JPS6038422B2 - Azamethine-metal complex compound - Google Patents
Azamethine-metal complex compoundInfo
- Publication number
- JPS6038422B2 JPS6038422B2 JP51000625A JP62576A JPS6038422B2 JP S6038422 B2 JPS6038422 B2 JP S6038422B2 JP 51000625 A JP51000625 A JP 51000625A JP 62576 A JP62576 A JP 62576A JP S6038422 B2 JPS6038422 B2 JP S6038422B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- atom
- hydrogen
- alkyl
- 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
- -1 trifluoromethyl- Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical group C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 2
- HVAXPRLYMAWEBL-UHFFFAOYSA-N 4-chlorobenzimidazol-2-one Chemical compound ClC1=CC=CC2=NC(=O)N=C12 HVAXPRLYMAWEBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 9
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LPRBZICETYEWOZ-UHFFFAOYSA-N 4-formyl-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C=O)=C(O)C(C(=O)O)=CC2=C1 LPRBZICETYEWOZ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical group 0.000 description 4
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000001238 wet grinding Methods 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QQDKXJSYZGJGKJ-UHFFFAOYSA-N 2-amino-3,4,6-trichlorophenol Chemical compound NC1=C(O)C(Cl)=CC(Cl)=C1Cl QQDKXJSYZGJGKJ-UHFFFAOYSA-N 0.000 description 1
- JEASLLCHQHBBGM-UHFFFAOYSA-N 2-amino-4,5-dimethylphenol Chemical compound CC1=CC(N)=C(O)C=C1C JEASLLCHQHBBGM-UHFFFAOYSA-N 0.000 description 1
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- GISWNAMJAQRJPC-UHFFFAOYSA-N 2-amino-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(N)=C1 GISWNAMJAQRJPC-UHFFFAOYSA-N 0.000 description 1
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 description 1
- MHAFRUMLQZZSIN-UHFFFAOYSA-N 2-amino-4-chloro-6-nitrophenol Chemical compound NC1=CC(Cl)=CC([N+]([O-])=O)=C1O MHAFRUMLQZZSIN-UHFFFAOYSA-N 0.000 description 1
- AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 description 1
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- QUIIUKFPLUUSGQ-UHFFFAOYSA-N 2-amino-6-chlorophenol Chemical compound NC1=CC=CC(Cl)=C1O QUIIUKFPLUUSGQ-UHFFFAOYSA-N 0.000 description 1
- ZDMBLPBTZZZSIW-UHFFFAOYSA-N 2-amino-6-methyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC(N)=C1O ZDMBLPBTZZZSIW-UHFFFAOYSA-N 0.000 description 1
- XLJMDBOKSZROPC-UHFFFAOYSA-N 2-methoxy-4,6-dinitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N XLJMDBOKSZROPC-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
- LHMQDVIHBXWNII-UHFFFAOYSA-N 3-amino-4-methoxy-n-phenylbenzamide Chemical compound C1=C(N)C(OC)=CC=C1C(=O)NC1=CC=CC=C1 LHMQDVIHBXWNII-UHFFFAOYSA-N 0.000 description 1
- INCJNDAQNPWMPZ-UHFFFAOYSA-N 3-amino-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1N INCJNDAQNPWMPZ-UHFFFAOYSA-N 0.000 description 1
- FDGAEAYZQQCBRN-UHFFFAOYSA-N 3-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1N FDGAEAYZQQCBRN-UHFFFAOYSA-N 0.000 description 1
- ZJNQRITVJGUHTL-UHFFFAOYSA-N 3-amino-n-(2,5-dichlorophenyl)-4-methoxybenzamide Chemical compound C1=C(N)C(OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl ZJNQRITVJGUHTL-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 description 1
- QODOLPZUMYLXKD-UHFFFAOYSA-N 4-formyl-3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C1=C2C=CC=CC2=C(C=O)C(O)=C1C(=O)NC1=CC=CC=C1 QODOLPZUMYLXKD-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- VNQABZCSYCTZMS-UHFFFAOYSA-N Orthoform Chemical compound COC(=O)C1=CC=C(O)C(N)=C1 VNQABZCSYCTZMS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 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
- 229920002125 Sokalan® Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical group [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 125000005363 dialkylsulfonamide group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GAUUPGVEVVWENO-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-4-formyl-3-hydroxynaphthalene-2-carboxamide Chemical compound COC1=CC=C(OC)C(NC(=O)C=2C(=C(C=O)C3=CC=CC=C3C=2)O)=C1 GAUUPGVEVVWENO-UHFFFAOYSA-N 0.000 description 1
- VENDXQNWODZJGB-UHFFFAOYSA-N n-(4-amino-5-methoxy-2-methylphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2C=CC=CC=2)=C1C VENDXQNWODZJGB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
【発明の詳細な説明】
本発明は下記一般式（１）
〔式中、Ｘ，、ＸＺ皮ぴＸ３は同一でも相異つてし、て
もよく、夫々水素−又はハロゲン−原子、アルキル一、
アルコキシー、フエニル−、トリルー、ニトロ一、力ル
ポアルコキシ−、スルホンアミドー、モノ−又はジーア
ルキルスルホンアミドー、カルボンアミド−、モノ−又
はジーアルキルカルボンアミドー、アルカ／ィルアミ／
−基、又は次式（式中、Ｇは−ＮＨＣＯ−、−Ｓ０がＨ
−又は−ＣＯＮＨ−を、Ｒは水素−又はクロルー原子、
アルキルー、アルコキシー、スルホンアミド−又はカル
ボンアミド−基を表わす。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the following general formula (1) [wherein,
Alkoxy, phenyl, tri-, nitro, polyalkoxy, sulfonamide, mono- or dialkyl sulfonamide, carbonamide, mono- or di-alkylcarbonamide, alkyl/ylamide/
- group, or the following formula (wherein, G is -NHCO-, -S0 is H
- or -CONH-, R is hydrogen- or chloro atom,
It represents an alkyl, alkoxy, sulfonamido or carbonamido group.
