AZO dyestuffs

Details AZO dyestuffs AZO dyestuffs

2000-10-31

2002-04-16

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S635000, C534S638000, C008S549000, C106S031480

Reexamination Certificate

active

06372893

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to novel azo dyes use as dyes, as an ingredient of an ink-jet printing ink and also substrates dyed with such compounds.
SUMMARY OF THE INVENTION
This invention relates to novel azo dyes of the formula (I)
where the substituents are each as defined below, their preparation, their use as dyes and as an ingredient of an ink-jet printing ink and also substrates dyed with such compounds.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
This invention relates to novel azo dyes of the formula (I)
where
R
1
and R
2
are independently H or —SO
3
H,
X is a halogen atom, especially F or Cl,
Y is an alkali-detachable group, especially —OSO
3
H, Cl, Br, —OPO
3
H
2
, —SSO
3
H, —OCOCH
3
, —OCOC
6
H
5
or —OSO
2
CH
3
R
3
is —NR
4
R
5
, where R
4
and R
5
are independently hydrogen, a linear or branched C
1-10
-alkyl group which may additionally be interrupted by one or more identical or different heteroatoms or functional groups, especially by —O— and/or —SO
2
—, and which may optionally be substituted; a phenyl group, which may optionally be substituted by one or more identical or different radicals, especially by C
1-4
-alkyl, preferably —CH
3
, —SO
3
H or —SO
2
—CH
2
CH
2
—Y, where Y is as defined above, or R
4
and R
5
may combine with the nitrogen to which they are bonded to form a C
3
-C
8
ring which may additionally contain one or more identical or different heteroatoms, especially O, S or N, preferably additionally an N or an O,
subject to the proviso that when R
4
or R
5
is an —SO
2
CH
2
CH
2
OSO
3
H-substituted phenyl group, R
1
is always —SO
3
H,
or R
3
has the formula (Ia)
where
X, Y, R
1
and R
2
are each as defined in the formula (I),
R
6
and R
6
′ are independently H or a linear or branched C
1-6
-alkyl group, preferably a linear C
1-4
-alkyl group, and B is a phenylene group or a linear or branched C
1-10
-alkylene group, which may optionally be substituted,
subject to the proviso that the position of the —NH— group on the naphthyl ring and the position of the —SO
2
(CH
2
)
2
—Y group on the phenyl ring are identical to those of the formula (I),
and also mixtures thereof and their salts.
Useful cations for salt formation include in particular alkali metal or alkaline earth metal cations.
In preferred compounds of the formula (I), R
3
is —NR
4
R
5
, where R
4
and R
5
are independently H, unsubstituted or HO—, HOOC—, HO
3
S—, HO
3
SO— or halogen-substituted —CH
3
and —CH
2
CH
3
, linear C
4-6
-alkyl groups which are interrupted by —O— and/or SO
2
— and which are additionally substituted by Y having the abovementioned meanings, preferably Cl or —OSO
3
H; or monosubstituted phenyl groups, substituted in particular by —CH
3
, —SO
3
H or —SO
2
CH
2
CH
2
Y, where Y is as defined above, preferably —OSO
3
H, although in the latter case the abovementioned proviso again applies that R
1
is always —SO
3
H.
In likewise preferred compounds of the formula (I), R
3
has the formula (Ia) where
R
6
and R
6
′ are independently H, —CH
3
or —CH
2
CH
3
,
B is a linear or branched C
2-6
-alkylene group or a phenylene group and
X is F.
In particularly preferred compounds of the formula (I), R
3
is —NR
4
R
5
, where NR
4
R
5
is
NHCH
3
, —NHCH
2
CH
3
, —N(CH
3
)
2
, —N(CH
2
CH
3
)
2
, —NHCH
2
COOH, —NHCH
2
CH
2
OH,
NHCH
2
CH
2
SO
3
H, —NHCH
2
CH
2
OSO
3
H, —N(CH
3
)CH
2
CH
2
OH,
NHCH
2
CH
2
SO
2
CH
2
CH
2
OSO
3
H, —NHCH
2
CH
2
CH
2
SO
2
CH
2
CH
2
OSO
3
H,
NHCH
2
CH
2
OCH
2
CH
2
SO
2
CH
2
CH
2
Cl,
 and Y is —OSO
3
H.
In particularly preferred compounds of the formula I, R
3
has the formula (Ia) where R
6
and R
6
′ are hydrogen, B is —CH
2
CH
2
—, —CH(CH
3
)CH
2
—, —abd T us —OSO
3
H.
and Y is —OSO
3
H.
