Basic azo and non-azo compounds having one or two disubstituted 1,3,5-triazine rings each of which is linked through a bridging radical to the 1-position of a pyrazole ring
AssigneeSandoz Ltd.
InventorReinhard Pedrazzi
Life of this patent
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Abstract
(i) Metal-free compounds of the formula ##STR1## (ii) tautomers thereof, (iii) 1:1 and 1:2 metal complexes of (i) and (ii), (iv) salts of (i), (ii), and (iii), and (v) mixtures of (i), (ii), (iii), and (iv), wherein the symbols are as defined in the Specification, are useful as dyes for, for example, polymers and copolymers of acrylonitrile, polyesters modified to contain acid groups, polyamides such as wool, leather, cotton, bast fibers such as hemp, flax, sisal jute, coir and straw, regenerated cellulose, glass fibers and paper (those wherein R.sub.o is other than hydrogen) or as intermediates for the synthesis of dyes.
Claims20
A metal-free compound of the formula ##STR171## a 1:1 or 1:2 metal complex of a metallizable metal-free azo compound of said formula or a salt or acid addition salt of a metal-free compound of said formula or of a 1:1 or 1:2 metal complex of a metallizable metal-free azo compound of said formula,
- wherein
- R.sub.o is R or --N.dbd.N--T--N.dbd.N--,
- wherein T is the radical of a tetrazo component,
- each Y is independently hydroxy;
- C.sub.1-4 alkoxy;
- phenoxy;
- amino;
- an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group;
- Z or ##STR172## and p is 1 when R.sub.o is R and is 2 when R.sub.o is --N.dbd.N--T--N.dbd.N--,
- wherein
- each A is independently phenylene;
- naphthylene;
- phenylene-phenylene;
- or phenylene, naphthylene or phenylene-phenylene each aromatic ring of which is substituted by 1 or 2 substituents selected from halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy and sulfo,
- each R is independently hydrogen or D--N.dbd.N--, wherein D is the radical of a diazo component,
- each R.sub.1 is independently O, NH or S,
- each R.sub.2 is independently C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --COOR.sub.3, --CONR.sub.4 R.sub.5 or --CO--Z,
- wherein R.sub.3 is hydrogen, C.sub.1-4 alkyl, phenyl or cyclohexyl,
- each of R.sub.4 and R.sub.5 is independently hydrogen;
- C.sub.1-4 alkyl;
- C.sub.2-4 alkyl monosubstituted in other than the the 1-position by hydroxy;
- or monosubstituted by cyano or chloro;
- phenyl;
- phenyl substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy;
- phenyl(C.sub.1-4 alkyl) or phenyl(C.sub.1-4 alkyl) the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy;
- or cyclohexyl, and
- Z is as defined below,
- each W is independently --NR.sub.6 -- or ##STR173## wherein R.sub.6 is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.2-4 alkyl monosubstituted in other than the 1-position by hydroxy or monosubstituted by cyano, chloro or C.sub.1-4 alkoxy;
- phenyl(C.sub.1-4 alkyl) or cyclohexyl,
- each X is independently linear or branched C.sub.1-6 alkylene, --*CONH-linear or branched C.sub.1-6 alkylene- or --*SO.sub.2 NH-linear or branched C.sub.1-6 alkylene, wherein the * denotes the atom attached to the --(A).sub.a -- radical,
- each Z is independently an N-bonded organic radical containing 1 to 5 nitrogen atoms at least one of which has basic character or forms an ammonium cation,
- each a is independently 0 or 1,
- each x is independently 0 or 1, with the proviso that the sum of each adjacent a and x is 1 or 2, and
- each halo is independently fluoro, chloro, bromo or iodo,
- or a mixture thereof.
A metal-free azo compound, a 1:1 or 1:2 metal complex or a salt or acid addition salt according to claim 33
- wherein
- D.sub.1 is --A.sub.ta --N.dbd.N--K.sub.ta,
- wherein A.sub.ta is ##STR202## wherein B.sub.a is a direct bond, --O--, --S--, --NH--, --(CH.sub.2).sub.c --, --NHCO--, --NHCONH--, --CH.dbd.CH--, ##STR203## wherein c is 1, 2 or 3,
- each d is 2 or 3, e is 2, 3 or 4, and
- the two groups attached to Ring D are meta or para to each other,
- R.sub.33 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, cyano, carbamoyl, (C.sub.1-4 alkyl)carbonylamino, ureido, carboxy or sulfo,
- each R.sub.34 is independently hydrogen, halo, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy or sulfo, and
- the two bonds denoted by an * attached to each Ring C are meta or para to each other, and
- K.sub.ta is ##STR204## wherein each Zd is --NH--Q.sub.1c --NR.sub.8c R.sub.9c or ##STR205## wherein each of R.sub.8c, R.sub.9c, R.sub.10c and R.sub.11c is independently methyl or ethyl,
- with the proviso that the two Zd groups are identical, and
- the --NH-- radical is in the 3- or 4-position of Ring E.
Dependencies are inferred from the claim text.