JP2007051219A - Antistatic cyclic olefin-based polymer composition - Google Patents
Antistatic cyclic olefin-based polymer composition Download PDFInfo
- Publication number
- JP2007051219A JP2007051219A JP2005237488A JP2005237488A JP2007051219A JP 2007051219 A JP2007051219 A JP 2007051219A JP 2005237488 A JP2005237488 A JP 2005237488A JP 2005237488 A JP2005237488 A JP 2005237488A JP 2007051219 A JP2007051219 A JP 2007051219A
- Authority
- JP
- Japan
- Prior art keywords
- group
- trifluoromethanesulfonyl
- bis
- imide
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 14
- -1 cyclic olefin Chemical class 0.000 title abstract description 85
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 19
- 229920000642 polymer Polymers 0.000 title abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 150000004010 onium ions Chemical class 0.000 claims abstract description 20
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 17
- 239000002216 antistatic agent Substances 0.000 claims abstract description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000002952 polymeric resin Substances 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 90
- 239000000178 monomer Substances 0.000 description 8
- 239000011342 resin composition Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 3
- WFKZGXKJFFOGPM-UHFFFAOYSA-N 1-butylthiolan-1-ium Chemical compound CCCC[S+]1CCCC1 WFKZGXKJFFOGPM-UHFFFAOYSA-N 0.000 description 3
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- XDGPPYJMOCHAGB-UHFFFAOYSA-N 1-methyl-1-octylpiperidin-1-ium Chemical compound CCCCCCCC[N+]1(C)CCCCC1 XDGPPYJMOCHAGB-UHFFFAOYSA-N 0.000 description 3
- JWPBORWCDZAHAU-UHFFFAOYSA-N 1-methyl-1-octylpyrrolidin-1-ium Chemical compound CCCCCCCC[N+]1(C)CCCC1 JWPBORWCDZAHAU-UHFFFAOYSA-N 0.000 description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 description 3
- 125000005917 3-methylpentyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 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 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- YPKUOQRBNZPMAE-UHFFFAOYSA-N 1-decyl-1-methylpyrrolidin-1-ium Chemical compound CCCCCCCCCC[N+]1(C)CCCC1 YPKUOQRBNZPMAE-UHFFFAOYSA-N 0.000 description 2
- FFWXFIDSMMQAQV-UHFFFAOYSA-N 1-decylthiolan-1-ium Chemical compound C(CCCCCCCCC)[S+]1CCCC1 FFWXFIDSMMQAQV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- XZDPRAGZNFQVIM-UHFFFAOYSA-N 1-heptyl-1-methylpyrrolidin-1-ium Chemical compound CCCCCCC[N+]1(C)CCCC1 XZDPRAGZNFQVIM-UHFFFAOYSA-N 0.000 description 2
- MSXLKHPWXBSHLC-UHFFFAOYSA-N 1-heptylthiolan-1-ium Chemical compound C(CCCCCC)[S+]1CCCC1 MSXLKHPWXBSHLC-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- FHZKIKVDRZVWKN-UHFFFAOYSA-N 1-hexyl-1-methylpiperidin-1-ium Chemical compound CCCCCC[N+]1(C)CCCCC1 FHZKIKVDRZVWKN-UHFFFAOYSA-N 0.000 description 2
- LMSPMULSARFKPJ-UHFFFAOYSA-N 1-methyl-1-nonylpyrrolidin-1-ium Chemical compound CCCCCCCCC[N+]1(C)CCCC1 LMSPMULSARFKPJ-UHFFFAOYSA-N 0.000 description 2
- RPWBQXPKTCIOTN-UHFFFAOYSA-M 1-methyl-1-octylpiperidin-1-ium;bromide Chemical compound [Br-].CCCCCCCC[N+]1(C)CCCCC1 RPWBQXPKTCIOTN-UHFFFAOYSA-M 0.000 description 2
- XEISMKAGBLMRAJ-UHFFFAOYSA-N 1-nonylthiolan-1-ium Chemical compound C(CCCCCCCC)[S+]1CCCC1 XEISMKAGBLMRAJ-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- LVZBZVQBEMOZNC-UHFFFAOYSA-N 1-octylthiolan-1-ium Chemical compound C(CCCCCCC)[S+]1CCCC1 LVZBZVQBEMOZNC-UHFFFAOYSA-N 0.000 description 2
- VIAXSPFGGOUOOQ-UHFFFAOYSA-N 1-pentylthiolan-1-ium Chemical compound CCCCC[S+]1CCCC1 VIAXSPFGGOUOOQ-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OHXOWTBGMKMMPD-UHFFFAOYSA-N C(CCCC)[S+]1CCCCC1 Chemical compound C(CCCC)[S+]1CCCCC1 OHXOWTBGMKMMPD-UHFFFAOYSA-N 0.000 description 2
- LWGDRAVYQPNEPF-UHFFFAOYSA-N C(CCCCCCC)[S+]1CCCCC1 Chemical compound C(CCCCCCC)[S+]1CCCCC1 LWGDRAVYQPNEPF-UHFFFAOYSA-N 0.000 description 2
- 0 CC1(C)C[N+](*)(*)C*(*)C*C1 Chemical compound CC1(C)C[N+](*)(*)C*(*)C*C1 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- KTQVJAPIQPIIPF-IOBHVTPZSA-N (1Z,2Z)-N,N'-dihydroxyethanediimidoyl dichloride Chemical compound O\N=C(/Cl)\C(\Cl)=N\O KTQVJAPIQPIIPF-IOBHVTPZSA-N 0.000 description 1
- SKDNDVDHYMEGNJ-UHFFFAOYSA-N (2-bromo-2-nitroethenyl)benzene Chemical compound [O-][N+](=O)C(Br)=CC1=CC=CC=C1 SKDNDVDHYMEGNJ-UHFFFAOYSA-N 0.000 description 1
- JAGYXYUAYDLKNO-GGWOSOGESA-N (2e,5e)-hepta-2,5-diene Chemical compound C\C=C\C\C=C\C JAGYXYUAYDLKNO-GGWOSOGESA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical class O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
- GYHKODORJRRYBU-CLFYSBASSA-N (z)-n-hydroxybenzenecarboximidoyl chloride Chemical compound O\N=C(/Cl)C1=CC=CC=C1 GYHKODORJRRYBU-CLFYSBASSA-N 0.000 description 1
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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229960001147 triclofos Drugs 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
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Abstract
Description
本発明は、帯電防止性環状オレフィン系重合体組成物に関する。 The present invention relates to an antistatic cyclic olefin polymer composition.
従来、ポリカーボネート樹脂等の熱可塑性樹脂にその透明性を損なうことなく帯電防止性を付与する方法として、帯電防止剤としてオニウム化合物を添加する方法が知られており、例えば、ポリカーボネート樹脂にアンモニウム塩系のオニウム化合物を添加し、混練する方法が知られている(例えば、特許文献1参照)。しかし、本発明者が熱可塑性樹脂の一種である環状オレフィン系重合体に、帯電防止性を付与するためにピリジニウム塩、イミダゾリウム塩及び脂肪族四級アンモニウム塩等のアンモニウム塩系のオニウム化合物を添加したところ、いずれの場合も透明性を維持することができなかった。
本発明は、透明性を損なうことなく帯電防止性が付与された、環状オレフィン系重合体樹脂組成物及びその組成物に用いる帯電防止剤を提供することを課題とする。 This invention makes it a subject to provide the antistatic agent used for the cyclic olefin polymer resin composition and its composition to which antistatic property was provided, without impairing transparency.
