Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
1999-12-17
2001-05-08
Green, Anthony (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S494000, C534S575000, C534S588000
Reexamination Certificate
active
06228162
ABSTRACT:
FIELD OF THE INVENTION
C.I. Pigment Red 53:2 (below: P.R.53:2) is defined as the compound of the formula (I) which forms from the coupling of diazotized 2-amino-5-chloro-4-methylbenzenesulfonic acid with &bgr;-naphthol and subsequent reaction of the resulting sulfo acid with a calcium salt (M=½ Ca
2+
).
In the solid state, the compound of the formula (1) may also be present in another tautomeric or cis/trans isomeric form and may also contain Na
+
ions, Cl
−
ions, water molecules, and solvent molecules.
The majority of organic pigments exist in a plurality of different crystal modifications, also referred to as phases. Crystal modifications have the same chemical composition but a different arrangement of the building blocks (molecules) in the crystal. The crystal structure determines the chemical and physical properties, and therefore the individual crystal modifications often differ in rheology, color, and other coloristic properties. The different crystal modifications can be identified by means of X-ray powder diffractometry.
To date only three crystal modifications of P.R.53:2 (M=½ Ca
2+
) have been disclosed, which are referred to as the &agr;-phase, &ggr;-phase and &dgr;-phase (German Patent Applications 198 27 272.3 and 198 27 273.1).
The alpha-phase is distinguished by the following characteristic lines in the X-ray powder pattern: 2&THgr; values in degrees (relative intensities): 5.1 (100); 6.6 (73); 10.2 (37); 12.2 (39); 13.8 (31); 14.4 (27); 17.8 (24); 18.4 (22); 20.4 (20); 24.6 (26); 25.8 (86).
The &ggr;-phase shows the following characteristic lines: 4.4 (49); 5.8 (100); 8.8 (23); 10.3 (25); 10.9 (33); 12.2 (15); 13.9 (16); 15.4 (15); 16.7 (28); 17.6 (16); 18.4/18.6 (18/18, double line); 19.7 (20); 20.8 (18); 23.2 (48); 24.0 (21); 24.8 (37); 25.2 (34); 26.6 (19); 27.3 (19); 27.9 (12); 29.3 (14).
The &dgr;-phase shows the following characteristic lines: 3.3 (32), 4.7 (100), 7.5 (14), 9.4 (19), 10.5 (13), 13.8 (10), 14.2 (9), 14.9 (10), 16.7 (11), 17.6 (9), 18.1 (16), 18.9 (10), 20.4 (7), 21.1 (9), 22.1 (9), 22.7 (12), 23.1 (9), 23.6 (13), 24.1 (9), 24.9 (10), 25.5 (23), 26.3 (9), 27.7 (9), 28.1 (6), 28.9 (6), 30.4 (6).
It has surprisingly been found that the phase of C.I. Pigment Red 53:2 can be transformed into new phases by heating the pigment in certain liquid media, with full or partial dissolution of the pigment, and subsequently reprecipitating the pigment.
SUMMARY OF THE INVENTION
The present invention therefore provides a process for the phase transformation of C.I. Pigment Red 53:2, which comprises heating C.I. Pigment Red 53:2 in one or more organic solvents or a mixture of said solvents with water, the water content being from 0 to 90% by weight, in particular from 1 to 50% by weight, with the exception of the solvents isopropanol, isobutanol, amyl alcohol, chlorobenzene, and N-methylpyrrolidone, at a temperature of from 30 to 300° C., preferably from 60 to 200° C., and reprecipitating the pigment.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preference is given to solvents from the group consisting of dimethylacetamide; methanol, ethanol, n-propanol, C
6
-C
16
alcohol; n-butanol; sec-butanol; acetone, butanone; xylene, trimethylbenzene, dichlorobenzene, chloronaphthalene, nitrobenzene, phenetol, pyridine, dimethyl phthalate, ethyl acetate, methyl isobutyl ketone, acetophenone; quinoline; morpholine; dimethylformamide, N-methylformamide; ethylene glycol; glycolic acid n-butyl ester, and dimethyl sulfoxide.
In accordance with the process of the invention it is possible to prepare crystal modifications of P.R.53:2 which are distinguished by the following characteristic lines (Cu—K
&agr;
radiation 2&THgr; values in degrees, d values in Å
−1
, relative Intensity (I
rel
) in %):
2&THgr;
d
I
rel
&egr;(epsilon)-phase:
4.48
19.7
55
5.87
15.1
36
7.08
12.5
61
7.87
11.2
100
9.01
9.8
32
9.84
9.0
49
11.84
7.5
25
12.47
7.1
32
14.31
6.2
26
14.80
6.0
27
15.29
5.8
26
15.82
5.6
58
16.80
5.3
27
17.23
5.1
29
18.80
4.7
40
19.40
4.6
27
19.82
4.5
46
20.66
4.3
33
21.44
4.1
29
21.88
4.1
36
22.69
3.9
17
23.14
3.8
19
23.85
3.7
40
24.63
3.6
34
25.48
3.5
32
26.12
3.4
76
26.42
3.4
65
27.91
3.2
26
28.76
3.1
29
29.88
3.0
12
30.30
2.9
12
31.68
2.8
20
31.98
2.8
13
32.36
2.8
16
32.60
2.7
17
&zgr;(,,zeta“)-phase:
5.10
17.3
24
7.13
12.4
62
7.97
11.1
100
10.09
8.8
68
14.27
6.2
54
14.67
6.0
24
15.92
5.6
14
17.13
5.2
18
17.84
5.0
40
18.70
4.7
18
19.07
4.7
20
19.93
4.5
29
21.53
4.1
26
22.76
3.9
56
23.58
3.8
92
24.58
3.6
28
25.25
3.5
16
25.95
3.4
99
27.38
3.3
29
27.95
3.2
14
28.62
3.1
48
&eegr;(,,eta“)-phase:
4.57
19.3
100
9.07
9.7
68
12.18
7.3
45
14.77
6.0
65
21.09
4.2
30
26.60
3.3
96
&thgr;(,,theta“)-phase:
5.17
17.0
26
10.34
8.5
13
12.17
7.3
9
13.24
6.7
10
14.60
6.1
23
15.79
5.6
15
16.63
5.3
27
17.80
5.0
28
18.04
4.9
16
19.71
4.5
13
21.06
4.2
17
24.08
3.7
12
24.47
3.6
12
25.82
3.4
100
26.67
3.4
33
27.81
3.2
10
28.52
3.1
17
&igr;(,,jota“)-phase:
4.20
21.1
100
8.35
10.6
93
10.86
8.1
60
11.42
7.7
35
12.37
7.2
56
13.84
6.4
32
15.48
5.7
64
15.94
5.6
40
16.45
5.4
43
17.05
5.2
33
17.50
5.1
31
18.59
4.8
63
19.58
4.5
47
19.86
4.5
52
20.80
4.3
42
21.13
4.2
32
21.30
4.1
35
21.64
4.1
34
22.14
4.0
26
22.33
4.0
29
22.77
3.9
36
23.25
3.8
39
23.59
3.8
93
24.07
3.7
45
25.49
3.5
64
26.46
3.4
55
26.69
3.3
35
29.49
3.0
45
&kgr;(,,kappa“)-phase:
6.55
13.5
32
12.62
7.0
26
12.99
6.8
28
13.73
6.4
50
14.33
6.2
36
15.01
5.9
32
15.47
5.7
30
16.30
5.4
24
16.78
5.3
23
17.14
5.2
38
18.31
4.8
60
18.70
4.7
44
20.39
4.4
25
24.33
3.4
22
24.70
3.6
38
25.34
3.5
48
26.14
3.4
100
27.24
3.3
27
28.00
3.2
24
28.25
3.2
24
29.91
3.0
22
&lgr;(,,lambda“)-phase:
5.03
17.5
100
5.35
16.5
57
6.88
12.8
26
9.43
9.4
23
11.09
8.0
30
13.78
6.4
17
14.36
6.2
21
15.70
5.6
15
18.25
4.9
18
18.90
4.7
19
20.36
4.4
16
20.68
4.3
16
21.38
4.2
15
22.90
3.9
18
24.46
3.6
22
25.00
3.6
18
26.14
3.4
28
28.54
