DE2535140A1 - NEW MONOAZO PIGMENTS, PROCESS FOR THEIR PRODUCTION AND USE - Google Patents
NEW MONOAZO PIGMENTS, PROCESS FOR THEIR PRODUCTION AND USEInfo
- Publication number
- DE2535140A1 DE2535140A1 DE19752535140 DE2535140A DE2535140A1 DE 2535140 A1 DE2535140 A1 DE 2535140A1 DE 19752535140 DE19752535140 DE 19752535140 DE 2535140 A DE2535140 A DE 2535140A DE 2535140 A1 DE2535140 A1 DE 2535140A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- atoms
- groups
- methyl
- amino
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims description 28
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 230000008878 coupling Effects 0.000 claims description 18
- 238000010168 coupling process Methods 0.000 claims description 18
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000007656 barbituric acids Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- PWXIOTZPLWVFNU-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-methyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)CC(=O)N1C1=CC=CC(Cl)=C1 PWXIOTZPLWVFNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- MJXYFLJHTUSJGU-UHFFFAOYSA-N 7-amino-4-methyl-1h-quinolin-2-one Chemical compound NC1=CC=C2C(C)=CC(=O)NC2=C1 MJXYFLJHTUSJGU-UHFFFAOYSA-N 0.000 description 2
- 241001292331 Choisya Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FBQJKKPQBMSWEP-UHFFFAOYSA-N 1,3-diphenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1 FBQJKKPQBMSWEP-UHFFFAOYSA-N 0.000 description 1
- PKJBRKTYYNRVSN-UHFFFAOYSA-N 10-(aminomethyl)-9,10-dihydroanthracene-1,2-diol Chemical compound OC1=CC=C2C(CN)C3=CC=CC=C3CC2=C1O PKJBRKTYYNRVSN-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KWMUSDDZNYHIBR-UHFFFAOYSA-N 3-amino-1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)C(N)=CC2=C1 KWMUSDDZNYHIBR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 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
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 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
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 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
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000001052 yellow pigment 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0048—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a six-membered heterocyclic ring with one nitrogen atom
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
■Γ * S f.. ^i ClBA-GEIGY AG, CH-4002 Basel■ Γ * S f .. ^ i ClBA-GEIGY AG, CH-4002 Basel
Dr. F, Zumstsm pen. - Dr. E. Assmann Dr. R. Koenigsf.ercjer - Dipl. Fh vs. i?. Hnli-bauer Dipl. . Ing. F. KI!::^Sciise.i - l"r. f:. ^u.üjicin jun.Dr. F, Zumstsm pen. - Dr. E. Assmann Dr. R. Koenigsf.ercjer - Dipl. Fh vs. i ?. Hnli-bauer Dipl.. Ing. F. KI! :: ^ Sciise.i - l "r. F :. ^ U.üjicin jun.
P a t e η I a ;ι ν/ .'ι f t ΰ 8 Münch a r 2, Brauh.iussliaBa 4 P ate η I a; ι ν / .'ι ft ΰ 8 Münch ar 2, Brauh.iussliaBa 4
2535H02535H0
Case 3-9545'/MA 1587
Deutschland Case 3-9545 '/ MA 1587
Germany
Neue Monoazopigraente, Verfahren zu deren Herstellung und VerwendungNew monoazopigraents, processes for their production and use
Die Erfindung betrifft wertvolle neuen MonoazopigmenteThe invention relates to valuable new monoazo pigments
der Formelthe formula
Z RZ R
Y R2Y R 2
worinwherein
X ein O- oder S-Atom oder eine Iminogruppe, Y und Z O-Atome oder Iminogruppen,X is an O or S atom or an imino group, Y and Z are O atoms or imino groups,
X, und Y^, H- oder Halogenatome, Alkyl- oder Alkoxygruppen enthaltend 1-4 C-Atome oder Nitrogruppen,X, and Y ^, H or halogen atoms, alkyl or alkoxy groups containing 1-4 carbon atoms or nitro groups,
R, und R2 Alkylgruppen enthaltend 1-4 C-Atome oder Arylgruppen, vorzugsweise Phenylgruppen bedeuten, die durch Nitrogruppen, Alkyl- oder Alkoxygruppen enthaltend 1-4 C-Atome oder Halogenatome, wie Chlor, Brom oder Jod substituiert sein können.R, and R2 are alkyl groups containing 1-4 carbon atoms or aryl groups, preferably phenyl groups substituted by nitro groups, alkyl or alkoxy groups containing 1-4 C atoms or halogen atoms, such as chlorine, bromine or iodine, can be substituted.
