Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1998-04-16
2002-06-18
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S406000, C008S410000, C008S412000, C008S416000, C008S421000, C008S423000, C008S409000
Reexamination Certificate
active
06406501
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to oxidation colorants containing special combinations of primary intermediates for coloring keratin fibers.
By virtue of their intensive colors and good fastness properties, so-called oxidation colorants play a prominent role in the coloring of keratin fibers, particularly human hair. Oxidation colorants contain oxidation dye precursors, so-called primary intermediates and secondary intermediates. The primary intermediates form the actual dyes with one another or by coupling with one or more secondary intermediates in the presence of oxidizing agents or atmospheric oxygen.
Good oxidation dye precursors are expected to satisfy above all the following requirements: they must form the required color tones with sufficient intensity and fastness during the oxidative coupling reaction. In addition, they must be readily absorbed onto the fibers with no significant differences—particularly in the case of human hair—between damaged and freshly regrown hair (levelling behavior). They must be resistant to light, heat and the effect of chemical reducing agents, for example permanent wave lotions. Finally, if they are used to color hair, they should not overly stain the scalp and, above all, should be toxicologically and dermatologically safe.
The primary intermediates normally used are primary aromatic amines containing another free or substituted hydroxy or amino group in the para position or the ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof.
Special representatives are, for example, p-tolulenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis-(2-hydroxyethyl)-p-phenylene-diamine, 2-(2,5-diaminophenyl)-ethanol, 2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido-4-amino-5-pyrazolone and 4-amino-3-methylphenol, 2-hydroxy4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminohydroxypyrimidine.
The secondary intermediates used are generally m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and pyridine derivatives. Particularly suitable secondary intermediates are &agr;-naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxy-naphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)-propane, 2-chlororesorcinol, 2-chloro6-methyl-3-aminophenol, 2-methyl resorcinol, 2,6-dihydroxypyridine and 2,6-diaminopyridine.
With regard to other dye components, reference is expressly made to the Colipa-Liste published by the Industrieverband Körperpflege und Waschmittel, Frankfurt.
By combination with various secondary intermediates, a certain primary intermediate can form a broad range of color tones. Nevertheless, it is often not possible to obtain the large range of natural color tones with a single primary intermediate. In practice, therefore, a combination of various primary intermediates and secondary intermediates has to be used to obtain a single natural-looking color. Accordingly, there is a constant need for new improved secondary intermediate/primary intermediate combinations. This applies in particular to the red range where conventional dyes are often not entirely satisfactory in their fastness to rubbing, their level-dyeing capacity and their resistance to cold waving and washing.
Accordingly, the problem addressed by the present invention was to provide new primary intermediate combinations and suitable secondary intermediates which would satisfy the requirements oxidation dye precursors are expected to meet to a particular degree.
It has now surprisingly been found that special combinations of known primary intermediates, especially in combination with certain, similarly known secondary intermediates, lead to intensive colors, above all in the red and orange range, which are distinguished inter alia by particularly high fastness to light, washing and rubbing and by surprisingly good levelling behavior.
DESCRIPTION OF THE INVENTION
Accordingly, the present invention relates to oxidation colorants for coloring keratin fibers containing primary intermediates and secondary intermediates in a water-containing carrier, characterized in that at least one pyrimidine derivative containing 2-4 amino substituents and 0-2 hydroxy substituents on the pyrimidine ring in combination with 1-(2′-hydroxyethyl)-2,5-diaminobenzene and/or 2-(2′-hydroxyethylamino)-5-aminotoluene is present as the primary intermediate.
In the context of the invention, keratin fibers are understood to include pelts, wool, feathers and, in particular, human hair. Although the oxidation colorants according to the invention are particularly suitable for coloring keratin fibers, there are no basic obstacles to their use in other fields, particularly in color photography.
Pyrimidine derivatives containing 2 to 4 amino substituents and 0 to 2 hydroxy substituents on the pyrimidine ring are used as primary intermediate in the oxidation colorants according to the invention. These pyrimidine derivatives, for example 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-tri-aminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine and 2,4-dihydroxy-5,6-diaminopyrimidine, are compounds familiar to the expert. DE-OS 23 59 399 and the book by Kh. Schrader entitled “Grundlagen und Rezepturen der Kosmetika”, Dr. Afred Hüthig Verlag, Heidelberg, 2nd Edition, are cited as representative of the numerous publications in which these compounds are disclosed.
More particularly, specific reference is made to DE-OS 23 59 399 where it discloses the production of the compounds.
Particularly preferred pyrimidine derivatives, which may be used both on their own and in combination with one another, are 2,4,5,6-tetraaminopyrimidine and 4-hydroxy-2,5,6-triaminopyrimidine.
So far as the component 1-(2′-hydroxyethyl)-2,5-diaminobenzene is concerned, reference is made in particular to the disclosure of DE-A1 39 17 304 which describes this component under the name of 2-(2,5-diamino-phenyl)-ethanol and also discloses its use in hair colorants.
So far as the component 2-(2′-hydroxyethylamino)-5-aminotoluene is concerned, reference is made in particular to the disclosure of DE-C1 43 01 663.
However, there is nothing in any of these documents which points to the combinations according to the invention.
The primary and secondary intermediates present in the formulations according to the invention may be used both as free bases and in the form of their inorganic or organic salts, for example hydrochlorides, sulfates and hydrobromides.
In addition, it has been found that colors exhibiting particularly favorable properties are obtained where the formulations according to the invention contain m-aminophenols corresponding to formula (I):
in which R
1
is hydrogen, a methyl group, an ethyl group or a hydroxyalkyl group containing 2 or 3 carbon atoms and R
2
and R
3
independently of one another are hydrogen or chlorine, as secondary intermediates.
Particularly suitable secondary intermediates corresponding to formula (I) are 2-methyl-5-aminophenol, 2-methyl-5-&bgr;-hydroxyethylaminophenol and 3-amino-2-chloro-6-methylphenol.
Formulations which contain certain other secondary intermediates in addition to those corresponding to formula (I) are also distinguished by unexpectedly good coloring results. These other secondary intermediates are preferably selected from
resorcinol and resorcinol derivatives,
naphthalene derivatives containing at least one OH group and
pyridine derivatives containing at least one C
1-4
alkyl group and at least one hydroxy group.
Particularly suitable other secondary intermediates are resorcinol, 2-methyl resorcinol, 5-methyl resorcinol, 2,5-dimethyl resorcinol, 4-chlororesorcinol, 1,5-, 1,7- and 2,7-dihydroxynaphthalene and 2,6-dihydroxy-3,4-dimethylpyridine.
The hair colorants according to the invention contain both the primary intermediates
Hoeffkes Horst
Hollenberg Detlef
Mueller Reinhard
Rose David
Elhilo Elisa B
Gupta Yogendra N.
Harper Stephen D.
Henkel Kommanditgesellschaft auf Aktien
Hild Kimberly R.
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