JP2000026842A - Antistatic agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an antistatic agent which has an excellent compatibility with base materials by using a polymer having a specific group in its side chain. SOLUTION: A polymer having a group of formula I in its side chain is used as an antistatic agent. In the formula, R1, R2 and R3 are each H or a 1-4C alkyl; and (n) is 2-4. The antistatic agent may comprise 1-99 wt.% of (A) a polymer having a group of formula I and 1-99 wt.% of (B) another polymer. The polymer A should contain 100-1 mol.% of a structural unit based on a monomer having a group of formula I in its side chain and 0-99 mol.% of a structural unit based on another monomer. The number average molecular weight of the polymer A is preferably 1,000-1,000,000. The monomer having a group of formula I in its side chain is preferably 2- methacryloyloxyethyl-2'-(triethylanmmonio)ethylphosphate. The agent is used for various polymer materials by impregnation or coating.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antistatic agent which is impregnated or coated on various polymer materials to reduce the electric resistance of the polymer surface, suppress the accumulation of static electricity, and have excellent antistatic performance. To obtain a polymer molded article such as a polymer film or fiber.

[0002]

2. Description of the Related Art Plastics such as polyethylene and polypropylene have a high insulation resistance and are easily charged with static electricity, which may cause static electricity damage during the processing step or cause fine powder to be attracted. In particular, plastic films and molded products that flow at high speed are easily charged by friction, and in applications related to plastic parts of computer-related equipment and packaging materials that dislike static electricity, the problem due to the accumulation of static electricity on the surface is that if only dust adheres, It cannot be ignored because it causes quality deterioration. However, it is known that the above-mentioned problem is unlikely to occur due to static electricity or the like when the humidity is high during the rainy season or when the surface resistivity is 10 ¹² Ω / cm ² or less. Further, in the case of polymer fibers and the like, there is a problem in that clothing such as clothing, which is a textile product, is clinged due to the electrostatic charge as described above.

[0003]

SUMMARY OF THE INVENTION It is a first object of the present invention to provide an antistatic agent having an excellent affinity for a substrate. A second object of the present invention is to provide an article obtained by treating the antistatic agent.

[0004]

Means for Solving the Problems In view of the above problems, the present inventors have conducted intensive studies, and as a result, have found that a polymer having a specific group exerts an excellent antistatic effect, and have achieved the present invention. completed. That is, the present invention includes the following (1) to (4). (1) The following general formula [1]

Embedded image (Wherein, R ¹ , R ² , R ³ and n are the same or different groups, and each is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n
Represents an integer of 2 to 4. An antistatic agent comprising the polymer A having a group represented by the formula (1) in the side chain. (2) As the component A, the following general formula [1]

Embedded image (Wherein, R ¹ , R ² , R ³ and n are the same or different groups, and each is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n
Represents an integer of 2 to 4. (1) The charge according to (1), comprising a polymer composition containing 1 to 99% by weight of a polymer A having a group represented by the side chain in the side chain and 99 to 1% by weight of another polymer B as a component B. Inhibitor. (3) As the component A, the following general formula [2]

Embedded image (In the formula, R ¹ , R ² , R ³ , n and R ⁴ are the same or different groups, each being a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is an integer of 2 to 4. , R ⁴ is a monomer represented by a hydrogen atom or a methyl group.), (a1 component) 100 to mol%, the other monomer (a2 component) 0-9
A polymer (A) obtained by polymerizing a monomer mixture containing 9 mol% and 1 to 99% by weight, and a polymer mixture containing another polymer B and 99 to 1% by weight as a B component. It is an antistatic agent. (4) An article obtained by treating the antistatic agent according to any one of the above (1) to (3).

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The polymer antistatic agent having a group represented by the general formula [1] in the side chain used in the present invention is represented by the following general formula [1]

Embedded image (Wherein, R ¹ , R ² , R ³ and n are the same or different groups, and each is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n
Represents an integer of 2 to 4. ) May be present in the side chain of the polymer. Here, R ¹ , R ² and R ³ may be the same or different and are a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is an integer of 2 to 4. When the carbon number of R ¹ , R ² and R ³ is 5 or more, it is not preferable because raw materials are difficult to obtain. When n is 1 or an integer of 5 or more, synthesis is difficult, which is not preferable.

