JPH11246623A - Terminal-modified polyolefin and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polyolefin having only a terminal of a polypropylene or an ethylene-propylene random copolymer, which is modified with a (meth) acrylic acid derivative unit of a cyclic amine compound, and which is close to monodisperse. SOLUTION: A polyolefin obtained by modifying the terminal of a polypropylene or an ethylene-propylene random copolymer obtained by living polymerization with a (meth) acrylic acid derivative unit of a cyclic amine compound. As the (meth) acrylic acid derivative of the cyclic amine compound, for example, a (meth) acrylate having a piperidine ring or a pyrrolidine ring structure is used.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a polyolefin in which a polymer terminal is modified with a (meth) acrylic acid derivative unit of a cyclic amine compound.

[0002]

2. Description of the Related Art In the conventional polymerization of α-olefins such as propylene with a Ziegler-Natta type catalyst, a chain transfer reaction or termination reaction occurs, and it is difficult to modify only the terminal of the obtained polymer with a substituent or the like. It is.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides a polyolefin in which only the terminal of a polypropylene or ethylene-propylene random copolymer is modified with a (meth) acrylic acid derivative unit of a cyclic amine compound and which is close to monodisperse. The purpose is to do.

[0004]

Means for Solving the Problems As a result of diligent studies, the present inventors have found that living polypropylene or ethylene-propylene random copolymer obtained using a vanadium complex catalyst which does not involve a chain transfer reaction or a termination reaction. It has been found that the object of the present invention can be achieved by reacting a (meth) acrylic acid derivative of a cyclic amine compound,
The present invention has been completed. That is, the present invention is a terminal-modified polyolefin obtained by modifying the terminal of a polypropylene or an ethylene-propylene random copolymer with a substituent represented by the general formula (1).

[0005]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. )

The preferred embodiments of the present invention are as follows. The molecular end of the terminal-modified polyolefin is represented by the general formula (4)
The above-mentioned terminal-modified polyolefin which is a mixture of polymers represented by the formula:

[0007]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group, m is a number of 0.1 to 100, and represents an average degree of polymerization. The above-mentioned terminal-modified polyolefin, wherein the (meth) acrylic acid derivative of the cyclic amine compound is a compound having a piperidyl ring structure or a pyrrolidine ring structure.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Terminal-Modified Polyolefin The terminal-modified polyolefin of the present invention is modified such that the terminal of polypropylene or an ethylene-propylene random copolymer is modified with a substituent of a (meth) acrylic acid derivative of a cyclic amine compound represented by the general formula (1). .

[0009]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. In the formula, examples of the alkyl group include a methyl group, an ethyl group, and a propyl group, and examples of the ring structure include a pyrrolidine ring structure and a piperidine ring structure.

[0010] The terminal-modified polyolefin of the present invention is preferably a mixture of polymers in which the molecular terminals of the terminal-modified polyolefin are represented by the general formula (4).

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group, m is a number of 0.1 to 100, and represents an average degree of polymerization. )

2. Method for Producing Terminal-Modified Polyolefin The terminal-modified polyolefin of the present invention is obtained by synthesizing a propylene living polymer using a catalyst comprising a vanadium chelate compound represented by the general formula (2) and an organic alkylaluminum compound, and then formula (3) )) And a (meth) acrylic acid derivative of a cyclic amine compound represented by formula (1).

[0012]

Embedded image (Wherein, R ^{1 to} R ³ represent a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms or an aryl group. However, at least one of R ^{1 to} R ³ needs to be a hydrogen atom, R ^{1 to} R ³
Must not be all hydrogen atoms. )

[0013]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. The following describes each item.

(1) Living polymerization catalyst (a) Vanadium compound The vanadium compound catalyst is represented by the general formula (2).

[0015]

Embedded image (In the formula, R ^{1 to} R ³ represent a hydrogen atom or a hydrocarbon having 1 to 8 carbon atoms, and at least one of R ^{1 to} R ³ is a hydrogen atom, but all of R ^{1 to} R ³ are hydrogen. It must not be an atom.)

