Process for the preparation of perylene pigments

Details Process for the preparation of perylene pigments Process for the preparation of perylene pigments

2000-12-22

2002-06-11

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C106S493000, C106S494000, C106S498000, C106S499000

Reexamination Certificate

active

06403797

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a process for preparing perylene pigment compositions using certain amphoteric surfactants and non-pigmentary cyclic anhydrides and 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 Dves 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. Schätfer, “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 been reported to improve the resultant pigments. 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 amphoteric 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 use of amphoteric surfactants.
U.S. Pat. No. 4,496,731 discloses a stepwise preparation of N,N-dialkylated perylene pigments in which a perylene-3,4,9,10-tetracarboxylic acid dianhydride first reacts with an alkylamine to form the corresponding ring-opened dialkyldiimide that is then thermally ring closed to form the pigment. Surfactants can optionally be added before, during, or after the cyclization reaction. Although anionic and cationic surfactants are disclosed, the patent does not mention amphoteric surfactants.
U.S. Pat. Nos. 6,015,458, 6,039,769, 6,143,068, and 6,153,764 and U.S. application Ser. No. 09/491,493 disclose the preparation of perylene pigments in the presence of certain non-pigmentary cyclic arihydrides and imides. Although anionic, cationic, and non-ionic surfactants are disclosed, amphoteric surfactants are not mentioned.
The treatment of organic pigments with nitrogen-containing surfactants is also known. For example, U.S. Pat. No. 5,662,739 describes a method for improving the dispersibility of quinacridone and dioxazine pigments using certain fatty acid taurides. This patent, however, does not disclose amphoteric surfactants such as used in the present invention. European Patent Application 758,004 describes a method for improving the dispersibility for a specific pigment, Pigment Yellow 12, by carrying out the preparative coupling reaction in the presence of certain cationic and amine oxide surfactants. The European application, however, does not mention other types of pigments. U.S. Pat. No. 5,900,050 describes a method for conditioning organic pigments with nitrogen-containing amphoteric surfactants such as those used in the present invention but does not disclose their inclusion in the pigment-forming process and does not describe their the use in conjunction with cyclic anhydrides and imides.
An object of the present invention was reducing or eliminating the use of strong acids and eliminating further surface treatment steps while at the same time providing organic pigments that can be easily dispersed in plastics. It has now been found that the presence of certain amphoteric surfactants during the conversion of perylene precursors to corresponding perylene pigments and subsequent treatment with certain non-pigmentary cyclic anhydrides and imides provides pigment compositions having improved color properties and dispersability, even in the unfinished form that is initially isolated.
SUMMARY OF THE INVENTION
This invention relates a process for preparing perylene pigment compositions comprising
(a) reacting, at a temperature of less than about 25° C. (preferably from about 0° C. to about 20° C.), a mixture comprising
(1) a perylene tetracarboxylic compound,
(2) at least about 0.1% by weight (preferably 0.1 to 100% by weight, more preferably 2 to 15% by weight), relative to the perylene tetracarboxylic compound, of one or more surfactants of formula (I)
 wherein
R
1
is a straight or branched chain C
8
-C
30
aliphatic group or a modified straight or branched chain C
8
-C
30
aliphatic group in which at least one carbon atom in the main chain of the aliphatic group is replaced with —O—, —S—, —CONH—, —NHCO—, —CH═CH—, —OSi(C
1
-C
4
alkyl)
2
—, or optionally substituted C
5
-C
7
cycloalkylene,
R
2
is hydrogen, C
1
-C
6
alkyl, or —Y—Z′,
R
3
is hydrogen or C
1
-C
6
alkyl, or R
2
and R
3
together are C
4
-C
7
alkylene,
X is a direct bond or —NHC(═NH)—, or X and R
2
taken together with the N
+
form a five- to seven-membered heterocyclic ring,
Y is difunctional C
1
-C
8
(cyclo)aliphatic,
Z is —COO
−
, —SO
3
−
, —PO
3
=
. 1
M
n+
(wherein M
n+
is a hydrogen ion or an n-valent cation), or OH, and
 Z′ is —COO
−
. 1
M
N+
, —SO
3
−
. 1
M
n+
, or —PO
3
=
.2
M
n+
(wherein M
n+
is a hydrogen ion and/or an n-valent cation) or OH, with the proviso that Z′ and Z cannot both be OH,
(3) an equivalent excess, relative to the amount of the perylene tetracarboxylic compound, of 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, and
(4) 0 to about 100 parts by weight, per part by weight of the perylene tetracarboxylic compound, of a solvent (preferably water),
 to form a perylene intermediate;
(b) heating the perylene intermediate at a temperature of about 50° C. to about 250° C. (preferably from about 120° C. to about 150° C.) in the presence of
(1) 0 to about 20% by weight (preferably 5 to 15% by weight), relative to the perylene intermediate, of a non-pigmentary cyclic anhydride or imide having the formula (II)
 wherein
W is O or NR
4
,
R
4
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
5
, R
6
, and R
7
are independently hydrogen, C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl, or R
5
and R
6
together are fused-on rings (preferably fused-on cycloalkane or aromatic rings) and R
7
is hydrogen, C
1
-C
6
alkyl, C
7
-C
16
aralkyl, or C
6
-C
10
aryl, or R
5
, R
6
, and R
7
together are fused-on rings (preferably fused-on cycloalkane or aromatic rings),
the dotted line is an optional double bond representing R
5
—C═C—R
6
or R
6
—C═C—R
7
(including a formal double bond of any fused-on aromatic ring formed by R
5
and R
6
taken together or by R
5
, R
6
, and R
7
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 cat

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