JPH05194660A - Maleimide-based copolymer - Google Patents

Abstract

PURPOSE:To provide the subject maleimide-based copolymer suitably usable as an antistatic agent and an intermediate useful therefor. CONSTITUTION:The objective linearly and irregularly arranged maleimide--based copolymer is composed of 50-98mol% olefinic structural unit, 1-15mol% acrylate structural unit and 1-35mol% maleimide structural unit. The weight-average molecular weight of this copolymer is 1000-50000. Furthermore, its intermediate is obtained.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a maleimide copolymer and an intermediate useful therein. More specifically, it relates to a maleimide-based copolymer that can be suitably used as an antistatic agent and an intermediate useful therein.

[0002]

2. Description of the Related Art Thermoplastic resins such as polyolefin resins, ABS resins and vinyl chloride resins have been used in conventional films,
It is widely used as a bag body for packaging materials, automobile parts, and other materials, but these thermoplastic resins generally have a large electrical resistance, and have the serious drawback of being easily charged by friction and sucking dust and the like. ..

Therefore, in recent years, as a method of imparting an antistatic ability to a thermoplastic resin by using an antistatic agent, (a) a method of applying an antistatic agent on the surface of the resin and then drying, (b) an internal addition type antistatic agent A method of kneading the agent into the resin has been proposed.

However, in the above method (a), a surfactant solution is generally used as the antistatic agent, but such an antistatic agent is easily removed by washing, so that a permanent electrostatic charge is obtained. There is a drawback in that the prevention ability cannot be imparted.

In the method (b), glycerin fatty acid ester, sorbitan fatty acid ester, alkyldiethanolamide, sodium alkylbenzenesulfonate, quaternary salt of alkylimidazole, etc. are used as the internal addition type antistatic agent. When these internally added antistatic agents are used, even if the antistatic agent on the surface is lost by washing, a new antistatic agent bleeds sequentially from the inside of the antistatic agent. There is an advantage that the preventive ability lasts for a relatively long time. However, in such an internal addition type antistatic agent, it takes a long time to recover the antistatic ability after washing, and when the antistatic agent excessively bleeds, tackiness occurs, rather In addition to the drawback that dust and the like tend to adhere, these antistatic agents have low molecular weights, so they volatilize due to heat during molding processing at high temperatures, so add more antistatic agents than necessary. The disadvantage of having to
There is a drawback that it is difficult to adjust the effective amount.

In recent years, a polymer type antistatic agent has been proposed as a solution to the drawbacks of the internal addition type antistatic agent. Examples of such a polymer type antistatic agent include (a) styrene-maleic anhydride copolymer imide-modified, then quaternized and cationized polymer (Japanese Patent Publication No. 1-29820), (b) anhydrous A copolymer of maleic acid and ethylene, propylene or styrene is imide-modified and then quaternized and cationized (JP-A-55-93883), and (c) a maleic anhydride-grafted polyolefin is imidized. There is a polymer compound having an antistatic functional group such as a polymer which has been modified and then quaternized and then cationized (JP-A-63-246750).

However, since the polymer (a) is extremely hard, when it is added to a resin having flexibility such as polyolefin, the flexibility of the resin is impaired, and the resin is not compatible with polyolefin. There are drawbacks such as poor compatibility, coloring caused by the benzene ring contained in the polymer, and deterioration of weather resistance.

The polymers (b) and (c) are A
The compatibility with styrene resins such as BS resin is poor, and there is a drawback that the mechanical properties of the resin are significantly reduced.

Further, in the polymer (c), since the antistatic functional group is introduced in a form grafted to the polymer main chain, the hydrolysis property is inferior to that of the copolymer type, and Although it has flexibility because the chain is a polyolefin, it has drawbacks such as poor film forming ability and adhesiveness.

[0010]

Therefore, in view of the above-mentioned prior art, the present inventors have not only semipermanently provided an excellent antistatic ability, but also have good compatibility with various resins. Suitable as an antistatic agent that hardly deteriorates the physical properties of the resin, hardly causes blocking of the molded product, has hydrolysis resistance, and is excellent in flexibility, film forming ability and adhesiveness. As a result of intensive studies to find a compound that can be used, a compound having all of the above physical properties was finally found, and the present invention was completed.

