AU2001291054B2

AU2001291054B2 - Yellow hair color dyeing composition having improved wear properties

Info

Publication number: AU2001291054B2
Application number: AU2001291054A
Authority: AU
Inventors: Gottfried Wenke; Y. M. Michael Wong
Original assignee: P&G Clairol Inc
Current assignee: P&G Hair Care Holding Inc
Priority date: 2000-09-21
Filing date: 2001-09-18
Publication date: 2004-11-25
Anticipated expiration: 2021-09-18
Also published as: EP1330231A4; CN1462183A; JP2004509140A; EP1330231A1; WO2002024155A1; MXPA03002461A; CA2422690A1; AU9105401A; CN1205910C

Description

WO 02/24155 PCT/US01/29084 YELLOW HAIR COLOR DYEING COMPOSITION HAVING IMPROVED WEAR PROPERTIES Field of the Invention This invention relates to hair coloring compositions for dyeing hair a yellow color, which dyed hair is characterized by improved wear properties.

More particularly, the invention relates to hair coloring compositions for dyeing hair a yellow or blonde color in which the dyed hair retains the dyed color intensity, color brightness and color vibrancy, even on exposure to light or shampooing.

Background of the Invention Coloration of hair is a procedure practiced from antiquity employing a variety of means. In modern times, the most extensively used method employed to color hair is to color hair by an oxidative dyeing process employing hair coloring systems utilizing one or more oxidative hair coloring agents in combination with one or more oxidizing agents.

Most commonly a peroxy oxidizing agent is used in combination with one or more oxidative hair coloring agents, generally small molecules capable of diffusing into hair and comprising one or more primary intermediates and one or more couplers. In this procedure, a peroxide material, such as hydrogen peroxide, is employed to activate the small molecules of primary intermediates so that they react with couplers to form larger sized complexes in the hair shaft to color the hair in a variety of shades and colors.

In order to provide a full palette of shades, a source for a yellow hair color is needed.

Oxidative hair color products sometimes employ o-aminophenol compounds, such as 6-amino-m-cresol or o-aminophenol for this purpose. However, the resulting yellow color has poor stability to light. This is noticeable for the consumer in a loss of vibrancy and drabbing of the color with time.

Sometimes yellow direct dye additives are used in oxidative hair color products as a source of yellow hair color. However, the drawback of utilising such a coloration process for dyeing of hair is the relative fast and large loss of the yellow coloration experienced after repeat shampooing. Again, the consumer will notice undesirable color changes and loss of vibrancy.

It would therefore be desirable if a hair coloring system and composition for dyeing of hair could be provided that produces a yellow coloration of the hair that retains its intensity, brightness and vibrancy over a period of time instead of showing a gradual loss and drabbing of the color.

The discussion of documents, acts, materials, devices, articles and the like is included in this specification solely for the purpose of providing a context for the present invention. It is not suggested or represented that any or all of these matters formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed in Australia before the priority date of each claim of this application.

SUMMARY OF THE INVENTION The present invention is directed to a human hair dyeing composition for the oxidative dyeing of human hair to a yellow color comprising, in a suitable carrier or vehicle, from 0.01% to 3.5% by weight of the composition of a 2,4,5,6tetraaminopyrimidine primary immediate, from 0.01% to 2.5% by weight of the composition of a 2,6-dihydroxypyridine coupler and at least one oxidizing agent.

Preferably the composition of the invention further comprises the a yellow direct dye or an oxidative yellow dye wherein the yellow direct dye is selected from the group consisting of amino-4-nitro-6-chlorophenol, and 5-nitro-8-hydroxyquinoline, and wherein the oxidative yellow dye is selected from the group consisting of 6amino-m-cresol, o-amino-phenol, and 2-amino-m-cresol.

In another aspect the present invention is directed to a process for the oxidative dyeing of human hair a yellow color which comprises applying to the hair a hair dyeing effective amount of the composition of the invention.

The rate of loss of hair coloration due to loss of the direct or known oxidative yellow dye will essentially match the increase in yellow coloration imparted by the oxidatively colored hair obtained by the hair coloring process and composition of this invention.