本発明者が上記課題を解決するために鋭意検討したところ、驚くべきことに帯電防止剤として特定のオニウム化合物を環状オレフィン系重合体に配合することで、透明性を損なうことなく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。 When the present inventor diligently studied to solve the above-mentioned problems, surprisingly, by adding a specific onium compound as an antistatic agent to the cyclic olefin polymer, antistatic properties can be obtained without impairing transparency. The inventors have found that it can be imparted, and have completed the present invention.
即ち、本発明は、帯電防止剤として、式(1): That is, the present invention provides an antistatic agent represented by the formula (1):
本発明によれば、透明性を損なうことなく帯電防止性が付与された帯電防止性環状オレフィン系重合体組成物が提供できるので、透明性が必要とされる様々な用途に用いることが可能となり、本発明の組成物および帯電防止剤は極めて有用である。 According to the present invention, it is possible to provide an antistatic cyclic olefin polymer composition imparted with antistatic properties without impairing transparency, so that it can be used for various applications where transparency is required. The compositions and antistatic agents of the present invention are extremely useful.
以下、本発明を詳細に説明する。
本発明の帯電防止性環状オレフィン系重合体組成物(以下、帯電防止樹脂組成物という)は、帯電防止剤としてアンモニウム塩(1)及びスルホニウム塩(2)から選ばれる1種以上のオニウム化合物を環状オレフィン系重合体に含有せしめて得られるものである。
Hereinafter, the present invention will be described in detail.
The antistatic cyclic olefin polymer composition of the present invention (hereinafter referred to as an antistatic resin composition) comprises at least one onium compound selected from an ammonium salt (1) and a sulfonium salt (2) as an antistatic agent. It is obtained by adding it to a cyclic olefin polymer.
式(1)及び式(2)中、R1はアルキル基又はアルキルオキシアルキル基を表す。アルキル基としては、通常直鎖状又は分岐鎖状の炭素数1〜16のアルキル基、好ましくは直鎖状又は分岐鎖状の炭素数4〜12のアルキル基である。具体的には、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、1−メチルブチル基、2−メチルブチル基、3−メチルブチル基、1−エチルプロピル基、1,1−ジメチルプロピル基、1,2−ジメチルプロピル基、2,2−ジメチルプロピル基、ヘキシル基、1−メチルペンチル基、2−メチルペンチル基、3−メチルペンチル基、4−メチルペンチル基、1,1−ジメチルブチル基、2,2−ジメチルブチル基、3,3−ジメチルブチル基、1,2−ジメチルブチル基、1,3−ジメチルブチル基、2,3−ジメチルブチル基、1−エチルブチル基、2−エチルブチル基、ヘプチル基、オクチル基、ノニル基、デシル基、ドデシル基、テトラデシル基、ヘキサデシル基等が挙げられる。アルキルオキシアルキル基としては、具体的には、例えばメチルオキシエチル基、エチルオキシエチル基、プロピルオキシエチル基、ブチルオキシエチル基、メチルオキシプロピル基、エチルオキシプロピル基、プロピルオキシプロピル基、ブチルオキシプロピル基、メチルオキシブチル基、エチルオキシブチル基、プロピルオキシブチル基、ブチルオキシブチル基等が挙げられる。 In Formula (1) and Formula (2), R 1 represents an alkyl group or an alkyloxyalkyl group. The alkyl group is usually a linear or branched alkyl group having 1 to 16 carbon atoms, preferably a linear or branched alkyl group having 4 to 12 carbon atoms. Specifically, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl Group, 1-ethylpropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methyl Pentyl group, 4-methylpentyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2 , 3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, tetradecyl group Group, hexadecyl group and the like. Specific examples of the alkyloxyalkyl group include a methyloxyethyl group, an ethyloxyethyl group, a propyloxyethyl group, a butyloxyethyl group, a methyloxypropyl group, an ethyloxypropyl group, a propyloxypropyl group, and a butyloxy group. Examples thereof include a propyl group, a methyloxybutyl group, an ethyloxybutyl group, a propyloxybutyl group, and a butyloxybutyl group.
式(1)中、R2は水素原子又は炭素数1〜4のアルキル基を表す。炭素数1〜4のアルキル基としては、通常直鎖状又は分岐鎖状の炭素数1〜4のアルキル基が挙げられ、具体的には、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基が挙げられる。 In formula (1), R 2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a normal or branched alkyl group having 1 to 4 carbon atoms, specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, A butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group are mentioned.
式(1)及び式(2)中、R3は炭素数1〜4のアルキル基を表す。炭素数1〜4のアルキル基としては、通常直鎖状又は分岐鎖状の炭素数1〜4のアルキル基が挙げられ、具体的には、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基が挙げられる。 In Formula (1) and Formula (2), R 3 represents an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a normal or branched alkyl group having 1 to 4 carbon atoms, specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, A butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group are mentioned.
アンモニウム塩(1)は、環状オレフィン系重合体の溶融温度付近で液体のものが好ましく、室温付近で液体のものが特に好ましい。室温付近で液体のものの具体例としては、1−ブチル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ペンチル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘキシル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘプチル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−オクチル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ノニル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−デシル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ドデシル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシエチル)−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシエチル)−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシプロピル)−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシプロピル)−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド、 The ammonium salt (1) is preferably liquid around the melting temperature of the cyclic olefin polymer, and particularly preferably liquid around room temperature. Specific examples of liquids near room temperature include 1-butyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide, 1-pentyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide, -Hexyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide, 1-heptyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide, 1-octyl-1-methylpyrrolidinium bis ( Trifluoromethanesulfonyl) imide, 1-nonyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide, 1-decyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide, 1-dodecyl-1- Methylpyrrolidinium bis ( Trifluoromethanesulfonyl) imide, 1- (methyloxyethyl) -1-methylpyrrolidinium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxyethyl) -1-methylpyrrolidinium = bis (trifluoromethanesulfonyl) ) Imide, 1- (methyloxypropyl) -1-methylpyrrolidinium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxypropyl) -1-methylpyrrolidinium = bis (trifluoromethanesulfonyl) imide,
1−ブチル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ペンチル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘキシル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘプチル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−オクチル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ノニル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−デシル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ドデシル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシエチル)−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシエチル)−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシプロピル)−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシプロピル)−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド、 1-butyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1-pentyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1-hexyl-1-methylpiperidinium = bis (Trifluoromethanesulfonyl) imide, 1-heptyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1-octyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1-nonyl-1 -Methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1-decyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1-dodecyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) Imide, -(Methyloxyethyl) -1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxyethyl) -1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1- (methyloxy Propyl) -1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxypropyl) -1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide,
1−ブチル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ペンチル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘキシル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘプチル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−オクチル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ノニル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−デシル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ドデシル−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシエチル)−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシエチル)−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシプロピル)−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシプロピル)−1−メチルモルホニウム=ビス(トリフルオロメタンスルホニル)イミド、 1-butyl-1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1-pentyl-1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1-hexyl-1-methylmorphonium = bis (Trifluoromethanesulfonyl) imide, 1-heptyl-1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1-octyl-1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1-nonyl-1 -Methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1-decyl-1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1-dodecyl-1-methylmorphonium = bis (trifluoromethanesulfonyl) Imido, 1- (methyloxy Ethyl) -1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxyethyl) -1-methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1- (methyloxypropyl) -1 -Methylmorphonium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxypropyl) -1-methylmorphonium = bis (trifluoromethanesulfonyl) imide,
1−ブチル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ペンチル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘキシル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘプチル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−オクチル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ノニル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−デシル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ドデシル−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシエチル)−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシエチル)−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(メチルオキシプロピル)−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド、1−(エチルオキシプロピル)−1−メチルピペラジニウム=ビス(トリフルオロメタンスルホニル)イミド等が挙げられる。これらの中でも式(3): 1-butyl-1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1-pentyl-1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1-hexyl-1-methylpiperazinium = bis (Trifluoromethanesulfonyl) imide, 1-heptyl-1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1-octyl-1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1-nonyl-1 -Methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1-decyl-1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1-dodecyl-1-methylpiperazinium = bis (trifluoromethanesulfonyl) Imide, -(Methyloxyethyl) -1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxyethyl) -1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1- (methyloxy Propyl) -1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, 1- (ethyloxypropyl) -1-methylpiperazinium = bis (trifluoromethanesulfonyl) imide, and the like. Among these, formula (3):
スルホニウム塩(2)は、環状オレフィン系重合体の溶融温度付近で液体のものが好ましく、室温付近で液体のものが特に好ましい。室温付近で液体のものの具体例としては、1−ブチル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ペンチル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘキシル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘプチル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−オクチル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ノニル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−デシル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ドデシル−テトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ブチル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ペンチル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘキシル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ヘプチル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−オクチル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ノニル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−デシル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド、1−ドデシル−テトラヒドロチオピラニウム=ビス(トリフルオロメタンスルホニル)イミド等が挙げられる。これらの中でも、式(4): The sulfonium salt (2) is preferably liquid around the melting temperature of the cyclic olefin polymer, and particularly preferably liquid around room temperature. Specific examples of liquids near room temperature include 1-butyl-tetrahydrothiophenium = bis (trifluoromethanesulfonyl) imide, 1-pentyl-tetrahydrothiophenium = bis (trifluoromethanesulfonyl) imide, 1-hexyl-tetrahydro. Thiophenium = bis (trifluoromethanesulfonyl) imide, 1-heptyl-tetrahydrothiophenium = bis (trifluoromethanesulfonyl) imide, 1-octyl-tetrahydrothiophenium = bis (trifluoromethanesulfonyl) imide, 1-nonyl- Tetrahydrothiophenium = bis (trifluoromethanesulfonyl) imide, 1-decyl-tetrahydrothiophenium = bis (trifluoromethanesulfonyl) imide, 1-dodecyl-tetrahydrothiol Ni = bis (trifluoromethanesulfonyl) imide, 1-butyl-tetrahydrothiopyranium = bis (trifluoromethanesulfonyl) imide, 1-pentyl-tetrahydrothiopyranium = bis (trifluoromethanesulfonyl) imide, 1-hexyl-tetrahydrothio Pyranium = bis (trifluoromethanesulfonyl) imide, 1-heptyl-tetrahydrothiopyranium = bis (trifluoromethanesulfonyl) imide, 1-octyl-tetrahydrothiopyranium = bis (trifluoromethanesulfonyl) imide, 1-nonyl-tetrahydro Thiopyronium = bis (trifluoromethanesulfonyl) imide, 1-decyl-tetrahydrothiopyranium = bis (trifluoromethanesulfonyl) imide, 1-dodecyl-te La hydro thio Pila hexafluorophosphate = bis (trifluoromethanesulfonyl) imide, and the like. Among these, the formula (4):
かかるオニウム化合物は、例えば本出願人の出願した特願2004−379548の明細書に記載の製造法により容易に製造できる。具体的には、三級アミン類又はスルフィド類を、アルキルハライド類と反応させて、それぞれ対応するオニウム=ハライドを製造した後、リチウム=ビス(トリフルオロメタンスルホニル)イミドとのイオン交換反応により容易に製造できる。 Such an onium compound can be easily produced, for example, by the production method described in the specification of Japanese Patent Application No. 2004-379548 filed by the present applicant. Specifically, tertiary amines or sulfides are reacted with alkyl halides to produce the corresponding onium = halides, and then easily exchanged with lithium = bis (trifluoromethanesulfonyl) imide. Can be manufactured.
本発明に用いる環状オレフィン系重合体は、分子内に単環構造、多環構造、縮合多環構造、橋架け環構造等の脂環式炭化水素構造を有する重合体である。脂環式炭化水素構造としては、シクロアルカン構造やシクロアルケン構造等が挙げられる。脂環式炭化水素構造を構成する炭素原子数は、特に制限はないが、通常4〜30個、好ましくは5〜20個、より好ましくは5〜15個の範囲である。 The cyclic olefin polymer used in the present invention is a polymer having an alicyclic hydrocarbon structure such as a monocyclic structure, a polycyclic structure, a condensed polycyclic structure, or a bridged ring structure in the molecule. Examples of the alicyclic hydrocarbon structure include a cycloalkane structure and a cycloalkene structure. The number of carbon atoms constituting the alicyclic hydrocarbon structure is not particularly limited, but is usually in the range of 4-30, preferably 5-20, more preferably 5-15.
環状オレフィン系重合体は、脂環式炭化水素構造を有するオレフィン(以下、脂環式オレフィンという。)由来の繰り返し単位を含有する。環状オレフィン系重合体中の脂環式オレフィン由来の繰り返し単位の割合は、使用目的に応じて適宜選択されるが、通常30〜100重量%、好ましくは50〜100重量%、より好ましくは70〜100重量%である。また、環状オレフィン系重合体は、極性基を有するものであってもよい。極性基としては、ヒドロキシル基、カルボキシル基、アルコキシル基、エポキシ基、グリシジル基、オキシカルボニル基、カルボニル基、アミノ基、エステル基、カルボン酸無水物基等が挙げられる。 The cyclic olefin-based polymer contains a repeating unit derived from an olefin having an alicyclic hydrocarbon structure (hereinafter referred to as alicyclic olefin). The ratio of the repeating unit derived from the alicyclic olefin in the cyclic olefin polymer is appropriately selected depending on the purpose of use, but is usually 30 to 100% by weight, preferably 50 to 100% by weight, more preferably 70 to 70%. 100% by weight. Further, the cyclic olefin polymer may have a polar group. Examples of the polar group include hydroxyl group, carboxyl group, alkoxyl group, epoxy group, glycidyl group, oxycarbonyl group, carbonyl group, amino group, ester group, carboxylic acid anhydride group and the like.