[0011]

That is, the present invention is
General formula (I):

[0012]

[Chemical 7]

50 to 98 mol% of an olefin structural unit represented by the formula (wherein R ¹ represents a hydrogen atom or a methyl group),
General formula (II):

[0014]

[Chemical 8]

1 to 15 mol% of the acrylate structural unit represented by the formula (wherein R ² represents an alkyl group having 1 to 4 carbon atoms) and the general formula (III):

[0016]

[Chemical 9]

(In the formula, R ³ is an alkylene group having 2 to 8 carbon atoms, R ⁴ and R ⁵ are each an alkyl group having 1 to 4 carbon atoms, R ⁶ is an alkyl group having 1 to 12 carbon atoms, and 6 carbon atoms. 12 arylalkyl group, alicyclic alkyl group of the epoxy group or C6-12 2 to 4 carbon atoms which may be substituted by an alkyl group, X is a halogen atom, CH ₃ OSO ₃ or C ₂ H ₅ maleimide copolymer having a weight average molecular weight from 1,000 to 50,000 were irregularly arranged linearly consisting maleimide structural unit 1-35 mol% represented by showing a OSO _3), and the general formula (I):

[0018]

[Chemical 10]

50 to 98 mol% of an olefin structural unit represented by the formula (wherein R ¹ represents a hydrogen atom or a methyl group),
General formula (II):

[0020]

[Chemical 11]

An acrylate structural unit represented by the formula (wherein R ² represents an alkyl group having 1 to 4 carbon atoms) and 1 to 15 mol% and the general formula (IV):

[0022]

[Chemical formula 12]

(In the formula, R ³ represents an alkylene group having 2 to 8 carbon atoms, R ⁴ and R ⁵ each represents an alkyl group having 1 to 4 carbon atoms) and is composed of 1 to 35 mol% of a maleimide structural unit. Weight average molecular weight of 1000 arranged randomly in a line
~ 50,000 maleimide-based copolymers.

[0024]

FUNCTION AND EXAMPLE As described above, the maleimide-based copolymer of the present invention has the general formula (I):

[0025]

[Chemical 13]

50 to 98 mol% of an olefin structural unit represented by the formula (wherein R ¹ represents a hydrogen atom or a methyl group),
General formula (II):

[0027]

[Chemical 14]

An acrylate structural unit represented by the formula (wherein R ² represents an alkyl group having 1 to 4 carbon atoms) and 1 to 15 mol% and a general formula (III):

[0029]

[Chemical 15]

(Wherein R ³ is an alkylene group having 2 to 8 carbon atoms, R ⁴ and R ⁵ are each an alkyl group having 1 to 4 carbon atoms, R ⁶ is an alkyl group having 1 to 12 carbon atoms, and 6 carbon atoms. 12 arylalkyl group, alicyclic alkyl group of the epoxy group or C6-12 2 to 4 carbon atoms which may be substituted by an alkyl group, X is a halogen atom, CH ₃ OSO ₃ or C ₂ H ₅ A maleimide copolymer having a weight average molecular weight of 1000 to 50,000 and linearly and irregularly arranged of 1 to 35 mol% of a maleimide structural unit represented by OSO ₃ ).

The proportion of the olefin structural unit in the maleimide-based copolymer of the present invention is 50 to 98 mol%. When the proportion of the olefin structural unit is less than 50 mol%, the softening point of the maleimide-based copolymer of the present invention becomes high, and the flexibility inherent to the resin is impaired when blended in a thermoplastic resin. On the other hand, when it exceeds 98 mol%, the antistatic ability of the maleimide-based copolymer of the present invention becomes too small. In the olefin structural unit, R ¹ is a hydrogen atom or a methyl group, and these groups may be mixed in one molecule. Further, in the present invention, the proportion of the olefin structural unit is preferably 85 to 97 mol% from the viewpoint of the balance between the softening point and the antistatic ability.

