Synthesis and characterization of novel renewable, diaminoisoidide-based polyamides
Jasinska, L. ; Villani, M. ; Wu, J. ; Es, D.S. van; Rastogi, S. ; Koning, C. - \ 2011
In: 41st National Meeting and Exposition of the American Chemical Society, Anaheim, CA, USA, 27 - 31 March, 2011. - - p. 302 - POLY.
Novel, Fully Biobased Semicrystalline Polyamides
Jasinska, L. ; Villani, M. ; Es, D.S. van; Klop, E. ; Rastogi, S. ; Koning, C.E. - \ 2011
Macromolecules 44 (2011)9. - ISSN 0024-9297 - p. 3458 - 3466.
folded lamellar crystals - x-ray-diffraction - brill transition - amino-acid - bioanalogous polymers - nylon-6 6 - behavior - amide)s - temperature - polycondensation
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.
|A new family of bio-based chiral building blocks
Wu, J. ; Jasinska, L. ; Es, D.S. van; Koning, C.E. - \ 2010