JPS6141910B2 - - Google Patents
Info
- Publication number
- JPS6141910B2 JPS6141910B2 JP58066584A JP6658483A JPS6141910B2 JP S6141910 B2 JPS6141910 B2 JP S6141910B2 JP 58066584 A JP58066584 A JP 58066584A JP 6658483 A JP6658483 A JP 6658483A JP S6141910 B2 JPS6141910 B2 JP S6141910B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- methylimidazole
- curing
- 2e4mz
- molar ratio
- 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
Links
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 37
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- QFZKVFCEJRXRBD-UHFFFAOYSA-N 2-ethyl-4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]-5-methyl-1h-imidazole Chemical compound N1C(CC)=NC(CC2=C(NC(CC)=N2)C)=C1C QFZKVFCEJRXRBD-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- -1 imidazole compound Chemical class 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- LHFIAMMRYGQCJH-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OC1CC2OC2CC1 LHFIAMMRYGQCJH-UHFFFAOYSA-N 0.000 description 1
- 229910018173 AlâAl Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009820 dry lamination Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- 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
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
æ¬çºæã¯æ°èŠã€ãããŸãŒã«ååç©ã該ååç©ã®
補é æ¹æ³åã³è©²ååç©ãçšããŠããªãšããã·æš¹è
ã硬åãªãã硬åä¿é²ãããæ¹æ³ã«é¢ãããã®ã§
ãããæ¬çºæè çã¯ããªãšããã·æš¹èã«å¯ŸããŠåª
ãã硬åæ§ãªãã硬åä¿é²æ§ã瀺ãååç©ãæ±ã
éæç 究ã®çµæã次åŒã§ç€ºãããïŒïŒ4â²âã¡ãã¬
ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒ
ã«ïŒãããã«çžåœããããšãèŠåºããã æ¬çºæè çã¯ïŒâãšãã«âïŒâã¡ãã«ã€ãããŸ
ãŒã«ïŒä»¥äž2E4MZãšç¥èšããïŒãšããªã«ã ã¢ã«
ãããåã¯ã¡ãã¬ã³åå€ã溶å€ãçšããããã¯çš
ããã«è§Šåªãšå ±ã«å ç±ããããšã«ãã次瀺ã®åå¿
ãèµ·ããããšãèŠåºãããå³ã¡ å㯠次ã«æ¬çºæã®åå¿ã®å®æœã®æ æ§ã«ã€ããŠè¿°ã¹
ãããœãŒãã©ã€ã å 填管ã§å€æ°äžã®çé žã¬ã¹ãé®
æïŒäœã觊åªãçé žã¢ã«ã«ãªã®å Žåã¯é®æäžèŠïŒ
ãã容åšäžã§é©åœã¢ã«æ¯ã®2E4MZãããªã«ã ã¢
ã«ãããïŒåã¯ã¡ãã¬ã³åå€ïŒåã³è§Šåªãé©åœé
ã®æº¶å€ãçšããããã¯çšããã«åžžå§ã§é©åœæéå
ç±æ¹æãè¡ãªããšããããŠåäžæº¶æ¶²ããçµæ¶ãæ
åºããŠæ¥ããæŽã«é©åœæéãã®å ç±æ¹æãè¡ãªã
åå¿ãå®äºãããã®ã¡ç³»ãå·åŽããçµæ¶ãåã
åçµæ¶ïŒç¬¬ïŒçµæ¶ãšåŒã¶ïŒãäžæŠé žæ§æ°Žæº¶æ¶²ãš
ãªããã€ãã§è©²æ°Žæº¶æ¶²ãã¢ã«ã«ãªæ§ãšããéã«æ
åºããçµæ¶ãåãæ°ŽæŽã也ç¥ããã°ç²Ÿè£œç©ãã
ããããä»æ¹ã第ïŒçµæ¶ãåããéã®æ¶²ãæž
å§èžçããæªåå¿2E4MZãååãããèžçæ®æž£
äžã®æ°Žäžæº¶æ§çµæ¶ãåããïŒç¬¬ïŒçµæ¶ãšåŒ
ã¶ïŒã第ïŒçµæ¶ã第ïŒçµæ¶ãšåæ§ã«åŠçãããšå
ãã粟補ç©ããããããå¿è«ã第ïŒçµæ¶åã³ç¬¬ïŒ
çµæ¶ãåžžæ³ïŒäŸãã°åçµåã¯æžå§æè¯ãªã©ïŒã«åŸ
ã€ãŠç²Ÿè£œããããšãåºæ¥ãã æ¬çºæã«ãããŠäœ¿çšãããåºçºç©è³ª2E4MZã¯
ãããã¬ã³ãžã¢ãã³ãšããããªãããªã«ããç¹å ¬
æ39â24965å·å ¬å ±ãç¹å ¬æ42â1548å·å ¬å ±åã³
ç¹å ¬æ41â151711å·å ¬å ±ã«åŸã€ãŠåæãããç©è³ª
ã§ããã æ¬çºæååç©ã®åæã«ãããŠäœ¿çšãããããªã«
ã ã¢ã«ãããã¯åžè²©ã®ããªã«ããªã³æ°Žæº¶æ¶²ã§å å
ã§ããããŸãã¡ãã¬ã³åå€ã¯ãã©ããªã«ã åã¯
ïŒïŒïŒâãžãªããœã©ã³âïŒããããµã¡ãã¬ã³ãã
ã©ãã³ããã³ã¬ãªããåã³ã¢ã«ã³ãŒã«ã®ããªã«
ããŒã«çã§ãããããããããµã¡ãã¬ã³ããã©ã
ã³åã³ãã³ã¬ãªããã®äœ¿çšã¯ããªã«ããªã³ã«æ¯
ãåçäžäœãã®å©ç¹ãã瀺ããªãã æ¬çºæååç©ã®è£œé å·¥çšã«ãããŠäœ¿çšããã溶
å€ã¯ãæ°Žåã³ã¡ã¿ããŒã«ããšã¿ããŒã«ãïœâãã¿
ããŒã«ããšãã¬ã³ã°ãªã³ãŒã«çã®ã¢ã«ã³ãŒã«é¡ã
奜ãŸããã觊åªã¯æ°Žé žåãªããŠã ãæ°Žé žåãããª
ãŠã ãæ°Žé žåã«ãªãŠã ãçé žãªããŠã ããããªãŠ
ã ã¢ãããçé žãããªãŠã ãçé žã«ãªãŠã ã
Triton çã§ãããäœããçé žãããªãŠã ã
çé žã«ãªãŠã åã³Triton ã®èœåã¯äžèšã®ä»
ã®è§Šåªã«æ¯ãå£ãã觊åªã®äœ¿çšéã¯ãã®çš®é¡ã«ã
ã€ãŠå€å°å€åããããäžæŠã«äºã€ãŠ2E4MZã«å¯Ÿ
ãã¢ã«æ¯0.2以äžã§å åã§ããããã以äžã®éã¯
äžå¿ èŠã§ãããåå¿æž©åºŠã¯æº¶å€ã®çš®é¡ã®åŠäœã«ã
ã€ãŠç°ãã70ä¹è³130âãé©åœã§ãããæ¬çºæã®
åå¿ã¯åžžå§ã§å åé²è¡ããã å¿è«ãå å§äžã®åå¿ãè¡ãããšãåºæ¥ãã ç²ç®çç©ïŒç¬¬ïŒçµæ¶åã³ç¬¬ïŒçµæ¶ïŒã®é žæ§æ°Žæº¶
液調補ã«äœ¿çšãããé žã¯ç¡æ©é žãããã¯ææ©é žã§
ãããäŸãã°å¡©é žãç¡é žãç¡«é žãçé žãé ¢é žã矩
é žçã§ãããç²ç®çç©ã溶解ãããé žæ§æ°Žæº¶æ¶²ã
ã¢ã«ã«ãªæ§ãšããããã«äœ¿çšãããå¡©åºã¯æ°Žé žå
ãããªãŠã ãæ°Žé žåã«ãªãŠã ãçé žãããªãŠã ã
çé žã«ãªãŠã ãæ°Žé žåã«ã«ã·ãŠã ãçé žã«ã«ã·ãŠ
ã ãã¢ã³ã¢ãã¢çã§ããã æ¬çºæååç©ã§ããïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒã®æ§è³ª
ã¯æ¬¡ã®éãã§ããã èç¹ïŒ260.5âïŒæè¯ã䌎ãªãïŒ ç¡è²çµæ¶ãå¡©åºæ§ã ã¢ã«ã³ãŒã«ã«å¯æº¶ãæ°Žã«äžæº¶ãã¢ã»ãã³åã³ãã«
ãšã³ã«é£å®¹ã TLCïŒã·ãªã«ãEtOHïŒïŒïŒ²f0.05ã0.35ïŒB.T.B
