JP2003073657A - Antistatic agent, process for production and method for antistatic treatment - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an antistatic agent that exhibits the excellent endurable antistatic performance and that can inhibit the deterioration of color fastness of a finished textile product. SOLUTION: The antistatic agent comprises a tertiary amine salt or a quaternary ammonium salt of a polyester produced by a condensation polymerization reaction of an ethylene oxide adduct of an amine with an 8-20C aromatic dicarboxylic acid or its derivative as essential components.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to fibers, films,
The present invention relates to an antistatic agent for synthetic resin products such as molded products. More specifically, an antistatic agent that exerts an excellent antistatic effect by post-processing synthetic resin products, particularly synthetic fibers, yarns, and fabrics, and has excellent durability, a method for producing the same, and an antistatic agent using the same. It relates to a processing method.

[0002]

2. Description of the Related Art Conventionally, as an antistatic agent for resin products, it is widely known that a tertiary amine salt or a quaternary ammonium salt compound exerts excellent performance. Further, the cationic surfactant has excellent antistatic property immediately after treatment, but has very poor durability and has a problem in practical use. Therefore, a cationic urethane is used as an antistatic agent having excellent durability. A heat-reactive antistatic agent composed of a prepolymer has been proposed (Japanese Patent Laid-Open No. 62-295986).

[0003]

However, these conventional antistatic agents are not sufficiently satisfactory in durability and antistatic property, and particularly when applied to textiles, the dyeing fastness is remarkably reduced. Therefore, it is necessary to perform a washing step after performing antistatic processing using these antistatic agents, which is a problem in practical use.

In order to solve the problems of the prior art, the present invention provides an antistatic agent which exhibits excellent durability, exhibits an excellent antistatic effect, and can suppress a decrease in dyeing fastness of a processed textile product. It is an object of the present invention to provide a manufacturing method thereof and an antistatic treatment method using the same.

[0005]

In order to solve the above-mentioned problems, the inventors of the present invention have conducted extensive studies and, as a result, have found that a polyester resin having a tertiary amine salt or quaternary ammonium salt structure causes a reduction in dyeing fastness. The present invention has been completed by finding that the antistatic property is suppressed and excellent in durability.

That is, the antistatic agent of the present invention comprises at least one amine compound selected from the group of amine compounds represented by the formulas (1), (2) and (3) and having 8 to 8 carbon atoms. It is characterized by containing a tertiary amine salt or a quaternary ammonium salt of a polyester compound obtained by polycondensation reaction of 20 aromatic dicarboxylic acids or derivatives thereof as an essential component.

[0007]

[Chemical 4]

The antistatic agent of the present invention is a polyester obtained by further subjecting an aliphatic dicarboxylic acid or a lower alkyl ester thereof, or a polyoxyalkylene represented by the formula (4) or (5) to a polycondensation reaction. It is characterized by containing a tertiary amine salt or a quaternary ammonium salt of the compound.

[0009]

[Chemical 5]

In the antistatic agent, the mass average molecular weight (Mw) of the polyester compound is 5,000 to 1
It is preferably in the range of 0,000.

Further, the antistatic treatment method of the present invention is characterized in that the substrate to be treated is brought into contact with a solution comprising the above-mentioned solution containing the antistatic agent.

The third polyester compound of the present invention
The method for producing a secondary amine salt or a quaternary ammonium salt comprises at least one amine compound selected from the group of amine compounds represented by formula (1), formula (2) and formula (3), and a carbon number of 8 To a compound containing 20 to 20 aromatic dicarboxylic acid or its derivative as an essential component are subjected to polycondensation reaction to obtain a polyester compound, and then reacted with a neutralizing agent or an alkylating agent to form a tertiary amine salt or a quaternary amine salt. It is characterized in that an ammonium salt is synthesized.

[Chemical 6]

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION The amine compound used as a raw material in the present invention is represented by the above formula (1), formula (2) or formula (3). Examples of the aliphatic hydrocarbon group having 1 to 22 carbon atoms represented by R ¹ , R ² , R ³ , R ⁴ and R ⁵ include hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, octadecyl. , Oleyl groups, beef tallow, coconut oil-derived aliphatic hydrocarbon groups which are a mixture thereof, and the like. Among them, from the viewpoint of imparting a good antistatic effect, R ¹ , R ² , R ³ and R ⁴ are preferably aliphatic hydrocarbon groups having 12 to 22 carbon atoms, and from the viewpoint of durability, having 16 to 16 carbon atoms. The aliphatic hydrocarbon group of 22 is more preferable, and the tallow-derived hydrocarbon group is particularly preferable. Further, R ⁵ is preferably an aliphatic hydrocarbon group having 1 to 6 carbon atoms.

