AGENT FOR REPIGMENTATION OF KERATIN FIBERS, IN PARTICULAR HUMAN HAIR
20260096976 ยท 2026-04-09
Assignee
Inventors
Cpc classification
A61K8/4953
HUMAN NECESSITIES
A61K2800/4324
HUMAN NECESSITIES
A61K2800/592
HUMAN NECESSITIES
International classification
Abstract
The present invention relates to a cosmetic formulation containing a coloring agent precursor selected from the group that consists of indole derivatives and indoline derivatives, and a xanthine derivative. The invention also relates to the use of the cosmetic formulation for repigmentation of keratin fibers, in particular human hair.
Claims
1. A cosmetic formulation comprising a dye precursor selected from the group consisting of indoline derivatives and indole derivatives, and a xanthine derivative as bioactive ingredient.
2. The cosmetic formulation according to claim 1, wherein the dye precursor is an indole derivative.
3. The cosmetic formulation according to claim 1, wherein the dye precursor is a derivative of 5,6-dihydroxyindole of formula (I), ##STR00004## wherein, independently of each other, R.sup.1 is hydrogen, a C.sub.1-C.sub.4-alkyl group or a C.sub.1-C.sub.4-hydroxyalkyl group, R.sup.2 is hydrogen or a COOH group, whereby the COOH group can also be present as a salt with a physiologically tolerated cation, R.sup.3 is hydrogen or a C.sub.1-C.sub.4-alkyl group, R.sup.4 is hydrogen, a C.sub.1-C.sub.4-alkyl group, an amino group or a group COR.sup.6 in which R.sup.6 is a C.sub.1-C.sub.4-alkyl group, and R.sup.5 is one of the groups mentioned under R.sup.4, or a physiologically tolerated salt of these compounds with an organic or inorganic acid.
4. The cosmetic formulation according to claim 3, wherein the compound of formula (I) is selected from 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole and physiologically tolerated salts thereof.
5. The cosmetic formulation according to claim 1, wherein the dye precursor is an indoline derivative.
6. The cosmetic formulation according to claim 1, wherein the dye precursor is a derivative of 5,6-dihydroxyindoline of formula (II), ##STR00005## wherein, independently of each other, R.sup.1 is hydrogen, a C.sub.1-C.sub.4-alkyl group or a C.sub.1-C.sub.4-hydroxyalkyl group, R.sup.2 is hydrogen or a COOH group, whereby the COOH group can also be present as a salt with a physiologically tolerated cation, R.sup.3 is hydrogen or a C.sub.1-C.sub.4-alkyl group, R.sup.4 is hydrogen, a C.sub.1-C.sub.4-alkyl group, an amino group or a group COR.sup.6 in which R.sup.6 denotes a C.sub.1-C.sub.4-alkyl group, and R.sup.5 is one of the groups mentioned under R.sup.4, or a physiologically tolerated salt of these compounds with an organic or inorganic acid.
7. The cosmetic formulation according to claim 6, wherein the compound of formula (II) is selected from 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline and physiologically tolerated salts thereof.
8. The cosmetic formulation according to claim 1, wherein the xanthine derivative is caffeine.
9. The cosmetic formulation according to claim 1, further comprising at least one direct dye.
10. The cosmetic formulation according to claim 9, wherein the direct dye is selected from the group consisting of 2-amino-6-chloro-4-nitrophenol, 1,4-bis-(-hydroxyethyl)-amino-2-nitrobenzene, Basic Yellow 57, Basic Red 76, Basic Brown 16, Basic Brown17, Basic Blue 99, HC Blue 2, HC Blue 12, HC Blue 16 and Acid Violet 43, preferably HC Blue 2.
11. Use of the cosmetic formulation according to claim 1 for the repigmentation of keratin fibers, in particular human hair.
12. The use according to claim 11 for the repigmentation of human hair, wherein the formulation is distributed in wet or dry hair and is rinsed out again after a dwell time of between 1 and 30 minutes.
13. The use according to claim 11 for the repigmentation of human hair, wherein the hair is permanently colored in a slow and gentle manner and at the same time the keratinocytes in the hair roots are stimulated so that they produce more natural pigment again.
