JP6054081B2 - 導電性重合体組成物及びその製造方法、該導電性重合体組成物を含む塗料及び制電性被覆物 - Google Patents
導電性重合体組成物及びその製造方法、該導電性重合体組成物を含む塗料及び制電性被覆物 Download PDFInfo
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- JP6054081B2 JP6054081B2 JP2012162034A JP2012162034A JP6054081B2 JP 6054081 B2 JP6054081 B2 JP 6054081B2 JP 2012162034 A JP2012162034 A JP 2012162034A JP 2012162034 A JP2012162034 A JP 2012162034A JP 6054081 B2 JP6054081 B2 JP 6054081B2
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- 229920001940 conductive polymer Polymers 0.000 title claims description 80
- 239000000203 mixture Substances 0.000 title claims description 58
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
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- 150000003839 salts Chemical class 0.000 claims description 34
- -1 methacryloyl group Chemical group 0.000 claims description 28
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- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 13
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- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 3
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- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
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- 150000002978 peroxides Chemical class 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Graft Or Block Polymers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Paints Or Removers (AREA)
- Conductive Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Description
水50mlに、ビス(トリフルオロメタンスルホニル)イミド((CF3SO2)2NH)14.0質量部、過硫酸ナトリウム4.8質量部を溶解し、常温で攪拌しながら、3,4−エチレンジオキシチオフェン2mlを徐々に滴下(滴下時間、1時間)し、滴下終了後、さらに24時間反応させた。得られた反応液をアンモニア水(25%)でpH7.5とした後、メタノールで再沈殿し、濾過、乾燥を行い、ポリ(3,4−エチレンジオキシチオフェン)からなる電子伝導性重合体(A)を得た。
次いで、メチルメタクリレート単量体100質量部に、イオン伝導性単量体組成物(ポリエチレングリコールジメタクリレートにリチウムビス(トリフルオロメタンスルホニル)イミドを50質量部%溶解してなる組成物(サンコノール(登録商標)A600−50R,三光化学工業(社)製、オキシエチレン単位14))5質量部と、光開始剤Luna100(日本シィベルヘグナー製)5質量部とを配合したイオン伝導性単量体体組成物100質量部に対して、上記電子伝導性重合体(A)1.5質量部を添加し、2時間攪拌して、液状導電性重合体組成物を得た。この液状導電性重合体組成物を、ポリエチレンテレフタレート(PET)フィルム(厚さ60μm)上に、バーコータを用いて、乾燥時の塗膜の厚さが6μmになるように塗布し、乾燥後、水銀ランプを用いて、紫外線(積算300mJ/cm2、15秒)を照射した。得られた塗膜の表面抵抗率は、1.6E+04Ω/sqであった。なお、上記電子伝導性重合体(A)を含まないイオン伝導性単量体組成物を単独に塗布し、紫外線硬化した塗膜の表面抵抗率は、1.0E+09Ω/sqであった。
Claims (8)
- チオフェンの3位および/又は4位の水素原子をエーテル酸素で置換したチオフェン誘導体が複数個連結してなる電子伝導性重合体が、フルオロ基及びスルホニル基を備える陰イオンを有する塩を溶解した、アクリロイル基、メタクリロイル基及びビニル基からなる群より選ばれた重合する官能基を有する化合物中に微液滴状になって散在あるいは溶込んでいる、導電性重合体組成物。
- 前記チオフェン誘導体は、3,4−エチレンジオキシチオフェンを含む、請求項1に記載の導電性重合体組成物。
- 前記フルオロ基及びスルホニル基を備える塩は、リチウムビス(フルオロスルホニル)イミド、リチウムビス(トリフルオロメタンスルホニル)イミド又はトリフルオロメタンスルホン酸リチウムを含む請求項1又は2に記載の導電性重合体組成物。
- 前記フルオロ基およびスルホニル基を備える陰イオンを有する塩を溶解した前記重合する官能基を有する化合物100質量部に対して、前記電子伝導性重合体を0.005〜50.0質量部含むことを特徴とする請求項1〜3のいずれか1項に記載の導電性重合体組成物。
- 請求項1〜4のいずれか1項に記載の導電性重合体組成物を含む塗料。
- 請求項1〜4のいずれか1項に記載の導電性重合体組成物を含む制電性被覆物。
- チオフェンの3位および/又は4位の水素原子をエーテル酸素で置換したチオフェン誘導体が複数個連結してなる電子伝導性重合体を準備する第1工程と、
アクリロイル基、メタクリロイル基及びビニル基からなる群より選ばれた重合する官能基を有する化合物中に、フルオロ基及びスルホニル基を備える陰イオンを有する塩を溶解した溶液を準備する第2工程と、
前記第1工程で準備した電子伝導性重合体を、前記第2工程で準備した前記溶液中に添加し攪拌する第3工程と、を備えた、導電性重合体組成物の製造方法。 - 前記アクリロイル基、メタクリロイル基及びビニル基からなる群より選ばれた重合する官能基を有する前記化合物は、ポリエチレングリコールジアクリレート又はポリエチレングリコールジメタクリレートを含む請求項1に記載の導電性重合体組成物。
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