JP5283863B2 - Quaternary ammonium salt - Google Patents
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- JP5283863B2 JP5283863B2 JP2007164670A JP2007164670A JP5283863B2 JP 5283863 B2 JP5283863 B2 JP 5283863B2 JP 2007164670 A JP2007164670 A JP 2007164670A JP 2007164670 A JP2007164670 A JP 2007164670A JP 5283863 B2 JP5283863 B2 JP 5283863B2
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- quaternary ammonium
- ammonium salt
- dodecylbenzenesulfonate
- hexyl
- antistatic agent
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 19
- -1 N-hexyl-4-methylpyridinium cation Chemical class 0.000 claims abstract description 20
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920000098 polyolefin Polymers 0.000 claims description 3
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 abstract description 20
- 239000011347 resin Substances 0.000 abstract description 9
- 229920005989 resin Polymers 0.000 abstract description 9
- 239000002216 antistatic agent Substances 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 8
- 150000001450 anions Chemical class 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 7
- KVUBRTKSOZFXGX-UHFFFAOYSA-N 1-hexyl-4-methylpyridin-1-ium Chemical compound CCCCCC[N+]1=CC=C(C)C=C1 KVUBRTKSOZFXGX-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- HEIQGUZVWWLUDQ-UHFFFAOYSA-M 1-hexyl-4-methylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCC[N+]1=CC=C(C)C=C1 HEIQGUZVWWLUDQ-UHFFFAOYSA-M 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- BAUDWMMATSUQQO-UHFFFAOYSA-M lithium;4-dodecylbenzenesulfonate Chemical compound [Li+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 BAUDWMMATSUQQO-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- CVZUNXUUYQKGKS-UHFFFAOYSA-M potassium;4-dodecylbenzenesulfonate Chemical compound [K+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 CVZUNXUUYQKGKS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JHJUUEHSAZXEEO-UHFFFAOYSA-M sodium;4-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 JHJUUEHSAZXEEO-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
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- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、新規な第４級アンモニウム塩に関する。 The present invention relates to a novel quaternary ammonium salt.
ｐ−ドデシルベンゼンスルホナートをアニオンとする第４級アンモニウム塩は公知である。このような化合物について、特許文献１及び２に記載されている。具体的に開示されたｐ−ドデシルベンゼンスルホナートをアニオンとする第４級アンモニウム塩は、テトラブチルアンモニウム＝ｐ−ドデシルベンゼンスルホナート、テトラフェニルアンモニウム＝ｐ−ドデシルベンゼンスルホナート、及びセチルピリジニウム＝ｐ−ドデシルベンゼンスルホナートである。かかる第４級アンモニウム塩はいずれも常温で固体であり、樹脂用の帯電防止剤として用いるとき、樹脂との相溶性に問題を生じやすい。
本発明は、常温で液体である新規な第４級アンモニウム塩を提供することを課題とする。 An object of the present invention is to provide a novel quaternary ammonium salt that is liquid at room temperature.
本発明者が上記課題を解決する為に鋭意検討したところ、驚くべきことに、トリオクチルメチルアンモニウム＝ｐ−ドデシルベンゼンスルホナート及びＮ−ヘキシル−４−メチルピリジニウム＝ｐ−ドデシルベンゼンスルホナートが常温で液体であり、しかも種々の樹脂に対して帯電防止剤として使用しうることが期待できることを見出し、本発明を完成するに至った。 When the present inventor diligently studied to solve the above-mentioned problems, surprisingly, trioctylmethylammonium = p-dodecylbenzenesulfonate and N-hexyl-4-methylpyridinium = p-dodecylbenzenesulfonate are room temperature. The present invention was completed by finding that it is liquid and can be expected to be used as an antistatic agent for various resins.
即ち本発明は、式（１）： That is, the present invention provides the formula (1):
本発明の第４級アンモニウム塩は、常温で液体であるので、種々の樹脂に対する帯電防止剤としての使用が期待できる。 Since the quaternary ammonium salt of the present invention is liquid at room temperature, it can be expected to be used as an antistatic agent for various resins.
以下、本発明を具体的に説明する。
本発明の第４級アンモニウム塩は、トリオクチルメチルアンモニウム＝ｐ−ドデシルベンゼンスルホナート及びＮ−ヘキシル−４−メチルピリジニウム＝ｐ−ドデシルベンゼンスルホナートである。
Hereinafter, the present invention will be specifically described.
The quaternary ammonium salts of the present invention are trioctylmethylammonium = p-dodecylbenzenesulfonate and N-hexyl-4-methylpyridinium = p-dodecylbenzenesulfonate.
