JP5099922B2 - Antistatic agent for polycarbonate resin and polycarbonate resin composition containing the antistatic agent - Google Patents

Description

  The present invention relates to an antistatic agent for a polycarbonate resin, and particularly includes an antistatic agent for a polycarbonate resin that does not impair the transparency of the polycarbonate resin even when added, and also has excellent heat resistance, and the antistatic agent. The present invention relates to a polycarbonate resin composition.

  Polycarbonate resins are excellent in heat resistance, moldability, mechanical properties, etc., and are widely used as electrical / electronic members, medical members, optical members, and other various molded products. Like other plastics, polycarbonate is characterized by high electrical insulation. On the other hand, it is difficult to dissipate static electricity once charged. There is a drawback that problems such as malfunction of instruments and IC chips occur. So far, effective antistatic agents have been developed for various plastics including polycarbonate.

  In general, there are kneading types and coating types of antistatic agents, but coating type antistatic agents are coated with a large amount of organic matter on the upper surface, which is inferior in durability, and those that touch the coated surface are contaminated. There was a problem. Therefore, conventionally, a kneading type antistatic agent has been mainly studied (for example, Patent Documents 1 and 2).

However, when these conventional kneading-type antistatic agents are added to the polycarbonate resin, there is a problem that the transparency of the resin is lowered. Polycarbonate resins are highly transparent, and many products make use of the transparency. Therefore, the product value decreases when the transparency decreases. In addition, since the polycarbonate resin has a high melting point, the antistatic agent is decomposed by heat in the step of molding by applying heat.
In order to solve the above disadvantages, an antistatic agent having excellent heat resistance has been proposed (Patent Document 3), but in order to obtain an effect that can satisfy the decrease in transparency when used in a polycarbonate resin. Not reached.

JP 7-292234 A JP 2002-60734 A JP 2008-174631 A

Therefore, the first object of the present invention is not only to reduce the transparency of the resin even when added to the polycarbonate resin, but also to have a heat resistance that can withstand the processing temperature of the polycarbonate resin, and has an excellent antistatic property. An object of the present invention is to provide an antistatic agent for polycarbonate resin which can impart performance.
The second object of the present invention is to provide a polycarbonate resin composition capable of obtaining a transparent polycarbonate resin product excellent in sustainability of antistatic performance.

  As a result of intensive studies to achieve the above-mentioned objects, the present inventors have found that a specific compound having an ester bond of a phenolic hydroxyl group and a carboxyl group as an essential bond can be added to a polycarbonate resin even if the resin is transparent. In addition to not lowering the properties, it has been found that it has good heat resistance and is suitable as an antistatic agent for polycarbonate resins, and has completed the present invention.

上記一般式（１）中のＲは、炭素原子数１〜１８の直鎖または分岐のアルキル基；炭素原子数３〜８のシクロアルキル基；炭素原子数３〜８のアルケニル基；炭素原子数６〜３０のアリール基；炭素原子数７〜３０のアリールアルキル基；又は炭素原子数７〜３０のアルキルアリール基を表す。但し、ヒドロキシ基、ハロゲン原子、シアノ基、ニトロ基、炭素原子数１〜１８のアルキル基又はアルコキシ基で置換されていてもよい。更にこれらの基は、酸素原子、硫黄原子、カルボニル基、エステル基、アミド基またはイミノ基で中断されていてもよく、これらの置換及び中断は組み合わされていてもよい。Ｍはアルカリ金属イオンまたはアルカリ土類金属イオンを表し、ｎは１又は２の数を表す。
また本発明のポリカーボネート樹脂組成物は、本発明のポリカーボネート樹脂用帯電防止剤を０．０１〜２０質量％含有するものである。 That is, the present invention is an antistatic agent for polycarbonate resin represented by the following general formula (1) represented by [Chemical Formula 1], and a polycarbonate resin composition containing the antistatic agent.

R in the general formula (1) is a linear or branched alkyl group having 1 to 18 carbon atoms; a cycloalkyl group having 3 to 8 carbon atoms; an alkenyl group having 3 to 8 carbon atoms; Represents an aryl group having 6 to 30 carbon atoms; an arylalkyl group having 7 to 30 carbon atoms; or an alkylaryl group having 7 to 30 carbon atoms. However, it may be substituted with a hydroxy group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group. Further, these groups may be interrupted by an oxygen atom, a sulfur atom, a carbonyl group, an ester group, an amide group or an imino group, and these substitutions and interruptions may be combined. M represents an alkali metal ion or an alkaline earth metal ion, and n represents a number of 1 or 2.
Moreover, the polycarbonate resin composition of this invention contains 0.01-20 mass% of antistatic agents for polycarbonate resins of this invention.

  The antistatic agent of the present invention not only lowers the transparency of the resin even when added to the polycarbonate resin, but also has heat resistance that can withstand molding, so the polycarbonate resin product has excellent antistatic performance with excellent durability. Can be granted.

上記一般式（１）中のＲは、炭素原子数１〜１８の直鎖又は分岐のアルキル基；炭素原子数３〜８のシクロアルキル基；炭素原子数３〜８のアルケニル基；炭素原子数６〜３０のアリール基；炭素原子数７〜３０のアリールアルキル基；又は炭素原子数７〜３０のアルキルアリール基を表す。但し、これらの基は、ヒドロキシ基、ハロゲン原子、シアノ基、ニトロ基、炭素原子数１〜１８のアルキル基またはアルコキシ基で置換されていてもよい。これらの基は更に、酸素原子、硫黄原子、カルボニル基、エステル基、アミド基又はイミノ基で中断されていてもよく、これらの置換及び中断は組み合わされていてもよい。Ｍはアルカリ金属イオン又はアルカリ土類金属イオンを表し、ｎは１又は２の数を表す。 The antistatic agent of the present invention is represented by the following general formula (1) shown in [Chemical Formula 1].

R in the general formula (1) is a linear or branched alkyl group having 1 to 18 carbon atoms; a cycloalkyl group having 3 to 8 carbon atoms; an alkenyl group having 3 to 8 carbon atoms; Represents an aryl group having 6 to 30 carbon atoms; an arylalkyl group having 7 to 30 carbon atoms; or an alkylaryl group having 7 to 30 carbon atoms. However, these groups may be substituted with a hydroxy group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group. These groups may be further interrupted by oxygen atoms, sulfur atoms, carbonyl groups, ester groups, amide groups or imino groups, and these substitutions and interruptions may be combined. M represents an alkali metal ion or an alkaline earth metal ion, and n represents a number of 1 or 2.

