A high-molecular-weight aromatic polyamide resin incorporating furan-rings (f-resin) was prepared by low-temperature solution polycondensation of bio-based 2,5-furandiformyl chloride and 3,4′-diaminodiphenyl ether, in N,N-dimethylacetamide. Further, an aromatic polyamide fibre containing furan-rings (f-fibre) was obtained from the fresin by dry-jet wet spinning, and its structure and properties were investigated. The prepared f-resin showed good solubility and possessed good spinnability in solution. The mechanical, heat-resistance, and flame-retardant properties of the f-fibre were found to be excellent – comparable to or exceeding those of meta-aramid fibre (m-fibre). In addition, the furan acid chloride monomer is bio-based and is derived from abundant resources, unlike petroleum-based monomers. Therefore, f-fibre has good potential and broad application prospects as an environment-friendly and sustainable high-performance material.
GarcíaJMGarcíaFCSernaF, et al.High-performance aromatic polyamides. Prog Polym Sci2010; 35: 623–686.
4.
WilsensCHRMDeshmukhYSNoordoverBAJ, et al.Influence of the 2,5-furandicarboxamide moiety on hydrogen bonding in aliphatic-aromatic poly (ester amide)s. Macromolecules2014; 47: 6196–6206.
5.
BurgessSKLeisenJEKraftschikBE, et al.Chain mobility, thermal, and mechanical properties of poly (ethylene furanoate) compared to poly (ethylene terephthalate). Macromolecules2014; 47: 1383–1391.
6.
SousaAFVilelaCFonsecaAC, et al.Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency. Polym Chem2015; 6: 5961–5983.
7.
ZhouJCaoFYuZ, et al.Research progress in preparation and application of bio-based 2,5-furandicarboxylic acid as polyester monomer. Acta Polym Sin2016; 1: 1–13.
8.
HopffVHKriegerA. Über polyamide aus heterocyclischen dicarbonsäuren. Die Makromolekulare Chemie1961; 47: 93–113.
9.
HopffVHKriegerA. Über decarboxylierung und dissoziation heterocyclischer dicarbonsäuren. Helv Chim Acta1961; 44: 1058–1063.
10.
HeertjesPMKokGJ. Polycondensation products of 2,5-furandicarboxylic acid. Delft Prog Rep Ser A1974; 1: 59–63.
11.
MitiakoudisAGandiniA. Synthesis and characterization of furanic polyamides. Macromolecules1991; 24: 830–835.
BeneckeHPKawczakAWGarbarkDB. Furanic-modified amine-based curatives. Patent application 11/903251, USA, 2008.
14.
BeneckeHPKawczakAWGarbarkDB. Furanic-modified amine-based curatives. Patent application 12/550349, USA, 2010.
15.
LuoKWangYYuJ, et al.Semi-bio-based aromatic polyamides from 2,5-furandicarboxylic acid: toward high-performance polymers from renewable resources. RSC Adv2016; 6: 87013–87020.
16.
CuretonLSTNapadenskyEAnnunziatoC, et al.The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides. J App Polym Sci2017; 134: 45514.
GandiniABelgacemMN. Furan in polymer chemistry. Prog Polym Sci1997; 22: 1203–1379.
19.
YuZDengRRaoG, et al.Synthesis and characterization of highly soluble wholly aromatic polyamides containing both furanyl and phenyl units. J Polym Sci2020; 58: 2140–2150.
20.
JiangYManiarDWoortmanA, et al.Enzymatic synthesis of 2,5-furandicarboxylic acid-based semi-aromatic polyamides: enzymatic polymerization kinetics, effect of diamine chain length and thermal properties. RSC Adv2016; 6: 67941–67953.
21.
RozasIAlkortaIElgueroJ. Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors. J Am Chem Soc2000; 122: 11154–11161.
22.
AbidSGharbiREGandiniA. Polyamides incorporating furan moieties. 5. Synthesis and characterisation of furan-aromatic homologues. Polymer2004; 45: 5793–5801.
