Reactive colorants, production and use thereof

Details Reactive colorants, production and use thereof Reactive colorants, production and use thereof

2001-03-19

2003-02-11

Powers, Fiona T. (Department: 1751)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S642000, C534S643000, C008S549000

Reexamination Certificate

active

06518408

ABSTRACT:

The present invention relates to novel reactive colorants, to a process for their production and to their use.
The practice of dyeing using reactive dyes has recently led to higher demands being made on the quality of the dyeings and the profitability of the dyeing process. As a result, there is still a need for novel reactive dyes having improved properties, especially in respect of their application.
Dyeing nowadays requires reactive dyes that have sufficient substantivity and at the same have good ease of washing off of unfixed dye. They should also have a good tinctorial yield and high reactivity, the objective being to provide especially dyeings having high degrees of fixing. The known dyes do not satisfy these requirements in all properties.
The problem underlying the present invention is accordingly to find, for the dyeing and printing of fibre materials, novel improved reactive dyes having the qualities characterised above to a high degree. The novel dyes should especially be distinguished by high fixing yields and high fibre-dye binding stability, and it should also be possible for dye that is not fixed to the fibre to be washed off easily. The dyes should also yield dyeings having good allround properties, for example fastness to light and to wetting.
It has been shown that the problem posed is largely solved by the novel reactive dyes defined below.
The present invention accordingly relates to compounds of formula (1)
wherein
K
1
and K
2
are each independently of the other the radical of a coupling component from the series benzene, naphthalene, 4-alkyl-6-hydroxypyridone-(2), 2,5-diamino-4-alkylpyridine, 1-arylpyrazolone-(5) and 1-aryl-5-aminopyrazole, at least one of the radicals K
1
and K
2
containing a fibre-reactive group,
with the proviso that
(i) the fibre-reactive group is not 2-(&bgr;-sulfatoethylsulfonyl)ethylamino when K
1
and K
2
are phenyl substituted by a fibre-reactive group, and
(ii) the fibre-reactive group is not &bgr;-sulfatoethylsulfonyl when K
1
and K
2
are N-(&bgr;-sulfatoethyl)aniline substituted on the phenyl ring by a fibre-reactive group.
The radicals K
1
and K
2
may contain substituents customary in dyes.
From the series of substituents there may be mentioned by way of example: alkyl groups having from 1 to 12 carbon atoms, especially from 1 to 4 carbon atoms, such as methyl, ethyl, n- or iso-propyl, and n-, iso-, sec- or tert-butyl, alkoxy groups having from 1 to 8 carbon atoms, especially from 1 to 4 carbon atoms, such as methoxy, ethoxy, n- or iso-propoxy, and n-, iso-, sec- or tert-butoxy, C
1
-C
4
alkoxy substituted in the alkyl moiety, for example, by hydroxy, C
1
-C
4
alkoxy or by sulfato, such as 2-hydroxyethoxy, 3-hydroxy-propoxy, 2-sulfatoethoxy, 2-methoxyethoxy or 2-ethoxyethoxy, alkanoylamino groups having from 2 to 8 carbon atoms, especially C
2
-C
4
alkanoylamino groups, such as acetyl-amino or propionylamino, benzoylamino or C
2
-C
4
alkoxycarbonylamino groups, such as methoxycarbonylamino or ethoxycarbonylamino, amino, N-mono- or N,N-di-C
1
-C
4
-alkylamino unsubstituted or substituted in the alkyl moiety, for example, by hydroxy, sulfo, sulfato or by C
1
-C
4
alkoxy, such as methylamino, ethylamino, N,N-dimethyl- or N,N-diethyl-amino, sulfomethylamino, &bgr;-hydroxyethylamino, N,N-di(2-hydroxyethylamino), N-&bgr;-sulfato-ethylamino, phenylamino unsubstituted or substituted in the phenyl moiety by methyl, methoxy, halogen or by sulfo, N—C
1
-C
4