In equations (1) to (3), o, p,
q, r, s, and t represent the number of moles of ethylene oxide added, and each is a number of 1 or more, and o + p is 5 to 50,
q is 5 to 50 and r + s + t is 3 to 50. When o + p is less than 5, antistatic performance is not exhibited, sufficient antistatic effect cannot be obtained, and the solubility of the reaction product in water is insufficient, so that it may be applied as an aqueous solution to fibers or films. This is because it becomes difficult to prepare a dipping solution for fibers, cloth, and the like. On the other hand, when o + p exceeds 50, the hydrophilicity becomes too high and the durability deteriorates. The value of o + p is preferably in the range of 10 to 45, more preferably in the range of 15 to 40. Also, q is 5 to
It is in the range of 50, and is preferably in the range of 10 to 45, and more preferably in the range of 15 to 40 for the same reason as limiting the range of o + p. Furthermore, r + s + t is 3 to 5
The range is 0, and for the same reason that the range of o + p is limited, the range of 10 to 45 is preferable, and 1 is more preferable.
It is in the range of 5 to 40.

As the amine compounds represented by the formulas (1) to (3), known mono- or dialkylamines and ethylenedioxide adducts of alkyldiamines can be appropriately used. Specifically, as the ethylene oxide adduct of mono- or dialkyl amine, ethylene oxide adduct of lauryl amine, ethylene oxide adduct of coconut oil amine, ethylene oxide adduct of stearyl amine, ethylene oxide adduct of beef tallow amine, ethylene oxide of hardened tallow amine. Examples thereof include adducts, ethylene oxide adducts of lauryl diamine, coconut oil diamines, ethylene oxide adducts of stearyl diamine, ethylene oxide adducts of beef tallow diamine, and ethylene oxide adducts of hardened tallow diamine. Examples of the ethylene oxide adduct of alkyldiamine include coconut oil diamine propylene diamine ethylene oxide adduct, stearyl propylene diamine ethylene oxide adduct, beef tallow propylene diamine ethylene oxide adduct, and hardened tallow propylene diamine ethylene oxide adduct. These may be used alone or in combination of two or more.

8 carbon atoms used as a raw material in the present invention
Examples of the aromatic dicarboxylic acid of 20 to 20 include phthalic acid, isophthalic acid, terephthalic acid, 2,6-naphthalenedicarboxylic acid, and methylterephthalic acid. As a derivative of an aromatic dicarboxylic acid having 8 to 20 carbon atoms,
Aromatic dicarboxylic acid anhydride, lower alkyl (1 carbon atom
~ 3) Esters, acid halides and the like can be mentioned. Examples of the lower alkyl ester of aromatic dicarboxylic acid include monomethyl ester, diethyl ester, monoethyl ester, diethyl ester and the like. Examples of the acid halide of aromatic dicarboxylic acid include monochloride, dichloride, monobromide, dibromide and the like. These may be used alone or in combination of two or more.

Among the aromatic dicarboxylic acids or their derivatives, aromatic dicarboxylic acids or their methyl esters are preferable from the viewpoint of durability, and aromatic dicarboxylic acids having 8 to 12 carbon atoms or their derivatives are more preferable. Specifically, terephthalic acid, dimethyl terephthalate, isophthalic acid, dimethyl isophthalate, phthalic acid and dimethyl phthalate are preferably used.

In the present invention, the amine compound, the aromatic dicarboxylic acid or the derivative thereof can be used alone or in a mixture of two or more kinds.
Further, at the time of polycondensation of the polyester resin, an aliphatic dicarboxylic acid or a lower alkyl ester thereof or a polyoxyalkylene such as polyethylene glycol may be copolycondensed as the third component raw material. Co-polycondensation of these third components has the advantage that the texture and water absorption of the work cloth can be imparted. These compounds may be used alone or in combination of two or more.

Examples of the aliphatic dicarboxylic acid or its lower alkyl ester include linear dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid and pimelic acid, or their methyl esters, methylmalonic acid and methylsuccinic acid. Examples thereof include acids, dicarboxylic acids having a side chain such as methylglutaric acid, and alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid.

