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Mono‐ and bifunctional six‐membered cyclic carbonates synthesized by diphenyl carbonate toward networked polycarbonate films
Author(s) -
Matsukizono Hiroyuki,
Endo Takeshi
Publication year - 2015
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.41956
Subject(s) - polycarbonate , bifunctional , selectivity , carbonate , diphenyl carbonate , reactivity (psychology) , polymerization , polymer chemistry , catalysis , dimethyl carbonate , chemistry , yield (engineering) , materials science , chemical engineering , organic chemistry , polymer , transesterification , composite material , medicine , alternative medicine , pathology , engineering
The synthesis of six‐membered cyclic carbonates from diols utilizing less toxic and easily‐handled diphenyl carbonate (DPC) is carried out based on the reactivity and selectivity at different conditions. Commercially‐available neopentylglycol (NPG) or di(trimethylolproapane) (DTMP) react effectively with DPC at 140°C and converted to their corresponding monofunctional NPG‐carbonate (NPGC) or bifunctional DTMPC‐carboante (DTMPC), respectively. The selectivity of these carbonates changes depending on a feed ratio of DPC and these diols. After a NPG/DPC mixture with the DPC/NPG feed ratio of 4 was heated at 140°C for 48 h, the NPGC is isolated with a yield of 74%. A 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU)‐catalyzed ring‐opening polymerization (ROP) of NPGC with DTMPC can form effectively networked structures. By only drying of THF solutions containing NPGC, DTMPC, and a catalytic amount of DBU at 60°C for 12 h, the ROP efficiently proceeds and networked polycarbonate films with well transparency and flexibility are easily obtained. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132 , 41956.