JP2000344815A - Olefin polymerization catalyst - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an olefin polymerization catalyst capable of controlling the stereostructure of the resulting polymer and synthesizing a polyolefin having desired physical properties, and a polyolefin copolymer produced by the polymerization using the catalyst. SOLUTION: An olefin polymerization catalyst comprises a metal atom and, coordinated thereto, an organic substance which has a planar skeleton represented by the formula in Figure. At least one of a combination of A- and B-positions, a combination of B- and C-positions and a combination of C- and D-positions in the skeleton forms a ring bond and substituent groups are attached to A-position and D-position. The skeleton is an phenanthroline skeleton which preferably has substituent groups attached to 2-position and 9-position. The substituent group is preferably selected from a 2,6-substituted benzene, a 2,6-substituted cyclohexane and a trimethylsilyl group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an olefin polymerization catalyst having a metal center and a polyolefin copolymer polymerized using the catalyst.

[0002]

2. Description of the Related Art As an olefin polymerization catalyst, DuPont discloses a polymerization catalyst 91 having a central metal (M) 95 such as Ni or Pd as shown in FIG. The polymerization catalyst 91 has a diimine ligand 92. The diimine ligand 92 has a single aromatic ring 921 at each of the two nitrogen atoms.
Are bonded, and the molecular structure is bulky. Therefore, the olefin transfer reaction (β-hydrogen elimination reaction) is suppressed,
As a result, a high molecular weight polyolefin is formed.

[0003]

However, in the polymerization catalyst 91, the single aromatic ring 921 can rotate with respect to the nitrogen atom. Therefore, it was difficult to control the three-dimensional structure (tacticity) of the produced polyolefin, and it was difficult to control the physical properties of the produced polyolefin. In addition, in the above polymerization catalyst, the space in which the olefin can be coordinated is wide and the degree of steric freedom in which the monomer can be coordinated is high.
Branching was likely to occur in the polyolefin.

[0004] In view of the above problems, the present invention aims to provide an olefin polymerization catalyst capable of controlling a steric structure and synthesizing a polyolefin having desired physical properties, and a polyolefin-based copolymer polymerized using the catalyst. Is what you do.

[0005]

The invention according to claim 1 is an olefin polymerization catalyst in which an organic substance having a skeleton represented by the general formula (I) in FIG. 1 and located on the same plane is coordinated to a metal atom,
At least one pair of the A-position and the B-position, the B-position and the C-position, and the C-position and the D-position in the skeleton form a cyclic bond, and a substituent is bonded to the A-position and the D-position. An olefin polymerization catalyst characterized by the following.

In the olefin polymerization catalyst of the present invention,
An organic substance having a planar skeleton represented by the general formula (I) in FIG. 1 is coordinated to a metal atom serving as a catalytic active center.
The skeleton has a cyclic bond.
A substituent is bonded to the position. Therefore, the bond axis of the substituent is sterically hindered by the skeleton having a cyclic bond,
Cannot rotate. Therefore, the configuration of the substituents at the A-position and the D-position can be asymmetrically symmetric. Therefore, an asymmetric structure centering on a metal atom can be introduced into the olefin catalyst.
Therefore, according to the olefin polymerization catalyst of the present invention, stereoregular polymerization of olefins is possible, and a produced polyolefin having a controlled steric structure such as isotactic and syndiotactic can be synthesized.

Further, by introducing a bulky substituent at the A and D positions, the space in which the olefin can be coordinated with the polymerization catalyst is reduced, and the degree of freedom of the olefin coordination is reduced. For this reason, a branched polyolefin is not easily generated, and a linear polyolefin can be synthesized with a high yield.

The skeleton of the organic substance blocks directly above the metal atom at the active center (apical position), and the bulky substituent blocks both sides of the metal atom. Therefore, the olefin transfer reaction (β-hydrogen elimination reaction) is further suppressed as compared with the conventional catalyst. Therefore, according to the olefin polymerization catalyst of the present invention, a polyolefin having a higher molecular weight can be synthesized as compared with the case where a conventional catalyst is used.

(Skeletal structure of organic substance)
At least one pair of the positions B and B, the positions B and C, and the positions C and D form a cyclic bond. A cyclic bond can be formed, for example, via one or more atoms such as carbon, oxygen, nitrogen, etc.
Is formed. The site that does not form a cyclic bond is the end of the skeleton, and in some cases, a side chain is bonded. A and B positions, B and C positions in the above skeleton,
It is preferable that both the C-position and the D-position form a cyclic bond. Thereby, the three-dimensional structure of the produced polyolefin can be controlled more effectively.

