JPH021187B2 - - Google Patents
Info
- Publication number
- JPH021187B2 JPH021187B2 JP19361881A JP19361881A JPH021187B2 JP H021187 B2 JPH021187 B2 JP H021187B2 JP 19361881 A JP19361881 A JP 19361881A JP 19361881 A JP19361881 A JP 19361881A JP H021187 B2 JPH021187 B2 JP H021187B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- represent
- halogen atom
- general formula
- nitroaniline
- 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
- 239000000049 pigment Substances 0.000 claims description 16
- -1 nitroaniline diazo compound Chemical class 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 3
- MMBYJYAFFGKUDC-UHFFFAOYSA-N 3-aminoisoindol-1-one Chemical compound C1=CC=C2C(N)=NC(=O)C2=C1 MMBYJYAFFGKUDC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000004040 coloring Methods 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- DMGFVJVLVZOSOE-UHFFFAOYSA-N 3-amino-4-chlorobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1Cl DMGFVJVLVZOSOE-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 description 1
- JBXZCPXEYAEMJS-UHFFFAOYSA-N 2,5-dichloro-4-nitroaniline Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl JBXZCPXEYAEMJS-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- JKDBEPYYWWSPKJ-UHFFFAOYSA-N 3-amino-4-chloro-n-phenylbenzamide Chemical compound C1=C(Cl)C(N)=CC(C(=O)NC=2C=CC=CC=2)=C1 JKDBEPYYWWSPKJ-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
- 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
- LPNBIVMNNQDVJP-UHFFFAOYSA-N 3-amino-n-(2,4-dichlorophenyl)benzamide Chemical compound NC1=CC=CC(C(=O)NC=2C(=CC(Cl)=CC=2)Cl)=C1 LPNBIVMNNQDVJP-UHFFFAOYSA-N 0.000 description 1
- KPSPULPPMWHXGE-UHFFFAOYSA-N 3-amino-n-phenylbenzamide Chemical compound NC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 KPSPULPPMWHXGE-UHFFFAOYSA-N 0.000 description 1
- LDSIOPGMLLPSSR-UHFFFAOYSA-N 3-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C(Cl)=C1 LDSIOPGMLLPSSR-UHFFFAOYSA-N 0.000 description 1
- QNAAQOLWUDNQFY-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1.NC1=CC=CC(Cl)=C1 QNAAQOLWUDNQFY-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- ZWWOYERTGZZDMF-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3,3-dimethoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(OC)(OC)NC2=O ZWWOYERTGZZDMF-UHFFFAOYSA-N 0.000 description 1
- UTFUHDBTROURBI-UHFFFAOYSA-N 4,5,7-trichloro-3,3,6-trimethoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(OC)=C(Cl)C2=C1C(OC)(OC)NC2=O UTFUHDBTROURBI-UHFFFAOYSA-N 0.000 description 1
- IAMMYRVIUQSRQI-UHFFFAOYSA-N 4,5,7-trichloro-3,3-dimethoxy-6-phenoxy-2h-isoindol-1-one Chemical compound COC1(OC)NC(=O)C(C=2Cl)=C1C(Cl)=C(Cl)C=2OC1=CC=CC=C1 IAMMYRVIUQSRQI-UHFFFAOYSA-N 0.000 description 1
- YZGXXESTJNQKOM-UHFFFAOYSA-N 4,5,7-trichloro-3,3-dimethoxy-6-propoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(OCCC)=C(Cl)C2=C1C(OC)(OC)NC2=O YZGXXESTJNQKOM-UHFFFAOYSA-N 0.000 description 1
