Synthesis and Properties of Novel Aromatic Poly(esterimide)s Bearing Naphthalene-2,7-Diyl Units

Abstract

Two series of 2,7-naphthalenediyl units-containing homoand copoly(ester imide)s were prepared from 2,7-bis(4-aminobenzoyloxy)naphthalene and 2,7-bis(3-aminobenzoyloxy)naphthalene, respectively, with six commercially available aromatic tetracarboxylic dianhydrides and their mixtures via a conventional two-stage synthesis that included ring-opening polyaddition to give poly(amic acid)s followed by chemical imidization to polyimides. The intermediate poly(amic acid)s obtained in the first stage had inherent viscosities of 0.59∼1.15 and 0.51∼1.20 dL g^-1, respectively. Some of the poly(ester imide)s derived from less rigid dianhydrides had excellent solubility in polar aprotic solvents such as N-methyl-2-pyrrolidone and N,N-dimethylacetamide and could be solution-cast into transparent, flexible, and tough films. The poly(ester imide)s derived from rigid dianhydrides such as pyromellitic dianhydride (PMDA) and 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA) were semicrystalline and showed less solubility. Except for some examples, most of the poly(ester imide)s displayed discernible glass-transition temperatures (T _gs) between 233 and 295°C in the differential scanning calorimetry traces. These poly(ester imide)s showed insignificant decomposition below 450°C in nitrogen or air. The investigation of the thermal decomposition of the poly(ester imide)s using pyrolysis-gas chromatography/mass spectrometry (pyrolysis-GC/MS) indicated that a dramatic breakage of the ester linkages occurred at around 450°C, which initiated the polymer chain scission.

Keywords

Naphthalene units diamino-diesters poly(ester imide)s pyrolysis-gas chromatography/mass spectrometry

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References

[1] Wilson D , Stenzenberger H D and Hergenrother P M (eds) 1990 Polyimides ( Glasgow and London: Blackie )

[2] Ghosh M K and Mittal K L (eds) 1996 Polyimides: Fundamentals and Applications ( New York: Marcel Dekker )

[3] Takekoshi T , Kochanowski J E , Manello J S and Webber M J 1986 J. Polym. Sci, Polym. Symp. 74 93-93

[4] Eastmond G C and Paprotny J 1996 React. Funct. Polym. 30 27-27

[5] Eastmond G C and Paprotny J 1997 J. Mater. Chem. 7 589-589

[6] Eastmond G C , Gibas M and Paprotny J 1999 Eur. Polym. J. 35 2097-2097

[7] Tamai S , Yamaguchi A and Ohta M 1996 Polymer 37 3683-3683

[8] Li F , Fang S , Ge J J , Honigfort P S , Chen JC , Harris F W and Cheng S Z D 1999 Polymer 40 4571-4571

[9] Li F , Ge J J , Honigfort P S , Fang S , Chen JC , Harris F W and Cheng S Z D 1999 Polymer 40 4987-4987

10.

[10] Hsiao SH and Li CT 1998 Macromolecules 31 7213-7213

11.

[11] Liou GS 1998 J. Polym. Sci. A: Polym. Chem. 36 1937-1937

12.

[12] Liou GS , Maruyama M , Kakimoto M and Imai Y 1998 J. Polym. Sci. A: Polym. Chem. 36 2021-2021

13.

[13] Liaw DJ , Liaw BY and Yang CM 1999 Acta Polym. 50 332-332

14.

[14] Ayala D , Lozano A E , Abajo J de and Campa J G de la 1999 J. Polym. Sci. A: Polym. Chem. 37 804-804

15.

[15] Yang CP and Chen WT 1993 Makromol. Chem. 194 3061-3061

16.

[16] Yang CP and Chen WT 1993 Macromolecules 26 4865-4865

17.

[17] Yang CP and Chen WT 1993 J. Polym. Sci. A: Polym. Chem. 31 2799-2799

18.

[18] Yang CP , Hsiao SH and Jang CC 1995 J. Polym. Sci. A: Polym. Chem. 33 1487-1487

19.

[19] Yang CP and Lin JH 1995 J. Polym. Sci. A: Polym. Chem. 33 2183-2183

20.

[20] Yang CP and Chen JA 1998 Polym. J. 30 571-571

21.

[21] Hsiao SH , Leu WT and Guo W 2002 Polym. J. 34 925-925

22.

[22] Hsiao SH , Yang CP and Chung CL 2003 J. Polym. Sci. A: Polym. Chem. 41 2001-2001