  Examples of the linear or branched alkyl group having 1 to 18 carbon atoms represented by R in the general formula (1) include methyl, ethyl, propyl, isopropyl, butyl, secondary butyl, and tertiary butyl. , Isobutyl, amyl, isoamyl, tertiary amyl, hexyl, heptyl, 2-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl, dodecyl , Tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, etc., and those having substitution or interruption include chloromethyl, dichloromethyl, trichloromethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl 2-methoxyethyl, 2-e Xylethyl, 2-butoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2,3-dihydroxypropyl, 2-hydroxy-3-methoxypropyl, 2,3-dimethoxypropyl, 2- (2-methoxyethoxy) ethyl, etc. Is mentioned.

  Examples of the cycloalkyl group having 3 to 8 carbon atoms represented by R in the general formula (1) include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like. Examples of the alkenyl group include linear and branched propenyl, butenyl, pentenyl, hexenyl, heptenyl and octenyl. In this case, the position of the unsaturated bond is not particularly limited.

  Examples of the aryl group having 6 to 18 carbon atoms or the alkylaryl group having 7 to 18 carbon atoms represented by R in the general formula (1) include phenyl, naphthyl, 2-methylphenyl, and 3-methylphenyl. 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tertiarybutylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4 -Octylphenyl, 4- (2-ethylhexyl) phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3, 5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl Nyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, biphenyl, 2 , 4,5-trimethylphenyl and the like.

  Examples of the arylalkyl group having 7 to 18 carbon atoms represented by R in the general formula (1) include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl and the like.

  When n in the general formula (1) is 2, R may be the same or different. In the present invention, from the viewpoint of heat resistance of the antistatic agent and transparency of the polycarbonate product, R in the general formula (1) is preferably an aryl group or an alkylaryl group, and particularly preferably an alkylaryl group. .

M in the general formula (1) is an alkali metal ion or an alkaline earth metal ion, and two or more of them may be used in the present invention. Examples of M include alkali metal ions such as lithium, sodium and potassium; alkaline earth metal ions such as magnesium, calcium, strontium and barium.
In the present invention, among these counter ions, alkali metal ions are preferable from the viewpoint of antistatic effect and heat resistance, and potassium ions are more preferable from the viewpoint of transparency.

  Specific examples of the antistatic agent represented by the general formula (1) of the present invention include the following compound Nos. Shown in [Chemical Formula 2] to [Chemical Formula 13]. 1-No. Although 12 compounds are mentioned, this invention is not limited to these compounds.

一般式（２）中のＭはカチオン性の対イオンを表し、ｎは１又は２の数を表す。

一般式（３）中のＲは、炭素原子数１〜１８の直鎖又は分岐のアルキル基；炭素原子数３〜８のシクロアルキル基；炭素原子数３〜８のアルケニル基；炭素原子数６〜３０のアリール基；炭素原子数７〜３０のアリールアルキル基；又は炭素原子数７〜３０のアルキルアリール基を表す。但し、これらの基は、ヒドロキシ基、ハロゲン原子、シアノ基、ニトロ基、炭素原子数１〜１８のアルキル基又はアルコキシ基で置換されていてもよい。これらの基は更に、酸素原子、硫黄原子、カルボニル基、エステル基、アミド基又はイミノ基で中断されていてもよく、これらの置換及び中断は組み合わされていてもよい。 The antistatic agent of the present invention can be appropriately produced by a known method, and is produced by reacting the compounds represented by the following general formulas (2) and (3) represented by [Chemical Formula 14] and [Chemical Formula 15]. It is preferable to do.

M in the general formula (2) represents a cationic counter ion, and n represents a number of 1 or 2.

R in the general formula (3) is a linear or branched alkyl group having 1 to 18 carbon atoms; a cycloalkyl group having 3 to 8 carbon atoms; an alkenyl group having 3 to 8 carbon atoms; Represents an aryl group having -30 atoms; an arylalkyl group having 7-30 carbon atoms; or an alkylaryl group having 7-30 carbon atoms. However, these groups may be substituted with a hydroxy group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group. These groups may be further interrupted by oxygen atoms, sulfur atoms, carbonyl groups, ester groups, amide groups or imino groups, and these substitutions and interruptions may be combined.

  Specific examples of the compound represented by the general formula (2) include 4-sulfobenzene-1,2-dicarboxylic acid, 4-sulfobenzene-1,3-dicarboxylic acid, 2-sulfobenzene-1, Carboxylic acid compounds such as 4-dicarboxylic acid, 3-sulfobenzene-1,2-dicarboxylic acid, 5-sulfobenzene-1,3-dicarboxylic acid, 2-sulfobenzoic acid and 4-sulfobenzoic acid are derived from the above M. And a salt neutralized with a basic compound.

  Moreover, as a specific compound represented by the said General formula (3), various ester compounds of salicylic acid are mentioned, for example. The antistatic agent of the present invention can be obtained by reacting the carboxyl group of the compound represented by the general formula (2) with the hydroxyl group of the compound represented by the general formula (3).

  The reaction ratio of the compound of the general formula (2) and the compound of the general formula (3) is such that the hydroxyl group of the latter compound is 0.5 to 2.0 equivalents relative to the former carboxyl group. What is necessary is just to make it react, It is more preferable to make it react by the ratio which becomes 0.95-1.05 equivalent, It is most preferable to make it react so that the said carboxyl group and a hydroxyl group may become equivalent.

  As a specific reaction method, a known esterification reaction can be appropriately used. For example, it can be obtained by adding a catalyst to the compound of the above general formula (2) and the compound of (3) and dehydrating at 100 to 350 ° C. for about 5 to 30 hours. Examples of the catalyst include strong acids such as sulfuric acid and toluene sulfonic acid; metals such as titanium tetrachloride, hafnium chloride, zirconium chloride, aluminum chloride, gallium chloride, indium chloride, iron chloride, tin chloride, and boron fluoride. Halides; hydroxides of alkali metals and alkaline earth metals such as sodium hydroxide, potassium hydroxide, sodium methylate, sodium carbonate; alcoholates; carbonates; aluminum oxide, calcium oxide, barium oxide, sodium oxide, etc. And metal oxides such as tetraisopropyl titanate, dibutyltin dichloride, and dibutyltin oxide. Among these, it is preferable to use an alkali metal or alkaline earth metal hydroxide or an organic metal compound because of its good reactivity. Moreover, it is preferable that the addition amount of a catalyst is 0.1-5 mass% with respect to the reactant whole quantity, and it is more preferable that it is 0.2-3 mass%.

