JPH05247119A - Terminal modified polyolefin - Google Patents

Abstract

PURPOSE:To obtain a terminal modified polyolefin useful as a solubilizer, a modifier, etc., by modifying only terminals of polypropylene or ethylene- propylene random copolymer with (meth)acrylic acid derivative units. CONSTITUTION:(A) A living polypropylene or living ethylene-propylene random copolymer obtained by polymerizing propylene or ethylene and propylene in the presence of a catalyst consisting of a vanadium compound of formula I (R<1> to R<3> are H or 1-8C hydrocarbon group and at least one thereof is H and they are not simultaneously H) and an/organoaluminum compound is reacted with (B) 1-1000 mol (meth)acrylic acid derivative of formula II based on 1mol Al and then a proton donor (e.g. alcohols or mineral acids) is brought into contact with the reaction product to provide the objective polypropylene or ethylene-propylene random copolymer, having 2 0.6 syndiotactic diad fraction, in which only terminals are modified with (meth)acrylic acid derivative units of formula III (R is H or methyl).

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a polyolefin having a polymer terminal modified with a (meth) acrylic acid derivative unit.

[0002]

2. Description of the Related Art In the polymerization of α-olefins such as propylene with conventional Ziegler-Natta type catalysts, chain transfer reaction and termination reaction occur, so that it is difficult to modify only the end of the obtained polymer with a substituent or the like. Is.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides a polyolefin in which only terminals of polypropylene or an ethylene-propylene random copolymer are modified with a methacrylic acid (acrylic acid) derivative unit and which is nearly monodisperse. To aim.

[0004]

As a result of intensive studies, the present inventors have found that living polypropylene or ethylene-propylene random copolymer obtained by using a specific polymerization catalyst without chain transfer reaction or termination reaction. The present invention has been completed by finding that the object of the present invention can be achieved by reacting methacrylic acid (acrylic acid) derivative with.

[0005] SUMMARY OF THE INVENTION Namely, the present invention is polypropylene or an ethylene - propylene random copolymer terminal is modified with a substituent represented by the following general formula I terminal modified polyolefin, the general formula I

[Chemical 2] [However, R represents a hydrogen atom or a methyl group. ] Is the gist.

The terminal-modified polyolefin of the present invention is usually obtained in the form of a composition whose terminal is represented by the following general formula II. General formula II

[Chemical 3] [However, R has the same meaning as described above, and n is 0.1 to 50.
Represents the number of 0]

The terminal-modified polyolefin of the present invention has the following general formula III and general formula III

[Chemical 4] [R ^{1 to} R ³ represent a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms. However, at least one of R ^{1 to} R ³ must be a hydrogen atom, but all of R ^{1 to} R ³ must not be hydrogen atoms. ] In the presence of a catalyst consisting of a vanadium compound and an organoaluminum compound represented by living polypropylene obtained by polymerizing propylene or a living ethylene-propylene random copolymer obtained by random copolymerization of ethylene and propylene, , Formula IV

[Chemical 5] [However, R is as defined above. ] It can manufacture by making it react with the methacrylic acid (acrylic acid) derivative represented by this.

The catalyst (a) vanadium compound The vanadium compound used in the present invention has the general formula III:

[Chemical 6][However, R¹~ R³Has the same meaning as above. ] Is represented.
A specific example included in the above formula will be described below.・ R²Is a hydrogen atom, and R¹And R³Is a hydrocarbon group
If R¹/ R³: CH₃/ CH₃, CH₃/ C₂H_Five, C₂
H_Five/ C₂H_Five, CH ₃/ C₆H_Five, C₂H_Five/ C₆H
_Five, C₆H_Five/ C₆H_Five, CH₃/ C₆H_FiveCH₂, C
₆H_FiveCH₂/ C₆H_FiveCH₂, C₂H_Five/ C₆H_FiveC
H₂, C₆H_Five/ C₆H_FiveCH₂．・ R²Is a hydrocarbon group, R¹, R³One of them is water
When the other is a hydrocarbon group in the elementary atom. R²/ R¹Or R³: CH₃/ CH₃, C₂H_Five/ CH
₃, CH₃/ C₂H_Five, C₂H_Five/ C₂H_Five, C₂H_Five
/ CH₃, CH₃/ C₆H_Five, C₆H_Five/ C₂H_Five, C
₂H_Five/ C₆H_Five, C₆H_Five/ C₆H_Five, C₆H_FiveCH
₂/ CH₃, CH₃/ C₆H_FiveCH₂, C₆H_FiveCH₂
/ C₆H_FiveCH₂, C₆H_FiveCH₂/ C ₂H_Five, C₂H
_Five/ C₆H_FiveCH₂, C₆H_FiveCH₂/ C₆H_Five, C₆
H_Five/ C ₆H_FiveCH₂．・ R²Is a hydrogen atom, and R¹, R³Is hydrogen
When an atom is another hydrocarbon group. R¹Or R³: CH₃, C₂H_Five, C₆H_Five, C₆H_Five
CH₂ The following compounds are particularly desirable among these
Good