çºè²ïŒã ÎœcmâïŒ ïŒ«ïŒ¢ïœïŒ2980ïŒ1618ïŒç¬¬ïŒåžåïŒ1533ïŒ1455ïŒ
第
ïŒåžåïŒïŒ1435ïŒç¬¬ïŒåžåïŒïŒ1372ïŒ1330ïŒ
1280ïŒ1242ïŒ1205ïŒ1145ïŒ1110ïŒ1072ïŒç¬¬ïŒ
åžåïŒïŒ1049ïŒç¬¬ïŒåžåïŒïŒ985ïŒ967ïŒ920ïŒ
880ïŒ822ïŒ788ïŒ697 NMRïŒCD3ODïŒïŒÎŽ3.68ïŒïœïŒ2HïŒïŒã¡ãã¬
ã³ïŒïŒ2.61ïŒïœïŒ4HïŒãšãã«åºã®ã¡ãã¬
ã³ïŒïŒ2.00ïŒïœïŒ6HïŒïŒã¡ãã«ïŒïŒ1.21ïŒ
ïœïŒ6HïŒãšãã«åºã®ã¡ãã«ïŒ MassïŒïœïŒïœ ïŒïŒ232ïŒM+ïŒã217ïŒM+âã¡ã
ã«ïŒïŒ203ïŒ217âã¡ãã¬ã³ïŒïŒ123ïŒ2E4MZâ
ïŒã¡ãã¬ã³ïŒïŒ110ïŒ2E4MZïŒ æ¬çºæååç©ã¯ååäžã«å¹³åïŒã±ããå€ãã®ãš
ããã·åºãæããããªãšããã·ååç©ãææã®é«
ãããã枩床ã§è¿ éäžã€å¹ççã«ç¡¬åãããããš
ãã§ããäžæåç³»ãšããã·æš¹èãå³ã¡ããªãšãã
ã·ååç©ã硬åå€ãšäºåæ··åãããç³»ã®ä¿å寿åœ
ãããã¯ä¿åå®å®æ§ã«å®è³ªçãªåœ±é¿ãåãŒããªã
æœåšæ§ç¡¬åå€ãªããæœåšæ§ç¡¬åä¿é²å€ãšããŠæ¥µã
ãŠæçšã§ããã æ¬çºæã®å®æœã«ããåŸãããäžæåç³»ãšããã·
æš¹èã¯ã宀枩ã«ãããŠã¯é·æéã«äºã€ãŠç²åºŠäžæ
ãªã©äœæ¥æ§èœã®äœäžãããããå€åãå°ãªãå®å®
ãªç¶æ ã§ä¿åãããé«æž©ã«ãããŠã¯è¿ éäžã€å¹ç
çã«ç¡¬åããé»æ°çµ¶çžæ§èœãæ©æ¢°ç匷床ç¹æ§ãè
ååŠè¬åæ§ãªã©ã®è«žç¹æ§ã«ãã©ã³ã¹ã®æ¡ããåªã
ã硬åç©ãåŸãããã æ¬çºæã¯ïŒïŒ4â²âã¡ãã¬ã³âãã¹âïŒïŒâãšã
ã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒãåç¬ã§ç¡¬åå€ãš
ããŠçšããå€ã«ãä»ã®ç¡¬åå€æåãäŸãã°ãèèª
æããªã¢ãã³ãè³éŠæããªã¢ãã³ãã¢ãã³å¡©ã第
åçŽã¢ã³ã¢ããŠã å¡©ããžã·ã¢ã³ãžã¢ãããå°¿çŽ ã
ã¡ã©ãã³ãããªã«ã«ãã³é žãããªã«ã«ãã³é žç¡æ°Ž
ç©ãããšããŒã«é¡ãšã¢ã«ãããé¡ã®ä»å çž®åäœã
å«ãå€äŸ¡ããšããŒã«ãããªã«ã«ãã³é žããã©ãž
ããã€ãããŸãŒã«ååç©ãªã©ã®ç¡¬åä¿é²å€ä¹è³ã¯
å ±ç¡¬åå€ãšããŠçšããããšãå å«ããã æ¬çºæã«ãããŠãïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒã硬å
å€ãšããŠäœ¿çšããå Žåãã®é©æ£é åå²åã¯ã0.5
ä¹è³30phrïŒããªãšããã·ååç©100éééšåœã
ãã®éééšïŒã§ãããä»ã®ç¡¬åå€ã®ä¿é²å€ä¹è³ã¯
å ±éåå€ãšããŠäœ¿çšããå Žåã®é©æ£é åå²åã¯
0.01ä¹è³30phrã§ããã奜ãŸããã¯0.05ä¹è³10phr
ã§ããã æ¬çºæã«ãããããªãšããã·ååç©ã¯ïŒåååœ
ããå¹³åïŒåããå€ãã®ãšããã·åºãå«æããã
ã®ã§ãã€ãŠããã®åºã¯ååæ«ç«¯äœçœ®ã«ãã ã§ããããæãã¯äžè¬ã«å éšãšããã·ããšåŒã°ã
ããåååŒã®éäžã«ä»åšã㊠ã®åœ¢ã®åºã圢æããŠãããããã®ããªãšããã·å
åç©ã¯èèªæãç°ç¶èèªæãè³éŠæããŸãã¯è€çŽ
ç°åŒã®ãã®ã§ãããããŸãæ°Žé žåºãã¢ã«ãã«åºã
ã¢ã«ã³ãã·åºããšã¹ãã«åºãã¢ã»ã¿ãŒã«åºããšãŒ
ãã«åºã®ãããªé劚害æ§ã®çœ®æåºã§çœ®æãããŠã
ãŠãè¯ãã æãæãŸããããªãšããã·ååç©ã¯ãã¹ããšã
ãŒã«ïŒ¡ããã¹ããšããŒã«ïŒŠãã¬ãŸã«ã·ã³ããã€ã
ãããã³ããã¹ããšããŒã«ïŒ³ãããšããŒã«ã»ãã«
ã ã¢ã«ãããæš¹èãã¯ã¬ãŸãŒã«ã»ãã«ã ã¢ã«ãã
ãæš¹èã®ãããªå€äŸ¡ããšããŒã«ã®ããªã°ãªã·ãžã«
ãšãŒãã«ããã ãã®ä»é©åœãªããªãšããã·ååç©ãäŸç€ºãããš
ïŒããªïŒãšãã¬ã³ã°ãªã³ãŒã«ãïŒããªïŒãããã¬ã³
ã°ãªã³ãŒã«ãã°ãªã»ãªã³ãããªã¡ãããŒã«ããã
ã³ãïŒïŒïŒâãã¿ã³ãžãªãŒã«ã®ãããªå€äŸ¡ã¢ã«ã³
ãŒã«ã®ã°ãªã·ãžã«ãšãŒãã«ããã¿ã«é žãããã©ã
ãããã¿ã«é žããããµããããã¿ã«é žãã¡ãã«â
ãšã³ãã¡ãã¬ã³âããã©ããããã¿ã«é žãã¢ãžã
ã³é žããã€ããŒé žã®ãããªå€äŸ¡ã«ã«ãã³é žã®ããª
ã°ãªã·ãžã«ãšã¹ãã«ãã¢ããªã³ããã«ã€ãžã³ã
ïŒïŒ4â²âãžã¢ãããžããšãã«ã¡ã¿ã³ã®ãããªããª
ã¢ãã³ããèªå°ãããã°ãªã·ãžã«ã¢ãã³é¡ããã
ã«ã·ã¯ãããã»ã³ãªããµã€ããïŒïŒïŒâãšããã·
ã·ã¯ãããã·ã«âïŒïŒïŒâãšããã·ã·ã¯ããããµ
ã³ã«ã«ããã·ã¬ãŒãããã¹âïŒïŒïŒïŒâãšããã·
âïŒâã¡ãã«ã·ã¯ãããã·ã«ã¡ãã«ïŒâã¢ãžããŒ
ãã®ãããªãšããã·åããªãªã¬ãã€ã³ããããã¯
ãšããã·åæ€ç©æ²¹ãªã©ã§ãããæ¬çºææ¹æ³ã¯å¿ çš
ã«å¿ããŠçè²é¡æãäœè³ªé¡æãå¯å¡å€ãããã³ã
ãã«ã°ãªã·ãžã«ãšãŒãã«ãããšãã«ã°ãªã·ãžã«ãš
ãŒãã«ã®ãããªã¢ããšããã·ååç©ã®åå¿æ§çšé
å€ããããã¯ã±ãã³ç³»ãã°ãªã³ãŒã«ç³»ãè³éŠæç³
æ²¹ãããµã®ãããªæº¶å€ãªã©ãæ·»å ãåŸãã æ¬çºæã®å®æœã«ããã60ä¹è³240âã奜ãŸãã
ã¯100ä¹è³180âã«æŒããŠçæéã«ç¡¬ååŠçãåŸã
ãšããã·æš¹èç³»ã¯ãã¹ãå¡æãæ¥çå€ã泚åæ
æã也åŒç©å±€çšããªãã¬ãã°ãæ圢çšã³ã³ããŠã³
ããç²æ«å¡æçã圢æåºæ¥ãã 以äžå®æœã®æ æ§ãå®æœäŸã«ãã€ãŠèª¬æããã å®æœäŸ ïŒ é»ç£æ¹ææ©ãéæµå·åŽåšã枩床èšåã³å€æ°ã®ç
é žã¬ã¹é®æçšãœãŒãã©ã€ã 管ãåããåå¿å®¹åšã«
åžè²©37ïŒ ããªã«ããªã³4.5ïœïŒ2E4MZã«å¯Ÿããã¢
ã«æ¯0.75ïŒã2E4MZ9ïœãæ°Žé žåã«ãªãŠã
ïŒKOHïŒ0.25ïœïŒ2E4MZã«å¯Ÿããã¢ã«æ¯0.05ïŒå
ã³æ°Ž27mlãä»èŸŒã¿ãæ¹æäžã«å ç±ãè¡ãªãåå¿æž©
床102âååŸã1.5æéç¶æããã®ã¡ãç³»ãå·åŽã
æåºçµæ¶ãåããã€ãã§ãã®ãã®ãå¡©é žé žæ§æ°Ž
溶液ãšãªãã該氎溶液ãçé žã«ãªãŠã ã§å åã¢ã«
ã«ãªæ§ãšãªããæåºçµæ¶ãåãæ°ŽæŽã也ç¥ãã
ç®çç©8.75ïœããããæ¬åã®2E4MZã«å¯Ÿããåç
ã¯92ïŒ ã§ãã€ãã å®æœäŸ ïŒ åžè²©37ïŒ ããªã«ããªã³3.9ïœïŒ2E4MZã«å¯Ÿãã
ã¢ã«æ¯0.65ïŒã2E4MZ9ïœãæ°Žé žåã«ãªãŠã 0.25ïœ
ïŒ2E4MZã«å¯Ÿããã¢ã«æ¯0.05ïŒåã³æ°Ž27mlãå®æœ
äŸïŒãšåæ§ã«åå¿ãããç³»ãå·åŽãæåºçµæ¶ïŒç¬¬
ïŒçµæ¶ïŒãåãã液ãæžå§èžçã«ä»ãçåºã
ãæªåå¿2E4MZ0.6ïœãååãããèžçæ®äžã®æ°Ž
äžæº¶ç©ïŒç¬¬ïŒçµæ¶ïŒãåããå ã®ç¬¬ïŒçµæ¶ãšå
䜵ããå¡©é žé žæ§æ°Žæº¶æ¶²ãšãªãã該氎溶液ãã¢ã³ã¢
ãã¢ã§ã¢ã«ã«ãªæ§ãšãªããæåºçµæ¶ãåãç±æ°Ž
