JP2009013295A - Ammonium salt and antistatic resin composition containing the same - Google Patents
Ammonium salt and antistatic resin composition containing the same Download PDFInfo
- Publication number
- JP2009013295A JP2009013295A JP2007176845A JP2007176845A JP2009013295A JP 2009013295 A JP2009013295 A JP 2009013295A JP 2007176845 A JP2007176845 A JP 2007176845A JP 2007176845 A JP2007176845 A JP 2007176845A JP 2009013295 A JP2009013295 A JP 2009013295A
- Authority
- JP
- Japan
- Prior art keywords
- thiocyanate
- resin
- resins
- ammonium salt
- ammonium
- 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
- 150000003863 ammonium salts Chemical class 0.000 title claims abstract description 33
- 239000011342 resin composition Substances 0.000 title claims abstract description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims abstract description 66
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims abstract description 51
- 229920005989 resin Polymers 0.000 claims abstract description 47
- 239000011347 resin Substances 0.000 claims abstract description 47
- 239000002216 antistatic agent Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940078672 didecyldimethylammonium Drugs 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229920000647 polyepoxide Polymers 0.000 claims description 12
- 239000003822 epoxy resin Substances 0.000 claims description 11
- 239000004925 Acrylic resin Substances 0.000 claims description 5
- 229920000178 Acrylic resin Polymers 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- 229920005992 thermoplastic resin Polymers 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 abstract description 7
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 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 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- -1 for example Chemical compound 0.000 description 25
- 150000001412 amines Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000001350 alkyl halides Chemical class 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 229940116357 potassium thiocyanate Drugs 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 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
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 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 2
- 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 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- LYYLWJOKAQADDU-UHFFFAOYSA-N n,n-dihexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC LYYLWJOKAQADDU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000002848 norbornenes Chemical class 0.000 description 2
- 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 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RSHBFZCIFFBTEW-UHFFFAOYSA-M tetrabutylazanium;thiocyanate Chemical compound [S-]C#N.CCCC[N+](CCCC)(CCCC)CCCC RSHBFZCIFFBTEW-UHFFFAOYSA-M 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ACXHIICURBSOEO-UHFFFAOYSA-N C(C)N(CCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCC Chemical compound C(C)N(CCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCC ACXHIICURBSOEO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- IVMGLEZNRBXXGG-UHFFFAOYSA-N S(C#N)[N+](CCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCC Chemical group S(C#N)[N+](CCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCC IVMGLEZNRBXXGG-UHFFFAOYSA-N 0.000 description 1
- LGVVGSRQRKSYSF-UHFFFAOYSA-N S(C#N)[N+](CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC Chemical group S(C#N)[N+](CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC LGVVGSRQRKSYSF-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- WOLKVEHHLOEZGG-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCC)(CCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCC)(CCCCC)CC WOLKVEHHLOEZGG-UHFFFAOYSA-M 0.000 description 1
- PQPHTMHLZFQDLM-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCC)(CCCCC)CCCCC Chemical compound [S-]C#N.C(C)[N+](CCCCC)(CCCCC)CCCCC PQPHTMHLZFQDLM-UHFFFAOYSA-M 0.000 description 1
- GIMILXXTTJPPPA-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCC)(CCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCC)(CCCCCC)CC GIMILXXTTJPPPA-UHFFFAOYSA-M 0.000 description 1
- JWONUYAGORJSNY-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCC)(CCCCCC)CCCCCC Chemical compound [S-]C#N.C(C)[N+](CCCCCC)(CCCCCC)CCCCCC JWONUYAGORJSNY-UHFFFAOYSA-M 0.000 description 1
- NWSWUMZZOQRDSL-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCC)(CCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCC)(CCCCCCC)CC NWSWUMZZOQRDSL-UHFFFAOYSA-M 0.000 description 1
- NXXOYPUKEJMPRZ-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCC)(CCCCCCC)CCCCCCC Chemical compound [S-]C#N.C(C)[N+](CCCCCCC)(CCCCCCC)CCCCCCC NXXOYPUKEJMPRZ-UHFFFAOYSA-M 0.000 description 1
- IHEUGNFYWNZWCR-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCC)(CCCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCC)(CCCCCCCC)CC IHEUGNFYWNZWCR-UHFFFAOYSA-M 0.000 description 1
- GVLCYQNLAAVCMC-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC GVLCYQNLAAVCMC-UHFFFAOYSA-M 0.000 description 1
- WXKAZTGRXHFZQP-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCCC)(CCCCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCCC)(CCCCCCCCC)CC WXKAZTGRXHFZQP-UHFFFAOYSA-M 0.000 description 1
- JZOFNSBDEBABMI-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC JZOFNSBDEBABMI-UHFFFAOYSA-M 0.000 description 1
- RPBJRYQJAFMYTP-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCCCCC)(CCCCCCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCCCCC)(CCCCCCCCCCC)CC RPBJRYQJAFMYTP-UHFFFAOYSA-M 0.000 description 1
- BAIVHZZSFXGDKQ-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCCCCCCC)(CCCCCCCCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCCCCCCC)(CCCCCCCCCCCCC)CC BAIVHZZSFXGDKQ-UHFFFAOYSA-M 0.000 description 1
- NUNTXIYYXWRNGL-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCCCCCCCC)(CCCCCCCCCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCCCCCCCC)(CCCCCCCCCCCCCC)CC NUNTXIYYXWRNGL-UHFFFAOYSA-M 0.000 description 1
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- YCDDZUNHSCEVBT-UHFFFAOYSA-M [S-]C#N.C(C)[N+](CCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCC)CC Chemical compound [S-]C#N.C(C)[N+](CCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCC)CC YCDDZUNHSCEVBT-UHFFFAOYSA-M 0.000 description 1
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- YMRAZJHFCSNDEF-UHFFFAOYSA-M [S-]C#N.C(CCC)[N+](CCCCC)(CCCCC)CCCCC Chemical compound [S-]C#N.C(CCC)[N+](CCCCC)(CCCCC)CCCCC YMRAZJHFCSNDEF-UHFFFAOYSA-M 0.000 description 1
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- OKUXMEJQPAIQBM-UHFFFAOYSA-M [S-]C#N.C(CCC)[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC Chemical compound [S-]C#N.C(CCC)[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC OKUXMEJQPAIQBM-UHFFFAOYSA-M 0.000 description 1
- ACDWCWMFIXQUJR-UHFFFAOYSA-M [S-]C#N.C(CCC)[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC Chemical compound [S-]C#N.C(CCC)[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC ACDWCWMFIXQUJR-UHFFFAOYSA-M 0.000 description 1
- ZKWCRYUBXAGATM-UHFFFAOYSA-M [S-]C#N.C(CCC)[N+](CCCCCCCCCCC)(CCCCCCCCCCC)CCCCCCCCCCC Chemical compound [S-]C#N.C(CCC)[N+](CCCCCCCCCCC)(CCCCCCCCCCC)CCCCCCCCCCC ZKWCRYUBXAGATM-UHFFFAOYSA-M 0.000 description 1
- MKPMNNKBDPPPSI-UHFFFAOYSA-N [S-]C#N.C(CCC)[NH2+]CCCCCCCCCCCCC Chemical compound [S-]C#N.C(CCC)[NH2+]CCCCCCCCCCCCC MKPMNNKBDPPPSI-UHFFFAOYSA-N 0.000 description 1
- PUQPBDZUIZQZGB-UHFFFAOYSA-M [S-]C#N.C(CCCC)[N+](CCC)(CCCCC)CCCCC Chemical compound [S-]C#N.C(CCCC)[N+](CCC)(CCCCC)CCCCC PUQPBDZUIZQZGB-UHFFFAOYSA-M 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920006259 thermoplastic polyimide Polymers 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- WIMCSFQYNXRDOM-UHFFFAOYSA-N tridodecyl(ethyl)azanium Chemical compound CCCCCCCCCCCC[N+](CC)(CCCCCCCCCCCC)CCCCCCCCCCCC WIMCSFQYNXRDOM-UHFFFAOYSA-N 0.000 description 1
- SBHRWOBHKASWGU-UHFFFAOYSA-M tridodecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC SBHRWOBHKASWGU-UHFFFAOYSA-M 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- NPVFKLJHSMLTCV-UHFFFAOYSA-N trioctadecyl(propyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](CCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC NPVFKLJHSMLTCV-UHFFFAOYSA-N 0.000 description 1
- JHUGGTBDRFUPCQ-UHFFFAOYSA-M trioctyl(propyl)azanium thiocyanate Chemical compound [S-]C#N.CCCCCCCC[N+](CCC)(CCCCCCCC)CCCCCCCC JHUGGTBDRFUPCQ-UHFFFAOYSA-M 0.000 description 1
- NACZPBOVCXPUJN-UHFFFAOYSA-N tris-decyl(methyl)azanium Chemical compound CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC NACZPBOVCXPUJN-UHFFFAOYSA-N 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
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、樹脂用帯電防止剤、帯電防止性樹脂組成物及び新規なアンモニウム塩に関する。 The present invention relates to an antistatic agent for resins, an antistatic resin composition, and a novel ammonium salt.
