KR102211932B1 - Antistatic additive composition for silicone rubber and antistatic silicone rubber composition containing the same - Google Patents

Abstract

An antistatic additive composition for silicone rubber and an antistatic silicone rubber composition comprising the same are disclosed. The antistatic additive composition can impart an antistatic function to silicone rubber by being mixed with the silicone rubber, and has a particularly low surface resistance value. Therefore, a silicone rubber composition including the antistatic additive composition can be widely applied and put to practical use in various industrial fields. The antistatic additive composition for silicone rubber includes compounds represented by chemical formula 1, chemical formula 2 and chemical formula 3.

Description

Antistatic additive composition for silicone rubber, and antistatic silicone rubber composition comprising the same {ANTISTATIC ADDITIVE COMPOSITION FOR SILICONE RUBBER AND ANTISTATIC SILICONE RUBBER COMPOSITION CONTAINING THE SAME}

The present invention relates to an antistatic additive composition for silicone rubber and an antistatic silicone rubber composition comprising the same.

Silicone rubber is a special rubber that has heat and cold resistance properties, and if it is given antistatic properties, demand is expected to increase in the semiconductor and display industries. However, due to the inherent characteristics of silicone resins, mixing with inorganic carbon materials and metal oxides is required to impart antistatic performance, which causes restrictions on the color of the molded product, decreases physical properties, and increases production costs. The reality is that there are difficulties in commercialization. Therefore, there is an urgent need to develop a silicone polymer with an antistatic function capable of solving the above problems.

Accordingly, the inventors of the present invention are studying to introduce an antistatic function to the silicone rubber, and when a mixture of compounds represented by Formulas 1 and 2 is used as an antistatic additive composition, it has an excellent antistatic function, and a silicone containing the same The present invention was completed by finding that the rubber has a significantly low surface resistance value.

In this regard, Korean Patent Registration No. 10-1106087 discloses a method of manufacturing an antistatic masterbatch and a method of manufacturing an antistatic thermoplastic resin composition.

The present invention has been devised to solve the above-described problem, and an embodiment of the present invention provides an antistatic additive composition for silicone rubber.

In addition, another embodiment of the present invention provides an antistatic silicone rubber composition comprising the antistatic additive composition for silicone rubber.

In addition, another embodiment of the present invention provides a method of preparing the antistatic additive composition for silicone rubber.

The technical problem to be achieved by the present invention is not limited to the technical problems mentioned above, and other technical problems that are not mentioned can be clearly understood by those of ordinary skill in the technical field to which the present invention belongs from the following description. There will be.

As a technical means for achieving the above technical problem, one aspect of the present invention,

It provides an antistatic additive composition for silicone rubber comprising a compound represented by the following Chemical Formula 1 and Chemical Formula 2.

[Formula 1]

[Formula 2]

In Formula 2, R1 to R8 are each independently hydrogen, halogen, hydroxy group, amino group, straight or branched C1-C10 alkyl, straight or branched C1-C10 alkoxy, straight or branched C1-C10 Aminoalkyl, straight or branched C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl or C1-C20 alkylcarbonyl, wherein m and n are each independently an integer from 0 to 100.

In Formula 2, R1 to R8 are each independently hydrogen, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy, or a straight or branched C2-C10 alkenyl, and m and n are Each independently may be an integer of 0 to 100.

In Formula 2, R1 to R8 are each independently hydrogen, straight or branched C1-C4 alkyl, straight or branched C1-C4 alkoxy, or straight or branched C2-C4 alkenyl, and m and n are Each independently may be an integer of 0 to 100.

The content of the compound represented by Formula 2 may be 150 parts by weight to 400 parts by weight based on 100 parts by weight of the compound represented by Formula 1 above.

The antistatic additive composition for silicone rubber may further include a compound represented by Formula 3 below.

[Formula 3]

In Formula 3, R1 to R6 are each independently hydrogen, a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C1-C10 carboxyalkyl.

In Formula 3, R1 to R4 are each independently a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C1-C10 carboxyalkyl, and R5 And R6 may each be hydrogen.

