JP5885621B2 - 2- (Methoxyphenyl) imidazole compound and antioxidant - Google Patents
2- (Methoxyphenyl) imidazole compound and antioxidant Download PDFInfo
- Publication number
- JP5885621B2 JP5885621B2 JP2012183809A JP2012183809A JP5885621B2 JP 5885621 B2 JP5885621 B2 JP 5885621B2 JP 2012183809 A JP2012183809 A JP 2012183809A JP 2012183809 A JP2012183809 A JP 2012183809A JP 5885621 B2 JP5885621 B2 JP 5885621B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- copper
- antioxidant
- methoxyphenyl
- compound
- 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.)
- Active
Links
- -1 2- (Methoxyphenyl) imidazole compound Chemical class 0.000 title claims description 51
- 230000003078 antioxidant effect Effects 0.000 title claims description 29
- 239000003963 antioxidant agent Substances 0.000 title claims description 28
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 26
- 239000010949 copper Substances 0.000 claims description 26
- 229910052802 copper Inorganic materials 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 19
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229910000679 solder Inorganic materials 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- AJOSDIDPIBJFAI-UHFFFAOYSA-N 4-methoxybenzenecarboximidamide;hydrochloride Chemical compound Cl.COC1=CC=C(C(N)=N)C=C1 AJOSDIDPIBJFAI-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- KQHLBMVGQBPSMT-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(Cl)C=C1Cl KQHLBMVGQBPSMT-UHFFFAOYSA-N 0.000 description 6
- JTKNCRAAATVMFV-UHFFFAOYSA-N 3,4-dimethoxybenzenecarboximidamide;hydrochloride Chemical compound [Cl-].COC1=CC=C(C(N)=[NH2+])C=C1OC JTKNCRAAATVMFV-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FBMTWRZQBRHOPF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Cl)C=C1Cl FBMTWRZQBRHOPF-UHFFFAOYSA-N 0.000 description 4
- OSEQIDSFSBWXRE-UHFFFAOYSA-N 3,4-dimethoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1OC OSEQIDSFSBWXRE-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- URCBCWXVRZLHMF-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-naphthalen-1-yl-1h-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC=C(C=2C3=CC=CC=C3C=CC=2)N1 URCBCWXVRZLHMF-UHFFFAOYSA-N 0.000 description 3
- WQCCRKVBECYLJY-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(3,4-dimethoxyphenyl)-5-methyl-1h-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C)N1 WQCCRKVBECYLJY-UHFFFAOYSA-N 0.000 description 3
- OAJWJQDYGPMKRL-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(4-methoxyphenyl)-5-methyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C)N1 OAJWJQDYGPMKRL-UHFFFAOYSA-N 0.000 description 3
- QQKZZYDFVKVSQC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(3,4-dimethoxyphenyl)-5-methyl-1h-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C=C(Cl)C(Cl)=CC=2)=C(C)N1 QQKZZYDFVKVSQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- FKGDMSJKLIQBQS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Cl)C(Cl)=C1 FKGDMSJKLIQBQS-UHFFFAOYSA-N 0.000 description 2
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 2
- OQLCVXVVASQZLX-UHFFFAOYSA-N 2-bromo-1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)CBr)=CC=CC2=C1 OQLCVXVVASQZLX-UHFFFAOYSA-N 0.000 description 2
- OWVMFLLVLFONOO-UHFFFAOYSA-N 3-butoxypropanoic acid Chemical compound CCCCOCCC(O)=O OWVMFLLVLFONOO-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-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
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000005476 soldering Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 150000003752 zinc compounds Chemical class 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RMIJMXPBQBQCHQ-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(Cl)=C1Cl RMIJMXPBQBQCHQ-UHFFFAOYSA-N 0.000 description 1
- KRBDEZHXQICPAA-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC(Cl)=CC=C1Cl KRBDEZHXQICPAA-UHFFFAOYSA-N 0.000 description 1
- HSCFVMFKUJTDHG-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2-iodopropan-1-one Chemical compound CC(I)C(=O)C1=CC(Cl)=CC(Cl)=C1 HSCFVMFKUJTDHG-UHFFFAOYSA-N 0.000 description 1
- KFXWPKDEAPLDKF-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC(Cl)=CC(Cl)=C1 KFXWPKDEAPLDKF-UHFFFAOYSA-N 0.000 description 1
- RVULVDCMPNAZQE-UHFFFAOYSA-N 2,2-dichloro-1-phenylpropan-1-one Chemical compound CC(Cl)(Cl)C(=O)C1=CC=CC=C1 RVULVDCMPNAZQE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- CLLLODNOQBVIMS-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetic acid Chemical compound COCCOCC(O)=O CLLLODNOQBVIMS-UHFFFAOYSA-N 0.000 description 1
- IFLXJUPOSSDQRR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-methyl-4-naphthalen-1-yl-1H-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C3=CC=CC=C3C=CC=2)=C(C)N1 IFLXJUPOSSDQRR-UHFFFAOYSA-N 0.000 description 1
- GOWPWPYUHCDACI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-methyl-4-naphthalen-2-yl-1H-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=C(C)N1 GOWPWPYUHCDACI-UHFFFAOYSA-N 0.000 description 1
- RDRRDQGMCGGALU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-4-naphthalen-1-yl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C3=CC=CC=C3C=CC=2)=C(C)N1 RDRRDQGMCGGALU-UHFFFAOYSA-N 0.000 description 1
- ORGZJXLBSQFXLN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-4-naphthalen-2-yl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=C3C=CC=CC3=CC=2)=C(C)N1 ORGZJXLBSQFXLN-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- FYRBJJHCFFXENF-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]acetic acid Chemical compound CCOCCOCCOCC(O)=O FYRBJJHCFFXENF-UHFFFAOYSA-N 0.000 description 1
- XJGUMLITIZHCGE-UHFFFAOYSA-N 2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]acetic acid Chemical compound CCOCCOCCOCCOCC(O)=O XJGUMLITIZHCGE-UHFFFAOYSA-N 0.000 description 1
- XWAIBCLYBCOGPX-UHFFFAOYSA-N 2-bromo-1-(2,3-dichlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=CC(Cl)=C1Cl XWAIBCLYBCOGPX-UHFFFAOYSA-N 0.000 description 1
- VLNACFMTJGOEPP-UHFFFAOYSA-N 2-bromo-1-(2,5-dichlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC(Cl)=CC=C1Cl VLNACFMTJGOEPP-UHFFFAOYSA-N 0.000 description 1
- YPKHWACIODYBCI-UHFFFAOYSA-N 2-bromo-1-(3,4-dichlorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(Cl)C(Cl)=C1 YPKHWACIODYBCI-UHFFFAOYSA-N 0.000 description 1
- FGZJTYQVOKKPSJ-UHFFFAOYSA-N 2-bromo-1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)C(Br)C)=CC=CC2=C1 FGZJTYQVOKKPSJ-UHFFFAOYSA-N 0.000 description 1
- BWABACVFJJBKOR-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)propan-1-one Chemical compound CC(Cl)C(=O)C1=CC=C(Cl)C=C1Cl BWABACVFJJBKOR-UHFFFAOYSA-N 0.000 description 1