æŽæ»ããã®ã¡ä¹Ÿç¥ãç®çç©8.75ïœã2E4MZã«å¯Ÿã
ãåç89ïŒ ãåå2E4MZãè£æ£ããåçïŒä»¥äž
è£æ£åçãšããïŒ93ïŒ ããããã å®æœäŸ ïŒ åžè²©37ïŒ ããªã«ããªã³ïŒïœïŒã¢ã«æ¯0.5ïŒã
2E4MZ9ïœïŒã¢ã«æ¯1.0ïŒãKOH0.25ïœïŒã¢ã«æ¯
0.05ïŒåã³æ°Ž27mlãå®æœäŸïŒãšå šãåæ§ã«åŠç
ãã2E4MZ1.3ïœãšç®çç©7.65ïœïŒåç81ïŒ ãè£
æ£åç94ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®ããªã«ããªã³ã®éã1.5ïœïŒã¢ã«æ¯
0.25ïŒã«ä»£ããå¡©é žãé ¢é žã«ä»£ãã以å€ã¯å šãå®
æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã2E4MZ4.65
ïœãååããç®çç©3.4ïœïŒåç36ïŒ ãè£æ£åç
74ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®KOHã®éã0.25ïœãã0.13ïœïŒã¢ã«
æ¯0.025ïŒã«ä»£ãã以å€ã¯å šãå®æœäŸïŒãšåäžæ¡
件äžã®åå¿ãè¡ãªãã2E4MZã0.75ïœååããç®
çç©7.1ïœïŒè£æ£åç82ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®KOHã®éã0.25ïœãã4.6ïœïŒã¢ã«
æ¯1.0ïŒã«ä»£ãã以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶
äžã®åå¿ãè¡ãªãã2E4MZ2.3ïœãšç®çç©4.65ïœ
ïŒè£æ£åç65ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®KOHã®éã0.25ïœãã0.13ïœïŒã¢ã«
æ¯0.025ïŒã«ä»£ããåæã«å¡©é žãçé žã«ä»£ãã以
å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã
2E4MZ1.05ïœãšç®çç©7.65ïœïŒè£æ£åç91ïŒ ïŒã
ããã å®æœäŸ ïŒ å®æœäŸïŒã®KOH0.25ïœãæ°Žé žåãªããŠã
ïŒLiOHïŒ0.3ïœïŒã¢ã«æ¯0.15ïŒã«å€ãã以å€ã¯å š
ãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã
2E4MZ0.85ïœãšç®çç©7.5ïœïŒè£æ£åç87ïŒ ïŒã
ããã å®æœäŸ ïŒ å®æœäŸïŒã®LiOH0.3ïœããããªãŠã ã¢ãã
ïŒNaNH2ïŒ0.5ïœïŒã¢ã«æ¯0.15ïŒã«å€ãã以å€ã¯å š
ãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã
2E4MZ0.7ïœãšç®çç©7.55ïœïŒè£æ£åç86ïŒ ïŒã
ããã å®æœäŸ 10 å®æœäŸïŒã®LiOH0.3ïœãçé žãªããŠã
ïŒLi2CO3ïŒ0.9ïœïŒã¢ã«æ¯0.15ïŒã«å€ããåæã«å¡©
é žãç¡«é žã«å€ãããŸãã¢ã³ã¢ãã¢ãNaOHã«å€ã
ã以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãª
ãã2E4MZ2.9ïœãšç®çç©6.5ïœïŒåç69ïŒ ïŒãã
ãã å®æœäŸ 11 å®æœäŸïŒã®LiOH0.3ïœãKOH0.7ïœïŒã¢ã«æ¯
0.15ïŒã«å€ãããŸãæ°Žãã¡ã¿ããŒã«27mlã«å€ãã
以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãª
ããïŒäœãåå¿æž©åºŠ69âïŒã2E4MZ0.65ïœãšç®çç©
8.1ïœïŒè£æ£åç92ïŒ ïŒãããã å®æœäŸ 12 å®æœäŸïŒã®LiOH0.3ïœãNaOH0.5ïœïŒã¢ã«æ¯
0.15ïŒã«å€ãããŸãæ°Žããšã¿ããŒã«27mlã«å€ãã
以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªã
ïŒäœãåå¿æž©åºŠã¯82âïŒã2E4MZ0.3ïœãšç®çç©8.4
ïœïŒè£æ£åç91ïŒ ïŒãããã å®æœäŸ 13 2E4MZ9ïœïŒã¢ã«æ¯1.0ïŒããã©ããªã«ã 1.2ïœ
ïŒã¢ã«æ¯0.5ïŒåã³KOH0.3ïœïŒã¢ã«æ¯0.1ïŒã®ïŒè
ãå®æœäŸïŒãšåäžã®åå¿è£ 眮ã«ä»èŸŒã¿ãåå¿æž©åºŠ
128âã1.5æéç¶æããã®ã¡ãåå¿æ··åç©ãæžå§
èžçã«ä»ã2E4MZ3.1ïœãšç®çç©3.2ïœïŒè£æ£åç
51ïŒ ïŒãããã å®æœäŸ 14 2E4MZïŒã¢ã«æ¯1.0ïŒããã©ããªã«ã 1.2ïœïŒã¢
ã«æ¯0.5ïŒãKOH0.5ïœïŒã¢ã«æ¯0.15ïŒåã³ãšãã¬
ã³ã°ãªã³ãŒã«27mlã128âã§1.5æéåå¿ãããã
ãšãã¬ã³ã°ãªã³ãŒã«ãš2E4MZïŒ0.5ïœïŒãæžå§èž
çãè¡ã€ãŠååãããèžçæ®æž£ãåžç¡é žæ°Žæº¶æ¶²ã«
溶ãããã€ãã§è©²æ°Žæº¶æ¶²ãçé žãããªãŠã ã§ã¢ã«
ã«ãªæ§ãšãªãæåºçµæ¶ãåãæ°ŽæŽã也ç¥ãç®ç
ç©7.9ïœïŒè£æ£åç88ïŒ ïŒãããã å®æœäŸ 15 å®æœäŸ14ã®ãšãã¬ã³ã°ãªã³ãŒã«ãïœâãã¿ããŒ
ã«ã«ä»£ãã以å€ã¯å šãå®æœäŸ14ãšåäžæ¡ä»¶äžã®å
å¿ãè¡ãªãïŒäœãåå¿æž©åºŠã¯116âïŒã2E4MZ1.1
ïœãšç®çç©7.7ïœïŒè£æ£åç91ïŒ ïŒãããã å®æœäŸ 16 2E4MZ3ïœïŒã¢ã«æ¯1.0ïŒãïŒïŒïŒâãžãªããœã©
ã³â21ïœïŒã¢ã«æ¯0.5ïœïŒåã³KOH0.1ïœïŒã¢ã«æ¯
0.15ïŒã®ïŒè ãå°ç®¡äžã§300âã§ïŒæéå ç±ã
ããåå¿çµäºåŸãå°ç®¡ãæŸå·ãéå£ããŠãæåºçµ
æ¶ãåããå¡©é žé žæ§æ°Žæº¶æ¶²ãšãªããã€ãã§è©²æ°Ž
溶液ãçé žã«ãªãŠã ã§ã¢ã«ã«ãªæ§ãšãªããæåºçµ
æ¶ãåãæ°ŽæŽã也ç¥ãç®çç©075ïœïŒåç24
ïŒ ïŒãããã å®æœäŸ 17â19 ããªãšããã·ååç©ïŒåååïŒãšãã³ãŒã828ã
æ²¹åã·ãšã«ã補ïŒã«ïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒãæå®
éæ·»å ããäžæ¬ããŒã«æ©ãéã硬åå€ç²åãïŒÎŒ
以äžãšããŠåäžãªèª¿åç©ãåŸãã ãã®èª¿åç©åã³ãã®èª¿åç©ã«ä»ã®å å¡«ææãæ·»
å ããŠåŸããã泚åææã®ä¿åå®å®æ§ãã²ã«åæ
éïŒç¡¬åæ§ïŒäžŠã³ã«ç¡¬åç©ã®æ§èœã枬å®ããçµæ
ãäžè¡šã«ç€ºãã ãªãã調åç©ã®é åéã¯ééåäœã§ç€ºãã硬å
æ¡ä»¶ã¯120âã®æž©åºŠã§ïŒæé150âã®æž©åºŠã§ïŒæé
å ç±ãããã®ã§ããã
補é æ¹æ³åã³è©²ååç©ãçšããŠããªãšããã·æš¹è
ã硬åãªãã硬åä¿é²ãããæ¹æ³ã«é¢ãããã®ã§
ãããæ¬çºæè çã¯ããªãšããã·æš¹èã«å¯ŸããŠåª
ãã硬åæ§ãªãã硬åä¿é²æ§ã瀺ãååç©ãæ±ã
éæç 究ã®çµæã次åŒã§ç€ºãããïŒïŒ4â²âã¡ãã¬
ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒ
ã«ïŒãããã«çžåœããããšãèŠåºããã æ¬çºæè çã¯ïŒâãšãã«âïŒâã¡ãã«ã€ãããŸ
ãŒã«ïŒä»¥äž2E4MZãšç¥èšããïŒãšããªã«ã ã¢ã«
ãããåã¯ã¡ãã¬ã³åå€ã溶å€ãçšããããã¯çš
ããã«è§Šåªãšå ±ã«å ç±ããããšã«ãã次瀺ã®åå¿
ãèµ·ããããšãèŠåºãããå³ã¡ å㯠次ã«æ¬çºæã®åå¿ã®å®æœã®æ æ§ã«ã€ããŠè¿°ã¹
ãããœãŒãã©ã€ã å 填管ã§å€æ°äžã®çé žã¬ã¹ãé®