The proportion of the acrylate structural unit in the maleimide copolymer of the present invention is 1 to 15 mol%. When the proportion of the acrylate structural unit is less than 1 mol%, the toughness and impact resistance of the maleimide copolymer of the present invention are impaired, and when it exceeds 15 mol%, the present invention is used. The maleimide-based copolymer (1) has a low softening point and causes tack and stickiness when blended with a thermoplastic resin. In the present invention, the inclusion of the acrylate structural unit is preferable because it imparts toughness, impact resistance, film forming property, and adhesiveness when blended with a thermoplastic resin. In the present invention, the proportion of the acrylate structural unit is preferably 3 to 7 mol% from the viewpoint of the balance between the softening point and the toughness and impact resistance.

In the acrylate structural unit, R ²
Is an alkyl group having 1 to 4 carbon atoms. Specific examples of R ² include, for example, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group and the like, and these groups are mixed in one molecule. May be. Among these groups, a methyl group and an ethyl group are particularly preferable for maintaining the softening point of the maleimide-based copolymer obtained.

The ratio of the maleimide structural unit in the maleimide copolymer of the present invention is 1 to 35 mol%. When the proportion of the maleimide structural unit is less than 1 mol%, the antistatic ability becomes too small, and when it exceeds 35 mol%, the maleimide copolymer of the present invention is used as a thermoplastic resin. When blended, hygroscopicity occurs, and it becomes difficult to be compatible with the thermoplastic resin. In the present invention, the proportion of the maleimide structural unit is preferably 3 to 15 mol% from the viewpoint of the balance between antistatic ability and hygroscopicity.

In the maleimide structural unit, R ³ is an alkylene group having 2 to 8 carbon atoms. Specific examples of R ³ include ethylene group, propylene group, hexamethylene group, neopentylene group and the like, and these groups may be mixed in one molecule. Among these groups, an ethylene group and a propylene group are preferable, and a propylene group is particularly preferable, from the viewpoint of easy production and economy.

R ⁴ and R ⁵ are each 1 to 1 carbon atoms.
4 is an alkyl group. Specific examples of R ⁴ and R ⁵ include methyl group, ethyl group, propyl group and butyl group, and these groups may be mixed in one molecule. Among these groups, a methyl group and an ethyl group are preferable from the viewpoint of imparting antistatic ability.

R ⁶ is an alkyl group having 1 to 12 carbon atoms, an arylalkyl group having 6 to 12 carbon atoms, an epoxy group having 2 to 4 carbon atoms which may be substituted with an alkyl group, or an alkyl group having 6 to 12 carbon atoms. It is an alicyclic alkyl group. Specific examples of R ⁶ include, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, n
An alkyl group such as an octyl group and an n-lauryl group; an arylalkyl group such as a benzyl group; an epoxyethyl group,
1,2-epoxypropyl group, 2,3-epoxypropyl group, 1,2-epoxybutyl group, 1,2-epoxy-
An epoxy group which may be substituted with an alkyl group such as a 2,3-epoxybutyl group; an alicyclic alkyl group such as a cyclohexyl group and a methylcyclohexyl group, and these groups may be mixed in one molecule. Good. In addition, the R
⁶ is preferably a linear alkyl group or an arylalkyl group from the viewpoint of heat resistance of the maleimide-based copolymer of the present invention, and is preferably a lower alkyl group from the viewpoint of imparting antistatic ability. Particularly preferred R ⁶ includes a methyl group and an ethyl group.

X is, for example, a halogen atom such as Cl, Br or I, CH ₃ OSO ₃ or C ₂ H ₅ OSO ₃
And these may be mixed in one molecule. Among these, from the viewpoint of antistatic ability, Cl, CH
₃ OSO ₃ and C ₂ H ₅ OSO ₃ are preferred.

