Pigment preparations

Details Pigment preparations Pigment preparations

1999-10-08

2001-07-17

Green, Anthony (Department: 1755)

Compositions: coating or plastic

Materials or ingredients

Pigment, filler, or aggregate compositions, e.g., stone,...

C008S466000, C008S494000, C524S089000, C524S092000, C524S100000

Reexamination Certificate

active

06261358

ABSTRACT:

The invention relates to new pigment preparations, 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-intensive dispersing processes to obtain the desired coloristics and hence the conforming particle size. Yet, such pigments still have some disadvantages in disperibility 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 solid pigment preparations comprising as pigment at least one metal complex 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,
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 complex hosts at least one other compound as guest compound, characterized in that a slurry of the solid pigment preparations with 20 times the amount of water has a pH of >6.5.
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
1
, —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 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, —CH, —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 has 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
-
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) and (V) with di- or trivalent metals, very particularly the nickel salts and complexes.
The metal complexes which contain at least one other compound, especially an 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 comforms to one of the tautomeric forms of the formula
and includes at least one other compound.
The invention further relates to metal complexes of an azo compound which in the form of its tautomeric structures conforms to the formula (V) and which contains at least one other compound as guest, characterized in that the metal complexes correspond to the mono-, di, tri- or tetraanions of the azo compounds of the formula (V) with the metals selected from the group consisting of Li, Cs, Mg, Cd, Co, Al, Cr, Sn, Pb, Na, K, Ca, Sr, Ba, Zn, Fe, Cu and Mn. The preferred included compounds are those identified hereinbelow.
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.
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 the nickel complex. In this case, in the formula (VI), for example, a portion 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 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 turn to those which have a boiling point of 100° C. or higher, preferably of not less than 150° C., at 1 bar. Suitable compounds are preferably acyclic and cyclic organic compounds, for example aliphatic and aromatic hydrocarbons, which may be substituted, for example by OH, COOH, NH
2
, substituted NH

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