DETAILED DESCRIPTION OF THE INVENTION It has been discovered that oxidative dyeing of hair to a natural blonde or yellow coloration with exceptional wearing properties can be obtained by the use of the present composition and process. The composition and 4 This page has been intentionally left blank WO 02/24155 PCT/US01/29084 process utilize 2,4,5,6-tetraaminopyrimidine as a primary intermediate, 2,6dihydroxypyridine as a coupler and at least one oxidizing agent. When hair is oxidatively colored according to the present invention, the colored hair retains its intensity of coloration and turns gradually brighter and more vibrant over a period of several days. The resulting bright yellow coloration has good wearing properties, especially with regard to exposure to light. The rate of loss of hair coloration due to loss of the direct or known oxidative yellow dye will essentially match the increase in yellow coloration imparted by the oxidatively colored hair obtained by the hair coloring process and composition of this invention.

The improved yellow hair coloring composition and method of this invention employs a pyrimidine compound of the formula

NH

2 N NH 2 N N NH2 R2 wherein R 1 and R 2 are independently H; C14 alkyl, optionally substituted with one or more hydroxy- or amino group;

R

1 and R 2 may form a 5- or 6-membered heterocyclic ring (such as piperidine or pyrrolidine), optionally containing one additional N- or 0- heteroatom in the ring (such as piperazine or morpholine) as a primary intermediate and WO 02/24155 PCT/US01/29084 a pyridine compound of the formula R1 R2 HO N OH wherein R 1 and R 2 are independently H; C1- 4 alkyl or hydroxy-alkyl as a coupler, and at least one oxidizing agent, preferably a peroxide providing agent, and most preferably hydrogen peroxide (H 2 0 2 or precursors therefor.

The oxidative hair coloring compositions will generally comprise from about 0.01 to about 3.5 weight percent of 2,4,5,6-tetraaminopyrimidine and from about 0.01 to about 2.5 weight percent of 2,6-dihydroxypyridine. The molar ratio of primary intermediate to coupler will generally range from about 5:1 to about 1:5 and be employed in any suitable carrier or vehicle, generally an aqueous or hydroalcoholic solution, preferably an aqueous solution. The carrier or vehicle will generally comprise up to about 40 weight percent of the composition.

Optionally, the hair coloring system and compositions of this invention may also utilize a yellow direct dye or a known oxidative yellow dye. Any suitable yellow direct or known oxidative yellow dye may be employed and will preferably be selected to provide the yellow coloration desired. The rate of loss of hair coloration due to loss of the direct or known oxidative yellow dye will essentially match the increase in yellow coloration imparted by the oxidatively colored hair obtained by the hair coloring process and composition WO 02/24155 WO 0224155PCT/USOI/29084 of this invention. Among the suitable yellow direct dyes that may be employed are N,O-bis(2-hydroxyethyl)-5-nitro-o-aminophenol, 2-amino-4nitro-6-chlorophenol, 2-am ino-5-n itro phenol, and 5-nitro-8-hydroxyquinoline.

The preferred known oxidative yellow dyes that may be employed are selected from the group consisting of 6-amino-m-cresol, 0-amino-phenol, and 2-amino-m-cresol.

According to a further aspect of this invention, one or more other primary intermediates and one or more other couplers may be employed in the hair coloring systems and compositions in addition to the 2,4,5,6tetraaminopyrimidine and 2,6-dihydroxypyridine.