609808/094609808/094
2535H02535H0
Die erfindungsgemässen Pigmente können erhalten werden wenn man eine Diazoverbindung eines Amins der FormelThe pigments of the present invention can be obtained when one is a diazo compound of an amine of the formula
X,X,
H 'I mit einer Verbindung der Formel Z R1 H 'I with a compound of the formula ZR 1
%=X% = X
y R2 y R 2
in welcher Formel X, Y, Z, X-,, Y-,, R-, und R2 die oben angegebene Bedeutung haben, kuppelt.in which formula X, Y, Z, X-, Y-, R-, and R 2 have the meaning given above, couples.
Von besonderem Interesse sind Monoazopigmente der Formel CH.Monoazo pigments of the formula are of particular interest CH.
worin einer der Reste X« und Y2 vorzugsweise Y2 eine Gruppewherein one of the radicals X «and Y 2, preferably Y 2 is a group
der Formelthe formula
0 R1 0 R 1
und der andere ein H- oder Halogenatom eine Nitrogruppe, oder eine Alkyl- oder Alkoxygruppe enthaltend 1-4 C-Atome bedeutet und worin R-· und R^ die angegebene Bedeutung haben.and the other is an H or halogen atom, a nitro group, or denotes an alkyl or alkoxy group containing 1-4 carbon atoms and in which R- · and R ^ have the meaning given.
609800/0943609800/0943
2535UO2535UO
Als Biazokomponenten verwendet man vorzugsweise Verbindungen der FormelCompounds are preferably used as biazo components the formula
worin einer der Reste Xo und Y-, vorzugsweise Y, eine Aminogruppe und der andere ein H- oder Halogenatom, eine Nitrogruppe, eine Alkyl- oder Alkoxygruppe enthaltend 1-4 C-Atome bedeutet.wherein one of the radicals Xo and Y-, preferably Y, a Amino group and the other containing an H or halogen atom, a nitro group, an alkyl or alkoxy group Means 1-4 carbon atoms.
Als Beispiele seien die folgen Amino-chinolone genannt:The following amino-quinolones are mentioned as examples:
4-Methyl-6-amino-chinolon-2 4-Methyl-6-amino-7-chlor-chinolon-2 4-Methyl-6-amino-8-chlor-chinolon-2 4,7-Dimethyl-6-amino-chinolon-2 4,8-Dimethyl-6-amino-chinolon-2 4,5,8-Trimethyl-6-amino-chinolon-2 4-Methyl-6-amino-7-methoxy~chinolon-2 4-Methyl-6-amino-5,8-dimethoxy-chinolon-2 4-Methy1-7-amino-chinolon-2 4-Methyl-7-amino-6-chlor-chinolon-2 4}6-Dimethy1-7-amino-chinolon-2 4,8-Dimethyl-7-amino-chinolon-2 4-Methyl-7-amino-6-methoxy-chinolon-24-methyl-6-amino-quinolone-2 4-methyl-6-amino-7-chloro-quinolone-2 4-methyl-6-amino-8-chloro-quinolone-2 4,7-dimethyl-6-amino -quinolone-2 4,8-dimethyl-6-amino-quinolone-2 4,5,8-trimethyl-6-amino-quinolone-2 4-methyl-6-amino-7-methoxy-quinolone-2 4-methyl -6-amino-5,8-dimethoxy-quinolone-2 4-methyl-7-amino-quinolone-2 4-methyl-7-amino-6-chloro-quinolone-2 4 } 6-dimethy1-7-amino- quinolone-2 4,8-dimethyl-7-amino-quinolone-2 4-methyl-7-amino-6-methoxy-quinolone-2
609808/0943609808/0943
2535U02535U0
Bei diesen Diazokomponenten handelt es sich um bekannte Verb indungen.These diazo components are known Links.
Als Kupplungskomponenten seien in erster Linie N,N1-disubstituierte Barbitursäuren genannt; daneben kommen auch deren funktionelle Derivate in Betracht, beispielsweise die Thio- und Iminoderivate der Formel N, N 1 -disubstituted barbituric acids are primarily mentioned as coupling components; in addition, their functional derivatives are also suitable, for example the thio and imino derivatives of the formula
0 R1 0 R1 00 R 1 0 R 1 0
0 R2 NH0 R 2 NH
Die Substituenten R, und 1L· sind zweckmässig identisch und, vorzugsweise beide Methylgruppen.The substituents R 1 and 1L · are expediently identical and, preferably, both are methyl groups.