In a likewise particularly preferred compound of the formula (I), R
3
has the formula (Ia) where R
6
is —CH
3
and R
6
′ is H, while B is —CH
2
CH
2
— and Y is —OSO
3
H.
A likewise particularly preferred compound has the formula (Ib)
where R
5
is H or a substituted or unsubstituted C
1-4
-alkyl group and X is Cl or F.
A further aspect of the present invention is the synthesis of the compounds according to the invention, which comprises coupling a compound of the formula
with the diazo compound of an amine of the formula (III)
where the substituents in the formula (II) and the substituents in the formula (III) are each as defined above, under generally known conditions.
This coupling takes place at a pH of 5-8, preferably 6-7. The reaction temperature is between 0 and 40° C., preferably between 10 and 30° C., particularly preferably between 20 and 30° C. The compounds according to the invention are isolated and aftertreated according to known methods.
The compounds of the formula (I) and mixtures thereof and their salts are reactive dyes; they are useful for dyeing or printing hydroxyl-containing or nitrogenous organic substrates.
Another aspect of the invention is accordingly a process for dyeing or printing hydroxyl-containing or nitrogenous organic substrates, which comprises dyeing or printing with the above-defined compounds, their salts or mixtures.
Preferred substrates are leather and fiber materials comprising natural or synthetic polyamides and especially natural or regenerated cellulose, such as cotton, filament viscose or staple viscose. The most preferred substrate is textile material comprising cotton.
Another aspect of the present invention is the use of the above-defined compounds, their salts or mixtures for dyeing or printing the above-described substrates.
The compounds of the formula (I) can be used in dyeing liquors or in print pastes according to all dyeing or printing methods customary for reactive dyes.
Preferably they are dyed up by the exhaust method in the temperature range of 40 to 100° C.
The compounds of the invention can be used as individual dyes or else, because of their excellent compatibility, as combination elements with other reactive dyes of the same class possessing comparable dyeing properties, for example their general fastnesses, their exhaustion and fixation value, etc. The combination dyeings obtained have similar fastnesses to the dyeings with the individual dye.
The compounds of the formula (I) provide good exhaustion and fixation values. The unfixed dye portion is readily washed off. The dyeings and prints obtained possess good lightfastness. They also have good wetfastness properties.
The present invention also provides a hydroxyl-containing or nitrogenous organic substrate, especially cellulose, polyamides and animal fibers, preferably cotton or cotton-containing substrates, dyed or printed by the above-described dyeing or printing processes.
Also claimed is the use of the compound of the formula (I) or mixtures thereof or their salts as a component in an ink-jet printing ink.
The examples hereinbelow serve to illustrate the invention.
Percentages and parts are by weight, unless otherwise stated. Temperatures are reported in degrees Celsius.


REFERENCES:
patent: 5175262 (1992-12-01), Loeffler et al.
patent: 5292870 (1994-03-01), Anderton
patent: 5304221 (1994-04-01), Schwarz et al.
patent: 5556435 (1996-09-01), Russ et al.
patent: 5559215 (1996-09-01), Dannheim et al.
patent: 5597902 (1997-01-01), Bootz et al.
patent: 5831038 (1998-11-01), Reichert
patent: 5925746 (1999-07-01), Lauk et al.
patent: 6015439 (2000-01-01), Pedemonte et al.
patent: 0 516 298 (1992-12-01), None
patent: 630946 (1994-12-01), None
patent: 0 733 679 (1996-09-01), None
patent: 07-324172 (1995-12-01), None
PCT Search Report, Feb. 9, 2001.
Derwent Patent Family Abstract for EP 0 733 679, Sep. 25, 1996.

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