14. A method for repigmenting keratin fibers, in particular human hair, wherein the cosmetic formulation according to claim 1 is applied to the hair and then the coloring is carried out.
Description
DESCRIPTION OF THE FIGURES
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EXPERIMENTAL PART
Formulations
[0124] The following formulations have been prepared by means known to a person skilled in the art.
Comparative Formulation
[0125] The Comparative Formulation contains caffeine as xanthine derivative and HC Blue 2 as direct dye.
TABLE-US-00002 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 11.5 Sodium cocoamphoacetate 3 Cocamidopropyl betaine 1.7 Caffeine 1.1 Panthenol 0.92 Sodium chloride 1 Phenoxyethanol 0.7 Cocoglucoside 0.5 Glyceryl oleate 0.5 Phosphoric acid 0.4 PEG-120 methyl glucose dioleate 0.3 HC Blue 2 0.22 Menthol 0.2 Polyquaternium-7 0.2 Sodium hydroxide 0.15 Niacinamide 0.1 Zinc PCA 0.1 Dye/colorant 0.1 Citric acid 0.06
Example Formulation 1
[0126] Example Formulation 1 contains dihydroxyindole and caffeine as xanthine derivative.
TABLE-US-00003 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 8.0 Sodium myreth sulfate 2.5 Laureth-2 2 Panthenol 1.7 Sodium chloride 1.65 Disodium lauryl sulfosuccinate 1.5 Sodium lauroyl glutamate 1.3 Caffeine 1.1 PEG-120 methyl glucose dioleate 0.75 Wheat protein hydrolyzate 0.7 Dihydroxyindole 0.49 Allantoin 0.4 Citric acid 0.38 Sodium benzoate 0.36 Propylene glycol 0.3 Potassium sorbate 0.3 PEG-40 hydrogenated castor oil 0.18 Cocoglucoside 0.18 Glyceryl oleate 0.17 Polyquaternium-7 0.17 Disodium EDTA 0.15 Zinc PCA 0.1 Niacinamide 0.1 Tocopherol 0.06
Example Formulation 2
[0127] Example Formulation 2 contains dihydroxyindole, caffeine as xanthine derivative and HC Blue 2 as direct dye.
TABLE-US-00004 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 11.5 Sodium cocoamphoacetate 3 Cocamidopropyl betaine 1.7 Caffeine 1.1 Panthenol 0.92 Sodium chloride 1 Phenoxyethanol 0.7 Cocoglucoside 0.5 Glyceryl oleate 0.5 Phosphoric acid 0.4 PEG-120 methyl glucose dioleate 0.3 HC Blue 2 0.22 Menthol 0.2 Polyquaternium-7 0.2 Sodium hydroxide 0.15 Dihydroxyindole 0.2 Niacinamide 0.1 Zinc PCA 0.1 Dye/colorant 0.1 Citric acid 0.06
Example Formulation 3
[0128] Example Formulation 3 contains dihydroxyindole, caffeine as xanthine derivative and HC Blue 2 as direct dye.
TABLE-US-00005 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 9 Sodium myreth sulfate 3 Sodium cocoamphoacetate 1 Laureth-2 2 Disodium lauryl sulfosuccinate 1 Sodium lauroyl glutamate 2 Caffeine 0.9 Sodium chloride 1 Wheat protein hydrolyzate 0.7 Phosphoric acid 0.3 Sodium benzoate 0.5 Potassium sorbate 0.2 HC Blue 2 1 Allantoin 0.4 PEG-40 hydrogenated castor oil 0.4 Polyquaternium-7 0.2 Disodium EDTA 0.2 Dihydroxyindole 0.3 Tocopherol 0.02
Example Formulation 4
[0129] Example Formulation 4 contains dihydroxyindole, caffeine as xanthine derivative and HC Blue 2 as direct dye.