Further, the antistatic agent of the present invention comprises, as an A component, 1 to 99% by weight of a polymer A having a group represented by the above general formula [1] in a side chain; It may contain 1 to 99% by weight of another polymer B.

Further, the antistatic agent of the present invention comprises, as an A component, the following general formula [2]:

Embedded image (Wherein, R ¹ , R ² , R ³ , R ⁴ and n are the same or different groups, and each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; n represents an integer of 2 to 4; , R ⁴ represents a hydrogen atom or a methyl group), (a1 component) 100 to 1 mol%, and another monomer (a2 component) 0 to
A polymer (A) obtained by polymerizing a monomer mixture containing 99 mol% of the polymer (A) can be obtained.
9% by weight, and as the B component, another polymer (B), 99 to
An antistatic agent comprising a polymer mixture containing 1% by weight.

Further, the present invention is an article obtained by treating with the above-mentioned antistatic agent.

The polymer A used in the present invention is a monomer having a group represented by the general formula [1] in the side chain (specifically, for example, a monomer represented by the general formula [2] 100 to 1 mol%, more preferably 100 to 10%, even more preferably 90 to 30 mol%
And, as the a2 component, 0 to 99 mol%, more preferably 0 to 90 mol%, and still more preferably 10 to 70 mol%, of a structural unit based on another monomer,
Usually, it is obtained by radical polymerization of a monomer mixture containing the a1 component and the a2 component.

As the monomer of the a1 component used in the present invention, a monomer having a group represented by the above general formula [1] in a side chain is used. A monomer having a double bond and a group represented by the general formula [1] is preferably used. Specific examples of the monomer include 2- (meth) acryloyloxyethyl-2 ′-(trimethylammonio) ethyl phosphate and 3- (meth) acryloyloxypropyl-
2 ′-(trimethylammonio) ethyl phosphate,
4- (meth) acryloyloxybutyl-2 ′-(trimethylammonio) ethyl phosphate, 5- (meth)
Acryloyloxypentyl-2 '-(trimethylammonio) ethyl phosphate, 2- (meth) acryloyloxyethyl-2'-(triethylammonio) ethylphosphate, 3- (meth) acryloyloxypropyl-2 '-(triethylammonium E) Ethyl phosphate, 4- (meth) acryloyloxybutyl-2′-
(Triethylammonio) ethyl phosphate, 5-
(Meth) acryloyloxypentyl-2 '-(triethylammonio) ethyl phosphate, 2- (meth) acryloyloxyethyl-2'-(tripropylammonio) ethylphosphate, 3- (meth) acryloyloxypropyl-2 ' -(Tripropylammonio) ethyl phosphate, 4- (meth) acryloyloxybutyl-2 ′-(tripropylammonio) ethylphosphate, 5- (meth) acryloyloxypentyl-
2 ′-(tripropylammonio) ethyl phosphate, 2- (meth) acryloyloxyethyl-2′-
(Tributylammonio) ethyl phosphate, 3-
(Meth) acryloyloxypropyl-2 '-(tributylammonio) ethyl phosphate, 4- (meth) acryloyloxybutyl-2'-(tripropylammonio) ethylphosphate, 5- (meth) acryloyloxypentyl-2 ' -(Tributylammonio) ethyl phosphate, 2- (meth) acryloyloxyethyl-3 ′-(trimethylammonio) propyl phosphate, 2- (meth) acryloyloxyethyl-4′-
(Trimethylammonio) butylethyl phosphate,
2- (meth) acryloyloxyethyl-3 ′-(triethylammonio) propyl phosphate, 2- (meth) acryloyloxyethyl-4 ′-(triethylammonio) butyl phosphate, 2- (meth) acryloyloxyethyl-3 '-(Tripropylammonio)
Propyl phosphate, 2- (meth) acryloyloxyethyl-4 ′-(tripropylammonio) butyl phosphate, and the like. Further, 2- (meth) acryloyloxyethyl-3 ′-(tributylammonio)
Propyl phosphate, 2- (meth) acryloyloxyethyl-4 ′-(tributylammonio) butyl phosphate, 3- (meth) acryloyloxypropyl-
3 '-(trimethylammonio) propyl phosphate, 3- (meth) acryloyloxypropyl-4'-
(Trimethylammonio) butyl phosphate, 3-
(Meth) acryloyloxypropyl-3 ′-(triethylammonio) propyl phosphate, 3- (meth)
Acryloyloxypropyl-4 ′-(triethylammonio) butyl phosphate, 3- (meth) acryloyloxypropyl-3 ′-(tripropylammonio)
Propyl phosphate, 3- (meth) acryloyloxypropyl-4 ′-(tripropylammonio) butyl phosphate, 3- (meth) acryloyloxypropyl-3 ′-(tributylammonio) propyl phosphate, 3- (meth) acryloyl Oxypropyl-4 '
-(Tributylammonio) butyl phosphate, 4-
(Meth) acryloyloxybutyl-3 '-(trimethylammonio) propyl phosphate, 4- (meth) acryloyloxybutyl-4'-(trimethylammonio) butylphosphate, 4- (meth) acryloyloxybutyl-3'- (Triethylammonio) propylethyl phosphate, 4- (meth) acryloyloxybutyl-4 ′-(triethylammonio) butylphosphate, 4- (meth) acryloyloxybutyl-3 ′
-(Tripropylammonio) propyl phosphate,
4- (meth) acryloyloxybutyl-4 '-(tripropylammonio) butylphosphate, 4- (meth) acryloyloxybutyl-3'-(tributylammonio) propylphosphate, 4- (meth) acryloyloxybutyl- 4 '-(tributylammonio)
Butyl phosphate. Furthermore, there may be mentioned maleic acid, fumaric acid, and derivatives of itaconic acid monomers in which one or two groups represented by the general formula [1] are esterified.