The weight average molecular weight of the maleimide copolymer of the present invention is 1,000 to 50,000. The weight average molecular weight is 10
When it is less than 00, the maleimide copolymer of the present invention is blended in the thermoplastic resin because the molecular weight becomes too small,
When it volatilizes when heated and exceeds 50,000, the viscosity of the maleimide-based copolymer of the present invention when melted becomes too large, resulting in poor workability. The preferred weight average molecular weight is 3000 to 35000.

The term "weight average molecular weight" as used herein means gel permeation chromatography (GP).
The monodisperse polystyrene-equivalent weight average molecular weight measured in C).

Since the maleimide copolymer of the present invention is hardly soluble in an eluent for normal gel permeation such as tetrahydrofuran (THF) or xylene, the weight average molecular weight of the maleimide copolymer can be easily measured. It is impossible to do this, but the ultrahigh temperature GPC method (Kinukawa, Polymers, 44
Volume 2, No. 2, pp. 139-141 (1987)).

An olefin structural unit represented by the above general formula (I), which is an intermediate of the maleimide copolymer of the present invention,
The acrylate structural unit represented by the general formula (II) and the general formula (IV):

[0043]

[Chemical 16]

(In the formula, R ³ , R ⁴ and R ⁵ are the same as those mentioned above) A maleimide copolymer having a weight average molecular weight of 1000 to 50000 and comprising a maleimide structural unit having an irregular arrangement is, for example, Obtained by the method.

The raw material for producing the intermediate of the maleimide copolymer of the present invention is not particularly limited, but for example, a solvent such as benzene or toluene is used in an autoclave, and acrylate, maleic anhydride, benzoyl peroxide, etc. are used. The radical polymerization initiator of is dissolved, and a predetermined amount of olefin is blown into the obtained solution, and 200 to 30 at 50 to 80 ° C.
Olefin-acrylate-maleic anhydride obtained by a known method such as reacting under a pressure of 0 kg / cm ² for 8 to 12 hours, and then introducing the content in the autoclave into a large amount of a solvent such as ether. A copolymer is used. Here, the charged molar ratio of each monomer is almost equal to the ratio of the structural units of the target copolymer.

The olefin-acrylate-maleic anhydride copolymer thus obtained is used as a raw material to obtain the maleimide copolymer of the present invention and its intermediate.

The method for producing the maleimide copolymer of the present invention and the intermediate thereof from the olefin-acrylate-maleic anhydride copolymer is not particularly limited, but one example thereof will be described below.

The olefin-acrylate-maleic anhydride copolymer is dissolved in, for example, an aromatic or aliphatic hydrocarbon such as benzene, toluene, xylene, cyclohexanone, decane, cumene or cymene, an inert solvent such as a ketone, The olefin-acrylate-
The acid anhydride group contained in the maleic anhydride structural unit is added by adding 100 to 150 mol% of dialkylaminoalkylamine to the maleic anhydride content of the maleic anhydride copolymer and reacting at 130 to 180 ° C. Is converted to a dialkylaminoalkylimide group to give an intermediate of a maleimide-based copolymer.

Next, the linear maleimide copolymer of the present invention is obtained by cation-modifying the intermediate with a known quaternizing agent such as an alkyl halide or a dialkyl sulfate.

The thus-obtained maleimide-type copolymer of the present invention exhibits not only excellent antistatic ability but also excellent heat resistance peculiar to the maleimide group. Although the reason for this is not clear, it is likely that the maleimide structural unit contained in the maleimide-based copolymer of the present invention takes in water in the air, and X ⁻ ionizes to exhibit electrical conductivity, thus exhibiting low electrical resistance. It is thought to be due to this.

Further, in the present invention, the maleimide structural unit does not exhibit volatility even at high temperature, and since it is chemically incorporated in the maleimide-based copolymer of the present invention, it is volatilized during processing. Therefore, it is considered that the occurrence of blocking and the deterioration of physical properties of the thermoplastic resin are not caused after the processing.

The thermoplastic resin to which the maleimide copolymer of the present invention can be applied includes, for example, polyolefin resins such as polyethylene and polypropylene; polystyrene resins such as polystyrene and ABS resin; polyamide resins; polybutylene terephthalate and the like. Examples of the polyester include polyethers such as modified polyphenylene ether, but the present invention is not limited to these examples.