  However, since these esterification reactions are carried out at a high temperature, there is a problem that the compound after the reaction is colored, and a problem that the reaction rate is lowered because the compound of the general formula (3) has a phenolic hydroxyl group. . That is, it is difficult to react a phenolic hydroxyl group with a carboxyl group unlike an alcoholic hydroxyl group. Therefore, it is preferable to carry out the reaction using an activator instead of the catalyst as described above.

  The reaction method using an activator is, for example, dissolving an activator and an organic base in a solvent, then adding the compound of general formula (2) and stirring uniformly, and then converting the compound of general formula (3) into In addition, it can carry out by making it react at 60-120 degreeC for 3 to 10 hours.

  Examples of the activator include phosphite-pyridine activator, triphenylphosphine-hexachloromethane activator, pentavalent phosphate derivative activator, thionyl chloride, phosphorus pentoxide, allylsulfonyl chloride. -Dimethylformamide (DMF) activator, diphenyl chlorophosphate-DMF activator, and triphenylphosphine dichloride. In the present invention, from the viewpoint of reactivity, it is preferable to use allylsulfonyl chloride-DMF activator, diphenyl chlorophosphate-DMF activator, and triphenylphosphine dichloride among them. The amount of the activator added is preferably 0.1 to 5 mol, particularly 0.5 to 3 mol, per 1 mol of the compound of the general formula (2). More preferred.

  Examples of the organic base include piperidine, pyridine, α-picoline, β-picoline, γ-picoline, 2,4-lutidine, 2,6-lutidine, quinoline, isoquinoline, 4-dimethylaminopyridine, 4,4 ′. -Bipyridine, diethylamine, triethylamine, aniline, tributylamine, dimethylaniline, diethylaniline, N-methylmorpholine and the like. Among these, pyridine and β-picoline are preferable because of good yield. The amount of the organic base added is preferably 10 to 500% by mass and more preferably 50 to 300% by mass with respect to the compound of the general formula (1).

  In the reaction method using the activator, it is not necessary to use a solvent, but the reaction is preferably carried out in a solvent from the viewpoint of improving the yield and shortening the reaction time. Examples of the solvent used in this case include octane, cyclohexanone, N-methylformamide, N, N-dimethylacetamide, DMF, N-methyl-2-pyrrolidone, acetonitrile, propylnitrile, benzonitrile, nitromethane, nitrobenzene, and pyridine. Morpholine, dimethyl sulfoxide, toluene, xylene, acetone, chloroform, chlorobenzene, dichlorobenzene, nitrobenzene and the like. Among these, pyridine is preferable because the treatment after the reaction is easy. The addition amount of the solvent is preferably 10 to 500% by mass, and particularly preferably 50 to 300% by mass with respect to the total amount of the reactants.

  The antistatic agent for polycarbonate resin of the present invention is characterized by not only excellent transparency when blended with polycarbonate resin but also excellent heat resistance. In general, the closer the refractive index of the antistatic agent is to the refractive index of the polycarbonate resin, the better the transparency. However, the antistatic agent having a substituent such as an alkyl group or an alkenyl group is better than the polycarbonate resin. The refractive index is lowered. On the other hand, an antistatic agent having an aryl group such as a benzene ring exhibits a refractive index equivalent to or higher than that of a polycarbonate resin. Therefore, in order to make the refractive index close to that of the polycarbonate resin, it is necessary to consider the ratio of alkyl groups and benzene rings in the antistatic agent.

  On the other hand, with respect to heat resistance, the proportion of contributions by substituents and bonds is large. An antistatic agent having a substituent such as an alkyl group or an alkenyl group has poor heat resistance, and an antistatic agent having an aryl group such as a benzene ring has good heat resistance. In particular, the heat resistance of an antistatic agent having an alkenyl group having a double bond is poor. Regarding the bond, an antistatic agent having an ester bond or an amide bond exhibits good heat resistance, but when these bonds are present, it does not always have sufficient heat resistance. Among these, the antistatic agent having an ester bond formed by a reaction between a phenolic hydroxyl group and a carboxyl group is excellent in heat resistance, and the antistatic agent having an ester bond formed by a reaction between an alcoholic hydroxyl group and a carboxyl group. In this case, the heat resistance is insufficient. For these reasons, it is essential for the antistatic agent of the present invention to have an ester bond between a phenolic hydroxyl group and a carboxyl group. In the present invention, an antistatic agent having two ester bonds of a phenolic hydroxyl group and a carboxyl group in its structure is particularly preferable.

  The antistatic agent for polycarbonate resin of the present invention can be added to the polycarbonate resin as it is, but it may be added after impregnating the carrier if necessary. When the antistatic agent for polycarbonate resin of the present invention is liquid at room temperature, it is particularly preferable to use it by impregnating the carrier. If it is added as a liquid, it may be difficult to uniformly mix it in the polycarbonate resin.

  In order to impregnate the carrier with the antistatic agent for polycarbonate resin of the present invention, the carrier and the liquid antistatic agent may be heated and mixed as they are, or if necessary, diluted with an organic solvent and then impregnated into the carrier. Thereafter, the solvent may be removed. As such a carrier, a carrier known as a synthetic resin filler or filler, or a flame retardant or light stabilizer that is solid at room temperature can be used. Specific examples of these substances that can be used as carriers (hereinafter simply referred to as carriers) include, for example, calcium silicate powder, silica powder, talc powder, alumina powder, titanium oxide powder, or chemically modified surfaces of these carriers. And those that are solid at room temperature among the flame retardants and antioxidants described below. Among these carriers, those in which the surface of the carrier is chemically modified are preferable in the present invention, and those in which the surface of the silica powder is chemically modified are particularly preferable. These carriers preferably have an average particle size of 0.1 to 100 μm, particularly preferably 0.5 to 50 μm.

