The aza-Michael reaction: towards semi-crystalline polymers from renewable itaconic acid and diamines
| Autor: | D. J. P. van Elk, Carolus H. R. M. Wilsens, C. Gilbert, Manta Roy, Geert Noordzij, Sanjay Rastogi, Y. J. G. van den Boomen |
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| Přispěvatelé: | Biobased Materials, RS: FSE Biobased Materials, Sciences, RS: FSE AMIBM, AMIBM, RS: FSE Sciences |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
BIOPOLYAMIDES
Condensation polymer Polymers and Plastics Diol Bioengineering 02 engineering and technology MONOMERS 010402 general chemistry BPDA 01 natural sciences Biochemistry PLASTICS chemistry.chemical_compound Organic chemistry Itaconic acid SURFACTANTS POLYESTERS chemistry.chemical_classification RESINS Organic Chemistry Polymer PERFORMANCE 021001 nanoscience & nanotechnology 0104 chemical sciences Polyester POLYAMIDES Monomer chemistry Polymerization POST-POLYMERIZATION MODIFICATION 0210 nano-technology VERSATILE BUILDING-BLOCK |
| Zdroj: | Polymer Chemistry, 10(29), 4049-4058. Royal Society of Chemistry |
| ISSN: | 1759-9954 |
| DOI: | 10.1039/c9py00463g |
| Popis: | This study reports, for the first time, semi-crystalline polymers based on bis-pyrrolidone dicarboxylic acids (BPDA) derived from renewable itaconic acid and various diamines. Rigid BPDA monomers could be obtained in high purity and yield from dimethyl itaconate, instead of the normally used itaconic acid as the starting material. The reduction in the melting point of dimethyl-BPDA monomers, compared to that of normal BPDA monomers, enables melt-polycondensation thus avoiding the need for a solvent in the oligomerization step. Under standard polycondensation conditions, the dimethyl-BPDA monomer with a rigid trans-cyclohexanediamine (t-CH-BPDA) could readily be polymerized with linear aliphatic diols (C6 to C12) to yield high molecular weight polyesters. These polyesters are the first in their class to be reported semi-crystalline, having a Tg between 65 and 33 °C and a Tm between 213 and 184 °C, with an increasing aliphatic chain length. Furthermore, even in the presence of hydrophilic pyrrolidone groups, semi-crystalline polyesters based on t-CH-BPDA showed high stability in water with no significant water uptake. Preliminary studies show that t-CH-BPDA monomers can also be polymerized into semi-crystalline polyamides, although insolubility and an unstable melt prevented the accurate characterization of the synthesized polyamides. Though trans-cyclohexanediamine is currently not available from biomass, the potential biomass content in the described semi-crystalline polyesters ranges from 71% for the C6 diol up to 81% for the C12 diol. |
| Databáze: | OpenAIRE |
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