Diese Barbitursäurederivate stellen bekannte Verbindungen dar.These barbituric acid derivatives are known compounds.
Die Kupplung findet zweckmässig durch allmähliche Zugabe der wässrigen Diazoniumsalzlösung zur Lösung der Kupplungskomponente in einem mit Wasser mischbaren organischen Lösungsmittel wie z.B. Dimethylformamid oder durch allmähliche Zugabe der wässerigalkalischen Lösung der Kupplungskomponente zur sauren Lösung- des Diazoniumsalzes statt. Die Kupplung wird zweckmässig bei einem pH-Wert von 4 bis 6 durchgeführt.The coupling expediently takes place by gradually adding the aqueous diazonium salt solution to the solution of the coupling component in a water-miscible organic solvent such as dimethylformamide or by gradually adding the aqueous alkaline solution of the coupling component to the acidic solution Diazonium salt instead. The clutch is useful in one pH from 4 to 6 carried out.
609808/0943609808/0943
2535H02535H0
Der pH-Wert wird vorteilhaft durch Zugabe eines Puffers eingestellt. Als Puffer kommen z.B. die Salze, insbesondere Alkalisalze der Ameisensäure, Phosphorsäure oder insbesondere der Essigsäure in Betracht. Die alkalische Lösung der Kupplungskomponente enthält zweckmässig ein Netz-, Dispergier- oder Emulgiermittel, beispielsweise ein Aralkylsulfonat, wie Dodecylbenzolsulfonat oder das Natriumsalz der l,l'-Naphthylmethansulfonsäure, Polykondensationsprodukte von Alkylenoxyden, wie das Einwirkungsprodukt von Aethylenoxyd auf p-tert.-Octylphenyl, ferner Alkylester von SuIforicinoleaten, beispielsweise n-Butylsulforicinoleat. Die Dispersion der Kupplungskomponente kann auch vorteilhaft Schutzkolloide, beispielsweise Methylcellulose oder kleinere Mengen inerter, in Wasser schwerlöslicher oder unlöslicher organische Lösungsmittel enthalten, beispielsweise gegebenenfalls halogenierte oder nitrierte aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzole oder Nitrobenzol, sowie aliphatische Halogenkohlenwasserstoffe wie z.B. Tetrachlorkohlenstoff oder Trichlorethylen, ferner mit Wasser mischbare organische Lösungsmittel, wie Aceton, Me thylathyIketon, Methanol, Aethanol oder Isopropanol, insbesondere Dimethylformamid.The pH is advantageous by adding a buffer set. For example, the salts, in particular alkali metal salts of formic acid, phosphoric acid or in particular, are used as buffers acetic acid into consideration. The alkaline solution of the coupling component expediently contains a wetting, dispersing or emulsifiers, for example an aralkyl sulfonate such as dodecylbenzenesulfonate or the sodium salt of l, l'-naphthylmethanesulfonic acid, Polycondensation products of alkylene oxides, such as the product of the action of ethylene oxide on p-tert.-octylphenyl, also alkyl esters of suIforicinoleates, for example n-butyl sulforicin oleate. The dispersion of the coupling component can also be advantageous protective colloids, for example methyl cellulose or smaller amounts of inert ones that are sparingly soluble in water or contain insoluble organic solvents, for example optionally halogenated or nitrated aromatic Hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzenes or nitrobenzene, as well as aliphatic ones Halogenated hydrocarbons such as carbon tetrachloride or trichlorethylene, as well as organic ones that are miscible with water Solvents such as acetone, methyl ethyl ketone, methanol, ethanol or isopropanol, especially dimethylformamide.
