Use of reactive dyes for dyeing hair

Details Use of reactive dyes for dyeing hair Use of reactive dyes for dyeing hair

2000-01-11

2002-11-26

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S411000, C008S412000, C424S401000, C424S407000, C424S060000, C424S070600

Reexamination Certificate

active

06485527

ABSTRACT:

The present invention relates to the use of reactive dyes of the formula I
where
a is 1 or 2,
b is 0 or 1,
Y is vinyl or a radical of the formula C
2
H
4
Q, where Q is an alkali-detachable group,
L
3
is a direct bond or a bridge member of the formula CO—NH—M
1
, where M
1
is C
2
-C
6
-alkylene with or without interruption by 1 or 2 unadjacent oxygen atoms, imino or C
1
-C
4
-alkylimino groups,
A
1
is hydroxysulfonyl or a radical of the formula SO
2
Y,
A
2
is hydrogen, hydroxysulfonyl, methoxy, chlorine, bromine or carboxyl,
W is either in case 1) the radical of a coupling component, of a monoazo dye or additionally, when b=0, of a disazo dye, which may each bear further fiber-reactive groups, or
 in case 2) the radical of a chromophore which optionally has further fiber-reactive groups and is derived from an optionally metallized mono- or disazo dye, from a triphendioxazine, from an anthraquinone, from a metallized formazan or from a metallized phthalocyanine,
L
1
is either in case 1) an azo bridge or
 in case 2) a bridge member of the formula O
2
S—NZ
1
, OC—NZ
1
, Z
1
N—SO
2
, Z
1
N—CO, Z
1
N—CO—NZ
2
, NZ
1
or
where M
2
is a direct bond or methylene, Z
1
and Z
2
are each independently of the other hydrogen, C
1
-C
6
-alkyl or phenyl and X is fluorine, chlorine or bromine, amino, C
1
-C
6
-alkylamino with or without interruption by 1 or 2 unadjacent oxygen atoms, imino or C
1
-C
4
-alkylimino groups and with or without hydroxyl substitution, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-piperazinyl or N—(C
1
-C
4
)-alkylpiperazinyl, or NZ
1
or Nz
2
each also represent 1,4-piperazinediyl,
L
2
is a radical of the formula
where Z
3
, Z
4
, Z
5
and Z
6
are each independently of the others hydrogen, C
1
-C
6
-alkyl or phenyl, L
4
is C
2
-C
8
-alkylene or unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy- or hydroxysulfonyl-substituted phenylene, and X is in each case as defined above,
for dyeing hair, to a method for hair dyeing and to cosmetic preparations for dyeing hair.
The use of reactive dyes falling within the general formula I for dyeing nitrogenous fibers such as wool is known, for example, from U.S. Pat. No. 4,066,638, EP-A-107 614, EP-A-559 617, DE-A-3,441,273 and DE-A-2,154,942. Depending on the dyeing process, dyeing prescriptions for cotton and wool involve a pH of 10-12, temperatures within the range from 60 to 80° C. and treatment times around the 10 hour mark.
U.S. Pat. No. 4,102,641 discloses the use of halotriazinyl reactive dyes for dyeing hair.
JP-A-75 025 529 describes dye formulations for use as hair dyes. The reactive dyes used therein are based on p-sulfatoethylsulfonylaniline as diazo component and fiber-reactive radical. Therefore dyeing with these dyes requires relatively long treatment times.
It is an object of the present invention to provide dyes for dyeing hair under benign dyeing conditions, such as mild pH, short treatment times and low temperatures.
We have found that this object is achieved by the use of reactive dyes of the general formula I for dyeing human hair.
The reactive dyes of the formula I are each indicated in the form of the free acid. It will be appreciated that the use of their physiologically acceptable salts is likewise encompassed by the present invention.
Suitable cations are derived from metal or ammonium ions. Metal ions are especially lithium, sodium or potassium ions. Ammonium ions for the purposes of the present invention are substituted or unsubstituted ammonium cations. Examples of substituted ammonium cations are monoalkyl-, dialkyl-, trialkyl-, tetraalkyl- or benzyltrialkyl-ammonium cations or those cations derived from nitrogenous five- or six-membered saturated heterocycles, such as pyrrolidinium, piperidinium, morpholinium, piperazinium or N-alkylpiperazinium cations or their N-monoalkyl- or N,N-dialkyl-substituted products. Alkyl is generally straight-chain or branched C