æïŒäœã觊åªãçé žã¢ã«ã«ãªã®å Žåã¯é®æäžèŠïŒ
ãã容åšäžã§é©åœã¢ã«æ¯ã®2E4MZãããªã«ã ã¢
ã«ãããïŒåã¯ã¡ãã¬ã³åå€ïŒåã³è§Šåªãé©åœé
ã®æº¶å€ãçšããããã¯çšããã«åžžå§ã§é©åœæéå
ç±æ¹æãè¡ãªããšããããŠåäžæº¶æ¶²ããçµæ¶ãæ
åºããŠæ¥ããæŽã«é©åœæéãã®å ç±æ¹æãè¡ãªã
åå¿ãå®äºãããã®ã¡ç³»ãå·åŽããçµæ¶ãåã
åçµæ¶ïŒç¬¬ïŒçµæ¶ãšåŒã¶ïŒãäžæŠé žæ§æ°Žæº¶æ¶²ãš
ãªããã€ãã§è©²æ°Žæº¶æ¶²ãã¢ã«ã«ãªæ§ãšããéã«æ
åºããçµæ¶ãåãæ°ŽæŽã也ç¥ããã°ç²Ÿè£œç©ãã
ããããä»æ¹ã第ïŒçµæ¶ãåããéã®æ¶²ãæž
å§èžçããæªåå¿2E4MZãååãããèžçæ®æž£
äžã®æ°Žäžæº¶æ§çµæ¶ãåããïŒç¬¬ïŒçµæ¶ãšåŒ
ã¶ïŒã第ïŒçµæ¶ã第ïŒçµæ¶ãšåæ§ã«åŠçãããšå
ãã粟補ç©ããããããå¿è«ã第ïŒçµæ¶åã³ç¬¬ïŒ
çµæ¶ãåžžæ³ïŒäŸãã°åçµåã¯æžå§æè¯ãªã©ïŒã«åŸ
ã€ãŠç²Ÿè£œããããšãåºæ¥ãã æ¬çºæã«ãããŠäœ¿çšãããåºçºç©è³ª2E4MZã¯
ãããã¬ã³ãžã¢ãã³ãšããããªãããªã«ããç¹å ¬
æ39â24965å·å ¬å ±ãç¹å ¬æ42â1548å·å ¬å ±åã³
ç¹å ¬æ41â151711å·å ¬å ±ã«åŸã€ãŠåæãããç©è³ª
ã§ããã æ¬çºæååç©ã®åæã«ãããŠäœ¿çšãããããªã«
ã ã¢ã«ãããã¯åžè²©ã®ããªã«ããªã³æ°Žæº¶æ¶²ã§å å
ã§ããããŸãã¡ãã¬ã³åå€ã¯ãã©ããªã«ã åã¯
ïŒïŒïŒâãžãªããœã©ã³âïŒããããµã¡ãã¬ã³ãã
ã©ãã³ããã³ã¬ãªããåã³ã¢ã«ã³ãŒã«ã®ããªã«
ããŒã«çã§ãããããããããµã¡ãã¬ã³ããã©ã
ã³åã³ãã³ã¬ãªããã®äœ¿çšã¯ããªã«ããªã³ã«æ¯
ãåçäžäœãã®å©ç¹ãã瀺ããªãã æ¬çºæååç©ã®è£œé å·¥çšã«ãããŠäœ¿çšããã溶
å€ã¯ãæ°Žåã³ã¡ã¿ããŒã«ããšã¿ããŒã«ãïœâãã¿
ããŒã«ããšãã¬ã³ã°ãªã³ãŒã«çã®ã¢ã«ã³ãŒã«é¡ã
奜ãŸããã觊åªã¯æ°Žé žåãªããŠã ãæ°Žé žåãããª
ãŠã ãæ°Žé žåã«ãªãŠã ãçé žãªããŠã ããããªãŠ
ã ã¢ãããçé žãããªãŠã ãçé žã«ãªãŠã ã
Triton çã§ãããäœããçé žãããªãŠã ã
çé žã«ãªãŠã åã³Triton ã®èœåã¯äžèšã®ä»
ã®è§Šåªã«æ¯ãå£ãã觊åªã®äœ¿çšéã¯ãã®çš®é¡ã«ã
ã€ãŠå€å°å€åããããäžæŠã«äºã€ãŠ2E4MZã«å¯Ÿ
ãã¢ã«æ¯0.2以äžã§å åã§ããããã以äžã®éã¯
äžå¿ èŠã§ãããåå¿æž©åºŠã¯æº¶å€ã®çš®é¡ã®åŠäœã«ã
ã€ãŠç°ãã70ä¹è³130âãé©åœã§ãããæ¬çºæã®
åå¿ã¯åžžå§ã§å åé²è¡ããã å¿è«ãå å§äžã®åå¿ãè¡ãããšãåºæ¥ãã ç²ç®çç©ïŒç¬¬ïŒçµæ¶åã³ç¬¬ïŒçµæ¶ïŒã®é žæ§æ°Žæº¶
液調補ã«äœ¿çšãããé žã¯ç¡æ©é žãããã¯ææ©é žã§
ãããäŸãã°å¡©é žãç¡é žãç¡«é žãçé žãé ¢é žã矩
é žçã§ãããç²ç®çç©ã溶解ãããé žæ§æ°Žæº¶æ¶²ã
ã¢ã«ã«ãªæ§ãšããããã«äœ¿çšãããå¡©åºã¯æ°Žé žå
ãããªãŠã ãæ°Žé žåã«ãªãŠã ãçé žãããªãŠã ã
çé žã«ãªãŠã ãæ°Žé žåã«ã«ã·ãŠã ãçé žã«ã«ã·ãŠ
ã ãã¢ã³ã¢ãã¢çã§ããã æ¬çºæååç©ã§ããïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒã®æ§è³ª
ã¯æ¬¡ã®éãã§ããã èç¹ïŒ260.5âïŒæè¯ã䌎ãªãïŒ ç¡è²çµæ¶ãå¡©åºæ§ã ã¢ã«ã³ãŒã«ã«å¯æº¶ãæ°Žã«äžæº¶ãã¢ã»ãã³åã³ãã«
ãšã³ã«é£å®¹ã TLCïŒã·ãªã«ãEtOHïŒïŒïŒ²f0.05ã0.35ïŒB.T.B
çºè²ïŒã ÎœcmâïŒ ïŒ«ïŒ¢ïœïŒ2980ïŒ1618ïŒç¬¬ïŒåžåïŒ1533ïŒ1455ïŒ
第
ïŒåžåïŒïŒ1435ïŒç¬¬ïŒåžåïŒïŒ1372ïŒ1330ïŒ
1280ïŒ1242ïŒ1205ïŒ1145ïŒ1110ïŒ1072ïŒç¬¬ïŒ
åžåïŒïŒ1049ïŒç¬¬ïŒåžåïŒïŒ985ïŒ967ïŒ920ïŒ
880ïŒ822ïŒ788ïŒ697 NMRïŒCD3ODïŒïŒÎŽ3.68ïŒïœïŒ2HïŒïŒã¡ãã¬
ã³ïŒïŒ2.61ïŒïœïŒ4HïŒãšãã«åºã®ã¡ãã¬
ã³ïŒïŒ2.00ïŒïœïŒ6HïŒïŒã¡ãã«ïŒïŒ1.21ïŒ
ïœïŒ6HïŒãšãã«åºã®ã¡ãã«ïŒ MassïŒïœïŒïœ ïŒïŒ232ïŒM+ïŒã217ïŒM+âã¡ã
ã«ïŒïŒ203ïŒ217âã¡ãã¬ã³ïŒïŒ123ïŒ2E4MZâ
ïŒã¡ãã¬ã³ïŒïŒ110ïŒ2E4MZïŒ æ¬çºæååç©ã¯ååäžã«å¹³åïŒã±ããå€ãã®ãš
ããã·åºãæããããªãšããã·ååç©ãææã®é«
ãããã枩床ã§è¿ éäžã€å¹ççã«ç¡¬åãããããš
ãã§ããäžæåç³»ãšããã·æš¹èãå³ã¡ããªãšãã
ã·ååç©ã硬åå€ãšäºåæ··åãããç³»ã®ä¿å寿åœ
ãããã¯ä¿åå®å®æ§ã«å®è³ªçãªåœ±é¿ãåãŒããªã
æœåšæ§ç¡¬åå€ãªããæœåšæ§ç¡¬åä¿é²å€ãšããŠæ¥µã
ãŠæçšã§ããã æ¬çºæã®å®æœã«ããåŸãããäžæåç³»ãšããã·
æš¹èã¯ã宀枩ã«ãããŠã¯é·æéã«äºã€ãŠç²åºŠäžæ
ãªã©äœæ¥æ§èœã®äœäžãããããå€åãå°ãªãå®å®
ãªç¶æ ã§ä¿åãããé«æž©ã«ãããŠã¯è¿ éäžã€å¹ç
çã«ç¡¬åããé»æ°çµ¶çžæ§èœãæ©æ¢°ç匷床ç¹æ§ãè
ååŠè¬åæ§ãªã©ã®è«žç¹æ§ã«ãã©ã³ã¹ã®æ¡ããåªã
ã硬åç©ãåŸãããã æ¬çºæã¯ïŒïŒ4â²âã¡ãã¬ã³âãã¹âïŒïŒâãšã
ã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒãåç¬ã§ç¡¬åå€ãš
ããŠçšããå€ã«ãä»ã®ç¡¬åå€æåãäŸãã°ãèèª
æããªã¢ãã³ãè³éŠæããªã¢ãã³ãã¢ãã³å¡©ã第
åçŽã¢ã³ã¢ããŠã å¡©ããžã·ã¢ã³ãžã¢ãããå°¿çŽ ã
ã¡ã©ãã³ãããªã«ã«ãã³é žãããªã«ã«ãã³é žç¡æ°Ž
ç©ãããšããŒã«é¡ãšã¢ã«ãããé¡ã®ä»å çž®åäœã
å«ãå€äŸ¡ããšããŒã«ãããªã«ã«ãã³é žããã©ãž
ããã€ãããŸãŒã«ååç©ãªã©ã®ç¡¬åä¿é²å€ä¹è³ã¯
å ±ç¡¬åå€ãšããŠçšããããšãå å«ããã æ¬çºæã«ãããŠãïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒã硬å
å€ãšããŠäœ¿çšããå Žåãã®é©æ£é åå²åã¯ã0.5
ä¹è³30phrïŒããªãšããã·ååç©100éééšåœã
ãã®éééšïŒã§ãããä»ã®ç¡¬åå€ã®ä¿é²å€ä¹è³ã¯
å ±éåå€ãšããŠäœ¿çšããå Žåã®é©æ£é åå²åã¯
0.01ä¹è³30phrã§ããã奜ãŸããã¯0.05ä¹è³10phr
ã§ããã æ¬çºæã«ãããããªãšããã·ååç©ã¯ïŒåååœ
ããå¹³åïŒåããå€ãã®ãšããã·åºãå«æããã
ã®ã§ãã€ãŠããã®åºã¯ååæ«ç«¯äœçœ®ã«ãã ã§ããããæãã¯äžè¬ã«å éšãšããã·ããšåŒã°ã
ããåååŒã®éäžã«ä»åšã㊠ã®åœ¢ã®åºã圢æããŠãããããã®ããªãšããã·å
