JPH08165438A - Antistatic agent - Google Patents

Abstract

PURPOSE: To obtain an antistatic agent composed of a water-soluble polymer containing specific two recurring units, capable of providing coating film free from deterioration of antistatic ability with the lapse of time and excellent in durability as well as water resistance, adhesiveness and transparence by applying to film, etc. CONSTITUTION: This antistatic agent comprises a water-soluble polymer (preferably having 10000-200000 weight-average molecular weight) containing recurring units of at least formulas I and II (R1 is H or methyl; L is a single bond or a divalent coupling group; X1 is a cation containing H<+> ; J is divalent coupling group; A is a nitrogen-containing heterocycle having mercapto). A polymerizable vinyl monomer capable of providing the unit of the formula I includes preferably sodium p-styrenesulfonate and the monomer capable of providing the unit of the formula II includes e.g. preferably 2-mercapto-5-(4'-vinylbenzyl)- mercapto-1,3,4-thiadiazole. Furthermore, a ratio of the unit I in the polymer is preferably 40-99wt.% and a ratio of the unit II is preferably 1-60wt.%.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an antistatic polymer useful as an antistatic layer for films.
From the point of being excellent in transparency and water resistance, for example, when provided on the surface of the support of a film-sensitive material, it gives good antistatic performance before and after development without adversely affecting the characteristics of the photosensitive material. The present invention provides a material for imparting antistatic performance to the film surface, which can be suitably used for film light-sensitive materials and the like utilizing a silver salt, and is excellent in transparency, flexibility, and charging. The present invention relates to an antistatic polymer which has a hydrophilic surface coated with an inhibitor and is excellent in adhesiveness and durability. Further, by coating the water-soluble polymer according to the present invention on the surface of various supports, the surface of the support is made hydrophilic, so that antifogging properties can be imparted and it can be used as an antifogging agent.

[0002]

2. Description of the Related Art Conventionally, various surfactants, water-soluble polymers, conductive carbons, metal oxides, etc. have been used as antistatic agents for preventing the electrification of insulating films such as films. Various attempts have been made to prevent electrification by coating or kneading these on the film surface. For example, in JP-A-3-229787, a copolymer of poly (styrene sulfonate) with N-methyl acrylamide is used as a water-soluble polymer, and this is coated on a film to prevent electrification. A method of exhibiting performance is disclosed. Alternatively, JP-A-55-8465
No. 8, No. 56-92535, No. 61-174542.
No. 61-174543, etc., the combination of an antistatic water-soluble polymer and a curing agent is applied to the surface of a support such as a film to provide excellent durability such as water resistance. It is disclosed that an antistatic film is made.

However, in the above-mentioned method, adhesion between the surface of the support and the support becomes a problem, and peeling may occur between the support-containing layer and the support depending on the conditions of use, or it may change over time. There was a problem that the antistatic performance was significantly deteriorated. Further, other coating liquids are often applied onto the layer coated with the antistatic agent for various purposes, but when the coating liquid to be coated contains water as a solvent, There is a problem in that the hydrophilicity is not sufficient and unevenness in coating occurs and film peeling occurs.

Although a method of coating or kneading a low-molecular-weight surfactant or the like on the surface of a support such as a film has been studied in the past, the problem of stickiness due to bleed-out from the surface, the problem of whitening, and the deterioration over time have been encountered. Etc. had occurred.

By using a metal oxide, an antistatic film having a surface resistance less dependent on humidity can be achieved by a coating or kneading method. In this case, the metal oxide is coated or kneaded in a finely dispersed state. However, in order to impart sufficient antistatic performance to the film, it is necessary to densely fill the metal oxide particles so that they are in contact with each other. Inevitably, there was a problem that the transparency of the film was lowered.

[0006]

It is an object of the present invention to coat a surface of a support such as a film with excellent antistatic performance, which is excellent in water resistance, solvent resistance, and transparency. To provide an antistatic polymer, and to find an antistatic polymer excellent in adhesiveness between the surface of the coated antistatic polymer itself and the adjacent layer. This is an issue.

[0007]

The above object can be achieved by the present invention described below. That is, the object of the present invention is achieved by using, as the antistatic agent, a copolymer containing at least the repeating units represented by Chemical Formulas 1 and 2.

