DE2130040C3 - Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE2130040C3 DE2130040C3 DE19712130040 DE2130040A DE2130040C3 DE 2130040 C3 DE2130040 C3 DE 2130040C3 DE 19712130040 DE19712130040 DE 19712130040 DE 2130040 A DE2130040 A DE 2130040A DE 2130040 C3 DE2130040 C3 DE 2130040C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- volume
- water
- yellow
- compounds
- 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
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [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 5
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 230000008878 coupling Effects 0.000 description 16
- 238000010168 coupling process Methods 0.000 description 16
- 238000005859 coupling reaction Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000049 pigment Substances 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- -1 5-amino-isophthalic acid ester amides Chemical class 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
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001052 yellow pigment Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000025 natural resin Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KXBUVWNTVMVSDB-UHFFFAOYSA-N 3-methoxycarbonyl-5-nitrobenzoic acid hydrochloride Chemical compound Cl.COC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 KXBUVWNTVMVSDB-UHFFFAOYSA-N 0.000 description 1
- UXPIWHPHEGRYLB-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=CC(N)=CC(C(N)=O)=C1 UXPIWHPHEGRYLB-UHFFFAOYSA-N 0.000 description 1
- OUBCLJMZKHTLFG-UHFFFAOYSA-N CN.COC(C1=CC(C(O)=O)=CC(N)=C1)=O Chemical compound CN.COC(C1=CC(C(O)=O)=CC(N)=C1)=O OUBCLJMZKHTLFG-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JWNLENFPVYTHAI-UHFFFAOYSA-N N-(7-methoxy-2-oxobenzimidazol-4-yl)-3-oxobutanamide Chemical compound C(CC(=O)C)(=O)NC1=CC=C(C2=NC(N=C21)=O)OC JWNLENFPVYTHAI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-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
- APWNYYNYWQJZHD-UHFFFAOYSA-N n-(7-methyl-2-oxobenzimidazol-5-yl)-3-oxobutanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=C(C)C2=NC(=O)N=C21 APWNYYNYWQJZHD-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712130040 DE2130040C3 (de) | 1971-06-18 | 1971-06-18 | Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| ES403780A ES403780A1 (es) | 1971-06-18 | 1972-06-13 | Procedimiento para la preparacion de colorantes monoazoicosinsolubles en agua. |
| NL7208054A NL7208054A (enExample) | 1971-06-18 | 1972-06-13 | |
| CH883572A CH569763A5 (enExample) | 1971-06-18 | 1972-06-14 | |
| BR392872A BR7203928D0 (pt) | 1971-06-18 | 1972-06-16 | Processo para a fabricacao de novos corantes monoazoicos insoluveis em agua |
| IT2582272A IT961229B (it) | 1971-06-18 | 1972-06-16 | Monoazocoloranti idroinsolu bili e processo per la loro prepa razione |
| AT517472A AT310320B (de) | 1971-06-18 | 1972-06-16 | Verfahren zur Herstellung von neuen wasserunlöslichen Monoazofarbstoffen |
| AU43519/72A AU465743B2 (en) | 1971-06-18 | 1972-06-16 | Process forthe preparation of novel water-insoluble monoazo dyestuffs |
| CA144,888A CA968790A (en) | 1971-06-18 | 1972-06-16 | Process for the preparation of novel water-insoluble monoazo dyestuffs |
| JP5960472A JPS5641661B1 (enExample) | 1971-06-18 | 1972-06-16 | |
| GB2831172A GB1398015A (en) | 1971-06-18 | 1972-06-16 | Water-insoluble monoazo dyestuffs and process for heir preparation |
| FR7222018A FR2142075B1 (enExample) | 1971-06-18 | 1972-06-19 | |
| BE785102A BE785102A (fr) | 1971-06-18 | 1972-06-19 | Colorants monoazoiques, leur preparation et leur utilisation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712130040 DE2130040C3 (de) | 1971-06-18 | 1971-06-18 | Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2130040A1 DE2130040A1 (de) | 1972-12-21 |
| DE2130040B2 DE2130040B2 (de) | 1979-01-04 |
| DE2130040C3 true DE2130040C3 (de) | 1979-08-30 |
Family
ID=5810998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712130040 Expired DE2130040C3 (de) | 1971-06-18 | 1971-06-18 | Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5641661B1 (enExample) |
| AT (1) | AT310320B (enExample) |
| AU (1) | AU465743B2 (enExample) |
| BE (1) | BE785102A (enExample) |
| BR (1) | BR7203928D0 (enExample) |
| CA (1) | CA968790A (enExample) |
| CH (1) | CH569763A5 (enExample) |
| DE (1) | DE2130040C3 (enExample) |
| ES (1) | ES403780A1 (enExample) |
| FR (1) | FR2142075B1 (enExample) |
| GB (1) | GB1398015A (enExample) |
| IT (1) | IT961229B (enExample) |