かかる環状オレフィン系重合体は、市販品[例えば、ゼオネックスやゼオノア(日本ゼオン株式会社製)、アートン(JSR株式会社製)、アペル(三井化学株式会社製)、トパス(ティコナ株式会社製)等の各登録商標名で知られる重合体]を用いてもよいし、又は1)脂環式オレフィンを付加重合又は開環重合し、そして必要に応じて不飽和結合部分を水素化することによって、或いは、2)芳香族オレフィンを付加重合し、そして該重合体の芳香環部分を水素化することによって得られたものを用いてもよい。 Such cyclic olefin-based polymers are commercially available products [for example, ZEONEX, ZEONOR (manufactured by ZEON CORPORATION), ARTON (manufactured by JSR Corporation), APPEL (manufactured by Mitsui Chemicals), TOPAS (manufactured by Ticona Corporation) A polymer known by each registered trade name], or 1) by addition polymerization or ring-opening polymerization of an alicyclic olefin, and optionally hydrogenating an unsaturated bond portion, or 2) You may use what was obtained by addition-polymerizing an aromatic olefin and hydrogenating the aromatic-ring part of this polymer.
脂環式オレフィンとしては、ノルボルネン、ジシクロペンタジエン、テトラシクロドデセン、エチルテトラシクロドデセン、エチリデンテトラシクロドデセン、テトラシクロ〔7,4,0,110,13,02,7〕トリデカ−2,4,6,11−テトラエン等の多環構造の不飽和炭化水素及びその誘導体、シクロブテン、シクロペンテン、シクロヘキセン、3,4−ジメチルシクロペンテン、3−メチルシクロヘキセン、2−(2−メチルブチル)−1−シクロヘキセン、シクロオクテン、3a,5,6,7a−テトラヒドロ−4,7−メタノ−1H−インデン、シクロヘプテン、シクロペンタジエン、シクロヘキサジエン等の単環構造の不飽和炭化水素及びその誘導体等が挙げられる。これら環状オレフィンには置換基として上述の極性基を有していてもよい。芳香族オレフィンとしては、スチレン、α−メチルスチレン、ジビニルベンゼン等が挙げられる。脂環式オレフィン及び/又は芳香族オレフィンは、それぞれ単独で、又は2種以上を混合して使用できる。 The alicyclic olefin, norbornene, dicyclopentadiene, tetracyclododecene, ethyl tetracyclododecene, ethylidene tetracyclododecene, tetracyclo [7,4,0,1 10,13, 0 2,7] trideca - Unsaturated hydrocarbons having a polycyclic structure such as 2,4,6,11-tetraene and derivatives thereof, cyclobutene, cyclopentene, cyclohexene, 3,4-dimethylcyclopentene, 3-methylcyclohexene, 2- (2-methylbutyl) -1 -Monocyclic unsaturated hydrocarbons such as cyclohexene, cyclooctene, 3a, 5,6,7a-tetrahydro-4,7-methano-1H-indene, cycloheptene, cyclopentadiene, cyclohexadiene and derivatives thereof . These cyclic olefins may have the above-mentioned polar group as a substituent. Examples of the aromatic olefin include styrene, α-methylstyrene, divinylbenzene and the like. The alicyclic olefin and / or aromatic olefin can be used alone or in admixture of two or more.
また必要に応じて、脂環式オレフィン又は芳香族オレフィンと共重合可能な単量体を付加共重合させることもできる。かかる単量体の具体例としては、エチレン、プロピレン、1−ブテン、1−ペンテン、1−ヘキセン、3−メチル−1−ブテン、3−メチル−1−ペンテン、3−エチル−1−ペンテン、4−メチル−1−ペンテン、4−メチル−1−ヘキセン、4,4−ジメチル−1−ヘキセン、4,4−ジメチル−1−ペンテン、4−エチル−1−ヘキセン、3−エチル−1−ヘキセン、1−オクテン、1−デセン、1−ドデセン、1−テトラデセン、1−ヘキサデセン、1−オクタデセン、1−エイコセン等の炭素数2〜20のエチレン又はα−オレフィン;1,4−ヘキサジエン、4−メチル−1,4−ヘキサジエン、5−メチル−1,4−ヘキサジエン、1,7−オクタジエン等の非共役ジエン、1,3−ブタジエン、イソプレン等が挙げられる。これらの単量体は、それぞれ単独で、又は2種以上を混合して使用できる。 If necessary, a monomer copolymerizable with an alicyclic olefin or an aromatic olefin can be addition-copolymerized. Specific examples of such monomers include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 3-methyl-1-pentene, 3-ethyl-1-pentene, 4-methyl-1-pentene, 4-methyl-1-hexene, 4,4-dimethyl-1-hexene, 4,4-dimethyl-1-pentene, 4-ethyl-1-hexene, 3-ethyl-1- Ethylene or α-olefin having 2 to 20 carbon atoms such as hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicocene; 1,4-hexadiene, 4 -Non-conjugated dienes such as methyl-1,4-hexadiene, 5-methyl-1,4-hexadiene, 1,7-octadiene, 1,3-butadiene, isoprene and the like. These monomers can be used alone or in admixture of two or more.
環状オレフィン系重合体の具体例としては、ノルボルネン系単量体の開環重合体及びその水素化物、ノルボルネン系単量体の付加重合体、ノルボルネン系単量体とビニル化合物(エチレン、α−オレフィン等)との付加重合体、単環シクロアルケンの重合体、脂環式共役ジエン系単量体の重合体、ビニル脂環式炭化水素系単量体の重合体及びその水素化物、芳香族オレフィン重合体の芳香環水素化物等が挙げられる。 Specific examples of cyclic olefin polymers include ring-opening polymers of norbornene monomers and their hydrides, addition polymers of norbornene monomers, norbornene monomers and vinyl compounds (ethylene, α-olefins). Etc.), polymer of monocyclic cycloalkene, polymer of alicyclic conjugated diene monomer, polymer of vinyl alicyclic hydrocarbon monomer and hydride thereof, aromatic olefin Examples thereof include aromatic ring hydrides of polymers.
本発明の帯電防止樹脂組成物に含まれるオニウム化合物の量は、環状オレフィン系重合体に対して、通常0.1〜20重量%、好ましくは0.5〜10重量%、特に好ましくは0.7〜7重量%である。 The amount of the onium compound contained in the antistatic resin composition of the present invention is usually from 0.1 to 20% by weight, preferably from 0.5 to 10% by weight, particularly preferably from 0.005% by weight based on the cyclic olefin polymer. 7 to 7% by weight.
本発明の帯電防止樹脂組成物および帯電防止剤には、本発明の効果を阻害しない範囲で、必要に応じて、導電性物質、着色料、充填剤、滑剤、可塑剤、難燃剤、分散剤、離型剤、酸化防止剤、紫外線吸収剤、抗菌剤等の樹脂用添加剤を適宜配合することができる。 In the antistatic resin composition and the antistatic agent of the present invention, a conductive substance, a colorant, a filler, a lubricant, a plasticizer, a flame retardant, and a dispersant are added as necessary within the range not inhibiting the effects of the present invention. Additives for resins such as mold release agents, antioxidants, ultraviolet absorbers, and antibacterial agents can be appropriately blended.