- XLSUKENQJDZSCX-UHFFFAOYSA-N 2-chloro-1-(3,4-dichlorophenyl)propan-1-one Chemical compound CC(Cl)C(=O)C1=CC=C(Cl)C(Cl)=C1 XLSUKENQJDZSCX-UHFFFAOYSA-N 0.000 description 1
- VYOLNYSIZIEAOP-UHFFFAOYSA-N 2-chloro-1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)CCl)=CC=CC2=C1 VYOLNYSIZIEAOP-UHFFFAOYSA-N 0.000 description 1
- XRCRRENQSPVZIB-UHFFFAOYSA-N 2-chloro-1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)C(Cl)C)=CC=CC2=C1 XRCRRENQSPVZIB-UHFFFAOYSA-N 0.000 description 1
- AJLOJLVEADHPJX-UHFFFAOYSA-N 2-chloro-1-naphthalen-2-ylpropan-1-one Chemical compound C1=CC=CC2=CC(C(=O)C(Cl)C)=CC=C21 AJLOJLVEADHPJX-UHFFFAOYSA-N 0.000 description 1
- YUNLQIAWOVSQCH-UHFFFAOYSA-N 2-iodo-1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)CI)=CC=CC2=C1 YUNLQIAWOVSQCH-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- SGUYGLMQEOSQTH-UHFFFAOYSA-N 2-propoxyacetic acid Chemical compound CCCOCC(O)=O SGUYGLMQEOSQTH-UHFFFAOYSA-N 0.000 description 1
- GRNBGCVJIQHIKG-UHFFFAOYSA-N 3,4-dimethoxybenzenecarboximidamide Chemical compound COC1=CC=C(C(N)=N)C=C1OC GRNBGCVJIQHIKG-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- HTNUUDFQRYBJPH-UHFFFAOYSA-N 3-methoxypropanehydrazide Chemical compound COCCC(=O)NN HTNUUDFQRYBJPH-UHFFFAOYSA-N 0.000 description 1
- YZLDXPLNKWTMOO-UHFFFAOYSA-N 3-propoxypropanoic acid Chemical compound CCCOCCC(O)=O YZLDXPLNKWTMOO-UHFFFAOYSA-N 0.000 description 1
- IPNDQWCHYRUQPM-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2-(3,4-dimethoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C(=C(Cl)C=CC=2)Cl)=C(C)N1 IPNDQWCHYRUQPM-UHFFFAOYSA-N 0.000 description 1
- MRLYQLQOAJHGDD-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2-(4-methoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=C(Cl)C=CC=2)Cl)=C(C)N1 MRLYQLQOAJHGDD-UHFFFAOYSA-N 0.000 description 1
- IDYIYVSJDWCOCO-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-[(3,4-dimethoxyphenyl)methyl]-5-methyl-1h-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C)N1 IDYIYVSJDWCOCO-UHFFFAOYSA-N 0.000 description 1
- GARBEZDSVCOIQT-UHFFFAOYSA-N 4-(2,5-dichlorophenyl)-2-(3,4-dimethoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C(=CC=C(Cl)C=2)Cl)=C(C)N1 GARBEZDSVCOIQT-UHFFFAOYSA-N 0.000 description 1
- BPYZBHCOYDSYII-UHFFFAOYSA-N 4-(2,5-dichlorophenyl)-2-(4-methoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=CC=C(Cl)C=2)Cl)=C(C)N1 BPYZBHCOYDSYII-UHFFFAOYSA-N 0.000 description 1
- OQMDESBUNZDIQI-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-2-(3,4-dimethoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C(=CC=CC=2Cl)Cl)=C(C)N1 OQMDESBUNZDIQI-UHFFFAOYSA-N 0.000 description 1
- HFPRKXXXRHCKJX-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-2-(4-methoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=CC=CC=2Cl)Cl)=C(C)N1 HFPRKXXXRHCKJX-UHFFFAOYSA-N 0.000 description 1
- UDQCVBNQSURTBG-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(4-methoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=C(Cl)C(Cl)=CC=2)=C(C)N1 UDQCVBNQSURTBG-UHFFFAOYSA-N 0.000 description 1
- QUKAXWNRAWRJPZ-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-(3,4-dimethoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C=C(Cl)C=C(Cl)C=2)=C(C)N1 QUKAXWNRAWRJPZ-UHFFFAOYSA-N 0.000 description 1
- GGAXAHJXANGLQB-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-(4-methoxyphenyl)-5-methyl-1H-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=C(Cl)C=C(Cl)C=2)=C(C)N1 GGAXAHJXANGLQB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CSISQILZUHMAJB-UHFFFAOYSA-N 4-methoxybenzenecarboximidamide Chemical compound COC1=CC=C(C(N)=N)C=C1 CSISQILZUHMAJB-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GGISFAVYQATCBV-UHFFFAOYSA-N C(C)Cl.COC1=CC=C(C(O)=N)C=C1 Chemical compound C(C)Cl.COC1=CC=C(C(O)=N)C=C1 GGISFAVYQATCBV-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- PMJYGTGNXLCKOE-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)C(C(C)I)=O Chemical compound ClC1=C(C(=CC=C1)Cl)C(C(C)I)=O PMJYGTGNXLCKOE-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 description 1
- RAOSIAYCXKBGFE-UHFFFAOYSA-K [Cu+3].[O-]P([O-])([O-])=O Chemical compound [Cu+3].[O-]P([O-])([O-])=O RAOSIAYCXKBGFE-UHFFFAOYSA-K 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000003139 buffering effect Effects 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
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000007788 liquid 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
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- WEZYFYMYMKUAHY-UHFFFAOYSA-N tert-butyl 2,4-dibenzylpiperazine-1-carboxylate Chemical compound C1C(CC=2C=CC=CC=2)N(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WEZYFYMYMKUAHY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
本発明は、新規な2−(メトキシフェニル)イミダゾール化合物及び該イミダゾール化合物を含有する銅又は銅合金の酸化防止剤に関するものである。 The present invention relates to a novel 2- (methoxyphenyl) imidazole compound and a copper or copper alloy antioxidant containing the imidazole compound.
本発明に類似のイミダゾール化合物として、例えば、特許文献1には、化学式(III)で示される4−(2,4−ジクロロフェニル)−2−(3,4−ジメトキシベンジル)−5−メチル−イミダゾールが開示されている。しかしながら、この文献には本発明のイミダゾール化合物の開示はない。 As an imidazole compound similar to the present invention, for example, Patent Document 1 discloses 4- (2,4-dichlorophenyl) -2- (3,4-dimethoxybenzyl) -5-methyl-imidazole represented by the chemical formula (III). Is disclosed. However, this document does not disclose the imidazole compound of the present invention.
本発明は、新規な2−(メトキシフェニル)イミダゾール化合物及び該イミダゾール化合物を含有する銅又は銅合金の酸化防止剤を提供することを目的とする。 An object of the present invention is to provide a novel 2- (methoxyphenyl) imidazole compound and a copper or copper alloy antioxidant containing the imidazole compound.
本発明者等は、前記の課題を解決するために鋭意検討を重ねた結果、化学式(I)又は化学式(II)で示される新規な2−(メトキシフェニル)イミダゾール化合物を合成し得ることを認め、また該イミダゾール化合物が銅又は銅合金表面の酸化防止効果を発揮することを見出し、本発明を完成するに至ったものである。
即ち、第1の発明は化学式(I)又は化学式(II)で示される2−(メトキシフェニル)イミダゾール化合物であり、第2の発明は該イミダゾール化合物を含有することを特徴とする銅又は銅合金の酸化防止剤である。
As a result of intensive studies to solve the above-mentioned problems, the present inventors have recognized that a novel 2- (methoxyphenyl) imidazole compound represented by the chemical formula (I) or the chemical formula (II) can be synthesized. In addition, the inventors have found that the imidazole compound exhibits an antioxidant effect on the surface of copper or a copper alloy, and have completed the present invention.
That is, the first invention is a 2- (methoxyphenyl) imidazole compound represented by the chemical formula (I) or the chemical formula (II), and the second invention is characterized by containing the imidazole compound. It is an antioxidant.
