N,N'-dimethylperylene-3,4,9,10-tetracarboxylic acid diimide pigm

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Details

106493, 546 37, C09B 6722, C09B 6708, C09B 562, C09D 502

Patent

active

060996366

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a novel N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide pigment which is suitable for aqueous basecoats and which is obtainable by coating the diimide, suspended in an aqueous medium, with a carboxyl-carrying resin in the presence of 3,4-dicarboximidoperylene-9-sulfonic acid or salts thereof and with a C.sub.8 -C.sub.18 -alkyl- or -alkenylamine, isolating and drying the coated diimide and then subjecting it to dry milling.
The invention additionally relates to the preparation of this pigment and to its use for pigmenting aqueous basecoats, and to aqueous basecoats comprising this pigment.
It is known that N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide (C.I. Pigment Red 179) is obtained in the synthesis in a form which when incorporated directly into coating systems or other high molecular mass organic systems leads to poor rheological properties and to unsatisfactory color properties of the pigmented systems. Additional treatment of the pigment is therefore carried out in an attempt to improve its performance properties.
For instance, DE-A-25 04 481 describes a process for preparing transparent C.I. Pigment Red 179 of good color strength where, during the synthesis if the diimide from perylene-3,4,9,10-tetracarboxylic dianhydride and aqueous methylamine, for completion of the reaction by heating a resin acid is added which is washed off again when the pigment is isolated or is precipitated as an alkaline earth metal salt onto the pigment.
DE-A-43 25 247 discloses the use of 3,4-dicarboximidoperylene-9-sulfonic or carboxylic acids and salts thereof as a pigment additive for C.I. Pigment Red 179, in which it is also possible in addition to employ polymers with polar anchor groups, such as polymers based on ethylene oxide and propylene oxide adducts with 2-(diethyl)-aminoethanol or block copolymers of polyethyleneimine and 6-caprolactone. The coating of the pigment with additive and, if desired, polymer is accomplished by stirring an aqueous suspension of the diimide, isolated in the course of synthesis as a water-moist filter cake, and of the coating agents and then carrying out heating, or by triturating or grinding the previously dried diimide with the coating agents in the presence or absence of water. C.I. Pigment Red 179 coated in this way indeed shows a marked improvement in rheology and color properties (bright, yellowish red, transparent colorations) when compared with the uncoated pigment, but no description is given of a pigment which can be employed specifically in aqueous basecoats.
It is therefore an object of the present invention to provide a N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide which is suitable for aqueous basecoats and has advantageous performance properties.
We have found that this object is achieved by a N,N'-dimethyl-perylene-3,4,9,10-tetracarboxylic diimide pigment which is suitable for aqueous basecoats and which is obtainable by coating the diimide, suspended in an aqueous medium, with a carboxyl-carrying resin in the presence of 3,4-dicarboximidoperylene-9-sulfonic acid or salts thereof and with a C.sub.8 -C.sub.18 -alkyl- or -alkenylamine, isolating and drying the coated diimide and then subjecting it to dry milling.
We have also found the process defined hereby for preparing the N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide pigment.
We have also discovered the use of this pigment for pigmenting aqueous basecoats.
The novel N,N'-dimethylperylene-3,4,9,10-tetracarboxylic diimide pigment can advantageously be obtained by the process according to the invention, in which the diimide, suspended in as fine a state of division as possible in an aqueous medium, is coated with a carboxyl-carrying resin, with 3,4-dicarboximidoperylene-9-sulfonic acid or salts thereof and with a C.sub.8 -C.sub.18 -alkyl- or -alkenylamine, or with the reaction products of these substances, and the diimide coated in this way is subjected, following its isolation, to dry milling.
Particularly suitable carboxyl-carrying resins are natural a

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