Particularly, from the viewpoint of availability, etc., the general formula [2]

Embedded image (Wherein, R ¹ , R ² and R ³ are the same or different groups, and each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
4 represents an integer, and R ⁴ represents a hydrogen atom or a methyl group. 2-)-acryloyloxyethyl-2 ′-(triethylammonio) ethyl phosphate (hereinafter abbreviated as MPC) represented by the following formula (1):

The polymer A contains 100 to 1 mol% of a monomer having a group represented by the above general formula [1] in a side chain and 0 to 99 mol of an a2 component as another monomer. % Of the monomer mixture obtained by radical polymerization. As the monomer of the a2 component (also referred to as “other monomer”) used in the present invention, a monomer that can be polymerized with the a1 component is used, and preferably has a double bond in the molecular structure. A suitable monomer is used. More specifically, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-dodecyl (meth) acrylate, cyclohexyl (meth) acrylate, and the like Of alkyl (meth)
Acrylates containing silyl groups such as 3-{(meth) acryloyloxypropyl} trimethoxysilane, 3-{(meth) acryloyloxypropyl} triethoxysilane, 3-{(meth) acryloyloxypropyl} tripropyloxysilane ( Meth) acrylate; 2-
(Perfluorohexyl) ethyl (meth) acrylate, 2- (perfluorooctyl) ethyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, 1H, 1H, 7H-dodecafluoroheptyl (meth) acrylate, Fluorine (meth) acrylate such as 2,2,2-trifluoro-1-trifluoromethylethyl (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, polyethylene glycol mono ( Hydroxyl-containing (meth) acrylates such as (meth) acrylate and polypropylene glycol mono (meth) acrylate; amide monomers such as (meth) acrylamide and N, N-dimethyl (meth) acrylamide; (meth) acryl Raise the acid Rukoto can.

