Reactive dyes with a combination anchor

Details Reactive dyes with a combination anchor Reactive dyes with a combination anchor

2000-09-07

2002-06-25

Powers, Flona T. (Department: 1626)

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

Organic compounds

Azo

C008S549000

Reexamination Certificate

active

06410698

ABSTRACT:

The present invention relates to novel red reactive dyes of the general formula I
where
n is 0 or 1,
m 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 is C
2
-C
6
-alkylene with or without interruption by 1 or 2 nonadjacent oxygen atoms or 1 or 2 imino groups or is cyclohexylene,
Hal is fluorine or chlorine,
R
1
is hydrogen or hydroxysulfonylmethyl,
R
2
is hydrogen or hydroxysulfonylmethyl, and
R
3
is carboxyl or hydroxysulfonyl and may also be hydrogen when R
1
and/or R
2
are each hydroxysulfonylmethyl,
their mixtures and their use for dyeing or printing hydroxyl-containing or nitrogenous substrates.
EP-A-074 928 describes similar azo dyes having a sulfato or hydroxyethylsulfonylethylaminochlorotriazineamino radical on the sulfophenyl diazo component.
EP-A-772 653 concerns azo dyes prepared from &ggr;-acid which has been sulfomethylated at the amino group and a diaminobenzenesulfonic acid diazo component in which one of the amino groups is joined through a chlorotriazineamino radical to sulfatoethylsulfonylbenzene.
EP-A-499 588 teaches dyes having a chloroethylsulfonylethylaminochlorotriazine radical on the sulfophenyl diazo component, which was coupled onto &ggr;-acid.
There continues to be a need for red lightfast reactive dyes to fill a large gap in the market. Prior art dyes are unsatisfactory with regard to their application properties, especially their lightfastnesses.
It is an object of the present invention to provide red dyes having an advantageous property profile, especially good wet- and lightfastnesses.
We have found that this object is achieved by the reactive dyes of the formula I defined at the beginning, their mixtures and their use for dyeing or printing hydroxyl-containing or nitrogenous substrates.
The novel reactive dyes of the formula I are each indicated in the form of the free acid. It will be appreciated that their salts are encompassed by the invention, too.
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-dialkylsubstituted 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, alkenyl and alkylene groups mentioned above and appearing in the formulae hereinbelow may be straight-chain or branched.
Q is 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 X
1
, X
2
and X
3
are identical or different and are each 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.
L is 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
, (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
or (CH
2
)
2
NH(CH
2
)
2
NH(CH
2
)
2
.
Aromatic diamines useful as diazo component and also attachment site to the cyanuric halide include for example 2,4-diaminobenzenesulfonic acid, 2,5-diaminobenzenesulfonic acid, 4,6-diaminobenzene-1,3-disulfonic acid and 2,5-diaminobenzene-1,4-disulfonic acid.
Suitable coupling components include for example the aminonaphthalenesulfonic acids 2-naphthylamine-3,6-disulfonic acid, 2-naphthylamine-5,7-disulfonic acid, 2-naphthylamine-6,8-disulfonic acid, 2-hydroxysulfonylmethylaminonaphthalene-5-sulfonic acid or 2-hydroxysulfonylmethylaminonaphthalene-6-sulfonic acid.
Suitable coupling components further include aminonaphtholsulfonic acids such as 2-amino-5-hydroxynaphthalene-7-sulfonic acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid, 2-amino-8-hydroxynaphthalene-3,6-disulfonic acid, 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid, 2-amino-7-hydroxysulfonylmethyl-8-hydroxynaphthalene-6-sulfonic acid, 2-hydroxysulfonylmethylamino-8-hydroxynaphthalene-6-sulfonic acid, 2-hydroxysulfonylmethylamino-7-hydroxysulfonyl-methyl-8-hydroxynaphthalene-6-sulfonic acid.
Preference is given to reactive dyes of the formula I wherein R
3
is carboxyl or preferably hydroxysulfonyl.
Preference is also given to reactive dyes of the formula I wherein R
1
is hydrogen.
Preference is further given to reactive dyes of the formula I wherein R
3
is hydrogen and R
1
is hydroxysulfonylmethyl.
Preference is moreover given to reactive dyes of the formula I where Y is vinyl or 2-sulfatoethyl, 2-thiosulfatoethyl, 2-chloroethyl or acetoxyethyl in the fiber-reactive radical —SO
2
Y.
Reactive dyes containing coupling components of the general formula II a-d
where R
1
and R
2
are each as defined above, are also preferred.
Preference is given especially to dyes of the general formula III
where R
1
, R
3
, Hal, L and Y are each as defined above.
Preference is further given to reactive dyes of the formula I where L is ethylene.
Preference is given particularly to dyes of the general formula I and III and also to those containing coupling components of the formula IIa-d, wherein R
1
is hydroxysulfonylmethyl.
Preference is also given to reactive dyes wherein the hydroxysulfonyl group in the phenyl ring is ortho to the diazo group.
The novel reactive dyes of the general formula I are obtainable in a conventional manner.
For example, a phenylenediamine of the formula
where R
3
is as defined above, can be reacted with a trihalotriazine to form compounds of the formula
These amines of the formula V are conventionally diazotized and acid-coupled onto coupling components of the formula II
where R
1
, R
2
, m and n are each as defined above. The resulting azo dye is reacted with an amine of the formula
H
2
N—L—SO
2
Y  (VI),
in aqueous solution at pH 5-6 to obtain the dyes of the invention.
The order of the elementary reactions is discretionary. Thus, in a further process variant, the halogen in the amine of the formula V is first replaced by the amine of the formula VI, prior to diazotization and coupling onto the naphthalenesulfonic acid of the formula II.
Hydroxysulfonyl-substituted naphthalenesulfonic acids are obtained in a conventional manner by reaction with hydroxymethanesulfonic acid.
The present invention further provides mixtures of the dyes of the formula I with from 0.1 to 30 parts by weight of one or more red, orange, yellow or blue dyes based on 100 parts by weight of reactive dye I.
Suitable yellow reactive dyes are described in U.S. Pat. No 5,182,371 for example. Further suitable dyes include: C.I. Reactive Yellow 145, C.I. Reactive Yellow 168 or C.I. Reactive Yellow 176.
Suitable orange reactive dyes conform for example to the formula
Further suitable dyes include: C.I. Reactive Orange 7 (17 756), C.I. Reactive Orange 15, C.I. Reactive Orange 16 (17 757), C.I. Reactive Orange 56, C.I. Reactive Orange 57, C.I. Reactive Orange 72 (17 754), C.I. Reactive Orange 74, C.I. Reactive Orange 82, C.I. Reactive Orange 83 or C.I. Reactive Orange 90.
Suitable red reactive dyes are described in U.S. Pat. No. 5,200,511, for example. Further suitable dyes include: C.I. Reactive Red 35, C.I. Reactive Red 103, C.I. Reactive Red 113, C.I. Reactive Red 180, C.I. Reactive Red 194, C.I. Reactive Red 195, C.I. Reactive Red 198, C.I. Reactive Red 222, C.I. Reactive Red 223, C.I. Reactive Red 227, C.I. Reactive Red 228 or C.I

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