Method for coloring keratin fibers

Details Method for coloring keratin fibers Method for coloring keratin fibers

2001-10-31

2004-06-01

Gupta, Yogendra (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S408000, C008S409000, C008S411000, C008S412000, C008S421000, C008S423000, C008S477000, C008S550000, C008S565000, C008S568000, C008S573000

Reexamination Certificate

active

06743263

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to an agent for dyeing keratin fibers, in particular human hair, which comprises pyrimidine derivatives in combination with special couplers, to the use of this combination as dyeing component in hair dyeing agents, and to a method of dyeing keratin fibers, in particular human hair.
BACKGROUND OF THE INVENTION
For the dyeing of keratin fibers, e.g. hair, wool or furs, use is generally made either of substantive dyes or oxidation dyes which are formed by oxidative coupling of one or more developer component with one another or with one or more coupler components. Coupler and developer components are also referred to as oxidation dye precursors.
The developer components usually used are primary aromatic amines having a further free or substituted hydroxyl or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives, and 2,4,5,6-tetraaminopyrimidine and derivatives thereof.
Specific representatives are, for example, p-phenylene-diamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)ethanol, 2-(2,5-diaminophenoxy)ethanol, 1-phenyl-3-carboxyamido-4-aminopyrazol-5-one, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
The coupler components usually used are m-phenylene-diamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols. Particularly suitable as coupler substances are &agr;-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthaline, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol, 1-phenyl-3-methylpyrazol-5-one, 2,4-dichloro-3-aminophenol, 1,3-bis(2,4-diaminophenoxy)propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.
German patent application DE-Al-41 15 148 discloses oxidation dyeing agents which, in a cosmetic carrier, comprise a 2,4,5,6-tetraaminopyrimidine or a 6-hydroxy-2,4-triaminopyridine as oxidation base (developer) and a combination of certain green couplers and violet couplers for producing brilliant and washfast black colorations.
With regard to further customary dye components, reference is made specifically to the “Dermatology” series, published by Ch. Culnan, H. Maibach, Verlag Marcel Dekker Inc., New York, Basle, 1986, vol. 7, Ch. Zviak, The Science of Hair Care, chapter 7, pages 248-250 (substantive dyes), and chapter B, pages 264-267 (oxidation dyes), and the “European Inventory of Cosmetic Raw Materials”, 1996, published by the European Commission, available in diskette format from the Bundesverband der deutschen Industrie-und Handelsunternehmen für Arzneimittel, Reformwaren und Körperpflegemittel e.V., Mannheim.
Although intensive colorations with good fastness properties can be achieved with oxidation dyes, the development of the color, however, generally takes place under the influence of oxidizing agents, such as, for example, H
2
O
2
, which in some cases can result in damage to the fibers. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can occasionally have a sensitizing effect in people with sensitive skin. Although substantive dyes are applied under more moderate conditions, their disadvantage is that the colorations frequently have inadequate fastness properties.
It is an object of the present invention to provide a dyeing agent for keratin fibers, in particular human hair, which is oxidizable by atmospheric oxygen, i.e. is not necessarily dependent on oxidizing agents, such as, for example, H
2
O
2
. The agent should be able to be applied to the fibers in a simple manner and, with regard to depth of color, gray coverage and fastness properties, are at least equal in qualitative terms to otherwise customary oxidation hair dyeing agents. Moreover, the dyeing agents must have no, or only a very low, sensitizing potential. It was a further object to find a dyeing system that allows blue shades to be produced on the keratin fiber by components specifically matched to one another.
SUMMARY OF THE INVENTION
Surprisingly, it has now been found that pyrimidine derivatives in combination with special couplers are highly suitable for the dyeing of keratin fibers, even in the absence of oxidizing agents i.e. in the presence of atmospheric oxygen. They produce colorations with excellent brilliance and depth of color and lead to a wide variety of color shades. However, the use of oxidizing agents should not in principle be excluded here.
The invention provides an agent for the dyeing of keratin fibers, in particular human hair, comprising
A) at least one pyrimidine derivative of the general formula I
 in which R
1
, R
2
, R
3
and R
4
may be identical or different and are hydrogen, OH, NH
2
or a group NR
5
R
6
, in which R
5
and R
6
may be identical or different and are C
1
-C
4
-alkyl, C
1
-C
4
-hydroxyalkyl having a primary and/or secondary hydroxyl group,
where two of the radicals R
1
, R
2
, R
3
or R
4
together can form an optionally substituted 5- and 6-membered heterocycle containing one or two nitrogen and/or oxygen atom(s) in the molecule,
with the proviso that at least two of the radicals R
1
, R
2
, R
3
or R
4
are a group NH
2
and/or NR
5
R
6
,
B) at least one compound chosen from the group consisting of
(a) m-phenylene derivatives of the formulae II and III
 in which R
7
and R
8
may be identical or different and are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-hydroxyalkyl,
R
9
is C
1
-C
4
-hydroxyalkyl or a radical of the general formula IV
 in which R
7
and R
8
are as defined above and m is an integer from 1 to 4,
R
10
is hydrogen or a radical of the general formula V
 in which R
7
and R
9
are as defined above and n is an integer from 1 to 4,
R
11
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-hydroxyalkyl,
(b) m-aminophenol derivatives
 in which R
12
is hydrogen or C
1
-C
4
-alkyl,
R
13
is hydrogen, fluorine, chlorine, OCH
3
or C
1
-C
4
-alkyl,
R
14
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-hydroxyalkyl or OCF
3
,
R
15
is hydrogen, fluorine, chlorine or OCH
3
,
with the provisos that R
12
, R
13
, R
14
and R
15
are not hydrogen at the same time and that, if R
12
is methyl, R
13
, R
14
and R
15
are not hydrogen at the same time,
(c) pyridine derivatives of the formulae VII and VIII
 in which R
16
and R
17
may be identical or different and are fluorine, chlorine or OCH
3
,
 in which R
18
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-hydroxyalkyl,
R
19
is OH or NH
2
,
R
20
is hydrogen, C
1
-C
4
-alkoxy or NH
2
,
X is hydrogen or OCH
3
,
with the provisos that, if R
19
is NH
2
, R
18
and R
20
are not C
1
-C
4
-alkyl or methoxy respectively at the same time, and if R
18
is hydrogen, R
19
and R
20
are not OH or hydrogen respectively at the same time,
(d) resorcinol derivatives of the formula IX
 in which R
21
, R
22
and R
23
may be identical or different and are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-hydroxyalkyl,
with the provisos that R
21
, R
22
and R
23
are not hydrogen at the same time, if R
21
and R
23
are hydrogen, R
22
is not methyl, and if R
21
is methyl, R
22
and R
23
are not hydrogen at the same time,
(e) methylenedioxybenzene derivatives of the formula X
 in which R
24
is OH, NH
2
or NHR
25
, in which R
25
is C
1
-C
4
-alkyl or C
1
-C
4
-hydroxyalkyl, and
(f) 3,4-diaminobenzoic acid.
DETAILED DESCRIPTION OF THE INVENTION
Keratin fibers are to be understood as meaning wool, furs, feathers and, in particular, human hair. In principle, however, the dyes according to the invention may also be used for the dyeing of other natural fibers, such as, for example, cotton, jute, sisal, linen or silk, modified natural fibers, such as, for example, regenerated cellulose, nitro-, alkyl- or hydroxyalkyl- or

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