[Chemical 7]

[Chemical 8]

[Chemical 9]

(B) Organoaluminum compound The organoaluminum compound has the general formula R _n AlX
_3-n (wherein R is an alkyl group or an aryl group, X is a halogen atom or a hydrogen atom, and n is an arbitrary number within the range of 1 ≦ n <3), and examples thereof include dialkyl. Particularly preferred are alkylaluminum compounds having 1 to 18 carbon atoms, preferably 2 to 6 carbon atoms such as aluminum monohalide, monoalkylaluminum dihalide and alkylaluminum sesquihalide, or a mixture or complex compound thereof. Specifically, dimethyl aluminum chloride, diethyl aluminum chloride, diethyl aluminum bromide, diethyl aluminum iodide, dialkyl aluminum monohalide such as diisobutyl aluminum chloride, methyl aluminum dichloride, ethyl aluminum dichloride, methyl aluminum dibromide, ethyl aluminum dibromide, Examples thereof include monoalkyl aluminum dihalides such as ethyl aluminum diiodide and isobutyl aluminum dichloride, and alkyl aluminum sesquihalides such as ethyl aluminum sesquichloride.

The proportion of the vanadium compound and the organoaluminum compound used is 1 to 1,000 moles of the organoaluminum compound per mole of the vanadium compound.

Living Polymerization of Propylene Living polymerization of propylene includes, in addition to homopolymerization of propylene, a small amount of ethylene or 1-butene, 1
It is also possible to polymerize in the presence of an α-olefin such as -hexene or 4-methyl-1-pentene.

The polymerization reaction is inert to the polymerization reaction,
And it is desirable to carry out in a liquid solvent at the time of polymerization, as the solvent, saturated aliphatic hydrocarbons such as propane, butane, pentane, hexane, heptane, saturated alicyclic hydrocarbons such as cyclopropane, cyclohexane, benzene. , And aromatic hydrocarbons such as toluene and xylene.

The amount of the polymerization catalyst used during the polymerization of propylene is 1 × 10 ^{−4 to} 0.1 mol of vanadium compound per 1 mol of propylene or propylene and a small amount of comonomer.
5 × 10 ^{−4 to} 5 × 10 ⁻² mol, preferably 1 × 10 ^{−4 to} 0.5 mol of organoaluminum compound, preferably 1 ×
It is 10 ^{−3 to} 0.1 mol. In addition, vanadium compound 1
The organoaluminum compound is preferably 4 to 4 moles.
100 mol is used.

Living polymerization is usually from -100 ° C to +10.
It is carried out at 0 ° C for 0.5 to 50 hours. The molecular weight and yield of the obtained living polypropylene 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. At −50 ° C. or lower, Mw (weight average molecular weight) / Mn (number average molecular weight)
Can be a living polymer having a ratio of 1.05 to 1.40.

A reaction accelerator may be used during the polymerization reaction. As the reaction accelerator, anisole, water, oxygen,
Examples thereof include alcohols (methanol, ethanol, isopropanol, etc.) and esters (ethyl benzoate, ethyl acetate, etc.). The amount of the accelerator used is usually 0.1 to 2 mol per mol of the vanadium compound. By the above method, a living polypropylene having a number average molecular weight of about 500 to about 500,000 and being nearly monodisperse can be produced.

Living random ethylene-propylene
The copolymerization polymerization reaction is preferably carried out in a solvent which is inert to the polymerization reaction and which is liquid at the time of the polymerization, and examples of the solvent include saturated aliphatic hydrocarbons such as propane, butane, pentane, hexane and heptane. Saturated cycloaliphatic hydrocarbons such as cyclopropane and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene. The method of contacting the polymerization catalyst with ethylene and propylene 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 contacting the organoaluminum. A method of adding ethylene and propylene to a solvent solution containing a compound and a vanadium compound and bringing them into contact with each other.