The content of the compound represented by Formula 3 may range from 50 parts by weight to 200 parts by weight based on 100 parts by weight of the compound represented by Formula 1 and the compound represented by Formula 2.

The silicone rubber may include a material selected from the group consisting of liquid silicone rubber (LSR), heat cured rubber (HCR), and combinations thereof.

In addition, another aspect of the present invention,

It provides an antistatic silicone rubber composition comprising the silicone rubber antistatic additive composition and silicone rubber.

The content of the antistatic additive composition for silicone rubber may be 1 to 10 parts by weight based on 100 parts by weight of the silicone rubber.

In addition, another aspect of the present invention,

Melting the compounds represented by the following Chemical Formulas 1 and 2, respectively; Mixing and stirring the molten compounds represented by Formula 1 and Formula 2, respectively; And it provides a method for producing an antistatic additive composition for silicone rubber comprising; and cooling the stirred material.

[Formula 1]

[Formula 2]

In Formula 2, R1 to R8 are each independently hydrogen, halogen, hydroxy group, amino group, straight or branched C1-C10 alkyl, straight or branched C1-C10 alkoxy, straight or branched C1-C10 Aminoalkyl, straight or branched C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl or C1-C20 alkylcarbonyl, wherein m and n are each independently an integer from 0 to 100.

The manufacturing method of the antistatic additive composition for rubber,

Mixing and stirring the molten compounds represented by Formula 1 and Formula 2, respectively; Thereafter, mixing and stirring the compound represented by the following formula (3) with the agitated material may be further included.

[Formula 3]

In Formula 3, R1 to R6 are each independently hydrogen, a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C1-C10 carboxyalkyl.

According to an embodiment of the present invention, the antistatic additive composition can impart an antistatic function to the silicone rubber by mixing it with silicone rubber, and in particular, since it has a low surface resistance value, a silicone rubber composition including the same can be used in various industries. It can be applied widely in the field and put into practical use.

In addition, since the antistatic additive composition has an antistatic effect and can suppress the generation of static electricity, product defects can be significantly reduced if the composition is used when manufacturing a general molded article.

The effects of the present invention are not limited to the above effects, and should be understood to include all effects that can be inferred from the configuration of the invention described in the detailed description or claims of the present invention.

Hereinafter, the present invention will be described in more detail. However, the present invention may be implemented in various different forms, and the present invention is not limited by the embodiments described herein, and the present invention is only defined by the claims to be described later.

In addition, terms used in the present invention are used only to describe specific embodiments, and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In the entire specification of the present invention, "including" a certain component means that other components may be further included rather than excluding other components unless otherwise specified.

The first aspect of the present application,

It provides an antistatic additive composition for silicone rubber comprising a compound represented by the following Chemical Formula 1 and Chemical Formula 2.

[Formula 1]

[Formula 2]

In Chemical Formula 2,

R1 to R8 are each independently hydrogen, halogen, hydroxy group, amino group, straight or branched C1-C10 alkyl, straight or branched C1-C10 alkoxy, straight or branched C1-C10 amino alkyl, straight chain or Branched C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl or C1-C20 alkylcarbonyl,

The m and n are each independently an integer of 0 to 100.

Hereinafter, the antistatic additive composition for silicone rubber according to the first aspect of the present application will be described in detail.

In one embodiment of the present application, the additive may mean a raw material in the form of a pellet obtained by concentrating and dispersing a basic rubber or plastic raw material and an additive to be added to a high concentration. That is, a rubber or plastic product having a desired function may be manufactured by processing and molding a rubber or plastic raw material and the additive.

In one embodiment of the present application, preferably, in Formula 2, R1 to R8 are each independently hydrogen, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C2 -C10 alkenyl, m and n may each independently be an integer of 0 to 100.

In one embodiment of the present application, more preferably, R1 to R8 in Formula 2 are each independently hydrogen, a straight or branched C1-C4 alkyl, a straight or branched C1-C4 alkoxy or a straight or branched chain C2-C4 alkenyl, and m and n may each independently be an integer of 0 to 100.