）なる基を意味し、又Ｘ，とＸ２とはフェニル環と一緒
になってペンズィミダゾロン環を形成することもできる
。), and X and X2 can also be combined with a phenyl ring to form a penzimidazolone ring.
Ｙは水素−、クロル−又はプロムー原子を意味し、〜は
ナフチル基、フェニル基（この基は１〜３個のアルキル
ー、アルコキシー、アルキルスルホニル−、力ルボアル
コキシ−、トリフルオルメチルー、ニトロ−、シアン一
、アルカノイルアミノ−、ベンゾイルアミノ−、力ルボ
ンアミノ−、モノ−又はジーアルキルカルポンアミドー
、スルホンアミド−、モノ−又はジーアルキルスルホン
アミド−基、又はハロゲン原子によって置換されていて
もよい）、ベンズイミダゾロンー、クロルベンズイミダ
ゾロンー、キナゾリンジオンー、キノキザリン−、フタ
ルイミドー又はフタラジンー基を意味し、Ｍは亜鉛−、
カドミウム−・コバルト−、ニッケル−又は鞠−原子を
意味する。〕なる新規な水不溶性アザメチン−金属鍵化
合物−ピグメントに関するものである。Y means a hydrogen, chloro, or promo atom, ~ is a naphthyl group, a phenyl group (this group has 1 to 3 alkyl, alkoxy, alkylsulfonyl, triboalkoxy, trifluoromethyl, nitro, (optionally substituted by cyanogen, alkanoylamino, benzoylamino, tricarbonamino, mono- or di-alkylcarponamide, sulfonamide, mono- or di-alkylsulfonamido groups, or halogen atoms) , benzimidazolone, chlorbenzimidazolone, quinazolinedione, quinoxaline, phthalimide or phthalazine group, M is zinc-,
Means a cadmium, cobalt, nickel or nickel atom. This invention relates to a novel water-insoluble azamethine-metal key compound-pigment.
特に好都合なピグメントは一般式（１）に於て、Ｘ，、
Ｘ２及び×３が同一でも相異つてし、てもよくて、夫々
水素−、クロルー又はブロムー原子、アルキルー、アル
コキシー、ニトロ−、アセチルアミノー、ベンゾイルア
ミノ−、カルポメトキシー、力ルボンアミドー、アルキ
ルカルボンアミド−又はフェニルカルボンアミドー基を
意味し、Ｙが水素一、クロム一又はプロム−原子を意味
し、〜がフェニル基（この基は１〜３個のアルキル−、
アルコキシー、アルキルスルホニル−、力ルボアルコキ
シー、トリフルオルメチル−、ニトロ一、シアン一、ア
ルカノイルアミノ−、力ルポンアミドー、モ／一又はジ
ーアルキルーカルボンアミドー、スルホンアミド−、モ
ノー又はジーアルキルスルホンアミドー基、ブロム−又
はクロム一原子によって置換されていてもよい）、ベン
ズィミダゾロンー又はク。Particularly advantageous pigments have the general formula (1) with X,
X 2 and or a phenylcarbonamido group, Y means one hydrogen, one chromium, or one promo atom, and ~ means a phenyl group (this group has 1 to 3 alkyl-,
Alkoxy, alkylsulfonyl, trifluoroalkoxy, trifluoromethyl, nitro, cyanogen, alkanoylamino, mono- or di-alkylcarbonamide, sulfonamide, mono- or di-alkyl sulfonamido group , bromo or chromium), benzimidazolone or chromium.
ルベンズィミダゾロン−基を意味し、Ｍがニッケル原子
好ましくは銅原子を意味するピグメントである。尚、こ
こに於て又以下に於てアルキル及びアルカノイルなる概
念の下に炭素原子１〜４個を含む基が了解さるべきであ
る。残基山としては例えばフェニル−・ｏ一・ｍ一、ｐ
ートリルー、ｏ−、ｍ−、ｐーメトキシフエニルー、０
−、ｍ−、Ｐ−エトキシフエニルー、ｏ一、ｍ一、ｐー
クロルフエニル−、０−、ｍ−、Ｐーフロムフエニル−
、ｏ−、ｍートリフルオルメチルフエニルー、ｏ一、ｍ
一、ｐ−ニトロフエニル−、２・４−ジメチルフヱニル
−、２・５ージメトキシフエニル−、２・４−ジクロル
フエニルー、２・５ージクロルフヱニルー、２・４・５
−トリク。It is a pigment in which a rubenzimidazolone group is meant and M is a nickel atom, preferably a copper atom. Here and in the following, radicals containing 1 to 4 carbon atoms are to be understood under the terms alkyl and alkanoyl. Examples of residue mountains include phenyl-・o1・m1, p
-trilu, o-, m-, p-methoxyphenyl, 0
-, m-, P-ethoxyphenyl, o-, m-, p-chlorophenyl-, 0-, m-, P-fromphenyl-
, o-, m-trifluoromethylphenyl, o-, m
1, p-nitrophenyl, 2,4-dimethylphenyl, 2,5-dimethoxyphenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,4,5
-Trick.