Further, as the “other monomer” of the component a2,
For example, substituted or unsubstituted styrene monomers such as styrene, methyl styrene, chloromethyl styrene, etc .; vinyl ether monomers such as ethyl vinyl ether and butyl vinyl ether; vinyl ester monomers such as vinyl acetate; trimethoxy vinyl silane Silane-based monomers such as ethylene, triethoxyvinylsilane, etc .; substituted or unsubstituted hydrocarbon-based monomers such as ethylene, propylene, isobutylene, vinyl chloride, and vinylidene chloride; dibasic acid esters such as diethyl fumarate and diethyl maleate N-vinylpyrrolidone; Of these monomers, more preferred are a hydroxyl group-containing (meth) acrylate, an alkyl (meth) acrylate, a styrene monomer, and a vinylsilane monomer.

The method for polymerizing the polymer A having a group represented by the general formula [1] in the side chain used in the present invention may be a conventional radical polymerization, and particularly preferably a solution polymerization method at 30 to 90 ° C. The polymerization can be carried out at the polymerization temperature. In this case, examples of the solvent used include alcohols such as methanol, ethanol, and isopropanol, water, and a mixed solvent thereof. As the radical polymerization initiator, those usually used may be used. Specifically, azobisisobutylnitrile, azobisvaleronitrile, lauroyl peroxide, benzoyl peroxide, t
Oil-soluble ones such as -butylperoxyneodecanoate and t-butylperoxypivalate; and water-soluble ones such as diacyl peroxide succinate, ammonium persulfate, potassium persulfate and hydrogen peroxide. The radical polymerization initiator is used at a ratio of 0.01 to 10% by weight of the total monomer raw materials.

The polymer A having a group represented by the general formula [1] in the side chain used in the present invention contains 100 to 1 structural units based on a monomer having a group represented by the general formula [1].
Mol%, preferably 100 to 10 mol%, more preferably 100 to 50 mol%. If the amount is less than 1 mol%, it is not preferable because the antistatic effect cannot be sufficiently exhibited.

The molecular weight of the polymer A having a group represented by the general formula [1] in the side chain used in the present invention is preferably from 1,000 to 1,000,000 as a number average molecular weight. If the molecular weight is less than 1,000,
It is not preferable because it is easily dissolved in water and it is difficult to exhibit a long-term antistatic effect.
Those larger than 000 are difficult to manufacture.

In addition to the component A of the present invention, as the polymer B used as the component B, for example, a polymerizable polymer is also used. In this case, the polymer B has a double bond copolymerizable with the polymer A. Such polymers are preferably used. In addition, a general polymer may be used for the purpose of simply blending. More specifically, for example, styrene, α-
Methyl styrene, sodium styrene sulfonate, (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 3- {(Meth) acryloyloxypropyl} trimethoxysilane, 3-{(meth) acryloyloxypropyl} triethoxysilane, 3-{(meth) acryloyloxypropyl} tripropyloxysilane, 2-hydroxyethyl (meth)
Acrylate, polyethylene glycol (meth) acrylate, glycidyl (meth) acrylate, (meth) acrylonitrile, (meth) acrylamide, N, N-dimethyl (meth) acrylamide, vinyl acetate, dimethyl fumarate, diethyl fumarate, di-n- Monofunctional polymers such as butyl fumarate, di-n-butyl malate, diethyl itaconate, N-vinylpyrrolidone, cyano (meth) acrylate, trimethoxyvinylsilane, triethoxyvinylsilane, vinyl chloride, vinylidene chloride, polysulfone, segmentation Polyurethane, polyvinyl chloride, polypropylene, polystyrene, polyethylene, ABS resin, polymethylpentene, styrene-butadiene block copolymer, polydimethylsiloxane, Ethylene terephthalate, polybutylene terephthalate, poly-allyl sulfones, polyether imide, polycarbonate, polyacetal, nylon, nylon -ABS resins, polysulfone - high molecular weight polymers of the thermoplastic polyester copolymer, and the like.
Although the molecular weight of the polymer B is not particularly limited, it is preferably 1,000 in terms of adhesion to a substrate, solubility in water and a solvent, and the like.
0 to 1,000,000 are preferred. As the B component, these other polymers B can be used alone or in combination of two or more.

