Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1998-10-08
2003-10-07
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S423000, C008S406000, C008S410000, C008S416000, C546S307000, C564S305000
Reexamination Certificate
active
06630004
ABSTRACT:
The present invention relates to a composition for dyeing keratinous fibers, in particular human keratinous fibers, comprising, as oxidation base, at least one compound of formula (I), defined below, which can be referred to, for convenience sake only, as an amino acid derivative substituted on an amino group by a group with an aromatic nucleus, to a dyeing process using such a composition and employing development by an oxidizing agent and to compounds of formula (I′), defined below, which can also be referred to, for convenience sake only, as amino acid derivatives in which an amino group is substituted by a group with an aromatic nucleus.
It is known to dye keratinous fibers, in particular human hair, with dyeing compositions comprising oxidation dye precursors comprising “oxidation bases”, in particular ortho- or para-phenylenediamines and ortho- or para-aminophenols, as well as couplers, also known as coloring modifiers, more particularly aromatic meta-phenylenediamines, meta-aminophenols and meta-diphenols, which make it possible to modify and to enrich with highlights the “base” colorations obtained with the condensation products of oxidation bases.
In the field of oxidation hair dyeing, it is essential to have available oxidation dye precursors having a high dyeing power, in order to allow the formulator to create a broad palette of shades. Furthermore, it is also important for the oxidation dye precursors to have a high dyeing power at neutral pH in the region of 7 rather than at basic pH (pH≧9), in order not to damage the keratinous fiber and to reduce irritation to the scalp.
It is as a result of much research that the inventors have discovered that it is possible to obtain intense natural shades on keratinous fibers, in particular at a pH in the region of neutrality, by using, as oxidation bases, compounds of the formula (I) set forth below which can also be characterized as amino acid derivatives substituted on an amino group by a group with an aromatic nucleus.
The subject-matter of the present invention is thus an oxidation dyeing composition for keratinous fibers, in particular for human keratinous fibers, such as hair, comprising, in a medium appropriate for dyeing, as oxidation base, at least one compound having the formula (I):
in which:
n is an integer ranging from 0 to 11;
R represents a hydrogen atom, an amino radical, a saturated or unsaturated, linear or branched, C
1
-C
6
alkyl radical or a radical chosen from:
R′ represents a saturated or unsaturated, linear or branched, C
1
-C
6
alkyl radical;
n′ is an integer ranging from 1 to 6;
X represents an aromatic group with one or two rings, wherein said ring or rings may comprise at least one heteroatom chosen from S, N or O; and further wherein said ring or rings are substituted, wherein at least one substituent on said ring or rings is an —NHR″ group or an —OH radical in the para or ortho position on the aromatic group X with respect to the —NH— group, wherein R″ denotes a hydrogen atom or an optionally hydroxylated, saturated or unsaturated, linear or branched, C
1
-C
6
alkyl radical,
or an acid addition salt thereof,
with the proviso that compounds in which n=0, R=H and X is a 4-hydroxyphenyl radical are not included within formula (I).
The compounds of the formula (I) can be optically active isomers or mixtures of such isomers.
The novel dyes thus obtained make it possible to obtain strong and non-toxic natural colorings at neutral pH in the region of 7.
These novel dyes, in addition, exhibit good resistance to light, washing, bad weather, perspiration and the various treatments to which hair may be subjected.
Another subject of the invention is the ready-for-use dyeing composition comprising at least one compound of formula (I) as defined above, as oxidation base, and at least one oxidizing agent.
The invention is also targeted at a process for dyeing keratinous fibers, in particular human keratinous fibers, such as hair, which involves applying, to these fibers, at least one composition (A) comprising, in a medium appropriate for dyeing, as oxidation base, at least one compound of formula (I) as defined above and in developing the color in alkaline, neutral or acidic medium using an oxidizing agent which is added only at the time of use to the composition (A) or which is present in a composition (B) applied simultaneously or sequentially in a separate fashion.