Dank ihrer Unlöslichkeit können die erhaltenen Pigmente aus den Reaktionsgemischen durch Abfiltrieren isoliertThanks to their insolubility, the pigments obtained can isolated from the reaction mixtures by filtration
werden. Es erweist sich als vorteilhaft, die erhaltenen Pigmente mit einem vorzugsweise über 100° C siedenden, organischenwill. It has been found to be advantageous to mix the pigments obtained with an organic, preferably boiling above 100.degree
609808/0943609808/0943
2535U02535U0
Lösungsmittel nachzubehandeln. Als besonders geeignete erweisen sich durch Halogenatome, Alkyl- oder Nitrogruppen substituierte Benzole, wie Xylole, Chlorbenzol, o-Dichlorbenzol oder Nitrobenzol sov?ie Pyridinbasen, wie Pyridin, Picolin oder Chinolin, ferner Ketone, wie Cyclohexanon, Aether, wie Aethylenglycolmonomethyl- oder -monoäthylather, Amide, wie Dimethy!formamid oder N-Methy!-pyrrolidon sowie Dimethylsulfoxyd.Post-treatment of solvents. Those substituted by halogen atoms, alkyl or nitro groups prove to be particularly suitable Benzenes, such as xylenes, chlorobenzene, o-dichlorobenzene or nitrobenzene as? ie pyridine bases, such as pyridine, picoline or quinoline, also ketones, such as cyclohexanone, ethers, such as ethylene glycol monomethyl or monoethyl ethers, amides, such as dimethyl formamide or N-methyl! -Pyrrolidone and dimethyl sulfoxide.
Die Nachbehandlung erfolgt vorzugsweise durch Erhitzen des Pigmentes im Lösungsmittel auf 100 bis 250° C, wobei in vielen Fällen eine Kornvergröberung eintritt, was sich günstig auf die Licht- und Migrationsechtheit der erhaltenen Pigmente auswirkt.The aftertreatment is preferably carried out by heating the pigment in the solvent to 100 to 250.degree. C., with in many cases a coarsening of the grain occurs, which is beneficial affects the light and migration fastness of the pigments obtained.
Man kann die Kupplung auch vorteilhaft in der Weise durchführen, dass man eine saure Lösung des Diazoniumsalzes mit einer alkalischen Lösung der Kupplungskomponente in einer Mischdüse kontinuierlich vereinigt, wobei eine sofortige Kupplung der Komponenten erfolgt. Die entstandene Farbstoffdispersion wird der Mischdrüse laufend entzogen und der Farbstoff durch Filtrieren abgetrennt.The coupling can also be carried out advantageously in such a way that an acidic solution of the diazonium salt is used an alkaline solution of the coupling component is continuously combined in a mixing nozzle, with an immediate coupling of the components takes place. The resulting dye dispersion is continuously withdrawn from the mixing gland and the dye through Separated by filtration.
Schliesslich kann die Kupplung auch so vollzogen werden, dass man das zu diazotierende Amin mit der Kupplungskomponente im Molverhä'ltnis 1 : 1 in einem organischen Lösungsmittel suspendiert und mit einem diazotierenden Mittel, insbesondere einem Ester der salpetrigen Säure, wie Methyl-, Aethyl-, Butyl-, Amyl- oder Oktylnitrit behandelt.Finally, the coupling can also be carried out in such a way that that the amine to be diazotized with the coupling component in a molar ratio of 1: 1 in an organic solvent suspended and with a diazotizing agent, especially an ester of nitrous acid, such as methyl, Treated ethyl, butyl, amyl or octyl nitrite.
609 8 0 8/0943609 8 0 8/0943
2535U02535U0
Die neuen Farbstoffe stellen wertvolle Pigmente dar, welche in feinverteilter Form zum Pigmentieren von hochmolekularem organischem Material verwendet werden können, z.B. CeI-luloseäthern und estern, wie Aethy!cellulose, Nitrocellulose, Celluloseacetat, Cellulosebutyrat, natürlichen Harzen oder Kunstharzen, wie Polymerisationsharzen oder Kondensationsharzen, z.B. Aminoplasten, insbesondere Harnstoff- und Melamin-Formaldehydharzen, Alkydharzen, Phenoplasten, Polycarbonaten, Polyolefinen, wie Polystyrol, Polyvinylchlorid, Polyäthylen, Polypropylen, Polyacrylnitril, Polyacrylsäureester, Polyamiden, Polyurethanen oder Polyester, Gummi, Casein, Silikon und Silikonharzen, einzeln oder in Mischungen.The new dyes are valuable pigments which, in finely divided form, are used for pigmenting high molecular weight organic material can be used, e.g. cellulose ethers and esters, such as ethyl cellulose, nitrocellulose, Cellulose acetate, cellulose butyrate, natural resins or synthetic resins, such as polymerization resins or condensation resins, e.g. aminoplasts, especially urea and melamine-formaldehyde resins, alkyd resins, phenoplasts, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid esters, polyamides, polyurethanes or polyester, rubber, casein, silicone and silicone resins, individually or in mixtures.