| NL (1) | NL7208054A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2302482C3 (de) * | 1973-01-19 | 1984-01-05 | Hoechst Ag, 6230 Frankfurt | Disazopigment, Verfahren zu seiner Herstellung und seine Verwendung |
| CH626906A5 (enExample) * | 1977-07-27 | 1981-12-15 | Ciba Geigy Ag | |
| US4442350A (en) * | 1981-08-17 | 1984-04-10 | The United States Of America As Represented By The Secretary Of The Navy | Fiber optic sensor with enhanced immunity to random environmental perturbations |
| JPS58165615U (ja) * | 1982-04-30 | 1983-11-04 | 大倉電気株式会社 | 防音形記録紙歩進装置 |
-
1971
- 1971-06-18 DE DE19712130040 patent/DE2130040C3/de not_active Expired
-
1972
- 1972-06-13 ES ES403780A patent/ES403780A1/es not_active Expired
- 1972-06-13 NL NL7208054A patent/NL7208054A/xx not_active Application Discontinuation
- 1972-06-14 CH CH883572A patent/CH569763A5/xx not_active IP Right Cessation
- 1972-06-16 AT AT517472A patent/AT310320B/de not_active IP Right Cessation
- 1972-06-16 CA CA144,888A patent/CA968790A/en not_active Expired
- 1972-06-16 IT IT2582272A patent/IT961229B/it active
- 1972-06-16 BR BR392872A patent/BR7203928D0/pt unknown
- 1972-06-16 AU AU43519/72A patent/AU465743B2/en not_active Expired
- 1972-06-16 GB GB2831172A patent/GB1398015A/en not_active Expired
- 1972-06-16 JP JP5960472A patent/JPS5641661B1/ja active Pending
- 1972-06-19 FR FR7222018A patent/FR2142075B1/fr not_active Expired
- 1972-06-19 BE BE785102A patent/BE785102A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU4351972A (en) | 1973-12-20 |
| DE2130040B2 (de) | 1979-01-04 |
| IT961229B (it) | 1973-12-10 |
| BE785102A (fr) | 1972-12-19 |
| JPS5641661B1 (enExample) | 1981-09-29 |
| ES403780A1 (es) | 1975-05-01 |
| FR2142075A1 (enExample) | 1973-01-26 |
| BR7203928D0 (pt) | 1973-06-28 |
| AT310320B (de) | 1973-09-25 |
| CA968790A (en) | 1975-06-03 |
| GB1398015A (en) | 1975-06-18 |
| FR2142075B1 (enExample) | 1977-12-23 |
| DE2130040A1 (de) | 1972-12-21 |
| CH569763A5 (enExample) | 1975-11-28 |
| AU465743B2 (en) | 1973-12-20 |
| NL7208054A (enExample) | 1972-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1808015C3 (de) | Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Ver wendung | |
| DE1795051A1 (de) | Neue wasserunloesliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2130040C3 (de) | Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1939466C3 (de) | Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel | |
| DE2203094C3 (de) | Monoazopigmente, Verfahren zu deren Herstellung und Verwendung | |
| EP0010273A1 (de) | Monoazoverbindungen der Acetoacetylaminobenzimidazolonreihe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2200112C3 (de) | Carbostyril-Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Pigmente | |
| DE1235468B (de) | Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen | |
| DE2329781A1 (de) | Neue azopigmente und verfahren zu ihrer herstellung | |
| DE2336915A1 (de) | Neue disazopigmente und verfahren zur herstellung und verwendung | |
| EP0010272B1 (de) | Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1795052C3 (de) | Wasserunlösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und Ihre Verwendung afs Pigmente | |
| DE2651919A1 (de) | Disazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel | |
| DE1644191C3 (de) | Wasserunlösliche Monoazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung. Ausscheidung aus: 1263202 | |
| DE2019827C3 (de) | Chromhaltige Komplexfarbstoffe und Verfahren zu deren Herstellung | |
| DE2200659B2 (de) | Wasserunlösliche Disazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Pigmentfarbstoffe | |
| DE1644231C (de) | Wasserunlöslicher Monoazofarbstoff und dessen Verwendung zum Farben und Be drucken | |
| CH472471A (de) | Farbstoffgemisch aus wasserunlöslichen Disazofarbstoffen und Verfahren zu dessen Herstellung | |
| DE2043483C3 (de) | Wasserunlösliche Monoazofarb stoffe, Verfahren zu ihrer Herstellung und Verwendung | |
| DE2328678C3 (de) | Neue Disazopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1644233C (de) | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1225321B (de) | Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen | |
| DE2338973C3 (de) | Monoazopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1208435B (de) | Verfahren zur Herstellung von wasserunloeslichen Monoazofarbstoffen | |
| DE2905937A1 (de) | Neue monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pigmente |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |