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Catalysts 2015, 5(4), 2001-2017; doi:10.3390/catal5042001

Synthesis of Ethylene or Propylene/1,3-Butadiene Copolymers Possessing Pendant Vinyl Groups with Virtually No Internal Olefins

1
Mitsui Chemicals Inc., 1-2, Waki 6-chome, Waki-cho, Kuga-gun, Yamaguchi 740-0061, Japan
2
Mitsui Chemicals Inc., 580-32 Nagaura, Sodegaura, Chiba 299-0265, Japan
*
Authors to whom correspondence should be addressed.
Academic Editor: Carl Redshaw
Received: 7 October 2015 / Accepted: 12 November 2015 / Published: 20 November 2015
(This article belongs to the Special Issue Molecular Catalysis for Precise Olefin Polymerization and ROP 2015)
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Abstract

In general, ethylene/1,3-butadiene copolymerizations provides copolymers possessing both pendant vinyls and vinylenes as olefinic moieties. We, at MCI, studied the substituent effects of C2-symmetric zirconocene complexes, rac-[Me2Si(Indenyl’)2]ZrCl2 (Indenyl’ = generic substituted indenyl), after activation on the ratio of the pendant vinyls and vinylenes of the resultant copolymers. Complexes examined in this study were rac-dimethylsilylbis (1-indenyl)zirconium dichloride (1), rac-dimethylsilyl-bis[1-(2-methyl-4,5-benzoindenyl)] zirconium dichloride (2), rac-dimethylsilyl-bis[l-(2-methyl -4-phenylindenyl)]zirconium dichloride (3), rac-dimethy1si1y1- bis(2-ethyl-4-phenylindenyl) zirconium dichloride (4), rac-dimethylsilyl-bis[l-(2-n-propyl -4-(1-naphthyl)indenyl)]zirconium dichloride (5), rac-dimethylsilyl-[1-(2-ethyl-4-(5-(2,2-dimethyl-2,3-dihydro-1H-cyclopenta [a]naphthalenyl)indenyl))][1-(2-n-propyl-4-(5-(2,2-dimethyl-2,3-dihydro-1H-cyclopenta[a] naphthalenyl)indenyl))]zirconium dichloride (6), rac-dimethylsilyl-bis[1-(2-ethyl-4-(9-phenanthryl)indenyl)]zirconium dichloride (7), and rac-dimethylsilyl-bis[l-(2-n-propyl-4-(9-phenanthryl)indenyl)]zirconium dichloride (8). We found that the ratio of the pendant vinyls and vinylenes is strongly affected by the bulkiness of the substituent on the complexes examined. The vinyl content increased linearly in the following order, 8 > 7 > 6 > 5 > 4 > 3 > 2 > 1. Notably, complex 8/DMAO formed ethylene/1,3-butadiene copolymers possessing predominant vinyl groups, which can be crucial precursors for functionalized polyolefins. Likewise, complex 8/DMAO afforded propylene/1,3-butadiene copolymers with predominant vinyl groups. View Full-Text
Keywords: 1,3-butadiene; C2-symmetric zirconocene; insertion mode; vinyl groups; internal olefins; vinylenes 1,3-butadiene; C2-symmetric zirconocene; insertion mode; vinyl groups; internal olefins; vinylenes
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Michiue, K.; Mitani, M.; Fujita, T. Synthesis of Ethylene or Propylene/1,3-Butadiene Copolymers Possessing Pendant Vinyl Groups with Virtually No Internal Olefins. Catalysts 2015, 5, 2001-2017.

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