ルフエニルー、２ークロルー３−メチルフエニル、２−
クロルー４−メチルフエニル−、２ークロルー５−メチ
ルフエニル−、３−クロル−２ーメチルフエニルー、４
ークロル−２ーメチルフエニルー、２ーメトキシー５−
クロルフエニルー、２・５ージメトキシー４−クロルフ
エニルー、２・４ージメトキシ−５ークロルフエニル−
、２−メトキシー４−クロル−５ーメチルフエニルー、
４ーアセチルアミノフエニル−、４ーベンゾイルアミノ
フエニルー、ベンズイミダゾリル−、フタルイミジルー
、キノキザリルー、キナゾリル−又はフタラジニルー基
が挙‘られる。本発明の対象は、更に、下記一般式（０
）〔式中、Ｘ，、Ｘ２、Ｘ３、Ｙ及びＡｒは前述の意味
を有し、Ｚは水素原子又はメチル基を意味する。lephenyl, 2-chloro-3-methylphenyl, 2-
Chloro-4-methylphenyl-, 2-chloro-5-methylphenyl-, 3-chloro-2-methylphenyl-, 4
-chloro-2-methylphenyl, 2-methoxy5-
Chlorphenyl, 2,5-dimethoxy-4-chlorphenyl, 2,4-dimethoxy-5-chlorphenyl-
, 2-methoxy4-chloro-5-methylphenyl,
Mention may be made of 4-acetylaminophenyl, 4-benzoylaminophenyl, benzimidazolyl, phthalimidyl, quinoxaryl, quinazolyl or phthalazinyl. The object of the present invention is furthermore the following general formula (0
) [In the formula, X,, X2, X3, Y and Ar have the above-mentioned meanings, and Z means a hydrogen atom or a methyl group.
〕なるアザメチン化合物を金属を付与する釘−、ーツケ
ルー、亜鉛−、カドミウム−又はコバルト一塩と処理す
ることによる一般式（１）なる化合物の製法である。金
属化は好ましくは２価の銅、コバルト又はニッケルの塩
、例えばそれらのク。This is a method for producing a compound of general formula (1) by treating an azamethine compound of formula (1) with metal-imparting salts such as nail, copper, zinc, cadmium, or cobalt monosalt. The metallization is preferably a divalent copper, cobalt or nickel salt, such as a divalent copper, cobalt or nickel salt.
ライド又はサルフェートを用いて、しかし又好ましくは
それらのアセテート、ホルミェート又はステアレートを
用いて、公３句の方法で有機溶剤中で行う。か）る溶剤
としては例えばグリコールモノメチルェーナル、ホルム
アミド、ジメチルホルムアミド、Ｎ−メチルピロリドン
、氷酢酸、アルコール又はこれらの溶剤と場合により水
との混合物が挙げられる。金属化は２〜６時間で７０〜
１８０℃の温度で行うのが好ましい。Ｚが水素原子であ
る錫合には１５ぴ０までの温度が好ましい。ＺがＣ比で
ある一般式（０）の化合物を金属化する場合には同時に
脱アルキル化が起る。It is carried out in an organic solvent in a conventional manner using the hydrides or sulfates, but also preferably their acetates, formates or stearates. Such solvents include, for example, glycol monomethylenal, formamide, dimethylformamide, N-methylpyrrolidone, glacial acetic acid, alcohol or mixtures of these solvents and optionally water. Metallization takes 2-6 hours to 70~
Preferably it is carried out at a temperature of 180°C. Temperatures up to 15°C are preferred for tin combinations where Z is a hydrogen atom. When a compound of general formula (0) in which Z is the C ratio is metallized, dealkylation occurs simultaneously.
脱アルキル化性の金属化は有機溶剤中で比較的商い温度
で殊に１００〜１８び０で行うのが好ましい。溶剤とし
ては例えばグリコールモノメチルー及びーモ／エチルエ
ーテル、双極性非プロトン性溶剤、例えばジメチルホル
ムアミド、ジメチルスルホキシド．スルホラン、Ｎーメ
チルビロリドンを使用するができる。金属鈴化合物はこ
れらの溶剤から炉過によって単離することができる。The dealkylating metallization is preferably carried out in an organic solvent at relatively moderate temperatures, especially between 100 and 180°C. Solvents include, for example, glycol monomethyl and mono/ethyl ethers, dipolar aprotic solvents such as dimethylformamide, dimethyl sulfoxide. Sulfolane and N-methylpyrrolidone can be used. Metallic compounds can be isolated from these solvents by filtration.
