US 6,211,346 B1Granted

Metal complex pigments

AssigneeBayer Aktiengesellschaft

InventorsFrank Linke, Kent Faubion, Udo Herrmann, Dirk Pfützenreuter, Ronald Göbel

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Abstract

Metal complexes of an azo compound which in the form of its tautomeric structures conforms to the formula (I) wherein the substituents are each as defined in the description, and which metal complexes host a compound as guest compound, characterized in that they have a dispersing harshness of less than 250.

Claims15

Dependent claims

A process for preparing a metal complex composition exhibiting a dispersing harshness less than 250 and comprising

(a) at least one metal complex of an azo compound conforming to the formula (I)
or a tautomeric form thereof,
wherein
rings X and Y independently are optionally substituted with one or two substituents selected from the group consisting of ═O, ═S, ═NR7, —NR6H7, —OR6, —SR6, —COOR6, —CN, —CONR6R7, —SO2R8,
alkyl, cycloalkyl, aryl, and aralkyl,
the dotted lines in each of the rings X and Y optionally represent one or two double bonds such that the total number of endocyclic and exocyclic double bonds is three for each of the rings X and Y,
R1, R2, R3, and R4 are independently hydrogen, alkyl, cycloalkyl, aryl, or aralkyl, or R1 and R2 together and/or R3 and R4 together form 5- or 6-membered rings, as indicated by the broken lines, to which further rings are optionally fused,
m, n, o, and p are 1 when the corresponding ring nitrogen atom is not part of a double bond or are zero when the corresponding ring nitrogen atom is part of a double bond, as indicated by the dotted lines,
R5 is —OH, —NR6R7, alkyl, cycloalkyl, aryl, or aralkyl,
R6 is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl,
R7 is hydrogen, cyano, alkyl, cycloalkyl, aryl, aralkyl, or acyl,
R8 is alkyl, cycloalkyl, aryl or aralkyl,
with the proviso that R1 to R8 are optionally further substituted by replacing the hydrogen atom of a CH group, and
(b) at least one guest compound, said process comprising
(1) preparing a metal complex of an azo compound conforming to the formula (I) in the presence of water and, optionally, an organic solvent at a pH of ≦2,
(2) forming an intermediate educt of the metal complex of the azo compound and at least one guest compound, wherein said educt is characterized by exhibiting a dispersing harshness greater than 250, at a pH of 1 to 7,
(3) heating the educt at a temperature of 80 to 180° C., with the proviso that if the heating step is carried out at a pH of <4, the heated educt is subsequently adjusted to a pH of >4.5,
(4) optionally additionally heating the educt, either in suspension or as an isolated solid, at a temperature of 80 to 180° C. at a pH of 1 to 4 or pH 9 to 13, and
(5) collecting the resultant metal complex composition.

16 more elements

Dependencies are inferred from the claim text.

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Abstract

A process for preparing a metal complex composition exhibiting a dispersing harshness less than 250 and comprising

(a) at least one metal complex of an azo compound conforming to the formula (I)
or a tautomeric form thereof,
wherein
rings X and Y independently are optionally substituted with one or two substituents selected from the group consisting of ═O, ═S, ═NR7, —NR6H7, —OR6, —SR6, —COOR6, —CN, —CONR6R7, —SO2R8,
alkyl, cycloalkyl, aryl, and aralkyl,
the dotted lines in each of the rings X and Y optionally represent one or two double bonds such that the total number of endocyclic and exocyclic double bonds is three for each of the rings X and Y,
R1, R2, R3, and R4 are independently hydrogen, alkyl, cycloalkyl, aryl, or aralkyl, or R1 and R2 together and/or R3 and R4 together form 5- or 6-membered rings, as indicated by the broken lines, to which further rings are optionally fused,
m, n, o, and p are 1 when the corresponding ring nitrogen atom is not part of a double bond or are zero when the corresponding ring nitrogen atom is part of a double bond, as indicated by the dotted lines,
R5 is —OH, —NR6R7, alkyl, cycloalkyl, aryl, or aralkyl,
R6 is hydrogen, alkyl, cycloalkyl, aryl, or aralkyl,
R7 is hydrogen, cyano, alkyl, cycloalkyl, aryl, aralkyl, or acyl,
R8 is alkyl, cycloalkyl, aryl or aralkyl,
with the proviso that R1 to R8 are optionally further substituted by replacing the hydrogen atom of a CH group, and
(b) at least one guest compound, said process comprising
(1) preparing a metal complex of an azo compound conforming to the formula (I) in the presence of water and, optionally, an organic solvent at a pH of ≦2,
(2) forming an intermediate educt of the metal complex of the azo compound and at least one guest compound, wherein said educt is characterized by exhibiting a dispersing harshness greater than 250, at a pH of 1 to 7,
(3) heating the educt at a temperature of 80 to 180° C., with the proviso that if the heating step is carried out at a pH of <4, the heated educt is subsequently adjusted to a pH of >4.5,
(4) optionally additionally heating the educt, either in suspension or as an isolated solid, at a temperature of 80 to 180° C. at a pH of 1 to 4 or pH 9 to 13, and
(5) collecting the resultant metal complex composition.

16 more elements