TWI399429B - Antistatic agent and antistatic resin composition containing the same - Google Patents

Antistatic agent and antistatic resin composition containing the same Download PDF

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TWI399429B
TWI399429B TW096110468A TW96110468A TWI399429B TW I399429 B TWI399429 B TW I399429B TW 096110468 A TW096110468 A TW 096110468A TW 96110468 A TW96110468 A TW 96110468A TW I399429 B TWI399429 B TW I399429B
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hydrazine
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TW200745318A (en
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Yasuhiro Shiomi
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Koei Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/50—Phosphorus bound to carbon only
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0075—Antistatics
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/16—Anti-static materials

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Description

抗靜電劑及含有該抗靜電劑之抗靜電性樹脂組成物Antistatic agent and antistatic resin composition containing the same

本發明係關於抗靜電劑及含有該抗靜電劑之抗靜電性樹脂組成物。The present invention relates to an antistatic agent and an antistatic resin composition containing the antistatic agent.

以往，第四級鏻鹽係以作為例如樹脂等之抗靜電劑而使用(例如，參照日本專利第3373398號公報、日本專利第3390665號公報、日本專利第3427848號公報、日本特開2004－002730號公報、WO2005/066259)。本發明人在只使用一種第四級鏻鹽於樹脂時，樹脂之表面電阻值係通常約1012 Ω左右以上，依據用途，期望能有更進一步降低樹脂之表面電阻值的抗靜電劑。In the past, the fourth-stage sulfonium salt is used as an antistatic agent such as a resin (for example, see Japanese Patent No. 3373398, Japanese Patent No. 3390665, Japanese Patent No. 3427848, and Japanese Patent Laid-Open No. 2004-002730 Bulletin, WO2005/066259). When the inventors of the present invention used only a fourth-grade cerium salt in a resin, the surface resistance value of the resin is usually about 10 12 Ω or more, and depending on the use, it is desired to have an antistatic agent which further lowers the surface resistance value of the resin.

本發明係提供一種相較於以往為更能降低表面電阻值、且含有具優良抗靜電能力之第四級鏻鹽的抗靜電劑，以及含有該抗靜電劑之抗靜電性樹脂組成物。The present invention provides an antistatic agent which is more capable of lowering the surface resistance value and contains a fourth-stage antimony salt having excellent antistatic ability, and an antistatic resin composition containing the antistatic agent.

本發明人為了解決上述課題而努力研究，結果令人吃驚地，發現將如式(1)所示之第四級鏻鹽之至少一種：(R1 )3 R2 P＋ ．A－ (1)(式中，R1 係碳數1至4之烷基或芳香基；當R1 為碳數1至4之烷基時，R2 係表示與R1 相同，或是表示芳香基或芳烷基(aralkyl)；當R1 為芳香基時，R2 係碳數1至16之烷基、芳香基或芳烷基；A－ 係表示貳(全氟烷磺醯基)醯亞胺離子或全氟烷磺酸離子)、及如式(2)所示之第四級鏻鹽之至少一種：(R3 )3 R4 P＋ ．B－ (2)(式中，R3 係碳數1至4之烷基或芳香基；當R3 為碳數1至4之烷基時，R4 係表示與R3 相同，或是表示芳香基或芳烷基；當R3 為芳香基時，R4 係碳數1至16之烷基、芳香基或芳烷基；B－ 係表示陰離子)進行併用(惟，如式(1)所示之鏻鹽(1)與如式(2)所示之鏻鹽不為相同之化合物)後，藉由此等之併用，相較於分別單獨使用之情況，表面電阻值係較為降低，因而完成本發明。The inventors of the present invention have diligently studied to solve the above problems, and as a result, it has been surprisingly found that at least one of the fourth-order phosphonium salts represented by the formula (1): (R 1 ) 3 R 2 P + . A - (1) (wherein R 1 is an alkyl group or an aromatic group having 1 to 4 carbon atoms; when R 1 is an alkyl group having 1 to 4 carbon atoms, R 2 represents the same as R 1 or represents An aryl group or an aralkyl group; when R 1 is an aryl group, R 2 is an alkyl group having 1 to 16 carbon atoms, an aryl group or an aralkyl group; and the A - line means fluorene (perfluoroalkylsulfonyl) At least one of a quinone imine ion or a perfluoroalkanesulfonate ion, and a fourth-order phosphonium salt represented by the formula (2): (R 3 ) 3 R 4 P + . B - (2) (wherein R 3 is an alkyl group or an aromatic group having 1 to 4 carbon atoms; when R 3 is an alkyl group having 1 to 4 carbon atoms, R 4 represents the same as R 3 or represents An aryl or aralkyl group; when R 3 is an aryl group, R 4 is an alkyl group having 1 to 16 carbon atoms, an aryl group or an aralkyl group; and a B - line represents an anion) is used in combination (however, as in the formula (1) When the sulfonium salt (1) is not the same as the sulfonium salt represented by the formula (2), the surface resistance value is lowered as compared with the case where the sulfonium salt is not the same as the compound. Thus the present invention has been completed.

亦即，即本發明係提供以下[1]至[6]者。That is, the present invention provides the following [1] to [6].

[1]一種抗靜電劑，其特徵係含有如式(1)所示之第四級鏻鹽(以下，以鏻鹽(1)稱之)之至少1種：(R1 )3 R2 P＋ ．A－ (1)(式中，R1 係碳數1至4之烷基或芳香基；當R1 為碳數1至4之烷基時，R2 係表示與R1 相同，或是表示芳香基或芳烷基；當R1 為芳香基時，R2 係表示碳數1至16之烷基、芳香基或芳烷基；A－ 係表示貳(全氟烷磺醯基)醯亞胺離子或全氟烷磺酸離子)、及如式(2)所示之第四級鏻鹽(以下，以鏻鹽(2)稱之)之至少1種：(R3 )3 R4 P＋ ．B－ (2)(式中，R3 係碳數1至4之烷基或芳香基；當R3 為碳數1至4之烷基時，R4 係表示與R3 相同，或是表示芳香基或芳烷基；當R3 為芳香基時，R4 係表示碳數1至16之烷基、芳香基或芳烷基；B－ 係表示陰離子)以作為有效成分(惟，鏻鹽(1)與鏻鹽(2)不為相同之化合物)。[1] An antistatic agent characterized by containing at least one of a fourth-order phosphonium salt (hereinafter referred to as a phosphonium salt (1)) represented by the formula (1): (R 1 ) 3 R 2 P + . A - (1) (wherein R 1 is an alkyl group or an aromatic group having 1 to 4 carbon atoms; when R 1 is an alkyl group having 1 to 4 carbon atoms, R 2 represents the same as R 1 or represents An aromatic group or an aralkyl group; when R 1 is an aromatic group, R 2 represents an alkyl group, an aromatic group or an aralkyl group having 1 to 16 carbon atoms; and A - represents a fluorene (perfluoroalkylsulfonyl) fluorene group. At least one of an amine ion or a perfluoroalkanesulfonate ion and a fourth-order phosphonium salt (hereinafter referred to as a phosphonium salt (2)) represented by the formula (2): (R 3 ) 3 R 4 P + . B - (2) (wherein R 3 is an alkyl group or an aromatic group having 1 to 4 carbon atoms; when R 3 is an alkyl group having 1 to 4 carbon atoms, R 4 represents the same as R 3 or represents An aromatic group or an aralkyl group; when R 3 is an aromatic group, R 4 means an alkyl group having 1 to 16 carbon atoms, an aromatic group or an aralkyl group; and B - means an anion) as an active ingredient (only, an onium salt) (1) A compound which is not the same as the sulfonium salt (2).

[2]如[1]所記載之抗靜電劑，其中，B－ 所示之陰離子係貳(全氟烷磺醯基)醯亞胺離子、全氟烷磺酸離子、全氟烷羧酸離子、烷磺酸離子、烷基苯磺酸離子、含氟無機酸離子或含氧酸離子。[2] [1] The antistatic agent described, wherein, B - II shown in the anionic (perfluoroalkyl sulfonic acyl) acyl imide ion, a perfluoroalkyl sulfonate ion, a carboxylate ion perfluoroalkyl , an alkane sulfonate ion, an alkylbenzene sulfonate ion, a fluorine-containing inorganic acid ion or an oxyacid ion.

[3]如[1]或[2]所記載之抗靜電劑，其中，式(1)及式(2)中，R1 、R2 、R3 及R4 ，任一者皆為碳數1至4之烷基。[3] The antistatic agent according to [1] or [2], wherein, in the formulae (1) and (2), R 1 , R 2 , R 3 and R 4 are each a carbon number. Alkyl groups of 1 to 4.

[4]如[1]至[3]中任一項所記載之抗靜電劑，其中，從鏻鹽(1)選擇之至少1種與從鏻鹽(2)選擇之至少1種的混合比例係重量比80：20至20：80之比例。[4] The antistatic agent according to any one of [1] to [3], wherein a mixture ratio of at least one selected from the onium salt (1) and at least one selected from the onium salt (2) The ratio of the weight ratio is from 80:20 to 20:80.

[5]一種抗靜電性樹脂組成物，係使樹脂中含有[1]至[4]中任一項所記載之抗靜電劑。[5] An antistatic resin composition according to any one of [1] to [4], wherein the antistatic resin composition is contained in the resin.

[6]如[5]所記載之抗靜電性樹脂組成物，其中，樹脂為環氧樹脂、聚碳酸酯、聚烯烴、(甲基)丙烯酸系樹脂或聚酯。[6] The antistatic resin composition according to [5], wherein the resin is an epoxy resin, a polycarbonate, a polyolefin, a (meth)acrylic resin or a polyester.

以下，詳細說明本發明。Hereinafter, the present invention will be described in detail.

式(1)中，R1 係碳數1至4之烷基或芳香基，以碳數1至4之烷基為較佳。以碳數1至4之烷基而言，具體而言可列舉如甲基、乙基、丙基、異丙基、丁基、異丁基、二級丁基、三級丁基。以芳香基而言，可列舉如可具有置換基之苯基、萘基、吡啶基(pyridyl)、喹啉基(quinolyl)及異喹啉基等，具體而言可列舉如苯基、2－甲基苯基、3－甲基苯基、4－甲基苯基、2,4－二甲基苯基、3,5－二甲基苯基、4－甲氧基苯基、4－三級丁氧基苯基、4－硝苯基、吡啶基、喹啉基及異喹啉基等。In the formula (1), R 1 is an alkyl group or an aromatic group having 1 to 4 carbon atoms, and preferably an alkyl group having 1 to 4 carbon atoms. Specific examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a secondary butyl group, and a tertiary butyl group. Examples of the aromatic group include a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group and the like which may have a substituent group, and specific examples thereof include a phenyl group and a 2- Methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 3,5-dimethylphenyl, 4-methoxyphenyl, 4-tri Butylated phenyl, 4-nitrophenyl, pyridyl, quinolyl and isoquinolyl.

式(1)中，當R1 為碳數1至4之烷基時，R2 係碳數1至4之烷基、芳香基或芳烷基，較佳為碳數1至4之烷基。以碳數1至4之烷基及芳香基而言，可分別列舉如與前述碳數1至4之烷基及前述芳香基相同者。以芳烷基而言，可列舉如將前述碳數1至4之烷基所具有之氫原子取代為前述芳香基而成之基，具體而言可例示如苯甲基、苯乙基、萘基甲基、二苯基甲基等。In the formula (1), when R 1 is an alkyl group having 1 to 4 carbon atoms, R 2 is an alkyl group having 1 to 4 carbon atoms, an aromatic group or an aralkyl group, preferably an alkyl group having 1 to 4 carbon atoms. . The alkyl group having 1 to 4 carbon atoms and the aromatic group may be the same as those of the above-mentioned alkyl group having 1 to 4 carbon atoms and the above-mentioned aromatic group. The aralkyl group may be a group obtained by substituting a hydrogen atom of the alkyl group having 1 to 4 carbon atoms to the above aromatic group, and specific examples thereof include a benzyl group, a phenethyl group, and a naphthalene group. Methyl, diphenylmethyl and the like.