The amount of the polymerization catalyst used is such that the vanadium compound is 1 × 10 ^{−4 to} 0.
1 mol, preferably 5 × 10 ⁻⁴ mol to 5 × 10 ⁻² mol,
The organoaluminum compound is 1 × 10 ^{−4 to} 0.5 mol, and preferably 1 × 10 ^{−3 to} 0.1 mol. The organoaluminum compound is preferably used in an amount of 4 to 100 mol per mol of the vanadium compound. The molecular weight and yield of the resulting living copolymer can be adjusted by changing the reaction temperature and the reaction time. In the present invention, a polymer having a molecular weight distribution close to monodispersion can be obtained by setting the polymerization temperature to a low temperature, particularly -30 ° C or less,
In the following, a living ethylene-propylene random copolymer having Mw (weight average molecular weight) / Mn (number average molecular weight) of 1.05 to 1.40 is obtained.

A reaction accelerator may be used during the polymerization reaction. As the reaction accelerator, anisole, water, oxygen,
Examples thereof include alcohols (methanol, ethanol, isopropanol), esters (ethyl benzoate, ethyl acetate, etc.). The amount of the accelerator used is usually 0.1 to 2 mol per mol of the vanadium compound. The proportion of ethylene and propylene in the living copolymer is usually up to 90 mol% ethylene. This can be adjusted by changing the use ratio of ethylene and propylene during living polymerization, but if the use ratio of ethylene is increased, the molecular weight distribution of the copolymer becomes wider, which is not desirable. When producing a living copolymer having a high ethylene content and a narrow molecular weight distribution, that is, a monodisperse living copolymer, a small amount of propylene is supplied to the polymerization system before the living copolymerization of ethylene and propylene. By holding for 1 hour, a large amount of ethylene can be introduced into the copolymer while the living copolymer has a narrow molecular weight distribution. As described above, a living ethylene-propylene random copolymer having a number average molecular weight of about 500 to 500,000 (converted to propylene, the same applies hereinafter) and being nearly monodisperse can be produced.

Reaction with methacrylic acid (acrylic acid) derivatives
Response living polypropylene or ethylene - methacrylic acid reacted with the propylene random copolymer (acrylic acid)
The derivative (hereinafter referred to as compound I) has the general formula IV,

[Chemical 10] It is represented by. In the formula, R is a hydrogen atom or a methyl group. The reaction between the living polypropylene or the ethylene-propylene random copolymer and the compound I is preferably carried out by supplying the compound I to the reaction system in which the living polypropylene or the ethylene-propylene random copolymer is present and causing the reaction. The reaction is carried out at a temperature of -100 ° C to + 150 ° C for 5 minutes to 50 hours. By increasing the reaction temperature or lengthening the reaction time, the modification rate of the polyolefin terminal with the compound I unit can be increased.
Compound I is based on 1 mol of living polyolefin,
It is used in an amount of 1 to 1,000 mol.

The reaction product of living polypropylene or ethylene-propylene random copolymer with compound I is then contacted 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. The alcohol and the mineral acid may be used at the same time. The proton donor is usually used in large excess. The contact with the proton donor is
Usually, it is carried out at -100 ° C to + 100 ° C for 1 minute to 10 hours.

The polyolefin of the present invention obtained as described above follows the number average molecular weight (Mn) of about 500 to about 500,000 and the living polypropylene or ethylene-propylene random copolymer itself. Very narrow molecular weight distribution (Mw / Mn = 1.05-1.
40) and each end is 0.1-500
Preferably 0.2 to 100, more preferably 0.
It is modified with 5 to 50 of the compound I units.
Further, the terminal-modified polyolefin of the present invention is characterized in that the syndiotactic dyad fraction is 0.6 or more.

