JP7363319B2 - ポリウレタン樹脂組成物、それを用いた成形体及び靴底 - Google Patents
ポリウレタン樹脂組成物、それを用いた成形体及び靴底 Download PDFInfo
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- JP7363319B2 JP7363319B2 JP2019182159A JP2019182159A JP7363319B2 JP 7363319 B2 JP7363319 B2 JP 7363319B2 JP 2019182159 A JP2019182159 A JP 2019182159A JP 2019182159 A JP2019182159 A JP 2019182159A JP 7363319 B2 JP7363319 B2 JP 7363319B2
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- polyurethane resin
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- 229920005749 polyurethane resin Polymers 0.000 title claims description 40
- 239000011342 resin composition Substances 0.000 title description 26
- -1 sulfate ester anions Chemical class 0.000 claims description 94
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 239000002608 ionic liquid Substances 0.000 claims description 36
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 26
- 150000001768 cations Chemical class 0.000 claims description 23
- 150000001450 anions Chemical class 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 7
- UQWLFOMXECTXNQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F UQWLFOMXECTXNQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
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- 125000001931 aliphatic group Chemical group 0.000 description 49
- 239000003795 chemical substances by application Substances 0.000 description 30
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 22
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- 229920005906 polyester polyol Polymers 0.000 description 19
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 18
- KQPPJWHBSYEOKV-UHFFFAOYSA-M dodecyl-ethyl-dimethylazanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCC[N+](C)(C)CC KQPPJWHBSYEOKV-UHFFFAOYSA-M 0.000 description 16
- 239000005056 polyisocyanate Substances 0.000 description 16
- 229920001228 polyisocyanate Polymers 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 13
- 239000002216 antistatic agent Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229920000570 polyether Polymers 0.000 description 11
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 11
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 10
- 239000001361 adipic acid Substances 0.000 description 10
- 235000011037 adipic acid Nutrition 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000005187 foaming Methods 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000006260 foam Substances 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000004088 foaming agent Substances 0.000 description 7
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- 239000000178 monomer Substances 0.000 description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 239000002075 main ingredient Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 3