Next, the maleimide copolymer of the present invention will be described in more detail with reference to Production Examples and Examples.
The present invention is not limited to such examples.

Production Example 1 58.6 g (0.597 mol) of maleic anhydride, 25.6 g (0.256 mol) of ethyl acrylate, and benzoyl peroxide 3 were placed in a stainless steel autoclave with an internal capacity of 3000 ml and equipped with a magnetic stirrer.
g was dissolved in 1000 ml of benzene and then charged. Then, the autoclave was cooled from the outside, and the inside of the autoclave was sufficiently replaced with ethylene to obtain 215.8 g (7.68 mol) of ethylene.
Was charged and reacted at 50 ° C. for 10 hours, then the content was put into a large amount of ether, and the formed precipitate was collected by filtration, washed with ether and dried to obtain ethylene-ethyl acrylate-maleic anhydride. A copolymer was obtained. The weight average molecular weight, the infrared absorption spectrum, and the structural unit in the copolymer were examined as the physical properties of the obtained copolymer according to the following methods. The weight average molecular weight and structural unit of the copolymer are shown in Table 1, and the infrared absorption spectrum is shown in FIG.

(Weight Average Molecular Weight) Polymer Papers, Vol. 44,
No. 2, pp. 139-141 (1987). Waters GPC-244 (column: Showa Denko KK, Shodex, A-80M / S (2)) was used, 1-chloronaphthalene was used as a solvent, flow rate 0.7 ml / min, column temperature 210. It was measured at ° C.

(Infrared absorption spectrum) FT-200 manufactured by Horiba, Ltd. was used to measure potassium bromide tablets.

[0057] ester carbonyl group of acrylate (co structural units in the polymer) in 1735 cm ^-1, The carbonyl group of the acid anhydride of maleic acid 1820 cm ^-1 and 1760 cm ^-1
Since it has a characteristic absorption value of infrared rays, a calibration curve of each characteristic absorption value with respect to the charged molar ratio of each monomer is prepared in advance, and the structure in the copolymer is determined from the correspondence relationship of the calibration curve of the infrared absorption spectrum. The unit ratio was calculated.

Production Examples 2 to 4 Production Example 1 except that ethylene, acrylate and maleic anhydride were changed as shown in Table 1 in Production Example 1.
An ethylene-acrylate-maleic anhydride copolymer was obtained in the same manner as in.

The weight average molecular weight, infrared absorption spectrum and structural unit of the obtained copolymer were examined in the same manner as in Production Example 1. Table 1 shows the weight average molecular weight and structural unit of the copolymer.

[0060]

[Table 1]

Example 1 400 ml of xylene and ethylene-ethyl acrylate-maleic anhydride obtained in Preparation Example 1 were placed in a four-necked flask having an internal capacity of 1000 ml equipped with a thermometer, a stirrer, a dropping funnel and a Dean-Stark water diverter. 150 g of an acid copolymer (raw material) was charged. Next, it was heated using an oil bath, and 20.4 g of N, N-dimethylaminopropylamine was gradually added dropwise under reflux (about 140 ° C). Immediate distillation of water was observed, and maleic anhydride was converted to maleimide anhydride. It was confirmed that the product had been denatured. The produced water was continuously removed by azeotropy with xylene, and after the completion of the dropping of N, N-dimethylaminopropylamine, the reaction was continued at 140 ° C. until the azeotrope of the produced water was not observed.

The obtained reaction mixture was cooled to 80 ° C., 10 g of the reaction mixture containing the target intermediate (hereinafter referred to as intermediate A) was collected, and 28.0 g of diethylsulfate was added to the remaining reaction mixture with a dropping funnel. Was gradually added dropwise over 1 hour. Although heat generation was observed during this period, the reaction temperature was maintained at 90 ° C. by cooling, and after completion of dropping, aging reaction was carried out at 100 ° C. for 4 hours.