  The polycarbonate resin composition of the present invention is obtained by adding and blending the antistatic agent of the present invention to a polycarbonate resin. The polycarbonate resin here includes not only a resin containing 100% polycarbonate but also a so-called polymer alloy obtained by mixing polycarbonate and another resin. Examples of such polymer alloys include polycarbonate / ABS resin, polycarbonate / AS resin, polycarbonate / rubber polymer compound, polycarbonate / ABS resin / rubber polymer compound, polycarbonate / polyethylene terephthalate, polycarbonate / polybutylene terephthalate, Examples include polycarbonate / ASA resin and polycarbonate / AES resin. The ratio of the polycarbonate contained in these polymer alloys is preferably 50 to 98% by mass in the polymer alloy.

  The polycarbonate that can be used in the present invention (the above-mentioned polycarbonate 100% resin) may be a commercially available product, for example, one obtained by reacting one or more bisphenols with phosgene or a carbonic acid diester, or One or more bisphenols and diphenyl carbonates are reacted by a transesterification method. Furthermore, the viscosity average molecular weight of these polycarbonates is preferably 10,000 to 100,000, and more preferably 10,000 to 50,000.

  Examples of the bisphenols include hydroquinone, 4,4-dihydroxyphenyl, bis- (4-hydroxyphenyl) -alkane, bis- (4-hydroxyphenyl) -cycloalkane, and bis- (4-hydroxyphenyl)- Sulfide, bis- (4-hydroxyphenyl) -ether, bis- (4-hydroxyphenyl) -ketone, bis- (4-hydroxyphenyl) -sulfone, bisphenolfluorene, or an alkyl or aryl substituent thereof, Examples include halogen substitution products. These bisphenols may be used alone or in combination of two or more.

  As the polycarbonate used in the present invention, a bisphenol A-based polycarbonate using 2,2-bis- (4-hydroxyphenyl) propane (so-called bisphenol A) as a raw material is particularly preferable because it can be easily obtained in the market.

  The amount of the antistatic agent of the present invention to be blended in the polycarbonate resin composition of the present invention is not particularly limited, but is 0.01 to 20% by mass with respect to the total amount of the polycarbonate resin and the antistatic agent. It is preferable to blend in. A more preferable amount is 0.05 to 15% by mass, and a most preferable amount is 1 to 10% by mass. When it mix | blends in large quantities exceeding 20 mass%, physical properties, such as mechanical strength of polycarbonate resin, may fall, or it may become difficult to mix | blend itself. On the other hand, if the blending amount is less than 0.01% by mass, the antistatic effect becomes insufficient, which is not preferable.

  The blending method when blending the antistatic agent to the polycarbonate resin composition of the present invention is not particularly limited, and any commonly used method such as roll kneading, bumper kneading, an extruder, a kneader or the like can be used. It can be used by mixing and kneading.

  The antistatic agent of the present invention can also be used as a coating mold applied to the surface of a polycarbonate resin molded product, in addition to the use as a so-called kneading mold that is kneaded into the polycarbonate resin as described above. In this case, the antistatic agent of the present invention may be dissolved in various solvents and applied as a solution.

  The polycarbonate resin composition of the present invention preferably contains a flame retardant from the viewpoint of improving the physical properties of the polycarbonate resin composition. Examples of the flame retardant that can be used here include tetrabromobisphenol A, hexabromobenzene, tris (2,3-dibromopropyl) isocyanurate, and 2,2-bis (4-hydroxyethoxy-3,5- Halogen flame retardants such as dibromophenyl) propane, decabromodiphenyl oxide, hexabromocyclodecane, tetrabromophthalic anhydride, chlorinated polyethylene, chlorinated paraffin, perchlorocyclopentadecane, chlorendic acid, tetrachlorophthalic anhydride; phosphoric acid Ammonium, tricresyl phosphate, triethyl phosphate, tris (β-chloroethyl) phosphate, trischloroethyl phosphate, trisdichloropropyl phosphate, cresyl diphenyl phosphate, xyl Nyldiphenyl phosphate, phenylene bis (diphenyl phosphate), phenylene bis (phenyl cresyl phosphate), phenylene bis (dicresyl phosphate), phenylene bis (dixylenyl phosphate), bisphenol A bis (diphenyl phosphate) Phosphorus flame retardants such as bisphenol A bis (dicresyl phosphate); red phosphorus, tin oxide, antimony trioxide, zirconium hydroxide, barium metaborate, zinc borate, aluminum hydroxide, magnesium hydroxide, nitrogenated guanidine And inorganic flame retardants.

上記一般式（４）中、Ｒ^１〜Ｒ^４はアリール基を表し、Ｙはアリーレン基を表し、ａ〜ｄは０又は１の数を表し、ｓは１〜５の数を表す。 Among these flame retardants, when blending halogen-containing flame retardants such as halogen-based flame retardants and halogen-containing phosphorus-based flame retardants, dioxins may be generated during combustion. Flame retardants containing halogens tend to be avoided. Further, some flame retardants may cause the synthetic resin to be colored by heat or the heat resistance to be lowered depending on the synthetic resin base material when used in combination with the antistatic composition of the present invention. Therefore, in the present invention, it is preferable to use a phosphorus compound represented by the following general formula (4) represented by [Chemical Formula 16] as a flame retardant having no such fear.

In said general formula (4), R < ¹ > -R < ⁴ > represents an aryl group, Y represents an arylene group, ad represents the number of 0 or 1, s represents the number of 1-5.

R ^{1 to} R ⁴ in the general formula (4) represent an aryl group, and they may be the same or different. Examples of the aryl group include a phenyl group, a tolyl group, a benzyl group, a xylyl group, a phenethyl group, a styryl group, a trimethylphenyl group, a cumenyl group, a cumyl group, a hydrocinnamyl group, a cinnamyl group, a tetramethylphenyl group, and a thymyl group. , Carbacrylyl group, cuminyl group, neophyll group, xenyl group, benzhydryl group, triphenylmethyl group, ethylphenyl group, propylphenyl group, butylphenyl group, pentylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonyl A phenyl group, a decylphenyl group, an undecylphenyl group, a dodecylphenyl group, a naphthyl group, etc. are mentioned. In the present invention, among these, a phenyl group, a cresyl group, and a xylenyl group are preferable.

  Y in the general formula (4) represents an arylene group which is a residue obtained by removing a hydroxyl group from a divalent phenol. Examples of the divalent phenols include resorcin, catechol, hydroquinone, bisphenol A, bisphenol F, bisphenol S, and biphenol. A to d represent the numbers 0 or 1 and may be the same or different. s is an average value of repeating units and represents a number of 1 to 5.

