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Abstract

N,N′-(4,4′-carbonyl-diphthaloyl)-bis-(L-phenylalanine)diol (p4) as novel chiral diol was prepared from L-phenylalaninol (2) and 4,4′-carbonyldiphthalic dianhydride (3) in dry acetic acid under refluxing conditions in high yield and characterized with Fourier transform infrared (FTIR), ¹H-NMR and ¹³C-NMR. The step-growth polymerization of this novel chiral diol (p4) containing an imide group and a chiral group with different diisocyanates in dry N-methylpyrrolidinone (NMP) was conducted under conventional heating conditions. The resulting new optically active polymers were obtained in good yields and their inherent viscosities ranged between 0.18 and 0.29 dL g^—1. The polymers were characterized with FTIR, ¹H-NMR, differential scanning calorimetry and thermogravimetric analysis. These polymers are soluble in aprotic-polar solvents such as N,N-dimethylacetamide, NMP, N,N-dimethylformamide, dimethyl sulfoxide and sulfuric acid. Thermogravimetric analysis showed that the 10% weight loss temperature under air atmosphere were more than 265°C and glass transition temperature (T _g) between 130 and 160°C.

Keywords

N,N′-(4,4′-carbonyl-diphthaloyl)-bis-(l-phenylalanine)diol poly(imide—urethane)s optically active polymers diisocyanate catalyst

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References

Findeisen, K. König, K. and Sundermann, R. (1983). In: Barth, H. and Falbe, J. (eds) Houben-Weyl Methoden derorganischen Chemie, E4 , Thieme Verlag, Stuttgart, 768.

Brochhagen, F.K. and Hutzinger , O. (1991). The Handbook of Environmental Chemistry, Part G, Springer-Verlag, Berlin, vol. 3, 73.

Bruice, P.Y. ( 2001). Organic Chemistry, University of California , Santa Cruz.

Ulrich, H. ( 1996). Chemistry and Technology of Isocyanates, Wiley, Chichester, UK.

Sroog, C.E. , Endrey, A.L. and Oliver, K.L. (1965). Aromatic Polypyromellitimides from Aromatic Polyamic Acid, J Polym. Sci. Polym. Chem, 3: 1373.

Cassidy, P.E. (1980). Thermally Stable Polymers - Synthesise and Properties, Marcel Dekker, New York.

Wulin, Q. , Can, L. , Wenxiang, Z. , Jinsong, L. , Lude, L. and Xin, W. ( 2003). Preparation and Characterization of Soluble Polyimides , J. Appl. Polym. Sci., 56: 1292.

Sato, M. , Hirata, T. and Mukaida, K. ( 1992). Copolymerization of ε-caprolactone and Morpholine-2,5-dione Derivatives, Makromol. Chem., 193: 1927.

Hung, T.C. and Chang, T.C. (1996). Studies on Thermotropic Liquid Crystalline Polymers. XIV. Synthesis and Properties of Liquid Crystalline Poly(imide-ester)s by the Direct Polycondensation, J. Polym. Sci., Polym. Chem. Ed., 34: 2455.

10.

Mallakpour, S.E. , and Shahmohammadi , M.H. (2004). Synthesis and Characterization of Novel Optically Active Poly(imide-urethane)s Derived from N,N′-(pyromellitoyl)-bis-(L-leucine) Diisocyanate and Aromatic Diols, Polym. Int., 53: 184-190.

11.

Caddic, S. (1995). Microwave Assisted Organic Reactions, Tetrahedron, 51: 10403-10432.

12.

Chen, Y.H. and Tseng, H. (1993). Synthesis, Characterization, and Chiroptical Property of Optically Active Poly(urea-urethane)s , J. Polym. Sci. Part A. Polym. Chem., 31: 1719-1721.

13.