- HOAHPZSWJZCHHN-UHFFFAOYSA-N 4,5,7-trichloro-6-ethoxy-3,3-dimethoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(OCC)=C(Cl)C2=C1C(OC)(OC)NC2=O HOAHPZSWJZCHHN-UHFFFAOYSA-N 0.000 description 1
- QHWDUJPWCGEBTH-UHFFFAOYSA-N 4-amino-n-phenylbenzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1 QHWDUJPWCGEBTH-UHFFFAOYSA-N 0.000 description 1
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- GNVBAYFCKSXVNQ-UHFFFAOYSA-N 6-butoxy-4,5,7-trichloro-3,3-dimethoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(OCCCC)=C(Cl)C2=C1C(OC)(OC)NC2=O GNVBAYFCKSXVNQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 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
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 238000010531 catalytic reduction reaction Methods 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
- IIGAELMXVLEZPM-GRVYQHKQSA-L cobalt(2+);(9z,12z)-octadeca-9,12-dienoate Chemical compound [Co+2].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O.CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O IIGAELMXVLEZPM-GRVYQHKQSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- DFXUJVLVUMQDDC-UHFFFAOYSA-N formamide;1,3,5-triazine-2,4,6-triamine Chemical compound NC=O.NC1=NC(N)=NC(N)=N1 DFXUJVLVUMQDDC-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- XYQXGZLLGNQFSL-UHFFFAOYSA-N methyl 2,3,4,5-tetrachloro-6-cyanobenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C#N XYQXGZLLGNQFSL-UHFFFAOYSA-N 0.000 description 1
- RAMPDACRJWTXEV-UHFFFAOYSA-N methyl 2-cyanobenzoate Chemical compound COC(=O)C1=CC=CC=C1C#N RAMPDACRJWTXEV-UHFFFAOYSA-N 0.000 description 1
- CPWKRSWUPXTENQ-UHFFFAOYSA-N n-(3-amino-4-chlorophenyl)benzamide Chemical compound C1=C(Cl)C(N)=CC(NC(=O)C=2C=CC=CC=2)=C1 CPWKRSWUPXTENQ-UHFFFAOYSA-N 0.000 description 1
- DDRCIGNRLHTTIW-UHFFFAOYSA-N n-(4-amino-2,5-dimethoxyphenyl)benzamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2C=CC=CC=2)=C1OC DDRCIGNRLHTTIW-UHFFFAOYSA-N 0.000 description 1
- HZXWADJABXBCOJ-UHFFFAOYSA-N n-(4-amino-3-chlorophenyl)benzamide Chemical compound C1=C(Cl)C(N)=CC=C1NC(=O)C1=CC=CC=C1 HZXWADJABXBCOJ-UHFFFAOYSA-N 0.000 description 1
- JFHQBECHISXXKM-UHFFFAOYSA-N n-(4-aminophenyl)-2,4-dichlorobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(Cl)C=C1Cl JFHQBECHISXXKM-UHFFFAOYSA-N 0.000 description 1
- LFTPGONCZMIVID-UHFFFAOYSA-N n-(4-aminophenyl)-2-chlorobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1Cl LFTPGONCZMIVID-UHFFFAOYSA-N 0.000 description 1
- CYSQNIFSCOEHDN-UHFFFAOYSA-N n-(4-aminophenyl)-4-chlorobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 CYSQNIFSCOEHDN-UHFFFAOYSA-N 0.000 description 1
- GTTFJYUWPUKXJH-UHFFFAOYSA-N n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 GTTFJYUWPUKXJH-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 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