  The phosphorus compound represented by the general formula (4) can be produced by a known method (for example, JP-A-59-202240). Specific examples of these phosphorus compounds include, for example, phenylene bis (diphenyl phosphate), phenylene bis (phenyl cresyl phosphate), phenylene bis (dicresyl phosphate), phenylene bis (dixylenyl phosphate), Examples thereof include bisphenol A bis (diphenyl phosphate) and bisphenol A bis (dicresyl phosphate).

  The blending amount of the flame retardant in the present invention can be appropriately set depending on the type and use of the polycarbonate resin, but is preferably 0.5 to 30% by mass of the polycarbonate resin substrate, and 1 to 25% by mass. The equivalent amount is more preferable, and the equivalent amount of 5 to 20% by mass is most preferable.

  The polycarbonate resin composition of the present invention is a known antioxidant, light stabilizer, ultraviolet absorber, fluoroolefin resin, other antistatic agent, antifogging agent, lubricant, plasticizer, as long as the effects of the present invention are not hindered. Agent, colorant, non-phosphorous flame retardant, flame retardant aid, antifungal agent, crystal nucleating agent, compatibilizer, anti-blocking agent, foaming agent, inorganic electrolyte, filler, filler, pigment, fragrance, silicone oil, You may contain other synthetic resin additives, such as a coupling agent. Furthermore, you may contain electroconductive substances, such as carbon fiber and stainless steel fiber. In the present invention, among these, it is preferable to contain an antioxidant, a fluoroolefin resin or a lubricant.

  Antioxidants that can be used in the present invention include phenolic antioxidants, phosphorus antioxidants, and sulfur antioxidants. Examples of the phenol-based antioxidant include 2,6-di-tert. -Butylphenol (hereinafter, tert.-butyl is abbreviated as t-butyl), 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol, 2, 4-dimethyl-6-tert-butylphenol, 4,4′-methylenebis (2,6-di-tert-butylphenol), 4,4′-bis (2,6-di-tert-butylphenol), 4,4 ′ -Bis (2-methyl-6-tert-butylphenol), 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2,2'-methylenebis (4-ethyl-6-tert-butylphenol), 4,4′-butylidenebis (3-methyl-6-tert-butylphenol), 4,4′-isopropylidenebis (2,6-di-tert-butylphenol), 2,2′-methylenebis (4-methyl-6) − Chlorylphenol), 2,2'-methylenebis (4-methyl-6-nonylphenol), 2,2'-isobutylidenebis (4,6-dimethylphenol), 2,6-bis (2'-hydroxy-) 3'-t-butyl-5'-methylbenzyl) 4-methylphenol, 3-t-butyl-4-hydroxyanisole, 2-t-butyl-4-hydroxyanisole, 3- (4-hydroxy-3,5 -Di-t-butylphenyl) stearyl propionate, 3- (4-hydroxy-3,5-di-t-butylphenyl) oleyl propionate, 3- (4-hydroxy-3,5-di-t-butyl) Phenyl) dodecyl propionate, octyl 3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrakis {3- (4-hydroxy-3,5- -T-butylphenyl) propionyloxymethyl} methane, 3- (4-hydroxy-3,5-di-t-butylphenyl) propionic acid glycerin monoester, 3- (4-hydroxy-3,5-di-t -Butylphenyl) propionic acid and glycerol monooleyl ether, 3- (4-hydroxy-3,5-di-t-butylphenyl) propionic acid butylene glycol ester, 3- (4-hydroxy-3,5- Di-t-butylphenyl) propionic acid thiodiglycol ester, 4,4′-thiobis (3-methyl-6-tert-butylphenol), 4,4′-thiobis (2-methyl-6-tert-butylphenol), 2,2′-thiobis (4-methyl-6-tert-butylphenol), 2,6-di-tert-butyl-α-dimethylamino- -Cresol, 2,6-di-t-butyl-4 (N, N'-dimethylaminomethylphenol), bis (3,5-di-t-butyl-4-hydroxybenzyl) sulfide, tris {(3, 5-di-t-butyl-4-hydroxyphenyl) propionyl-oxyethyl} isocyanurate, tris (3,5-di-t-butyl-4-hydroxyphenyl) isocyanurate, 1,3,5-tris (3 ′ , 5′-di-tert-butyl-4-hydroxybenzoyl) isocyanurate, bis {2-methyl-4- (3-n-alkylthiopropionyloxy) -5-tert-butylphenyl} sulfide, 1,3,5 -Tris (4-di-t-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, tetraphthaloyl-di (2,6-dimethyl) 4-t-butyl-3-hydroxybenzyl sulfide), 6- (4-hydroxy-3,5-di-t-butylanilino) -2,4-bis (octylthio) -1,3,5-triazine, 2, 2-thio- {diethyl-bis-3- (3,5-di-t-butyl-4-hydroxyphenyl)} propionate, N, N'-hexamethylenebis (3,5-di-t-butyl-4 -Hydroxy-hydrocinnamide), 3,5-di-tert-butyl-4-hydroxy-benzyl-phosphate diester, bis (3-methyl-4-hydroxy-5-tert-butylbenzyl) sulfide, 3,9-bis [1,1-dimethyl-2- {β- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy} ethyl] -2,4,8,10-tetraoxaspiro [5,5] Undecane, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t -Butyl-4-hydroxybenzyl) benzene, bis {3,3′-bis- (4′-hydroxy-3′-t-butylphenyl) butyric acid} glycol ester, and the like.

  Examples of the phosphorus antioxidant include triphenyl phosphite, diphenylisodecyl phosphite, phenyl diisodecyl phosphite, 4,4-butylidenebis (3-methyl-6-t-butylphenyldiisotridecyl) phosphite, Distearyl pentaerythritol diphosphite, diisodecyl pentaerythritol diphosphite, tris (nonylphenyl) phosphite, tris (dinonylphenyl) phosphite, tris (2,4-di-t-butylphenyl) phosphite, bis ( 2,6-di-t-butyl-4-methylphenyl) pentaerythritol phosphite, 2,2-methylenebis (4,6-di-t-butylphenyl) octyl phosphite, 1,1,3-butyridine tris (3-Methyl-6-t-butyl Enyldiisotridecyl) phosphite, 2,2-propylidenebis (3-methyl-6-tert-butylphenyldiisotridecyl) phosphite, tetrakis (2,4-di-tert-butylphenyl) -4,4-biphenylene -Diphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (3,5-di-t-butyl-4-hydroxybenzyl) -9,10-dihydro-9- And oxa-10-phosphaphenanthrene-10-oxide, 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene, and the like.

