Agent for coloring fibers and method for temporarily...

Details Agent for coloring fibers and method for temporarily... Agent for coloring fibers and method for temporarily...

2001-12-21

2003-12-30

Gupta, Yogendra N. (Department: 3732)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S409000, C008S424000, C008S426000, C008S454000, C008S462000, C008S565000, C008S657000, C008S659000, C548S511000, C548S455000

Reexamination Certificate

active

06669739

ABSTRACT:

The object of the present invention is a preparation for coloring fibers, especially of human hair, which contains enamines and Schiff's bases, it also being possible, if so desired, to decolorize the coloring obtained gently at any later time.
Coloring preparations are divided into the areas of oxidation dyeing agents or of tints, depending on the original color of the hair, which is to be colored, and the desired end result. Oxidation hair dyes are outstandingly suitable for covering higher proportions of gray. The oxidation dyeing agents, which are used for gray portions up to 50%, usually are referred to as oxidative tints. On the other hand, the oxidation dyeing agents, which are used when the proportion of gray exceeds 50% or for “lightening” the color, usually are referred to as so-called oxidative dyes. Direct dyes are mainly contained in non-oxidative dyeing agents (so-called tinting agents). Because of their small size, some direct dyes, such as nitro dyes, can penetrate into the hair and dye it directly, at least in the outer regions. Such tints are very gentle to the hair and usually withstand 6 to 8 washings and enable up to about 20% gray to be covered.
In general, direct and oxidative tints are washed out when the hair is washed a few times. Among other factors, the period depends greatly on the structure of the hair and on the shade used. In some cases, oxidative dyes can fade over time. Usually, however, they remain in the hair until the next time the hair is cut. However, a hair coloring, which can be removed at any time, may be desirable for persons who wish to have a particular color only for a certain time or do not like the coloring achieved. Likewise, in the event that the hair is colored for the first time, the possibility of removing the coloring gently and completely reduces the fear of a too drastic change in color (“test coloring”).
The German Offenlegungsschriften 197 17 280 and 197 17 281 disclose the use of a combination of certain heterocyclic carbonyl compounds or benzylidene ketones with amines and/or hydroxy compounds and/or acidic CH compounds for coloring hair without the addition of oxidizing agents. Likewise, the German utility patent 299 08 464 discloses that hair can be dyed permanently by a combination of certain 1,2,3,3-tetramethyl-3H-indolium salts and carbonyl compounds even without the addition of oxidizing agents.
There is however a great need for dyeing agents, which make intensive as well as gentle colorings possible under mild conditions and, if desired, can be decolorize once again at a later time.
It is therefore an object of the present invention, to provide a dyeing agent, which has a very long shelf life and makes possible, on the one hand, a gentle, intensive and stable coloring of the fibers in the yellow, brown, green and violet areas with good fastness properties (wash fastness, crocking fastness, etc.) and, on the other, a gentle and complete removal of this coloring at any time.
Surprisingly, it has now been found that this objective can be accomplished by the use a dyeing agent, which is obtained by mixing two components, the first component containing at least one enamine of Formula (I) or its acid addition salt of Formula (Ia) and the second component containing at least one Schiff's base of Formula (II).
An object of the present invention therefore is a preparation for coloring fibers (A), such as wool, silk, cotton or hair and especially human hair, which is produced by mixing two components (A1) and (A2), wherein the component (A1) has an acidic pH and contains at least one enamine of Formula (I) or its acid addition salt of Formula (Ia)
wherein R1 represents a single ring or multi-ring aromatic group, especially an unsubstituted 5-membered or 6-membered aryl group (preferably a phenyl group or naphthyl group), an unsubstituted 5-membered or 6-membered heterocyclic group (preferably a pyridyl group), a 5-membered or 6-membered aryl group, substituted with a C1 to C4 alkyl group, a C1 to C4 hydroxyalkyl group, a hydroxy group, a methoxy group, substituted with a dialkylamino group or a halogen group (F, Cl, Br, I) (preferably a substituted phenyl group), or a 5-membered or 6-membered heterocyclic group, substituted with a C1 to C4 alkyl group, a C1 to C4 hydroxyalkyl group, a hydroxy group, a methoxy group, a dialkylamino group or a halogen group (F, Cl, Br, I) (preferably a substituted pyridyl group or naphthyl group), R2 is a linear or branched C1 to C8 alkyl group, a linear or branched C1 to C8 hydroxyalkyl group or a C1 to C8 alkoxyalkyl group, wherein oxygen atoms may be located between the carbon atoms of the alkyl chain, R3 is a linear or branched C1 to C8 alkyl group, a C1 to C8 alkoxyalkyl group, a linear or branched C1 to C8 alkylene group, a C1 to C8 alkoxyalkylene group, an oxygen atom, a sulfur atom, an —NH group, or an —NR group, wherein R is an alkyl group, an alkoxyalkyl group, a hydroxyalkyl group or hydrogen, the R1 and R3 groups, together with the nitrogen atom and the carbon atom of the basic enamine structure being able to form a cyclic compound and R4 being hydrogen, a linear C1 to C4 alkyl group or a branched C1 to C4 alkyl group, A
−
being the anion of an organic or inorganic acid, and the component (A2) having an alkaline pH and containing at least one Schiff's base of Formula (II)
R
7
HC═NR
8
  (II)
wherein R7 is a group of the following formulas
wherein Y and Z in each case are 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 hydroxyl 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 —NR
a
H
2
+
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
represents a hydrogen atom, a linear or branched C1 to C4 alkyl group, an optionally substituted aromatic carbon ring or heterocyclic ring, with the proviso that at least one of the R1′ to R7′ groups is not hydrogen, and R8 is a group of the following formulas
wherein R1″, R2″, R3″, R4″, R5″, R6″ and R7″ independently of one another are a hydrogen atom, a methyl group, a halogen atom, a hydroxy group, a C1 to C4 hydroxyalkyl group, a benzyl group, an optionally substituted aromatic carbon ring or heterocyclic ring, a methoxy group, an ethoxy group, a carboxy group, an —NH
2
group, an —NHR
b
group, an —N(R
b
)
2
group, in which R
b
is a hydrogen atom, a linear or branched C1 to C4 alkyl group, a C1 to C4 hydroxyalkyl group, an optionally substituted aromatic carbon ring or an optionally substituted aromatic heterocyclic ring and R8″ is a group, required to form a natural &agr;-amino acid (such as the (CH
2
)
3
-guanidinyl group for forming the &agr;-amino acid arginine, the CH
2
-imidazoyl group for forming the &agr;-amino acid histidine or the CH
2
-indolyl group for forming the &agr;-amino acid tryptophan).
Preferred are compounds of Formula (I), in which the R1 and R3 groups together with the nitrogen atom and the carbon atom of the basic enamine structure form a cyclic compound, R3 preferably being linked to the aromatic R1 group at the carbon, which is in the ortho position to the enamine-substituted carbon.
Especially preferred are the following enamines of Formula (III) to (X), in which X is a carbon atom, substituted with two C1 to C4 alkyl groups, which may be the same or different and, in particular, are two methyl groups, a carbon atom, substituted with a C1 to C4 alkyl group and a hydroxyl group, a sulfur atom, an alkylated nitrogen atom, a not-alkylated nitrogen atom or an oxygen atom, and R2 is a linear or branched C1 to C8 alkyl group, a linear or branched C1 to C8 hydroxyalkyl group, or a C1 to C8 alkoxyalkyl group, in which there may be oxyg

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