Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2002-03-08
2004-02-17
Shah, Mukund J. (Department: 1624)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S498000, C544S245000, C546S031000
Reexamination Certificate
active
06692562
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to a process for making perylene pigment compositions containing, in addition to a perylene pigment component, certain asymmetric perylene dicarboxamidine imides that can serve as crystal growth inhibitors during the preparation of the pigment compositions.
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. However, perylenes as initially isolated, 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. Schafer, “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).
Perylene diimides in which at least one of the imide groups is derived from a diamine that does not further react to form a dicarboxamidine imide are known. E.g., U.S. Pat. Nos. 5,958,129 and 5,248,774; European Patent Application EP 283,436; and T. Deligeorgiev et al, “Synthesis and Properties of Fluorescent Bis-Quaternized Perylene Dyes” in
Dyes and Pigments
, 24, 75-81 (1994).
Symmetric perylenes in which both of the imide groups are in the form of a dicarboxamidine have been reported. E.g., U.S. Pat. Nos. 4,556,622 and 2,473,015. These patents do not describe asymmetric perylene diimides in which only one of the imide groups is in the form of a dicarboxamidine.
Asymmetric perylene diimides in which one of the imide groups is in the form of a dicarboxamidine group have been reported but are not described as being used in admixture with perylene pigments. E.g., U.S. Pat. Nos. 5,508,137 and 4,714,666; German Patentschrift DD 299,733; H. Langhals et al, “Imidazoleperylenimide—ein starck fluoreszierender, stabiler Ersatz für Terrylen” in
Angew. Chem
., 111, 143-144 (1999); “Novel Dyes for Electrophotographic Processes with Perylene Structure Element” in
IS
&
T's Tenth International Congress on Advances in Non
-
Impact Printing Technologies
, 192-195 (1994); Y. Nagao, “Synthesis and properties of perylene pigments” in
Progress in Organic Chemistry
, 31, 43-49 (1997); H. Quante et al, “Synthesis of Soluble Perylenebisamidine Derivatives. Novel Long-Wavelength Absorbing and Fluorescent Dyes” in
Chem. Mater
., 9, 495-500 (1997); H. Langhals, “Novel Perylene Derivatives as Highly Photostable Fluorescent Dyes” in
Chimia
, 48, 503-505 (1994); G. Tamizhmani et al, “Photoelectrochemical Characterization of Thin Films of Perylenetetracarboxylic Acid Derivatives” in
Chem. Mater
., 3, 1046-1053 (1991); Y. Nagao et al, “Synthesis of Unsymmetrical Perylenebis(dicarboxamide) Derivatives” in
Chemistry Letters
, 151-154 (1979); K. Venkataraman et al, “Anthraquinoid Vat Dyes” in
Chemistry of Synthetic Dyes
, ed. K. Venkataraman, 5 (New York: Academic Press, 1971), page 233. Some of the compounds have been prepared by unrelated synthetic methods. E.g., U.S. Pat. No. 4,336,383.
Perylene dicarboxamidines derived from perylene dicarboxylic compounds rather than perylene tetracarboxylic compounds are also known but have not been described as being used in admixture with perylene pigments. E.g., U.S. Pat. No. 5,650,513 and L. Feiler et al, “Synthesis of Perylene-3,4-dicarboximides—Novel Highly Photostable Fluorescent Dyes” in
Liebigs Ann
., 1229-1244 (1995).
Perylene dicarboxamidine hydrazamides are known and have been described as being used in admixture with perylene pigments. See PCT application WO 00/40657. However, the hydrazamide moiety is structurally different from the imide moiety of the perylene dicarboxamidine imides of the present invention, and the PCT application does not disclose the preparation of co-precipitated blends of perylene diimides and perylene dicarboxamidine hydrazamides.
Compositions containing mixtures of perylene diimides and perylene dicarboxamidine imides are known. For example, U.S. Pat. Nos. 6,022,656, 5,019,473, and 4,968,571 describe blending the separately prepared components in polymeric binders for use in electrophotographic elements and U.S. Pat. No. 4,762,569 describes dispersing the separately prepared components non-aqueous paints or inks. None of these patents describes the preparation of co-precipitated blends of perylene diimides and perylene dicarboxamidine imides having small particle sizes of uniform particle size distribution.
In copending application Ser. No. 09/729,257 it has been disclosed that reactive co-precipitation of perylene pigments with certain asymmetric perylene dicarboxamidine imides provides pigment compositions having small-sized crystals that exhibit improved transparency and color properties, even in the unfinished form that is initially isolated without further physical manipulation to modify crystal size. A process for making these co-precipitated perylene pigments has been described.
An improved process for making these co-precipitated perylene pigments has now been found.
SUMMARY OF THE INVENTION
This invention relates to a process for the preparation of perylene pigment compositions comprising forming the perylene dicarboxamidine imide structure by
(A) reacting
(1) a perylene tetracarboxylic acid compound of formula (I)
wherein
R is hydrogen, C
1
-C
6
alkyl, C
5
-C
8
cycloalkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl,
A is C
1
-C
6
alkyl, C
1
-C
6
alkoxy, a sulfonyl group, amino, ammonium, hydroxy, nitro, or halogen, and
m is zero or a number from 1 to 8
(2) about 0.1 to about 25 mol % (preferably 0.5 to 10 mol %), based on the total amount of component (A)(i) of a perylene dicarboxamidine imide of formula (II),
wherein
W is C
2
-C
3
alkylene that is optionally substituted or modified,
(3) an alkylating agent of formula (V) or (VI)
R
1
—X (V)
R
1
—Y—R
1
(VI)
wherein
R
1
is C
1
-C
6
alkyl, C
5
-C
8
cycloalkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl,
X is a halogen, and
Y is sulfate (i.e., O—S(═O)
2
—O) or carbonate (i.e., O—C(═O)—O), and
(4) optionally, a solvent;
thereby forming a perylene pigment composition as a reactive co-precipitated blend; and
(B) isolating the perylene pigment composition.
The invention also relates to a process of preparing the perylene of formula (II) comprising
(C) reacting
(i) a perylene tetracarboxylic compound having the formula (III) wherein
E
1
and E
2
are independently OR or together are O,
each R is independently H (i.e., for carboxylic acids), C
1
-C
6
alkyl or C
5
-C
8
cycloalkyl (i.e., for alkyl esters), C
7
-C
16
aralkyl (i.e., for aralkyl esters), or C
6
-C
10
aryl (i.e., for aryl esters),
(ii) about 100 to 300 mol % (preferably 150 to 300 mol %) based on the total amount of (C)(i) of a diamine having the formula (IV),
H
2
N—W—NH
2
(IV)
wherein W is C
2
-C
3
alkylene that is optionally substituted or modified, and
(iii) optionally, a solvent; and
(D) isolating the perylene dicarboxamidine imide.
DETAILED DESCRIPTION OF THE INVENTION
Perylene tetracarboxylic compounds that can be used according to this invention, some of which are crude or conditioned perylene pigments and some of which are precursors of perylene pigment, can be prepared by any of various methods known in the art. E.g., W. Herbst and K. Hunge
McKenzie Thomas
Shah Mukund J.
Sidney Persley
Sun Chemical Corporation
LandOfFree
Process for making perylene pigment compositions does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for making perylene pigment compositions, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for making perylene pigment compositions will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3283514