Synthesis of 2,5-Furandicarboxylic Acid-Based Heat-Resistant Polyamides Under Existing Industrialization Process

Min Cao; Chuanhui Zhang; Bo He; Mujun Huang; Mujun Huang

Macromolecular Research, Vol.25, No.7, 722-729, July, 2017

DOI10.1007/s13233-017-5070-4 Export Citation

Synthesis of 2,5-Furandicarboxylic Acid-Based Heat-Resistant Polyamides Under Existing Industrialization Process

Min Cao, Chuanhui Zhang^†, Bo He¹, Mujun Huang¹, and Mujun Huang¹

Kingfa Sci. & Tech. Co., LTD., 33 Kefeng Road, Science Town, Guangzhou, 510663, P. R. China
¹Zhuhai Vanteque Specialty Engineering Plastics Co., Ltd., No. 177, Petrochemical Road 9, Nanshui Town, Jinwan District, Zhuhai, 519050, P. R. China

E-mail:

As a bio-based material, 2,5-furandicarboxylic acid (FDCA) has been used widely as alternative material to terephthalic acid to produce polyesters or polyamides. In this study, PA10T/10F with melting point higher than 280 oC was produced under existing industrialization process (prepolymerization+solid state polymerization (SSP)), viscosity of which was affected greately by decarboxylation of FDCA. TGIR technique was used to study decarboxylation, and 1,10-decanediamine, CO2, H2O and furan derivates can be found, verifying decarboxylation scheme. 1H NMR, 13C NMR and 2D NMR analysis showed that nearly half of the feeding FDCA monomers decarboxylates during SSP, instead of entering the polyamide chain, leading to the lower furan moiety ratio in polymers compared to that of feeding ratio. However, thermal stability of PA10T/10F polyamide is comparable to PA10T homopolymer, which indicates that FDCA can be a promising base material for heat-resistant polyamide production.

Keywords:2,5-furandicarboxylic acid;semi-aromatic polyamide;PA10T;heat-resistant polyamide

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[2] Zhang C, Mai K, Cao M, Chen J, Shi Z, Jiang S, Eng. Plastics Appl., 40, 95 (2012)

[3] Kohan MI, in Nylon Plastics Handbook, Hanser Publishers, New York, 1995.

[4] Fink JK, in High Performance Polymers, William Andrew Publishing, Norwich, 2008, pp 391-422.

[5] Kemmish DJ, in Practical Guide to High Performance Engineering PlasticsiSmithers, Shropshire, 2011, pp 47-56.

[6] Kashimura T, The Plastics, 44, 15 (1998)

[7] Introduction of Stanyl® (http://www.dsm.com/products/stanyl/ en_US/home.html).

[8] Vestamid® HT plus M3000 (http://www.vestamid.com/sites/lists/ PP-HP/Documents/VESTAMID-HTplus-M3000-Base-polymer-EN.pdf).

[9] Grivory® XE database (http://www.emsgrivory.com/en/ems-material- database/).

[10] Introduction of Vicnyl® (http://www.kingfa.com/siteen/cpml/59/ list_1702.html).

[11] Kabasci S, in Bio-based Plastics: Materials and ApplicationsJohn, Wiley & Sons, Ltd., West Sussex, 2014.

[12] Mittal V, Scrivener Publishing LLC, Massachusetts, 2012.

[13] Chum HL, Noyes Data Corporation, New Jersey, 1991.

[14] Belgacem MN, Gandini A, Elsevier Ltd., Amsterdam, 2008.

[15] Brown BR, Q. Rev. Chem. Soc., 5, 131 (1951)

[16] Hopff H, Krieger A, Helv. Chim. Acta, 44, 1058 (1961)

[17] Moore JA, Bunting W, Polym. Sci. Technol., 31, 51 (1985)

[18] Mitiakoudis A, Gandini A, Macromolecules, 24, 830 (1991)

[19] Gharbi S, Afli A, Gharbi RE, Gandini A, Polym. Int., 50, 509 (2001)

[20] Yutaka K, Miura T, Matsuda K, Komuro T, Canon Kabushiki Kaisha, WO2012132792 (2012).

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[23] Grosshardt O, Fehrenbacher U, Kowollik K, Tubke B, Dingenouts N, Wilhelm M, Chem. Ing. Tech., 81(11), 1829 (2009)

[24] Jiang Y, Maniar D, Woortman AJJ, van Ekenstein GORA, Loos K, Biomacromolecules, 16(11), 3674 (2015)

[25] Papaspyrides CD, Vouyiouka SN, in Solid State Polymerization, John Wiley & Sons, Inc., Hoboken, 2009.

[26] Endah YK, Han SH, Kim JH, Kim NK, Kim WN, Lee HS, Lee H, J. Appl. Polym. Sci., 133, DOI: 10.1002/app.43391 (2016).

[27] Cao M, Xia S, Huang X, Cai T, Zeng X, Kingfa Science & Technology Co. Ltd., Guangzhou, Guangdong, CN, US20100267923AU (2010).

[28] ISO 307. Plastics -- Polyamides -- Determination of Viscosity Number, 2007.

[29] ISO 11357-3. Plastics -- Differential Scanning Calorimetry (DSC) -- Part 3: Determination of Temperature and Enthalpy of Melting and Crystallization, 2011.

[30] Novitsky T, Lange C, Jarrett W, Mathias L, Osborn S, Ayotte R, Manning S, J. Appl. Polym. Sci., 116(6), 3388 (2010)

[31] Novitsky TF, Lange CA, Mathias LJ, Osborn S, Ayotte R, Manning S, Polymer, 51(11), 2417 (2010)

[32] Novitsky TF, Mathias LJ, Osborn S, Ayotte R, Manning S, Macromol. Symp., 313-314, 90 (2012)

[33] Zhang C, Huang X, Zeng X, Cao M, Cai T, Jiang S, Yi Q, J. Appl. Polym. Sci., 131, DOI: 10.1002/app.40058 (2014).

[34] 2,5-Furandicarboxylic acid ($264.87-25g, from Aladdin) (http:// www.aladdin-e.com/us_en/f119129.html).

[35] Murakami M, Togashi O, Yamamoto S, TORAY IND INC, JP8325376A (1996).

[36] National Institute of Standards and Technology, NIST (http://webbook. nist.gov/chemistry/).

[37] Cao M, Zhang M, Huang X, Zeng X, Shi Z, Chen J, Petrochem. Technol., 37, 714 (2008)

[38] Cousin T, Synthesis and Molecular Modelling of Bio-based Polyamides, Ph. D. Thesis, INSA de Lyon, 2013.

[39] Mitchell TN, Costisella B, in NMR - From Spectra to Structures: An Experimental Approach, Springer-Verlag, Berlin Heidelberg, 2007, p 20.