åç©ã¯èèªæãç°ç¶èèªæãè³éŠæããŸãã¯è€çŽ
ç°åŒã®ãã®ã§ãããããŸãæ°Žé žåºãã¢ã«ãã«åºã
ã¢ã«ã³ãã·åºããšã¹ãã«åºãã¢ã»ã¿ãŒã«åºããšãŒ
ãã«åºã®ãããªé劚害æ§ã®çœ®æåºã§çœ®æãããŠã
ãŠãè¯ãã æãæãŸããããªãšããã·ååç©ã¯ãã¹ããšã
ãŒã«ïŒ¡ããã¹ããšããŒã«ïŒŠãã¬ãŸã«ã·ã³ããã€ã
ãããã³ããã¹ããšããŒã«ïŒ³ãããšããŒã«ã»ãã«
ã ã¢ã«ãããæš¹èãã¯ã¬ãŸãŒã«ã»ãã«ã ã¢ã«ãã
ãæš¹èã®ãããªå€äŸ¡ããšããŒã«ã®ããªã°ãªã·ãžã«
ãšãŒãã«ããã ãã®ä»é©åœãªããªãšããã·ååç©ãäŸç€ºãããš
ïŒããªïŒãšãã¬ã³ã°ãªã³ãŒã«ãïŒããªïŒãããã¬ã³
ã°ãªã³ãŒã«ãã°ãªã»ãªã³ãããªã¡ãããŒã«ããã
ã³ãïŒïŒïŒâãã¿ã³ãžãªãŒã«ã®ãããªå€äŸ¡ã¢ã«ã³
ãŒã«ã®ã°ãªã·ãžã«ãšãŒãã«ããã¿ã«é žãããã©ã
ãããã¿ã«é žããããµããããã¿ã«é žãã¡ãã«â
ãšã³ãã¡ãã¬ã³âããã©ããããã¿ã«é žãã¢ãžã
ã³é žããã€ããŒé žã®ãããªå€äŸ¡ã«ã«ãã³é žã®ããª
ã°ãªã·ãžã«ãšã¹ãã«ãã¢ããªã³ããã«ã€ãžã³ã
ïŒïŒ4â²âãžã¢ãããžããšãã«ã¡ã¿ã³ã®ãããªããª
ã¢ãã³ããèªå°ãããã°ãªã·ãžã«ã¢ãã³é¡ããã
ã«ã·ã¯ãããã»ã³ãªããµã€ããïŒïŒïŒâãšããã·
ã·ã¯ãããã·ã«âïŒïŒïŒâãšããã·ã·ã¯ããããµ
ã³ã«ã«ããã·ã¬ãŒãããã¹âïŒïŒïŒïŒâãšããã·
âïŒâã¡ãã«ã·ã¯ãããã·ã«ã¡ãã«ïŒâã¢ãžããŒ
ãã®ãããªãšããã·åããªãªã¬ãã€ã³ããããã¯
ãšããã·åæ€ç©æ²¹ãªã©ã§ãããæ¬çºææ¹æ³ã¯å¿ çš
ã«å¿ããŠçè²é¡æãäœè³ªé¡æãå¯å¡å€ãããã³ã
ãã«ã°ãªã·ãžã«ãšãŒãã«ãããšãã«ã°ãªã·ãžã«ãš
ãŒãã«ã®ãããªã¢ããšããã·ååç©ã®åå¿æ§çšé
å€ããããã¯ã±ãã³ç³»ãã°ãªã³ãŒã«ç³»ãè³éŠæç³
æ²¹ãããµã®ãããªæº¶å€ãªã©ãæ·»å ãåŸãã æ¬çºæã®å®æœã«ããã60ä¹è³240âã奜ãŸãã
ã¯100ä¹è³180âã«æŒããŠçæéã«ç¡¬ååŠçãåŸã
ãšããã·æš¹èç³»ã¯ãã¹ãå¡æãæ¥çå€ã泚åæ
æã也åŒç©å±€çšããªãã¬ãã°ãæ圢çšã³ã³ããŠã³
ããç²æ«å¡æçã圢æåºæ¥ãã 以äžå®æœã®æ æ§ãå®æœäŸã«ãã€ãŠèª¬æããã å®æœäŸ ïŒ é»ç£æ¹ææ©ãéæµå·åŽåšã枩床èšåã³å€æ°ã®ç
é žã¬ã¹é®æçšãœãŒãã©ã€ã 管ãåããåå¿å®¹åšã«
åžè²©37ïŒ ããªã«ããªã³4.5ïœïŒ2E4MZã«å¯Ÿããã¢
ã«æ¯0.75ïŒã2E4MZ9ïœãæ°Žé žåã«ãªãŠã
ïŒKOHïŒ0.25ïœïŒ2E4MZã«å¯Ÿããã¢ã«æ¯0.05ïŒå
ã³æ°Ž27mlãä»èŸŒã¿ãæ¹æäžã«å ç±ãè¡ãªãåå¿æž©
床102âååŸã1.5æéç¶æããã®ã¡ãç³»ãå·åŽã
æåºçµæ¶ãåããã€ãã§ãã®ãã®ãå¡©é žé žæ§æ°Ž
溶液ãšãªãã該氎溶液ãçé žã«ãªãŠã ã§å åã¢ã«
ã«ãªæ§ãšãªããæåºçµæ¶ãåãæ°ŽæŽã也ç¥ãã
ç®çç©8.75ïœããããæ¬åã®2E4MZã«å¯Ÿããåç
ã¯92ïŒ ã§ãã€ãã å®æœäŸ ïŒ åžè²©37ïŒ ããªã«ããªã³3.9ïœïŒ2E4MZã«å¯Ÿãã
ã¢ã«æ¯0.65ïŒã2E4MZ9ïœãæ°Žé žåã«ãªãŠã 0.25ïœ
ïŒ2E4MZã«å¯Ÿããã¢ã«æ¯0.05ïŒåã³æ°Ž27mlãå®æœ
äŸïŒãšåæ§ã«åå¿ãããç³»ãå·åŽãæåºçµæ¶ïŒç¬¬
ïŒçµæ¶ïŒãåãã液ãæžå§èžçã«ä»ãçåºã
ãæªåå¿2E4MZ0.6ïœãååãããèžçæ®äžã®æ°Ž
äžæº¶ç©ïŒç¬¬ïŒçµæ¶ïŒãåããå ã®ç¬¬ïŒçµæ¶ãšå
䜵ããå¡©é žé žæ§æ°Žæº¶æ¶²ãšãªãã該氎溶液ãã¢ã³ã¢
ãã¢ã§ã¢ã«ã«ãªæ§ãšãªããæåºçµæ¶ãåãç±æ°Ž
æŽæ»ããã®ã¡ä¹Ÿç¥ãç®çç©8.75ïœã2E4MZã«å¯Ÿã
ãåç89ïŒ ãåå2E4MZãè£æ£ããåçïŒä»¥äž
è£æ£åçãšããïŒ93ïŒ ããããã å®æœäŸ ïŒ åžè²©37ïŒ ããªã«ããªã³ïŒïœïŒã¢ã«æ¯0.5ïŒã
2E4MZ9ïœïŒã¢ã«æ¯1.0ïŒãKOH0.25ïœïŒã¢ã«æ¯
0.05ïŒåã³æ°Ž27mlãå®æœäŸïŒãšå šãåæ§ã«åŠç
ãã2E4MZ1.3ïœãšç®çç©7.65ïœïŒåç81ïŒ ãè£
æ£åç94ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®ããªã«ããªã³ã®éã1.5ïœïŒã¢ã«æ¯
0.25ïŒã«ä»£ããå¡©é žãé ¢é žã«ä»£ãã以å€ã¯å šãå®
æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã2E4MZ4.65
ïœãååããç®çç©3.4ïœïŒåç36ïŒ ãè£æ£åç
74ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®KOHã®éã0.25ïœãã0.13ïœïŒã¢ã«
æ¯0.025ïŒã«ä»£ãã以å€ã¯å šãå®æœäŸïŒãšåäžæ¡
件äžã®åå¿ãè¡ãªãã2E4MZã0.75ïœååããç®
çç©7.1ïœïŒè£æ£åç82ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®KOHã®éã0.25ïœãã4.6ïœïŒã¢ã«
æ¯1.0ïŒã«ä»£ãã以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶
äžã®åå¿ãè¡ãªãã2E4MZ2.3ïœãšç®çç©4.65ïœ
ïŒè£æ£åç65ïŒ ïŒãããã å®æœäŸ ïŒ å®æœäŸïŒã®KOHã®éã0.25ïœãã0.13ïœïŒã¢ã«
æ¯0.025ïŒã«ä»£ããåæã«å¡©é žãçé žã«ä»£ãã以
å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã
2E4MZ1.05ïœãšç®çç©7.65ïœïŒè£æ£åç91ïŒ ïŒã
ããã å®æœäŸ ïŒ å®æœäŸïŒã®KOH0.25ïœãæ°Žé žåãªããŠã
ïŒLiOHïŒ0.3ïœïŒã¢ã«æ¯0.15ïŒã«å€ãã以å€ã¯å š
ãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã
2E4MZ0.85ïœãšç®çç©7.5ïœïŒè£æ£åç87ïŒ ïŒã
ããã å®æœäŸ ïŒ å®æœäŸïŒã®LiOH0.3ïœããããªãŠã ã¢ãã
ïŒNaNH2ïŒ0.5ïœïŒã¢ã«æ¯0.15ïŒã«å€ãã以å€ã¯å š
ãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªãã
2E4MZ0.7ïœãšç®çç©7.55ïœïŒè£æ£åç86ïŒ ïŒã
ããã å®æœäŸ 10 å®æœäŸïŒã®LiOH0.3ïœãçé žãªããŠã
ïŒLi2CO3ïŒ0.9ïœïŒã¢ã«æ¯0.15ïŒã«å€ããåæã«å¡©
é žãç¡«é žã«å€ãããŸãã¢ã³ã¢ãã¢ãNaOHã«å€ã
ã以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãª
ãã2E4MZ2.9ïœãšç®çç©6.5ïœïŒåç69ïŒ ïŒãã
ãã å®æœäŸ 11 å®æœäŸïŒã®LiOH0.3ïœãKOH0.7ïœïŒã¢ã«æ¯
0.15ïŒã«å€ãããŸãæ°Žãã¡ã¿ããŒã«27mlã«å€ãã
以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãª
ããïŒäœãåå¿æž©åºŠ69âïŒã2E4MZ0.65ïœãšç®çç©
8.1ïœïŒè£æ£åç92ïŒ ïŒãããã å®æœäŸ 12 å®æœäŸïŒã®LiOH0.3ïœãNaOH0.5ïœïŒã¢ã«æ¯
0.15ïŒã«å€ãããŸãæ°Žããšã¿ããŒã«27mlã«å€ãã
以å€ã¯å šãå®æœäŸïŒãšåäžæ¡ä»¶äžã®åå¿ãè¡ãªã
ïŒäœãåå¿æž©åºŠã¯82âïŒã2E4MZ0.3ïœãšç®çç©8.4
ïœïŒè£æ£åç91ïŒ ïŒãããã å®æœäŸ 13 2E4MZ9ïœïŒã¢ã«æ¯1.0ïŒããã©ããªã«ã 1.2ïœ
ïŒã¢ã«æ¯0.5ïŒåã³KOH0.3ïœïŒã¢ã«æ¯0.1ïŒã®ïŒè
ãå®æœäŸïŒãšåäžã®åå¿è£ 眮ã«ä»èŸŒã¿ãåå¿æž©åºŠ
128âã1.5æéç¶æããã®ã¡ãåå¿æ··åç©ãæžå§
èžçã«ä»ã2E4MZ3.1ïœãšç®çç©3.2ïœïŒè£æ£åç
51ïŒ ïŒãããã å®æœäŸ 14 2E4MZïŒã¢ã«æ¯1.0ïŒããã©ããªã«ã 1.2ïœïŒã¢
ã«æ¯0.5ïŒãKOH0.5ïœïŒã¢ã«æ¯0.15ïŒåã³ãšãã¬
ã³ã°ãªã³ãŒã«27mlã128âã§1.5æéåå¿ãããã
ãšãã¬ã³ã°ãªã³ãŒã«ãš2E4MZïŒ0.5ïœïŒãæžå§èž
çãè¡ã€ãŠååãããèžçæ®æž£ãåžç¡é žæ°Žæº¶æ¶²ã«
溶ãããã€ãã§è©²æ°Žæº¶æ¶²ãçé žãããªãŠã ã§ã¢ã«
ã«ãªæ§ãšãªãæåºçµæ¶ãåãæ°ŽæŽã也ç¥ãç®ç
ç©7.9ïœïŒè£æ£åç88ïŒ ïŒãããã å®æœäŸ 15 å®æœäŸ14ã®ãšãã¬ã³ã°ãªã³ãŒã«ãïœâãã¿ããŒ
ã«ã«ä»£ãã以å€ã¯å šãå®æœäŸ14ãšåäžæ¡ä»¶äžã®å
å¿ãè¡ãªãïŒäœãåå¿æž©åºŠã¯116âïŒã2E4MZ1.1
ïœãšç®çç©7.7ïœïŒè£æ£åç91ïŒ ïŒãããã å®æœäŸ 16 2E4MZ3ïœïŒã¢ã«æ¯1.0ïŒãïŒïŒïŒâãžãªããœã©
ã³â21ïœïŒã¢ã«æ¯0.5ïœïŒåã³KOH0.1ïœïŒã¢ã«æ¯
0.15ïŒã®ïŒè ãå°ç®¡äžã§300âã§ïŒæéå ç±ã
ããåå¿çµäºåŸãå°ç®¡ãæŸå·ãéå£ããŠãæåºçµ
æ¶ãåããå¡©é žé žæ§æ°Žæº¶æ¶²ãšãªããã€ãã§è©²æ°Ž
溶液ãçé žã«ãªãŠã ã§ã¢ã«ã«ãªæ§ãšãªããæåºçµ
æ¶ãåãæ°ŽæŽã也ç¥ãç®çç©075ïœïŒåç24
ïŒ ïŒãããã å®æœäŸ 17â19 ããªãšããã·ååç©ïŒåååïŒãšãã³ãŒã828ã
æ²¹åã·ãšã«ã補ïŒã«ïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒãæå®
éæ·»å ããäžæ¬ããŒã«æ©ãéã硬åå€ç²åãïŒÎŒ
以äžãšããŠåäžãªèª¿åç©ãåŸãã ãã®èª¿åç©åã³ãã®èª¿åç©ã«ä»ã®å å¡«ææãæ·»
å ããŠåŸããã泚åææã®ä¿åå®å®æ§ãã²ã«åæ
éïŒç¡¬åæ§ïŒäžŠã³ã«ç¡¬åç©ã®æ§èœã枬å®ããçµæ
ãäžè¡šã«ç€ºãã ãªãã調åç©ã®é åéã¯ééåäœã§ç€ºãã硬å
æ¡ä»¶ã¯120âã®æž©åºŠã§ïŒæé150âã®æž©åºŠã§ïŒæé
å ç±ãããã®ã§ããã
ãè¡šã
ãè¡šã
ãªããä¿åå®å®æ§ã«ã€ããŠã¯èª¿åç©ã25âã§è²¯
èµãããã®ç²åºŠå€åã枬å®ãç²åºŠãåæã®ïŒåã«
éããæç¹ããã€ãŠçµç¹ãšãããã®ã§ããã²ã«å
æéã¯150±0.5âã«äºã調ç¯ãããç±éæ¿äžã«è©Š
æçŽ0.7ïœïœã眮ãã¹ãã³ã¬ã¹è£œãžãã§è©ŠæãçŽ
20Ã30mm2ã®å€§ããã«æ¡ããçŽïŒç§éã«ïŒåŸåŸ©ã®é
ãã§è©Šæãåçã«æŒãä»ããªããç·Žãåããã
æã ãžããæã¡äžããŠè©Šæãšãžãã®éã«ç³žãæµã
ãªãç¶æ ã«ãªããŸã§ã®æéã枬å®ãæ±ãããã®ã§
ããã å®æœäŸ 20 ããªãšããã·ååç©ïŒ¡ïŒåååïŒãšãã³ãŒã
828ãæ²¹åã·ãšã«ã補ïŒ70éšãããªãšããã·åå
ç©ïŒ¢ïŒåååïŒãšãã³ãŒã834ãåïŒ30éšãæºå€
æ§éäžå€ïŒåååïŒãã³ãã³38ããã·ãšãã«ã¬ã
ã補ïŒïŒéšãäœè³ªé¡æïŒåååïŒæºã¿ã«ïŒ°ãåå±
ã«ãªãªã³ã補ïŒ30éšããžã·ã¢ã³ãžã¢ããïŒæ¥æ¬ã«
ãŒãã€ã補ïŒïŒéšãïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒïŒéšã
äžæ¬ããŒã«æ©ã«ãã€ãŠåäžã«æ··ç·Žããæ¥çå€çµæ
ç©ãåŸãããã®æ¥çå€ã¯å®€æž©ã§ïŒã±æ以äžã®ä¿å
æ§ãæãã120â以äžã®ç±åŠçã§è¿ éã«ç¡¬åãã
匷åºãªæ¥çåã瀺ããã ä¿åå®å®æ§ãæ¥ïŒ25â ïŒ60 ã²ã«åæéãminïŒ120â 6.4 minïŒ150â 1.8 minïŒ180â 0.7 åªææ¥ç匷ããKgïŒmm 硬åæ¡ä»¶0.5hrïŒ150â éŒâéŒïŒ20â 236 AlâAlïŒ20â 93 äœç©æµæçãΩâcmïŒ20â ïŒ1015 絶çžç Žå£é»å§ãKVïŒmm ïŒ20 å®æœäŸ 21â22 æ¬äŸã¯ïŒïŒïŒâã¡ãã¬ã³âãã¹âïŒïŒâãšãã«
âïŒâã¡ãã«ã€ãããŸãŒã«ïŒãåç¬ç¡¬åå€åã³é ž
ç¡æ°Žç©ã®ç¡¬åä¿é²å€ãšããŠçšããç²æ«å¡æé åäŸ
ã§ããã è¡šäžèšèŒã®æåã85ã95âã«äºç±ãããäºæ¬ã
ãŒã«æ©ã§å åã«çèæ··ç·ŽããŠåŸããã調åç©ãæ¥
å·ããç²ç ãåçŽã«ãã80ã270ã¡ãã·ãŠã®ç¯å²
ãæµå浞挬çšç²æ«å¡æãšããŠåŸãã該å¡æã¯ç®è
æµæåšãããªã¹ã¿ãã³ã³ãã³ãµããã€ããªãã
ICãªã©ã®ã»ã©ããã¯éšåã®è¢«èŠã«æçšã§ããã ãªãããããã®æš¹èã®ç¡¬åæ¡ä»¶ã¯150âã®æž©åºŠ
ã§ïŒæéå ç±ãããã®ã§ããã
èµãããã®ç²åºŠå€åã枬å®ãç²åºŠãåæã®ïŒåã«
éããæç¹ããã€ãŠçµç¹ãšãããã®ã§ããã²ã«å
æéã¯150±0.5âã«äºã調ç¯ãããç±éæ¿äžã«è©Š
æçŽ0.7ïœïœã眮ãã¹ãã³ã¬ã¹è£œãžãã§è©ŠæãçŽ
20Ã30mm2ã®å€§ããã«æ¡ããçŽïŒç§éã«ïŒåŸåŸ©ã®é
ãã§è©Šæãåçã«æŒãä»ããªããç·Žãåããã
æã ãžããæã¡äžããŠè©Šæãšãžãã®éã«ç³žãæµã
ãªãç¶æ ã«ãªããŸã§ã®æéã枬å®ãæ±ãããã®ã§
ããã å®æœäŸ 20 ããªãšããã·ååç©ïŒ¡ïŒåååïŒãšãã³ãŒã
828ãæ²¹åã·ãšã«ã補ïŒ70éšãããªãšããã·åå
ç©ïŒ¢ïŒåååïŒãšãã³ãŒã834ãåïŒ30éšãæºå€
æ§éäžå€ïŒåååïŒãã³ãã³38ããã·ãšãã«ã¬ã
ã補ïŒïŒéšãäœè³ªé¡æïŒåååïŒæºã¿ã«ïŒ°ãåå±
ã«ãªãªã³ã補ïŒ30éšããžã·ã¢ã³ãžã¢ããïŒæ¥æ¬ã«
ãŒãã€ã補ïŒïŒéšãïŒïŒ4â²âã¡ãã¬ã³âãã¹â
ïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒïŒéšã
äžæ¬ããŒã«æ©ã«ãã€ãŠåäžã«æ··ç·Žããæ¥çå€çµæ
ç©ãåŸãããã®æ¥çå€ã¯å®€æž©ã§ïŒã±æ以äžã®ä¿å
æ§ãæãã120â以äžã®ç±åŠçã§è¿ éã«ç¡¬åãã
匷åºãªæ¥çåã瀺ããã ä¿åå®å®æ§ãæ¥ïŒ25â ïŒ60 ã²ã«åæéãminïŒ120â 6.4 minïŒ150â 1.8 minïŒ180â 0.7 åªææ¥ç匷ããKgïŒmm 硬åæ¡ä»¶0.5hrïŒ150â éŒâéŒïŒ20â 236 AlâAlïŒ20â 93 äœç©æµæçãΩâcmïŒ20â ïŒ1015 絶çžç Žå£é»å§ãKVïŒmm ïŒ20 å®æœäŸ 21â22 æ¬äŸã¯ïŒïŒïŒâã¡ãã¬ã³âãã¹âïŒïŒâãšãã«