本発明の第４級アンモニウム塩は、例えば式（２）：
Ｑ＋・Ｘ− （２）
（式中、Ｑ＋は前記に同じ。Ｘはハロゲン原子を示す。）で表される第４級アンモニウム＝ハライド（以下、アンモニウム＝ハライド（２）という）をｐ−ドデシルベンゼンスルホン酸又はそのアルカリ金属塩（以下、ｐ−ドデシルベンゼンスルホン酸類という）を用いてアニオン交換反応をすることで製造できる。
The quaternary ammonium salt of the present invention has, for example, formula (2):
Q + · X − (2)
(Wherein Q + is the same as described above, X represents a halogen atom) a quaternary ammonium halide (hereinafter referred to as ammonium = halide (2)) is p-dodecylbenzenesulfonic acid or an alkali thereof. It can be produced by an anion exchange reaction using a metal salt (hereinafter referred to as p-dodecylbenzenesulfonic acid).
アンモニウム＝ハライド（２）は、市販品を用いても良いし、例えばトリオクチルメチルアンモニウム＝ハライドの場合には、トリオクチルアミンをハロゲン化メチルと反応させることで製造できる。またＮ−ヘキシル−４−メチルピリジニウム＝ハライドの場合には、４−メチルピリジンをハロゲン化ヘキシルと反応させることで製造できる。 As the ammonium halide (2), a commercially available product may be used. For example, in the case of trioctylmethylammonium halide, it can be produced by reacting trioctylamine with methyl halide. In the case of N-hexyl-4-methylpyridinium = halide, it can be produced by reacting 4-methylpyridine with hexyl halide.
ハロゲン化メチルとしてはメチルクロリド、メチルブロミド、メチルヨージドが、またハロゲン化ヘキシルとしてはヘキシルクロリド、ヘキシルブロミド、ヘキシルヨージドが挙げられる。 Examples of the methyl halide include methyl chloride, methyl bromide, and methyl iodide. Examples of the halogenated hexyl include hexyl chloride, hexyl bromide, and hexyl iodide.
ｐ−ドデシルベンゼンスルホン酸アルカリ金属塩としては、ｐ−ドデシルベンゼンスルホン酸ナトリウム、ｐ−ドデシルベンゼンスルホン酸リチウム、ｐ−ドデシルベンゼンスルホン酸カリウムが挙げられる。 Examples of the alkali metal salt of p-dodecylbenzenesulfonic acid include sodium p-dodecylbenzenesulfonate, lithium p-dodecylbenzenesulfonate, and potassium p-dodecylbenzenesulfonate.
ｐ−ドデシルベンゼンスルホン酸類の使用量は、アンモニウム＝ハライド（２）１モルに対して、通常０．９モル以上、好ましくは０．９モル〜１．１モルであり、より好ましくは０．９５〜１．０５モルである。 The usage-amount of p-dodecylbenzenesulfonic acid is 0.9 mol or more normally with respect to 1 mol of ammonium halides (2), Preferably it is 0.9 mol-1.1 mol, More preferably, it is 0.95. -1.05 mol.
アニオン交換反応は通常水溶媒中で行われる。水の使用量は特に制限はないが、アンモニウム＝ハライド（２）１重量部に対して通常２０重量部以下、好ましくは０．５〜１０重量部であり、特に好ましくは１〜５重量部である。 The anion exchange reaction is usually performed in an aqueous solvent. The amount of water used is not particularly limited, but is usually 20 parts by weight or less, preferably 0.5 to 10 parts by weight, particularly preferably 1 to 5 parts by weight with respect to 1 part by weight of ammonium halide (2). is there.
アンモニウム＝ハライド（２）、ｐ−ドデシルベンゼンスルホン酸類及び水の混合順序は特に限定されず、アンモニウム＝ハライド（２）と水を混合した後にｐ−ドデシルベンゼンスルホン酸類を添加してもよいし、ｐ−ドデシルベンゼンスルホン酸類と水を混合した後にアンモニウム＝ハライド（２）を添加してもよい。また、着色が問題となる場合には、アンモニウム＝ハライド（２）と水を混合した後に、活性炭等の脱色剤を用いて処理し、濾過して得られた濾液をアニオン交換反応に用いることもできる。 The mixing order of ammonium halide (2), p-dodecylbenzenesulfonic acid and water is not particularly limited, and after mixing ammonium halide (2) and water, p-dodecylbenzenesulfonic acid may be added, Ammonium halide (2) may be added after mixing p-dodecylbenzenesulfonic acid and water. In addition, when coloring is a problem, it is possible to mix ammonium = halide (2) and water, then treat with a decolorizing agent such as activated carbon, and use the filtrate obtained by filtration for anion exchange reaction. it can.