Specific examples of the compounds contained in the above formula are represented by R ¹ to
To illustrate as R ³ below, R ² is hydrogen atom, when R ¹ and R ³ is a hydrocarbon ^{group, R 1 / R 3: CH} 3 / CH 3, CH 3 / C 2 H 5, CH ₃ / C
_{6 H 5, CH 3 / C} 6 H 5 CH 2, C 2 H 5 / C 2 H 5, C 2 H 5 /
_{C 6 H 5, C 2 H} 5 / C 6 H 5 CH 2, C 6 H 5 / C 6 H 5, C 6 H
₅ / C ₆ H ₅ CH ₂ , C ₆ H ₅ CH ₂ / C ₆ H ₅ CH ₂ , R ² is a hydrocarbon group, one of R ¹ and R ³ is a hydrogen atom and the other is a hydrocarbon group. In some cases, R ² / R ¹ or R ³ : CH ₃ / CH ₃ , C ₂ H ₅ / CH ₃ , C
_{6 H 5 / CH 3, C} 6 H 5 CH 2 / CH 3, CH 3 / C 2 H 5, C
_{6 H 5 / C 2 H 5} , C 6 H 5 CH 2 / C 2 H 5, CH 3 / C 6 H 5,
_{C 2 H 5 / C 6 H} 5, C 6 H 5 / C 6 H 5, C 6 H 5 CH 2 / C 6 H
_{5, CH 3 / C 6 H} 5 CH 2, C 2 H 5 / C 6 H 5 CH 2, C 6 H 5
/ C ₆ H ₅ CH ₂ , C ₆ H ₅ CH ₂ / C ₆ H ₅ CH ₂ , where R ² is hydrogen, one of R ¹ and R ³ is a hydrogen atom, and the other is a hydrocarbon group , R ¹ or R ³ : CH ₃ , C ₂ H ₅ , C ₆ H ₅ , C ₆ H ₅ CH ₂ , etc. Among them, the following compounds are particularly desirable.

[0017]

Embedded image

(B) Organoaluminum Compound The organoaluminum compound is represented by the general formula: R ¹⁰ _3-n AlX
_n (wherein, R ¹⁰ represents an alkyl group having 1 to 18 carbon atoms, X represents a halogen atom or a hydrogen atom, and n represents 0 ≦ n
Indicates an arbitrary number in the range of ≦ 3. ).

The compounds included in the above formula include, for example, those having 1 to 8 carbon atoms, preferably 2 to 6 carbon atoms.
Is an organoaluminum compound having three alkyl groups. Specifically, dimethylaluminum chloride, diethylaluminum chloride, diethylaluminum bromide, diethylaluminum iodide, dialkylaluminum monohalide such as diisobutylaluminum chloride, methylaluminum dichloride, ethylaluminum dichloride, isobutylaluminum dichloride, methylaluminum dibromide, Monoalkyl dihalides such as ethylaluminum dibromide, isobutylaluminum dibromide and ethylaluminum diiodide, and alkylaluminum sesquihalides such as ethylaluminum sesquichloride and isobutylaluminum sesquichloride.

(2) Living Polymerization of Propylene In the living polymerization of propylene, a small amount of ethylene or 1-butene,
It is also possible to carry out polymerization in the presence of α-olefins such as -hexene and 4-methyl-1-pentene.

The living polymerization reaction of propylene is desirably carried out in a solvent which is inert to the polymerization reaction and is liquid at the time of polymerization. The solvent may be a saturated solvent such as propane, butane, pentane, hexane or heptane. Examples thereof include aliphatic hydrocarbons, saturated alicyclic hydrocarbons such as cyclopropane and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, and mixed solvents thereof.

The amount of the polymerization catalyst used in the polymerization of propylene is as follows: (a) 1 × 10 ^{−4 to} 0.1% of the vanadium compound per mole of propylene or a small amount of comonomer.
Mol, desirably 5 × 10 ^{−4 to} 5 × 10 ⁻² mol, and the organoaluminum compound (b) is 1 × 10 ^{−4 to} 0.5 mol, desirably 1 × 10 ^{−3 to} 0.1 mol. The organoaluminum compound (b) is preferably used in an amount of 4 to 100 mol per 1 mol of the vanadium compound (a).