Examples of the good solvent for blending the polymer A and the polymer B include, for example, methanol, ethanol, propanol, isopropanol, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, water, Examples include methylene chloride, chloroform and a mixed solvent thereof. The use amount of these solvents is 2 to 1,000,000 times (weight) with respect to the total amount of the polymers A and B. If the amount is less than 2 times, it is difficult to dissolve in a solvent, so that it is
If it is more than 000 times, it takes time to remove the solvent, which is not preferable.

The polymer A and the polymer B in the antistatic agent of the present invention may be simply mixed and blended to form a polymer mixture, or they may be copolymerized to form a single polymer to form a high polymer. The molecular composition may be either or both, and any antistatic agent containing them may be included in the category of the antistatic agent of the present invention.

In the present invention, the article treated with an antistatic agent is, for example, an article obtained by impregnating or coating a polymer material with the antistatic agent of the present invention.

The antistatic agent of the present invention can be used by coating it on the surface of a substrate exhibiting an antistatic effect. As a coating method, an existing method such as a brush coating method, a roll coating method, a bar coater method, a spray method, a spin coating method, and a dip coating method can be used.

When performing the coating, it is preferable to dissolve the polymer A alone or to dissolve the polymer A and the polymer B in a solvent before coating. Specific examples of the good solvent in this case include, for example, methanol, ethanol, propanol, isopropanol, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, water, methylene chloride, chloroform and a mixed solvent thereof. . Of these solvents, alcohol solvents are particularly preferred.
The amount of these solvents used is 2 to 1,000,000 times (weight) the amount of the antistatic agent. If the amount is less than 2 times, it is difficult to dissolve in a solvent, so that it is
If it is more than 000 times, it takes time to remove the solvent, which is not preferable. After applying the solvent solution of the polymer, an antistatic film can be formed on the substrate surface of the article by drying such as natural drying or forced drying.

As a substrate of an article to which the surface of the antistatic agent of the present invention can be applied, a plastic or the like which easily causes an antistatic failure can be exemplified. The shape can be any shape such as a lens, film, sheet, fiber, and the like. Furthermore, a coating film, a plastic coat film,
The present invention can be applied to those provided with a special coating such as silane coupling and fluorine coating. According to the present invention, by impregnating or applying the antistatic agent to various polymer materials, the electric resistance of the polymer surface is reduced, the accumulation of static electricity is suppressed, and a polymer film or fiber excellent in antistatic performance is used. Can be obtained.

[0024]

The present invention will be described below in more detail with reference to examples. Synthesis Example 1; <MPC / BMA = 50/50 polymer> As a1, 2- (methacryloyloxy) ethyl-
14.8 g (50 mmol) of 2 '-(trimethylammonio) ethyl phosphate (hereinafter abbreviated as MPC) and a
As 2, butyl methacrylate (hereinafter abbreviated as BMA)
7.1 g (50 mmol) was weighed into a glass polymerization tube,
Azobisisobutyronitrile 0.82 as a polymerization initiator
g was added and dissolved in 100 ml of ethanol. After bubbling argon gas into the solution for 5 minutes, the polymerization tube was sealed and sealed.
The polymerization reaction was performed at 0 ° C. for 6 hours. After completion of the reaction, the reaction mixture was dropped into ether, and the precipitated copolymer was filtered off.
After removing unreacted monomers, the residue was dried under reduced pressure.
A copolymer was obtained. For the obtained copolymer, the composition ratio of MPC in the copolymer was determined by phosphorus determination. Further, the molecular weight was determined by gel permeation chromatography (GPC) using standard polystyrene. The analysis results are shown below. Yield 65% Molar ratio MPC / BMA = 49/51 Weight average molecular weight 14.6 × 10 ⁴

Synthesis Example 2 <MPC / BMA = 70/30
Polymer> Synthesis Example 1 except that the amount of BMA used in Synthesis Example 1 was changed from 7.1 g (50 mmol) to 3.04 g (21 mmol), and the reaction time was further changed from 6 hours to 2 hours.
The reaction was carried out in the same manner as described above to obtain an MPC-BMA copolymer.
The analysis results are shown below. Yield 62% Molar ratio MPC / BMA = 71/29 Weight average molecular weight 13.1 × 10 ⁴