By coating such an antistatic agent alone on the surface of a support such as a film, the surface resistance value of the surface of the support is lowered, whereby the antistatic function is exerted. Alternatively, an antistatic function is imparted by coating the surface of the support in the same manner as another water-soluble polymer together with such an antistatic agent, for example, a polymer of gelatin and its derivatives, various derivatives of cellulose, various derivatives of starch. You can also

R ₁ in the chemical formula ₁ represents a hydrogen atom or a methyl group, L represents a single bond or a divalent linking group, for example, alkylene, phenylene, --COO--, --CONH.
-, - SO ₂ NH-, and it may be in the form which they are Kumia'. X _{1 in} Chemical formula ₁ represents a cation including a hydrogen ion, and examples thereof include potassium ion, sodium ion and ammonium ion. The antistatic function is exhibited by having the repeating unit having a sulfonic acid group represented by the chemical formula 1 in the polymer, and a preferable example of the monomer for providing the repeating unit represented by the chemical formula 1. Examples thereof include chemical formulas 3 to 6.

[0010]

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[0011]

[Chemical 4]

[0012]

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[0013]

[Chemical 6]

As a ratio of these repeating units in the polymer, the polymerizable vinyl monomer having a sulfonic acid group or its salt as a substituent, which gives the repeating unit shown in Chemical formula 1, is 40% by weight or more in the polymer composition. It is preferably less than 99% by weight, and when incorporated in this composition range, the performance as an antistatic agent is sufficiently exhibited. When the content of the antistatic agent is less than 40% by weight below the above range, the antistatic property itself may be insufficient, or the humidity dependence of the performance may become remarkable, and the antistatic performance is particularly low. There is a case where there is a problem that it is not practically applicable, because of the remarkable decrease of Also,
When a copolymer containing 99% by weight or more of the above range is used as the antistatic agent, the effect of introducing the repeating unit represented by the following chemical formula 2 is not recognized, and the water solubility of the antistatic agent is further reduced. Water resistance of the antistatic film is lowered due to the increase in the antistatic property, and when used as an antistatic agent for a light-sensitive material, for example, there may be a problem that the antistatic performance is significantly deteriorated after development processing.

Further, the repeating unit containing a nitrogen-containing heterocyclic group having a mercapto group represented by Chemical Formula 2 must be in the range of preferably 1% by weight or more and less than 60% by weight in the polymer. The water resistance of the antistatic agent itself can be greatly improved without impairing the antistatic performance of the polymer as the antistatic agent obtained in (1) and the transparency of the layer containing the antistatic agent. That is, by introducing the repeating unit represented by Chemical Formula 2 into the polymer as the antistatic agent, a crosslinking reaction occurs due to formation of a disulfide bond due to aerial oxidation of the mercapto group in Chemical Formula 2, and such a polymer is produced. By forming an antistatic layer containing the above on the support, crosslinking and water resistance of the layer progress from the progress of the crosslinking reaction, and a permanent antistatic layer excellent in water resistance and solvent resistance is formed on the surface of the support. Therefore, an extremely preferable effect is exhibited. Furthermore, by introducing such a mercapto group into the antistatic agent itself, it is possible to obtain a very favorable effect of improving the adhesiveness between the layer containing the antistatic agent and the layer adjacent thereto. That is, the antistatic treatment of the surface of the support is required to prevent various troubles due to the electrification of the support such as the film (adhesion of dust, deterioration of workability due to electrostatic attraction between the films). However, rather than using such a support such as an antistatic film alone, it is possible to further print on the surface of such a support, or to use a photosensitive material such as a silver halide emulsion or various In many cases, a layer having functionality is further formed and used. In such a case, the adhesion to the printing ink or the adhesion between various functional layers often becomes a problem, and when the adhesion is insufficient, problems such as peeling of the printing ink and the upper layer may occur. It was also often seen that various troubles occurred. As a means for solving these problems, the polymer having the above-mentioned substituent introduced with a mercapto group as shown in Chemical formula 2 is used as an antistatic agent, and an antistatic layer containing such a polymer is used as a support. It has been found that the above-mentioned formation significantly improves the adhesion between the support itself and this layer or the layer adjacent to the antistatic layer.

