Tetrakisazo dyes, their production and use

Details Tetrakisazo dyes, their production and use Tetrakisazo dyes, their production and use

2002-03-27

2004-06-08

Powers, Flona T. (Department: 1626)

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

Organic compounds

Azo

C534S582000, C534S743000, C534S754000, C534S806000, C534SDIG001, C008S437000, C008S641000

Reissue Patent

active

RE038531

ABSTRACT:

The invention relates to defined tetrakisazo dyes and mixtures thereof with defined trisazo dyes, their production and their use, especially for the dyeing of leather.
In U.S. Pat. No. 4,479,906 there are described trisazo dyes of the formula
in which
A
O
is the radical of an aromatic-carbocyclic diazo component,
B
O
is the radical of a coupling component which contains hydroxyl and/or amino groups,
n is the integer 1 or 2,
one X
O
is hydroxyl and the other X
O
is amino,
Z
O
is
T
O
is hydrogen, methyl, ethyl, benzyl, &bgr;-hydroxyethyl, &bgr;-hydroxypropyl, &bgr;-cyanoethyl, &bgr;-carboxyethyl or &bgr;-carbalkoxyethyl of a total of two to five carbon atoms,
R
O
is hydrogen, hydroxyl, chloro, bromo, nitro, methyl, ethyl or carboxyl and
R
1
O
is hydrogen, methyl, ethyl, chloro, bromo, cyano, nitro, hydroxysulphonyl, carboxyl or alkoxycarbonyl,
there being described in particular also some tetrakisazo dyes in which in the above formula n is 2, the two sulpho groups are in the positions meta to each X
O
(as corresponds to H-acid), Z
O
is a radical of formula (2). A
O
is the radical of an aminoazobenzene diazocomponent and B
O
is the radical of certain aminobenzene coupling components. These dyes are described also for the dyeing of leather in green to black shades.
It has now been found that tetrakisazo dyes of the below indicated structure of formula (I) are particularly valuable anionic dyes for obtaining dyeings of intensive dark shades, in particular for the penetration dyeing of leather in dark shades of high fastnesses, especially when combined with the below defined trisazo dyes of formula (X).
The invention relates to the defined dyes and dye mixtures, their production and their use.
The invention, thus, provides a tetrakisazo dye of formula
wherein
one of the two symbols X and Y signifies —OH and the other signifies —NH
2
,
Z signifies a radical of formula
—W
1
—N═N—B
2
  (&agr;)
or, if Y signifies —OH, also a radical of formula
—W
2
—N═N—D   (&bgr;),
Q
1
signifies —SO
2
— or —CO—,
Q
2
signifies the direct bond or, if Q
1
is —SO
2
—, also a group —SO
2
—,
B
1
signifies the radical of a coupling component H—B
1
,
B
2
signifies the radical of a coupling component H—B
2
,
D signifies the radical of a diazo component D—NH
2
,
W
1
signifies the radical of a bicyclic bisdiazo component,
W
2
signifies the radical of a bicyclic middle component and
M signifies hydrogen or a cation,
or a mixture of two or more tetrakisazo dyes of formula (I).
Formula (I) comprises in particular the following formulae
Thus, the invention provides in particular a dye of formula (Ia), (Ib) or (Ic) or a mixture of two or more thereof.
A particular further feature of the invention is represented by a mixture of at least one dye of the above formula (I) and at least one trisazo dye of formula
in which B
1
, D, Q
1
, Q
2
and M have the significances indicated above for formula (I).
The dyes of the invention may be produced by means of diazotization and coupling reactions, in order to form the azo groups, in a manner conventional per se. In particular, a process for the production of the tetrakisazo dyes of the invention is characterized in that for the production of a dye of formula (Ia) the bisdiazocompound of a diamine of formula
is coupled at one side to the 3-position of a bis-coupling component of formula
the obtained azodiazocompound is either first coupled to a coupling component H—B
1
, to give an intermediate of formula
and the diazocompound of an amine of formula
D—N═N—W
2
—NH
2
  (V)
is coupled to the 6-position of the intermediate of formula (IV), or the azodiazocompound is first coupled in the 6-position with the diazocompound of an amine of formula (V) and then coupled to a coupling component H—B
1