Synthesis Example 3; <MPC / BMA = 80/20
Polymer> Synthesis Example 1 except that the amount of BMA used in Synthesis Example 1 was changed from 7.1 g (50 mmol) to 1.78 g (13 mmol), and the reaction time was further changed from 6 hours to 1 hour.
The reaction was carried out in the same manner as described above to obtain an MPC-BMA copolymer.
The analysis results are shown below. Yield 57% Molar ratio MPC / BMA = 81/19 Weight average molecular weight 16.4 × 10 ⁴

Synthesis Example 4; <MPC / DMA = 50/50
Polymer> 7.1 g of BMA of the monomer of Synthesis Example 1 as a2 component
12.7 g (50 mmol) of n-dodecyl methacrylate (hereinafter abbreviated as DMA) instead of (50 mmol)
The polymerization reaction was carried out in the same manner as in Synthesis Example 1 except that the reaction time was changed to 5 hours to obtain a copolymer of MPC-DMA. The analysis results are shown below. Yield 50% Molar ratio MPC / DMA = 52/48 Weight average molecular weight 12.5 × 10 ⁴

Synthesis Example 5: <MPC / St = 70/30 Polymer> 2.2 g of styrene (hereinafter abbreviated as St) in place of 7.1 g (50 mmol) of monomer BMA of a2 in Synthesis Example 1
(21 mmol) and a polymerization reaction was carried out in the same manner as in Synthesis Example 1 except that the reaction time was changed to 14 hours, to obtain a copolymer of MPC-St. The analysis results are shown below. Yield 45% Molar ratio MPC / St = 69/31 Weight average molecular weight 10.3 × 10 ⁴ The results are shown in Table 1.

[0029]

[Table 1]

Example 1 The MPC-BMA copolymer synthesized in Synthesis Example 1 (50/5
0) was diluted with ethanol to adjust the concentration of the MPC-BMA copolymer to 0.1% by weight. After applying an MPC-BMA copolymer solution to one surface of a polymethyl methacrylate plate (10 cm × 10 cm × 5 mm) using a doctor blade having a gap of 0.1 mm, ethanol was evaporated by natural drying. Next, the sample pieces were dried at 70 ° C. for 6 hours. <Evaluation test method of antistatic property> After the sample piece treated by the above method was left at 25 ° C. and 60% RH for 3 hours, the sample was applied using a digital super insulation meter DSM-8103 (manufactured by Toa Denpa Kogyo Co., Ltd.) The surface resistance was measured at a voltage of 100 V (based on JIS K6911).
The results are shown in Table 2.

Example 2 The MPC-BMA copolymer (50/5) used in Example 1
After the treatment was performed in the same manner as in Example 1 except that the MPC-BMA copolymer (70/30) synthesized in Synthesis Example 2 was used instead of (0), the surface resistance of the treated surface was measured. The results are shown in Table 2.

Example 3 The MPC-BMA copolymer (50/5) used in Example 1 was used.
After treating in the same manner as in Example 1 except that MPC-BMA copolymer (80/20) synthesized in Synthesis Example 3 was used instead of 0), the surface resistance of the treated surface was measured. The results are shown in Table 2.

Example 4 The MPC-BMA copolymer (50/5) used in Example 1
After the treatment was performed in the same manner as in Example 1 except that the MPC-DMA copolymer (50/50) synthesized in Synthesis Example 4 was used instead of (0), the surface resistance of the treated surface was measured. The results are shown in Table 2.

Example 5 The MPC-BMA copolymer used in Example 1 (50/5
After the treatment was performed in the same manner as in Example 1 except that MPC-St copolymer (70/30) synthesized in Synthesis Example 5 was used instead of (0), the surface resistance of the treated surface was measured. The results are shown in Table 2.

Comparative Example 1 An untreated polymethyl methacrylate plate was used in place of the treated polymethyl methacrylate plate of Example 1, and the surface resistance was measured in the same manner. The results are shown in Table 1.

