Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1998-07-22
2000-10-10
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534654, 534797, 534819, 8549, 8681, C09B 62513, C09B 3110
Patent
active
061303208
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel disazo dyes of the formula I ##STR2## where one of the two radicals X.sup.1 and X.sup.2 is hydroxyl and the other is amino, CO--Alk, SO.sub.2 --Ar, SO.sub.2 --Alk, SO.sub.2 --OAr, ##STR3## R.sup.2 is hydrogen or R.sup.2 and R.sup.1 together are a radical of the formula ##STR4## R.sup.3 is hydrogen, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkyl, halogen or a radical of the formula SO.sub.2 --OAr, SO.sub.2 --N(Ar)Alk or SO.sub.2 --NHAr or R.sup.3 and R.sup.2 together are a radical of the formula CO--NZ.sup.1 --Y, piperidinylsulfonyl, morpholinylsulfonyl or a radical of the formula CO--Ar, CO--OAlk, CO--NHAr, CO--N(Ar)Alk, CO--N(Alk).sub.2, SO.sub.2 --Alk, SO.sub.2 --OAr, SO.sub.2 --N(Alk).sub.2, SO.sub.2 --NHAlk, SO.sub.2 --N(Ar)Alk or SO.sub.2 --NHAr, and C.sub.1 -C.sub.4 -alkyl, halogen, cyano, nitro, hydroxysulfonyl, pyrrolidinylsulfonyl, piperidinylsulfonyl, morpholinylsulfonyl or a radical of the formula CO--Ar, CO--OAr, CO--OAlk, CO--N(Ar)Alk, CO--N(Alk).sub.2, SO.sub.2 --Ar, SO.sub.2 --Alk, SO.sub.2 --CH.sub.2 CH.dbd.CH.sub.2, SO.sub.2 --CH.dbd.CH.sub.2, SO.sub.2 --C.sub.2 H.sub.4 --Q, SO.sub.2 --OAr, SO.sub.2 --N(Alk).sub.2, SO.sub.2 --NHAlk, SO.sub.2 --N(Ar)Alk, SO.sub.2 --NHAr, ##STR5## where Alk is C.sub.1 -C.sub.8 -alkyl which may be interrupted by from 1 to 3 oxygen atoms in ether function or by 1 sulfur atom or 1 sulfonyl group and may be substituted by hydroxyl, C.sub.1 -C.sub.4 -alkanoyloxy, benzoyloxy, sulfato, halogen, cyano, carbamoyl, carboxyl, hydroxysulfonyl, phenoxy, phenyl or hydroxysulfonylphenyl, or is C.sub.5 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -alkyl, phenyl-(C.sub.1 -C.sub.4)-alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-(C.sub.1 -C.sub.4)-alkyl, phenoxy, hydroxyl, carboxyl, C.sub.1 -C.sub.4 -alkanoylamino with or without interruption by 1 oxygen atom in ether function in the alkyl chain, benzoylamino, hydroxysulfonyl, pyrrolidinylsulfonyl, piperidinylsulfonyl, morpholinylsulfonyl or a radical of the formula SO.sub.2 --Alk, SO.sub.2 --CH.sub.2 CH.dbd.CH.sub.2, SO.sub.2 --CH.dbd.CH.sub.2, SO.sub.2 --C.sub.2 H.sub.4 --Q, SO.sub.2 --NHAlk, SO.sub.2 --N(Alk).sub.2, SO.sub.2 --G, SO.sub.2 --OG, SO.sub.2 --NHG or SO.sub.2 --N(Alk)G, hydroxysulfonyl or C.sub.1 -C.sub.4 -alkanoylamino or is naphthyl which may be substituted by hydroxysulfonyl, R.sup.5 and at least one of the radicals R.sup.6, R.sup.7 or R.sup.8 are not hydrogen, dyeing natural or synthetic substrates.
It is an object of the present invention to provide novel disazo-based acid dyes having advantageous application properties.
We have found that this object is achieved by the acid disazo dyes of the formula I defined at the beginning.
If R.sup.3 and R.sup.2 together are a radical of the formula CO--NZ.sup.1 --Y, this radical can be bonded to the ring positions of R.sup.2 and R.sup.3 via Y or CO, or vice versa.
Any alkyl appearing in the abovementioned formula I may be straight-chain or branched.
Any substituted alkyl appearing in the abovementioned formula generally contains 1 or 2 substituents.
Any alkyl appearing in the abovementioned formulae with interruption by oxygen atoms in ether function is preferably alkyl interrupted by 1 or 2 oxygen atoms in ether function.
Any substituted phenyl appearing in the abovementioned formulae generally contains from 1 to 3 substituents. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, fluorine, chlorine or bromine.
Alk may also be for example pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, 1-ethylpentyl, octyl, 2-ethylhexyl, isooctyl (the above designation isooctyl is a trivial name derived from the oxo process alcohols--cf. Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 1, pages 290 to 293, and Vol. A 10, pages 284 and 285), 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl,
REFERENCES:
Dyes and Pigments 24 (1994) 125-141, Elsevier Science Limited, England, Printed in Great Britain.
Chemical Abstracts, vol. 99, No. 4, Jul. 25, 1983, Abs. No. 23999r, "disazo reactive dyes".
Lamm Gunther
Reichelt Helmut
Wagenblast Gerhard
BASF - Aktiengesellschaft
Powers Fiona T.
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