alkyl-N-phenylamino unsubstituted or substituted in the alkyl moiety by hydroxy, sulfo or by sulfato or unsubstituted or substituted in the phenyl moiety by methyl, methoxy, halogen or by sulfo, such as N-methyl-N-phenylamino, N-ethyl-N-phenylamino, N-&bgr;-hydroxyethyl-N-phenylamino or N-&bgr;-sulfoethyl-N-phenylamino, unsubstituted or sulfo-substituted naphthylamino, alkanoyl groups having from 2 to 8 carbon atoms, especially from 2 to 4 carbon atoms, such as acetyl or propionyl, benzoyl, alkoxy-carbonyl having from 1 to 4 carbon atoms in the alkoxy moiety, such as methoxycarbonyl or ethoxycarbonyl, alkylsulfonyl having from 1 to 4 carbon atoms, such as methylsulfonyl or ethylsulfonyl, phenyl- or naphthyl-sulfonyl, trifluoromethyl, nitro, cyano, hydroxy, halogen, such as fluorine, chlorine or bromine, carbamoyl, N—C
1
-C
4
alkylcarbamoyl, such as N-methyl-carbamoyl or N-ethylcarbamoyl, sulfamoyl, N—C
1
-C
4
alkylsulfamoyl, such as N-methyl-sulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl or N-butylsulfamoyl, N-(&bgr;-hydroxyethyl)sulfamoyl, N,N-di(&bgr;-hydroxyethyl)sulfamoyl, N-phenylsulfamoyl, ureido, carboxy, sulfomethyl, sulfo or sulfato, and fibre-reactive radicals. The alkyl radicals may additionally be interrupted by oxygen (—O—) or by an amino group (—NH—, —N(C
1
-C
4
alkyl)-).
The term “sulfo” here generally includes both the free acid —SO
3
H and any desired salt form, for example an alkali metal, alkaline earth metal or ammonium salt or the salt of an organic amine. Examples thereof include the sodium, potassium, lithium or ammonium salt or the salt of triethanolamine.
Preferably each of the radicals K
1
and K
2
in the compounds according to the invention contains at least one fibre-reactive group, and especially one fibre-reactive group. “Fibre-reactive radicals” are to be understood as meaning those that are capable of reacting with the hydroxy groups of cellulose, with the amino, carboxy, hydroxy and thiol groups in wool and silk, or with the amino and, where present, carboxy groups of synthetic polyamides, with the formation of covalent chemical bonds. The fibre-reactive radicals are generally bound to the dye radical directly or by way of a bridge member. Suitable fibre-reactive radicals include, for example, those containing at least one removable substituent on an aliphatic, aromatic or heterocyclic radical or wherein the mentioned radicals contain a radical suitable for reaction with the fibre material, such as, for example, a vinyl radical. A fibre-reactive radical present in K
1
or K
2
preferably corresponds to formula (2a), (2b), (2c), (2d) or (2e)
—SO
2
—Y  (2a),
—CONR
2
—(CH
2
)
n
—SO
2
—Y  (2b),
—N—CO—CH(Hal)—CH
2
-Hal (2c),
 —NH—CO—C(Hal)═CH
2
  (2d) or
wherein
Hal is chlorine or bromine and
X is halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl,
T independently thereof has a meaning given for X or is hydroxy, C
1
-C
4
alkoxy, phenoxy, C
1
-C
4
alkylthio, morpholino, amino unsubstituted or substituted by non-fibre-reactive radicals, or a fibre-reactive radical of formula (3a), (3b), (3c), (3d), (3e) or (3f)
R
1
and R
1a
are each independently of the other hydrogen or C
1
-C
4
alkyl,
R
2
is hydrogen, C
1
-C
4
alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or by cyano, or a radical
R
3
is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
alkanoyloxy, carbamoyl or the group —SO
2
—Y,
alk and alk, are each independently of the other C
1
-C
6
alkylene,
arylene is a phenylene or naphthylene radical unsubstituted or substituted by sulfo, carboxy, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or by halogen,
Y
1
is a group —CH(Hal)—CH
2
—Hal or —C(Hal)═CH
2
and Hal is chlorine or bromine,
Q is a radical —O— or —NR
1
—, wherein R
1
is as defined above,
W is a group —SO
2
—NR
2
—, —CONR
2
— or —NR
2
CO—,
n is an integer from 1 to 6 and m is 0 or 1 and
Y is vinyl or a radical —CH
2
—CH
2
—U and U is a group removable under alkaline conditions.
As a leaving group U there come into consideration, for example, —Cl, —Br, —F, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OPO
3
H
2
, —OCO—C
6
H
5
, —OSO
2
—C
1
-C
4
alkyl or —OSO
2
—N(C
1
-C
4
alkyl)
2
. U is preferably a group of formula —Cl, —OSO
3
H, —SSO
3
H, —OCO—CH
3
,—OCO—C
6
H
5
or —OPO
3
H
2
, especially —Cl or —OSO
3
H and more especially —OSO
3
H.
Examples of suitable radicals Y are accordingly vinyl, &bgr;-bromo- or &bgr;-chloroethyl, &bgr;-acetoxy-ethyl, &bgr;-benzoyloxyethyl, &bgr;-phosphatoethyl, &bgr;-sulfatoethyl and &bgr;-thiosulfatoethyl. Y is preferably vinyl, &bgr;-c

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