本発明によるピグメントの最善の着色性を得るためには
完成ビグメントを溶剤中で、場合により水又は塩溶液の
存在下に、微細化した形に変えることが時として有利で
ある。In order to obtain the best coloring properties of the pigments according to the invention, it is sometimes advantageous to convert the finished pigments into finely divided form in a solvent, optionally in the presence of water or a salt solution.
この目的に対する溶剤としては染料は不溶であるが仕上
げ条件下にある程度の溶解を可能にするもの、例えば脂
肪族アルコール（例えばエタノール、イソプロパノール
、イソー又はｎ−プタ／−ル）、塩素化芳香族化合物（
例えばクロルベンゾール及びートルオール又はジクロル
ベンゾール）、並びに双極性非プロトン性溶剤（例えば
ジメチルホルムアミド、ジメチルーアセトアミド、ジメ
チルスルフオキシド、ポリアルキル尿素及び燐酸トリス
ジメチルアミド）などが適する。Solvents for this purpose include those in which the dye is insoluble but which allow some solubility under the finishing conditions, such as aliphatic alcohols (e.g. ethanol, isopropanol, iso or n-butyl), chlorinated aromatic compounds. (
For example, chlorbenzole and -toluol or dichlorobenzole), and dipolar aprotic solvents (for example dimethylformamide, dimethylacetamide, dimethylsulfoxide, polyalkylureas and trisdimethylamide phosphate) are suitable.
多くの場合に塩又は溶剤を用いての粉砕による微細化も
有利である。その際前者の場合には特に振動ミル上での
乾式粉砕及び続いての水による塩の溶出が行われ、続い
て場合により溶剤による湿式粉砕又は温度処理を行うこ
とができる。塩としては大体に於てハロゲン化水素酸又
は硫酸のアルカリ一及びアルカリ士類−塩、例えば塩化
ナトリウム、塩化カリウム、硫酸ナトリウム又は硫酸マ
グネシウムが使用される。Micronization by grinding, often using salts or solvents, is also advantageous. In the first case, dry grinding on a vibrating mill and subsequent elution of the salt with water is carried out, which can optionally be followed by wet grinding with a solvent or temperature treatment. As salts, the alkali mono- and alkali mono- and alkali salts of hydrohalic acids or sulfuric acids, such as sodium chloride, potassium chloride, sodium sulfate or magnesium sulfate, are generally used.
湿式粉砕に使用しうる溶剤は大体に於て上述の溶剤、例
えばアルコール、酸アミド又はジメチルスルフオキシド
である。Solvents that can be used for wet milling are generally those mentioned above, such as alcohols, acid amides or dimethyl sulfoxide.
一般式（０）の金属化されていないアザメチン化合物は
ドイツ公開明細書第２４０８２９１号に記載の方法によ
って製造することができる。The unmetallized azamethine compounds of general formula (0) can be produced by the method described in DE 2408291.
その際下記一般式（ｍ）なるアルデヒドの１モルを常法
で下記一般式（Ｗ）なるｏーアミノフエノール又はｏー
アミノフエノールェーテルの１モルと縮合せしめる。At this time, 1 mole of an aldehyde represented by the following general formula (m) is condensed with 1 mole of o-aminophenol or o-aminophenol ether represented by the following general formula (W) in a conventional manner.
式（ｍ）なるアルデヒド‘こ対する例としては次のもの
が挙げられる：１ーホルミルー２ーヒドロキシー３−ナ
フトエ酸ーアニリド、１−ホルミル−２ーヒドロキシ−
３−ナフトエ酸−２−クロルアニリド、１ーホルミルー
２−ヒドロキシー３ーナフトエ酸ー４′ークロルアニリ
ド、１ーホルミル−２ーヒドロキシー３−ナフトエ酸一
〆・４′ージクロルアニリド、１−ホルミルー２−ヒド
ロキシー３−ナフトエ酸一２・５−ジクロルアニリド、
１ーホルミルー２−ヒドロキシ−３ーナフトエ酸−Ｚ−
メチルアニリド、１ーホルミルー２−ヒドロキシ−３−
ナフトエ酸一４′ーメチルアニリド、１ーホルミル−２
ーヒドロキシー３ーナフトエ酸−２−メトキシアニリド
、１ーホルミルー２ーヒドロキシー３ーナフトエ酸−２
−ェトキシアニリド、１ーホルミル−２ーヒドロキシ−
