COMPOSITION FOR DYEING KERATIN FIBERS CONTAINING A COMBINATION OF A P-PHENYLENE DERIVATIVE AND 2,7-NAPHTHALENEDIOL AND USE THEREOF FOR REDUCING A YELLOW TINGE IN A HAIRSTYLE

Abstract

The present invention relates to a composition for dyeing keratin fibers, for example human hair, with oxidative hair dyes. The composition contains as oxidative dyes a combination of a p-phenylenediamine derivative as the developer substance and 2,7-naphthalenediol as the coupler substance in a suitable base. An oxidizing agent such as hydrogen peroxide is used as an additional component for developing the dye. The invention relates to a use of the composition for gray coloration, with a long-lasting reduction of a yellow tinge in a hairstyle of gray, previously dark hair.

Claims

1. An agent for oxidatively dyeing keratin fibers, characterized in that said agent contains a combination of a p-phenylenediamine derivative and 2,7-naphthalenediol as the sole couplers or the physiologically compatible water-soluble salts thereof.

2. The agent as per claim 1, characterized in that the p-phenylenediamine derivative is selected from 1,4-diaminobenzene (p-phenylenediamine), 1,4-diamino-2-methylbenzene (p-toluenediamine), 1,4-diamino-2-methoxymethylbenzene, 1,4-diamino-2-hydroxyethylbenzene or N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, or mixtures thereof.

3. The agent of claim 1, characterized in that said ready-made agent contains the p-phenylenediamine derivative and the 2,7-naphthalenediol in an overall amount of from 0.05 to 2 percent by weight in each case.

4. The agent of claim 1, characterized in that said ready-made agent contains the p-phenylenediamine derivative and the 2,7-naphthalenediol in an overall amount of from 0.2 to 1 percent by weight in each case.

5. The use of the agent of claim 1 for dyeing human hair gray, the natural color of which hair is dark blond to black and the proportion of white hair of which is more than 10%.

6. The use as per claim 5, wherein the hair has never before been dyed prior to being dyed gray and therefore only contains intrinsic pigments of the user.

7. The use as per claim 6, wherein the hair has a yellow tinge before being dyed gray, which is no longer noticeable after being dyed.

Description

EXAMPLES

Examples 1 to 5: Hair Dye Solution

[0035]

TABLE-US-00001 x g p-phenyldiamine derivative 0.44 g 2,7-naphthalenediol 10.0 g potassium oleate (8% aqueous solution) 4.25 g monoethanolamine (100%) 10.0 g ethanol 0.3 g ascorbic acid to 100.0 g water

[0036] 30 g of the above hair dye solution was mixed with 30 g of a 6% aqueous hydrogen peroxide solution immediately before use. The mixture was then applied to bleached hair. After an application time of 30 minutes at 40 C., the hair was rinsed with water, washed with a commercially available shampoo and dried. The dyeing results are summarized in Table 1.

TABLE-US-00002 TABLE 1 color results from dye solution p-phenylene Example derivative Conc. (x) Color result 1 1,4-diamino-benzene 0.295 g Gray (slightly violet) 2 1,4-diamino-2-methyl- 0.600 g Steel gray benzene sulfate 3 1,4-diamino-2- 0.415 g Gray (slightly methoxymethylbenzene reddish) 4 1,4-diamino-2- 0.683 g Gray (slightly hydroxyethyl-benzene reddish) 5 N,N-Bis-(2- 0.852 g Gray (slightly hydroxyethyl)-p- turquoise) phenylenediamine sulfate

Examples 6 to 8: Color Stabilities

Inventive Product (IP)

[0037]

TABLE-US-00003 0.600 g p-phenylenediamine derivative 0.44 g 2,7-naphthalenediol 15.0 g cetyl alcohol 0.3 g ascorbic acid 3.5 g sodium lauryl alcohol diglycol ether sulfate, 28% aqueous solution 3.0 g ammonia, 22% aqueous solution 0.3 g sodium sulfite, anhydrous to 100.0 g water

[0038] 30 g of the above hair dye cream was mixed with 30 g of a 6% hydrogen peroxide solution immediately before use. The mixture was then applied to the hair. After an application time of 20 minutes, the hair was rinsed with water, washed with a commercially available shampoo and dried.

[0039] For comparison, three market products from the IGORA ABSOLUTES SILVERWHITE range by Henkel, Dusseldorf, Germany are likewise used to color hair according to the instructions for use:

Market Product 1 (MP1): Gray Lilac

[0040] According to the INCI, colorants as the developer are: 1,4-diamino-2-methyl-benzene sulfate and N,N-Bis-(2-hydroxyethyl)-p-phenylenediamine sulfate, and as the coupler are: resorcinol, 4-chlororesorcinol, 2-methylresorcinol, m-aminophenol and 4-amino-2-hydroxytoluene

Market Product 2 (MP2): Dove Gray

[0041] According to the INCI, colorants as the developer are: 1,4-diamino-2-methyl-benzene sulfate and N,N-Bis-(2-hydroxyethyl)-p-phenylenediamine sulfate, and as the coupler are: resorcinol, m-aminophenol and 2,7-naphthalenediol

Market Product 3 (MP3): Slate Gray

[0042] According to the INCI, colorants as the developer are: 1,4-diamino-2-methyl-benzene sulfate and N,N-Bis-(2-hydroxyethyl)-p-phenylenediamine sulfate, and as the coupler are: resorcinol, m-aminophenol and 2,7-naphthalenediol.

Testing Light Stability

[0043] The laboratory measured values were determined from the strands (yak hair) treated using the four products (IP, MP1, MP2, MP3). The strands were then exposed to sunlight for three days. After this time, the lab values were re-measured. The results are shown in Table 2.

Testing Wash Stability

[0044] The laboratory measured values were determined from the strands (bleached, blond natural hairs) treated with the four products (IP, MP1, MP2 MP3). The strands were then added to a 20% shampoo solution for 24 h. The strands were then rinsed with water and dried. The lab values were then re-measured.

[0045] The results are shown in Table 3.

Testing Carrying Stability on the Model

[0046] The formula according to the invention was compared with the formula MP3 in a half-head test on a model (medium-blond initial hair color, 80-90% gray proportion). After the use according to the instructions for use, the lab values were measured at 10 points in each case and an average was generated.

[0047] After 14 days the values were measured again.

[0048] The results are shown in Table 4.

TABLE-US-00004 TABLE 2 color stability after the action of light Starting values Values after treatment Product L a b L a b L a b E IP 33.86 0.06 0.77 35.38 1.90 2.52 1.52 1.84 1.75 2.96 MP1 39.72 1.33 4.10 44.37 0.92 0.24 4.65 0.41 4.34 6.37 MP2 41.60 1.60 2.66 42.57 1.08 3.09 0.97 0.52 5.75 5.85 MP3 30.65 1.30 2.15 27.09 0.70 1.10 3.56 0.60 3.25 4.86

[0049] The result shows that the formula according to the invention (IP) has a substantially lower overall color deviation (SE) and therefore better stability against the action of light.

TABLE-US-00005 TABLE 3 color stability after the action of shampoo Starting values Values after treatment Product L a b L a b L a b E IP 23.17 4.36 2.82 23.74 4.86 3.74 0.57 0.50 0.92 1.19 MP1 35.64 1.25 0.66 42.42 1.16 0.23 3.78 0.09 0.89 6.84 MP2 39.00 1.56 2.25 43.66 2.82 2.39 4.66 1.26 0.15 4.83 MP3 2.775 2.07 1.35 36.66 2.41 3.91 4.35 0.08 0.51 4.38

[0050] The result shows that the formula according to the invention (IP) has a substantially lower overall color deviation (E) and therefore better stability against the action of shampoo.

TABLE-US-00006 TABLE 4 color stability on the model Starting values Values after treatment Product L a b L a b L a b E IP 46.36 3.02 6.23 46.15 3.78 9.76 0.21 0.76 3.53 3.61 MP3 60.57 3.00 7.34 52.63 2.89 8.34 7.64 0.10 1.00 8.00

Hairdressers' Evaluation of the Invention

[0051] For the hairdressers' evaluation, 2 models were each treated with the gray color according to the invention and a market product. The conventional half-head treatment was not possible in this case, since the difference in the result was so significant and easily noticeable that suitable models were not available therefor until a comparative color was offered for the market product in a reduced portion of the head (in this case, the above-mentioned MP3). The resultant results are therefore not classical half-head comparisons, but comparisons between a full-head treatment with the inventive dye, leaving a partial surface of the head, and treatment with MP3 in this partial surface.

[0052] The hairdressers' evaluation was carried out by 3 experienced hairdressers with over 10 years' experience in each case in dyeing work using test models and the conventional techniques for evaluating hair color results.

