DESCRIPTION

RANDOM COPOLYMER AND PRODUCTION PROCESS THEREOF

Technical Field

The present invention relates to a random copolymer comprising polymerization units derived from each of two or more kinds of diene compounds , and a process for producing a random copolymer.

Background Art

As a copolymer whose main chain comprises polymerization units containing a cyclopentane ring structure, Macromolecules Vol. 35, pages 9640-9647 (2002) discloses an alternating copolymer consisting of (i) a polymerization unit of 1,2-cyclopentylene whose five carbon atoms forming a cyclopentane ring are linked to one or two hydrogen atoms , respectively, and (ii) a polymerization unit of ethylene (-CH ₂ -CH ₂ -), both polymerization units (i) and (ii) being arranged alternately. The above term "polymerization unit" means a unit of a polymerized monomer.

Disclosure of Invention

However, there is no random copolymer known in the art, whose main chain comprises two or more kinds of polymerization units, each of those polymerization units containing a

cyclopentane ring structure and being arranged randomly.

In view of the above-mentioned circumstances, the present invention has an object to provide (i) a random copolymer superior in its heat resistance, whose main chain comprises two or more kinds of polymerization units, each of those polymerization units containing a cyclopentane ring structure and being arranged randomly, and (ii) a process producing a random copolymer.

The present invention is a random copolymer comprising two or more kinds of polymerization units represented by the following formula ( 1 ) :

wherein Y ¹ and Y ² are independently of each another a hydrogen atom, a halogen atom, an alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, a hydroxyl group, a nitrile group, an aldehyde group, an alkyl group, an aralkyl group, an aryl group, a silyl group, a siloxy group, an alkoxy group, an aralkyloxy group, an aryloxy group, an acyl group, an amino group, a substituted amino group, an amide group, an imide group, a thiol group, an alkylthio group, an aralkylthio group, an arylthio group, an

alkylthioxycarbonyl group, or an arylthioxycarbonyl group, and Y ¹ and Y ² may be linked with each other to form a ring; A ¹ , A ² , A ³ , A ⁴ , A ⁵ . A ⁶ , A ⁷ , A ⁸ , A ⁹ , A ¹⁰ and A ¹¹ are independently of one another a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group, an aryloxy group, an amino group, a substituted amino group, an amide group, an imide group or an alkylthio group, and A ³ and A ⁴ and/or A ⁵ and A ⁶ may be linked with each other to form a ring; m is 0 or 1; and n is an integer of 1 to 20. Also, the present invention is a process for producing the above-mentioned random copolymer, comprising the step of copolymerizing two or more kinds of diene compounds represented by the following formula ( 3 ) :

wherein all the symbols are the same as those defined in the formula (1); and A ⁸ preferably has a cis-form configuration with -(CH ₂ ) _n (CA ⁹ A ¹⁰ ) _m H as shown in the formula (3). In the present invention, the above-mentioned term "polymerization unit" means a unit of a polymerized monomer.

which is also referred to as a "repeating unit".

Best Mode for Carrying Out the Invention

Examples of the halogen atom of A ¹ to A ¹¹ in the formulas (1) and (3) are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, preferred is a fluorine atom.

Examples of the alkyl group of A ¹ to A ¹¹ in the formulas

( 1 ) and ( 3 ) are linear alkyl groups such as a methyl group , an ethyl group, and a n-butyl group; branched alkyl groups such as an isopropyl group, an isobutyl group, a tert-butyl group, and a neopentyl group; and cyclic alkyl groups such as a cyclohexyl group and a cyclooctyl group.

Examples of the aralky group of A ¹ to A ¹¹ in the formulas

(1) and (3) are a benzyl group, a phenethyl group, a 2-methylbenzyl group, a 3-methylbenzyl group, a

4-methylbenzyl group, a 2 , 6-dimethylbenzyl group, and a

3,5-dimethylbenzyl group.

Examples of the aryl group of A ¹ to A ¹¹ in the formulas

( 1 ) and ( 3 ) are a phenyl group, a tolyl group, a 1-biphenyl group, a 2-biphenyl group, a 3-biphenyl group, a 1-naphthyl group, a

2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a mesityl group.

Examples of the alkoxy group of A ¹ to A ¹¹ in the formulas

(1) and (3) are linear alkoxy groups such as a methoxy group, an ethoxy group, and a n-butoxy group; branched alkoxy groups such as an isopropoxy group, an isobutoxy group, a tert-butoxy

group, and a neopentoxy group; and cyclic alkoxy groups such as a cyclohexyloxy group and a cyclooctyloxy group.

Examples of the aralkyloxy group of A ¹ to A ¹¹ in the formulas ( 1 ) and ( 3 ) are a benzyloxy group , a phenethyloxy group, a 2-methylbenzyloxy group, a 3-methylbenzyloxy group, a

4-methylbenzyloxy group, a 2,6-dimethylbenzyloxy group, and a

3 , 5-dimethylbenzyloxy group .

Examples of the aryloxy group of A ¹ to A ¹¹ in the formulas (1) and (3) are a phenoxy group, a 2-methylphenoxy group, a 2-ethylphenoxy group, a 2-n-propylphenoxy group, a 2-isopropylphenoxy group, a 2-n-butylphenoxy group, a 2-isobutylphenoxy group, a 2-tert-butylphenoxy group, a 3-methylphenoxy group, a 3-isopropylphenoxy group, a 3-n-butylphenoxy group, a 3-tert-butylphenoxy group, a 4-methylphenoxy group, a 4-isopropylphenoxy group, a 4-n-butylphenoxy group, a 4-tert-butylphenoxy group, a 2, 3-dimethylphenoxy group, a 2,4-dimethylphenoxy group, a 2, 5-dimethylphenoxy group, a 2,6-dimethylphenoxy group, a 3,5-dimethylphenoxy group, a 2, 6-diisopropylphenoxy group, a 2,6-di-tert-butylphenoxy group, and a naphthoxy group.

Examples of the substituted amino group of A ¹ to A ¹¹ in the formulas (1) and (3) are an N-methylamino group, an N-ethylamino group, an N-n-butylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N,N-di-n-butylamino group, an N-isopropylamino group, an N-isobutylamino group, an N-tert-butylamino group, an

N-neopentylamino group, an N,N-diisopropylamino group, an N,N-diisobutylamino group, an N,N-di-tert-butylamino group, an N,N-dineopentylamino group, an N-cyclohexylamino group, an N-cyclooctylamino group, an N,N-dicyclohexylamino group, and an N,N-dicyclooctylamino group.

Examples of the amide group of A ¹ to A ¹¹ in the formulas (1) and (3) are an ethanamide group, a n-butanamide group, an N-methylethanamide group, an N-ethylethanamide group, an N-n-butylethanamide group, an isopropanamide group, an isobutanamide group, a tert-butanamide group, a neopentanamide , an N-isopropylethanamide group, an N-isobutylmethanamide group, an N-tert-butylethanamide group, an N-neopentylethanamide group, an N-cyclohexylethanamide group, and an N-cyclooctylethanamide group .

Examples of the imide group of A ¹ to A ¹¹ in the formulas ( 1 ) and ( 3 ) are a succinimide group, a maleimide group , and a phthalimide group .

Examples of the alkylthio group of A ¹ to A ¹¹ in the formulas (1) and (3) are linear alkylthio groups such as a methylthio group, an ethylthio group, and a n-butylthio group; branched alkylthio groups such as an isopropylthio group, an isobutylthio group, a tert-butylthio group, and a neopentylthio group; and cyclic alkylthio groups such as a cyclohexylthio group and a cyclooctylthio group.

The above-mentioned groups of A ¹ to A ¹¹ may have a

substituent such as a halogen atom, a hydroxyl group, a thiol group, an amino group, a carboxyl group, a carbamoyl group, a formyl group, a nitro group, a sulfonate group, a silyl group, a siloxy group, and a cyano group. Among them. A ¹ to A ¹¹ are preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or a methyl group, and further preferably a hydrogen atom.

A ³ and A ⁴ and/or A ⁵ and A ⁶ may be linked with each other to form a ring. Examples of the ring are aliphatic rings such as a cyclobutane ring, a cyclopentane ring and a cyclohexane ring, and aromatic rings. Those rings may have one or more substituents.

Examples of the halogen atom of Y ¹ and Y ² in the formulas (1) and (3) are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, preferred is a fluorine atom.

Examples of the alkoxycarbonyl group of Y ¹ and Y ² in the formulas ( 1 ) and ( 3 ) are linear alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group and a n-butoxycarbonyl group; branched alkoxycarbonyl groups such as an isopropoxycarbonyl group, an isobutoxycarbonyl group, a tert-butoxycarbonyl group and a neopentoxycarbonyl group; cyclic alkoxycarbonyl groups such as a cyclohexyloxycarbonyl group and a cyclooctyloxycarbonyl group.

Examples of the aralkyloxycarbony1 group of Y ¹ and Y ² in

the formulas (1) and (3) are a benzyloxycarbonyl group, a phenethyloxycarbonyl group, a 2-methylbenzyloxycarbonyl group, a 3-methylbenzyloxycarbonyl group, a 4-methylbenzyloxycarbonyl group, a 2, 6-dimethylbenzyloxycarbonyl group, and a 3 , 5-dimethylbenzyloxycarbonyl group .

Examples of the aryloxycarbonyl group of Y ¹ and Y ² in the formulas ( 1 ) and ( 3 ) are a phenoxycarbonyl group, a tolyloxycarbonyl group and a mesityloxycarbonyl group. Examples of the alkyl group of Y ¹ and Y ² in the formulas (1) and (3) are linear alkyl groups such as a methyl group, an ethyl group, and a n-butyl group; branched alkyl groups such as an isopropyl group, an isobutyl group, a tert-butyl group, and a neopentyl group; and cyclic alkyl groups such as a cyclohexyl group and a cyclooctyl group.

Examples of the aralkyl group of Y ¹ and Y ² in the formulas (1) and (3) are a benzyl group, a phenethyl group, a 2-methylbenzyl group, a 3-methylbenzyl group, a 4-methylbenzyl group, a 2,6-dimethylbenzyl group, and a 3,5-dimethylbenzyl group.

Examples of the aryl group of Y ¹ and Y ² in the formulas

( 1 ) and ( 3 ) are a phenyl group , a tolyl group and a mesityl group .

Examples of the silyl group of Y ¹ and Y ² in the formulas

(1) and (3) are mono-substituted silyl groups such as a methylsilyl group, an ethylsilyl group, and a phenylsilyl group; di-substituted silyl groups such as a dimethylsilyl

group, a diethylsilyl group, and a diphenylsilyl group; and tri-substituted silyl groups such as a trimethylsilyl group, a trimethoxysilyl group, a dimethylmethoxysilyl group, a methyldimethoxysilyl group, a triethylsilyl group, a triethoxysilyl group, a tri-n-propylsilyl group, a triisopropylsilyl group, a tri-n-butylsilyl group, a tri-sec-butylsilyl group, a tert-butyldimethylsilyl group, a triisobutylsilyl group, a tert-butyldiphenylsilyl group, a cyclohexyldimethylsilyl group, a tricyclohexylsilyl group, and a triphenylsilyl group. Among them, preferred is a tri-substituted silyl group, and further preferred is a trimethylsilyl group, a triethylsilyl group, a triphenylsilyl group, a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group, a cyclohexyldimethylsilyl group, or a triisopropylsilyl group.

Examples of the siloxy group of Y ¹ and Y ² in the formulas (1) and (3) are a trimethylsiloxy group, a trimethoxysiloxy group, a dimethylmethoxysiloxy group, a methyldimethoxysiloxy group, a triethylsiloxy group, a triethoxysiloxy group, a tri-n-propylsiloxy group, a triisopropylsiloxy group, a tri-n-butylsiloxy group, a tri-sec-butylsiloxy group, a tert-butyldimethylsiloxy group, a triisobutylsiloxy group, a tert-butyldiphenylsiloxy group, a cyclohexyldimethylsiloxy group, a tricyclohexylsiloxy group, and a triphenylsiloxy group. Among them, preferred is a trimethylsiloxy group, a triethylsiloxy group, a

triphenylsiloxy group, a tert-butyldimethylsiloxy group, a tert-butyldiphenylsiloxy group, a cyclohexyldimethylsiloxy group, or a triisopropylsiloxy group.

Examples of the alkoxy group of Y ¹ and Y ² in the formulas (1) and (3) are linear alkoxy groups such as a methoxy group, an ethoxy group, and a n-butoxy group; branched alkoxy groups such as an isopropoxy group, an isobutoxy group, a tert-butoxy group, and a neopentoxy group; and cyclic alkoxy groups such as a cyclohexyloxy group and a cyclooctyloxy group . Those alkoxy groups may have a substituent such as a halogen atom, an alkoxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

Examples of the aralkyloxy group of Y ¹ and Y ² in the formulas (1) and (3) are a benzyloxy group , a phenethyloxy group, a 2-methylbenzyloxy group, a 3-methylbenzyloxy group, a 4-methylbenzyloxy group, a 2, 6-dimethylbenzyloxy group, and a 3,5-dimethylbenzyloxy group. Those aralkyloxy groups may have a substituent such as a halogen atom, an alkoxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group. Examples of the aryloxy group of Y ¹ and Y ² in the formulas (1) and (3) are a phenoxy group, a 2-methylphenoxy group, a 2-ethylphenoxy group, a 2-n-propylphenoxy group, a 2-isopropylphenoxy group, a 2-n-butylphenoxy group, a 2-isobutylphenoxy group, a 2-tert-butylphenoxy group, a 3-methylphenoxy group, a 3-isopropylphenoxy group, a 3-n-butylphenoxy group, a 3-tert-butylphenoxy group, a 4-methylphenoxy group, a 4-isopropylphenoxy group, a

4-n-butylphenoxy group, a 4-tert-butylphenoxy group, a 2,3-dimethylphenoxy group, a 2, 4-dimethylphenoxy group, a 2,5-dimethylphenoxy group, a 2, 6-dimethylphenoxy group, a 3,5-dimethylphenoxy group, a 2, 6-diisopropylphenoxy group, a 2 , 6-di-tert-butylphenoxy group, and a naphthoxy group. Those aryloxy groups may have a substituent such as a halogen atom, an alkoxy group, a nitro group, a sulfonate group, a silyl group, and a cyano group.