３ーナフトエ酸一４′−メトキシアニリド、１−ホルミ
ルー２ーヒドロキシー３ーナフトエ酸−４′ーェトキシ
アニリド、１−ホルミルー２ーヒドロキシー３ーナフト
ヱ酸ーズ・４′−ジメチルアニリド、１−ホルミルー２
ーヒドロキシ−３ーナフトエ酸−２−メチル−ゴークロ
ルアニリド、１ーホルミルー２−ヒドロキシー３ーナフ
トエ酸−２ーメチルー４′ークロルアニリド、１−ホル
ミルー２ーヒドロキシ−３ーナフトエ酸−２・５−ジメ
トキシアニリド、１ーホルミルー２ーヒドロキシー３ー
ナフトエ酸−Ｚ・５′−ジメトキシー４′−クロルアニ
リド、１ーホルミル−２ーヒドロキシー３ーナフトエ酸
一Ｚ・４′ージメトキシー５′−クロルアニリド、１−
ホルミル−２ーヒドロキシ−３ーナフトエ酸−４′ーア
セチルアミノアニリド、１ーホルミル−２ーヒドロキシ
−３−ナフトエ酸−イーベンゾィルアミノアニリド、１
−ホルミルー２−ヒドロキシー３−ナフトエ酸−３′ー
トリフルオルメチルアニリド、１−ホルミル−２−ヒド
ロキシー３ーナフトエ酸−２ーニトロアニリド、１ーホ
ルミル−２ーヒドロキシー６ーフロム−３ーナフトェ酸
アニリド、１ーホルミルー２−ヒドロキシ−３ーナフト
イルー５′ーアミノベンズイミダゾロン１−ホルミル−
２−ヒドロキシー３ーナフトイルー５−アミノープーク
ロルベンズイミダソロン１−ホルミル−２ーヒドロキシ
ー３ーナフトイル−６′−アミノーキナゾリンジオン１
−ホルミル−２−ヒドロキシー３ーナフトイルーナーア
ミノーキナゾリンジオン１−ホルミルー２ーヒドロキシ
ー３ーナフトイルー６′ーアミノキノキザリン１ーホル
ミルー２−ヒドロキシ−３−ナフトイル−４′一アミノ
ナフタルイミド１−ホルミル−２ーヒドロキシー３−ナ
フトイルー６−アミノフタラジンー般式（Ｗ）なる２ー
ヒドロキシ−又は２−アルコキシーアミンに対する例と
しては次のものが挙げられる：２−アミノフヱノール、
２−アミノー４ークロルーフヱノール、２−アミノー５
ークロルフエノール、２−アミノー６−クロルフエノー
ル、２ーアミノー４−フロムフエノール、１ーアミノ−
２−ナフトール、２−アミノ−４−ニトロフエ／−ル、
２−アミ／一５−ニトローフエノール、２ーメトキシー
５−アセチルアミノアニリン、２ーメトキシー５ーメチ
ル−４ーベンゾイルアミノアニリン、５−アミノー４−
ヒドロキシー１・２ーキシロール、５ーアミノ−４ーヒ
ドロキシ−１・３ーキシロール、６ークロル−４−アミ
／一３ーヒドロキシ−トルオール、４・６ージクロルー
２−アミノフエノール、３・４・６−トリクロルー２−
アミノフエノール、５ーニトロ−３−アミノー２一ヒド
ロキシトルオール、５ーニトロ−３ーアミノ−４一ヒド
ロキシトルオール、４・６．−ジニトロー２ーアミノフ
エノール、６ークロルー４ーニトロ−２−アミノフエ／
−ル、４ークロルー５−ニトロ−２ーアミノーフエノー
ル、４−クロルー６−ニトロ一２ーアミノフエノール、
５ークロル−２ーアミノアニソール、６−クロル−２ー
フミノーアニソール、４ーニトロ−２ーアミノアニソー
ル、５ーニトロ−２ーアミノアニソール、３・５ージニ
トロ−２ーアミノアニソール、４−クロル−５ーニトロ
ー２ーアミノアニール、２ーアミノー１・４一ジメトキ
シベンゾール、２ーアミノー４−アセトアミノアニソー
ル、３ーアミノ−４−ヒドロキシ安息香酸メチルェステ
ル、３ーアミノー４−メトキシ安息香酸アミド、３−ア
ミノー４ーメトキシ安息香酸アニリド、３ーアミノー４
−メトキシ−安息香酸−３′ークロルー２−メチルアニ
リド、３ーアミノ−４−メトキシ安息香酸−２・５−ジ
クロルアニリド、５−アミノ−６−ヒドロキシベンズイ
ミダゾロンー２、５ーアミノー６−ヒドロキシー７−ク
ロルベンズイミダゾロンー２０本発明による新規化合物
は価値あるピグメントで、印刷インキ、デイスパージョ
ンベイント、塗料に途し、又高分子有機材料、例えばセ
ルローズーェーテル及びーェステル、ポリアミド、ポリ
ウレタン、ポリエステル、アセチルセルローズ、ニトロ
セルローズ、天然樹脂又は人造樹脂、例えばアミ／プラ
スチック、殊に尿素−及びメラミンーホルムアルデヒド
樹脂、アルキド樹脂、フェノールプラスチック、ポリカ
ーポネ−ト、ポリオレフイン、例えばポリエチレン又は
ポリプロピレン、ポリピニルクロリド、ポリアクリルニ
トリル、ボリアクリル酸ェステル、ゴム、カゼイン、シ
リコーン、シリコーン樹脂などの単独又は混合物を着色
するのに適する。Examples of aldehydes of formula (m) include: 1-formyl-2-hydroxy-3-naphthoic acid anilide, 1-formyl-2-hydroxy-
3-naphthoic acid-2-chloranilide, 1-formyl-2-hydroxy-3-naphthoic acid-4'-chloranilide, 1-formyl-2-hydroxy-3-naphthoic acid mono-4'-dichloranilide, 1-formyl-2-hydroxy-3- naphthoic acid mono-2,5-dichloroanilide,
1-formy-2-hydroxy-3-naphthoic acid-Z-
Methylanilide, 1-formyl-2-hydroxy-3-
Naphthoic acid 4'-methylanilide, 1-formyl-2
-Hydroxy-3-naphthoic acid-2-methoxyanilide, 1-formyl-2-hydroxy-3-naphthoic acid-2
-ethoxyanilide, 1-formyl-2-hydroxy-
3 naphthoic acid-4'-methoxyanilide, 1-formyl-2-hydroxy-3 naphthoic acid-4'-ethoxyanilide, 1-formyl-2-hydroxy-3 naphthoic acid-4'-dimethylanilide, 1-formyl-2