導電性物質としては、例えばカーボンナノチューブ、カーボンブラック、ホワイトカーボン等が挙げられる。 Examples of the conductive substance include carbon nanotubes, carbon black, white carbon, and the like.
着色料としては、例えば無機顔料、有機顔料、染料が挙げられる。無機顔料としては、例えば白色顔料(例えば酸化チタン、リトポン、鉛白、亜鉛華等)、コバルト化合物(例えばオーレオリン、コバルトグリーン、セルリアンブルー、コバルトブルー、コバルトバイオレット等)、鉄化合物(例えば酸化鉄、紺青等)、クロム化合物(例えば酸化クロム、クロム酸鉛、クロム酸バリウム等)、硫化物(例えば硫化カドミウム、カドミウムイエロー、ウルトラマリン等)等が挙げられる。有機顔料としては、例えばアゾ顔料(例えばアゾレーキ系、モノアゾ系、ジスアゾ系、キレートアゾ系等)、多環式顔料(例えばベンゾイミダゾロン系、フタロシアニン系、キナクリドン系、ジオキサジン系、イソインドリノン系、チオインジゴ系、ペリレン系、キノフタロン系、アンスラキノン系等)等が挙げられる。染料としては、例えばアゾ系、アントラキノン系、インジゴイド系、硫化系、トリフェニルメタン系、ピラゾロン系、スチルベン系、ジフェニルメタン系、キサンテン系、アリザリン系、アクリジン系、キノンイミン系、チアゾール系、メチン系、ニトロ系、ニトロソ系、アニリン系等が挙げられる。 Examples of the colorant include inorganic pigments, organic pigments, and dyes. Examples of inorganic pigments include white pigments (eg, titanium oxide, lithopone, lead white, zinc white), cobalt compounds (eg, aureoline, cobalt green, cerulean blue, cobalt blue, cobalt violet, etc.), iron compounds (eg, iron oxide, Bitumen, etc.), chromium compounds (eg, chromium oxide, lead chromate, barium chromate, etc.), sulfides (eg, cadmium sulfide, cadmium yellow, ultramarine, etc.) and the like. Examples of organic pigments include azo pigments (eg, azo lake, monoazo, disazo, chelate azo, etc.), polycyclic pigments (eg, benzimidazolone, phthalocyanine, quinacridone, dioxazine, isoindolinone, thioindigo). System, perylene system, quinophthalone system, anthraquinone system, etc.). Examples of the dye include azo, anthraquinone, indigoid, sulfide, triphenylmethane, pyrazolone, stilbene, diphenylmethane, xanthene, alizarin, acridine, quinoneimine, thiazole, methine, nitro System, nitroso system, aniline system and the like.
充填剤としては、例えば無機充填剤(例えば炭酸カルシウム、タルク、クレー、ケイ酸、ケイ酸塩、アスベスト、マイカ、ガラス繊維、ガラスバルーン、カーボン繊維、金属繊維、セラミックウィスカ、チタンウィスカ等)、有機充填剤[例えば尿素、ステアリン酸カルシウム、有機架橋微粒子(例えばエポキシ系、ウレタン系等)等]等が挙げられる。 Examples of the filler include inorganic fillers (for example, calcium carbonate, talc, clay, silicic acid, silicate, asbestos, mica, glass fiber, glass balloon, carbon fiber, metal fiber, ceramic whisker, titanium whisker, etc.), organic Fillers [for example, urea, calcium stearate, organic crosslinked fine particles (for example, epoxy-based, urethane-based, etc.)] and the like.
滑剤としては、例えば炭化水素(流動パラフィン、天然パラフィン、マイクロワックス、ポリエチレンワックス等)、高級脂肪酸(例えばステアリン酸、オキシ脂肪酸等)、脂肪酸アミド(例えばステアリン酸アミド、パルミチン酸アミド、メチレンビスステアリルアミド等)、脂肪酸エステル(例えばステアリン酸ブチル、ステアリン酸エチル等)、脂肪酸多価アルコールエステル(例えば硬化ヒマシ油等)、脂肪酸グリコールエステル(例えばエチレングリコールモノステアレート等)が挙げられる。 Examples of the lubricant include hydrocarbons (liquid paraffin, natural paraffin, micro wax, polyethylene wax, etc.), higher fatty acids (eg, stearic acid, oxy fatty acid, etc.), fatty acid amides (eg, stearic acid amide, palmitic acid amide, methylene bisstearyl amide). Etc.), fatty acid esters (eg butyl stearate, ethyl stearate etc.), fatty acid polyhydric alcohol esters (eg hardened castor oil etc.), fatty acid glycol esters (eg ethylene glycol monostearate etc.).
可塑剤としては、例えばモノカルボン酸エステル[例えば脂肪酸エステル(例えばステアリン酸ブチル、オレイン酸メトキシエチル等)、芳香族カルボン酸エステル(例えばジエチレングリコールジベンゾエート、トリエチレングリコールジベンゾエート等)等]、ジカルボン酸エステル[例えば芳香族ジカルボン酸エステル(例えばフタル酸ジブチル、フタル酸ジ−2−エチルヘキシル等)等]、脂肪族ジカルボン酸エステル[例えばアジピン酸エステル(例えばアジピン酸ジ−2−エチルヘキシル、アジピン酸ジイソデシル等)、アゼライン酸エステル(例えばアゼライン酸ジ−n−ヘキシル、アゼライン酸ジ−2−エチルヘキシル等)、セバシン酸エステル(例えばセバシン酸ジブチル、セバシン酸ジ−2−エチルヘキシル等)等]、トリカルボン酸エステル[例えば脂肪族トリカルボン酸エステル(例えばクエン酸トリエチル、アセチルクエン酸トリブチル等)]、エポキシド(例えばエポキシ化大豆油、4,5−エポキシシクロヘキサン−1,2−ジカルボン酸ジ−2−エチルヘキシル等)、リン酸エステル(例えばリン酸トリブチル、リン酸トリブトキシエチル、リン酸トリクロルエチル等)、含塩素系炭化水素[例えば芳香族炭化水素(例えば塩素化ナフタリン、塩素化ジフェニル)、塩素化パラフィン等]等が挙げられる。 Examples of the plasticizer include monocarboxylic acid esters [for example, fatty acid esters (for example, butyl stearate, methoxyethyl oleate, etc.), aromatic carboxylic acid esters (for example, diethylene glycol dibenzoate, triethylene glycol dibenzoate, etc.), etc., dicarboxylic acids Esters [eg, aromatic dicarboxylic acid esters (eg, dibutyl phthalate, di-2-ethylhexyl phthalate, etc.)], aliphatic dicarboxylic acid esters [eg, adipic acid esters (eg, di-2-ethylhexyl adipate, diisodecyl adipate, etc.) ), Azelaic acid ester (eg, azelaic acid di-n-hexyl, azelaic acid di-2-ethylhexyl, etc.), sebacic acid ester (eg, dibutyl sebacate, di-2-ethylhexyl sebacate, etc.)], Recarboxylate [for example, aliphatic tricarboxylic acid ester (for example, triethyl citrate, tributyl acetyl citrate, etc.)], epoxide (for example, epoxidized soybean oil, di-2-ethylhexyl 4,5-epoxycyclohexane-1,2-dicarboxylate) Etc.), phosphate esters (eg tributyl phosphate, tributoxyethyl phosphate, trichloroethyl phosphate, etc.), chlorinated hydrocarbons (eg aromatic hydrocarbons (eg chlorinated naphthalene, chlorinated diphenyl), chlorinated paraffins) Etc.].
