Synthesis and radical copolymerization of novel propyl cyanoacrylate monomers
| Autor: | Daniel H. Possley, Gregory B. Kharas, Taylor L. Vacala, Adrian A. Pater, Nicholas W. Woo, Nicole M. Jazdzewski, Kaela N. Rivera, Cesar Saucedo, Kelly O. Conger, Edgar J. Crespo, William S. Schjerven, Jonathon D. Knight, Justin E. Spitz, Lissette Arellano, Jordan E. Hollembeak |
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| Rok vydání: | 2019 |
| Předmět: |
Polymers and Plastics
02 engineering and technology General Chemistry Carbon-13 NMR 010402 general chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics 01 natural sciences 0104 chemical sciences Cyanoacrylates law.invention chemistry.chemical_compound Residue (chemistry) Monomer Cyanoacetic acid chemistry Cyanoacrylate law Polymer chemistry Materials Chemistry Copolymer Fourier transform infrared spectroscopy 0210 nano-technology |
| Zdroj: | Polymer Bulletin. 77:1433-1448 |
| ISSN: | 1436-2449 0170-0839 |
| Popis: | Novel phenyl-trisubstituted propyl 3-(R-phenyl)-2-cyanoacrylates (where R is 2,4,5-trimethyl, 2,4,6-trimethyl, 2,3-dimethyl-4-methoxy, 2,5-dimethyl-4-methoxy, 2,4-dimethoxy-3-methyl, 2,4-dimethoxy-6-methyl, 4-hydoxy-3,5-dimethyl, 2,3,4-trimethoxy, 2,4,5-trimethoxy, 2,4,6-trimethoxy, 3,4,5-trimethoxy) were prepared using piperidine-catalyzed condensation of substituted benzoic aldehydes and propyl ester of cyanoacetic acid with good yields (72–97 wt%). The ethenylbenzene copolymerization of cyanoacrylates (at 3/1 mol feed ratio) in solution with radical initiation at 70 °C resulted in formation of copolymers having MW 3.9 to 27.8 kD and 8.4–25.8 mol% of cyanoacrylate. FTIR, 1H and 13C NMR were used to analyze the structure. Thermal behavior of the copolymers was analyzed by DSC, Tg (81–129 °C) and TGA. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 200–500 °C range with residue (0.5–7.3 wt%)and then in the 500–800 °C range. |
| Databáze: | OpenAIRE |
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