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Process for Isolation of Monophenolic-Bisaryl Triazines

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Process for Isolation of Monophenolic-Bisaryl Triazines (19) TZZ ¥¥_T (11) EP 2 835 368 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 11.02.2015 Bulletin 2015/07 C07D 251/24 (2006.01) (21) Application number: 14187901.5 (22) Date of filing: 21.05.2002 (84) Designated Contracting States: • SINGH, Hargurpreet AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU SEYMOUR, CT Connecticut 06483 (US) MC NL PT SE TR • CAPPADONA, Russell, C. NORWALK, CT Connecticut 06851 (US) (30) Priority: 22.06.2001 US 887128 (74) Representative: Deckers, Hellmuth Alexander (62) Document number(s) of the earlier application(s) in European Patent Attorney accordance with Art. 76 EPC: Breitbachstrasse 15 10184470.2 / 2 289 884 55218 Ingelheim am Rhein (DE) 02726905.9 / 1 397 352 Remarks: (71) Applicant: CYTEC TECHNOLOGY CORP. This application was filed on 07-10-2014 as a Wilmington, Delaware 19801 (US) divisional application to the application mentioned under INID code 62. (72) Inventors: • GUPTA, Ram, B. STAMFORD, CT Connecticut 06902 (US) (54) Process for Isolation of Monophenolic-Bisaryl Triazines (57) This invention relates to a novel, efficient, eco- ing the monophenolic- bisaryl triazinecompounds by con- nomic and general-purpose process for isolating tacting it with an organic base, or with an organic base, monophenolic-bisaryl triazine compounds from polyphe- and at least one component selected from the group con- nolic-triazines compounds and other impurities. More sisting of an alcohol and a hydrocarbon solvent. specifically, this invention relates to a process for isolat- EP 2 835 368 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 835 368 A1 Description FIELD OF THE INVENTION 5 [0001] This invention relates to a novel, efficient, economic and general-purpose process for isolating monophenolic- bisaryl triazine compounds from polyphenolic-triazines compounds and other impurities. More specifically, this invention relates to a process for isolating the monophenolic-bisaryl triazine compounds by contacting it with a base, an alcohol and/or a hydrocarbon solvent. 10 BACKGROUND OF THE INVENTION [0002] Exposure to sunlight and other sources of ultraviolet (UV) radiation is known to cause degradation of a wide variety of materials, especially polymeric materials. For example, polymeric materials such as plastics often discolor and/or become brittle as a result of prolonged exposure to UV light. Accordingly, a large body of art has been developed 15 directed towards materials such as UV light absorbers and stabilizers which are capable of inhibiting such degradation. Other areas of applications for the UV light absorbers include cosmetics (as sunscreen agents), fibers, spandex, inks, photographic materials, and dyes. [0003] A class of materials known to be UV light absorbers are compounds which have aromatic substituents at the 2-, 4-, and 6- positions of the 1,3,5-triazine ring, and in which at least one of the aromatic rings has a hydroxyl substituent 20 at the ortho position to the point of attachment to the triazine ring. In general, this class of compounds is well known in the art. Disclosures of a number of such triazine UV light absorbers (UVA’s) as well as processes for preparing can be found in the following references and references cited therein, all of which are incorporated by reference as fully set forth herein: U.S. Patent No. 6,239,275; U.S. Patent No. 6, 239,276; U.S. Patent No. 6,242,597; U.S. Patent No. 6,225,468 and WO 00/29392. 25 [0004] A preferred class of triazine UVA’s are asymmetrical monophenolic-bisaryl triazines UVA’s based on the 2-(2,4- dihydroxyaryl)-4,6-bisaryl-1,3,5-triazines, e.g., compounds where there are two non-phenolic aromatic groups, and one phenolic aromatic group that is derived from resorcinol, or substituted resorcinol. The 4-hydroxyl group of the parent compound, 2-(2,4-dihydroxyaryl)-4,6-bisaryl-1,3,5-triazine, is generally functionalized to make 2-(2-hydroxy-4-oxyaryl)- 4,6-bisaryl-1,3,5-triazine derivatives for end use. 30 35 40 [0005] There are several approaches reported in the literature to make the preferred 2-(2,4-dihydroxyaryl)-4,6-bisaryl- 1,3,5-triazine UVA’s. (For a review of the previously known methods for making triazine UVA’s, please see the following articles: 1. H. Brunetti and C. E. Luethi, Helvetica Chimica Acta, vol 55, 1972, pages 1566-1595; 2. S. Tanimoto and M. 45 Yamagata, Senryo to Yakahin, vol. 40(12), 1995, pages 325-339.) [0006] A majority of the approaches consists of three stages. The first stage, which can involve single or multi-steps from the commercial raw materials, deals with the preparation of the key intermediate, 2-chloro-4,6-bisaryl-1,3,5-triazine, which is subsequently arylated in the second stage with 1,3-dihydroxybenzene (resorcinol) or a substituted 1,3-dihy- droxybenzene in the presence of Lewis acid to form the parent compound 2-(2,4-dihydroxyaryl)-4,6-bisaryl-1,3,5-triazine. 