Synthesis of poly(amide-imide)s from new diacid monomers

Abstract

Two new diacid monomers 4,4′-bis[5-(trimellitimido)napthyloxy]diphenyl sulfone and 4,4′-bis[5-(trimellitimido)napthyloxy]benzophenone were synthesized and characterized by spectroscopic analysis. A series of poly(amide-imide)s (PAIs) were prepared from these diacids and aromatic diamines through phosphorylation reaction. The structures of the PAIs were characterized by infrared and ¹H-NMR. The PAIs were characterized by X-ray diffraction, thermogravimetric analysis, differential scanning calorimetry, electrical properties, solution viscosity and solubility test. The flexible linkages and pendant groups in the PAIs chain will disturb chain–chain packing and their effects on solubility, thermal stability and electrical properties were investigated. PAIs showed excellent thermal stability and good solubility. The dielectric constants of the PAIs were in the range 4.15–4.77. The PAIs have electrical insulation character and the film can be used in insulation of electrical items operating at elevated temperatures.

Keywords

high performance polymers poly(amide-imide)s diacids monomer phosphorylation reaction structure–property relationship

Get full access to this article

View all access options for this article.

References

Perry

Scott

Tunny

. Polyimides formation through the palladium-mediated carbonylation and coupling of Bis(o-iodo amides) and diamines. Macromolecules 1996; 29: 1014–1020.

Zhang

S-J

Y-F

Wang

X-L

. Synthesis and characterization of soluble polyimides derived from the polycondensation of 2,6-bis (4-amino-2-trifluoromethylphenoxy-4′-benzoyl)pyridine with some aromatic dianhydrides. High Perform Polym 2007; 19: 462–476.

Kuznets

. One-pot polyimides synthesis in carboxylic acid medium. High Perform Polym 2000; 12: 445–460.

Buzin

Yablokova

MYu

Kuzenetsov

. New AB polyetherimides obtained by direct polycyclocondensation of aminophenoxy phthalic acids. High Perform Polym 2004; 16: 505–514.

Denton

Ray

Priore

. Moisture diffusion in polyimides films in integrated circuit. J Electron Mater 1985; 14: 119–136.

Wilson

Stenzenberger

Hergenrother

. Polyimide. New York: Chapman and Hall, 1990.

Zahoor

. A soluble aromatic polyamide bearing ether linkages: synthesis and characterization. Colloid Polym Sci 2007; 285: 1749–1754.

Moslem

Masoud

. Synthesis of polyamides from p-xylylene glycol and dinitriles. J Polym Res 2009; 16: 681–686.

Sharam

M-A

Samanesh

. Preparation and characterisation of sulfone–based polyimide nanofoams grafted with poly (propylene glycol). e-Polymers 2007; no 112.

10.

Sharam

M-A

Yagoub

Mehdi

. Naphthalene-ring containing diamine and resulting thermally stable polyamides. Eur Polym J 2005; 41: 2887–2892.

11.

Thiruvasagam

Venkatesan

. Synthesis and characterization of processable aromatic polyimides. High Perform Polym 2010; 22: 682–693.

12.

Thiruvasagam

Venkatesan

. Synthesis and characterization of polyetherimides derived from AB monomers. J Macromol Sci, Part A: Pure Appl Chem 2009; 46: 419–424.

13.

Thiruvasagam

Venkatesan

. Synthesis and characterization of polyetherimides via nitrodisplacement reaction. High Perform Polym. 2011; 23: 22–21.

14.

Venkatesan

Srinivasan

. Synthesis and characterization of polyesterimides containing ether linkages. J Macromol Sci Part A: Chem 1993; A30 (11): 801–814.

15.

Rusu

Nechifor

. Polyamides with pendant cinnamoyloxy ethyl units. High Perform Polym 2003; 15: 197–206.

16.

Sojitra

Patel

. High performance polyamides based on s-triazine ring: synthesis and characterization. High Perform Polym 2010; 22: 974–988.

17.

Saxena

Prabhakaran

Lakshmana Rao

. Synthesis and characterization of polamides and poly(amide-imide)s derived from 2,6-bis(3-aminophenoxy) benzonotrile or 2,6-bis(4-aminophenoxy) benzonitrile. Polym Int 2005; 54: 544–552.

18.

Zaitsev

Goldman

. Self- extinguishing polymer/organoclay nanocomposites. Polym Degrad Stabil 2007; 92: 86–93.

19.

Miyagawa

Fukushima

Oyama

. Photosensitive fluorinated polyimides with a low dielectric constant based on reaction development patterning. J Polym Sci Part A: Polym Chem 2003; 41: 861–871.