JP5476502B2 - イオン結合性塩並びにこれを含む帯電防止剤および防曇剤 - Google Patents
イオン結合性塩並びにこれを含む帯電防止剤および防曇剤 Download PDFInfo
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- JP5476502B2 JP5476502B2 JP2013126936A JP2013126936A JP5476502B2 JP 5476502 B2 JP5476502 B2 JP 5476502B2 JP 2013126936 A JP2013126936 A JP 2013126936A JP 2013126936 A JP2013126936 A JP 2013126936A JP 5476502 B2 JP5476502 B2 JP 5476502B2
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- ion
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- ammonium
- ionic liquid
- ammonium ion
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- 239000003795 chemical substances by application Substances 0.000 title claims description 94
- 239000002216 antistatic agent Substances 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title claims description 6
- -1 monoethyl diethanol ammonium ion Chemical compound 0.000 claims description 618
- 150000002500 ions Chemical class 0.000 claims description 130
- 239000000126 substance Substances 0.000 claims description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 description 134
- 238000012360 testing method Methods 0.000 description 36
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- 230000000052 comparative effect Effects 0.000 description 20
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- 125000000542 sulfonic acid group Chemical group 0.000 description 16
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- CZPWVGJYEJSRLH-UHFFFAOYSA-P pyrimidine-1,3-diium Chemical group C1=C[NH+]=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-P 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical group C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical group C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 5
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- OADIZUFHUPTFAG-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCO OADIZUFHUPTFAG-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- AQIIVEISJBBUCR-UHFFFAOYSA-N 4-(3-phenylpropyl)pyridine Chemical compound C=1C=NC=CC=1CCCC1=CC=CC=C1 AQIIVEISJBBUCR-UHFFFAOYSA-N 0.000 description 2
- CVLHGLWXLDOELD-UHFFFAOYSA-N 4-(Propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C=C1 CVLHGLWXLDOELD-UHFFFAOYSA-N 0.000 description 2
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- QEFRNWWLZKMPFJ-YGVKFDHGSA-N L-methionine S-oxide Chemical compound CS(=O)CC[C@H](N)C(O)=O QEFRNWWLZKMPFJ-YGVKFDHGSA-N 0.000 description 2
- 241001272720 Medialuna californiensis Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