The intermediate A and the reaction mixture obtained above were taken out, and each of them was separately charged into a large amount of methanol, and the produced precipitate was recovered and dried under vacuum to obtain the product. The yield is 3.5 g of intermediate A, maleimide-based copolymer 1
The yield was 91.2 g, and the yields were 96.7% and 98%, respectively, based on the raw material ethylene-ethyl acrylate-maleic anhydride copolymer.

Next, the yield, infrared absorption spectrum and weight average molecular weight of the obtained intermediate A and maleimide type copolymer were examined. Tables 2 and 3 show the yields and weight average molecular weights of both and the infrared absorption spectra of the maleimide copolymers. Moreover, the infrared absorption spectrum of the intermediate A is shown in FIG. 2, and the infrared absorption spectrum of the maleimide-based copolymer is shown in FIG.

Examples 2 to 4 Instead of the copolymer obtained in Production Example 1, the copolymer obtained in Production Example 2 was used in Example 2, and the copolymer obtained in Production Example 3 was used. Intermediate B, intermediate C and intermediate D were prepared in the same manner as in Example 1 except that the copolymer obtained in Production Example 4 was used in Example 4 and the copolymer obtained in Production Example 4 was used in Example 4.

Then, the intermediate B, the intermediate C and the intermediate D and the quaternizing agent shown in Table 2 were used in the same manner as in Example 1 in place of the quaternizing agent used in Example 1. A maleimide-based copolymer was obtained.

The yield, infrared absorption spectrum and weight average molecular weight of the thus obtained intermediate B, intermediate C and intermediate D and the maleimide copolymer were examined in the same manner as in Example 1. Table 2 shows the measurement results of the yield and the weight average molecular weight of both, and the infrared absorption spectrum of the maleimide-based copolymer.
~ 3.

[0068]

[Table 2]

[0069]

[Table 3]

Experimental Examples 1 to 4 The maleimide copolymer obtained in each Example or 10 parts by weight of the copolymer and polypropylene (manufactured by Mitsui Toatsu Co., Ltd .: JS
1429) 90 parts by weight of the blended product was introduced into a T-die type film forming apparatus heated to 200 ° C. to obtain an unstretched film having a thickness of 50 μm and a width of 500 mm.

The obtained film was cut into a size of 10 cm × 10 cm to prepare a test film. Next, the obtained test film was examined for surface specific resistance, water resistance, blocking resistance, transparency and strength and elongation according to the following methods. The results are shown in Tables 4-5.

(A) Specific surface resistance The specific surface resistance test film was set at 20 ° C., 30% RH (relative humidity) or 20%.
After standing for 24 hours at 60 ° C and 60% RH, the surface resistivity was measured using a super insulation meter R-503 manufactured by Kawaguchi Electric Co., Ltd.

Sustainability After the test film was stored at room temperature for 30 days, it was allowed to stand under conditions of 20 ° C. and 60% RH for 24 hours, and then the surface resistivity was measured in the same manner as described above.

Water resistance For the film made of the maleimide copolymer of the present invention, after storage at room temperature for 30 days, and for the film made of the maleimide copolymer of the present invention and polypropylene,
After aging for 14 days in an oven at 40 ° C, the surface was thoroughly washed with an aqueous solution of Mama Lemon (manufactured by Lion Corporation) as a detergent, then rinsed thoroughly with deionized water, and then at 20 ° C, 60% RH. After being left in the atmosphere for 24 hours, the surface resistivity was measured in the same manner as above.

(B) Blocking resistance Two films prepared by blending the maleimide-based copolymer of the present invention with polypropylene were sandwiched between 20 cm × 20 cm glass plates, placed in an oven at 40 ° C. and aged for 14 days.
After 14 days, the film was taken out and manually peeled off, and the presence or absence of blocking was measured.

A: No blocking B: Some blocking C: Blocking (c) Transparency The transparency of the film prepared by blending the maleimide copolymer of the present invention with polypropylene was visually evaluated.