另外，當R1 為芳香基時，R2 係碳數1至16之烷基、芳香基或芳烷基。以碳數1至16之烷基而言，可列舉如碳數1至16之直鏈狀、支鏈狀之烷基，具體而言可列舉如甲基、乙基、丙基、異丙基、丁基、異丁基、二級丁基、三級丁基、戊基、己基、環己基、庚基、辛基、2－乙基己基、壬基、癸基、十二基、十四基、十六基等。以芳香基及芳烷基而言，可分別列舉如與前述芳香基及前述芳烷基相同者。Further, when R 1 is an aromatic group, R 2 is an alkyl group, an aromatic group or an aralkyl group having 1 to 16 carbon atoms. The alkyl group having 1 to 16 carbon atoms may, for example, be a linear or branched alkyl group having 1 to 16 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group and an isopropyl group. , butyl, isobutyl, secondary butyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, decyl, decyl, dodecyl, fourteen Base, sixteen base, etc. The aromatic group and the aralkyl group may be the same as those of the above-mentioned aromatic group and the aforementioned aralkyl group, respectively.

式(1)中，A－ 係貳(全氟烷磺醯基)醯亞胺離子或全氟烷磺酸離子。以貳(全氟烷磺醯基)醯亞胺離子而言，係如式(3)所示之陰離子：(Rf 1 SO2 )(Rf 2 SO2 )N－ (3)(式中，Rf 1 及Rf 2 係可相同亦可相異，表示碳數1至4之全氟烷基)，以如Rf 1 及Rf 2 所示之碳數1至4之全氟烷基而言，可列舉如三氟甲基、五氟乙基、七氟丙基、九氟丁基等。具體而言可列舉如貳(三氟甲磺醯基)醯亞胺離子[(CF3 SO2 )2 N－ ]、貳(五氟乙磺醯基)醯亞胺離子[(CF3 CF2 SO2 )2 N－ ]、貳(七氟丙磺醯基)醯亞胺離子[(CF3 CF2 CF2 SO2 )2 N－ ]、貳(九氟丁磺醯基)醯亞胺離子[(CF3 CF2 CF2 CF2 SO2 )2 N－ ]、(三氟甲磺醯基)(五氟乙磺醯基)醯亞胺離子[(CF3 SO2 )(CF3 CF2 SO2 )N－ ]、(三氟甲磺醯基)(七氟丙磺醯基)醯亞胺離子[(CF3 SO2 )(CF3 CF2 CF2 SO2 )N－ ]、(三氟甲磺醯基)(九氟丁磺醯基)醯亞胺離子[(CF3 SO2 )(CF3 CF2 CF2 CF2 SO2 )N－ ]等，較佳為貳(三氟甲磺醯基)醯亞胺離子[(CF3 SO2 )2 N－ ]、貳(五氟乙磺醯基)醯亞胺離子[(CF3 CF2 SO2 )2 N－ ]。In the formula (1), A - system (perfluoroalkylsulfonyl) quinone imine ion or perfluoroalkanesulfonate ion. In the case of hydrazine (perfluoroalkylsulfonyl) quinone imine ion, it is an anion represented by formula (3): (R f 1 SO 2 )(R f 2 SO 2 )N - (3) (wherein , R f 1 and R f 2 may be the same or different, and represent a perfluoroalkyl group having 1 to 4 carbon atoms, and a perfluoroalkane having 1 to 4 carbon atoms as shown by R f 1 and R f 2 The base may, for example, be a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group or a nonafluorobutyl group. Specifically, for example, ruthenium (trifluoromethanesulfonyl) quinone imine ion [(CF 3 SO 2 ) 2 N - ], ruthenium (pentafluoroethanesulfonyl) ruthenium ion [(CF 3 CF 2 ) SO 2 ) 2 N - ], hydrazine (heptafluoropropylsulfonyl) quinone imine ion [(CF 3 CF 2 CF 2 SO 2 ) 2 N - ], hydrazine (nonafluorobutylsulfonyl) quinone imine ion [(CF 3 CF 2 CF 2 CF 2 SO 2 ) 2 N - ], (trifluoromethanesulfonyl) (pentafluoroethanesulfonyl) quinone imine ion [(CF 3 SO 2 ) (CF 3 CF 2 SO 2 )N - ], (trifluoromethanesulfonyl) (heptafluoropropylsulfonyl) quinone imine ion [(CF 3 SO 2 )(CF 3 CF 2 CF 2 SO 2 )N - ], (three Fluoromethanesulfonyl)(nonafluorobutylsulfonyl) quinone imine ion [(CF 3 SO 2 )(CF 3 CF 2 CF 2 CF 2 SO 2 )N - ], etc., preferably 贰 (trifluoromethyl) Sulfhydryl) quinone imine ion [(CF 3 SO 2 ) 2 N - ], hydrazine (pentafluoroethanesulfonyl) quinone imine ion [(CF 3 CF 2 SO 2 ) 2 N - ].

以全氟烷磺酸離子而言，可列舉如碳數1至8之全氟烷磺酸離子，具體而言可列舉如三氟甲磺酸離子(CF3 SO3 － )、五氟乙磺酸離子(CF3 CF2 SO3 － )、七氟丙磺酸離子[CF3 (CF2 )2 SO3 － ]、九氟丁磺酸離子[CF3 (CF2 )3 SO3 － ]、十七氟辛磺酸離子[CF3 (CF2 )7 SO3 － ]等，較佳為九氟丁磺酸離子[CF3 (CF2 )3 SO3 － ]。The perfluoroalkanesulfonic acid ion may, for example, be a perfluoroalkanesulfonic acid ion having a carbon number of 1 to 8, and specifically, for example, a trifluoromethanesulfonic acid ion (CF 3 SO 3 - ) or pentafluoroethanesulfonate Acid ions (CF 3 CF 2 SO 3 - ), heptafluoropropanesulfonic acid ions [CF 3 (CF 2 ) 2 SO 3 - ], nonafluorobutanesulfonic acid ions [CF 3 (CF 2 ) 3 SO 3 - ], Heptafluorooctanesulfonic acid ion [CF 3 (CF 2 ) 7 SO 3 - ] or the like is preferably a nonafluorobutanesulfonic acid ion [CF 3 (CF 2 ) 3 SO 3 - ].

式(2 )中，R3 係碳數1至4之烷基或芳香基，較佳為碳數1至4之烷基。此等可列舉如分別與前述所示之碳數1至4之烷基或芳香基相同者。In the formula ( 2 ), R 3 is an alkyl group or an aromatic group having 1 to 4 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms. These may be exemplified by the same as the alkyl group or the aryl group having 1 to 4 carbon atoms as described above.

當R3 為碳數1至4之烷基時，R4 係碳數1至4之烷基、芳香基或芳烷基，較佳為碳數1至4之烷基。此等可列舉如分別與前述所示之碳數1至4之烷基、芳香基或芳烷基相同者。當R3 為芳香基時，此等可列舉如分別與前述碳數1至16之烷基、前述芳香基或前述芳烷基相同者。When R 3 is an alkyl group having 1 to 4 carbon atoms, R 4 is an alkyl group, an aromatic group or an aralkyl group having 1 to 4 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms. These may be exemplified by the same as the alkyl group, the aryl group or the aralkyl group having 1 to 4 carbon atoms as described above. When R 3 is an aromatic group, these may be exemplified by the same as the above-mentioned alkyl group having 1 to 16 carbon atoms, the above-mentioned aromatic group or the aforementioned aralkyl group.

式(2)中，以B－ 所示之陰離子而言，除了前述貳(全氟烷磺醯基)醯亞胺離子或前述全氟烷磺酸離子以外，其他還有全氟烷羧酸離子、無機酸離子、烷磺酸離子、烷基苯磺酸離子、烷羧酸離子、烷基苯羧酸離子、含氰離子或鹵素離子，較佳為貳(全氟烷磺醯基)醯亞胺離子、全氟烷磺酸離子、全氟烷羧酸離子、烷磺酸離子、烷基苯磺酸離子、含氟無機酸離子或含氧酸離子。In the formula (2), in addition to the aforementioned anthracene (perfluoroalkanesulfonyl) quinone imine ion or the above perfluoroalkanesulfonate ion, a perfluoroalkanecarboxylic acid ion is present in the anion represented by B - , inorganic acid ion, alkane sulfonate ion, alkylbenzene sulfonate ion, alkanoic acid ion, alkyl benzene carboxylic acid ion, cyanide ion or halogen ion, preferably fluorene (perfluoroalkanesulfonyl) fluorene Amine ion, perfluoroalkanesulfonate ion, perfluoroalkane acid ion, alkanesulfonate ion, alkylbenzenesulfonate ion, fluorine-containing inorganic acid ion or oxyacid ion.

以全氟烷羧酸離子而言，可列舉如碳數1至8之全氟烷羧酸離子。具體而言可列舉如三氟乙酸離子(CF3 COO－ )、五氟丙酸離子(CF3 CF2 COO－ )、七氟丁酸離子[CF3 (CF2 )2 COO－ ]、十五氟辛酸離子[CF3 (CF2 )6 COO－ ]等，較佳為三氟乙酸離子(CF3 COO－ )。The perfluoroalkanecarboxylic acid ion may, for example, be a perfluoroalkanecarboxylic acid ion having a carbon number of 1 to 8. Specific examples thereof include trifluoroacetic acid ion (CF 3 COO - ), pentafluoropropionic acid ion (CF 3 CF 2 COO - ), heptafluorobutyric acid ion [CF 3 (CF 2 ) 2 COO - ], fifteen The fluorooctanoic acid ion [CF 3 (CF 2 ) 6 COO - ] or the like is preferably a trifluoroacetic acid ion (CF 3 COO - ).

以無機酸離子而言，可列舉如四氟硼酸離子(BF4 － )、六氟磷酸離子(PF6 － )、六氟銻酸離子(SbF6 － )、六氟鉭酸離子(TaF6 － )等含氟無機酸離子，如過氯酸離子(ClO4 － )、硝酸離子(NO3 － )、硫酸離子(SO4 2－ )、磷酸離子(PO4 3－ )、硼酸離子(BO3 3－ )等含氧酸離子；較佳為四氟硼酸離子(BF4 － )、過氯酸離子(ClO4 － )及硝酸離子(NO3－ )。Examples of the inorganic acid ion include tetrafluoroboric acid ion (BF 4 - ), hexafluorophosphate ion (PF 6 - ), hexafluoroantimonate ion (SbF 6 - ), and hexafluoroantimonic acid ion (TaF 6 - Fluorine-containing inorganic acid ions such as perchloric acid ions (ClO 4 - ), nitrate ions (NO 3 - ), sulfate ions (SO 4 2- ), phosphate ions (PO 4 3- ), boric acid ions (BO 3 ) 3- ) an oxo acid ion; preferably a tetrafluoroborate ion (BF 4 - ), a perchlorate ion (ClO 4 - ), and a nitrate ion (NO 3- ).

以烷磺酸離子而言，能舉出如甲磺酸離子(CH3 SO3 － )、乙磺酸離子(CH3 CH2 SO3 － )、丁磺酸離子[CH3 (CH2 )3 SO3 － ]、辛磺酸離子[CH3 (CH2 )7 SO3 － ]等。以烷基苯磺酸離子而言，可列舉如對甲苯磺酸離子(p－CH3 C6 H4 SO3 － )、癸基苯磺酸離子[p－CH3 (CH2 )9 C6 H4 SO3 － ]、十二基苯磺酸離子[p－CH3 (CH2 )11 C6 H4 SO3 － ]、十四基苯磺酸離子[p－CH3 (CH2 )13 C6 H4 SO3 － ]、或此等之支鏈型，較佳為十二基苯磺酸離子[p－CH3 (CH2 )11 C6 H4 SO3 － ]。Examples of the alkanesulfonic acid ion include a methanesulfonic acid ion (CH 3 SO 3 - ), an ethanesulfonic acid ion (CH 3 CH 2 SO 3 - ), and a butanesulfonic acid ion [CH 3 (CH 2 ) 3 . SO 3 - ], octanesulfonic acid ion [CH 3 (CH 2 ) 7 SO 3 - ], and the like. Examples of the alkylbenzenesulfonic acid ion include p-CH 3 C 6 H 4 SO 3 - , decylbenzenesulfonate ion [p-CH 3 (CH 2 ) 9 C 6 H 4 SO 3 - ], dodecylbenzenesulfonic acid ion [p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetradecylbenzenesulfonate ion [p-CH 3 (CH 2 ) 13 C 6 H 4 SO 3 - ], or a branched type thereof, preferably a dodecylbenzenesulfonic acid ion [p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ].

