1:2 chromium complex dyes, their production and use

Details 1:2 chromium complex dyes, their production and use 1:2 chromium complex dyes, their production and use

2000-09-28

2004-07-20

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Nontextile, dyeing process or product, including inorganic...

Inorganic substrate

C008S685000, C008S687000, C534S696000, C534S721000, C534S723000, C534S725000, C534S692000

Reexamination Certificate

active

06764524

ABSTRACT:

BACKGROUND OF THE INVENTION
Aluminium and aluminium alloy structures, articles and parts which have been provided with a protective oxide layer, especially with an oxide layer produced electrochemically by anodization, are nowadays increasingly used in engineering and building construction, for example as constituting or/and decorative components of buildings and means of private or public transport, or for utility or art objects. A popular way of improving the aesthetic appeal of such structures, articles and parts is to colour them or respectively their oxide layers. It is accordingly desirable that the coloured layers should retain their colour for as long as possible and consequently have very high fastnesses to environmental influences, especially to the action of sunlight. To fit in with the colour of the immediate surroundings, for example other structural components, which are e.g. white to grey or even black, or to create a contrast to parts in other, intensive or luminous colours, or else to emulate the self-colour of the metal, it is frequently desirable to confer a grey colour on such oxide layers. However, it is difficult to create a truly neutral grey shade, especially of a high hue constancy over various dyeing stages. For instance, when a black dye (e.g. such as described in GB-A-2268183 or JP-A-55-97429) is used in dilute form, an undesirable secondary hue of the black dye, for example green, reddish or blue, may become apparent, so that the grey produced is not neutral. There has been many an attempt to produce a truly neutral grey, for example as textile dyes. However, the dyeing and fastness requirements of dyeings on the abovementioned oxide layers and the requirements of the bath durability of the dyes are much higher than and in part also significantly different from those relating to textiles, so that a neutral grey in a fastness level which is suitable for the abovementioned substrates and in a suitable hue constancy and bath durability remains an hitherto unmet want of the market.
SUMMARY OF THE INVENTION
It has now surprisingly been found that the hereinbelow defined asymmetrical 1:2 chromium complex dyes are outstandingly suitable as grey dyes of a very neutral grey hue for such oxide layers, especially for anodized aluminium and anodized aluminium alloys, and are notable in this use for their surprisingly high fastnesses and bath durability.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention concerns the defined asymmetrical 1:2 chromium complex dyes, their production and their use, in particular for dyeing artificially (chiefly galvanically) produced oxide layers on aluminium or aluminium alloys and to compositions containing these dyes. The invention also concerns a dye composition having at least one asymmetrical 1:2 chromium complex dye.
In a first aspect, the invention accordingly provides asymmetrical 1:2 chromium complex dyes of the formula
wherein
X signifies —SO
3
M, —SO
2
NR
1
R
2
or chlorine,
Y signifies hydrogen, —SO
3
M or chlorine,
R
1
signifies hydrogen, C
1-6
-alkyl, C
2-3
-hydroxyalkyl or a radical of the formula
R
2
signifies hydrogen, C
1-6
alkyl or C
2-3
-hydroxyalkyl, or R
1
and R2 together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocycle,
R
3
signifies hydrogen, C
1-2
-alkyl, chlorine, —COOM or —SO
3
M,
R
4
signifies hydrogen, C
1-2
-alkyl, C
1-2
-alkoxy, chlorine or —SO
3
M,
n signifies from 0 to 3,
M signifies in each case hydrogen or a non-chromophoric cation, and M
+
signifies hydrogen or a non-chromophoric cation.
The alkyl radicals occurring in the formula (I) may be linear or, if they contain three or more carbon atoms, may also be branched, or, if they contain six carbon atoms, may also be cyclic. Among the alkyl radicals the lower-molecular ones are preferred, in particular ethyl and especially methyl.
In the radicals of the formula (a) the respective substituents may be located in any desired positions on the phenyl radical; if R
3
stands for a sulpho group —SO
3
M, this group is preferably located in meta position or para position; if R
3
stands for a carboxyl group —COOM, this group is preferably located in ortho position or para position; if R
3
stands for alkyl or chlorine or/and if R
4
is alkyl, alkoxy or chlorine, these substituents may be located in any of the available positions, with preferably at least one of the two ortho positions on the phenyl radical being unsubstituted. R
3
signifies particularly preferably hydrogen or —COOM. R
4
signifies particularly preferably hydrogen.
The free bond on the sulpho-substituted naphthalene radical (b) may be located arbitrarily in a or &bgr; position, the &agr; position being preferred. For n=1 to 3 the n sulpho groups in the formula (b) may be located in n arbitrary available positions, with preferably the vicinal positions to the bond to N being unsubstituted. Mention may be made in particular of &agr;-naphthyl and the following naphthylsulphonic acid radicals of the formula (b): 2-naphthyl4,6,8-trisulphonic acid, 1-naphthyl-3,6-disulphonic acid, 1-naphthyl-3,7-disulphonic acid, 1-naphthyl4,6-disulphonic acid, 1-naphthyl4,7-disulphonic acid, 2-naphthyl4,8-disulphonic acid, 2-naphthyl-5,7-disulphonic acid, 2-naphthyl-6,8-disulphonic acid, 1-naphthyl-3-, -4-, -5-, -6- or -7-sulphonic acid and 2-naphthyl-5- or -6-sulphonic acid. Among these radicals, preference is given to those in which n=1, especially 1-naphthyl4- or -5-sulphonic acid.
Y signifies advantageously hydrogen, chlorine or —SO
3
M, preferably hydrogen. X preferably signifies —SO
2
NR
1
R
2
. When one of the two symbols X and Y signifies chlorine, the other one signifies preferably a sulpho group. When X stands for —SO
2
NR
1
R
2
, Y signifies preferably hydrogen. R
1
stands preferably for R
1
′, i.e. hydrogen, C
1-2
-alkyl or a radical of the formula (a), particularly preferably hydrogen, phenyl or carboxyphenyl. R
2
signifies advantageously R
2
′, i.e. hydrogen or C
1-2
-alkyl, preferably hydrogen. X signifies particularly preferably —SO
2
NR
1
′R
2
′.
The sulphonic and carboxylic acid groups may be in the form of the free acid or, preferably, in the form of salts of non-chromophoric cations.
M and M
+
may each signify hydrogen or a non-chromophoric cation. Hydrogen as ion is present as the hydronium ion. Examples of suitable non-chromophoric cations are alkali metal cations, ammonium cations and alkaline earth metal cations. As alkaline earth metal cations mention may be made, for example, of calcium and magnesium. As ammonium cations mention may be made of unsubstituted ammonium or also ammonium ions of low-molecular amines, chiefly mono-, di- or tri-C
1-2
-alkyl-and/or -&bgr;-hydroxy-C
2-3
-alkyl-ammonium, e.g. mono-, di- or tri-isopropanolammonium, mono-, di- or triethanolammonium and N-methyl-N-ethanol-ammonium. Suitable alkali metal cations are customary such cations, e.g. lithium, sodium and/or potassium ions. Among the mentioned cations the alkali metal cations and ammonium cations are preferred. In one embodiment of the invention some of the symbols M and M
+
signify hydrogen and the rest of them signify alkali metal cations and/or ammonium cations.
Preferred asymmetrical 1:2 chromium complex dyes of the formula (I) conform to the formula
The 1:2 chromium complex dyes of the formula (I) may be produced in analogy to chromation reactions which are known per se. In particular, the process for the production of the 1:2 chromium complex dyes of the formula (I) is characterized in that a 1:1 chromium complex of a monoazo compound of the formula
is reacted with a metallizable compound of the formula
or a 1:1 chromium complex of a monoazo compound of the formula (III) is reacted with a metallizable compound of the formula (II).
The compounds of the formulae (II) and (III) are known or may be produced in analogy to known methods, especially by coupling the diazo compound of 2-amino-1-hydroxybenzene-4-nitro-6-sulphonic acid, or respectively of an amine of the formula
onto a coupling

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