Examples of the acyl group of Y ¹ and Y ² in the formulas (1) and (3) are an acetyl group, a n-propanoyl group, a n-butanoyl group, a n-pentanoyl group, a n-hexanoyl group, a 2-methylpropanoyl group, a pivaloyl group, a 2-methylbutanoyl group, a benzoyl group, a 1-naphthoxyl group, and a 2-naphthoyl group . Examples of the substituted amino group of Y ¹ and Y ² in the formulas (1) and (3) are linear alkylamino groups such as an N-methylamino group, an N-ethylamino group, an N-n-butylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, and an N,N-di-n-butylamino group; branched alkylamino groups such as an N-isopropylamino group, an N-isobutylamino group, an N-tert-butylamino group, an N-neopentylamino group, an N,N-diisopropylamino group, an N,N-diisobutylamino group, an N,N-di-tert-butylamino group, and an N,N-dineopentylamino group; and cyclic alkylamino groups such as an N-cyclohexylamino group, an N-cyclooctylamino group, an N,N-dicyclohexylamino group.

and an N.N-dicyclooctylamino group.

Examples of the amide group of Y ¹ and Y ² in the formulas (1) and (3) are an ethanamide group, a n-butanamide group, an N-methylethanamide group, an N-ethylethanamide group, an N-n-butylethanamide group, an isopropanamide group, an isobutanamide group, a tert-butanamide group, a neopentanamide group, an N-isopropylethanamide group, an N-isobutylethanamide group, an N-tert-butylethanamide group, and an N-neopentylethanamide group. Examples of the imide group of Y ¹ and Y ² in the formulas (1) and (3) are a maleimide group, a phthalimide group and a succinimide group.

Examples of the alkylthio group of Y ¹ and Y ² in the formulas ( 1 ) and ( 3 ) are linear alkylthio groups such as a methylthio group, an ethylthio group, and a n-butylthio group; branched alkylthio groups such as an isopropylthio group, an isobutylthio group, a tert-butylthio group, and a neopentylthio group; and cyclic alkylthio groups such as a cyclohexylthio group and a cyclooctylthio group. Examples of the aralkylthio group of Y ¹ and Y ² in the formulas (1) and (3) are a benzylthio group, a 1-naphthylmethylthio group, a 2-naphthylmethylthio group, and a 9-fluorenylmethylthio group.

Examples of the arylthio group of Y ¹ and Y ² in the formulas (1) and (3) are a phenylthio group, a 1-naphthyltio group, a 2-naphthylthio group, and a 9-fluorenylthio group.

Examples of the alkylthioxycarbony1 group of Y ¹ and Y ² in the formulas ( 1 ) and ( 3 ) are a methylthioxycarbonyl group , an ethylthioxycarbonyl group, an isopropylthioxycarbonyl group, a tert-butylthioxycarbonyl group, and a cyclohexylthioxycarbonyl group.

An examples of the arylthioxycarbonyl group of Y ¹ and

Y ² in the formulas ( 1 ) and ( 3 ) is a phenylthioxycarbonyl group .

Y ¹ and Y ² in the formulas (1) and (3) may have a substituent independently of each other. Examples of the substituent are a hydrogen atom, a halogen atom, a hydroxyl group, a nitrile group, an aldehyde group, an alkyl group, an aralkyl group, an aryl group, a silyl group, a siloxy group, an alkoxy group, an aralkyloxy group, an aryloxy group, an acyl group, an amino group, an amide group, an imide group, a thiol group, an alkylthio group, an aralkylthio group, an arylthio group, an alkylthioxycarbonyl group, and an arylthioxycarbonyl group.

Y ¹ and Y ² in the formulas ( 1 ) and ( 3 ) may be linked with each other to form a ring. Examples of the ring are hydrocarbon rings such as a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, a cyclodecane ring, a decahydronaphthalene ring, a norbornane ring, a 1,2,3,4-tetrahydronaphthalene ring, a norbornene ring, an ethylidenenorbornene ring, an indane ring, a fluorene ring, and an acenaphthylene ring; ketone group-carrying rings such

as a cyclopropan-1-one ring, a cyclobutan-1-one ring, a cyclopentan-1-one ring, a cyclohexan-1-one ring, a cycloheptan-1-one ring, a cyclooctan-1-one ring, a cyclononan-1-one ring, a cyclodecan-1-one ring, a cyclopropan-1 , 2-dione ring, a cyclobutan-l,3-dione ring, a cyclopentan-1 , 3-dione ring, a cyclohexan-1 ,3-dione ring, a cycloheptan-l,3-dione ring, a cyclooctan-1, 3-dione ring, a cyclononan-1, 3-dione ring, a cyclodecan-1, 3-dione ring, an indan-1-one ring, an indan-2-one ring, an indan-1, 3-dione ring, a tetralin-1-one ring, a tetralin-1, 3-dione ring, and a tetralin-1 , 4-dione ring; ether bond-carrying rings such as an oxirane ring, an oxetane ring, an oxolane ring, an oxane ring, a 1,3-dioxetane ring, a 1,3-dioxolane ring, a 1,3-dioxane ring, a 1,4-dioxane ring, a 1,3, 5-trioxane ring, a phthalan ring, a coumaran ring, a chromane ring, an isochromane ring, a xanthene ring, a 1 , 3-benzodioxane ring, a 1,4-benzodioxane ring, and a benzodioxolane ring; amino group or substituted amino group-carrying rings such as a pyrazolidine ring, a morpholine ring, an imidazolidine ring, a pyrrolidine ring, a piperidine ring, a hexahydropyrimidine ring, a piperadine ring, an indoline ring, an indazolin ring, a 1 , 2, 3 , 4-tetrahydroquinoline ring, a

1,2,3,4-tetrahydroisoquinoline ring, an

N-methylpyrazolidine ring, an N-methylmorpholine ring, an N,N' -dimethylpyrazolidine ring, an N-methylimidazolidine ring, an N,N' -dimethylimidazolidine ring, an

N-methylpyrrolidine ring, an N-methylpiperidine ring, an N-methylhexahydropyrimidine ring, an

N,N' -dimethylhexahydropyrimidine ring, an N-methylpiperadine ring, an N,N' -diethylpiperadine ring, an N-ethylpyrazolidine ring, an N,N' -diethylpyrazolidine ring, an N-ethylimidazolidine ring, an N,N' -diethylimidazolidine ring, an N-ethylpyrrolidine ring, an N-ethylpiperidine ring, an N-ethylpiperadine ring, an N-ethylhexahydropyrimidine ring, an N,N' -diethylhexahydropyrimidine ring, an N,N ' -diethylpiperadine ring, an N-phenylpyrazolidine ring, an N,N' -diphenylpyrazolidine ring, an N-phenylimidazolidine ring, an N,N' -diphenylimidazolidine ring, an N-phenylpyrrolidine ring, an N-phenylpiperidine ring, an N-phenylhexahydropyrimidine ring, an N,N' -diphenylhexahydropyrimidine ring, an N-phenylpiperadine ring, an N-methylindoline ring, an N-methylindazolin ring, an N,N' -dimethylindazolin ring, an N-methyl-1, 2,3, 4-tetrahydroquinoline ring, and an N-methyl-l,2,3,4-tetrahydroisoquinoline ring; ester bond-carrying rings such as an CK -lactone ring, a β -lactone ring, a T -lactone ring, a δ -lactone ring, an ε -caprolactone ring, a l,3-dioxolan-4-one ring, a 1 , 4-dioxan-2-one ring, a 1 , 4-dioxan-2 , 5-dione ring, a 1 , 3-dihydroisobenzofuran-l-one ring, a 2 , 3-dihydro-l-benzofuran-2-one ring, a 3 , 4-dihydro-2H-l-benzopyran-3-one ring, and a 3,4-dihydro-lH-2-benzopyran-3-one ring; carbonate

bond-carrying rings such as a 1, 3-dioxan-2-one ring and a 1 , 3-dioxolan-2-one ring; amide group-carrying rings such as an a -lactam ring, a β -lactam ring, a 7 -lactam ring, a δ -lactam ring, an ε -caprolactam ring, an imidazolidin-4-one ring, a pyrazolidin-3-one ring, a piperadin-2-one ring, a piperadin-2,5-dione ring, a l,2,3,4-tetrahydroquinolin-3-one ring, a

1 , 2, 3 , 4-tetrahydroisoquinolin-l-one ring, a 1 , 2, 3 , 4-tetrahydro-l-isoquinolin-3-one ring, an N-methyl- CK -lactam ring, an N-methyl- β -lactam ring, an N-methyl- T -lactam ring, an N-methyl- δ -lactam ring, an N-methyl- ε -caprolactam ring, an N-methylimidazolidin-4-one ring, an N-methylpiperadin-2-one ring, an

N-methylpiperadin-2,5-dione ring, an N-methyl-l,2,3,4-tetrahydroquinolin-3-one ring, an N-methyl-1, 2 , 3 , 4-tetrahydroisoquinolin-l-one ring, and an N-methyl-1 , 2 , 3 , 4-tetrahydro-l-isoquinolin-3-one ring; imide group-carrying rings such as a hexahydropyrimidin-2,4,6-trione ring, an N-methylhexahydropyrimidin-2,4,6-trione ring, an N,N' -dimethylhexahydropyrimidin-2 , 4 , 6-trione ring, an N-ethylhexahydropyrimidin-2,4,6-trione ring, an N,N' -diethylhexahydropyrimidin-2, 4, 6-trione ring, an N-phenylhexahydropyrimidin-2 , 4 , 6-trione ring, and an N,N ' -diphenylhexahydropyrimidin-2,4,6-trione ring; urethane bond-carrying rings such as a 1, 3-oxazolidin-2-one

ring; and urea bond-carrying rings such as an imidazolidin-2-one ring and a hexahydropyrimidin-2-one ring. Those rings may have one or more substituents .

Among them, preferred are hydrocarbon rings, ketone group-carrying rings, ether bond-carrying rings, ester bond-carrying rings, amide group-carrying rings, imide group-carrying rings, or urea bond-carrying rings.

Compounds represented by the formula ( 3 ) may be known in the art. Examples thereof are Meldrum's acid derivatives such as 5,5-diallyl Meldrum's acid, 5-allyl-5-( (2E)-2-butenyl) Meldrum's acid, 5-allyl-5-( (2E) -2-pentenyl) Meldrum's acid, 5-allyl-5-( (2E) -2-hexenyl) Meldrum's acid, 5-allyl-5-( (2E) -2-heptenyl) Meldrum's acid, 5-allyl-5-((2E)-2-octenyl) Meldrum's acid, 5-allyl-5-( (2E) -2-nonenyl) Meldrum's acid, 5-allyl-5-( (2E) -2-decenyl) Meldrum's acid, 5-allyl-5-( (2E) -2-undecenyl) Meldrum's acid, and 5-allyl-5- ( ( 2E) -2-dodecenyl) Meldrum's acid; malonic diester derivatives such as dimethyl 2,2-diallylmalonate, diethyl 2,2-diallylmalonate, di-n-propyl 2,2-diallylmalonate, diisopropyl 2,2-diallylmalonate, di-n-butyl 2,2-diallylmalonate, diisobutyl 2,2-diallylmalonate, di-tert-butyl 2,2-diallylmalonate, diethyl 2-allyl-2- ( (2E) -2-butenyl)malonate, diethyl 2-allyl-2-( (2E) -2-pentenyl)malonate, diethyl

2-allyl-2- ( (2E) -2-hexenyl)malonate, diethyl

2-allyl-2-( (2E)-2-heptenyl)malonate, diethyl

2-allyl-2-( (2E) -2-octenyl)malonate, diethyl

2-allyl-2-( (2E)-2-nonenyl)malonate, diethyl 2-allyl-2-( (2E)-2-decenyl)malonate, diethyl

2-allyl-2- ( (2E) -2-undecenyl)malonate, and diethyl 2-allyl-2- ( (2E) -2-dodecenyl)malonate; ether bond-containing compounds such as 2, 2-diallyl-l, 3-dioxane, 4,4-diallyl-1,3-dioxane , 5,5-diallyl-1,3-dioxane , 2, 2-diallyl-1,4-dioxane, 2 , 2-diallyl-l , 3-dioxolane, 4,4-diallyl-1,3-dioxolane , 2 , 2-dimethyl-5 , 5-diallyl-1 , 3-dioxane, 2-allyl-2-((2E)-2-butenyl)-l, 3-dioxane, 4-allyl-4- ( (2E) -2-butenyl) -1, 3-dioxane, 5-allyl-5-( (2E)-2-butenyl)-l, 3-dioxane, 2-allyl-2-( (2E) -2-butenyl) -1.4-dioxane, 2-allyl-2-((2E)-2-butenyl) -1 , 3-dioxolane, 4-allyl-4-( (2E) -2-butenyl) -1, 3-dioxolane, 2, 2-dimethyl-5-allyl-5-( (2E) -2-butenyl)-l, 3-dioxane, 2-allyl-2-( (2E) -2-pentenyl)-l.3-dioxane, 5-allyl-5- ( (2E) -2-pentenyl) -1 , 3-dioxane. 2-allyl-2-((2E)-2-pentenyl) -1 , 4-dioxane , 2-allyl-2-( (2E) -2-pentenyl)-l, 3-dioxolane. 4-allyl-4-( (2E) -2-pentenyl) -1 , 3-dioxolane, 2, 2-dimethyl-5-allyl-5- ( ( 2E) -2-pentenyl) -1 , 3-dioxane, 2,2-dimethyl-5-allyl-5-( (2E) -2-hexenyl) -1 , 3-dioxane,

