he effect of the pyromellitimide moieties in the increasing of the thermal stability of poly (glycidyl methacrylate). Also the TG scheme shows the temperature of 10% weight loss (T10) and the temperature of 50% weight loss (T50) are at 356˚C and 473˚C respectively.

3.2. Solubility and Viscosity

The polymer shows good solubility in aprotic polar solvents such as NMP, DMAc, DMF, and DMSO, while insoluble with common organic solvents such as tetrahydrofuran, chloroform, acetone and benzene. The polymer had good transparency and its inherent viscosity (η inh) is 0.82 dL/g.

Figure 4. FT-IR of the cured difunctional monomer BHPMEPM.

Figure 5. TG and DTG thermograms of crosslinked BHPMEPM.

4. Conclusion

The diacid-diimide was used as a building block of poly(imide-ester) by its reaction with glycidylmethacrylate to produce a new bifunctional monomer. The structure of this monomer was confirmed by FT-IR, 1H FT-NMR, and elemental analysis. The curing reaction of this bifunctional monomer was monitored by DSC scanning which shows that one reaction exotherm represents the crosslinking cured product depending on the reactivity of methacrylic two double bonds with a maximum of the exothermic peak at 180.2˚C. The cured product shows good thermal properties and good solubility in aprotic polar solvents. The crosslinked products can be used as moulding compounds and encapsulating materials in electric or electronic industry.

Cite this paper
Saedi, H. (2016) Synthesis and Polymerization of N,N'-[Bis(4,4'-Hydroxypropyl Methacrylate Phenylester) Pyromellitimide] Thermoset Polymer by Microwave Irradiation. Advances in Chemical Engineering and Science, 6, 183-189. doi: 10.4236/aces.2016.62019.
References
[1]   Sroog, C.E. (1996) History of the Invention and Development of the Polyimides. In: Ghosh, M.K. and Mittal, K.L., Eds., Polyimides: Fundamentals and Applications, Marcel Dekker, New York.

[2]   Bessonov, M.I., Koton, M.M., Kudryavtsev, V.V. and Laius, L.A. (1987) Polyimides. Thermally Stable Polymers, Consultants Bureau, New York.

[3]   Wilson, D., Stenzenzenberger, H.D. and Hergenrother, P.M. (1990) Polyimides. Blackie & Son, Glasgow and London.
http://dx.doi.org/10.1007/978-94-010-9661-4

[4]   Spiliopoulos, I.K., Mikroyannidis, J.A. and Tsivgoulis, G.M. (1998) Rigid-Rod Polyamides and Polyimides Derived from 4,3”-Diamino-2’,6’-Diphenyl-P-Terphenyl or Di(4-biphemyl)-P-Terphenyl and 4-Amino-4” Carboxy-2’-6’-Diphenyl-P-Terphenyl. Macromolecules, 31, 522-529.
http://dx.doi.org/10.1021/ma9709664

[5]   Mittal, K.L. (2003) Polyimides and Other High Temperature Polymers: Synthesis, Characterization and Applications. Vol. 2, VSP, Utrecht.

[6]   Huang, S.J. and Hoyt, A.E. (1995) Synthesis of Soluble Polyimides. Trends in Polymer Science, 3, 262.

[7]   Cella, J.A. (1992) Degradation and Stability of Polyimides. Polymer Degradation and Stability, 36, 99-110.
http://dx.doi.org/10.1016/0141-3910(92)90145-U

[8]   Volksen, W. (1994) Condensation Polyimides: Synthesis, Solution Behavior, and Imidization Characteristics. Advances in Polymer Science, 117, 111-164.
http://dx.doi.org/10.1007/BFb0021198

[9]   Takekoshi, T. (1990) Polyimides. Advances in Polymer Science, 94, 1-25.
http://dx.doi.org/10.1007/BFb0043059

[10]   Gohsh, M.K. and Mittal, K.L. (1996) Polyimides Fundamentals and Applications. Marcel Dekker, New York.

[11]   Bessonov, M.I. and Zubkov, V.A. (1993) Polyamic Acids and Polyimides, Synthesis, Transformation and Structure. CRC Press, Boca Raton.