Such an improvement in the adhesiveness can be adjusted by changing the ratio of the repeating units (1) and (2) in the polymer as the antistatic agent according to the present invention. For example, when the antistatic agent according to the present invention is used by coating it on a support having a hydrophilic surface such as a film subjected to an aqueous undercoating treatment, or on the antistatic layer thus formed. When a layer is further formed by applying an aqueous coating to the above, the hydrophilicity as an antistatic agent is increased by increasing the content ratio of Chemical formula 1 and the affinity with the support or the upper layer is further increased. The adhesiveness of can be improved. In particular, when the repeating unit represented by the chemical formula 1 exceeds 50% by weight, the hydrophilicity of the layer containing the antistatic agent is increased, the wettability with water is improved, and both the coatability and the adhesiveness are improved. Is preferred. Alternatively, since the lipophilicity can be increased to some extent by increasing the ratio of the repeating unit represented by Chemical Formula 2 in the polymer, for example, the polyester film surface, various printing inks, solvent-based coating liquids, etc. The affinity is improved, and the coatability, printability, and adhesiveness can be improved. In this way, the ratio of Chemical formula 1 and Chemical formula 2 can be appropriately adjusted according to the purpose. A in Chemical formula 2 represents a nitrogen-containing heterocyclic group having at least one mercapto group, and preferable examples thereof include substituents shown in Chemical formulas 7 to 12, and J in Chemical formula 2 is divalent. Represents a linking group of, for example, alkylene, phenylene, -COO-, -C
ONH -, - SO ₂ NH-, and may be in the form which they are Kumia' not particularly limited as long as it is a divalent linking group.

[0017]

[Chemical 7]

[0018]

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[0019]

[Chemical 9]

[0020]

[Chemical 10]

[0021]

[Chemical 11]

[0022]

[Chemical 12]

Examples of preferable monomers for introducing such a functional group into the polymer as the antistatic agent include the monomers shown in Chemical formulas 13 to 19. These monomers can be conveniently obtained by a known synthetic method. For example, in the case of Chemical formula 14, a high yield can be obtained by reacting bismuthiol with sodium hydroxide as a sodium salt and reacting with chloromethylstyrene. You can It can be obtained in high yield including other monomers, and the mercapto group can be effectively introduced into the polymer.

[0024]

[Chemical 13]

[0025]

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[0026]

[Chemical 15]

[0027]

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[0028]

[Chemical 17]

[0029]

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[0030]

[Chemical 19]

When the proportion of the repeating unit of the chemical formula 2 in the polymer exceeds the above range and is introduced into the polymer in a proportion of 60% by weight or more, the crosslinking reactivity of the polymer as an antistatic agent increases. However, when it is used as an aqueous coating liquid because the antistatic performance itself is lowered or the solubility in water is lowered, it is not preferable because it may hinder the coating. Further, if the repeating unit of Chemical formula 2 is introduced only at a ratio of 1% by weight or less outside the above range,
Crosslinking and water resistance due to the repeating unit of the above-mentioned chemical formula 2 is unlikely to occur, and a problem may occur in water resistance which is one of the objects of the present invention, which is not preferable. Thus, in order to simultaneously satisfy the performance as an antistatic agent and the properties such as transparency of the water resistant film, the repeating units of Chemical formula 1 and Chemical formula 2 are simultaneously contained in the polymer in a ratio within the above range. It is very important that each repeating unit alone does not achieve the object of the present invention.

The water-soluble polymer as the antistatic agent according to the present invention preferably has a molecular weight in the range of 1,000 to 1,000,000, and more preferably has a weight average molecular weight in the range of 10,000 to 200,000. preferable. When the molecular weight is less than 1000, the water resistance of the obtained antistatic layer may be insufficient or the above-mentioned adhesiveness may be poor, which is not preferable. Alternatively, when the molecular weight exceeds 1,000,000, there is no problem in the properties as an antistatic agent, but when used as a coating liquid for processing the surface of a support, the viscosity of the coating liquid increases and the coating It is not preferable because it may adversely affect sex. For this reason, particularly when the weight average molecular weight of the water-soluble polymer is in the range of 10,000 to 200,000, the coating property of the coating liquid and the coating property as the antistatic agent can be kept good. It is preferable because it is possible.

The water-soluble polymer as the antistatic agent shown in the present invention can be easily produced by a usual radical polymerization method. However, since the water-soluble polymer has a mercapto group known as a chain transfer group, in order to obtain a polymer having a molecular weight range described above, the chain transfer property of such a mercapto group is reduced or prevented by various methods. There is a need. For this purpose, for example, all the functional groups represented by Chemical formula 2 have a mercapto group bonded to a heterocycle, and therefore, under alkaline conditions, such a mercapto group is converted into a salt form inactive to a chain transfer reaction. It is possible to For example, by converting such a mercapto group into a salt form with various alkaline substances such as sodium hydroxide and potassium hydroxide, the desired polymer can be stably obtained without the mercapto group participating in the chain transfer reaction during polymerization. Obtainable. Alternatively, known protection such as esterification is carried out for the purpose of protecting the mercapto group,
After completion of the polymerization, deprotection can be performed to regenerate the mercapto group.

