JP2000007719A - Production of polymer by using copper compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a polymer having a narrow mol.wt. distribution easily in a high yield at a low cost by using a copper compd. contg. a monovalent copper atom as a catalyst and/or a polymn. initiator. SOLUTION: This copper compd. is represented by the formula: LCuX, LCu, or L(L')Cu. In the formulas, L and L' are each a ligand; and X is a halogen, alkoxy, thioxy, aryloxy, amino, cyano, or the like. Examples of the ligands L and L' are one that is coordinated by an unpaired electron of an N, S, O, or P atom present in the ligand and one that is coordinated by a cyclopentadienyl group present in the ligand. Bipyridine, substd. bipyridines, and bisoxazoline are examples of an N-coordination compd. Pref., the copper compd. is used together with an organometallic compd. selected from among aluminoxanes, organoaluminum compds. represented by the formula: AlRmZ3-m (wherein R is a 1-20C hydrocarbon group; Z is H or a halogen; and m is 0-3), and ionic compds. having a boron atom.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for producing a polymer using a copper compound.

[0002]

2. Description of the Related Art Vinyl monomers have been conventionally polymerized by various methods. Industrially, a method of adding a radical generator to a vinyl monomer and performing radical polymerization under high temperature and high pressure is almost used. Recently, as a polymerization method capable of controlling the molecular weight and molecular weight distribution, for example, anionic polymerization,
Coordination polymerization and group transfer polymerization have been proposed at the laboratory level.

However, the compounds used in these catalyst systems are transition metal complexes, which are generally unstable to oxygen and moisture, are easily decomposed, and are synthesized through more reaction steps. Moreover, the synthesis is difficult due to its instability, resulting in a low yield, resulting in an expensive catalyst system.

On the other hand, as the metal of the transition metal complex used in the catalyst system, the transition metals such as titanium, zirconium and hafnium are generally used. Recently, nickel, palladium, and the like, which are late transition metals, are also used as the center metal of the complex, although the reactivity is slightly lowered [JACS 117, No 236414.
(1995) etc.].

A complex containing copper as a central metal has the advantage of being excellent in stability and easy to synthesize, but has low activity due to its stability and has not been studied as a polymerization catalyst. However, recently, the inventors have announced that a copper complex can be used as a polymerization catalyst for a carbodiimide which is a highly polar monomer, and a living polymer can be obtained [Macromolecules 30, 31].
59 (1997)]. However, there has been no example in which a copper complex was applied as a polymerization catalyst for a relatively low-polarity monomer requiring reactivity.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing a polymer using a copper compound which is easy to synthesize and uses a stable copper compound as a polymerization catalyst.

[0007]

Means for Solving the Problems The present inventors have solved the above-mentioned problems by using a monovalent copper compound as a polymerization catalyst component among copper compounds that can be easily synthesized.

In the method for producing a polymer using a copper compound according to the first aspect of the present invention, when a vinyl monomer is polymerized, monovalent copper is used as a catalyst and / or a polymerization initiator. General formula LCuX, LCu or L
(L ′) a copper compound represented by Cu (wherein L and L ′ each represent a ligand, X represents a halogen atom, an alkoxy group, a thioxy group, an allyloxy group, an amino group, a secondary amino group, A tertiary amino group, a cyano group, a nitro group, an alkyl group or an allyl group).

In the method for producing a polymer using a copper compound according to the second aspect of the present invention, an aluminoxane, a general formula AlR _m Z _3-m (where R represents 1 to carbon atoms) is used together with the copper compound. A hydrocarbon atom, Z represents a hydrogen atom, a halogen atom, an alkoxy group, an allyloxy group or a siloxy group; m is an integer of 0 to 3); a Lewis acid having a boron atom And at least one organometallic compound selected from the group consisting of ionic compounds having a boron atom.
A method for producing a polymer using the copper compound described above.

The method for producing a polymer using a copper compound according to the third aspect of the present invention is represented by the general formulas LCuX, LC
At least one of the ligands of the copper compound represented by u or L (L ') Cu is a ligand coordinated by an unpaired electron of an N atom in the structure. A method for producing a polymer using the copper compound according to item 1 or 2.

A method for producing a polymer using a copper compound according to the invention of claim 4 of the present invention comprises the general formulas LCuX, LC
4. The polymer using the copper compound according to claim 1, wherein at least one of the ligands of the copper compound represented by u or L (L ′) Cu is an amidinate group. It is a manufacturing method of.