Further, as the polyoxyalkylenes,
A compound containing ethylene oxide or propylene oxide represented by formula (4) or formula (5) as a constituent unit is preferable. In the formula, x, y, and z are each 0 or a number of 1 or more. However, x, y, and z never become 0 at the same time. Considering reactivity and durability of the antistatic agent, it is preferable to use a compound having a molecular weight of 400 to 6000, preferably 1000 to 2000 as the polyoxyalkylene.

Examples of the polyoxyalkylenes represented by the formula (4) include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, polyethylene glycol, ethylene oxide.
Examples thereof include propylene oxide block copolymer. Examples of the polyoxyalkylene represented by the formula (5) include ethylene oxide propylene oxide adducts of ethylene diamine, such as Tetronic TR manufactured by Asahi Denka Co., Ltd.
A series etc. can be mentioned.

In the present invention, the reaction ratio of the amine compound and the aromatic dicarboxylic acid or its derivative is not particularly limited, but the aromatic dicarboxylic acid or its derivative and the amine compound may be reacted at 5:95 to 60:40. (Mass ratio), preferably 10:90 to 50:50 (mass ratio). The third component raw material is preferably reacted in an amount of 20 parts by mass or less, preferably 15 parts by mass or less, with respect to 100 parts by mass of the aromatic dicarboxylic acid or its derivative. It is particularly preferable to use 1 to 15 parts by mass.

In the present invention, the order of reacting the amine compound with the aromatic dicarboxylic acid or its derivative is not particularly limited, and a usual polycondensation reaction may be carried out, and the reaction order and the like are appropriately selected according to the reaction mode. be able to. The molecular weight (Mw) of the polyester compound is 5,000 to 100,0.
The range of 00 is preferable, and more preferably 8,000 to 8
Range of 10,000, more preferably 10,000 to 6
It is in the range of 10,000. The reason why the molecular weight is limited in this way is that if it is less than 5,000, the durability of the antistatic performance is significantly lowered and the dyeing fastness is also lowered. On the other hand, if it exceeds 100,000, the reaction efficiency at the time of neutralizing or alkylating the tertiary amine after the polycondensation reaction is reduced, and the resulting tertiary amine salt or quaternary ammonium salt is water-soluble. This is because the stability of the product deteriorates due to the deterioration of the product.

The mass average molecular weight (Mw) is a polystyrene equivalent molecular weight measured by gel permeation chromatography (GPC).

The reaction mode will be described below with reference to specific examples.

Aromatic dicarboxylic acid and aliphatic dicarboxylic acid or polyoxyalkylenes are mixed at a predetermined ratio and transesterified at a temperature of about 120 to 180 ° C. for 1 to 2 hours, and then an amine compound is added. Add (add antioxidant etc. if necessary), temperature about 220-28
A polyester compound is obtained by reacting at 0 ° C. and a pressure of 1 to 2 kPa for 4 to 5 hours. In the polyesterification reaction, a usual esterification catalyst may be used, and examples thereof include antimony trioxide, dibutyltin oxide, tetrabutyl titanate and zinc acetate.

Then, a tertiary amine salt can be obtained by adding a neutralizing agent to the polyester compound, and by reacting with the polyester compound at about 80 to 120 ° C. using an alkylating agent. , A quaternary ammonium salt can be obtained.

For the preparation of the tertiary amine salt, hydrochloric acid, acetic acid, sulfuric acid, phosphoric acid or the like can be used as a neutralizing agent. For the preparation of the quaternary ammonium salt, dimethyl sulfate, diethyl sulfate, epichlorohydrin, methyl chloride or the like can be used as an alkylating agent. The alkylating agent is preferably used in an amount of 0.5 to 1.0 mol with respect to 1 mol of the amine compound.

The antistatic agent of the present invention may be used as it is as a molded product or may be used as a powder, and is dissolved or dispersed in a solvent (particularly an aqueous solvent) or water to prepare a solution such as an aqueous solution or dispersion. You may use. When the antistatic agent of the present invention is dissolved in the above-mentioned solvent or water and used as a solution, it is added as a solid component in order to enhance the durability of the antistatic agent.
It is preferable to dissolve or disperse it at a concentration of 10% by mass.
An antistatic treatment can also be performed by contacting this with a substrate to be treated.