  Examples of the sulfur-based antioxidant include dioctyl thiodipropionate, didecyl thiodipropionate, dilauryl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, lauryl stearyl thiodipropionate. , Distearyl-β, β'-thiodibutyrate, (3-octylthiopropionic acid) pentaerythritol tetraester, (3-decylthiopropionic acid) pentaerythritol tetraester, (3-laurylthiopropionic acid) pentaerythritol Tetraester, (3-stearylthiopropionic acid) pentaerythritol tetraester, (3-oleylthiopropionic acid) pentaerythritol tetraester, (3-laurylthiopropionic acid) -4,4'-thio Di (3-methyl -5-t-butyl-4-phenol) ester, 2-mercaptobenzimidazole, 2-mercaptomethyl benzimidazole, 2-benzimidazole disulfide, dilauryl sulfide, Ami Lucio glycol.

  Although the compounding quantity of these antioxidants used by this invention can be suitably set with the kind and use of the polycarbonate resin used as a base material, it is 0.001-15 mass% equivalent amount of a polycarbonate resin base material. It is preferably 0.005 to 10% by mass, and most preferably 0.01 to 5% by mass.

  The polycarbonate resin composition of the present invention may contain a fluoroolefin resin, but in that case, the transparency may be lowered. In general, a synthetic resin composition containing a fluoroolefin resin is prevented from dripping at the time of melting, so that it is difficult to ignite and burn when a fire occurs. The fluoroolefin resin here is a polymer containing a fluoroethylene structure, for example, a difluoroethylene polymer, a tetrafluoroethylene polymer, a tetrafluoroethylene-hexafluoropropylene polymer, and does not contain tetrafluoroethylene and fluorine. Examples thereof include a copolymer with an ethylene monomer.

  In the present invention, it is preferable to use polytetrafluoroethylene (PTFE) as the fluoroolefin resin, and it is preferable to use PTFE having an average molecular weight of 500,000 or more, particularly 500,000 to 10,000,000. Specific examples of the PTFE include, for example, Teflon (registered trademark), 6-J (manufactured by Mitsui DuPont Fluorochemical Co., Ltd.), Polyflon D-1, Polyflon FA-100, Polyflon F-103, Polyflon F-201, Polyflon MPA (All are trade names made by Daikin Industries, Ltd.), CD076 (made by Asahi IC Fluoropolymers), Argoflon F5 (trade names made by Montefluos), and the like.

  Although the compounding quantity of the fluoro olefin resin used by this invention can be suitably set with the kind and use of the polycarbonate resin used as a base material, it is 0.05-5 mass% equivalent amount of a polycarbonate resin base material. The amount is preferably 0.1 to 2% by mass, and most preferably 0.5 to 1.5% by mass.

  Examples of the lubricant that can be used in the present invention include hydrocarbon lubricants such as liquid paraffin, paraffin wax, and polyethylene wax; aliphatic lubricants such as stearyl alcohol, stearic acid, and 12-hydroxystearic acid; stearamide Amide lubricants such as oleic acid amide, erucic acid amide, methylenebis stearic acid amide, ethylene stearic acid amide; calcium stearate, zinc stearate, magnesium stearate, lead stearate, aluminum stearate, barium stearate, stearic acid Metal soap lubricants such as barium / zinc stearate complex, zinc stearate / calcium stearate complex; hardened oil, glycerin monostearate, butyl stearate, pentaerythritol Teareto include ester lubricant such as stearyl stearate.

  The blending amount of these lubricants can be appropriately set depending on the type and use of the polycarbonate resin as the base material, but is preferably 0.001 to 15% by mass of the polycarbonate resin base material, 0.005 It is more preferably an amount corresponding to -10% by mass, and most preferably an amount corresponding to 0.01-5% by mass.

  Examples of ultraviolet absorbers that can be used in the present invention include benzotriazole ultraviolet absorbers, benzophenone ultraviolet absorbers, and other ultraviolet absorbers. Examples of the benzotriazole ultraviolet absorber include 2- (2′-hydroxy-5′-methylphenyl) benzotriazole, 2- (2′-hydroxy-5′-t-butylphenyl) benzotriazole, 2- ( 2'-hydroxy-3 ', 5'-di-t-butylphenyl) benzotriazole, 2- (2'-hydroxy-3'-t-butyl-5'-methylphenyl) benzotriazole, 2- {2' -Hydroxy-3 ′, 5′-bis (α, α-dimethylbenzyl) phenyl} benzotriazole, 2- (2′-hydroxy-3′-tert-butyl-5′-methylphenyl) -5-chlorobenzotriazole 2- (2′-hydroxy-3 ′, 5′-di-t-butylphenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3 ′, 5′-di-t-amylphenyl) Nzotriazole, 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole, 2- {2′-hydroxy-3 ′-(3 ″, 4 ″, 5 ″, 6 ″ -tetrahydrophthalimidomethyl ) -5′-methylphenyl} benzotriazole, 2,2-methylenebis {4- (1,1,3,3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol}, 2- (2′-hydroxy-5′-methacryloxyphenyl) -2H-benzotriazole and the like.

  Examples of the benzophenone-based ultraviolet absorber include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2 '-Dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-methoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone, bis (5-benzoyl-4-hydroxy-2-methoxy) Phenylmethane) and the like.

  Examples of the other ultraviolet absorbers described above include salicylate-based ultraviolet absorbers such as phenyl salicylate, 4-t-butylphenyl salicylate, 4-octylphenyl salicylate; ethyl-2-cyano-3,3-diphenyl acrylate, 2 -Cyanoacrylate ultraviolet absorbers such as ethylhexyl-2-cyano-3,3-diphenyl acrylate; Oxalic acid ultraviolet absorbers such as 2-ethoxy-2'-ethyl oxalic acid bisanilide, etc. .

