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(12) United States Patent (10) Patent No.: US 6,562,121 B2 Nickel Et Al

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(12) United States Patent (10) Patent No.: US 6,562,121 B2 Nickel Et Al USOO6562121B2 (12) United States Patent (10) Patent No.: US 6,562,121 B2 Nickel et al. (45) Date of Patent: *May 13, 2003 (54) CONDITIONING OF ORGANIC PIGMENTS 5,110,931 A 5/1992 Dietz et al. ................... 546/37 5,492,564 A 2/1996 Wooden et al. ............. 106/493 (75) Inventors: UWe Nickel, Bad Homburg (DE); 5,534,328 A 7/1996 Ashmead et al. ........... 428/166 Klaus Kund, Langenscheid (DE); 5,591.258 A 1/1997 Urban et al. ................ 106/497 5,755,874. A 5/1998 Urban et al. ................ 106/497 ESSE SPE Maim 5,811,062 A 9/1998 Wegeng et al. ............. 422/129 (DE); Olaf Schupp,s Frankfurt am Main 5,910,577 A 6/1999 Metz et al. ................. 534/742 (DE) FOREIGN PATENT DOCUMENTS (73) Assignee: Clariant Finance (BVI) Limited, DE 1261 106 9/1968 Tortola (VG) DE 39 26 466 2/1991 EP O O77 O25 4/1983 (*) Notice: Subject to any disclaimer, the term of this EP O 318 O22 5/1989 patent is extended or adjusted under 35 EP O 655 485 5/1995 EP O 672 729 9/1995 U.S.C. 154(b) by 0 days. EP O 799 863 10/1997 EP O894 831 2/1999 This patent is Subject to a terminal dis EP 1162 240 * 12/2001 claimer. EP 1 167461 * 1/2002 (21) Appl. No.: 09/892,588 OTHER PUBLICATIONS (22) Filed: Jun. 27, 2001 Derwent Abstract of DE 3926466 (Feb./1991). (65) Prior Publication Data Derwent Abstract of EP 0 077 025 (Apr./8193). US 2002/0014179 A1 Feb. 7, 2002 Derwent Abstract of EP 0 894831 (Feb./1999). (30) Foreign Application Priority Data Derwent Abstract of EP 0 799863 (Oct./1997). Jun. 28, 2000 (DE) ......................................... 1OO 31558 Derwent Abstract of EP 0 655 485 (May/1995). (51) Int. Cl. ................................................ C09B 67/00 Derwent Abstract of EP 0 672 729 (Sep/1995). (52) U.S. Cl. ....................... 106/493; 106/412; 106/413; Derwent Abstract of EPO 318 0225 (May/1989). 106/494; 106/495; 106/497; 106/498; 106/496; Derwent Abstract of DE 1261 106 (Sep/1968). 534/588; 540/122; 544/249; 544/339; 54.6/37; 546/49; 546/56; 548/306.4; 548/453: 548/457; * cited by examiner 548/482; 552/208; 552/276; 552/282; 552/284; 585/25 Primary Examiner Anthony J. Green (58) Field of Search ................................. 106/412, 413, (74) Attorney, Agent, or Firm- Anthony A. Bisulca 106/493, 494, 495, 496, 497, 498; 534/588; 540/122; 544/339, 245; 54.6/37, 49,56; (57) ABSTRACT 548/306.4, 453 Organic pigments are conditioned by introducing a liquid (56) References Cited prepigment Suspension into a miniaturized continuous reac tor and thermally treating therein. U.S. PATENT DOCUMENTS 4906,735 A 3/1990 Hunger ....................... 534/575 15 Claims, 1 Drawing Sheet U.S. Patent May 13, 2003 US 6,562,121 B2 US 6,562,121 B2 1 2 CONDITIONING OF ORGANIC PGMENTS It is known to carry out certain chemical reactions in microreactors. Micro-reactors are constructed from Stacks of grooved plates and are described in DE 39 26 466 C2 and BACKGROUND OF THE INVENTION U.S. Pat. No. 5,534,328. It is pointed out in U.S. Pat. No. 5 5,811,062 that microchannel reactors are preferably used for The present invention describes a process for conditioning reactions that do not require or produce materials or Solids organic pigments in microreactors. that would clog the microchannels. Organic pigments are well known and widely used for pigmenting macro-molecular organic materials. Such as SUMMARY OF THE INVENTION paints, plastics or printing inkS. ASSynthesized, they are usually either very fine prepigments or coarse crude It has now been found, that, Surprisingly, microreactors pigments, which do not meet industrial requirements. Finely are useful for conditioning organic pigments by thermal divided prepigments frequently have to be Subjected to a treatment of their prepigment Suspensions. thermal treatment to obtain the required properties. Coarsely AS used herein, the term “microreactor” is representative divided crude pigments are frequently Subjected to 15 of miniaturized, preferably continuous, reactors which are comminution, which usually has to be followed by thermal known under the terms of microreactor, minireactor, micro treatment in order that pigments meeting the industrial mixer or minimixer and which differ by reason of the requirements may be obtained. dimensions and construction of the channel Structures. It is The thermal treatment may produce various desired possible to use, for example, microreactors as known from effects, for example narrow the particle Size distribution; the cited references or from publications of the Institut fucr shift the average particle size to higher values, deagglom Mikrotechnik Mainz GmbH, Germany, or of the Fraunhofer erate as-ground comminuted and Strongly