反応温度は、通常１０℃以上、好ましくは１５〜６０℃、特に好ましくは２０〜４０℃である。 The reaction temperature is usually 10 ° C. or higher, preferably 15 to 60 ° C., particularly preferably 20 to 40 ° C.
反応終了後の反応液は、本発明の第４級アンモニウム塩の水溶解性が低いので、水層と有機層とに分液している。この反応液から第４級アンモニウム塩を分離するには、所望により有機層を水洗した後、有機層を乾燥することによって第４級アンモニウム塩が得られる。また、必要であれば水不溶の有機溶剤（例えば、トルエン、酢酸エチル、塩化メチレン等）を反応中又は反応終了後に添加し、第４級アンモニウム塩を水不溶の有機溶剤に抽出してもよく、得られた抽出層を所望により水洗し、次いで有機溶剤を留出除去して抽出層を濃縮すれば残渣として、本発明の第４級アンモニウム塩が得られる。 The reaction solution after completion of the reaction is separated into an aqueous layer and an organic layer because the water solubility of the quaternary ammonium salt of the present invention is low. In order to separate the quaternary ammonium salt from the reaction solution, the organic layer is washed with water if desired, and then the organic layer is dried to obtain a quaternary ammonium salt. If necessary, a water-insoluble organic solvent (for example, toluene, ethyl acetate, methylene chloride, etc.) may be added during or after the reaction to extract the quaternary ammonium salt into the water-insoluble organic solvent. The obtained extraction layer is washed with water if desired, and then the organic solvent is distilled off and the extraction layer is concentrated to obtain the quaternary ammonium salt of the present invention as a residue.
つぎに、本発明を実施例に基づいて具体的に説明するが、本発明はなんらこれらに限定されるものではない。なお、以下の応用例中、表面抵抗値は三菱化学株式会社製ヒレスタＨＴ−２１０を用い、印加電圧５００Ｖにて測定した。 Next, the present invention will be specifically described based on examples, but the present invention is not limited thereto. In the following application examples, the surface resistance value was measured at an applied voltage of 500 V using Hillesta HT-210 manufactured by Mitsubishi Chemical Corporation.
実施例１
８１．３％トリオクチルメチルアンモニウム＝クロリド水溶液４９．６ｇ（０．１００モル）、塩化メチレン６９．３ｇ及びイオン交換水６９．３ｇを混合した後、ｐ−ドデシルベンゼンスルホン酸３４．３ｇ（０．１０５モル）を添加し、２５℃で４時間撹拌した。反応終了後、得られた有機層を分液操作により分離し、イオン交換水６９．３ｇで２回洗浄した。有機層を濃縮して塩化メチレンを除去後、残渣を減圧下で乾燥し、常温で液状のトリオクチルメチルアンモニウム＝ｐ−ドデシルベンゼンスルホナート（以下、ＴＯＭＡ−ＤＢＳと略記する）を６２．５ｇを得た（収率９０．２％）。以下にＴＯＭＡ−ＤＢＳのＮＭＲデータを示す。
Example 1
After mixing 49.6 g (0.100 mol) of an 81.3% trioctylmethylammonium chloride aqueous solution, 69.3 g of methylene chloride and 69.3 g of ion-exchanged water, 34.3 g of p-dodecylbenzenesulfonic acid (0.3. 105 mol) was added and stirred at 25 ° C. for 4 hours. After completion of the reaction, the obtained organic layer was separated by a liquid separation operation and washed twice with 69.3 g of ion-exchanged water. After the organic layer was concentrated to remove methylene chloride, the residue was dried under reduced pressure, and 62.5 g of trioctylmethylammonium = p-dodecylbenzenesulfonate (hereinafter abbreviated as TOMA-DBS) that was liquid at room temperature. Obtained (yield 90.2%). The NMR data of TOMA-DBS is shown below.
