Method for producing ring-opening metathesis polymer hydride, and resin composition

A method for producing a hydrogenated ring-opening metathesis polymer comprising

• subjecting a cyclic olefin to ring-opening metathesis polymerization in the presence of a polymerization catalyst to produce a ring-opening metathesis polymer, and hydrogenating at least some of carbon-carbon double bonds of the ring-opening metathesis polymer, the cyclic olefin comprising:
• (i) a monomer represented by the following formula (2),
• wherein
• R28 is a C1-C20 alkyl group, a C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a group represented by the following formula (3),
• wherein
• R29 is a C1-C3 alkylene group, and
• R30 and R31 are independently a C1-C10 alkyl group or a C1-C10 alkyl halide group, and
• (ii) a cyclic olefin that includes a protonic polar group, the proportion of the cyclic olefin including a protonic polar group being 10-90 mol % based on the total cyclic olefins, the polymerization catalyst being a ruthenium compound shown by the following formula (I),
• wherein
• X1 and X2 are independently a halogen atom;
• L1 represents a group represented by any of the following formulas (1-1) to (1-3),
• wherein
• R17 and R18 are independently a phenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, 2,4,6-trimethylphenyl group, biphenyl group, 1-naphthyl group, 2-naphthyl group, or methylnaphthyl group,
• R19 to R22 are independently a hydrogen atom or a C1-C10 alkyl group, and
• R23 to R25 are independently
• a C1-C20 alkyl group,
• a C1-C20 alkoxy group,
• a C3-C20 cycloalkyl group,
• a C6-C20 aryl group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group,
• a C6-C20 aryloxy group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group, or
• a C2-C20 heterocyclic group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group;
• R0 is
• a hydrogen atom,
• a halogen atom,
• a nitro group,
• a cyano group,
• a C1-C20 alkyl group,
• a C1-C20 alkoxy group,
• a C1-C20 alkylthio group,
• a tri-C1-C20 alkylsilyl group,
• a tri-C1-C20 alkylsilyloxy group,
• a C6-C20 aryl group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group,
• a C6-C20 aryloxy group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group,
• a C2-C20 heterocyclic group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group,
• a C1-C20 alkylsulfonyl group,
• a C1-C20 alkylsulfinyl group,
• a formyl group,
• a C1-C20 alkylcarbonyl group,
• a C1-C20 alkoxycarbonyl group,
• a di-C1-C20 alkylcarbamoyl group,
• a di-C1-C20 alkylureido group, or
• a di-C1-C20 alkylsulfonylamino group;
• R1 is
• a group represented by (Rb1)(Rb2)NSO2—,
• a formyl group,
• a C1-C20 alkylcarbonyl group,
• a C1-C20 alkoxycarbonyl group,
• a group represented by (Rc1)(Rc2)NCO—,
• an amide group,
• a halogen atom,
• a di-C1-C20 alkylureido group, or
• a C1-C20 alkylsulfonylamino group, wherein
• Rb1 and Rc1 are
• a hydrogen atom,
• a C1-C20 alkyl group, or
• an aryl group, which may be substituted with a halogen atom a C1-C6 alkyl group, C1-C16 alkoxy group, a nitro group, or a cyano group, and
• Rb2 and Rc2 are
• a hydrogen atom,
• a C1-C20 alkyl group, or an aryl group, which may be substituted with a halogen atom a C1-C6 alkyl group, C1-C16 alkoxy group, a nitro group, or a cyano group,
• provided that Rb1 and Rb2 or Rc1 and Rc2 optionally bond to each other to form a ring;
• R2 and R3 are independently a hydrogen atom, a halogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a tri-C1-C20 alkylsilyloxy group, a C6-C20 aryloxy group, a C6-C20 aryl group, a C2-C20 heterocyclic group, a C1-C20 alkoxycarbonyl group, a di-C1-C20 alkylcarbamoyl group, a di-C1-C20 alkylureido group, or a C1-C20 alkylsulfonylamino group;
• R4 is
• a hydrogen atom,
• a C1-C20 alkyl group,
• a C1-C20 alkoxy group,
• a C1-C20 alkylthio group,
• a tri-C1-C20 alkylsilyl group,
• a tri-C1-C20 alkylsilyloxy group,
• a C6-C20 aryl group, which may be substituted with a halogen atom, C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group,
• a C6-C20 aryloxy group, which may be substituted with a halogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, a nitro group, or a cyano group, or
• a C2-C20 heterocyclic group, which may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, or a cyano group,
• a C1-C20 alkylsulfonyl group,
• a C1-C20 alkylsulfinyl group,
• a C1-C20 alkylcarbonyl group,
• a C1-C20 alkoxycarbonyl group,
• a di-C1-C20 alkylcarbamoyl group,
• a di-C1-C20 alkylureido group,
• a C1-C20 alkylsulfonylamino group, or
• a C6-C20 arylcarbonyl group that is optionally substituted with a halogen atom;
• and
• Y1 is an oxygen atom, a sulfur atom, NRb, or PRb, where Rb is a hydrogen atom or a C1-C20 alkyl group;
• wherein
• the reaction of polymerizing the cyclic olefin by ring-opening metathesis polymerization is conducted in the presence of the polymerization catalyst in an ether-based solvent wherein the ether-based solvent is present in an amount of 0.5-100 parts by weight per one part by weight of the cyclic olefin.