Reactive dyes with a heterocyclic anchor

Details Reactive dyes with a heterocyclic anchor Reactive dyes with a heterocyclic anchor

1999-03-29

2001-03-06

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S634000, C534S635000, C534S641000, C544S076000, C540S127000, C548S125000

Reexamination Certificate

active

06197941

ABSTRACT:

The present invention relates to novel 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,
Het is the radical of a 5- or 6-membered aromatic hetero-cyclic ring having from 1 to 3 hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen,
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, a triphendioxazine, an anthraquinone, a metallized formazan or 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 Z
1
and Z
2
are independently of each other hydrogen, C
1
-C
6
-alkyl or phenyl and Hal is fluorine, chlorine or bromine, or NZ
1
or NZ
2
also represents 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 Hal is in each case as defined above,
L
3
is a direct bond or C
1
-C
6
-alkylene with or without interruption by 1 or 2 oxygen or sulfur atoms in ether function or 1 or 2 unadjacent imino, C
1
-C
4
-alkylimino or C
1
-C
4
-alkanoylimino groups, and
A
1
and A
2
are independently of each other hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, halogen, nitro, amino, hydroxysulfonyl or a radical of the formula L
3
—SO
2
—Y, where L
3
and Y are each as defined above
and also to a process for dyeing and printing hydroxyl-containing or nitrogenous substrates with the novel dyes.
It is an object of the present invention to provide novel reactive dyes having advantageous application properties. The novel dyes shall be especially suitable for the exhaust and cold pad-batch process and shall be notable in particular for high yield, high wetfastness properties and brilliant dyeings. In addition, the unfixed portions shall be easy to wash off.
We have found that this object is achieved by the reactive dyes of the formula I defined at the beginning and also their use for dyeing or printing hydroxyl-containing or nitrogenous organic 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 likewise encompassed by the claims.
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 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-methyl-pentyl.
A
1
and A
2
are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, fluorine, chlorine or bromine.
L
3
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
.
L
3
may also be methylene, (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
S(CH
2
)
2
, (CH
2
)
3
S(CH
2
)
2
, (CH
2
)
2
S(CH
2
)
2
S(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.
Het is the radical of a 5- or 6-membered aromatic heterocyclic ring containing from 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen.
Suitable heterocyclic parent species, which may bear substituents, for derivations of the Het radicals include for example pyrrole, furan, thiophene, pyrazole, imidazole, oxazole, thiazole, isothiazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine or pyrazine. Suitable substituents include for example C
1
-C
4
-alkyl, phenyl, halogen, cyano, carboxyl or C
1
-C
4
-alkoxycarbonyl.
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 trichloracetate, 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
, Het, L
3
and Y are each as defined above, will hereinafter be referred to as “E”.
Preference is given to reactive dyes of the formula I where L
3
is C
1
-C
4
-alkylene with or without interruption by one oxyen atom in ether function.
Preference is further given to reactive dyes of the formula I where A
1
and A
2
are independently of each other hydrogen, nitro, amino, hydroxysulfonyl or a radical of the formula SO
2
C
2
H
4
OSO
3
H. Preferred substituents A
1
and/or A
2
are in particular hydrogen and hydroxysulfonyl.
Preference is further given to reactive dyes of the formula I where Het is the radical of a 5-membered heterocycle. Emphasis is given in this connection to those radicals which have 3 heteroatoms, in particular those which are derived from 1,3,4-oxadiazole, 1,2,4-thiadiazole or 1,3,4-thiadiazole, especially 1,2,4-oxadiazole-3,5-diyl.
Preference 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 also in particular —C
2
H
4
OSO
3
H or vinyl. Particular technical interest pertains to the fiber-reactive groups of the formula IIa or IIb
where
A
1
and A
2
are independently of each other hydrogen, nitro, amino, hydroxysulfonyl or a radical of the formula SO
2
C
2
H
4
OSO
3
H,
L
3
is C
1
-C
4
-alkylene, and
Y is as defined above.
Preference is further given to reactive dyes of the formula I where L
1
is a bridge member of the formula
in case 2).
Preference is further given to reactive dyes of the formula I where L
1
is ortho-disposed to the heterocycle in case 1).
Preference is additionally given to 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 aliphatic fiber-reactive groups as distinct from heterocyclic fiber-reactive groups. Fiber-reactive groups are the groups which

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