Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2002-07-18
2004-12-28
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S409000, C008S410000, C008S412000, C008S574000, C008S602000, C008S611000, C548S480000, C548S461000
Reexamination Certificate
active
06835212
ABSTRACT:
The present invention relates to an agent and to a method for dyeing keratin fibers, especially human hair.
The reaction between ketones or aldehydes, especially aromatic aldehydes such as benzaldehyde and various substituted benzaldehydes, with compounds having an active CH group, water being split off and compounds formed, which are suitable for dyeing keratin fibers, has already been described earlier, for example, in the German Offenlegungsschrift 197 17 281 and the German utility patent 299 08 464. The possibility of sensitizing when the ketone or the aldehyde is applied directly on the hair or the scalp is a disadvantage of using this reaction between ketones or aldehydes and compounds with active CH groups. Furthermore, it is difficult to incorporate especially aldehydes into the dyeing agents and to keep such agents for longer periods, since the aldehydes tend to oxidize in air, forming carboxylic acids, which do not participate in the color-forming reaction.
The present application avoids the direct use of ketones or aldehydes by employing primary or secondary alcohols as aldehyde or ketone precursors for the aforementioned reaction, the alcohols being oxidized enzymatically in situ to the corresponding aldehydes or ketones.
The object of the present application therefore is an agent for dyeing keratin fibers, especially wool, silk or hair, especially human hair, wherein at least one compound with a nucleophilic reaction center, at least one alcohol from the group comprising aryl alcohol derivatives and benzyl alcohol derivatives and at least one oxidizing enzyme is contained.
As inventive alcohol, especially aryl alcohols or benzyl alcohols of formula (I) may be named, which can be converted by enzyme-catalyzed oxidation to the corresponding carbonyl compounds;
Ar—(CH═CH)
n
—CH
2
OH (I)
in which n=0, 1 or 2;
and Ar is a group of formula
in which Y is an oxygen atom, a sulfur atom or an NR
a
group; R1′, R2′, R3′, R4′, R5′, R6′ and R7′ independently of one another are a hydrogen atom, a hydroxy group, a methoxy group, an aryl group, a halogen atom (F, Cl, Br, I), a —CHO— group, a —COR
a
group, a —CO
2
R
a
group, an NO
2
— group, an —OCOR
a
group, an —OCH
2
aryl group, an —NH
2
group, an —NH
3
+
group, an —NHR
a
group, an —NH
2
R
a+
group, an —N(R
a
)
2
group, an —N(R
a
)
3
+
group, an —NHCOR
a
group, an —NHCOOR
a
group, in which R
a
is a hydrogen atom, a linear or branched C1 to C4 alkyl group, an optionally substituted, aromatic, carbocyclic group or heterocyclic group, or R4′ and R5′ together with the carbon atom of the aromatic ring form a 5-membered or 6-membered alicyclic or aromatic ring, which optionally may contain one or more sulfur, nitrogen or oxygen atoms.
The following compounds of formula (I) are particularly preferred: benzyl alcohol, 4-hydroxy-benzyl alcohol, 4-hydroxy-3-methoxy-benzyl alcohol (vanillyl alcohol), 3-hydroxy-4-methoxy-benzyl alcohol (isovanillyl alcohol), 3,5-dimethoxy-4-hydroxybenzyl alcohol, 3,4-dihydroxy-benzyl alcohol, 2-hydroxy-3-methoxy-benzyl alcohol, 4-ethoxy-benzyl alcohol, 4-carboxy-benzyl alcohol, 2,5-dihydroxy-benzyl alcohol, 2,4-dihydroxy-benzyl alcohol, 2-hydroxy-benzyl alcohol, 3,5-dimethoxy-4-hydroxy-benzyl alcohol, 4-hydroxy-2-methoxy-benzyl alcohol, 2,4-dimethoxy-benzyl alcohol, 2,3-dimethoxy-benzyl alcohol, 2,5-dimethoxy-benzyl alcohol, 3,5-dimethoxy-benzyl alcohol, 3,4-methylenedioxy-benzyl alcohol, 3,4-dimethoxy-benzyl alcohol, 3-ethoxy-4-hydroxy-benzyl alcohol, 3,5-dimethyl-4-hydroxy-benzyl alcohol, 3,4-dimethoxy-5-hydroxy-benzyl alcohol, 3,4,5-trimethoxy-benzyl alcohol, 2,4,6-trihydroxy-benzyl alcohol, 3,4,5-trihydroxy-benzyl alcohol, 2,3,4-trihydroxy-benzyl alcohol, 3,5-di-t-butyl-4-hydroxy-benzyl alcohol, 2-nitro-benzyl alcohol, 3-nitro-benzyl alcohol, 4-nitro-benzyl alcohol, 