Hair Condition Before Dyeing

[0053] Model H: natural tone of the hair 5/0, medium brown, 100% white proportion on the contour, 50% on the top of the head and 30% on the back of the head. Hair length up to 30 cm. Section for the MP3 comparative color on the back of the head. A very strong and clearly noticeable yellow tinge effect of the hair was confirmed by all the hairdressers and was particularly noticeable in the white proportion of the hair.

[0054] Model Z: natural tone of the hair 4/0, medium brown, 100% white proportion on the contour, 25% on the top of the head and 20% on the back of the head. Hair length up to 25 cm. Section for the MP3 comparative color on the back of the head. A strong and clearly noticeable yellow tinge effect of the hair was confirmed by all the hairdressers, particularly in the white proportion of the hair, which was less evident as a result of the smaller white proportion compared with Model H.

Dye Use

[0055] For the color as per the invention, the hair dye cream mentioned under IP was prepared and used as stated below, while, for comparison, the hair dye cream prepared from the market product MP3 was used according to the instructions for use.

[0056] In order to prepare the ready-made dye, the IP cream was diluted with a 1.9% peroxide solution in a ratio of 1 to 4 and mixed therewith. The resultant dye was applied to the hair using a brush and left for 20 minutes, then rinsed with water, washed with a commercially available shampoo and dried.

Evaluation and Results:

[0057] The evaluation follows the German school grading principle, with 1 as very good, 2 as good, 3 as satisfactory, 4 as sufficient, 5 as poor and 6 as insufficient. The evaluation by the hairdressers relates to the quality of the dyeing result including the perceived reduction in or elimination of a yellow tinge that was clear prior to dyeing.

Evaluation of the Color According to the Invention for Model H

[0058]

TABLE-US-00007 Before Day of After 7 After 14 After 21 After 28 Hairdresser dyeing dyeing days days days days Miss L. 4.5 2.0 2.0 2.0 2.0 2.5 Mr B. 4.5 2.5 2.5 2.5 3.0 3.0 Mr H. 4.3 2.0 2.0 2.5 2.5 2.5 average 4.5 2.1 2.1 2.3 2.5 2.7

Evaluation of the Comparative Color for Model H

[0059]

TABLE-US-00008 Before Day of After 7 After 14 After 21 After 28 dyeing dyeing days days days days Miss A L. 4.0 3.5 3.5 3.5 4.0 4.0 Mr B B. 4.5 3.5 3.5 4.0 4.0 4.0 Mr S H. 4.3 3.0 3.5 4.0 4.0 4.0 average 4.3 3.3 3.5 3.8 4.0 4.0

Noticeability of the Yellow Tinge in Model H

[0060]

TABLE-US-00009 1 2 3 not difficult easy 4 notice- to to very 5 Agent able notice notice visible obvious Color SH, BB, AL according to the invention Comparative SH, BB, AL dyeing process

Evaluation of the Color According to the Invention for Model Z

[0061]

TABLE-US-00010 Before Day of After 7 After 14 After 21 After 28 Hairdresser dyeing dyeing days days days days Miss L. 3.5 2.0 2.0 2.0 2.0 2.5 Mr B. 4.0 2.5 2.5 2.5 3.0 3.0 Mr H. 4.5 1.5 2.0 2.5 2.5 2.5 average 4.0 2.0 2.2 2.3 2.5 2.8

Evaluation of the Comparative Color for Model Z

[0062]

TABLE-US-00011 Before Day of After 7 After 14 After 21 After 28 dyeing dyeing days days days days Miss A L. 3.5 3.5 3.5 4.0 4.0 4.5 Mr B B. 4.0 3.0 3.0 3.5 4.0 4.0 Mr S H. 4.5 2.5 3.0 3.5 4.0 4.0 average 4.0 3.0 3.2 3.7 4.0 4.2

Noticeability of the Yellow Tinge in Model Z

[0063]

TABLE-US-00012 1 2 3 not hard easy 4 notice- to to very 5 Agent able notice notice visible obvious Color SH, BB, AL according to the invention Comparative BB, AL SH dyeing process

[0064] It is clearly apparent from these random results that both the quality of the color according to the invention and the permanency thereof has improved considerably. Furthermore, it is apparent that a yellow tinge is almost eliminated and does not reappear as strongly, even after 4 weeks, due to the quality of the dyeing process.