以烷羧酸離子而言，能舉出如甲酸離子(HCOO－ )、乙酸離子(CH3 COO－ )、丙酸離子(CH3 CH2 COO－ )、丁酸離子[CH3 (CH2 )2 COO－ ]、辛酸離子[CH3 (CH2 )6 COO－ ]、癸酸離子[CH3 (CH2 )8 COO－ ]等。以烷基苯羧酸離子而言，可列舉如苯甲酸離子(C6 H5 COO－ )、柳酸[o－C6 H4 (OH)COO－ ]等。Examples of the alkanoic acid ion include formic acid ion (HCOO - ), acetic acid ion (CH 3 COO - ), propionic acid ion (CH 3 CH 2 COO - ), butyric acid ion [CH 3 (CH 2 ) 2 COO - ], octanoic acid ion [CH 3 (CH 2 ) 6 COO - ], decanoic acid ion [CH 3 (CH 2 ) 8 COO - ], and the like. Examples of the alkylbenzenecarboxylic acid ion include a benzoic acid ion (C 6 H 5 COO - ), a salicylic acid [o-C 6 H 4 (OH) COO - ], and the like.

以含氰離子而言，可列舉如二氰胺離子[N(CN2 )－ ]，硫氰酸離子(SCN－ )等。以鹵素離子而言，可列舉如氟離子(F－ )、氯離子(Cl－ )、溴離子(Br－ )或碘離子(I－ )。Examples of the cyanide-containing ion include dicyanamide ion [N(CN 2 ) - ], thiocyanate ion (SCN - ), and the like. Examples of the halogen ion include a fluoride ion (F - ), a chloride ion (Cl - ), a bromide ion (Br - ), or an iodide ion (I - ).

以鏻鹽(1)之具體例而言，可列舉如以下所示者。而且，以下分別表示為：Me為甲基、Et為乙基、Pr為丙基、Bu為丁基、Ph為苯基、Bn為苯甲基、Hep為庚基、Ddec為十二基、Hdec為十六基。Specific examples of the onium salt (1) include those shown below. Further, the following are respectively represented by Me being methyl, Et being ethyl, Pr being propyl, Bu being butyl, Ph being phenyl, Bn being benzyl, Hep being heptyl, Ddec being dodecyl, Hdec It is a sixteen base.

例如可列舉如四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]、四丁鏻＝貳(五氟乙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 CF2 SO2 )2 N－ ]、四丁鏻＝貳(七氟丙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 CF2 CF2 SO2 )2 N－ ]、四丁鏻＝貳(九氟丁磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 CF2 CF2 CF2 SO2 )2 N－ ]、四丁鏻＝(三氟甲磺醯基)(五氟乙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )(CF3 CF2 SO2 )N－ ]、四丁鏻＝(三氟甲磺醯基)(七氟丙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )(CF3 CF2 CF2 SO2 )N－ ]、四丁鏻＝(三氟甲磺醯基)(九氟丁磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )(CF3 CF2 CF2 CF2 SO2 )N－ ]、四甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Me4 P＋ ．(CF3 SO2 )2 N－ ]、四乙鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Et4 P＋ ．(CF3 SO2 )2 N－ ]、四丙鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Pr4 P＋ ．(CF3 SO2 )2 N－ ]、三甲基苯鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Me3 PhP＋ ．(CF3 SO2 )2 N－ ]、三乙基苯鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Et3 PhP＋ ．(CF3 SO2 )2 N－ ]、三丙基苯鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Pr3 PhP＋ ．(CF3 SO2 )2 N－ ]、三丁基苯鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu3 PhP＋ ．(CF3 SO2 )2 N－ ]、三甲基苯甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Me3 BnP＋ ．(CF3 SO2 )2 N－ ]、三乙基苯甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Et3 BnP＋ ．(CF3 SO2 )2 N－ ]、三丙基苯甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Pr3 BnP＋ ．(CF3 SO2 )2 N－ ]、三丁基苯甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu3 BnP＋ ．(CF3 SO2 )2 N－ ]、四苯鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph4 P＋ ．(CF3 SO2 )2 N－ ]、三苯基甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 MeP＋ ．(CF3 SO2 )2 N－ ]、三苯基乙鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 EtP＋ ．(CF3 SO2 )2 N－ ]、三苯基丙鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 PrP＋ ．(CF3 SO2 )2 N－ ]、三苯基丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 BuP＋ ．(CF3 SO2 )2 N－ ]、三苯基庚鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 HepP＋ ．(CF3 SO2 )2 N－ ]、三苯基十二鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 DdecP＋ ．(CF3 SO2 )2 N－ ]、三苯基十六鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 HdecP＋ ．(CF3 SO2 )2 N－ ]、三苯基苯甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 BnP＋ ．(CF3 SO2 )2 N－ ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]、四丁鏻＝五氟乙磺酸鹽[Bu4 P＋ ．CF3 CF2 SO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]、四丁鏻＝十七氟辛磺酸鹽[Bu4 P＋ ．CF3 (CF2 )7 SO3 － ]、四甲鏻＝三氟甲磺酸鹽[Me4 P＋ ．CF3 SO3 － ]、四乙鏻＝三氟甲磺酸鹽[Et4 P＋ ．CF3 SO3 － ]、四丙鏻＝三氟甲磺酸鹽[Pr4 P＋ ．CF3 SO3 － ]、三甲基苯鏻＝三氟甲磺酸鹽[Me3 PhP＋ ．CF3 SO3 － ]、三乙基苯鏻＝三氟甲磺酸鹽[Et3 PhP＋ ．CF3 SO3 － ]、三丙基苯鏻＝三氟甲磺酸鹽[Pr3 PhP＋ ．CF3 SO3 － ]、三丁基苯鏻＝三氟甲磺酸鹽[Bu3 PhP＋ ．CF3 SO3 － ]、三甲基苯甲鏻＝三氟甲磺酸鹽[Me3 BnP＋ ．CF3 SO3 － ]、三乙基苯甲鏻＝三氟甲磺酸鹽[Et3 BnP＋ ．CF3 SO3 － ]、三丙基苯甲鏻＝三氟甲磺酸鹽[Pr3 BnP＋ ．CF3 SO3 － ]、三丁基苯甲鏻＝三氟甲磺酸鹽[Bu3 BnP＋ ．CF3 SO3 － ]、四苯鏻＝三氟甲磺酸鹽[Ph4 P＋ ．CF3 SO3 － ]、三苯基甲鏻＝三氟甲磺酸鹽[Ph3 MeP＋ ．CF3 SO3 － ]、三苯基乙鏻＝三氟甲磺酸鹽[Ph3 EtP＋ ．CF3 SO3 － ]、三苯基丙鏻＝三氟甲磺酸鹽[Ph3 PrP＋ ．CF3 SO3 － ]、三苯基丁鏻＝三氟甲磺酸鹽[Ph3 BuP＋ ．CF3 SO3 － ]、三苯基庚鏻＝三氟甲磺酸鹽[Ph3 HepP＋ ．CF3 SO3 － ]、三苯基十二鏻＝三氟甲磺酸鹽[Ph3 DdecP＋ ．CF3 SO3 － ]、三苯基十六鏻＝三氟甲磺酸鹽[Ph3 HdecP＋ ．CF3 SO3 － ]、三苯基苯甲鏻＝三氟甲磺酸鹽[Ph3 BnP＋ ．CF3 SO3 － ]、四乙鏻＝五氟乙磺酸鹽[Et4 P＋ ．CF3 CF2 SO3 － ]、三乙基苯鏻＝五氟乙磺酸鹽[Et3 PhP＋ ．CF3 CF2 SO3 － ]、三丁基苯鏻＝五氟乙磺酸鹽[Bu3 PhP＋ ．CF3 CF2 SO3 － ]、三乙基苯甲鏻＝五氟乙磺酸鹽[Et3 BnP＋ ．CF3 CF2 SO3 － ]、三丁基苯甲鏻＝五氟乙磺酸[Bu3 BnP＋ ．CF3 CF2 SO3 － ]、四乙鏻＝九氟丁磺酸鹽[Et4 P＋ ．CF3 (CF2 )3 SO3 － ]、三乙基苯鏻＝九氟丁磺酸鹽[Et3 PhP＋ ．CF3 (CF2 )3 SO3 － ]、三丁基苯鏻＝九氟丁磺酸鹽[Bu3 PhP＋ ．CF3 (CF2 )3 SO3 － ]、三乙基苯甲鏻＝九氟丁磺酸鹽[Et3 BnP＋ ．CF3 (CF2 )3 SO3 － ]、三丁基苯甲鏻＝九氟丁磺酸鹽[Bu3 BnP＋ ．CF3 (CF2 )3 SO3 － ]、四苯鏻＝九氟丁磺酸鹽[Ph4 P＋ ．CF3 (CF2 )3 SO3 － ]、三苯基甲鏻＝九氟丁磺酸鹽[Ph3 MeP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基乙鏻＝九氟丁磺酸鹽[Ph3 EtP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基丙鏻＝九氟丁磺酸鹽[Ph3 PrP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基丁鏻＝九氟丁磺酸鹽[Ph3 BuP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基庚鏻＝九氟丁磺酸鹽[Ph3 HepP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基十二鏻＝九氟丁磺酸鹽[Ph3 DdecP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基十六鏻＝九氟丁磺酸鹽[Ph3 HdecP＋ ．CF3 (CF2 )3 SO3 － ]、三苯基苯甲鏻＝九氟丁磺酸鹽[Ph3 BnP＋ ．CF3 (CF2 )3 SO3 － ]、四乙鏻＝十七氟辛磺酸鹽[Et4 P＋ ．CF3 (CF2 )7 SO3 － ]、三乙基苯鏻＝十七氟辛磺酸鹽[Et3 PhP＋ ．CF3 (CF2 )7 SO3 － ]、三丁基苯鏻＝十七氟辛磺酸鹽[Bu3 PhP＋ ．CF3 (CF2 )7 SO3 － ]、三乙基苯甲鏻＝十七氟辛磺酸鹽[Et3 BnP＋ ．CF3 (CF2 )7 SO3 － ]、三丁基苯甲鏻＝十七氟辛磺酸鹽[Bu3 BnP＋ ．CF3 (CF2 )7 SO3 － ]等；較佳為四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]、四丁鏻＝貳(五氟乙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 CF2 SO2 )2 N－ ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]、四丁鏻＝五氟乙磺酸鹽[Bu4 P＋ ．CF3 CF2 SO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]；特佳為四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]。