Metal complex pigments

Details Metal complex pigments Metal complex pigments

1999-10-08

2001-04-03

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C008S637100, C106S496000, C524S190000

Reexamination Certificate

active

06211346

ABSTRACT:

This invention relates to new metal complex pigments, processes for producing them and their use.
EP-A-73 463 discloses coloristically valuable pigments. These still have application disadvantages, however. For instance, pigments prepared in the manner described are very harsh in texture and have to be comminuted in relatively time-consuming dispersing processes to obtain the desired coloristics and hence the conforming particle size. Yet, such pigments still have some disadvantages in dispersibility and colour strength.
It is accordingly an object of the present invention to provide new pigmentary forms free of the above-described disadvantages.
According to the invention there are provided metal complexes of an azo compound which in the form of its tautomeric structures conforms to the formula (I)
wherein
the rings X and Y may each independently bear one or two substituents selected from the group consisting of ═O, ═S, ═NR
7
, —NR
6
H
7
, —OR
6
, —SR
6
, —COOR
6
, —CN, —CONR
6
R
7
, —SO
2
R
8
,
alkyl, cycloalkyl, aryl and aralkyl, the sum total of the endo- and exocyclic double bonds being three for each of the rings X and Y,
R
6
is hydrogen, alkyl, cycloalkyl, aryl or aralkyl,
R
7
is hydrogen, cyano, alkyl, cycloalkyl, aryl, aralkyl or acyl,
R
8
is alkyl, cycloalkyl, aryl or aralkyl,
R
1
, R
2
, R
3
and R
4
are each independently hydrogen, alkyl, cycloalkyl, aryl or aralkyl and furthermore, as indicated by the broken lines in the formula (I), may form 5- or 6-membered rings to which further rings may be fused,
R
5
is —OH, —NR
6
R
7
, alkyl, cycloalkyl, aryl or aralkyl, the substituents mentioned for R
1
to R
8
which contain CH bonds may in turn be substituted, and m, n, o and p are each 1 or, if the ring nitrogen atoms are the starting points for double bonds, as indicated by the dotted lines in the formula (I), may also be zero,
and which metal complexes host at least one compound as guest compound, characterized in that they have a dispersing harshness of less than 250 (measured according to DIN 53 775).
Preferred organic metal complexes are those of azo compounds which in the form of their free acid conform to one of the tautomeric forms of the formula (I) where the X ring represents a ring of the formula
where
L and M are each independently ═O, ═S or ═NR
6
,
L
1
is hydrogen, —OR
6
, —SR
6
, —NR
6
R
7
, —COOR
6
, —CONR
6
R
7
, —CN, alkyl, cycloalkyl, aryl or aralkyl,
M
1
is —OR
6
, —SR
6
, —NR
6
R
7
, —COOR
6
, —CONR
6
R
7
, —CN, —SO
2
R
8
,
alkyl, cycloalkyl, aryl or aralkyl, and the substituents M
1
and R
1
or M
1
and R
2
may form a 5- or 6-membered ring.
Particularly preferred organic metal complexes are those of azo compounds which in the form of their free acids conform to one of their tautomeric structures of the formulae (II) or (III)
where
R′
5
is —OH or —NH
2
,
R′
1
, R″
1
, R′
2
and R″
2
are each hydrogen, and
M′
1
, and M″
1
are each independently hydrogen, —OH, —NH
2
, —NHCN, arylamino or acylamino.
Very particularly preferred metal complexes are those of azo compounds of the formula (I) which in the form of their free acid conform to one of the tautomeric structures of the formula (IV)
where
M′″
1
and M
IV
1
are each independently OH or NHCN.
Preference is given especially to organic metal complexes of those azo compounds of the formula (I) which in the form of their free acid conform to one of the tautomeric structures of the formula (V)
In the foregoing formulae, the substituents preferably have the following meanings:
Alkyl substituents are preferably C
1
-C
6
-alkyl, which may be substituted for example by halogen, such as chlorine, bromine or fluorine, —OH, —CN, —NH
2
or C
1
-C
6
-alkoxy.
Cycloalkyl substituents are preferably C
3
-C
7
-cycloalkyl, especially C
5
-C
6
-cycloalkyl, which may be substituted for example by C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen such as Cl, Br or F, C
1
-C
6
-alkoxy, —OH, —CN or NH
