JP3772897B2 - ポリウレタン樹脂成形体及びその製造方法 - Google Patents
ポリウレタン樹脂成形体及びその製造方法 Download PDFInfo
- Publication number
- JP3772897B2 JP3772897B2 JP2004220002A JP2004220002A JP3772897B2 JP 3772897 B2 JP3772897 B2 JP 3772897B2 JP 2004220002 A JP2004220002 A JP 2004220002A JP 2004220002 A JP2004220002 A JP 2004220002A JP 3772897 B2 JP3772897 B2 JP 3772897B2
- Authority
- JP
- Japan
- Prior art keywords
- antistatic
- agent
- polyurethane resin
- lactone monomer
- molded article
- 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.)
- Expired - Lifetime
Links
- 229920005749 polyurethane resin Polymers 0.000 title claims description 44
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 45
- 239000002216 antistatic agent Substances 0.000 claims description 42
- 150000002596 lactones Chemical class 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 32
- 150000001875 compounds Chemical group 0.000 claims description 31
- 239000006260 foam Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 20
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 18
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 238000000465 moulding Methods 0.000 claims description 12
- 239000012752 auxiliary agent Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000004088 foaming agent Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 238000010097 foam moulding Methods 0.000 claims description 8
- 229920000768 polyamine Polymers 0.000 claims description 8
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 52
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 16
- -1 alkali metal salt Chemical class 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 13
- 238000005187 foaming Methods 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
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- 239000004014 plasticizer Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
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- 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 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- 229920005906 polyester polyol Polymers 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 5
- 239000004970 Chain extender Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 238000005520 cutting process Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 230000002159 abnormal effect Effects 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MYIAPBDBTMDUDP-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 MYIAPBDBTMDUDP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 150000005676 cyclic carbonates Chemical class 0.000 description 3
- 150000003997 cyclic ketones Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920003225 polyurethane elastomer Polymers 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 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
- 239000005062 Polybutadiene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011231 conductive filler Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 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 2
- 239000000428 dust Substances 0.000 description 2
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- 239000003063 flame retardant Substances 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- IOEDDFFKYCBADJ-UHFFFAOYSA-M lithium;4-methylbenzenesulfonate Chemical compound [Li+].CC1=CC=C(S([O-])(=O)=O)C=C1 IOEDDFFKYCBADJ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
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- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002323 Silicone foam Polymers 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- FAHKLOAQKILNBR-UHFFFAOYSA-N [K].FC(S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(F)F Chemical compound [K].FC(S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(F)F FAHKLOAQKILNBR-UHFFFAOYSA-N 0.000 description 1
- CBYFDSYXYZYNTQ-UHFFFAOYSA-N [Na].FC(S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(F)F Chemical compound [Na].FC(S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)(F)F CBYFDSYXYZYNTQ-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- KQUVYHRORKUYQZ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane;lithium Chemical compound [Li].FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F KQUVYHRORKUYQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000001739 density measurement Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- ODGXMRVMAFAHQH-UHFFFAOYSA-M dodecyl(trimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCC[N+](C)(C)C ODGXMRVMAFAHQH-UHFFFAOYSA-M 0.000 description 1
- QIFDCNKZFVLJSC-UHFFFAOYSA-M dodecyl-ethyl-dimethylazanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCC[N+](C)(C)CC QIFDCNKZFVLJSC-UHFFFAOYSA-M 0.000 description 1
- AZRTWXAIYRCDFE-UHFFFAOYSA-M dodecyl-ethyl-dimethylazanium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCCCCCCCCCC[N+](C)(C)CC AZRTWXAIYRCDFE-UHFFFAOYSA-M 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BXZBTVQISKPBLE-UHFFFAOYSA-M ethyl-dimethyl-octadecylazanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCCCCCCC[N+](C)(C)CC BXZBTVQISKPBLE-UHFFFAOYSA-M 0.000 description 1
- ZLRFCDPQKAYWOF-UHFFFAOYSA-M ethyl-dimethyl-octadecylazanium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CC ZLRFCDPQKAYWOF-UHFFFAOYSA-M 0.000 description 1
- AQUIHEJDEHMKGF-UHFFFAOYSA-M ethyl-dimethyl-tetradecylazanium 4-methylbenzenesulfonate Chemical compound CCCCCCCCCCCCCC[N+](C)(C)CC.CC1=CC=C(C=C1)S(=O)(=O)[O-] AQUIHEJDEHMKGF-UHFFFAOYSA-M 0.000 description 1
- HCGFVYVDYBMCLG-UHFFFAOYSA-M ethyl-dimethyl-tetradecylazanium methanesulfonate Chemical compound CCCCCCCCCCCCCC[N+](C)(C)CC.CS(=O)(=O)[O-] HCGFVYVDYBMCLG-UHFFFAOYSA-M 0.000 description 1
- LKHWQEOUPGUICK-UHFFFAOYSA-M ethyl-dimethyl-tetradecylazanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCC[N+](C)(C)CC LKHWQEOUPGUICK-UHFFFAOYSA-M 0.000 description 1