2-amino-benzyl alcohol, 3-amino-benzyl alcohol, 3-amino-4-methyl-benzyl alcohol, 3,5-diamino-benzyl alcohol, 4-amino-benzyl alcohol, 4-dimethylamino-benzyl alcohol, 4-diethylamino-2-hydroxy-benzyl alcohol, 4-diethylamino-3-methoxy-benzyl alcohol, 4-dimethylamino-2-methoxy-benzyl alcohol, 4-dibutyl-amino-benzyl alcohol, 3-methoxy-4-(1-pyrrolidinyl)-benzyl alcohol, (4-methoxy-naphthalene-1-yl)-methanol, (4-dimethylamino-naphthalene-1-yl)-methanol, 2-(hydroxymethyl)-1-naphthol, 1-naphthalene-methanol, 2-naphthalene-methanol, (2-methoxy-naphthalene-1-yl)-methanol, 4-hydroxy-methyl-naphthalene-1-ol, 4′-hydroxymethyl-biphenyl-4-ol, (4-hydroxymethylphenyl)-methanol, 4-(3-hydroxy-propenyl)-2-methoxy-phenol, 4-(3-hydroxy-propenyl)-2,6-dimethoxy-phenol, 3-(4-dimethylaminophenyl)-prop-2-ene-1-ol, 5-(4-(diethylamino-phenyl)-penta-2,4-diene-1-ol, thiophene-2-yl-methanol, (5-hydroxymethyl-thiophene-2-yl)-methanol, thiophene-3-yl-methanol, (1H-pyrrole-2-yl)-methanol, (1-methyl-1H-pyrrole-2-yl)-methanol, (5-methyl-furan-2-yl)-methanol, (1H-indole-3-yl)-methanol, and (6-methyl-1H-indole-3-yl)-methanol.
The use of the alcohol instead of the corresponding carbonyl compound of the present invention makes a rapid intensive dyeing of the fibers, especially of the keratin fibers possible in the presence of a compound with a nucleophilic center with the addition of an oxidizing enzyme. “An oxidizing enzyme” is understood here to be an enzyme, which is able to catalyze the oxidation of the alcohol to an aldehyde or ketone. The following are named as examples of such enzymes, which are, however, not limited to these: alcohol dehydrogenases (E.C. Classification 1.1.1.-), alcohol oxidases (E.C. Classification 1.1.2- and 1.1.3- and 1.1.99-), flavinoxidases (E.C. Classification 1.2.--), laccases (E.C. Classification 1.4.---), peroxidases (E.C. Classification 1.11.1.-), hydroxylases and monooxygenases (E.C. Classification 1.13.12- and 1.13.99-).
The enzyme is used preferably in an amount of 5 to 100 units per millimole of substrate (alcohol). A unit of enzyme activity refers here to the amount of enzyme, which is required to catalyze the oxidation of 1 micromole of alcohol per minute.
“Compounds with a nucleophilic reaction center” are understood to be compounds, which are able to form unsaturated carbon-carbon or carbon-nitrogen bonds by reaction with the electrophilic carbonyl carbon of the aldehyde or ketone. Suitable compounds with a nucleophilic reaction center of the present invention are, for example, primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides with 2 to 9 amino acid groups, aromatic hydroxy compounds and compounds with active CH group.
Suitable compounds with primary or secondary amino groups are, for example, primary aromatic amines such as N,N-dimethyl-p-phenylenediamine, N,N-diethyl-p-phenylenediamine, N-(2-hydroxyethyl)-N-ethyl-p-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, N-(2-methoxyethyl)-p-phenylenediamine, 2,3-dichloro-p-phenylenediamine, 2,4-dichloro-p-phenylenediamine, 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-toluylenediamine, m-toluylenediamine, 2,5-diaminotoluene, 2,5-diaminophenol, 2,5-diaminophenethol, 4-amino-3-methylphenol, 2,4-diaminophenoxyethanol, 2-(2,5-diamino-phenyl)-ethanol, 2-(2,5-diaminophenoxy)-ethanol, 4-methylaminoaniline, 3-amino-(2-hydroxyethyloxy)aniline, 3,4-methylenediaminoaniline, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro-phenol, 4-methylamino-phenol, 2-methyl-5-amino-phenol, 3-methyl-4-amino-phenol, 2-methyl-5-(2-hydroxyethylamino)-phenol, 6-methyl-3-amino-2-chloro-phenol, 2-methyl-5-amino-4-chloro-phenol, 5-(2-hydroxyethylamino)-4-methoxy-2-methyl-phenol, 1,3-diamino-2,4-dimethoxybenzene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2,3-diaminobenzoic acid, 2,4-diaminobenzoic acid, 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, 3,4-diaminobenzoic acid, 3,5-diamin
Braun Hans-Juergen
Rozzell David
Sauter Guido
Einsmann Margaret
Elhilo Eisa
Striker Michael J.
Wella Aktiengesellschaft
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