US-12624265-B2 - Antistatic agent, antistatic composition comprising same, antistatic resin composition comprising same, and molded article thereof

Abstract

Provided are: an antistatic agent which can continuously impart an excellent antistatic effect to a synthetic resin and has excellent storage stability and productivity (cutting property); an antistatic agent composition containing the same; an antistatic resin composition containing the antistatic agent or the antistatic agent composition; and a molded article thereof. The antistatic agent contains at least one polymer compound (E) which is obtained by a reaction of a polyester (a) obtained by a reaction between a diol (a1) and a dicarboxylic acid (a2), a compound (b) containing at least one ethyleneoxy group and having hydroxy groups at both ends, and an epoxy compound (D) containing two or more epoxy groups. The diol (a1) is at least either of 1,4-butanediol and ethylene glycol, and the dicarboxylic acid (a2) is succinic acid or a dicarboxylic acid mixture containing succinic acid.

Inventors

• Naoki ENJO
• Kazukiyo Nomura

Assignees

• ADEKA CORPORATION

Dates

Publication Date

20260512

Application Date

20191205

Priority Date

20190329

Claims (20)

1. 1 . An antistatic agent, comprising at least one polymer compound (E) which is obtained by a reaction of a polyester (a) obtained by a reaction between a diol (a1) and a dicarboxylic acid (a2), a compound (b) comprising at least one ethyleneoxy group and having hydroxy groups at both ends, and an epoxy compound (D) comprising two or more epoxy groups, wherein the diol (a1) is at least either of 1,4-butanediol and ethylene glycol, and the dicarboxylic acid (a2) is succinic acid or a dicarboxylic acid mixture comprising succinic acid.
2. 2 . The antistatic agent according to claim 1 , wherein the polymer compound (E) comprises: a polyester block (A) constituted by the polyester (a); and a polyether block (B) constituted by the compound (b), and the polymer compound (E) has a structure in which the polyester block (A) and the polyether block (B) are bound via ester bonds or ether bonds which are each formed by a reaction of a terminal hydroxy group or carboxyl group of the polyester (a), a terminal hydroxy group of the compound (b), and an epoxy group of the epoxy compound (D) or a hydroxy group formed by a reaction of the epoxy group.
3. 3 . The antistatic agent according to claim 2 , wherein the polymer compound (E) has a structure in which a block polymer (C) having carboxyl groups at both ends, in which the polyester block (A) and the polyether block (B) are repeatedly and alternately bound via ester bonds, and the epoxy compound (D) are bound via ester bonds.
4. 4 . The antistatic agent according to claim 3 , wherein the block polymer (C) of the polymer compound (E) has a number-average molecular weight of 5,000 to 50,000 in terms of polystyrene.
5. 5 . The antistatic agent according to claim 3 , wherein the polyester (a) of the polymer compound (E) has a structure comprising carboxyl groups at both ends.
6. 6 . The antistatic agent according to claim 3 , wherein the compound (b) of the polymer compound (E) is a polyethylene glycol.
7. 7 . The antistatic agent according to claim 3 , wherein the polymer compound (E) has a crystallization temperature in a range of 20 to 70° C.
8. 8 . The antistatic agent according to claim 2 , wherein the polyester (a) of the polymer compound (E) has a structure comprising carboxyl groups at both ends.
9. 9 . The antistatic agent according to claim 2 , wherein the compound (b) of the polymer compound (E) is a polyethylene glycol.
10. 10 . The antistatic agent according to claim 2 , wherein the polymer compound (E) has a crystallization temperature in a range of 20 to 70° C.
11. 11 . The antistatic agent according to claim 1 , wherein the polyester (a) of the polymer compound (E) has a structure comprising carboxyl groups at both ends.
12. 12 . The antistatic agent according to claim 11 , wherein the compound (b) of the polymer compound (E) is a polyethylene glycol.
13. 13 . The antistatic agent according to claim 1 , wherein the compound (b) of the polymer compound (E) is a polyethylene glycol.
14. 14 . The antistatic agent according to claim 1 , wherein the polymer compound (E) has a crystallization temperature in a range of 20 to 70° C.
15. 15 . The antistatic agent according to claim 1 , wherein the polyester (a) of the polymer compound (E) has a number-average molecular weight of 1,000 to 10,000 in terms of polystyrene.
16. 16 . An antistatic agent composition, obtained by incorporating at least one selected from the group consisting of alkali metal salts and ionic liquids into the antistatic agent according to claim 1 .
17. 17 . An antistatic resin composition, obtained by incorporating the antistatic agent composition according to claim 16 into a synthetic resin.
18. 18 . An antistatic resin composition, obtained by incorporating the antistatic agent according to claim 1 into a synthetic resin.
19. 19 . The antistatic resin composition according to claim 18 , wherein the synthetic resin is at least one selected from the group consisting of polyolefin-based resins, polystyrene-based resins, and copolymers thereof.
20. 20 . A molded article, comprising the antistatic resin composition according to claim 18 .

