US 4,307,015 AGranted

Azo compounds having a 2-acyloxy-, alkoxy-, substituted alkoxy-or hydroxy-3-alkynyloxy or substituted alkenyloxy-propyl group

AssigneeSandoz Ltd.

InventorKlaus Koerte

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Abstract

Compounds of the formula ##STR1## wherein D is a diazo component radical, K is the radical of a coupling component of the 1,4-phenylene or 1,4-naphthylene series, R.sub.1 is hydrogen; alkyl; or alkenyl; and when K is a coupling component radical of the 1,4-phenylene series, R.sub.1 is also alkenyl monosubstituted by halogen; or alkyl which is substituted by a halogen, hydroxy, alkoxy, acyloxy, phenyl, phenoxy, cyano, alkenyloxy, alkynyloxy or alkoxyalkynyloxy group and is optionally further substituted by a hydroxy group, R.sub.2 is hydrogen, acyl, alkyl or alkyl monosubstituted by halogen, alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy and ##STR2## with the proviso that when R.sub.4 is ##STR3## K is a coupling component radical of the 1,4-naphthylene series, R.sub.5 is hydrogen, or ##STR4## each of R.sub.3 and R.sub.3 ' is independently hydrogen or alkyl, or R.sub.3 and R.sub.3 ' together with the carbon atom to which they are bound form a cyclohexane ring, with the proviso that when R.sub.3 and R.sub.3 ' form a cyclohexane R.sub.5 is hydrogen, one of R.sub.6 and R.sub.6 ' is hydrogen and the other is hydrogen or halogen, R.sub.7 is hydrogen or alkyl, each of R.sub.8 and R.sub.8 ' independently, is hydrogen or alkyl and R.sub.9 is hydrogen, acyl, alkyl or alkyl monosubstituted by alkoxy, alkoxyalkoxy or acyloxy, wherein all alkyl and alkoxy moieties contain 1 to 6 carbon atoms, and all alkenyl and alkynyl moieties contain 2-6 carbon atoms, which compounds are useful as disperse dyes for dyeing or printing substrates comprising synthetic or semi-synthetic, hydrophobic, high molecular weight organic textile materials.

Claims31

Dependent claims

A disperse dye of the formula ##STR59## wherein D is a diazo component radical, ##STR60## or 1,4-naphthylene, wherein R.sub.10 is hydrogen, chloro, bromo, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, 2-hydroxyethoxy, 2-methoxyethoxy or cyano(C.sub.1-2 alkoxy), and

R.sub.11 is hydrogen, chloro, bromo, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-2 chloroalkyl)carbonylamino, (C.sub.1-2 -bromoalkyl)carbonylamino, cyano, formamido, (C.sub.1-2 alkoxy) (C.sub.1-4 alkyl)-carbonylamino, (C.sub.1-4 alkoxy)carbonylamino, phenoxy(C.sub.1-2 alkyl)carbonylamino, 2-(C.sub.1-2 alkoxy) (C.sub.2-3 -alkoxy)carbonylamino, 3-(C.sub.1-2 alkoxy)propoxycarbonylamino, (C.sub.1-4 alkoxy)carbonyl (C.sub.1-3 alkyl)aminocarbonylamino, benzamido or phenyl-(C.sub.1-2 alkyl)carbonylamino, R.sub.11 being ortho to the --N.dbd.N-- radical,
R.sub.1 is hydrogen;
C.sub.1-6 alkyl;
C.sub.2-6 alkenyl;
C.sub.2-6 haloalkenyl;
C.sub.1-6 alkyl monosubstituted by halo, hydroxy, C.sub.1-6 alkoxy, acyloxy, phenyl, phenoxy, cyano, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy or (C.sub.1-6 alkoxy)C.sub.2-6 alkynyloxy;
or C.sub.1-6 alkyl substituted by hydroxy and one further substituent selected from the group consisting of halo, hydroxy, C.sub.1-6 alkoxy, acyloxy, phenyl, phenoxy, cyano, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy and (C.sub.1-6 alkoxy)C.sub.2-6 alkynyloxy, with the proviso that R.sub.1 must be hydrogen, C.sub.1-6 alkyl or C.sub.2-6 alkenyl when K' is 1,4-naphthylene,
R.sub.2 is hydrogen, acyl, C.sub.1-6 alkyl or C.sub.1-6 alkyl monosubstituted by halo, C.sub.1-6 alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy,
each of
R.sub.3 and R.sub.3 ' is independently hydrogen or C.sub.1-6 alkyl or
R.sub.3 and R.sub.3 ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and
R.sub.5 is hydrogen or ##STR61## wherein each of R.sub.8 and R.sub.8 ' is independently hydrogen or C.sub.1-6 alkyl, and
R.sub.9 is hydrogen, acyl, C.sub.1-6 alkyl or C.sub.1-6 alkyl monosubstituted by C.sub.1-6 alkoxy, (C.sub.1-6 alkoxy)C.sub.1-6 alkoxy or acyloxy,
with the proviso that R.sub.5 must be hydrogen when R.sub.3 and R.sub.3 ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring,
wherein each acyl and the acyl moiety of each acyloxy is independently R--O--CO--, R--SO.sub.2 --, R'--CO--, R'--NR"--CO-- or R'--NR"--SO.sub.2 --,
wherein R is C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and
each of R' and R" is independently hydrogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and
each halo is independently fluoro, chloro, bromo or iodo.

15 more elements

A compound of the formula ##STR62## wherein D' is phenyl;

substituted phenyl having 1 to 4 substituents each of which is independently chloro, bromo, iodo (maximum of two), cyano (maximum of two), trifluoromethyl (maximum of two), C.sub.1-2 alkylsulfonyl (maximum of two), nitro (maximum of two), methyl (maximum of two), methoxy (maximum of two), formyl (maximum of one), (C.sub.1-4 alkyl)carbonyl (maximum of one), (C.sub.1-2 alkoxy)carbonyl (maximum of one), carbamoyl (maximum of one), (C.sub.1-2 alkyl)carbamoyl (maximum of one), di-(C.sub.1-2 alkyl)carbamoyl (maximum of one), phenylcarbamoyl (maximum of one), (C.sub.1-2 alkyl)carbonylamino (maximum of one), phenyl (maximum of one), benzoyl (maximum of one), benzylcarbonyl (maximum of one), phenylsulfonyl (maximum of one), tolylsulfonyl (maximum of one), sulfamoyl (maximum of one), C.sub.1-2 alkylsulfamoyl (maximum of one), di-(C.sub.1-2 alkyl)sulfamoyl (maximum of one), thiocyano (maximum of one), phenylazo or substituted phenylazo having 1 to 3 substituents each of which is independently chloro, bromo, methyl (maximum of two), C.sub.1-2 alkoxy (maximum of two), cyano (maximum of two), nitro (maximum of two) or phenyl (maximum of one) (maximum number of phenylazo and substituted phenylazo together is one);
benzothiazolyl;
substituted benzothiazolyl having 1 or 2 substitutents each of which is independently chloro, bromo, cyano, nitro, methyl (maximum of one), C.sub.1-2 alkylsulfonyl (maximum of one), sulfamoyl (maximum of one) or thiocyano (maximum of one);
benzoisothiazolyl;
substituted benzoisothiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, nitro (maximum of one) or C.sub.1-2 alkylsulfonyl (maximum of one);
thienyl;
substituted thienyl having 1 to 3 substituents each of which is independently chloro (maximum of two), bromo (maximum of two), cyano (maximum of two), nitro (maximum of two), methyl (maximum of one), phenyl (maximum of one), C.sub.1-3 alkyl)carbonyl (maximum of one), hydroxy (maximum of one) or methoxycarbonyl (maximum of one);
thiazolyl;
substituted thiazolyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, methyl (maximum of one), nitro (maximum of one) or C.sub.1-2 alkylsulfonyl (maximum of one);
3-phenyl-1,2,4-thiadiazolyl-5 or 2-phenyl-1,3,4-thiadiazolyl-5, ##STR63## or 1,4-naphthylene, wherein:
R.sub.10 is hydrogen, chloro, bromo, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, 2-hydroxyethoxy, 2-methoxyethoxy or cyano(C.sub.1-2 alkoxy), and