難燃剤としては、リン酸エステル系[例えば、トリクレジルホスフェート、トリス(2,3−ジブロモプロピル)ホスフェート等]、臭素系(例えばデカブロモビフェニルエーテル、テトラブロモビスフェノールA等)、三酸化アンチモン、水酸化マグネシウム、ホウ酸塩系(例えばホウ酸亜鉛、メタホウ酸バリウム等)、水酸化アルミニウム、赤リン、ポリリン酸アンモニウム、ヘット酸等が挙げられる。 Examples of the flame retardant include phosphate ester type [eg, tricresyl phosphate, tris (2,3-dibromopropyl) phosphate, etc.], bromine type (eg, decabromobiphenyl ether, tetrabromobisphenol A, etc.), antimony trioxide, Examples thereof include magnesium hydroxide, borates (for example, zinc borate, barium metaborate, etc.), aluminum hydroxide, red phosphorus, ammonium polyphosphate, and het acid.
分散剤としては、平均分子量(Mn)1,000〜100,000の分散剤、例えばナフタレンスルホン酸ホルマリン縮合物(Mn1,000〜10,000)、ポリスチレンスルホン酸のアルカリ金属(例えばナトリウム、カリウム)塩(Mn1,000〜100,000)、ポリアクリル酸のアルカリ金属(例えばナトリウム、カリウム)塩(Mn2,000〜50,000)、カルボキシメチルセルロース、ポリビニルアルコール等が挙げられる。 Examples of the dispersant include a dispersant having an average molecular weight (Mn) of 1,000 to 100,000, such as naphthalene sulfonic acid formalin condensate (Mn 1,000 to 10,000), an alkali metal of polystyrene sulfonic acid (for example, sodium, potassium). Examples thereof include salts (Mn 1,000 to 100,000), alkali metal (for example, sodium, potassium) salts of polyacrylic acid (Mn 2,000 to 50,000), carboxymethyl cellulose, polyvinyl alcohol and the like.
離型剤としては、例えばストレートシリコーンオイル(例えばMn800〜500,000の、ジメチルポリシロキサン、メチルフェニルポリシロキサン等)、有機変性シリコーンオイル(例えばポリオキシアルキレン基、水酸基、アミノ基、エポキシ基、カルボキシル基及び/又はメルカプト基を有するMn800〜50,000のシリコーンオイル)が挙げられる。 Examples of the release agent include straight silicone oil (for example, dimethylpolysiloxane and methylphenylpolysiloxane having Mn of 800 to 500,000), organic modified silicone oil (for example, polyoxyalkylene group, hydroxyl group, amino group, epoxy group, carboxyl group). Group and / or mercapto group Mn 800-50,000 silicone oil).
酸化防止剤としては、フェノール系[例えば2,6−ジ−tert−ブチル−p−クレゾール(BHT)、2,2’−メチレンビス(4−メチル−6−tert−ブチルフェノール)、テトラキス[メチレン−(3,5−ジ−tert−ブチル−4−ヒドロキシハイドロシンナメート)]メタン[商品名:イルガノックス1010、チバスペシャリティーケミカルズ株式会社製]等]、硫黄系[例えばジラウリル3,3’−チオジプロピオネート(DLTDP)、ジステアリル3,3’−チオジプロピオネート(DSTDP)等]、リン系[例えばトリフェニルホスファイト(TPP)、トリイソデシルホスファイト(TDP)、トリス(2,4−ジ−tert−ブチルフェニル)ホスファイト、モノ−、ジステアリルアシッドホスフェート等]、アミン系(例えばオクチル化ジフェニルアミン、N−n−ブチル−p−アミノフェノール、N,N−ジイソプロピル−p−フェニレンジアミン等)等が挙げられる。 Antioxidants include phenolic [eg, 2,6-di-tert-butyl-p-cresol (BHT), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), tetrakis [methylene- ( 3,5-di-tert-butyl-4-hydroxyhydrocinnamate)] methane [trade name: Irganox 1010, manufactured by Ciba Specialty Chemicals Co., Ltd.], etc.], sulfur [for example, dilauryl 3,3′-thiodipro Pionate (DLTDP), distearyl 3,3′-thiodipropionate (DSTDP), etc.], phosphorous [for example, triphenyl phosphite (TPP), triisodecyl phosphite (TDP), tris (2,4- Di-tert-butylphenyl) phosphite, mono-, distearyl acid phosphate ], Amine-based (e.g., octyl diphenylamine, N-n-butyl -p- aminophenol, N, N-diisopropyl -p- phenylenediamine), and the like.
紫外線吸収剤としては、ベンゾフェノン系(例えば2−ヒドロキシベンゾフェノン、2,4−ジヒドロキシベンゾフェノン等)、サリチレート系(例えばフェニルサリチレート、2,4−ジ−tert−ブチルフェニル−3,5−ジ−tert−ブチル−4−ヒドロキシベンゾエート等)、ベンゾトリアゾール系[例えば(2’−ヒドロキシフェニル)ベンゾトリアゾール、(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール等]、アクリル系[例えばエチル−2−シアノ−3,3−ジフェニルアクリレート、メチル−2−カルボメトキシ−3−(パラメトキシベンジル)アクリレート等]等が挙げられる。 Examples of the ultraviolet absorber include benzophenone (eg, 2-hydroxybenzophenone, 2,4-dihydroxybenzophenone), salicylate (eg, phenyl salicylate, 2,4-di-tert-butylphenyl-3,5-di-). tert-butyl-4-hydroxybenzoate, etc.), benzotriazoles [for example (2′-hydroxyphenyl) benzotriazole, (2′-hydroxy-5′-methylphenyl) benzotriazole, etc.], acrylics [for example ethyl-2 -Cyano-3,3-diphenyl acrylate, methyl-2-carbomethoxy-3- (paramethoxybenzyl) acrylate, etc.].
