Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
2001-01-24
2003-03-25
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S641000, C008S918000, C008S924000
Reexamination Certificate
active
06537332
ABSTRACT:
The present invention relates to novel reactive colorants and mixtures of reactive colorants, to processes for their production and to their use.
The practice of dyeing using reactive dyes has recently led to higher demands being made of 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 time 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 and mixtures of reactive dyes that possess the qualities characterised above to a high degree. The novel dyes and dye mixtures should especially be distinguished by high fixing yields and high fibre-dye binding stability; 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 dyes and dye mixtures defined below.
The present invention accordingly relates to dyes of formula (1)
wherein
R
1
and R
2
are each independently of the other hydrogen or C
1
-C
4
alkyl, and
D
1
and D
2
are each independently of the other a radical of formula (2)
wherein
(R
3
)
0-3
denotes from 0 to 3 identical or different substituents selected from the group halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, carboxy, nitro and sulfo, and
X
1
is a radical of formula (3a), (3b), (3c), (3d), (3e) or (3f)
—SO
2
—Z (3a),
—NH—CO—(CH
2
)
m
—SO
2
—Z (3b),
—CONH—(CH
2
)
n
—SO
2
—Z (3c),
—NH—CO—CH(Hal)—CH
2
—Hal (3d),
—NH—CO—C(Hal)═CH
2
(3e) or
wherein
Y is halogen, T independently thereof has a meaning given for Y or is a non-fibre-reactive substituent or is a fibre-reactive radical of formula (4a), (4b), (4c), (4d) or (4e)
—NH—(CH
2
)
2-3
—SO
2
—Z (4a),
—NH—(CH
2
)
2-3
—O—(CH
2
)
2-3
—SO
2
—Z (4b),
wherein
Z is vinyl or a radical —CH
2
—CH
2
—U and U is a group removable under alkaline conditions,
Z′ is a group —CH(Hal)—CH
2
—Hal or —C(Hal)═CH
2
,
m and n are each independently of the other the number 2, 3 or 4, and
Hal is halogen.
As C
1
-C
4
alkyl for R
1
and R
2
, each independently of the other, there come into consideration, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl, especially methyl and ethyl.
Preferably, one of the radicals R
1
or R
2
is hydrogen and the other is methyl or ethyl.
Special preference is given to R
1
and R
2
as hydrogen.
As halogen for R
3
there come into consideration, for example, fluorine, chlorine, bromine and iodine, preferably chlorine and bromine, and especially chlorine.
As C
1
-C
4
alkyl for R
3
there come into consideration, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl, preferably methyl and ethyl, and especially methyl.
As C
1
-C
4
alkoxy for R
3
there come into consideration, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy and tert-butoxy, preferably methoxy and ethoxy, and especially methoxy.
Preferably, T is a non-fibre-reactive substituent or is a fibre-reactive radical of formula (4a), (4b), (4c), (4d) or (4e).
If T is a non-fibre-reactive substituent, it may be, for example, hydroxy; C
1
-C
4
alkoxy; unsubstituted or hydroxy-, carboxy- or sulfo-substituted C
1
-C
4
alkylthio; amino; amino mono- or di-substituted by C
1
-C
8
alkyl, wherein the alkyl is unsubstituted or is further substituted, e.g. by sulfo, sulfato, hydroxy, carboxy or by phenyl, especially by sulfo or by hydroxy and is uninterrupted or interrupted by an —O— radical; cyclohexylamino; morpholino; N—C
1
-C
4
alkyl-N-phenylamino or phenylamino or naphthylamino, wherein the phenyl or naphthyl is unsubstituted or substituted, e.g. by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, carboxy, sulfo or by halogen.