従来、帯電防止剤として用いることのできるチオシアナートをアニオンとする化合物には、チオシアン酸金属塩、例えばチオシアン酸ナトリウム、チオシアン酸カリウムなどが知られている（例えば、特許文献１）。しかし、チオシアナートをアニオンとするアンモニウム塩を樹脂用帯電防止剤として用いることは知られていない。
本発明は、樹脂の透明性を損なうことなく、樹脂に優れた帯電防止能を付与できる、チオシアナートイオンをアニオンとするアンモニウム塩を有効成分として含有する樹脂用帯電防止剤及び該樹脂用帯電防止剤を含む帯電防止性樹脂組成物を提供することを課題とする。また、本発明は、チオシアナートイオンをアニオンとする新規なアンモニウム塩を提供することも課題とする。 The present invention relates to an antistatic agent for resins containing an ammonium salt having thiocyanate ions as an anion, which can impart excellent antistatic ability to the resin without impairing the transparency of the resin, and the charging for the resin. It is an object of the present invention to provide an antistatic resin composition containing an inhibitor. Another object of the present invention is to provide a novel ammonium salt having a thiocyanate ion as an anion.
本発明は、式（１）：
Ｒ１Ｒ２Ｒ３Ｒ４Ｎ＋ＳＣＮ− （１）
（式中、Ｒ１及びＲ２は炭素数４〜１８のアルキル基、Ｒ３は炭素数１〜１８のアルキル基、Ｒ４は炭素数１〜４のアルキル基を示し、Ｒ１〜Ｒ４は互いに同じであっても、異なっていてもよい。）で表されるアンモニウム塩（以下、アンモニウム塩（１）という。）を有効成分として含有することを特徴とする樹脂用帯電防止剤、並びに該樹脂用帯電防止剤を含有することを特徴とする帯電防止性樹脂組成物に関する。さらに、式（１）中、Ｒ１とＲ２がデシル基、Ｒ３とＲ４がメチル基であるアンモニウム塩（すなわち、ジデシルジメチルアンモニウム＝チオシアナート）に関する。
The present invention relates to formula (1):
R 1 R 2 R 3 R 4 N + SCN − (1)
(In the formula, R 1 and R 2 represent an alkyl group having 4 to 18 carbon atoms, R 3 represents an alkyl group having 1 to 18 carbon atoms, R 4 represents an alkyl group having 1 to 4 carbon atoms, and R 1 to R 4 May be the same as or different from each other.) An antistatic agent for resins characterized by containing as an active ingredient an ammonium salt (hereinafter referred to as ammonium salt (1)), and The present invention relates to an antistatic resin composition comprising the antistatic agent for resin. Further, the present invention relates to an ammonium salt in which R 1 and R 2 are decyl groups and R 3 and R 4 are methyl groups in formula (1) (that is, didecyldimethylammonium thiocyanate).
本発明の樹脂用帯電防止剤は、樹脂の透明性を損なうことなく、樹脂に優れた帯電防止能を付与することができ、また、この樹脂用帯電防止剤を含有する樹脂組成物は、透明性を有し、低い表面抵抗値を示す帯電防止性のものである。 The antistatic agent for resin of the present invention can impart excellent antistatic ability to the resin without impairing the transparency of the resin, and the resin composition containing the antistatic agent for resin is transparent. And antistatic properties exhibiting low surface resistance.
以下、本発明を具体的に説明する。
式（１）中、Ｒ１及びＲ２で示される炭素数４〜１８のアルキル基としては、直鎖状又は分枝鎖状の炭素数４〜１８のアルキル基が挙げられ、好ましくは直鎖状又は分枝鎖状の炭素数４〜１０のアルキル基であり、特に好ましくは、直鎖状の炭素数４〜１０のアルキル基である。具体的には、例えば、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、ヘキシル基、ヘプチル基、オクチル基、２−エチルヘキシル基、ノニル基、デシル基等が挙げられる。
The present invention will be specifically described below.
In the formula (1), examples of the alkyl group having 4 to 18 carbon atoms represented by R 1 and R 2 include linear or branched alkyl groups having 4 to 18 carbon atoms, preferably linear. Or a branched alkyl group having 4 to 10 carbon atoms, particularly preferably a linear alkyl group having 4 to 10 carbon atoms. Specific examples include a butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, and decyl group.
Ｒ３で示される炭素数１〜１８のアルキル基としては、直鎖状又は分枝鎖状の炭素数１〜１８のアルキル基が挙げられ、好ましくは直鎖状又は分枝鎖状の炭素数１〜１６のアルキル基であり、特に好ましくは、直鎖状の炭素数１〜１０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、イソペンチル基、ｓｅｃ−ペンチル基、ヘキシル基、イソヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基等が挙げられる。 Examples of the alkyl group having 1 to 18 carbon atoms represented by R 3 include a linear or branched alkyl group having 1 to 18 carbon atoms, and preferably a linear or branched carbon number. It is a 1-16 alkyl group, Most preferably, it is a linear C1-C10 alkyl group. Specifically, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, hexyl group, isohexyl group , Heptyl group, octyl group, nonyl group, decyl group and the like.
Ｒ４で示される炭素数１〜４のアルキル基としては、直鎖状又は分枝鎖状の炭素数１〜４のアルキル基が挙げられ、具体的には、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。 Examples of the alkyl group having 1 to 4 carbon atoms represented by R 4 include a linear or branched alkyl group having 1 to 4 carbon atoms, specifically, a methyl group, an ethyl group, and a propyl group. Isopropyl group, butyl group, isobutyl group, sec-butyl group, and tert-butyl group.