The purpose of the present invention is basically to
This can be achieved by using a copolymer containing the repeating unit of as an antistatic agent. In addition to the repeating units shown in Chemical formulas 1 and 2, vinyl-based monomers copolymerizable for various purposes can be used. It is also possible to introduce units into the polymer.

Examples of such copolymerizable vinyl monomer units include ethylene, propylene, butylene,
Ethylene unsaturated monoolefins such as isobutylene, vinyl halides such as vinyl chloride, vinylidene chloride, vinyl bromide, vinyl acetate, vinyl propionate, vinyl benzoate, vinyl butyrate, and other vinyl esters, methyl, Alkyl esters of acrylic acid or methacrylic acid such as ethyl, propyl, isobutyl, n-butyl, n-octyl and 2-ethylhexyl, acrylic acid or methacrylic acid derivatives such as acrylonitrile, methacrylonitrile and acrylamide, vinyl methyl ether, Vinyl ethyl ether, vinyl isobutyl ether
Vinyl ethers such as ter, vinyl methyl ketone, vinyl hexyl ketone, vinyl such as methyl isopropyl ketone, N-vinyl pyrrole, N-vinyl carbazole,
N-vinyl compounds such as N-vinylpyrrolidone, styrene and derivatives thereof, carboxyl group-containing monomers such as acrylic acid, methacrylic acid, crotonic acid, maleic acid and itaconic acid, or N, N-dimethylaminoethyl (meth) acryl -, N, N-diethylaminoethyl (meth) acrylate, dimethylaminopropylacrylamide, and other amino group-containing monomers, and in addition to these, diallylamine, allylamine, N-methyldiallylamine, N, N- Dimethylallylamine,
Containing hydroxyl group or ethyleneoxy group, propyleneoxy group such as vinyl imidazole, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, methoxyethylene glycol (meth) acrylate It is also possible to introduce various monomers such as the above-mentioned monomers into the copolymer.

When such a monomer component is introduced as a copolymerization component into the polymer, it is preferable to introduce it in the range of 40% by weight or less. If it is introduced in excess of this range, the resulting antistatic agent is charged. The prevention performance is reduced,
Alternatively, it may be unfavorable in that it adversely affects the intended improvement in adhesiveness.

The object of the present invention is basically achieved by a polymer obtained by using the above-mentioned monomer in the specified range. Although the preventive film is formed, it is also preferable to use various additives in combination for the purpose of further improving the wear resistance, blocking resistance, water resistance and the like of the film. Examples of such additives include polymer emulsions such as styrene-butadiene latex, styrene-acrylic latex, various acrylic emulsions, vinyl acetate latex, polyester emulsion, polyurethane emulsion, and the like,
Polyvinyl alcohol, hydroxyethyl cellulose,
Hydroxypropyl cellulose, various cellulose derivatives such as carboxymethyl cellulose, various water-soluble polymers such as starch, gelatin, polyvinylpyrrolidone and chitosan, or silica, colloidal silica, titanium oxide,
The above object can be preferably achieved by adding inorganic fine particles such as zinc oxide, polystyrene fine particles, polymethyl methacrylate fine particles, and organic polymer fine particles such as silicone fine particles. When such an additive is used, the ratio of the two in the combination with the antistatic agent becomes a problem, but the antistatic agent for the entire coating layer in the coating layer for forming the antistatic layer is Ratio is 1
It is preferably 0% by weight or more, and if it is less than this, the antistatic performance may be insufficient.

The antistatic film obtained by adding an epoxy curing agent or an aziridine curing agent to the antistatic agent obtained in the present invention and three-dimensionally cross-linking the antistatic film provides durability of antistatic performance. It is preferable to further improve the sex. Compounds represented by Chemical Formulas 20 to 29 are particularly preferable examples of the curing agent used for such a purpose, and curing by reaction with at least two or more reactive epoxy groups or aziridinyl groups in the molecule. Is effectively generated between various functional groups having a mercapto group represented by Chemical formula 2 contained in the antistatic agent according to the present invention, and various curing is achieved by containing the repeating unit of Chemical formula 2 in the polymer itself. Even if the reaction with the agent is carried out at a relatively low temperature of 60 ° C. or less, the crosslinking reaction proceeds rapidly within several hours, which is particularly preferable for easily producing an antistatic film having excellent durability.