Dabei spielt es keine Rolle, ob die erwähnten hochmolekularen Verbindungen als plastische Massen, Schmelzen oder in Form von Spinnlösungen, Lacken, Anstrichstoffen oder Druckfarben vorliegen. Je nach Verwendungszweck erweist es sich als vorteilhaft, die neuen Pigmente als Toner oder in Form von Präparaten zu verwenden.It does not matter whether the mentioned high molecular compounds as plastic masses, melts or in the form of spinning solutions, lacquers, paints or printing inks. Depending on the intended use, it turns out to be It is advantageous to use the new pigments as toners or in the form of preparations.
Die erfindungsgemässen Pigmente haben bessere Alkaliechtheit als die in der DT-OL 2 420 941 beschriebenen Pigmente aus unsubstituierten Barbitursäuren.The pigments according to the invention have better ones Alkali fastness than the pigments from unsubstituted barbituric acids described in DT-OL 2 420 941.
In den nachfolgenden Beispielen bedeuten die Teile, sofern nichts anderes angegeben wird, Gewichtsteile, die Prozente Gewichtsprozente, und die Temperaturen sind in Celsiusgraden angegeben.In the examples below, the parts mean, unless otherwise stated, parts by weight, the Percentages by weight and temperatures are given in degrees Celsius.
609808/0943609808/0943
2535H02535H0
20,85 Teile 4-Methyl-6-amino-7-chlor-chinolon-(2) werden in einem Gemisch von 400 Volumteilen Eisessig, 400 Volumenteilen Wasser und 25 Volumteilen cone. Salzsäure bei 0-50C in ca. 15 Minuten mit 25 Volumteilen 4n-Natriumnitritlösung diazotiert. Dann giesst man diese Diazolösung in dünnem Strahl zu einer Lösung von 15,6 Teilen Ν,Ν-Dimethyl-barbitursäure in 1000 Volumteilen Dimethylformamid, welcher man noch 30 Teile wasserfreies Natriumacetat zugegeben hat. Die Kupplung erfolgt sofort. Man rührt noch einige Stunden bei Raumtemperatur nach, filtriert dann das gebildete Pigment ab, wäscht es mit heissem Wasser und Methanol und trocknet es.20.85 parts of 4-methyl-6-amino-7-chloro-quinolone- (2) are in a mixture of 400 parts by volume of glacial acetic acid, 400 parts by volume of water and 25 parts by volume of cone. Hydrochloric acid at 0-5 0 C in about 15 minutes with 25 parts by volume of 4N sodium nitrite solution. This diazo solution is then poured in a thin stream into a solution of 15.6 parts of Ν, Ν-dimethylbarbituric acid in 1000 parts by volume of dimethylformamide, to which 30 parts of anhydrous sodium acetate have been added. The coupling takes place immediately. The mixture is stirred for a few more hours at room temperature, then the pigment formed is filtered off, washed with hot water and methanol and dried.
Zur Gewinnung eines coloristisch brauchbaren Pigmentes wird das Kupplungsprodukt in 1300 Volumteilen N-Methy!pyrrolidon während 30 Minuten zum Sieden erhitzt. Nach dem Erkalten wird das Pigment durch Filtration abgetrennt, mit Methanol gewaschen und getrocknet. Man erhält 27 Teile eines grünst ichig gelben, weichen Pigmentpulvers. Das Pigment hat die folgende Konstitution:To obtain a coloristically useful pigment is the coupling product in 1300 parts by volume of N-methyl pyrrolidone heated to boiling for 30 minutes. After cooling, the pigment is separated off by filtration using methanol washed and dried. 27 parts of a greenish yellow, soft pigment powder are obtained. The pigment has the following constitution:
II.
\\
Λ\. tst y Y
Λ \. tst y
0 H 0 H
Es färbt Polyvinylchlorid in sehr farbstarkem, reinem gelbem Ton mit sehr guter Migrations- und guter Licht-Echtheit.It colors polyvinyl chloride in a very strong, pure yellow Clay with very good migration and light fastness.
609808/0943609808/0943
17,4 Teile 4-Methyl-7-amino-chinolon~(2) werden mit17.4 parts of 4-methyl-7-amino-quinolone ~ (2) are mixed with
6,9 Teilen Natriumnitrit und 25 ml konzentrierte Salzsäure6.9 parts of sodium nitrite and 25 ml of concentrated hydrochloric acid
wie im Beispiel 1 diazotiert.diazotized as in Example 1.