Example 6 and Comparative Example 2 The MPC-BMA copolymer synthesized in Synthesis Example 1 (50 /
50) was diluted with ethanol to adjust the concentration of the MPC-BMA copolymer (50/50) to 10% by weight, and used as a treatment liquid. Polyether sulfone (10cm × 10cm × 0.15
mm) The film was immersed in the treatment solution prepared by the above method, pulled up, and after removing ethanol by natural drying, the film was dried at 70 ° C. for 6 hours. The surface resistance of the sample before and after the treatment was evaluated in the same manner as in <Evaluation Test Method 1 for Antistatic Property> described above. Table 3 shows the results.

Example 7 and Comparative Example 3 The MPC-BMA copolymer synthesized in Synthesis Example 2 (70 /
30) was diluted with ethanol to adjust the concentration of the MPC-BMA copolymer (70/30) to 5% by weight, and used as a treatment liquid. Polyethylene terephthalate (10cm × 10cm ×
0.1 mm) The film was treated in the same manner as in Example 6.
The surface resistance of the sample before and after the treatment was evaluated in the same manner as in <Evaluation Test Method 1 for Antistatic Property> described above. Table 3 shows the results.
It was shown to.

Example 8 and Comparative Example 4 The MPC-BMA copolymer synthesized in Synthesis Example 3 (80 /
20) was diluted with water, and the MPC-BMA copolymer (80 /
The concentration of 20) was adjusted to 5% by weight and used as a processing solution. Nylon mesh (10cm x 10cm, 150 mesh)
Was subjected to the same treatment as in Example 6. The surface resistance of the sample before and after the treatment was evaluated in the same manner as in <Evaluation Test Method 1 for Antistatic Property> described above. Table 3 shows the results.

From the above results, Examples 1 to 5 of the present invention
Clearly shows a remarkable antistatic effect on the PMMA plate as compared with Comparative Example 1. Further, it is apparent that Examples 6 to 8 of the present invention show a remarkable antistatic effect on various substrates as compared with Comparative Examples 2 to 4.

[0040]

[Table 2]

[0041]

[Table 3]

[0042]

The antistatic agent of the present invention has excellent water retention due to the monomer having a side chain represented by the general formula [1]. In the present invention, the adhesion to the substrate can be controlled by selecting the type and composition ratio of the other monomer of the a2 component. Furthermore, in the antistatic agent of the present invention, the adhesion to the substrate can be controlled by selecting another polymer B of the B component. Therefore, the antistatic agent of the present invention has excellent durability and can maintain the antistatic effect for a long time.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Hirofumi Irie 2-17-14 Kasuga, Tsukuba, Ibaraki Prefecture (72) Inventor Nobuo Nakabayashi 5-6-20 Koganehara, Matsudo City, Chiba Prefecture (72) Inventor Kazuhiko Ishihara 3-16-37, Josuihoncho, Kodaira-shi, Tokyo

Claims (6)

[Claims] 1. A compound represented by the following general formula [1] (Wherein, R ¹ , R ² and R ³ are the same or different groups, and each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Indicates an integer of 4. An antistatic agent comprising the polymer A having a group represented by the formula (1) in the side chain. 2. A compound represented by the following general formula [1]: (Wherein, R ¹ , R ² and R ³ are the same or different groups, and each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
Indicates an integer of 4. 1) to 99% by weight of a polymer A having a group represented by a side chain as a B component, and another polymer B;
An antistatic agent comprising 99 to 1% by weight. 3. A component represented by the following general formula [2]: (Wherein, R ¹ , R ² and R ³ are the same or different groups, and each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
4 represents an integer, and R ⁴ represents a hydrogen atom or a methyl group. (A1 component) 100-1
Mol%, a polymer A1 to 99% by weight obtained by polymerizing 0 to 99% by mol of another monomer (a2 component), and 99 to 1% by weight of another polymer B as a B component. Antistatic agent. 4. An article treated with the antistatic agent according to claim 1. 5. An article treated with the antistatic agent according to claim 2. 6. An article treated with the antistatic agent according to claim 3.