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Azo compounds having at least one 6-hydroxypyrid-2-one coupling component radical metal complexes thereof and intermediates therefor

  • US 4,673,735 A
  • Filed: 04/09/1984
  • Issued: 06/16/1987
  • Est. Priority Date: 04/15/1982
  • Status: Expired due to Term
First Claim
Patent Images

1. A metal-free compound of the formula ##STR275## or a 1:

  • 1 or 1;

    2 metal complex thereof, or an acid addition salt of a metal-free compound of said formula or a 1;

    1 or 1;

    2 metal complex thereof,whereinB is hydrogen;

    C1-4 alkyl;

    C1-4 alkyl monosubstituted by C1-4 alkoxy;

    C2-4 alkyl substituted by hydroxy;

    C5-6 cycloalkyl;

    C5-6 cycloalkyl substituted by 1 to 3 C1-4 alkyl groups;

    phenyl(C1-3 alkyl);

    phenyl(C1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C1-4 alkyl, C1-4 alkoxy and halo;

    --A--NH--R2 ;

    --A4 '"'"'--N(R7)2 ;

    --A4 --N.sup.⊕

    (R8)2 R9 A.sup.⊖

    or --N(R7)2,whereinA is linear or branched C2-8 alkylene;

    linear or branched C2-8 alkylene interrupted by 1 or 2 hetero atoms;

    linear or branched C2-8 alkenylene;

    linear or branched C2-8 alkenylene interrupted by 1 or 2 hetero atoms;

    phenylene or cyclohexylene,A4 is linear or branched C2-8 alkylene or linear or branched C2-8 alkenylene,A4 '"'"' is linear or branched C1-8 alkylene or linear or branched C2-8 alkenylene, andR2 is ##STR276## wherein R11 is hydrogen, halo, nitro, C1-4 alkyl or C1-4 alkoxy, andR12 is --CO--(CH2)a --Z or ##STR277## wherein Z is --N(R7)2 or --N.sup.⊕

    (R8)2 R9 A.sup.⊖

    , and a is 1, 2 or 3,R is hydrogen;

    C1-4 alkyl;

    C5-6 cycloalkyl;

    C5-6 cycloalkyl substituted by 1 or 2 C1-4 alkyl groups;

    phenyl;

    phenyl substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy;

    benzyl;

    phenylethyl;

    or benzyl or phenylethyl the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy,R1 is hydrogen or --N═

    N--D,wherein D is a diazo component radical, with the proviso that R1 must be ##STR278## when B is other than --A--NH--R2, whereinA1 is a tetrazo component radical,R17 is hydrogen, --N═

    N--K1, --N═

    N--A10 --N═

    N--K1, ##STR279## wherein A10 is a tetrazo component radical or a coupling/diazo component radical,K1 is a diazo component radical or a coupling component radical,R20 is --(NR5)q --Q1 --N(R7)2, --(NR5)q --Q2 --N.sup.⊕

    (R8)2 R9 A.sup.⊖

    or ##STR280## wherein Q1 is linear or branched C2-6 alkylene, --CH2 C*O-- or --CH2 --CON*H--, wherein the * denotes the atom attached to the --(NR5)q -- radical, andQ2 is linear or branched C2-6 alkylene, --CH2 C*O--, --CH2 CON*H-- or --CH2 CONHC*O--, wherein the * denotes the atom attached to the --(NR5)q -- radical,Xo is a bridging radical,R19 is hydrogen;

    hydroxy;

    amino;

    (C1-4 alkyl)carbonylamino;

    benzoylamino;

    phenylamino;

    or benzoylamino or phenylamino the phenyl group of which is substituted by 1 or 2 substituents selected from halo, nitro, amino, C1-4 alkyl and C1-4 alkoxy, with the proviso that R19 must be hydrogen when R17 is other than --N═

    N--K1 and --N═

    N--A10 --N═

    N--K1, andR60 is hydroxy or amino, andR60a is hydrogen, hydroxy or amino, with the proviso that R60a is hydrogen or amino when R60 is hydroxy and is hydroxy when R60 is amino, andT is hydrogen, cyano, --COOR4, --CO--N(R5)2, --SO2 --N(R5)2, ##STR281## wherein each R3 is independently hydrogen, C1-4 alkyl, --N(R5)2 or --CO--N(R5)2,R4 is C1-6 alkyl or phenyl(C1-3 alkyl),R6 is C1-4 alkyl, andXa is --O--, --NR5 -- or --S--,whereineach R5 is independently hydrogen or C1-4 alkyl or, when two R5 '"'"'s are attached to a nitrogen atom, both R5 '"'"'s taken together and with the nitrogen atom may form a saturated ring containing 1 to 3 hetero atoms,each R7 is independently hydrogen;

    C1-6 alkyl;

    C2-6 alkyl monosubstituted by halo, hydroxy or cyano;

    phenyl(C1-3 alkyl);

    phenyl(C1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from halo, C1-4 alkyl and C1-4 alkoxy;

    C5-6 cycloalkyl or C5-6 cycloalkyl substituted by 1 or 3 C1-4 alkyl groups, or both R7 '"'"'s taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated ring containing 1 to 3 hetero atoms,each R8 is independently C1-6 alkyl;

    C2-6 alkyl monosubstituted by halo, hydroxy or cyano;

    phenyl(C1-3 alkyl);

    phenyl(C1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from halo, C1-4 alkyl and C1-4 alkoxy;

    C5-6 cycloalkyl or C5-6 cycloalkyl substituted by 1 or 3 C1-4 alkyl groups,each R9 is independently C1-4 alkyl or C1-4 alkyl substituted by phenyl or both R8 '"'"'s and R9 taken together and with the nitrogen atom to which they are attached are pyridinium;

    pyridinium substituted by 1 or 2 C1-4 alkyl groups;

    or a 5- or 6-membered saturated ring containing 1 to 3 hetero atoms,each R13 is independently amino;

    an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group the nitrogen atom of which is attached to the 1,3,5-triazine ring;

    halo;

    hydroxy;

    C1-4 alkoxy;

    phenyl or ##STR282## wherein A2 is linear or branched C2-6 alkylene or --N*HCOCH2 --,wherein the * denotes the atom attached to the --NR5 -- radical, and R, R1, R5 and T are as defined above,each R14 is independently an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group the nitrogen atom of which is attached to the 1,3,5-triazine ring,each n is independently 0, 1 or 2,each q is independently 0 or 1, andeach A.sup.⊖

    is independently a non-chromophoric anion,with the provisos that (i) when the compound of Formula I is a monoazo compound free of sulfo groups, it contains at least one water-solubilizing basic or cationic group, (ii) when the compound of Formula I is free of sulfo groups and is other than a monoazo compound, it contains at least two water-solubilizing groups, and (iii) when the compound of Formula I contains one or more sulfo groups, the total number of basic and cationic groups exceeds the number of sulfo groups by at least one.

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