Gong, A.J. , Chen, Y.M. , Zhang, X. , Chen, C.F. and Xi, F. ( 1998). Optically Active Cyclic Poly(ether sulfone)s based on Chiral 1,1′-bi-2-naphthol, Tetrahedron Asymm., 9: 4175-4181.

14.

Yeganeh, H. , Tamami, B. and Ghazi, I. ( 2002). Synthesis and Properties of Novel Diisocyanate-based Optically Active Polyimides, Eur. Polym. J., 38: 2179-2185.

15.

Chen, J. , Zhou, Y. , Nan, Q. , Ye, X. , Sun, Y. , Zhang, F. and Wang, Z. ( 2007). Preparation and Properties of Optically Active Polyurethane/TiO2 Nanocomposites Derived from Optically Pure 1,1′-binaphthyl , Eur. Polym. J., 43: 4151-4159.

16.

McKennon, M.J. and Meyers, A.I. (1993). A Convenient Reduction of Amino Acids and their Derivatives, J. Org. Chem. , 58: 3568-3571.

17.

Mallakpour, S.E. , Hajipour, A.R. and Habibi, S. (2001). Facile Synthesis of New Optically Active Poly (amide-imide)s Derived from N,N′-(pyromellitoyl)-bis-L-leucine Diacid Chloride and Aromatic Diamines under Microwave Irradiation, Eur. Polym . J., 37: 2435-2442.

18.

Mallakpour, S.E. , Hajipour, A.R. and Zamanlou, M.R. (2002). Novel Optically Active Poly(amide- imide)s from N,N′-(4,4′-carbonyldiphthaloyl)-bis-L-phenylalanine Diacid Chloride and Aromatic Diamines by Microwave Irradiation, Eur. Polym. J., 38: 475-485.

19.

Mallakpour, S.E. , Hajipour, A.R. and Khoee, S. (2002). Novel Optically Active Poly(amide-imide)s from N,N′-(4,4′-carbonyldiphthaloyl)-bis-L-phenylalanine Diacid Chloride and Aromatic Diamines by Microwave Irradiation, Eur. Polym. J., 38: 2011-2016.

20.

Dondoni, A. , Marra, A. , Rossi , M. and Scoponi, M. (2004). Synthesis and Characterization of Calix[4] arene-based Copolyethers and Polyurethanes. Ionophoric Properties and Extraction Abilities towards Metal Cations of Polymeric Calix[4]arene urethanes, Polymer, 45: 6195-6206.

21.

Senich, G.A. and MacKnight, W.J. (1980). Fourier Transform Infrared Thermal Analysis of a Segmented Polyurethane, Macromolecules , 13: 106.

22.

Fu. B. , Feger, C. and Scheider, W.J. ( 1985). Synthesis and Properties of Monodisperse Hydroxy-terminated Oligomers of 1,4-butanediol and 2,4-toluene Diisocyanate, Polymer, 26: 889.

23.

Abiko, A. and Masamune, S. (1992). An Improved, Convenient Procedure for Reduction of Amino Acids to Aminoalcohols: Use of NaBH4-H2SO4, Tetrahed. Lett., 33: 5517-5518.

24.

Narasimhan, S. , Madhavan, S. and Ganeshvar Prasad , K. (1996 ). Unusual Reactivity of Zinc Borohydride - Conversion of Amino Acids to Amino Alcohols, Synth. Comm., 26: 703-706.

25.

Cary, F.A. and Sundberg, R.J. ( 2000). Advanced Organic Chemistry. Part A., University of Virginia, Charlottesville, VA.

26.

Dong, A. , Wan, T. and Feng, S. ( 1999). IR Spectra Studies of Core-shell Type Waterborne Polyacrylate-Polyurethane Microemulsions, J. Polym. Sci.: Part B: Polym. Phys., 37: 2642-2650.

Synthesis and Characterization of Novel Chiral Poly(imide-urethane) Derived from N,N′-(4,4′-carbonyl-diphthaloyl)-bis-(L-phenylalanine)diol with Different Diisocyanates

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