23.
YuxinLiuWanshunLiLinyuanWang, et al.Spectrum analysis[M]. Chengdu: Sichuan University Press, 2004.
24.
MoranCSBarthelonAPearsallA, et al.Biorenewable blends of polyamide-4,10 and polyamide-6,10. J Appl Polym Sci2016; 133: 43626.
25.
WintersJDehaenWBinnemansK, Solvation structure of poly-m-phenyleneisophthalamide (PMIA) in ionic liquids. Phys Chem Chem Phys2019; 21: 4053–4062.
26.
KwolekSLMorganPWSorensonWR. Process of making wholly aromatic polyamides. Patent 3063966, USA, 1962.
27.
LuoLYaoJWangX, et al.The evolution of macromolecular packing and sudden crystallization in rigid-rod polyimide via effect of multiple H-bonding on charge transfer (CT) interactions. Polymer2014; 55: 4258–4269.
28.
KonstantopoulouMTerzopoulouZNerantzakiM, et al.Poly(ethylene furanoate-co-ethylene terephthalate) biobased copolymers: synthesis, thermal properties and cocrystallization behavior. Eur Polym J2017; 89: 349–366.
29.
AllegraGBassiIW. Isomorphism in synthetic macromolecular systems. In: Fortschritte der Hochpolymeren-Forschung. Berlin and Heidelberg: Springer, 1969, pp. 549–574.
30.
SousaAFMatosMFreireCSR, et al.New copolyesters derived from terephthalic and 2,5-furandicarboxylic acids: a step forward in the development of biobased polyesters. Polymer2013; 54: 513–519.
31.
ZhengHZhangJDuB, et al.Effect of treatment pressure on structures and properties of PMIA fibre in supercritical carbon dioxide fluid. J Appl Polym Sci2015; 132: 41756.
32.
JiangYManiarDWoortmanAJJ, et al.Enzymatic polymerization of furan-2,5-dicarboxylic acid-based furanic-aliphatic polyamides as sustainable alternatives to polyphthalamides. Biomacromolecules2015; 16: 3674–3685.
33.
CousinTGalyJRousseauA, et al.Synthesis and properties of polyamides from 2,5-furandicarboxylic acid. J Appl Polym Sci2018; 135: 45901.
34.
BrownJREnnisBC. Thermal analysis of Nomex and Kevlar fibres. Text Res J1977; 47: 62–66.
35.
ShablyginMVNikitinaOABelousavaTA, et al.The hydrogen bond and its effect on spontaneous orientation during the heating of aromatic polyamides. Polym Sci USSR1982; 24: 1109–1115.
36.
ShablyginMVSluginIVMamonovaTS, et al.The hydrogen bond in thermal strengthening of aramid systems containing polyamide-benzimidazole fragments. Fibre Chem2009; 41: 254–256.
37.
AbroninIABandurkinAVVolkovaLV, et al.Features of hydrogen bonds in aromatic polyamides containing benzimidazole groups according to ab initio quantum chemical calculations. Fibre Chem2016; 47: 375–377.
38.
CaoMZhangCHeB, et al.Synthesis of 2,5-furandicarboxylic acid-based heat-resistant polyamides under existing industrialization process. Macromol Res2017; 25: 722–729.
39.
CaoKLiuYYangY, et al.The preparation and characterization of a heterocyclic meta-aramid fiber with outstanding thermal stability. High Perform Polym2020: 0954008320974415. DOI: 10.1177/0954008320974415.
40.
Villar-RodilSMartinez-AlonsoATasconJMD. Studies on pyrolysis of Nomex polyaramid fibers. J Anal Appl Pyrolysis2001; 58: 105–115.
41.
WangXWHuZMLiuZF. Thermal degradation of meta- and para-aramid fibres in different atmospheres. Intern Polym Proc2008; 23: 81–87.
42.
Le BrasMBourbigotSCaminoG, et al.Fire retardancy of polymers: the use of intumescence. Cambridge: The Royal Society of Chemistry, 1998.
