JP2013071933A - New polyoxyalkylene ammonium salt and antistatic agent containing the same - Google Patents
New polyoxyalkylene ammonium salt and antistatic agent containing the same Download PDFInfo
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本発明は、新規なポリオキシアルキレンアンモニウム塩及びそれを含有する帯電防止剤に関する。 The present invention relates to a novel polyoxyalkylene ammonium salt and an antistatic agent containing the same.
ポリオキシアルキレンアンモニウム塩としては、ポリオキシアルキレンアンモニウム=ビス(トリフルオロメタンスルホニル)イミドが公知であり、該ポリオキシアルキレンアンモニウム=ビス(トリフルオロメタンスルホニル)イミドは、帯電防止剤として使用されることが知られている(例えば、特許文献1参照)。 As the polyoxyalkylene ammonium salt, polyoxyalkylene ammonium = bis (trifluoromethanesulfonyl) imide is known, and it is known that the polyoxyalkylene ammonium = bis (trifluoromethanesulfonyl) imide is used as an antistatic agent. (For example, refer to Patent Document 1).
本発明は、樹脂に対して優れた帯電防止性能を付与できる新規なポリオキシアルキレンアンモニウム塩及びそれを含有する帯電防止剤を提供することを課題とする。 An object of the present invention is to provide a novel polyoxyalkylene ammonium salt capable of imparting excellent antistatic performance to a resin and an antistatic agent containing the same.
本発明者が、上記課題を解決するために鋭意検討を行ったところ、式(1)で表わされるポリオキシアルキレンアンモニウム塩(以下、ポリオキシアルキレンアンモニウム塩(1)という。)が、樹脂に対して優れた帯電防止性を付与できることを見出し、本発明を完成するに至った。 As a result of intensive studies by the inventor in order to solve the above-described problems, a polyoxyalkylene ammonium salt represented by the formula (1) (hereinafter referred to as polyoxyalkylene ammonium salt (1)) is used for the resin. The present inventors have found that excellent antistatic properties can be imparted and have completed the present invention.
即ち本発明は、式(1): That is, the present invention provides the formula (1):
本発明のポリオキシアルキレンアンモニウム塩(1)は、樹脂に対して優れた帯電防止性を付与できるため、有用な化合物である。 The polyoxyalkylene ammonium salt (1) of the present invention is a useful compound because it can impart excellent antistatic properties to the resin.
以下、本発明を具体的に説明する。 Hereinafter, the present invention will be specifically described.
式(1)中、R1及びR2は炭素数1〜18のアルキル基を表し、R1は炭素数1〜6のアルキル基が好ましく、炭素数1〜3のアルキル基がより好ましい。R2は炭素数3〜18のアルキル基が好ましく、炭素数8〜18のアルキル基がより好ましい。R1及びR2の具体例としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基等が挙げられる。m及びnは1以上の整数であり、m+nは15である。 In Formula (1), R 1 and R 2 represent an alkyl group having 1 to 18 carbon atoms, and R 1 is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. R 2 is preferably an alkyl group having 3 to 18 carbon atoms, and more preferably an alkyl group having 8 to 18 carbon atoms. Specific examples of R 1 and R 2 include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, Examples include a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group. m and n are integers of 1 or more, and m + n is 15.
本発明のポリオキシアルキレンアンモニウム塩(1)は、式(2): The polyoxyalkylene ammonium salt (1) of the present invention has the formula (2):
M+・(FSO2)2N− (3)
(式中、M+は水素イオン又はアルカリ金属イオンを表す。)で示される酸又はそのアルカリ金属塩(以下、酸類(3)という。)とアニオン交換反応させることにより製造することができる。
M +. (FSO 2 ) 2 N − (3)
(In the formula, M + represents a hydrogen ion or an alkali metal ion.) It can be produced by an anion exchange reaction with an acid or an alkali metal salt thereof (hereinafter referred to as acids (3)).
酸類(3)の使用量は、ポリオキシアルキレンアンモニウム=ハライド(2)1モルに対し、通常0.6モル以上、好ましくは0.8モル〜1.1モルであり、より好ましくは1.0〜1.02モルである。 The amount of the acids (3) used is usually 0.6 mol or more, preferably 0.8 mol to 1.1 mol, more preferably 1.0 mol, per 1 mol of polyoxyalkylene ammonium = halide (2). -1.02 mol.
