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Reactivity of cyclosiloxane with 3,3,4,4,5,5,6,6,6‐nonafluorohexyl group and its application to fluorosilicone synthesis
Author(s) -
Furukawa Yutaka,
ShinYa Seiji,
Miyake Haruhisa,
Kishino Hideharu,
Yamada Minoru,
Kato Hitoshi,
Sato Masakuni
Publication year - 2001
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.2192
Subject(s) - copolymer , polymer chemistry , polymerization , depolymerization , reactivity (psychology) , octamethylcyclotetrasiloxane , molar mass distribution , chemistry , polymer , organic chemistry , medicine , alternative medicine , pathology
The reactivity of cyclosiloxane with 3,3,4,4,5,5,6,6,6‐nonafluorohexyl group and its application to fluorosilicone synthesis were studied. In contrast to the polymerization of the commercially available 1,3,5‐tris(3,3,3‐trifluoropropyl)‐1,3,5‐trimethylcyclotrisiloxane (CF 3 –D3), the polymerization of 1,3,5‐tris(3,3,4,4,5,5,6,6,6‐nonafluorohexyl)‐1,3,5‐trimethylcyclotrisiloxane (C 4 F 9 –D3) with sodium hydroxide yielded 1,3,5,7‐tetrakis(3,3,4,4,5,5,6,6,6‐nonafluorohexyl)‐1,3,5,7‐tetramethylcyclotetrasiloxane {[C 4 F 9 CH 2 CH 2 (CH 3 )SiO] 4 (C 4 F 9 –D4)} as the major product, which was the result of the depolymerization by a backbiting mechanism. On the other hand, the polymerization of C 4 F 9 –D3 with trifluoromethanesulfonic acid yielded a polymer with good reproducibility, although the distribution of molecular weight tended to be bimodal. C 4 F 9 –D3 was also successfully copolymerized with octamethylcyclotetrasiloxane (D4). The properties of the obtained copolymers changed almost linearly with the amount of [C 4 F 9 C 2 H 4 (CH 3 )SiO] units, except for the surface tension. The surface tension of the copolymer containing more than 50% [C 4 F 9 C 2 H 4 (CH 3 )SiO] units by weight was almost as low as that of the homopolymer. When the copolymer containing 50% [C 4 F 9 C 2 H 4 (CH 3 )SiO] units by weight was examined for an antifoaming agent, it worked as effectively as the homopolymer in the toluene foaming system. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 3333–3340, 2001