The compound represented by Formula 2 according to an exemplary embodiment of the present disclosure may include a repeating unit of Si-O, and may preferably be polydimethylsiloxane (PDMS).

In one embodiment of the present application, the compound represented by Formula 1 may be added to the silicone as an ionic liquid to provide an antistatic function to the silicone rubber by contributing to ion jumping, and the compound represented by Formula 2 is It may have a function of more smoothly mixing the compound represented by Chemical Formula 1 and the silicone rubber.

In one embodiment of the present application, the content of the compound represented by Formula 2 may be 150 parts by weight to 400 parts by weight, and preferably 200 parts by weight to 300 parts by weight per 100 parts by weight of the compound represented by Formula 1 It may be, and more preferably 200 parts by weight to 250 parts by weight. If the content of the compound represented by Formula 2 relative to 100 parts by weight of the compound represented by Formula 1 is out of the above range, the physical properties of the silicone rubber may deteriorate when mixed with the silicone rubber, and migration may occur after molding. There may be a problem.

In one embodiment of the present application, the antistatic additive composition for silicone rubber may further include a compound represented by Formula 3 below.

[Formula 3]

In Formula 3, R1 to R6 are each independently hydrogen, a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C1-C10 carboxyalkyl.

In one embodiment of the present application, preferably, in Formula 3, R1 to R4 are each independently a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched chain Of C1-C10 carboxyalkyl, and R5 and R6 may each be hydrogen.

In one embodiment of the present application, more preferably, in Formula 3, R1, R2, and R4 may be linear or branched C1-C10 carboxyalkyl, and R3, R5 and R6 may each be hydrogen.

In one embodiment of the present application, a preferred example of the compound represented by Formula 3 is shown in Formula 4 below.

[Formula 4]

In one embodiment of the present application, the compound represented by Formula 3 may serve as a carrier by being included in the antistatic additive composition for silicone rubber, and specifically, the compound represented by Formulas 1 and 2 and the silicone rubber When mixed with, it may contribute to network formation. Meanwhile, the content of the compound represented by Formula 3 may be 50 parts by weight to 200 parts by weight based on 100 parts by weight of the compound represented by Formula 1 and the compound represented by Formula 2, preferably 50 parts by weight to It may be 150 parts by weight, more preferably 80 parts by weight to 120 parts by weight. When the content of the compound represented by Formula 3 is out of the above range with respect to the compound represented by Formula 1 and 100 parts by weight of the compound represented by Formula 2, the antistatic additive composition for silicone rubber and The network formation between the silicone rubbers may be poor.

In one embodiment of the present application, the silicone rubber includes a material selected from the group consisting of liquid silicone rubber (LSR), heat cured rubber (HCR), and combinations thereof. I can. That is, as will be described later in the second aspect of the present application, by mixing the silicone rubber antistatic additive composition with the silicone rubber, the silicone rubber may be given an antistatic function.

In one embodiment of the present application, the additive may further include a fluorine-based surfactant and an ionic salt represented by Formula 5 below.

[Formula 5]

_{(nC 4 H 9) 3 (} CH 3) N + (SO 2 CF 3) 2 N -

In one embodiment of the present application, the fluorine-based surfactant may include a perfluorobutane sulfonate group surfactant.

In one embodiment of the present application, 2-hydroxyethylammonium bis(trifluoromethylsulfonyl)imide, octyldimethyl-2-hydroxyethylammonium in place of or in addition to the ionic salt Trifluoromethanesulfonate, triethylammonium bis(perfluoroethanesulfonyl)imide, 1,3-ethylmethylimidazolium nonafluorobutanesulfonate, 1,3-ethylmethylimidazolium bis(tri A material selected from the group consisting of fluoromethanesulfonyl)imide, 1,3-ethylmethylimidazolium trifluoromethanesulfonate, and combinations thereof may be used.

In one embodiment of the present application, the ionic salt may be used as an additive (internal antistatic agent) or a local treatment agent (external antistatic agent) that imparts antistatic properties to a polymer or other insulating material, and the ionic salt is different It may have an effect of dissipating electrostatic charges that may accumulate in the insulating substrate (eg, a polymer film or a master batch, etc.).

