Azo dye mixtures

Details Azo dye mixtures Azo dye mixtures

2000-09-18

2003-04-22

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dye or potential dye composition, additive, treatment,...

Mixed dyes, noncomplexed

C008S691000, C008S922000

Reexamination Certificate

active

06551363

ABSTRACT:

The present invention relates to mixtures of azo dyes, to their preparation and to their use in the dyeing or printing of semi-synthetic or synthetic hydrophobic fiber materials.
Azo dyes and their use in the dyeing of semi-synthetic or synthetic hydrophobic fiber materials are known. It has been shown, however, that the known dyes do not entirely cover the full range of shades and there is therefore a need for new dyes or dye mixtures that make it possible to obtain the shades lacking hitherto, especially bluish red shades.
It has now been found, surprisingly, that the mixtures according to the invention meet the criteria given above to a considerable degree.
The present invention accordingly relates to a dye mixture comprising
as component (A) at least one dye of formula
 and
as component (B) at least one dye of formula
 wherein
R
1
is C
1
-C
6
alkyl unsubstituted or substituted by hydroxy, cyano, phenyl, acyloxy or
 it being possible for the alkyl chain from C
3
to be interrupted one or more times by oxygen, or is allyl,
R
2
is C
1
-C
4
alkyl substituted by C
1
-C
4
alkoxycarbonyl, or is n-hexyl,
R
3
is C
1
-C
4
alkyl, and
R
4
is hydrogen, halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy.
R
1
as C
1
-C
6
alkyl is e.g. methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, amyl, tert-amyl (1,1-dimethylpropyl), 1,1,3,3-tetramethylbutyl, hexyl, 1-methylpentyl, neopentyl, cyclopentyl, cyclohexyl, or a respective isomer.
R
2
, R
3
and R
4
as C
1
-C
4
alkyl are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
R
2
as C
1
-C
4
alkoxycarbonyl is e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or butoxycarbonyl.
R
4
as C
1
-C
4
alkoxy is e.g. methoxy, ethoxy, propoxy or butoxy.
R
4
as halogen is fluorine, bromine, iodine or preferably chlorine.
R
1
is preferably methyl, unsubstituted or cyano-,hydroxy- or acyloxy-substituted ethyl, allyl, cyclohexyl or benzyl.
R
2
is preferably a radical of formula —CH
2
—COOCH
3
, —CH
2
—COOCH
2
CH
3
, —CH(CH
3
)—COOCH
3
or —CH(CH
3
)—COOCH
2
CH
3
.
R
3
is preferably ethyl or isopropyl and especially methyl.
R
4
is preferably methyl or methoxy and especially hydrogen or chlorine.
Acyl is preferably formyl, acetyl or propionyl. The ratio of components (A) and (B) in the dye mixtures according to the invention may vary within a wide range, for example from 99:1 to 1:99, especially from 60:40 to 40:60, more especially from 55:45 to 45:55. A dye mixture having a ratio of components (A) and (B) of 50:50 is very especially preferred.
Preference is given to a dye mixture comprising the dyes of formulae (1) and (2) wherein R
1
is methyl, unsubstituted or cyano-, hydroxy- or acyloxy-substituted ethyl, allyl, cyclohexyl or benzyl, R
2
is a radical of formula —CH
2
—COOCH
3
, —CH
2
—COOCH
2
CH
3
, —CH(CH
3
)—COOCH
3
or —CH(CH
3
)—COOCH
2
CH
3
, R
3
is methyl, ethyl or isopropyl and R
4
is hydrogen, methyl, methoxy or chlorine.
Special preference is given to a dye mixture comprising
as component (A) the dye of formula
and as component (B) the dye of formula
Special preference is also given to a dye mixture comprising the dyes of formulae (1) and (2) wherein R
1
is ethyl, R
2
is n-hexyl, R
3
is methyl and R
4
is hydrogen.
Very special preference is given to a dye mixture comprising the dyes of formulae (3) and (4) in a ratio of 50:50.
Very special preference is also given to dye mixtures of the dyes of formulae (1) and (2) having CIELAB coordinates a* of from 37 to 60, especially from 55 to 58, and b* of from −5 to 25, especially from −2 to 20.
The determination of the CIELAB coordinates a* and b* is described in the German standard DIN 6174 “Farbmetrische Bestimmung von Farbabstanden bei Körperfarben nach der CIELAB-Formel” (“Colorimetric determination of colour distances in surface colours in accordance with the CIELAB formula”) of January 1979. The present invention relates also to the process for the preparation of the dye mixtures of formulae (1) and (2) according to the invention.