For example, tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ], tetrabutyl hydrazine = hydrazine (pentafluoroethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 CF 2 SO 2 ) 2 N - ], tetrabutyl hydrazine = hydrazine (heptafluoropropylsulfonyl) quinone imide salt [Bu 4 P + . (CF 3 CF 2 CF 2 SO 2 ) 2 N - ], tetrabutyl hydrazine = hydrazine (nonafluorobutylsulfonyl) quinone imide salt [Bu 4 P + . (CF 3 CF 2 CF 2 CF 2 SO 2 ) 2 N - ], tetrabutyl hydrazine = (trifluoromethanesulfonyl) (pentafluoroethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 )(CF 3 CF 2 SO 2 )N - ], tetrabutyl hydrazine = (trifluoromethanesulfonyl) (heptafluoropropylsulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 )(CF 3 CF 2 CF 2 SO 2 )N - ], tetrabutyl hydrazine = (trifluoromethanesulfonyl) (nonafluorobutsulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 )(CF 3 CF 2 CF 2 CF 2 SO 2 )N - ], tetramethyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Me 4 P + . (CF 3 SO 2 ) 2 N - ], tetraethyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Et 4 P + . (CF 3 SO 2 ) 2 N - ], tetrapropyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Pr 4 P + . (CF 3 SO 2 ) 2 N - ], Trimethyl benzoquinone = 三氟 (trifluoromethanesulfonyl) quinone imide salt [Me 3 PhP + . (CF 3 SO 2 ) 2 N - ], triethyl benzoquinone = fluorene (trifluoromethanesulfonyl) quinone imide salt [Et 3 PhP + . (CF 3 SO 2 ) 2 N - ], tripropyl benzoquinone = fluorene (trifluoromethanesulfonyl) quinone imide salt [Pr 3 PhP + . (CF 3 SO 2 ) 2 N - ], Tributylphthalide = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 3 PhP + . (CF 3 SO 2 ) 2 N - ], trimethylbenzhydrazide = fluorene (trifluoromethanesulfonyl) quinone imide salt [Me 3 BnP + . (CF 3 SO 2 ) 2 N - ], triethyl benzamidine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Et 3 BnP + . (CF 3 SO 2 ) 2 N - ], tripropyl benzamidine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Pr 3 BnP + . (CF 3 SO 2 ) 2 N - ], tributyl benzamidine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 3 BnP + . (CF 3 SO 2 ) 2 N - ], tetraphenylphosphonium = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 4 P + . (CF 3 SO 2 ) 2 N - ], triphenylformamidine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 MeP + . (CF 3 SO 2 ) 2 N - ], triphenylacetamidine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 EtP + . (CF 3 SO 2 ) 2 N - ], triphenylpropanoid = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 PrP + . (CF 3 SO 2 ) 2 N - ], triphenylbutyrene = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 BuP + . (CF 3 SO 2 ) 2 N - ], triphenylheptane = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 HepP + . (CF 3 SO 2 ) 2 N - ], triphenyldodecanium = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 DdecP + . (CF 3 SO 2 ) 2 N - ], triphenyl hexadecane = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 HdecP + . (CF 3 SO 2 ) 2 N - ], triphenyl benzamidine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 BnP + . (CF 3 SO 2 ) 2 N - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ], tetrabutyl hydrazine = pentafluoroethanesulfonate [Bu 4 P + . CF 3 CF 2 SO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ], tetrabutyl hydrazine = heptadecafluorooctane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 7 SO 3 - ], tetramethyl hydrazine = triflate [Me 4 P + . CF 3 SO 3 - ], tetraethyl hydrazine = triflate [Et 4 P + . CF 3 SO 3 - ], tetrapropyl hydrazine = triflate [Pr 4 P + . CF 3 SO 3 - ], trimethylphenylhydrazine = triflate [Me 3 PhP + . CF 3 SO 3 - ], triethyl benzoquinone = triflate [Et 3 PhP + . CF 3 SO 3 - ], tripropyl benzoquinone = triflate [Pr 3 PhP + . CF 3 SO 3 - ], tributylphthalide = triflate [Bu 3 PhP + . CF 3 SO 3 - ], trimethyl benzamidine = triflate [Me 3 BnP + . CF 3 SO 3 - ], triethyl benzamidine = triflate [Et 3 BnP + . CF 3 SO 3 - ], tripropyl benzamidine = triflate [Pr 3 BnP + . CF 3 SO 3 - ], tributyl benzamidine = triflate [Bu 3 BnP + . CF 3 SO 3 - ], tetraphenylphosphonium = triflate [Ph 4 P + . CF 3 SO 3 - ], triphenylformamidine = triflate [Ph 3 MeP + . CF 3 SO 3 - ], triphenylacetamidine = triflate [Ph 3 EtP + . CF 3 SO 3 - ], triphenylpropionamidine = triflate [Ph 3 PrP + . CF 3 SO 3 - ], triphenylbutyrene = triflate [Ph 3 BuP + . CF 3 SO 3 - ], triphenylheptane = triflate [Ph 3 HepP + . CF 3 SO 3 - ], triphenyldodecanium = triflate [Ph 3 DdecP + . CF 3 SO 3 - ], triphenyl hexadecane = triflate [Ph 3 HdecP + . CF 3 SO 3 - ], triphenyl benzamidine = triflate [Ph 3 BnP + . CF 3 SO 3 - ], tetraethyl hydrazine = pentafluoroethanesulfonate [Et 4 P + . CF 3 CF 2 SO 3 - ], triethylphenylhydrazine = pentafluoroethanesulfonate [Et 3 PhP + . CF 3 CF 2 SO 3 - ], tributylphthalide = pentafluoroethanesulfonate [Bu 3 PhP + . CF 3 CF 2 SO 3 - ], triethyl benzamidine = pentafluoroethanesulfonate [Et 3 BnP + . CF 3 CF 2 SO 3 - ], tributyl benzamidine = pentafluoroethanesulfonic acid [Bu 3 BnP + . CF 3 CF 2 SO 3 - ], tetraethyl hydrazine = nonafluorobutane sulfonate [Et 4 P + . CF 3 (CF 2 ) 3 SO 3 - ], triethylphenylhydrazine = nonafluorobutanesulfonate [Et 3 PhP + . CF 3 (CF 2 ) 3 SO 3 - ], tributylphthalide = nonafluorobutanesulfonate [Bu 3 PhP + . CF 3 (CF 2 ) 3 SO 3 - ], triethyl benzamidine = nonafluorobutanesulfonate [Et 3 BnP + . CF 3 (CF 2 ) 3 SO 3 - ], tributyl benzamidine = nonafluorobutanesulfonate [Bu 3 BnP + . CF 3 (CF 2 ) 3 SO 3 - ], tetraphenylphosphonium = nonafluorobutanesulfonate [Ph 4 P + . CF 3 (CF 2 ) 3 SO 3 - ], triphenylformamidine = nonafluorobutanesulfonate [Ph 3 MeP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenylacetamidine = nonafluorobutanesulfonate [Ph 3 EtP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenylpropionamidine = nonafluorobutanesulfonate [Ph 3 PrP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenylbutyrene = nonafluorobutanesulfonate [Ph 3 BuP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenylheptane = nonafluorobutanesulfonate [Ph 3 HepP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenyldodecanium = nonafluorobutanesulfonate [Ph 3 DdecP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenylhexadecane = nonafluorobutanesulfonate [Ph 3 HdecP + . CF 3 (CF 2 ) 3 SO 3 - ], triphenyl benzamidine = nonafluorobutanesulfonate [Ph 3 BnP + . CF 3 (CF 2 ) 3 SO 3 - ], tetraethyl hydrazine = heptadecafluorooctane sulfonate [Et 4 P + . CF 3 (CF 2 ) 7 SO 3 - ], triethyl benzoquinone = heptadecafluorooctane sulfonate [Et 3 PhP + . CF 3 (CF 2 ) 7 SO 3 - ], tributylphthalide = heptadecafluorooctane sulfonate [Bu 3 PhP + . CF 3 (CF 2 ) 7 SO 3 - ], triethyl benzamidine = heptadecafluorooctane sulfonate [Et 3 BnP + . CF 3 (CF 2 ) 7 SO 3 - ], tributyl benzamidine = heptadecafluorooctane sulfonate [Bu 3 BnP + . CF 3 (CF 2 ) 7 SO 3 - ] and the like; preferably tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ], tetrabutyl hydrazine = hydrazine (pentafluoroethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 CF 2 SO 2 ) 2 N - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ], tetrabutyl hydrazine = pentafluoroethanesulfonate [Bu 4 P + . CF 3 CF 2 SO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ]; especially preferred is tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ].

以鏻鹽(2)之具體例而言，除了在前述已舉出之例以外，其他可列舉如四丁鏻＝三氟乙酸鹽[Bu4 P＋ ．CF3 COO－ ]、四丁鏻＝四氟硼酸鹽[Bu4 P＋ ．BF4 － ]、四丁鏻＝六氟磷酸鹽[Bu4 P＋ ．PF6 － ]、四丁鏻＝甲磺酸鹽[Bu4 P＋ ．CH3 SO3 － ]、四丁鏻＝對甲苯磺酸鹽[Bu4 P＋ ．p－CH3 C6 H4 SO3 － ]、四丁鏻＝十二基苯磺酸鹽[Bu4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四丁鏻＝過氯酸鹽[Bu4 P＋ ．ClO4 － ]、四丁鏻＝硝酸鹽[Bu4 P＋ ．NO3 － ]、溴化四丁鏻[Bu4 P＋ ．Br－ ]、四乙鏻＝三氟乙酸鹽[Et4 P＋ ．CF3 COO－ ]、四乙鏻＝四氟硼酸鹽[Et4 P＋ ．BF4 － ]、四乙鏻＝六氟磷酸鹽[Et4 P＋ ．PF6 － ]、四乙鏻＝甲磺酸鹽[Et4 P＋ ．CH3 SO3 － ]、四乙鏻＝對甲苯磺酸鹽[Et4 P＋ ．p－CH3 C6 H4 SO3 － ]、四乙鏻＝十二基苯磺酸鹽[Et4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四乙鏻＝過氯酸鹽[Et4 P＋ ．ClO4 － ]、四乙鏻＝硝酸鹽[Et4 P＋ ．NO3 － ]、三乙基苯甲鏻＝三氟乙酸鹽[Et3 BnP＋ ．CF3 COO－ ]、三乙基苯甲鏻＝四氟硼酸鹽[Et3 BnP＋ ．BF4 － ]、三乙基苯甲鏻＝六氟磷酸鹽[Et3 BnP＋ ．PF6 － ]、三乙基苯甲鏻＝甲磺酸鹽[Et3 BnP＋ ．CH3 SO3 － ]、三乙基苯甲鏻＝對甲苯磺酸鹽[Et3 BnP＋ ．p－CH3 C6 H4 SO3 － ]、三乙基苯甲鏻＝十二基苯磺酸鹽[Et3 BnP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三乙基苯甲鏻＝過氯酸鹽[Et3 BnP＋ ．ClO4 － ]、三乙基苯甲鏻＝硝酸鹽[Et3 BnP＋ ．NO3 － ]、三丁基苯甲鏻＝三氟乙酸鹽[Bu3 BnP＋ ．CF3 COO－ ]、三丁基苯甲鏻＝四氟硼酸鹽[Bu3 BnP＋ ．BF4 － ]、三丁基苯甲鏻＝六氟磷酸鹽[Bu3 BnP＋ ．PF6 － ]、三丁基苯甲鏻＝甲磺酸鹽[Bu3 BnP＋ ．CH3 SO3 － ]、三丁基苯甲鏻＝對甲苯磺酸鹽[Bu3 BnP＋ ．p－CH3 C6 H4 SO3 － ]、三丁基苯甲鏻＝十二基苯磺酸鹽[Bu3 BnP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三丁基苯甲鏻＝過氯酸鹽[Bu3 BnP＋ ．ClO4 － ]、三丁基苯甲鏻＝硝酸鹽[Bu3 BnP＋ ．NO3 － ]、四苯鏻＝三氟乙酸鹽[Ph4 P＋ ．CF3 COO－ ]、四苯鏻＝四氟硼酸鹽[Ph4 P＋ ．BF4 － ]、四苯鏻＝六氟磷酸鹽[Ph4 P＋ ．PF6 － ]、四苯鏻＝甲磺酸鹽[Ph4 P＋ ．CH3 SO3 － ]、四苯鏻＝對甲苯磺酸鹽[Ph4 P＋ ．p－CH3 C6 H4 SO3 － ]、四苯鏻＝十二基苯磺酸鹽[Ph4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四苯鏻＝過氯酸鹽[Ph4 P＋ ．ClO4 － ]、四苯鏻＝硝酸鹽[Ph4 P＋ ．NO3 － ]、三苯基甲鏻＝三氟乙酸鹽[Ph3 MeP＋ ．CF3 COO－ ]、三苯基甲鏻＝四氟硼酸鹽[Ph3 MeP＋ ．BF4 － ]、三苯基甲鏻＝六氟磷酸鹽[Ph3 MeP＋ ．PF6 － ]、三苯基甲鏻＝甲磺酸鹽[Ph3 MeP＋ ．CH3 SO3 － ]、三苯基甲鏻＝對甲苯磺酸鹽[Ph3 MeP＋ ．p－CH3 C6 H4 SO3 － ]、三苯基甲鏻＝十二基苯磺酸鹽[Ph3 MeP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三苯基甲鏻＝過氯酸鹽[Ph3 MeP＋ ．ClO4 － ]、三苯基甲鏻＝硝酸鹽[Ph3 MeP＋ ．NO3 － ]、三苯基乙鏻＝三氟乙酸鹽[Ph3 EtP＋ ．CF3 COO－ ]、三苯基乙鏻＝四氟硼酸鹽[Ph3 EtP＋ ．BF4 － ]、三苯基乙鏻＝六氟磷酸鹽[Ph3 EtP＋ ．PF6 － ]、三苯基乙鏻＝甲磺酸鹽[Ph3 EtP＋ ．CH3 SO3 － ]、三苯基乙鏻＝對甲苯磺酸鹽[Ph3 EtP＋ ．p－CH3 C6 H4 SO3 － ]、三苯基乙鏻＝十二基苯磺酸鹽[Ph3 EtP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三苯基乙鏻＝過氯酸鹽[Ph3 EtP＋ ．ClO4 － ]、三苯基乙鏻＝硝酸鹽[Ph3 EtP＋ ．NO3 － ]、三苯基丁鏻＝三氟乙酸鹽[Ph3 BuP＋ ．CF3 COO－ ]、三苯基丁鏻＝四氟硼酸鹽[Ph3 BuP＋ ．BF4 － ]、三苯基丁鏻＝六氟磷酸鹽[Ph3 BuP＋ ．PF6 － ]、三苯基丁鏻＝甲磺酸鹽[Ph3 BuP＋ ．CH3 SO3 － ]、三苯基丁鏻＝對甲苯磺酸鹽[Ph3 BuP＋ ．p－CH3 C6 H4 SO3 － ]、三苯基丁鏻＝十二基苯磺酸鹽[Ph3 BuP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三苯基丁鏻＝過氯酸鹽[Ph3 BuP＋ ．ClO4 － ]、三苯基丁鏻＝硝酸鹽[Ph3 BuP＋ ．NO3 － ]、三苯基庚鏻＝三氟乙酸鹽[Ph3 HepP＋ ．CF3 COO－ ]、三苯基庚鏻＝四氟硼酸鹽[Ph3 HepP＋ ．BF4 － ]、三苯基庚鏻＝六氟磷酸鹽[Ph3 HepP＋ ．PF6 － ]、三苯基庚鏻＝甲磺酸鹽[Ph3 HepP＋ ．CH3 SO3 － ]、三苯基庚鏻＝對甲苯磺酸鹽[Ph3 HepP＋ ．p－CH3 C6 H4 SO3 － ]、三苯基庚鏻＝十二基苯磺酸鹽[Ph3 HepP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三苯基庚鏻＝過氯酸鹽[Ph3 HepP＋ ．ClO4 － ]、三苯基庚鏻＝硝酸鹽[Ph3 HepP＋ ．NO3 － ]、三苯基苯甲鏻＝三氟乙酸鹽[Ph3 BnP＋ ．CF3 COO－ ]、三苯基苯甲鏻＝四氟硼酸鹽[Ph3 BnP＋ ．BF4 － ]、三苯基苯甲鏻＝六氟磷酸鹽[Ph3 BnP＋ ．PF6 － ]、三苯基苯甲鏻＝甲磺酸鹽[Ph3 BnP＋ ．CH3 SO3 － ]、三苯基苯甲鏻＝對甲苯磺酸鹽[Ph3 BnP＋ ．p－CH3 C6 H4 SO3 － ]、三苯基苯甲鏻＝十二基苯磺酸鹽[Ph3 BnP＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、三苯基苯甲鏻＝過氯酸鹽[Ph3 BnP＋ ．ClO4 － ]、三苯基苯甲鏻＝硝酸鹽[Ph3 BnP＋ ．NO3 － ]等。Specific examples of the onium salt (2) include, in addition to the above-exemplified examples, tetrabutylphosphonium = trifluoroacetate [Bu 4 P + . CF 3 COO - ], tetrabutyl hydrazine = tetrafluoroborate [Bu 4 P + . BF 4 - ], tetrabutyl hydrazine = hexafluorophosphate [Bu 4 P + . PF 6 - ], tetrabutyl hydrazine = mesylate [Bu 4 P + . CH 3 SO 3 - ], tetrabutyl hydrazine = p-toluenesulfonate [Bu 4 P + . p-CH 3 C 6 H 4 SO 3 - ], tetrabutyl hydrazine = dodecylbenzenesulfonate [Bu 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetrabutyl hydrazine = perchlorate [Bu 4 P + . ClO 4 - ], tetrabutyl hydrazine = nitrate [Bu 4 P + . NO 3 - ], tetrabutyl bromide [Bu 4 P + . Br - ], tetraethyl hydrazine = trifluoroacetate [Et 4 P + . CF 3 COO - ], tetraethyl hydrazine = tetrafluoroborate [Et 4 P + . BF 4 - ], tetraethyl hydrazine = hexafluorophosphate [Et 4 P + . PF 6 - ], tetraethyl hydrazine = mesylate [Et 4 P + . CH 3 SO 3 - ], tetraethyl hydrazine = p-toluenesulfonate [Et 4 P + . p-CH 3 C 6 H 4 SO 3 - ], tetraethyl hydrazine = dodecylbenzene sulfonate [Et 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetraethyl hydrazine = perchlorate [Et 4 P + . ClO 4 - ], tetraethyl hydrazine = nitrate [Et 4 P + . NO 3 - ], triethyl benzamidine = trifluoroacetate [Et 3 BnP + . CF 3 COO - ], triethyl benzamidine = tetrafluoroborate [Et 3 BnP + . BF 4 - ], triethyl benzamidine = hexafluorophosphate [Et 3 BnP + . PF 6 - ], triethyl benzamidine = mesylate [Et 3 BnP + . CH 3 SO 3 - ], triethyl benzamidine = p-toluenesulfonate [Et 3 BnP + . p-CH 3 C 6 H 4 SO 3 - ], triethyl benzamidine = dodecylbenzenesulfonate [Et 3 BnP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], triethyl benzamidine = perchlorate [Et 3 BnP + . ClO 4 - ], triethyl benzamidine = nitrate [Et 3 BnP + . NO 3 - ], tributyl benzamidine = trifluoroacetate [Bu 3 BnP + . CF 3 COO - ], tributyl benzamidine = tetrafluoroborate [Bu 3 BnP + . BF 4 - ], tributyl benzamidine = hexafluorophosphate [Bu 3 BnP + . PF 6 - ], tributyl benzamidine = mesylate [Bu 3 BnP + . CH 3 SO 3 - ], tributyl benzamidine = p-toluenesulfonate [Bu 3 BnP + . p-CH 3 C 6 H 4 SO 3 - ], tributyl benzamidine = dodecylbenzenesulfonate [Bu 3 BnP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tributyl benzamidine = perchlorate [Bu 3 BnP + . ClO 4 - ], tributyl benzamidine = nitrate [Bu 3 BnP + . NO 3 - ], tetraphenylphosphonium = trifluoroacetate [Ph 4 P + . CF 3 COO - ], tetraphenyl hydrazine = tetrafluoroborate [Ph 4 P + . BF 4 - ], tetraphenylphosphonium = hexafluorophosphate [Ph 4 P + . PF 6 - ], tetraphenyl hydrazine = mesylate [Ph 4 P + . CH 3 SO 3 - ], tetraphenylphosphonium = p-toluenesulfonate [Ph 4 P + . p-CH 3 C 6 H 4 SO 3 - ], tetraphenylphosphonium = dodecylbenzenesulfonate [Ph 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetraphenylphosphonium = perchlorate [Ph 4 P + . ClO 4 - ], tetraphenyl hydrazine = nitrate [Ph 4 P + . NO 3 - ], triphenylformamidine = trifluoroacetate [Ph 3 MeP + . CF 3 COO - ], triphenylformamidine = tetrafluoroborate [Ph 3 MeP + . BF 4 - ], triphenylformamidine = hexafluorophosphate [Ph 3 MeP + . PF 6 - ], triphenylformamidine = mesylate [Ph 3 MeP + . CH 3 SO 3 - ], triphenylformamidine = p-toluenesulfonate [Ph 3 MeP + . p-CH 3 C 6 H 4 SO 3 - ], triphenylformamidine = dodecylbenzenesulfonate [Ph 3 MeP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], triphenylformamidine = perchlorate [Ph 3 MeP + . ClO 4 - ], triphenylformamidine = nitrate [Ph 3 MeP + . NO 3 - ], triphenylacetamidine = trifluoroacetate [Ph 3 EtP + . CF 3 COO - ], triphenylacetamidine = tetrafluoroborate [Ph 3 EtP + . BF 4 - ], triphenylacetamidine = hexafluorophosphate [Ph 3 EtP + . PF 6 - ], triphenylacetamidine = mesylate [Ph 3 EtP + . CH 3 SO 3 - ], triphenylacetamidine = p-toluenesulfonate [Ph 3 EtP + . p-CH 3 C 6 H 4 SO 3 - ], triphenylacetamidine = dodecylbenzenesulfonate [Ph 3 EtP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], triphenylacetamidine = perchlorate [Ph 3 EtP + . ClO 4 - ], triphenylacetamidine = nitrate [Ph 3 EtP + . NO 3 - ], triphenylbutyrene = trifluoroacetate [Ph 3 BuP + . CF 3 COO - ], triphenylbutyrate = tetrafluoroborate [Ph 3 BuP + . BF 4 - ], triphenylbutyrate = hexafluorophosphate [Ph 3 BuP + . PF 6 - ], triphenylbutyrate = mesylate [Ph 3 BuP + . CH 3 SO 3 - ], triphenylbutyrate = p-toluenesulfonate [Ph 3 BuP + . p-CH 3 C 6 H 4 SO 3 - ], triphenylbutyrene = dodecylbenzenesulfonate [Ph 3 BuP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], triphenylbutyrene = perchlorate [Ph 3 BuP + . ClO 4 - ], triphenylbutyrate = nitrate [Ph 3 BuP + . NO 3 - ], triphenylheptane = trifluoroacetate [Ph 3 HepP + . CF 3 COO - ], triphenylheptane = tetrafluoroborate [Ph 3 HepP + . BF 4 - ], triphenylheptane = hexafluorophosphate [Ph 3 HepP + . PF 6 - ], triphenylheptane = methanesulfonate [Ph 3 HepP + . CH 3 SO 3 - ], triphenylheptane = p-toluenesulfonate [Ph 3 HepP + . p-CH 3 C 6 H 4 SO 3 - ], triphenylheptane = dodecylbenzenesulfonate [Ph 3 HepP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], triphenylheptane = perchlorate [Ph 3 HepP + . ClO 4 - ], triphenylheptane = nitrate [Ph 3 HepP + . NO 3 - ], triphenyl benzamidine = trifluoroacetate [Ph 3 BnP + . CF 3 COO - ], triphenyl benzamidine = tetrafluoroborate [Ph 3 BnP + . BF 4 - ], triphenyl benzamidine = hexafluorophosphate [Ph 3 BnP + . PF 6 - ], triphenyl benzamidine = mesylate [Ph 3 BnP + . CH 3 SO 3 - ], triphenyl benzamidine = p-toluenesulfonate [Ph 3 BnP + . p-CH 3 C 6 H 4 SO 3 - ], triphenyl benzamidine = dodecylbenzenesulfonate [Ph 3 BnP + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], triphenyl benzamidine = perchlorate [Ph 3 BnP + . ClO 4 - ], triphenyl benzamidine = nitrate [Ph 3 BnP + . NO 3 - ] and so on.