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- 238000007754 air knife coating Methods 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 2
- JMJRNNLOJLYQLM-UHFFFAOYSA-N azane;propan-1-ol Chemical compound N.CCCO JMJRNNLOJLYQLM-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
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- XDSGMUJLZDSCPA-UHFFFAOYSA-N diazanium;phenoxybenzene;sulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 XDSGMUJLZDSCPA-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
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- 125000005561 phenanthryl group Chemical group 0.000 description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
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- LAGVOJJKZPIRMS-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-3-yl) 2-methylprop-2-enoate Chemical compound CN1C(C)(C)CCC(OC(=O)C(C)=C)C1(C)C LAGVOJJKZPIRMS-UHFFFAOYSA-N 0.000 description 1
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 1
- GJTKPHVLTWGDSF-UHFFFAOYSA-N 1,2-diethylcyclopentan-1-amine Chemical compound CCC1CCCC1(N)CC GJTKPHVLTWGDSF-UHFFFAOYSA-N 0.000 description 1
- PEAVKOUMCANJQN-UHFFFAOYSA-N 1,2-dimethylcycloheptan-1-amine Chemical compound CC1CCCCCC1(C)N PEAVKOUMCANJQN-UHFFFAOYSA-N 0.000 description 1
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- PJEIKNFCVJAVQI-UHFFFAOYSA-N 1-ethyl-2-methylcycloheptan-1-amine Chemical compound CCC1(N)CCCCCC1C PJEIKNFCVJAVQI-UHFFFAOYSA-N 0.000 description 1
- LMPYMFIXYDCTCK-UHFFFAOYSA-N 1-ethyl-2-methylcyclohexan-1-amine Chemical compound CCC1(N)CCCCC1C LMPYMFIXYDCTCK-UHFFFAOYSA-N 0.000 description 1
- YACUHNJCVLMTQE-UHFFFAOYSA-N 1-ethyl-2-methylcyclopentan-1-amine Chemical compound CCC1(N)CCCC1C YACUHNJCVLMTQE-UHFFFAOYSA-N 0.000 description 1
- FOSIQLDTYDZKKS-UHFFFAOYSA-N 1-ethyl-n-(1-ethyl-2-methylcyclopentyl)-2-methylcyclopentan-1-amine Chemical compound C1CCC(C)C1(CC)NC1(CC)CCCC1C FOSIQLDTYDZKKS-UHFFFAOYSA-N 0.000 description 1
- FPKZICLABSGXHK-UHFFFAOYSA-N 1-ethyl-n-(1-ethylcyclohexyl)cyclohexan-1-amine Chemical compound C1CCCCC1(CC)NC1(CC)CCCCC1 FPKZICLABSGXHK-UHFFFAOYSA-N 0.000 description 1
- WHMYVOTYNLLHRM-UHFFFAOYSA-N 1-ethyl-n-(1-ethylcyclopentyl)cyclopentan-1-amine Chemical compound C1CCCC1(CC)NC1(CC)CCCC1 WHMYVOTYNLLHRM-UHFFFAOYSA-N 0.000 description 1
- WJKBJDQVXXTCDN-UHFFFAOYSA-N 1-ethylcycloheptan-1-amine Chemical compound CCC1(N)CCCCCC1 WJKBJDQVXXTCDN-UHFFFAOYSA-N 0.000 description 1
- FUCXRENHTUFVDM-UHFFFAOYSA-N 1-ethylcyclohexan-1-amine Chemical compound CCC1(N)CCCCC1 FUCXRENHTUFVDM-UHFFFAOYSA-N 0.000 description 1
