Patent ID: 6403797
Filing Date: 2002-06-11
Classification: C09B

Abstract:
A process for preparing perylene pigment compositions comprising(a) reacting, at a temperature of less than about 25Â° C., a mixture comprising (1) a perylene tetracarboxylic compound, (2) at least about 0.1% by weight, relative to the perylene tetracarboxylic compound, of one or more surfactants of formula (I) â€ƒwherein R1 is a straight or branched chain C8-C30 aliphatic group or a modified straight or branched chain C8-C30 aliphatic group in which at least one carbon atom in the main chain of the aliphatic group is replaced with â€”Oâ€”, â€”Sâ€”, â€”CONHâ€”, â€”NHCOâ€”, â€”CH&boxH;CHâ€”, â€”OSi(C1-C4 alkyl)2â€”, or optionally substituted C5-C7 cycloalkylene, R2 is hydrogen, C1-C6 alkyl, or â€”Yâ€”Zâ€², R3 is hydrogen or C1-C6 alkyl, or R2 and R3 together are C4-C7 alkylene, X is a direct bond or â€”NHC(&boxH;NH)â€”, or X and R2 taken together with the N+ form a five- to seven-membered heterocyclic ring, Y is difunctional C1-C8 (cyclo)aliphatic, Z is â€”COOâˆ’, â€”SO3âˆ’, â€”PO3=.1/n Mn+ (wherein Mn+ is a hydrogen ion or an n-valent cation), or OH, and Zâ€² is â€”COOâˆ’.1/n Mn+, â€”SO3âˆ’.1/n Mn+, or â€”PO3=.2/n Mn+(wherein Mn+ is a hydrogen ion and/or an n-valent cation) or OH, with the proviso that Zâ€² 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 RAâ€”NH2, wherein RA is C1-C6 alkyl, C7-C16 aralkyl, or C6-C10 aryl, and (4) 0 to about 100 parts by weight, per part by weight of the perylene tetracarboxylic compound, of a solvent, to form a perylene intermediate; (b) heating the perylene intermediate at a temperature of about 50Â° C. to about 250Â° C. in the presence of (1) 0 to about 20% by weight, relative to the perylene intermediate, of a non-pigmentary cyclic anhydride or imide having the formula (II) â€ƒwherein W is O or NR4, R4 is hydrogen, a metal, C1-C6 alkyl, C5-C8 cycloalkyl, C7-C16 aralkyl, C6-C10 aryl, or â€”Alkâ€”X, R5, R6, and R7 are independently hydrogen, C1-C6 alkyl, C7-C16 aralkyl, or C8-C10 aryl, or R5 and R6 together are fused-on rings and R7 is hydrogen, C1-C6 alkyl, C7-C16 aralkyl, or C6-C10 aryl, or R5, R6, and R7 together are fused-on rings, the dotted line is an optional double bond representing R5â€”C&boxH;Câ€”R6 or R6â€”C&boxH;Câ€”R7, Alk is C1-C18 alkylene or C5-C8 cycloalkylene, and X is (i) an anionic group selected from â€”SO3âˆ’, â€”COOâˆ’, â€”PO3=, â€”PO(ORx)Oâˆ’ (wherein Rx is C1-C6 alkyl), â€”Oâ€”PO3=, and â€”Oâ€”PO(ORy)Oâˆ’ (wherein Ry is C1-C6 alkyl), each such anionic group being electrically balanced with a stoichiometric amount of a cation, (ii) a cationic group having the formula â€”NRaRbRc+ (wherein Ra, Rb, and Rc, are independently hydrogen, C1-C6 alkyl, C7-C16 aralkyl, or C6-C10 aryl), each such cationic group being electrically balanced with a stoichiometric amount of an anion, (iii) NRdRe, wherein Rd is hydrogen, C1-C6 alkyl, C7-C16 aralkyl, C6-C10 aryl, C2-C6 alkanoyl, C7-C11 aroyl, or sulfonyl and Re is hydrogen, C1-C6 alkyl, C7-C16 aralkyl, or C6-C10 aryl, (iv) ORf, wherein Rf is hydrogen, C1-C6 alkyl, or C6-C10 aryl, (v) COORg, wherein Rg is C1-C6 alkyl, C7-C16 aralkyl, or C6-C10 aryl, (vi) sulfonyl, or (vii) C6-C10 aryl; and (2) 0 to about 30% by weight, relative to the perylene intermediate, of a solvent, â€ƒthereby forming the perylene pigment composition; and (c) collecting the perylene pigment composition.