[0022]

EXAMPLES The present invention will be described below with reference to examples. The characterization of the polymer was carried out by the following method. -Molecular weight and molecular weight distribution A GPC (gel permeation chromatography) model 150 manufactured by Waters was used. Solvent: o-dichlorobenzene, measurement temperature: 135 ° C, solvent flow rate: 1.0
ml / min. Column is Tohso GMH6HT (trade name)
It was used. In the measurement, a standard curve of polystyrene was obtained using a monodisperse polystyrene standard sample manufactured by Tosoh Corporation, and a standard curve of polypropylene was prepared by the universal method. -Structural determination of polymer ( ¹ H-NMR spectrum): JSX-4 manufactured by JEOL Ltd.
00 (trade name), Fourier transform type NMR spectrometer was used under the conditions of 400 MHz, 30 ° C. and pulse interval of 15 seconds. The sample was prepared by dissolving it in deuterated chloroform. ( ¹³ C-NMR spectrum): VFT XL-200 type (trade name) with PFT pulse Fourier transform device
50MHz, 120 ° C, pulse width 8.2μs
The measurement was performed under the conditions of π / 3, pulse interval of 4 seconds, and integration number of 5,000. Samples were trichlorobenzene and benzene (2:
It was adjusted by dissolving it in the mixed solvent of 1). (Infrared absorption spectrum): The polymer was cast on a KBr plate and measured using a Model IR-810 (trade name) infrared spectrophotometer manufactured by JASCO Corporation.

Example 1 Living Polymerization of Propylene In a 300 ml flask sufficiently replaced with nitrogen gas, n-
100 ml of heptane was added and cooled to -60 ° C. 200 mmol of propylene was added at the same temperature and dissolved in n-heptane. Then 15 mmol of Al (C ₂ H ₅ ) ₂ C
1 n-heptane solution and 1.5 mmol V (2-methyl-1,3-butanedionate) ₃ toluene solution were added, and polymerization was started with stirring. Polymerization of propylene-
It was carried out at 60 ° C. for 1 hour.

Reaction with Glycidyl Methacrylate In the above reaction system, glycidyl methacrylate (GMA) is used.
100 mmol was added at −60 ° C., the temperature in the system was raised to 25 ° C. over 1 hour, and the mixture was stirred at the same temperature to GM.
Reaction with A was carried out. After 5 hours, the reaction solution was put into 500 ml of ethanol to precipitate a polymer. The obtained polymer was dissolved again in n-heptane and centrifuged to obtain a supernatant. The supernatant was poured into 500 ml of methanol to precipitate the polymer again. The obtained polymer was washed 5 times with methanol and then dried under reduced pressure at room temperature to obtain 1.15 g of a polymer.

The GPC outflow curve of the obtained polymer is unimodal.
It was sex. Mn of this polymer was 4.2 × 10.³And
The Mw / Mn was 1.17, which was a value close to monodispersion.
Infrared absorption spectrum (IR) analysis of this polymer was carried out.
By the way, 1740 cm ^-1Based on the stretching vibration of the carbonyl group
Subsequent absorption was observed. Further¹As a result of 1 H-NMR analysis,
Peak due to proton of polypropylene (δ = 0.
7 to 1.7 ppm) other than the following chemical shift values
Peaks were observed.

[Chemical 11] Proton signal of polypropylene part (δ = 0.7 ~
1.7 ppm) and the area ratio of the signal (d),
The resulting polymer was found to have 13 GMA units introduced at the ends of polypropylene, as described below.

[Chemical 12] In order to measure the syndiotactic dyad fraction of the obtained polypropylene, living polymerization of propylene was separately carried out by the same operation as above, and then the reaction solution was cooled to −78 ° C.
Polymerization was quickly stopped by pouring into 500 ml of an ethanol-hydrochloric acid solution cooled to 50 ° C.
It was washed 5 times with 1 L of ethanol and dried at room temperature to obtain polypropylene. Next, the resulting polypropylene ¹³ C-N
MR analysis was performed. The stereoregularity of polypropylene calculated from the multiplex intensity ratio of methyl carbon in the spectrum is shown below. Triad fraction Diad fraction ^a) [rr] [rm] [mm] [r] 0.625 0.320 0.055 0.785 a) Calculated from the triad fraction

Examples 2 to 4 Terminal-modified polypropylene was obtained in the same manner as in Example 1 except that the reaction conditions for propylene and GMA were as shown in Table 1. The results are shown in Table 1.

Example 5 400 ml of n-heptane was placed in a 1.5 liter autoclave sufficiently replaced with nitrogen gas and cooled to -60 ° C. 200 g of propylene was added at the same temperature and liquefied and dissolved in n-heptane. Then 50 mmol Al
A solution of (C ₂ H ₅ ) ₂ Cl in n-heptane and a solution of 0.6 mmol of V (2-methyl-1,3-butanedionate) _{3 in} toluene were added, and the polymerization was started with stirring and continued for 15 hours. Then, after adding 500 mmol of GMA at the same temperature, the temperature of the reaction system was raised to 0 ° C. over 1 hour,
The reaction with GMA was carried out at 0 ° C. for 15 hours. Thereafter, the same treatment as in Example 1 was carried out to obtain a terminal-modified polypropylene having the properties shown in Table 1.