2 , 2 -dimethyl- 5 -allyl- 5 - ( ( 2E ) - 2 -heptenyl ) - 1 , 3 -dioxane ,

2 , 2-dimethyl-5-allyl-5- ( ( 2E ) -2-octenyl) -1 , 3-dioxane ,

2,2-dimethyl-5-allyl-5-( (2E) -2-nonenyl) -1 , 3-dioxane,

2 , 2-dimethyl-5-allyl-5- ( ( 2E) -2-decenyl) -1 , 3-dioxane, 2,2-dimethyl-5-allyl-5-( (2E) -2-undecenyl) -1 , 3-dioxane,

2 , 2-dimethyl-5-allyl-5-((2E)-2-dodecenyl) -1 , 3-dioxane ,

2,2-dimethyl-5-allyl-5-( (2E) -2-tridecenyl) -1, 3-dioxane,

2 , 2-dimethyl-4 , 4-diallyl-1 , 3-dioxane ,

2 , 2-dimethyl-4 , 4-diallyl-1 , 3-dioxolane , 2, 2-diethyl-4,4-diallyl-l, 3-dioxane,

2,2-diethyl-5,5-diallyl-1,3-dioxane ,

2,2-diethyl-4,4-diallyl-1,3-dioxolane ,

2-methyl-4, 4-diallyl-1,3-dioxane,

2-methyl-5, 5-diallyl-1 , 3-dioxane, 2-methyl-4,4-diallyl-1,3-dioxolane ,

2-ethyl-4, 4-diallyl-1,3-dioxane,

2-ethyl-5.5-diallyl-1,3-dioxane ,

2-ethyl-4,4-diallyl-1,3-dioxolane ,

2-n-propyl-4,4-diallyl-1,3-dioxane , 2-n-propyl-5,5-diallyl-1,3-dioxane ,

2-n-propyl-4,4-diallyl-l,3-dioxolane,

2-isopropyl-4 , 4-diallyl-1 , 3-dioxane,

2-isopropyl-5,5-diallyl-1,3-dioxane ,

2-isopropyl-4 , 4-diallyl-1 , 3-dioxolane , 2-n-butyl-4 , 4-diallyl-1 , 3-dioxane ,

2-n-butyl-5,5-diallyl-1,3-dioxane , and

2-n-butyl-4, 4-diallyl-l, 3-dioxolane; ketone group-containing compounds such as 2,2-diallylcyclobutan-1,3-dione , 2, 2-diallylcyclopentan-l , 3-dione, 2,2-diallylcyclohexan-1,3-dione, 2,2-diallylcycloheptan-1,3-dione, 2 , 2-diallylcyclooctan-l, 3-dione, 2 , 2-diallylcyclononan-l, 3-dione, 2-allyl-2-((2E)-2-butenyl ) cyclohexan-1,3-dione , 2-allyl-2-( (2E)-2-pentenyl) cyclohexan-1,3-dione, 2-allyl-2- ( (2E) -2-hexenyl) cyclohexan-1, 3-dione, 2-allyl-2- ( ( 2E) -2-heptenyl) cyclohexan-1 , 3-dione, 2-allyl-2- ( ( 2E) -2-octenyl) cyclohexan-1 , 3-dione, 2-allyl-2- ( (2E)-2-nonenyl) cyclohexan-1,3-dione, 2-allyl-2- ( (2E) -2-decenyl)cyclohexan-1 , 3-dione,

2-allyl-2-((2E)-2-undecenyl)cyclohexan-1,3-dione , 2-allyl-2-((2E)-2-dodecenyl)cyclohexan-1,3-dione , 2-allyl-2- ( ( 2E ) -2-tridecenyl)cyclohexan-1,3-dione , 2-allyl-2-((2E)-2-tetradecenyl)cyclohexan-1,3-dione , 2-allyl-2-((2E)-2-hexadecenyl)cyclohexan-1,3-dione , 2,2-diallylindan-1,3-dione , 2-allyl-2-((2E)-2-butenyl) indan- 1,3-dione , 2-allyl-2-( (2E) -2-pentenyl) indan- 1, 3-dione, 2-allyl-2-( ( 2E) -2-hexenyl) indan- 1 , 3-dione, 2-allyl-2-( (2E) -2-heptenyl) indan-1,3-dione, 2-allyl-2-( (2E) -2-octenyl) indan-1, 3-dione,

2 -allyl- 2 - ( ( 2E ) - 2 -nonenyl ) indan- 1 , 3 -dione ,

2-allyl-2-((2E)-2-decenyl) indan-1 , 3-dione,

2-allyl-2-((2E)-2-undecenyl) indan-1,3-dione ,

2-allyl-2- ( (2E) -2-dodecenyl) indan-1, 3-dione, 2-allyl-2-( (2E) -2-tridecenyl) indan-1 , 3-dione,

2-allyl-2- ( ( 2E) -2-tetradecenyl) indan-1,3-dione, and

2-allyl-2-( (2E) -2-hexadecenyl) indan-1 , 3-dione; propanediamide derivatives such as

2,2-diallylpropanediamide and 2-allyl-2-( ( 2E) -2-butenyl)propanediamide;

N-alkylpropanediamide derivatives such as

N-methyl-2,2-diallylpropanediamide,

N-ethyl-2 , 2-diallylpropanediamide and

N-methyl-2-allyl-2-((2E)-2-butenyl )propanediamide; N,N-dialkylpropanediamide derivatives such as

N,N-dimethyl-2 , 2-diallylpropanediamide and

N,N-dimethyl-2-allyl-2- ( ( 2E) -2-butenyl)propanediamide;

N.N' -dialkylpropanediamide derivatives such as

N,N ' -dimethyl-2,2-diallylpropanediamide , N,N' -diethyl-2, 2-diallylpropanediamide.

N,N' -di-n-propyl-2 , 2-diallylpropanediamide,

N,N ' -diisopropyl-2,2-diallylpropanediamide,

N,N ' -di-n-butyl-2,2-diallylpropanediamide ,

N,N' -diisobutyl-2 , 2-diallylpropanediamide, N,N ' -di-tert-butyl-2,2-diallylpropanediamide ,

N,N ' -dineopentyl-2,2-diallylpropanediamide ,

N,N ' -dicyclohexyl-2,2-diallylpropanediamide , N,N' -di-n-hexyl-2 , 2-diallylpropanediamide, N,N ' -dicyclopentyl-2,2-diallylpropanediamide , N,N' -diethyl-2-allyl-2- ( (2E) -2-butenyl)propanediamide, N,N' -diethyl-2-allyl-2- ( (2E) -2-pentenyl)propanediamide, N,N' -diethyl-2-allyl-2- ( (2E) -2-hexenyl)propanediamide, N,N' -diethyl-2-allyl-2- ( (2E) -2-heptenyl)propanediamide, N,N ' -diethyl-2-allyl-2-((2E)-2-octenyl )propanediamide , N,N ' -diethyl-2-allyl-2-((2E)-2-nonenyl )propanediamide , N,N'-diethyl-2-allyl-2-((2E)-2-decenyl)propanediamide,

N,N ' -diethyl-2-allyl-2-((2E)-2-undecenyl )propanediamide , and

N,N' -diethyl-2-ally1-2- ( (2E) -2-dodecenyl)propanediamide;

N,N,N' -trialkylpropanediamide derivatives such as N,N,N ' -trimethyl-2, 2-diallylpropanediamide and

N,N,N'-trimethyl-2-allyl-2-( (2E) -2-butenyl)propanediamide; N,N,N' ,N' -tetraalkylpropanediamide derivatives such as N,N,N' ,N ^f -tetramethyl-2, 2-diallylpropanediamide and N,N,N' ,N'-tetramethyl-2-allyl-2-((2E)-2-butenyl) propanediamide; N-arylpropanediamide derivatives such as N-phenyl-2 , 2-diallylpropanediamide and

N-phenyl-2-aryl-2- ( ( 2E) -2-butenyl)propanediamide ; N,N' -diarylpropanediamide derivatives such as N,N ' -diphenyl-2,2-diallylpropanediamide and N,N ^r -diphenyl-2-aryl-2-( (2E) -2-butenyl)propanediamide;

N-aralkypropanediamide derivatives such as

N-benzyl-2 , 2-diallylpropanediamide and N-benzyl-2-aryl-2- ( ( 2E) -2-butenyl)propanediamide;

N,N' -diaralkylpropanediamide derivatives such as

N,N' -dibenzyl-2 , 2-diallylpropanediamide and N.N' -dibenzyl-2-aryl-2- ( (2E) -2-butenyl )propanediamide; barbituric acid derivatives such as 5, 5-diallylbarbituric acid and 5-ally-5- ( (2E) -2-butenyl)barbiturc acid;

N-alkylbarbituric acid derivatives such as

N-methyl-5 , 5-diallylbarbituric acid, N-ethyl-5, 5-diallylbarbituric acid, and

N-methyl-5-ally-5-( (2E) -2-butenyl)barbiturc acid;

N,N' -dialkylbarbiturc acid derivatives such as

N,N' -dimethyl-5, 5-diallylbarbituric acid,

N,N ' -diethyl-5.5-diallylbarbituric acid. N,N'-di-n-propyl-5, 5-diallylbarbituric acid.

N.N' -diisopropyl-5, 5-diallylbarbituric acid,

N.N' -di-n-butyl-5, 5-diallylbarbituric acid,

N,N' -diisobutyl-5, 5-diallylbarbituric acid,

N,N' -di-tert-butyl-5, 5-diallylbarbituric acid, N,N ' -dineopentyl-5,5-diallylbarbituric acid,

N,N' -dicyclohexyl-5, 5-diallylbarbituric acid,

N,N'-di-n-hexyl-5, 5-diallylbarbituric acid, N.N'-dicyclopentyl-5,5-diallylbarbituric acid,

N,N'-dimethyl-5-ally-5-((2E)-2-butenyl)barbituric acid, N,N'-dimethyl-5-ally-5-((2E)-2-pentenyl) barbituric acid,

N,N'-dimethyl-5-ally-5-( (2E) -2-hexenyl) barbituric acid.

N,N' -dimethyl-5-ally-5-( (2E) -2-heptenyl) barbituric acid, N,N'-dimethyl-5-ally-5-((2E)-2-octenyl) barbituric acid, N,N'-dimethyl-5-ally-5-( (2E) -2-nonenyl) barbituric acid, N,N' -dimethyl-5-ally-5-( (2E) -2-decenyl) barbituric acid, N,N' -dimethyl-5-ally-5-( (2E) -2-undecenyl) barbituric acid, and N,N' -dimethyl-S-ally-5- ( (2E) -2-dodecenyl) barbituric acid; N-arylbarbituric acid derivatives such as N-phenyl-5, 5-diallylbarbituric acid and

N-phenyl-5-ally-5- ( (2E) -2-butenyl)barbituric acid; N,N' -diarylbarbituric acid derivatives such as N,N ' -diphenyl-5, 5-diallylbarbituric acid and N,N ^f -diphenyl-5-ally-5- ( (2E) -2-butenyl)barbituric acid; N-aralkylbarbituric acid derivatives such as N-benzyl-5, 5-diallylbarbituric acid and N-benzyl-5-ally-5-( ( 2E) -2-butenyl )barbituric acid; N,N ^f -diaralkylbarbituric acid derivatives such as N,N ' -dibenzyl-5, 5-diallylbarbituric acid and N,N'-dibenzyl-5-ally-5- ( (2E) -2-butenyl)barbituric acid; pyrazolidine-3,5-dione derivatives such as 4,4-diallylpyrazolidine-3,5-dione and

4-allyl-4- ( (2E) -2-butenyl)pyrazolidine-3 , 5-dione; N-alkylpyrazolidine-3,5-dione derivatives such as N-methyl-4 , 4-diallylpyrazolidine-3 , 5-dione and

N-methyl-4-allyl-4- ( ( 2E ) -2-butenyl )pyrazolidine-3 , 5-dione; N,N' -dialkylpyrazolidine-3, 5-dione derivatives such as N ₁ N ¹ -dimethyl-4,4-diallylpyrazolidine-3,5-dione ,

N,N' -diethyl-4 , 4-diallylpyrazolidine-3 , 5-dione , N,N' -di-n-propyl-4 , 4-diallylpyrazolidine-3 , 5-dione, N,N' -diisopropyl-4 , 4-diallylpyrazolidine-3 , 5-dione, N,N' -di-n-butyl-4, 4-diallylpyrazolidine-3, 5-dione, N,N ^f -diisobutyl-4 , 4-diallylpyrazolidine-3 , 5-dione,

N,N'-di-tert-butyl-4, 4-diallylpyrazolidine-3, 5-dione,

N,N' -dineopentyl-4,4-diallylpyrazolidine-3,5-dione ,

N,N' -dicyclopentyl-4 , 4-diallylpyrazolidine-3 , 5-dione,

N,N' -di-n-hexyl-4, 4-diallylpyrazolidine-3, 5-dione, and N,N' -dicyclohexyl-4 , 4-diallylpyrazolidine-3, 5-dione;