1
-C
20
-alkyl, which may be substituted by 1 or 2 hydroxyl groups and/or interrupted by from 1 to 4 oxygen atoms in ether function.
In general, all alkyl and alkylene groups mentioned above and appearing in the formulae which follow may be straight-chain or branched.
Substituted alkyl radicals preferably contain, unless otherwise stated, 1, 2 or 3 substituents, especially 1 or 2 substituents, in any desired position.
Z
1
, Z
2
, Z
3
, Z
4
, Z
5
and Z
6
are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
M
1
and L
4
are each for example (CH
2
)
2
, (CH
2
)
3
, (CH
2
)
4
, CH(CH
3
)CH
2
, CH(CH
3
)CH(CH
3
), (CH
2
)
5
, (CH
2
)
6
.
M
1
may also be (CH
2
)
2
O(CH
2
)
2
, (CH
2
)
3
O(CH
2
)
2
, (CH
2
)
2
O(CH
2
)
2
O(CH
2
)
2
, (CH
2
)
2
NH(CH
2
)
2
, (CH
2
)
3
NH(CH
2
)
2
, (CH
2
)
2
NH(CH
2
)
2
NH(CH
2
)
2
,
L
4
may also be for example (CH
2
)
7
, (CH
2
)
8
, 1,2-, 1,3- or 1,4-phenylene, which may be mono- or disubstituted by methyl, methoxy or hydroxysulfonyl.
X is methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, tert-butylamino, pentylamino, hexylamino, hydroxymethylamino, 2-hydroxyethylamino, 2- or 3-hydroxypropylamino, 2- or 4-hydroxybutylamino, methoxymethylamino, 2-methoxyethylamino, 2- or 3-methoxypropylamino, 2- or 4-methoxybutylamino, ethoxymethylamino, ethoxyethylamino, ethoxypropylamino, ethoxybutylamino, propoxyethylamino or propoxypropylamino.
Q is an alkali-detachable group. Such groups include for example chlorine, bromine, C
1
-C
4
-alkylsulfonyl, phenylsulfonyl, OSO
3
H, SSO
3
H, OP(O)(OH)
2
, C
1
-C
4
-alkylsulfonyloxy, phenylsulfonyloxy, C
1
-C
4
-alkanoyloxy, C
1
-C
4
-dialkylamino or a radical of the formula
where Z
7
, Z
8
and Z
9
are identical or different and each is independently of the others C
1
-C
4
-alkyl or benzyl and An
⊖
is in each case one equivalent of an anion. Suitable anions include for example fluoride, chloride, bromide, iodide, mono-, di- or trichloroacetate, methanesulfonate, benzenesulfonate or 2- or 4-methylbenzenesulfonate.
When a is 2, the radicals
can be identical or different.
When b is 1, the radicals W can likewise be identical or different.
The fiber-reactive group of the formula II
where A
1
, A
2
, L
3
and Y are each as defined above, will hereinafter be referred to as “E”.
Preference for use in the dyeing of hair is given to reactive dyes of the formula I where L
3
is a direct bond.
Preference is further given to the use of reactive dyes of the formula I where A
1
is hydroxysulfonyl.
Preference is likewise given to the use of reactive dyes of the formula I where L
3
is a direct bond and A
1
is a radical of the formula SO
2
Y.
Preference for the use in dyeing hair is also given to reactive dyes of the formula I where A
2
is hydrogen or especially hydroxysulfonyl.
Preference for use in the dyeing of hair is further given to reactive dyes of the formula I where L
1
is an azo bridge.
Preference is also given to the use of reactive dyes of the formula I where L
1
is a bridge member of the formula
and X is as defined above.
Particular preference is given to the use of reactive dyes of the formula I where the hydroxysulfonyl radical is disposed ortho or para to L
1
and the fiber-reactive radical is disposed para or ortho to L
1
or para to the hydroxysulfonyl radical.
Reactive dyes of the formula I whose fiber-reactive radical conforms to the formula II a-g
are very particularly preferred for dyeing hair.
Preference for use in the dying of hair is further given to reactive dyes of the formula I where Y is a radical of the formula —C
2
H
4
SSO
3
H, —C
2
H
4
Cl, —C
2
H
4
OCOCH
3
and particularly —C
2
H
4
OSO
3
H or especially vinyl.
Preference is also given to the use of dyes of the formula I where the substituents are selected from a combination of the above-recited preferred substituents.
The SO
2
Y radicals are additively reacting fiber-reactive radicals, which are distinguished from the substitutively reacting fiber-reactive radicals.
Substitutive reaction of the fiber-reactive group with th

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