3.1
14
&ngr;(,,ny“)-phase:
4.76
18.5
64
7.70
11.5
43
9.22
9.6
24
9.50
9.3
46
11.64
7.6
15
12.74
6.9
21
13.43
6.6
33
13.76
6.4
15
14.11
6.3
13
14.27
6.2
15
15.72
5.6
16
16.26
5.4
10
17.37
5.1
12
17.73
5.0
20
18.95
4.7
20
19.91
4.5
20
20.45
4.3
12
20.87
4.3
19
21.51
4.1
13
22.79
3.9
21
23.12
3.8
28
23.44
3.8
20
24.59
3.6
17
25.26
3.5
49
25.96
3.4
29
26.35
3.4
100
27.05
3.3
44
28.03
3.2
14
28.72
3.1
10
29.38
3.0
8
29.89
3.0
7
31.30
2.9
9
32.12
2.8
7
32.50
2.8
9
33.27
2.7
8
&xgr;(,,xi“)-phase:
4.88
18.1
ca. 50
7.83
11.3
100
8.59
10.3
39
11.57
7.6
21
15.76
5.6
34
17.06
5.2
46
17.40
5.1
24
19.66
4.5
36
19.99
4.4
54
20.40
4.4
27
21.41
4.1
28
21.83
4.1
31
24.49
3.6
68
25.00
3.6
ca. 70
26.83
3.3
21
27.15
3.3
17
31.33
2.9
20
31.60
2.8
18
&ogr;(,,omikron“)-phase:
12.54
7.1
58
13.61
6.5
44
17.33
5.1
47
18.64
4.8
52
19.48
4.6
26
24.56
3.6
100
25.43
3.5
56
&pgr;(,,pi“)-phase:
5.60
15.8
100
9.09
9.7
82
9.62
9.2
72
11.21
7.9
27
11.65
7.6
4
12.86
6.9
5
15.24
5.8
6
15.88
5.6
22
16.85
5.3
14
18.23
4.9
21
19.07
4.7
35
19.40
4.6
54
20.82
4.3
20
22.23
4.0
24
23.02
3.9
27
23.49
3.8
23
24.79
3.6
98
26.01
3.4
41
27.66
3.2
75
28.20
3.2
10
30.12
3.0
9
30.85
2.9
9
31.34
2.9
9
31.52
2.8
6
31.59
2.8
6
&rgr;(,,rho“)-phase:
4.96
17.8
100
6.05
14.6
60
8.48
10.4
22
9.95
8.9
14
13.93
6.4
13
15.12
5.9
13
15.51
5.7
13
17.54
5.1
14
19.41
4.6
14
20.99
4.2
12
21.50
4.1
14
24.64
3.6
13
25.44
3.5
23
26.00
3.4
40
26.89
3.3
16
28.15
3.2
11
All line positions are associated with an uncertainty of ±0.2°.
In addition to Ca ions, the phases of the invention may also include Na ions, Cl ions, water molecules, and solvent molecules in the crystal lattice.
The new phases differ from the known crystal modifications in terms of their properties. They are of low solubility and are distinguished by orange to red hues, in some cases brown, high color strengths, and good coloristic properties.
In order to obtain a phase transformation, P.R.53:2 starting material is present in a phase which differs from that to be prepared, preferably in the alpha phase. It is also possible to use phase mixtures. The P.R.53:2 used as starting material can be used in the form of a dry pigment, a water-moist presscake, or an aqueous suspension.
The epsilon phase
Clariant GmbH
Green Anthony
Hanf Scott E.
Jackson Susan S.
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