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United States Patent 19 11 Patent Number: 5,683,502 Badejo Et Al

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United States Patent 19 11 Patent Number: 5,683,502 Badejo Et Al US005683.502A United States Patent 19 11 Patent Number: 5,683,502 Badejo et al. 45 Date of Patent: Nov. 4, 1997 54 NCORPORATION OF AROMATIC Attorney Agent, or Firm-Joseph C. Gil; Richard E. L. POLYCYCLC COMPOUNDS IN Henderson QUINACREDONE PROCESSES 57 ABSTRACT 75 Inventors: Ibraheem T. Badejo, N. Charleston; Daphne J. Rice, Charleston, both of This invention relates to a process for the preparation of S.C. quinacridone pigments by 73) Assignee: Bayer Corporation, Pittsburgh, Pa. (a) heating, at a temperature of about 80° C. to about 145° C., a reaction mixture containing (21 Appl. No.: 639,599 (i) 2.5-dianilinoterephthalic acid, a 2,5-dianilino-3,6- 22 Filled: Apr. 29, 1996 dihydroterephthalic acid ester, and/or a derivative thereof, (51) Int. Cla. CO9B 48/06; CO9B 67/52 (ii) about 3 to about 15 parts by weight, per part of 52 U.S. C. ............................ 106495; 106/497; 546/49; component (a)(i), of a dehydrating agent, and 54.6/56 (iii) about 0.1 to about 15 percent by weight, based on 58) Field of Search ..................................... 106/495, 497; component (a)(i), of one or more non-pigmentary aro 546/49, 56 matic polycyclic compounds and/or derivatives 56 References Cited thereof, with the proviso that if component (a)(i) is a 2,5-dianilino U.S. PATENT DOCUMENTS 3,6-dihydroterephthalic acid ester or a derivative thereof, 3,157,659 11/1964 Deuschel et al. ..................... 546/56 reaction step (a) additionally comprises an oxidation step; 3,256,285 6/1966 Fuchs et al. ........................... 54.628 3,257,405 6/1966 Gerson et al. ........................... 546/29 3,317,539 5/1967 Jaffe .............. 54657 (b) drowning the reaction mixture from step (a) by adding 4,317,682 3/1982 Katsura et al. ... 106,496 said reaction mixture to about 3 to about 15 parts by weight, 4,455,173 6/1984 Jaffe ................. 106,495 per part of component (a)(i), of a liquid in which the 4,810,304 3/1989 Jaffe et al. ... 106,495 quinacridone pigment is substantially insoluble; 5,084,100 1/1992 Bauman ...... 106,495 5,236,498 8/1993 Zaloum et al. ... ... 10649. (c) isolating the quinacridone pigment; 5,368,641 11/1994 Dietz et al. ... ... 106,495 5,457,203 10/1995 Hendi et al. ... 546/56 5,472.496 12/1995 Hendi et al. ............................ 106,497 (d) optionally, conditioning the quinacridone pigment; and OTHER PUBLICATIONS (e) optionally, blending the resultant pigment with one or S.S. Labana and L.L. Labana, "Quinacridones" in Chemical more quinacridone derivatives. Review, 67, 1-18 Jan. 25, 1967. Primary Examiner Mark L. Bell Assistant Examiner-Scott Hertzog 15 Claims, No Drawings 5,683,502 1. 2 NCORPORATION OFAROMATC size growth inhibitor. U.S. Pat. No. 5,084.100 discloses a POLYCYCLC COMPOUNDS IN method in which crude quinacridone is ball milled in the QUINACRIDONE PROCESSES presence of aluminum sulfate and esters of alkanedicarboxy lic acids. BACKGROUND OF THE INVENTION The addition of certain quinacridone derivatives to the This invention relates to a process for the preparation of ring-closure step has also been reported. For example, U.S. quinacridone pigments having reduced particle size, Pat. No. 5.368,641 discloses the use of various quinacridone improved coloristic properties, and improved rheological derivatives in the manufacture of 2,9-dimethylquinacridone. properties. The addition of certain aromatic polycyclic com The present invention, in contrast, uses classes of certain pounds and/or their derivatives during quinacridone synthe O aromatic polycyclic compounds rather than quinacridones in sis provides quinacridone pigments having deeper, brighter, the ring-closure step. European Patent Application 643, 110 and more transparent masstones, increased metallic (counterpart of U.S. Pat. No. 5,457.203) describes the use of brightness, and improved theological properties. quinacridone derivatives during the oxidation of dihydro Processes for the preparation of quinacridone are known. quinacridone (prepared from 2,5-dianilino-3,6- E.g., S. S. Labana and L. L. Labana, "Quinacridones" in 15 dihydroterephthalic acid) to quinacridone. The present Chemical Review, 67, 1-18 (1967), and U.S. Pat. Nos. invention, in contrast, not only uses aromatic polycyclic 3,157.659, 3,256.285, and 3,317.539. The quinacridones compounds other than quinacridones as additives but also thus obtained, known as crude quinacridones, are generally uses the additives in the ring-closure step. unsuitable for use as pigments and must undergo one or Compounds suitable for the present invention have been more additional finishing steps to modify the particle size, described as useful for treating various pigments, including