The living polymerization in the present invention is usually carried out by -1
Performed at 00 ° C to 0 ° C for 0.2 to 50 hours. The molecular weight and yield of the obtained living polypropylene can be adjusted by changing the reaction temperature and reaction time.
In particular, by setting the temperature to −30 ° C. or lower, a polymer having a molecular weight distribution close to monodispersion can be obtained. At −40 ° C. or lower, a living polymer having a molecular weight distribution Mw (weight average molecular weight) / Mn (number average molecular weight) of 1.05 to 1.40 can be obtained.

Before or during the polymerization reaction, a reaction accelerator can be used. Examples of the reaction accelerator include anisole, water, oxygen, alcohol (such as methanol, ethanol, and isopropanol), ester (such as ethyl benzoate and ethyl acetate), unsaturated alicyclic hydrocarbon (such as cyclopentene and cyclohexene), and unsaturated fatty acid. Group hydrocarbons (eg, 2-pentene, 2-hexene), ketones (eg, acetone, acetylacetone, methyl ethyl ketone, cyclohexanone), and ethers (eg, dimethyl ether, diethyl ether, acetal, dioxane).
The amount of the accelerator used is usually 0.001 to 2 mol per 1 mol of the vanadium compound. By the above method, about 80
Living polypropylene having a number average molecular weight of 0 to about 400,000 and close to monodispersion can be produced.

(2) Living Random Copolymerization of Ethylene-Propylene The living random copolymerization of ethylene-propylene is preferably carried out in a solvent which is inert to the polymerization reaction and is liquid at the time of polymerization. As a saturated aliphatic hydrocarbon such as propane, butane, pentane, hexane and heptane; a saturated alicyclic hydrocarbon such as cyclopropane and cyclohexane; an aromatic hydrocarbon such as benzene, toluene and xylene; or a mixed solvent thereof. And the like. The method of contacting ethylene and propylene with the polymerization catalyst can be arbitrarily selected, but is preferably a method of sequentially adding a solution of an organoaluminum compound and a solution of a vanadium compound to a solvent solution of ethylene and propylene, or For example, a method in which ethylene and propylene are added to a solvent solution containing a compound and a vanadium compound and brought into contact with each other is used.

The amount of the polymerization catalyst used in the living random copolymerization reaction of ethylene-propylene is such that the vanadium compound is (a) 1 × 10 ^-4 per mole of ethylene and propylene.
0.1 mol, preferably 5 × 10 ^{−4 to} 5 × 10 ⁻² mol,
The amount of the organoaluminum compound (b) is 1 × 10 ^{−4 to} 0.5 mol, preferably 1 × 10 ^{−3 to} 0.1 mol. In addition,
The organoaluminum compound (b) is preferably used in an amount of 4 to 100 mol per 1 mol of the vanadium compound (a).

The molecular weight and yield of the obtained ethylene-propylene living random copolymer can be adjusted by changing the reaction temperature and the reaction time. By setting the polymerization temperature to a low temperature, particularly -30 ° C or lower, a polymer having a molecular weight distribution close to monodispersion can be obtained. -40
C. or lower, the molecular weight distribution Mw (weight average molecular weight) / Mn
A living ethylene-propylene random copolymer having a (number average molecular weight) of 1.05 to 1.40 is obtained.