在鏻鹽(1)之至少1種與鏻鹽(2)之至少1種的併用中，特佳係R1 及R2 同時為碳數1至4之烷基之鏻鹽(1)之至少1種與R3 及R4 同時為碳數1至4之烷基之鏻鹽(2)之至少1種的併用。In combination of at least one of the cerium salt (1) and at least one of the cerium salt (2), at least one of the sulfonium salts (1) in which the R 1 and R 2 are simultaneously an alkyl group having 1 to 4 carbon atoms. One type of at least one of the sulfonium salts (2) having an alkyl group having 1 to 4 carbon atoms at the same time as R 3 and R 4 is used in combination.

以具體例而言，可列舉例如：四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝貳(五氟乙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 CF2 SO2 )2 N－ ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝五氟乙磺酸鹽[Bu4 P＋ ．CF3 CF2 SO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝三氟乙酸鹽[Bu4 P＋ ．CF3 COO－ ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝四氟硼酸鹽[Bu4 P＋ ．BF4 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝六氟磷酸鹽[Bu4 P＋ ．PF6 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝甲磺酸鹽[Bu4 P＋ ．CH3 SO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝對甲苯磺酸鹽[Bu4 P＋ ．p－CH3 C6 H4 SO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝十二基苯磺酸鹽[Bu4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝過氯酸鹽[Bu4 P＋ ．C1 O4 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝硝酸鹽[Bu4 P＋ ．NO3 － ]、四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]與溴化四丁鏻[Bu4 P＋ ．Br－ ]、四乙鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Et4 P＋ ．(CF3 SO2 )2 N－ ]與四丁鏻＝十二基苯磺酸鹽[Bu4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝五氟乙磺酸鹽[Bu4 P＋ ．CF3 CF2 SO3 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝三氟乙酸鹽[Bu4 P＋ ．CF3 COO－ ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝四氟硼酸鹽[Bu4 P＋ ．BF4 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝六氟磷酸鹽[Bu4 P＋ ．PF6 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝甲磺酸鹽[Bu4 P＋ ．CH3 SO3 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝對甲苯磺酸鹽[Bu4 P＋ ．p－CH3 C6 H4 SO3 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝十二基苯磺酸鹽[Bu4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝過氯酸鹽[Bu4 P＋ ．ClO4 － ]、四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]與四丁鏻＝硝酸鹽[Bu4 P＋ ．NO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝五氟乙磺酸鹽[Bu4 P＋ ．CF3 CF2 SO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝三氟乙酸鹽[Bu4 P＋ ．CF3 COO－ ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝四氟硼酸鹽[Bu4 P＋ ．BF4 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝六氟磷酸鹽[Bu4 P＋ ．PF6 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝甲磺酸鹽[Bu4 P＋ ．CH3 SO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝對甲苯磺酸鹽[Bu4 P＋ ．p－CH3 C6 H4 SO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝十二基苯磺酸鹽[Bu4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝過氯酸鹽[Bu4 P＋ ．ClO4 － ]、四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]與四丁鏻＝硝酸鹽[Bu4 P＋ ．NO3 － ]等。Specific examples include, for example, tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = hydrazine (pentafluoroethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 CF 2 SO 2 ) 2 N - ], tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ], tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] and tetrabutyl hydrazine = pentafluoroethanesulfonate [Bu 4 P + . CF 3 CF 2 SO 3 - ], tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ], tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = trifluoroacetate [Bu 4 P + . CF 3 COO - ], tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] and tetrabutyl hydrazine = tetrafluoroborate [Bu 4 P + . BF 4 - ], tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] and tetrabutyl hydrazine = hexafluorophosphate [Bu 4 P + . PF 6 - ], tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = mesylate [Bu 4 P + . CH 3 SO 3 - ], tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = p - toluene sulfonate [Bu 4 P + . p-CH 3 C 6 H 4 SO 3 - ], tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = dodecylbenzene sulfonate [Bu 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] and tetrabutyl hydrazine = perchlorate [Bu 4 P + . C 1 O 4 - ], tetrabutyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] and tetrabutyl hydrazine = nitrate [Bu 4 P + . NO 3 - ], tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ] and tetrabutylphosphonium bromide [Bu 4 P + . Br - ], tetraethyl hydrazine = fluorene (trifluoromethanesulfonyl) quinone imide salt [Et 4 P + . (CF 3 SO 2 ) 2 N - ] with tetrabutyl hydrazine = dodecylbenzene sulfonate [Bu 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetrabutyl sulfonium = trifluoromethanesulfonate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = pentafluoroethanesulfonate [Bu 4 P + . CF 3 CF 2 SO 3 - ], tetrabutyl sulfonium = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = trifluoroacetate [Bu 4 P + . CF 3 COO - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = tetrafluoroborate [Bu 4 P + . BF 4 - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = hexafluorophosphate [Bu 4 P + . PF 6 - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = mesylate [Bu 4 P + . CH 3 SO 3 - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = p - toluene sulfonate [Bu 4 P + . p-CH 3 C 6 H 4 SO 3 - ], tetrabutyl sulfonium = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = dodecylbenzenesulfonate [Bu 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetrabutyl sulfonium = trifluoromethanesulfonate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = perchlorate [Bu 4 P + . ClO 4 - ], tetrabutyl hydrazine = triflate [Bu 4 P + . CF 3 SO 3 - ] and tetrabutyl hydrazine = nitrate [Bu 4 P + . NO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = pentafluoroethanesulfonate [Bu 4 P + . CF 3 CF 2 SO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = trifluoroacetate [Bu 4 P + . CF 3 COO - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = tetrafluoroborate [Bu 4 P + . BF 4 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = hexafluorophosphate [Bu 4 P + . PF 6 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = mesylate [Bu 4 P + . CH 3 SO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = p - toluene sulfonate [Bu 4 P + . p-CH 3 C 6 H 4 SO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = dodecylbenzenesulfonate [Bu 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = perchlorate [Bu 4 P + . ClO 4 - ], tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ] and tetrabutyl hydrazine = nitrate [Bu 4 P + . NO 3 - ] and so on.

鏻鹽(1)之至少1種與鏻鹽(2)之至少1種的混合比例係以重量比計，通常為95：5至5：95，較佳為80：20至20：80。The mixing ratio of at least one of the phosphonium salt (1) and at least one of the phosphonium salt (2) is usually 95:5 to 5:95, preferably 80:20 to 20:80 by weight.

以調製本發明之抗靜電劑之方法而言，可列舉例如：1)將鏻鹽(1)之至少1種與鏻鹽(2)之至少1種，通常在100℃以上(較佳為100℃至150℃)，若有需要可同時攪拌而混合之方法；2)在適當溶劑中，使鏻鹽(1)之至少1種與鏻鹽(2)之至少1種溶解後，依需要可同時攪拌混合，而去除溶劑之方法等；但只要是能均勻混合此等有效成分之方法，則沒有特別限定。1)方法之情況係在混合後，2)方法之情況係在去除溶劑後，只要依需要冷卻至室溫左右(約10℃至30℃)，即以固體或液體狀得到抗靜電劑。The method for preparing the antistatic agent of the present invention may, for example, be 1) at least one of at least one of the phosphonium salt (1) and the phosphonium salt (2), usually at 100 ° C or higher (preferably 100). °C to 150 ° C), if necessary, can be stirred and mixed at the same time; 2) in a suitable solvent, at least one of the cerium salt (1) and at least one of the cerium salt (2), if necessary, At the same time, the method of stirring and mixing, and removing the solvent is not particularly limited as long as it is a method of uniformly mixing the active ingredients. 1) The case of the method is that after the mixing, the method of 2) is to obtain an antistatic agent in a solid or liquid form after cooling the solvent to about room temperature (about 10 ° C to 30 ° C) as needed.

本發明之抗靜電劑亦可依需要而混合使用安定化劑等添加劑或溶劑等。將此種抗靜電劑，以在製造樹脂組成物時調配入樹脂組成物材料中等方法，即可製造抗靜電性樹脂組成物。The antistatic agent of the present invention may be used by mixing an additive such as a stabilizer or a solvent or the like as needed. An antistatic resin composition can be produced by blending such an antistatic agent into a resin composition material in the production of a resin composition.

以用於本發明之抗靜電性樹脂組成物之樹脂而言，通常，可列舉如熱塑性樹脂、熱固性樹脂及光固性樹脂(例如丙烯酸系光固性樹脂)。The resin used for the antistatic resin composition of the present invention is usually, for example, a thermoplastic resin, a thermosetting resin, or a photocurable resin (for example, an acrylic photocurable resin).

以熱塑性樹脂而言，可列舉如聚乙烯、聚丙烯、乙烯或丙烯與其他乙烯單體(例如乙酸乙烯酯、α－烯烴、(甲基)丙烯酸酯等)之共聚物、降冰片烯(norbornene)類之加成聚合物、降冰片烯類與α－烯烴之加成共聚物、降冰片烯類之開環聚合物氫化聚合物、環戊二烯之開環聚合物氫化聚合物、環己二烯之開環聚合物氫化聚合物等聚烯烴；聚氯乙烯、聚二氯亞乙烯等含氯樹脂；聚苯乙烯、AS樹脂、ABS樹脂、MS樹脂、MBS樹脂等苯乙烯樹脂；聚丙烯酸、聚甲基丙烯酸、聚甲基丙烯酸甲酯等(甲基)丙烯酸系樹脂；由芳香族二羥基化合物(例如雙酚A)與氯化羰基(carbonyl chloride)或碳酸二苯酯所製造之芳香族聚碳酸酯等聚碳酸酯；耐綸4、耐綸6、耐綸8、耐綸11、耐綸12、耐綸66等聚醯胺；聚醚醯亞胺等熱塑性聚醯亞胺；聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯等聚酯；此等之混合物等。在此等之樹脂中，以聚碳酸酯、聚烯烴、(甲基)丙烯酸系樹脂及聚酯為較理想。Examples of the thermoplastic resin include copolymers of polyethylene, polypropylene, ethylene or propylene with other ethylene monomers (for example, vinyl acetate, α-olefin, (meth) acrylate, etc.), norbornene (norbornene) Addition polymer, addition copolymer of norbornene and α-olefin, ring-opening polymer hydrogenated polymer of norbornene, ring-opening polymer hydrogenated polymer of cyclopentadiene, cyclohexene Polyolefin such as diene ring-opening polymer hydrogenated polymer; chlorine-containing resin such as polyvinyl chloride or polydivinylidene; styrene resin such as polystyrene, AS resin, ABS resin, MS resin, MBS resin; polyacrylic acid (meth)acrylic resin such as polymethacrylic acid or polymethyl methacrylate; aroma made of an aromatic dihydroxy compound (for example, bisphenol A) and carbonyl chloride or diphenyl carbonate Polycarbonate such as polycarbonate; nylon 4, nylon 6, nylon 8, nylon 11, nylon 12, nylon 66, etc.; thermoplastic polyimine such as polyether phthalimide; Polyester such as ethylene terephthalate or polybutylene terephthalate; Thereof and the like. Among these resins, polycarbonate, polyolefin, (meth)acrylic resin and polyester are preferred.

以熱固性樹脂而言，可例示如環氧樹脂(例如雙酚A型環氧樹脂、雙酚F型環氧樹脂、氫化雙酚A型環氧樹脂、酚醛清漆型環氧樹脂等)、熱固性聚醯亞胺(例如苯均四酸二酐(pyromellitic dianhydride)與貳(4－胺基苯基)醚之縮聚物等)、聚胺酯、酚樹脂、胺基樹脂(例如三聚氰胺樹脂、尿素樹脂等)，其中以環氧樹脂為較理想。Examples of the thermosetting resin include epoxy resins (for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, hydrogenated bisphenol A type epoxy resin, novolac type epoxy resin, etc.), thermosetting polymerization. a quinone imine (for example, a polycondensate of pyromellitic dianhydride and fluorene (4-aminophenyl) ether), a polyurethane, a phenol resin, an amine resin (for example, a melamine resin, a urea resin, etc.), Among them, epoxy resin is preferred.

在本發明中，在樹脂組成物中之本發明之抗靜電劑之含有量，相對於樹脂，係0.1至30重量%，較佳為1至25重量%，特佳為2至20重量%。In the present invention, the content of the antistatic agent of the present invention in the resin composition is 0.1 to 30% by weight, preferably 1 to 25% by weight, particularly preferably 2 to 20% by weight based on the total amount of the resin.

本發明之抗靜電性樹脂組成物，可在樹脂之製造或加工時藉由直接添加並混合抗靜電劑而製造。The antistatic resin composition of the present invention can be produced by directly adding and mixing an antistatic agent during the production or processing of the resin.

在本發明之抗靜電性樹脂組成物中，除了樹脂及抗靜電劑以外，在不損及樹脂組成物性質之範圍內，可依需要而加入周知之添加劑。以添加劑而言，可列舉如染料、顏料、強化劑、填充劑、塑化劑、抗氧化劑、阻燃劑(flame retardant)、紫外線吸收劑等。In the antistatic resin composition of the present invention, in addition to the resin and the antistatic agent, a known additive may be added as needed within a range not impairing the properties of the resin composition. Examples of the additives include dyes, pigments, reinforcing agents, fillers, plasticizers, antioxidants, flame retardants, ultraviolet absorbers, and the like.

[實施例][Examples]

以下，列舉實施例，更為具體地說明本發明，但本發明當然並不被實施例所限定。而且，以下之實施例中，表面電阻值係使用三菱化學股份有限公司製Hiresta HT－210，以外加電壓(applied voltage)500V所測定。Hereinafter, the present invention will be specifically described by way of examples, but the present invention is of course not limited by the examples. Further, in the following examples, the surface resistance value was measured using Hiresta HT-210 manufactured by Mitsubishi Chemical Corporation, and an applied voltage of 500 V.

另外，在以下實施例中，各省略記號係分別表示下述之鏻鹽。Further, in the following examples, each of the omitted symbols indicates the following onium salt.