TABLE-US-00006 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 11 Sodium myreth sulfate 2 Laureth-2 3 Cocoamidopropyl betaine 2 Disodium lauryl sulfosuccinate 1 Sodium lauroyl glutamate 1 Panthenol 0.5 Caffeine 1 Sodium chloride 0.9 Phenoxyethanol 0.5 Wheat protein hydrolyzate 0.5 Cocoglucoside 0.3 Glyceryl oleate 0.4 Phosphoric acid 0.25 Sodium benzoate 0.2 PEG-120 methyl glucose dioleate 0.1 Potassium sorbate 0.5 HC Blue 2 0.8 Allantoin 0.1 PEG-40 hydrogenated castor oil 0.2 Menthol 0.2 Sodium hydroxide 0.1 Disodium EDTA 0.2 Dihydroxyindole 0.1 Citric acid 0.03 Niacinamide 0.2 Zinc PCA 0.2 Dye/colorant 0.1
Example Formulation 5
[0130] Example Formulation 5 contains dihydroxyindole and caffeine as xanthine derivative.
TABLE-US-00007 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 12 Sodium cocoamphoacetate 2 Cocoamidopropyl betaine 2 Panthenol 1 Caffeine 1.1 Sodium chloride 0.9 Phenoxyethanol 0.8 Cocoglucoside 0.4 Glyceryl oleate 0.3 Phosphoric acid 0.3 PEG-120 methyl glucose dioleate 0.2 Menthol 0.2 Polyquaternium-7 0.1 Sodium hydroxide 0.2 Disodium EDTA 0.1 Dihydroxyindole 0.2 Citric acid 0.06 Niacinamide 0.2 Zinc PCA 0.2 Dye/colorant 0.5
Example Formulations 6-8
[0131] In contrast to Example Formulation 2, the additional dye for coloring the formulation was completely omitted in Example Formulations 6-8. Example Formulation 6 contains dihydroxyindole and caffeine as xanthine derivative, Example Formulation 7 contains dihydroxyindole, caffeine as xanthine derivative and HC Blue 2 as direct dye and Example Formulation 8 contains caffeine as xanthine derivative and HC Blue 2 as direct dye.
TABLE-US-00008 Example Example Example Example Formulation 2 Formulation 6 Formulation 7 Formulation 8 Quantity in % Quantity in % Quantity in % Quantity in % Component by weight by weight by weight by weight Aqua [water] ad 100 ad 100 ad 100 ad 100 Sodium lauryl ether sulfate 11.5 11.5 11.5 11.5 Sodium cocoamphoacetate 3 3 3 3 Cocamidopropyl betaine 1.7 1.7 1.7 1.7 Caffeine 1.1 1.1 1.1 1.1 Panthenol 0.92 0.92 0.92 0.92 Sodium chloride 1 1 1 1 Phenoxyethanol 0.7 0.7 0.7 0.7 Cocoglucoside 0.5 0.5 0.5 0.5 Glyceryl oleate 0.5 0.5 0.5 0.5 Phosphoric acid 0.4 0.4 0.4 0.4 PEG-120 methyl glucose dioleate 0.3 0.3 0.3 0.3 HC Blue 2 0.22 0.22 0.22 Menthol 0.2 0.2 0.2 0.2 Polyquaternium-7 0.2 0.2 0.2 0.2 Sodium hydroxide 0.15 0.15 0.15 0.15 Dihydroxyindole 0.2 0.2 0.2 - Niacinamide 0.1 0.1 0.1 0.1 Zinc PCA 0.1 0.1 0.1 0.1 Dye/colorant 0.1 Citric acid 0.06 0.06 0.06 0.06
Neutral Formulation
[0132] The neutral formulation contains neither caffeine nor DHI nor HC Blue 2.
TABLE-US-00009 Component Quantity in % by weight Aqua [water] ad 100 Sodium lauryl ether sulfate 10 Laureth-2 1.9 Disodium lauryl sulfosuccinate 1.5 Sodium chloride 1.3 Sodium lauroyl glutamate 1.3 Panthenol 1.2 PEG-120 methyl glucose dioleate 0.5 Wheat protein hydrolyzate 0.49 Citric acid 0.4 Sodium citrate 0.35 Propylene glycol 0.2 Menthol 0.2 PEG-40 hydrogenated castor oil 0.2 Potassium sorbate 0.19 Polyquaternium-7 0.17 Disodium EDTA 0.11 Sodium benzoate 0.1 Zinc PCA 0.06 Niacinamide 0.055 Tocopherol 0.032 Dye/colorant 0.0005
Application Examples
[0133] To evaluate the color performance in terms of quality, intensity and duration, the following washing tests (wash-on and wash-out tests) were carried out.
