Cationic azo-dyes

Details Cationic azo-dyes Cationic azo-dyes

2001-05-04

2002-02-12

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S677000, C534S688000, C534S757000, C534S806000, C534S829000, C534S830000, C534SDIG003, C008S639000

Reexamination Certificate

active

06346609

ABSTRACT:

The present invention relates to cationic azo dyes of the general formula I
where
R
1
and R
2
are independently hydrogen, nitro, halogen, C
1
-C
6
-alkyl,
R
3
is hydrogen, C
1
-C
6
-alkyl with or without interruption by 1 or 2 nonadjacent oxy, imino, C
1
-C
6
-alkylimino groups or by a
 radical,
A
1
and A
2
are independently oxy, imino or substituted or unsubstituted C
1
-C
6
-alkylimino,
B
1
and B
2
are independently C
1
-C
6
-alkylene with or without interruption by 1 or 2 nonadjacent oxy, imino, substituted or unsubstituted C
1
-C
6
-alkylimino groups or by a
 radical,
An
⊖
is the equivalent of an anion,
n is 1, and
K is the radical of a coupling component or the radical of a monoazo dye of the formula
 where
R
4
′ and R
5
′ are independently hydroxyl, amino, morpholino or mono- or di(C
1
-C
6
)alkylamino, whose alkyl radicals are unsubstituted or substituted by hydroxyl, amino, cyano, C
1
-C
6
-alkoxycarbonyl, carbamoyl or mono- or di(C
1
-C
6
)alkylcarbamoyl and uninterrupted or interrupted by oxy, and
Q
1
, Q
2
and Q
3
are independently hydrogen, C
1
-C
10
-alkyl with or without interruption by from 1 to 4 nonadjacent oxy, imino and substituted or unsubstituted C
1
-C
4
-alkylimino groups and with or without hydroxyl, halogen or phenyl substitution, or Q
1
and Q
2
combine with the linking nitrogen atom to form a 5- or 6-membered heterocyclic radical which optionally contains nitrogen or oxygen as further hetero atom,
and additionally n is from 2 to 8 when K is the radical of a coupling component of the formula IIIa′
 where
R
6
′, is hydrogen, C
1
-C
6
-alkoxy with or without oxy interruption in its alkyl radical, mono- or di(C
1
-C
6
)alkylamino, C
1
-C
6
-alkoxycarbonyl, carbamoyl, mono- or di(C
1
-C
6
)alkylcarbamoyl, sulfamoyl, mono- or di(C
1
-C
6
)alkylsulfamoyl,
processes for their preparation, their use for dyeing and printing natural or synthetic substrates and also their mixtures.
DE-A-2 218 645 describes water-insoluble trisazo pigments which are monoazo dyes linked via triethanolamine.
DE-A-2 160 590 describes anthranilic acid derivatives bridged with a diethanolamine via the ester group. These diamines are useful for preparing polyurethanes.
It is an object of the present invention to provide novel dyes which have advantageous application properties, especially high affinities for the substrates used, and also good fastness to bleeding and lightfastness.
We have found that this object is achieved by the dyes of the formula I which are defined at the beginning.
Alkyl and alkylene appearing in the abovementioned formula may be straight-chain or branched.
Substituted alkyl appearing in the abovementioned formula may have as substituents for example hydroxyl and methoxy. The number of substituents in the substituted alkyl is generally 1 or 2.
Q
1
and Q
2
combining with the joining nitrogen atom to form a 5- or 6-membered heterocyclic radical which optionally contains nitrogen or oxygen as further hetero atom may be saturated radicals such as pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl with or without methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-hydroxyethyl or 2- or 3-hydroxypropyl substitution on the nitrogen. Further possibilities are unsaturated radicals such as pyrrolyl, pyrazolyl, oxazolyl, isooxazolyl or imidazolyl with or without methyl, ethyl, propyl or butyl substitution in 2- and/or 4-position or N-3(C
1
-C
4
)alkylimidazolyl with or without methyl, ethyl, propyl or butyl substitution in 2- and/or 4-position.
Halogen is fluorine, chlorine or bromine.
R
1
, R
2
, R
3
, Q
1
, Q
2
and Q
3
are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
R
3
, Q
1
, Q
2
and Q
3
may each also be for example 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 3,7-dioxaoctyl, 4,7-dioxaoctyl, N,N-dimethylaminoethyl, N,N-diethylaminoethyl, 3-(N,N-dimethylamino)propyl, 3-(N,N-diethylamino)propyl, 2-methylaminoethyl, 2-ethylaminoethyl, 3-propylaminoethyl, 2- or 3-methylaminopropyl, 2- or 3-ethylaminopropyl or 2- or 3-propylaminopropyl.
Q
1
, Q
2
and Q
3
may each also be for example heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl (the above designations isooctyl, isononyl and isodecyl are trivial names derived from the alcohols obtained by the oxo process - cf. Ullmanns Encyklopädie der technischen Chemie, 4th edition, volume 7, pages 215 to 217, and also volume 11, pages 435 and 436), 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 2-chloroethyl, 2- or 3-chloropropyl, 2- or 4-chlorobutyl, benzyl, 1- or 2-phenylethyl, 2- or 3-butoxypropyl, 2- or 4-propoxybutyl, 4,8-dioxadecyl, 3,7-dioxanonyl, 4,7-dioxanonyl, 2- or 4-butoxybutyl, 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9-trioxadodecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl, 4-hydroxy-2-methyl-3-azabutyl, 4-hydroxy-3-hydroxymethyl-2-methyl-3-azabutyl, 5-hydroxy-2-methyl-3-azapentyl, 5-hydroxy-3-(2-hydroxy-ethyl)-2-methyl-3-azapentyl, 8-hydroxy-2-methyl-3-aza-6-oxaoctyl, 11-hydroxy-2-methyl-3-aza-6,9-dioxaundecyl, 8-hydroxy-(5-hydroxy-3-oxapentyl)-2-methyl-3-aza-6-oxaoctyl or 11-hydroxy-3-(8-hydroxy-3,6-dioxaoctyl)-2-methyl-3-aza-6,9-dioxaundecyl, N,N-dipropylaminoethyl, N,N-dibutylaminoethyl,3-(N,N-dipropylamino)propyl or 3-(N,N-dibutylamino)propyl.
A is for example methylimino, ethylimino, propylimino, isopropylimino, butylimino, isobutylimino, sec-butylimino, tert-butylimino, pentylimino, isopentylimino, neopentylimino, tert-pentylimino, hexylimino or 2-methylpentylimino.
B
1
and B
2
are each for example methylene, ethylene, 1,2- or 1,3-propylene, 1,2-, 2,3- or 1,4-butylene, (CH
2
)
2
O(CH
2
)
2
, (CH
2
)
3
O(CH
2
)
2
, (CH
2
)
3
O(CH
2
)
3
, (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
,
An
⊖
, the equivalent of an anion, is derived for example from the following anions: fluoride, chloride, bromide, iodide, sulfate, phosphate, formate, acetate, propionate, mono-, di- or trichloroacetate, lactate, methoxyacetate, citrate, succinate, methanesulfonate, benzenesulfonate, 2- or 4-methylbenzenesulfonate or naphthalenesulfonate.
Suitable coupling components KH are compounds of the benzene, naphthalene, quinolene, pyridone, barbituric acid or pyrazolone series and correspond for example to the compounds of the formulae III a-f
where
R
4
is hydroxyl, amino, morpholino, mono- or di(C
1
-C
6
)alkylamino whose alkyl radicals are unsubstituted or substituted by hydroxyl, amino, cyano, C
1
-C
6
-alkoxycarbonyl, carbamoyl or mono or di(C
1
-C
6
)alkylcarbamoyl and are uninterrupted or interrupted by oxy or is C
1
-C
6
-alkoxy,
R
5
is hydrogen, C
1
-C
6
-alkyl or R
4
,
R
6
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy with or without oxy interruption in its alkyl radical, mono or di(C
1
-C
6
)alkylamino, C
1
-C
6
-alkoxycarbonyl, carbamoyl, mono or di(C
1
-C
6
)alkylcarbamoyl whose alkyl radicals are unsubstituted or substituted by hydroxyl or amino and are uninterrupted or oxy interrupted, sulfamoyl, mono or di(C
1
-C
6
)alkylsulfamoyl whose alkyl radicals are unsubstituted or hydroxyl or amino substituted and uninterrupted or oxy interrupted, or is carboxyl,
R
7
is hydroxyl, amino, mono or di(C
1
-C
12
)alkylamino, cyclohexylamino,
R
8
is hydrogen, hydroxyl, amino, formylamino, acetylamino, C
1
-C
6
-alkyl,
R
9
is hydrogen, C
1
-C
6
-alkyl, phenyl, hydroxyl, cyano, acetyl, benzoyl, methoxycarbonyl, carbamoyl,
R
10
is hydrogen, chlorine, bromine, acetylamino, amino, nitro, sulfamoyl, methylsulfonyl, phenylsulfonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkanoyl, benzoyl, carbamoyl, cyano, N-methylimidazolyl, pyridinio,
R
11
is hydrogen, C
1
-C
6
-alkyl with or without phenyl, hydroxyl, amino, C
1
-C
6
-alkoxy, acetylamino, benz

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