50 The parent compound 2-(2,4-dihydroxyaryl)-4,6-bisaryl-1,3,5-triazine, as mentioned above, is generally functionalized further, e.g., alkylated, to make the final product 2-(2-hydroxy-4-oxyaryl)-4,6-bisaryl-1,3,5-triazine. 55 2 EP 2 835 368 A1 5 10 15 20 25 30 35 40 45 [0007] It has been recognized that the most versatile and economical method to prepare asymmetrical monophenolic- bisaryl triazine UVA’s is to use a Friedel-Crafts reaction on cyanuric chloride with non-phenolic aromatics to first form 2-chloro-4,6-bisaryl-1,3,5-triazine, followed by another Friedel-Crafts reaction with the phenolic aromatic, in this case resorcinol, to make the desired monophenolic-bisaryl-triazine. However, it has been realized in the prior art (see, U.S. Patent No. 3,394,134) that this known process as disclosed in U.S. Patent No. 3,268,474 gives, only in exceptional 50 cases, rise to the desired disubstituted derivatives of cyanuric chloride with some selectivity. Even when the aromatic compound and cyanuric chloride are reacted in molar proportions (1:1), the result is in general a mixture which contains mono-, di-, and tri-aryl substituted products, and, in addition, unreacted cyanuric chloride (U.S. Patent No. 3,394,134) (Scheme 1). 55 3 EP 2 835 368 A1 5 10 15 [0008] Using the above mentioned process, a useful yield of the desired intermediate 2-chloro-4,6-bisaryl-1,3,5-triazine is obtained only with m-xylene as the aromatic reactant (GB 884802). 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphe- 20 nyl)-1,3,5-triazine, free of polyresorcinol-triazine impurities, was prepared from the isolated 2-chloro-4,6-bis(2,4-dimeth- ylphenyl)-1,3,5-triazine that was purified by recrystallization, before reacting with resorcinol in a second step (see U.S. Patent No. 3,244,708). The isolation and recrystallization of the 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine re- sults in yield loss. With other aromatics, a difficult to separate mixture of all possible products are formed with no selectiv ity for the desired 2-chloro-4,6-bisaryl-1,3,5-triazine (For example, see H. Brunetti and C. E. Luethi, Helvetica Chimica Acta, 25 vol 55, 1972, page 1575 and S. Tanimoto and M. Yamagata, Senryo to Yakahin, vol. 40(12), 1995, pages 325-339). [0009] When the reaction mixture from the first Friedel-Crafts reaction (Scheme 1) without any purification is treated in a subsequent Friedel-Crafts reaction with resorcinol, the bisaryl- derivative leads to the formation of desired monore- sorcinol-bisaryl-triazine, and the monoaryl-substituted product leads to the formation of monoaryl-bisresorcinol derivative. Whereas, the unreacted cyanuric chloride leads to the formation of bis-and tris-resorcinol-triazine derivatives, i.e. polyr- 30 esorcinol-triazines (see Scheme 2). 35 40 45 50 55 4 EP 2 835 368 A1 5 10 15 20 25 30 35 40 45 50 [0010] These polyresorcinol-triazine impurities (triazine ring with more than one resorcinol attached) lead to yellowing in the use of the UV absorbers prepared from the monoresorcinol-bisaryl-triazine in various polymer substrates, e.g., in polycarbonates, in lacquers, in automotive top-coatings, etc. Thus it is highly desirable for many such applications that the monoresorcinol-bisaryl-triazine derivative is free of these impurities. Unfortunately, there has been no process known 55 in the literature to isolate monoresorcinol-bisaryl-triazine derivative from the mixture containing polyresorcinol impurities. The lack of selectivity for the bisaryl substitution in the Friedel-Crafts reaction of cyanuric chloride, coupled with the problems associated with the isolation of the bisaryl intermediate and the monoresorcinol-bisaryl-triazine derivative, had severely limited the usefulness of the most versatile and economic approach to the preferred class of triazine UVA’s. 5 EP 2 835 368 A1 [0011] To overcome this obstacle, and to exclude the formation of polyresorcinol-triazines, other economically less attractive routes have been developed in which either cyanuric chloride was not used as starting material, and the triazine ring was synthesized by different methods, or the formation of polyresorcinol impurities was excluded by means of the circuitous routes (For example, see: A. Ostrogovich, Chemiker-Zeitung No. 78, page 738, 1912; von R. Hirt, H. Nidecker 5 and R. Berchtold, Helvitica Chimica Acta, vol. 33, page 1365, 1950; H. Brunetti and C. E. Luethi, Helvetica Chimica Acta, vol 55, 1972, page 1575; U.S. Patent No. 4,092,466; U.S. Patent No. 5,084,570; U.S. Patent No.
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