particle shape, or crystal structure to achieve pigmentary quinacridones (e.g., British Patent 2,058,813), but such quality. derivatives have previously been added only to fully formed A preferred method for preparing quinacridones involves quinacridone pigments. The present invention differs from thermally inducing ring closure of 2,5-dianilinoterephthalic such methods in that non-pigmentary aromatic polycyclic acid intermediates, as well as known aniline-substituted 25 compounds are added during the ring-closure step of quina derivatives thereof, in the presence of polyphosphoric acid. cridone synthesis. When added to the ring-closure step, and E.g., U.S. Pat. No. 3.257,405. Afterring closure is complete, optionally also during the finishing step, such compounds the melt is drowned by pouring into a liquid in which the can provide quinacridone pigments having desirable color quinacridone is substantially insoluble, usually water and/or istic properties that are particularly desirable for automotive an alcohol. The resultant crystalline pigment is then further 30 finishes, conditioned by solvent treatment or milling in combination The present invention provides smaller particle size with solvent treatment. quinacridones having improved performance properties by It is also possible to use 2,5-dianilino-3,6- the addition of certain aromatic polycyclic compounds and/ dihydroterephthalic acid as a starting material in the ring or their derivatives to the ring-closure step of the quinacri closure reaction. The resultant dihydroquinacridone must, 35 done synthesis, and optionally also to the subsequent con however, be oxidized and then conditioned, ditioning steps. The addition of such compounds during Final particle size of quinacridone pigments can be con quinacridone synthesis (i.e., ring-closure) before precipita trolled by the methods used in both synthesis and aftertreat tion results in a deeper, brighter pigment having improved ment. For example, quinacridone pigments can be made transparency and rheological properties, as well as brighter more transparent by reducing the particle size or more metallics. The process of the invention is in principle opaque by increasing the particle size. In known methods, applicable to all quinacridone pigment manufacturing pro particle size is generally controlled during precipitation of cesses that include an "acid pasting" step, but the greatest the pigment by drowning or during milling or solvent improvement in coloristic properties is expected for ring closure processes, including processes used to prepare treatment of the crude pigment. Tinctorial strength and 45 transparency of pigments can also be affected by solvent quinacridone solid solutions. treatment. Aftertreatment steps that manipulate the crude pigments particle size are often referred to as conditioning SUMMARY OF THE INVENTON methods. This invention relates to a process for the preparation of quinacridone pigments comprising Several suitable conditioning methods are known. 50 However, the most commonly used methods involve milling (a) heating, at a temperature of about 80° C. to about 145° the dried crude quinacridone, generally in the presence of C. (preferably 100° C. to 130° C) (preferably for about undesirably large amounts of an inorganic salt that must one to about 24 hours), a reaction mixture comprising Subsequently be removed. Pigmentary quinacridones can (i) 2,5-dianilinoterephthalic acid, a 2,5-dianilino-3,6- also be obtained by first premilling the dried crude material 55 dihydroterephthalic acid ester, a derivative of 2.5- and then treating the milled material with an organic liquid. dianilinoterephthalic acid or a 2.5-dianilino-3,6- Other methods involve a premilling step followed by dihydroterephthalic acid ester having one or more another milling step using water and small amounts of an substituents in at least one aniline ring, or a mixture organic liquid. Pigmentary quinacridones can also be thereof, obtained by heat treatment of crude presscake in large 60 (ii) about 3 to about 15 parts by weight (preferably 3 to 10 quantities of solvent. Various additives have been added parts by weight), per part of component (a)(i), of a during the milling, solvent treatment, or post-solvent treat dehydrating agent (preferably polyphosphoric acid), ment steps to further improve pigment properties. For and example, U.S. Pat No. 4,455.173 discloses a process in (iii) about 0.5 to about 15 percent by weight (preferably which crude quinacridone pigments are acid pasted or ball 65 1 to 10 percent by weight), based on component (a)(i), milled and then milled in an organic liquid, preferably in the of one or more non-pigmentary (preferably colorless or presence of a 2-phthalimidomethylquinacridone particle substantially colorless) aromatic polycyclic com 5,683,502 3 4 pounds and/or derivatives thereof
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