N-arylpyrazolidine-3, 5-dione derivatives such as N-phenyl-4 , 4-diallylpyrazolidine-3 , 5-dione, N-phenyl-4-ally-4-((2E)-2-butenyl)pyrazolidine-3,5-dione , N- ( 2-naphthyl) -4 , 4-diallylpyrazolidine-3,5-dione, and N- ( 2-anthracenyl ) -4 , 4-diallypyrazolidine-3 , 5-dione;

N,N' -diarylpyrazolidine-3, 5-dione derivatives such as N,N' -diphenyl-4 , 4-diallylpyrazolidine-3, 5-dione, N,N' -diphenyl-4-ally-4-((2E)-2-butenyl )pyrazolidine-3,5- dione , N,N'-diphenyl-4-ally-4-( ( 2E) -2-pentenyl)pyrazolidine-3, 5- dione,

N,N ' -diphenyl-4-ally-4- ( ( 2E ) -2-hexenyl )pyrazolidine-3 , 5- dione, N,N' -diphenyl-4-ally-4- ( ( 2E) -2-heptenyl)pyrazolidine-3 , 5- dione,

N ₁ N ¹ -diphenyl-4-ally-4- ( ( 2E ) -2-octenyl )pyrazolidine-3 , 5-

dione ,

N,N ' -diphenyl-4-ally-4-((2E)-2-nonenyl)pyrazolidine-3,5- dione ,

N,N ^F -diphenyl-4-ally-4-( (2E) -2-decenyl)pyrazolidine-3 , 5- dione,

N,N ' -diphenyl-4-ally-4- ( ( 2E) -2-undecenyl)pyrazolidine-3,5- dione ,

N,N' -diphenyl-4-ally-4-( (2E) -2-dodecenyl)pyrazolidine-3, 5- dione , N,N'-bis(2-naphthyl)-4,4-diallylpyrazolidine-3,5-dione, and

N,N' -di(2-anthracenyl)-4,4-diallylpyrazolidine-3,5-dione;

N-aralkylpyrazolidine-3,5-dione derivatives such as

N-benzyl-4 , 4-diallylpyrazolidine-3 , 5-dione,

N-benzyl-4-ally-4-( (2E) -2-butenyl)pyrazolidine-3 , 5-dione, and N- (9-fluorenylmethyl) -4 , 4-diallylpyrazolidine-3, 5-dion;

N,N' -diaralkylpyrazolidine-3, 5-dione derivatives such as

N,N' -dibenzyl-4,4-diallylpyrazolidine-3,5-dione,

N,N' -dibenzyl-4-ally-4- ( (2E) -2-butenyl)pyrazolidine-3 , 5- dione , and N,N' -bis ( 9-fluorenylmethyl) -4, 4-diallylpyrazolidine-3, 5- dione; and fluorene derivatives such as 9, 9-diallylfluorene,

2 , 7-di-tert-butyl-9 , 9-diallylfluorene,

2 , 7-difluoro-9 , 9-diallylfluorene,

2,7-dichloro-9,9-diallylfluorene , 2 , 7-dibromo-9 , 9-diallylfluorene,

2 , 7-diiodo-9 , 9-diallylfluorene,

2-iodo-7-bromo-9 , 9-diallylfluorene, 2- (N,N-diphenylamino) -7-bromo-9 , 9-diallylfluorene, 3, 6-di-tert-butyl-9, 9-diallylfluorene, 3,6-difluoro-9,9-diallylfluorene , 3, 6-dichloro-9, 9-diallylfluorene, 3,6-dibromo-9,9-diallylfluorene , 3,6-diiodo-9,9-diallylfluorene , 3-iodo-6-bromo-9 , 9-diallylfluorene, 3- (N,N-diphenylamino) -6-bromo-9 , 9-diallylfluorene, 9-allyl-9-( (2E)-2-butenyl)-fluorene, 9-allyl-9-( (2E)-2-pentenyl)-fluorene, 9-allyl-9- ( (2E) -2-hexenyl) -fluorene, 9-allyl-9- ( (2E) -2-octenyl) -fluorene, 9-allyl-9-((2E)-2-nonenyl) -fluorene , 9-allyl-9-( (2E) -2-decenyl) -fluorene,

9-allyl-9- ( ( 2E) -2-undecenyl) -fluorene,

9-allyl-9-( (2E)-2-dodecenyl) -fluorene, and

9-allyl-9- ( (2E) -2-tridecenyl) -fluorene. Among them, particularly preferred are barbituric acid derivatives, N-alkylbarbituric acid derivatives, N,N' -dialkylbarbiturc acid derivatives, N-arylbarbituric acid derivatives, N,N' -diarylbarbituric acid derivatives, N-aralkylbarbituric acid derivatives, N,N ' -diaralkylbarbituric acid derivatives, N,N' -dialkylpyrazolidine-3 , 5-dione derivatives , N,N' -diarylpyrazolidine-3, 5-dione derivatives, or fluorene derivatives .

Major examples of the random copolymer of the present invention are a random copolymer of 5,5-diallyl Meldrum's acid and 2 , 2-dimethyl-5, 5-diallyl-l , 3-dioxane, a random copolymer of 5,5-diallyl Meldrum's acid and dimethyl 2 , 2-diallylmalonate, a random copolymer of 5,5-diallyl Meldrum's acid and 2, 2-diallyl-1, 3-dioxane, a random copolymer of 5,5-diallyl Meldrum's acid and 5, 5-diallylbarbituric acid, a random copolymer of 5,5-diallyl Meldrum' s acid and N,N' -dimethyl-4 , 4-diallylpyrazolidine-3, 5-dione, a random copolymer of 5,5-diallyl Meldrum's acid and 9,9-diallylfluorene, a random copolymer of 2, 2-dimethy1-5, 5-diallyl-1, 3-dioxane and dimethyl 2, 2-diallylmalonate, a random copolymer of 2, 2-dimethyl-5, 5-diallyl-1, 3-dioxane and

2, 2-diallyl-1, 3-dioxane, a random copolymer of 2,2-dimethyl-5,5-diallyl-1,3-dioxane and

5, 5-diallylbarbituric acid, a random copolymer of 2,2-dimethyl-5,5-diallyl-1,3-dioxane and N,N' -dimethyl-4,4-diallylpyrazolidine-3, 5-dione, a random copolymer of 2, 2-dimethyl-5, 5-diallyl-l, 3-dioxane and 9,9-diallylfluorene, a random copolymer of dimethyl 2, 2-diallylmalonate and 2, 2-diallyl-1 , 3-dioxane, a random copolymer of dimethyl 2 , 2-diallylmalonate and 5 , 5-diallylbarbituric acid, a random copolymer of dimethyl 2 , 2-diallylmalonate and

N,N' -dimethyl-4 , 4-diallylpyrazolidine-3, 5-dione, a random copolymer of dimethyl 2,2-diallylmalonate and 9 , 9-diallylfluorene, a random copolymer of 2,2-diallyl-l,3-dioxane and 5, 5-diallylbarbituric acid, a random copolymer of 2,2-diallyl-l,3-dioxane and N,N' -dimethyl-4,4-diallylpyrazolidine-3, 5-dione, a random copolymer of 2,2-diallyl-l,3-dioxane and 9 , 9-diallylfluorene, a random copolymer of 5 , 5-diallylbarbituric acid and N,N' -dimethyl-4 , 4-diallylpyrazolidine-3 , 5-dione, a random copolymer of 5, 5-diallylbarbituric acid and 9, 9-diallylfluorene, and a random copolymer of N,N' -dimethyl-4 , 4-diallylpyrazolidine-3 , 5-dione and 9 , 9-diallylfluorene . In order to raise the above-mentioned heat resistance of the random copolymer of the present invention, one or more kinds of polymerization units among two or more kinds of polymerizationunits , whicharecontainedin therandomcopolymer of the present invention, and are represented by the formula (1) , have preferably a trans-form configuration between A ⁷ and A ⁸ represented by the following formula ( 2 ) :

(2)

wherein all the symbols are the same as those defined in the formula ( 1 ) .

A proportion of the polymerization units having the above-mentioned trans-form configuration is measured by a ¹³ C-NMR spectrum using a solution of the random copolymer of the present invention in chloroform-di. A peak (i) appearing at 45 to 48 ppm in the ¹³ C-NMR spectrum is assigned to two carbon atoms linking with each of A ⁷ and A ⁸ having a trans-form configuration represented by the formula (2), and a peak (ii) appearing at 39 to 42 ppm therein is assigned to two carbon atoms linking with each of A ⁷ and A ⁸ having a cis-form configuration, provided that a peak assigned to chloroform-di (solvent) appears at 77 ppm. Therefore, the proportion of the polymerization units having the trans-form configuration is calculated from the following formula:

proportion (%) of polymerization units having trans-form configuration = area of peak (i) X 100/ [area of peak (i) + area of peak (ϋ)].

The random copolymer of the present invention may comprise olefin units besides two or more kinds of polymerization units represented by the formula (1). The term

"olefin unit" means a polymerization unit of an olefin. The

olefin unit has a chemical structure formed by a cleavage-polymerization reaction of a carbon-to-carbon double bond contained in an olefin, and is the same as a polymerization unit contained in an addition polymer of an olefin, such as an ethylene unit (-CH ₂ CH ₂ -) contained in an addition polymer of ethylene, polyethylene.

Examples of the olefin are linear olefins such as ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene and 1-decene; branched olefins such as 3-methyl-l-butene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, and vinylcyclohexane; and cyclic olefins such as cyclopropene , cyclobutene, cyclopentene , cyclohexene, cycloheptene , norbornene, limonene, a -pinene, β -pinene, camphene, cis-cyclooctene, trans-cyclooctene, cis-cyclononene, trans-cyclononene, cis-cyclodecene, and trans-cyclodecene. Among them, preferred is an olefin having 2 to 20 carbon atoms, further preferred is an olefin having 2 to 8 carbon atoms , and particularly preferred is ethylene, propylene, 1-butene, 1-pentene, cyclopentene, 1-hexene, 4-methyl-1-pentene, or 1-octene.

Those olefins may be used in combination with a diene compound. Examples of the diene compound are conjugated dienes such as butadiene and isoprene; linear non-conjugated dienes such as 1, 4-pentadiene and 1 , 5-hexadiene; and cyclic non-conjugated dienes such as cyclopentadiene.

cyclohexadiene , cycloheptadiene , cyclooctadiene , cyclononadiene , ethylidene norbornene, norbornadiene, and dicyclopentadiene .

When the random copolymer of the present invention comprises the above-mentioned olefin units, the olefin units are contained in an amount of preferably 0.1 to 99.9% by weight , in order to, for example, improve processability of the random copolymer, the total amount of the olefin units and two or more kinds of polymerization units represented by the formula (1) being 100% by weight.

The random copolymer of the present invention can be produced by copolymerization of two or more kinds of diene compounds represented by the formula (3) . The copolymerization is carried out preferably in the presence of a polymerization catalyst formed by contacting a transition metal compound with an organoaluminum compound and/or boron compound, namely, is carried out by contacting the polymerization catalyst with two or more kinds of diene compounds represented by the formula ( 3 ) .

The transition metal compound may be known in the art . Examples thereof are transition metal compounds containing one or more atoms selected from the group consisting of an iron atom, a cobalt atom, a nickel atom, a palladium atom and a cupper atom; transition metal compounds represented by the following respective formulas [I], [II] and [III]; and a combination of two or more of those transition metal compounds , the formula {II] being a subordinate position concept of the formula [I]:

wherein M ¹ is an iron atom, a cobalt atom, a nickel atom, a palladium atom or a cupper atom; R ³ and R ⁴ are independently of each other a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group or an aryloxy group; and R ⁵ , R ⁶ , R ⁷ and R ⁸ are independently of one other a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group, an aryloxy group , an acyl group, an alkoxycarbonyl group , an aralkyloxycarbonyl group, an aryloxycarbonyl group, an amino group, a substituted amino group, an amide group or an alkylthio group, and R ⁷ and R ⁸ may be linked with each other to form a ring;

wherein M ¹ is an iron atom, a cobalt atom, a nickel atom, a palladium atom or a cupper atom; R ³ and R ⁴ are independently

of each other a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group or an aryloxy group; and R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are independently of one other a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, an amino group, a substituted amino group, an amide group or an alkylthio group, and R ⁷ and R ⁸ may be linked with each other to form a ring; and

wherein M ¹ is an iron atom, a cobalt atom, a nickel atom, a palladium atom or a cupper atom; R ³ and R ⁴ are independently of each other a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group or an aryloxy group; and R ¹⁵ to R ²¹ are independently of one other a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aralkyloxy group , an aryloxy group , an acyl group , an alkoxycarbonyl group , an aralkyloxycarbonyl group, an aryloxycarbonyl group, an

amino group, a substituted amino group, an amide group or an alkylthio group, and any two of R ¹⁵ to R ²¹ may be linked with each other to form a ring.

M ¹ in the formulas [I] and [II] is preferably a nickel atom or a palladium atom.

M ¹ in the formula [III] is preferably an iron atom or a cobalt atom.

The above defined alkyl group, aralkyl group, aryl group, alkoxy group, aralkyloxy group and aryloxy group of R ³ and R ⁴ in the formulas [I] , [II] and [III] may have a substituent such as a halogen atom, an alkoxy group, an aryloxy group, an aralkyloxy group , a nitro group, an amino group, an amide group , an imide group, a sulfonyl group and an alkylthio group.

The above defined alkyl group, aralkyl group, aryl group, alkoxy group, aralkyloxy group, aryloxy group, acyl group, an alkoxycarbonyl group, an aralkyloxycarbonyl group, an aryloxycarbonyl group, an amino group, a substituted amino group, an amide group and alkylthio group of R ⁵ to R ²¹ in the formulas [I], [II] and [III] may have a substituent such as a halogen atom, an alkoxy group, an aryloxy group, an aralkyloxy group, a nitro group, an amino group, a substituted amino group, an amide group , an imide group , a sulfonyl group and an alkylthio group .