agglomerated Institut für Chemische Technologie, Pfinztal, or else com pigments, add auxiliaries and distribute them homoge mercially available microreactors, for example Selecto TM neously over the pigment Surface; and effect a change (based on CytosTM) from Cellular Process Chemistry between various crystal forms in Some cases. These effects 25 GmbH, Frankfurt/Main. then lead to the desired industrial requirements, for example The invention accordingly provides a proceSS for condi the desired hue, increased color Strength or cleanneSS of hue, tioning organic pigments, which comprises thermally treat improved dispersibility, rheology, lightfastness, gloSS or ing a liquid prepigment Suspension in a microreactor. weatherfastness, or control over light Scattering properties Advantageously, the prepigment Suspension is fed to the and hence over the hiding power. microreactor continuously. The conventional Sequence of Literature discloses thermal treatment processes for a adding prepigment Suspension, Water, organic Solvents, wide variety of organic pigments: acids and/or bases can be realized; Similarly, the auxiliaries DE-A-12 61 106 discloses a batch process for thermal used in conventional processes may likewise be used in the treatment of Substituted quinacridone pigments by heating process of the invention. the crude pigments in Solvents under pressure. 35 Useful organic pigments include, for example perylene, EP-A-0318022 discloses a batch process for producing pe rinone, quin a cridone, quin a cridone quinone, a hiding dimethyl-perylimide pigment where the hiding anthraquinone, anthanthrone, benzimidazolone, disaZo power is provided by thermal treatment. condensation, a Zo, indanthrone, phthalocyanine, EP-A-0 672 729 discloses a batch process for producing triarylcarbonium, dioxazine, aminoanthraquinone, a hiding diketopyrrolo-pyrrole pigment where the hiding 40 diketopyrrolopyrrole, thioindigo, thia Zine indigo, power is provided by thermal treatment. isolindoline, isoindolinone, pyranthrone or isoViolanthrone EP-A-0 655 485 and EP-A-0 799 863 disclose batch pigments or mixtures thereof. processes for producing quinacridone pigments where the DESCRIPTION OF THE DRAWINGS transformation from the alpha-phase to the beta-phase is 45 effected by thermal treatment with an organic Solvent and in FIG. 1 is an exploded view of a microreactor useful for the the presence of aqueous alkali. preparation of organic pigments by thermal treatment, Batch processes are known for producing an azo pigment according to the present invention. where a thermal treatment is carried out in an aqueous DESCRIPTION OF THE PREFERRED medium (EP-A-0 077 025) or in organic solvents 50 (EP-A-0 894831). EMBODIMENTS A feature common to these batch processes is the need to Preferred organic pigments for the purposes of the present control the process parameters. For example, temperature invention include for example C.I. Pigment Red 123 (C.I. and duration of the thermal treatment, Suspension No. 71145), C.I. Pigment Red 149 (C.I. No. 71137), C.I. concentration, use of Solvents or presence of acids or bases 55 Pigment Red 178 (C.I. No. 71155), C.I. Pigment Red 179 are decisive for the color properties of the pigments obtained (C.I. No. 71130), C.I. Pigment Red 190 (C.I. 71140), C.I. and their quality constancy. Moreover, the Scaleup of new Pigment Red 224 (C.I. No. 71127), C.I. Pigment Violet 29 products from the laboratory Scale to the large industrial (C.I. No. 71129), C.I. Pigment Orange 43 (C.I. No. 71 105), Scale is inconvenient with batch processes and can present C.I. Pigment Red 194 (C.I. No. 71 100), C.I. Pigment Violet problems, Since for example vessel and Stirrer geometries or 60 19 (C.I. No. 73 900), C.I. Pigment Red 122 (C.I. No. 73 heat transferS have a Substantial effect on particle Size, 915), C.I. Pigment Red 192, C.I. Pigment Red 202 (C.I. No. particle size distribution and color properties. 73907), C.I. Pigment Red 207, C.I. Pigment Red 209 (C.I. It is an object of the present invention to provide an No. 73905), C.I. Pigment Red 206 (C.I. No. 73 900/73 920), environmentally friendly, economical and technically reli C.I. Pigment Orange 48 (C.I. No. 73 900/73 920), C.I. able process for preparing organic pigments by thermal 65 Pigment Orange 49 (C.I. No. 73 900/73 920), C.I. Pigment treatment that provides very constant adherence to the Orange 42, C.I. Pigment Yellow 147, C.I. Pigment Red 168 desired process parameters and Simplifies Scaleup. (C.I. No. 59300), C.I. Pigment Yellow 120 (C.I. No. 11 US 6,562,121 B2 3 4 783), C.I. Pigment Yellow 151 (C.I. No. 13 980), C.I. phenol; aromatic heterocycles, Such as pyridine, Pigment Brown 25 (C.I. No. 12510), C.I. Pigment Violet 32 morpholine, picoline or quinoline; and also dimethyl Sul (C.I. No. 12 517), C.I. Pigment Orange 64; C.I. Pigment foxide and Sulfolane.
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