- 239000002861 polymer material Substances 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
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 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
- 239000005060 rubber Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
本発明は、一般式：
（但し、式中、R1及びR2は水素原子またはハロ
ゲン原子を表す）で表されるニトロアニリンのジ
アゾ化合物を、次式：
〔但し、式中、X1，X2及びX3は水素原子、ハロ
ゲン原子、炭素原子数１ないし４のアルコキシ基
または次式
The present invention is based on the general formula: (However, in the formula, R 1 and R 2 represent a hydrogen atom or a halogen atom.) A nitroaniline diazo compound represented by the following formula: [However, in the formula, X 1 , X 2 and X 3 are hydrogen atoms, halogen atoms, alkoxy groups having 1 to 4 carbon atoms, or the following formula:
【式】または
（式中、Z1、Z2、Z3、Z4及びZ5は、水素原子また
はハロゲン原子を表す）で表される基を表す〕で
表されるアセトアセトアミドとカツプリングさ
せ、得られたニトロアゾ化合物を接触還元して、
一般式：
（但し、式中、R1、R2、X1、X2及びX3は前記の
意味を表す）で表されるアミノアゾ化合物とし、
最後に、
一般式：
（式中、R′は炭素原子数１ないし４のアルキル
基を表し、Ｘはハロゲン原子を表し、Ｙ及びＺは
ハロゲン原子または炭素原子数１ないし４のアル
コキシ基を表す）で表されるイソインドリノンと
縮合させることを特徴とする、一般式：
（但し、式中、Ｘ，Ｙ，Ｚ，R1，R2，X1，X2及
びX3は前記の意味を表す）で表されるイミノイ
ソインドリノン顔料の製法に関する。
この反応において、一般式：
（式中、R1及びR2は前記の意味を表わす）で表
わされるニトロアニリンを使用することが好まし
い。これらのニトロアニリン類の例としては、
３―または４―ニトロアニリン、
２―または３―クロロ―４―ニトロアニリン及
び２，５―ジクロロ―４―ニトロアニリンなどを
挙げることができる。
カツプリング成分としては、次式：
〔式中、X1、X2及びX3は水素原子、ハロゲン原
子、炭素原子数１ないし４のアルコキシ基、ある
いは次式：[expression] or (In the formula, Z 1 , Z 2 , Z 3 , Z 4 and Z 5 represent a hydrogen atom or a halogen atom) By catalytically reducing the compound,
General formula: (However, in the formula, R 1 , R 2 , X 1 , X 2 and X 3 represent the above-mentioned meanings),
Finally, the general formula: (In the formula, R' represents an alkyl group having 1 to 4 carbon atoms, X represents a halogen atom, and Y and Z represent a halogen atom or an alkoxy group having 1 to 4 carbon atoms.) General formula, characterized by condensation with indolinone: The present invention relates to a method for producing an iminoisoindolinone pigment represented by the formula (wherein, X, Y, Z, R 1 , R 2 , X 1 , X 2 and X 3 have the above-mentioned meanings). In this reaction, the general formula: Preference is given to using nitroaniline represented by the formula (wherein R 1 and R 2 have the meanings given above). Examples of these nitroanilines include 3- or 4-nitroaniline, 2- or 3-chloro-4-nitroaniline, and 2,5-dichloro-4-nitroaniline. As a coupling component, the following formula: [In the formula, X 1 , X 2 and X 3 are a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or the following formula:
【式】または
（式中、Z1、Z2、Z3、Z4及びZ5は水素原子または
ハロゲン原子を表す）で表される基を表わす〕で
表されるアセトアセトアニリドを使用する。
具体的な例として下記のアミン類のアセトアセ
チル化合物をあげることができる。
アニリン、２―または４―クロロアニリン、
２，３―、２，４―または２，５―ジクロロアニ
リン、２，４，５―トリクロロアニリン、２―ま
たは４―メトキシアニリン、４―エトキシアニリ
ン、２，４―ジメトキシアニリン、４―クロロ―
２，５―ジメトキシアニリン、２―メトキシ―５
―クロロアニリン、
４―ベンゾイルアミノ―アニリン、
２―クロロ―４―ベンゾイルアミノ―アニリ
ン、４―（ｏ―クロロベンゾイルアミノ）―アニ
リン、
４―（ｐ―クロロベンゾイルアミノ）―アニリ
ン、
４―（2′，4′―ジクロロベンゾイルアミノ）―