本発明のアンモニウム塩（１）の具体例としては、テトラブチルアンモニウム＝チオシアナート、トリブチルメチルアンモニウム＝チオシアナート、メチルトリペンチルアンモニウム＝チオシアナート、トリヘキシルメチルアンモニウム＝チオシアナート、トリヘプチルメチルアンモニウム＝チオシアナート、トリオクチルメチルアンモニウム＝チオシアナート、メチルトリノニルアンモニウム＝チオシアナート、トリデシルメチルアンモニウム＝チオシアナート、メチルトリウンデシルアンモニウム＝チオシアナート、トリドデシルメチルアンモニウム＝チオシアナート、メチルトリトリデシルアンモニウム＝チオシアナート、メチルトリテトラデシルアンモニウム＝チオシアナート、メチルトリペンタデシルアンモニウム＝チオシアナート、トリヘキサデシルメチルアンモニウム＝チオシアナート、トリヘプタデシルメチルアンモニウム＝チオシアナート、トリオクタデシルメチルアンモニウム＝チオシアナート、 Specific examples of the ammonium salt (1) of the present invention include tetrabutylammonium thiocyanate, tributylmethylammonium thiocyanate, methyltripentylammonium thiocyanate, trihexylmethylammonium thiocyanate, triheptylmethylammonium thiocyanate, trioctylmethyl Ammonium = thiocyanate, methyltrinonylammonium = thiocyanate, tridecylmethylammonium = thiocyanate, methyltriundecylammonium = thiocyanate, tridodecylmethylammonium = thiocyanate, methyltritridecylammonium = thiocyanate, methyltritetradecylammonium = thiocyanate, methyltri Pentadecylammonium thiocyaner , Tri-hexadecyl ammonium = thiocyanato, tri heptadecyl ammonium = thiocyanato, trioctadecyl ammonium = thiocyanate,
トリブチルエチルアンモニウム＝チオシアナート、エチルトリペンチルアンモニウム＝チオシアナート、エチルトリヘキシルアンモニウム＝チオシアナート、エチルトリヘプチルアンモニウム＝チオシアナート、エチルトリオクチルアンモニウム＝チオシアナート、エチルトリノニルアンモニウム＝チオシアナート、トリデシルエチルアンモニウム＝チオシアナート、エチルトリウンデシルアンモニウム＝チオシアナート、トリドデシルエチルアンモニウム＝チオシアナート、エチルトリトリデシルアンモニウム＝チオシアナート、エチルトリテトラデシルアンモニウム＝チオシアナート、エチルトリペンタデシルアンモニウム＝チオシアナート、エチルトリヘキサデシルアンモニウム＝チオシアナート、エチルトリヘプタデシルアンモニウム＝チオシアナート、エチルトリオクタデシルアンモニウム＝チオシアナート、 Tributylethylammonium thiocyanate, ethyltripentylammonium thiocyanate, ethyltrihexylammonium thiocyanate, ethyltriheptylammonium thiocyanate, ethyltrioctylammonium thiocyanate, ethyltrinonylammonium thiocyanate, tridecylethylammonium thiocyanate, ethyltri Undecyl ammonium = thiocyanate, tridodecyl ethyl ammonium = thiocyanate, ethyl tritridecyl ammonium = thiocyanate, ethyl tritetradecyl ammonium = thiocyanate, ethyl tripentadecyl ammonium = thiocyanate, ethyl trihexadecyl ammonium = thiocyanate, ethyl triheptadecyl ammonium = Thiocyanate, ethyl tri ammonium = thiocyanate,
トリブチルプロピルアンモニウム＝チオシアナート、トリペンチルプロピルアンモニウム＝チオシアナート、トリヘキシルプロピルアンモニウム＝チオシアナート、トリヘプチルプロピルアンモニウム＝チオシアナート、トリオクチルプロピルアンモニウム＝チオシアナート、トリノニルプロピルアンモニウム＝チオシアナート、トリデシルプロピルアンモニウム＝チオシアナート、プロピルトリウンデシルアンモニウム＝チオシアナート、トリドデシルプロピルアンモニウム＝チオシアナート、プロピルトリトリデシルアンモニウム＝チオシアナート、プロピルトリテトラデシルアンモニウム＝チオシアナート、トリペンタデシルプロピルアンモニウム＝チオシアナート、トリヘキサデシルプロピルアンモニウム＝チオシアナート、トリヘプタデシルプロピルアンモニウム＝チオシアナート、トリオクタデシルプロピルアンモニウム＝チオシアナート、 Tributylpropylammonium thiocyanate, tripentylpropylammonium thiocyanate, trihexylpropylammonium thiocyanate, triheptylpropylammonium thiocyanate, trioctylpropylammonium thiocyanate, trinonylpropylammonium thiocyanate, tridecylpropylammonium thiocyanate, propyltri Undecylammonium thiocyanate, tridodecylpropylammonium thiocyanate, propyltritridecylammonium thiocyanate, propyltritetradecylammonium thiocyanate, tripentadecylpropylammonium thiocyanate, trihexadecylpropylammonium thiocyanate Data decyl propylammonium = thiocyanate, trioctadecyl propyl ammonium = thiocyanate,
ブチルトリペンチルアンモニウム＝チオシアナート、ブチルトリヘキシルアンモニウム＝チオシアナート、ブチルトリヘプチルアンモニウム＝チオシアナート、ブチルトリオクチルアンモニウム＝チオシアナート、ブチルトリノニルアンモニウム＝チオシアナート、ブチルトリデシルアンモニウム＝チオシアナート、ブチルトリウンデシルアンモニウム＝チオシアナート、ブチルトリドデシルアンモニウム＝チオシアナート、ブチルトリトリデシルアンモニウム＝チオシアナート、ブチルトリテトラデシルアンモニウム＝チオシアナート、ブチルトリペンタデシルアンモニウム＝チオシアナート、ブチルトリヘキサデシルアンモニウム＝チオシアナート、ブチルトリヘプタデシルアンモニウム＝チオシアナート、ブチルトリオクタデシルアンモニウム＝チオシアナート、 Butyltripentylammonium thiocyanate, butyltrihexylammonium thiocyanate, butyltriheptylammonium thiocyanate, butyltrioctylammonium thiocyanate, butyltrinonylammonium thiocyanate, butyltridecylammonium thiocyanate, butyltriundecylammonium thiocyanate, Butyl tridodecyl ammonium = thiocyanate, butyl tritridecyl ammonium = thiocyanate, butyl tritetradecyl ammonium = thiocyanate, butyl tripentadecyl ammonium = thiocyanate, butyl trihexadecyl ammonium = thiocyanate, butyl triheptadecyl ammonium = thiocyanate, butyl trioctadecyl an Bromide = thiocyanate,
