Production method of polar group-containing olefin polymers

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

CH 2 ═CHR 1   (1)

in the formula, R 1 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); R 5 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, R 6 and R 7 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 R 6 and R 7 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; R 9 , R 10 and R 11 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 R 9 and R 10 is not a hydrogen atom; R 9 , R 10 , R 11 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; R 6 or R 7 optionally bond to Y to form a ring structure; L represents an electron-donating ligand and q is 0, ½, 1 or 2.

2. The method for producing a polymer as claimed in claim 1 , wherein the copolymer is the copolymer of olefin represented by formula (1)

CH 2 ═CHR 1   (1)

and a polar group-containing olefin represented by formula (2)

CH 2 ═CR 2 R 3   (2)

in the formula, R 2 represents a hydrogen atom or a methyl group; R 3 represents —COOR 12 , —CN, —OCOR 12 , —OR 12 , —CH 2 —OCOR 12 , —CH 2 OH, —CH 2 —N(R 13 ) 2 or —CH 2 -Hal, wherein R 12 represents a hydrogen atom or hydrocarbon group having 1 to 5 carbon atoms; R 13 represents a hydrogen atom, hydrocarbon group having 1 to 5 carbon atoms, aromatic substituent having 6 to 18 carbon atoms or alkoxy carbonyl group; and Hal represents a halogen atom.

3. The method for producing a polymer as claimed in claim 1 , wherein the number of carbon atoms of the alkylene group R in formula (5) is 2 to 6.

4. The method for producing a polymer as claimed in claim 1 , wherein the number of carbon atoms of the alkylene group R in formula (5) is 4.

5. The method for producing a polymer as claimed in claim 1 , wherein at least one of R 9 and R 10 in formula (5) is an alkyl group having 1 to 6 carbon atoms or cycloalkyl group having 3 to 8 carbon atoms.

6. The method for producing a polymer as claimed in claim 1 , wherein at least one of R 9 and R 10 in formula (5) is an isopropyl group.

7. The method for producing a polymer as claimed in claim 1 , wherein at least one of R 6 and R 7 in formula (C1) is 2-isopropyl-5-methylcyclohexyl group (menthyl group) represented by the following formula

in the formula, the bond between the carbon atom and X is also shown and X has the same meaning as described in formula (C1).

8. The method for producing a polymer as claimed in claim 1 , wherein both of R 6 and R 7 in formula (C1) are 2-isopropyl-5-methylcyclohexyl group (menthyl group).

9. The method for producing a polymer as claimed in claim 1 , wherein the catalyst represented by formula (C1) is represented by formula (C2)

in the formula, Y 1 represents a halogen atom or bivalent hydrocarbon group having 1 to 70 carbon atoms which is optionally substituted by one or more groups selected from alkoxy group and aryloxy group; Q, M, X, R 5 , R 6 , R 7 , L and q have the same meaning as described in formula (C1).

10. The method for producing a polymer as claimed in claim 9 , wherein Q in formula (C2) is —SO 2 —O—, provided that S bonds to Y 1 and O bonds to M.

11. The method for producing a polymer as claimed in claim 9 , wherein the catalyst represented by formula (C2) is represented by formula (C3)

in the formula, four R 8 s independently represent a hydrogen atom, alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, aryloxy group having 6 to 18 carbon atoms or a halogen atom; and M, X, R 5 , R 6 , R 7 , L and q have the same meanings as described in formula (C1).

12. The method for producing a polymer as claimed in claim 11 , wherein all of R 8 s in formula (C3) are a hydrogen atom.

13. The method for producing a polymer as claimed in claim 1 , wherein M is Pd.

14. The method for producing a polymer as claimed in claim 1 , wherein X is P.

15. The method for producing a polymer as claimed in claim 1 , wherein the olefin represented by formula (1) is ethylene.

16. The method for producing a polymer as claimed in claim 1 , wherein the polar group-containing olefin represented by formula (2) is an allyl compound in which R 3 represents —CH 2 —OCOR 12 , —CH 2 OH, —CH 2 N—(R 13 ) 2 or —CH 2 -Hal, wherein R 12 , R 13 and Hal have the same meanings as described in formula (2).

17. The method for producing a polymer as claimed in claim 1 , wherein the polar group-containing olefin represented by formula (2) is allyl acetate.

18. The method for producing a polymer as claimed in claim 10 , wherein the catalyst represented by formula (C2) is represented by formula (C3)

in the formula, four R 8 s independently represent a hydrogen atom, alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, aryloxy group having 6 to 18 carbon atoms or a halogen atom; and M, X, R 5 , R 6 , R 7 , L and q have the same meanings as described in formula (C1).

19. The method for producing a polymer as claimed in claim 18 , wherein all of R 8 s in formula (C3) are a hydrogen atom.