[0039]

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[0040]

[Chemical 21]

[0041]

[Chemical formula 22]

[0042]

[Chemical formula 23]

[0043]

[Chemical formula 24]

[0044]

[Chemical 25]

[0045]

[Chemical formula 26]

[0046]

[Chemical 27]

[0047]

[Chemical 28]

[0048]

[Chemical 29]

Preferred examples of the water-soluble antistatic polymer according to the present invention include the polymers shown in Chemical formulas 30 to 34.
However, the present invention is not limited to these.

[0050]

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[0051]

[Chemical 31]

[0052]

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[0053]

[Chemical 33]

[0054]

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[0055]

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[0056]

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[0057]

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[0058]

[Chemical 38]

[0059]

The present invention will be described in more detail with reference to the following synthetic examples and examples, but the present invention is not limited to these examples in addition to the effects.

Synthesis Example 1 93 parts of sodium p-styrenesulfonate, 2-mercapto-5- (4'-vinylbenzyl) mercapto-1,
3,4-thiadiazole 7 parts, sodium hydroxide 1.2
Part was dissolved in 200 parts of distilled water and 60 parts of ethanol, and V was used as a polymerization initiator while heating and stirring at 70 ° C. in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen introduction tube, and a reflux condenser. Polymerization was started by adding 1 part of -65 (2,2'-azobis (2,4-dimethylvaleronitrile), manufactured by Wako Pure Chemical Industries, Ltd.). Polymerization was carried out at this temperature for 4 hours to obtain a polymer solution having a weight average molecular weight of about 100,000.

Synthesis Example 2 70 parts of sodium p-styrenesulfonate, 30 parts of 2,4-dimercapto-6- (4'-vinylbenzyl) mercapto-1,3,5-triazine and 5.2 parts of sodium hydroxide were added. It was dissolved in 200 parts of distilled water and 60 parts of ethanol, and V-65 was used as a polymerization initiator while heating and stirring at 70 ° C. in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen introduction tube, and a reflux condenser. Polymerization was initiated by adding 1 part of (2,2′-azobis (2,4-dimethylvaleronitrile), manufactured by Wako Pure Chemical Industries, Ltd.). Polymerization was carried out at this temperature for 4 hours to obtain a polymer solution having a weight average molecular weight of about 100,000.

Synthesis Example 3 2-Acrylamido-2-methylpropanesulfonic acid 7
0 part, 2-mercapto-5- (4'-vinylbenzyl)
20 parts of mercapto-1,3,4-thiadiazole, 2-
Hydroxyethyl methacrylate (10 parts) and sodium hydroxide (17.6 parts) were dissolved in distilled water (200 parts) and ethanol (60 parts), and equipped with a stirrer, a thermometer, a nitrogen introduction tube, and a reflux cooling tube. V-65 (2,2'-azobis (2,4,4
-Dimethylvaleronitrile), manufactured by Wako Pure Chemical Industries, Ltd.) to start the polymerization. Polymerization was carried out at this temperature for 4 hours to obtain a polymer solution having a weight average molecular weight of about 100,000.

Synthesis Example 4 30 parts of sodium p-styrenesulfonate, 60 parts of sodium allylsulfonate, 2-mercapto-5- (4 '
-Vinylbenzyl) mercapto-1,3,4-thiadiazole 10 parts, sodium hydroxide 1.7 parts and distilled water 20
Dissolve in 0 parts and 60 parts of ethanol, stirrer, thermometer,
7 in a 4-neck flask equipped with a nitrogen inlet tube and a reflux condenser.
V-65 as a polymerization initiator while heating and stirring at 0 ° C
Polymerization was initiated by adding 1 part of (2,2′-azobis (2,4-dimethylvaleronitrile), manufactured by Wako Pure Chemical Industries, Ltd.). Polymerization was carried out at this temperature for 4 hours, and the weight average molecular weight was about 10
A good polymer solution was obtained.

