied to the keratin fibres, and is rinsed out again optionally after a reaction time of from about 0.1 to about 60 minutes.

11. A method for oxidative dyeing and/or lightening of keratin fibres, comprising the following method steps: I. providing a composition (A), comprising a) at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms, selected from malic acid, D-tartaric acid, L-tartaric acid, meso-tartaric acid, racemic acid, alpha-ketoglutaric acid, beta-ketoglutaric acid, oxaloacetic acid, maleic acid and fumaric acid, and/or at least one salt of these acids, b) at least one amino acid of formula (VI) ##STR00035## in which X stands for a hydrogen atom or a monovalent or bivalent cation; n stands for zero, 1, 2 or 3; R.sup.1 stands for a group which is selected from an amino group, a guanidine group, a (1H-imidazol-4-yl) group, a carboxylic acid amide group, a 1H-indol-3-yl group, a thiol group, and a methylsulfanyl group, or at least one salt of this amino acid, c) water, and d) optionally at least one substance which is selected from compounds of general formula (III), ##STR00036## wherein R1 stands for a hydrogen atom or for a structural element of formula (IV), ##STR00037## wherein x stands for an integer from about 1 to about 100, the group R2 in each of the structural elements of formula (IV) is selected in each case independently of the previous structural element of formula (IV), R2 stands for a hydrogen atom, a methyl group, an isopropyl group, a 2-methylpropyl group, a 1-methyl-propyl group, a benzyl group, a 4-hydroxybenzyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 4-aminobutyl group, a 3-carbamimidamidopropyl group, a 2-carboxyethyl group, a carboxymethyl group, a 2-carbamoylethyl group, a carbamoylmethyl group, a sulfanylmethyl group, a 2-(methylsulfanyl)ethyl group, a 1H-imidazol-4-ylmethyl group, a 1H-indol-3-ylmethyl group, or a (sulfosulfanyl)methyl group, M1 stands for the grouping OM2 or for a structural element of formula (V) ##STR00038## wherein y stands for an integer of from about 1 to about 100, the group R3 in each of the structural elements of formula (V) is selected in each case independently of the previous structural elements of formula (V), R3 stands for a hydrogen atom, a methyl group, an isopropyl group, a 2-methylpropyl group, a 1-methyl-propyl group, a benzyl group, a 4-hydroxybenzyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 4-aminobutyl group, a 3-carbamimidamidopropyl group, a 2-carboxyethyl group, a carboxymethyl group, a 2-carbamoylethyl group, a carbamoylmethyl group, a sulfanylmethyl group, a 2-(methylsulfanyl)ethyl group, a 1H-imidazol-4-ylmethyl group, a 1H-indol-3-ylmethyl group, or a (sulfosulfanyl)methyl group, M2 stands for a hydrogen atom, an equivalent of a monovalent or polyvalent cation, or an ammonium ion (NH.sub.4).sup.+, and polymers (A) which comprise at least ten constitutive units of formula (I), ##STR00039## in which X stands for nitrogen or oxygen, and R1 and R2, in each case independently of one another, stand for hydrogen or a C2-C10 acyl group, or R1 and R2 together with X form a five- or six-membered, saturated or unsaturated ring, which optionally comprises further heteroatoms, which are selected from N and O, and/or optionally is substituted with at least one C1-C6 alkyl group and/or optionally substituted with at least one functional group, and p=0 when X stands for oxygen, and p=1 when X stands for nitrogen, wherein the polymer A does not contain any permanently ionic constitutive units, II. providing a composition (B) comprising e) at least one alkalising agent, selected from ammonium hydroxide, monoethanolamine, sodium silicate, and mixtures hereof, f) optionally water, and g) optionally at least one oxidation dye precursor product and/or at least one substantive dye, III. providing a composition (C), comprising h) at least one peroxide compound, IV. mixing the compositions (A), (B) and (C) with one another, then directly thereafter V. applying the mixture of (A), (B) and (C) to the keratin fibres, and VI. rinsing it out after a reaction time of from about 0.1 to about 60 minutes, VII. optionally further keratin fibre treatments, chosen from deforming, conditioning, and/or drying.