[12]   Kricheldorf, H.R., Schwarz, G., Domschke, A. and Linzer, V. (1993) Liquid Crystalline Polyimides. 15. Role of Conformation and Donor-Acceptor Interactions for the Nematic Order of Poly(ester-imide)s. Macromolecules, 26, 5161-5168.
http://dx.doi.org/10.1021/ma00071a028

[13]   Kricheldorf, H.R. and Pakull, R. (1987) New Polymer Syntheses: 21. LC-Poly(ester imide)s Prepared from Trimellitic Acid, α,θ-diaminoalkanes and Various Hydroquinones or Dihydroxynaphthalenes. Polymer, 28, 1772-1778.
http://dx.doi.org/10.1016/0032-3861(87)90023-1

[14]   Yang, C.P. and Hsiao, S.H. (1989) Preparation of Poly(amide-imide)s by Means of Triphenyl Phosphite, 1. Aliphatic-Aromatic Poly(amide-imide)s Based on Trimellitimide. Die Makromolekulare Chemie, 190, 2119-2131.
http://dx.doi.org/10.1002/macp.1989.021900912

[15]   Hsiao, S.H. and Yang, C.P. (1990) Preparation of Poly(amide-imide)s via the Phosphorylation Reaction. II. Synthesis of Wholly Aromatic Polyamide-Imides from N-[p-(or m-)carboxyphenyl]trimellitimides and Various Aromatic Diamines. Journal of Polymer Science Part A: Polymer Chemistry, 28, 1149-1159.
http://dx.doi.org/10.1002/pola.1990.080280515

[16]   de Abajo, J. and de la Campa, J.G. (1999) Processable Aromatic Polyimides. In: Kricheldorf, H.R., Ed., Progress in Polyimide Chemistry I, Advances in Polymer Science, Vol. 140, Springer, Berlin, 23-59.
http://dx.doi.org/10.1007/3-540-49815-X_2

[17]   Mallakpour, S. and Kolahdoozan, M. (2006) Preparation and Characterization of Novel Optically Active Poly(amide-ester-imide)s Based on Bis(p-aminobezoic acid)-Ntrimellitylimido-S-valine via Direct Polyesterification. Iranian Polymer Journal, 15, 307-315.

[18]   Larhed, M. and Hallberg, A. (2001) Microwave-Assisted High-Speed Chemistry: A New Technique in Drug Discovery. Drug Discovery Today, 6, 406-441.
http://dx.doi.org/10.1016/s1359-6446(01)01735-4

[19]   Mingos, D.M.P. and Whittaker, A.G.P. (1997) Microwave Dielectric Heating Effects in Chemical Synthesis. In: Van Malik, R.V. and Hubbard, C.D., Eds., Chemistry under Extreme or Non-Classical Conditions, John Wiley and Sons and Spektrum Akade-mischer Verlag Co-Publication, New York and Heidelberg, 479-514.

[20]   Saedi, H. (2014) Using Microwave Irradiation for Synthesis of Imides Consist of Pyromellitimide. Journal of Advances in Chemistry, 10, 2276-2282.

[21]   Bakhshi, H., Zohuriaan-Mehr, M.J., Bouhendi, H. and Kabiri, K. (2009) Spectral and Chemical Determination of Copolymer Composition of Poly(butyl acrylate-co-glycidyl methacrylate) from Emulsion Polymerization. Polymer Testing, 28, 730-736.
http://dx.doi.org/10.1016/j.polymertesting.2009.06.003

[22]   Hanifah, S.A., Hamzah, N. and Yook, H.L. (2013) Rapid Synthesis of Magnetic Microspheres Poly(glycidyl methacrylate-co-styrene) by Photopolymerization. Sains Malaysiana, 42, 487-493.

[23]   Vijayanand, P.S., Kato, S., Satokawa, S. and Kojima, T. (2007) Homopolymer and Copolymers of 4-nitro-3-methyl-phenyl Methacrylate with Glycidyl Methacrylate: Synthesis, Characterization, Monomer Reactivity Ratios and Thermal Properties. European Polymer Journal, 43, 2046-2056.
http://dx.doi.org/10.1016/j.eurpolymj.2007.01.042

 
 
Top