本発明の2−(メトキシフェニル)イミダゾール化合物は、金属、特に銅又は銅合金(以下、両者を併せて単に銅と云う)の表面の酸化防止剤や、エポキシ樹脂の硬化剤又は硬化促進剤として、また医農薬分野の中間原料としても有用なものである。また、本発明の2−(メトキシフェニル)イミダゾール化合物を含有する銅の酸化防止剤は、銅表面をはんだ付けする際のはんだ付け性を良好なものとすることができる。 The 2- (methoxyphenyl) imidazole compound of the present invention is used as an antioxidant on the surface of a metal, particularly copper or a copper alloy (hereinafter simply referred to as copper), or as a curing agent or curing accelerator for an epoxy resin. It is also useful as an intermediate material in the medical and agrochemical field. Moreover, the antioxidant of copper containing the 2- (methoxyphenyl) imidazole compound of the present invention can improve the solderability when soldering the copper surface.
以下、本発明について詳細に説明する。
本発明の2−(メトキシフェニル)イミダゾール化合物は、
4−(2,3−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾール、
4−(2,4−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾール、
4−(2,5−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾール、
4−(2,6−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾール、
4−(3,4−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾール、
4−(3,5−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾール、
2−(4−メトキシフェニル)−5−メチル−4−(1−ナフチル)イミダゾール、
2−(4−メトキシフェニル)−5−メチル−4−(2−ナフチル)イミダゾール、
4−(2,3−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾール、
4−(2,4−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾール、
4−(2,5−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾール、
4−(2,6−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾール、
4−(3,4−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾール、
4−(3,5−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾール、
2−(3,4−ジメトキシフェニル)−5−メチル−4−(1−ナフチル)イミダゾール、
2−(3,4−ジメトキシフェニル)−5−メチル−4−(2−ナフチル)イミダゾール及び
2−(3,4−ジメトキシフェニル)−4−(1−ナフチル)イミダゾールである。
Hereinafter, the present invention will be described in detail.
The 2- (methoxyphenyl) imidazole compound of the present invention is
4- (2,3-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole,
4- (2,4-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole,
4- (2,5-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole,
4- (2,6-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole,
4- (3,4-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole,
4- (3,5-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole,
2- (4-methoxyphenyl) -5-methyl-4- (1-naphthyl) imidazole,
2- (4-methoxyphenyl) -5-methyl-4- (2-naphthyl) imidazole,
4- (2,3-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole,
4- (2,4-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole,
4- (2,5-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole,
4- (2,6-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole,
4- (3,4-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole,
4- (3,5-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole,
2- (3,4-dimethoxyphenyl) -5-methyl-4- (1-naphthyl) imidazole,
2- (3,4-dimethoxyphenyl) -5-methyl-4- (2-naphthyl) imidazole and 2- (3,4-dimethoxyphenyl) -4- (1-naphthyl) imidazole.
本発明の2−(メトキシフェニル)イミダゾール化合物は、公知の方法に準拠して合成することができる。例えば、反応式(A)に示されるように、2位ハロゲン化アルキルアリールケトン化合物及びメトキシベンズアミジン化合物を脱ハロゲン化水素剤の存在下、有機溶媒中で加熱反応をさせることにより合成することができる。 The 2- (methoxyphenyl) imidazole compound of the present invention can be synthesized according to a known method. For example, as shown in the reaction formula (A), a 2-position halogenated alkylaryl ketone compound and a methoxybenzamidine compound can be synthesized by heating in an organic solvent in the presence of a dehydrohalogenating agent. it can.
前述の反応においてメトキシベンズアミジン化合物の使用量は、2位ハロゲン化アルキルアリールケトン化合物に対して、0.8〜1.5倍モルが好ましく、より好ましくは0.9〜1.1倍モルの割合とすればよい。脱ハロゲン化水素剤の使用量は、2位ハロゲン化アルキルアリールケトン化合物に対して、1〜10倍当量の割合が好ましい。 In the above reaction, the amount of the methoxybenzamidine compound used is preferably 0.8 to 1.5 moles, more preferably 0.9 to 1.1 moles, relative to the 2-position halogenated alkylaryl ketone compound. What is necessary is just a ratio. The amount of the dehydrohalogenating agent used is preferably a ratio of 1 to 10 times equivalent to the 2-position halogenated alkyl aryl ketone compound.
前記の2位ハロゲン化アルキルアリールケトン化合物としては、2−ブロモ−2′,3′−ジクロロプロピオフェノン、2,2′,4′−トリクロロプロピオフェノン、2−ブロモ−2′,4′−ジクロロプロピオフェノン、2−ブロモ−2′,5′−ジクロロプロピオフェノン、2′,6′−ジクロロ−2−ヨードプロピオフェノン、2,3′,4′−トリクロロプロピオフェノン、2−ブロモ−3′,4′−ジクロロプロピオフェノン、3′,5′−ジクロロ−2−ヨードプロピオフェノン、2−クロロ−1′−アセトナフトン、2−ブロモ−1′−アセトナフトン、2−ヨード−1′−アセトナフトン、2−クロロ−1′−プロピオナフトン、2−ブロモ−1′−プロピオナフトン、2−クロロ−2′−プロピオナフトン及び2−ブロモ−2′−プロピオナフトン等が挙げられる。 Examples of the 2-position halogenated alkyl aryl ketone compound include 2-bromo-2 ', 3'-dichloropropiophenone, 2,2', 4'-trichloropropiophenone, 2-bromo-2 ', 4'. -Dichloropropiophenone, 2-bromo-2 ', 5'-dichloropropiophenone, 2', 6'-dichloro-2-iodopropiophenone, 2,3 ', 4'-trichloropropiophenone, 2 -Bromo-3 ', 4'-dichloropropiophenone, 3', 5'-dichloro-2-iodopropiophenone, 2-chloro-1'-acetonaphthone, 2-bromo-1'-acetonaphthone, 2-iodo -1'-acetonaphthone, 2-chloro-1'-propionnaphthone, 2-bromo-1'-propionnaphthone, 2-chloro-2'-propionnaphthone and 2-bromine 2'-Puropionafuton, and the like.
これらの2位ハロゲン化アルキルアリールケトン化合物は、アルキルアリールケトン化合物の2位をハロゲン化することにより合成することができる。2位ハロゲン化の内、2位塩素化及び2位ヨウ素化も可能であるが、アルキルアリールケトン化合物1モルに対し、1モルの臭素を反応させる2位臭素化が最も簡便である。 These 2-position halogenated alkyl aryl ketone compounds can be synthesized by halogenating the 2-position of the alkyl aryl ketone compound. Among the 2-position halogenations, 2-position chlorination and 2-position iodination are possible, but 2-position bromination in which 1 mole of bromine is reacted with 1 mole of alkyl aryl ketone compound is the simplest.
前記のアルキルアリールケトン化合物としては、2′,3′−ジクロロプロピオフェノン、2′,4′−ジクロロプロピオフェノン、2′,5′−ジクロロプロピオフェノン、2′,6′−ジクロロプロピオフェノン、3′,4′−ジクロロプロピオフェノン、3′,5′−ジクロロプロピオフェノン、1−アセトナフトン、1−プロピオナフトン及び2−プロピオナフトンが挙げられる。これらは公知の化合物であり、試薬として市販されているものを使用することができる。 Examples of the alkyl aryl ketone compound include 2 ', 3'-dichloropropiophenone, 2', 4'-dichloropropiophenone, 2 ', 5'-dichloropropiophenone, 2', 6'-dichloroprone. Piophenone, 3 ', 4'-dichloropropiophenone, 3', 5'-dichloropropiophenone, 1-acetonaphthone, 1-propionnaphthone and 2-propionnaphthone are mentioned. These are known compounds, and those commercially available as reagents can be used.
前記のメトキシベンズアミジン化合物は、公知の方法に準拠して合成することが出来る。すなわち、反応式(B)に示されるように、前駆体のニトリル化合物を塩化水素ガス及びエタノール等の低級アルコールと反応させ、イミデート・塩酸塩化合物に変換し、更にアンモニアと反応させることによってアミジン化合物を合成することができる。 The methoxybenzamidine compound can be synthesized according to a known method. That is, as shown in the reaction formula (B), the precursor nitrile compound is reacted with a lower alcohol such as hydrogen chloride gas and ethanol, converted into an imidate / hydrochloride compound, and further reacted with ammonia to form an amidine compound. Can be synthesized.
前記のアミジン化合物としては、4−メトキシベンズアミジン、3,4−ジメトキシベンズアミジン及びこれらの塩酸塩等の無機酸塩や酢酸塩等の有機酸塩が挙げられる。 Examples of the amidine compounds include inorganic acid salts such as 4-methoxybenzamidine, 3,4-dimethoxybenzamidine and their hydrochlorides, and organic acid salts such as acetates.
前記のニトリル化合物としては、4−メトキシベンゾニトリル及び3,4−ジメトキシベンゾニトリルが挙げられる。これらは公知の化合物であり、試薬として市販されているものを使用することができる。 Examples of the nitrile compound include 4-methoxybenzonitrile and 3,4-dimethoxybenzonitrile. These are known compounds, and those commercially available as reagents can be used.
前記の脱ハロゲン化水素剤としては、公知のものを制限なく使用できる。このような脱ハロゲン化水素剤としては、例えば、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウム、重炭酸カリウムのような無機アルカリ類、トリエチルアミン、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン(DBU)のような有機塩基類、ナトリウムメトキシド、カリウムtert−ブトキシドのような金属アルコキシド類等が挙げられる。 As the dehydrohalogenating agent, known ones can be used without limitation. Examples of such a dehydrohalogenating agent include inorganic alkalis such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, 1,8 -Organic bases such as diazabicyclo [5,4,0] -7-undecene (DBU), metal alkoxides such as sodium methoxide and potassium tert-butoxide, and the like.
前記の有機溶媒としては、2位ハロゲン化アルキルアリールケトン化合物及びメトキシベンズアミジン化合物を溶解することができ、かつ反応に関与しないものであれば公知のものを制限なく使用できる。このような溶媒として、例えば、イソプロピルアルコール、tert−ブタノールなどのアルコール類、ヘキサン、トルエンなどの炭化水素類、クロロホルム、クロロベンゼンなどのハロゲン化炭化水素類、酢酸エチルなどのエステル類、アセトニトリルなどのニトリル類、テトラヒドロフラン、ジオキサン、エチレングリコールジメチルエーテルなどのエーテル類、N,N−ジメチルホルムアミド(DMF)、N,N−ジメチルアセトアミド(DMAC)などのアミド類、ジメチルスルホキシド(DMSO)などが挙げられ、これらの溶媒を組合わせて使用してもよい。 As the organic solvent, any known organic solvent can be used without limitation as long as it can dissolve the halogenated alkylaryl ketone compound and methoxybenzamidine compound and does not participate in the reaction. Examples of such solvents include alcohols such as isopropyl alcohol and tert-butanol, hydrocarbons such as hexane and toluene, halogenated hydrocarbons such as chloroform and chlorobenzene, esters such as ethyl acetate, and nitriles such as acetonitrile. , Ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, amides such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), dimethyl sulfoxide (DMSO), and the like. A combination of solvents may be used.
反応温度については、室温〜還流温度とすることが好ましく、反応時間については、1〜10時間とすることが好ましい。反応は、通常大気圧下で行えばよい。 The reaction temperature is preferably room temperature to reflux temperature, and the reaction time is preferably 1 to 10 hours. The reaction may be usually performed under atmospheric pressure.
以上の反応条件下で生成した2−(メトキシフェニル)イミダゾール化合物は、通常の後処理によって単離することができる。
例えば、反応終了後の反応混合物を水層と有機溶媒層に分配し、有機溶媒層を水で洗浄することにより結晶として析出する粗製の2−(メトキシフェニル)イミダゾール化合物を得ることができ、それを再結晶操作等により精製することができる。
The 2- (methoxyphenyl) imidazole compound produced under the above reaction conditions can be isolated by ordinary post-treatment.
For example, a crude 2- (methoxyphenyl) imidazole compound that precipitates as crystals can be obtained by partitioning the reaction mixture after completion of the reaction into an aqueous layer and an organic solvent layer, and washing the organic solvent layer with water. Can be purified by a recrystallization operation or the like.
この2−(メトキシフェニル)イミダゾール化合物は、水に溶解させて調製される銅の酸化防止剤の有効成分として使用される。該イミダゾール化合物は酸化防止剤中に、0.01〜10重量%の割合、好ましくは0.1〜5重量%の割合で含有される。該イミダゾール化合物の含有割合が0.01重量%より少ないと、銅表面に形成される化成皮膜の膜厚が薄くなり、銅表面の酸化を十分に防止することができない。また、10重量%より多い場合には酸化防止剤中に該イミダゾール化合物が溶け残ったり、あるいは完溶したとしても再析出する虞があり好ましくない。 This 2- (methoxyphenyl) imidazole compound is used as an active ingredient of a copper antioxidant prepared by dissolving in water. The imidazole compound is contained in the antioxidant in a proportion of 0.01 to 10% by weight, preferably in a proportion of 0.1 to 5% by weight. When the content ratio of the imidazole compound is less than 0.01% by weight, the film thickness of the chemical conversion film formed on the copper surface becomes thin, and oxidation of the copper surface cannot be sufficiently prevented. On the other hand, when the amount is more than 10% by weight, the imidazole compound may remain undissolved in the antioxidant or may be reprecipitated even if it is completely dissolved.
本発明の実施において、当該イミダゾール化合物を水に溶解(水溶液化)するに当たっては、通常、酸として有機酸又は無機酸を使用するが、少量の有機溶媒を併用しても良い。この際に使用される代表的な有機酸としては、蟻酸、酢酸、プロピオン酸、酪酸、グリオキシル酸、ピルビン酸、アセト酢酸、レブリン酸、ヘプタン酸、カプリル酸、カプリン酸、ラウリン酸、グリコール酸、グリセリン酸、乳酸、グルコン酸、アクリル酸、メトキシ酢酸、エトキシ酢酸、プロポキシ酢酸、ブトキシ酢酸、2−(2−メトキシエトキシ)酢酸、2−[2−(2−エトキシエトキシ)エトキシ]酢酸、2−{2−[2−(2−エトキシエトキシ)エトキシ]エトキシ}酢酸、3−メトキシプロピオン酸、3−エトキシプロピオン酸、3−プロポキシプロピオン酸、3−ブトキシプロピオン酸、安息香酸、パラニトロ安息香酸、パラトルエンスルホン酸、サリチル酸、ピクリン酸、蓚酸、コハク酸、マレイン酸、フマール酸、酒石酸、アジピン酸等が挙げられ、無機酸としては、塩酸、リン酸、硫酸、硝酸等が挙げられる。これらの酸は、酸化防止剤中に0.1〜50重量%の割合、好ましくは1〜30重量%の割合で含有される。 In the practice of the present invention, an organic acid or an inorganic acid is usually used as the acid when the imidazole compound is dissolved (made into an aqueous solution) in water, but a small amount of an organic solvent may be used in combination. Typical organic acids used in this case include formic acid, acetic acid, propionic acid, butyric acid, glyoxylic acid, pyruvic acid, acetoacetic acid, levulinic acid, heptanoic acid, caprylic acid, capric acid, lauric acid, glycolic acid, Glyceric acid, lactic acid, gluconic acid, acrylic acid, methoxyacetic acid, ethoxyacetic acid, propoxyacetic acid, butoxyacetic acid, 2- (2-methoxyethoxy) acetic acid, 2- [2- (2-ethoxyethoxy) ethoxy] acetic acid, 2- {2- [2- (2-Ethoxyethoxy) ethoxy] ethoxy} acetic acid, 3-methoxypropionic acid, 3-ethoxypropionic acid, 3-propoxypropionic acid, 3-butoxypropionic acid, benzoic acid, paranitrobenzoic acid, para Toluenesulfonic acid, salicylic acid, picric acid, succinic acid, succinic acid, maleic acid, fumaric acid, liquor Acid, and adipic acid. Examples of the inorganic acids, hydrochloric acid, phosphoric acid, sulfuric acid, and nitric acid. These acids are contained in the antioxidant in a proportion of 0.1 to 50% by weight, preferably 1 to 30% by weight.