In one embodiment of the present application, the antistatic additive composition may further include amorphous silica, and may further include an antioxidant or a coupling agent.

In one embodiment of the present application, the antistatic additive composition may further include a UV stabilizer to improve weather resistance when kneading the compounds. At this time, the content of the ultraviolet stabilizer may be 0.01 parts by weight to 1 part by weight relative to the total 100 parts by weight of the compound represented by Formulas 1 to 3, and if it is less than 0.01 parts by weight, weather resistance may be lowered and exceed 1 part by weight. In this case, the weather resistance improvement effect may not appear any more.

In one embodiment of the present application, the ultraviolet stabilizer is 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol (2-(2HBenzotriazol-2-yl)-4,6 -di-tert-pentylphenol}, 3-(2H-benzotriazol-2-yl)-4-hydroxyphenethyl-alcohol {3-2HBenzotriazol-2-yl)-4-hydroxyphenethyl-alcohol}, 2-( 2H-Benzotriazol-2-yl)-4- (1,1,3,3-tetramethylbutyl)phenol (2-(2H-Benzotriazol-2-yl)-4-(1,1,3,3 -tetramethylbutyl)phenol}, 2, 4-di-tert-butyl-6-(5-chlorobenzotriazol-2-yl)phenol {2,4-di-tert-butyl-6-(5-chlorobenzotriazol-2) -yl)phenol}, 2-(2H-benzotriazol-2-yl)-4-(tert-butyl)-6-(sec-butyl)phenol {2-(2Hbenzotriazol-2-yl)-4-( tert-butyl)-6-(sec-butyl)phenol}, 3-(3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate{3- (3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate}, 2-benzotriazol-2-yl-4,6-di-tert-butylphenol {2-benzotriazol -2-yl-4,6-di-tert-butylphenol} and combinations thereof may include a material selected from the group consisting of.

In one embodiment of the present application, the antistatic additive composition may further include a polyethylene glycol-based compound represented by Formula 6 below.

[Formula 6]

R ₉ O(CH ₂ CH ₂ ) _n OR ₉

In Formula 6, R9 is hydrogen or a methyl group, and n is an integer of 11 to 110.

In one embodiment of the present application, the polyethylene glycol-based compound may serve as an auxiliary dispersant, and the average molecular weight may be 500 to 5,000, and the content is based on 100 parts by weight of the total compound represented by Formulas 1 to 3 It may be 20 parts by weight compared to 10 parts by weight.

The second aspect of the present application,

It provides an antistatic silicone rubber composition comprising the silicone rubber antistatic additive composition and silicone rubber of the first aspect of the present application.

Detailed descriptions of portions overlapping with the first aspect of the present application have been omitted, but the description of the first aspect of the present application may be equally applied even if the description is omitted in the second aspect.

Hereinafter, the antistatic silicone rubber composition according to the second aspect of the present application will be described in detail.

In one embodiment of the present application, the antistatic additive composition for silicone rubber according to the first aspect of the present application may be used to prepare a silicone rubber composition having an antistatic function by mixing with silicone rubber. That is, the antistatic additive composition for silicone rubber is used for the same purpose as an additive in the silicone rubber composition, and the material used in the actual industry may be the silicone rubber composition. In this case, the silicone rubber may include a material selected from the group consisting of liquid silicone rubber (LSR), heat cured rubber (HCR), and combinations thereof. .

In one embodiment of the present application, the antistatic silicone rubber composition has an excellent antistatic function by including the additive composition, and thus may be widely applicable in various industrial fields.

In one embodiment of the present application, the content of the antistatic additive composition for silicone rubber may be 1 part by weight to 10 parts by weight based on 100 parts by weight of the silicone rubber, preferably 1 part by weight to 5 parts by weight, More preferably, it may be 4 parts by weight.

The third aspect of the present application,

Melting the compounds represented by the following Chemical Formulas 1 and 2, respectively;

Mixing and stirring the molten compounds represented by Formula 1 and Formula 2, respectively; And

Cooling the stirred material;

It provides a method for producing an antistatic additive composition for silicone rubber comprising a.