TBP－TFSI：四丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 SO2 )2 N－ ]TBP－TF：四丁鏻＝三氟甲磺酸鹽[Bu4 P＋ ．CF3 SO3 － ]TBP－PFSI：四丁鏻＝貳(五氟乙磺醯基)醯亞胺鹽[Bu4 P＋ ．(CF3 CF2 SO2 )2 N－ ]TBP－PF：四丁鏻＝五氟乙磺酸鹽[Bu4 P＋ ．CF3 CF2 SO3 － ]TBP－NF：四丁鏻＝九氟丁磺酸鹽[Bu4 P＋ ．CF3 (CF2 )3 SO3 － ]TBP－TFA：四丁鏻＝三氟乙酸鹽[Bu4 P＋ ．CF3 COO－ ]TBP－BF4 ：四丁鏻＝四氟硼酸鹽[Bu4 P＋ ．BF4 － ]TBP－PF6：四丁鏻＝六氟磷酸鹽[Bu4 P＋ ．PF6 － ]TBP－MS：四丁鏻＝甲磺酸鹽[Bu4 P＋ ．CH3 SO3 － ]TBP－PTS：四丁鏻＝對甲苯磺酸鹽[Bu4 P＋ ．p－CH3 C6 H4 SO3 － ]TBP－DBS：四丁鏻＝十二基苯磺酸鹽[Bu4 P＋ ．p－CH3 (CH2 )11 C6 H4 SO3 － ]TBP－ClO4：四丁鏻＝過氯酸鹽[Bu4 P＋ ．ClO4 － ]TBP－NO3：四丁鏻＝硝酸鹽[Bu4 P＋ ．NO3 － ]TEP－TFSI：四乙鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Et4 P＋ ．(CF3 SO2 )2 N－ ]TPhBnP－TFSI：三苯基苯甲鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 BnP＋ ．(CF3 SO2 )2 N－ ]TPhHepP－TF：三苯基庚鏻＝三氟甲磺酸鹽[Ph3 HepP＋ ．CF3 SO3 － ]TPhP－NF：四苯鏻＝九氟丁磺酸鹽[Ph4 P＋ ．CF3 (CF2 )3 SO3 － ]TPhHepP－NO3：三苯基庚鏻＝硝酸鹽[Ph3 HepP＋ ．NO3 － ]TPhBP－TFSI：三苯基丁鏻＝貳(三氟甲磺醯基)醯亞胺鹽[Ph3 BuP＋ ．(CF3 SO2 )2 N－ ]TBP-TFSI: tetrabutyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 SO 2 ) 2 N - ]TBP-TF: tetrabutyl sulfonium = triflate [Bu 4 P + . CF 3 SO 3 - ]TBP-PFSI: tetrabutyl hydrazine = hydrazine (pentafluoroethanesulfonyl) quinone imide salt [Bu 4 P + . (CF 3 CF 2 SO 2 ) 2 N - ]TBP-PF: tetrabutyl hydrazine = pentafluoroethanesulfonate [Bu 4 P + . CF 3 CF 2 SO 3 - ]TBP-NF: tetrabutyl hydrazine = nonafluorobutane sulfonate [Bu 4 P + . CF 3 (CF 2 ) 3 SO 3 - ]TBP-TFA: tetrabutyl hydrazine = trifluoroacetate [Bu 4 P + . CF 3 COO - ]TBP-BF 4 : tetrabutyl hydrazine = tetrafluoroborate [Bu 4 P + . BF 4 - ]TBP-PF6: tetrabutyl hydrazine = hexafluorophosphate [Bu 4 P + . PF 6 - ]TBP-MS: tetrabutyl hydrazine = mesylate [Bu 4 P + . CH 3 SO 3 - ]TBP-PTS: tetrabutyl hydrazine = p-toluenesulfonate [Bu 4 P + . p-CH 3 C 6 H 4 SO 3 - ]TBP-DBS: tetrabutyl hydrazine = dodecylbenzenesulfonate [Bu 4 P + . p-CH 3 (CH 2 ) 11 C 6 H 4 SO 3 - ]TBP-ClO4: tetrabutyl hydrazine = perchlorate [Bu 4 P + . ClO 4 - ]TBP-NO3: tetrabutyl hydrazine = nitrate [Bu 4 P + . NO 3 - ]TEP-TFSI: tetraethyl hydrazine = hydrazine (trifluoromethanesulfonyl) quinone imide salt [Et 4 P + . (CF 3 SO 2 ) 2 N - ]TPhBnP-TFSI: triphenylbenzhydrazide = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 BnP + . (CF 3 SO 2 ) 2 N - ]TPhHepP-TF: triphenylheptane = triflate [Ph 3 HepP + . CF 3 SO 3 - ]TPhP-NF: tetraphenylphosphonium = nonafluorobutanesulfonate [Ph 4 P + . CF 3 (CF 2 ) 3 SO 3 - ]TPhHepP-NO3: triphenylheptane = nitrate [Ph 3 HepP + . NO 3 - ]TPhBP-TFSI: triphenylbutyrene = fluorene (trifluoromethanesulfonyl) quinone imide salt [Ph 3 BuP + . (CF 3 SO 2 ) 2 N - ]

[實施例1至7，比較例1及2][Examples 1 to 7, Comparative Examples 1 and 2]

將雙酚A型環氧樹脂「Epikote 82 8」(環氧當量186g/eq，註冊商標，Japan Epoxy Resins股份有限公司製)8.80g、硬化劑亞胺雙丙胺1.20g、及如表1所示重量混合比之TBP－TFSI與TBP－TF之混合物0.50g(相對於樹脂，為5重量%)或TBP－TFSI單獨0.50g或TBP－TF單獨0.50g予以混合而得到環氧樹脂組成物。將該環氧樹脂組成物灌入直徑50mm×深度10mm之圓形模中，以50℃ 1小時，再以100℃ 6小時使其熱固化而製作試驗片。將試驗片靜置於23℃、50% RH之蒙氣環境中6小時後，以23℃、50% RH測定試驗片之表面電阻值。此等之測定結果如表1所示。8.80 g of bisphenol A type epoxy resin "Epikote 8 2 8" (epoxy equivalent: 186 g/eq, registered trademark, manufactured by Japan Epoxy Resins Co., Ltd.), 1.20 g of hardener imide dipropylamine, and Table 1 0.50 g of a mixture of TBP-TFSI and TBP-TF (5% by weight relative to the resin) or 0.50 g of TBP-TFSI alone or 0.50 g of TBP-TF alone was added to obtain an epoxy resin composition. The epoxy resin composition was poured into a circular mold having a diameter of 50 mm and a depth of 10 mm, and heat-cured at 50 ° C for 1 hour and then at 100 ° C for 6 hours to prepare a test piece. The test piece was allowed to stand in an atmosphere of 23 ° C and 50% RH for 6 hours, and then the surface resistance value of the test piece was measured at 23 ° C and 50% RH. The measurement results of these are shown in Table 1.

從表1之結果得知，調配有本發明之抗靜電劑的環氧樹脂組成物的表面電阻值，在TBP－TFSI與TBP－TF之重量混合比之廣範圍，相較於分別單獨使用TBP－TFSI及TBP－TF之情形為較低。From the results of Table 1, it was found that the surface resistivity of the epoxy resin composition prepared with the antistatic agent of the present invention was in a wide range of the weight ratio of TBP-TFSI to TBP-TF, and TBP was used alone. - The case of TFSI and TBP-TF is lower.

[實施例8至25][Examples 8 to 25]

除了將TBP－TFSI及TBP－TF分別替換為如表2所示之鏻鹽(1)及鏻鹽(2)以外，其餘與實施例4施行相同操作，進行試驗片之製作、靜置及測定表面電阻值。此等之測定結果如表2所示。Except that the TBP-TFSI and TBP-TF were replaced with the onium salt (1) and the onium salt (2) as shown in Table 2, the same operation as in Example 4 was carried out, and the test piece was prepared, allowed to stand and measured. Surface resistance value. The results of these measurements are shown in Table 2.

[實施例26至31][Examples 26 to 31]

除了將TBP－TFSI及TBP－TF分別替換為如表3所示之鏻鹽(1)及鏻鹽(2)以外，其餘與實施例4施行相同操作，進行試驗片之製作、靜置及測定表面電阻值。此等之測定結果如表3所示。Except that the TBP-TFSI and TBP-TF were replaced with the onium salt (1) and the onium salt (2) as shown in Table 3, the same operation as in Example 4 was carried out, and the test piece was prepared, allowed to stand and measured. Surface resistance value. The results of these measurements are shown in Table 3.

[比較例3至19][Comparative Examples 3 to 19]

除了將TBP－TFSI替換為如表4所示之鏻鹽以外，其餘與比較例1施行相同操作，進行試驗片之製作、靜置及測定表面電阻值。此等之測定結果如表4所示。Except that the TBP-TFSI was replaced with the onium salt shown in Table 4, the same operation as in Comparative Example 1 was carried out, and the test piece was prepared, allowed to stand, and the surface resistance value was measured. The results of these measurements are shown in Table 4.

[實施例20至26][Examples 20 to 26]

除了將TBP－TFSI及TBP－TF分別替換為如表5所示之鏻鹽及鏻鹽(2)以外，其餘與實施例4施行相同操作，進行試驗片之製作、靜置及測定表面電阻值。此等之測定結果如表5所示。Except that the TBP-TFSI and TBP-TF were replaced with the onium salt and the onium salt (2) as shown in Table 5, the same operation as in Example 4 was carried out, and the test piece was prepared, allowed to stand, and the surface resistance value was measured. . The results of these measurements are shown in Table 5.

從表2、表3、表4及表5之結果得知，調配有本發明之抗靜電劑的環氧樹脂組成物的表面電阻值，相較於單獨使用鏻鹽之情形以及併用其他鏻鹽之情形為較低。From the results of Table 2, Table 3, Table 4 and Table 5, the surface resistance value of the epoxy resin composition formulated with the antistatic agent of the present invention is compared with the case of using the onium salt alone and other onium salts. The situation is lower.

[實施例32至34，比較例27及28][Examples 32 to 34, Comparative Examples 27 and 28]

使丸狀(pellet)之聚碳酸酯「Calibre」(註冊商標，住友DOW股份有限公司製)30g溶解於N－甲基－2－吡咯啶酮(N－methyl－2－pyrrolidone)/THF(50/50)之混合溶液270g中，調製10重量%之Calibre溶液。在Calibre溶液10g中添加如表6所示之重量混合比之TBP－TFSI與TBP－TF之混合物0.025g(相對於樹脂，為2.5重量%)或TBP－TFSI單獨0.025g或TBP－TF單獨0.025g，以室溫混合1小時。將所得到之混合液灌入直徑50mm之鋁盒中，以160℃ 1小時，接著以210℃ 1小時去除溶劑，製作厚度約0.4mm之試驗薄片。將試驗薄片靜置於23℃、50% RH之蒙氣環境中6小時後，以23℃、50% RH測定試驗薄片之背面與表面之表面電阻值。此等之結果如表6所示。30 g of pelletized polycarbonate "Calibre" (registered trademark, manufactured by Sumitomo DOW Co., Ltd.) was dissolved in N-methyl-2-pyrrolidone/THF (50). In a mixed solution of /50), a 10% by weight Calibre solution was prepared. To 10 g of the Calibre solution, a mixture of TBP-TFSI and TBP-TF in a weight mixing ratio as shown in Table 6 was added in an amount of 0.025 g (2.5% by weight relative to the resin) or TBP-TFSI alone 0.025 g or TBP-TF alone 0.025. g, mixed at room temperature for 1 hour. The obtained mixture was poured into an aluminum case having a diameter of 50 mm, and the solvent was removed at 160 ° C for 1 hour, followed by removal at 210 ° C for 1 hour to prepare a test piece having a thickness of about 0.4 mm. The test piece was allowed to stand in an atmosphere of 23 ° C and 50% RH for 6 hours, and then the surface resistance of the back surface and the surface of the test piece was measured at 23 ° C and 50% RH. The results of these are shown in Table 6.

從表6之結果得知，調配有本發明之抗靜電劑的聚碳酸酯樹脂組成物的表面電阻值，在TBP－TFSI與TBP－TF之重量混合比之廣範圍，相較於分別單獨使用TBP－TFSI及TBP－TF之情形為較低。From the results of Table 6, it was found that the surface resistivity of the polycarbonate resin composition to which the antistatic agent of the present invention was formulated was in a wide range of the weight ratio of TBP-TFSI to TBP-TF, and was used alone. The case of TBP-TFSI and TBP-TF is lower.