  The blending amount of these ultraviolet absorbers can be appropriately set depending on the type and use of the polycarbonate resin as the base material, but is preferably equivalent to 0.001 to 15% by mass of the polycarbonate resin base material. More preferably, the amount is 0.005 to 10% by mass, and most preferably 0.01 to 5% by mass.

  Examples of hindered amine light stabilizers that can be used in the present invention include bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate and bis (N-methyl-2,2,6,6). -Tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) -2- (3,5-di-t-butyl-4-hydroxybenzyl) -2- n-butyl malonate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, tetrakis (1,2,2,6,6-pentamethyl) -4-piperidyl) -1,2,3,4-butanetetracarboxylate, (mixed-2,2,6,6-tetramethyl-4-piperidyl / tridecyl) -1,2,3,4-butyl Tetracarboxylate, (mixed-1,2,2,6,6-pentamethyl-4-piperidyl / tridecyl) -1,2,3,4-butanetetracarboxylate, mixed- {2,2,6 , 6-Tetramethyl-4-piperidyl / β, β, β ′, β′-tetramethyl-3,9- (2,4,8,10-tetraoxaspiro [5,5] undecane) diethyl} -1 , 2,3,4-Butanetetracarboxylate, mixed- {1,2,2,6,6-pentamethyl-4-piperidyl / β, β, β ′, β′-tetramethyl-3,9- ( 2,4,8,10-tetraoxaspiro [5,5] undecane) diethyl} -1,2,3,4-butanetetracarboxylate, poly {6- (1,1,3,3, -tetramethyl) Butyl) imino-1,3,5-tria 2,4-diyl} {(2,2,6,6-tetramethyl-4-piperidyl) imino} hexamethylene {(2,2,6,6-tetramethyl-4-piperidyl) imino}, dimethyl Succinate / 4-hydroxy-2,2,6,6-tetramethyl-1-piperidine ethanol polymer, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 1,2,2,6,6 -Pentamethyl-4-piperidyl methacrylate, ethylenebis (2,2,6,6-tetramethyl-3-oxa-4-piperidine) and the like.

  Examples of other light stabilizers that can be used in the present invention include {2,2′-thiobis (4-t-octylphenolate)}-2-ethylhexylamine nickel (II), nickel dibutyl, and the like. Dithiocarbamate, {2,2′-thiobis (4-t-octylphenolate)}-2-butylamine nickel (II), nickel bis (octylphenyl) sulfide, 3,5-di-t-butyl-4-hydroxy Nickel light stabilizers such as benzyl phosphate monoethylate nickel complex; 2,4-di-t-butylphenyl-3,5′-di-t-butyl-4′-hydroxybenzoate and the like.

  The blending amount of these light stabilizers can be appropriately set depending on the type and use of the polycarbonate resin as the base material, but is preferably equivalent to 0.001 to 15% by mass of the polycarbonate resin base material. More preferably, the amount is 0.005 to 10% by mass, and most preferably 0.01 to 5% by mass.

  Examples of the other antistatic agents that can be used in the present invention include glycerin monofatty acid ester, polyglycerin fatty acid ester, diethanolamine fatty acid amide, polyalkylene glycol alkyl ether, N-alkylammonium chloride, and alkylbenzene sulfonate. And dialkylsulfosuccinates, and the like, but these are inferior in heat resistance, so it is preferable to reduce the amount used as much as possible and avoid the use if possible.

  Examples of the other additives that can be used in the present invention include dibenzylidene sorbitol, bis (p-methylbenzylidene) sorbitol, bis (p-ethylbenzylidene) sorbitol, and hydroxy-di (t-butylbenzoic acid). ) Nucleating agents such as aluminum, sodium bis (4-t-butylphenyl) phosphate, sodium 2,2-methylenebis (4,6-di-t-butylphenyl) phosphate; phthalates, dibasic acids Plasticizers such as ester, chlorinated paraffin, polyester, epoxidized ester, phosphate ester, trimellitic acid ester; metal soap, organotin, organolead, phosphite, epoxide, β-diketone, polyol, perchlorate, Stabilizers such as hydrotalcite and zeolite compounds, and colorants such as titanium compounds Calcium silicate powder, silica powder, talc powder, mica powder, alumina powder, titanium oxide powder, fillers such as glass flakes and the like.

Hereinafter, the present invention will be described more specifically with reference to examples. In the following examples and the like,% and ppm are based on mass unless otherwise specified.

５００mlの４つ口ナスフラスコに、トルエンスルホニルクロリド 21.39 g(112.1 mmol)、DMF 8.19 g(112mmol)、及びピリジン 200 mlを加え、室温で30分間攪拌して溶解させた(黄色透明溶液)。次いで、ｍ-スルホ安息香酸Naを25.0 g(112mmol)加えて室温で30分間攪拌した後、110 ℃まで昇温した。サリチル酸-４-tert-ブチルフェニル(20.00 g;93.4mmol)を加え、100~120 ℃で還流しながら5.5時間攪拌した。その間、溶液は黄色の透明で均一な状態から乳白色懸濁液へと変化した。その後溶媒を減圧留去し、乾燥して褐色油状物を得た。アセトン（120ml×3）及びエタノール（100ml×3）で洗浄して白色固体21ｇを得た。NMRにより、該白色固体がｍ-スルホ安息香酸サリチル酸フェニルエステル ピリジニウム塩であることを確認した。 [Production Example 1]
<Synthesis of m-sulfobenzoic acid salicylic acid-4-tert-Bu-phenyl ester pyridinium salt>

To a 500 ml four-necked eggplant flask, 21.39 g (112.1 mmol) of toluenesulfonyl chloride, 8.19 g (112 mmol) of DMF, and 200 ml of pyridine were added and dissolved by stirring at room temperature for 30 minutes (yellow transparent solution). Next, 25.0 g (112 mmol) of m-sulfobenzoic acid Na was added and stirred at room temperature for 30 minutes, and then heated to 110 ° C. Salicylic acid-4-tert-butylphenyl (20.00 g; 93.4 mmol) was added, and the mixture was stirred for 5.5 hours while refluxing at 100 to 120 ° C. Meanwhile, the solution changed from a yellow, transparent and uniform state to a milky white suspension. Thereafter, the solvent was distilled off under reduced pressure and dried to obtain a brown oily substance. Washing with acetone (120 ml × 3) and ethanol (100 ml × 3) gave 21 g of a white solid. NMR confirmed that the white solid was m-sulfobenzoic acid salicylic acid phenyl ester pyridinium salt.