- 101000812677 Homo sapiens Nucleotide pyrophosphatase Proteins 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 102100039306 Nucleotide pyrophosphatase Human genes 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
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- 229930195729 fatty acid Natural products 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
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- PXELHGDYRQLRQO-UHFFFAOYSA-N 1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1 PXELHGDYRQLRQO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 235000011187 glycerol Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000000383 hazardous chemical Substances 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
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- ZIRHAFGGEBQZKX-UHFFFAOYSA-N pentyl hydrogen sulfate Chemical compound CCCCCOS(O)(=O)=O ZIRHAFGGEBQZKX-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 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
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- UZZYXUGECOQHPU-UHFFFAOYSA-N sulfuric acid monooctyl ester Natural products CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
R5、R7は、それぞれ独立に、炭素原子数1~20の脂肪族炭化水素基を表す。
R6、R8~R9は、それぞれ独立に、水素原子又は炭素原子数1~20の脂肪族炭化水素基を表す。
ただし、R5~R9の少なくとも1つは、炭素原子数3以上のアルキル基を表す。]
R10は、炭素原子数1~20の脂肪族炭化水素基を表す。
R11~R15は、それぞれ独立に、水素原子、又は炭素原子数1~20の脂肪族炭化水素基を表す。]
R16~R17は、それぞれ独立に、炭素原子数1~20の脂肪族炭化水素基を表す。
R18~R25は、それぞれ独立に、水素原子又は炭素原子数1~20の脂肪族炭化水素基を表す。
ただし、R16~R25の少なくとも1つは、炭素原子数3以上のアルキル基を表す。
R26~R27は、それぞれ独立に、炭素原子数1~20の脂肪族炭化水素基を表す。
R28~R37は、それぞれ独立に、水素原子又は炭素原子数1~20の脂肪族炭化水素基を表す。
ただし、R26~R37の少なくとも1つは、炭素原子数3以上のアルキル基を表す。]
ただし、R38~R41の少なくとも1つは、炭素原子数3以上のアルキル基を表す。]
反応容器に、イソシアネート(A2)として、4,4’-ジフェニルメタンジイソシアネート(以下「4,4’MDI」と略称。商標:ミリオネート MT、日本ポリウレタン工業株式会社製。)560部を仕込み、攪拌を開始した。
次いで、ポリオール(A1)として、ポリオールa(エチレングリコール(EG)/1,4-ブチレングリコール(1,4BG)とアジピン酸(AA)から合成された水酸基価56.1mgKOH/gのポリエステルポリオール。EG/1,4BG=5/5モル比のもの。)443.5質量部を分割で仕込み混合し、窒素気流下60℃で8時間反応を行い、NCO当量250のイソシアネート基末端ウレタンプレポリマー(A)を含有する主剤(X)を得た。
イソシアネート基と反応しうる官能基を2個以上有する化合物(B1)としてポリオールb(EG/1,4BGとAAから合成された水酸基価112mgKOH/gのポリエステルポリオール。EG/1,4BG=5/5モル比のもの。)65.0質量部と、ポリオールc(ジエチレングリコール(DEG)/トリメチロールプロパン(TMP)とAAから合成された水酸基価60mgKOH/gのポリエステルポリオール。DEG/TMP=15/1モル比のもの。)5.0質量部と、ポリオールd(2-メチル-1,3―プロパンジオールとAAから合成された水酸基価56mgKOH/gのポリエステルポリオール。)30.0質量部と、EG7.0質量部、発泡剤として水(C)0.18質量部、触媒(D)としてトリエチレンジアミン(TEDA)1.0質量部を配合し、充分に撹拌、混合して、硬化剤(Y1)を調製した。
イソシアネート基反応性化合物(B2)としてポリオールe(EG/1,4BGとAAから合成された水酸基価66mgKOH/gのポリエステルポリオール。EG/1,4BG=5/5モル比のもの。)91.5質量部と、ポリオールc(ジエチレングリコール(DEG)/トリメチロールプロパン(TMP)とAAから合成された水酸基価60mgKOH/gのポリエステルポリオール。DEG/TMP=15/1モル比のもの。)4.8質量部と、EG10.7質量部、発泡剤として水(C)0.40質量部、触媒(D)としてトリエチレンジアミン(TEDA)1.0質量部を配合し、充分に撹拌、混合して、硬化剤(Y2)を調製した。
≪2液硬化型発泡ポリウレタン樹脂組成物(P1)の製造≫
混合容器に、前記硬化剤(Y1)107.0質量部、帯電防止剤としてN-エチル-N,N-ジメチル-N-ドデシルアンモニウムエチル硫酸塩(E1)8.2質量部と(E2K1)1-ブチル-3-メチルーイミダゾリウムと(E2A1)ビス(トリフルオロメチルスルホニル)イミドからなるイオン液体(E2)を1.26質量部配合し、充分に撹拌、混合し、硬化剤(Y1)と帯電防止剤を含むアウトソール用ポリオールコンパウンド(PCA1)を得た。
イオン液体(E2)のカチオン成分とアニオン成分の組合せ及び量と、主剤と前記ポリオールコンパウンドとの質量比を表1に示すように変更したこと以外は、実施例1と同様にして、発泡成形品を得た。