Hereinafter, the present invention will be described in detail. Examples of the vinyl monomer used in the present invention include olefins and α-substituted olefins. These may be used alone, two or more of them may be used in combination, or they may be copolymerized. In the case of copolymerization, random copolymerization and block copolymerization are also possible.

The above-mentioned olefin has one or more carbon-carbon double bonds in the molecule. For example, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1- Octene, 4-methyl-1-
Α-olefins such as pentene; and dienes such as butadiene. .

In the production method of the present invention, a copper compound alone or a combination of a copper compound and an organometallic compound is used as a catalyst to obtain a polymer from the vinyl monomer.

The above copper compound has monovalent copper in its structure and is represented by the general formula LCuX, LCu or L (L ') Cu. In the formula, L and L ′ represent a ligand, X represents a halogen atom, an alkoxy group, a thioxy group, an allyloxy group, an amino group, a secondary amino group, a tertiary amino group, a cyano group, a nitro group, An alkyl group or an allyl group, preferably a halogen atom such as chlorine or bromine; a methoxy group,
An alkoxy group such as an ethoxy group, an isopropoxy group, and a t-butoxy group; and a tertiary amino group such as a dimethylamino group and a diethylamino group.

The ligands L and L 'are not particularly limited, but are coordinated by unpaired electrons of N, S, O and P atoms existing in the structure of the ligand, and coordinated by a cyclopentadienyl group. The position can be exemplified. Specific examples include coordination with amines, secondary alkylamines and tertiary alkylamines; N coordination such as amidinate coordination; and O coordination such as coordination with alkoxy and aryloxy. Among the above-mentioned ligands, those which coordinate with N atoms are particularly preferred.

Examples of the N-coordination compound include bipyridine, substituted bipyridine, bisoxazoline, substituted bisoxazoline, N, N'-dimethylamidinate,
N′-diethylamidinate, N, N′-diisopropylamidinate, N, N′-di-t-butylamidinate,
N, N'-trifluoromethylamidinate, N, N'-
Diphenylamidinate, N, N'-disubstituted phenylamidinate, N, N'-ditrimethylsilylamidinate,
N, N′-dimethylbenzamidinate, N, N′-diethylbenzamidinate, N, N′-diisopropylbenzamidinate, N, N′-di-t-butylbenzamidinate, N, N N'-trifluoromethylbenzamidinato, N, N'-diphenylbenzamidinato, N, N '
-Ditrimethylsilylbenzamidinato, N, N'-disubstituted phenylbenzamidinato coordination compound and the like.

As a compound which performs both coordination by N atoms and coordination by O atoms, for example, 8-quinolinol coordination compounds can be mentioned.

The above-mentioned copper compound has a general formula of LCuX, which has monovalent copper in its structure and contains two or more copper atoms in one molecule.
A dimer of a copper compound represented by LCu or L (L ′) Cu,
It may be a trimer or a binuclear complex. These complexes are
Even in the solid state, even if it is a dimer, trimer or dinuclear complex, it often exists as a monomer in a solution at the time of reaction or in a monomer, and the state of this monomer is represented by the general formula LCuX. ,
Any material corresponding to LCu or L (L ') Cu can be used in the present invention.

The above copper compound can be easily synthesized from an inexpensive copper halide, for example, copper (I) chloride.
As an example of the synthesis of the N-coordination compound and copper (I) amidinato complex, for example, an equivalent amount of an amidine compound is added to copper (I) chloride anhydride, and the mixture is stirred in a dry organic solvent for several hours. Can be synthesized.

The above-mentioned copper compounds may be used alone or in combination of two or more. Further, it may be used after being diluted with a hydrocarbon or a halogenated hydrocarbon.

The above-mentioned copper compound may be supported on a particulate carrier. As the particulate carrier, for example, Si
O ₂ , Al ₂ O ₃ , MgO, CaO, TiO ₂ , Zn
Inorganic carriers such as O and MgCl ₂ ; resins such as polyethylene, polypropylene and styrene-divinylbenzene copolymer can be used.

The organometallic compound used in combination with the copper compound includes aluminoxane, a general formula AlR _m Z _3-m (wherein
R represents a hydrocarbon group having 1 to 20 carbon atoms, Z represents a hydrogen atom, a halogen atom, an alkoxy group, an allyloxy group or a siloxy group. m is an integer of 0 to 3), at least one selected from the group consisting of an organoaluminum compound represented by the following formula: a Lewis acid having a boron atom; and an ionic compound having a boron atom.