Application Example 1
[0134] Kerling strands were subjected to a wash-on test with a shampoo containing 5,6-DHI, caffeine and HC Blue 2 (Example Formulation 2) and with a shampoo containing HC Blue 2 and caffeine (Comparative Formulation), respectively, in order to examine the color performance in terms of quality and intensity.
Washing Protocol:
[0135] Moisten strands with lukewarm water for 30 seconds, brush out excess water between two fingers [0136] Massage in a total of 5 g shampoo for 1 minute per 5 strands [0137] Leave for a total of 5 minutes [0138] Rinse with lukewarm water for 1 minute, then squeeze out in kitchen roll [0139] Combing, spread out individually to air dry [0140] The next day, scan strands with the Konica (Konica-Minolta Spectrophotometer CM600d, measuring geometry d/8, Specular Component Excluded (SCE), standard illuminant D65, visual field) 10 (photograph sample strands every 5 washes); then repeat washing cycle
Used Hair Strands:
[0141] Kerling white selected, adhesive braid 2 cm wide, 12 cm long, 3 g/pc
Used Shampoos:
TABLE-US-00010 Example Formulation 2 Strands D1-D5 Comparative Formulation Strands E1-E5
[0142] For each product, 5 strands were used and 28 washes were carried out.
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[0144] The comparison of the color preview for the two shampoos used is shown in
Application Example 2
[0145] Kerling strands were subjected to a wash-on and wash-out test with a shampoo containing 5,6-DHI, caffeine and HC Blue 2 (Example Formulation 2) and with a shampoo containing HC Blue 2 and caffeine (Comparative Formulation), respectively, in order to examine the color performance in terms of quality, intensity and duration.
Washing Protocol:
[0146] Moisten strands with lukewarm water for 30 seconds, brush out excess water between two fingers [0147] Massage in a total of 5 g shampoo for 1 minute per 5 strands [0148] Leave for a total of 5 minutes [0149] Rinse with lukewarm water for 1 minute, then squeeze out in kitchen roll [0150] Combing, spread out individually to air dry [0151] The next day, scan strands with the Konica (Konica-Minolta Spectrophotometer CM600d, measuring geometry d/8, Specular Component Excluded (SCE), standard illuminant D65, visual field) 10, photograph; then repeat washing cycle
Used Hair Strands:
[0152] Kerling white selected, adhesive braid 2 cm wide, 12 cm long
Used Color Shampoos:
TABLE-US-00011 Example Formulation 2 Strands B1-B15 Comparative Formulation Strands C1-C15
[0153] The neutral formulation was used for washing out.
[0154] For each product, 15 strands were treated in portions of 5 pieces.
[0155] The color change was monitored throughout the subsequent wash-on and wash-out cycles: [0156] 5 washes each with color shampoo to wash on, followed by 14 washes with neutral formulation (
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Application Example 3
[0160] White Virgin strands (Imhair company) were subjected to a wash-on test with a shampoo containing 5,6-DHI and caffeine (Example Formulation 1) and with a shampoo containing 5,6-DHI, caffeine and HC Blue 2 (Example Formulation 2), respectively, and with a shampoo containing HC Blue 2 and caffeine (Comparative Formulation), respectively, in order to examine the color performance in terms of quality and intensity.
Washing Protocol:
[0161] Moisten strands with lukewarm water for 30 seconds, brush out excess water between two fingers [0162] Massage in a total of 2 g shampoo for 30 seconds per 3 strands [0163] Leave for a total of 5 minutes [0164] Rinse with lukewarm water for 1 minute [0165] Combing, air drying [0166] The next day, scan strands with the Konica, photograph; then repeat washing cycle
Used Hair Strands:
[0167] White Virgin (Imhair company)
Used Shampoos:
TABLE-US-00012 Example Formulation 1 Strands 1-3 Example Formulation 2 Strands 4-6 Comparative Formulation Strands 7-9
[0168] For each product, 3 strands each were used and 15 washing cycles each were carried out.
[0169] The comparison of the color preview for the shampoos used is shown for a single strand of hair in
Application Example 4
[0170] To examine the dyed shade over time, the Kerling white and Imhair bleached strands were dyed for 15 min with 10 g of Example Formulation 2, rinsed for 1 min and air-dried for 1.5 h (residual moisture was then blow-dried). Measurements were taken on the day of treatment after 15 min exposure time (initial shade) and after 1, 2, 3, 8, 9, 10, 11, 14 and 15 days.