-Hydroxy-3-naphthoic acid-2-methyl-2-methyl-chloranilide, 1-formyl-2-hydroxy-3-naphthoic acid-2-methyl-4'-chloranilide, 1-formyl-2-hydroxy-3-naphthoic acid-2,5-dimethoxyanilide, 1-formyl-2-hydroxy- 3 Naphthoic acid Z.5'-dimethoxy 4'-chloranilide, 1-formyl-2-hydroxy-3 naphthoic acid Z.4'-dimethoxy5'-chloranilide, 1-
Formyl-2-hydroxy-3-naphthoic acid-4'-acetylaminoanilide, 1-formyl-2-hydroxy-3-naphthoic acid-benzoylaminoanilide, 1
-Formy-2-hydroxy-3-naphthoic acid-3'-trifluoromethylanilide, 1-formyl-2-hydroxy-3-naphthoic acid-2-nitroanilide, 1-formyl-2-hydroxy-6-from-3-naphthoic acid anilide, 1-formyl-2-hydroxy -3 naphthoyl 5'-aminobenzimidazolone 1-formyl-
2-hydroxy-3-naphthoyl-5-aminopochlorbenzimidasolone 1-formyl-2-hydroxy-3-naphthoyl-6'-aminoquinazolinedione 1
-Formyl-2-hydroxy-3-naphthoylunaminor-quinazolinedione 1-formyl-2-hydroxy-3-naphthoyl-6'-aminoquinoxaline 1-formyl-2-hydroxy-3-naphthoyl-4'-monoaminonaphthalimide 1-formyl-2-hydroxy- Examples for 3-naphthoyl-6-aminophthalazine-2-hydroxy- or 2-alkoxyamines of the general formula (W) include: 2-aminophenol,
2-amino-4-chlorofluorenol, 2-amino-5
-Chlorphenol, 2-amino-6-chlorophenol, 2-amino-4-fromphenol, 1-amino-
2-naphthol, 2-amino-4-nitropher/-ol,
2-amino/5-nitrophenol, 2-methoxy5-acetylaminoaniline, 2-methoxy5-methyl-4-benzoylaminoaniline, 5-amino-4-
Hydroxy-1,2-xylol, 5-amino-4-hydroxy-1,3-xylol, 6-chloro-4-amino/1-3-hydroxy-toluol, 4,6-dichloro-2-aminophenol, 3,4,6-trichloro-2-
Aminophenol, 5-nitro-3-amino-2-hydroxytoluol, 5-nitro-3-amino-4-hydroxytoluol, 4.6. -dinitro-2-aminophenol, 6-chloro-4-nitro-2-aminophenol/
-ol, 4-chloro-5-nitro-2-aminophenol, 4-chloro-6-nitro-2-aminophenol,
5-Chlor-2-aminoanisole, 6-chloro-2-huminoanisole, 4-nitro-2-aminoanisole, 5-nitro-2-aminoanisole, 3,5-dinitro-2-aminoanisole, 4-chloro-5-nitro 2-amino anil, 2-amino-1,4-dimethoxybenzole, 2-amino-4-acetaminoanisole, 3-amino-4-hydroxybenzoic acid methyl ester, 3-amino-4-methoxybenzoic acid amide, 3-amino-4-methoxybenzoic acid anilide, 3-amino 4
-Methoxy-benzoic acid-3'-chloro-2-methylanilide, 3-amino-4-methoxybenzoic acid-2,5-dichloroanilide, 5-amino-6-hydroxybenzimidazolone-2, 5-amino-6-hydroxy-7 - Chlorbenzimidazolone - 20 The novel compounds according to the invention are valuable pigments and can be used in printing inks, dispersion paints, paints, and also in polymeric organic materials such as cellulose ethers and esters, polyamides, polyurethanes, Polyesters, acetylcellulose, nitrocellulose, natural or artificial resins, such as amino/plastics, especially urea- and melamine-formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, such as polyethylene or polypropylene, polypynyl chloride , polyacrylonitrile, polyacrylic acid ester, rubber, casein, silicone, silicone resin, etc., singly or in combination.
