JP3307699B2 - Antistatic resin products - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antistatic resin product, and more particularly, to a product having a high antistatic property for a long period of time and free from surface contamination due to bleed out of an antistatic agent. The present invention relates to an antistatic resin product having excellent optical characteristics and mechanical characteristics.

[0002]

2. Description of the Related Art In general, a polymer sheet or film (hereinafter referred to as a "resin substrate") is excellent in electrical insulation and is easily charged, so that not only dust adheres and its appearance is impaired, but also it causes static electricity. Cause various troubles. Also, O
When used in an electrical product such as an A device, a malfunction is likely to be caused by the accumulated static electricity.

Conventionally, as a method for preventing static charge on a resin substrate, a method of applying a surfactant (antistatic agent) to the surface of the resin substrate has been known. Such method has a fast-acting in a simple, has the disadvantage that the surface of the resin base material is said to assume a tacky, also easily antistatic agent has a problem called lack to durability flaking.

On the other hand, as a method of obtaining stable antistatic performance over a long period of time, a method has been adopted in which an antistatic agent is previously kneaded into the resin itself. The kneading method is different from the above-mentioned coating method, in that even if the antistatic agent layer on the surface is lost, the internal antistatic agent diffuses to the surface due to the concentration gradient, and a new antistatic agent layer is formed. It is said that antistatic performance can be maintained for a long time.

[0005] However, the kneading method is based on the premise that the antistatic agent bleeds out to the surface, and thus often has the same problem as the coating method. That is, since the surface of the resin base material into which the antistatic agent has been kneaded is easily contaminated, it is often necessary to wipe the surface of the resin base material with water. It is lost and temporarily loses its antistatic properties.

[0006] In order to solve the above problems, there has been proposed a method of applying a high molecular weight antistatic agent obtained by copolymerizing a monomer having an antistatic property and various monomers or macromonomers. However, conventional high molecular weight antistatic agents have insufficient adhesion to a resin base material, and it is difficult to achieve both compatibility and antistatic properties at a high level, and further improvement is desired. ing. The present inventors, first,
A copolymer of a polyester macromer and a vinyl monomer has been proposed (JP-A-4-161415). This copolymer is extremely useful as a polymer antistatic agent, but does not have sufficient adhesiveness or applicability to a resin substrate.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide a high antistatic property for a long period of time, avoid contamination of the surface by bleeding out of an antistatic agent, and have excellent optical and mechanical properties. To provide an antistatic resin product.

[0008]

That is, the gist of the present invention consists of repeating units represented by the following general formulas [I] and [II], wherein the ratio between [I] and [II] is expressed in terms of weight ratio. 10:
In the range of 90 to 90:10 and the intrinsic viscosity η _inh
Is formed on the surface of a resin product (excluding a polyvinyl chloride resin product) by forming an antistatic layer comprising a copolymer having 0.02 or more and a binder resin. Exist.

[0009]

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In the above general formula [I], R ¹ has 1 to ¹ carbon atoms.
20 alkyl group or an aralkyl group, R2 is an aliphatic hydrocarbon group, R ⁴ is a hydrogen atom or a methyl radical, n is 2-2
Represents an integer of 00, R ³ represents any of the following groups (a) to (e) , and in these groups, R ⁵ represents an alkyl group having 1 to 20 carbon atoms, a hydrogen atom or a halogen atom. , M represents an integer of 1 to 4, and l (ell) represents an integer of 1 to 10. And, the -CONH- moiety is represented by-in the general formula [I].
A urethane bond is formed adjacent to —O— in the CO—R ² —O— portion.

[0011]

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[0012]

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In the general formula [II], R ⁶ represents a hydrogen atom or a methyl group, and X represents an ionic residue having a quaternary ammonium salt or a metal salt.

Hereinafter, the present invention will be described in detail. In the present invention, it is composed of repeating units represented by the above general formulas [I] and [II], and the ratio of [I] and [II] is in the range of 10:90 to 90:10 by weight, In addition, a copolymer having an intrinsic viscosity η _inh of 0.02 or more is used as a polymer antistatic agent.

The above copolymer is usually represented by the following general formula [II
It is obtained by copolymerizing a polyester macromonomer represented by the formula [I] and a vinyl monomer represented by the following general formula [IV] in the presence of a radical initiator.