12. A composition (A) comprising at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms, selected from malic acid, D-tartaric acid, L-tartaric acid, meso-tartaric acid, racemic acid, alpha-ketoglutaric acid, beta-ketoglutaric acid, oxaloacetic acid, maleic acid or fumaric acid, in a total amount of from about 2 to about 20% by weight, calculated with respect to the undissociated dicarboxylic acid and based on the weight of the composition (A), at least one amino acid of formula (VI) and/or a salt hereof ##STR00040## in which X stands for a hydrogen atom or a monovalent or divalent cation; n stands for zero, 1, 2 or 3; R.sup.1 stands for a group which is selected from an amino group, a guanidine group, a (1H-imidazol-4-yl) group, a carboxylic acid amide group, a 1H-indol-3-yl group, a thiol group, and a methylsulfanyl group, or at least one salt of this amino acid, in a total amount of from about 0.4 to about 7.0% by weight, calculated with respect to the undissociated amino acid and based on the weight of the composition (A), and water in an amount of from about 50 -to about 92% by weight, based on the weight of the composition (A), optionally at least one polymer A which comprises at least ten constitutive units of formula (I), ##STR00041## in which X stands for nitrogen or oxygen, and R.sup.1 and R.sup.2, in each case independently of one another, stand for hydrogen or a C2-C10 acyl group, or R1 and R2 together with X form a five- or six-membered, saturated or unsaturated ring, which optionally comprises further heteroatoms, which are selected from N and O, and/or optionally is substituted with at least one C1-C6 alkyl group and/or optionally substituted with at least one functional group, and p=0 when X stands for oxygen, and p=1 when X stands for nitrogen, wherein the polymer A does not contain any permanently ionic constitutive units, wherein the at least one polymer A is included in a total amount of from about 0.5 to about 14% by weight, based on the weight of the composition (A), wherein the composition (A) has a pH value in the range of from about 3.5 to about 7.1, measured at 20 C.

13. A method for oxidative dyeing and/or lightening of keratin fibres, comprising the following method steps: I. providing a composition (AB) comprising a) at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms, selected from malic acid, D-tartaric acid, L-tartaric acid, meso-tartaric acid, racemic acid, alpha-ketoglutaric acid, beta-ketoglutaric acid, oxaloacetic acid, maleic acid and fumaric acid, and/or at least one salt of these acids, b) at least one amino acid of formula (VI), ##STR00042## in which X stands for a hydrogen atom or a monovalent or divalent cation; n stands for zero, 1, 2 or 3; R.sup.1 stands for a group which is selected from an amino group, a guanidine group, a (1H-imidazol-4-yl) group, a carboxylic acid amide group, a 1H-indol-3-yl group, a thiol group, and a methylsulfanyl group, or at least one salt of this amino acid, c) optionally at least one substance which is selected from compounds of general formula (III), ##STR00043## wherein R1 stands for a hydrogen atom or for a structural element of formula (IV), ##STR00044## wherein x stands for an integer from about 1 to about 100, the group R2 in each of the structural elements of formula (IV) is selected in each case independently of the previous structural element of formula (IV), R2 stands for a hydrogen atom, a methyl group, an isopropyl group, a 2-methylpropyl group, a 1-methyl-propyl group, a benzyl group, a 4-hydroxybenzyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 4-aminobutyl group, a 3-carbamimidamidopropyl group, a 2-carboxyethyl group, a carboxymethyl group, a 2-carbamoylethyl group, a carbamoylmethyl group, a sulfanylmethyl group, a 2-(methylsulfanyl)ethyl group, a 1H-imidazol-4-ylmethyl group, a 1H-indol-3-ylmethyl group, or a (sulfosulfanyl)methyl group, M1 stands for the grouping OM2 or for a structural element of formula (V) ##STR00045## wherein y stands for an integer of from about 1 to about 100, the group R3 in each of the structural elements of formula (V) is selected in each case independently of the previous structural elements of formula (V), R3 stands for a hydrogen atom, a methyl group, an isopropyl group, a 2-methylpropyl group, a 1-methyl-propyl group, a benzyl group, a 4-hydroxybenzyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 4-aminobutyl group, a 3-carbamimidamidopropyl group, a 2-carboxyethyl group, a carboxymethyl group, a 2-carbamoylethyl group, a carbamoylmethyl group, a sulfanylmethyl group, a 2-(methylsulfanyl)ethyl group, a 1H-imidazol-4-ylmethyl group, a 1H-indol-3-ylmethyl group, or a (sulfosulfanyl)methyl group, M2 stands for a hydrogen atom, an equivalent of a monovalent or polyvalent cation, or an ammonium ion (NH.sub.4).sup.+, and polymers (A) which comprise at least ten constitutive units of formula (I), ##STR00046## in which X stands for nitrogen or oxygen, and R.sup.1 and R.sup.2, in each case independently of one another, stand for hydrogen or a C2-C10 acyl group, or R1 and R2 together with X form a five- or six-membered, saturated or unsaturated ring, which optionally comprises further heteroatoms, which preferably are selected from N and O, and/or optionally is substituted with at least one C1-C6 alkyl group and/or optionally substituted with at least one functional group, and p=0 when X stands for oxygen, and p=1 when X stands for nitrogen, wherein the polymer A does not contain any permanently ionic constitutive units, d) at least one alkalising agent, selected from ammonium hydroxide, monoethanolamine and sodium silicates and mixtures hereof, e) water, and f) optionally at least one oxidation dye precursor product and/or at least one substantive dye, II. providing a composition (C), comprising g) at least one peroxide compound, III. mixing the compositions (AB) and (C) with one another, then directly thereafter IV. applying the mixture of (AB) and (C) to the keratin fibres, and V. rinsing it out after a reaction time of from about 0.1 to about 60 minutes, VI. optionally further keratin fibre treatments chosen from deforming, conditioning, and/or drying.

14. The method according to claim 11, wherein the at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms is malic acid.

15. The colourant or bleaching agent according to claim 8, wherein the at least one polymer (A) is selected from polyvinylpyrrolidone, polyvinyl alcohol and mixtures hereof.

16. The colourant or bleaching agent according to claim 1, wherein the at least one saturated dicarboxylic acid having from about 2 to about 10 carbon atoms, is included in a total amount of from about 0.5 to 2% by weight, calculated with respect to the undissociated dicarboxylic acid and based on the weight of the colourant or bleaching agent.

17. The treatment agent according to claim 1, wherein the at least one amino acid of formula (VI) is a mixture of arginine and lysine.

18. The treatment agent according to claim 6, wherein one or more compounds of formula (III) is/are included in a total amount of from about 0.001 to about 2.5% by weight, based on the weight of the colourant or bleaching agent.

19. The treatment agent according to claim 6, wherein one or more compounds of formula (III) is/are included in a total amount of from about 0.02 to about 0.1% by weight, based on the weight of the colourant or bleaching agent.

20. The treatment agent according to claim 8, wherein the at least one polymer A with at least ten constitutive units of formula (I) is included in a total amount of from about 0.2 to about 5% by weight, in relation to the weight of the colourant or bleaching agent.

Description

EXAMPLES

[0333] The following examples of oxidative treatment agents as contemplated herein are intended to explain the present disclosure without limiting it.

TABLE-US-00001 TABLE 1 Oxidative treatment agent (developer) for oxidative hair dyes and bleaching agents (all stated values in % by weight) Ingredient no. 1 no. 2 no. 3 no. 4 no. 5 cetearyl alcohol 2.8 2.2 5 5 5 PEG-40 castor oil 0.6 0.4 1.5 1.5 1.5 sodium cetearyl sulfate 0.4 0.3 1.0 1.0 1.0 paraffin oil 21.0 13.0 31.0 isopropyl myristate 15.0 31.0 etidronic acid 0.15 0.15 0.15 0.15 0.15 L-arginine 0.4 0.4 0.4 L-lysine hydrochloride 0.7 0.7 malic acid 1.0 1.0 1.0 1.0 1.0 disodium 0.1 0.1 0.1 0.1 0.1 pyrophosphate dipicolinic acid 0.1 0.1 0.1 0.1 0.1 sodium benzoate 0.04 0.04 0.04 0.04 0.04 potassium hydroxide 0.12 0.12 0.12 0.12 0.12 hydrogen peroxide 6.0 9.0 12.0 9.0 12.0 water (demineralised) to 100 to 100 to 100 to 100 to 100

TABLE-US-00002 TABLE 2 Oxidative treatment agent (developer) for oxidative hair dyes and bleaching agents (all stated values in % by weight) Ingredient no. 1 no. 2 no. 3 no. 4 no. 5 cetearyl alcohol 2.8 2.2 5 5 5 PEG-40 castor oil 0.6 0.4 1.5 1.5 sodium cetearyl sulfate 0.4 0.3 1.0 paraffin oil 21.0 13.0 31.0 isopropyl myristate 15.0 31.0 trident-2 carboxamide 2.0 2.0 MEA etidronic acid 0.15 0.15 0.15 0.15 0.15 L-arginine 0.4 0.4 0.4 L-lysine hydrochloride 0.7 0.7 racemic acid 1.0 1.0 1.0 1.0 potassium tartrate 1.0 (racemic) disodium 0.1 0.1 0.1 0.1 0.1 pyrophosphate dipicolinic acid 0.1 0.1 0.1 0.1 0.1 sodium benzoate 0.04 0.04 0.04 0.04 0.04 potassium hydroxide 0.12 0.12 0.12 0.12 0.12 hydrogen peroxide 6.0 9.0 12.0 9.0 12.0 water (demineralised) to 100 to 100 to 100 to 100 to 100