ジブチルジメチルアンモニウム＝チオシアナート、ジメチルジペンチルアンモニウム＝チオシアナート、ジヘキシルジメチルアンモニウム＝チオシアナート、ジヘプチルジメチルアンモニウム＝チオシアナート、ジメチルジオクチルアンモニウム＝チオシアナート、ジメチルジノニルアンモニウム＝チオシアナート、ジデシルジメチルアンモニウム＝チオシアナート、ジメチルジウンデシルアンモニウム＝チオシアナート、ジドデシルジメチルアンモニウム＝チオシアナート、ジメチルジトリデシルアンモニウム＝チオシアナート、ジメチルジテトラデシルアンモニウム＝チオシアナート、ジメチルジペンタデシルアンモニウム＝チオシアナート、ジヘキサデシルジメチルアンモニウム＝チオシアナート、ジヘプタデシルジメチルアンモニウム＝チオシアナート、ジメチルジオクタデシルアンモニウム＝チオシアナート、 Dibutyldimethylammonium thiocyanate, dimethyldipentylammonium thiocyanate, dihexyldimethylammonium thiocyanate, diheptyldimethylammonium thiocyanate, dimethyldioctylammonium thiocyanate, dimethyldinonylammonium thiocyanate, didecyldimethylammonium thiocyanate, dimethyldiundecylammonium Thiocyanate, didodecyldimethylammonium thiocyanate, dimethylditridecylammonium thiocyanate, dimethylditetradecylammonium thiocyanate, dimethyldipentadecylammonium thiocyanate, dihexadecyldimethylammonium thiocyanate, diheptadecyldimethylammonium = Thiocyanate, dimethyl dioctadecyl ammonium = thiocyanate,
ジブチルジエチルアンモニウム＝チオシアナート、ジエチルジペンチルアンモニウム＝チオシアナート、ジエチルジヘキシルアンモニウム＝チオシアナート、ジエチルジヘプチルアンモニウム＝チオシアナート、ジエチルジオクチルアンモニウム＝チオシアナート、ジエチルジノニルアンモニウム＝チオシアナート、ジデシルジエチルアンモニウム＝チオシアナート、ジエチルジウンデシルアンモニウム＝チオシアナート、ジドデシルジエチルアンモニウム＝チオシアナート、ジエチルジトリデシルアンモニウム＝チオシアナート、ジエチルジテトラデシルアンモニウム＝チオシアナート、ジエチルジペンタデシルアンモニウム＝チオシアナート、ジエチルジヘキサデシルアンモニウム＝チオシアナート、ジエチルジヘプタデシルアンモニウム＝チオシアナート、ジエチルジオクタデシルアンモニウム＝チオシアナート等が挙げられる。 Dibutyldiethylammonium thiocyanate, diethyldipentylammonium thiocyanate, diethyldihexylammonium thiocyanate, diethyldiheptylammonium thiocyanate, diethyldioctylammonium thiocyanate, diethyldinonylammonium thiocyanate, didecyldiethylammonium thiocyanate, diethyldiundecylammonium Thiocyanate, didodecyldiethylammonium thiocyanate, diethylditridecylammonium thiocyanate, diethylditetradecylammonium thiocyanate, diethyldipentadecylammonium thiocyanate, diethyldihexadecylammonium thiocyanate, diethyldiheptadecylammonium = Thiocyanate, diethyl-di-octadecyl ammonium = thiocyanate and the like.
本発明のアンモニウム塩（１）は、例えば式（２）：
Ｒ１Ｒ２Ｒ３Ｒ４Ｎ＋Ｘ− （２）
（式中、Ｒ１〜Ｒ４は前記に同じ。Ｘはハロゲン原子を示す。）で表されるアンモニウム＝ハライド（以下、アンモニウム＝ハライド（２）という。）をチオシアン酸又はそのアルカリ金属塩（以下、チオシアン酸類という。）を用いて、アニオン交換することにより製造することができる。
The ammonium salt (1) of the present invention is represented, for example, by the formula (2):
R 1 R 2 R 3 R 4 N + X − (2)
(Wherein R 1 to R 4 are the same as described above, X represents a halogen atom) ammonium halide (hereinafter referred to as ammonium = halide (2)) represented by thiocyanic acid or an alkali metal salt thereof ( Hereinafter, it can be produced by anion exchange using thiocyanic acid).
アンモニウム＝ハライド（２）は、市販品を用いても良いし、例えば、式（３）：
Ｒ１Ｒ２Ｒ３Ｎ （３）
（式中、Ｒ１〜Ｒ３は前記に同じ。）で表されるアミン（以下、アミン（３）という。）を
式（４）：
Ｒ4Ｘ （４）
（式中、Ｒ４及びＸは前記に同じ。）で表されるアルキルハライド（以下、アルキルハライド（４）という。）と反応させることで製造できる。
As the ammonium halide (2), a commercially available product may be used, for example, the formula (3):
R 1 R 2 R 3 N (3)
(Wherein R 1 to R 3 are the same as above), an amine (hereinafter referred to as amine (3)) represented by formula (4):
R 4 X (4)
(In the formula, R 4 and X are the same as those described above.) It can be produced by reacting with an alkyl halide (hereinafter referred to as alkyl halide (4)).
アミン（３）としては、例えば、トリブチルアミン、トリペンチルアミン、トリヘキシルアミン、トリヘプチルアミン、トリオクチルアミン、トリノニルアミン、トリデシルアミン、トリウンデシルアミン、トリドデシルアミン、トリトリデシルアミン、トリテトラデシルアミン、トリペンタデシルアミン、トリヘキサデシルアミン、トリヘプタデシルアミン、トリオクタデシルアミン、 Examples of the amine (3) include tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, triundecylamine, tridodecylamine, tritridecylamine, Tetradecylamine, tripentadecylamine, trihexadecylamine, triheptadecylamine, trioctadecylamine,
ジブチルメチルアミン、メチルジペンチルアミン、ジヘキシルメチルアミン、ジヘプチルメチルアミン、メチルジオクチルアミン、メチルジノニルアミン、ジデシルメチルアミン、メチルジウンデシルアミン、ジドデシルメチルアミン、メチルジトリデシルアミン、メチルジテトラデシルアミン、メチルジペンタデシルアミン、ジヘキサデシルメチルアミン、ジヘプタデシルメチルアミン、メチルジオクタデシルアミン、 Dibutylmethylamine, methyldipentylamine, dihexylmethylamine, diheptylmethylamine, methyldioctylamine, methyldinonylamine, didecylmethylamine, methyldiundecylamine, didodecylmethylamine, methylditridecylamine, methylditetradecyl Amine, methyldipentadecylamine, dihexadecylmethylamine, diheptadecylmethylamine, methyldioctadecylamine,
ジブチルエチルアミン、エチルジペンチルアミン、エチルジヘキシルアミン、エチルジヘプチルアミン、エチルジオクチルアミン、エチルジノニルアミン、ジデシルエチルアミン、エチルジウンデシルアミン、ジドデシルエチルアミン、エチルジトリデシルアミン、エチルジテトラデシルアミン、エチルジペンタデシルアミン、エチルジヘキサデシルアミン、エチルジヘプタデシルアミン、エチルジオクタデシルアミン等が挙げられる。 Dibutylethylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, didecylethylamine, ethyldiundecylamine, didodecylethylamine, ethylditridecylamine, ethylditetradecylamine, ethyl Examples include dipentadecylamine, ethyldihexadecylamine, ethyldiheptadecylamine, and ethyldioctadecylamine.
アルキルハライド（４）としては、例えば、メチルクロリド、メチルブロミド、メチルヨージド、エチルクロリド、エチルブロミド、エチルヨージド、プロピルクロリド、プロピルブロミド、プロピルヨージド、ブチルクロリド、ブチルブロミド、ブチルヨージド等が挙げられる。 Examples of the alkyl halide (4) include methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, propyl chloride, propyl bromide, propyl iodide, butyl chloride, butyl bromide, butyl iodide and the like.