また、有機溶媒としては、メタノール、エタノール、イソプロピルアルコールなどの低級アルコールあるいはアセトン、N,N−ジメチルホルムアミド、エチレングリコール等の水と自由に混和するものが適している。 As the organic solvent, those which are freely miscible with water such as lower alcohols such as methanol, ethanol and isopropyl alcohol or water such as acetone, N, N-dimethylformamide and ethylene glycol are suitable.
本発明の酸化防止剤には、銅の表面における化成皮膜の形成速度を速めるために銅化合物を添加することができ、また形成された化成皮膜の耐熱性を更に向上させるために亜鉛化合物を添加しても良い。
前記銅化合物の代表的なものとしては、酢酸銅、塩化第一銅、塩化第二銅、臭化第一銅、臭化第二銅、ヨウ化銅、水酸化銅、リン酸銅、硫酸銅、硝酸銅等が挙げられる。
また、前記亜鉛化合物の代表的なものとしては、酸化亜鉛、蟻酸亜鉛、酢酸亜鉛、蓚酸亜鉛、乳酸亜鉛、クエン酸亜鉛、硫酸亜鉛、硝酸亜鉛、リン酸亜鉛等が挙げられ、何れも酸化防止剤中に0.01〜10重量%の割合、好ましくは0.02〜5重量%の割合で含有させれば良い。
To the antioxidant of the present invention, a copper compound can be added in order to increase the formation rate of the chemical conversion film on the surface of copper, and a zinc compound is added to further improve the heat resistance of the formed chemical conversion film. You may do it.
Representative examples of the copper compound include copper acetate, cuprous chloride, cupric chloride, cuprous bromide, cupric bromide, copper iodide, copper hydroxide, copper phosphate, copper sulfate. And copper nitrate.
Representative examples of the zinc compound include zinc oxide, zinc formate, zinc acetate, zinc oxalate, zinc lactate, zinc citrate, zinc sulfate, zinc nitrate, zinc phosphate, etc. What is necessary is just to make it contain in the ratio of 0.01-10 weight% in an agent, Preferably it is a ratio of 0.02-5 weight%.
本発明の酸化防止剤には、化成皮膜の形成速度及び該皮膜の耐熱性を更に向上させるために、ハロゲン化合物を酸化防止剤中に0.001〜1重量%、好ましくは0.01〜0.1重量%の含有割合となるように添加することができる。ハロゲン化合物としては、例えばフッ化ナトリウム、フッ化カリウム、フッ化アンモニウム、塩化ナトリム、塩化カリウム、塩化アンモニウム、臭化ナトリウム、臭化カリウム、臭化アンモニウム、ヨウ化ナトリム、ヨウ化カリウム、ヨウ化アンモニウム等が挙げられる。 In the antioxidant of the present invention, in order to further improve the formation rate of the chemical conversion film and the heat resistance of the film, the halogen compound is added in an amount of 0.001 to 1% by weight, preferably 0.01 to 0% in the antioxidant. .1% by weight can be added. Examples of the halogen compound include sodium fluoride, potassium fluoride, ammonium fluoride, sodium chloride, potassium chloride, ammonium chloride, sodium bromide, potassium bromide, ammonium bromide, sodium iodide, potassium iodide, and ammonium iodide. Etc.
本発明の酸化防止剤を用いて銅の表面を処理する際には、酸化防止剤のpHを調整することが好ましい。このpHは、酸化防止剤の組成(成分の種類と含有量)や後述する処理温度と処理時間に応じて適宜設定される。
pHを下げる場合には、前述の有機酸又は無機酸を使用することができ、pHを上げる場合には、水酸化ナトリウムや水酸化カリウムの他、アンモニアあるいはモノエタノールアミン、ジエタノールアミン、トリエタノールアミンなどのアミン類等の緩衝作用を有する物質が好ましく使用できる。
When treating the surface of copper using the antioxidant of the present invention, it is preferable to adjust the pH of the antioxidant. This pH is appropriately set according to the composition (type and content of components) of the antioxidant and the processing temperature and processing time described below.
When lowering the pH, the above-mentioned organic acid or inorganic acid can be used, and when raising the pH, in addition to sodium hydroxide or potassium hydroxide, ammonia or monoethanolamine, diethanolamine, triethanolamine, etc. Substances having a buffering action such as amines can be preferably used.
本発明の酸化防止剤を用いて銅の表面を処理する際の条件としては、酸化防止剤の液温を10〜70℃、接触時間を1秒〜10分とすることが好ましい。接触方法としては、浸漬、噴霧、塗布等の方法が挙げられる。 As conditions for treating the surface of copper using the antioxidant of the present invention, the liquid temperature of the antioxidant is preferably 10 to 70 ° C., and the contact time is preferably 1 second to 10 minutes. Examples of the contact method include dipping, spraying, and application methods.
以下、本発明を実施例によって具体的に説明するが、本発明はこれらに限定されるものではない。なお、2−ブロモ−2′,4′−ジクロロプロピオフェノン及び4−メトキシベンズアミジン塩酸塩の合成例を、参考例1及び2に示す。 EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples. Reference Examples 1 and 2 show synthesis examples of 2-bromo-2 ′, 4′-dichloropropiophenone and 4-methoxybenzamidine hydrochloride.
〔参考例1〕
<2−ブロモ−2′,4′−ジクロロプロピオフェノン/トルエン溶液の調製>
2′,4′−ジクロロプロピオフェノン50.7g(0.250mol)及びメタノール56gからなる溶液に、50〜55℃にて、臭素40.3g(0.252mol)を1時間20分かけて滴下した。次いで、反応液を冷却後、濃縮物が75.0gになるまで減圧濃縮した。濃縮物をトルエン97g及び水130gに分配し、トルエン層を水130gで洗浄した後、硫酸ナトリウムで乾燥して、黄褐色透明の2−ブロモ−2′,4′−ジクロロプロピオフェノン(0.250mol)/トルエン溶液を得た。
[Reference Example 1]
<Preparation of 2-bromo-2 ', 4'-dichloropropiophenone / toluene solution>
To a solution composed of 50.7 g (0.250 mol) of 2 ′, 4′-dichloropropiophenone and 56 g of methanol, 40.3 g (0.252 mol) of bromine was dropped over 1 hour and 20 minutes at 50 to 55 ° C. did. Subsequently, the reaction liquid was cooled and then concentrated under reduced pressure until the concentrate became 75.0 g. The concentrate was partitioned between 97 g of toluene and 130 g of water, and the toluene layer was washed with 130 g of water and then dried over sodium sulfate to give a tan transparent 2-bromo-2 ', 4'-dichloropropiophenone (0. 250 mol) / toluene solution was obtained.