≪2液硬化型発泡ポリウレタン樹脂組成物(P8)の製造≫
イオン液体として(E2K5)1-エチル-3-メチル-
イミダゾリウムと(E2A4)エチルスルファートからなるイオン液体(E2)を用いたこと以外は、実施例1と同様にして、発泡成形品を得た。
イオン液体(E2)のカチオン成分とアニオン成分の組合せ及び量と、主剤と前記ポリオールコンパウンドとの質量比を表1に示すように変更したこと以外は、実施例1と同様にして、発泡成形品を得た。
得られたウレタン成形体の質量を体積で割ることにより、密度(g/cm3)を算出した。
得られたウレタン成形体の硬度を日本工業規格 JIS K 7312-1996(硬さ試験)に準拠して、スプリング硬さ試験(タイプC)にて評価した。
温度30℃、相対湿度80%RHの条件下、アウトソール樹脂を100mm×200mm×5mm金型内に注入し、2.5分脱型後、金型から取り出した。成形品を30℃、相対湿度80%の雰囲気下に3分静置し、その後、100mm×200mm×15mm金型にアウトソールを入れ、空間にミッドソール樹脂を射出成形した。3.5分後に脱型し、常温にて24時間静置した。成形品を25mm×150mmに打ち抜き、アウトソールとミッドソールの剥離強度を株式会社島津オートグラフ AG-1にて剥離試験速度100mm/minで剥離強度を測定した。
電池式絶縁抵抗計(横河電機株式会社製、2604 01型)を使用し、上記で作成した測定試料(75mm×75mm×10mm)の下面に鉄板(300mm×200mm×1mm)を上面に鉄板(75mm×75mm×3mm)をそれぞれ接触させて、成形後7費時点の電気抵抗値を測定し、帯電防止性を評価した。なお、成形後の試料は温度23℃、相対湿度50%の室内環境下で保存し、ついで常温条件(23℃、相対湿度65%)、及び低温低湿条件(0℃)の2条件にて電気抵抗値(単位:MΩ)を測定した。
4,4’MDI:4,4’-ジフェニルメタンジイソシアネート
EG :エチレングリコール
1,4BG :1,4-ブチレングリコール
AA :アジピン酸
DEG :ジエチレングリコール
TMP :トリメチロールプロパン
TEDA :トリエチレンジアミン
(E1) :アルキル置換第4級アンモニウム塩
(AM1):N-エチル-N,N-ジメチル-N-ドデシルアンモニウムエチル硫酸塩
(E2) :イオン液体
カチオン成分として
(E2K1)1-ブチル-3-メチルイミダゾリウム
(E2K2)1-ブチル-1-メチルピロリジニウム
(E2K3)ブチルトリメチルアンモニウム
(E2K4)トリオクチルメチルアンモニウム
(E2K5)1-エチル-3-メチルイミダゾリウム
アニオン成分として
(E2A1)ビス(トリフルオロメチルスルホニル)イミド
(E2A2)トリフルオロメチルスルホネート
(E2A3)テトラフルオロボレート
(E2A4)エチルスルファート
Claims (4)
- ポリウレタン樹脂と、第4級アンモニウム塩(E1)と、イオン液体(E2)とを含み、
前記第4級アンモニウム塩(E1)が、アニオン成分として、硫酸エステルアニオン及びスルホン酸アニオンからなる群から選ばれる1種以上を含むものであり、前記イオン液体(E2)が、カチオン成分として、炭素原子数3以上のアルキル基を有するイミダゾリウムカチオン、炭素原子数3以上のアルキル基を有するピリジニウムカチオン、炭素原子数3以上のアルキル基を有するピロリジニウムカチオン、炭素原子数3以上のアルキル基を有するピペリジニウムカチオン及び炭素原子数3以上のアルキル基を有する第4級アンモニウムカチオンからなる群より選ばれる1種以上を含むものであり、前記イオン液体が、アニオン成分として、ビス(トリフルオロメタンスルホニル)イミドアニオン、ビス(ペンタフルオロエタンスルホニル)アニオン、トリス(トリフルオロメタンスルホニル)メチドアニオン、トリフルオロメタンスルホネートアニオン及びテトラフルオロボレートアニオンからなる群より選ばれる1種以上を含むものであるポリウレタン樹脂成形体。 - 前記第4級アンモニウム塩(E1)と、イオン液体(E2)の含有量比((E1)/(E2))が、質量基準で、1/1以上20/1以下である請求項1記載のポリウレタン樹脂成形体。
- 前記第4級アンモニウム塩(E1)と、イオン液体(E2)との合計の含有量が、0.5質量%以上10質量%以下である請求項1記載のポリウレタン樹脂成形体。
- 靴底である請求項1記載のポリウレタン樹脂成形体。
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Citations (4)
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JP2012255120A (ja) | 2011-06-10 | 2012-12-27 | Fujimori Kogyo Co Ltd | 帯電防止剤を含有する粘着剤組成物、及び粘着フィルム |
JP2013216738A (ja) | 2012-04-05 | 2013-10-24 | Fujimori Kogyo Co Ltd | 粘着剤組成物及び表面保護フィルム |
JP2015157883A (ja) | 2014-02-21 | 2015-09-03 | 藤森工業株式会社 | 粘着剤組成物及び表面保護フィルム |
JP2015165027A (ja) | 2015-04-15 | 2015-09-17 | 藤森工業株式会社 | 帯電防止剤を含有する粘着剤組成物、及び粘着フィルム |
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JP2012255120A (ja) | 2011-06-10 | 2012-12-27 | Fujimori Kogyo Co Ltd | 帯電防止剤を含有する粘着剤組成物、及び粘着フィルム |
JP2013216738A (ja) | 2012-04-05 | 2013-10-24 | Fujimori Kogyo Co Ltd | 粘着剤組成物及び表面保護フィルム |
JP2015157883A (ja) | 2014-02-21 | 2015-09-03 | 藤森工業株式会社 | 粘着剤組成物及び表面保護フィルム |
JP2015165027A (ja) | 2015-04-15 | 2015-09-17 | 藤森工業株式会社 | 帯電防止剤を含有する粘着剤組成物、及び粘着フィルム |
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