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US 5,037,964 AGranted
Metal-free sulfo group-free basis disazo and trisazo compounds containing two different 6-hydroxypyrid-2-one coupling component radicals
AssigneeSandoz Ltd.
InventorsHelmut A. Moser, Roland Wald
Life of this patent
Estimating the term…
Abstract
(i) Metal-free compounds of the formula ##STR1## These compounds are useful as dyes for paper and textiles.
Claims19
A compound of the formula ##STR34## or an acid addition salt thereof, wherein
- B is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy or hydroxy;
- C.sub.5-6 cycloalkyl;
- C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups;
- phenyl(C.sub.1-3 alkyl);
- phenyl(C.sub.1-3 alkyl) the phenyl ring of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo;
- --N(R.sub.7).sub.2 ;
- --A.sub.2 --N(R.sub.7).sub.2 or --A.sub.1 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar.,
- wherein
- A.sub.1 is linear or branched C.sub.2-8 alkylene;
- linear or branched C.sub.2-8 alkylene interrupted by one --NR.sub.5 --;
- linear or branched C.sub.2-8 alkylene monosubstituted by hydroxy;
- linear or branched C.sub.2-8 alkylene monosubstituted by hydroxy and interrupted by one --NR.sub.5 --;
- or linear or branched C.sub.2-8 alkenylene,
- A.sub.2 is linear or branched C.sub.1-8 alkylene;
- linear or branched alkylene having a maximum of 8 carbon atoms and interrupted by one --NR.sub.5 --;
- linear or branched C.sub.1-8 alkylene monosubstituted by hydroxy;
- linear or branched alkylene having a maximum of 8 carbon atoms monosubstituted by hydroxy and interrupted by one --NR.sub.5 --;
- or linear or branched C.sub.2-8 alkenylene,
- each R.sub.7 is independently hydrogen;
- C.sub.1-6 alkyl;
- C.sub.2-6 alkyl monosubstituted by halo, hydroxy or cyano;
- phenyl (C.sub.1-3 alkyl);
- phenyl(C.sub.1-3 alkyl) the phenyl ring of which is substituted by 1 to 3 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy;
- C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1 or 3 C.sub.1-4 alkyl groups, or
- --N(R.sub.7).sub.2 is a 5- or 6-membered saturated ring containing a total of 1 to 3 hetero atoms,
- each R.sub.8 is independently C.sub.1-6 alkyl;
- C.sub.2-6 alkyl monosubstituted by halo, hydroxy or cyano;
- phenyl(C.sub.1-3 alkyl);
- phenyl(C.sub.1-3 alkyl) the phenyl ring of which is substituted by 1 to 3 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy;
- C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups, or
- --N.sup..sym. (R.sub.8).sub.2 -- is a 5- or 6-membered saturated ring containing a total of 1 to 3 hetero atoms, and R.sub.9 is C.sub.1-4 alkyl or phenyl(C.sub.1-4 alkyl), or
- --N.sup..sym. (R.sub.8).sub.2 R.sub.9 is pyridinium or pyridinium substituted by 1 or 2 C.sub.1-4 alkyl groups,
- B.sub.1 is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy or hydroxy;
- C.sub.5-6 cycloalkyl;
- C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups;
- phenyl(C.sub.1-3 alkyl) or phenyl (C.sub.1-3 alkyl) the phenyl ring of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo,
- each R is independently hydrogen;
- C.sub.1-4 alkyl;
- C.sub.5-6 cycloalkyl;
- C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.1-4 alkyl groups;
- phenyl;
- phenyl substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy;
- benzyl;
- phenylether;
- or benzyl or phenylethyl the phenyl ring of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy,
- each R.sub.28 is independently hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- T" is hydrogen, cyano or ##STR35## wherein R.sub.3 " is hydrogen or methyl, T.sub.1 " is hydrogen, cyano or --CONH.sub.2, and
- x is a direct bond, linear or branched C.sub.1-4 alkylene, ##STR36## with the provisos that (i) when X is asymetric, either end is attached to Ring A and (ii) when at least one R.sub.28 is other than hydrogen, X is a direct bond, linear or branched C.sub.1-4 alkylene, --CO--NH--, ##STR37## wherein R.sub.42 is halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- each R.sub.43 is independently linear or branched C.sub.1-4 alkylene,
- each R.sub.44 is independently hydrogen or C.sub.1-4 alkyl,
- each R.sub.45 is independently halo, hydroxy, methoxy, ethoxy, amino, 2-hydroxyethylamino, N,N-di-(2-hydroxyethyl)amino, --NH--(CH.sub.2).sub.a --N(C.sub.2 H.sub.5).sub.2, N-methyl-N-phenylamino, N-cyclohexyl-N-Methylamino, piperidino or N-aminoethylpiperazino, wherein a is 2 or 3, and
- each g is independently 1, 2, 3 or 4,
- wherein R.sub.5 is hydrogen or C.sub.1-4 alkyl,
- each A.sup..crclbar. is independently a non-chromophoric anion, and each halo is independently fluoro, chloro, bromo or iodo,
- with the proviso that at least one of B and R" is or contains a water-solubilizing protonatable group or a water-solubilizing cationic group.
56 more elements
Dependencies are inferred from the claim text.