TABLE-US-00003 TABLE 3 Oxidative treatment agent (developer) for oxidative hair dyes and bleaching agents (all stated values in % by weight) Ingredient no. 1 no. 2 no. 3 no. 4 no. 5 1,2-propylene glycol 2.0 2.0 2.0 2.0 2.0 cetearyl alcohol 1.5 1.5 3.6 1.5 3.6 ceteareth-20 0.6 0.4 1.5 1.5 1.5 trident-2 carboxamide 2.0 2.0 MEA paraffin oil 2.0 13.0 31.0 isopropyl myristate 2.0 31.0 etidronic acid 0.15 0.15 0.15 0.15 0.15 L-arginine 0.4 0.4 0.4 L-lysine hydrochloride 0.7 0.7 malic acid 1.5 2.0 2.0 2.0 1.5 steardimonium 0.1 0.1 0.1 0.1 0.1 hydroxypropyl hydrolysed keratin disodium 0.1 0.1 0.1 0.1 0.1 pyrophosphate dipicolinic acid 0.1 0.1 0.1 0.1 0.1 sodium benzoate 0.04 0.04 0.04 0.04 0.04 potassium hydroxide 0.2 0.2 0.2 0.2 0.2 hydrogen peroxide 6.0 9.0 12.0 6.0 9.0 water (demineralised) to 100 to 100 to 100 to 100 to 100

TABLE-US-00004 TABLE 4 Colouring creams (all stated values in % by weight) Formulation constituents (colouring cream) 1 2 cetyl alcohol 3.6 4.6 behenyl alcohol 2.4 3.0 paraffinum liquidum 2.1 2.1 Eumulgin B 3 (INCI: Ceteareth-30) 1.2 1.8 Brij S 100 PA (Stearyl alcohol ethoxylated 0.6 1.0 (100 EO)) Cutina GMS (INCI: Glyceryl Stearate) 0.6 0.6 propylene glycol 6.0 6.0 p-toluene diamine sulfate 1.50 1.50 resorcinol 0.58 0.58 m-aminophenol 0.16 0.16 3-amino-2-methylamino-6-methoxypyridine 0.05 0.05 potassium hydroxide (50%) 0.7 0.7 ethylenediaminetetraacetic acid, tetrasodium 0.20 0.20 salt sodium sulfite (anhydrous) 0.30 0.30 vitamin C 0.05 0.05 product W 37194 (N,N,N-trimethyl-3-[(1- 3.75 3.0 oxo-2-propenyl)amino]-1-propanaminium chloride, polymer with sodium 2-propenoate) (INCI: Acrylamidopropyltrimonium chloride/ Acrylate Copolymer), 20% by weight aqueous solution ammonia (25% by weight aqueous solution) 5.80 5.80 fragrance 0.40 0.40 water to 100 to 100

[0334] Colouring creams 1 and 2 according to table 4 correspond to compositions (B) as presented in the description. They were each mixed in a ratio by weight of 1:1 with one of the oxidative treatment agents from tables 1, 2 or 3, then directly applied to strands of human hair, and rinsed out using water and a shampoo after a reaction time of 45 minutes. The hair was then dried first using a towel and then using a hair-dryer.

TABLE-US-00005 TABLE 5 bleaching powder (powdered composition (B)) Formulation constituents (% by weight) sodium silicate (SiO.sub.2:Na.sub.2O = 2:1) 36.00 magnesium carbonate 12.85 sodium hexametaphosphate 0.20 Rohagit S hv (methylmethacrylate, methacrylic acid 1.00 copolymer) EDTA disodium salt (ethylenediaminetetraacetic acid, 0.60 disodium salt) Polyquatemium-4 0.30 silicic acid, hydrophilic 0.40 glycine 0.60 potassium persulfate 32.00 ammonium persulfate 10.00 CI 77007 (ULTRAMARINES) 0.15 dimethicone (85% by weight),dimethiconol (15% by 1.50 weight) paraffinum liquidum 3.80

[0335] In order to produce the ready-to-use bleaching agent, 2 parts by weight of an oxidative treatment agent from tables 1, 2 or 3 were in each case mixed with one part by weight of the bleaching powder according to table 5, then applied directly to strands of human hair, and rinsed out using water and a shampoo after a reaction time of 500 minutes. The hair was then dried first using a towel and then using a hair-dryer.