Further, other known additives may be added to the antistatic agent of the present invention depending on various uses, within the range not deteriorating the purpose of the antistatic agent of the present invention. Examples of such additives include pigments, dyes, plasticizers, release agents,
Antioxidants, flame retardants, ultraviolet absorbers, antibacterial agents and the like can be mentioned.

The object of use of the antistatic agent of the present invention is not particularly limited, but it is an antistatic agent for synthetic resin products such as fibers, films and molded articles, especially antistatic agents for post-processing of synthetic fibers, yarns and fabrics. It is suitable as an agent. Therefore, it can be applied to any substrate as a coating agent. Such base materials include high / medium / low density polyethylene, ethylene /
Vinyl acetate copolymer, olefin resin such as polypropylene, acrylic resin such as poly (meth) acrylic acid ester, polystyrene, high impact polystyrene, A
Styrene resin such as BS resin, polyester such as polyethylene terephthalate and polybutylene terephthalate,
Polyamide such as nylon 6, nylon 66, polycarbonate, thermoplastic resin such as polyvinyl chloride, phenol resin, thermosetting resin such as polyurethane, metal such as iron, steel, aluminum, stainless steel, wood, paper, rayon, leather, etc. The natural materials and the like can be mentioned. The above-mentioned substrate can be applied to various processed products such as films, sheets, molded products, woven fabrics and non-woven fabrics.

The method of applying the aqueous solution or the like to the substrate is not particularly limited, and a brush coating method, a spray coating method, a dipping method, a flow coating method and the like can be adopted. After coating, heat treatment is appropriately performed to remove the solvent,
A polymer film is formed on the surface of the base material. It is preferable that the thickness of the coating film after drying is 0.1 to 1 μm. The base material may be subjected to a pretreatment such as an undercoating agent coating or a corona treatment, if necessary. Further, after coating, for the purpose of improving water resistance, durability, etc., crosslinking treatment by heat / light may be performed.

In the method of imparting the antistatic effect by dipping the above-mentioned base material in the above-mentioned antistatic agent solution of the present invention using a dipping method and adsorbing the antistatic agent on the surface of the base material, 1 to 20 ~ 130 ℃ solution
It is better to soak for 0 to 60 minutes.

[0034]

EXAMPLES Next, the present invention will be specifically described by way of examples, but the present invention is not limited to these examples. In addition, in the following examples and the like, "mass%" and "parts by mass" are abbreviated as "%" and "parts", respectively, unless otherwise specified.

In the examples and comparative examples, the antistatic agents were evaluated by the following methods.

(1) Method of Processing Antistatic Agent A 3% aqueous solution of each antistatic agent was prepared, and a test cloth was immersed in the solution under the following processing conditions and dried to prepare each processed cloth. Test cloth: Polyester tropical treatment bath: 3% aqueous solution (solid content conversion) Treatment method: pad-dry method (1 dip., 1 nip.
Squeezing rate: 50%) Drying condition: 100 ° C. × 2 minutes Set condition: 160 ° C. × 2 minutes (2) Durability evaluation (washing method) JIS L-0217 In accordance with the washing method 103 method, 20
I washed it twice. Then, rinse 10 times, and after 2 minutes of dehydration,
It was dried in a dryer at 70 ° C. for 1 hour. (3) Test of antistatic performance Each of the work cloths subjected to the above test is subjected to room temperature of 20 ° C and humidity of 40%.
JIS L-1094 after leaving for 24 hours under the environment
Friction electrification voltage was measured by method B, and antistatic performance was evaluated.

(4) Dyeing fastness test (rubbing fastness test) (a) Test cloth preparation method: A test cloth was prepared by dyeing under the following conditions using polyester tropical as the test cloth. (Dyeing conditions) Test cloth: Polyester tropical dyeing material: Sumikaron Black S-XE 300% 3% o. w. f. Drug: Benerap HG (level dyeing agent manufactured by Meitetsusha Yushi Kogyo Co., Ltd.) 0.5 g / l acetic acid (90%) 0.3 ml / l Bath ratio: 1:20 Dyeing color: 130 ° C. × 60 minutes → washing with hot water -> Washing with water and reducing washing: Visnor SK (cleaning agent manufactured by Yatasha Oil and Fats Industry Co., Ltd.) 2g / l Hydrosulfite 2g / l Caustic soda 2g / l Bath ratio: 1:20 Treatment: 80 ° C x 20 Min → Wash with water → Wash with water (b) Antistatic agent processing method: Each processing cloth was prepared under the following processing conditions, and the antistatic performance was evaluated by the friction fastness test (dry and wet) of JIS L-0849. did. Test cloth: the above-mentioned dyeing test cloth treatment bath: 3% aqueous solution (solid content conversion) treatment method: pad-dry method (1 dip., 1 nip.
Squeeze ratio 50%) Drying conditions: 100 ° C x 2 minutes Set conditions: 160 ° C x 2 minutes

