Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2002-09-12
2003-09-09
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S494000
Reexamination Certificate
active
06616750
ABSTRACT:
The present invention relates to ternary pigment compositions comprising compounds of formulae (I), (II) and (III)
obtainable by the reaction of succinic acid diesters with a mixture of from 90 to 15 mol %, preferably from 80 to 25 mol %, more preferably from 75 to 25 mol %, 4-methylbenzonitrile and from 10 to 85 mol %, preferably from 20 to 75 mol %, more preferably from 25 to 75 mol %, 3-methylbenzonitrile, the molar amounts of the 4-methyl- and 3-methylbenzonitriles totalling 100 mol %, and to a process for the preparation thereof and to the use thereof for pigmenting organic material.
There are known from U.S. Pat. No. 4,720,305 pigment compositions of diketopyrrolopyrroles (DPPs) that can be prepared by mixed synthesis of two different nitrites A and B with succinic acid diester, the molar amounts of the nitrites disclosed in the Examples lying in the range from 90 to 99.9 mol % A relative to from 10 to 0.1 mol % B. 3- and 4-methylbenzonitriles are not specifically described.
There are known from U.S. Pat. No. 4,579,949 (examples 30, 36 and 37) processes for the preparation of pigment compositions of diketopyrrolopyrroles by the reaction of a succinic acid diester with a mixture of 4-methylbenzonitrile with benzonitrile, 4-methoxybenzonitrile or 4-chlorobenzonitrile in a molar ratio of 1:1. The preparation of DPP (I), a red pigment, is described in example 4 of that patent.
There is known from U.S. Pat. No. 4,783,540 (example 2) a red pigment composition of DPP (I) and DPP (III) in a molar ratio of 83:17, which is prepared in a two-step process by the preparation of the individual pigments (I) and (III) and subsequent co-precipitation thereof.
There is known from U.S. Pat. No. 5,708,188, example 2, a red pigment composition of DPP (III) and 1,4-diketo-3,6-di(4-chlorophenyl)pyrrolo[3,4-c]pyrrole in a molar ratio of 1:1.
In U.S. Pat. No. 4,415,685, the DPPs of formulae (I) and (III) (examples 28 and 31) are described as individual pigments having a red shade.
The problem underlying the present invention was to provide pigment compositions, preferably having high saturation and high hiding power, preferably colourants for industrial paint, that are distinguished by their yellowish-red to orange shade and that are obtainable by a simple and economically attractive preparation procedure. The finished colouration (in pressed PVC sheets containing 0.5% by weight pigment, see definition hereinbelow) of the pigment compositions should especially have a colour shade angle h in the range from 35 to 45, without the other desirable pigment characteristics being adversely affected.
The pigment compositions defined at the outset were accordingly discovered.
Also discovered were the use of such compositions for pigmenting high molecular weight material, especially for industrial paints, and a process for the preparation thereof.
A preferred embodiment of the present invention relates to those pigment compositions according to the invention that have a hiding power &Dgr;E*−S/W of <8, preferably <7 and more preferably <5, and most preferably of <3. The analytical samples (pressed PVC plates (1 mm thick), containing 0.5% by weight of a pigment composition according to the invention) for measurement of the &Dgr;E*−S/W values are prepared according to DIN 53 775 part 7. The &Dgr;E*−S/W value indicates the amount of colour difference of the analytical samples in the L*C*h system of the Commission Internationale de I{acute over ( )}Eclairage, over black (“S”) and white backgrounds; the smaller the value, the more opaque/the better the hiding power of the analytical sample.
In a preferred embodiment of the present invention, the pigment compositions according to the invention are obtainable by using the 4-methyl- and 3-methylbenzonitriles in a molar ratio of from 80 to 55 mol % 4-methylbenzonitrile to from 20 to 45 mol % 3-methylbenzonitrile, the pigment compositions so obtainable having a colour shade angle h in the range from 35 to 42, preferably in the range from 36 to 39 and more preferably in the range from 37 to 38.5.