[0016]

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First, the polyester macromonomer represented by the general formula [III] will be described. General formula [III]
In the formula, R ¹ represents an alkyl group or an aralkyl group having 1 to 20 carbon atoms, and R ² represents an aliphatic hydrocarbon group. As R ² , a branched or linear aliphatic hydrocarbon group having 3 to 8 carbon atoms is preferable, and specific examples include the aliphatic hydrocarbon groups described below. These correspond to the aliphatic hydrocarbon groups of the polyester obtained by ring-opening polymerization of the lactone compound described below.

[0018]

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In the general formula [III], R ³ represents the following (a) to
It represents any of the groups shown in (e) . In these groups, R ⁵ represents an alkyl group having 1 to 20 carbon atoms, a hydrogen atom or a halogen atom, m represents an integer of 1 to 4, and 1 (ell) represents an integer of 1 to 10. Then, -CONH- parts are formulas adjacent to the -O- of -CO-R ² -O- parts in [I] to form a urethane bond.

[0020]

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In the general formula [III], R ⁴ is a hydrogen atom or a methyl group. When R ³ is a group having a —CO—NH— group, R ⁴ is preferably a methyl group. N represents an integer of 2 to 200, and represents the degree of polymerization of the polyester structure. Preferred n is 2 to 100, and particularly preferred n is 2 to 50. Particularly preferred polyester macromonomers are:

[0022]

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[0023]

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[0024]

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The polyester macromonomer represented by the general formula [III] is usually produced by the following two steps. (1) First Step In this step, R ¹ —OH (R ¹ is a group represented by the general formula [I]
And a ring-opening polymerization of a lactone compound represented by the following general formula [V] to obtain a polyester alcohol represented by the following general formula [VI]. (R ¹ in each general formula has the same meaning as in the above general formula [I], and n is an integer of 2 to about 200).

[0026]

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As the above alcohol compound, methanol, n-butanol, n-hexanol, n-octanol, 2-ethylhexanol and the like are preferable. Also,
As the lactone compound, a lactone having 3 to 8 carbon atoms is preferable, and particularly, ε-caprolactone, β-methyl-δ-
Valerolactone and β - ethyl-δ-valerolactone are preferred.

The above reaction is usually carried out in the presence of a catalyst. As the catalyst, known catalysts used in ring-opening polymerization of lactones, for example, sulfuric acid, mineral acids such as phosphoric acid, alkali metals such as lithium, sodium, potassium, alkyl metal compounds such as n-butyllithium, Metal alkoxides such as titanium tetrabutoxide can be used.

The above reaction can be carried out without solvent, but a solvent may be used if necessary. As the solvent, for example, toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran, chloroform, carbon tetrachloride and the like can be used. The reaction temperature is usually from 0 to 200 ° C, and the reaction time is usually from 10 minutes to 30 hours. Further, n in the general formula [VI] is a degree of polymerization, and can be controlled by the molar ratio of the initiator and the lactone compound.

(Second Step) In this step, the general formula [V
I] and a compound represented by the following general formula [VII] or a compound represented by the following general formula [VIII]
With the compound represented by

[0031]

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In the above general formula [VII], R ⁴ has the same meaning as in the above general formula [I], and R ⁷ represents any of the following groups. ⁵ ,
m and l have the same meanings as in the general formula [I].

[0033]

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Specific examples of the compound represented by the general formula [VII] include the following compounds.

[0035]

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In the above formula [VIII], R ⁴ has the same meaning as in the above formula [I], and Y represents a halogen atom, an alkoxy group having 1 to 8 carbon atoms or a phenoxy group. In addition, specific examples of the compound represented by the general formula [VIII] include the following compounds.

[0037]

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The reaction between the polyester alcohol represented by the general formula [VI] and the compound represented by the general formula [VII] is a urethane bond formation reaction, and the two are reacted in an equimolar ratio. The reaction proceeds without a catalyst,
To increase the reaction rate, a tin catalyst such as dibutyltin dilaurate, dibutyltin dioctoate, dibutyltin mercaptide may be used.

The reaction between the polyester alcohol represented by the general formula [VI] and the compound represented by the general formula [VIII] is a condensation reaction or a transesterification reaction, and the two are reacted at an equimolar ratio. Can be When a condensation reaction is employed, the reaction may be carried out in the presence of a deoxidizing agent such as a tertiary amine or in a stream of an inert gas because hydrogen halide is by-produced. When an ester exchange reaction is employed, a known ester exchange catalyst, for example, a mineral acid such as hydrochloric acid or sulfuric acid, a metal salt such as zinc, calcium, or magnesium, or a metal alkoxide such as titanium tetrabutoxide may be used.

The above reaction can be carried out without any solvent, but a solvent may be used if necessary. Examples of the solvent include toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran, chloroform, carbon tetrachloride and the like. The reaction temperature is usually 0 to 200 ° C., and the reaction time is usually 30 minutes to 50 hours.

Next, the vinyl monomer represented by the general formula [IV] will be described. In the general formula [IV], R ⁶ represents a hydrogen atom or a methyl group, and X represents an ionic residue having a quaternary ammonium salt or a metal salt. General formula [I
The vinyl monomer represented by V] is a conventionally known radical polymerizable monomer. Such a vinyl monomer is not particularly limited as long as it is a vinyl monomer having an anionic or cationic ionic residue, or a vinyl monomer capable of easily introducing an ionic group after polymerization. .

Examples of the vinyl monomer having a cationic group include dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dipropylaminoethyl (meth) acrylate, diisopropylamino (meth) acrylate, dibutylamino Examples include quaternized nitrogen-containing monomers such as ethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminovinyl sulfide, diethylaminoethyl vinyl ether, vinylbenzyl-N, N'-dimethylamine, vinylpyridine, and vinylquinoline. Can be

The above quaternization reaction is carried out by a known method.
It can be carried out by allowing a quaternizing agent to act on the tertiary amino group. As quaternizing agents, inorganic acids such as hydrogen chloride, hydrogen bromide, sulfuric acid, benzyl chloride, benzyl bromide,
Methyl chloride, methyl bromide and the like can be mentioned.
The quaternization reaction may be performed at any stage before and after the copolymerization.

Examples of the vinyl monomer having an anionic group include (meth) acrylic acid and α-chloro (meth)
Acrylic acid, vinyl sulfonic acid, sulfonated styrene,
2-acrylamido-2-methylpropanesulfonic acid,
Sulfomethyl (meth) acrylate, 2-sulfoethyl (meth) acrylate, 3-sulfoethyl (meth) acrylate, 3-sulfopropyl (meth) acrylate,
Allylsulfonic acid, 1-phenylvinylsulfonic acid, acid phosphooxyethyl (meth) acrylate, 3-
Vinyl monomers having a carboxyl group, a sulfonic acid group, a phosphoric acid group such as chloro-2-amidophosphooxypropyl (meth) acrylate and acid phosphooxypropyl (meth) acrylate, or alkali metal salts thereof, ammonium Examples thereof include salts, organic amine salts such as dimethylamine, triethylamine, and triethanolamine, and tetrabutylphosphonium salts.

When a metal salt or an organic salt is used as the vinyl monomer represented by the general formula [IV], the corresponding monomer may be directly subjected to polymerization. Is also good.

Particularly preferable monomers having an ionic residue are dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate and dipropylaminoethyl (meth) acrylate.
Quaternary ammonium salts and metal salts of (meth) acrylic acid.

Next, the copolymerization of the polyester macromonomer represented by the general formula [III] and the vinyl monomer represented by the general formula [IV] will be described. The polyester macromonomer and the vinyl monomer are in a weight ratio of 10:90 to
90:10 range, preferably 20:80 to 80: 2
Copolymerization is performed in the range of 0. If the ratio of the vinyl monomer is less than 10, a copolymer having excellent antistatic properties cannot be obtained, and the ratio of the polyester macromonomer is 10
When the ratio exceeds the above, the affinity of the obtained copolymer to the binder resin becomes poor.

The above copolymerization can be easily carried out by a usual radical polymerization method. As the radical polymerization initiator, an azo compound, a peroxide or the like is used, and its use ratio is usually 0.1 to 10% by weight. The reaction temperature is from 0 to 200 ° C, and the reaction time is from 1 to 24 hours. In order to control the degree of polymerization, a chain transfer agent such as an alkyl mercaptan can be used. As the polymerization method, any polymerization method usually used in radical polymerization, such as bulk polymerization, solution polymerization, emulsion polymerization, and suspension polymerization, may be employed.

The above-mentioned copolymer is methyl ethyl ketone /
Using a mixed solvent of methanol (7/3), concentration 0.5g
/ Dl, intrinsic viscosity η _inh measured at 25 ° C
Must be greater than or equal to 0.02. When the intrinsic viscosity of the copolymer is lower than 0.02, the advantage due to the increase in the molecular weight is lost, the copolymer easily bleeds out of the resin substrate, and the antistatic performance is reduced.