アニオン交換反応は、通常、溶媒中で行われる。溶媒はポリオキシアルキレンアンモニウム=ハライド(2)および酸類(3)を溶解させる溶媒であれば特に限定されないが、好ましくはメタノール、エタノール、ブタノール等のアルコール類、アセトニトリル等のニトリル類又は水が挙げられ、より好ましくはアセトニトリルである。溶媒の使用量は特に制限はないが、ポリオキシアルキレンアンモニウム=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1〜10量部である。 The anion exchange reaction is usually performed in a solvent. The solvent is not particularly limited as long as it dissolves polyoxyalkylene ammonium = halide (2) and acids (3), and preferably includes alcohols such as methanol, ethanol, butanol, nitriles such as acetonitrile, or water. More preferably, it is acetonitrile. Although there is no restriction | limiting in particular in the usage-amount of a solvent, It is 20 weight part or less normally with respect to 1 weight part of polyoxyalkylene ammonium = halide (2), Preferably it is 1-10 weight part.
ポリオキシアルキレンアンモニウム=ハライド(2)、酸類(3)及び溶媒の混合順序は特に限定されず、ポリオキシアルキレンアンモニウム=ハライド(2)と溶媒を混合した後に酸類(3)を添加してもよいし、酸類(3)と溶媒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。 The order of mixing the polyoxyalkylene ammonium = halide (2), acids (3) and the solvent is not particularly limited, and the acids (3) may be added after mixing the polyoxyalkylene ammonium = halide (2) and the solvent. The ammonium halide (2) may be added after mixing the acids (3) and the solvent.
アニオン交換反応における反応温度は、通常0℃以上、好ましくは10〜80℃、特に好ましくは20〜60℃である。 The reaction temperature in the anion exchange reaction is usually 0 ° C. or higher, preferably 10 to 80 ° C., particularly preferably 20 to 60 ° C.
反応終了後の反応液からポリオキシアルキレンアンモニウム塩(1)を取り出す方法としては、反応液を濃縮後、メンブランフィルター等でろ過し、ポリオキシアルキレンアンモニウム塩(1)を得る方法が挙げられる。また溶媒として水を用いた場合は、反応液をメチルイソブチルケトン等の水と混和しない有機溶媒で抽出後、得られた有機層を濃縮、乾燥してポリオキシアルキレンアンモニウム塩(1)を得る方法が挙げられる。 As a method for taking out the polyoxyalkylene ammonium salt (1) from the reaction solution after the completion of the reaction, a method in which the reaction solution is concentrated and then filtered through a membrane filter or the like to obtain the polyoxyalkylene ammonium salt (1). When water is used as the solvent, the reaction solution is extracted with an organic solvent that is not miscible with water such as methyl isobutyl ketone, and then the resulting organic layer is concentrated and dried to obtain a polyoxyalkylene ammonium salt (1). Is mentioned.
本発明の帯電防止剤は、ポリオキシアルキレンアンモニウム塩(1)を有効成分として含有してなるものであり、単独であっても帯電防止剤として用いることができるが、必要に応じて安定化剤等の添加剤又は溶媒等を混合して用いることもできる。本発明の帯電防止剤を使用できる絶縁物としては樹脂組成物等が挙げられる。帯電防止性を付与するには、本発明の帯電防止剤を樹脂組成物等の製造時にそれらの材料に添加、混合する等の方法または樹脂組成物等に塗布する方法等が挙げられ、本発明の帯電防止剤を用いた場合、従来のポリオキシアルキレンアンモニウム塩を含有する帯電防止剤を用いた場合に比べて、樹脂組成物等の表面抵抗値をより低下させることができる。 The antistatic agent of the present invention comprises the polyoxyalkylene ammonium salt (1) as an active ingredient and can be used alone as an antistatic agent, but if necessary, a stabilizer It is also possible to use a mixture of additives such as solvents or solvents. Examples of the insulator that can use the antistatic agent of the present invention include a resin composition. In order to impart antistatic properties, the antistatic agent of the present invention may be added to or mixed with those materials during the production of the resin composition or the like, or may be applied to the resin composition or the like. When the antistatic agent is used, the surface resistance value of the resin composition or the like can be further reduced as compared with the case where the antistatic agent containing a conventional polyoxyalkylene ammonium salt is used.
