DE2228674A1 - Azofarbstoffe - Google Patents
AzofarbstoffeInfo
- Publication number
- DE2228674A1 DE2228674A1 DE19722228674 DE2228674A DE2228674A1 DE 2228674 A1 DE2228674 A1 DE 2228674A1 DE 19722228674 DE19722228674 DE 19722228674 DE 2228674 A DE2228674 A DE 2228674A DE 2228674 A1 DE2228674 A1 DE 2228674A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- methyl
- free
- amino
- phenyl
- 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
- 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
- 239000000049 pigment Substances 0.000 claims description 14
- 239000000987 azo dye Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- 239000000123 paper Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- -1 alkyl radicals Chemical class 0.000 description 16
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical class C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZPSRGJNVWFQHPK-UHFFFAOYSA-N CC(C=C(N1)O)=CC1(C(O)=O)O Chemical compound CC(C=C(N1)O)=CC1(C(O)=O)O ZPSRGJNVWFQHPK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- YQGHJCYLMLPCCB-UHFFFAOYSA-N 2,4-diaminopyrimidin-5-ol Chemical class NC1=NC=C(O)C(N)=N1 YQGHJCYLMLPCCB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PRIUALOJYOZZOJ-UHFFFAOYSA-L 2-ethylhexyl 2-[dibutyl-[2-(2-ethylhexoxy)-2-oxoethyl]sulfanylstannyl]sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS[Sn](CCCC)(CCCC)SCC(=O)OCC(CC)CCCC PRIUALOJYOZZOJ-UHFFFAOYSA-L 0.000 description 1
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- VDULOAUXSMYUMG-UHFFFAOYSA-N 2-phenyl-1h-quinazolin-4-one Chemical compound N=1C2=CC=CC=C2C(O)=NC=1C1=CC=CC=C1 VDULOAUXSMYUMG-UHFFFAOYSA-N 0.000 description 1
- GLVQDYSGMRVBBV-UHFFFAOYSA-N 3-(5-amino-3-methylpyrazol-1-yl)propanenitrile Chemical compound CC=1C=C(N)N(CCC#N)N=1 GLVQDYSGMRVBBV-UHFFFAOYSA-N 0.000 description 1
- ARZJEBXFTPBYCK-UHFFFAOYSA-N 3-amino-2-(4-methoxyphenyl)quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=CC=C2C(=O)N1N ARZJEBXFTPBYCK-UHFFFAOYSA-N 0.000 description 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- WKGSLYHMRQRARV-UHFFFAOYSA-N 4-hydroxy-6-methyl-1h-pyridin-2-one Chemical compound CC1=CC(=O)C=C(O)N1 WKGSLYHMRQRARV-UHFFFAOYSA-N 0.000 description 1
- INZPKLIRWQFSQE-UHFFFAOYSA-N 5-amino-2-phenyl-1h-quinazolin-4-one Chemical compound N=1C(O)=C2C(N)=CC=CC2=NC=1C1=CC=CC=C1 INZPKLIRWQFSQE-UHFFFAOYSA-N 0.000 description 1
- JSVFGUVEXOEQEC-UHFFFAOYSA-N 5-imino-1,3-diazinane-2,4,6-trione Chemical class N=C1C(=O)NC(=O)NC1=O JSVFGUVEXOEQEC-UHFFFAOYSA-N 0.000 description 1
- BJRNCQZJTXPXOF-UHFFFAOYSA-N 6-amino-2-(4-methoxyphenyl)-1h-quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(N)C=C2C(=O)N1 BJRNCQZJTXPXOF-UHFFFAOYSA-N 0.000 description 1
- PQIQEIAYUXUQDK-UHFFFAOYSA-N 6-amino-2-(4-methylphenyl)-1h-quinazolin-4-one Chemical compound C1=CC(C)=CC=C1C1=NC2=CC=C(N)C=C2C(=O)N1 PQIQEIAYUXUQDK-UHFFFAOYSA-N 0.000 description 1
- UBJQZWMEDLQQNF-UHFFFAOYSA-N 6-amino-2-phenyl-1h-quinazolin-4-one Chemical compound N1=C(O)C2=CC(N)=CC=C2N=C1C1=CC=CC=C1 UBJQZWMEDLQQNF-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- SJTNHUVFIGLSKM-UHFFFAOYSA-N COC1=C(NC(CC(=O)C)=O)C=C(C(=C1)NC(C1=CC=C(C=C1)Cl)=O)OC Chemical compound COC1=C(NC(CC(=O)C)=O)C=C(C(=C1)NC(C1=CC=C(C=C1)Cl)=O)OC SJTNHUVFIGLSKM-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ZXUSQOYCALFTBR-UHFFFAOYSA-N N-(4-acetamido-2-chlorophenyl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=C(C=C(C=C1)NC(C)=O)Cl ZXUSQOYCALFTBR-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- HCIFGRJFNROOGH-UHFFFAOYSA-N NC(C=C(N1)O)=CC1(C(O)=O)O Chemical compound NC(C=C(N1)O)=CC1(C(O)=O)O HCIFGRJFNROOGH-UHFFFAOYSA-N 0.000 description 1
- OQVDTZOBCKIDNV-UHFFFAOYSA-N NC1=C(C=C2C(NC(=NC2=C1)C1=CC=CC=C1)=O)OC Chemical compound NC1=C(C=C2C(NC(=NC2=C1)C1=CC=CC=C1)=O)OC OQVDTZOBCKIDNV-UHFFFAOYSA-N 0.000 description 1
- OBAYJTHXBWNHKJ-UHFFFAOYSA-N NC=1C=C2C(NC(=NC2=CC=1Br)C1=CC=CC=C1)=O Chemical compound NC=1C=C2C(NC(=NC2=CC=1Br)C1=CC=CC=C1)=O OBAYJTHXBWNHKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- YTKNYOWCICFXOW-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1Cl YTKNYOWCICFXOW-UHFFFAOYSA-N 0.000 description 1
- FGVXALCWFWMFBD-UHFFFAOYSA-N n-(2,4-dinitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O FGVXALCWFWMFBD-UHFFFAOYSA-N 0.000 description 1