Examples of the halogen atom of R ³ to R ²¹ in the formulas [I], [II] and [III] are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the alkyl group of R ³ to R ²¹ in the formulas [I], [II] and [III] are linear alkyl groups such as a methyl group, an ethyl group, and a n-butyl group; branched alkyl groups such as an isopropyl group, an isobutyl group, a tert-butyl group, and a neopentyl group; and cyclic alkyl groups such as a cyclohexyl group and a cyclooctyl group. Among them, preferred is an alkyl group having 1 to 16 carbon atoms, more preferred is a linear alkyl group having 1 to 8 carbon atoms , and further preferred is a methyl group or an ethyl group. Examples of the aralkyl group of R ³ to R ²¹ in the formulas [I], [II] and [III] are a benzyl group, a ( 2-methylphenyl)methyl group, a ( 3-methylphenyl)methyl group, a (4-methylphenyl)methyl group, a (2,3-dimethylphenyl)methyl group , a ( 2 , 4-dimethylphenyl)methyl group , a (2,5-dimethylphenyl)methyl group , a ( 2 , 6-dimethylphenyl)methyl group , a (3,4-dimethylphenyl)methyl group , a (3,5-dimethylphenyl)methyl group , a (2,3,4-trimethylphenyl)methyl group, a (2,3 , 5-trimethylphenyl)methyl group , a (2,3,6-trimethylphenyl)methyl group , a (2,4,5-trimethylphenyl)methyl group , a (2,4 , 6-trimethylphenyl)methyl group , a (3,4,5-trimethylphenyl )methyl group, a

(2,3,4,5-tetramethylphenyl )methyl group, a

(2,3,4,6-tetramethylphenyl)methyl group, a (2,3,5,6-tetramethylphenyl)methyl group, a (pentamethylphenyl)methyl group, an (ethylphenyl)methyl group, a (n-propylphenyl)methyl group, an (isopropylphenyl)methyl group, a (n-butylphenyl)methyl group, a (sec-butylphenyl)methyl group, a (tert-butylphenyl)methyl group, a (n-hexylphenyl)methyl group, a (n-octylphenyl)methyl group, a (n-decylphenyl)methyl group, a naphthylmethyl group, and an anthracenylmethyl group. Among them, preferred is an aralkyl group having 7 to 20 carbon atoms, and more preferred is a benzyl group .

Examples of the aryl group of R ³ to R ²¹ in the formulas [I], [II] and [III] are a 3-methylphenyl group, a 4-isopropylphenyl group, a 4-tert-butylphenyl group, a 2,3-dimethylphenyl group, a 2 , 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 3,6-dimethylphenyl group, a 2, 6-di-tert-butylphenyl group, amesityl group, a phenyl group , a 2-methylphenyl group, a 2-ethylphenyl group, a 2-n-propylphenyl group, a 2-isopropylphenyl group, a 2-n-butylphenyl group, a 2-isobutylphenyl group, a 2-n-hexylphenyl group, a 4-methylphenyl group, a 2,6-dimethylphenyl group, a 2,6-diethylphenyl group, a 2 , 6-di-n-propylphenyl group, a 2,6-diisopropylphenyl group, a 2,6-di-n-butylphenyl group, a 2, 6-diisobutylphenyl group, a

2, 6-di-n-hexylphenyl group, a 2-methyl-6-ethylphenyl group, a 2-methyl-6-n-propylphenyl group, a 2-methyl-6-isopropylphenyl group, a 2-methyl-6-butylphenyl group, a 2-ethyl-6-n-propylphenyl group, a 2-ethyl-6-isopropylphenyl group, a 2-ethyl-6-n-butylphenyl group, a 2-n-propyl-6-isopropylphenyl group, a 2-n-propyl-6-n-butylphenyl group, a

2-isopropyl-6-n-butylphenyl group, a 2,4, 6-trimethylphenyl group, a 2, 4-dimethyl-6- ( 2-methylphenyl)phenyl group, a 2 , 4-dimethyl-6- ( 2-ethylphenyl)phenyl group, a 2,4-dimethyl-6-(2-n-propylphenyl)phenyl group, a 2,4-dimethyl-6-(2-isopropylphenyl)phenyl group, a 2 , 4-dimethyl-6- (2 , 6-dimethylphenyl)phenyl group, a 2,4-dimethyl-6-(2,6-diethylphenyl)phenyl group, a 2,4-dimethyl-6-(2,6-di-n-propylphenyl)phenyl group, a 2,4-dimethyl-6-(2,6-diisopropylphenyl)phenyl group, a 2, 4-dimethyl-6- (2-methyl-6-ethylphenyl)phenyl group, a 2, 4-dimethyl-6- (2-methyl-6-n-propylphenyl)phenyl group, a 2,4-dimethyl-6-(2-methyl-6-isopropylphenyl)phenyl group, a 2,4-dimethyl-6-(2-ethyl-6-n-propylphenyl)phenyl group, a 2 , 4-dimethyl-6- (2-ethyl-6-isopropylphenyl)phenyl group, a 2,4-dimethyl-6-(l-naphthyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 2-methyl-1-naphthyl group, a 3-methyl-1-naphthyl group, a 4-methyl- 1-naphthyl group, a 2, 3-dimethyl-1-naphthyl group, a 2 , 4-dimethyl-1-naphthyl

group, a 2, 5-dimethyl-1-naphthyl group, a 2 , 6-dimethyl-1-naphthyl group, a 3, 4-dimethyl-1-naphthyl group, a 3, 5-dimethyl-1-naphthyl group, a 3, 6-dimethyl-1-naphthyl group, a 2-methyl-1-anthracenyl group, a 3-methyl-lO-anthracenyl group, a 4-methyl-lO-anthracenyl group, a

2 , 3-dimethyl-10-anthracenyl group, a

2,4-dimethyl-lO-anthracenyl group, a

2, 5-dimethyl-10-anthracenyl group, a 2, 6-dimethyl-10-anthracenyl group, a

3, 4-dimethyl- 10-anthracenyl group, a

3, 5-dimethyl-10-anthracenyl group, a

3, 6-dimethyl- 10-anthracenyl group, and a 2-methyl- 10-anthracenyl group. Among them, preferred is an aryl group having 6 to 20 carbon atoms, more preferred is a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-isopropylphenyl group, a 4-tert-butylphenyl group, a 2, 6-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 3, 6-dimethylphenyl group, a 2,6-diisopropylphenyl group, a 2,6-di-tert-butylphenyl group, a 3,5-di-tert-butylphenyl group, or a mesityl group, and further preferred is a phenyl group, a 2 , 6-dimethylphenyl group, a mesityl group or a 2,6-diisopropylphenyl group.

Examples of the alkoxy group of R ³ to R ²¹ in the formulas [I], [II] and [III] are linear alkoxy groups such as a methoxy group, an ethoxy group, and a n-butoxy group; branched alkoxy

groups such as an isopropoxy group, an isobutoxy group, a tert-butoxy group, and a neopentoxy group; and cyclic alkoxy groups such as a cyclohexyloxy group and a cyclooctyloxy group.

Among them, preferred is an alkoxy group having 1 to 16 carbon atoms , more preferred is a linear alkoxy group having 1 to 8 carbon atoms , and further preferred is a methoxy group or an ethoxy group.

Examples of the aralkyloxy group of R ³ to R ²¹ in the formulas [I], [II] and [III] are a benzyloxy group, a (2-methylphenyl)methoxy group, a ( 3-methylphenyl)methoxy group, a (4-methylphenyl)methoxy group, a

(2,3-dimethylphenyl)methoxy group, a

(2,4-dimethylphenyl )methoxy group , a

(2,5-dimethylphenyl )methoxy group , a (2,6-dimethylphenyl)methoxy group , a

( 3 , 4-dimethylphenyl)methoxy group , a

(3,5-dimethylphenyl)methoxy group , a

(2,3,4-trimethylphenyl)methoxy group, a

(2,3 , 5-trimethylphenyl)methoxy group, a (2,3,6-trimethylphenyl)methoxy group, a

(2,4, 5-trimethylphenyl)methoxy group , a

(2,4,6-trimethylphenyl)methoxy group, a

(3,4,5-trimethylphenyl )methoxy group, a

(2,3,4,5-tetramethylphenyl)methoxy group, a (2,3,4,6-tetramethylphenyl)methoxy group, a

(2,3,5,6-tetramethylphenyl)methoxy group , a

(pentamethylphenyl)methoxy group, an (ethylphenyl)methoxy group, a (n-propylphenyl)methoxy group, an (isopropylphenyl)methoxy group, a (n-butylphenyl)methoxy group, a (sec-butylphenyl)methoxy group, a ( tert-butylphenyl)methoxy group, a (n-hexylphenyl)methoxy group, a (n-octylphenyl)methoxy group, a (n-decylphenyl)methoxy group, a naphthylmethoxy group, and an anthracenylmethoxy group. Among them, preferred is an aralkyloxy group having 7 to 20 carbon atoms , and more preferred is a benzyloxy group.

Examples of the aryloxy group of R ³ to R ²¹ in the formulas [I], [II] and [III] are a phenoxy group, a 2-methylphenoxy group, a 3-methylphenoxy group, a 4-methylphenoxy group, a 2,3-dimethylphenoxy group, a 2, 4-dimethylphenoxy group, a 2,5-dimethylphenoxy group, a 2, 6-dimethylphenoxy group, a 3 , 4-dimethylphenoxy group, a 3, 5-dimethylphenoxy group, a 2-tert-butyl-3-methylphenoxy group, a 2-tert-butyl-4-methylphenoxy group, a 2-tert-butyl-5-methylphenoxy group, a 2-tert-butyl-6-methylphenoxy group, a

2,3,4-trimethylphenoxy group, a 2,3,5-trimethylphenoxy group, a 2, 3, 6-trimethylphenoxy group, a 2,4,5-trimethylphenoxy group, a 2,4,6-trimethylphenoxy group, a 2-tert-butyl-3, 4-dimethylphenoxy group, a 2-tert-butyl-3, 5-dimethylphenoxy group, a

2-tert-butyl-3, 6-dimethylphenoxy group, a

2 , 6-di-tert-butyl-3-methylphenoxy group, a 2-tert-butyl-4,5-dimethylphenoxy group, a 2 , 6-di-tert-butyl-4-methylphenoxy group, a 3,4,5-trimethylphenoxy group, a 2,3,4,5-tetramethylphenoxy group, a 2-tert-butyl-3,4, 5-trimethylphenoxy group, a 2,3,4,6-tetramethylphenoxy group, a

2-tert-butyl-3, 4, 6-trimethylphenoxy group, a 2,6-di-tert-butyl-3,4-dimethylphenoxy group, a 2,3,5,6-tetramethylphenoxy group, a 2-tert-butyl-3, 5, 6-trimethylphenoxy group, a 2 , 6-di-tert-butyl-3, 5-dimethylphenoxy group, a pentamethylphenoxy group, an ethylphenoxy group, a n-propylphenoxy group, an isopropylphenoxy group, a n-butylphenoxy group, a sec-butylphenoxy group, a tert-butylphenoxy group, a n-hexylphenoxy group, a n-octylphenoxy group, a n-decylphenoxy group, a naphthoxy group, and an anthracenoxy group. Among them, preferred is an aryloxy group having 6 to 20 carbon atoms.

Examples of the acyl group of R ⁵ to R ²¹ in the formulas [I], [II] and [III] are an acetyl group, a propanoyl group, a butanoyl group, an isobutanoyl group, a pentanoyl group, an isopentanoyl group, a benzoyl group, and a phenylacetyl group.

Examples of the alkoxycarbonyl group of R ⁵ to R ²¹ in the formulas [I], [II] and [III] are a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an isopropoxycarbonyl group, a n-butoxycarbonyl group, an

isobutoxycarbonyl group, a tert-butoxycarbonyl group, a n-pentoxycarbonyl group, a neopentoxycarbonyl group, a cyclopentoxycarbonyl group, a n-hexoxycarbonyl group, and a cyclohexoxycarbonyl group . Examples of the aralkyloxycarbonyl group of R ⁵ to R ²¹ in the formulas [I] , [II] and [III] are a benzyloxycarbonyl group, a phenethyloxycarbonyl group, and a cumyloxycarbonyl group.

An example of the aryloxycarbonyl group of R ⁵ to R ²¹ in the formulas [I], [II] and [III] is a phenoxycarbonyl group. Examples of the substituted amino group of R ⁵ to R ²¹ in the formulas [I], [II] and [III] are linear alkylamino groups such as an N-methylamino group, an N-ethylamino group, an N-n-butylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, and an N,N-di-n-butylamino group; branched amino groups such as an N,N-diisopropylamino group, an N,N-diisobutylamino group, an N,N-di-tert-butylamino group, and an N,N-dineopentylamino group; and cyclic alkylamino groups such as an N,N-dicyclohexylamino group and an N,N-dicyclooctylamino group. Examples of the amide group of R ⁵ to R ²¹ in the formulas [I], [II] and [III] are an ethanamide group, an N-n-butylethanamide group, an N-methylethanamide group, an N-ethylethanamide group, an N-n-butylhexanamide group, an isopropanamide group, an isobutanamide group, a tert-butanamide group, and a neopentanamide .

Examples of the alkylthio group of R ⁵ to R ²¹ in the

formulas [I], [II] and [III] are a methylthio group, an ethylthio group, an isopropylthio group, a tert-butylthio group, a benzylthio group, and a 9-fluorenylmethylthio group.