樹脂組成物への本発明の帯電防止剤の添加量は、本発明のポリオキシアルキレンアンモニウム塩(1)換算で樹脂基材に対して0.01〜40重量%であり、好ましくは0.1〜20重量%、特に好ましくは0.5〜10重量%である。 The addition amount of the antistatic agent of this invention to a resin composition is 0.01 to 40 weight% with respect to the resin base material in conversion of the polyoxyalkylene ammonium salt (1) of this invention, Preferably it is 0.1. -20% by weight, particularly preferably 0.5-10% by weight.
樹脂組成物には、樹脂及び帯電防止剤以外に樹脂組成物の性質を損なわない範囲で、必要に応じて公知の添加剤を加えることができる。添加剤としては、染料、顔料、補強剤、充填剤、可塑剤、酸化防止剤、難燃剤、紫外線吸収剤等が挙げられる。 In addition to the resin and the antistatic agent, a known additive can be added to the resin composition as necessary within a range that does not impair the properties of the resin composition. Examples of the additive include dyes, pigments, reinforcing agents, fillers, plasticizers, antioxidants, flame retardants, ultraviolet absorbers and the like.
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。下記の実施例中、1H−NMRは日本電子データム株式会社製核磁気共鳴装置AL−400を使用し、溶媒にCDCl3を用いて400MHzで測定した。表面抵抗率は三菱化学株式会社製抵抗率計ハイレスター(MCP−HT450)を用い、印加電圧500Vにて測定した。熱分解開始温度(試料の重量が当初の5%減となったときの温度)はセイコーインスツルメンツ株式会社製示差熱熱重量同時測定装置TG/DTA220を用い、窒素雰囲気下で測定した。 Next, the present invention will be specifically described based on examples, but the present invention is not limited thereto. In the following examples, 1 H-NMR was measured at 400 MHz using a nuclear magnetic resonance apparatus AL-400 manufactured by JEOL Datum Co., Ltd. and using CDCl 3 as a solvent. The surface resistivity was measured at an applied voltage of 500 V using a resistivity meter Hi-Lester (MCP-HT450) manufactured by Mitsubishi Chemical Corporation. The thermal decomposition starting temperature (temperature when the weight of the sample was reduced by 5% at the beginning) was measured under a nitrogen atmosphere using a differential thermothermal gravimetric simultaneous measurement device TG / DTA220 manufactured by Seiko Instruments Inc.
実施例1
反応容器に塩化ポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム(ライオン株式会社製、エソカードC/25)92.5g(0.11mol)、ビス(フルオロスルホニル)イミドカリウム23.0g(0.11mol)及びアセトニトリル138.8gをはかりとり、室温で3時間攪拌した。得られた反応液をろ過した後、ろ液を濃縮・乾燥してポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(フルオロスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2F)2](m+n=15)106.3g(収率98.6%)を得た。
得られたポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(フルオロスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2F)2](m+n=15)の1H−NMR分析データ及び熱分析データを以下に示す。
Example 1
In a reaction vessel, 92.5 g (0.11 mol) of polyoxyethylene alkyl chloride (C8-C18) methylammonium chloride (manufactured by Lion Corporation, Esocard C / 25), 23.0 g (0.11 mol) of potassium bis (fluorosulfonyl) imide And 138.8 g of acetonitrile was weighed and stirred at room temperature for 3 hours. After filtering the obtained reaction liquid, the filtrate was concentrated and dried to obtain polyoxyethylene alkyl (C8 to C18) methylammonium bis (fluorosulfonyl) imide [C 8-18 H 17-37 N + (CH 3 ) (CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [- to give n a (SO 2 F) 2] ( m + n = 15) 106.3g (98.6% yield).