アルキルハライド（４）の使用量は、アミン（３）1モルに対して０．５モル〜５モル、好ましくは０．６モル〜３モルであり、より好ましくは０．８モル〜２モルである。 The amount of the alkyl halide (4) used is 0.5 mol to 5 mol, preferably 0.6 mol to 3 mol, more preferably 0.8 mol to 2 mol, relative to 1 mol of the amine (3). is there.
アミン（３）とアルキルハライド（４）との反応は、溶媒を使用してもしなくても良く、溶媒を使用する場合の溶媒としては、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、アセトニトリル、プロピオニトリル等の二トリル系溶媒、酢酸エチル、酢酸ブチル等のエステル系溶媒、テトラヒドロフラン、１，４−ジオキサン等のエーテル系溶媒、トルエン、キシレン等の芳香族系溶媒、ヘキサン、シクロヘキサン等の脂肪族又は脂環式炭化水素系溶媒等が挙げられる。溶媒の使用量は、特に制限はないが、アミン（３）１重量部に対して、通常１０重量部以下、好ましくは０．１〜５重量部、より好ましくは０．１〜１重量部である。 The reaction of the amine (3) and the alkyl halide (4) may or may not use a solvent. Examples of the solvent used include alcohol solvents such as methanol, ethanol, isopropanol, acetonitrile, Nitrile solvents such as pionitrile, ester solvents such as ethyl acetate and butyl acetate, ether solvents such as tetrahydrofuran and 1,4-dioxane, aromatic solvents such as toluene and xylene, and aliphatic solvents such as hexane and cyclohexane Or an alicyclic hydrocarbon-type solvent etc. are mentioned. Although there is no restriction | limiting in particular in the usage-amount of a solvent, It is 10 weight part or less normally with respect to 1 weight part of amine (3), Preferably it is 0.1-5 weight part, More preferably, it is 0.1-1 weight part. is there.
アミン（３）とアルキルハライド（４）との反応を実施するには、例えば、アミン（３）、アルキルハライド（４）及び溶媒の混合物を通常２０℃以上、好ましくは６０℃〜１４０℃で加熱攪拌するだけで良い。 In order to carry out the reaction between the amine (3) and the alkyl halide (4), for example, the mixture of the amine (3), the alkyl halide (4) and the solvent is usually heated at 20 ° C. or higher, preferably 60 ° C. to 140 ° C. Just stir.
上記のようにして、アンモニウム＝ハライド（２）を含む反応混合物を得た後、得られた反応混合物を本発明のアンモニウム塩（１）を製造するための反応にそのまま用いてもかまわない。また必要であれば、濃縮してアンモニウム＝ハライド（２）を主成分とする残渣を得、この残渣を本発明のアンモニウム塩（１）を製造するための反応にそのまま用いてもかまわない。また、さらに必要であれば、残渣を有機溶媒と混合し、残渣に含まれる未反応原料等を有機溶媒に溶解した後ろ過して得られる、精製されたアンモニウム＝ハライド（２）を用いることもできる。 After obtaining the reaction mixture containing ammonium = halide (2) as described above, the obtained reaction mixture may be used as it is for the reaction for producing the ammonium salt (1) of the present invention. If necessary, it can be concentrated to obtain a residue containing ammonium halide (2) as a main component, and this residue can be used as it is in the reaction for producing the ammonium salt (1) of the present invention. Further, if necessary, it is also possible to use a purified ammonium halide (2) obtained by mixing the residue with an organic solvent, dissolving unreacted raw materials contained in the residue in the organic solvent and then filtering. it can.
チオシアン酸類としては、例えば、チオシアン酸、チオシアン酸ナトリウム、チオシアン酸カリウム、チオシアン酸リチウム等が挙げられ、好ましくはチオシアン酸ナトリウム、チオシアン酸カリウムである。かかるチオシアン酸類の使用量は、アンモニウム＝ハライド（２）１モルに対し、通常０．５モル以上であり、好ましくは１〜２モルである。 Examples of thiocyanic acids include thiocyanic acid, sodium thiocyanate, potassium thiocyanate, lithium thiocyanate, and the like, preferably sodium thiocyanate and potassium thiocyanate. The amount of thiocyanic acid to be used is usually 0.5 mol or more, preferably 1 to 2 mol, per 1 mol of ammonium halide (2).
アニオン交換反応は、通常水溶媒中で行われる。水の使用量は特に制限はないが、通常アンモニウム＝ハライド（２）１重量部に対して通常２０重量部以下、好ましくは０．３〜１０重量部、より好ましくは０．５〜３重量部である。 The anion exchange reaction is usually performed in an aqueous solvent. The amount of water used is not particularly limited, but is usually 20 parts by weight or less, preferably 0.3 to 10 parts by weight, more preferably 0.5 to 3 parts by weight with respect to 1 part by weight of ammonium halide (2). It is.
アンモニウム＝ハライド（２）、チオシアン酸類及び水の混合順序は特に限定されず、アンモニウム＝ハライド（２）と水を混合した後にチオシアン酸類を添加しても良いし、チオシアン酸類と水を混合した後に、活性炭等の脱色剤を用いて処理し、濾過して得られた濾液をアニオン交換反応に用いることもできる。 The mixing order of ammonium halide (2), thiocyanic acid and water is not particularly limited, and thiocyanic acid may be added after mixing ammonium = halide (2) and water, or after mixing thiocyanic acid and water. The filtrate obtained by treating with a decoloring agent such as activated carbon and filtering can also be used for the anion exchange reaction.
反応温度は、生成するアンモニウム塩（１）の融点より高い温度で反応させることが好ましく、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 is preferably higher than the melting point of the produced ammonium salt (1), and 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アンモニウム塩（１）を取り出す方法としては、反応液を有機層と水層に分離し、所望により有機層を水洗した後、有機層を濃縮することによってアンモニウム塩（１）を得る方法、水に不溶の有機溶媒（例えば、トルエン、酢酸エチル、ジクロロメタン等）を反応中又は反応後に添加し、アンモニウム塩（１）を水に不溶の有機溶媒に抽出、得られた抽出層を所望により水洗し、次いで有機溶媒を留去することによりアンモニウム塩（１）を得る方法等が挙げられる。 As a method for removing the ammonium salt (1) from the reaction solution after completion of the reaction, the reaction solution is separated into an organic layer and an aqueous layer, the organic layer is washed with water if desired, and then the organic layer is concentrated to give an ammonium salt (1). ), An organic solvent insoluble in water (for example, toluene, ethyl acetate, dichloromethane, etc.) is added during or after the reaction, and the ammonium salt (1) is extracted into an organic solvent insoluble in water, and the resulting extraction Examples thereof include a method of obtaining the ammonium salt (1) by washing the layer with water if desired and then distilling off the organic solvent.
本発明の樹脂用帯電防止剤は、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、単独であっても樹脂用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。かかる樹脂用帯電防止剤を樹脂組成物製造時に樹脂に添加する等の方法で、樹脂組成物に含有させることで、樹脂の透明性を損なうことなく、樹脂の表面抵抗値を低下させた樹脂組成物を製造することができる。 The antistatic agent for resins of the present invention contains an ammonium salt (1) as an active ingredient and can be used alone as an antistatic agent for resins, but can be stabilized as necessary. An additive such as an agent or a solvent may be mixed and used. A resin composition in which the surface resistance value of the resin is reduced without impairing the transparency of the resin by adding the antistatic agent for resin to the resin during the production of the resin composition. Can be manufactured.
