A Semicrystalline Furanic Polyamide Made from Renewable Feedstocks.

Woroch, Cristian P; Cox, India W; Kanan, Matthew W

Woroch, Cristian P; Cox, India W; Kanan, Matthew W.

Affiliation

Woroch CP; Department of Chemistry, Stanford University, 337 Campus Drive, Stanford, California 94305, United States.
Cox IW; Department of Chemistry, Stanford University, 337 Campus Drive, Stanford, California 94305, United States.
Kanan MW; Department of Chemistry, Stanford University, 337 Campus Drive, Stanford, California 94305, United States.

J Am Chem Soc ; 145(1): 697-705, 2023 01 11.

Article in En | MEDLINE | ID: mdl-36573894

ABSTRACT

ABSTRACT

Semi-aromatic polyamides (SAPs) synthesized from petrochemical diacids and diamines are high-performance polymers that often derive their desirable properties from a high degree of crystallinity. Attempts to develop partially renewable SAPs by replacing petrochemical diacids with biobased furan-2,5-dicarboxylic acid (FDCA) have resulted in amorphous materials or polymers with low melting temperatures. Herein, we report the development of poly(5-aminomethyl-2-furoic acid) (PAMF), a semicrystalline SAP synthesized by the polycondensation of CO2 and lignocellulose-derived monomer 5-aminomethyl-2-furoic acid (AMF). PAMF has glass-transition and melting temperatures comparable to that of commercial materials and higher than that of any previous furanic SAP. Additionally, PAMF can be copolymerized with conventional nylon 6 and is chemically recyclable. Molecular dynamics (MD) simulations suggest that differences in intramolecular hydrogen bonding explain why PAMF is semicrystalline but many FDCA-based SAPs are not.

Subject(s)

Dicarboxylic Acids; Nylons; Nylons/chemistry; Dicarboxylic Acids/chemistry; Temperature

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