その際上記高分子化合物が可塑性物質又は熔融物として
或は抜糸溶液、ラッカー又は印漆ペーストの形で存在す
るか否かは問題ではない。使用目的の如何により該新規
ピグメントをトーナーとして又は調製物の形で使用する
のが有利である。該ビグメントは温度の着色力及び透明
度、極めて良好な上塗り堅牢性及び卓越した日光塗牢性
を有することで特にすぐれており、そしてこれらの性質
に基き特にメタリックラッカーを着色するのに適する。It does not matter whether the polymeric compound is present as a plastic material or melt or in the form of a suture removal solution, lacquer or lacquer paste. Depending on the intended use, it is advantageous to use the new pigments as toners or in the form of preparations. The pigments are particularly distinguished by their temperature tinctorial strength and transparency, very good topcoat fastness and outstanding sunlight fastness, and because of these properties are particularly suitable for pigmenting metallic lacquers.
以下の例は本発明を一層詳細に説明するためのものであ
る。The following examples are intended to explain the invention in more detail.
例１
１ーホスミル−２ーヒドロキシー３ーナフトエ酸アニリ
ド２９．２夕をエタノール２００の‘と水２０．０の‘
との中に加え、１５分間激しく澄拝する。Example 1 1-phosmyl-2-hydroxy-3-naphthoic acid anilide 29.2% of ethanol and 20.0% of water
In addition to this, pray intensely for 15 minutes.
ついで２−アミノフェノール１１．４夕を加え、更に１
時間激しく縄拝する。その際反応容器を窒素で重畳せし
める。ついで加熱して９０分間６び０に保った後冷却し
、結晶を吸引炉敬し、水洗し、６び○で乾燥する。かく
して黄色のアザメチンが袷んど定量的収量で得られる（
斑の。得られたアザメチン１９．１夕をジメチルホルム
アミド１００凧【中に熔解し、酢酸鋤く０）１０夕をグ
リコールジメチルェーテル１００の【に加えたものを添
加する。Next, 11.4 hours of 2-aminophenol was added, and another 1 hour was added.
I worship the rope intensely for a long time. At this time, the reaction vessel is flooded with nitrogen. Then, it is heated and kept at 60°C for 90 minutes, then cooled, the crystals are taken up in a suction oven, washed with water, and dried at 600°C. Thus yellow azamethine is obtained in quantitative yield (
Spotted. 19.1 parts of the obtained azamethine was dissolved in 100 parts of dimethylformamide, and 10 parts of acetic acid was added to 10 parts of glycol dimethyl ether.
ついで４時間１０５ｑｏで蝿拝し、冷却し、生成物を室
温で吸引炉取する。これを一度ジメチルホルムアミドで
、続いて水で洗練し、乾燥る。かくして次式なる濃黄色
のアザメチン−鋼鰭化合物１８．３夕が得られた。It is then heated for 4 hours at 105 qo, cooled and the product is sucked off at room temperature. This is purified once with dimethylformamide and then with water and dried. In this way, a dark yellow azamethine-steel fin compound 18.3 having the following formula was obtained.
例 ２〜４２
例１に従い式（ｍ）のアルデヒドを式（Ｗ）のアミンと
縮合せしめて得られる一般式（ロ）のアザメチン化合物
を例１に従って金属塩と反応せしめると、その他のアザ
メチンー金属鍔化合物（１）が得られる。Examples 2 to 42 When the azamethine compound of the general formula (b) obtained by condensing the aldehyde of the formula (m) with the amine of the formula (W) according to Example 1 is reacted with a metal salt according to Example 1, other azamethine-metal Compound (1) is obtained.
なお以下の例に於て使用された金属塩は例２、３、８〜
１１及び１９に於ては酢酸鋼であり、例４及び２６に於
てはステアリン酸鋼であり、例５〜７、１２〜１も １
０ １７、２０〜２５及び２７〜４２に於ては硫酸鍵で
あり、例１５に於てはステアリン酸亜鉛であり、例１８
に於ては酢酸ニッケルである。The metal salts used in the following examples are Examples 2, 3, 8 to
11 and 19 are acetate steels, Examples 4 and 26 are stearate steels, and Examples 5-7 and 12-1 are also 1
In 0 17, 20-25 and 27-42 it is sulfuric acid key, in example 15 it is zinc stearate and in example 18
In this case, it is nickel acetate.