Example 1 In a glass reaction vessel equipped with a thermometer, a stirrer, a reflux condenser, a nitrogen inlet tube and a dropping funnel, dimethyl terephthalate (50 g), dimethyl isophthalate (10 g) and ethylene glycol (60 g). )
And zinc acetate (0.5g) as a catalyst,
The temperature was gradually raised to 2 hours. Reaction temperature is 120 ℃
Methanol began to distill from the vicinity and was collected. After reaching 180 ° C., the transesterification reaction was further performed for 1 hour. After the transesterification reaction, stearylamine ethylene oxide 25 mol adduct (140 g) was added to the reaction vessel,
Antioxidant Adeka AO-330 (10 manufactured by Asahi Denka Co., Ltd.
g) was added and the temperature was raised to 220 ° C. Then, the pressure was reduced with a vacuum pump and the reaction was performed under a reduced pressure of 2.7 kPa. The temperature was raised to 280 ° C. over 3 hours after starting the pressure reduction. Then, the mixture was aged for 1 hour to obtain a thermoplastic polyester resin having a molecular weight (Mw) of 35,000. The obtained thermoplastic polyester resin is heated to 70 ° C., acetic acid as a neutralizing agent equimolar to the above amine, and ion-exchanged water so that the solid content is 10% are added, and stirred and dissolved for 1 hour. An aqueous polyester resin solution was obtained.

(Example 2) A thermoplastic polyester resin having a molecular weight (Mw) of 38,000 was obtained in the same manner as in Example 1 except that each raw material compound used in Example 1 was replaced with the compound shown in Table 1. . To this thermoplastic polyester resin, dimethylsulfuric acid in an amount equal to that of the amine compound (stearylamine ethylene oxide 25 mol adduct) shown in Table 1 was added,
Alkylation was carried out by stirring at ℃ for 1 hour. After that, the solid content is 1
Add ion-exchanged water to 0% and add 70 ℃
The mixture was stirred for 1 hour to obtain a polyester resin aqueous solution.

Example 3 An antistatic agent was obtained in the same manner as in Example 2 except that each raw material compound used in Example 2 was replaced with the compound shown in Table 1. The molecular weight (Mw) of the obtained polyester resin was 15,000. In addition, the compounding mass g is shown in the parentheses in the table.

Example 4 An antistatic agent was obtained in the same manner as in Example 1 except that each raw material compound used in Example 1 was replaced with the compound shown in Table 1. The molecular weight (Mw) of the obtained polyester resin was 42,000. In addition, the compounding mass g is shown in the parentheses in the table.

Example 5 An antistatic agent was obtained in the same manner as in Example 2 except that each raw material compound used in Example 2 was replaced with the compound shown in Table 1. The molecular weight (Mw) of the obtained polyester resin was 35,000. In addition, the compounding mass g is shown in the parentheses in the table.

[0043]

[Table 1] Example 2 Example 3 Example 4 Example 5 Amine compound Beef tallow amine Stearyl coconut oil net beef tallow diami EO15 moamine EO-EO15-EO15-l adduct 45 mol with mol adduct (220) adduct (75) (240) (120) Aromatic dical terephthale terephthale terephthale terephthalbonic acid dimethyl acid dimethyl acid dimethyl acid dimethyl acid dimethyl acid (50) / (50) (50) (50) isophthalic acid phthalic acid dimethyl acid dimethyl acid (5) Three-component PEG1000-PEG2000 Adipic acid (30) (5) Dimethyl (20) Neutralizer-Acetic acid- Alkylating agent Dimethylsulfate Diethylsulfate-Dimethylsulfate Condensation conditions Temperature (° C) 280 250 280 270 Pressure (Decompression degree) ( kPa) 2 2 1 1.5 molecular weight (Mw) 38,000 15,000 42,000 35,000 * EO: ethylene oxide * PEG 1000: polyethylene glycol (molecular weight 1000) * P G2000: polyethylene glycol (molecular weight 2000)

(Comparative Examples 1 to 3) Antistatic agents were obtained in the same manner as in Example 1 except that the raw material compounds used in Example 1 were replaced with the compounds shown in Table 2. It is shown in Table 2 together with the molecular weight (Mw) of the obtained polyester resin. In addition, the compounding mass g is shown in the parentheses in the table.