- HLMZZYYGOKOOTA-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=CC=C1Cl HLMZZYYGOKOOTA-UHFFFAOYSA-N 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- IMQLJGSUKJTCMD-UHFFFAOYSA-N n-(2-methoxy-4-methylphenyl)-3-oxobutanamide Chemical compound COC1=CC(C)=CC=C1NC(=O)CC(C)=O IMQLJGSUKJTCMD-UHFFFAOYSA-N 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- JTVHJWVDFCVGBG-UHFFFAOYSA-N n-(2-methyl-5-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC([N+]([O-])=O)=CC=C1C JTVHJWVDFCVGBG-UHFFFAOYSA-N 0.000 description 1
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
- PNVSDRLLBNUJBE-UHFFFAOYSA-N n-(4-acetamidophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(NC(C)=O)C=C1 PNVSDRLLBNUJBE-UHFFFAOYSA-N 0.000 description 1
- ODFRAIZRJMUPCP-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1C ODFRAIZRJMUPCP-UHFFFAOYSA-N 0.000 description 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
- QBHQQQKWEKZEHK-UHFFFAOYSA-N n-(4-methoxy-2-nitrophenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C([N+]([O-])=O)=C1 QBHQQQKWEKZEHK-UHFFFAOYSA-N 0.000 description 1
- MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- KZNSYVINVBDMMP-UHFFFAOYSA-N n-(6-methoxy-1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical compound COC1=CC=C2N=C(NC(=O)CC(C)=O)SC2=C1 KZNSYVINVBDMMP-UHFFFAOYSA-N 0.000 description 1
- YEABGCGOKBCPBX-UHFFFAOYSA-N n-[2,5-dichloro-4-(3-oxobutanoylamino)phenyl]benzamide Chemical compound C1=C(Cl)C(NC(=O)CC(=O)C)=CC(Cl)=C1NC(=O)C1=CC=CC=C1 YEABGCGOKBCPBX-UHFFFAOYSA-N 0.000 description 1
- IECFWZLECDGGSU-UHFFFAOYSA-N n-[4-(3-oxobutanoylamino)phenyl]benzamide Chemical compound C1=CC(NC(=O)CC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1 IECFWZLECDGGSU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C09B29/0051—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 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
- C08K5/3465—Six-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722228674 DE2228674A1 (de) | 1972-06-13 | 1972-06-13 | Azofarbstoffe |
| JP6489473A JPS4962540A (it) | 1972-06-13 | 1973-06-11 | |
| IT5066873A IT985409B (it) | 1972-06-13 | 1973-06-11 | Coloranti azoici |
| NL7308152A NL7308152A (it) | 1972-06-13 | 1973-06-12 | |
| BE132139A BE800767A (fr) | 1972-06-13 | 1973-06-12 | Colorants azoiques |
| CH847773A CH583279A5 (it) | 1972-06-13 | 1973-06-12 | |
| GB2790773A GB1382205A (en) | 1972-06-13 | 1973-06-12 | Azo dyestuffs |
| FR7321467A FR2187854B1 (it) | 1972-06-13 | 1973-06-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722228674 DE2228674A1 (de) | 1972-06-13 | 1972-06-13 | Azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2228674A1 true DE2228674A1 (de) | 1973-12-20 |
Family
ID=5847596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722228674 Pending DE2228674A1 (de) | 1972-06-13 | 1972-06-13 | Azofarbstoffe |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4962540A (it) |
| BE (1) | BE800767A (it) |
| CH (1) | CH583279A5 (it) |
| DE (1) | DE2228674A1 (it) |
| FR (1) | FR2187854B1 (it) |
| GB (1) | GB1382205A (it) |
| IT (1) | IT985409B (it) |
| NL (1) | NL7308152A (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH611642A5 (it) * | 1976-11-09 | 1979-06-15 | Ciba Geigy Ag | |
| DE10331890A1 (de) * | 2003-07-14 | 2005-02-03 | Clariant Gmbh | Azofarbmittel auf der Basis von 2-Phenyl-6-amino-7-methoxycarbonyl(3,4H)-chinazolin-4-on |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH552034A (de) * | 1971-03-03 | 1974-07-31 | Ciba Geigy Ag | Verfahren zur herstellung von neuen azopigmenten. |
-
1972
- 1972-06-13 DE DE19722228674 patent/DE2228674A1/de active Pending
-
1973
- 1973-06-11 JP JP6489473A patent/JPS4962540A/ja active Pending
- 1973-06-11 IT IT5066873A patent/IT985409B/it active
- 1973-06-12 GB GB2790773A patent/GB1382205A/en not_active Expired
- 1973-06-12 NL NL7308152A patent/NL7308152A/xx unknown
- 1973-06-12 BE BE132139A patent/BE800767A/xx unknown
- 1973-06-12 CH CH847773A patent/CH583279A5/xx not_active IP Right Cessation
- 1973-06-13 FR FR7321467A patent/FR2187854B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH583279A5 (it) | 1976-12-31 |
| NL7308152A (it) | 1973-12-17 |
| IT985409B (it) | 1974-11-30 |
| GB1382205A (en) | 1975-01-29 |
| FR2187854B1 (it) | 1977-02-11 |
| BE800767A (fr) | 1973-12-12 |
| FR2187854A1 (it) | 1974-01-18 |
| JPS4962540A (it) | 1974-06-18 |
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| OHN | Withdrawal |