Abstract
Carboxy- and carbomethoxy derivatives of resorcinols with two benzotriazole substituents have been synthesized. 2(2,4-Dihydroxyphenyl)2H-1,3-bis-(4-carboxybenzotriazole) [2,4-bis(2H-4′-carboxybenzotriazole-2-yl)-1,3-dihydroxybenzene] (DCBDH) was prepared by azo coupling of 4-carboxy-2-nitrobenzene diazonium chloride with resorcinol followed by reductive cyclization. 2(2,4-Dihydroxyphenyl)2H-1,3-bis(4-carbomethoxy-benzotriazole) [2,4-bis-(2H-4′-carbomethoxy-benzotriazole-2-yl)-1,3-dihydroxybenzene] (DCMBDH) was obtained by esterification of the free dicarboxylic acid with methanol. The compounds were characterized by their elemental analyses and melting points, and by their IR, UV,1H NMR, and13C NMR spectra.
Copolycondensations were carried out to incorporateDCBDH orDCMBDH into polyamides or polyesters. The condensation copolymers were briefly characterized.
Zusammenfassung
Es wurden Carboxy- und Carbomethoxy-Derivate von Resorcin mit zwei Benzotriazol-Substituenten dargestellt. 2(2,4-Dihydroxyphenyl)2H-1,3-bis-(4-carboxybenzotriazol) [2,4-Bis(2H-4′-carboxybenzotriazol-2-yl)-1,3-dihydroxybenzol] (DCBDH) wurde über Azokupplung von 4-Carboxy-2-nitrobenzol-diazoniumchlorid mit Resorcin, gefolgt von reduktiver Cyclisierung, synthetisiert. 2(2,4-Dihydroxyphenyl)2H-1,3-bis-(4-carbomethoxybenzotriazol) [2,4-Bis-(2H-4′-carbomethoxybenzotriazol-2-yl)-1,3-dihydroxybenzol] (DCMBDH) erhielt man mittels Veresterung der freien Dicarbonsäure mit Methanol. Die Verbindungen wurden mittels Elementaranalysen und spektroskopisch charakterisiert (IR, UV,1H und13C NMR). Es wurden Copolymerisationen zur Inkorporierung vonDCBDH undDCMBDH in Polyamide und Polyester durchgeführt. Die Kondensationskopolymeren werden kurz charakterisiert.
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References
Bailey D, Vogl O (1976) J Macromol Sci Macromol Reviews C14(2), 267
Tirrell D, Bailey DB, Vogl O (1977) Polymer Preprints, ACS Division of Polymer Chemistry 18(1): 542
Vogl O, Yoshida S (1980) Rev Roum de Chimie 25: 1123
Yoshida S, Vogl O (1982) Makromol Chem 183: 259
Yoshida S, Lillya CP, Vogl O (1982) J Polym Sci, Polym Chem Ed 20: 2215
Nir Z, Gupta A, Vogl O (1982) J Polym Sci, Polym Chem Ed 20: 2735
Li SJ, Albertsson AC, Gupta A, Bassett Jr W, Vogl O (1984) Monatsh Chem 115: 853
Vogl O,Albertsson AC,Janovic Z (1985) In:Klemchuk PP (ed) Polymer stabilization and degradation. Symposium Series 200: 195
Xi F, Bassett Jr W, Vogl O (1984) Polymer Bulletin 11: 329
Vogl O (1984) Makromol Chem Suppl 7: 1
Vogl O, Albertsson AC, Janovic Z (1985) Polymer 26: 1288
Li SJ, Gupta A, Vogl O (1983) Monatsh Chem 114: 937
Li SJ, Gupta A, Albertsson AC, Bassett Jr W, Vogl O (1984) Polymer Bulletin 12: 237
Fu SK, Gupta A, Albertsson AC, Vogl O (1985) In:Norman SA, Rabek JF (eds) New trends in the photochemistry of polymers. Elsevier Applied Science Publishers, London, New York, p 247
Xi F, Bassett Jr W, Vogl O (1984) Makromol Chem 185: 2497
Li SJ, Bassett Jr W, Gupta A, Vogl O (1983) J Macromol Sci Chem A20: 309
Kitayama M, Vogl O (1982) Polymer J (Japan) 14: 537
Fu SK, Li SJ, Vogl O (1986) Monatsh Chem 117: 805
Gomez PM, Vogl O (1986) Polymer J 18: 429
Gomez PM, Hu LP, Vogl O (1986) Polymer Bulletin 15: 135
Gomez PM, Fu SK, Gupta A, Vogl O (1985) Polymer Preprints. ACS Division of Polymer Chemistry 26(1): 100
Borel E, Deuel H (1953) Helvetica Chimica Acta 36: 801
Ross JM (1965) U.S. Patent 3,177,247
Ewing DF (1979) Organic Magnetic Resonance 12: 514
Jacquet B,Papantonious C,DuFaure P,Mahieux C (1978) Germ Offen DE 2,734 149
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Functional Polymers LI:M. D. Purgett,W. J. MacKnight, andO. Vogl, Polym. Eng. and Sci.27(19), 1461 (1987)
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Fu, S., Li, S. & Vogl, O. Functional polymers LII Synthesis and polycondensation of 2(2,4-Dihydroxyphenyl)2H-1,3-bis[4-carboxy (or 4-carbomethoxy)2H-benzotriazole]. Monatsh Chem 119, 1299–1309 (1988). https://doi.org/10.1007/BF00808310
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DOI: https://doi.org/10.1007/BF00808310