〔参考例2〕
<4−メトキシベンズアミジン塩酸塩の合成>
4−メトキシベンゾニトリル51.1g(0.384mol)を脱水エタノール18.6g(0.404mol)及び脱水ジクロロメタン103gに溶解させ、冷却下3〜10℃にて、塩化水素ガス20.1g(0.551mol)を1時間30分間かけて吹き込んだ。次いで、同温度で5時間撹拌した後、冷蔵庫に4℃/5日間放置して得られた粘性のある溶液を減圧乾固して、白色結晶性固体の4−メトキシベンゾイミド酸エチル塩酸塩72.8g(0.338mol、収率87.9%)を得た。
該固体を粉砕し、氷冷下に振とうしながら、アンモニア14.2g(0.833mol)及び脱水エタノール90.3gからなる溶液を少量ずつ加えた。その後、氷冷下にて3時間撹拌し、更に室温に戻して一晩撹拌した。
得られた懸濁液を減圧濃縮して92.9gの結晶を得た。該結晶にヘキサン/ジクロロメタン溶液(1:1体積比)150mlを加えて分散洗浄し、結晶をろ取した。そして、同ヘキサン/ジクロロメタン溶液でケーキ洗浄し、減圧下に乾燥して白色結晶の4−メトキシベンズアミジン塩酸塩46.5g(0.249mol、収率64.8%)を得た。
[Reference Example 2]
<Synthesis of 4-methoxybenzamidine hydrochloride>
4-Methoxybenzonitrile (51.1 g, 0.384 mol) was dissolved in dehydrated ethanol (18.6 g, 0.404 mol) and dehydrated dichloromethane (103 g). 551 mol) was blown in over 1 hour 30 minutes. Next, after stirring at the same temperature for 5 hours, the viscous solution obtained by leaving in a refrigerator at 4 ° C. for 5 days was dried under reduced pressure to give white crystalline solid 4-methoxybenzoimidate ethyl hydrochloride 72 0.8 g (0.338 mol, yield 87.9%) was obtained.
The solid was pulverized and a solution consisting of 14.2 g (0.833 mol) of ammonia and 90.3 g of dehydrated ethanol was added little by little while shaking under ice cooling. Thereafter, the mixture was stirred for 3 hours under ice-cooling, and further returned to room temperature and stirred overnight.
The obtained suspension was concentrated under reduced pressure to obtain 92.9 g of crystals. To the crystals, 150 ml of a hexane / dichloromethane solution (1: 1 volume ratio) was added and dispersed and washed, and the crystals were collected by filtration. The cake was washed with the same hexane / dichloromethane solution, and dried under reduced pressure to obtain 46.5 g (0.249 mol, yield 64.8%) of 4-methoxybenzamidine hydrochloride as white crystals.
〔実施例1〕
<4−(2,4−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾールの合成>
4−メトキシベンズアミジン塩酸塩46.5g(0.249mol)をN,N−ジメチルアセトアミド130gに43℃にて加温懸濁させ、炭酸カリウム95g(0.687mol)を加えて5分間撹拌後、参考例1で調製した2−ブロモ−2′,4′−ジクロロプロピオフェノン/トルエン溶液を43〜52℃にて70分間かけて滴下した。滴下終了後、66〜70℃にて3時間撹拌した。
次いで、反応懸濁液を冷却後、水600mlと撹拌し、分液した有機層を水600mlで洗浄し結晶を析出させた。該結晶をろ取し、トルエンでケーキ洗浄し、減圧下に乾燥してクリーム色粉末を得た。該粉末をアセトニトリル547g及びN,N−ジメチルホルムアミド246gの混合溶媒より再結晶して、乳白色粉末44.1gを得た。
[Example 1]
<Synthesis of 4- (2,4-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole>
4-Methoxybenzamidine hydrochloride 46.5 g (0.249 mol) was suspended in N, N-dimethylacetamide 130 g by heating at 43 ° C., potassium carbonate 95 g (0.687 mol) was added, and the mixture was stirred for 5 minutes. The 2-bromo-2 ′, 4′-dichloropropiophenone / toluene solution prepared in Reference Example 1 was added dropwise at 43 to 52 ° C. over 70 minutes. After completion of dropping, the mixture was stirred at 66 to 70 ° C. for 3 hours.
Next, the reaction suspension was cooled and stirred with 600 ml of water, and the separated organic layer was washed with 600 ml of water to precipitate crystals. The crystals were collected by filtration, washed with cake with toluene, and dried under reduced pressure to obtain a cream powder. The powder was recrystallized from a mixed solvent of 547 g of acetonitrile and 246 g of N, N-dimethylformamide to obtain 44.1 g of milky white powder.
得られた粉末の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp227−229℃
・TLC(シリカゲル,アセトン):Rf=0.74
・1H NMR(DMSO-d6):δ=3.40(s,3H),4.28(s,3H),7.00−7.87(m,7H).
・MS(EI):m/z(%)=334(M+2,65),332(M+,100),317(36),289(8),253(2),186(2),166(5),149(2),134(4),119(5),102(3).
これらのスペクトルデータから、得られた粉末は、化学式(IV)で示される4−(2,4−ジクロロフェニル)−2−(4−メトキシフェニル)−5−メチルイミダゾールであるものと同定した。収率52.9%。
The melting point of the obtained powder, Rf value of thin layer chromatography, 1 H NMR and mass spectrum data were as follows.
・ Mp227-229 ℃
・ TLC (silica gel, acetone): Rf = 0.74
-1 H NMR (DMSO-d 6 ): δ = 3.40 (s, 3H), 4.28 (s, 3H), 7.00-7.87 (m, 7H).
MS (EI): m / z (%) = 334 (M + 2, 65), 332 (M + , 100), 317 (36), 289 (8), 253 (2), 186 (2), 166 (5), 149 (2), 134 (4), 119 (5), 102 (3).
From these spectral data, the obtained powder was identified as 4- (2,4-dichlorophenyl) -2- (4-methoxyphenyl) -5-methylimidazole represented by the chemical formula (IV). Yield 52.9%.
〔実施例2〕
<4−(2,4−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾールの合成>
まず、参考例2の4−メトキシベンゾニトリルを3,4−ジメトキシベンゾニトリルに代えて、参考例2の方法に準拠して3,4−ジメトキシベンズアミジン塩酸塩を調製した。
次いで、実施例1の4−メトキシベンズアミジン塩酸塩を3,4−ジメトキシベンズアミジン塩酸塩に代えて、実施例1の方法に準拠して合成試験を行い、白色粉末を得た。
[Example 2]
<Synthesis of 4- (2,4-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole>
First, 3,4-dimethoxybenzamidine hydrochloride was prepared according to the method of Reference Example 2 by replacing 4-methoxybenzonitrile of Reference Example 2 with 3,4-dimethoxybenzonitrile.
Subsequently, the 4-methoxybenzamidine hydrochloride of Example 1 was replaced with 3,4-dimethoxybenzamidine hydrochloride, and a synthesis test was performed according to the method of Example 1 to obtain a white powder.
得られた粉末の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp211−213℃
・TLC(シリカゲル,アセトン):Rf=0.67
・1H NMR(DMSO-d6):δ=2.08(s,3H),3.80(s,3H),3.82(s,3H),7.02−7.67(m,6H).
・MS(EI):m/z(%)=364(M+2,67),362(M+,100),347(21),319(11),304(3),291(4),276(4),181(7),165(9),149(3),137(3),123(2),102(3).
これらのスペクトルデータから、得られた粉末は、化学式(V)で示される4−(2,4−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾールであるものと同定した。収率31.9%。
The melting point of the obtained powder, Rf value of thin layer chromatography, 1 H NMR and mass spectrum data were as follows.
・ Mp211-213 ℃
・ TLC (silica gel, acetone): Rf = 0.67
1 H NMR (DMSO-d 6 ): δ = 2.08 (s, 3H), 3.80 (s, 3H), 3.82 (s, 3H), 7.02-7.67 (m, 6H).
MS (EI): m / z (%) = 364 (M + 2, 67), 362 (M + , 100), 347 (21), 319 (11), 304 (3), 291 (4), 276 (4), 181 (7), 165 (9), 149 (3), 137 (3), 123 (2), 102 (3).