The transition metal compound is preferably a compound represented by the formula [II] , from a viewpoint of producing a random copolymer containing polymerization units represented by the formula ( 2 ) ; more preferably a compound represented by the formula [II] wherein R ⁹ and R ¹⁰ are independently of each other an aryl group, and R ¹¹ and R ¹² are independently of each other a hydrogen atom, a halogen atom, an alkyl group , an aralkyl group, an alkoxy group, an aralkyloxy group, an amino group, a substituted amino group or an alkylthio group, from a viewpoint of producing a random copolymer containing a large amount of polymerization units represented by the formula ( 2 ) ; and further preferably a compound represented by the formula [II] wherein R ⁹ and R ¹⁰ are independently of each other an aryl group, and R ¹¹ and R ¹² are independently of each other a hydrogen atom, an alkyl group or an aralkyl group. Examples of the ring formed by linking of R ⁷ with R ⁸ in the formulas [I] and [II], and examples of the ring formed by linking of any two of R ¹⁵ to R ²¹ with each other in the formula [III] are aliphatic rings and aromatic rings. Those rings may have a substituent such as a halogen atom, an alkoxy group, an aryloxy group, an aralkyloxy group, a nitro group, an amino group, a substituted amino group, an amide group, a sulfonyl

group and an alkylthio group.

Examples of a divalent group making the above-mentioned aliphatic rings formed by linking of R ⁷ with R ⁸ , or formed by linking of any two of R ¹⁵ to R ²¹ with each other are a methylene group, an ethane-l,2-diyl group, a propane-l,3-diyl group, a propane-l,2-diyl group, a butane-l,2-diyl group, a butane-l,3-diyl group, a butane-1 , 4-diyl group, a pentane-1 , 2-diyl group, a pentane-l,3-diyl group, a pentane-1 , 4-diyl group, a pentane-1, 5-diyl group, an ethylene-1, 2-diyl group, a cyclohexane-1, 2-diyl group, a cyclohexane-1 , 3-diyl group, a norbornane-1, 2-diyl group, a norbornan-l-ene-1 , 2-diyl group, a butan-1-ene-1,2-diyl group, a butan-1-ene-1,3-diyl group, a butan-1-ene-2, 3-diyl group, a butan-2-ene-1, 2-diyl group, a butan-2-ene-l, 3-diyl group, a butan-2-ene-2, 3-diyl group, a butan-l,3-diene-l, 2-diyl group, a butan-1, 3-diene-1,3-diyl group, a butan-1, 3-diene-1, 4-diyl group, a dimethyl-2 , 3-butene-2 , 3-diyl group, and a pentene-2, 4-diyl group . Examples of a divalent group making the above-mentioned aromatic rings formed by linking of R ⁷ with R ⁸ , or formed by linking of any two of R ¹⁵ to R ²¹ with each other are a benzene-1, 2-diyl group, a 3-methylbenzene-l , 2-diyl group, a 4-methylbenzene-l , 2-diyl group, a 3-ethylbenzene-l, 2-diyl group, a 4-ethylbenzene-1, 2-diyl group, a 3-n-propylbenzene-l,2-diyl group, a

4-n-propylbenzene-l, 2-diyl group, a

3-n-butylbenzene-l, 2-diyl group, a

4-n-butylbenzene-l, 2-diyl group, a

3-isopropylbenzene-1, 2-diyl group, a 4-isopropylbenzene-1, 2-diyl group, a

3-isobutylbenzene-1, 2-diyl group, a

4-isobutylbenzene-l , 2-diyl group, a

3-tert-butylbenzene-l , 2-diyl group, a

4-tert-butylbenzene-l , 2-diyl group, a benzene- 1,3-diyl group, a 2-methylbenzene-1,3-diyl group, a 4-methylbenzene-1,3-diyl group, a methylenebenzene-l,2-dily group, a benzene-1, 2-dimethylene group, a benzene-1, 3-dimethylene group, and an acenaphthene-1, 2-diyl group . Examples of the transition metal compound represented by the formula [I] or [II] , wherein M ¹ is a palladium atom, are chloro(methyl) [N.N ¹ - (ethane-1 , 2-diylidene)bis (aniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis (2-methylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis (2-ethylaniline- KN) ]palladium, chloro(methyl) [N, N ¹ - ( ethane-1 , 2-diylidene)bis (2-n-propylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1, 2-diylidene)bis (2-isopropylaniline- /CN) ]palladium.

chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis (2-n-butylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1 , 2-diylidene)bis (2-isobutylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1, 2-diylidene)bis (2-n-hexylaniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - (ethane- 1 , 2-diylidene)bis (4-methylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane- 1 , 2-diylidene)bis (2,6-dimethylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1 , 2-diylidene)bis (2,6-diethylaniline- /CN) ]palladium, chloro(methyl) [N,N ' - ( ethane-1,2-diylidene)bis (2,6-di-n-propylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1 , 2-diylidene)bis ( 2 , 6-diisopropylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1, 2-diylidene)bis (2,6-di-n-butylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1, 2-diylidene)bis (2,6-diisobutylaniline- /CN) ]palladium, chloro(methyl) [N,N' - ( ethane-1 , 2-diylidene)bis ( 2 , 6-di-n-hexylaniline- /CN) ]palladium, chloro(methyl) [N,N ' - ( ethane-1 , 2-diylidene)bis (2-methyl-6-ethylaniline- /CN) Jpalladium, chloro(methyl) [N.N ¹ - (ethane-1, 2-diylidene )bis (2-methyl-6-n-propylaniline- /CN) Jpalladium,

chloro(methyl) [N,N ' - ( ethane-1,2-diylidene)bis (2-methyl-6-isopropylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (ethane- 1 , 2-diylidene)bis (2-methyl-6-butylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - ( ethane-1 , 2-diylidene)bis (2-ethyl-β-n-propylaniline- KN) ]palladium, chloro(methyl) [N,N' - (ethane-1,2-diylidene)bis (2-ethyl-6-isopropylaniline- KN) ]palladium, chloro(methyl) [N,N ^• - (ethane-1,2-diylidene)bis (2-ethyl-β-n-butylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - ( ethane-1 , 2-diylidene)bis (2-n-propyl-6-isopropylaniline- KN) ]palladium, chloro(methyl) [N,N ^• - (ethane-1 , 2-diylidene)bis ( 2-n-propyl-6-n-butylaniline- KN) ]palladium, chloro(methyl) [N.N ¹ - (ethane-1, 2-diylidene)bis (2-isopropyl-6-n-butylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis (2,4,6-1rimethylaniline-KN)]palladium, chloro(methyl) [N.N ¹ - (ethane-1 , 2-diylidene)bis {2,4-dimethyl-6-(2-methylphenyl)aniline- K N}]palladium, chloro(methyl) [N,N ¹ - (ethane-1 , 2-diylidene)bis {2,4-dimethyl-6-(2-ethylphenyl)aniline- K N} ]palladium, chloro(methyl) [N.N ^• - (ethane-1 , 2-diylidene)bis {2 , 4-dimethyl-6- ( 2-n-propylphenyl) aniline- KN) ]palladium, chloro(methyl) [N.N ¹ - ( ethane-1 , 2-diylidene)bis

{ 2 , 4-dimethyl-6- ( 2-isopropylphenyl) aniline- KN)]palladium.

chloro(methyl ) [N,N' - (ethane-1,2-diylidene)bis {2 , 4-dimethyl-6- ( 2 , 6-dimethylphenyl)aniline- /c N} ]palladium, chloro(methyl) [N,N' - (ethane-1 , 2-diylidene )bis {2,4-dimethyl-6-(2,6-diethylphenyl)aniline- KN) ]palladium, chloro(methyl ) [N,N ^• - (ethane-1 , 2-diylidene)bis{ 2 , 4-dimethyl- 6-(2,6-di-n-propylphenyl)aniline- /CN} ]palladium, chloro(methyl ) [N,N' - (ethane-1,2-diylidene)bis{2 , 4-dimethyl- 6- (2 , 6-diisopropylphenyl)aniline- /CN} ]palladium, chloro(methyl) [N,N ¹ - (ethane-1, 2-diylidene )bis{ 2, 4-dimethyl- 6-(2-methyl-6-ethylphenyl)aniline- /C N} ]palladium, chloro(methyl) [N,N' - (ethane-1,2-diylidene)bis{2,4-dimethyl- 6- ( 2-methyl-6-n-propylphenyl)aniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis{2, 4-dimethyl- 6- ( 2-methyl-6-isopropylphenyl)aniline- /c N} ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis{2, 4-dimethyl- 6- (2-ethyl-6-n-propylphenyl) aniline- /CN} ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis{ 2, 4-dimethyl- 6- ( 2-ethyl-6-isopropylphenyl)aniline- K N} ]palladium, chloro(methyl) [N,N ¹ - (ethane-1,2-diylidene)bis {2,4-dimethyl-6- ( 1-naphthyl) aniline- /c N} ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene )bis (aniline- KN) ]palladium, chloro(methyl) [N.N ¹ - (butane-2 , 3-diylidene )bis (2-methylaniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - (butane-2, 3-diylidene)bis ( 2-ethylaniline- /CN) ]palladium.

chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis (2-n-propylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2-isopropylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis (2-n-butylaniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - (butane-2 , 3-diylidene)bis (2-isobutylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2-n-hexylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (4-methylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis (2,6-dimethylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2.3-diylidene)bis (2,6-diethylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2 , 6-di-n-propylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2,3-diylidene)bis (2,6-diisopropylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2,6-di-n-butylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2,6-diisobutylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2,6-di-n-hexylaniline- KN) ]palladium.

chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2-methyl-6-ethylaniline- /CN) ]palladium, chloro (methyl) [N,N ' - (butane-2,3-diylidene )bis ( 2-methyl-6-n-propylaniline- ACN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis (2-methyl-6-isopropylaniline- /CN) ]palladium, chloro(methyl) [N,N' - (butane-2,3-diylidene)bis (2-methyl-6-butylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis (2-ethyl-6-n-propylaniline- KU) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis (2-ethyl-6-isopropylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis (2-ethyl-6-n-butylaniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - (butane-2 , 3-diylidene)bis ( 2-n-propyl-6-isopropylaniline- /CN) ]palladium, chloro(methyl) [N,N' - (butane-2 , 3-diylidene)bis (2-n-propyl-6-n-butylaniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - (butane-2 , 3-diylidene)bis (2-isopropyl-6-n-butylaniline- /CN) ]palladium, chloro(methyl)[N,N'- (butane-2, 3-diylidene)bis (2,4,6-trimethylaniline- /CN) ]palladium, chloro(methyl ) [N,N ' - (butane-2,3-diylidene )bis {2 , 4-dimethyl-6- ( 2-methylphenyl ) aniline- /C N} ]palladium, chloro(methyl) [N.N' - (butane-2,3-diylidene)bis

{ 2 , 4-dimethyl-6- ( 2-ethylphenyl ) aniline- /C N} ]palladium.

chloro(methyl) [N ₁ N ¹ - (butane-2 , 3-diylidene)bis {2, 4-dimethyl-6- ( 2-n-propylphenyl)aniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2 , 3-diylidene)bis {2 , 4-dimethyl-6- ( 2-isopropylphenyl)aniline- KN}]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis

{2 , 4-dimethyl-6- ( 2 , 6-dimethylphenyl)aniline- K N} ]palladium, chloro(methyl) [N,N ' - (butane-2,3-diylidene )bis {2,4-dimethyl-6- ( 2 , 6-diethylphenyl)aniline- K N} ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis{ 2, 4-dimethyl- 6-(2,6-di-n-propylphenyl)aniline- /CN}]palladium, chloro(methyl ) [N,N' - (butane-2,3-diylidene)bis{2 , 4-dimethyl- 6- (2, 6-diisopropylphenyl)aniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene )bis{ 2, 4-dimethyl- 6- ( 2-methy1-6-ethylphenyl) aniline- KN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2, 3-diylidene)bis{2 , 4-dimethyl- 6- (2-methyl-6-n-propylphenyl) aniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - (butane-2,3-diylidene)bis{2, 4-dimethyl- 6- ( 2-methyl-6-isopropylphenyl)aniline-/CN)]palladium, chloro(methyl) [N,N ' - (butane-2,3-diylidene)bis{2 , 4-dimethyl- 6-(2-ethyl-6-n-propylphenyl)aniline- /CN)]palladium, chloro(methyl) [N,N ' - (butane-2 , 3-diylidene)bis{ 2.4-dimethyl- 6- ( 2-ethyl-6-isopropylphenyl)aniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - (butane-2 , 3-diylidene)bis {2,4-dimethyl-6- ( 1-naphthyl) aniline-KN)]palladium, chloro(methyl) [N.N ¹ - ( 1 , 2-dihydroacenaphthylene-l , 2- diylidene)bis (aniline- /c N) ]palladium.

chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-methylaniline- K N) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-ethylaniline- /CN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-n-propylaniline- KN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-isopropylaniline- /CN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-n-butylaniline- KN) Jpalladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-isobutylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ -(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-n-hexylaniline- KN) ]palladium, chloro(methyl) [N,N ¹ - ( 1 , 2-dihydroacenaphthylene-1, 2- diylidene)bis(4-methylaniline- KN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2,6-dimethylaniline- KN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2,6-diethylaniline- KN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2,6-di-n-propylaniline- KN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene )bis (2,6-diisopropylaniline- KN)]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis ( 2 , 6-di-n-butylaniline-KN)]palladium,

chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis( 2 , 6-diisobutylaniline- /CN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2,6-di-n-hexylaniline- /CN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2,6-dichloroaniline- /CN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-methyl-6-ethylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - ( 1 , 2-dihydroacenaphthylene-1 , 2- diylidene)bis(2-methyl-6-n-propylaniline- /CN) ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-methyl-6-isopropylaniline- /CN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-methyl-6-butylaniline- /CN) ]palladium, chloro(methyl) [N,N ¹ - ( 1 , 2-dihydroacenaphthylene-1 , 2- diylidene)bis( 2-ethyl-6-n-propylaniline- /CN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-ethyl-6-isopropylaniline- /CN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-ethyl-6-n-butylaniline- /CN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-n-propyl-6-isopropylaniline- /CN) ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2-n-propyl-6-n-butylaniline- /CN) ]palladium, chloro(methyl) [N.N ¹ - ( 1 , 2-dihydroacenaphthylene-1 , 2- diylidene)bis(2-isopropyl-6-n-butylaniline- /CN) ]palladium.

chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis(2,4,6-trimethylaniline- /CN) ]palladium, chloro(methyl) [N,N ' - ( 1 , 2-dihydroacenaphthylene-1,2- diylidene)bis{ 2 , 4-dimethyl-6- ( 2-methylphenyl)aniline- K N}]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{ 2 , 4-dimethyl-6- ( 2-ethylphenyl)aniline- K N)]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2 , 4-dimethyl-6- ( 2-n-propylphenyl)aniline- K N)]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2 , 4-dimethyl-6- (2-isopropylphenyl)aniline- /c N} ]palladium, chloro(methyl) [N,N ¹ - (1,2-dihydroacenaphthylene-1,2- diylidene)bis{ 2 , 4-dimethyl-6- ( 2 , 6-dimethylphenyl)aniline- K N}]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2 , 4-dimethyl-6- ( 2 , 6-diethylphenyl)aniline- K N}]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2,4-dimethyl-6-(2,6-di-n-propylphenyl)aniline

- /CN)]palladium, chloro(methyl) [N,N ¹ - ( 1 , 2-dihydroacenaphthylene-1 , 2- diylidene)bis{2 , 4-dimethyl-6- ( 2 , 6-diisopropylphenyl) aniline

- KN)]palladium.

chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2 , 4-dimethyl-6- ( 2-methyl-6-ethylphenyl) aniline- K N} ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2 , 4-dimethyl-6- (2-methyl-6-n-propylphenyl) aniline- KN} ]palladium, chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2 , 4-dimethyl-6- ( 2-methyl-6-isopropylphenyl ) aniline- /C N} ]palladium, chloro(methyl )[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene)bis{2,4-dimethyl-6-(2-ethyl-6-n-propylphenyl) aniline- K N} ]palladium, chloro(methyl) [N, N ¹ - ( 1 , 2-dihydroacenaphthylene-1 , 2- diylidene )bis{ 2,4-dimethyl-6- ( 2-ethyl-6-isopropylphenyl) aniline- K N}]palladium, and chloro(methyl)[N,N'-(1,2-dihydroacenaphthylene-1,2- diylidene )bis{ 2,4-dimethyl-6- ( 1-naphthyl) aniline-

K N}]palladium.

Examples of the transition metal compound represented by the formula [I] or [II] , wherein M ¹ is a nickel atom, an iron atom, a copper atom or a cobalt atom, are compounds named by replacing the term "palladium" contained in the above-exemplified palladium compounds with the term "nickel",

"iron", "copper" or "cobalt". Examples of the transition metal compound represented by the formula [III], wherein M ¹ is an iron, are

2 , 6-bis- [ 1- ( 2 , 6-dimethylphenylimino)ethyl]pyridineiron dichloride ,

2 , 6-bis- [ 1- (2 , 6-diisopropylphenylimino)ethyl]pyridineiron dichloride , 2 , 6-bis- [ 1- ( 2-tert-butylphenylimino) ethyl ]pyridineiron dichloride ,

[hydrotris ( 3 , 5-dimethylpyrazolyl)borate] iron chloride, [hydrotris( 3, 5-dimethylpyrazolyl)borate] iron bromide, [hydrotris ( 3, 5-dimethylpyrazolyl)borate] iron iodide, [hydrotris (3, 5-dimethylpyrazolyl)borate] iron methyl, [hydrotris (3,5-dimethylpyrazolyl)borate ] iron ethyl , [hydrotris (3,5-dimethylpyrazolyl)borate] iron allyl , [hydrotris (3 , 5-dimethylpyrazolyl)borate] iron methallyl, [hydrotris (3,5-diethylpyrazolyl )borate] iron chloride , [hydrotris (3, 5-diethylpyrazolyl)borate] iron bromide, [hydrotris ( 3 , 5-diethylpyrazolyl)borate] iron iodide, [hydrotris (3 , 5-diethylpyrazolyl)borate] iron methyl, [hydrotris ( 3 , 5-diethylpyrazolyl)borate] iron ethyl, [hydrotris ( 3 , 5-diethylpyrazolyl)borate] iron allyl, [hydrotris (3, 5-diethylpyrazolyl)borate] iron methallyl,

[hydrotris ( 3 , 5-di-tert-butylpyrazolyl)borate] iron chloride, [hydrotris(3,5-di-tert-butylpyrazolyl)borate]iron bromide, [hydrotris ( 3 , 5-di-tert-butylpyrazolyl)borate] iron iodide, [hydrotris ( 3 , 5-di-tert-butylpyrazolyl)borate] iron methyl, [hydrotris (3, 5-di-tert-butylpyrazolyl)borate] iron ethyl,

[hydrotris(3,5-di-tert-butylpyrazolyl)borate]iron allyl, and

[hydrotris ( 3 , 5-di-tert-butylpyrazolyl )borate] iron methallyl .

Examples of the transition metal compound represented by the formula [III] , wherein M ¹ is a nickel atom, a palladium atom, a copper atom, or a cobalt atom, are compounds named by replacing the term "iron" contained in the above-exemplified iron compounds with the term "nickel", "palladium", "copper" or "cobalt".

The above-mentioned transition metal compounds may be used in combination of two or more thereof.

The above-mentioned organoaluminum compound may be a compound known in the art. Examples thereof are the following compounds (Al) to (A3) , and a combination of two or more thereof:

(Al) an organoaluminum compound represented by the formula, E ¹ _d AlX ² ₃ . _d ;

(A2) a cyclic alumoxane represented by the formula, {-Al(E ² )-O-} _β ; and

(A3) a linear alumoxane represented by the formula, E ³ {-A1(E ³ ) -0-} _f AlE ³ ₂ , whereinE ¹ , E ² andE ³ are independentlyof one another ahydrocarbyl group, and when plural E ¹ S, E ² S or E ³ S exist, they are the same as, or different from one another; X ² is a hydrogen atom or a halogen atom, and when plural X ² S exist, they are the same as, or different from each another; d is a number satisfying 0 < d -5 3; e is an integer of 2 or more, and preferably an integer of 2 to 40; and f is an integer of 1 or more, and preferably

an integer of 1 to 40.

The hydrocarbyl group of E ¹ , E ² and E ³ is preferably a hydrocarbyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 8 carbon atoms . Examples of the alkyl group of E ¹ , E ² and E ³ are a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a n-pentyl group, and a neopentyl group.

Among them, preferred is a methyl group or an isobutyl group.

Examples of the above-mentioned organoaluminum compound (Al) are trialkylaluminums such as trimethylaluminum, triethylaluminum, tripropylaluminum, triisobutylaluminum, and trihexylaluminum; dialkylaluminum chlorides such as dimethylaluminum chloride, diethylaluminum chloride, dipropylaluminum chloride, diisobutylaluminum chloride and dihexylaluminum chloride; alkylaluminum dichlorides such as methylaluminum dichloride, ethylaluminum dichloride, propylaluminum dichloride, isobutylaluminum dichloride and hexylaluminum dichloride; and dialkylaluminum hydrides such as dimethylaluminum hydride , diethylaluminum hydride, dipropylaluminum hydride, diisobutylaluminum hydride and dihexylaluminum hydride. Among them, preferred is a trialkylaluminum, and more preferred is triethylaluminum or triisobutylaluminum.

The above-mentioned cyclic alumoxane (A2) and linear alumoxane (A3) can be produced according to various processes. Those processes are not particularly limited, and may be those

known in the art. Examples of the process are (i) a process comprising the step of contacting water with a solution of a trialkylaluminum such as trimethylaluminum in a suitable organic solvent such as benzene and an aliphatic hydrocarbon, and (ii) a process comprising the step of contacting a trialkylaluminum such as trimethylaluminum with a crystal water-containing metal salt such as copper sulfate hydrate.

The above-mentioned boron compound may be known in the art. Examples thereof are the following compounds (Bl) to (B3) , and a combination of two or more thereof:

(Bl) a boron compound represented by the formula, BQ ¹ Q ² Q ³ ;

(B2) a boron compound represented by the formula, G ⁺ (BQ ¹ Q ² Q ³ Q ⁴ ) ^" ; and (B3) a boron compound represented by the formula, (J-H) ⁺ (BQ ¹ Q ² Q ³ Q ⁴ ) ^" ; wherein B is a trivalent boron atom; Q ¹ , Q ² , Q ³ and Q ⁴ are independently of one another a halogen atom, a hydrocarbyl group, a halogenated hydrocarbyl group, a silyl group, a siloxy group, an alkoxy group, an amino group, a substituted amino group, an amide group, or an imide group; G ⁺ is an inorganic or organic cation; J is a neutral Lewis base; and (J-H) ⁺ is a Broensted acid.

Q ¹ , Q ² / Q ³ and Q ⁴ in the above-mentioned formulas are preferably a halogen atom, a hydrocarbyl group having 1 to 20 carbon atoms, a halogenated hydrocarbyl group having 1 to 20

carbon atoms, a silyl group having 1 to 20 carbon atoms, a siloxy group having 1 to 20 carbon atoms, a C2-2 ₀ hydrocarbyl group-carrying amino group, a C2-20 hydrocarbyl group-carrying amide group, or a C2-20 hydrocarbyl group-carrying imide group; more preferably a halogen atom, a hydrocarbyl group having 1 to 20 carbon atoms, or a halogenated hydrocarbyl group having 1 to 20 carbon atoms; further preferably a fluorinated Ci_ ₂ o hydrocarbyl group containing one or more fluorine atoms ; and particularly preferably a fluorinated C ₆ -2o aryl group containing one or more fluorine atoms .

Examples of the above-mentioned boron compound (Bl) are tris (pentafluorophenyl)borane , tris (2,3,5,6-tetrafluorophenyl )borane , tris (2,3,4,5-tetrafluorophenyl )borane , tris (3,4,5-trifluorophenyl)borane , tris (2,3,4-trifluorophenyl)borane , and phenylbis(pentafluorophenyl)borane. Among them, most preferred is tris (pentafluorophenyl)borane.

Examples of the inorganic cation of G ⁺ in the above-mentioned boron compound (B2) are a ferrocenium cation, an alkyl group-having ferrocenium cation, and a silver cation. An example of the organic cation of G ⁺ therein is a triphenylmethyl cation. Among them, G ⁺ is preferably a carbenium cation, and particularly preferably a triphenylmethyl cation.

Examples of (BQ ¹ Q ² Q ³ Q ⁴ ) ^' in the above-mentioned boron

compound (B2) are tetrakis(pentafluorophenyl)borate, tetrakis (2,3,5,6-tetrafluorophenyl )borate , tetrakis (2,3,4,5-tetrafluorophenyl)borate , tetrakis (3,4,5-trifluorophenyl)borate , tetrakis (2,3,4-trifluorophenyl)borate , phenyltris (pentafluorophenyl)borate , and tetrakis ( 3 , 5-bistrifluoromethylphenyl )borate .

Examples of the above-mentioned boron compound (B2) are lithium tetrakis ( 3 , 5-bistrifluoromethylphenyl)borate , sodium tetrakis (3, 5-bistrifluoromethylphenyl)borate, potassium tetrakis (3 , 5-bistrifluoromethylphenyl)borate, silver tetrakis (pentafluorophenyl)borate, ferrocenium tetrakis (pentafluorophenyl)borate ,

1,1' -dimethyIferrocenium tetrakis (pentafluorophenyl)borate, tetrabutylphosphponium tetrakis (pentafluorophenyl)borate, tetraphenylphosphponium tetrakis (pentafluorophenyl)borate , tetramethylammonium tetrakis (pentafluorophenyl )borate , trimethylsulphonuim tetrakis (pentafluorophenyl)borate , diphenyliodonium tetrakis (pentafluorophenyl)borate , triphenylcarbenium tetrakis (pentafluorophenyl)borate, and triphenylcarbenium tetrakis ( 3, 5-bistrifluoromethylphenyl)borate. Among them, most preferred is triphenylcarbenium tetrakis (pentafluorophenyl )borate . Examples of (J-H) ⁺ in the above-mentioned boron compound (B3) are a trialkylammonium, an N,N-dialkylanilinium,

a dialkylammonium, and a triarylphosphonium. Examples of the (BQ ¹ Q ² Q ³ Q ⁴ ) ^' therein are the same as those mentioned above.