2
.
Aryl substituents are preferably phenyl or naphthyl, which may each be substituted for example by halogen such as F, Cl or Br, —OH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
or —CN.
Aralkyl substituents are preferably phenyl- or naphthyl-C
1
-C
4
-alkyl, which may be substituted in the aromatic radicals by halogen such as F, Cl or Br, —OH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
or —CN, for example.
Acyl substituents are preferably (C
1
-C
6
-alkyl)carbonyl, phenylcarbonyl, C
1
-C
6
-alkylsulphonyl, phenylsulphonyl, optionally C
1
-C
6
-alkyl-, phenyl- or naphthyl-substituted carbamoyl, optionally C
1
-C
6
-alkyl-, phenyl- or naphthyl-substituted sulphamoyl or optionally C
1
-C
6
-alkyl-, phenyl- or naphthyl-substituted guanyl, where the alkyl radicals mentioned may be substituted for example by halogen such as Cl, Br or F, —OH, —CN, —NH
2
or C
1
-C
6
-alkoxy and the phenyl and naphthyl radicals mentioned may be substituted for example by halogen such as F, Cl or Br, —OH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
or —CN.
If M
1
R
1
or M
1
R
2
or M
1
R
2
and R
1
, R
2
, R
3
, R
4
, as indicated by the broken lines in the formula (I), form 5- or 6-membered rings, these are preferably triazole, imidazole or benzimidazole, pyrimidine or quinazoline ring systems.
Metal complexes, which is also to be understood as meaning metal salts, of the formulae (I) to (V) preferably include the salts and complexes of the mono-, di-, tri- and tetraanions with the metals Li, Cs, Mg, Cd, Co, Al, Cr, Sn, Pb, particularly preferably Na, K, Ca, Sr, Ba, Zn, Fe, Ni, Cu and Mn.
Particular preference is given to salts and complexes of the formulae (I) to (V) with di- or trivalent metals, very particularly the nickel salts and complexes.
The metal complexes which contain at least one compound, especially organic compound, as guest can be present as host-guest compounds, intercalation compounds and also as solid solutions.
They are very particularly preferably inclusion compounds, intercalation compounds and solid solutions in which the azobarbituric acid
ickel 1:1 complex conforms to one of the tautomeric forms of the formula
and includes at least one other organic compound.
In general, the metal complex forms a layered crystal lattice in which the bonding within a layer is essentially via hydrogen bonds and/or metal ions. Preferably, the metal complexes are metal complexes which form a crystal lattice which consists essentially of planar layers.
For the purposes of the present invention, the metal complexes of the azo compounds of the formula (I) which contain at least one compound as guest compound and have a dispersing harshness of less than 250 are referred to as pigments according to the invention. In a preferred embodiment, the pigments according to the invention have a dispersing harshness of less than 200, especially less than 150.
The dispersing harshness is measured according to DIN 53 775 Part 7, the cold rolling temperature being 25° C. and the hot rolling temperature 150° C.
All the dispersing harshnesses reported herein were determined by this modified DIN method.
In a preferred embodiment, the pigment according to the invention has a BET specific surface area of less than 150 m
2
/g, especially of 50 to 130 m
2
/g.
Useful metal complexes also include metal complexes in which a metal-containing compound, for example a salt or metal complex, is incorporated into the crystal lattice of another metal complex, for example of the nickel complex. In this case, in the formula (VI), a portion of the metal, for example of the nickel can be replaced by other metal ions, or further metal ions can enter into a more or less pronounced interaction with the metal, preferably nickel complex.
Included compounds may be organic compounds and inorganic compounds. Compounds which can be included come from a very wide variety of classes of compounds. For purely practical reasons, preference is given to such compounds as are liquid or solid under normal conditions (25° C., 1 bar).
Of the liquid substances, preference is given in tur

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