[實施例35至37，比較例29及30][Examples 35 to 37, Comparative Examples 29 and 30]

使丸狀之聚烯烴「ZEONOR1020R」(註冊商標，日本ZEON股份有限公司製)30g溶解於環己烷/THF(80/20)之混合溶液270g中，調製10重量%之ZEONOR1020R溶液。在ZEONOR溶液10g中添加如表7所示之重量混合比之TBP－TFSI與TBP－TF之混合物0.02g(相對於樹脂，為2重量百分比)或TBP－TFSI單獨0.02g或TBP－TF單獨0.02g，以室溫混合1小時。將所得到之混合液，用棒式塗布器(Bar coater)(# 32)，塗布於鋁薄片上後，以120℃使其乾燥1小時，製作厚度約5 μm之ZEONOR1020R之試驗薄膜。將試驗薄膜靜置於23℃、50% RH之空氣中6小時後，以23℃、50% RH測定試驗薄膜之背面與表面之表面電阻值。此等之結果如表7所示。30 g of a pelletized polyolefin "ZEONOR 1020R" (registered trademark, manufactured by ZEON Co., Ltd., Japan) was dissolved in 270 g of a mixed solution of cyclohexane/THF (80/20) to prepare a 10% by weight solution of ZEONOR 1020R. To 10 g of the ZEONOR solution, a mixture of TBP-TFSI and TBP-TF in a weight mixing ratio as shown in Table 7 was added in an amount of 0.02 g (2 wt% with respect to the resin) or TBP-TFSI alone 0.02 g or TBP-TF alone 0.02. g, mixed at room temperature for 1 hour. The obtained mixed solution was applied onto an aluminum foil by 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 the test film was allowed to stand in air at 23 ° C and 50% RH for 6 hours, the surface resistance of the back surface and the surface of the test film was measured at 23 ° C and 50% RH. The results of these are shown in Table 7.

從表7之結果得知，調配有本發明之抗靜電劑的聚烯烴樹脂組成物的表面電阻值，在TBP－TFSI與TBP－TF之重量混合比之廣範圍，相較於分別單獨使用TBP－TFSI及TBP－TF之情形為較低。From the results of Table 7, it was found that the surface resistance value of the polyolefin resin composition to which the antistatic agent of the present invention was formulated was in a wide range of the weight ratio of TBP-TFSI to TBP-TF, and TBP was used alone. - The case of TFSI and TBP-TF is lower.

[實施例38至40，比較例31及32][Examples 38 to 40, Comparative Examples 31 and 32]

在丙烯酸系樹脂「SK－DYNE 1435」(註冊商標，綜研化學股份有限公司製)10重量份中，添加如表8所示之重量混合比之TBP－TFSI與TBP－TF之混合物2重量份或TBP－TFSI單獨2重量份或TBP－TF單獨2重量份、及作為稀釋溶劑之乙酸乙酯190重量份，調製成塗膜液。用棒式塗布器(# 16)，將塗膜液在聚酯薄膜上以乾燥厚度為約1.2 μm之厚度塗布後，以60℃使其乾燥1小時，製作試驗薄膜。將試驗薄膜靜置於15至20℃、50% RH之蒙氣環境中24小時後，以20℃、50% RH測定塗布面之表面電阻值。此等之結果如表8所示。To 10 parts by weight of the acrylic resin "SK-DYNE 1435" (registered trademark, manufactured by K.K., Ltd.), 2 parts by weight of a mixture of TBP-TFSI and TBP-TF, as shown in Table 8, was added or 2 parts by weight of TBP-TFSI alone or 2 parts by weight of TBP-TF alone and 190 parts by weight of ethyl acetate as a diluent solvent were prepared to prepare a coating liquid. The coating liquid was applied onto the polyester film with a thickness of about 1.2 μm using a bar coater (#16), and then dried at 60 ° C for 1 hour to prepare a test film. The test film was allowed to stand in an atmosphere of 15 to 20 ° C and 50% RH for 24 hours, and then the surface resistance value of the coated surface was measured at 20 ° C and 50% RH. The results of these are shown in Table 8.

從表8之結果得知，調配有本發明之抗靜電劑的丙烯酸系樹脂組成物的表面電阻值，在TBP－TFSI與TBP－TF之重量混合比之廣範圍，相較於分別單獨使用TBP－TFSI及TBP－TF之情形為較低。From the results of Table 8, it was found that the surface resistivity of the acrylic resin composition to which the antistatic agent of the present invention was formulated was in a wide range of the weight ratio of TBP-TFSI to TBP-TF, and TBP was used alone. - The case of TFSI and TBP-TF is lower.

[實施例41至43，比較例33及34][Examples 41 to 43, Comparative Examples 33 and 34]

在聚酯「Vylon 20SS」(註冊商標，東洋紡績股份有限公司製)10重量份中，添加如表9所示之重量混合比之TBP－TFSI與TBP－TF之混合物1重量份或TBP－TFSI單獨1重量部或TBP－TF單獨1重量部、及作為稀釋溶劑之甲基乙基酮/甲苯(20/80)190重量份，調製塗膜液。用棒式塗布器(# 16)，將塗膜液在聚酯薄膜上以乾燥厚度為約1.2 μm之厚度塗布後，以60℃使其乾燥1小時製作試驗薄膜。將試驗薄膜靜置於15至20℃、50% RH之蒙氣環境中24小時後，以20℃、50% RH測定塗布面之表面電阻值。此等之結果如表9所示。To 10 parts by weight of polyester "Vylon 20SS" (registered trademark, manufactured by Toyobo Co., Ltd.), 1 part by weight or TBP-TFSI of a mixture of TBP-TFSI and TBP-TF in a weight mixing ratio as shown in Table 9 was added. The coating liquid was prepared by using 1 part by weight or 1 part by weight of TBP-TF alone, and 190 parts by weight of methyl ethyl ketone/toluene (20/80) as a diluent solvent. The coating liquid was applied onto the polyester film by a bar coater (#16) to a thickness of about 1.2 μm, and then dried at 60 ° C for 1 hour to prepare a test film. The test film was allowed to stand in an atmosphere of 15 to 20 ° C and 50% RH for 24 hours, and then the surface resistance value of the coated surface was measured at 20 ° C and 50% RH. The results of these are shown in Table 9.

從表9之結果得知，調配有本發明之抗靜電劑的聚酯樹脂組成物之表面電阻值，在TBP－TFSI與TBP－TF之重量混合比之廣範圍，相較於分別單獨使用TBP－TFSI及TBP－TF之情形為較低。From the results of Table 9, it was found that the surface resistivity of the polyester resin composition to which the antistatic agent of the present invention was formulated was in a wide range of the weight ratio of TBP-TFSI to TBP-TF, and TBP was used alone. - The case of TFSI and TBP-TF is lower.

(產業上之利用可能性)(industrial use possibility)

若根據本發明，藉由鏻鹽(1)之至少1種與鏻鹽(2)之至少1種的併用，相較於以往單獨使用之情況，能提供更優良之抗靜電劑。另外，若將該抗靜電劑調配入樹脂中，則可製造使表面電阻值較為降低之抗靜電性樹脂組成物。According to the present invention, by using at least one of the phosphonium salt (1) and at least one of the phosphonium salts (2), it is possible to provide a more excellent antistatic agent than in the case of conventional use alone. Further, when the antistatic agent is blended into the resin, an antistatic resin composition which lowers the surface resistance value can be produced.

Claims (6)

一種抗靜電劑，其特徵係含有如式(1)所示之第四級鏻鹽(以下，以鏻鹽(1)稱之)之至少1種：(R1 )3 R2 P+ ．A- (1)(式中，R1 係碳數1至4之烷基或芳香基；當R1 為碳數1至4之烷基時，R2 係表示與R1 相同，或是表示芳香基或芳烷基；當R1 為芳香基時，R2 係表示碳數1至16之烷基、芳香基或芳烷基；A- 係表示貳(全氟烷磺醯基)醯亞胺離子或全氟烷磺酸離子)、及如式(2)所示之第四級鏻鹽(以下，以鏻鹽(2)稱之)之至少1種：(R3 )3 R4 P+ ．B- (2)(式中，R3 係碳數1至4之烷基或芳香基；當R3 為碳數1至4之烷基時，R4 係表示與R3 相同，或是表示芳香基或芳烷基；當R3 為芳香基時，R4 係表示碳數1至16之烷基、芳香基或芳烷基；B- 係表示陰離子)以作為有效成分(惟，鏻鹽(1)與鏻鹽(2)不為相同之化合物)；鏻鹽(1)之至少1種與鏻鹽(2)之至少1種的混合比例以重量比計為95：5至5：95。An antistatic agent characterized by containing at least one of a fourth-order phosphonium salt (hereinafter referred to as a phosphonium salt (1)) represented by the formula (1): (R 1 ) 3 R 2 P + . A - (1) (wherein R 1 is an alkyl group or an aromatic group having 1 to 4 carbon atoms; when R 1 is an alkyl group having 1 to 4 carbon atoms, R 2 represents the same as R 1 or represents An aromatic group or an aralkyl group; when R 1 is an aromatic group, R 2 represents an alkyl group, an aromatic group or an aralkyl group having 1 to 16 carbon atoms; and A - represents a fluorene (perfluoroalkylsulfonyl) fluorene group. At least one of an amine ion or a perfluoroalkanesulfonate ion and a fourth-order phosphonium salt (hereinafter referred to as a phosphonium salt (2)) represented by the formula (2): (R 3 ) 3 R 4 P + . B - (2) (wherein R 3 is an alkyl group or an aromatic group having 1 to 4 carbon atoms; when R 3 is an alkyl group having 1 to 4 carbon atoms, R 4 represents the same as R 3 or represents An aromatic group or an aralkyl group; when R 3 is an aromatic group, R 4 means an alkyl group having 1 to 16 carbon atoms, an aromatic group or an aralkyl group; and B - means an anion) as an active ingredient (only, an onium salt) (1) a compound which is not the same as the cerium salt (2); a mixing ratio of at least one of the cerium salt (1) and at least one of the cerium salt (2) is 95:5 to 5:95 by weight. . 如申請專利範圍第1項之抗靜電劑，其中，B- 所示之陰離子係貳(全氟烷磺醯基)醯亞胺離子、全氟烷磺酸離子、全氟烷羧酸離子、烷磺酸離子、烷基苯磺酸離子、含氟無機酸離子或含氧酸離子。The patentable scope of application of an antistatic agent according to Item 1, wherein, B - II shown in the anionic (perfluoroalkyl sulfonic acyl) acyl imide ion, a perfluoroalkyl sulfonate ion, a carboxylate ion perfluoroalkyl, alkoxy Sulfonic acid ion, alkylbenzenesulfonic acid ion, fluorine-containing inorganic acid ion or oxyacid ion. 如申請專利範圍第1項或第2項之抗靜電劑，其中，式(1)及式(2)中，R1 、R2 、R3 及R4 ，任一者皆為碳數1至 4之烷基。An antistatic agent according to claim 1 or 2, wherein in the formulas (1) and (2), R 1 , R 2 , R 3 and R 4 are each a carbon number of 1 to 4 alkyl. 如申請專利範圍第1項至第2項之抗靜電劑，其中，從鏻鹽(1)選擇之至少1種與從鏻鹽(2)選擇之至少1種的混合比例係重量比80：20至20：80之比例。 The antistatic agent of claim 1 to 2, wherein a mixing ratio of at least one selected from the cerium salt (1) to at least one selected from the cerium salt (2) is 80:20 The ratio to 20:80. 一種抗靜電性樹脂組成物，係使樹脂中含有申請專利範圍第1項至第4項中任一項之抗靜電劑，相對於樹脂，抗靜電劑之含有量係0.1至30重量%。 An antistatic resin composition containing the antistatic agent according to any one of claims 1 to 4, wherein the antistatic agent is contained in an amount of 0.1 to 30% by weight based on the resin. 如申請專利範圍第5項所記載之抗靜電性樹脂組成物，其中，樹脂為環氧樹脂、聚碳酸酯、聚烯烴、(甲基)丙烯酸系樹脂或聚酯。 The antistatic resin composition according to claim 5, wherein the resin is an epoxy resin, a polycarbonate, a polyolefin, a (meth)acrylic resin or a polyester.
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