Examples of suitable non-fibre-reactive substituents T include amino, methylamino, ethylamino, &bgr;-hydroxyethylamino, N-methyl-N-&bgr;-hydroxyethylamino, N-ethyl-N-&bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, &bgr;-sulfoethylamino, cyclohexylamino, morpholino, 2-, 3- or 4-chlorophenylamino, 2-, 3- or 4-methylphenylamino, 2-, 3- or 4-methoxyphenylamino, 2-, 3- or 4-sulfophenylamino, disulfophenylamino, 2-, 3- or 4-carboxyphenylamino, 1- or 2-naphthylamino, 1-sulfo-2-naphthylamino, 4,8-disulfo-2-naphthylamino, N-ethyl-N-phenylamino, N-methyl-N-phenylamino, methoxy, ethoxy, n- or iso-propoxy and hydroxy.
As non-fibre-reactive radical, T is preferably C
1
-C
4
alkoxy, unsubstituted or hydroxy-, carboxy- or sulfo-substituted C
1
-C
4
alkylthio, hydroxy, amino, N-mono- or N,N-di-C
1
-C
4
-alkylamino unsubstituted or substituted in the alkyl moiety by hydroxy, sulfato or by sulfo, morpholino, or phenylamino or N—C
1
-C
4
alkyl-N-phenylamino (wherein the alkyl is unsubstituted or substituted by hydroxy, sulfo or by sulfato) wherein the phenyl ring is in each case unsubstituted or substituted by sulfo, carboxy, acetylamino, chlorine, methyl or by methoxy, or naphthylamino unsubstituted or substituted by from 1 to 3 sulfo groups.
Especially preferred non-fibre-reactive radicals T are amino, N-methylamino, N-ethylamino, N-&bgr;-hydroxyethylamino, N-methyl-N-&bgr;-hydroxyethylamino, N-ethyl-N-&bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, &bgr;-sulfoethylamino, morpholino, 2-, 3- or 4-carboxyphenylamino, 2-, 3- or 4-sulfophenylamino or N—C
1
-C
4
alkyl-N-phenylamino.
In the case of the fibre-reactive radicals T of formulae (4a) and (4b), Z is preferably &bgr;-chloroethyl. In the case of the fibre-reactive radicals T of formulae (4c) and (4d), Z is preferably vinyl or &bgr;-sulfatoethyl.
If T is a fibre-reactive radical, T is preferably a radical of formula (4c) or (4d), and especially of formula (4c).
Hal in the fibre-reactive radicals of formulae (3d), (3e) and (4e) is preferably chlorine or bromine, especially bromine.
Y in the fibre-reactive radical of formula (3f) is, for example, fluorine, chlorine or bromine, preferably fluorine or chlorine, and especially chlorine.
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 and —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 Z accordingly include vinyl, &bgr;-bromo- or &bgr;-chloroethyl, &bgr;-acetoxyethyl, &bgr;-benzoyloxyethyl, &bgr;-phosphatoethyl, &bgr;-sulfatoethyl and &bgr;-thiosulfatoethyl. Z is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl.
D
1
and D
2
preferably are each independently of the other a radical of formula (2a), (2b), (2c), (2d) or (2e)
especially of formula (2a) or (2e), wherein
(R
3a
)
0-2
denotes from 0 to 2 identical or different substituents selected from the group halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy and sulfo, especially methyl, methoxy and sulfo,
X
1a
is &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino,
m is the number 2 or 3, especially 3,
n is the number 2 or 3, especially 2, and
Z
1
, Z
2
, Z
3
and Z
4
are each independently of the others vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl.
Z
1
and Z
2
are preferably each independently of the other vinyl or &bgr;-sulfatoethyl.
Z
3
is preferably &bgr;-chloroethyl or &bgr;-sulfatoethyl, especially &bgr;-chloroethyl.
Z
4
is preferably &bgr;-chloroethyl or &bgr;-sulfatoethyl, especi
Klier Herbert
Tzikas Athanassios
Ciba Speciality Chemicals Corporation
Einsmann Margaret
Mansfield Kevin T.
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