A: good transparency B: little transparency C: almost no transparency (d) Strength and elongation The film prepared by blending the maleimide copolymer of the present invention has a width of 10 mm and a length of 100 mm. It was cut out and the thickness (Tmm) was measured. This sample was applied to a Tensilon type tensile tester with a chuck distance set to 50 mm, pulled at a speed of 300 mm / min, the breaking strength (S) and breaking elongation (s) were measured, and the tensile strength and elongation were determined by the following equations. ..

[0078]

[Equation 1]

Comparative Experimental Example 1 A test film was prepared in the same manner as in Experimental Example 1 except that polypropylene was used in place of the blended material,
Various physical properties were measured. The results are shown in Tables 4-5.

Comparative Experimental Example 2 A test film was prepared in the same manner as in Experimental Example 2 except that a mixture of 100 parts by weight of polypropylene and 3 parts by weight of stearyl diethanolamide as an antistatic agent was used in place of the blended product. The physical properties were measured. The results are shown in Tables 4-5.

[0081]

[Table 4]

[0082]

[Table 5]

As is clear from the results shown in Tables 4 to 5, the maleimide copolymer of the present invention imparts excellent antistatic ability to the thermoplastic resin, and further, the transparency and the strong elongation of the thermoplastic resin. It can be seen that the anti-blocking property does not decrease and the blocking resistance is excellent.

[0084]

The maleimide-based copolymer of the present invention has thermoplasticity and imparts excellent antistatic ability, and a film molded using a thermoplastic resin,
Since it does not deteriorate the physical properties such as transparency and strength and elongation of molded articles and has excellent blocking resistance, it can be widely applied to various thermoplastic resins.

[Brief description of drawings]

FIG. 1 is an infrared absorption spectrum of an ethylene-ethyl acrylate-maleic anhydride copolymer obtained in Production Example 1.

2 is an infrared absorption spectrum of the intermediate A obtained in Example 1. FIG.

FIG. 3 is an infrared absorption spectrum of the maleimide-based copolymer obtained in Example 1.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shigeo Kameshishi 1-1-1, Sonoyama, Otsu-shi, Shiga Toray Co., Ltd. Shiga Plant (72) Inventor Masashi Takeda 1-1-1, Sonoyama, Otsu-shi, Shiga Toray Co., Ltd. Shiga Plant (72) Inventor Osamu Wada 1-1-1, Sonoyama, Otsu City, Shiga Toray Co. Ltd. Shiga Plant

Claims (2)

[Claims] 1. General formula (I): (In the formula, R ¹ represents a hydrogen atom or a methyl group) 50 to 98 mol% of an olefin structural unit represented by the general formula (II): (Wherein, R ² represents an alkyl group having 1 to 4 carbon atoms) and 1 to 15 mol% of an acrylate structural unit represented by the general formula (III): (In the formula, R ³ is an alkylene group having 2 to 8 carbon atoms, R ⁴ and R ⁵ are each an alkyl group having 1 to 4 carbon atoms, R ⁶ is an alkyl group having 1 to 12 carbon atoms, and 6 to 12 carbon atoms. Arylalkyl group, 2 to 2 carbon atoms which may be substituted with an alkyl group
An epoxy group having 4 or an alicyclic alkyl group having 6 to 12 carbon atoms,
X is a halogen atom, CH ₃ OSO ₃ or C ₂ H ₅ OS
A maleimide structural unit represented by O ₃ ) and a weight average molecular weight of 10 to 35 mol% linearly and irregularly arranged.
A maleimide copolymer of 00 to 50000. 2. A compound represented by the general formula (I): (In the formula, R ¹ represents a hydrogen atom or a methyl group) 50 to 98 mol% of an olefin structural unit represented by the general formula (II): (Wherein R ² represents an alkyl group having 1 to 4 carbon atoms) and 1 to 15 mol% of an acrylate structural unit represented by the general formula (IV): (Wherein R ³ represents an alkylene group having 2 to 8 carbon atoms, R ⁴ and R ⁵ each represent an alkyl group having 1 to 4 carbon atoms), and a linear structure composed of 1 to 35 mol% of a maleimide structural unit is represented. A maleimide copolymer having a weight average molecular weight of 1,000 to 50,000, which is irregularly arranged.