Copper complex azo dyes, their preparation and their use

Details Copper complex azo dyes, their preparation and their use Copper complex azo dyes, their preparation and their use

2000-09-25

2001-07-24

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C008S506000, C008S543000, C106S031510, C347S001000

Reexamination Certificate

active

06265554

ABSTRACT:

The present invention relates to novel magenta dyes obtainable from reactive copper complex azo dyes by the addition or substitution of certain nitrogen-containing nucleophilic compounds. The present invention relates also to the preparation of those dyes and inks comprising the dyes according to the invention.
The dyes underlying the present invention are especially suitable for the printing of paper, textile fibre materials, plastics films or aluminium foils, especially using the ink-jet printing method, and for the dyeing of textile fibre materials, wood, paper, aluminium sheets or aluminium foils using traditional dyeing and printing methods and yield magenta dyeings having good light-fastness properties and a high colour brilliance, the shade of which is markedly shifted into the blue region.
Ink compositions, especially for use in multicolour printing, are nowadays subject to high demands. For example, it is of considerable importance that the dyes on which the inks are based correspond as accurately as possible to the three primary colours yellow, cyan and magenta. At the same time, the choice of suitable dyes is limited not only by the purity of the hue and the desired brilliance of the colour reproduction but also by the required shade.
The present invention is therefore based on the problem of providing new, improved magenta dyes for the dyeing and printing of paper, textile fibre materials, plastics films or aluminium foils, preferably using the ink-jet printing method, that yield pure, brilliant hues of a markedly bluish-red shade and that are at the same distinguished by good fastness to light.
It has now been found, surprisingly, that certain derivatives of C.I. Reactive Red 23 yield a very brilliant, bluish magenta which also has good fastness to light.
The present invention accordingly relates to
dyes of formula (1)
wherein
Z is C
10
-C
20
terpeneamino; or N-mono-C
1
-C
16
alkylamino or N,N-di-C
1
-C
16
alkylamino unsubstituted or substituted in the alkyl moiety by phenyl (which may itself be substituted by carboxy, carbamoyl, sulfo or by sulfamoyl), amino, C
2
-C
4
alkanoylamino, hydroxy, sulfo, sulfato, carboxy, carbamoyl or by sulfamoyl, which further may be interrupted in the alkyl moiety by one, two or three oxygen atoms or —NH— groups.
Z as N-mono- or N,N-di-C
1
-C
16
alkylamino is, for example, methylamino, ethylamino, N,N-di-methylamino, N,N-diethylamino, isopropylamino, n-butylamino, sec-butylamino, isobutyamino or tert-butylamino, linear or branched pentylamino, hexylamino, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, tridecylamino or tetradecyamino. The mentioned radicals are unsubstituted or substituted in the alkyl moiety, e.g. by phenyl (which may itself be substituted by carboxy, carbamoyl, sulfo or by sulfamoyl), amino, C
2
-C
4
alkanoylamino, e.g. acetylamino or propionylamino, hydroxy, sulfo, sulfato, carboxy, carbamoyl or by sulfamoyl. The mentioned radicals are uninterrupted or interrupted in the alkyl moiety by from one to three oxygen atoms or —NH— groups.
Examples of radicals that are substituted in the alkyl moiety and which further may be interrupted in the alkyl moiety by oxygen or by —NH— include N-&bgr;-aminoethylamino, N-&bgr;-aminopropylamino, N-&bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, N-2-(&bgr;-hydroxyethoxy)ethylamino, N-2-[2-(&bgr;-hydroxyethoxy)ethoxy]-ethylamino, N-2-(&bgr;-hydroxyethylamino)ethyl-N-(&bgr;-hydroxyethyl)amino, N-2-(&bgr;-aminoethylamino)ethylamino, N-&bgr;-sulfatoethylamino, N-&bgr;-sulfoethylamimo, N-carboxymethylamino, N-methyl-N-carboxymethylamino, N,N-dicarboxymethylamino, N-&agr;-carboxyethylamino, N-&bgr;-carboxyethylamino, N-&agr;,&bgr;-dicarboxyethylamino, N-&agr;-carboxy-&ggr;-carbamoylpropylamino, N-&agr;-carboxy-&bgr;-hydroxyethylamino, N-&agr;-carboxy-&bgr;-phenylethylamino, N-&agr;,&ggr;-dicarboxypropylamino, N-ethyl-N-&bgr;-hydroxyethylamino and N-methyl-N-&bgr;-hydroxyethylamino, especially N,N-di-&bgr;-hydroxyethylamino, N-2-(&bgr;-hydroxyethylamino)ethyl-N-(&bgr;-hydroxyethyl)amino, N-carboxymethylamino, N-methyl-N-carboxymethylamino, N,N-dicarboxymethylamino, N-&agr;-carboxyethylamino, N-&bgr;-carboxyethylamino, N-&agr;,&bgr;-dicarboxyethylamino, N-&agr;-carboxy-&ggr;-carbamoylpropylamino, N-&agr;-carboxy-&bgr;-hydroxyethylamino, N-&agr;-carboxy-&bgr;-phenylethylamino and N-&agr;,&bgr;-dicarboxypropylamino.