製造例１で得られたｍ-スルホ安息香酸-サリチル酸フェニルエステル ピリジニウム塩の27g(51.4mmol)を蒸留水200mlに溶解した。次いで、NaClを3.0 g添加し、室温で１時間攪拌した。沈殿物が析出したので吸引ろ過によってろ別し、白色の固体を１８g得た。得られた固体は、NMRよりｍ-スルホ安息香酸サリチル酸-４-tert-Bu-フェニルエステル Na塩（化合物No.１）であると確認された。 [Production Example 2]
<Ion exchange reaction to m-sulfobenzoic acid salicylic acid-4-tert-Bu-phenyl ester sodium salt (synthesis of compound No. 1)>

27 g (51.4 mmol) of m-sulfobenzoic acid-salicylic acid phenyl ester pyridinium salt obtained in Production Example 1 was dissolved in 200 ml of distilled water. Next, 3.0 g of NaCl was added and stirred at room temperature for 1 hour. A precipitate was deposited, and was filtered off by suction filtration to obtain 18 g of a white solid. The obtained solid was confirmed to be m-sulfobenzoic acid salicylic acid-4-tert-Bu-phenyl ester Na salt (Compound No. 1) by NMR.

[Production Example 3]
<Ion exchange reaction to m-sulfobenzoic acid salicylic acid-4-tert-Bu-phenyl ester K salt (synthesis of compound No. 2)>
27 g (51.4 mmol) of m-sulfobenzoic acid-salicylic acid phenyl ester pyridinium salt obtained in Production Example 1 was dissolved in a mixed solvent of MeOH / water. Next, 38.3 mg of KCl was added and stirred at room temperature for 1 hour. A precipitate was deposited, and was filtered by suction filtration to obtain 18 g of a white solid. The obtained solid was confirmed by NMR to be m-sulfobenzoic acid salicylic acid-4-tert-Bu-phenyl ester K salt (Compound No. 2).

[Production Example 4]
In the same manner as in Production Examples 1 to 3, m-sulfobenzoic acid salicylic acid octylphenyl ester K salt (Compound No. 7) was synthesized.

[Production Example 5]
In the same manner as in Production Examples 1 to 3, m-sulfobenzoic acid salicylic acid toluyl ester K salt (Compound No. 8) was synthesized.

[Examples 1 to 3, Comparative Example 1]
Test pieces were prepared using the compounds of the present invention under the following conditions, and performance evaluation was performed under the following conditions. The results are shown in Table 1. Moreover, it evaluated similarly using the dodecyl benzene sulfonic acid Na salt as the comparative product-1.

<Processing conditions>
2 parts of the compound of the present invention described in Table 1 (dried at 120 ° C. for 4 hours) with respect to 100 parts by mass of the polycarbonate resin (Iupilon S-3000 manufactured by Mitsubishi Engineering Plastics) dried at 120 ° C. for 4 hours. Mass parts were added and mixed well to obtain a polycarbonate resin composition.
The obtained polycarbonate resin composition was melt kneaded at 260 ° C. using a single screw with a single screw extruder 2D25W manufactured by Toyo Seiki Seisakusho (trade name: Labo Plast Mill). Obtained.

<Specimen creation>
Using a small vacuum heating press (trade name: IMC-1824 type) manufactured by Imoto Seisakusho, press plate molding was performed under the following conditions.
Temperature conditions: Both the upper plate and the lower plate were set to 270 ° C.
Mold: 10cm x 10cm x 1mm
Amount of polycarbonate resin composition: 13 g

<Transparency evaluation>
The test piece obtained above was observed with the naked eye, and compared with a blank (without adding an antistatic agent), and evaluated according to the following criteria.
○: The same level of transparency as the blank.
(Triangle | delta): It is cloudy clearly from a blank.
×: Remarkably cloudy than blank

<Evaluation of antistatic properties>
The test piece obtained above was stored under conditions of a temperature of 25 ° C. and a humidity of 60%, and after 1 day, 1 week and 2 weeks after molding, the R8340 resistance manufactured by Advantest was used in the above atmosphere. Using a meter, the surface resistivity (Ω) was measured under the conditions of an applied voltage of 500 V and an applied time of 1 minute. The measurement was performed for five points, and the average value is shown in Table 1.

表１の結果は、本発明の帯電防止剤がポリカーボネート樹脂に対して特に好適であることを実証するものである。

The results in Table 1 demonstrate that the antistatic agent of the present invention is particularly suitable for polycarbonate resins.

By using the antistatic agent of the present invention, it is possible to obtain a molded polycarbonate resin product having not only excellent transparency but also long-lasting antistatic performance. Therefore, the present invention is extremely significant industrially.

Claims (6)

An antistatic agent for polycarbonate resin, represented by the following general formula (1):

In the general formula (1), R represents a linear or branched alkyl group having 1 to 18 carbon atoms; a cycloalkyl group having 3 to 8 carbon atoms; an alkenyl group having 3 to 8 carbon atoms; a carbon atom. An aryl group having 6 to 30 carbon atoms; an arylalkyl group having 7 to 30 carbon atoms; or an alkylaryl group having 7 to 30 carbon atoms. These groups may be substituted with a hydroxy group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 18 carbon atoms or an alkoxy group, and an oxygen atom, a sulfur atom, a carbonyl group, an ester group. , May be interrupted by an amide group or an imino group, and these substitutions and interruptions may be combined. M represents an alkali metal ion or an alkaline earth metal ion, and n represents a number of 1 or 2.   The antistatic agent for polycarbonate resins according to claim 1, wherein R in the general formula (1) is an aryl group or an alkylaryl group.   The antistatic agent for polycarbonate resin according to claim 2, wherein R in the general formula (1) is an alkylaryl group.   The antistatic agent for polycarbonate resins according to any one of claims 1 to 3, wherein M in the general formula (1) is an alkali metal ion.   The antistatic agent for polycarbonate resins according to claim 4, wherein M in the general formula (1) is a potassium ion.   A polycarbonate resin composition obtained by adding the antistatic agent for polycarbonate resin according to claim 1 to the polycarbonate resin, wherein the content of the antistatic agent for polycarbonate resin in the composition is the polycarbonate resin. A polycarbonate resin composition characterized by being 0.01 to 20% by mass based on the total mass of the resin and the antistatic agent.