Example 6 In a 300 ml flask sufficiently replaced with nitrogen gas, n-
100 ml of heptane was added and cooled to -78 ° C. 200 mmol of propylene was added at the same temperature, and liquefied and dissolved in n-heptane. Then, 15 mmol of Al (C
A n-heptane solution of ₂ H ₅ ) ₂ Cl and a 1.5 mmol V (acetylacetonato) ₃ toluene solution were added, and the polymerization was started with stirring. Polymerize propylene at -78 ° C
I went there for 3 hours. Then, a reaction with GMA was performed in the same manner as in Example 1 except that the reaction time was 5 hours, to obtain a terminal-modified polypropylene having the properties shown in Table 1.

[Table 1]

[0029]Example 7 Synthesis of Living Ethylene-Propylene Random Copolymer 500 ml autoclave fully replaced with nitrogen gas
250 ml of n-heptane, and cooled to -60 ° C.
Then, at the same temperature, 15 mmol of Al (C₂H_Five) ₂Cl
N-heptane solution and 1.5 mmol of V (2-methyl
Le-1,3-butane dionato)₃Toluene solution
It was Next, after reducing the pressure in the system to 700 mmHg,
Mixed gas of ethylene and propylene (40/60 molar ratio)
Is continuously supplied to carry out ethylene-propylene copolymerization-
Living for 1 hour at 60 ℃, living ethylene-propylene
Random copolymer (hereinafter, ethylene-propylene random
This copolymer is called EPR. ) Was synthesized. On the other hand, Echi
Molecular weight, molecular weight distribution and
And the same as above for measuring propylene content
Copolymerization of ethylene and propylene by the method
Was obtained. Mn of the obtained copolymer was 6.8 × 1.
0³, Mw / Mn was 1.21. Furthermore, this
Copolymer¹³C-NMR measurement is carried out and it belongs to secondary carbon.
Of the peak (S) and the peak (T) belonging to tertiary carbon
Calculate the propylene content from the product based on the following formula:
It was As a result, the propylene content in the copolymer was 5
It was 2.7 mol%. Propylene content (mol%) = {T / 1/2 (S + T)}
× 100 In addition, this copolymer was analyzed by a differential scanning calorimeter (DSC).
As a result of thermal analysis, the amount of glass caused by the propylene homopolymer
No transition temperature (about -10 ° C) was observed.

Reaction with Glycidyl Methacrylate In the above reaction system, glycidyl methacrylate (GMA) is used.
250 mmol was added at −60 ° C., the temperature in the system was raised to 0 ° C. over 1 hour, and the mixture was stirred at the same temperature and GMA was added.
With the reaction. After 5 hours, the reaction solution was put into 500 ml of methanol to precipitate a polymer. The obtained polymer was dissolved again in n-heptane and centrifuged to obtain a supernatant. The supernatant was poured into 500 ml of methanol to precipitate the polymer again. The obtained polymer was washed 5 times with methanol and then dried under reduced pressure at room temperature to obtain 1.92 g of a polymer.

The GPC efflux curve of the resulting polymer was unimodal. Mn of this polymer was 7.1 × 10 ³ , and Mw / Mn was 1.23, which was a value close to monodispersion.
IR analysis of this polymer showed that it was 1740 cm ^-1.
Absorption due to stretching vibration of the carbonyl group was observed.
Further, as a result of ¹ H-NMR analysis, peaks having the following chemical shift values were observed in addition to the peak (δ = 0.7 to 1.7 ppm) attributable to protons in the EPR part.

[Chemical 13] Proton signal of EPR part (δ = 0.7 to 1.7 p
pm), the area ratio of the signal (c), the propylene content and the molecular weight of the EPR, the obtained polymer has the seven GMA units introduced at the end of the EPR as described below. It has been found.