Further, a reaction accelerator can be used before or during the polymerization reaction. Examples of the reaction accelerator include anisole, water, oxygen, alcohol (such as methanol, ethanol, and isopropanol), ester (such as ethyl benzoate and ethyl acetate), unsaturated alicyclic hydrocarbon (such as cyclopentene and cyclohexene), and unsaturated fatty acid. Group hydrocarbons (eg, 2-pentene, 2-hexene), ketones (eg, acetone, acetylacetone, methyl ethyl ketone, cyclohexanone), and ethers (eg, dimethyl ether, diethyl ether, acetal, dioxane).
The amount of the accelerator used is usually 0.001 to 2 mol per 1 mol of the vanadium compound. The proportion of ethylene and propylene in the living copolymer is usually 90 mol% ethylene.
Up to. This can be adjusted by changing the use ratio of ethylene and propylene during living polymerization. However, when the use amount of ethylene is increased, the molecular weight distribution of the copolymer becomes undesirably wide. Ethylene content is high, the molecular weight distribution is narrow, that is, when producing a living copolymer close to monodisperse, before living copolymerization of ethylene and propylene, supply a small amount of propylene to the polymerization system,
By holding for 0.1 to 1 hour, a large amount of ethylene can be introduced into the copolymer while the molecular weight distribution of the living copolymer remains narrow. As above, about 50
A living ethylene-polypropylene random copolymer having a number average molecular weight of 0 to about 500,000 and almost monodisperse can be produced.

3. Reaction of cyclic amine compound with (meth) acrylic acid derivative (1) (meth) acrylic acid derivative of cyclic amine compound (meth) acrylic acid derivative of cyclic amine compound to be reacted with living polypropylene or ethylene-polypropylene random copolymer is And a compound represented by the general formula (3).

[0030]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. In the formula, examples of the alkyl group include a methyl group, an ethyl group, and a propyl group, and examples of the ring structure include a pyrrolidine ring structure and a piperidine ring structure. A typical example is a compound having the following structural formula.

[0031]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. )

[0032]

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. )

(2) Modification Reaction The reaction between the living polypropylene or the ethylene-propylene random copolymer and the (meth) acrylic acid derivative of the cyclic amine compound is carried out in a system where the living polypropylene or the ethylene-propylene random copolymer is present. ,
A method of supplying and reacting an acrylic acid derivative compound is preferred. The reaction is carried out at a temperature between -100 ° C and + 150 ° C for 5 minutes to 50 hours. By increasing the reaction temperature or increasing the reaction time, the modification rate of the polyolefin terminal can be increased. The (meth) acrylic acid derivative of the cyclic amine compound is used in an amount of 1 to 1000 mol per 1 mol of the living polyolefin, and may be used alone or as a mixture of two or more compounds represented by the general formula (3). You may use it.

A reaction product of a living polypropylene or a random copolymer of ethylene-polypropylene and a (meth) acrylic acid derivative of the above cyclic amine compound is then brought into contact with a proton donor to obtain the terminal-modified polyolefin of the present invention. . Examples of the proton donor include alcohols such as methanol, ethanol and phenol, and mineral acids such as hydrochloric acid and sulfuric acid. Alcohols and mineral acids may be used simultaneously. The contact with the proton donor is usually performed at -100 ° C to + 100 ° C for 1 minute to 10 minutes.

The terminal-modified polyolefin of the present invention obtained as described above has a number average molecular weight (Mn) of about 800 to about 4,000,000, and the living polypropylene or ethylene-polypropylene random copolymer described above. Had a very narrow molecular weight distribution (Mw / Mn =
1.05 to 1.40), and has a terminal weight of 0.1 to 100, preferably 0.2 to 5
The cyclic amine compound is modified with 0, more preferably 0.3 to 25, (meth) acrylic acid derivatives. One feature of the terminal-modified polyolefin of the present invention is that the syndiotactic dyad fraction is 0.6 or more.

The terminal-modified polyolefin obtained as described above is a mixture of polymers in which the molecular terminals of the terminal-modified polyolefin are represented by the general formula (4).

Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group, m is a number of 0.1 to 100, and represents an average degree of polymerization. )

[0037]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail with reference to embodiments. In addition, the characterization of the polymer in an Example was performed by the following method. (1) Molecular weight and molecular weight distribution: GPC manufactured by Waters
(Gel permeation chromatography) Model 1
50 was used. The solvent used was o-dichlorobenzene, the measurement conditions were 135 ° C., the solvent flow rate was 1.0 ml / min, the column was a monodisperse polystyrene standard sample manufactured by Tosoh Corporation, and a calibration curve of polystyrene was obtained. A calibration curve of polypropylene was prepared. (2) Determination of structure of polymer: Infrared absorption spectrum: Model IR-810 (trade name) manufactured by JASCO Corp.
It was measured using an infrared spectrophotometer. Elemental analysis: Regarding the nitrogen content, a 1.5 mg sample was collected using EA1108 manufactured by Carlo Elba, pyrolyzed (about 1300 ° C.) in a combustion tube in an oxygen stream, further reduced, and introduced into a separation column. And quantified with a detector. ¹³ C-NMR spectrum: XL-200 (trade name) manufactured by Varian with a PFT pulse Fourier transform device, 50 MHz, 120 ° C., pulse width 8.2 μs π /
3, the measurement was performed under the conditions of a pulse interval of 4 seconds and an integration frequency of 5000. Samples were trichlorobenzene and benzene (2: 1)
And dissolved in a mixed solution of the above.

Example 1 In a 1.5-liter autoclave sufficiently purged with nitrogen gas,
400 ml of toluene was added and cooled to -60 ° C. At the same temperature, 200 g of propylene was added and liquefied and dissolved in toluene. Then 50 mmol of diethylaluminum chloride in toluene and 1.5 mmol of V
Toluene solution of (2-methyl-1,3-butanedionate) ₃ was added, and polymerization of propylene was started with stirring.
Continued for 2 hours. Next, 500 mmol of 1,2,2,6,6-pentamethyl-4-piperidyl-methacrylate was added and reacted at the same temperature for 1 hour. Then 50m
1 ethanol / hydrochloric acid mixture (45/5 / ml / ml)
Was added to stop the reaction. After removing unreacted propylene by raising the reactor temperature to 25 ° C. over 24 hours, the reaction solution was poured into 3.0 l of ethanol to precipitate a polymer. The obtained polymer was washed with hexane 20
After re-dissolving in 0 ml, the mixture was filtered. Hexane insolubles caused by a homopolymer of 1,2,2,6,6-pentamethyl-4-piperidyl-methacrylate, which could be considered as a by-product, were not observed. The hexane solution of the filtrate was poured into 3.0 l of ethanol to precipitate the polymer again. By repeating this operation five times, the catalyst residue and unreacted 1,2,2,6,6-pentamethyl-4-piperidyl-
After removing the methacrylate, the residue was dried at room temperature under reduced pressure to give 1
5.1 g of polymer were obtained. The GPC curve of the obtained polymer was monomodal. The number average molecular weight (M
n) was 2.5 × 10 ⁴ , and Mw / Mn was 1.13, a value close to monodispersion. The infrared absorption spectrum (IR) of this polymer was measured. As a result, a peak at 1730 cm ^-1 based on the absorption of a carbonyl group was observed. Further, when the nitrogen content of this polymer was measured by elemental analysis, it was 510 ppm, and an average of 0.9 cyclic amine compounds were bound per molecule.

Example 2 In a 1.0-liter autoclave sufficiently purged with nitrogen gas,
250 ml of toluene was added and cooled to -50 ° C. At the same temperature, 140 g of propylene was added and liquefied and dissolved in toluene. Then 35 mmol of diethylaluminum chloride in toluene and 2.5 mmol of V
(Acetylacetonate) A toluene solution of ₃ was added, and polymerization of propylene was started with stirring and continued for 2 hours. Next, after 350 mmol of 2,2,6,6-tetramethyl-4-piperidyl-methacrylate was added, the temperature of the reaction system was raised to 0 ° C. over 1 hour, and the reaction was further performed at this temperature for 3 hours. Was. Hereinafter, processing is performed in the same manner as in Example 1,
20.3 g of a terminal-modified polypropylene having a number average molecular weight (Mn) of 4.8 × 10 ⁴ and Mw / Mn of 1.20 was obtained.
When the polymer was subjected to elemental analysis, the nitrogen content was found to be 380.
ppm, and an average of 1.3 cyclic amine compounds were bound per polymer molecule.

Example 3 100 ml of xylene was placed in a 300 ml flask sufficiently purged with nitrogen gas, and cooled to -60 ° C. At the same temperature, 100 mmol of propylene was added and liquefied and dissolved in xylene. Then a solution of 15 mmol of diethylaluminum chloride in xylene and 0.5 mmol of V
A xylene solution of (2-methyl-1,3-butanedionato) ₃ was added, and polymerization of propylene was started with stirring.
Continued for hours. Then, 1,2,5-trimethyl-4-
100 mmol of pyrrolidyl-methacrylate was added and reacted at the same temperature for 1 hour. Thereafter, the same treatment as in Example 1 was performed to obtain a number average molecular weight (Mn) of 5.3 × 10 ³ , Mw / M.
1.9 g of terminal-modified polypropylene having n of 1.18 was obtained. When the polymer was subjected to elemental analysis, the nitrogen content was 0.21% by weight, and an average of 0.8% per molecule of the polymer.
Cyclic amine compounds were bound.

Example 4 In a 1.0-liter autoclave sufficiently purged with nitrogen gas,
After adding 500 ml of toluene and cooling to −60 ° C., 25 mmol of a toluene solution of diethylaluminum chloride and 1.5 mmol of V (2-methyl-
1,3-Butandionato) ₃ in toluene was added.
Next, after the pressure in the system was reduced to 680 mmHg, a mixed gas of ethylene and propylene (20/80 molar ratio) was continuously supplied, and then 1,2,2,6,6-pentamethyl-4-piperidyl-methacrylic acid was supplied. After adding 500 mmol of the latet, the temperature of the reaction system was raised to -40 ° C, and the reaction was carried out at the same temperature for 3 hours. Thereafter, the same treatment as in Example 1 was performed, and the number average molecular weight (Mn) was 3.5 × 10 ⁴ , Mw / M
13.1 g of a terminal-modified ethylene-propylene random copolymer having n of 1.22 was obtained. Elemental analysis of this polymer revealed that the nitrogen content was 440 ppm, and that an average of 0.8 cyclic amine compounds were bonded per molecule of polymer. The obtained copolymer was subjected to ¹³ C-NMR measurement, and the propylene content was calculated from the area of the peak belonging to the secondary carbon and the area of the peak belonging to the tertiary carbon. As a result, the propylene content in the copolymer was 60.1 mol%
Met. In addition, this copolymer was used as a differential scanning calorimeter (D
As a result of thermal analysis by SC), a glass transition temperature (about 0 ° C.) due to the propylene homopolymer was not observed.

[0042]

The terminal-modified polyolefin of the present invention having a (meth) acrylic acid derivative of a cyclic amine compound at the terminal of the polyolefin has excellent weather resistance without bleeding out, for example, when used as a light stabilizer for general-purpose polyolefins. Show. Further, it can be used as a polyolefin modifier such as a coatability improver and an adhesion improver, or as a compatibilizer for a polymer alloy of a polyolefin and an engineering plastic.

Claims (2)

[Claims] 1. A terminal-modified polyolefin obtained by modifying the terminal of polypropylene or an ethylene-propylene random copolymer with a substituent represented by the general formula (1). Embedded image (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. ) 2. A living polymer of propylene is synthesized using a catalyst comprising a vanadium compound and an organoaluminum compound represented by the general formula (2), and then a (meth) amine of the cyclic amine compound represented by the general formula (3) is synthesized. 2. The method for producing a terminal-modified polyolefin according to claim 1, wherein the method is brought into contact with an acrylic acid derivative. Embedded image (Wherein, R ^{1 to} R ³ represent a hydrogen atom, a hydrocarbon group having 1 to 8 carbon atoms or an aryl group. However, at least one of R ^{1 to} R ³ needs to be a hydrogen atom, R ^{1 to} R ³
Must not be all hydrogen atoms. ) (Wherein, R ⁴ represents a hydrogen atom or an alkyl group, R ⁵
Represents a hydrogen atom, an alkyl group, a phenyl group or a phenoxy group, and R ^{6 to} R ⁹ represent a hydrogen atom or an alkyl group. )