[Formula 1]

[Formula 2]

In Formula 2, R1 to R8 are each independently hydrogen, halogen, hydroxy group, amino group, straight or branched C1-C10 alkyl, straight or branched C1-C10 alkoxy, straight or branched C1-C10 Aminoalkyl, straight or branched C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl or C1-C20 alkylcarbonyl, wherein m and n are each independently an integer from 0 to 100.

Detailed descriptions of the portions overlapping with the first and second aspects of the present application have been omitted, but the descriptions of the first and second aspects of the present application may be equally applied even if the description is omitted in the third aspect. .

Hereinafter, a method of manufacturing the antistatic resin composition for silicone rubber according to the third aspect of the present application will be described in detail step by step.

First, in one embodiment of the present application, the method of preparing the antistatic additive composition for silicone rubber includes the steps of melting the compounds represented by Chemical Formulas 1 and 2, respectively.

In one embodiment of the present application, the melting may be applied to each of the compounds represented by Chemical Formulas 1 and 2, and the device for performing is not limited, but may be performed using, for example, an oven. have. In this case, the melting step may be performed at a temperature of about 30°C to 50°C for about 30 minutes to 2 hours.

Next, in one embodiment of the present application, the method of preparing the antistatic additive composition for silicone rubber includes the steps of mixing and stirring the molten compounds represented by Chemical Formulas 1 and 2, respectively.

In one embodiment of the present application, the stirring is not limited as long as it is a device capable of performing stirring, but may be performed through, for example, a stirrer, wherein the stirring speed of the stirrer is 30 rpm to 60 rpm It may be, and the stirring time may be performed for 1 minute to 20 minutes. On the other hand, the weight mixing ratio of the molten compounds represented by Formula 1 and Formula 2 is that 150 parts by weight to 400 parts by weight of the compound represented by Formula 2 are mixed with respect to 100 parts by weight of the compound represented by Formula 1 It may be, and preferably 200 parts by weight to 300 parts by weight may be mixed, and more preferably 200 parts by weight to 250 parts by weight may be mixed. If the weight mixing ratio of the compound represented by Formula 2 to 100 parts by weight of the compound represented by Formula 1 is out of the above range, the physical properties of the silicone rubber may be deteriorated when mixed with the silicone rubber, and migration after molding There may be a problem with this occurring.

In one embodiment of the present application, preferably, in Formula 2, R1 to R8 are each independently hydrogen, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C2 -C10 alkenyl, m and n may each independently be an integer of 0 to 100.

In one embodiment of the present application, more preferably, R1 to R8 in Formula 2 are each independently hydrogen, a straight or branched C1-C4 alkyl, a straight or branched C1-C4 alkoxy or a straight or branched chain C2-C4 alkenyl, and m and n may each independently be an integer of 0 to 100.

The compound represented by Formula 2 according to an exemplary embodiment of the present disclosure may include a repeating unit of Si-O, and may preferably be polydimethylsiloxane (PDMS).

Next, in one embodiment of the present application, the method of preparing the antistatic additive composition for silicone rubber may include mixing and stirring a compound represented by the following Formula 3 with the stirred material.

[Formula 3]

In Formula 3, R1 to R6 are each independently hydrogen, a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched C1-C10 carboxyalkyl.

In one embodiment of the present application, the compound represented by Chemical Formula 3 may be in the form of a powder, and the stirring is not limited as long as it is using a device capable of performing stirring, but, for example, a homogenizer mixer It may be performed through, in this case, the stirring speed of the mixer may be 500 rpm to 1,000 rpm, the stirring time may be performed for 1 minute to 10 minutes. On the other hand, the weight mixing ratio of the agitated material and the compound represented by Formula 3 may be mixing 50 parts by weight to 200 parts by weight of the compound represented by Formula 3 with respect to the total 100 parts by weight of the stirred material, Preferably 50 parts by weight to 150 parts by weight may be mixed, and more preferably 80 parts by weight to 120 parts by weight may be mixed. When the weight mixing ratio of the compound represented by Formula 3 is out of the above range with respect to the total 100 parts by weight of the agitated material, the formation of a network between the silicone rubber antistatic additive composition and the silicone rubber prepared when mixing with the silicone rubber later It may not work well.