Of the above organometallic compounds, aluminoxa
Is represented by the general formula R¹(Al (R¹) -O) _pAlR¹ _TwoOr
It is a compound represented by the following general formula (1). Where R¹
Represents a hydrocarbon group having 1 to 3 carbon atoms, and p is an integer of 2 or more.
Is shown.

[0025]

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The aluminoxane is preferably a methylaluminoxane wherein R ¹ is a methyl group, and p is preferably 5 or more, more preferably p is 10 or more. Aluminoxane is usually commercially available as a toluene solution. As for the production method, a direct reaction between trialkylaluminum and water and a reaction with a hydrate of a metal salt are known.

As the organoaluminum compound represented by the general formula AlR _m Z _3-m , various compounds can be exemplified.
Specifically, trialkylaluminums such as trimethylaluminum, triethylaluminum, triisopropylaluminum, triisobutylaluminum and trioctylaluminum; alkenylaluminums such as isoprenylaluminum; dimethylaluminum chloride, diethylaluminum chloride, diisopropylaluminum chloride, diisobutylaluminum Dialkylaluminum monochlorides such as chloride and dioctylaluminum chloride; alkylaluminum sesquichlorides such as methylaluminum sesquichloride, ethylaluminum sesquichloride, isopropylaluminum sesquichloride, isobutylaluminum sesquichloride and octylaluminum sesquichloride Alkyl aluminum dichlorides such as methylaluminum dichloride, ethylaluminum dichloride, isopropylaluminum dichloride, isobutylaluminum dichloride, octylaluminum dichloride; and alkoxy group-containing aluminum compounds such as methoxydiethylaluminum, diisopropoxymethylaluminum, and triisopropoxyaluminum. Can be

Of the above organometallic compounds, those having a boron atom
The Lewis acid having the general formula BR ^Two _ThreeCompound represented by
Things. Where R^TwoIs a fluorine atom, methyl
Group, may have a substituent such as a trifluoromethyl group
Phenyl group; represents a fluorine atom. Specifically, the trifle
Oroborane, triphenylboron, tris (4-fluorofuran
Enyl) boron, tris (3,5-difluorophenyl)
Boron, tris (4-fluoromethylphenyl) boron,
Lis (pentafluorophenyl) boron, tris (p-to
Ril) boron, tris (o-tolyl) boron, tris (3,
5-dimethylphenyl) boron and the like. In this
So, tris (pentafluorophenyl) boron is preferred
No.

Among the organometallic compounds, the ionic compounds having a boron atom include trialkyl-substituted ammonium salts, N, N-dialkylanilinium salts,
Examples thereof include dialkylammonium salts and triarylphosphonium salts. Specifically, triethylammonium tetra (phenyl) boron, tripropylammonium tetra (phenyl) boron, tri (n-butyl) ammonium tetra (phenyl) boron, trimethylammonium tetra (p-tolyl) boron, trimethylammonium tetra (o) -Tolyl) boron, tributylammoniumtetra (pentafluorophenyl) boron, tripropylammoniumtetra (o, p-dimethylphenyl) boron, tributylammoniumtetra (m, m-dimethylphenyl) boron, tributylammoniumtetra (p-trifluorophenyl) Trialkyl-substituted ammonium salts such as methylphenyl) boron and tri (n-butyl) ammoniumtetra (o-tolyl) boron; N, N-dimethylaniliniumtetra (phenyl) boron, N, N-die Le tetra (phenyl) boron, N, N, such as N-2,4,6-pentamethylanilinium tetra (phenyl) boron,
N-dialkylanilinium salts; dialkylammonium salts such as di (1-propyl) ammonium tetrapentafluorophenylboron and dicyclohexylammonium tetra (phenyl) boron; triphenylphosphonium tetra (phenyl) boron, tri (dimethylphenyl)
Examples include triarylphosphonium salts such as phosphonium tetra (phenyl) boron. Further, triphenylcarbenium tetrakis (pentafluorophenyl) boronate, N, N-dimethylanilinium tetrakis (pentafluorophenyl) borate, ferrocenium tetra (pentafluorophenyl) borate and the like can be exemplified.