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- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HXXZMGHBGGBDJE-UHFFFAOYSA-N 1-methyl-n-(1-methylcycloheptyl)cycloheptan-1-amine Chemical compound C1CCCCCC1(C)NC1(C)CCCCCC1 HXXZMGHBGGBDJE-UHFFFAOYSA-N 0.000 description 1
- RAPPNZGHYYLTNI-UHFFFAOYSA-N 1-methyl-n-(1-methylcyclohexyl)cyclohexan-1-amine Chemical compound C1CCCCC1(C)NC1(C)CCCCC1 RAPPNZGHYYLTNI-UHFFFAOYSA-N 0.000 description 1
- OPVKVFCUSDCBLK-UHFFFAOYSA-N 1-methyl-n-(1-methylcyclopentyl)cyclopentan-1-amine Chemical compound C1CCCC1(C)NC1(C)CCCC1 OPVKVFCUSDCBLK-UHFFFAOYSA-N 0.000 description 1
- PIBQUPOHNJFBQR-UHFFFAOYSA-N 1-methylcycloheptan-1-amine Chemical compound CC1(N)CCCCCC1 PIBQUPOHNJFBQR-UHFFFAOYSA-N 0.000 description 1
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- NXLACVVNHYIYJN-UHFFFAOYSA-N 1-phenyl-n-(1-phenylethyl)ethanamine Chemical compound C=1C=CC=CC=1C(C)NC(C)C1=CC=CC=C1 NXLACVVNHYIYJN-UHFFFAOYSA-N 0.000 description 1
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- 125000003163 2-(2-naphthyl)ethyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(C([H])=C([H])C2=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
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- VXDUTIRBTKJEMV-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethyl dihydrogen phosphate Chemical compound CCCCC(CC)COCCOCCOP(O)(O)=O VXDUTIRBTKJEMV-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
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- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- RILXNFANUHPQEP-UHFFFAOYSA-N pentadec-1-en-1-amine Chemical compound CCCCCCCCCCCCCC=CN RILXNFANUHPQEP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NSCBFOVRSLSEIW-UHFFFAOYSA-O pyrazin-1-ium-1-carboxamide Chemical compound NC(=O)[N+]1=CC=NC=C1 NSCBFOVRSLSEIW-UHFFFAOYSA-O 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- RZYFONVAFJSMQJ-UHFFFAOYSA-N tetradec-1-en-1-amine Chemical compound CCCCCCCCCCCCC=CN RZYFONVAFJSMQJ-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ASLXNOZOXWPTNG-UHFFFAOYSA-N tricosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCN ASLXNOZOXWPTNG-UHFFFAOYSA-N 0.000 description 1
- YJXXVMUUYWWHNC-UHFFFAOYSA-N tridec-1-en-1-amine Chemical compound CCCCCCCCCCCC=CN YJXXVMUUYWWHNC-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WQCRINVIOJTXSE-UHFFFAOYSA-N trimethyl(nonadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCCC[N+](C)(C)C WQCRINVIOJTXSE-UHFFFAOYSA-N 0.000 description 1
- ZVFDPYZBJGKPII-UHFFFAOYSA-N trimethyl(nonyl)azanium Chemical compound CCCCCCCCC[N+](C)(C)C ZVFDPYZBJGKPII-UHFFFAOYSA-N 0.000 description 1
- FSWHKYOVBASSCG-UHFFFAOYSA-N trimethyl(pentadecyl)azanium Chemical compound CCCCCCCCCCCCCCC[N+](C)(C)C FSWHKYOVBASSCG-UHFFFAOYSA-N 0.000 description 1
- ACZOGADOAZWANS-UHFFFAOYSA-N trimethyl(pentyl)azanium Chemical compound CCCCC[N+](C)(C)C ACZOGADOAZWANS-UHFFFAOYSA-N 0.000 description 1
- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 description 1
- QKRNEEOLHKKGMA-UHFFFAOYSA-N trimethyl(tricosyl)azanium Chemical compound CCCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C QKRNEEOLHKKGMA-UHFFFAOYSA-N 0.000 description 1
- CUHTWKRYGOJCEX-UHFFFAOYSA-N trimethyl(tridecyl)azanium Chemical compound CCCCCCCCCCCCC[N+](C)(C)C CUHTWKRYGOJCEX-UHFFFAOYSA-N 0.000 description 1
- QDUATGYYXKDLEI-UHFFFAOYSA-N trimethyl(undecyl)azanium Chemical compound CCCCCCCCCCC[N+](C)(C)C QDUATGYYXKDLEI-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZMKXDWIJLNQLPW-UHFFFAOYSA-N undec-1-en-1-amine Chemical compound CCCCCCCCCC=CN ZMKXDWIJLNQLPW-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-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
- 238000004065 wastewater treatment Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Secondary Cells (AREA)
Description
前記化学式(1)で表わされるイオン液体は、スルホン酸アニオンを含む。
本発明に係る処理剤は、プラスチック、金属、CO2等のガスなどに対して、物理的な作用または化学的な作用を及ぼす処理剤である。より具体的には、例えば、二次電池用電解液、液体電解質またはゲル電解質、電気メッキ浴、環境低負荷型溶媒(リサイクル可能な反応溶媒)、潤滑剤、帯電防止剤、防曇剤、分散剤、酸性ガス吸収剤、廃水処理剤、合成触媒、難溶性物質の可溶化溶媒、分離抽出溶媒、高速液体クロマトグラフィー(HPLC)用溶媒、ドラッグデリバリーシステム(DDS)、金属加工、ポリマー加工、セルロース溶解剤などの用途が挙げられる。
前記イオン液体を含む処理剤の一実施形態として、帯電防止剤を提供する。
前記イオン液体を含む処理剤の一実施形態として、防曇剤を提供する。
前記イオン液体を含む処理剤の一実施形態として、分散剤・乳化剤を提供する。
(潤滑剤)
前記イオン液体を含む処理剤の一実施形態として、潤滑剤を提供する。
前記イオン液体を含む処理剤の一実施形態として、電解液を提供する。
前記イオン液体を含む処理剤の一実施形態として、セルロース溶解剤を提供する。
キシレンスルホン酸(o−,m−,p−キシレン異性体混合物のスルホン酸)(テイカ株式会社製、商品名:テイカトックス110、略称:Xyl−SO3H)186.2質量部にN−モノエチルエタノールアミン(日本乳化剤株式会社製、商品名:アミノアルコールMEM、略称:MEM)89.1質量部を滴下した後に1時間反応させて、目的とするイオン液体(略称:[MEM][Xyl−SO3])を275.3質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
MEMの代わりにN,N−ジエチルエタノールアミン(日本乳化剤株式会社製、商品名:アミノアルコール2A、略称:2A)117.2質量部を用いたことを除いては実施例1と同様にして目的とするイオン液体(略称:[2A][Xyl−SO3])を303.4質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
Xyl−SO3Hの代わりにクメンスルホン酸(o−,m−,p−クメンスルホン酸異性体混合物)(テイカ株式会社製、商品名:テイカトックス500、略称:Cum−SO3H)199.3質量部を用いたことを除いては実施例1と同様にして目的とするイオン液体(略称:[MEM][Cum−SO3])を288.4質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
MEMの代わりに2A117.2質量部を用いたことを除いては実施例3と同様にして目的とするイオン液体(略称:[2A][Cum−SO3])を316.5質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
MEMの代わりにN,N−ジメチルエタノールアミン(日本乳化剤株式会社製、商品名:アミノアルコール2Mabs、略称:2Mabs)89.1質量部を用いたことを除いては実施例3と同様にして目的とするイオン液体(略称:[2Mabs][Cum−SO3])を288.4質量部得た。