In one embodiment of the present application, preferably, in Formula 3, R1 to R4 are each independently a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy or a straight or branched chain Of C1-C10 carboxyalkyl, and R5 and R6 may each be hydrogen.

In one embodiment of the present application, more preferably, in Formula 3, R1, R2, and R4 may be linear or branched C1-C10 carboxyalkyl, and R3, R5 and R6 may each be hydrogen.

In one embodiment of the present application, a preferred example of the compound represented by Formula 3 is shown in Formula 4 below.

Next, in one embodiment of the present application, the method for preparing the antistatic additive composition for silicone rubber includes cooling the stirred material. The cooling may be performed through natural cooling, and the cooled material may be packed at room temperature to obtain an antistatic additive composition for silicone rubber.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. However, the present invention may be implemented in various different forms and is not limited to the embodiments described herein.

<Example 1> Preparation of an antistatic silicone rubber composition containing an antistatic additive composition for silicone rubber (using liquid silicone rubber)

1. Preparation of antistatic additive composition for silicone rubber

The first compound (Bis (trifluoromethane) sulfonamide lithium salt compound) and the second compound (Methyl (propylhydroxy) bis (trimethyl silane) were each melted for 1 hour at a temperature of 30° C. to 50° C. using an oven. The first compound and the second compound were put into a stirrer at a weight mixing ratio of 3:7, and then stirred for 10 minutes at a stirring speed of 30 rpm to 60 rpm, and then, a powder in the form of a powder to the stirred material. After adding 3 compound (1,2,4-benzenetricarboxylic acid) at the same weight as the total weight of the first compound and the second compound, high-speed mixing for 5 minutes at a stirring speed of 500 rpm to 1,000 rpm using a homogenizer mixer The mixed material was naturally cooled and then packed at room temperature to prepare an antistatic additive composition for silicone rubber.

2. Preparation of antistatic silicone rubber composition

The antistatic additive composition prepared in 1 was mixed with liquid silicone rubber (LSR) in a weight ratio of 4:96 to prepare an antistatic silicone rubber composition.

<Example 2> Preparation of an antistatic silicone rubber composition containing an antistatic additive composition for silicone rubber (using a heat curing silicone rubber)

An antistatic silicone rubber composition was prepared in the same manner as in Example 1, except that a heat cured silicone rubber (HCR) was used instead of the liquid silicone rubber in Example 1.

<Comparative Example 1> Preparation of silicone rubber composition not containing antistatic additive composition (using liquid silicone rubber)

Commercially available liquid silicone rubber was purchased and prepared.

<Comparative Example 2> Preparation of a silicone rubber composition that does not contain an antistatic additive composition (using a heat curing silicone rubber)

Commercially available hot curing silicone rubber was purchased and prepared.

<Experimental Example 1> Measurement of surface resistance of antistatic resin composition

4 parts by weight of the antistatic silicone rubber composition prepared in Examples 1 and 2 and Comparative Examples 1 and 2 were added and compounded for each composition, and a 100 mm x 100 mm x 2 mm specimen was injection-molded, and then the surface resistance was measured. It is shown in Table 1 below.

[Table 1]

As shown in Table 1, it was confirmed that the silicone rubber compositions of Examples 1 and 2 exhibited a surface resistance of about 1.0E+9 to 1.0E+10, whereas the silicone rubber compositions of Comparative Examples 1 and 2 were about It was confirmed that it exhibited a surface resistance of 1.0E+15. That is, in the case of the silicone rubber composition including the antistatic additive composition for silicone rubber according to the embodiment of the present invention, it was confirmed that the antistatic function was excellent by showing very small surface resistance.

<Experimental Example 2> Evaluation of physical properties of the silicone rubber compositions of Examples 1 and 2 and the silicone rubber compositions of Comparative Examples 1 and 2

The properties of the antistatic silicone rubber composition prepared in Example 1 and the silicone rubber composition of Comparative Example 1 were evaluated and shown in Table 2 below, and the antistatic silicone rubber composition prepared in Example 2 and the silicone of Comparative Example 2 The physical properties of the rubber composition were evaluated and shown in Table 3 below.