抗菌剤としては、イソチアゾロン系化合物、ハロゲン化脂肪族ニトロ化合物(例えば2−ブロモ−2−ニトロ−1,3−プロパンジオール、2,2−ジブロモ−2−ニトロエタノール等)、該ニトロ化合物のエステル、ジブロモニトリルプロピオンアミド、アルキレンビスチオシアネート(例えばメチレンビスチオシアネート等)、1,4−ビスブロモアセトキシ−2−ブテン、ヘキサブロモジメチルスルホン、イソフタロニトリル化合物(例えば5−クロロ−2,4,6−トリフルオロイソフタロニトリル、テトラクロロイソフタロニトリル等)、ジメチルジチオカルバメート、4,5−ジクロロ−1,2−ジオール−3−オン、3,3,4,4−テトラクロロテトラヒドロチオフェン−1,1−ジオキシド、トリヨードアリルアルコール、ブロモニトロスチレン、アルデヒド化合物(例えばグルタルアルデヒド、フタルアルデヒド、イソフタルアルデヒド、テレフタルアルデヒド等)、ジクロログリオキシム、ベンズアルドキシム化合物(例えばα−クロロベンズアルドキシム、α−クロロベンズアルドキシムアセテート等)、ハロゲン化ヒダントイン化合物(例えば1,3−ジクロロ−5,5−ジメチルヒダントイン、1,3−ジブロモ−5,5−ジメチルヒダントイン等)等が挙げられる。 Antibacterial agents include isothiazolone compounds, halogenated aliphatic nitro compounds (for example, 2-bromo-2-nitro-1,3-propanediol, 2,2-dibromo-2-nitroethanol, etc.), esters of the nitro compounds , Dibromonitrile propionamide, alkylene bis thiocyanate (eg, methylene bis thiocyanate), 1,4-bisbromoacetoxy-2-butene, hexabromodimethyl sulfone, isophthalonitrile compound (eg, 5-chloro-2,4,6- Trifluoroisophthalonitrile, tetrachloroisophthalonitrile, etc.), dimethyldithiocarbamate, 4,5-dichloro-1,2-diol-3-one, 3,3,4,4-tetrachlorotetrahydrothiophene-1,1 -Dioxide, triiodoallyl alcohol Bromonitrostyrene, aldehyde compounds (eg glutaraldehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde, etc.), dichloroglyoxime, benzaldoxime compounds (eg α-chlorobenzaldoxime, α-chlorobenzaldoxime acetate, etc.), halogen And hydantoin compounds such as 1,3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin.
本発明の帯電防止樹脂組成物の製造方法としては、1)オニウム化合物、環状オレフィン系重合体、及び必要に応じて上述した樹脂用添加剤(樹脂用添加剤についてはオニウム化合物及び/又は環状オレフィン系重合体に予め含有させておいてもよい。)を配合し、溶融混練する方法、2)オニウム化合物、環状オレフィン系重合体及び必要に応じて上述した樹脂用添加剤(樹脂用添加剤についてはオニウム化合物及び/又は環状オレフィン系重合体に予め含有させておいてもよい。)を、適当な溶媒に溶解せしめた後、溶媒を除去する方法等が挙げられる。 The production method of the antistatic resin composition of the present invention includes: 1) an onium compound, a cyclic olefin polymer, and, if necessary, an additive for a resin described above (for an additive for a resin, an onium compound and / or a cyclic olefin) 2) a method of blending, melt-kneading, and 2) an onium compound, a cyclic olefin polymer, and, if necessary, an additive for a resin (additive for a resin). May be preliminarily contained in the onium compound and / or the cyclic olefin polymer.
溶融混練するには、例えばペレット状または粉体状の環状オレフィン系重合体、及び各種成分を適切な混合機(例えばリボンブレンダー、ヘンシェルミキサー、ドラムブレンダー等)で配合した後、各種押出機、ブラベンダープラストグラフ、ラボプラストミル、ニーダー、バンバリーミキサー等を用いて、通常150〜360℃で溶融混練せしめればよい。このようにすれば本発明の帯電防止樹脂組成物が得られる。 For melt kneading, for example, a pellet or powdery cyclic olefin polymer and various components are blended in an appropriate mixer (for example, a ribbon blender, a Henschel mixer, a drum blender, etc.), and then various extruders, What is necessary is just to melt-knead normally at 150-360 degreeC using a lavender plastograph, a lab plast mill, a kneader, a Banbury mixer, etc. If it does in this way, the antistatic resin composition of this invention will be obtained.
また、溶媒としては、環状オレフィン系重合体が溶解するものであれば特に限定されないが、例えばヘキサン、ヘプタン等の脂肪族炭化水素溶媒、シクロヘキサン、シクロヘプタン等の脂環式炭化水素溶媒等が挙げられる。かかる溶媒の使用量は、環状オレフィン系重合体が十分に溶解できる量であれば特に制限されないが、環状オレフィン系重合体1重量部に対して、通常5重量部以上、好ましくは5重量部〜20重量部である。 The solvent is not particularly limited as long as it can dissolve the cyclic olefin polymer, and examples thereof include aliphatic hydrocarbon solvents such as hexane and heptane, and alicyclic hydrocarbon solvents such as cyclohexane and cycloheptane. It is done. The amount of the solvent used is not particularly limited as long as the cyclic olefin polymer can be sufficiently dissolved, but is usually 5 parts by weight or more, preferably 5 parts by weight to 1 part by weight of the cyclic olefin polymer. 20 parts by weight.
各種成分を溶解して得られた溶液を適当な型に流し込み、その後溶媒を除去し、乾燥することで本発明の帯電防止樹脂組成物を得ることができる。 The antistatic resin composition of the present invention can be obtained by pouring a solution obtained by dissolving various components into an appropriate mold, then removing the solvent and drying.
以下に実施例を挙げて本発明をより詳細に説明するが、本発明はかかる実施例に限定されるものではない。なお、帯電防止性は表面抵抗値を指標として評価し、デジタル抵抗計(三菱油化株式会社製;HT−210)を用いて、温度25℃、相対湿度65%の条件下で行った。また、透明性は目視及びヘーズ(曇価)を指標として評価し、ヘーズはヘーズメーター(スガ試験機株式会社製;HGM−2DP)を用いて測定した。 Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to such examples. The antistatic property was evaluated using the surface resistance value as an index, and was performed using a digital resistance meter (manufactured by Mitsubishi Yuka Co., Ltd .; HT-210) under conditions of a temperature of 25 ° C. and a relative humidity of 65%. Transparency was evaluated using visual and haze (cloudiness value) as indices, and haze was measured using a haze meter (manufactured by Suga Test Instruments Co., Ltd .; HGM-2DP).
実施例1[オニウム化合物の製造]
1−メチルピペリジン150.8g(1.52モル)、オクチルブロミド351.5g(1.82モル)及びアセトニトリル360.0gを混合し、80℃で24時間反応させた。反応終了後、得られた反応混合物を濃縮し、残渣に2−ブタノン300.0gを加え、ろ過後、得られた結晶を減圧下で乾燥し、1−オクチル−1−メチルピペリジニウム=ブロミド400.0g(収率90%)を得た。
Example 1 [Production of onium compound]
150.8 g (1.52 mol) of 1-methylpiperidine, 351.5 g (1.82 mol) of octyl bromide and 360.0 g of acetonitrile were mixed and reacted at 80 ° C. for 24 hours. After completion of the reaction, the obtained reaction mixture was concentrated, 300.0 g of 2-butanone was added to the residue, and after filtration, the obtained crystal was dried under reduced pressure to give 1-octyl-1-methylpiperidinium bromide 400.0 g (90% yield) was obtained.