From these spectral data, the obtained powder was identified as 4- (2,4-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole represented by the chemical formula (V). . Yield 31.9%.
〔実施例3〕
<4−(3,4−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾールの合成>
まず、参考例1の2′,4′−ジクロロプロピオフェノンを3′,4′−ジクロロプロピオフェノンに代えて、参考例1の方法に準拠して2−ブロモ−3′,4′−ジクロロプロピオフェノン/トルエン溶液を調製し、参考例2の4−メトキシベンゾニトリルを3,4−ジメトキシベンゾニトリルに代えて、参考例2の方法に準拠して3,4−ジメトキシベンズアミジン塩酸塩を調製した。
次いで、実施例1の4−メトキシベンズアミジン塩酸塩を3,4−ジメトキシベンズアミジン塩酸塩に代えて、2−ブロモ−2′,4′−ジクロロプロピオフェノン/トルエン溶液を2−ブロモ−3′,4′−ジクロロプロピオフェノン/トルエン溶液に代えて、実施例1の方法に準拠して合成試験を行い、乳白色粉末を得た。
Example 3
<Synthesis of 4- (3,4-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole>
First, 2 ', 4'-dichloropropiophenone of Reference Example 1 was replaced with 3', 4'-dichloropropiophenone, and 2-bromo-3 ', 4'- was prepared according to the method of Reference Example 1. A dichloropropiophenone / toluene solution was prepared, and 4-methoxybenzonitrile of Reference Example 2 was replaced with 3,4-dimethoxybenzonitrile, and 3,4-dimethoxybenzamidine hydrochloride was used in accordance with the method of Reference Example 2. Was prepared.
Next, the 4-methoxybenzamidine hydrochloride of Example 1 was replaced with 3,4-dimethoxybenzamidine hydrochloride, and a 2-bromo-2 ′, 4′-dichloropropiophenone / toluene solution was added to 2-bromo-3 Instead of the '4'-dichloropropiophenone / toluene solution, a synthetic test was performed according to the method of Example 1 to obtain a milky white powder.
得られた粉末の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp113−115℃
・TLC(シリカゲル,アセトン):Rf=0.71
・1H NMR(DMSO-d6):δ=2.38(s,3H),3.74(s,3H),3.86(s,3H),6.81−7.77(m,6H).
・MS(EI):m/z(%)=364(M+2,68),362(M+,100),347(18),319(11),304(4),291(4),276(5),181(8),165(9),149(3),137(2),124(2),102(3).
これらのスペクトルデータから、得られた粉末は、化学式(VI)で示される4−(3,4−ジクロロフェニル)−2−(3,4−ジメトキシフェニル)−5−メチルイミダゾールであるものと同定した。収率41.2%。
The melting point of the obtained powder, Rf value of thin layer chromatography, 1 H NMR and mass spectrum data were as follows.
・ Mp113-115 ℃
・ TLC (silica gel, acetone): Rf = 0.71
1 H NMR (DMSO-d 6 ): δ = 2.38 (s, 3H), 3.74 (s, 3H), 3.86 (s, 3H), 6.81-7.77 (m, 6H).
MS (EI): m / z (%) = 364 (M + 2,68), 362 (M + , 100), 347 (18), 319 (11), 304 (4), 291 (4), 276 (5), 181 (8), 165 (9), 149 (3), 137 (2), 124 (2), 102 (3).
From these spectral data, the obtained powder was identified as 4- (3,4-dichlorophenyl) -2- (3,4-dimethoxyphenyl) -5-methylimidazole represented by the chemical formula (VI). . Yield 41.2%.
〔実施例4〕
<2−(3,4−ジメトキシフェニル)−4−(1−ナフチル)イミダゾールの合成>
まず、参考例1の2′,4′−ジクロロプロピオフェノンを1−アセトナフトンに代えて、参考例1の方法に準拠して2−ブロモ−1′−アセトナフトン/トルエン溶液を調製し、参考例2の4−メトキシベンゾニトリルを3,4−ジメトキシベンゾニトリルに代えて、参考例2の方法に準拠して3,4−ジメトキシベンズアミジン塩酸塩を調製した。
次いで、実施例1の4−メトキシベンズアミジン塩酸塩を3,4−ジメトキシベンズアミジン塩酸塩に代えて、2−ブロモ−2′,4′−ジクロロプロピオフェノン/トルエン溶液を2−ブロモ−1′−アセトナフトン/トルエン溶液に代えて、実施例1の方法に準拠して合成試験を行い、暗ベージュ色粉末を得た。
Example 4
<Synthesis of 2- (3,4-dimethoxyphenyl) -4- (1-naphthyl) imidazole>
First, a 2-bromo-1′-acetonaphthone / toluene solution was prepared according to the method of Reference Example 1 by replacing 2 ′, 4′-dichloropropiophenone of Reference Example 1 with 1-acetonaphthone. 2,4-methoxybenzonitrile was replaced with 3,4-dimethoxybenzonitrile, and 3,4-dimethoxybenzamidine hydrochloride was prepared according to the method of Reference Example 2.
Subsequently, 4-methoxybenzamidine hydrochloride of Example 1 was replaced with 3,4-dimethoxybenzamidine hydrochloride, and 2-bromo-2 ′, 4′-dichloropropiophenone / toluene solution was replaced with 2-bromo-1 Instead of the '-acetonaphthone / toluene solution, a synthesis test was performed according to the method of Example 1 to obtain a dark beige powder.
得られた粉末の融点、薄層クロマトグラフィーのRf値、1H NMR及びマススペクトルデータは、以下のとおりであった。
・mp186−188℃
・TLC(シリカゲル,アセトン):Rf=0.59
・1H NMR(DMSO-d6):δ=3.82(s,3H),3.86(s,3H),7.07−8.66(m,10H).
・MS(EI):m/z(%)=330(M+,100),315(9),287(4),271(4),257(2),243(6),167(47),152(3),139(11),122(4).
これらのスペクトルデータから、得られた粉末は、化学式(VII)で示される2−(3,4−ジメトキシフェニル)−4−(1−ナフチル)イミダゾールであるものと同定した。収率24.8%。
The melting point of the obtained powder, Rf value of thin layer chromatography, 1 H NMR and mass spectrum data were as follows.
・ Mp186-188 ℃
・ TLC (silica gel, acetone): Rf = 0.59
-1 H NMR (DMSO-d 6 ): δ = 3.82 (s, 3H), 3.86 (s, 3H), 7.07-8.66 (m, 10H).
MS (EI): m / z (%) = 330 (M + , 100), 315 (9), 287 (4), 271 (4), 257 (2), 243 (6), 167 (47) , 152 (3), 139 (11), 122 (4).
From these spectral data, the obtained powder was identified as 2- (3,4-dimethoxyphenyl) -4- (1-naphthyl) imidazole represented by the chemical formula (VII). Yield 24.8%.