[0010] As in the invention of claim 2, the skeleton is a phenanthroline skeleton, and it is preferable that a substituent is bonded to the 2, 9-position in the phenanthroline skeleton.

The phenanthroline skeleton has the chemical structure shown in FIG. 2, and the 2- and 9-positions correspond to the A-position and D-position in the general formula (I) of the skeleton in FIG. As shown in FIG. 3, the phenanthroline skeleton 1 is coordinated to a metal atom (M) 3 which is an active center. A substituent 2 such as a phenyl group is bonded to the 2- and 9-positions of the phenanthroline skeleton 1. Substituent 2 is bulky and sterically hindered by the phenanthroline skeleton 1;
Cannot rotate. Therefore, the configuration of the substituents at the 2-position and the 9-position can be asymmetrically symmetric (C2 symmetry). Therefore, an asymmetric structure centering on a metal atom can be introduced into the olefin catalyst. Therefore, according to the olefin polymerization catalyst, a product polyolefin having a controlled three-dimensional structure such as a branch amount, a branch distribution, and a geometric structure can be synthesized.

Further, by introducing a bulky substituent at the 2-position and the 9-position, the space in which the olefin can be coordinated with the polymerization catalyst is reduced, and the degree of freedom of the olefin coordination is reduced. Therefore, according to the olefin polymerization catalyst, a product polyolefin having a controlled steric structure can be synthesized.

As shown in FIG. 4, when the bond axis of the substituent 2 is rotatable, the steric configuration of the substituent 2 is not determined, and the asymmetric structure disappears. When synthesizing a polyolefin by the above method, the three-dimensional structure of the produced polyolefin cannot be controlled.

In the present invention, the phenanthroline skeleton 1 is located just above the metal atom 3 at the active center (apical position).
And the bulky substituent 2 blocks both sides of the metal atom 3. Therefore, the olefin transfer reaction (β-hydrogen elimination reaction) is further suppressed as compared with the conventional catalyst. Therefore, according to the polymerization catalyst, a polyolefin having a high molecular weight can be synthesized.

As the organic substance of the olefin polymerization catalyst, an organic substance having a skeleton shown in FIG. 5 can be used.

(Substituents) Substituents bonded to the A and D positions (corresponding to positions 2 and 9 in the case of the skeletons of FIGS. 2 and 5) of the skeleton of FIG. 1 will be described. As in the third aspect of the present invention, the substituent at the A and D positions of the skeleton is preferably a hydrocarbon having at least two carbon atoms. As a result, the substituent becomes bulky and it becomes easy to introduce an asymmetric structure into the olefin polymerization catalyst.

According to a fourth aspect of the present invention, A,
The substituent at the D-position is preferably selected from any of a 2,6-substituted benzene, a 2,6-substituted cyclohexane, and a trimethylsilyl group. Since these are bulky substituents, it becomes easy to introduce an asymmetric structure.

The above substituents are based on, for example, a hydrocarbon skeleton, and further include carbon, hydrogen, boron, nitrogen, oxygen, halogen, phosphorus (P), sulfur (S), and tin (Sn). It may be replaced with, for example. Examples of the substituent include an alkyl group and an aryl group. Allyl, alkene, alkyne, alkoxy, hydroxy, hydroxyl, hydroxylate, thiocarboxy,
Dithiocarboxy group. Sulfo group, sulfino group, sulfeno group, oxycarbonyl group, haloformyl group, carbamoyl group, hydrazinocarbonyl group, amidino group, cyano group, isocyanate group, cyanato group, isocyanato group, thiocyanato group, inthiocyanato group, formyl group, It is preferable to use an oxo group, a thioformyl group, a thioxo group, a mercapto group, an amino group, an imino group, a hydrazino group, an alkoxy group, an allyloxy group, a sulfide group, a halogen, a nitro group, or the like. Thereby, the tacticity (stereoscopic) control of the produced polyolefin can be effectively performed.

It is preferable that the substituents at the A and D positions of the skeleton have different chemical, geometric and steric structures. As a result, an asymmetric structure centering on the metal atom is formed, and the three-dimensional structure of the resulting polyolefin can be controlled.

[0020] A bond having an asymmetric structure introduced at the A and D positions of the skeleton.
As a result, the entire polymerization catalyst may have an asymmetric structure.
No. For example, if the skeleton is phenanthroline,
As shown, positions 2 and 9 of the phenanthroline skeleton 1 were
2,6-dialkylbenzene ring as a substituent 2 is bonded
If it is, alkyl attached to the benzene ring
Group R₁~ R₄By any one of the different
(For example, R₁= R₄, R ₃= R₂, R₁≠ R₂,
R₁≠ R₂≠ R₃≠ R₄Etc.), the entire polymerization catalyst is asymmetric
Will be built.

The substituents bonded to the A and D positions of the skeleton may have the same chemical, geometric and steric structure. In this case, an atactic linear polyolefin with few branches can be synthesized. A substituent may be bonded to a position other than the A and D positions of the skeleton.

For controlling the branching of the olefin, the structure of the substituent is important. When the coordination space of the olefin is large, that is, when the substituent of the ligand is large, a less branched olefin is formed.

(Metal atom) The metal atom of the olefin polymerization catalyst of the present invention is Ni, Pd, Ti, Fe, Co, Zr,
Hf, V, Sc, Mn, Cr, Sn, Y, etc.
Among them, Ni or Pd is preferable. This makes it possible to synthesize a copolymer of an olefin and a polar monomer such as acryl and methacryl in addition to the olefin. A ligand other than the above phenanthroline may be bonded to the metal atom. As a ligand, for example,
There are almin, phosphine, phenol and amine ligands.

(Polymerization Reaction Conditions) In synthesizing a polyolefin using the olefin polymerization catalyst of the present invention,
An olefin is added to a reaction solution in which an olefin polymerization catalyst has been dissolved to carry out a polymerization reaction. The conditions for this polymerization reaction are:
−86 to 200 ° C., inert atmosphere (for example, N ₂ , Ar)
It is preferred that

The content of the olefin polymerization catalyst in the reaction solution is preferably 0.001% to 30%. If it is less than 0.001%, the reaction efficiency may decrease. If it exceeds 30%, the molecular weight of the produced polymer may decrease. The olefin to be polymerized may be cyclic, chain, or branched.

(Polyolefin) Polyolefins synthesized using the olefin polymerization catalyst include polyolefins having controlled polymer main chain structures such as tacticity and branching. Specific examples thereof include α, including polyethylene and polypropylene. -Olefins (atactic, syndiotactic, isotactic),
There are cyclic polyolefins.

According to the olefin polymerization catalyst,
As in the invention of claim 5, a novel polyolefin copolymer characterized by copolymerizing a polyolefin having regularity in the polymer main chain with a polar monomer can be synthesized.

The phrase "having regularity in the polymer main chain" means that, for example, the polyolefin has a stereoregularity such as atactic, syndiotactic and isotactic, and a linear regularity with few branches. Having an array. Examples of the polar monomer include methacryl and acrylic.

The polyolefin synthesized using the olefin polymerization catalyst of the present invention can be controlled, for example, in the form of an adhesive, a paint, a compatibilizer, a tackifier, because it can control steric control and physical properties and can synthesize an olefin-acrylic copolymer. Suitable for use in chemicals, structural materials and thickeners.

[0030]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiment 1 In this embodiment, as shown in FIGS. 6 to 11, an olefin polymerization catalyst according to an embodiment of the present invention was manufactured, and olefin polymerization was performed using the catalyst. .

First, an olefin polymerization catalyst was produced by the following method. (2,9-diphenylphenanthroline (hereinafter, Ph-
Ph)) Phenanthroline monohydrate 1.0
0 g was heated under vacuum at 80 ° C. for 5 minutes. 15 ml of dehydrated toluene was added under an argon atmosphere, and 11.5 ml of a 1.8 M phenyllithium solution (cyclohexane-ether solution) was added over 15 minutes while stirring and cooling with ice. After slowly raising the temperature to room temperature and stirring overnight, 25 ml of water was slowly added. The mixture was stirred for 30 minutes, 15 g of manganese dioxide was added, and the mixture was stirred for 3 hours. Filtration, evaporation and vacuum drying. It was isolated by silica gel column chromatography (solvent chloroform) and 560 mg of Ph-Ph (FIG. 8)
(A)) was obtained. This reaction is shown in the reaction formula (I) in FIG.

((2,9-diphenylphenanthroline) nickel (II) dibromide (hereinafter Ph-PhN
It is called i. Ph) Ph in a glove box
254.6 mg and 236 mg of (dimethoxyethylene) nickel (II) bromide ((DME) NiBr ₂ )
9. In a mixture of the above, dehydrated THF (tetrahydrofuran)
3 g was added and stirred overnight. The precipitate was collected by filtration and dried in vacuo to obtain 150 mg of Ph-PhNi (FIG. 8B) as a pink solid. This reaction is represented by the reaction formula (I) in FIG.
This is shown in I).

(Synthesis of 2,5-diisopropyliodobenzene)
It was dissolved in 0 ml of acetic acid and 30 ml of concentrated sulfuric acid was added. The mixture was cooled on ice with stirring, and an aqueous solution (10 ml) of 5.06 g of sodium nitrite (NaNO ₂ ) was added while maintaining the temperature at 0 to 5 ° C.
It was added dropwise over 0 minutes. After stirring for 15 minutes, add ice cold water for 10 minutes.
0 ml was added. This suspension was added to an aqueous potassium iodide solution (100 g / 250 ml) and heated at 60 to 80 ° C. for 30 minutes with stirring. After cooling to room temperature, the reaction mixture was extracted with 200 ml of hexane. The product remaining in the aqueous layer was extracted again with 100 ml of hexane, and this extract was combined with the hexene extract. The combined extract (organic layer) was washed with an aqueous solution of potassium hydroxide, an aqueous solution of sodium bisulfite and water in this order. The extract was dried over sodium sulfate and filtered over silica gel. The solution was evaporated to give 2.75 g of 2,5-diisopropyliodobenzene (FIG. 8 (c)). This reaction is shown in the reaction formula (III) in FIG.

(Synthesis of 2,9-di (2,5-diisopropylphenyl) phenanthroline (hereinafter referred to as Ph-iPr)) 8.9 g of 2,5-
30 ml of dehydrated ether from diisopropyl iodobenzene
And 14.9 ml of 1.53 M n-butyllithium (BuLi) was added over 20 minutes at room temperature. 20
After stirring for an hour, it was evaporated and dried under vacuum.
While cooling with liquid nitrogen, a solution of 1.03 g of 1,10-phenanthroline (sublimated and purified hydrate) in 40 ml of toluene was added. The mixture was returned to room temperature with gentle stirring, and allowed to stand with stirring overnight. After stirring at 70 ° C. for 3 hours, the mixture was stirred for 2 days. Add 50 ml of water under ice cooling,
Separate the toluene layer and wash the aqueous layer with 30 ml of chloroform.
The organic layer was combined with the one extracted twice. 15 g of manganese dioxide (MnO ₂ ) was added to the organic layer, and the mixture was stirred for one day. After filtration and evaporation, silica gel column chromatography (solvent chloroform / hexane = 3 /
Purified in 1), 350 mg of Ph-iPr (FIG. 9)
(A)) was obtained. This reaction is represented by the reaction formula (IV, V) shown in FIG.
It was shown to.

(Synthesis of 2,9-di (2,5-diisopropyliodobenzene) phenanthroline nickel (II) dibromide (hereinafter referred to as Ph-iPrNi)) In a probe box, 150 mg of Ph-iPr and (dimethoxyethylene) Nickel (II) bromide ((DM
E) ₂ g of dehydrated THF was added to a mixture of 92 mg of NiBr ₂ ).
Was added and stirred overnight. The reddish-brown solution was evaporated and dried under vacuum to obtain a red solid Ph-iPrNi (FIG. 9).
(B)) was obtained in quantitative yield. This reaction is shown in the reaction formula (VI) in FIG.

(Polymerization Reaction of Ethylene Using Ph-PhNi) Under an argon atmosphere, the Ph-P shown in FIG.
hNi (10 mg) was suspended in 2.2 mg of dehydrated toluene, and 2.5 g of methylaluminoxane (hereinafter, referred to as MAO; purchased from Tosoh Akzo) was added. The red-black solution was transferred to a 100 ml pressure vessel with stirring, and 2 MPa of ethylene was introduced with stirring. Twenty hours later, hydrochloric acid-ethanol was added, and the precipitate was filtered and washed with ethanol. After vacuum drying, wash with 1N hydrochloric acid and ethanol, 10.1m
g of polymer were obtained. This polymer was polyethylene and had a molecular weight of 50,000.

(Polymerization Reaction of Ethylene Using Ph-iPrNi) Under an argon atmosphere, the Ph-iPrNi shown in FIG.
iPrNi (5 mg) was suspended in 3 mg of dehydrated toluene,
MAO (0.24 g) was added. The red-black solution was transferred to a 100 ml pressure vessel with stirring, and 2M of ethylene was stirred.
Pa was introduced. Six days later, concentrated hydrochloric acid was added, the toluene layer was separated, washed with water, evaporated and dried under vacuum.
59 mg of polymer were obtained. FIG. 10 shows the result of carbon NMR (nuclear magnetic resonance analysis). This polymer was polyethylene, had a molecular weight of 30,000, and had a linear main chain.

(Comparative Example) Brookhart under an argon atmosphere
5 mg of the catalyst were suspended in 3 mg of dehydrated toluene,
(0.24 g) was added. The red-black solution is stirred for 100
Then, the mixture was transferred to a pressure-resistant container of 2 ml, and 2 MPa of ethylene was introduced under stirring. One day later, concentrated hydrochloric acid was added, and the toluene layer was separated.
After washing with water, evaporate and dry under vacuum,
mg of polymer were obtained. FIG. 11 shows the results of carbon NMR (nuclear magnetic resonance analysis). This polymer was polyethylene, the molecular weight was 10,000, and the main chain had a branched structure.

FIGS. 10 and 11 show that the polyethylene obtained by polymerization with Ph-iPhNi has less branches than the polyethylene obtained by the conventional method using a Brookhart catalyst.

Embodiment 2 First, an olefin polymerization catalyst was produced by the following method. (Synthesis of 2,9-di (2-methyl-6-isopropylbenzene) phenanthroline (hereinafter referred to as Ph-MiPr)) Under argon atmosphere, 7.9 g of 2-methyl
-6-isopropylbromobenzene was dissolved in dehydrated ether, and 14.9 ml of 1.53 M n-buthyllithium was added at room temperature.
Added over 5 minutes. After stirring for 20 hours, evaporation and vacuum drying were performed. With cooling with liquid nitrogen,
A solution of 1.03 g of 1,10-phenanthroline (sublimated and purified hydrate) in 40 ml of toluene was added. The temperature was returned to room temperature with gentle stirring and left overnight with stirring.
After stirring at 70 ° C. for 3 hours, the mixture was stirred for 2 days. Under ice-cooling, 50 ml of water was added, the toluene layer was separated, and the aqueous layer was extracted twice with 50 ml of chloroform to obtain an organic layer. 13 g of manganese dioxide was added to the organic layer and stirred for one day. After filtration and evaporation, purification was performed by silica gel column chromatography (solvent: chloroform-hexane 3: 1), and 290 mg of Ph-MiPr (FIG. 1)
2 (a)) was obtained.

(Synthesis of 2,9-di (2-methyl-6-isopropylbenzene) phenanthroline nickel (II) diclomide (hereinafter referred to as Ph-MiPrNi (t))) In a glove box, Ph-MiPr 130 was used.
mg, (dimethoxyethylene) nickel (II) bromide92mg
Was added to 2 g of dehydrated THF, and the mixture was stirred overnight. The red-brown solution was evaporated and dried in vacuo to give a red solid in quantitative yield. Recrystallized from hexane-toluene, 100 mg of Ph-MiPrN shown in FIG.
i (t) was obtained.

(Polymerization of Propylene Using Ph-MiPrNi (t)) Ph-MiPrNi under argon atmosphere
(T) 10 mg was suspended in 2 ml of dehydrated toluene,
(2.5 g) was added. 100m red and black solution with stirring
Then, it was transferred to the pressure-resistant container No. 1 and propylene was introduced at 2 MPa with stirring. Twenty hours later, hydrochloric acid-ethanol was added, and the precipitate was filtered and washed with ethanol. After vacuum drying, the precipitate was washed with 1N hydrochloric acid and ethanol to obtain 120 mg of a white solid polymer. Mm% (meaning the ratio of chains; hereinafter the same) was 97%, indicating that the polymer was rich in isotactic chains.

(Comparative Example) Brookhart under an argon atmosphere
10 mg of the catalyst was suspended in 2 ml of dehydrated toluene, and
(2.5 g) was added. 100m red and black solution with stirring
Then, 2 MPa of propylene was introduced under stirring. Twenty hours later, hydrochloric acid-ethanol was added, and the precipitate was filtered and washed with ethanol. After vacuum drying, the product was washed with 1N hydrochloric acid and ethanol to obtain 100 mg of an oily polymer. The resulting polymer was an atactic polymer.

(Copolymerization of propylene and methyl methacrylate (MMA) using Ph-MiPrNi (t))
Ph-MiPrNi (t) 10m under argon atmosphere
g in 2 ml of dehydrated toluene and MAO (2.5 g)
Was added. The reddish black solution was transferred to a 100 ml pressure vessel under stirring, and propylene was added at 2 MPa and MMA 20 m2 under stirring.
g was introduced. Twenty hours later, hydrochloric acid-ethanol was added, and the precipitate was filtered and washed with ethanol. After vacuum drying,
After washing with 1N hydrochloric acid and ethanol, 150 mg of a white solid polymer was obtained. Mm% was 80%, a polymer rich in isotactic chains, and 5% of acrylic monomer was copolymerized.

[0045]

According to the present invention, the three-dimensional structure can be controlled,
Further, it is possible to provide an olefin polymerization catalyst capable of synthesizing a polyolefin having desired physical properties, and a polyolefin-based copolymer polymerized using the catalyst.

[Brief description of the drawings]

FIG. 1 is an explanatory view of an organic substance represented by the general formula (I) in the present invention.

FIG. 2 is an explanatory diagram showing a phenanthroline skeleton in the present invention.

FIG. 3 is an explanatory view of an olefin polymerization catalyst according to the present invention.

FIG. 4 is an explanatory diagram showing a three-dimensional structure of an olefin polymerization catalyst when a rotation axis of a substituent is rotatable.

FIG. 5 is an explanatory view showing an example of a skeleton of an organic substance in the present invention.

FIG. 6 is an explanatory view showing reaction formulas (I) to (II) in the method for producing an olefin polymerization catalyst in the first embodiment.

FIG. 7 is an explanatory view of Reaction Formulas (III) to (VI) following FIG. 6;

FIGS. 8A and 8C are explanatory diagrams showing a chemical structure of an intermediate product in a method for producing an olefin polymerization catalyst in Embodiment 1 and FIGS. 8B and 8B are explanatory diagrams showing a chemical structure of an olefin polymerization catalyst.

FIG. 9 is an explanatory diagram (a) showing a chemical structure of an intermediate product in the method for producing an olefin polymerization catalyst in Embodiment 1, and an explanatory diagram (b) showing a chemical structure of an olefin polymerization catalyst.

FIG. 10 is an explanatory diagram showing the results of carbon NMR analysis of a polyolefin synthesized using the olefin polymerization catalyst shown in FIG.

FIG. 11 shows Br as Comparative Example 1 in Embodiment 1;
Explanatory drawing which shows the analysis result of the carbon NMR of the polyolefin synthesize | combined using the ookhart catalyst.

FIG. 12 is an explanatory diagram (a) showing a chemical structure of an intermediate product in a method for producing an olefin polymerization catalyst in Embodiment 2, and an explanatory diagram (b) showing a chemical structure of an olefin polymerization catalyst.

FIG. 13 is an explanatory view showing a chemical structure of an olefin polymerization catalyst in a conventional example.

[Explanation of symbols]

 1. . . 1. phenanthroline skeleton, . . 2. a substituent; . . Metal atom,

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Mitsuru Nakano 41-cho, Yokomichi, Nagakute-cho, Aichi-gun, Aichi Prefecture Inside of Toyota Central Research Laboratory Co., Ltd. (72) Inventor Yumitsu Usuki Nagakute-machi, Aichi-gun No. 41, Chochu-Yokomichi 1 Toyota Central Research Laboratory Co., Ltd. F-term (reference) 4J028 AA01A AB00A AB01A AC01A AC08A AC18A AC26A AC29A AC37A AC42A AC45A AC46A AC47A AC48A BA00A BA01B BB00A BB01B BC25B EB01 A02P02 GA04 AL03Q CA01 CA04 CA11 CA12 DA19 FA09

Claims (5)

[Claims] 1. A metal atom having the following general formula (I): An olefin polymerization catalyst in which an organic substance having a skeleton having the same plane and having a skeleton is coordinated, wherein at least one pair of the A position and the B position, the B position and the C position, and the C position and the D position in the skeleton is An olefin polymerization catalyst, wherein a cyclic bond is formed and a substituent is bonded to the A-position and the D-position. 2. The olefin polymerization catalyst according to claim 1, wherein the skeleton is a phenanthroline skeleton, and a substituent is bonded to positions 2 and 9 of the phenanthroline skeleton. 3. The olefin polymerization catalyst according to claim 1, wherein the substituent is a hydrocarbon having at least two carbon atoms. 4. The method according to claim 3, wherein the substituent is 2,2.
An olefin polymerization catalyst selected from 6-substituted benzene, 2,6-substituted cyclohexane, and trimethylsilyl groups. 5. A polyolefin-based copolymer obtained by copolymerizing a polyolefin having a regular polymer main chain with a polar monomer.