The following anionic salts can also be exemplified as the ionic compound having a boron atom.
In the ionic compounds listed below, the counter ion is
Although tri (n-butyl) ammonium is shown as a general example, it is not limited to this. Examples of the salt of the above anion include bis [tri (n-butyl) ammonium]
Nonaborate, bis [tri (n-butyl) ammonium] decaborate, bis [tri (n-butyl) ammonium] undecaborate, bis [tri (n-butyl) ammonium] dodecaborate, bis [tri (n-butyl) ammonium ] Decachlorodecaborate, bis [tri (n-butyl) ammonium] dodecachlorododecaborate, tri (n-butyl) ammonium 1-carbadecaborate, tri (n-butyl) ammonium 1-carboundecaborate, tri ( n-butyl) ammonium 1-carbadodecaborate, tri (n-butyl) ammonium 1-trimethylsilyl-1-carbadecaborate, tri (n-butyl) ammonium bromo-1-carbadodecaborate and the like, furthermore for example borane and Carborane complex; cal Salts of the run anion; and carboranes and salts of carboranes can be exemplified.

Further, the following metal borane salts and metal borane anions can also be exemplified as ionic compounds having a boron atom. [In the ionic compounds listed below, the counter ion is tri (n) as a general example. −
Butyl) ammonium, but is not limited to this. Examples of the metal borane salt and metal borane anion include tri (n-butyl) ammonium bis (nonahydride-1,3-dicarbanonaborate) cobaltate (III) and tri (n-butyl) ammonium bis (un). Decahydride-7,8-dicarboundecaborate) ferrate (ferrate) (III), tri (n-butyl) ammonium bis (undecahydride-7,8-dicarboundecaborate) cobaltate
(III), tri (n-butyl) ammonium bis (undecahydride-7,8-dicarboundecaborate)
Nickelate (III), tri (n-butyl) ammonium bis (undecahydride-7,8-dicarboundecaborate) cuprate (cuprate) (III) and the like can be exemplified.

If necessary, an electron donating compound such as ethyl benzoate or a compound having a phenol group in the molecule may be added to the catalyst system of the present invention. When these compounds are added, the polymerization activity may be significantly improved.

Examples of the compound having a phenol group in the molecule include 2,6-di-t-butyl-p-cresol.

Although the details of the polymerization mechanism in the production method of the present invention are not clear, the copper compound acts as a catalyst and / or a polymerization initiator, and the copper compound and a vinyl monomer (hereinafter, referred to as a monomer), or Copper compounds,
It is considered that the interaction between the organometallic compound and the monomer accelerates the coordination and insertion reaction of the monomer.

The timing of adding the copper compound alone or the copper compound and the organometallic compound to the reaction system may be before, simultaneously with or after the introduction of the monomer, but is most preferably before the introduction. . The polymerization method and conditions are not particularly limited, and may be continuous polymerization or discontinuous polymerization.

The polymerization for obtaining the above polymer is preferably performed in an inert gas atmosphere. As the inert gas, nitrogen, helium, argon or the like is used.

As the solvent used for the polymerization, for example,
Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and dichloroethane; hydrocarbons such as benzene, toluene, and xylene; tetrahydrofuran, dioxane, and dimethylformamide are used. is there.

The polymerization temperature is preferably in the temperature range from the melting point to the boiling point of the solvent used. Under pressure, the polymerization can be carried out in a wide temperature range from the boiling point at normal pressure to the boiling point. For example, a polymer having a narrow molecular weight distribution can be obtained even at room temperature. The specific polymerization temperature is usually-
20 ° C to 200 ° C is preferred, and more preferably 0 ° C to 1 ° C.
20 ° C. Further, specific polymerization pressure is generally preferably atmospheric pressure to 100 kg / cm ^2, more preferably atmospheric pressure to 50 kg / cm ^2.

The amounts of the copper compound and the organometallic compound used will be described below.

When a copper compound is used alone as a catalyst, the amount thereof is generally preferably about 0.00005 to 0.5 mmol, more preferably about 0.00005 mmol, in terms of copper atoms per liter of polymerization volume. 0.0001-0.05
Millimoles.

When a copper compound and an organometallic compound are used together as a catalyst, the amount of the copper compound used is preferably the same as that when the above-mentioned copper compound is used alone. In the case of the aluminum compound, the aluminum atom is usually about 1 to 1 per mole of the atom.
000 mol is preferred, and more preferably 10 to 5,
000 mol. In the case of a Lewis acid or an ionic compound having a boron atom, the boron atom is usually preferably 1 to 500 mol, more preferably 1 to 100 mol, per 1 mol of the copper atom of the copper compound. .