〔実施例5〕
まず、実施例1〜4において合成した2−(メトキシフェニル)イミダゾール化合物と、これらとは別に2−フェニルイミダゾール(2PZ、四国化成工業製)を有効成分とする銅の酸化防止剤を各々調製した。次いで、該防止剤に銅を接触させることにより銅の表面に化成皮膜を形成させた。そして、銅に対する溶融半田の濡れ時間を測定して、イミダゾール化合物が作用する銅表面への酸化防止性能を評価した。この場合、溶融半田の濡れ時間が短い程、イミダゾール化合物の酸化防止性能が優れているものと判定される。
評価試験の詳細は、次のとおりである。
(1)酸化防止剤の調製
イミダゾール化合物、酸、金属塩及びハロゲン化合物を、表1記載の組成となるようにイオン交換水に溶解させた後、アンモニア水でpHを調整して酸化防止剤を調製した。
(2)表面処理方法
材質が金属銅の試験片(5mm×50mm×0.3mmの銅版)を脱脂し、次いでソフトエッチングを行い、所定温度の酸化防止剤に所定時間浸漬して、銅の表面に化成皮膜を形成させた後、水洗して乾燥した。
(3)濡れ時間の測定
表面処理を行った試験片を、ポストフラックス(JS−64MSS、弘輝製)に浸漬して、半田濡れ性試験器(SAT−2000、レスカ製)を使用して半田濡れ時間(秒)を測定した。使用した半田は錫−鉛系共晶半田(H63A−B20、千住金属工業製)であり、測定条件は半田温度240℃、浸漬深さ2mm、浸漬スピード16mm/秒とした。
なお、半田濡れ時間を測定した試験片は、(A)表面処理直後のものと、(B)温度40℃、湿度90%RHの恒温恒湿器に入れて96時間放置したものと、(C)さらに200℃で10分間加熱したものである。
得られた試験結果は、表1に示したとおりであった。
Example 5
First, a 2- (methoxyphenyl) imidazole compound synthesized in Examples 1 to 4 and a copper antioxidant each containing 2-phenylimidazole (2PZ, manufactured by Shikoku Kasei Kogyo Co., Ltd.) as an active ingredient were prepared. . Next, a chemical conversion film was formed on the surface of copper by bringing the inhibitor into contact with copper. And the wetting time of the molten solder with respect to copper was measured, and the antioxidant performance to the copper surface on which an imidazole compound acts was evaluated. In this case, it is determined that the shorter the wet time of the molten solder, the better the antioxidant performance of the imidazole compound.
The details of the evaluation test are as follows.
(1) Preparation of antioxidant After dissolving an imidazole compound, an acid, a metal salt, and a halogen compound in ion-exchanged water so as to have the composition shown in Table 1, the pH is adjusted with ammonia water to thereby add an antioxidant. Prepared.
(2) Surface treatment method A test piece (copper plate of 5 mm × 50 mm × 0.3 mm) made of metallic copper is degreased, then soft-etched, and immersed in an antioxidant at a predetermined temperature for a predetermined time to obtain a copper surface. After the chemical conversion film was formed on, it was washed with water and dried.
(3) Measurement of wetting time The surface-treated test piece is immersed in post flux (JS-64MSS, manufactured by Hiroki) and solder wetted using a solder wettability tester (SAT-2000, manufactured by Resuka). Time (seconds) was measured. The solder used was tin-lead eutectic solder (H63A-B20, manufactured by Senju Metal Industry), and the measurement conditions were a solder temperature of 240 ° C., an immersion depth of 2 mm, and an immersion speed of 16 mm / second.
In addition, the test piece which measured the solder wetting time includes (A) a sample immediately after the surface treatment, (B) a sample left in a constant temperature and humidity chamber at a temperature of 40 ° C. and a humidity of 90% RH for 96 hours, and (C ) Further heated at 200 ° C. for 10 minutes.
The test results obtained were as shown in Table 1.
表1に示した試験結果によれば、本願発明の2−(メトキシフェニル)イミダゾール化合物を有効成分として含有する酸化防止剤は、銅の表面に耐湿性及び耐熱性に優れた化成皮膜を形成させることができるので、銅表面の酸化防止に有用である。 According to the test results shown in Table 1, the antioxidant containing the 2- (methoxyphenyl) imidazole compound of the present invention as an active ingredient forms a chemical conversion film excellent in moisture resistance and heat resistance on the surface of copper. Therefore, it is useful for preventing oxidation of the copper surface.
本発明によれば、金属、特に銅(銅合金を含む)の表面の酸化防止剤や、エポキシ樹脂の硬化剤又は硬化促進剤として、また医農薬分野の中間原料としても有用な2−(メトキシフェニル)イミダゾール化合物を提供することができる。また、銅表面をはんだ付けする際のはんだ付け性を良好なものとする酸化防止剤を提供することができる。 According to the present invention, 2- (methoxy) is useful as an antioxidant on the surface of metals, particularly copper (including copper alloys), as a curing agent or curing accelerator for epoxy resins, and as an intermediate material in the field of medicine and agrochemicals. Phenyl) imidazole compounds can be provided. Moreover, the antioxidant which makes the solderability at the time of soldering the copper surface favorable can be provided.
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012183809A JP5885621B2 (en) | 2012-08-23 | 2012-08-23 | 2- (Methoxyphenyl) imidazole compound and antioxidant |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012183809A JP5885621B2 (en) | 2012-08-23 | 2012-08-23 | 2- (Methoxyphenyl) imidazole compound and antioxidant |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014040395A JP2014040395A (en) | 2014-03-06 |
JP5885621B2 true JP5885621B2 (en) | 2016-03-15 |
Family
ID=50392998
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012183809A Active JP5885621B2 (en) | 2012-08-23 | 2012-08-23 | 2- (Methoxyphenyl) imidazole compound and antioxidant |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5885621B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3573957B1 (en) * | 2017-01-24 | 2023-04-26 | Rivara, Mirko | Compositions and methods for blocking sodium channels |
-
2012
- 2012-08-23 JP JP2012183809A patent/JP5885621B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP2014040395A (en) | 2014-03-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2018535263A (en) | 4-((6- (2- (2,4-difluorophenyl) -1,1-difluoro-2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl) pyridine-3 -Yl) oxy) benzonitrile and preparation method | |
JP5313044B2 (en) | Surface treatment agent for copper or copper alloy and use thereof | |
EP1753728B1 (en) | Phenylnaphthylimidazoles for use on copper surfaces during soldering | |
JP5858884B2 (en) | Imidazole compounds having a thiophene ring | |
EP1605078B1 (en) | Soldering process using imidazole compound | |
JP5484795B2 (en) | 2-Benzyl-4- (3,4-dichlorophenyl) -5-methylimidazole compound | |
JP5885621B2 (en) | 2- (Methoxyphenyl) imidazole compound and antioxidant | |
JP5918079B2 (en) | 4-naphthylimidazole compounds and antioxidants | |
JP5368241B2 (en) | 2-Benzyl-4- (2,4-dichlorophenyl) -5-methylimidazole compound | |
JP5885620B2 (en) | 2- (2-Furyl) imidazole compound and antioxidant | |
JP5368244B2 (en) | 2- (2,4-dichlorobenzyl) -4-aryl-5-methylimidazole compound | |
JP5368271B2 (en) | 4- (4-Biphenylyl) -2- (2,4-dichlorobenzyl) imidazole and surface treatment solution | |
JP5260208B2 (en) | 2- (2,4-Dichlorobenzyl) -4- (halogenated phenyl) imidazole compound | |
JP5892605B2 (en) | 4- (2-Thienyl) imidazole compound | |
JP5368263B2 (en) | 4- (2,4-dichlorophenyl) -5-methylimidazole compound | |
JP5260357B2 (en) | 2- (2,4-dichlorobenzyl) -4-phenyl-5-alkylimidazole compound | |
JP5398076B2 (en) | 2- (Bromobenzyl) -4- (bromophenyl) -5-methylimidazole compound | |
JP5398075B2 (en) | 4- (dichlorophenyl) -2- (4-fluorobenzyl) -5-methylimidazole compound | |
JP5204028B2 (en) | 2-Benzyl-4- (4-alkylphenyl) imidazole compound | |
JP5260367B2 (en) | 2- (Chlorobenzyl) -4-phenylimidazole compound | |
JP2010077071A (en) | 2-alkyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound | |
JP2010070479A (en) | 4-aryl-2-(1-naphthylmethyl)imidazole compound | |
JP2010254586A (en) | 2-benzyl-4-phenyl-5-alkylimidazole compound | |
JP2010090105A (en) | 2-benzyl-4-naphthylimidazole compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150421 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20151224 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160201 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160209 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5885621 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |