Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2000-01-25
2001-05-01
Green, Anthony (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C008S576000, C106S493000, C106S494000, C106S499000, C546S037000, C549S247000
Reexamination Certificate
active
06224665
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to a process for preparing perylene pigment compositions in the presence of certain non-pigmentary cyclic anhydrides or imides. Perylenes, including diimides of perylene-3,4,9,10-tetracarboxylic acid, can be prepared by methods known in the art. E.g., W. Herbst and K. Hunger,
Industrial Organic Pigments,
2nd ed. (New York: VCH Publishers, Inc., 1997), pages 9 and 476-479; H. Zollinger,
Color Chemistry
(VCH Verlagsgessellschaft, 1991), pages 227-228 and 297-298; and M. A. Perkins, “Pyridines and Pyridones” in
The Chemistry of Synthetic Dyes and Pigments
, ed. H. A. Lubs (Malabar, Fla.: Robert E. Krieger Publishing Company, 1955), pages 481-482; see also U.S. Pat. Nos. 4,431,806, 4,496,731, 4,797,162, 5,248,774, 5,264,034, and 5,466,807. Perylenes as initially isolated in the process of the present invention, often referred to as crude perylenes, are generally unsuitable for use as pigments and thus must be subjected to one or more additional finishing steps that modify particle size, particle shape, and/or crystal structure in such a way that provides good pigmentary quality. See, for example, K. Merkle and H. Schäfer, “Surface Treatment of Organic Pigments” in
Pigment Handbook
, Vol. III (New York: John Wiley & Sons, Inc., 1973), page 157; R. B. McKay, “The Development of Organic Pigments with Particular Reference to Physical Form and Consequent Behavior in Use” in
Rev. Prog. Coloration,
10, 25-32 (1979); and R. B. McKay, “Control of the application performance of classical organic pigments” in
JOCCA,
89-93 (1989).
The addition of certain perylene derivatives to the ring-closure step has also been reported. For example, U.S. Pat. No. 5,264,034 discloses the use of certain perylene bis-imides or imide-anhydrides to improve the coloristic and rheological properties of perylene pigments. U.S. Pat. No. 5,248,774 discloses certain zwitterionic perylene bis-imide derivatives for use as colorants or as surface-modifying agents for known perylene pigments. U.S. Pat. No. 5,472,494 discloses the use of certain perylene mono-imide derivatives to modify the properties of organic pigments. These patents do not, however, disclose the non-pigmentary cyclic anhydrides and imides of the present invention.
It has now been found that the presence of certain non-pigmentary cyclic anhydrides and imides during the chemical synthesis of perylene bis-imides provides perylene pigment compositions that have improved transparency and color properties, even in the unfinished form that is initially isolated, and that are especially suitable for use in metallic paints.
Non-pigmentary cyclic anhydrides and imides of the type used in the present invention are known. E.g., U.S. Pat. No. 4,992,204 and J. M. Chapman, Jr. et al,
J. Pharm. Sci.,
78, 903-909 (1989). Such compounds have not, however, been used in combination with organic pigments.
Non-pigmentary naphthalimide derivatives have been disclosed in a journal article describing computer design of additives for improving the pigment properties of Pigment Red 179, an N,N-disubstituted perylene pigment. P. Erk et al,
Eur. Coat. J.,
10, 906-910 (1997). The article describes the naphthalimides as being poor growth inhibitors compared to perylene derivatives and does not disclose their incorporation during pigment synthesis. Furthermore, non-pigmentary cyclic anhydrides and imides of the type used in the present invention are not disclosed.
