DE2329781C2 - Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel - Google Patents
Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als FarbmittelInfo
- Publication number
- DE2329781C2 DE2329781C2 DE19732329781 DE2329781A DE2329781C2 DE 2329781 C2 DE2329781 C2 DE 2329781C2 DE 19732329781 DE19732329781 DE 19732329781 DE 2329781 A DE2329781 A DE 2329781A DE 2329781 C2 DE2329781 C2 DE 2329781C2
- Authority
- DE
- Germany
- Prior art keywords
- acetoacetylamino
- amino
- yellow
- benzoxazine
- bis
- 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 title description 17
- 238000000034 method Methods 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 239000003086 colorant Substances 0.000 title 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000005859 coupling reaction Methods 0.000 description 16
- 230000008878 coupling Effects 0.000 description 15
- 238000010168 coupling process Methods 0.000 description 15
- -1 bromo, methyl Chemical group 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- DNWVUFSWMQIGJX-UHFFFAOYSA-N 7-amino-1,3-benzoxazine-2,4-dione Chemical compound O1C(=O)NC(=O)C=2C1=CC(N)=CC=2 DNWVUFSWMQIGJX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 230000005012 migration Effects 0.000 description 6
- 238000013508 migration Methods 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- OQBHIDQYRBFXNI-UHFFFAOYSA-N 6-amino-1,3-benzoxazine-2,4-dione Chemical compound O1C(=O)NC(=O)C2=CC(N)=CC=C21 OQBHIDQYRBFXNI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 description 3
- UDVBSBBJXJZCAL-UHFFFAOYSA-N 5-amino-1,2-benzoxazine-3,4-dione Chemical compound O1NC(=O)C(=O)C2=C1C=CC=C2N UDVBSBBJXJZCAL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IQWUCASGTZCNKK-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C(OC)=C1 IQWUCASGTZCNKK-UHFFFAOYSA-N 0.000 description 3
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 229920000297 Rayon Polymers 0.000 description 2
- 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 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 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
- 229940081735 acetylcellulose Drugs 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 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 2
- 235000021240 caseins Nutrition 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BZKDEDRZTISGLD-UHFFFAOYSA-N n-(2-methoxy-5-methylphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(C)C=C1NC(=O)CC(C)=O BZKDEDRZTISGLD-UHFFFAOYSA-N 0.000 description 2
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SWAJJKROCOJICG-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C=C1 SWAJJKROCOJICG-UHFFFAOYSA-N 0.000 description 2
- UTAJOMREBNYBAJ-UHFFFAOYSA-N n-[2,5-dichloro-4-(3-oxobutanoylamino)phenyl]-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=C(NC(=O)CC(C)=O)C=C1Cl UTAJOMREBNYBAJ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 229920002554 vinyl polymer Chemical class 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
- IZDNNHOZVXRIGA-UHFFFAOYSA-N 2h-1,2-benzoxazin-3-amine Chemical compound C1=CC=C2ONC(N)=CC2=C1 IZDNNHOZVXRIGA-UHFFFAOYSA-N 0.000 description 1
- OWGNKUKYZPVEFS-UHFFFAOYSA-N 3-oxo-n-[4-(3-oxobutanoylamino)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(NC(=O)CC(C)=O)C=C1 OWGNKUKYZPVEFS-UHFFFAOYSA-N 0.000 description 1
- CNDFNBVEGJXFPU-UHFFFAOYSA-N C(CC(=O)C)(=O)NC1=C(C=C(C(=C1)Cl)NC(C)=O)C Chemical compound C(CC(=O)C)(=O)NC1=C(C=C(C(=C1)Cl)NC(C)=O)C CNDFNBVEGJXFPU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000008236 heating water Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- NRVXULLHSFITHB-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=C(C)C=CC=C1Cl NRVXULLHSFITHB-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
- 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
- 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
- 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
- SCRLPLRQYAPVDC-UHFFFAOYSA-N n-(7-chloro-2-oxobenzimidazol-5-yl)-3-oxobutanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=C(Cl)C2=NC(=O)N=C21 SCRLPLRQYAPVDC-UHFFFAOYSA-N 0.000 description 1