[Chemical 14]

Example 8 800 ml of n-heptane was placed in a 1.5 liter autoclave sufficiently replaced with nitrogen gas, cooled to -60 ° C, 1.5 g of propylene was added at the same temperature, and liquefied in n-heptane. Dissolved. Then 40 mmol Al
An n-heptane solution of (C ₂ H ₅ ) ₂ Cl and a 0.8 mmol V (2-methyl-1,3-butanedionate) ₃ toluene solution were added, and the mixture was stirred at -60 ° C for 10 minutes. Then, after reducing the pressure in the system to 680 mmHg, a mixed gas of ethylene and propylene (50/50 molar ratio) was continuously supplied, ethylene-propylene copolymerization was performed at -60 ° C for 10 hours, and a living EPR was performed. Synthesized. Then
After adding 500 mmol of GMA at the same temperature, the temperature of the reaction system was raised to 20 ° C. over 1 hour, and the reaction with GMA was performed for 10 hours. Thereafter, the same treatment as in Example 7 was carried out to obtain a terminal-modified EPR having the properties shown in Table 2. On the other hand, copolymerization of ethylene and propylene was carried out in the same manner as above, and 2
3.9 g of EPR was obtained. The Mn of this copolymer is 10
It was 1.4 × 10 ³ , Mw / Mn was 1.26, and the propylene content was 48.6 mol%.

[0033]Example 9 500 ml autoclave fully replaced with nitrogen gas
To the flask, 250 ml of toluene was added and cooled to -60 ° C.
Then, 0.2 g of propylene was added at the same temperature, and the mixture was added to toluene.
Liquefied and dissolved. Then, 15 mmol of Al (C₂
H_Five)₂A solution of Cl in n-heptane and 2.0 mmol
V (2-methyl-1,3-butanedionate) ₃toluene
The solution was added and stirred at -60 ° C for 10 minutes. Then the system
After reducing the pressure to 720 mmHg, ethylene and
Continuous supply of mixed gas of pyrene (60/40 molar ratio)
And ethylene-propylene copolymerization at -60 ° C for 2 hours.
And the living EPR was synthesized. Then at the same temperature
After adding 250 mmol of GMA, the reaction with GMA
It carried out at -60 degreeC for 3 hours. Hereinafter, the same process as in Example 7 was performed.
The end-modified EPR having the properties shown in Table 2 was obtained. on the other hand,
Copolymerize ethylene and propylene by the same method as above.
2.14 g of EPR was obtained. Mn of this copolymer is
5.1 x 10³, Mw / Mn is 1.26, including propylene
The content was 38.6 mol%.

Example 10 250 ml of toluene was placed in a 500 ml autoclave sufficiently replaced with nitrogen gas, cooled to -78 ° C., and then 15 mmol of Al (C ₂ H ₅ ) ₂ Cl in n-heptane solution and A 1.5 mmol V (acetylacetonato) ₃ toluene solution was added. Next, 700 mm in the system
After reducing the pressure to Hg, a mixed gas of ethylene and propylene (40/60 molar ratio) was continuously supplied to obtain ethylene-
Copolymerization of propylene was carried out at -78 ° C for 3 hours to synthesize living EPR. Next, after adding 250 mmol of GMA at the same temperature, the temperature of the reaction system was kept at -2 for 1 hour.
The temperature was raised to 0 ° C., and the reaction with GMA was performed for 5 hours. Thereafter, the same treatment as in Example 7 was carried out to obtain a terminal-modified EPR having the properties shown in Table 2. On the other hand, copolymerization of ethylene and propylene was carried out by the same method as above to obtain 1.54 g of EPR. Mn of this copolymer was 8.7 × 10 ³ , Mw / Mn
Was 1.26 and the propylene content was 55.3 mol%.

Example 11 A polymer was obtained in the same manner as in Example 7, except that glycidyl acrylate (GA) was used in place of GMA and the reaction conditions were as shown in Table 2. .
IR analysis of this polymer showed that it was 1740 cm ^-1.
Absorption due to stretching vibration of carbonyl group was observed.
Furthermore, as a result of ¹ H-NMR analysis, the obtained polymer was
It was confirmed that the following two substituent units were bonded to the end of PR.

[Chemical 15]

[Table 2]

[0036]

INDUSTRIAL APPLICABILITY The polymer of the present invention can be used as a compatibilizing agent for different polymers, a polymer modifier for imparting dyeability or adhesiveness to a polymer, a viscosity index improving material for lubricating oil and the like.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Satoshi Ueki 1-3-1 Nishitsurugaoka, Oi-cho, Iruma-gun, Saitama Tonen Research Institute

Claims (1)

[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 following general formula I. General formula I [However, R represents a hydrogen atom or a methyl group. ]