The resulting polyoxyethylene alkyl (C8 to C18) methylammonium = bis (fluorosulfonyl) imide [C 8~18 H 17~37 N + ( CH 3) (CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [- it shows n a (SO 2 F) 2] ( m + n = 15 1 H-NMR analysis data and thermal analysis data) below.
1H−NMR(CDCl3) δ:ppm4.06−3.59(brm,66H)、3.42(brm,4H)、3.20(m,4H)、2.78(s、3H)、1.32−1.26(m,23H)、0.88(t,3H)
熱分解開始温度:302℃
1 H-NMR (CDCl 3 ) δ: ppm 4.06-3.59 (brm, 66H), 3.42 (brm, 4H), 3.20 (m, 4H), 2.78 (s, 3H), 1.32-1.26 (m, 23H), 0.88 (t, 3H)
Thermal decomposition start temperature: 302 ° C
比較例1
反応容器に塩化ポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム(ライオン株式会社製、エソカードC/25)854.9g(0.97mol)、ビス(トリフルオロメタンスルホニル)イミドカリウム390.7g(1.02mol)及びイオン交換水2015.2gをはかりとり、室温で3時間攪拌した。得られた反応液にメチルイソブチルケトン2137.8gを加えて抽出、分液し、有機層をイオン交換水2137.5gを用いて3回洗浄した。得られた有機層を濃縮・乾燥してポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(トリフルオロメタンスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2C4F9)2](m+n=15)707.0g(収率64.7%)を得た。
得られたポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(トリフルオロメタンスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2C4F9)2](m+n=15)の11H−NMR分析データ及び熱分析データを以下に示す。
Comparative Example 1
In a reaction vessel, polyoxyethylene alkyl (C8-C18) methylammonium chloride (manufactured by Lion Corporation, Esocard C / 25) 854.9 g (0.97 mol), potassium bis (trifluoromethanesulfonyl) imide 390.7 g (1.02 mol) ) And ion-exchanged water (155.2 g) were weighed and stirred at room temperature for 3 hours. 2137.8 g of methyl isobutyl ketone was added to the obtained reaction liquid, extracted and separated, and the organic layer was washed 3 times with 2137.5 g of ion-exchanged water. The obtained organic layer was concentrated and dried to obtain polyoxyethylenealkyl (C8-C18) methylammonium bis (trifluoromethanesulfonyl) imide [C 8-18 H 17-37 N + (CH 3 ) (CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [- n (SO 2 C 4 F 9) 2] was obtained (m + n = 15) 707.0g (64.7% yield).
The resulting polyoxyethylene alkyl (C8 to C18) methylammonium = bis (trifluoromethanesulfonyl) imide [C 8~18 H 17~37 N + ( CH 3) (CH 2 CH 2 O) m H (CH 2 CH 11 H-NMR analysis data and thermal analysis data of 2 O) n H] [ — N (SO 2 C 4 F 9 ) 2 ] (m + n = 15) are shown below.
1H−NMR(CDCl3) δ:ppm4.04−3.62(brm,66H)、3.41(brm,4H)、3.15(m,4H)、2.95(s、3H)、1.32−1.26(m,18H)、0.88(t,3H)
熱分解開始温度:284℃
1 H-NMR (CDCl 3 ) δ: ppm 4.04-3.62 (brm, 66H), 3.41 (brm, 4H), 3.15 (m, 4H), 2.95 (s, 3H), 1.32-1.26 (m, 18H), 0.88 (t, 3H)
Thermal decomposition start temperature: 284 ° C
応用例1
SKダイン909A(総研化学株式会社製粘着剤)100重量部、実施例1で得られたポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(フルオロスルホニル)イミド[C12H25N+(CH3)[(CH2CH2O)mH(CH2CH2O)nH][−N(SO2F)2](m+n=15)10重量部及び希釈溶剤として酢酸エチル100重量部を加えて溶解しコート液を調整した。このコ−ト液をポリエステルフィルム上にバーコーターを用いて乾燥厚み約10μmの厚みでコートし、80℃で3分間加熱させて試験片を作成した。得られた試験片を23℃、50%RHの雰囲気中に5間保持した後、25℃、76%RHで試験片の表面抵抗率を測定した。その結果を表1に示す。
Application example 1
100 parts by weight of SK Dyne 909A (adhesive manufactured by Soken Chemical Co., Ltd.), polyoxyethylene alkyl (C8 to C18) methylammonium bis (fluorosulfonyl) imide [C 12 H 25 N + (CH 3) [(CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [- n (SO 2 F) 2] a (m + n = 15) 10 parts by weight and 100 parts by weight of ethyl acetate as a diluting solvent In addition, it was dissolved to prepare a coating solution. This coating solution was coated on a polyester film with a bar coater to a dry thickness of about 10 μm and heated at 80 ° C. for 3 minutes to prepare a test piece. The obtained test piece was held in an atmosphere of 23 ° C. and 50% RH for 5 hours, and then the surface resistivity of the test piece was measured at 25 ° C. and 76% RH. The results are shown in Table 1.