16,4 Teile N,N1-Dimethylbarbitursäure werden in verdünnter Natronlauge gelöst und der pH-Wert durch Zugabe von verdünnter Essigsäure auf 7.0 herabgesetzt. 27 Teile Natronlauge werden zur Pufferung der Lösung auf pH 4-5 zugegeben. Die Diazolösung wird nun der gepufferten Lösung der Kupplungskomponente im Laufe von 30-60 Minuten zugegeben, wobei kein Ueberschuss an Diazokomponente mehr vorhanden sein darf. Die erhaltene gelbe Pigmentsuspension wird filtriert und der Filterkuchen bei 50° während 16 Stunden getrocknet.16.4 parts of N, N 1 -dimethylbarbituric acid are dissolved in dilute sodium hydroxide solution and the pH value is reduced to 7.0 by adding dilute acetic acid. 27 parts of sodium hydroxide solution are added to buffer the solution to pH 4-5. The diazo solution is then added to the buffered solution of the coupling component in the course of 30-60 minutes, with no excess of the diazo component being allowed to be present. The yellow pigment suspension obtained is filtered and the filter cake is dried at 50 ° for 16 hours.
Beispiele 3-19Examples 3-19
Die folgende Tabelle enthält weitere Pigmentfärbstoffe, die nach dem Verfahren des Beispiels 1 erhalten wurden. Kolonne I bezeichnet die Diazobase, Kolonne 1 die Kupplungskomponente und Kolonne III gibt den Farbton des mit dem Pigment gefärbten Polyvinylchlorids an.The following table contains other pigment dyes that following the procedure of Example 1. Column I denotes the diazo base, column 1 the coupling component and column III indicates the hue of the polyvinyl chloride colored with the pigment.
6098Ώ8/0943-6098Ώ8 / 0943-
gelbyellow
yellow
gelb
trotstichig-
gelb
gelbgreenish-
yellow
defiant
yellow
yellow
dodo
99
4,6-Dimethyl-8-chlor-7-amino-chinolon-(2)4-methyl-6-phenoKy-7-amino-quinolone- (2)
4,6-dimethyl-8-chloro-7-amino-quinolone- (2)
MM.
gelb
gelb
orangereddish
yellow
yellow
orange
GdGd
QQ
(£>(£>
■Ρ-■ Ρ-
OiOi
11
1210
11
12th
4-Methyl-7-amino-chinolon~(2)
4,6-DiInethyl-7-amino-chinolon- (2)4,5,8-trimethyl-6-amino-quinolone- (2)
4-methyl-7-amino-quinolone ~ (2)
4,6-diethyl-7-aminoquinolone- (2)
N-Methyl-N' (m-chlorphenyl)
barbituric acid
Il H
N-methyl-N '(m-chlorophenyl)
barbituric acid
Il
gelb
gelbgreenish
yellow
yellow
CJI LO CJI LO
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3514674A GB1459547A (en) | 1974-08-09 | 1974-08-09 | Monoazo pigments from amino quinolones and barbituric acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2535140A1 true DE2535140A1 (en) | 1976-02-19 |
Family
ID=10374368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752535140 Pending DE2535140A1 (en) | 1974-08-09 | 1975-08-06 | NEW MONOAZO PIGMENTS, PROCESS FOR THEIR PRODUCTION AND USE |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2535140A1 (en) |
| FR (1) | FR2281406A1 (en) |
| GB (1) | GB1459547A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0761764A1 (en) * | 1995-08-09 | 1997-03-12 | Hoechst Aktiengesellschaft | Water-insoluble azo colouring agents derived from aminoquinazolinediones |
-
1974
- 1974-08-09 GB GB3514674A patent/GB1459547A/en not_active Expired
-
1975
- 1975-08-06 DE DE19752535140 patent/DE2535140A1/en active Pending
- 1975-08-08 FR FR7524784A patent/FR2281406A1/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0761764A1 (en) * | 1995-08-09 | 1997-03-12 | Hoechst Aktiengesellschaft | Water-insoluble azo colouring agents derived from aminoquinazolinediones |
| US5747566A (en) * | 1995-08-09 | 1998-05-05 | Hoechst Aktiengesellschaft | Water-insoluble azo colorants based on aminoquinazolinediones |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2281406A1 (en) | 1976-03-05 |
| FR2281406B1 (en) | 1977-12-16 |
| GB1459547A (en) | 1976-12-22 |
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