Metal complex pigments

Details Metal complex pigments Metal complex pigments

1999-10-08

2002-02-26

Green, Anthony (Department: 1755)

Compositions: coating or plastic

Materials or ingredients

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

C534S602000, C534S707000

Reexamination Certificate

active

06350307

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. In particular, strong lightfast red pigments are not disclosed therein.
It is accordingly an object of the present invention to provide new pigments which are free of the above-described disadvantages.
The invention accordingly provides metal complexes of an azo compound which conforms to the formula (I) or one of its tautomeric structures
wherein
R and R′ are independently OH, NH
2
, NH—CN, arylamino or acylamino,
R
1
and R
1′
are independently —H or —NH
2
,
and which contain at least one guest compound,
characterized in that the metal complexes correspond to the mono-, di-, tri- and tetraanions of the azo compounds of the formula (I) with the metals selected from the group consisting of Ca, Zn, Cu, Fe, Co, Sr, Ba, Cr, Sn, Al, Mg, Cd, Pb and La.
Aryl substituents in the formula (I) are preferably phenyl or naphthyl, which may each be substituted for example by halogen such as F, Cl, Br, —OH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
and —CN.
Acyl substituents in the formula (I) are preferably (C
1
-C
6
-alkyl)-carbonyl, phenylcarbonyl, C
1
-C
6
-alkylsulphonyl, phenylsulphonyl, optionally C
1
-C
6
-alkyl-, phenyl- and naphthyl-substituted carbamoyl, optionally C
1
-C
6
-alkyl-, phenyl- and 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, F, —H, —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, Br, —H, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
and —CN.
The term “metal complexes” is herein also to be understood as meaning metal salts.
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 its tautomeric structures of the formula (II)
where
R and R′ are independently selected from the group consisting of OH and NHCN,
and include at least one other compound.
Preference is given here in particular to organic metal complexes of those azo compounds of the formula (II) which in the form of their free acid correspond to one of the tautomeric structures of the formulae (IIa to IIc)
Particularly preferably, the compounds of the formula (I) are the 1:1 azo metal complexes which conform to the formula (Ia) or one of its tautomeric forms
wherein
Me corresponds to one of the above-mentioned metal centres,
R and R′ are each as defined above, and
R
1
and R
1′
are independently=O or —NH.
In general, the metal complex compound forms a layered crystal lattice in which the bonding within a layer is essentially via hydrogen bonds and/or metal ions. Preferably, the metal complex compounds are metal compounds which form a crystal lattice which consists of essentially planar layers.
The metal complexes hosting other guest compounds can be present in the form of inclusion compounds, intercalation compounds and also as solid solutions.
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 metal complex. In this case, in the formula (I), a portion of the metal may be replaced by other metal ions, or further metal ions can enter into a more or less pronounced interaction with the metal 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 (1 bar) of 100° C. or higher, preferably of 150° C. and higher. 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
2
, CONH
2
, substituted CONH
2
, SO
2
NH
2
, substituted SO
2
NH
2
, SO
3
H, halogen, NO
2
, CN, —SO
2
-alkyl, —SO
2
-aryl, —O-alkyl, —O-aryl, —O-acyl.
Aryl substituents are preferably phenyl or naphthyl, which may each be substituted for example by halogen such as F, Cl, Br, —H, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO and —CN.
Alkyl substituents are preferably C
1
-C
6
-alkyl, which may be substituted for example by halogen, such as chlorine, bromine, 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, F, C
1
-C
6
-alkoxy, —OH, —CN and NH
2
.
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, Br, —OH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
and —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- and naphthyl-substituted carbamoyl, optionally C
1
-C
6
-alkyl-, phenyl- and 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, 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, Br, —OH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, —NH
2
, —NO
2
and —CN.
Specific examples are paraffins and paraffin oils; triisobutylene, tetraisobutylene, mixtures of aliphatic and aromatic hydrocarbons as produced in petroleum fractionation for example; chlorinated paraffin hydrocarbons such as dodecyl chloride or stearyl chloride; C
10
-C
30
-alcohols such as 1-decanol, 1-dodecanol, 1-hexadecanol, 1-octadecanol and their mixtures, olein alcohol, 1,12-octadecanediol, fatty acids and their salts and mixtures, for example formic acid, acetic acid, dodecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, fatty acid esters, for example the methyl esters of C
10
-C
20
-fatty acids, fatty acid amides, such as stearamide, stearic acid monoethanolamide, stearic acid diethanolamide, stearonitrile, fatty amines, for example dodecylamine, cetylamine, hexadecylamine, octadecylamine and others; salts of fatty amines with sulphonic and carboxylic acids, isocyclic hydrocarbons such as cyclododecane, decahydronaphthalene, o-, m-, p-xylene, mesitylene, dodecylbenzene mixture, tetralin, naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, biphenyl, diphenylmethane, acenaphthene, fluorene, anthracene, phenanthrene, m-, p-terphenyl, o-, p-dichlorobenzene, nitrobenzene, 1-chloronaphthalene, 2-chloronaphthalene, 1-nitronaphthalene, isocyclic alcohols and phenols and their derivatives such as benzyl alcohol, decahydro-2-naphthol, diphenyl ether, sulphones, for example diphenyl sulphone, methyl phenyl sulphone, 4,4′-bis-2-(hydroxyethoxy)diphenyl sulphone; isocyclic carboxylic acids and their derivatives such as be,nzoic acid, 3-nitrobenzoic acid, cinnamic acid, 1-naphthalenecarboxylic acid, phthalic acid, dibutyl phthalate, dioctyl phthalate, tetrachlorophthalic acid, 2-nitrobenzamide, 3-nitrobenzamide, 4-nitrobenzamide, 4-chlorobenzamide, sulphonic acids, such as 2,5-dichlorobenzenesulphonic acid, 3-nitro-, 4-nitro-benzenesulphonic acid, 2,4-dimethylbenzenesulphollic acid, 1- and 2-naphthalenesulphonic acid, 5-nitro-1- and 5-nitro-2-naphthalenesulphonic acid, di-sec-butylnaphthalenesulphonic acid mixture, biphenyl-4-sulphonic acid, 1,4-, 1,5-, 2,6-, 2,7-naphthalenedisulphonic acid, 3-nitro-1,5-naphthalenedisulphonic acid, 1-anthraquinonesulphonic acid, 2-anthraquinonesulphon

Affiliated with

Also associated with

Rating

Metal complex pigments does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Metal complex pigments, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Metal complex pigments will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2936902