SYNTHESIS OF NEW OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S DERIVED FROM N,N'-(PYROMELLITOYL)-BIS-S-VALINE DIACID CHLORIDE AND AROMATIC DIAMINES UNDER MICROWAVE IRRADIATION AND CLASSICAL HEATING

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MALAKPOUR SH.; SHAH MOHAMMADI M.H.

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Journal: Iranian Polymer Journal Year:2005 | Volume:14 | Issue:5 (59) Page(s): 473-483

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Title

SYNTHESIS OF NEW OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S DERIVED FROM N,N'-(PYROMELLITOYL)-BIS-S-VALINE DIACID CHLORIDE AND AROMATIC DIAMINES UNDER MICROWAVE IRRADIATION AND CLASSICAL HEATING

Author(s)

MALAKPOUR SH. | SHAH MOHAMMADI M.H. | Issue Writer Certificate

Keywords

OPTICALLY ACTIVE POLYMERS

PYROMELLITIC DIANHYDRIDE

MICROWAVE-ASSISTED RAPID POLYCONDENSATION

POLY(AMIDE-IMIDE)S

SOLUTION POLYMERIZATION

THERMALLY STABLE POLYMERS

Abstract

Pyromellitic dianhydride (benzene-1,2,4,5-tetracarboxylic dianhydride) (1) was reacted with s-valine (2) in acetic acid and the resulting imide-acid [N,N'-(pyromellitoyl)-bis-s-valine] (4) was obtained in high yield. The compound (4) was converted to the N,N"-(pyromellitoyl)-bis-s-valine diacid chloride (5) by reaction with thionyl chloride. The polycondensation reaction of this diacid chloride with several aromatic diamines such as 1,4-phenylenediamine (6a), 4,4'-diaminodiphenyl methane (6b), 4,4'-diaminodiphenylsulphone (4,4'-sulphonyldianiline) (6c), 4,4'-diaminodiphenylether (6d), 2,4-diaminotoluene (6e), and 1,3-phenylenediamine (6f) was developed by using a domestic microwave oven in the presence of a small amount of a polar organic medium such as o-cresol and trimethylsilyl chloride as an activating agent for diamines. The polymerization reactions were also performed with two other methods: low-temperature and high-temperature solution polycondensation in the presence of trimethylsilyl chloride. The polymerization reactions proceeded fast and produced a series of optically active poly(amide-imide)s with good yield and moderate inherent viscosity of 0.25-0.43 dLg-1. One of the polymers (7b) showed high thermal resistance, the temperature of 5% weight loss for (7b) was 490°C and the residual weight at 600°C was 76%. All of the above polymers were fully characterized by IR, elemental analysis and specific rotation. Some structural characterizations and physical properties of these optically active poly(amide-imide)s are reported.

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APA: Copy

MALAKPOUR, SH., & SHAH MOHAMMADI, M.H.. (2005). SYNTHESIS OF NEW OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S DERIVED FROM N,N'-(PYROMELLITOYL)-BIS-S-VALINE DIACID CHLORIDE AND AROMATIC DIAMINES UNDER MICROWAVE IRRADIATION AND CLASSICAL HEATING. IRANIAN POLYMER JOURNAL (ENGLISH), 14(5 (59)), 473-483. SID. https://sid.ir/paper/529000/en

Vancouver: Copy

MALAKPOUR SH., SHAH MOHAMMADI M.H.. SYNTHESIS OF NEW OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S DERIVED FROM N,N'-(PYROMELLITOYL)-BIS-S-VALINE DIACID CHLORIDE AND AROMATIC DIAMINES UNDER MICROWAVE IRRADIATION AND CLASSICAL HEATING. IRANIAN POLYMER JOURNAL (ENGLISH)[Internet]. 2005;14(5 (59)):473-483. Available from: https://sid.ir/paper/529000/en

IEEE: Copy

SH. MALAKPOUR, and M.H. SHAH MOHAMMADI, “SYNTHESIS OF NEW OPTICALLY ACTIVE POLY(AMIDE-IMIDE)S DERIVED FROM N,N'-(PYROMELLITOYL)-BIS-S-VALINE DIACID CHLORIDE AND AROMATIC DIAMINES UNDER MICROWAVE IRRADIATION AND CLASSICAL HEATING,” IRANIAN POLYMER JOURNAL (ENGLISH), vol. 14, no. 5 (59), pp. 473–483, 2005, [Online]. Available: https://sid.ir/paper/529000/en

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