本発明の帯電防止性樹脂組成物に用いる樹脂としては、通常、熱可塑性樹脂、熱硬化性樹脂及び光硬化性樹脂（例えば、アクリル系光硬化性樹脂）が挙げられる。熱可塑性樹脂としては、ポリエチレン、ポリプロピレン、エチレン又はプロピレンと他のビニルモノマー、例えば酢酸ビニル、α−オレフィン、(メタ)アクリル酸エステル等との共重合体、ノルボルネン類の付加重合体、ノルボルネン類とα−オレインとの付加共重合体、ノルボルネン類の開環重合体水添ポリマー、シクロペンタジエンの開環重合体水添ポリマー、シクロヘキサジエンの開環重合体水添ポリマー等のポリオレフィン；ポリ塩化ビニル、ポリ塩化ビニリデン等の塩素含有樹脂；ポリスチレン、ＡＳ樹脂、ＡＢＳ樹脂、ＭＳ樹脂、ＭＢＳ樹脂等のスチレン樹脂；ポリアクリル酸、ポリメタアクリル酸、ポリメタクリル酸メチル等の（メタ）アクリル樹脂；芳香族ジヒドロキシ化合物（例えばビスフェノールＡ）と塩化カルボニル又はジフェニルカーボネートから製造される芳香族ポリカーボネート等のポリカーボネート；ナイロン４、ナイロン６、ナイロン８、ナイロン１１、ナイロン１２、ナイロン６６等のポリアミド；ポリエーテルイミド等の熱可塑性ポリイミド；ポリエチレンテレフタレート、ポリブチレンテレフタレート等のポリエステル；これらの混合物等が挙げられる。これらの樹脂の中で (メタ)アクリル樹脂が好ましい。熱硬化性樹脂としては、エポキシ樹脂（例えば、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、水添ビスフェノールＡ型エポキシ樹脂、フェノールノボラック型エポキシ樹脂等）、熱硬化性ポリイミド（例えば、ピロメリット酸無水物とビス（４−アミノフェニル）エーテルとの重縮合物等）、ポリウレタン、フェノール樹脂、アミノ樹脂（例えばメラミン樹脂、ウレア樹脂等）、が例示でき、中でもエポキシ樹脂が好ましい。 Examples of the resin used in the antistatic resin composition of the present invention usually include a thermoplastic resin, a thermosetting resin, and a photocurable resin (for example, an acrylic photocurable resin). Thermoplastic resins include polyethylene, polypropylene, copolymers of ethylene or propylene and other vinyl monomers such as vinyl acetate, α-olefins, (meth) acrylic acid esters, norbornene addition polymers, norbornenes, and the like. Polyolefins such as addition copolymers with α-olein, ring-opening polymer hydrogenated polymers of norbornenes, ring-opening polymer hydrogenated polymers of cyclopentadiene, ring-opening polymer hydrogenated polymers of cyclohexadiene; polyvinyl chloride, Chlorine-containing resins such as polyvinylidene chloride; styrene resins such as polystyrene, AS resin, ABS resin, MS resin and MBS resin; (meth) acrylic resins such as polyacrylic acid, polymethacrylic acid and polymethyl methacrylate; aromatic Dihydroxy compounds (eg bisphenol A) and carbonyl chloride or Polycarbonates such as aromatic polycarbonates produced from diphenyl carbonate; polyamides such as nylon 4, nylon 6, nylon 8, nylon 11, nylon 12 and nylon 66; thermoplastic polyimides such as polyetherimide; polyethylene terephthalate, polybutylene terephthalate, etc. A polyester thereof; and a mixture thereof. Of these resins, (meth) acrylic resins are preferred. Examples of thermosetting resins include epoxy resins (for example, bisphenol A type epoxy resins, bisphenol F type epoxy resins, hydrogenated bisphenol A type epoxy resins, phenol novolac type epoxy resins, etc.), thermosetting polyimides (for example, pyromellitic acid). An anhydride and a bis (4-aminophenyl) ether polycondensate, etc.), polyurethane, phenol resin, amino resin (for example, melamine resin, urea resin, etc.) can be illustrated, and an epoxy resin is particularly preferable.
本発明における樹脂組成物への本発明の樹脂用帯電防止剤の含有量は、樹脂に対して０．０５〜５０重量％であり、好ましくは０．５〜２５重量％、特に好ましくは２〜１０重量％である。 The content of the antistatic agent for resins of the present invention in the resin composition of the present invention is 0.05 to 50% by weight, preferably 0.5 to 25% by weight, particularly preferably 2 to 2%, based on the resin. 10% by weight.
次に、本発明を実施例に基づいて具体的に説明するが、本発明は何らこれらに限定されるものではない。なお、以下の実施例中、表面抵抗値は三菱化学株式会社製ＨｉｒｅｓｔａＨＴ−２１０を用い、印加電圧５００Ｖにて測定した。 EXAMPLES Next, although this invention is demonstrated concretely based on an Example, this invention is not limited to these at all. In the following examples, the surface resistance value was measured with an applied voltage of 500 V using Hiresta HT-210 manufactured by Mitsubishi Chemical Corporation.
実施例１
テトラブチルアンモニウム＝クロリド１１１．２ｇ（０．４モル）、チオシアン酸ナトリウム４８．６ｇ（０．６モル）、イオン交換水１００ｇ及び塩化メチレン１００ｇを混合して２５℃で１時間攪拌した。反応終了後、有機層を分液操作により分離し、イオン交換水１００ｇで２回洗浄した。得られた有機層を減圧下で濃縮して塩化メチレンを除去し、固体のテトラブチルアンモニウム＝チオシアナート（以下、ＴＢＡ−ＳＣＮと略記する。）１１７．７ｇを得た（収率９７．９％）。以下にＴＢＡ−ＳＣＮのＮＭＲデータを示す。
Example 1
Tetrabutylammonium chloride (111.2 g, 0.4 mol), sodium thiocyanate (48.6 g, 0.6 mol), ion-exchanged water (100 g) and methylene chloride (100 g) were mixed and stirred at 25 ° C. for 1 hour. After completion of the reaction, the organic layer was separated by a liquid separation operation and washed twice with 100 g of ion-exchanged water. The obtained organic layer was concentrated under reduced pressure to remove methylene chloride to obtain 117.7 g of solid tetrabutylammonium thiocyanate (hereinafter abbreviated as TBA-SCN) (yield 97.9%). . The NMR data of TBA-SCN is shown below.
