Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1996-02-12
1997-03-18
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
546119, C09B 2936, C07D47104
Patent
active
056124651
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/02634 filed Aug. 9, 1994.
The present invention relates to novel azo dyestuffs of the formula I ##STR3## where R.sup.1 is C.sub.1 -C.sub.20 -alkyl which is unsubstituted or substituted and can be interrupted by 1 to 4 ether oxygen atoms, or is unsubstituted or substituted phenyl, or mercapto or unsubstituted or substituted alkylthio, consisting of the radicals of the formulae ##STR4## where L.sup.1 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, or is C.sub.1 -C.sub.4 -alkanoylamino, C.sub.1 -C.sub.4 -alkylsulfonylamino or a radical of the formula NY.sup.1 Y.sup.2, where Y.sup.1 and Y.sup.2 independently of one another in each case are hydrogen or C.sub.1 -C.sub.4 -alkyl or, together with the nitrogen bonding them, are a 5 - or 6 -membered saturated heterocyclic radical, one of the two radicals L.sup.2 and L.sup.3 is hydrogen and the other is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, or is C.sub.1 -C.sub.4 -alkanoylamino, C.sub.1 -C.sub.4 -alkylsulfonylamino or a radical of the formula NY.sup.1 Y.sup.2, in which Y.sup.1 and Y.sup.2 in each case have the abovementioned meanings, L.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, L.sup.5 is C.sub.1 -C.sub.4 -alkoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, or is C.sub.1 -C.sub.4 -alkylthio and L.sup.6 is C.sub.8 -C.sub.13 -alkyl which can be interrupted by 1 to 4 ether oxygen atoms, or is phenoxy, mercaptotriazolopyridines.
Triazolopyridine azo dyestuffs containing diazo components from the aniline series have already been disclosed in DE-A-4 020 768. However, it has been shown that the dyestuffs described there still have applicational deficiencies.
It is an object of the present invention to make available novel azo dyestuffs containing a coupling component from the triazolopyridine series and a diazo component from the aniline series and which have a high fastness to dry heat and pleating, high brilliance and high dyeing power.
We have now found that this object can be achieved by the azo dyestuffs of the formula I described in greater detail at the beginning.
The dyestuffs of the formula I can occur in several tautomeric forms, which are all covered by the patent claims. For example, the dyestuffs can occur in the following tautomeric forms: ##STR5##
If R.sup.1 in formula I is a substituted C.sub.1 -C.sub.20 -alkyl radical; suitable substituents can be eg. phenyl, phenoxy, carboxyl or C.sub.1 -C.sub.20 -alkoxycarbonyl whose alkyl chain can be interrupted by 1 to 4 ether oxygen atoms and is unsubstituted or substituted by phenyl or phenoxy. The alkyl radicals as a rule then have 1 or 2 substituents.
If in formula I alkyl radicals occur which are interrupted by ether oxygen atoms, those alkyl radicals are preferred which are interrupted by 1 or 2 ether oxygen atoms.
If in formula I substituted phenyl radicals occur, suitable substituents, if not stated otherwise, can be eg. C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, in this case in particular chlorine or bromine, cyano, nitro or carboxyl. The phenyl radicals as a rule then have 1 to 3 substituents.
If the radicals Y.sup.1 and Y.sup.2, together with the nitrogen bonding them, are a 5- or 6-membered saturated heterocyclic radical, suitable radicals for this purpose are eg. pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N-(C.sub.1 -C.sub.4 -alkyl)piperazinyl.
The radicals R.sup.1, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Y.sup.1 and Y.sup.2 are eg. methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
The radicals R.sup.1 are furthermore eg. pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, heptyl, 1-ethylpentyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl (the above names isooctyl, isononyl, isodecyl and isotridecyl are trivial names and o
REFERENCES:
patent: 5101028 (1992-03-01), Schefczik et al.
Etzbach Karl-Heinz
Grund Clemens
Reichelt Helmut
Schefczik Ernst
Sens Ruediger
BASF - Aktiengesellschaft
Powers Fiona T.
LandOfFree
Phenylazotriazolopyridine dyestuffs does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Phenylazotriazolopyridine dyestuffs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenylazotriazolopyridine dyestuffs will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1707372