Description

TECHNICAL FIELD The present invention relates to: an antistatic agent; an antistatic agent composition containing the same; an antistatic resin composition containing the antistatic agent or the antistatic agent composition (the antistatic resin composition is hereinafter also simply referred to as “resin composition”); and a molded article thereof. More particularly, the present invention relates to: an antistatic agent which can continuously impart an excellent antistatic effect to a synthetic resin and has excellent storage stability and productivity; an antistatic agent composition containing the same; an antistatic resin composition containing the antistatic agent or the antistatic agent composition; and a molded article thereof. BACKGROUND ART Synthetic resins such as thermoplastic resins are important materials that are indispensable today since they not only are lightweight and easy to process but also have excellent properties in that, for example, their base materials can be designed in accordance with the intended use. In addition, thermoplastic resins have excellent electrical insulation properties and are thus often utilized in the components of electric appliances and the like. However, there is a problem that thermoplastic resins are easily electrically charged by friction and the like because of their excessively high insulation performance. An electrically charged thermoplastic resin attracts dust and dirt in the surroundings and thus causes a problem of deteriorating the external appearance of its molded article. In addition, among electronic products, for example, in precision instruments such as computers, an electric charge may interfere with normal operation of a circuit. Moreover, there are also problems caused by an electric shock. An electric shock to a person from a resin not only causes discomfort but also potentially induces accidental explosion in the presence of a flammable gas or dust. In order to solve these problems, synthetic resins are conventionally subjected to an antistatic treatment. The most common antistatic treatment method is an addition of an antistatic agent to a synthetic resin of interest. Examples of the antistatic agent include coating-type antistatic agents that are coated on the surface of a resin molded article and kneading-type antistatic agents that are added when a resin is molded; however, the coating-type antistatic agents have poor persistence, and coating of a large amount of such an organic substance on a surface leads to a problem that objects coming into contact with the surface are contaminated. From these viewpoints, conventionally, polymer-type antistatic agents which are kneaded into synthetic resins for use have been mainly examined and, for example, Patent Documents 1 and 2 propose the use of a polyether ester amide for the purpose of imparting antistaticity to a polyolefin-based resin. Further, Patent Document 3 proposes a block polymer having a structure in which a polyolefin block and a hydrophilic polymer block are repeatedly and alternately bound with each other. Moreover, Patent Document 4 proposes a polymer-type antistatic agent containing a polyester block. RELATED ART DOCUMENTS Patent Documents [Patent Document 1] JPS58-118838A[Patent Document 2] JPH03-290464A[Patent Document 3] JP2001-278985A[Patent Document 4] JP2016-023254A SUMMARY OF THE INVENTION Problems to be Solved by the Invention However, these conventional antistatic agents are not necessarily said to have sufficient antistatic performance and, therefore, a further improvement is desired at present. In addition, conventional polymer-type antistatic agents have a problem in terms of storage stability in that, for example, they become sticky and cause blocking during long-term storage or storage under a high-temperature condition. Particularly, polymer-type antistatic agents are often used by cutting the polymers thereof obtained by polymerization into the form of pellets, and such polymer-type antistatic agents have a problem in terms of storage stability in that, for example, their pellets become sticky and cause blocking during long-term storage or storage under a high-temperature condition. Moreover, when the polymer-type antistatic agents are cut into the form of pellets, there is a problem that a defective cutting occurs and the productivity is thereby largely deteriorated since, for example, the resulting pellets have uneven and irregular shapes, some of the pellets remain in a state of being connected without being completely cut, the pellets have rough surfaces, and/or the pellets are observed with burrs and cracks. In view of the above, an object of the present invention is to provide: an antistatic agent which can continuously impart an excellent antistatic effect to a synthetic resin and has excellent storage stability and productivity (cutting property); an antistatic agent composition containing the same; an antistatic resin composition containing the antista