Anthraquinone-azo dyes and use of such compounds

Details Anthraquinone-azo dyes and use of such compounds Anthraquinone-azo dyes and use of such compounds

2001-11-16

2004-02-24

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S655000, C008S506000, C008S522000, C008S676000, C106S031440

Reexamination Certificate

active

06696553

ABSTRACT:

In GB-A-478665, in U.S. Pat. No. 2,108,126 and in DE-A-1914192 there are described dyes of the anthraquinone series containing a radical of aminoazobenizene linked over the amino group to the 4position of 1-aminoanthraquinone-2-sulphonic acid and where the phenylazo group may bear a sulpho group, for the dyeing of textile fibers. Typically there is described the dye of formula
in Example 1 of U.S. Pat. No. 2,108,126 for the dyeing of wool, in Example 4 of GB-A-478665 (Complete Specification) for the dyeing of cotton and wool and in Example 1 of DE-A-1914192 for dyeing textile fabrics of polyamide fibers (polyamide 6) or polyurethane fibers. In Example 4 of DE-A-1914192 there is further described the dye of formula
for dyeing textile fabrics of polyamide fibers (polyamide 66).
U.S. Pat. No. 3,202,550 relates to the dyeing of aluminium oxide layers with dyes containing phosphonate, arsonate or stibonate groups. The mentioned and described dyes are of most various categories, e.g. phithalocyanine, monoazo, disazo, aniline, anthraquinone, naphthalimide, quinoline, triphenylmethane and azo copper complex dyes, and in one of the examples (Example 35) there is described the anthraquinone dye of formula
Dyes not containing these phosphonate, arsonate or stibonate groups are stated in U.S. Pat. No. 3,202,550 to be disadvantageous in the dyeing of aluminium oxide layers, due to loss of affinity of the dye in the presence of the usual salts used in the dyeing of aluminium oxide layers
In the above azo-anthraquinone dyes the sulphophenyl or phosphonophenyl radicals are radicals of diazo components.
It has now surprisingly been found that the anionic anthraquinone azo dyes below are not only particularly suitable for the dyeing of oxide layers on metal surfaces, especially oil aluminium, but are also particularly suitable for colouring other non-fibrous substrates, such as plastic compositions and coatings, or free-flowing bulk materials.
The invention relates to the use of the defined dyes for colouring non-fibrous substrates, to the novel dyes and their production and use, and to corresponding dye preparations and their use.
A first subject-matter of the invention is thus the use of water-soluble dyes of the formula
in which
R
1
is hydrogen, hydroxyl, C
1-4
-alkyl C
1-4
-alkoxy, halogen or SO
3
M.
R
2
is hydrogen, C
1-4
-alkyl or C
3-6
-cycloalkyl,
B is the radical of a carbocyclic, heterocyclic or methylene-active non-cyclic coupling component having at most two optionally fused carbocyclic rings, and
M is hydrogen or a non-chromophoric cation,
the ring A has no further substituents or is substituted with from one to four of the following substituents: C
1-4
-alkyl, C
1-4
-alkoxy, halogen, —NO
2
, —COOM and —SO
3
M, and the group —N═N—B is bonded to position 3 or 4 of the ring A, with the proviso that the molecule contains at least two —SO
3
M groups, for dyeing or colouring non-fibrous substrates.
The anthraquinone azo dyes of the formula (I) can be produced in a manner known per se by diazotization, coupling and condensation reactions. The process for the production of the compounds of the formula (I) is, in particular, characterized in that the diazo compound of at least one amine of the formula
is coupled to at least one coupling component of the formula
H—B  (III)
or a compound of the formula
is reacted with a compound of the formula
The compounds of the formulae (II) to (V) are known or can be produced by methods known per se. The compounds of the formula (V) can, in particular, be produced by a process in which the diazo compound of an amine of the formula
in which G is a nitro group or a primary amino group protected by acylation, is coupled to a coupling component H—B, and, when the coupling is complete, either the nitro group G is reduced to a primary amino group or the amino group G protected by acylation (preferably acetylation) is hydrolyzed to the primary amino group.
The said reactions (diazotization, coupling, condensation, reduction and hydrolysis) can be carried out in a manner known per se.
The diazotization of the amines of the formula (II) or (VI) can be carried out in a manner known per se. in particular with sodium nitrite in acidic medium (for example pH 1 to 3) and at low temperature, for example in the range from −5 to +15° C. The coupling of the diazonium compound to a coupling component of the formula H—B can be carried out in a manner known per se, advantageously at temperatures in the range from −5 to +30° C., preferably below 25° C., particularly preferably in the range from 0 to 10° C., and, depending on the coupling component H—B, under acidic to clearly alkaline conditions, for example in the pH range from 3 to 12, preferably from 4 to 11. The reactions can be carried out in aqueous medium or also in aqueous/organic medium, where the organic medium is preferably a water-miscible inert solvent (for example an alcohol or dioxane).
The reaction of a compound of the formula (IV) with a compound of the formula (V) is a condensation which takes place under dehydrobrominating conditions. It advantageously takes place in aqueous medium in the presence of a base, for example an alkali metal hydroxide or carbonate, in particular in the presence of sodium hydroxide or carbonate, and at elevated temperature, for example in the range from 40 to 100° C.
The reduction of a nitro group G expediently takes place under mild conditions, for example with a sulphide, hydrazine or sulphite or by the Béchamps method; the hydrolysis of an acylated amino group G expediently likewise takes place under mild conditions, for example at temperatures in the range from 30 to 80° C. and in the pH range from 8 to 10.
The dyes of the formula (I) are essentially purely anionic dyes, in particular they are free from cationic or fiber-reactive substituents, i.e. in particular —B is free from such substituents.
Halogen stands, for example, for fluorine, chlorine or bromine, preferably for chlorine.
Of the C
1-4
-alkyl and -alkoxy groups, the low-molecular-weight ones are preferred, principally methyl, ethyl, methoxy and ethoxy.
If R
1
is chlorine or a sulpho group, it is preferably in one of positions 6 and 7 of the anthraquinone ring.
R
1
preferably stands for hydrogen or a sulpho group;
R
2
advantageously stands for methyl, ethyl or particularly preferably hydrogen.
Of the up to four possible further substituents on the ring A, advantageously at most two are electro-negative substituents (—NO
2
, —COOM, —SO
3
M). The ring A preferably carries a total of at most two further substituents of those mentioned above, preferably a sulpho group and optionally a further substituent, which is advantageously a methyl, ethyl, methoxy, carboxyl, hydroxyl or sulpho group. If the ring A carries a sulpho group, this is advantageously in the ortho- or preferably meta-position to the NH group; further substituents can be located in one or more of the available positions on the ring A.
The radical B is the radical of a coupling component H—B as defined above. B is preferably the radical of a coupling component HB
1
, HB
2
, HB
3
or HB
4
, in which
HB
1
is a methylene-active, non-cyclic coupling component in which any carbocyclic rings that may be present are unsubstituted or are substituted with one or more of the substituents C
1-4
-alkyl, C
1-4
-alkoxy, halogen and —SO
3
M;
HB
2
is a methylene-active, carbocyclic non-aromatic coupling component;
HB
3
is a heterocyclic coupling component in which any carbocyclic ring that may be present is unsubstituted or is substituted with one or more of the substituents C
1-4
-alkyl, C
1-4
-alkoxy. halogen and —SO
3
M; and
HB
4
is a coupling component of the formula
in which the amino group is bonded to position 6 or 7 of the naphthalene radical.
Preferred coupling components HB
1
are, in particular, those which contain two carbonyl groups or two nitrile groups or one carbonyl group and one nitrile group bonded to a methylene CH
2
, in particular those which, in one of their tautomeric forms, conform to the formu

Affiliated with

Also associated with

Rating

Anthraquinone-azo dyes and use of such compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Anthraquinone-azo dyes and use of such compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Anthraquinone-azo dyes and use of such compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3311731