In the present invention, it is important to use the above copolymer as a high molecular weight antistatic agent and to use it together with a binder resin. As the binder resin, one or more binder resins selected from a thermoplastic resin, a urethane-curable resin, and an ultraviolet-curable resin are preferable.

The thermoplastic resin is not particularly limited as long as it is soluble in a solvent, and may be appropriately selected according to the type of the resin base material to be applied. Specific examples of the thermoplastic resin include polyvinyl chloride, polyester, polyamide, polyacrylate, and polyurethane. In the present invention, the antistatic layer is formed by dissolving a high molecular weight antistatic agent and a thermoplastic resin in a solvent common to both, applying the solution to a resin substrate, and then drying.

When a coating film is required to have high strength and chemical resistance, it is effective to use a thermosetting resin as a binder resin. That is, the high molecular weight antistatic agent of the present invention is mixed with a polyol generally used in the urethane industry, and further mixed with a curing agent containing an isocyanate compound, and then applied to a resin substrate, cured, and dried. If this is the case, a highly durable coating film having more excellent wear resistance can be formed. At this time, additives such as a solvent and a curing catalyst generally used in the urethane industry may be used.

When a quick-drying and high-hardness coating film is required, the use of an ultraviolet curable resin as the binder resin is effective. That is, a high-molecular weight antistatic agent of the present invention is blended with a known ultraviolet-curable resin composition, applied to a resin substrate, and then cured with ultraviolet rays according to a conventional method to form a coating film having good surface properties in a short time. Can be formed. The UV-curable resin is not particularly limited, and examples thereof include monofunctional monomers such as butyl acrylate, tetrahydrofurfuryl acrylate, and vinylpyrrolidone, and polyfunctional oligomers such as polyurethane acrylate and polyester acrylate.

The proportion of the high molecular weight antistatic agent used is 1 to 9
A range of 9% by weight is good. If the proportion of the high molecular weight antistatic agent is less than 1% by weight, sufficient antistatic performance cannot be obtained, and if it exceeds 99% by weight, the ability to form a coating film is inferior and cracks and wrinkles occur. The preferred proportion of the high molecular weight antistatic agent used is in the range of 10 to 90% by weight.

The coating film can be formed by a known method, for example, a spray method, a bar coating method, a roll coating method, a spin coating dipping method and the like. The thickness of the coating film to be formed is preferably in the range of 0.1 to 20 μm. When the thickness of the coating film is less than 0.1 μm, the antistatic performance is poor,
If it exceeds, the cost is high for the performance obtained.
The thickness of the coating film is preferably in the range of 1 to 10 μm.

In the present invention, examples of the resin substrate include various products of a thermoplastic resin or a thermosetting resin, such as a film and a sheet. The thermoplastic resin is not particularly limited, and examples thereof include a polyolefin resin such as polyethylene and polypropylene, a polystyrene resin, a polystyrene-acrylonitrile copolymer resin, an ABS resin, a polyester resin, a polyamide resin, a polyacrylate resin, and a polyurethane resin. Is mentioned.

Examples of the polyamide resin include nylon 6, nylon 6-6, nylon 6-10, nylon 11, nylon 12, and the like. As polyester resin,
Examples include polyethylene terephthalate, polybutylene terephthalate, and polycarbonate. Examples of the thermosetting resin include an epoxy resin, a phenol resin, a urea resin, and a melamine resin.

In the present invention, the above-mentioned copolymer used as a polymer antistatic agent exhibits high compatibility with various binder resins, and thus forms a uniform coating film. Therefore, the film or sheet on which such a coating film is formed has no tackiness, is robust, and has excellent durability.

[0059]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist. In addition, the measurement of the surface resistance value is performed by using Yokogawa-HEWLETT-PACKARD 23
Using a 29A-type insulation resistance meter, the measurement voltage was set to 100 V, and the measurement was performed at 25 ° C. and 50% RH.

Reference Example A (Synthesis of Polyester Alcohol) After thoroughly replacing a flask equipped with a stirring blade, a dropping funnel and a gas inlet with dry nitrogen, 5.7 g of 2-ethylhexanol and 0.1 g of metallic sodium were charged. The metal sodium was dissolved by stirring. Next, the flask was immersed in an oil bath at 40 ° C., and 50 g of β-methyl-δ-valerolactone was dropped from the dropping funnel while stirring. After one hour, stirring was stopped, the contents of the flask were taken out, and dissolved in 500 ml of purified chloroform. The obtained solution was poured into 500 ml of deionized water, washed, and the chloroform layer was separated. After repeating such washing once again, the solvent was distilled off from the chloroform solution under reduced pressure,
A colorless and transparent polyester alcohol was obtained. The hydroxyl value of the polyester alcohol is 58.6 KOHmg / g,
The acid value was 0.03 KOHmg / g.