Another subject of the invention is multi-compartment dyeing devices or kits, the first compartment of which comprises a composition (A) comprising at least one compound of formula (I) as defined above as oxidation base and the second compartment of which comprises a composition (B) comprising an oxidizing agent in a medium appropriate for dyeing.
A glycine derivative, namely N-(4-aminophenyl)glycine, is known in thermography as transfer reagent in a duplication process disclosed in French Patent FR-A-1,506,081 and in photography according to Patent GB-A-1,227,395 or Patent Application JP-A-02068546.
Another subject of the present invention is compounds of formula (I′):
in which:
n is an integer ranging from 0 to 11;
R represents a hydrogen atom, an amino radical, a saturated or unsaturated, linear or branched, C
1
-C
6
alkyl radical or a radical chosen from:
R′ represents a saturated or unsaturated, linear or branched, C
1
-C
6
alkyl radical;
n′ is an integer ranging from 1 to 6;
X represents an aromatic group with one or two rings, wherein said ring or rings may comprise at least one heteroatom chosen from S, N and O; and said ring or rings are substituted, wherein at least one substituent on said ring or rings is an —NHR″ group or an —OH radical in the para or ortho position on the aromatic group X with respect to the —NH— group, wherein R″ denotes a hydrogen atom or an optionally hydroxylated, saturated or unsaturated, linear or branched, C
1
-C
6
alkyl radical, with the proviso that said ring or rings are not substituted by any nitro groups,
or an acid addition salt thereof
with the further proviso that compounds in which
n=0, R=H and X is a 4-aminophenyl, 4-hydroxyphenyl, 3-hydroxy-2-pyridyl or 4-hydroxy-3-pyridyl radical;
n=0, R=−CH
3
and X is a 3-hydroxy-2-pyridyl radical; and
n=0, R=−CH
2
OH and X is a 3,4-dihydroxy-6-methylphenyl radical
are not included within formula (I′).
These compounds of the formula (I′) can be optically active isomers or mixtures of such isomers.
In the formula (I) or (I′), X preferably represents a phenyl or pyridyl ring substituted by an amino group —NH
2
.
The preferred compounds of the formula (I′) are:
N&egr;-(4-aminophenyl)-L-lysine;
N&egr;-(4-amino-2-pyridyl)-L-lysine;
N&agr;-(4-aminophenyl)-L-lysine;
N&agr;,N&egr;-di(4-aminophenyl)-L-lysine;
N-(4-aminophenyl)-L-serine;
6-[N-(4-aminophenyl)amino]caproic acid;
&agr;-N-(4-aminophenyl)amino-&egr;-caprolactam; and
their acid addition salts.
The acid addition salts are preferably chosen from hydrochlorides, sulphates, hydrobromides and tartrates.
The preferred compounds of the formula (I) for being used in oxidation dyeing according to the invention are: N&egr;-(4-aminophenyl)-L-lysine, N&egr;-(4-amino-2-pyridyl)-L-lysine, N-(4-aminophenyl)glycine, N&agr;-(4-aminophenyl)-L-lysine, N&agr;,N&egr;-di(4-aminophenyl)-L-lysine, N-(4-aminophenyl)-L-serine, 6-[N-(4-aminophenyl)amino]caproic acid, &agr;-N-(4-aminophenyl)amino-&egr;-caprolactam, and their acid addition salts.
The compounds of formula (I) or (I′) are prepared according to the following procedures, depending on whether they are lysine derivatives, glycine derivatives or other derivatives, such as w-amino acids and lactam derivatives.
LYSINE DERIVATIVES
Preparation of Aromatic Nitro Derivatives at the N&egr; Position of Lysine
General Procedure:
10 g (54.75 mmol) of L-lysine monohydrochloride are dissolved in 44 ml (2 eq) of a 10% aqueous sodium hydroxide solution and 120 ml of water in a 500 ml three-necked flask eq
Bordier Thierry
Philippe Michel
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner LLP
L'Oreal (S.A.)
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