上記で得られた1−オクチル−1−メチルピペリジニウムブロミド400.0g(1.37モル)、リチウム=ビス(トリフルオロメタンスルホニル)イミド396.1g(1.38モル)および水400.0gを混合し、25℃で1時間反応させた。反応終了後、反応混合物にジクロロメタン400.0gを加えて抽出、分液し、得られた有機層を水200.0gで2回洗浄した。水洗後の有機層を濃縮してジクロロメタンを除去後、残渣を減圧下で乾燥した。室温でオイル状の1−オクチル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド639.7g(収率95%)を得た。以下に1−オクチル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミドのNMRデータを示す。 400.0 g (1.37 mol) of 1-octyl-1-methylpiperidinium bromide obtained above, 396.1 g (1.38 mol) of lithium bis (trifluoromethanesulfonyl) imide and 400.0 g of water The mixture was mixed and reacted at 25 ° C. for 1 hour. After completion of the reaction, 400.0 g of dichloromethane was added to the reaction mixture for extraction and liquid separation, and the resulting organic layer was washed twice with 200.0 g of water. The organic layer after washing with water was concentrated to remove dichloromethane, and the residue was dried under reduced pressure. There was obtained 639.7 g (yield 95%) of 1-octyl-1-methylpiperidinium bis (trifluoromethanesulfonyl) imide oily at room temperature. The NMR data of 1-octyl-1-methylpiperidinium = bis (trifluoromethanesulfonyl) imide is shown below.
1H−NMR(CDCl3) δ:0.88(t,3H),1.27−1.35(m,10H),1.70−1.71(m,4H),1.89−1.90(m,4H),3.04(s,3H),3.25−3.30(m,2H),3.34−3.37(m,4H) 1 H-NMR (CDCl 3 ) δ: 0.88 (t, 3H), 1.27-1.35 (m, 10H), 1.70-1.71 (m, 4H), 1.89-1 .90 (m, 4H), 3.04 (s, 3H), 3.25-3.30 (m, 2H), 3.34-3.37 (m, 4H)
実施例2〜5
実施例1の1−メチルピペリジンおよびオクチルブロミドを表1に示す三級アミン類又はスルフィド類とアルキルハライド類に代えた以外は、実施例1と同様にして行い、対応するオニウム化合物を得た。これらは何れも室温でオイル状である。以下にそれらのNMRデータを示す。
Examples 2-5
A corresponding onium compound was obtained in the same manner as in Example 1 except that 1-methylpiperidine and octyl bromide in Example 1 were replaced with tertiary amines or sulfides and alkyl halides shown in Table 1. These are all oily at room temperature. The NMR data are shown below.
1−ヘキシル−1−メチルピペリジニウム=ビス(トリフルオロメタンスルホニル)イミド
1H−NMR(CDCl3) δ:0.90(t,3H),1.32−1.37(m,6H),1.69−1.73(m,4H),1.89−1.90(m,4H),3.04(s,3H),3.26−3.30(m,2H),3.35−3.37(m,4H)
1-hexyl-1-methylpiperidinium bis (trifluoromethanesulfonyl) imide
1 H-NMR (CDCl 3 ) δ: 0.90 (t, 3H), 1.32-1.37 (m, 6H), 1.69-1.73 (m, 4H), 1.89-1 .90 (m, 4H), 3.04 (s, 3H), 3.26-3.30 (m, 2H), 3.35-3.37 (m, 4H)
1−オクチル−1−メチルピロリジニウム=ビス(トリフルオロメタンスルホニル)イミド
1H−NMR(CDCl3) δ:0.88(t,3H),1.27−1.35(m,10H),1.70−1.80(m,2H),3.05(s,3H),3.29−3.32(m,2H),3.51−3.54(m,4H)
1-octyl-1-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide
1 H-NMR (CDCl 3 ) δ: 0.88 (t, 3H), 1.27-1.35 (m, 10H), 1.70-1.80 (m, 2H), 3.05 (s , 3H), 3.29-3.32 (m, 2H), 3.51-3.54 (m, 4H)
4−ヘキシル−4−メチルモルホリニウム=ビス(トリフルオロメタンスルホニル)イミド
1H−NMR(CDCl3) δ:0.90(t,3H),1.32−1.38(m,6H),1.71−1.78(m,2H),3.18(s,3H),3.35−3.44(m,6H),3.97−3.99(m,4H)
4-hexyl-4-methylmorpholinium bis (trifluoromethanesulfonyl) imide
1 H-NMR (CDCl 3 ) δ: 0.90 (t, 3H), 1.32-1.38 (m, 6H), 1.71-1.78 (m, 2H), 3.18 (s , 3H), 3.35-3.44 (m, 6H), 3.97-3.99 (m, 4H)
1−ブチルテトラヒドロチオフェニウム=ビス(トリフルオロメタンスルホニル)イミド
1H−NMR(CDCl3) δ:0.99(t,3H),1.50−1.55(m,2H),1.75−1.79(m,2H),2.30−2.47(m,4H),3.18−3.22(m,2H),3.38−3.41(m,2H),3.60−3.65(m,2H)
1-butyltetrahydrothiophenium bis (trifluoromethanesulfonyl) imide
1 H-NMR (CDCl 3 ) δ: 0.99 (t, 3H), 1.50-1.55 (m, 2H), 1.75-1.79 (m, 2H), 2.30-2 .47 (m, 4H), 3.18-3.22 (m, 2H), 3.38-3.41 (m, 2H), 3.60-3.65 (m, 2H)
実施例6
10重量%ZEONOR1020R(登録商標;日本ゼオン株式会社製環状オレフィン系重合体)/シクロヘキサン溶液10gに表2に記載のオニウム化合物を添加し、室温で1時間攪拌混合した。得られた混合液3gを直径50mm、深さ5mmの円盤形の型に流し込み、減圧下(300mmHg)で1時間脱気後、オーブンを用いて50℃で3時間乾燥し、さらに100℃で3時間乾燥後、本発明および比較の帯電防止樹脂組成物を得た。かかる帯電防止樹脂組成物(直径50mm、厚さ0.1mmの円盤形)を試験片とし、表面抵抗値及びヘーズを測定した。その結果を表2に示す。
Example 6
The onium compounds listed in Table 2 were added to 10 g of 10 wt% ZEONOR1020R (registered trademark; Nippon Zeon Co., Ltd. cyclic olefin polymer) / cyclohexane solution, and the mixture was stirred and mixed at room temperature for 1 hour. After pouring 3 g of the obtained mixed solution into a disk-shaped mold having a diameter of 50 mm and a depth of 5 mm, degassing under reduced pressure (300 mmHg) for 1 hour, drying in an oven at 50 ° C. for 3 hours, and further at 100 ° C. for 3 hours. After time drying, the present invention and comparative antistatic resin compositions were obtained. Using such an antistatic resin composition (disk shape having a diameter of 50 mm and a thickness of 0.1 mm) as a test piece, the surface resistance value and haze were measured. The results are shown in Table 2.
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