１Ｈ−ＮＭＲ（ＣＤＣｌ３） σ：１．０３（ｔ，１２Ｈ）、１．４５−１．５１（ｍ，８Ｈ）、１．６９−１．７３（ｍ，８Ｈ）、３．３４−３．３８（ｍ，８Ｈ） 1 H-NMR (CDCl 3 ) σ: 1.03 (t, 12H), 1.45-1.51 (m, 8H), 1.69-1.73 (m, 8H), 3.34-3 .38 (m, 8H)
実施例２
アーカード２１０−８０Ｅ（ジデシルジメチルアンモニウム＝クロリドのエタノール含有水溶液（濃度８０．２％）、登録商標、ライオンアグゾ株式会社製）１８０．６ｇ（０．４モル）、チオシアン酸ナトリウム４８．６ｇ（０．６モル）及びイオン交換水１１５．４ｇを混合し、２５℃で１時間攪拌した。反応終了後、有機層を分液操作により分離し、イオン交換水１１５．４ｇで２回洗浄した。得られた有機層を減圧下で濃縮し、液体のジデシルジメチルアンモニウム＝チオシアナート（以下、ＤＭＤＤＡ−ＳＣＮと略記する。）１４６．２ｇを得た（収率９５．０％）。以下にＤＭＤＤＡ−ＳＣＮのＮＭＲデータを示す。
Example 2
ARCARD 210-80E (didecyldimethylammonium chloride ethanol-containing aqueous solution (concentration: 80.2%), registered trademark, Lion Azo Co., Ltd.) 180.6 g (0.4 mol), sodium thiocyanate 48.6 g (0. 6 mol) and 115.4 g of ion-exchanged water were mixed and stirred at 25 ° C. for 1 hour. After completion of the reaction, the organic layer was separated by a liquid separation operation and washed twice with 115.4 g of ion-exchanged water. The obtained organic layer was concentrated under reduced pressure to obtain 146.2 g of liquid didecyldimethylammonium thiocyanate (hereinafter abbreviated as DMDDA-SCN) (yield 95.0%). The NMR data of DMDDA-SCN is shown below.
１Ｈ−ＮＭＲ（ＣＤＣｌ３） σ：０．８９（ｔ，６Ｈ）、１．２６−１．３９（ｍ，２８Ｈ）、１．７５−１．７８（ｍ，４Ｈ）、３．３０（ｓ，６Ｈ）、３．４２−３．４６（ｍ，４Ｈ） 1 H-NMR (CDCl 3 ) σ: 0.89 (t, 6H), 1.26-1.39 (m, 28H), 1.75-1.78 (m, 4H), 3.30 (s , 6H), 3.42-3.46 (m, 4H)
実施例３
８１．１％メチルトリオクチルアンモニウム＝クロリド水溶液１９９．３ｇ（０．４モル）、チオシアン酸ナトリウム４８．６ｇ（０．６モル）及びイオン交換水１３３ｇを混合し、２５℃で１時間攪拌した。反応終了後、有機層を分液操作により分離し、イオン交換水１３３ｇで２回洗浄した。得られた有機層を減圧下で濃縮し、液体のメチルトリオクチルアンモニウム＝チオシアナート（以下、ＴＯＭＡ−ＳＣＮと略記する。）１６４．２ｇを得た（収率９６．２％）。以下にＴＯＭＡ−ＳＣＮのＮＭＲデータを示す。
Example 3
89.3% methyltrioctylammonium chloride aqueous solution 199.3 g (0.4 mol), sodium thiocyanate 48.6 g (0.6 mol) and ion-exchanged water 133 g were mixed and stirred at 25 ° C. for 1 hour. After completion of the reaction, the organic layer was separated by a liquid separation operation and washed twice with 133 g of ion-exchanged water. The obtained organic layer was concentrated under reduced pressure to obtain 164.2 g of liquid methyltrioctylammonium thiocyanate (hereinafter abbreviated as TOMA-SCN) (yield 96.2%). The NMR data of TOMA-SCN is shown below.
１Ｈ−ＮＭＲ（ＣＤＣｌ３） σ：０．８８（ｔ，９Ｈ）、１．２８−１．４０（ｍ，３０Ｈ）、１．６９−１．７８（ｍ，６Ｈ）、３．２２（ｓ，３Ｈ）、３．３３−３．３９（ｍ，６Ｈ） 1 H-NMR (CDCl 3 ) σ: 0.88 (t, 9H), 1.28-1.40 (m, 30H), 1.69-1.78 (m, 6H), 3.22 (s , 3H), 3.33-3.39 (m, 6H)
実施例４
２液架橋型アクリル粘着剤ＳＫダイン９０９Ａ（登録商標、綜研化学株式会社製）１００重量部に、ＴＢＡ−ＳＣＮ５重量部、アクリル樹脂用硬化剤Ｌ−４５（綜研化学株式会社製）を０．２重量部、希釈溶剤として酢酸エチル／メチルエチルケトン（５０／５０）１５０重量部を添加して粘着剤コート液を調製した。本コー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でコートした後、８０℃で２分間加熱硬化させて評価用試験フィルムを作成した。作成した試験フィルムを１５〜２０℃、５０％ＲＨの雰囲気中に２４時間保持した後、２０℃、５０％ＲＨでコート面の表面抵抗値を測定した。透明性については、目視で観察し、透明な場合を「○」、不透明な場合を「×」とした。その結果を表１に示す。
Example 4
Two parts cross-linking acrylic adhesive SK Dyne 909A (registered trademark, manufactured by Soken Chemical Co., Ltd.) 100 parts by weight, TBA-SCN 5 parts by weight, acrylic resin curing agent L-45 (manufactured by Soken Chemical Co., Ltd.) 0.2 An adhesive coating solution was prepared by adding 150 parts by weight of ethyl acetate / methyl ethyl ketone (50/50) as a diluent solvent. The coating solution was coated on a polyester film with a bar coater at a dry thickness of about 10 μm, and then heat-cured at 80 ° C. for 2 minutes to prepare a test film for evaluation. The prepared test film was held 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. About transparency, it observed visually, the case where it was transparent was set to "(circle)", and the case where it was opaque was set to "x". The results are shown in Table 1.
実施例５及び６
実施例４に記載のＴＢＡ−ＳＣＮに代えて、表１に示す帯電防止剤を使用した以外は実施例４と同様にして試験フィルムを作製し、かかる試験フィルムの表面抵抗値の測定を実施例４と同様にして行った。透明性についても、実施例４と同様の方法により測定した。それらの結果を表１に示す。
Examples 5 and 6
A test film was prepared in the same manner as in Example 4 except that the antistatic agent shown in Table 1 was used instead of the TBA-SCN described in Example 4, and the surface resistance value of the test film was measured. This was carried out in the same manner as in 4. The transparency was also measured by the same method as in Example 4. The results are shown in Table 1.
比較例１〜５
実施例４に記載のＴＢＡ−ＳＣＮに代えて、表１に示す帯電防止剤を使用した以外は実施例４と同様にして試験フィルムを作製し、かかる試験フィルムの表面抵抗値の測定を実施例４と同様にして行った。透明性についても、実施例４と同様の方法により測定した。それらの結果を表１に示す。なお表１中、ＴＢＡ−ＰＴＳはテトラブチルアンモニウム＝ｐ−トルエンスルホナートを、ＤＭＤＤＡ−ＮＯ３はジデシルジメチルアンモニウム＝ナイトレートを、ＤＭＤＤＡ−ＰＴＳはジデシルジメチルアンモニウム＝ｐ−トルエンスルホナートを、ＴＯＭＡ−ＮＯ３はメチルトリオクチルアンモニウム＝ナイトレートを、ＴＯＭＡ−ＰＴＳはメチルトリオクチルアンモニウム＝ｐ−トルエンスルホナートを、それぞれ表す。
Comparative Examples 1-5
A test film was prepared in the same manner as in Example 4 except that the antistatic agent shown in Table 1 was used instead of the TBA-SCN described in Example 4, and the surface resistance value of the test film was measured. This was carried out in the same manner as in 4. The transparency was also measured by the same method as in Example 4. The results are shown in Table 1. In Table 1, TBA-PTS is tetrabutylammonium = p-toluenesulfonate, DMDDA-NO 3 is didecyldimethylammonium nitrate, DMDDA-PTS is didecyldimethylammonium = p-toluenesulfonate, TOMA-NO 3 represents methyl trioctyl ammonium = nitrate, and TOMA-PTS represents methyl trioctyl ammonium = p-toluenesulfonate.