When a copper compound, an organometallic compound and a compound having a phenol structure in the molecule are used in combination as a catalyst, the amount of the copper compound and the organometallic compound used is the same as that when the above-mentioned copper compound and the organometallic compound are used in combination. The amount of the compound having a phenol structure in the molecule is preferably about 1 to 100 mol, more preferably 1.5 to 50 mol, based on 1 mol of copper atom of the copper compound. is there.

The molecular weight of the obtained polymer can be adjusted by changing conditions such as the polymerization temperature, or by known means, for example, using hydrogen.

Using the polymerization catalyst as described above, a polymer having an excellent composition distribution can be obtained in the same manner as when using another transition metal complex-based catalyst. Specifically, in the analysis of the polymer by gel permeation chromatography (GPC), when the molecular weight distribution (Mw / Mn) of the polymer obtained by the production method of the present invention is determined, it is 1.1 to 1.1.
It is as narrow as 3.5, and it can be confirmed that the polymerization is controlled precisely.

[0045]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

REFERENCE EXAMPLE 1 Synthesis of Copper Compound A dry-distilled reagent was used below unless otherwise specified. N, N'-ditrimethylsilylbenzamidinato copper
(I) Synthesis of Compound Synthesis of N, N, N'-tris (trimethylsilyl) benzamidine 40 ml of tetrahydrofuran was added to a 250 ml Schlenk flask sufficiently purged with argon, and cooled to -78 ° C. To this flask was added 10 ml of 1,1,1,3,3,3-hexamethyldisilazane, and a commercially available 1.6 M n
30.5 ml of -butyllithium-hexane solution was added dropwise over 20 minutes. After stirring for 30 minutes, benzonitrile 4.9
ml was added dropwise over 10 minutes. Next, the temperature of the system was returned to room temperature, followed by stirring for 10 hours. The solvent was distilled off under reduced pressure, 50 ml of toluene was added to the solid remaining in the flask, and 12.2 ml of trimethylsilyl chloride was added dropwise. Further, a cooling tube was attached to the flask, and after heating and refluxing for 10 hours, filtration was performed, and the solvent was distilled off from the filtrate under reduced pressure to obtain an intended product. The target product was purified by distillation under reduced pressure to obtain 11 g of N, N, N'-tris (trimethylsilyl) benzamidine as white crystals.

Synthesis of N, N'-ditrimethylsilylbenzamidinato copper (I) compound In a 50 ml Schlenk flask sufficiently purged with argon,
1.35 g of N, N, N'-tris (trimethylsilyl) benzamidine prepared above and anhydrous copper (I) chloride
0.39 g was added, anhydrous acetonitrile (manufactured by Wako Pure Chemical Industries, Ltd.) was distilled over calcium hydride, and then dried over active molecular sieves for 2 weeks, 20 ml of the mixture was added, and the mixture was heated and refluxed under argon. After 4 hours, the resulting precipitate was filtered under argon to give a slightly yellowish white powder. This powder is recrystallized from a mixed solution of methylene chloride / tetrahydrofuran to obtain a copper complex of a white needle-like crystal [having a dimer structure with a compound represented by the following formula (2)]. (2)
In the formula, TMS represents a trimethylsilyl group] 0.60 g
I got Identification was performed by NMR, IR and elemental analysis.

[0048]

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REFERENCE EXAMPLE 2 Synthesis of Copper Compound A dry-distilled reagent was used below unless otherwise specified. N, N'-ditrimethylsilylbenzamidinato copper (I
I) Synthesis of Compound Synthesis of N, N, N'-tris (trimethylsilyl) benzamidine Prepared in the same manner as in Reference Example 1.

Synthesis of N, N'-ditrimethylsilylbenzamidinato copper (II) compound In a 50 ml Schlenk flask sufficiently purged with argon,
1.3 g of N, N, N'-tris (trimethylsilyl) benzamidine prepared above and 0.28 g of anhydrous copper chloride
, And anhydrous acetonitrile (Wako Pure Chemical Industries, Ltd.) 15
ml was added to make a homogeneous solution. After 15 hours, the solvent was distilled off from the filtered filtrate by distillation under reduced pressure to obtain the desired product.
The target substance is recrystallized in a mixed solvent of tetrahydrofuran / n-hexane to obtain a green crystalline copper complex [compound represented by the following formula (3). (3) In the formula, TMS represents a trimethylsilyl group.] 0.65 g was obtained. Identification was performed by IR and elemental analysis.