The colour shade angle h is defined in the L*C*h system of the Commission Internationale de I{acute over ( )}Eclairage, L* being a measure of the brightness and C* a measure of the saturation. The h and C* values used in the present invention are determined in accordance with the measuring method DIN 53 775 part 7 using 0.5% by weight pigment in pressed PVC sheets.
A further more preferred embodiment of the pigment compositions according to the invention is obtainable by using the 4-methyl- and 3-methyl-benzonitriles in a molar ratio of from 80 to 55 mol % 4-methylbenzonitrile to from 20 to 45 mol % 3-methylbenzonitrile, the pigment compositions having a colour shade angle h in the range from 35 to 42, and a saturation value C* in the range from 65 to 80.
In a further preferred embodiment, pigment compositions according to the invention are furthermore obtainable by using the 4-methyl- and 3-methyl-benzonitriles in a molar ratio of from 45 to 25 mol % 4-methylbenzonitrile to from 55 to 75 mol % 3-methylbenzonitrile, the pigment compositions having a colour shade angle h in the range from 35 to 45, preferably in the range from 36 to 43 and more preferably in the range from 38 to 43.
A further preferred embodiment of the present invention relates to pigment compositions according to the invention that are obtainable by using the 4-methyl- and 3-methyl-benzonitriles in a molar ratio of from 80 to 55 mol % 4-methylbenzonitrile to from 20 to 45 mol % 3-methylbenzonitrile, the crystal lattice of which compositions substantially corresponds to that of compound (I) and preferably has twice the glancing angle (2 theta) at 7.4; 15.5; 20.1; 22.2; 22.9; 24.3; 26; 7; 31.2 and 32.6 (+/−0.5 theta) in the X-ray spectrum.
A further preferred embodiment of the present invention relates to pigment compositions according to the invention that are obtainable by using 4-methyl- and 3-methyl-benzonitrile in a molar ratio of from 45 to 25 mol %, preferably from 40 to 25 mol %, 4-methylbenzonitrile, to from 55 to 75 mol %, preferably from 60 to 75 mol %, 3-methylbenzonitrile, the crystal lattice of which compositions substantially corresponds to that of compound (II) and preferably has twice the glancing angle (2 theta) at 7.8; 12.5; 14.0; 15.5; 19.1; 21.1; 23.7; 26.1 and 32.3 (+/−0.5 2 theta) in the X-ray spectrum.
An more preferred embodiment of the present invention relates to the pigment compositions according to the invention that have a colour shade angle h in the range from 35 to 45, preferably in the range from 36 to 43, and of which the crystal lattice substantially corresponds to that of compound (II), the X-ray spectrum preferably having twice the glancing angle (2 theta) at 7.8; 12.5; 14.0; 15.5; 19.1; 21.1; 23.7; 26.1 and 32.3 (+/−0.5 2 theta), which compositions are obtainable by using 4-methyl- and 3-methyl-benzonitrile in a molar ratio of from 40 to 25 mol % 4-methylbenzonitrile to from 60 to 75 mol % 3-methyl-benzonitrile.
Most preferred are pigment compositions that have a colour shade angle h in the range from 38 to 43 and of which the crystal lattice substantially corresponds to that of compound (II), the X-ray spectrum preferably having twice the glancing angle (2 theta) at 7.8; 12.5; 14.0; 15.5; 19.1; 21.1; 23.7; 26.1 and 32.3 (+/−0.5 2 theta), which compositions are obtainable by using 70 mol % 4-methylbenzonitrile relative to 30 mol % 3-methylbenzonitrile. The term “substantially” indicates that the X-ray spectrum of the pigment compositions according to the invention corresponds to the X-ray spectrum of the individual compound (I), (II) or (III) as the case may be (depending on the composition), except that characteristic glancing angle shifts of the individual reflections may be possible as a result of lattice expansion (shift toward smaller glancing angles) or lattice contraction (shift toward larger glancing angles) in the region of +/−0.5 theta, or as a result of variations in
Lenz Roman
Schlöder Ingo
Wallquist Olof
Ciba Specialty Chemicals Corporation
Crichton David R.
Green Anthony J.
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