表１の結果から、本発明の樹脂用帯電防止剤を添加したアクリル樹脂組成物は、チオシアナートイオン以外のものをアニオンとするアンモニウム塩を用いた場合に比べて、表面抵抗値については同程度の値を示すものの、樹脂の透明性については良好であることがわかった。 From the results in Table 1, the acrylic resin composition to which the antistatic agent for resin of the present invention was added had the same surface resistance value as compared with the case of using an ammonium salt having an anion other than thiocyanate ion. Although it shows a value of the degree, it was found that the transparency of the resin is good.
実施例７
ビスフェノールＡ型エポキシ樹脂エピコート８２８（エポキシ当量１８６ｇ／ｅｑ、登録商標、ジャパンエポキシレジン株式会社製）１００重量部、硬化剤としてイミノビスプロピルアミン１４．１重量部及び、ＤＭＤＤＡ−ＳＣＮ５．７重量部（樹脂に対して５重量％）を混合し、エポキシ樹脂組成物を得た。かかるエポキシ樹脂組成物を直径５０ｍｍ×深さ５ｍｍの円形金型に流し込み、５０℃で１時間、さらに１００℃で６時間熱硬化させて評価用試験片を作成した。作成した試験片を２３℃、５０％ＲＨの雰囲気中に６時間放置した後、２３℃、５０％ＲＨで試験片の表面抵抗を測定した。透明性については、目視で観察し、透明な場合を「○」、不透明な場合を「×」とした。その結果を表２に示す。
Example 7
100 parts by weight of bisphenol A type epoxy resin Epicoat 828 (epoxy equivalent 186 g / eq, registered trademark, manufactured by Japan Epoxy Resins Co., Ltd.), 14.1 parts by weight of iminobispropylamine as a curing agent, and 5.7 parts by weight of DMDDA-SCN ( 5 wt% with respect to the resin) was mixed to obtain an epoxy resin composition. Such an epoxy resin composition was poured into a circular mold having a diameter of 50 mm and a depth of 5 mm, and heat-cured at 50 ° C. for 1 hour and further at 100 ° C. for 6 hours to prepare an evaluation test piece. The prepared test piece was left in an atmosphere of 23 ° C. and 50% RH for 6 hours, and then the surface resistance of the test piece was measured at 23 ° C. and 50% RH. About transparency, it observed visually, the case where it was transparent was set to "(circle)", and the case where it was opaque was set to "x". The results are shown in Table 2.
実施例８
実施例７に記載のＤＭＤＤＡ−ＳＣＮに代えて、表２に示す帯電防止剤を使用した以外は実施例７と同様にして試験片を作製し、かかる試験片の表面抵抗値の測定を実施例７と同様にして行った。透明性についても、実施例７と同様の方法により測定した。その結果を表２に示す。
Example 8
A test piece was prepared in the same manner as in Example 7 except that the antistatic agent shown in Table 2 was used instead of the DMDDA-SCN described in Example 7, and the surface resistance value of the test piece was measured. This was carried out in the same manner as in 7. The transparency was also measured by the same method as in Example 7. The results are shown in Table 2.
比較例６〜１０
実施例７に記載のＤＭＤＤＡ−ＳＣＮに代えて、表２に示す帯電防止剤を使用した以外は実施例７と同様にして試験片を作製し、かかる試験片の表面抵抗値の測定を実施例７と同様にして行った。透明性についても、実施例７と同様の方法により測定した。それらの結果を表２に示す。
Comparative Examples 6-10
A test piece was prepared in the same manner as in Example 7 except that the antistatic agent shown in Table 2 was used instead of the DMDDA-SCN described in Example 7, and the surface resistance value of the test piece was measured. This was carried out in the same manner as in 7. The transparency was also measured by the same method as in Example 7. The results are shown in Table 2.
表２の結果から、本発明の樹脂用帯電防止剤を添加したエポキシ樹脂組成物は、チオシアナートイオン以外のものをアニオンとするアンモニウム塩を用いた場合と比べて、同等の透明性および低い表面抵抗値を示すことがわかった。 From the results of Table 2, the epoxy resin composition to which the antistatic agent for resins of the present invention is added is equivalent in transparency and low as compared with the case of using an ammonium salt having an anion other than thiocyanate ions. It was found to show a surface resistance value.
Claims (5)
Ｒ１Ｒ２Ｒ３Ｒ４Ｎ＋ＳＣＮ− （１）
（式中、Ｒ１及びＲ２は炭素数４〜１８のアルキル基、Ｒ３は炭素数１〜１８のアルキル基、Ｒ４は炭素数１〜４のアルキル基を示し、Ｒ１〜Ｒ４は互いに同じであっても、異なっていてもよい。）で表されるアンモニウム塩を有効成分として含有することを特徴とする樹脂用帯電防止剤。 Formula (1):
R 1 R 2 R 3 R 4 N + SCN − (1)
(In the formula, R 1 and R 2 represent an alkyl group having 4 to 18 carbon atoms, R 3 represents an alkyl group having 1 to 18 carbon atoms, R 4 represents an alkyl group having 1 to 4 carbon atoms, and R 1 to R 4 May be the same as or different from each other.) An antistatic agent for a resin comprising an ammonium salt represented by
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| JPH03261747A (en) * | 1990-03-12 | 1991-11-21 | Agency Of Ind Science & Technol | Quaternary ammonium salt and production thereof |
| JPH06157818A (en) * | 1992-11-24 | 1994-06-07 | Tosoh Corp | Crosslinking agent |
| JPH06172586A (en) * | 1992-12-08 | 1994-06-21 | Tosoh Corp | Vulcanizable elastomer composition |
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| JPH11157034A (en) * | 1997-11-27 | 1999-06-15 | Unitika Ltd | Polyester film with antistatic property and blocking resistivity |
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| JPH06175250A (en) * | 1992-12-09 | 1994-06-24 | Konica Corp | Silver halide emulsion and silver halide color photosensitive material |
| JP2006176648A (en) * | 2004-12-22 | 2006-07-06 | Kao Corp | Antistatic agent for biodegradable resin |
| US20070114034A1 (en) * | 2005-11-18 | 2007-05-24 | Chevron U.S.A. Inc. | Controlling pressure and static charge build up within an annular volume of a wellbore |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH03261747A (en) * | 1990-03-12 | 1991-11-21 | Agency Of Ind Science & Technol | Quaternary ammonium salt and production thereof |
| JPH06157818A (en) * | 1992-11-24 | 1994-06-07 | Tosoh Corp | Crosslinking agent |
| JPH06172586A (en) * | 1992-12-08 | 1994-06-21 | Tosoh Corp | Vulcanizable elastomer composition |
| JPH07171931A (en) * | 1993-12-20 | 1995-07-11 | Tosoh Corp | Rubber laminate |
| JPH11157034A (en) * | 1997-11-27 | 1999-06-15 | Unitika Ltd | Polyester film with antistatic property and blocking resistivity |
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