Nitro dyes

Details Nitro dyes Nitro dyes

1997-01-21

1998-04-14

Gerstl, Robert

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

8649, C09B 5100, C07D27106

Patent

active

057393435

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/02745 filed Jul. 13, 1995. The present invention relates to novel nitro dyes of the formula I ##STR3## where X.sup.1 and X.sup.2 are independently of each other hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or pyrrolidin-2-on-1-yl, ##STR4## where R.sup.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl with or without interruption by from 1 to 3 oxygen atoms in ether function and with or without phenyl, phenoxy or acetyl substitution, C.sub.3 -C.sub.7 -cycloalkyl, which may be C.sub.1 -C.sub.4 -alkyl-substituted, or phenyl, which may be C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -alkoxy- or halogen-substituted, -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy, preparation, and their use for dyeing or printing textile materials.
The nitro dye C. I. Disperse Yellow 42 (10338) is commercially available. It comprises 2-nitro-4-phenylsulfamoyldiphenylamine.
It is an object of the present invention to provide novel nitro dyes which have advantageous application properties.
We have found that this object is achieved by the nitro dyes of the formula I defined at the beginning.
Any alkyl appearing in the abovementioned formula can be straight-chain or branched.
In any substituted alkyl or cycloalkyl appearing in the abovementioned formula I the number of substituents is generally 1 or 2.
In any substituted phenyl appearing in the abovementioned formula I the number of substituents is generally from 1 to 3, preferably 1 or 2.
X.sup.1, X.sup.2, X.sup.3, R.sup.1, R.sup.2, R.sup.3 and R.sup.5 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methyl-pentyl.
R.sup.1 may also be for example heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl or dodecyl (the above designations isooctyl, isononyl and isodecyl are trivial names derived from the oxo process alcohols--cf. Ullmann's Encyclopedia of Industrial Chemistry, 5.sup.th Edition, Vol. A1, pages 290 to 293, and also Vol. A10, 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, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 2- or 4-butoxybutyl, 4,8-dioxadecyl, 4,7-dioxaundecyl, 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9-trioxadodecyl, 4,7,10-trioxaundecyl, benzyl, 1- or 2-phenylethyl, phenoxymethyl, 1- or 2-phenoxyethyl, 2- or 3-phenoxypropyl, acetylmethyl, cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, cycloheptyl, phenyl, 2-, 3- or 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-ethylphenyl, 2,6-diethylphenyl, 2-, 3- or 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,6-diethoxyphenyl, 2-, 3- or 4-chlorophenyl or 2,4-dichlorophenyl.
X.sup.1, X.sup.2, R.sup.2 and R.sup.3 may each also be for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy or hexyloxy.
Preference is given to nitro dyes of the formula I where X.sup.1 and X.sup.2 are independently of each other hydrogen or C.sub.1 -C.sub.4 -alkyl and X.sup.3 is hydrogen.
Preference is further given to nitro dyes of the formula I, where X.sup.4 is a radical of the formula ##STR5## where R.sup.1 is in each case as defined above.
Preference is further given to nitro dyes of the formula Ia ##STR6## where X.sup.1, X.sup.2 and X.sup.4 are each as defined above.
Preference is further given to nitro dyes of the formula I where X.sup.4 is a radical of the formula ##STR7## where R.sup.1 is C.sub.1 -C.sub.4 -alkyl, cyclohexyl or phenyl.
Particular preference is given to nitro dyes of the formula Ia where X.sup.1 and X.sup.2 are independently of each other hydrogen or C.sub.1 -C.sub.4 -alkyl and X.sup.4 is a radical

REFERENCES:
patent: 2708149 (1955-05-01), Kartinos et al.
patent: 3957777 (1976-05-01), Toth
Colour Index, Third Edition, vol. 4 C.I. Disperse Yellow 42 (10338) (no date).
Chemical Abstracts, vol. 76, No. 18, May 1, 1972, p. 84, Columbus, Ohio, US .

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