Examples of the above-mentioned boron compound (B3) are triethylammonium tetrakis (pentafluorophenyl)borate , tripropylammonium tetrakis (pentafluorophenyl)borate, tri(n-butyl) ammonium tetrakis (pentafluorophenyl)borate , tri(n-butyl)ammonium tetrakis ( 3 , 5-bistrifluoromethylphenyl ) borate, N,N-dimethylanilinium tetrakis (pentafluorophenyl) borate, N,N-diethylanilinium tetrakis (pentafluorophenyl) borate, N,N-dimethyl-2,4, 6-trimethylanilinium tetrakis

(pentafluorophenyl)borate, N,N-dimethylanilinium tetrakis (3, 5-bistrifluoromethylphenyl)borate, diisopropylammonium tetrakis (pentafluorophenyl)borate, dicyclohexylammonium tetrakis (pentafluorophenyl)borate, triphenylphosphonium tetrakis (pentafluorophenyl)borate, tri(methylphenyl) phosphonium tetrakis (pentafluorophenyl)borate, and tri(dimethylphenyl )phosphonium tetrakis (pentafluorophenyl) borate. Among them, most preferred is tri(n-butyl)ammonium tetrakis (pentafluorophenyl)borate, or N,N-dimethylanilinium tetrakis (pentafluorophenyl)borate .

The boron compound is preferably the above-mentioned boron compound (B2) or (B3), and particularly preferably triphenylcarbenium tetrakis (pentafluorophenyl )borate , tri(n-butyl) ammonium tetrakis (pentafluorophenyl)borate, or N,N-dimethylanilinium tetrakis (pentafluorophenyl)borate.

The random copolymer of the present invention has a

weight-average molecular weight (Mw) of preferably 1,000 to 10,000,000, more preferably 2,000 to 5,000,000, and most preferably 4,000 to 3,000,000.

Under the definition that a molecular weight distribution is defined as a ratio of a weight-average molecular weight (Mw) to a number-average molecular weight (Mn), the random copolymer of the present invention has a molecular weight distribution (Mw/Mn) of preferably 1.0 to 100, more preferably 1.0 to 50, and most preferably 1.0 to 20. The random copolymer of the present invention preferably has a glass-transition point, preferably one or more glass-transition points of -20 "C or higher, more preferably one or more glass-transition points of 20 ¹ C or higher, and most preferably one or more glass-transition points of 50 ¹ C or higher.

Examples of a method for feeding two or more kinds of diene compounds represented by the formula ( 3 ) to a polymerization system such as a polymerization reactor, in order to produce the random copolymer of the present invention, are (1) a method comprising the step of feeding those two or more kinds of diene compounds separately however simultaneously to a polymerization reactor, and (2) a method comprising the step of feeding a mixture of those two or more kinds of diene compounds thereto. Incidentally, the random copolymer of the present invention cannot be produced by a method comprising the steps of (i) feeding a first kind of diene

compound to a polymerization reactor, thereby polymerizing the first kind, of diene compound to form a homopolymer thereof, and (ii) feeding a second kind of diene compound thereto, thereby polymerizing the second kind of diene compound completely in the presence of the above-produced homopolymer, which results in a production of a blend of two kinds of homopolymers , because the step (ii) also forms a homopolymer of the second kind of diene compound.

In the present invention, there is not a particular limitation in a method for contacting with one another (i) the diene compound represented by the formula (3), (ii) the transition metal compound, and (iii) the organoaluminum compound and/or boron compound.

When forming a polymerization catalyst by contacting the transition metal compound with the organoaluminum compound, the organoaluminum compound is preferably the above-mentioned cyclic alumoxane (A2) , linear alumoxane (A3) , or a combination thereof, from a viewpoint of producing a highly active polymerization catalyst. When forming a polymerization catalyst by contacting the transition metal compound, the organoaluminum compound and the boron compound with one another, the organoaluminum compound is preferably the above-mentioned organoaluminum compound (Al), from a viewpoint of producing a highly active polymerization catalyst .

The organoaluminum compound is used in amount of

generally 0.1 to 10,000 parts by mol, and preferably 5 to 2,000 parts by mol, per one part by mol of the transition metal compound. The boron compound is used in amount of generally 0.01 to 100 parts by mol, and preferably 0.5 to 10 parts by mol, per one part by mol of the transition metal compound.

Each of the transition metal compound, the organoaluminum compound, and the boron compound may be used as a solution thereof. Examples of a solvent for the solution are methylene chloride, chloroform, toluene, pentane, hexane, and heptane. Among them, preferred is methylene chloride, chloroform, or toluene.

A solution of the transition metal compound has a concentration of generally 0.01 to 500 Mmol/L, preferably 0.05 to 100 /imol/L, and more preferably 0.05 to 50 Mraol/L. A solution of the organoaluminum compound has a concentration of generally 0.01 to 10,000 Mmol/L, preferably 0.1 to 5,000 H mol/L, and more preferably 0.1 to 2,000, in terms of an amount of an aluminum atom contained in the solution. A solution of the boron compound has a concentration of generally 0.01 to 500 Umol/L, preferably 0.05 to 200 Umol/L, and more preferably 0.05 to 100 Mmol/L.

The above-mentioned polymerization catalyst may be combined with a carrier or a support comprising particles of an inorganic or organic compound. The carrier or the support may be known in the art . Examples of the inorganic compound are silica gel and alumina, and an example of the organic compound

is a styrene unit-containing polymer.

Examples of a polymerization method in the present invention are a gas-phase polymerization method, a bulk polymerization method, and a solution or suspension polymerization method using a suitable polymerization solvent, which are a batch-wise polymerization method or a continuous polymerization method. The polymerization solvent is a solvent non-deactivating a polymerization catalyst. Examples of the solvent are a hydrocarbon solvent such as benzene, toluene, pentane, hexane, heptane, and cyclohexane; and a halogenated solvent such as dichloromethane and chloroform.

A polymerization temperature in the present invention is generally -100 to 25OtD, and preferably -50 to 200°C . A polymerization time is generally one minute to 72 hours. The process of the present invention may use a chain transfer agent such as hydrogen in order to regulate a molecular weight of a random copolymer produced.

The present invention is explained with reference to the following Examples, which do not limit the scope of the present invention.

Example 1

There were put 6.6 mg (0.01 mmol) of chloro(methyl) [N,N ¹ - ( 1 , 2-dihydroacenaphthylene-l , 2- diylidene)bis(2,6-diisopropylaniline- K N)]palladium (transition metal compound: prepared according to Recueil des

Travaux Chimiques de Pays-Bas, Vol. 113, page 88 (1994)), 10.6 mg of sodium tetrakis{3, 5-bis (trifluoromethyl)phenyl)borate (boron compound: prepared according to Organometallics , Vol. 11, page 3920 (1992)), and 0.5 mL of methylene chloride, in a Schlenk flask. To the Schlenk flask, 0.137 g (0.7 mmol) of 2,2-dimethyl-5,5-diallyl-l,3-dioxane (compound represented by the formula (3)) and 0.156 g (0.7 mmol) of 5,5-diallyl Meldrum's acid (compound represented by the formula (3)) were added. The mixture was agitated for 6 hours at a room temperature . The obtained reaction mixture in a solution state was analyzed to find that 2, 2-dimethyl-5, 5-diallyl-l , 3-dioxane was copolymerized in a polymerization rate of nearly 100%, and 5,5-diallyl Meldrum's acid was copolymerized in a polymerization rate of 33%. The reaction mixture was poured into methanol, and the precipitated copolymer was filtered off and then dried, thereby obtaining a random copolymer of 2, 2-dimethyl-5, 5-diallyl-l, 3-dioxane with 5,5-diallyl Meldrum's acid. The random copolymer had a number-average molecular weight (Mn) of 3,600; a molecular weight distribution (Mw/Mn) of 1.70; 75% by mol of 2, 2-dimethyl-5, 5-diallyl-l, 3-dioxane units represented by the formula (1), and 25% by mol of 5,5-diallyl Meldrum's acid units represented thereby, the total of both units being 100% by mol; and 87% by mol of a trans-form regarding 2, 2-dimethyl-5, 5-diallyl-l, 3-dioxane units, and 100% by mol

of a trans-form regarding 5,5-diallyl Meldrum's acid units, in view of its relative configuration between A ⁷ and A ⁸ .

The above-mentioned number-average molecular weight (Mn) and molecular weight distribution (Mw/Mn) were measured according to a gel permeation chromatography (GPC) under the following conditions using an equipment manufactured by JASCO

Corporation having a degasser (DG-980-50) , a pump (PU-980) , an auto-sampler (AS-950), a column oven (CO-966), an RI detector (RI-930) and a UV detector (UV-975), with a calibration curve prepared using standard polystyrenes :

- two columns, SHODEX-806L, manufactured by Showa Denko K.K. ;

- measurement temperature of 40"C; - solvent of chloroform; and

- sample concentration of 1 mg-sample/mL-solution.

The above-mentioned amount of the polymerization units represented by the formula ( 1 ) was measured according to a ¹ H-NMR method under the following conditions using an equipment , LA-500, manufactured by JEOL LTD:

- measurement solvent of chloroform-di;

- measurement temperature of room temperature;

- sample concentration of 50 mg-sample/0.5 mL-solution; and

- reference material of chloroform-di (7.26 ppm) .

The above-mentioned proportion of the trans-form was measured under the following conditions according to a ¹³ C-NMR method using an equipment, LA-500, manufactured by JEOL LTD; and the above-mentioned existence of the unit represented by the formula (1) was confirmed by assigning signals in the range of 23 to 50 ppm of a ¹³ C-NMR spectrum obtained by the ¹³ C-NMR method to a linear hydrocarbyl structure and a 5-membered hydrocarbyl structure contained in the unit represented by the formula ( 1 ) :

- measurement solvent of chloroform-di;

- measurement temperature of room temperature;

- sample concentration of 50 mg-sample/0.5 mL-solution; and - reference material of chloroform-di (77 ppm).

Example 2

Example 1 was repeated except that (1) 0.156 g (0.7 mmol) of 5,5-diallyl Meldrum's acid was changed to 0.172 g (0.7 mmol) of 9 , 9-diallylfluorene (compound represented by the formula

(3)), and (2) the agitation time of 6 hours was changed to 4 hours , thereby obtaining a reaction mixture in a solution state .

The reaction mixture was analyzed to show that

2 , 2-dimethyl-5, 5-diallyl-l , 3-dioxane was copolymerized in a polymerization rate of 9%, and 9, 9-diallylfluorene was copolymerized in a polymerization rate of 57%.

The reaction mixture was poured into methanol, and the precipitated copolymer was filtered off and then dried, thereby obtaining a random copolymer of 2,2-dimethyl-5,5-diallyl-l,3-dioxane with 9, 9-diallylfluorene. The random copolymer had a number-average molecular weight (Mn) of 8,400; a molecular weight distribution (Mw/Mn) of 1.94; 88% by mol of 2 , 2-dimethyl-5, 5-diallyl-l , 3-dioxane units represented by the formula (1), and 12% by mol of 9 , 9-diallylfluorene units represented thereby, the total of both units being 100% by mol; and a glass-transition point of 63C in a range of 0 to 200 ¹ C.

The above-mentioned glass-transition point was measured according to a differential scanning calorimetry (DSC) using an equipment, SSC-5200, manufactured by Seiko

Instruments & Electronics Ltd. under the following conditions:

- heating from 25 ^* C to 200 ¹ C at a rate of loT^/minute, and keeping at 200"C for 5 minutes; then,

- cooling from 2Oθ"C to -60 ¹ C at a rate of 20"C/minute, and keeping at -βo'C for 5 minutes; and then,

- measuring under heating from -60 ¹ C to 200"C at a rate of IOC/minute.

Example 3 Example 1 was repeated except that (1) 0.156 g (0.7 mmol ) of 5,5-diallyl Meldrum's acid was changed to 0.091 g (0.4 mmol)

of 2, 2-diallylindan-l, 3-dione (compound represented by the formula (3)). (2) 0.137 g (0.7 mmol) of 2 , 2-dimethyl-5, 5-diallyl-l , 3-dioxane (compound represented by the formula (3)) was changed to 0.079 g (0.4 mmol) thereof, and (3) the agitation temperature was changed from a room temperature to -10 ¹ C, and (4) the agitation time was changed from 6 hours to 24 hours, thereby obtaining a reaction mixture in a solution state. The reaction mixture was analyzed to show that 2, 2-diallylindan-l, 3-dione was copolymerized in a polymerization rate of 58%, and 2, 2-dimethyl-5 , 5-diallyl-l, 3-dioxane was copolymerized in a polymerization rate of 71%.

The reaction mixture was poured into methanol, and the precipitated copolymer was filtered off and then dried, thereby obtaining a random copolymer of 2, 2-diallylindan-l, 3-dione with

2 , 2-dimethyl-5, 5-diallyl-l , 3-dioxane. The random copolymer had a number-average molecular weight (Mn) of 10,000; a molecular weight distribution (Mw/Mn) of 1.21; 48% by mol of 2, 2-diallylindan-l, 3-dione units represented by the formula (1), and 52% by mol of 2, 2-dimethyl-5 , 5-diallyl-l , 3-dioxane units represented thereby, the total of both units being 100% by mol; 100% by mol of a trans-form regarding the 2, 2-diallylindan-l, 3-dione units, and 89% by mol of a trans-form regarding the

2 , 2-dimethyl-5 , 5-diallyl-l, 3-dioxane units, in view of its

relative configuration between A ⁷ and A ⁸ ; and a glass-transition point of 116"C in a range of 0 to 200 ¹ C.

Industrial Applicability The random copolymer of the present invention can be molded according to an extrusion molding method or an injection molding method. Those methods may be known in the art. Examples of the extrusion molding method are (1) an inflation molding method comprising the steps of (1-1) extruding a molten resin through a circular die, thereby forming an extruded product, (1-2) blowing the extruded product into a cylindrical film or sheet , and ( 1-3 ) rewinding the film or sheet , ( 2 ) a T-die molding method comprising the steps of (2-1) extruding a molten resin through a linear die, thereby forming a film or sheet, and (2-2) rewinding the film or sheet, and (3) a calender molding method.