R.sub.11 is hydrogen, chloro, bromo, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-2 chloroalkyl)carbonylamino, (C.sub.1-2 bromoalkyl)carbonylamino, cyano, formamido, (C.sub.1-2 alkoxy) (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-4 alkoxy)carbonylamino, phenoxy (C.sub.1-2 alkyl)carbonylamino, 2-(C.sub.1-2 alkoxy) (C.sub.2-3 alkoxy)carbonylamino, 3-(C.sub.1-2 alkoxy)propoxycarbonylamino, (C.sub.1-4 alkoxy)carbonyl (C.sub.1-3 alkyl)aminocarbonylamino, benzamido or phenyl(C.sub.1-2)carbonylamino, R.sub.11 being ortho to the --N.dbd.N-- radical,
R.sub.1 is hydrogen;
C.sub.1-6 alkyl;
C.sub.2-6 alkenyl;
C.sub.2-6 haloalkenyl;
C.sub.1-6 alkyl monosubstituted by halo, hydroxy, C.sub.1-6 alkoxy, acyloxy, phenyl, phenoxy, cyano, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy or (C.sub.1-6 alkoxy)C.sub.2-6 alkynyloxy;
or C.sub.1-6 alkyl substituted by hydroxy and one further substituent selected from the group consisting of halo, hydroxy, C.sub.1-6 alkoxy, acyloxy, phenyl, phenoxy, cyano, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy and (C.sub.1-6 alkoxy)C.sub.2-6 alkynyloxy, with the proviso that R.sub.1 must be hydrogen, C.sub.1-6 alkyl or C.sub.1-6 alkenyl when K' is 1,4-naphthylene,
R.sub.2 is hydrogen, acyl, C.sub.1-6 alkyl or C.sub.1-6 alkyl monosubstituted by halo, C.sub.1-6 alkoxy, phenyl, phenoxy, benzyloxy, hydroxy or acyloxy,
each of
R.sub.3 and R.sub.3 ' is independently hydrogen or C.sub.1-6 alkyl or
R.sub.3 and R.sub.3 ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring, and
R.sub.5 is hydrogen or ##STR64## wherein each of R.sub.8 and R.sub.8 ' is independently hydrogen or C.sub.1-6 alkyl, and
R.sub.9 is hydrogen, acyl, C.sub.1-6 alkyl or C.sub.1-6 alkyl monosubstituted by C.sub.1-6 alkoxy, (C.sub.1-6 alkoxy)C.sub.1-6 alkoxy or acyloxy,
with the proviso that R.sub.5 must be hydrogen when R.sub.3 and R.sub.3 ' taken together and with the carbon atom to which they are joined form a cyclohexyl ring,
wherein each acyl and the acyl moiety of each acyloxy is independently R--O--CO--, R--SO.sub.2 --, R'--CO--, R'--NR"--CO-- or R'--NR"--SO.sub.2 --,
wherein R is C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and
each of R' and R" is independently hydrogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, phenyl, tolyl or benzyl, and
each halo is independently fluoro, chloro, bromo or iodo.

26 more elements

Dependencies are inferred from the claim text.

Facts

Application: 06/070,762Filed 30 Aug 1979 · continuation in part
Priority: CH 10800/775 Sep 1977
Granted: 22 Dec 1981
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C09B 29/0813
Further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino: substituted by OH, O-C-R, O-C-X-R, O-R
C09B 29/0003
Monoazo dyes prepared by diazotising and coupling: from diazotized anilines
C09B 29/095
From coupling components containing amino as the only directing group: amino naphthalenes
C09B
Organic dyes or closely-related compounds for producing dyes