Reference Example B (Synthesis of Polyester Macromonomer) In a reactor equipped with a stirring blade and a reflux condenser, 20.00 g of the polyester alcohol synthesized in Reference Example A, m-isopropenyl-α, α'-dimethylbenzyl isocyanate 4.25 g of nate and 0.12 g of dibutyltin dioctoate (1% by weight in toluene solution) were charged and heated to 80 ° C.
A time reaction was performed. IR spectrum and H-NM of product
From the measurement results of R, it was confirmed that a polyester macromonomer having the following structure was obtained.

[0062]

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Reference Example C (Synthesis of Polyester Alcohol) A polyester alcohol was obtained in the same manner as in Reference Example A, except that β-methyl-δ-valerolactone was changed to ε-caprolactone. The hydroxyl value of the obtained polyester alcohol was 56.78 KOHmg.
/ G, acid value was 0.50 KOHmg / g.

Reference Example D (Synthesis of Polyester Macromonomer) In a reactor equipped with a stirring blade and a reflux condenser, 20.00 g of the polyester alcohol synthesized in Reference Example C, m-isopropenyl-α, α'-dimethylbenzyl isocyanate 4.11 g of nate and 0.12 g of dibutyltin dioctoate (1% by weight in toluene solution) were charged and heated to 80 ° C.
A time reaction was performed to synthesize a caprolactone-based macromonomer.

Reference Example E (Synthesis of random copolymer) 10.0 g of methyl methacrylate and 10.0 g of methacryloyloxyethyltrimethylammonium chloride were placed in a flask equipped with a stirring blade, a reflux condenser and a gas inlet.
g, azobisisobutyronitrile 0.9 g,
Further, 13 g of toluene and 7 g of n-hexane were added as a solvent to form a uniform solution, and then polymerization was performed at 80 ° C. for 8 hours under a nitrogen stream. After the polymerization, the reaction solution was poured into methanol to precipitate a product, which was sufficiently washed with methanol and then dried. The yield was almost 100%.

Example 1 In a flask equipped with a stirring blade, a reflux condenser and a gas inlet, the polyester macromonomer synthesized in Reference Example B 10.0 was added.
g, methacryloyloxyethyltrimethylammonium chloride 10.0 g, azobisisobutyronitrile 0.2 g, and isopropyl alcohol 40 g were charged, and polymerized at 70 ° C. for 8 hours under a nitrogen stream. After the polymerization, the reaction solution was poured into hexane to precipitate a product and dried. The yield was 83%. The intrinsic viscosity η _inh of the obtained copolymer was 0.15 dl / g.

3 g of the above copolymer and 7 g of PMMA resin powder ("BR-80" manufactured by Mitsubishi Rayon Co., Ltd.) were mixed in a 9/1 mixture of methyl ethyl ketone / methanol at a concentration of 10% by weight.
And coated on a nylon sheet (manufactured by Mitsubishi Kasei) so as to have a thickness of 2 mm using a # 8 bar coater, and dried by heating at 120 ° C. for 2 minutes to form an antistatic layer. . The surface resistance of the antistatic layer is 7.5 × 10
It was ⁸ Ω / □.

Example 2 A polyester macromonomer 40.0 synthesized in Reference Example D was placed in a flask equipped with a stirring blade, a reflux condenser, and a gas inlet.
g, 17.0 g of methacrylic acid, 0.6 g of azobisisobutyronitrile and 85 g of isopropyl alcohol, and polymerized at 70 ° C. for 8 hours under a nitrogen stream. After the polymerization, isopropyl alcohol was distilled off and dried under reduced pressure. The intrinsic viscosity η _inh of the obtained copolymer was 0.11 dl / g.

20 g of the above copolymer was dissolved in 200 g of a 9/1 mixed solvent of methyl ethyl ketone / methanol.
41.6 g of a methanol solution of KOH by weight was added, and the mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was distilled off under reduced pressure.
g of the copolymer was obtained. This copolymer was coated on a polyethylene terephthalate sheet (manufactured by Mitsubishi Kasei Co., Ltd.) in a thickness of 2 mm in the same manner as in Example 1,
After heating and drying for an minute, an antistatic layer was formed. The surface resistance of the antistatic layer was 8.0 × 10 ⁸ Ω / □.