MEMの代わりにN−モノエチルジエタノールアミン(日本乳化剤株式会社製、商品名:アミノアルコールMED、略称:MED)133.2質量部を用いたことを除いては実施例3と同様にして目的とするイオン液体(略称:[MED][Cum−SO3])を332.5質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
MEMの代わりにN−モノブチルエタノールアミン(日本乳化剤株式会社製、商品名:アミノアルコールMBM、略称:MBM)117.2質量部を用いたことを除いては実施例3と同様にして目的とするイオン液体(略称:[MBM][Cum−SO3])を316.5質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
MEMの代わりにN、N−ジブチルエタノールアミン(日本乳化剤株式会社製、商品名:アミノアルコール2B、略称:2B)173.3質量部を用いたことを除いては実施例3と同様にして目的とするイオン液体([2B][Cum−SO3])を372.6質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
ジオクチルフマレート200.0質量部、50%亜硫酸水素アンモニウム水溶液116.4質量部、メタノール37.0質量部、水15.6質量部をオートクレーブに仕込み、120℃に昇温して24時間反応させた。この時の最大圧力は0.25MPaであった。
MEMの代わりにN,N−ジエチルアミノエチルアクリレート(略称:2A−A)171.2質量部を用いたことを除いては実施例1と同様にして目的とするイオン液体(略称:[2A−A][Xyl−SO3])を357.5質量部得た。
Xyl−SO3Hの代わりにCum−SO3H199.3質量部を用いたことを除いては実施例10と同様にして目的とするイオン液体(略称:[2A−A][Cum−SO3])を370.5質量部得た。
MEMの代わりにN,N−ジエチルアミノエチルメタクリレート(略称:2A−MA)185.3質量部、Xyl−SO3Hの代わりにドデシルベンゼンスルホン酸(o−,m−,p−ドデシルベンゼンスルホン酸異性体混合物)(テイカ株式会社製、商品名:テイカトックス120、略称:DB−SO3H)326.5質量部を用いたことを除いては実施例1と同様にして目的とするイオン液体(略称:[2A−MA][DB−SO3])を511.8質量部得た。
2A−MAの代わりにMEM89.1質量部を用いたことを除いては実施例12と同様にして目的とするイオン液体(略称:[MEM][DB−SO3])を415.6質量部得た。
2A−MAの代わりにN−メチル−2,2,6,6−テトラメチルピペリジニルメタクリレート(日本乳化剤株式会社製、商品名:ニューコールLS−3410、略称:LS−3410)240.4質量部を用いたことを除いては実施例12と同様にして目的とするイオン液体(略称:[LS−3410][DB−SO3])を566.9質量部得た。
Xyl−SO3Hの代わりにメタンスルホン酸(東京化成工業株式会社製、略称:Met−SO3H)96.1質量部を用いたことを除いては実施例1と同様にして目的とするイオン液体(略称:[MEM][Met−SO3])を185.2質量部得た。また、得られたイオン液体は常温(25℃)で液体であった。
ジエチレングリコールモノ2−エチルヘキシルエーテル(日本乳化剤株式会社製、商品名:2エチルヘキシルジグリコール、略称:EHDG)150.0質量部にトルエン150.0質量部を加え、110℃に昇温した。これにスルファミン酸80.2質量部を加え3時間反応させた。反応後、過剰のスルファミン酸を濾別して、ジエチレングリコールモノ2−エチルヘキシルエーテル硫酸エステルアンモニウム塩(略称:EHDG−SF)のトルエン溶液を得た。
比較例1で得られたEHDG−SFの50%トルエン溶液100.0質量部に、2Aを27.9質量部(EHDG−SFと2Aとのモル比は1:1.5)を用いたことを除いては比較例1と同様にして目的とするイオン液体(略称:[2A][EHDG−S])を65.3質量部得た。
ジオクチルスルフォサクシネートナトリウム塩のメタノール水溶液(日本乳化剤株式会社製、商品名:ニューコール291−M、略称:N−291−M)100.0質量部を減圧留去し(温度:150℃、減圧度:1.33kPa(10mmHg))、目的物(略称:[Na][DOSS])を65.0質量部得た。
DB−SO3Hを精製せずにそのまま使用した。
ジエチレングリコールモノ2−エチルヘキシルエーテル(日本乳化剤株式会社製、商品名:2−エチルヘキシルジグリコール、略称:EHDG)586.9質量部に無水リン酸127.2質量部を加え、70℃で5時間反応させてジエチレングリコールモノ2−エチルヘキシルエーテルリン酸エステル(略称:EHDG−P)を含む反応液を得た。
一部の実施例および比較例に係るイオン液体の10%重量減少温度を、示差熱熱重量同時測定装置(TG−DTA)(マックサイエンス社製 TG−DTA2000S)を用いて測定し、耐熱性を評価した。測定結果を表1に示す。ここで、10%重量減少温度とは、室温から400℃まで10℃/分で昇温した際に、イオン液体の重量が初期重量から10%減少した時点の温度である。
以下のように作製した一部の実施例および比較例に係るイオン液体を含む処理剤を用いて得られる試験片の表面固有抵抗率を測定し、帯電防止性を評価した。測定結果を表2に示す。
1−1)アクリレート系樹脂(P1)の作製
冷却管、窒素導入管、温度計、テフロン半月攪拌翼を備えたフラスコに、トルエン300.0質量部、n−ブチルアクリレート105.0質量部、メチルメタクリレート195.0質量部を仕込み、重合触媒としてアゾビスイソブチロニトリルを3.0質量部添加し、90℃で3時間重合を行い固形分50%トルエン溶液の樹脂(P1)を得た。
メチルメタクリレートの代わりにスチレン195.0質量部を用いたことを除いては樹脂(P1)の作製と同様にして樹脂(P2)を得た。
