Imbalance condensation of diaminophenylbenzimidazole, DAPBI, with terephthaloyl chloride, TPC was conducted for the purpose of synthesis of macromonomers, expected to be used in syntheses of aromatic polyamides with structural regularities. The products are soluble in dimethylsulfoxide—d6, and their 1H NMR spectra indicate that all the products are carboxyl-terminated. The signal of carboxyphenyl linked to chain ends is different from that of terephthaloyl in the 1H NMR spectra. By use of the ratio of the signal intensity of the former to that of the latter, the number-average degree of polymerization, DPNMR is determined. With the mole ratio in feed, DPNMR of the product increases. The TG thermograms of the products are a multistage one. Each stage is classified by temperature and mass loss at an inflection point. Mass loss of each stage classified by temperature at an inflection point corresponds to mass fraction of an aromatic amide with a characteristic degree of polymerization, DP, and that is, the DP distribution of the products is roughly estimated from the TG thermograms. The DP distribution of macromonomers influences performance of aromatic polyamides with structural regularities, derived from the macromonomers. The convenient estimation method of DP distribution by TG is useful in industries of high-performance polymers. To the knowledge, such convenient technique has never reported.
1. Abematsu, H, Tsuchiya, M, Iseri, Y, Kojima, T. Thermogravimetric analysis of aromatic polyamides with benzimidazolyl side group. J Therm Anal Cal. 1999;56:1093–1096. .
2. Fujimura, T, Tsuchiya, M, Koizumi, T, Ishimaru, K, Kojima, T. Synthesis and fluorescence in solution of polybenzimidazolyl phenylenephthalamides. J Appl Polym Sci. 2003;89:1412–1416. .
3. Kojima, T, Ichinose, K, Nakamura, T, Hosaka, Y. Synethesis and thermal stability of isomeric aromatic amide oligomers. Kobunshi Ronbunshu. 1978;35:629–633.
4. Kojima, T, Nakamura, T, Hosaka, Y. Thermal stability of poly(phenylenephthalamide) copolymers. Kobunshi Ronbunshu. 1981;38:791–796.
5. Miyamoto, Y, Kojima, T, Hosaka, Y. Synthesis and thermal stability of isomeric benzaqmide oligomers. Kobunshi Ronbunshu. 1981;39:41–47.
6. Wongjuntaramanee, K, Tsuchiya, M, Ishimaru, K, Kojima, T. Effects of dilution with PMMA and network formation on fluorescence from benzimidazolylphenylenes linked to PMMA network. J Appl Polym Sci. 2010;115:1841–1845. .
7. Hajmirsadeghi, SS, Teimouri, MB, Rahimi-Nasrabadi, M, Dehghanpour, SJ. Non-isothermal kinetic study of the thermal decomposition of N-{bis[benzyl(methyl)amino]phosphoryl}- 2, 2-dichloroacetamide and N-{bis[dibenzylamino]phosphoryl}- 2, 2-dichloroacetamide. Therm Anal Cal. 2009;98:463–468. .
8. Khalil, MH, Ismail, HE, Azim, SA, Sowaya, ER. Synthesis, characterization, and thermal analysis of ternary complexes of nitrilotriacetic acid and alanine or phenylalanine with some transition metals. J Therm Anal Cal. 2010;101:129–135. .
9. Grand, LM, Palmer, SJ, Frost, L. Synthesis and thermal stability of hydrotalcites based upon gallium. J Therm Anal Cal. 2010;101:195–198. .
10. Avsar, G, Altinel, H, Yilmaz, M. Synthesis, characterization, and thermal decomposition of fluorinated salicylaldehyde Schiff base derivatives (salen) and their complexes with copper (II). J Therm Anal Cal. 2010;101:199–203. .
11. Hatakeyama, H, Tsujimoto, Y, Zarubin, MJ, Kurutov, SM, Hatakeyama, T. Thermal decomposition and glass transition of industrial hydrolysis lignin. J Therm Anal Cal. 2010;101:289–295. .
12. Kojima, T. Proton NMR studies of a polybenzimidazole in solution. J Polym Sci Polym Chem Ed. 1980;18:1791–1800.
13. Chatfield, DA, Einhorn, IN, Mickelson, RW, Futrell, JH. Analysis of the products of thermal decomposition of an aromatic polyamide fabric. J Polym Sci Polym Chem Ed. 1979;17:1367–1381. .
14. Khanna, YP, Pearce, EM. Aromatic polyamides. II. Thermal degradation of some aromatic polyamides and their model diamines. J Polym Sci Polym Chem Ed. 1981;19:2817–2834. .