[0045]

[Table 2] Comparative Example 2 Comparative Example 3 Amine compound - stearyl amine EO 45 mol-added product (200) an aromatic dicarboxylic terephthalic - Bonn acid dimethyl (50) / isophthalate (5) third component PEG3000 adipic acid (140) dimethyl ( 50) Neutralizer-Acetic acid alkylating agent- Condensation conditions Temperature (° C) 280 280 Pressure (pressure reduction degree) (kPa) 22 Molecular weight (Mw) 40,000 38,000 * PEG 3000: Polyethylene glycol (molecular weight 3000)

The evaluation results of the antistatic agents of Examples and Comparative Examples are shown in Table 3 together with the evaluation results of commercially available urethane antistatic agents.

[0047]

[Table 3] Durability Antistatic Performance (V) Rubbing Fastness Test Wash 0 Wash 20 Wash Dry Example 1 50 670 3-4 3 Example 2 38 500 3-4 3 Example 3 40 770 3-4 3 Example 4 50 640 3-4 3 Example 5 45 690 3-4 3 Comparative example 1 200 5500 2 1 Comparative example 2 40 4900 3-4 3 Urethane type antistatic agent 50 660 21 1 * Urethane type antistatic agent: "Elastron W- 22 "(manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.)

As is clear from Table 3, the antistatic agent of this example maintains the antistatic property after washing and is excellent in durability as compared with the antistatic agent of the comparative example. . In addition, compared with a commercially available urethane-based antistatic agent, good results were obtained in a friction fastness test when antistatic treatment was performed after dyeing, and it was found that a reduction in dyeing fastness of a processed textile product can be suppressed. .

[0049]

As described above, the antistatic agent of the present invention is obtained by subjecting an ethylene oxide adduct of an alkylamine and an aromatic dicarboxylic acid having 7 to 20 carbon atoms or a derivative thereof to polycondensation reaction as an essential constituent component. Since it contains a tertiary amine salt or a quaternary ammonium salt of the polyester compound obtained as described above, it has an excellent antistatic effect and
Highly washable and highly durable. In particular, when used for synthetic fibers, yarns, and fabrics, the dyeing fastness is less likely to decrease, so that a washing step after dyeing is not necessary, which contributes to improvement in productivity. Therefore, it can be widely applied to prevent static electricity and prevent adhesion of dirt to industrial textile products and household textile products.

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 4J029 AA01 AC02 AE18 BF25 BH01                       CA03 CA04 CA05 CA06 CB04A                       CB05A CB06A CB06B CC06A                       DA07 FA12 FA17 FC02 FC45                       KH01                 4L033 AC06 BA85 CA45

Claims (5)

[Claims] 1. At least one amine compound selected from the group of amine compounds represented by formula (1), formula (2) and formula (3), and an aromatic dicarboxylic acid having 8 to 20 carbon atoms or a compound thereof. An antistatic agent comprising a tertiary amine salt or a quaternary ammonium salt of a polyester compound obtained by subjecting a derivative to a polycondensation reaction as an essential component. [Chemical 1] 2. An aliphatic dicarboxylic acid or a lower alkyl ester thereof, or a polyoxyalkylene represented by the formula (4) or (5) is subjected to a polycondensation reaction. Antistatic agent. [Chemical 2] 3. The antistatic agent according to claim 1, wherein the mass average molecular weight (Mw) of the polyester compound is in the range of 5,000 to 100,000. 4. An antistatic treatment method, which comprises bringing a substrate to be treated into contact with a solution containing the antistatic agent according to claim 1. 5. At least one amine compound selected from the group of amine compounds represented by formula (1), formula (2) and formula (3), and an aromatic dicarboxylic acid having 8 to 20 carbon atoms or a compound thereof. A polyester compound is obtained by subjecting a compound containing a derivative as an essential component to polycondensation reaction, and then reacted with a neutralizing agent or an alkylating agent to synthesize a tertiary amine salt or a quaternary ammonium salt. To produce a tertiary amine salt or quaternary ammonium salt of the polyester compound. [Chemical 3]