Novel, Fully Biobased Semicrystalline Polyamides

• Published in: Macromolecules Vol. 44; no. 9; pp. 3458 - 3466
• Main Authors: Jasinska, Lidia, Villani, Maurizio, Wu, Jing, van Es, Daan, Klop, Enno, Rastogi, Sanjay, Koning, Cor E
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 10.05.2011
• Subjects: amide)s; amino-acid; Applied sciences; behavior; bioanalogous polymers; brill transition; Exact sciences and technology; folded lamellar crystals; nylon-6 6; Organic polymers; Physicochemistry of polymers; Polycondensation; Preparation, kinetics, thermodynamics, mechanism and catalysts; temperature; x-ray-diffraction; Heat of transformation; Nylon; Preparation; Supramolecular structure; Amide copolymer; Bicyclic compound; Interfacial polymerization; Condensation polymerization; Experimental study; Oxygen heterocycle; Transformation temperature
• DOI: 10.1021/ma200256v
• ISSN: 0024-9297

Novel, semicrystalline polyamides and co(polyamides) were synthesized from biobased sebacic acid (SA), 2,5-diamino-2,5-dideoxy-1,4;3,6-dianhydroiditol (diaminoisoidide, DAII) as well as from 1,4-diaminobutane (DAB), also known as putrescine in nature. Low molecular weight polyamides were obtained by melt polycondensation of the salts based on these monomers or by interfacial polycondensation. In order to increase their molecular weights the polyamide prepolymers were submitted to a solid state polymerization (SSP) process. The chemical structure of the polymers was confirmed by 2D NMR correlation spectra (COSY), heteronuclear multiple-bond correlation spectra (HMBC) and by FT-IR spectroscopy. In the present work, FT-IR and X-ray techniques were used as a tool for the investigation of the crystal structure of the polymers after SSP. The X-ray diffractograms of the polyamides point to crystals containing both 4.10- and DAII.10-based repeat units. Because of the presence of diaminoisoidide residues the synthesized fully renewable products exhibit tunable polarities and melting points. Since most commercial polyamides have a much higher melting point than their end application requires, especially for fiber applications, this simple adaption can result in a significant reduction of energy consumption during processing.