Suitable optional primary intermediates include, for example, p-phenylenediamine derivatives such as: 2-methyl-pphenylenediamine, p-phenylenediamine, 2-chloro-p-phenylenediamine, Nphenyl-p-phenylenediamine, N-(2-methoxyethyl)-p-phenylenediamine, N ,Nbis(2-hyd roxyethyl)-p-ph enylenred iamine, 2-hydroxymethyl-pphenylenediamine, 2-(1 -hydroxyethyl)-p-phenylenediamine, -2 hydroxyethyl)-p-phenylenediamine, 4,4'diamino-diphenylamine, 2 ,6-dimethylp-phenylenediamine, 2-isopropyl-p-phenylenediamine, N-(2-hyd roxypropyl)-pphenylene-d iamine, 2-propyl-p-phenylenediamine, I ,3-bis[(N-hydroxyethyl)- N-(4-aminophenyl)-amino]-2-propanol, 2-methyl-4-dimethylamino-aniline, 2methoxy-p-phenylenediamine, 2 ,3-d imethyl-p-phenylened iamine, 2-(I ,2dihydroxyethyl)-p-phenylened amine and 2-thiophen-2-yl-benzene-1,4diamine; p-aminophenol derivatives such as: p-aminophenol, pmethylaminophenol, 3-methyl-4-aminophenol, 2-hydroxymethyl-4amninophenol, 2-methyl-4-am ino phenol, 2-(2'-hydroxyethylaminomethyl)-4- WO 02/24155 WO 0224155PCT/USOI/29084 aminophenol, 2-methoxymethyl-4-aminophenol, 5-aminosalicylic acid and 1- (5-amino-2-hydroxyphenyl)-ethane-l ,2-diol; o-aminophenol derivatives such as: o-aminophenol, 2,4diaminophenol, 5-methyl-2-a mino phenol, 6-methyl-2-aminophenol, 2ethylamino-p-cresol and 2-amino-5-acetaminophenoi and 4-methyl-2aminophenol; and heterocyclic derivatives such as: 4,5-diamino-1-methylpyrazole, 2d imethyla mino-5-aminopyridine, I -(2-hydroxyethyl)-4 ,5-diaminopyrazole, 4hyd roxy-2,5,6-triaminopyrimidime, 2-(2-hydroxyethylamino)-6-methoxy-3aminopyridime and 3-amino-2-methylamino-6-methoxypyridine.

The primary intermediates can be employed in the form of a free base or in the form of an acid additive salt thereof, such as, for example, as a hydrochloride, a hyd robromide, a sulfate or the like.

Suitable optional additional couplers include, for example, phenols, resorcinol and naphthol derivatives such as: 1,7dihydroxynaphthalene, resorcinol, 4-chlororesorcinol, 1 -naphthol, 2-methyl-i naphthol, I -acetoxy-2-methyl naphthalene, I ,5-d ihydroxynaphthalene, 2,7dihydroxynaphthalene, hydroquinone, 2-methylresorcinol, I -hydroxy-6aminonaphthalene-3-sulfonic acid, 2-isopropyl-5-methylphenol, I ,5-dihyd roxy- I ,2,3,4-tetrahyd ronaphthalene, 2-chloro-resorcinol, 2,3-dihydroxy-1,4naphthoquinone and I -naphthol-4-sulfonic acid, I ,2,3-trihyd roxybenzene; m-phenylenediamines such as: m-phenylenediamine, 2,4-diaminophenoxyethanol, N,N-bis(2-hydroxyethyl)-m-phenylenediamine, -2,6d jaminotoluene, 2-N ,N-bis(hydroxyethyl)-2,4-diaminophenetole, I ,3-bis(2,4- WO 02/24155 WO 0224155PCT/USO1/29084 diaminophenoxy)propane, I -hydroxyethyl-2,4-diaminobenzene, 2-amino-4-(2hydroxyethylamino)anisole, 4-(2-aminoethoxy)-1 ,3-diamiriobenzene, 2,4d jaminophenoxyacetic acid, 4,6-bis(2-hydroxyethoxy)-m-phenylened lamine, 2,4-diamino-5-methylphenetole, 2,4-diamino-5-hydroxyethoxy-toluene, 2,4d imethoxy- 1,3-d ia mino benzene and 2,6-bis(2-hydroxyethylamino)-toluene, 3- (2,4-diaminophenoxy)-1 -propanol; m-aminophenols such as: m-aminophenol, 2-hydroxy-4-(carbamoylmethylamino)toluene, m-carbamoylmethylaminophenol, 6hydroxybenzomorpholine, 2-hydroxy-4-aminotoluene, 2-hyd roxy-4-(2hyd roxyethylamino)toluene, 4,6-d ichlo ro-m-am ino- phenol, 2-methyl-rnaminophenol, 2-c-hloro-6-methyl-m-aminophenol, 2-(2-hydroxyethoxy)-5aminophenol, 2-chloro-5-trifluoroethylaminophenol, 4-chloro-6-methyl-rnarninophenol, N-cyclopentyl-3-aminophenol, N-hydroxyethyl-4-methoxy-6methyl-m-a min ophenol and 5-amino-4-methoxy-2-methylphenol; and heterocyclic derivatives such as: 1 -phenyl-3-methyl-5-pyrazolone, 6methoxy-8-aminoquinoline, 2,6-dihydroxy-4-methylpyridine, 5-hydroxy-1 ,4benzodioxane, 3,4-methylenedioxyphenol, 4-(2-hydroxyethylamino)-1 ,2methylene-d ioxybenzene, 2,6-dihyd roxy-3 ,4-d imethyl pyrid ine, 5-chloro-2 ,3d ihydroxypyridine, 3,5-d iamino-2,6-dimethoxypyridine, 3,4-methylenedioxyaniline, 2,6-bis(2-hyd roxyethoxy)-3,5-diaminopyridine, 4-hydroxyindole, 3-amino-5-hydroxy-2,6-dimethoxypyridine, 5,6-d ihydroxyindole, 7hydroxyindole, 5-hydroxyindole, 2-bromo-4,5-methylenedioxyphenol, 6hydroxyindole, 2-amino-3-hydroxypyridine, 2,6-diaminopyridine, 5-(3 d iamino-2-pyridyloxy)-1 ,3-d ihydroxypentane, 3-(3 ,5-d lami no-2-pyridyloxy)-2hydroxypropanol and isatin.

WO 02/24155 WO 0224155PCT/USOI/29084 Preferred optional primary intermediates include: p-phenylenediamine derivatives such as: 2-methyl-pphenylenediamine, p-phenylenediamine, N-(2-methoxyethyl)-pphenylenediamine, N ,N-bis(2-hyd roxyethyl)-p-phenylenediamine, 2-(1 hyd roxyethyl)-p-phenylened jamine, 2-(2-hydroxyethyl)-p-phenylenediamine, and 2-(1 ,2-dihyd roxyethyl)-p-phenylenediamine; p-aminophenol derivatives such as: p-aminophenol, pmethylaminophenol, 3-methyl-4-aminophenol, 2-methoxymethyl-4aminophenol and I -(5-amino-2-hydroxy-phenyl)-ethane-I ,2-diol; o-aminophenol derivatives such as: o-aminophenol, 2-ethylamino-pcresol, 5-methyl-2-aminophenol, 6-methyl-2-ami no phenol and acetamino-phenol, 4-methyl-2-aminophenol; and heterocyclic derivatives such as: 4,5-d iamino-1 -methylpyrazole, 1 and Preferred optional additional couplers include: phenols, resorcinol and naphthol derivatives such as: 2-methyl-Inaphthol, I -acetoxy-2-methylnaphthalene, I ,7-dihyd roxynaphthalene, resorcinol, 4-chloro-resorcinol, 1-naphthol, 1 ,5-dihydroxynaphthalene, 2,7dihydroxynaphthalene, hydroquinone, 2-methylresorcinol and methylphenol; mn-phenylened ia mines such as: m-phenylenediamine, 2,4-diaminophenoxyethanol, 1 ,3-bis(2,4-d iaminophenoxy)propane, 2-amino-4-(2- WO 02/24155 WO 0224155PCT/USOI/29084 hydroxyethyl-amino)anisole and 4,6-bis(2-hydroxyethoxy)-mphenylenediamine, 3-(2 ,4-diamino-phenoxy)-1 -propanol; m-aminophenols such as: m-aminophenol, 6-hydroxybenzomorpholine, 2-hydroxy-4-aminotoluene, 2-hydroxy-4-(2-hyd roxyethylamino)toluene and 2methyl-m-aminophenol; and heterocyclic derivatives such as: 1-phenyl-3-methyl-5-pyrazolone, 3,4methylenedioxyphenol, 3,4-methylenedioxyaniline, 4-hyd roxyindole, 5,6dihydroxyindole, 7-hydroxyindole, 5-hydroxyindole, 6-hydroxyindole, isatin, 2,6-diamino-pyridine and 2-amino-3-hyd roxypyridine.

Most preferred optional primary intermediates include: p-phenylenediamine derivatives such as: 2-methyl-pphenylenediamine, p-phenylenediamine, N, N-bis(2-hydroxyethyl)-pphenylenediamine, 2-(1 -hydroxyethyi)-p-phenylened iamine and 2-(2hyd roxyethyl)-p-phenylenediamine; p-aminophenol derivatives such as: p-aminophenol, pmethylaminophenol, 3-methyl-4-aminophenol and 1 -(5-amino-2hydroxyphenyl)-ethane-1 ,2-diol; 0-amino derivatives such as: o-aminophenol, 2-ethylamino-p-cresol, methyl-2-aminophenol, 6-methyl-2-aminophenol and acetaminophenol; and heterocyclic derivatives such as: I -(2-hydroxyethyl)-4,5diamninopyrazole.

WO 02/24155 PCT/US01/29084 Most preferred optional additional couplers include: phenols, resorcinol and naphthol derivatives such as: 2-methyl-1naphthol, 1-acetoxy-2-methylnaphthalene, resorcinol, 4-chlororesorcinol, 1naphthol and 2-methylresorcinol; m-phenylenediamines such as: 2,4-diaminophenoxyethanol, 2-amino- 4-(2-hydroxyethylamino)anisole and 4,6-bis(2-hydroxyethoxy)-mphenylenediamine and 3-(2,4-diaminophenoxy)-1-propanol; m-aminophenols such as: m-aminophenol, 6-hydroxybenzomorpholine, 2-hydroxy-4-aminotoluene, 2-hydroxy-4-(2-hydroxyethylamino)toluene and 2methyl-m-aminophenol; and heterocyclic derivatives such as: 1-phenyl-3-methyl-5-pyrazolone, 2amino-3-hydroxypyridine and 6-hydroxyindole.

The dye composition in this invention can be formulated in a lotion or in a cream or gel by including the appropriate types and amounts of surfactants, emulsifiers or polymers and alkalizing agents. The surfactants and emulsifiers can be anionic, cationic or nonionic, and they can be hydrophobic or hydrophilic. Examples of these surfactants and emulsifiers are: Sodium lauryl sulfate, ammonium lauryl sulfate, cetyl alcohol, cetearyl alcohol, oleic acid, dilinoeic acid, polyethylene glycols of various fatty alcohols, lauramide DEA, lauramide MEA, behenetrimonium chloride, cetrimonium chloride, and cocamidopropyl betaine. Examples of alkalizing agents are monoethanolamine, ammonium hydroxide, sodium hydroxide and sodium carbonate. The composition is mixed with an oxidizing agent, such as hydrogen peroxide, prior to use on hair. At the end of the coloring period, which can range from 5 minutes to 40 minutes, the composition is washed WO 02/24155 PCT/US01/29084 from the hair with ordinary water rinse followed by a shampoo. Typical dye compositions are described in the following examples: INGREDIENTS EXAMPLE 1 EXAMPLE 2 EXAMPLE 3 Cocamidopropyl betaine 7 Cetyl alcohol 7 Propylene glycol 15 3 Oleic acid 1 15 Octylpolyglycoside Steareth-21 3 C12-15 Pareth-3 Ammonium hydroxide 5 10 7 Monoethanolamine 2 3 EDTA 0.1 0.1 0.1 Sodium sulfite 0.1 0.1 0.1 Fragrance 0.5 0.5

DYES:

2,4,5,6-tetraaminopyrimidine 1.0 1.0 2,6 dihydroxypyridine 1.0 1.0 Water qs to 100 qs to 100 qs to 100 In the following examples untreated Piedmont hair was dyed with an oxidative dyeing composition of this invention and with comparative prior art compositions. For comparison purposes, dyeing results are presented for typical prior art oxidative dyeing compositions employed to produce yellow coloration, namely compositions employing o-aminophenol, as the primary intermediate, and 1-naphthol, 5-amino-o-cresol or resorcinol as couplers. The dyeing solution comprised the primary intermediate and coupler at 1 weight percent in 100 g of a typical common dye base.

The dyeing solution was mixed with an equal amount of 6% hydrogen peroxide. The resulting dyeing formulation was applied to the hair and permitted to remain in contact with the hair for 30 minutes. The dyed hair was then shampooed and rinsed with water and dried. After dyeing and after WO 02/24155 PCT/US01/29084 exposure to a fade-o-meter, an instrument that simulates sun exposure, coloration results were measured using a Minolta spectrophotometer Chroma Meter 3700d reflectometer. The Minolta Chroma Meter 3700d spectrophotometer uses reflected light from a surface and gives results in terms of the CIE (International Commission on Illumination) tristimulus values.