東洋紡績(株)製バイロン(登録商標)(バイロン20SS)(P3)を用いた。
2−1)
冷却管、窒素導入管、温度計、テフロン半月攪拌翼を備えたフラスコに、水100.0質量部を仕込み、80℃まで昇温した。三角フラスコにn−ブチルアクリレート100.0質量部、メチルメタクリレート70.0質量部、スチレン30.0質量部、アクリル酸4.0質量部、乳化剤としてDB−SO3H4.08質量部、水86.3質量部、10%ペルオキソ二硫酸アンモニウム水溶液10.2質量部を仕込み、混合した。これをフラスコに15.7質量部仕込み、80℃に昇温して30分間の初期重合を行った。その後3時間かけて三角フラスコ中のモノマーを80℃で滴下した。さらに80℃で1時間熟成を行い、28%アンモニア水2.0質量部を使用して中和し、エマルジョン(E1)を得た。
DB−SO3Hの代わりに実施例13で得られた[MEM][DB−SO3]4.08質量部を混合したことを除いては2−1)と同様にしてエマルジョン(E2)を得た。
DB−SO3Hの代わりに実施例14で得られた[LS−3410][DB−SO3]3.06質量部ならびにポリオキシエチレン多環フェニルエーテル硫酸エステルアンモニウム塩(略称:707−SF)1.02質量部を混合したことを除いては2−1)と同様にしてエマルジョン(E3)を得た。なお、前記707−SFは、ポリオキシエチレン多環フェニルエーテル硫酸エステルアンモニウム塩の30%水溶液(日本乳化剤株式会社製、商品名:ニューコール707−SF、略称:N−707−SF)を減圧留去して調製した。
3−1)溶液重合型試験片
樹脂(樹脂(P1)、樹脂(P2)または樹脂(P3))20.0質量部にイオン液体0.4質量部(樹脂固形分に対し2%)を混合した。得られた混合液をガラス板上に膜厚75μmで塗布し110℃の乾燥機にて10分間乾燥し、膜厚約15μmである試験片を得た。
エマルジョン(E1〜E3)をガラス板上に膜厚75μmで塗布し110℃の乾燥機にて3分間乾燥し、膜厚約15μmである試験片を得た。
4−1)試験片作製後の表面固有抵抗率(R1)
作製後の試験片の表面固有抵抗率(Ω/□(square))を(株)三菱化学アナリテック製高抵抗率計ハイレスターUPおよびURSプローブを用い、印加電圧250Vにて測定した。
水1Lに中性洗剤5滴を加えた洗浄水をスポンジに湿らせ、このスポンジで試験片を10回擦り、水道水に次いでイオン交換水の順にすすぎ、水滴を拭き取った後に110℃で5分間乾燥させた。この工程を5回繰り返した後の試験片の表面固有抵抗率を測定したことを除いては、前記4−1)試験片作製後の表面固有抵抗率の測定と同様にして表面固有抵抗率を測定した。
試験片に水道水を30秒間流水(約1L)させ、次いでイオン交換水ですすぎ、水滴を拭き取った後に110℃で5分間乾燥させた。この工程を1回行った後の試験片の表面固有抵抗率を測定したことを除いては、前記4−1)試験片作製後の表面固有抵抗率の測定と同様にして表面固有抵抗率を測定した。
一部の実施例および比較例に係るイオン液体を用いて作製した試験片について、試験片の表面の曇りの有無より、防曇性を以下のようにして評価した。評価結果を表3に示す。
△:斑点状に曇る
×:曇りまたは液滴が確認される
一部の実施例および比較例に係るイオン液体を含む処理剤について、乳化重合用乳化剤として用い、重合安定性、エマルジョンの平均粒子径および110℃の乾燥機にて10分間乾燥した代わりに3分間乾燥したことを除いては3−2)と同様にして作製した試験片の耐水性を評価した。測定結果を表4に示す。
◎:全体が透明
〇:部分的に青白濁
△:全体が青白濁
×:全体が白濁
剥離の有無(密着性)
◎:剥離なし(指で擦っても剥離せず)
○:剥離なし(指で擦ると剥離する)
△:部分的に剥離
×:全体が剥離
一部の実施例に係るイオン液体の動摩擦係数fを以下のように測定し、潤滑性能を評価した。測定結果を表6に示す。
ボール:SUJ2(3/16インチ)
ローラピン:SUJ2
温度:25℃
荷重:左右各80g、中央40g。
一部の実施例に係るイオン液体のイオン伝導率およびサイクリックボルタンメトリー(CV)を測定し、電解液としての評価を行った。測定結果をそれぞれ表7および図1に示す。
イオン液体15mlを25mlビーカーセルに入れ、ポテンショ/ガルバノスタットVSP(バイオロジック社製)を用いてイオン液体の抵抗を測定した。
作用極、対極:Pt
周波数:500kHz〜10MHz
印加電圧:10mV
イオン液体15mlを25mlビーカーセルに入れ、ポテンショ/ガルバノスタットVSP(バイオロジック社製)を用いてイオン液体のサイクリックボルタンメトリー(CV)を測定した。
作用極:GC、対極:Pt
参照極:Ag/Ag+
電位の掃引速度:10mV/秒。
一部の実施例および比較例に係るイオン液体のセルロース溶解性を測定し、セルロース溶解剤としての評価を行った。測定結果を表8に示す。
容量20mLのスクリューバイアル瓶にイオン液体10gを量りとり、イオン液体の重量に対して約0.06重量%のセルロース製の濾紙(3mm×3mm)をスクリューバイアル瓶中に投入した。マグネチックスターラー付きのホットプレートを用いて、100℃で15時間撹拌した。濾紙およびイオン液体の外観を目視で観察し、下記評価基準に従って、セルロース溶解性の評価を行った。
〇:濾紙の原形はないが、イオン液体にセルロースが分散している
△:濾紙の原形があり、イオン液体中にセルロースが分散している
×:濾紙の原形があり、イオン液体は透明である。
Claims (4)
- 下記化学式(1)で表わされるイオン結合性塩:
- 下記化学式(3):
- 請求項1または2に記載のイオン結合性塩を含む、帯電防止剤。
- 請求項1または2に記載のイオン結合性塩を含む、防曇剤。
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