- UQLYURZGMOQXCD-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCCCCC[N+](C)(C)CC UQLYURZGMOQXCD-UHFFFAOYSA-M 0.000 description 1
- UUHBNESUDPIHCI-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)CC UUHBNESUDPIHCI-UHFFFAOYSA-M 0.000 description 1
- SVKARTCOZWAWCP-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)CC SVKARTCOZWAWCP-UHFFFAOYSA-M 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- OSJQADLXTFUATC-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)C OSJQADLXTFUATC-UHFFFAOYSA-M 0.000 description 1
- OEWKLERKHURFTB-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)C OEWKLERKHURFTB-UHFFFAOYSA-M 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 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 1
- 239000004611 light stabiliser Substances 0.000 description 1
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NAIDMDJMSSDWOZ-UHFFFAOYSA-M methanesulfonate trimethyl(tetradecyl)azanium Chemical compound CS([O-])(=O)=O.CCCCCCCCCCCCCC[N+](C)(C)C NAIDMDJMSSDWOZ-UHFFFAOYSA-M 0.000 description 1
- GOGIIHZYZHEBEA-UHFFFAOYSA-M methanesulfonate;trimethyl(octadecyl)azanium Chemical compound CS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)C GOGIIHZYZHEBEA-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WYTNTFGZBBTWNR-UHFFFAOYSA-M methyl sulfate;trimethyl(octadecyl)azanium Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)C WYTNTFGZBBTWNR-UHFFFAOYSA-M 0.000 description 1
- VXBSKVAMQMBCCA-UHFFFAOYSA-M methyl sulfate;trimethyl(tetradecyl)azanium Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCC[N+](C)(C)C VXBSKVAMQMBCCA-UHFFFAOYSA-M 0.000 description 1
- KZSYVMUYJSAHLZ-UHFFFAOYSA-N n,n'-bis(2,3-dichlorophenyl)methanediamine Chemical compound ClC1=CC=CC(NCNC=2C(=C(Cl)C=CC=2)Cl)=C1Cl KZSYVMUYJSAHLZ-UHFFFAOYSA-N 0.000 description 1
- GMKSMTJXIGEYLX-UHFFFAOYSA-N n,n'-bis(2-ethyl-6-methylphenyl)methanediamine Chemical compound CCC1=CC=CC(C)=C1NCNC1=C(C)C=CC=C1CC GMKSMTJXIGEYLX-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000013514 silicone foam Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0075—Antistatics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/16—Making expandable particles
- C08J9/18—Making expandable particles by impregnating polymer particles with the blowing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/04—Antistatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
更に、本発明は、成形型内において、(1)有機ポリイソシアネートと(2)ポリオールとを反応させるポリウレタン樹脂発泡成形体の製造方法であって、
前記ポリオール(2)が、炭化水素基又はオキシ炭化水素基で置換されたスルホン酸第四級アンモニウム系のカチオン系制電性化合物及び金属塩系のアニオン系制電性化合物から選ばれる少なくとも1種の帯電防止剤と、γ−ブチロラクトン及びε−カプロラクトンから選ばれる少なくとも1種のラクトン系単量体からなる帯電防止助剤、発泡剤とを含有することを特徴とするポリウレタン樹脂発泡成形体の製造方法を提供する。
本発明のポリウレタン樹脂成形体としては、例えば、熱可塑性ポリウレタン樹脂、注型ポリウレタン樹脂、発泡ポリウレタン(ポリウレタンエラストマーフォーム、硬質・軟質ポリウレタンフォーム)等のポリウレタン樹脂成形体が挙げられ、特に好ましくは、ポリウレタン樹脂発泡成形体である。
これらポリオールの数平均分子量は、好ましくは500〜10000、より好ましくは1000〜5000である。
ポリウレタン樹脂成形体又は同発泡成形体を製造する際に前記末端イソシアネート基含有ウレタンプレポリマーを使用する場合は、帯電防止剤、ラクトン系単量体、必要により発泡剤及びウレタン化触媒を含有する末端イソシアネート基含有ウレタンプレポリマーとポリアミン系硬化剤とを反応させることが好ましい。