These values are subsequently transformed mathematically into the L* a* b* color space, wherein the magnitude of changes in hue and intensity of color correspond closely with those perceived by the human eye.

being achromatic, ranges from black to white this term is called "metric lightness" and is a measure of how light or dark a color is, relative to a matching shade of gray. Hue is measured in terms of the chromaticity coordinates a* and where a* indicates redness and b* indicates yellowness The values of a* and b* can be plotted with a* as the x-axis and b* as the y-axis to give quantitative color information: "metric chroma" is the length of a line from the origin to the point of a sample reading while metric hue angle is the angle between the a* axis and the metric chroma line. Metric chroma indicates the strength of a color response the extent to which a color differs from its matching shade of gray). Metric hue angle quantifies hue in degrees, with larger values indicating more yellow hues and smaller values indicating more red (or less yellow) hues.

The results of the tests are set forth in the following Table 1 for the comparative compositions and in Table 2 for the composition of this invention.

The baseline average values of a* and b* for undyed, untreated Piedmont hair were L* 72.32, a* 2.0, b* 23.2.

WO 02/24155 WO 0224155PCT/USOI/29084 Table I Comparative Dyeing Components L* a* b Example A 1 -Naphthol/o-aminophenol 66.9 5.2 36.8 after 12 hr fade-o-meter 66.1 5.2 29.3 after 24 hr fadle-o-meter 67.3 5.2 27.9 B 5-Amino-o-cresol/o-aminophenol 64.9 9.6 34.9 after 12 hr fade-o-meter 64.0 8.3 29.5 after 24 hr fade-o-meter 65.5 7.6 27.8 C Resorcinol/o-aminophenol 63.2 4.4 36.5 after 12 hr fade-o-meter 65.1 3.1 30.1 after 24 hr fade-o-meter 67.1 2.0 26.5 Table 2 Example Dyeing Components 1* a* b* 2,6-Dihydroxypyridine! 2,4,5,6-tetraaminooyrimidine 55.4 -1.5 20.5 after 1 day 58.1 0.5 37.5 after 4 days 61.2 1.1 44.9 after 5 days 63.2 0.6 45.2 after 10 days 63.8 1.6 48.1 after 10 days and subsequent 24 hour fade-o-meter 66.7 2.6 46.8 1 16 The spectophotometer readings in Table 1 demonstrate the poor yellow coloring and poor light stability of the oxidatively dyed yellow coloring of the prior art. In contrast, the spectrophotometer readings in Table 2 demonstrate the increasing brightness of the yellow coloration of the composition of the invention over a period of ten days following dyeing, and the light stability of the coloration even after ten days and subsequent exposure to 24 hours of the fade-o-meter.

With the foregoing description of the invention, those skilled in the art will appreciate that modifications may be made to the invention without departing from the spirit thereof. Therefore, it is not intended that the scope of the invention be limited to the specific embodiments illustrated and described.

Throughout the description and the claims of this specification the word "comprise" and variations of the word, such as "comprising" and "comprises" is not intended to exclude other additives, components, integers or steps.

Claims

1. A human hair dyeing composition for the oxidative dyeing of human hair to a yellow color comprising, in a suitable carrier or vehicle, from 0.01% to 3.5% by weight of the composition of a 2,4,5,6-tetraaminopyrimidine primary immediate, from 0.01% to 2.5% by weight of the composition of a 2,6-dihydroxypyridine coupler and at least one oxidizing agent.

2. The composition according to Claim 2 further comprising a yellow direct dye or an oxidative yellow dye wherein the yellow direct dye is selected from the group consisting of amino-4-nitro-6-chlorophenol, and

5-nitro-8-hydroxyquinoline, and wherein the oxidative yellow dye is selected from the group consisting of

6-amino-m-cresol, o-amino-phenol, and 2-amino-m-cresol. 3. The process of the oxidative dyeing of human hair a yellow color which comprises applying to the hair a hair-dyeing effective amount of the composition of claim 1 or claim 2. 4. A human hair dyeing composition of claim 1 or claim 2, substantially as hereinbefore described with reference to any one of the Examples. A process of claim 3 for the oxidative dyeing of human hair a yellow color which process is substantially as hereinbefore described with reference to any one of the Examples. I Dated: 29 September 2004 PHILLIPS ORMONDE FITZPATRICK Attorneys for: P&G Clairol, Inc. 0