Synthesis Example 5 Sodium p-styrenesulfonate 50 parts, 2,4-dimercapto-6- (4'-vinylbenzyl) mercapto-1,3,5-triazine 20 parts, acrylic acid 30 parts,
20 parts of sodium hydroxide, 200 parts of distilled water and ethanol
V-65 (2,2'-azobis) as a polymerization initiator while being heated and stirred at 70 ° C in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen inlet tube, and a reflux condenser tube. Polymerization was started by adding 1 part of (2,4-dimethylvaleronitrile), manufactured by Wako Pure Chemical Industries, Ltd. Polymerization was carried out at this temperature for 4 hours to obtain a polymer solution having a weight average molecular weight of about 100,000.

Comparative Synthesis Example 85 parts of sodium p-styrenesulfonate, 10 parts of methacrylic acid and 5-hydroxyethyl methacrylate 5
Part was dissolved in 200 parts of distilled water and 60 parts of ethanol, and V was used as a polymerization initiator while heating and stirring at 70 ° C. in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen introduction tube, and a reflux condenser. Polymerization was started by adding 1 part of -65 (2,2'-azobis (2,4-dimethylvaleronitrile), manufactured by Wako Pure Chemical Industries, Ltd.). Polymerization was carried out at this temperature for 4 hours to obtain a polymer solution having a weight average molecular weight of about 100,000.

Example 1 Polymer concentration 7.5% (solid content), as a curing agent
The compound shown in (4) was added so as to be 10% by weight with respect to the polymer to prepare a coating liquid. The pH of the coating solution is 1N hydrochloric acid aqueous solution or 1N sodium hydroxide aqueous solution.
Adjusted to 7.0. The coating liquid thus prepared was applied to a PET film which had been subjected to an aqueous undercoating treatment with gelatin and dried at 40 ° C. for 24 hours to obtain an antistatic film. This was cut into a 15 cm square and subjected to a physical property test.

The antistatic ability of the obtained antistatic film was measured by subjecting the sample before washing and after washing (washing with water at 40 ° C. for 1 minute) to 25 ° C. and 50% RH (relative humidity) in an atmosphere of 2.
Leave it for a while, and measure its surface resistance by Mitsubishi Yuka Co., Ltd. Hire
It was measured with a sta surface resistance meter model HT-210. A surface resistance of 10 ¹² ohms or more is impossible and 10
Below ¹¹ ohms is a good level.

The adhesiveness was evaluated in three grades of ◯ Δ × by scratching the surface of the sample with a knife in a square shape at intervals of 5 mm and rubbing the surface with a moistened tissue. The mark ○ indicates that it does not peel off at all, the mark Δ indicates that it peels off slightly, and the mark × indicates that it peels off considerably.

The hydrophilicity of the surface of the antistatic film was evaluated by measuring the contact angle with water. Table 2 shows the results.

[0070]

[Table 1]

Example 2 A PET film provided with an antistatic polymer layer was further coated with the following gelatin aqueous solution and dried at 50 ° C. for 12 hours.
Hardened. The compound shown in Chemical formula 39 was used as the hardener and the compound shown in Chemical formula 40 was used as the surfactant.

[0072]

[Chemical Formula 39]

[0073]

[Chemical 40]

<Gelatin aqueous solution> Gelatin 5.0 g Hardener 0.05 g Surfactant 0.1 g Water to 100 g.

The adhesion between the antistatic layer and the gelatin layer was evaluated according to the method described in Example 1. Table 2 shows the results.

[0076]

[Table 2]

[0077]

EFFECT OF THE INVENTION By using the antistatic polymer according to the present invention, it is possible to obtain a coating film which is excellent in durability without deterioration of antistatic performance and is excellent in adhesion, water resistance and transparency. it can.

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Claims (3)

[Claims] 1. An antistatic agent, which is a water-soluble polymer containing at least the repeating units shown in Chemical formulas 1 and 2 as the antistatic agent. Embedded image In the chemical formula 1, R ₁ represents a hydrogen atom or a methyl group. L represents a single bond or a divalent linking group. X ₁ represents a cation including a hydrogen ion. Embedded image In Chemical formula 2, R ₁ represents a hydrogen atom or a methyl group, and J is 2
Represents a valent linking group, and A represents a nitrogen-containing heterocyclic group having a mercapto group. 2. The water-soluble polymer contains at least 40% by weight and less than 99% by weight of the repeating unit represented by Chemical formula 1 and at least 1% by weight and 60 by weight of the repeating unit represented by Chemical formula 2.
The antistatic agent according to claim 1, wherein the antistatic agent is a copolymer containing less than 5% by weight. 3. An antistatic agent characterized by being cured by adding an epoxy compound or an aziridine compound to the water-soluble polymer according to claim 1 or 2.