, for the production of a dye of formula (Ib) the bisdiazocompound of a diamine of formula (II) is coupled at one side to the 3-position of a bis-coupling component of formula (III) and the obtained azodiazocompound is either first coupled to a coupling component H—B
1
, to give an intermediate of formula (IV), and then the bisdiazocompound of a diamine of formula
H
2
N—W
1
—NH
2
  (VI)
is coupled at one side to the 6-position of the intermediate of formula (IV) and the obtained trisazodiazocompound is coupled to a coupling component H—B
2
, or the azodiazocompound is first coupled in the 6-position with the bisdiazocompound of a diamine of formula (VI) and then the obtained disazobisdiazocompound is coupled to coupling components H—B
1
, and H—B
2
or for the production of a dye of formula (Ic) the bisdiazocompound of a diamine of formula (VI) is coupled at one side to the 3-position of a bis-coupling component of formula (III) and the obtained azodiazocompound is either first coupled to a coupling component H—B
2
to give an intermediate of formula
and then the bisdiazocompound of a diamine of formula (II) is coupled at one side to the 6-position of the intermediate of formula (VII) and the obtained trisazodiazocompound is coupled to a coupling component H—B
1
, or it is first coupled in the 6-position with the bisdiazocompound of a diamine of formula (II) and then the obtained disazobisdiazocompound is coupled to H—B
1
, and H—B
2
.
The compounds of formula (V) may be produced by coupling the diazocompound of a diazocomponent of formula
D—NH
2
  (VIII)
to a middle component of formula (IX)
H—W
2
—NH
2
  (IX).
The trisazo dyes of formula (X) may be synthetized by coupling the diazocompound of a diazocomponent of formula (VIII) to a compound of formula (IV) or to its precursor azodiazocompound, before coupling of the diazoazocompound to H—B
1
. If the starting compounds are the same as the corresponding ones employed for the production of the dyes of formula (I), this reaction sequence may be carried out together with the production of the tetrakisazo dye or dye mixture, choosing the molar ratios in a suitable way.
In the mixtures of tetrakisazo dyes of formula (I) and trisazodyes of formula (X) the molar ratio of tetrakisazo dye or tetrakisazo dye mixture to trisazo dye or trisazo dye mixture is e.g. in the range of 95/5 to 20/80, prferably 80/20 to 30/70, more preferably 75/25 to 40/60.
As diazocomponents of formula (VIII) there may be employed any known diazotizable amines, in particular of the benzene of naphthalene series, preferably containing at least one solubilizing substituent, which preferably is a sulpho group, a carboxy group, a carbamoyl group and/or a sulphamoyl group.
As diazo components of formula (VIII) come, in particular, into consideration those of the following formulae
wherein
R
1
signifies hydrogen, nitril, trifluoromethyl, nitro, —SO
3
M, —SO
2
NR
4
R
5
, —COOM or —CONR
4
R
5
,
R
2
signifies hydrogen, nitro, —SO
3
M, —SO
2
NR
4
R
5
, trifluoromethyl, nitril, —COOM, —CONR
4
R
5
, C
1-4
-alkyl, C
1-4
-alkoxy, halogen or C
1-2
-mercaptoalkyl,
R
3
signifies hydrogen, C
1-4
-alkyl, C
1-4
-alkoxy, halogen, C
1-2
-mercaptoalkyl, —NH—Ac, —NH—CO—O—CH
3
or a radical of formula
R
4
signifies hydrogen, C
1-4
-alkyl, C
1-3
-alkylene-R′ or C
2-3
-3-hydroxyalkyl,
R
5
signifies hydrogen, C
1-4
-alkyl, C
1-3
-alkylene-R′, C
2-3
-hydroxyalkyl, benzyl or a radical of formula
R′ signifies nitril, carbamoyl or —COOM,
R
6
signifies hydrogen, nitro or —SO
3
M,
R
7
signifies hydrogen, methyl, chlorine, nitro, —COOM or —SO
3
M,
R
8
signifies hydrogen, halogen, nitro, —SO
3
M, —SO
2
NR
4
R
5
, methylsulphonyl, C
1-4
-alkyl or —NH—Ac,
R
9
signifies hydrogen, halogen, nitro, —SO
3
M, —SO
2
NR
4
R
5
, methylsulphonyl, C
1-4
-alkyl or —NH—Ac,
R
10
signifies nitro, —SO
3
M or —SO
2
NR
4
R
5
,
Ac signifies an aliphatic acyl group,
p signifies 0 or 1 and
r signifies 0 or 1,
R
1
preferably signifies hydrogen or —COOM.
Of the alkyl and alkoxy groups with 1 to 4 carbon atoms, the lower molecular ones are preferred, in particular ethyl, methyl, ethoxy and methoxy. Halogen may in particular be fluorine, chlorine or bromine of which fluorine and, before all, chlor

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