SUMMARY OF THE INVENTION
This invention relates to a process for preparing perylene pigment compositions comprising reacting
(a) a perylene tetracarboxylic compound;
(b) about 0.01 to about 20% by weight (preferably 5 to 15% by weight), relative to the perylene tetracarboxylic compound, of a non-pigmentary cyclic anhydride or imide having the formula (I)
wherein
W is O or NR
1
,
R
1
is hydrogen, a metal, C
1
-C
6
alkyl, C
5
-C
8
cycloalkyl, C
7
-C
16
aralkyl, C
6
-C
10
aryl, or —Alk—X,
R
2
and R
3
are independently hydrogen, C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl, or R
2
and R
3
together are fused-on rings (preferably fused-on cycloalkane or aromatic rings),
the dotted line is an optional double bond representing R
2
—C═C—R
3
(including a formal double bond of any fused-on aromatic ring formed by R
2
and R
3
taken together);
Alk is C
1
-C
18
alkylene or C
5
-C
8
cycloalkylene, and
X is
(i) an anionic group selected from —SO
3
−
, —COO
−
, —PO
3
=
, —PO(OR
X
)O
−
(wherein R
x
is C
1
-C
6
alkyl), —O—PO
3
=
, and —O—PO(OR
Y
)O
−
(wherein R
y
is C
1
-C
6
alkyl), each such anionic group being electrically balanced with a stoichiometric amount of a cation (preferably a hydrogen, metal, and/or ammonium ion),
(ii) a cationic group having the formula —NR
a
R
b
R
c+
(wherein R
a
, R
b
, and R
c
, are independently hydrogen, C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl), each such cationic group being electrically balanced with a stoichiometric amount of an anion (preferably halide, sulfate, phosphate, nitrate, mesylate, or tosylate or, less preferably, hydroxide),
(iii) NR
d
R
e
, wherein R
d
is hydrogen, C
1
-C
6
alkyl, C
7
-C
16
aralkyl, C
6
-C
10
aryl, C
2
-C
6
alkanoyl, C
7
-C
11
aroyl, or sulfonyl and R
e
is hydrogen, C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl,
(iv) OR
f
, wherein R
f
is hydrogen, C
1
-C
6
alkyl, or C
6
-C
10
aryl,
(v) COOR
g
, wherein R
g
is C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl,
(vi) sulfonyl, or
(vii) C
6
-C
10
aryl; and
(c) ammonia or a primary amine having the formula R
A
—NH
2
wherein R
A
is C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl;
optionally in the presence of
(d) a solvent and/or
(e) one or more additives.
The invention further relates to perylene pigment compositions prepared in this manner.
REFERENCES:
patent: 3976649 (1976-08-01), Fabian et al.
patent: 4256507 (1981-03-01), Kranz et al.
patent: 4431806 (1984-02-01), Spietschka et al.
patent: 4460410 (1984-07-01), Spietschka et al.
patent: 4496731 (1985-01-01), Spietschka et al.
patent: 4797162 (1989-01-01), Spietschka et al.
patent: 4831140 (1989-05-01), Spietschka et al.
patent: 4992204 (1991-02-01), Kluger et al.
patent: 5248774 (1993-09-01), Dietz et al.
patent: 5264032 (1993-11-01), Dietz et al.
patent: 5264034 (1993-11-01), Dietz et al.
patent: 5466807 (1995-11-01), Dietz et al.
patent: 5472494 (1995-12-01), Hetzenegger et al.
W. Herbst & K. Hunger, Industrial Organic Pigments, 2nd ed. (NY: VCH Publishers, Inc., month unavailable, 1997) pp. 9 and 476-479.
H. Zollinger, Color Chemistry (VCH Verlagsgessellschaft, month unavailable, 1991), pp. 227-228 and 297-298.
M.A. Perkins, “Pyridines and Pyridones” in the Chemistry of Synthetic Dyes and Pigments, ed. H.A. Lubs (Malabar, Florida: Robert E. Krieger Publishing Co., month unavailable, 1955, pp. 481-482.
K. Merkle & H. Schäfer, Surface Treatment of Organic Pigments in Pigment Handbook, vol. III (NY: John Wiley & Sons, Inc. month unavailable, 1973), p. 157.
R.B. McKay, “The Development of Organic Pigments with Particular Reference to Physical Form and Consequent Behavior in Use” in Rev. Prog. Coloration, 10, 25-32 (month unavailable) 1979.
R.B. McKay, “Control of the application performance of classical organic pigments” in JOCCA, 89-93 (month unavailable) 1989.
J. M. Chapman, Jr. et al, J. Pharm. Sci., 78, 903-909 (month unavailable) 1989.
P. Erk et al Eur. Coat J., 10, 906-910 (month unavailable) 1997.
F. Graser, Perylenes in Pigment Handbook, 2nd edition, vol. III, (NY: John Wiley & Sons, Inc., month unavailable 1988), pp. 653-658.
Database WPI, Week 8740, Derwent Publications Ltd., London GB; AN 1987-282034 [40] XP002137397, M. Toshiyuki et al, “Method of Dispersing Perylene or Perinone Pigment” & JP 62 197461 A (Sanyo Shikiso KK), Sep. 1, 1987, Abstract.
Greene Michael J.
Schulz Gregory R.
Bayer Corporation
Gil Joseph C.
Green Anthony
Henderson Richard E.L.
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