Claims (1)
いてもよく、夫々水素−又はハロゲン−原子、アルキル
−、アルコキシ−、フエニル−、トリル−、ニトロ−、
カルボアルコキシ−、スルホンアミド−、モノ−又はジ
−アルキルスルホンアミド−、カルボンアミド−、モノ
−又はジ−アルキルカルボンアミド−、アルカノイルア
ミノ−基、又は次式▲数式、化学式、表等があります▼
（式中、Ｇは−ＮＨＣＯ−又は−ＣＯＮＨ−を、Ｒは水
素原子を表わす。 ）なる基を意味するか又はＸ＿１とＸ＿２とはフエニル
環と一緒になつてベンズイミダゾロン環を形成し且つＸ
＿３は水素原子を意味する。 Ｙは水素−、クロル−又はブロム−原子を意味し、Ａｒ
はナフチル基、フエニル基（この基は１〜３個のアルキ
ル−、アルコキシ−、アルキルスルホニル−、カルボア
ルコキシ−、トリフルオルメチル−、ニトロ−、シアン
−アルカノイルアミノ−、ベンゾイルアミノ−、カルボ
ンアミド−、スルホンアミド−、モノ−又はジ−アルキ
ルカルボン−又は−スルホン−アミド−基、又はハロゲ
ン原子によつて置換されていてもよい）、ベンズイミダ
ゾロン−、クロルベンズイミダゾロン−、キナゾリンジ
オン−、キノキザリン−、フタルイミド−又はフタラジ
ン−基を意味し、Ｍは亜鉛−、ニツケル−、又は銅−原
子を意味する。その際アルキル−、アルコキシ−及びア
ルカノイル−基は４個までの炭素原子を含む。〕で示さ
れるアザメチン−金属錯化合物。 ただし下記式▲数式、化学式、表等があります▼ 〔式中、Ｒ＿１は水素原子又はメチル基を意味し、Ｒ＿
２は水素−又はハロゲン−原子、アルキル−、アルコキ
シ−、ニトロ−、カルボアルコキシ−、カルボンアミド
−、モノ−又はジ−アルキルカルボンアミド−、フエニ
ルアミノカルボニル−、アルカノイルアミノ−、アルキ
シカルボニルアミノ−、ベンゾイルアミノ−又はベンジ
ルカルボニルアミノ−基を意味し、Ｒ＿３は水素−、ク
ロル−又はブロム−原子を意味し、Ｒ＿４はベンズイミ
ダゾロン基、フエニル基又は−クロル、ブロム及びメチ
ルの群から選ばれる３個までとシアン、ニトロ、メトキ
シ、エトキシ及びトリフルオルメチルの群から選ばれる
２個までとから選ばれる３個までの置換基をもつ−フエ
ニル基を意味する〕で示される化合物の場合を除く。[Claims] 1 The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X_1, X_2 and X_3 may be the same or different, and each represents a hydrogen or halogen atom , alkyl, alkoxy, phenyl, tolyl, nitro,
Carboalkoxy, sulfonamide, mono- or di-alkyl sulfonamide, carbonamide, mono- or di-alkylcarbonamide, alkanoylamino group, or the following formula ▲ Numerical formula, chemical formula, table, etc.
(In the formula, G represents -NHCO- or -CONH- and R represents a hydrogen atom.) or X_1 and X_2 together with a phenyl ring form a benzimidazolone ring, and X
_3 means a hydrogen atom. Y means a hydrogen, chloro or brome atom, Ar
is a naphthyl group, a phenyl group (this group has 1 to 3 alkyl-, alkoxy-, alkylsulfonyl-, carbalkoxy-, trifluoromethyl-, nitro-, cyan-alkanoylamino-, benzoylamino-, carbonamido- , sulfonamido-, mono- or di-alkylcarbon- or -sulfonamido- groups, or optionally substituted by halogen atoms), benzimidazolone-, chlorbenzimidazolone-, quinazolinedione-, It means a quinoxaline, phthalimide or phthalazine group, M means a zinc, nickel or copper atom. The alkyl, alkoxy and alkanoyl radicals contain up to 4 carbon atoms. ] An azamethine-metal complex compound represented by: However, the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1 means a hydrogen atom or a methyl group, and R_
2 is a hydrogen or halogen atom, alkyl, alkoxy, nitro, carbalkoxy, carbonamide, mono- or di-alkylcarbonamide, phenylaminocarbonyl, alkanoylamino, alkoxycarbonylamino -, benzoylamino- or benzylcarbonylamino- group, R_3 means a hydrogen-, chloro- or bromo- atom and R_4 is a benzimidazolone group, a phenyl group or selected from the group -chloro, bromo and methyl. and up to 3 substituents selected from the group consisting of cyan, nitro, methoxy, ethoxy and trifluoromethyl - phenyl group] except.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51000625A JPS6038422B2 (en) | 1976-01-01 | 1976-01-01 | Azamethine-metal complex compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51000625A JPS6038422B2 (en) | 1976-01-01 | 1976-01-01 | Azamethine-metal complex compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5285216A JPS5285216A (en) | 1977-07-15 |
| JPS6038422B2 true JPS6038422B2 (en) | 1985-08-31 |
Family
ID=11478900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51000625A Expired JPS6038422B2 (en) | 1976-01-01 | 1976-01-01 | Azamethine-metal complex compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6038422B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05275132A (en) * | 1992-03-27 | 1993-10-22 | Mitsubishi Denki Shomei Kk | Connection terminal block with earth terminal |
| US6914114B2 (en) | 2000-07-17 | 2005-07-05 | Honeywell International Inc. | Absorbing compounds for spin-on-glass anti-reflective coatings for photolithography |
| US8992806B2 (en) | 2003-11-18 | 2015-03-31 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
-
1976
- 1976-01-01 JP JP51000625A patent/JPS6038422B2/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05275132A (en) * | 1992-03-27 | 1993-10-22 | Mitsubishi Denki Shomei Kk | Connection terminal block with earth terminal |
| US6914114B2 (en) | 2000-07-17 | 2005-07-05 | Honeywell International Inc. | Absorbing compounds for spin-on-glass anti-reflective coatings for photolithography |
| US8992806B2 (en) | 2003-11-18 | 2015-03-31 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285216A (en) | 1977-07-15 |
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