- NPISXGVUUHHCHZ-UHFFFAOYSA-N n-[2,5-dimethyl-4-(3-oxobutanoylamino)phenyl]-3-oxobutanamide Chemical group CC(=O)CC(=O)NC1=CC(C)=C(NC(=O)CC(C)=O)C=C1C NPISXGVUUHHCHZ-UHFFFAOYSA-N 0.000 description 1
- RDHJAUVESAEJQX-UHFFFAOYSA-N n-[3-chloro-4-(3-oxobutanoylamino)phenyl]-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(NC(=O)CC(C)=O)C(Cl)=C1 RDHJAUVESAEJQX-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- JMRJWEJJUKUBEA-UHFFFAOYSA-N p-Chloroacetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1 JMRJWEJJUKUBEA-UHFFFAOYSA-N 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
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
-
- 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/337—Carbocyclic arylides
-
- 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732329781 DE2329781C2 (de) | 1973-06-12 | 1973-06-12 | Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel |
| IT2380674A IT1014921B (it) | 1973-06-12 | 1974-06-10 | Azopigmenti e processo per la lo ro preparazione |
| CH797074A CH612987A5 (en) | 1973-06-12 | 1974-06-11 | Process for the preparation of novel azo pigments |
| JP49065650A JPS50138019A (OSRAM) | 1973-06-12 | 1974-06-11 | |
| GB2605374A GB1472137A (en) | 1973-06-12 | 1974-06-12 | Azo pigments and process for their preparation |
| FR7420339A FR2233373B1 (OSRAM) | 1973-06-12 | 1974-06-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732329781 DE2329781C2 (de) | 1973-06-12 | 1973-06-12 | Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2329781A1 DE2329781A1 (de) | 1975-01-23 |
| DE2329781C2 true DE2329781C2 (de) | 1986-06-05 |
Family
ID=5883711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732329781 Expired DE2329781C2 (de) | 1973-06-12 | 1973-06-12 | Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS50138019A (OSRAM) |
| CH (1) | CH612987A5 (OSRAM) |
| DE (1) | DE2329781C2 (OSRAM) |
| FR (1) | FR2233373B1 (OSRAM) |
| GB (1) | GB1472137A (OSRAM) |
| IT (1) | IT1014921B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2544568C3 (de) * | 1975-10-04 | 1979-02-08 | Basf Ag, 6700 Ludwigshafen | Sulfonsäuregruppenfreie Azofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung als Pigmente in Lacken, Druckfarben oder Kunststoffen |
| CH611642A5 (OSRAM) * | 1976-11-09 | 1979-06-15 | Ciba Geigy Ag | |
| EP0000737B1 (de) * | 1977-08-04 | 1981-04-29 | Ciba-Geigy Ag | Monoazopigmente der Acetoacetylaminobenzimidazolonreihe, Verfahren zu deren Herstellung, und deren Verwendung zum Pigmentieren von hochmolekularem organischem Material |
| DE2841532C2 (de) * | 1978-09-23 | 1983-01-05 | Basf Farben + Fasern Ag, 2000 Hamburg | Neue Disazopigmentfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung zur Färbung von Kunststoffen, Lacken und Druckfarben |
| DE2847285A1 (de) * | 1978-10-31 | 1980-05-14 | Hoechst Ag | Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| DE10227527A1 (de) | 2002-06-20 | 2004-01-08 | Clariant Gmbh | Verfahren zur Herstellung von Disazopigmenten |
Family Cites Families (2)
| 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. |
| BE788571A (fr) * | 1971-09-08 | 1973-03-08 | Hoechst Ag | Colorants azoiques insolubles dans l'eau |
-
1973
- 1973-06-12 DE DE19732329781 patent/DE2329781C2/de not_active Expired
-
1974
- 1974-06-10 IT IT2380674A patent/IT1014921B/it active
- 1974-06-11 JP JP49065650A patent/JPS50138019A/ja active Pending
- 1974-06-11 CH CH797074A patent/CH612987A5/xx not_active IP Right Cessation
- 1974-06-12 GB GB2605374A patent/GB1472137A/en not_active Expired
- 1974-06-12 FR FR7420339A patent/FR2233373B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2233373A1 (OSRAM) | 1975-01-10 |
| JPS50138019A (OSRAM) | 1975-11-04 |
| FR2233373B1 (OSRAM) | 1977-10-07 |
| DE2329781A1 (de) | 1975-01-23 |
| GB1472137A (en) | 1977-05-04 |
| CH612987A5 (en) | 1979-08-31 |
| IT1014921B (it) | 1977-04-30 |
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| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |