Abstract
N,N′-Pyromelliticdiimido-di-l-amino acids (1a–1d) were prepared from the reaction of pyromellitic dianhydride with the corresponding l-amino acids in a solution of glacial acetic acid/pyridine (3:2) at refluxing temperature. 4,4′-sulfonyl bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol, 4,4′-oxy bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol and 4,4′-methylene bis(4,1-phenylene) bis(diazene-2,1-diyl) diphenol, were prepared from 4,4′-diamino diphenyl sulfone, 4,4′-diamino diphenyl ether, 4,4′-diamino diphenyl methane, sodium nitrite and phenol following the general procedure of diazo coupling. Interfacial polycondensation method was used to prepare the corresponding poly(azo-ester-imid)s (PAEI 1–12 ) in biphasic solution of water/dichloromethane. The resulting polymers (PAEIs) have been obtained in high yields having good inherent viscosities (0.32–0.57 dl g−1), optical activities and thermal stabilities.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Banihashemi A, Pourabbas B (2000) New thermally stable polyamides derived from 2,9-diamino benzofuro[2,3-b]benzofuran, a new monomer. Eur Polym J 36:2031–2038
Billiot E, Warner IM (2000) Examination of structural changes of polymeric amino acid-based surfactants on enantioselectivity: effect of amino acid order, steric factors, and number and position of chiral centers. Anal Chem 72:1740–1748
Bluhm L, Huang JM, Li TY (2005) Recent advances in peptide chiral selectors for electrophoresis and liquid chromatography. Anal Bioanal Chem 382:592–598
Chen Y, Fang J, Kao SC (1995) Preparation of polyamides derived from 1,6-diamantane dicarboxylic chloride by solution polycondensation and interfacial polycondensation. J Polym Sci Part A 33:2833–2840
Feng L, Hu J, Liu ZH, Zhao F, Liu G (2007) Preparation and properties of optically active poly(N-methacryloyl l-leucine methyl ester). Polymer 48(13):3616–3623
Finch CA (1993) Encapsulation controlled release. Royal Soc Chem 138:1
Ghassemi H, Hay AS (1993) Novel poly(ether imides) utilizing hydrazine as the diamine. Macromolecules 26:5824–5826
Gup R, Giziroglu E, Kirkan B (2007) Synthesis and spectroscopic properties of new azo-dyes and azometal complexes derived from barbituric acid and aminoquinoline. Dyes Pigments 73:40–46
Hallas G, Choi JH (1999) Synthesis and properties of novel aziridinyl azo dyes from 2-aminothiophenes—Part 2: application of some disperse dyes to polyester fibres. Dyes Pigments 40:119–129
Kaplan SL, Hirsch SS (1974) In: New Industrial Polymers, ACS Symposium Series 4. American Chemical Society, Washington DC, p 100
Kim K, Lee S, Ryu K, Lee K (1995) The effect of temperature and solvent on the polymerization of 2-propenylfuran. Polym Bull 35:57–62
Koh J, Greaves AJ (2001) Synthesis of heteroaryl pyridone methine dyes. Dyes Pigments 50:13–19
Kumar GS, Neckers DC (1989) Photochemistry of azobenzene-containing polymers. Chem Rev 89:1915–1925
Kurita K, Mikawa N, Ishii SH, Nishimura SH (1991) Polymers based on p-aminophenol. 7. New synthetic approaches to the simplest wholly aromatic poly(imide ester) via the corresponding poly(amic acid) precursor. Macromolecules 24:6853–6855
Lando JB, Rickert SE (1987) Phase-controlled surface reactions. Thin Solid Films 152:327–333
Morgan PW (1965) Condensation polymers: by interfacial and solution methods. John Wiley, New York
Noll W (1968) Chemistry and technology of silicon. Academic Press, New York
Provatas A, Matisons J, Clarke S (2000) Synthesis of poly (methylphenylsiloxane)-block-poly(dimethylsiloxane) block copolymers by interfacial polymerization. Macromolecules 33:9156−9159
Sroog CE (1990) In: Wilson D, Stenzenberger HD, Hergenrother PM (eds) Polyimides. Chapman and Hall, New York, p 252
Takekoshi T (1990) Polyimides, advances in polymer science, vol 94. Springer, Berlin, p 1
Wang C, Nakamura S (1995) Synthesis of reactive copolyesters derived from isophthaloyl chloride, bisphenol a, and aliphatic diols with additional reactive groups. J Polym Sci Part A 33:2027−2031
Wilson D (1990) In: Wilson D, Stenzenberger HD, Hergenrother PM (eds) Polyimides. Chapman and Hall, New York, p 187
Wu L, Tuo X, Cheng H, Chen ZH, Wang X (2001) Synthesis, photoresponsive behavior, and self-assembly of poly(acrylic acid)-based azo polyelectrolytes. Macromolecules 34:8005–8013
Xin Z, Sanda F, Endo T (2001) Synthesis and characterization of coloured monomers based on 2-methylresorcinol. Dyes Pigments 49:1−7
Zollinger H (1961) Azo and diazo chemistry. Interscience Publishers Inc., New York
Acknowledgments
We gratefully acknowledge the funding support received for this project from Isfahan University of Technology (IUT), IR Iran (ARH) and grant GM 33138(AER) from the national Institute of health, USA. Further financial support from center of Excellency in chemistry research (IUT) is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hajipour, A.R., Zahmatkesh, S., Roosta, P. et al. Synthesis and characterization of new optically active poly(azo-ester-imide)s via interfacial polycondensation. Amino Acids 36, 511–518 (2009). https://doi.org/10.1007/s00726-008-0113-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-008-0113-y