比較応用例1
応用例1のポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(フルオロスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2F)2](m+n=15)を用いなかった場合以外は応用例1と同様にして試験片を作成し、かかる試験片の粘着剤の表面抵抗値を応用例1と同様にして測定した。その結果を表1に示す。
Comparative application example 1
Application Example 1 Polyoxyethylene alkyl (C8 to C18) methylammonium = bis (fluorosulfonyl) imide [C 8~18 H 17~37 N + ( CH 3) (CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [- n (SO 2 F) 2] (m + n = except when not used 15) to prepare a test piece in the same manner as in application example 1, the surface resistance of the pressure-sensitive adhesive according specimens The value was measured in the same manner as in Application Example 1. The results are shown in Table 1.
比較応用例2
応用例1のポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(フルオロスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2F)2](m+n=15)の代わりに、比較例1のポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(トリフルオロメタンスルホニル)イミド[C8〜18H17〜37N+(CH3)(CH2CH2O)mH(CH2CH2O)nH][−N(SO2C4F9)2](m+n=15)を用いた場合以外は応用例1と同様にして試験片を作成し、かかる試験片の粘着剤の表面抵抗値を応用例1と同様にして測定した。その結果を表1に示す。
Comparative application example 2
Application Example 1 Polyoxyethylene alkyl (C8 to C18) methylammonium = bis (fluorosulfonyl) imide [C 8~18 H 17~37 N + ( CH 3) (CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [ — N (SO 2 F) 2 ] (m + n = 15) instead of polyoxyethylene alkyl (C8-C18) methylammonium bis (trifluoromethanesulfonyl) imide [C 8~18 H 17~37 n + (CH 3 ) (CH 2 CH 2 O) m H (CH 2 CH 2 O) n H] [- n (SO 2 C 4 F 9) 2] (m + n = 15) A test piece was prepared in the same manner as in Application Example 1 except that was used, and the surface resistance value of the adhesive of the test piece was measured in the same manner as in Application Example 1. The results are shown in Table 1.
表1の結果から、本発明のポリオキシアルキレンアンモニウム塩(1)を帯電防止剤として使用したポリエステルフィルムは、公知のポリオキシエチレンアルキル(C8〜C18)メチルアンモニウム=ビス(トリフルオロメタンスルホニル)イミドと比較して、優れた帯電防止性能を示すことがわかった。 From the results in Table 1, the polyester film using the polyoxyalkylene ammonium salt (1) of the present invention as an antistatic agent is known to be a known polyoxyethylene alkyl (C8-C18) methyl ammonium bis (trifluoromethanesulfonyl) imide. In comparison, it was found that excellent antistatic performance was exhibited.
Claims (8)
M+・(FSO2)2N− (3)
(式中、M+は水素イオン又はアルカリ金属イオンを表す。)で示される酸又はそのアルカリ金属塩とアニオン交換反応させることを特徴とする請求項1〜3のいずれかに記載のポリオキシアルキレンアンモニウム塩の製造方法。 Formula (2):
M +. (FSO 2 ) 2 N − (3)
The polyoxyalkylene according to any one of claims 1 to 3, which is subjected to an anion exchange reaction with an acid represented by (wherein M + represents a hydrogen ion or an alkali metal ion) or an alkali metal salt thereof. A method for producing an ammonium salt.
Priority Applications (1)
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