JP5286807B2 - 反応性イソシアネート乳化剤 - Google Patents
反応性イソシアネート乳化剤 Download PDFInfo
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- JP5286807B2 JP5286807B2 JP2008023141A JP2008023141A JP5286807B2 JP 5286807 B2 JP5286807 B2 JP 5286807B2 JP 2008023141 A JP2008023141 A JP 2008023141A JP 2008023141 A JP2008023141 A JP 2008023141A JP 5286807 B2 JP5286807 B2 JP 5286807B2
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- 239000012948 isocyanate Substances 0.000 title claims description 26
- 150000002513 isocyanates Chemical class 0.000 title claims description 22
- 239000003995 emulsifying agent Substances 0.000 title claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 150000004693 imidazolium salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- -1 isocyanate compound Chemical class 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 43
- 239000005056 polyisocyanate Substances 0.000 description 34
- 229920001228 polyisocyanate Polymers 0.000 description 34
- 150000002430 hydrocarbons Chemical group 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229940100198 alkylating agent Drugs 0.000 description 13
- 239000002168 alkylating agent Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000009257 reactivity Effects 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000004945 emulsification Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 5
- AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical compound OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 4
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 3
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 3
- SVNWKKJQEFIURY-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazole Chemical compound CC(C)CN1C=CN=C1C SVNWKKJQEFIURY-UHFFFAOYSA-N 0.000 description 3
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 description 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 3
- 125000005917 3-methylpentyl group Chemical group 0.000 description 3
- 125000006043 5-hexenyl group Chemical group 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000001804 emulsifying effect Effects 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- SGIKRGDBBXWNRI-UHFFFAOYSA-N (1-benzylimidazol-2-yl)methanol Chemical compound OCC1=NC=CN1CC1=CC=CC=C1 SGIKRGDBBXWNRI-UHFFFAOYSA-N 0.000 description 2
- 0 *C1*(*)C(*)N(*)C1* Chemical compound *C1*(*)C(*)N(*)C1* 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 2
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 2
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 2
- DZMDPHNGKBEVRE-UHFFFAOYSA-N 1-chloroheptane Chemical compound CCCCCCCCl DZMDPHNGKBEVRE-UHFFFAOYSA-N 0.000 description 2