アニリン、
２，５―ジメトキシ―４―ベンゾイルアミノ―
アニリン、
２―クロロ―５―ベンゾイルアミノ―アニリ
ン、
１―アミノベンゼン―４―カルボン酸アニリ
ド、
１―アミノベンゼン―３―カルボン酸アニリ
ド、
１―アミノ―２―クロロベンゼン―５―カルボ
ン酸アニリド、
１―アミノ―２―クロロベンゼン―５―カルボ
ン酸―ｏ―，―ｍ―またはｐ―クロロアニリド、
１―アミノ―２―クロロベンゼン―５―カルボ
ン酸―2′―5′―または―2′，4′―ジクロロアニリ
ド、
１―アミノ―２―クロロベンゼン―５―カルボ
ン酸―2′，4′，5′―トリクロロアニリド、１―ア
ミノ―２―メトキシベンゼン―５―カルボン酸ア
ニリド、
１―アミノ―２―メトキシベンゼン―５―カル
ボン酸―ｏ―，―ｍ―または―ｐ―クロロアニリ
ド、
１―アミノベンゼン―３―カルボン酸―２，４
―ジクロロアニリド、
１―アミノベンゼン―３―または―４―カルボ
ン酸―2′―4′―、―3′，4′―または―2′，5′―ジ
ク
ロロアニリド、
１―アミノベンゼン―３―または―４―カルボ
ン酸―2′，4′，5′―トリクロロアニリド。
ニトロアニリンのジアゾ化及びアセトアセトア
ニリドとのカツプリング反応は通常の方法で行う
ことができる。
イソインドリノンとしては、次式
（式中、R′は炭素原子数１ないし４のアルキル
基をＸ，Ｙ及びＺは前記式で与えられた意味を
表す）
で表される化合物を使用する。
対応する２―シアノ安息香酸エステルをメタノ
ール中にとかしたナトリウムメチラートで変換し
てナトリウム塩の形で使用するのが適当である。
特に、式（）で表されるイソインドリノン類
においてＸ，Ｙ及びＺが塩素原子を表すものを用
いる。具体例として次のものをあげることができ
る。
３，３，―ジメトキシ―４，５，６，７―テト
ラクロロ―イソインドリノン、３，３―ジメトキ
シ―４，５，７―トリクロロ―６―メトキシ―イ
ソインドリノン、
３，３―ジメトキシ―４，５，７―トリクロロ
―６―エトキシ―イソインドリノン、
３，３―ジメトキシ―４，５，７―トリクロロ
―６―ｎ―プロポキシ―イソインドリノン、
３，３―ジメトキシ―４，５，７―トリクロロ
―６―ｎ―ブトキシ―イソインドリノン、
３，３―ジメトキシ―４，５，７―トリクロロ
―６―フエノキシ―イソインドリノン、
３，５―ジメトキシ―５，７―ジクロロ―４，
６―ジメトキシ―イソインドリノン、
これらは公知化合物である。
式で表わされる顔料を製造するには３，３―
ジアルコキシ―４，５，７―テトラクロロイソイ
ンドリノン―１―オンから出発し、高沸点有機溶
媒、例えばｏ―ジクロロベンゼン中で、好ましく
はメチルセロソルブ、ジメチルホルムアミドまた
はＮ―メチルピロリドンなどの溶媒助剤の存在下
で80乃至180℃、好ましくは100―150℃の温度で
アミノアゾ染料化合物と、縮合させる。この反応
は、塩基の結合剤、例えば低級脂肪酸、特に酢酸
の存在下で行うことが好ましい。
この顔料は生成した後、合成媒体から直接沈澱
する。この顔料は、必要ならば粉砕操作の後（ま
たは直接）、多くの顔料用途に使用することがで
き、これにより、最初に条件を整えることによつ
て顔料として成立することのできる、英国特許出
願第2019871号の方法によつて得られた顔料より
も有利であることを特徴としている。得られた染
料はすぐれた顔料を与える。
得られた顔料は微粉砕して有機高分子材料の着
色に使用される。例えば、エチルセルローズ、ア
セチルセルローズ、ニトロセルローズのようなセ
ルローズエーテル及びセルローズエステル；ポリ
アミド、ポリウレタン、またはポリエステル、天
然または合成樹脂、例えばアミノプラスター、特
に尿素―ホルムアミド樹脂及びメラミン―ホルム
アミド樹脂、アルキド樹脂、フエノプラスター、
ポリカーボネート、ポリオレフイン、ポリスチロ
ール、ポリ塩化エチレン、ポリエチレン、ポリプ
ロピレン、ポリアクリロニトリル、ポリアクリル
酸エステル、熱可塑性及び熱硬化性アクリル樹
脂、ゴム、カゼイン、シリコーン及びシリコン樹
脂などの着色に、単独で、または混合物として使
用される。この場合、上記の高分子化合物は塊
状、溶融状態、あるいは紡糸液、ラツカーまたは
印刷インクの形で存在しても差異はない。使用目
的によつて、新しい顔料をトーナーとして、また
はプレパラートの形で使用することも適当であ
る。
得られた着色物は、高い着色強度、高い色調純
粋性、及び良好な耐上塗り性、移行安定性、光安
定性、熱安定性及び耐候性を示す。
下記の実施例においては％は重量％を表わし、
温度は摂氏温度を示す。
実施例 １
４―ニトロアニリンを公知の方法でジアゾ化
し、アセトアセチル―２，５―ジメトキシ―４―
クロロアニリドとカツプリングさせる。生成した
ニトロアゾ染料をジメチルホルムアミドから再結
晶する。融点298〜300℃。
上記のようにして得た染料57.3ｇをジメチルホ
ルムアミド1080c.c.中で、ラネーニツケル触媒18ｇ
の存在下、30―35℃の温度で常圧接触還元する。
生成した4′―アミノフエニールアゾ―アセトアセ
トアミド―２，５―ジメトキシ―４―クロロアニ
リドは融点239―241℃を示し、収量は95％であ
る。
３，４，５，６―テトラクロロ―２―シアノ安
息香酸メチルエステル12.95ｇとINナトリウムメ
チラートのメタノール溶液43.2mlとを３，３―ジ
メトキシ―４，５，６，７―テトラクロロイソイ
ンドリン―１―オンのナトリウム塩の透明溶液中
に撹拌下に加える。4′―アミノフエニルアゾ―ア
セトアセトアミド―２，５―ジメトキシ―４―ク
ロロアニリド14.6ｇとｏ―ジクロロベンゼン200
ml及びエチレングリコールモノメチルエーテル10
mlを加えた後、浴温120℃で１時間以内にメタノ
ールを溜去するように内温を100℃まで上げ、１
時間その温度に保つ。酢酸15mlを加えて酸性と
し、温度を140―150℃まで上げる。この温度で２
時間撹拌した後、不溶の顔料を120℃で過し、
メタノール、アセトン次に水で洗う。乾燥後、
23.6ｇのオレンジ色顔料を得る。このもはそのま
まで、または公知の方法により粉砕した後に合成
樹脂の着色、或いは印刷用ペースト及び着色ラツ
カーなどの製造に使用することができる。得られ
たオレンジ色着色物は良好な着色強度と安定した
色調を示す。
実施例 ２―５
実施例１の方法に従つて、下記の第１表、第１
欄に記載したニトロアニリン使用し、第３欄に記
載したアセトアセトアニリドとカツプリングさせ
た後、生成したニトロアゾ色素を還元し、３，
４，５，６―テトラクロロ―シアノ安息香酸メチ