１Ｈ−ＮＭＲ（ＣＤＣｌ３） δ：０．７９−１．６５（ｍ，７０Ｈ）、３．２５（Ｓ，３Ｈ）、３．３４（ｔ，６Ｈ）、７．０９（ｄ，２Ｈ）、７．８０（ｄ，２Ｈ） 1 H-NMR (CDCl 3 ) δ: 0.79-1.65 (m, 70H), 3.25 (S, 3H), 3.34 (t, 6H), 7.09 (d, 2H), 7.80 (d, 2H)
実施例２
Ｎ−ヘキシル−４−メチルピリジニウム＝ブロミド２５．８ｇ（０．１００モル）、塩化メチレン５０．４ｇ及びイオン交換水５０．４ｇを混合した後、ｐ−ドデシルベンゼンスルホン酸３４．３ｇ（０．１０５モル）を添加し、２５℃で４時間撹拌した。反応終了後、得られた有機層を分液操作により分離し、イオン交換水５０．４ｇで２回洗浄した。有機層を濃縮して塩化メチレンを除去後、残渣を減圧下で乾燥し、常温で液状のＮ−ヘキシル−４−メチルピリジニウム＝ｐ−ドデシルベンゼンスルホナート（以下、ＨＭＰ−ＤＢＳと略記する。）４６．０ｇを得た（収率９１．３％）。以下にＨＭＰ−ＤＢＳのＮＭＲデータを示す。
Example 2
After mixing 25.8 g (0.100 mol) of N-hexyl-4-methylpyridinium bromide, 50.4 g of methylene chloride and 50.4 g of ion-exchanged water, 34.3 g of p-dodecylbenzenesulfonic acid (0.105) Mol) was added and stirred at 25 ° C. for 4 hours. After completion of the reaction, the obtained organic layer was separated by a liquid separation operation and washed twice with 50.4 g of ion-exchanged water. After the organic layer was concentrated to remove methylene chloride, the residue was dried under reduced pressure, and liquid N-hexyl-4-methylpyridinium = p-dodecylbenzenesulfonate (hereinafter abbreviated as HMP-DBS) at room temperature. 46.0 g was obtained (yield 91.3%). The NMR data of HMP-DBS is shown below.
１Ｈ−ＮＭＲ（ＣＤＣｌ３） δ：０．７２−１．９０（ｍ，３６Ｈ）、２．５６（Ｓ，３Ｈ）、４．７０（ｔ，２Ｈ）、７．１２（ｄ，２Ｈ）、７．７７（ｄ，２Ｈ）、７．７９（ｄ，２Ｈ）、９．０４（ｄ，２Ｈ） 1 H-NMR (CDCl 3 ) δ: 0.72-1.90 (m, 36H), 2.56 (S, 3H), 4.70 (t, 2H), 7.12 (d, 2H), 7.77 (d, 2H), 7.79 (d, 2H), 9.04 (d, 2H)
応用例１及び２並びに参考例
ペレット状のポリオレフィン「ＺＥＯＮＯＲ１０２０Ｒ」（登録商標、日本ゼオン株式会社製）３０ｇをシクロヘキサン／ＴＨＦ（８０／２０）の混合溶液２７０ｇに溶解させ、１０重量％ＺＥＯＮＯＲ１０２０Ｒ溶液を調製した。ＺＥＯＮＯＲ溶液１０ｇに表１に示す本発明の第４級アンモニウム塩を帯電防止剤として０．０２ｇ（樹脂に対して２重量％）添加し、室温で１時間混合した。得られた混合液を、バーコーター（＃３２）を用いて、アルミシート上にコートした後、１２０℃で１時間乾燥させ、厚さ約５μｍのＺＥＯＮＯＲ１０２０Ｒの試験フィルムを作製した。試験フィルムを２３℃、５０％ＲＨの雰囲気中に６時間保持した後、２３℃、５０％ＲＨで試験フィルムの裏面と表面の表面抵抗値を測定した。その測定結果を表１に示す。また、帯電防止剤を添加しないものの表面抵抗値も表１に示す。
Application Examples 1 and 2 and Reference Example 30 g of pelleted polyolefin “ZEONOR1020R” (registered trademark, manufactured by Nippon Zeon Co., Ltd.) was dissolved in 270 g of a mixed solution of cyclohexane / THF (80/20) to prepare a 10 wt% ZEONOR1020R solution. did. 0.02 g (2% by weight based on the resin) of the quaternary ammonium salt of the present invention shown in Table 1 was added to 10 g of ZEONOR solution as an antistatic agent, and mixed at room temperature for 1 hour. The obtained mixed solution was coated on an aluminum sheet using a bar coater (# 32), and then dried at 120 ° C. for 1 hour to prepare a test film of ZEONOR 1020R having a thickness of about 5 μm. After holding the test film in an atmosphere of 23 ° C. and 50% RH for 6 hours, the surface resistance values of the back surface and the surface of the test film were measured at 23 ° C. and 50% RH. The measurement results are shown in Table 1. Further, Table 1 also shows the surface resistance values of those not added with the antistatic agent.
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