(ポリオール)
・ポリオールA:エチレングリコール/1,4−ブチレングリコールとアジピン酸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。エチレングリコール/1,4−ブチレングリコールのモル比 5/5。
・ポリオールB:ジエチレングリコール/トリメチロールプロパンとアジピン酸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。ジエチレングリコール/トリメチロールプロパンのモル比 15/1。
NCO基末端プレポリマー<1>:NCO%=16.8重量%含有のアジピン酸、エチレングリコール、1,4−ブチレングリコールから得られるポリエステルポリオールと4,4’−ジフェニルメタンジイソシアネートとを反応して得られるウレタンプレポリマー。
NCO基末端プレポリマー<2>:NCO%=3.1重量%含有、ポリプロピレングリコールとトリレンジイソシアネートとを反応して得られるウレタンプレポリマー。
NCO基末端プレポリマー<3>:NCO%=4.4重量%含有、ポリテトラメチレングリコールとトリレンジイソシアネートとを反応して得られるウレタンプレポリマー。
・制電性化合物A90重量%含有エチレングリコール:エチル硫酸−N−エチル−N,N−ジメチル−N−ドデシルアンモニウムを90重量%含有するエチレングリコール溶液。
・制電性化合物B50重量%含有エチレングリコール:ビス(トリフルオロメチルスルホニル)イミドリチウムを50重量%含有するエチレングリコール溶液。
・制電性化合物C20重量%含有可塑剤溶液:ビス(トリフルオロメチルスルホニル)イミドリチウムを20重量%含有するアジペート系可塑剤溶液。
シリコーン整泡剤:SH−193、東レ・ダウ・コーニングシリコーン(株)製品
発泡剤:水
ウレタン化触媒:トリエチレンジアミン(以後TEDAという)
表1、2に示す配合表に従って、前記ポリオール、発泡剤、触媒、整泡剤、鎖伸長剤、制電性組成物とからなるポリオール成分(以後A液という)と前記有機ポリイソシアネートからなるイソシアネート成分(以後B液という)を調製した。
A液/B液を低圧発泡機にて所定の混合比率で混合攪拌し、混合発泡液150gを100×100×50Hmmの木製発泡箱に注入しフリー発泡させた。混合発泡液の吐出開始から2.5分後に発泡箱からフォームを取り出し、直ちに拳でフォームに強圧をかけた後、屈曲させ、フォームの潰れ度合いからフォームの強度出現を以下の判定基準で評価した。
×:フォームの強圧面が窪んだ状態
サンプルの重量(g)を測定し、体積150cm3で除して算出した。
サンプルの硬度をAsker C硬度計にて測定した。
電池式絶縁抵抗計(横河電機(株)製、2604 01型)を使用して、サンプルの下面に300×200×1tmmの鉄板、上面に75mm×75mm×3tmmの鉄板を接触させて、成形後、1日及び7日経過時点の電気抵抗値を測定した。なお、成形後のサンプルはデシケータ内で保存し、常温低湿度状態(25℃×15%RH)と低温低湿度状態(10℃×15%RH)の2条件で電気抵抗値を測定した。結果は表1及び表2のとおりである。
A液をブレンド直後より4日間、50℃乾燥機内に保存した。50℃での保存日数が4日経過したA液について、それぞれ上記方法にて発泡混合液を作製し、発泡成形し、サンプルを得た。このサンプルについて、2.5分後強圧テスト、モールド密度、アスカーC硬度、電気抵抗値、引張強度、引裂強度及び耐屈曲性を評価した。それぞれの項目の評価は上記方法と同様の方法で行った。2.5分後強圧テスト、モールド密度、アスカーC硬度及び電気抵抗値については、前記の方法と同様の方法で行い、引張強度、引裂強度及び耐屈曲性については、次ぎの方法で行った。結果は表1及び表2に示すとおりである。
JIS K 6252−93に準じて試験装置AUTOGRAPH AG−I(島津製作所製品)を用い、試験片をダンベル形状3号形の形状にサンプリングして、引張速度= 500 mm/minで試験片が切断に至るまでの最大引張力を引張強度とし、切断時の標線間距離を測定し破断伸びを求めた。引張強度試験では100%モジュラス、300%モジュラス、破断時の伸度も併せて測定した。
前記サンプルを用い、JIS K 6251−93に準じて試験装置AUTOGRAPH AG−I(島津製作所製品)を用い、試験片を切込無しアングル形の形状にサンプリングして、引裂速度= 500 mm/minで試験片が切断に至るまでの最大引裂力を引裂強度とした。
JIS K 6260−93準じて試験装置デマッテアフレックスクラッキングテスタ(DE MATTIA FLEX CRACKING TESTER、東洋精機製品)を用い、試験片を150×25×6 mmの短冊状にサンプリングし、屈曲部に2 mmのノッチを入れ、屈曲速度= 300 rpm、常温下で行った。屈曲回数2万回毎に、亀裂成長度合いをノギスで測定し成長巾を記録した。試験回数は、最大10万回まで行った。以下の判定基準に従って評価した。
○:亀裂の生長なし。
×:亀裂の生長あり。
−常温−
○: 25℃での1日目の電気抵抗値が30MΩ以下で、発現率が60%以上
×: 25℃での1日目の電気抵抗値が30MΩを越える値で、発現率が60%未満
−低温−
○: 10℃での1日目の電気抵抗値が90MΩ以下で、発現率が60%以上
×: 10℃での1日目の電気抵抗値が90MΩを越える値で、発現率が60%未満
25℃における[(7日目の電気抵抗値/1日目の電気抵抗値)×100]の値(%)
10℃における[(7日目の電気抵抗値/1日目の電気抵抗値)×100]の値(%)
表3、4に示す配合表に従って、末端イソシアネート基含有ウレタンプレポリマーは80℃に、MBOCA(ポリアミン硬化剤)は120℃に温調し、ウレタンプレポリマーに対して制電性化合物Cとγ−ブチロラクトンとを、プレポリマーと硬化剤とのR値(NH2/NCO比)=0.9で撹拌混合、充分脱泡した後に、型温110℃の金型に注型し、表3、表4に示すようなキュア条件で成形を行い、サンプルを得た。
硬さ試験方法(成形品硬度)
エラストマーの硬度は、デュロメーター(DUROMETER)硬さ試験のタイプAを用いて測定した。
試験装置AUTOGRAPH AG−I(島津製作所製品)を用い、試験片は厚み2mmのエラストマー成形品で、試験片の形状はダンベル状3号試験片を用いた。エラストマーの切断に至る最大応力(引張強度)および切断時の伸び、並びに特定の伸びに対する応力(100%モジュラス,300%モジュラス)を測定した。
試験装置AUTOGRAPH AG−I(島津製作所製品)を用い、試験片は厚み2 mmのエラストマー成形品で、形状は切込みなしアングル形で切断に至るまでの引裂強度を測定した。
試験片は厚さ(高さ)12.5mm、直径29mmの直円柱形のエラストマー成形品で、反発弾性試験機(上島製作所製品)を使用し、4本の釣り糸によって水平に懸垂された鉄棒(長さ356mm、直径12.5mm、質量0.35kgの丸棒)を上から懸垂高さ2000mmの位置でつり、鉄棒の水平位置から落下高さ垂直方向に100mmとして、自由落下させ該成形品に当てて反発弾性率を求めた。
試験片は厚さ12.5mm、直径29mmの直円柱形のエラストマー成形品で、70℃で22時間、厚み方向に対して25%圧縮を行い、圧縮永久歪みを計算により求めた。
Claims (5)
- 帯電防止剤及び帯電防止助剤を含有するポリウレタン樹脂発泡成形体であって、
前記帯電防止剤が、炭化水素基又はオキシ炭化水素基で置換されたスルホン酸第四級アンモニウム系のカチオン系制電性化合物及び金属塩系のアニオン系制電性化合物から選ばれる少なくとも1種であり、
帯電防止助剤が、γ−ブチロラクトン及びε−カプロラクトンから選ばれる少なくとも1種のラクトン系単量体であり、かつ、
前記帯電防止剤に対する前記ラクトン系単量体の成形体中の含有割合が、重量比で前記帯電防止剤/前記ラクトン系単量体=1/2〜20/1であることを
特徴とするポリウレタン樹脂発泡成形体。 - 成形型内において、(1)有機ポリイソシアネートと(2)ポリオールとを反応させるポリウレタン樹脂発泡成形体の製造方法であって、
前記ポリオール(2)が、炭化水素基又はオキシ炭化水素基で置換されたスルホン酸第四級アンモニウム系のカチオン系制電性化合物及び金属塩系のアニオン系制電性化合物から選ばれる少なくとも1種の帯電防止剤と、γ−ブチロラクトン及びε−カプロラクトンから選ばれる少なくとも1種のラクトン系単量体からなる帯電防止助剤、発泡剤とを含有することを特徴とするポリウレタン樹脂発泡成形体の製造方法。 - 成形型内において、(1)末端イソシアネート基含有ウレタンプレポリマーと(2)ポリアミン系硬化剤とを反応させる注型ポリウレタン樹脂成形体の製造方法であって、前記末端イソシアネート基含有ウレタンプレポリマー(1)が、炭化水素基又はオキシ炭化水素基で置換されたスルホン酸第四級アンモニウム系のカチオン系制電性化合物及び金属塩系のアニオン系制電性化合物から選ばれる少なくとも1種の帯電防止剤と、γ−ブチロラクトン及びε−カプロラクトンから選ばれる少なくとも1種のラクトン系単量体からなる帯電防止助剤とを含有することを特徴とする注型ポリウレタン樹脂成形体の製造方法。
- 末端イソシアネート基含有ウレタンプレポリマーとポリアミン類とから得られる、帯電防止剤及び帯電防止助剤を含有する注型ポリウレタン樹脂成形体であって、
前記帯電防止剤が、炭化水素基又はオキシ炭化水素基で置換されたスルホン酸第四級アンモニウム系のカチオン系制電性化合物及び金属塩系のアニオン系制電性化合物から選ばれる少なくとも1種であり、
前記帯電防止助剤が、γ−ブチロラクトン及びε−カプロラクトンから選ばれる少なくとも1種であるラクトン系単量体であり、
前記帯電防止剤および前記帯電防止助剤がいずれも、前記末端イソシアネート基含有ウレタンプレポリマーを含有し、かつ、
前記帯電防止剤に対する前記ラクトン系単量体の成形体中の含有割合が、重量比で前記帯電防止剤/前記ラクトン系単量体=1/2〜20/1である
ことを特徴とする注型ポリウレタン樹脂成形体。 - 前記帯電防止剤のポリウレタン樹脂成形体中の含有量が、1〜7重量%である請求項1記載のポリウレタン樹脂発泡成形体。
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JP4487930B2 (ja) * | 2003-12-24 | 2010-06-23 | 日本ポリウレタン工業株式会社 | 軟質ポリウレタンフォームの製造方法、導電性軟質ポリウレタンフォームの製造方法、導電性ロールおよびその製造方法 |
DE102004042033A1 (de) * | 2004-08-31 | 2006-03-02 | Bayer Materialscience Ag | Polyurethanelastomere mit verbessertem antistatischen Verhalten |
CN101486890B (zh) * | 2008-04-30 | 2012-11-14 | 上海工程技术大学 | 一种抗静电剂及其抗静电聚氨酯弹性体材料 |
KR101105874B1 (ko) * | 2009-07-28 | 2012-01-16 | 최진국 | 롤러 제작용 폴리우레탄 코팅 장치 |
US9012590B2 (en) * | 2009-10-15 | 2015-04-21 | Lubrizol Advanced Materials, Inc. | Electrostatic dissipative TPU and compositions thereof |
KR100986969B1 (ko) | 2010-01-29 | 2010-10-11 | 차윤종 | 연마 패드용 대전방지성 폴리우레탄 다공질체 및 그 제조 방법 및 이를 이용한 연마패드 |
CN102161742A (zh) * | 2011-03-24 | 2011-08-24 | 上海科华聚氨酯制品有限公司 | 一种有机高分子聚氨酯弹性体及其制备方法 |
CN102337020B (zh) * | 2011-06-24 | 2013-03-20 | 苏州新纶超净技术有限公司 | 较低湿度条件下使用的防静电聚氨酯弹性体材料及其制备方法 |
JP5810767B2 (ja) * | 2011-09-06 | 2015-11-11 | Dic株式会社 | 2液硬化型発泡ポリウレタン樹脂組成物、ウレタン成形体、靴底、及び工業部材 |
WO2013062990A2 (en) * | 2011-10-28 | 2013-05-02 | Lubrizol Advanced Materials, Inc. | Polyurethane based membranes and/or separators for electrochemical cells |
WO2013161854A1 (ja) * | 2012-04-26 | 2013-10-31 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | ポリウレタン発泡組成物および軟質ポリウレタンフォームの製造方法 |
CN102717660B (zh) * | 2012-06-14 | 2015-04-01 | 青岛富盛德塑胶有限公司 | 防静电脚轮结构、生产脚轮的防静电聚氨酯材料及方法 |
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