ルエステルと反応させて得られたアミノアゾ染料
を第１表に記載する。表中、第４欄に着色顔料：
二酸化チタン＝５：95を含む顔料によつて着色し
たアルキド―メラミン樹脂ラツカーの色調を示
す。これらのラツカーはすぐれた耐候性を示す。[expression] or (Representing a group represented by the following formula, Z 1 , Z 2 , Z 3 , Z 4 and Z 5 represent a hydrogen atom or a halogen atom) is used. Specific examples include the following amine acetoacetyl compounds. Aniline, 2- or 4-chloroaniline,
2,3-, 2,4- or 2,5-dichloroaniline, 2,4,5-trichloroaniline, 2- or 4-methoxyaniline, 4-ethoxyaniline, 2,4-dimethoxyaniline, 4-chloro-
2,5-dimethoxyaniline, 2-methoxy-5
-chloroaniline, 4-benzoylamino-aniline, 2-chloro-4-benzoylamino-aniline, 4-(o-chlorobenzoylamino)-aniline, 4-(p-chlorobenzoylamino)-aniline, 4-(2 ′,4′-dichlorobenzoylamino)—
Aniline, 2,5-dimethoxy-4-benzoylamino-
Aniline, 2-chloro-5-benzoylamino-aniline, 1-aminobenzene-4-carboxylic acid anilide, 1-aminobenzene-3-carboxylic acid anilide, 1-amino-2-chlorobenzene-5-carboxylic acid anilide, 1 -amino-2-chlorobenzene-5-carboxylic acid -o-, -m- or p-chloroanilide, 1-amino-2-chlorobenzene-5-carboxylic acid -2'-5'- or -2',4' -dichloroanilide, 1-amino-2-chlorobenzene-5-carboxylic acid-2',4',5'-trichloroanilide, 1-amino-2-methoxybenzene-5-carboxylic acid anilide, 1-amino-2- Methoxybenzene-5-carboxylic acid-o-, -m- or -p-chloroanilide, 1-aminobenzene-3-carboxylic acid-2,4
-dichloroanilide, 1-aminobenzene-3- or -4-carboxylic acid-2'-4'-, -3',4'- or -2',5'-dichloroanilide, 1-aminobenzene-3- or -4-carboxylic acid-2',4',5'-trichloroanilide. Diazotization of nitroaniline and coupling reaction with acetoacetanilide can be carried out by conventional methods. As isoindolinone, the following formula (wherein R' is an alkyl group having 1 to 4 carbon atoms, and X, Y and Z have the meanings given in the above formula) is used. It is suitable to convert the corresponding 2-cyanobenzoic acid ester with sodium methylate dissolved in methanol and use it in the form of the sodium salt. In particular, isoindolinones represented by the formula () in which X, Y and Z represent chlorine atoms are used. The following are specific examples: 3,3-dimethoxy-4,5,6,7-tetrachloro-isoindolinone, 3,3-dimethoxy-4,5,7-trichloro-6-methoxy-isoindolinone, 3,3-dimethoxy- 4,5,7-trichloro-6-ethoxy-isoindolinone, 3,3-dimethoxy-4,5,7-trichloro-6-n-propoxy-isoindolinone, 3,3-dimethoxy-4,5, 7-trichloro-6-n-butoxy-isoindolinone, 3,3-dimethoxy-4,5,7-trichloro-6-phenoxy-isoindolinone, 3,5-dimethoxy-5,7-dichloro-4,
6-dimethoxy-isoindolinone, these are known compounds. To produce the pigment represented by the formula 3,3-
