Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-10-05
2000-02-22
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C09B 2900
Patent
active
060281790
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to trisazo dyes of the general formula I ##STR2## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen, nitro, hydroxysulfonyl, sulfamoyl, mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl, C.sub.1 -C.sub.4 -alkylsulfonyl or C.sub.1 -C.sub.4 -alkoxysulfonyl, R.sup.1 and R.sup.2 being nitro, mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkoxysulfonyl or carboxyl, mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkoxysulfonyl, SO.sub.2 N(CH.sub.2 COOH).sub.2 or carboxyl, -alkoxy, halogen or nitro, SO.sub.3 H and when R.sup.5 or R.sup.7 is SO.sub.3 H the other is COOH, or R.sup.3 and/or R.sup.4 are each amino or R.sup.1 is hydrogen or R.sup.6 is alkyl, leather, textile fibers and paper.
Acid trisazo dyes which produce brown hues are well known and are used for example for dyeing leather, textiles and paper (see for example DE-A-22 38 159, U.S. Pat. No. 2,259,734 and WO 81/03179). The dyes were used either in free form or in the form of metal complexes, especially as copper complexes.
However, the known dyes leave something to be desired as regards their lightfastness, washfastness and perspiration fastness and their dyeing behavior, for example as regards the degree of liquor exhaustion.
It is an object of the present invention to provide novel trisazo dyes which are superior to the known dyes as regards lightfastness, washfastness and perspiration fastness and/or dyeing behavior.
We have found that this object is achieved by the trisazo dyes of the general formula I mentioned at the beginning.
Suitable R.sup.1, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 include for example the C.sub.1 -C.sub.4 -alkyl radicals methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. Methyl is preferred.
Suitable R.sup.1, R.sup.5 and R.sup.7 include for example mono- or di-C.sub.1 -C.sub.4 -alkylsulfamoyl radicals, C.sub.1 -C.sub.4 -alkylsulfonyl radicals and C.sub.1 -C.sub.4 -alkoxysulfonyl radicals with the alkyl radicals mentioned.
Suitable R.sup.8 includes for example C.sub.1 -C.sub.4 -alkoxy radicals with the alkyl groups mentioned.
Suitable R.sup.1, R.sup.2 and R.sup.8 include the halogens fluorine, chlorine, bromine and iodine, preferably chlorine and bromine.
Preferred R.sup.1 and R.sup.2 are hydrogen, hydroxysulfonyl and nitro, in particular hydrogen and nitro, at least one of the radicals R.sup.1 or R.sup.2, preferably both, being nitro. R.sup.1 and R.sup.2 are each preferably disposed meta to the diazo group.
R.sup.3 and R.sup.4 are preferably identical. The diazo groups coupled to the same phenyl ring are both preferably disposed ortho to them, resulting in a 1,2,4,5-substituted phenyl ring.
Preferred R.sup.5 is COOH, SO.sub.3 H, methyl and hydrogen, of which carboxyl is particularly preferred.
Preferred R.sup.6 is hydrogen and methyl. Hydrogen is the preferred R.sup.6 in combination with COOH, SO.sub.3 H or hydrogen as R.sup.5. R.sup.6 is preferably methyl when R.sup.5 is methyl too.
Preferred R.sup.7 is SO.sub.3 H and COOH.
Particularly preferred dyes are those in which either R.sup.5 or R.sup.7 is carboxyl.
Preferred R.sup.8 is hydrogen, methyl and hydroxyl.
The trisazo dyes of the present invention can be used in the free form or in the form of their metal salts.
Suitable transition metals for complexing with the trisazo dyes are in particular the elements of subgroups 6, 7 and 8 of the periodic table and also copper, especially chromium, iron, cobalt, nickel and copper, and iron complexes are particularly preferred.
Particular preference is given to the iron complexes of the following trisazo dyes, which are obtained by reacting one mol equivalent of dye with 0.5 to 2 mol equivalents of iron salt: ##STR3##
Preference is given to iron complexes of the dyes Ia-d with a 1:1 stoichiometry and to the iron complexes of the dyes Ia and b with a 2:1 stoichiometry of the starting materials (iron salt/dye).
Suitable iron salts are water-soluble iron(II) salts such as iro
REFERENCES:
patent: 2220397 (1940-11-01), Crossley et al.
patent: 2259734 (1941-10-01), Crossley et al.
patent: 2259735 (1941-10-01), Crossley et al.
patent: 2259736 (1941-10-01), Crossley et al.
patent: 5270455 (1993-12-01), Schlesinger
Lamm Gunther
Scholz Gerhard
BASF - Aktiengesellschaft
Powers Fiona T.
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