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 2
- RKAMCQVGHFRILV-UHFFFAOYSA-N 1-chlorononane Chemical compound CCCCCCCCCCl RKAMCQVGHFRILV-UHFFFAOYSA-N 0.000 description 2
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 2
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 2
- LGAJYTCRJPCZRJ-UHFFFAOYSA-N 2-bromopentane Chemical compound CCCC(C)Br LGAJYTCRJPCZRJ-UHFFFAOYSA-N 0.000 description 2
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 2
- NFRKUDYZEVQXTE-UHFFFAOYSA-N 2-chloropentane Chemical compound CCCC(C)Cl NFRKUDYZEVQXTE-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- AOPMHPFNYCNHJU-UHFFFAOYSA-N (1-butylimidazol-2-yl)methanol Chemical compound CCCCN1C=CN=C1CO AOPMHPFNYCNHJU-UHFFFAOYSA-N 0.000 description 1
- QYEQHVNOKQUFFM-UHFFFAOYSA-N (1-ethylimidazol-2-yl)methanol Chemical compound CCN1C=CN=C1CO QYEQHVNOKQUFFM-UHFFFAOYSA-N 0.000 description 1
- ZOIUWQHEYBRVMG-UHFFFAOYSA-N (1-hexylimidazol-2-yl)methanol Chemical compound CCCCCCN1C=CN=C1CO ZOIUWQHEYBRVMG-UHFFFAOYSA-N 0.000 description 1
- CDQDMLWGTVLQEE-UHFFFAOYSA-N (1-methylimidazol-2-yl)methanol Chemical compound CN1C=CN=C1CO CDQDMLWGTVLQEE-UHFFFAOYSA-N 0.000 description 1
- GMYMEKBDZLQAAN-UHFFFAOYSA-N (1-propylimidazol-2-yl)methanol Chemical compound CCCN1C=CN=C1CO GMYMEKBDZLQAAN-UHFFFAOYSA-N 0.000 description 1
- JUGRTVJQTFZHOM-UHFFFAOYSA-N 1,1,1-tribromo-2-methylpropan-2-ol Chemical compound CC(C)(O)C(Br)(Br)Br JUGRTVJQTFZHOM-UHFFFAOYSA-N 0.000 description 1
- NPOZBHCPELPGKW-UHFFFAOYSA-N 1-(2-methylpropyl)imidazole Chemical compound CC(C)CN1C=CN=C1 NPOZBHCPELPGKW-UHFFFAOYSA-N 0.000 description 1
- PEPIOVUNFZBCIB-UHFFFAOYSA-N 1-Decylimidazole Chemical compound CCCCCCCCCCN1C=CN=C1 PEPIOVUNFZBCIB-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
- RVAKKBXFXGFILL-UHFFFAOYSA-N 1-bromodecan-1-ol Chemical compound CCCCCCCCCC(O)Br RVAKKBXFXGFILL-UHFFFAOYSA-N 0.000 description 1
- MKESNCMVMCTBAC-UHFFFAOYSA-N 1-bromooctan-1-ol Chemical compound CCCCCCCC(O)Br MKESNCMVMCTBAC-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- WHLZPGRDRYCVRQ-UHFFFAOYSA-N 1-butyl-2-methylimidazole Chemical compound CCCCN1C=CN=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- LORZEOQACCXJLI-UHFFFAOYSA-N 1-chlorodecan-1-ol Chemical compound CCCCCCCCCC(O)Cl LORZEOQACCXJLI-UHFFFAOYSA-N 0.000 description 1
- HUBPTZAIVRQPLP-UHFFFAOYSA-N 1-chlorooctan-1-ol Chemical compound CCCCCCCC(O)Cl HUBPTZAIVRQPLP-UHFFFAOYSA-N 0.000 description 1
- BKFRZOZNMWIFLH-UHFFFAOYSA-N 1-decyl-2-methylimidazole Chemical compound CCCCCCCCCCN1C=CN=C1C BKFRZOZNMWIFLH-UHFFFAOYSA-N 0.000 description 1
- GMOKBQLJIIVDQQ-UHFFFAOYSA-N 1-dodecyl-2-methylimidazole Chemical compound CCCCCCCCCCCCN1C=CN=C1C GMOKBQLJIIVDQQ-UHFFFAOYSA-N 0.000 description 1
- JMTFLSQHQSFNTE-UHFFFAOYSA-N 1-dodecylimidazole Chemical compound CCCCCCCCCCCCN1C=CN=C1 JMTFLSQHQSFNTE-UHFFFAOYSA-N 0.000 description 1
- YFSQYUBYYKHCQV-UHFFFAOYSA-N 1-hexyl-2-methylimidazole Chemical compound CCCCCCN1C=CN=C1C YFSQYUBYYKHCQV-UHFFFAOYSA-N 0.000 description 1
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical compound CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 description 1
- KLMZKZJCMDOKFE-UHFFFAOYSA-N 1-octylimidazole Chemical compound CCCCCCCCN1C=CN=C1 KLMZKZJCMDOKFE-UHFFFAOYSA-N 0.000 description 1
- UPYVYJSWGZMBOU-UHFFFAOYSA-N 1-pentylimidazole Chemical compound CCCCCN1C=CN=C1 UPYVYJSWGZMBOU-UHFFFAOYSA-N 0.000 description 1
- HFMGGRZXHPSOJX-UHFFFAOYSA-N 2-(2-ethylimidazol-1-yl)ethanol Chemical compound CCC1=NC=CN1CCO HFMGGRZXHPSOJX-UHFFFAOYSA-N 0.000 description 1
- KDUUAAQFXVENJT-UHFFFAOYSA-N 2-(2-methyl-1h-imidazol-3-ium-5-yl)acetate Chemical compound CC1=NC=C(CC(O)=O)N1 KDUUAAQFXVENJT-UHFFFAOYSA-N 0.000 description 1
- JJWKKSUCSNDHNJ-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethanol Chemical compound CC1=NC=CN1CCO JJWKKSUCSNDHNJ-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- OWOSSTCHCATHMM-UHFFFAOYSA-N 2-methyl-1-octylimidazole Chemical compound CCCCCCCCN1C=CN=C1C OWOSSTCHCATHMM-UHFFFAOYSA-N 0.000 description 1
- WYGYPEMNIUDFBC-UHFFFAOYSA-N 2-methyl-1-pentylimidazole Chemical compound CCCCCN1C=CN=C1C WYGYPEMNIUDFBC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NGZFCGYJVRAKQY-UHFFFAOYSA-N OCCN1C(=NC=C1)CCCC Chemical compound OCCN1C(=NC=C1)CCCC NGZFCGYJVRAKQY-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical class CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical class COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000012978 lignocellulosic material Substances 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
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical class COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3848—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the ring
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
- C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
[式中、R1は炭素数4〜12の炭化水素基、R2は水酸基で置換されていてもよい炭素数1〜12の炭化水素基又は水素原子、R3は水酸基で置換されていてもよい炭素数1〜18の炭化水素基、をそれぞれ示し、R4及びR5は、それぞれ独立に、水素原子、炭素数1〜18の炭化水素基、水酸基、アミノ基、ニトロ基、シアノ基又はカルボキシル基を示し、X−は、Cl−、Br−、I−、BF4 −、NO3 −、CH3SO4 −、C2H5SO4 −、C3H7SO4 −、C4H9SO4 −、CH3C6H4SO3 −、又はCH3SO3を示す。但し、R2及びR3の少なくとも一方は水酸基を有していなければならない。]
[式中、R1は炭素数4〜12の炭化水素基、R2は水酸基で置換されていてもよい炭素数1〜12の炭化水素基又は水素原子、nは1〜18の数、X−は、Cl−又はBr−を示す。]
[式中、R1は炭素数4〜12の炭化水素基、R2は水酸基で置換されていてもよい炭素数1〜12の炭化水素基又は水素原子、R3は水酸基で置換されていてもよい炭素数1〜18の炭化水素基、をそれぞれ示し、R4及びR5は、それぞれ独立に、水素原子、炭素数1〜18の炭化水素基、水酸基、アミノ基、ニトロ基、シアノ基又はカルボキシル基を示し、X−は、Cl−、Br−、I−、BF4 −、NO3 −、CH3SO4 −、C2H5SO4 −、C3H7SO4 −、C4H9SO4 −、CH3C6H4SO3 −、又はCH3SO3 −を示す。但し、R2及びR3の少なくとも一方は水酸基を有していなければならない。]
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器に1−(2−ヒドロキシエチル)−イミダゾール100.0gと、1−クロロオクタン198.9gを仕込み、100℃にて攪拌しながら、46時間反応させた。その後1H―NMRで未反応の1−(2−ヒドロキシエチル)−イミダゾールが無いことを確認した。この反応混合物から未反応の1−クロロオクタンを140℃・1.3kPaにて留去することによりオニウム塩(イミダゾリム塩)「A1」を得た。
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器に1−イソブチル−2−メチルイミダゾール100.0gと、2−ブロモエタノール119.0gを仕込み、100℃にて攪拌しながら、20時間反応させた。その後1H―NMRで未反応の1−イソブチル−2−メチルイミダゾールが無いことを確認した。この反応混合物から未反応の2−ブロモエタノールを140℃・1.3kPaにて留去することによりオニウム塩(イミダゾリム塩)「A2」を得た。
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器に1−(2−ヒドロキシエチル)−イミダゾール100.0gと、1−クロロドデカン237.4gを仕込み、100℃にて攪拌しながら、40時間反応させた。その後1H―NMRで未反応の1−(2−ヒドロキシエチル)−イミダゾールが無いことを確認した。この反応混合物から未反応の1−クロロドデカンを140℃・1.3kPaにて留去することによりオニウム塩(イミダゾリム塩)「A3」を得た。
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器にN,N−ジメチルアミノエタノール100.0gと、1−ブロモドデカン307.5gとエタノール300gを仕込み、70℃にて攪拌しながら、24時間反応させた。その後1H―NMRで未反応のN,N−ジメチルアミノエタノールが無いことを確認した。この反応混合物を再結晶することによりオニウム塩「B1」を得た。
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器に1−メチルイミダゾール100.0gと、2−クロロエタノール117.7gを仕込み、100℃にて攪拌しながら、42時間反応させた。その後1H―NMRで未反応の1−メチルイミダゾールが無いことを確認した。この反応混合物から未反応の2−クロロエタノールを140℃・1.3kPaにて留去することによりオニウム塩「B2」を得た。
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器に1−メチルイミダゾール100.0gと、2−ブロモエタノール183.6gを仕込み、100℃にて攪拌しながら、16時間反応させた。その後1H―NMRで未反応の1−メチルイミダゾールが無いことを確認した。この反応混合物から未反応の2−ブロモエタノールを140℃・1.3kPaにて留去することによりオニウム塩「B3」を得た。
(実施例4)
攪拌機、冷却管、窒素導入管、温度計を備えた反応器を窒素置換した後、この反応器にポリメリックMDI(日本ポリウレタン工業社製、商品名「MR−200」)を990g仕込んだ。次いでイミダゾリム塩組成物「A1」10gを室温で攪拌しながら仕込み、室温(25℃)にて攪拌しながら反応させ,ポリメリックMDIのイソシアネート含有量とA1の水酸基含有量から計算された目標のイソシアネート含量になるまでの時間を測定した。1時間後に目標のイソシアネート含有量となり,変性量1%、イソシアネート(NCO)含量30.4%、25℃での粘度300mPa・sの自己乳化型ポリイソシアネート化合物「P1」を得た。
実施例4と同様の方法で表2に記載の量のポリメリックMDIとオニウム塩を仕込み、ポリメリックMDIのイソシアネート含有量とA1の水酸基含有量から計算された目標のイソシアネート含量になるまでの時間を測定した。目標のイソシアネート含量にならなかったものを反応せずとした。目標のイソシアネート含量になるまでの時間が5時間未満のものを合格,目標のイソシアネート含量になるまでの時間が5時間以上のもの及び反応しなかったものを不合格とした。反応性の評価結果をまとめて以下の表2に示した。
Claims (5)
- 下記一般式(1)で表されるイミダゾリウム塩からなる反応性イソシアネート乳化剤。
[式中、R1は炭素数4〜12の炭化水素基、R2は水酸基で置換されていてもよい炭素数1〜12の炭化水素基又は水素原子、R3は水酸基で置換されていてもよい炭素数1〜18の炭化水素基、をそれぞれ示し、R4及びR5は、それぞれ独立に、水素原子、炭素数1〜18の炭化水素基、水酸基、アミノ基、ニトロ基、シアノ基又はカルボキシル基を示し、X−は、Cl−、Br−、I−、BF4 −、NO3 −、CH3SO4 −、C2H5SO4 −、C3H7SO4 −、C4H9SO4 −、CH3C6H4SO3 −、又はCH3SO3 −を示す。但し、R2及びR3の少なくとも一方は水酸基を有していなければならない。] - R4及びR5はいずれも水素原子であり、X−は、Cl−又はBr−である請求項1記載の反応性イソシアネート乳化剤。
- R1は炭素数4〜12のアルキル基、R2は水酸基で置換されていてもよい炭素数1〜12のアルキル基又は水素原子、R3は水酸基で置換されていてもよい炭素数1〜18のアルキル基である請求項1又は2記載の反応性イソシアネート乳化剤。
- R1は炭素数4〜12のアルキル基、R2は水酸基で置換されていてもよい炭素数1〜12のアルキル基又は水素原子である請求項4記載の反応性イソシアネート乳化剤。
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