Suitable unsubstituted and uninterrupted radicals are preferably N-mono-C
8
-C
14
alkylamino and especially N-mono-C
11
-C
14
alkylamino radicals, such as the radicals that are branched in the alkyl moiety that correspond, for example, to the formula
wherein the sum of the carbon atoms R
a
+R
b
+R
c
is from 11 to 14. An example of an amine forming the basis of the radical of the formula given above is ®Primene 81 R (Rohm & Haas).
Z as N-mono- or N,N-di-C
1
-C
16
alkylamino that is substituted in the alkyl moiety and which further may be interrupted in the alkyl moiety by oxygen or by —NH— is preferably N-mono- or N,N-di-C
1
-C
6
alkylamino and especially N-mono- or N,N-di-C
1
-C
4
alkylamino.
Preference is given to the radicals that are substituted in the alkyl moiety and which further may be interrupted in the alkyl moiety by oxygen or by —NH—.
Z as C
10
-C
20
terpeneamino, preferably C
20
diterpeneamino, is an amino group mono-substituted at the nitrogen atom by a terpene hydrocarbon radical. Examples of terpene hydrocarbon radicals that come into consideration are acyclic, monocyclic or bicyclic Cloterpenes, acyclic, monocyclic, bicyclic or tricyclic C
15
sesquiterpenes, acyclic, monocyclic or tricyclic C
20
diterpenes, especially tricyclic C
20
diterpenes and more especially dehydrogenated tricyclic C
20
diterpenes, such as those derived from dehydroabietic acid. An example of such a dehydrogenated tricyclic C
20
diterpeneamino radical that may be mentioned is the radical of formula
Preference is given to the dyes according to the invention wherein Z is C
20
diterpeneamino; N-mono-C
8
-C
14
alkylamino; or N-mono-C
1
-C
6
alkylamino or N,N-di-C
1
-C
6
alkylamino substituted in the alkyl moiety by phenyl (which may itself be substituted by carboxy), amino, hydroxy, sulfo, sulfato, carboxy or by carbamoyl, which further may be interrupted in the alkyl moiety by one or two oxygen atoms or —NH— groups.
Special preference is given to the dyes according to the invention wherein
Z is C
20
diterpeneamino; N-mono-C
11
-C
14
alkylamino; or N-mono-C
1
-C
6
alkylamino or N,N-di-C
1
-C
6
alkylamino substituted in the alkyl moiety by phenyl (which may itself be substituted by carboxy), hydroxy, sulfo, sulfato, carboxy or by carbamoyl, which further may be interrupted in the alkyl moiety by one or two oxygen atoms or —NH— groups.
Very special preference is given to the dyes according to the invention wherein Z is N-mono-C
1
-C
4
alkylamino or N,N-di-C
1
-C
4
alkylamino substituted in the alkyl moiety by phenyl, hydroxy, carboxy or by carbamoyl, which further may be interrupted in the alkyl moiety by oxygen or by —NH—.
In a preferred embodiment of the dyes according to the invention, the dye of formula (1) corresponds to a dye of formula (2)
wherein
Z has the definitions and preferred meanings given above.
Special preference is given to the dyes according to the invention wherein the dye of formula (1) is a dye of formula (2) and
Z is N-mono-C
1
-C
4
alkylamino or N,N-di-C
1
-C
4
alkylamino substituted in the alkyl moiety by phenyl, hydroxy, carboxy or by carbamoyl, preferably by hydroxy, carboxy or by carbamoyl, which further may be interrupted in the alkyl moiety by oxygen or by —NH—.
Very special preference is given to the dyes according to the invention wherein the dye of formula (1) is a dye of formula (2) and
Z is N,N-di-&bgr;-hydroxyethylamino, N-2-(&bgr;-hydroxyethylamino)ethyl-N-(&bgr;-hydroxyethyl)amino, N-carboxymethylamino, N-methyl-N-carboxymethylamino, N,N-dicarboxymethylamino, N-&agr;-carboxyethylamino, N-&bgr;-carboxyethylamino, N-&agr;,&bgr;-dicarboxyethylamino, N-&agr;-carboxy-&ggr;-carbamoylpropylamino, N-&agr;

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