They are prepared, for example, as follows: a compound of formula
is reacted with Br
2
and KSCN in acetic acid analogously to a procedure described on pages 57 to 64 of “Dyes and Pigments”, Vol. 38 to form a mixture comprising the compounds of formulae
the resulting mixture is diazotised in accordance with a customary procedure and then coupled to a coupling component of formula
R
1
, R
2
, R
3
and R
4
being as defined above.
The diazotisation of the compounds of formulae (51) and (51a) is carried out in a manner known per se, for example with sodium nitrite in an acidic, e.g. hydrochloric-acid-containing or sulfuric-acid-containing, aqueous medium. The diazotisation may, however, also be carried out using other diazotisation agents, e.g. with nitrosylsulfuric acid. In the diazotisation, an additional acid may be present in the reaction medium, e.g. phosphoric acid, sulfuric acid, acetic acid, propionic acid or hydrochloric acid or a mixture of such acids, e.g. a mixture of propionic acid and acetic acid. The diazotisation is advantageously carried out at temperatures of from −10 to 30° C., for example from −10° C. to room temperature. The coupling of the mixture of the diazotised compounds of formulae (51) and (51a) to the coupling component of formula (52) is likewise effected in known manner, for example in an acidic, aqueous or aqueous-organic medium, advantageously at temperatures of from −10 to 30° C., especially below 10° C. Examples of acids used are hydrochloric acid, acetic acid, propionic acid, sulfuric acid and phosphoric acid.
The compound of formula (50) is known and can be prepared in a manner known per se.
The coupling component of formula (52) can be prepared in a manner known per se by reacting, for example, a compound of formula
wherein R
1
and R
3
are as defined above, with ClCH
2
COOCH
3
, ClCH
2
COOC
2
H
5
, ClCH(CH
3
)COOCH
3
or ClCH(CH
3
)COOC
2
H
5
in the presence of sodium carbonate at elevated temperature.
The dye mixtures according to the invention may also be prepared by simply mixing the dyes of formulae (1) and (2) together.
The dye mixtures according to the invention can be used as dyes in the dyeing and printing of semi-synthetic and, especially, synthetic hydrophobic fiber materials, more especially textile materials. Textile materials composed of blends that contain such semi-synthetic and/or synthetic hydrophobic textile materials can likewise be dyed or printed using the compounds according to the invention.
Semi-synthetic textile materials that come into consideration are especially cellulose 2½-acetate and cellulose triacetate.
Synthetic hydrophobic textile materials consist especially of linear, aromatic polyesters, for example those of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane; of polycarbonates, e.g. those of &agr;,&agr;-dimethyl-4,4-dihydroxy-diphenylmethane and phosgene, and of fibers based on polyvinyl chloride and on polyamide.
The application of the compounds according to the invention to the textile materials is effected in accordance with known dyeing procedures. For example, polyester fiber materials are dyed in the exhaust process from an aqueous dispersion in the presence of customary anionic or non-ionic dispersants and optionally customary swelling agents (carriers) at temperatures of from 80 to 140° C. Cellulose 2½-acetate is dyed preferably at about from 65 to 85° C. and cellulose triacetate at temperatures of up to 115° C.
The dye mixtures according to the invention will not stain wool and cotton present at the same time in the dyebath or will stain such materials only slightly (very good reservation), so that they can also be used satisfactorily to dye polyester/wool and polyester/cellulose fiber blend fabrics.
The dye mixtures according to the invention are suitable for dyeing in accordance with the thermosol process, in the exhaust and continuous process and for printing pr

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