US 9,499,644 B2Granted

Production method of polar group-containing olefin polymers

AssigneesShowa Denko K.K., The University of Tokyo

InventorsShingo Ito, Kyoko Nozaki, Yusuke Ota, Yoshikuni Okumura, Junichi Kuroda

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Abstract

The present invention relates to a method for producing a homopolymer of olefin represented by formula (1): CH2═CHR1 (R1 is a hydrogen atom or hydrocarbon group having 1 to 20 carbon atoms) or a copolymer of two or more thereof or a method for producing a copolymer of olefin represented by formula (1) with olefin containing a polar group represented by formula (2): CH2═CHR2R3 (R2 is a hydrogen atom or methyl group, R3 is —COOR12, —CN, —OCOR12, —OR12, —CH2—OCOR12, —CH2OH, —CH2—N(R13)2 or —CH2-Hal (R12, R13 and Hal have the same meanings as stated in the description), using as a catalyst a metal complex of group 10 elements in the periodic system typified by the structure represented by formula 1 (“Men” represents a menthyl group and “Me” represents a methyl group). The present invention enables the production of high molecular weight polymers of the polar group-containing monomers such as polar group-containing allyl compounds.

A method for producing a homopolymer or copolymer of monomers comprising olefin represented by formula (1)

CH2═CHR1 (1)
in the formula, R1 represents a hydrogen atom or hydrocarbon group having 1 to 20 carbon atoms, using as a polymerization catalyst a metal complex represented by formula (C1)
in the formula, M represents a metal atom of group 10 element in the periodic system;
X represents a phosphorous atom (P) or an arsenic atom (As);
R5 represents a hydrogen atom or hydrocarbon group having 1 to 30 carbon atoms which is optionally substituted by one or more groups selected from a halogen atom, alkoxy group, aryloxy group and acyloxy group;
Y, R6 and R7 independently represent a hydrogen atom, alkoxy group, aryloxy group, silyl group, amino group or hydrocarbon group having 1 to 30 carbon atoms which is optionally substituted by one or more groups selected from a halogen atom, alkoxy group and aryloxy group;
and at least one of R6 and R7 represents a cycloalkyl group represented by formula (5)
in the formula, R represents an alkylene group having 1 to 14 carbon atoms which optionally have a substituent;
R9, R10 and R11 independently represent a hydrogen atom, alkoxy group, aryloxy group, silyl group, amino group or hydrocarbon group having 1 to 30 carbon atoms which is optionally substituted by one or more groups selected from a halogen atom, alkoxy group and aryloxy group;
at least one of R9 and R10 is not a hydrogen atom;
R9, R10, R11 and the above-mentioned alkylene group R optionally bond to each other to form a ring structure;
in the formula, the bond of the carbon atom to X in formula (C1) is also shown;
Q represents a bivalent group indicated in the brackets of Z[—S(═O)2—O-]M, Z[—C(═O)—O-]M, Z[—P(═O)(—OH)—O-]M or Z[—S-]M, wherein Z and M at the beginning and at the end of the formulae are described to show the coupling direction of the groups;
Z represents a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms which is optionally substituted by one or more groups selected from a halogen atom, alkoxy group and aryloxy group;
Y and Z optionally bond to each other to form a ring structure;
R6 or R7 optionally bond to Y to form a ring structure;
L represents an electron-donating ligand and q is 0, ½, 1 or 2.

14 more elements

Abstract

Claims19