Example 3 A 7/3 mixed solvent of methyl ethyl ketone / methanol of the copolymer obtained in Example 1 (resin solid content: 10% by weight)
1.5 g and 3.5 g of a urethane acrylate-based UV-curable resin (50 wt% methyl ethyl ketone solution, “PR-202” manufactured by Mitsubishi Kasei Co., Ltd.) were mixed, and the resin solid content was 23
A solution by weight was obtained. This solution was applied on an ABS resin sheet (manufactured by Monsanto Kasei Co., Ltd.) using a # 5 bar coater,
An ultraviolet lamp of 120 W / cm was irradiated for 12 seconds for curing to form an antistatic layer. The surface resistance of the antistatic layer was 7.0 × 10 ⁸ Ω / □. This value did not change even after washing for 5 minutes.

Example 4 An antistatic layer was formed in the same manner as in Example 1 except that a bisphenol A type epoxy resin sheet (manufactured by Yuka Shell Epoxy) was used instead of the nylon sheet. did. The surface resistance of the antistatic layer was 7.8.
× 10 ⁸ Ω / □.

Comparative Example 1 3 g of the random copolymer obtained in Reference Example E and 7 g of PMMA resin powder ("BR-80" manufactured by Mitsubishi Rayon Co., Ltd.) were mixed at a concentration of 10 in a 9/1 mixture of methyl ethyl ketone / methanol.
% By weight, and coated on a nylon sheet (manufactured by Mitsubishi Kasei) to a thickness of 2 mm using a # 8 bar coater, and dried by heating at 120 ° C. for 2 minutes to form a coating film. did. The surface resistance of the coating film is 7.4.0 × 10 ¹⁴
Met. Further, the coating film was slightly cloudy.

Comparative Example 2 Polyester Macromonomer 1.5 Synthesized in Reference Example B
g and a quaternary ammonium salt-based monomer 1.5 g were dissolved as is in a 9/1 mixture of methyl ethyl ketone / methanol to a concentration of 10% by weight, and a nylon sheet (Mitsubishi Kasei Corporation) using a # 8 bar coater. Co., Ltd.), and dried by heating at 120 ° C. for 2 minutes to form a coating film. The surface resistance immediately after the formation of the coating film was 1.3 × 10 ⁶ Ω / □, but increased to 2.6 × 10 ¹² Ω / □ after washing with water for 5 minutes.

[0074]

According to the present invention described above, the antistatic agent has high antistatic properties for a long period of time, does not contaminate the surface due to bleed-out of the antistatic agent, and has excellent optical and mechanical properties. An antistatic resin product is provided. The antistatic resin product of the present invention is a housing for electrical products, flooring,
It can be suitably used for all products that dislike the adverse effects of static electricity, such as various film products.

────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-5-25463 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08J ⁷ /04-7/06 C09K 3 / 16

Claims (4)

(57) [Claims] 1. A composition comprising a repeating unit represented by the following general formulas [I] and [II], wherein the ratio of [I] to [II] is in the range of 10:90 to 90:10 by weight, Further, an antistatic layer comprising a copolymer having a limiting viscosity η _inh of 0.02 or more and a binder resin is formed on the surface of a resin product (excluding a polyvinyl chloride resin product). Antistatic resin products. Embedded image In the above general formula [I], R ¹ is an alkyl group or aralkyl group having 1 to 20 carbon atoms, R ² is an aliphatic hydrocarbon group, R
⁴ represents a hydrogen atom or a methyl group, n represents an integer of 2 to 200, R ³ represents any of the following groups (a) to (e) , and in these groups, R ⁵ represents the number of carbon atoms. 1-20
An alkyl group, a hydrogen atom or a halogen atom, m is 1 to
An integer of 4 and l (ell) represent an integer of 1 to 10. And, the -CONH- moiety is represented by -CO-R ² in the general formula [I].
A urethane bond is formed adjacent to -O- in the -O- portion. Embedded image Embedded image In the general formula [II], R ⁶ represents a hydrogen atom or a methyl group, and X represents an ionic residue having a quaternary ammonium salt or a metal salt. 2. The antistatic resin product according to claim 1, wherein the resin product is a film or a sheet. 3. The antistatic resin product according to claim 1, wherein the binder resin is a thermosetting resin. 4. The antistatic resin product according to claim 1, wherein the binder resin is an ultraviolet curable resin.