âïŒâã¡ãã«ã€ãããŸãŒã«ïŒãåç¬ç¡¬åå€åã³é ž
ç¡æ°Žç©ã®ç¡¬åä¿é²å€ãšããŠçšããç²æ«å¡æé åäŸ
ã§ããã è¡šäžèšèŒã®æåã85ã95âã«äºç±ãããäºæ¬ã
ãŒã«æ©ã§å åã«çèæ··ç·ŽããŠåŸããã調åç©ãæ¥
å·ããç²ç ãåçŽã«ãã80ã270ã¡ãã·ãŠã®ç¯å²
ãæµå浞挬çšç²æ«å¡æãšããŠåŸãã該å¡æã¯ç®è
æµæåšãããªã¹ã¿ãã³ã³ãã³ãµããã€ããªãã
ICãªã©ã®ã»ã©ããã¯éšåã®è¢«èŠã«æçšã§ããã ãªãããããã®æš¹èã®ç¡¬åæ¡ä»¶ã¯150âã®æž©åºŠ
ã§ïŒæéå ç±ãããã®ã§ããã
ãè¡šã
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ æ§é åŒ ã§ç€ºãããïŒïŒ4â²âã¡ãã¬ã³âãã¹âïŒïŒâãš
ãã«âïŒâã¡ãã«ã€ãããŸãŒã«ïŒã ïŒ ïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ãšããª
ã«ã ã¢ã«ãããåã¯ã¡ãã¬ã³åå€ã觊åªã®ååšäž
ã§å ç±åå¿ãããããšãç¹åŸŽãšããïŒïŒ4â²âã¡ã
ã¬ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸ
ãŒã«ïŒã®è£œé æ¹æ³ã ïŒ ã¡ãã¬ã³åå€ããã©ããªã«ã ãŸãã¯ïŒïŒïŒâ
ãžãªããœã©ã³âïŒã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èš
èŒã®æ¹æ³ã ïŒ æº¶å€ãæ°Žãããã¯ã¡ã¿ããŒã«ããšã¿ããŒã«ã
ïœâãã¿ããŒã«ããšãã¬ã³ã°ãªã³ãŒã«çã®ã¢ã«ã³
ãŒã«é¡ã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ è§ŠåªãšããŠæ°Žé žåãªããŠã ãæ°Žé žåãããªãŠ
ã ãæ°Žé žåã«ãªãŠã ããããªãŠã ã¢ãããçé žãª
ããŠã ãçšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹
æ³ã ïŒ å ç±æž©åºŠã20ã150âãç¹ã«å¥œãŸããã¯70ã
130âã®ç¯å²ã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®
æ¹æ³ã ïŒ ããªã«ã ã¢ã«ããããããã¯ã¡ãã¬ã³åå€ã®
ïŒâãšãã«âïŒâã¡ãã«ã€ãããŸãŒã«ã«å¯Ÿããã¢
ã«æ¯ãïŒïŒïŒãªãã0.13ïŒïŒã®ç¯å²ã§ããç¹ã«å¥œ
ãŸããã¯ãããã0.5ïŒïŒã®ç¯å²ã§ããç¹èš±è«æ±
ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ ç²ç®ççæç©ãé žæ§æ°Žæº¶æ¶²ãšããã€ãã§è©²æ°Ž
溶液ãã¢ã«ã«ãªæ§ãšããŠæåºããçµæ¶ãåãæ°Ž
æŽã也ç¥ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ ç¡¬åå€ãããã¯ç¡¬åä¿é²å€ãšããŠïŒïŒ4â²âã¡
ãã¬ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãã
ãŸãŒã«ïŒãçšããããšãç¹åŸŽãšããååäžã«å¹³å
ïŒåããå€ãã®ãšããã·åºãæããããªãšããã·
ååç©ã硬åãªãã硬åä¿é²ãããæ¹æ³ã
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58066584A JPS59190972A (ja) | 1983-04-14 | 1983-04-14 | ïŒïŒïŒâ²âã¡ãã¬ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸâã«ïŒã該ååç©ã®è£œé æ¹æ³åã³è©²ååç©ãçšããŠããªãšããã·ååç©ã硬åãªãã硬åä¿é²ãããæ¹æ³ |
| US06/594,902 US4514556A (en) | 1983-04-14 | 1984-03-29 | 4,4'-Methylene-bis-(2-ethyl-5-methyl imidazole) and methods of producing and using the same |
| EP84302138A EP0126531A3 (en) | 1983-04-14 | 1984-03-29 | 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) and methods of producing and using the same |
| CA000451388A CA1220207A (en) | 1983-04-14 | 1984-04-05 | 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) and methods of producing and using the same |
| KR1019840001888A KR860001763B1 (ko) | 1983-04-14 | 1984-04-10 | 4,4'-ë©ížë -ë¹ì€-(2-ìíž-5-ë©ížìŽë¯žë€ì¡ž)ì ì ì¡°ë°©ë² |
| KR1019840001890A KR840008329A (ko) | 1983-04-14 | 1984-04-10 | 2-ìíž-4-ë©ížìŽë¯žë€ì¡žì ê²°ì í ë°©ì§ë°©ë² |
| KR1019840001889A KR860001171B1 (ko) | 1983-04-14 | 1984-04-10 | ìíìíí©ë¬Œì 겜íë°©ë² ë° ê²œíìŽì§ ë°©ë² |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58066584A JPS59190972A (ja) | 1983-04-14 | 1983-04-14 | ïŒïŒïŒâ²âã¡ãã¬ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸâã«ïŒã該ååç©ã®è£œé æ¹æ³åã³è©²ååç©ãçšããŠããªãšããã·ååç©ã硬åãªãã硬åä¿é²ãããæ¹æ³ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59190972A JPS59190972A (ja) | 1984-10-29 |
| JPS6141910B2 true JPS6141910B2 (ja) | 1986-09-18 |
Family
ID=13320142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58066584A Granted JPS59190972A (ja) | 1983-04-14 | 1983-04-14 | ïŒïŒïŒâ²âã¡ãã¬ã³âãã¹âïŒïŒâãšãã«âïŒâã¡ãã«ã€ãããŸâã«ïŒã該ååç©ã®è£œé æ¹æ³åã³è©²ååç©ãçšããŠããªãšããã·ååç©ã硬åãªãã硬åä¿é²ãããæ¹æ³ |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4514556A (ja) |
| EP (1) | EP0126531A3 (ja) |
| JP (1) | JPS59190972A (ja) |
| KR (3) | KR840008329A (ja) |
| CA (1) | CA1220207A (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4581421A (en) * | 1985-05-06 | 1986-04-08 | Texaco, Inc. | Epoxy resin composition containing a curing agent which is a reaction product of imidazole and an aldehyde |