[0051]

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Example 1 Synthesis of Polyethylene A 300 ml pressure-resistant glass container was purged with argon, and 100 ml of toluene was added.
10 mg of N'-ditrimethylsilylbenzamidinato copper (I) compound, 60 mg of 2,6-di-t-butyl-p-cresol and 3 ml of a 10% methylaluminoxane (manufactured by Aldrich) toluene solution were added. Next, ethylene gas was introduced into the container, and the inside of the system was 1.1 kg / cm ^2.
After polymerization was carried out at 0 ° C. for 4 hours while maintaining at G, the reaction was stopped by adding 150 ml of methanol to the reaction solution, and the precipitated polymer was recovered to obtain 1.3 g of polyethylene.

The polymer of the obtained polyethylene was analyzed by gel permeation chromatography (GPC) and differential scanning calorimetry (DSC). GP
O-Dichlorobenzene was used as the solvent for C. The weight average molecular weight is 390,000 and the number average molecular weight is 165,000.
Mw / Mn, which is the ratio of the weight average molecular weight to the number average molecular weight, indicating the molecular weight distribution, was 2.36. Also, DS
The melting temperature, which is the peak of the melting curve by C, was 139 ° C., and no melting peak could be observed below 60 ° C.

Example 2 10% methylaluminoxane
The same conditions as in Example 1 except that 16.4 mg of N, N-dimethylluanilinium tetrakis (pentafluorophenyl) borate and 1 ml of a 1M toluene solution of triisobutylaluminum (manufactured by Aldrich) were used instead of 3 ml of the toluene solution. Was carried out to obtain 1.5 g of polyethylene.

When the obtained polyethylene was evaluated in the same manner as in Example 1, the weight average molecular weight was 330,
000, the number average molecular weight is 160,000, showing the molecular weight distribution, the ratio of the weight average molecular weight to the number average molecular weight, Mw / M
n was 2.06. The melting temperature, which is the peak of the melting curve by DSC, was 138 ° C., and no melting peak could be observed below 60 ° C. as in Example 1.

(Comparative Example 1) N, N'-Ditrimethylsilylbenzamidinato copper (II) prepared in Reference Example 2 above was used in place of 10 mg of the N, N'-ditrimethylsilylbenzamidinato copper (I) compound. ) Polymerization was performed under the same conditions as in Example 1 except that 17 mg of the compound was used to obtain 0.2 g of polyethylene.

[0057]

The method for producing a polymer using a copper compound of the present invention has the above-mentioned constitution, and uses an inexpensive copper-based catalyst which is excellent in stability and easy to handle as a polymerization catalyst. Therefore, a polymer having a narrow molecular weight distribution can be easily and inexpensively provided in a high yield.

Claims (4)

[Claims] When a vinyl monomer is polymerized, monovalent copper is contained in the structure as a catalyst and / or a polymerization initiator, and is represented by a general formula LCuX, LCu or L (L ') Cu. A copper compound (wherein L and L ′ represent a ligand, X represents a halogen atom, an alkoxy group, a thioxy group, an allyloxy group, an amino group, a secondary amino group, a tertiary amino group, a cyano group, A nitro group, an alkyl group or an allyl group). 2. Aluminoxane, a general formula AlR _m Z _3-m (where R is a hydrocarbon group having 1 to 20 carbon atoms, Z is a hydrogen atom, a halogen atom, an alkoxy group, an allyloxy group, Represents a siloxy group, m is an integer of 0 to 3), at least one organic metal selected from the group consisting of an organoaluminum compound represented by the following formula: a Lewis acid having a boron atom; and an ionic compound having a boron atom. The method for producing a polymer using a copper compound according to claim 1, wherein a compound is used. 3. Formula LCuX, LCu or L (L ′) C
3. The copper according to claim 1, wherein at least one of the ligands of the copper compound represented by u is a ligand coordinated by an unpaired electron of an N atom in the structure. A method for producing a polymer using a compound. 4. Formula LCuX, LCu or L (L ′) C
3. At least one of the ligands of the copper compound represented by u is an amidinato group.
Or a method for producing a polymer using the copper compound according to 3.