Starting from dialkoxy-4,5,7-tetrachloroisoindolinon-1-one, in a high-boiling organic solvent such as o-dichlorobenzene, preferably a solvent such as methylcellosolve, dimethylformamide or N-methylpyrrolidone. Condensation is carried out with the aminoazo dye compound in the presence of auxiliaries at a temperature of 80-180°C, preferably 100-150°C. This reaction is preferably carried out in the presence of a basic binder, such as a lower fatty acid, especially acetic acid. After the pigment has been produced, it is precipitated directly from the synthesis medium. This pigment can be used in a number of pigmentary applications, if necessary after a grinding operation (or directly), and can thus be established as a pigment by first providing the conditions for which the UK patent application is being applied. It is characterized by advantages over the pigments obtained by the method of No. 2019871. The dyes obtained give excellent pigments. The obtained pigment is pulverized and used for coloring organic polymer materials. For example, cellulose ethers and cellulose esters such as ethyl cellulose, acetyl cellulose, nitrocellulose; polyamides, polyurethanes or polyesters, natural or synthetic resins such as amino plasters, especially urea-formamide resins and melamine-formamide resins, alkyd resins, noplaster,
For coloring polycarbonate, polyolefin, polystyrene, polychlorinated ethylene, polyethylene, polypropylene, polyacrylonitrile, polyacrylic ester, thermoplastic and thermosetting acrylic resin, rubber, casein, silicone and silicone resin, alone or in mixtures. used as. In this case, it makes no difference whether the above-mentioned polymeric compounds are present in bulk, molten state, or in the form of a spinning solution, lacquer or printing ink. Depending on the intended use, it is also suitable to use the fresh pigments as toners or in the form of preparations. The resulting colorations exhibit high color strength, high tonal purity, and good overcoat resistance, migration stability, light stability, heat stability and weather resistance. In the examples below, % represents weight %,
Temperatures are in degrees Celsius. Example 1 4-nitroaniline was diazotized by a known method to form acetoacetyl-2,5-dimethoxy-4-
Combine with chloroanilide. The nitroazo dye formed is recrystallized from dimethylformamide. Melting point 298-300℃. 57.3 g of the dye obtained as above was added to 18 g of Raney nickel catalyst in 1080 c.c. of dimethylformamide.
Atmospheric pressure catalytic reduction at a temperature of 30-35℃ in the presence of
The produced 4'-aminophenyl azo-acetoacetamide-2,5-dimethoxy-4-chloroanilide has a melting point of 239-241°C and a yield of 95%. 12.95 g of 3,4,5,6-tetrachloro-2-cyanobenzoic acid methyl ester and 43.2 ml of a methanol solution of IN sodium methylate were added to 3,3-dimethoxy-4,5,6,7-tetrachloroisoindoline. Add under stirring into a clear solution of the sodium salt of -1-one. 14.6 g of 4'-aminophenylazo-acetoacetamide-2,5-dimethoxy-4-chloroanilide and 200 g of o-dichlorobenzene
ml and ethylene glycol monomethyl ether 10
ml, the internal temperature was raised to 100°C to distill off the methanol within 1 hour at a bath temperature of 120°C.
Keep at that temperature for an hour. Acidify by adding 15 ml of acetic acid and raise the temperature to 140-150°C. At this temperature 2
After stirring for an hour, the undissolved pigment was filtered at 120°C,
Wash with methanol, acetone and then water. After drying,
23.6 g of orange pigment are obtained. This product can be used as it is or after being pulverized by a known method for coloring synthetic resins or for producing printing pastes, coloring lacquers, and the like. The obtained orange colored product exhibits good coloring strength and stable color tone. Example 2-5 According to the method of Example 1, the following Table 1,
After coupling the nitroaniline listed in column 3 with acetoacetanilide listed in column 3, the resulting nitroazo dye is reduced, and 3.
Aminoazo dyes obtained by reaction with 4,5,6-tetrachloro-cyanobenzoic acid methyl ester are listed in Table 1. Colored pigments in column 4 in the table:
The color of an alkyd-melamine resin lacquer colored with a pigment containing titanium dioxide = 5:95 is shown. These lacquers exhibit excellent weather resistance.
【表】
実施例 ６―９
実施例２と同様にして、下記第２表第２欄に記
載したニトロアニリンをジアゾ化し、第３欄に記
載したアセトアセトアミドとカツプリングさせ、
得られたニトロアゾ染料を還元し、生成したアミ
ノアゾ染料を実施例２の方法によつて第３欄に記
載したシアノ安息香酸メチルエステルと反応させ
て得られた着色力良好な顔料の例を第２表に示
す。第２表第４欄にポリ塩化ビニル（PVC）を
１％で着色したものの色調を示す。[Table] Example 6-9 In the same manner as in Example 2, nitroaniline listed in the second column of Table 2 below was diazotized and coupled with acetoacetamide listed in the third column,
Examples of pigments with good tinting power obtained by reducing the obtained nitroazo dye and reacting the produced aminoazo dye with the cyanobenzoic acid methyl ester described in the third column by the method of Example 2 are shown in the second example. Shown in the table. Column 4 of Table 2 shows the color tone of products colored with 1% polyvinyl chloride (PVC).
【表】
実施例 10
実施例９で製造した顔料２ｇを、アルミナ水和
物36ｇ、中位の粘度のアマニ油ワニス60ｇ及びリ
ノール酸コバルト２ｇと混合して３本ロールスト
ールですりつぶす。生成した染料ペーストで作つ
たオレンジ色のプリントは強い着色と耐光性を示
す。
実施例 11
実施例２で製造した顔料0.6ｇをポリ塩化ビニ
ル67ｇ、ジオクチルフタレート33ｇ、ジブチル錫
ジラウレート２ｇ及び二酸化チタン２ｇと混合
し、ロールストール上、160℃で15分間でうすい
フイルムにする。このようにして生成した黄色着
色物は強い着色を示し耐移行性、耐熱性及び耐光
性にすぐれている。
実施例 12
二酸化チタン10ｇと実施例１で製造した樹脂２
ｇとを、ココナツツアルキド樹脂26.4ｇ、メラミ
ン―ホルムアルデヒド樹脂（固型分50％含有）
24.0ｇ、エチレングリコールモノメチルエーテル
8.8ｇ及びキシレン28.8ｇの混合物88ｇとボール
ミル中で48時間磨砕する。
このラツカーをアルミニウム箔上にスプレーコ
ートし、室温で30分間乾燥し、次に120℃で30分
間焼付けを行うと、オレンジ色の着色物を得る。
このものは高い着色強度と非常にすぐれた耐オー
バーラツカー性、耐光性及び耐候性を示した。Table: Example 10 2 g of the pigment prepared in Example 9 are mixed with 36 g of alumina hydrate, 60 g of medium viscosity linseed oil varnish and 2 g of cobalt linoleate and ground in a three-roll stall. Orange prints made with the resulting dye paste exhibit strong coloring and lightfastness. Example 11 0.6 g of the pigment prepared in Example 2 is mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyltin dilaurate and 2 g of titanium dioxide and formed into a thin film on a roll stall at 160° C. for 15 minutes. The yellow colored product thus produced has strong coloring and is excellent in migration resistance, heat resistance and light resistance. Example 12 10 g of titanium dioxide and resin 2 produced in Example 1
g, coconut alkyd resin 26.4g, melamine-formaldehyde resin (contains 50% solids)
24.0g, ethylene glycol monomethyl ether
Mill with 88 g of a mixture of 8.8 g and 28.8 g xylene in a ball mill for 48 hours. The lacquer is spray coated onto aluminum foil, dried for 30 minutes at room temperature, and then baked for 30 minutes at 120°C to give an orange coloring.
This product exhibited high coloring strength and excellent overlacquer resistance, light fastness and weather resistance.
Claims (1)
ゲン原子を表す）で表されるニトロアニリンのジ
アゾ化合物を、式： 〔但し、式中、X1、X2及びX3は水素原子、ハロ
ゲン原子、炭素原子数１ないし４のアルコキシ基
または次式 【式】または （式中、Z1、Z2、Z3、Z4及びZ5は、水素原子また
はハロゲン原子を表す）で表される基を表す〕で
表されるアセトアセトアミドとカツプリングさ
せ、得られたニトロアゾ化合物を接触還元して、
一般式： （但し、式中、R1、R2、X1、X2及びX3は前記の
意味を表す）で表されるアミノアゾ化合物とし、
最後に、 一般式： （式中、R′は炭素原子数１ないし４のアルキル
基を表し、Ｘはハロゲン原子を表し、Ｙ及びＺは
ハロゲン原子または炭素原子数１ないし４のアル
コキシ基を表す）で表されるイソインドリノンと
縮合させることを特徴とする、一般式： （但し、式中、Ｘ，Ｙ，Ｚ，R1，R2，X1，X2及
びX3は前記の意味を表す）で表されるイミノイ
ソインドリノン顔料の製法。 ２ 次式： （但し、式中、R1及びR2は前記の意味を表わす） で表されるニトロアニリンを使用することを特徴
とする特許請求の範囲第１項記載の方法。 ３ 前記一般式において、Ｘ，Ｙ及びＺが塩素原
子を表わすイソインドリノンを使用することを特
徴とする特許請求の範囲第１項記載の方法。[Claims] 1. General formula: (However, in the formula, R 1 and R 2 represent a hydrogen atom or a halogen atom.) A nitroaniline diazo compound represented by the formula: [However, in the formula, X 1 , X 2 and X 3 are a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or the following formula [formula] or (In the formula, Z 1 , Z 2 , Z 3 , Z 4 and Z 5 represent a hydrogen atom or a halogen atom) By catalytically reducing the compound,
General formula: (However, in the formula, R 1 , R 2 , X 1 , X 2 and X 3 represent the above-mentioned meanings),
Finally, the general formula: (In the formula, R' represents an alkyl group having 1 to 4 carbon atoms, X represents a halogen atom, and Y and Z represent a halogen atom or an alkoxy group having 1 to 4 carbon atoms.) General formula, characterized by condensation with indolinone: A method for producing an iminoisoindolinone pigment represented by the formula (wherein, X, Y, Z, R 1 , R 2 , X 1 , X 2 and X 3 have the above-mentioned meanings). Quadratic formula: The method according to claim 1, characterized in that a nitroaniline represented by the following formula is used: (wherein R 1 and R 2 have the meanings defined above). 3. The method according to claim 1, characterized in that in the general formula, isoindolinone is used in which X, Y and Z represent chlorine atoms.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH888480A CH643870A5 (en) | 1980-12-01 | 1980-12-01 | Process for preparing iminoisoindolinone dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57119954A JPS57119954A (en) | 1982-07-26 |
| JPH021187B2 true JPH021187B2 (en) | 1990-01-10 |
Family
ID=4345831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19361881A Granted JPS57119954A (en) | 1980-12-01 | 1981-12-01 | Iminoisoindoline pigment and manufacture |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS57119954A (en) |
| CH (1) | CH643870A5 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014383447B2 (en) * | 2014-02-19 | 2017-11-30 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Near infrared-reflecting/transmitting azo pigment, method for manufacturing near infrared-reflecting/transmitting azo pigment, colorant composition using said azo pigments, item-coloring method and colored item |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5430221A (en) * | 1977-08-11 | 1979-03-06 | Dainichi Seika Kogyo Kk | Preparation of azo pigments |
| JPS54141821A (en) * | 1978-04-27 | 1979-11-05 | Dainichi Seika Kogyo Kk | Azo pigment |
-
1980
- 1980-12-01 CH CH888480A patent/CH643870A5/en not_active IP Right Cessation
-
1981
- 1981-12-01 JP JP19361881A patent/JPS57119954A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH643870A5 (en) | 1984-06-29 |
| JPS57119954A (en) | 1982-07-26 |
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