TABLE-US-00013 L*(D65) a*(D65) b*(D65) dL*(D65) da*(D65) db*(D65) dE*ab(D65) Kerling strand, white 76.58 2.15 21 Initial shade 62.32 1.58 5.02 14.27 0.57 15.98 21.43 (after 15 min exposure time) read in after 1 d 62.11 2.05 5.23 14.48 0.1 15.77 21.41 read in after 2 d 63.06 2.22 4.59 13.52 0.07 16.42 21.27 read in after 3 d 63.02 2.44 5.09 13.56 0.29 15.91 20.91 read in after 8 d 62.95 2.53 5.57 13.64 0.38 15.44 20.6 read in after 9 d 62.86 2.35 5.5 13.73 0.21 15.51 20.71 read in after 10 d 62.63 2.57 5.87 13.95 0.42 15.13 20.58 read in after 11 d 62.59 2.61 5.47 14 0.46 15.53 20.91 read in after 14 d 63.16 3.1 6.34 13.43 0.95 14.67 19.91 read in after 15 d 63.59 3.16 6.26 12.99 1.02 14.74 19.68
TABLE-US-00014 L*(D65) a*(D65) b*(D65) dL*(D65) da*(D65) db*(D65) dE*ab(D65) Imhair strand, 76.9 3.5 24.61 bleached Initial shade 51.51 1.01 2.73 25.38 2.49 21.88 33.61 (after 15 min exposure time) read in after 1 d 51.71 1.6 2.8 25.19 1.9 21.82 33.38 read in after 2 d 52.11 1.61 2.79 24.78 1.89 21.82 33.08 read in after 3 d 51.57 2.06 3.23 25.33 1.43 21.38 33.17 read in after 8 d 52.21 2.22 3.78 24.68 1.28 20.84 32.33 read in after 9 d 51.98 2.13 3.84 24.92 1.36 20.78 32.47 read in after 10 d 52 2.29 4.16 24.9 1.21 20.46 32.24 read in after 11 d 52.11 2.29 4.16 24.79 1.21 20.46 32.16 read in after 14 d 52.69 2.65 4.86 24.21 0.84 19.75 31.25 read in after 15 d 53.23 2.68 5.01 23.67 0.82 19.61 30.74
[0171] The measured values show aalso visually perceptibleshift in shade from the original graphite to a more natural, more brownish color.
Application Example 5
[0172] Kerling strands were subjected to a wash-on test with a shampoo containing 5,6-DHI and caffeine (Example Formulation 6) and with a shampoo containing 5,6-DHI, caffeine and HC Blue 2 (Example Formulation 7), respectively, and with a shampoo containing HC Blue 2 and caffeine (Example Formulation 8), respectively, in order to examine the color performance in terms of quality and intensity.
Washing Protocol:
[0173] Moisten 5 strands with lukewarm water for 30 s, squeeze out excess water between two fingers [0174] Massage in a total of 5 g shampoo for 1 min per 5 strands [0175] Leave for a total of 5 minutes [0176] Rinse with lukewarm water for 1 minute, then squeeze out with kitchen roll [0177] Comb, spread out individually to air dry [0178] The next day, scan strands with the Konica (Konica-Minolta Spectrophotometer CM600d, measuring geometry d/8, Specular Component Excluded (SCE), standard illuminant D65, visual field) 10, photograph; then repeat washing cycle
Used Hair Strands:
[0179] Kerling white selected, adhesive braid 2 cm wide, 12 cm long, 3 g/pc,
Used Coloring Shampoos:
TABLE-US-00015 Example Formulation 6 strands DHI-A to E Example Formulation 7 strands Combi-A to E Example Formulation 8 strands Blue-A to E
[0180] 5 strands were used per product, 15 washes were carried out in each case.
[0181] The comparison of the color preview for the shampoos used is shown for a single strand of hair in
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[0183] In
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[0185] The figures show the gradual build-up of the color effect with repeated application and the improved coloring result compared to a Comparative Formulation only containing HC Blue 2 and caffeine (Example Formulation 8).