[Table 2]

[Table 3]

As shown in Tables 2 and 3, the silicone rubber composition containing the antistatic additive composition for silicone rubber prepared in Examples 1 and 2 of the present invention was obtained from Comparative Examples 1 and 2 and the physical properties, respectively There was no significant difference. Therefore, it was confirmed that the silicone rubber composition including the antistatic additive composition for silicone rubber prepared in the embodiment of the present invention has an improved antistatic function without showing a significant difference in physical properties compared to the existing rubber composition.

Claims (12)

Antistatic additive composition for silicone rubber comprising a compound represented by the following Formula 1, Formula 2 and Formula 3:
[Formula 1]

[Formula 2]

(In Chemical Formula 2,
R1 to R8 are each independently hydrogen, halogen, hydroxy group, amino group, straight or branched C1-C10 alkyl, straight or branched C1-C10 alkoxy, straight or branched C1-C10 amino alkyl, straight chain or Branched C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl or C1-C20 alkylcarbonyl,
The m and n are each independently an integer of 0 to 100.)

[Formula 3]

(In Chemical Formula 3,
R1 to R6 are each independently hydrogen, a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy, or a straight or branched C1-C10 carboxyalkyl.)
The method of claim 1,
In Formula 2, R1 to R8 are each independently hydrogen, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy, or a straight or branched C2-C10 alkenyl, and m and n are Each independently an integer of 0 to 100, the antistatic additive composition for silicone rubber.
The method of claim 1,
In Formula 2, R1 to R8 are each independently hydrogen, straight or branched C1-C4 alkyl, straight or branched C1-C4 alkoxy, or straight or branched C2-C4 alkenyl, and m and n are Each independently an integer of 0 to 100, the antistatic additive composition for silicone rubber.
The method of claim 1,
The content of the compound represented by Formula 2 is 150 parts by weight to 400 parts by weight based on 100 parts by weight of the compound represented by Formula 1, wherein the antistatic additive composition for silicone rubber.
delete The method of claim 1,
In Formula 3, R1 to R4 are each independently a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy, or a straight or branched C1-C10 carboxyalkyl,
The antistatic additive composition for silicone rubber, wherein R5 and R6 are each hydrogen.
The method of claim 1,
The content of the compound represented by Formula 3 is 50 parts by weight to 200 parts by weight based on 100 parts by weight of the compound represented by Formula 1 and the compound represented by Formula 2.
The method of claim 1,
The silicone rubber is an antistatic additive composition for silicone rubber comprising a material selected from the group consisting of liquid silicone rubber (LSR), heat cured rubber (HCR), and combinations thereof .
An antistatic silicone rubber composition comprising the antistatic additive composition for silicone rubber of claim 1 and the silicone rubber.
The method of claim 9,
The content of the antistatic additive composition for silicone rubber is 1 to 10 parts by weight based on 100 parts by weight of the silicone rubber.
Melting the compounds represented by the following Formulas 1 and 2, respectively;
Mixing and stirring the molten compound represented by Formula 1 and Formula 2; mixing and stirring the compound represented by Formula 3 to the stirred material; And cooling the stirred material.
Method for producing an antistatic additive composition for silicone rubber comprising:
[Formula 1]

[Formula 2]

(In Chemical Formula 2,
R1 to R8 are each independently hydrogen, halogen, hydroxy group, amino group, straight or branched C1-C10 alkyl, straight or branched C1-C10 alkoxy, straight or branched C1-C10 amino alkyl, straight chain or Branched C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl or C1-C20 alkylcarbonyl,
The m and n are each independently an integer of 0 to 100.)
[Formula 3]

(In Chemical Formula 3,
R1 to R6 are each independently hydrogen, a hydroxy group, a straight or branched C1-C10 alkyl, a straight or branched C1-C10 alkoxy, or a straight or branched C1-C10 carboxyalkyl.)



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