| DE3700287A1 (de) * | 1986-01-10 | 1987-07-16 | Hitachi Chemical Co Ltd | Epoxyharz-zusammensetzung fuer kupfer-plattierte laminate |
| JPS6445444A (en) * | 1987-08-12 | 1989-02-17 | Denki Kagaku Kogyo Kk | Rubber composition |
| DE4042191C1 (ja) * | 1990-12-29 | 1992-07-30 | Skw Trostberg Ag, 8223 Trostberg, De | |
| US7037367B2 (en) * | 2003-10-20 | 2006-05-02 | W.R. Grace & Co.-Conn. | Concrete surface retarders |
| CN108586709A (zh) * | 2018-05-10 | 2018-09-28 | æµæ±é¿å°æ³åå·¥ç§ææéå ¬åž | 延é¿ç¯æ°§æ èäœç³»éçšæ§çæ¹æ§é žé åºååçå¶å€æ¹æ³ |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6504681A (ja) * | 1965-04-13 | 1965-06-25 | ||
| FR1566468A (ja) * | 1968-03-04 | 1969-05-09 | ||
| US4041007A (en) * | 1976-03-05 | 1977-08-09 | Youngstown Sheet And Tube Company | Epoxy composition and article of manufacture thereof |
| US4205156A (en) * | 1977-03-18 | 1980-05-27 | Shikoku Chemicals Corporation | Novel imidazole-isocyanuric acid adducts and utilization thereof |
| US4209608A (en) * | 1978-12-11 | 1980-06-24 | Ciba-Geigy Corporation | Adducts containing epoxide groups, from hydantoin polyepoxide and binuclear hydantoin compounds |
| US4210744A (en) * | 1978-12-11 | 1980-07-01 | Ciba-Geigy Corporation | Adducts containing epoxide groups, from hydantoin trisepoxides and binuclear hydantoins |
| US4323453A (en) * | 1980-01-03 | 1982-04-06 | Monsanto Company | Tube sheets for permeators |
| US4417010A (en) * | 1982-02-08 | 1983-11-22 | Celanese Corporation | Polyol/imidazole curing agents for epoxy resins |
-
1983
- 1983-04-14 JP JP58066584A patent/JPS59190972A/ja active Granted
-
1984
- 1984-03-29 US US06/594,902 patent/US4514556A/en not_active Expired - Lifetime
- 1984-03-29 EP EP84302138A patent/EP0126531A3/en not_active Withdrawn
- 1984-04-05 CA CA000451388A patent/CA1220207A/en not_active Expired
- 1984-04-10 KR KR1019840001890A patent/KR840008329A/ko not_active Ceased
- 1984-04-10 KR KR1019840001889A patent/KR860001171B1/ko not_active Expired
- 1984-04-10 KR KR1019840001888A patent/KR860001763B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR860001171B1 (ko) | 1986-08-20 |
| US4514556A (en) | 1985-04-30 |
| EP0126531A3 (en) | 1987-01-14 |
| JPS59190972A (ja) | 1984-10-29 |
| KR840008329A (ko) | 1984-12-14 |
| CA1220207A (en) | 1987-04-07 |
| KR840008648A (ko) | 1984-12-17 |
| EP0126531A2 (en) | 1984-11-28 |
| KR840008328A (ko) | 1984-12-14 |
| KR860001763B1 (ko) | 1986-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4202920A (en) | Cyanoacetic acid derivatives as epoxy resin curing agents | |
| EP0097979B1 (en) | Amino-triazine derivative and its use in heat-curable compositions | |
| GB2052513A (en) | Storage table homogeneous mixture containing epoxide resin curing agent and curing accelerator and the use of the mixture for producing cured products | |
| US5872196A (en) | Liquid epoxy resin composition | |
| WO2011111723A1 (ja) | æš¹èçµæç© | |
| JPH04225971A (ja) | âã°ãªã·ãžã«ååç©ãå«æãã硬åæ§æš¹èçµæç© | |
| KR860001763B1 (ko) | 4,4'-ë©ížë -ë¹ì€-(2-ìíž-5-ë©ížìŽë¯žë€ì¡ž)ì ì ì¡°ë°©ë² | |
| JPS6138732B2 (ja) | ||
| JPS62178564A (ja) | ã¡ã«ã«ãã¿ã³å«æããªããšãâã«ã該ããªããšãâã«ãå«æããçµæç©åã³è©²çµæç©ã®äœ¿çšæ¹æ³ | |
| US3620983A (en) | {11 -methylglycidyl-isocyanurates | |
| JP3369323B2 (ja) | åå°äœå°æ¢çšãšããã·æš¹èçµæç© | |
| JP3650637B2 (ja) | ãšããã·æš¹èçµæç© | |
| US4435549A (en) | N-Cyano amide compositions and adducts thereof | |
| JPS6141911B2 (ja) | ||
| JPS5821632B2 (ja) | ã·ã¯ãã¢ã«ã«ãã³ ã ã»ã€ãŸãŠããŠã㊠| |
| JP2004018452A (ja) | ã€ãœã·ã¢ãã«é žç°ãæããæ°èŠãªãšã¹ãã«ååç©ããã³è©²ååç©ãçšãããšããã·æš¹èçµæç© | |
| JPH06128352A (ja) | ãšããã·æš¹èçµæç© | |
| JPS6055071B2 (ja) | ã€ãããŸãªã«ç¥çé žååç©ããã³è©²ååç©ãçšãããšããã·æš¹è硬åæ¹æ³ | |
| JPS61148228A (ja) | äžæ¶²æ§ãšããã·æš¹èçµæç© | |
| JP3410762B2 (ja) | äžæ¶²åèªå·±ç¡¬åæ§ãšããã·æš¹èçµæç© | |
| JPS6224006B2 (ja) | ||
| JPH0651783B2 (ja) | ãšããã·æš¹èã®ç¡¬åå€ | |
| JPS60255820A (ja) | ãšããã·æš¹èçµæç© | |
| JP3761919B2 (ja) | ãšããã·æš¹èçšç¡¬åä¿é²å€ | |
| JP2777761B2 (ja) | ãšããã·æš¹èã®ç¡¬åæ¹æ³ |