DE2365361A1 - Triazinylverbindungen, ihre herstellung und verwendung - Google Patents
Triazinylverbindungen, ihre herstellung und verwendungInfo
- Publication number
- DE2365361A1 DE2365361A1 DE2365361*A DE2365361A DE2365361A1 DE 2365361 A1 DE2365361 A1 DE 2365361A1 DE 2365361 A DE2365361 A DE 2365361A DE 2365361 A1 DE2365361 A1 DE 2365361A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- bromine
- amino group
- substituents
- parts
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 Methyl-chlorophenyl- Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000005425 toluyl group Chemical group 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000000049 pigment Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LBHYOONLWAWEAA-UHFFFAOYSA-N 2-chloro-3-oxo-n-phenylbutanamide Chemical compound CC(=O)C(Cl)C(=O)NC1=CC=CC=C1 LBHYOONLWAWEAA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- XNJVKBMQMYMVKU-UHFFFAOYSA-N NC(N(C#N)S(O)(=O)=O)=N[N+]([O-])=O Chemical compound NC(N(C#N)S(O)(=O)=O)=N[N+]([O-])=O XNJVKBMQMYMVKU-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- DSSKDXUDARIMTR-UHFFFAOYSA-N dimethyl 2-aminobenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(N)=C1 DSSKDXUDARIMTR-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 1
- 229960004257 sulfaguanidine Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/005—Pyrocolline; Phthalcoylpyrrocolline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1603572A CH558415A (de) | 1972-11-03 | 1972-11-03 | Verfahren zur herstellung von naphthochinonverbindungen. |
| CH1838272 | 1972-12-18 | ||
| CH43573 | 1973-01-12 | ||
| US05/411,086 US3931163A (en) | 1972-11-03 | 1973-10-30 | Naphthoquinone derivatives |
| US05/613,336 US4033963A (en) | 1972-11-03 | 1975-09-15 | Naphthoquinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2365361A1 true DE2365361A1 (de) | 1974-08-15 |
Family
ID=27508835
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2365361*A Withdrawn DE2365361A1 (de) | 1972-11-03 | 1973-10-30 | Triazinylverbindungen, ihre herstellung und verwendung |
| DE19732354198 Withdrawn DE2354198A1 (de) | 1972-11-03 | 1973-10-30 | Schwer loesliche naphthochinonverbindungen, ihre herstellung und verwendung als farbstoffe |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732354198 Withdrawn DE2354198A1 (de) | 1972-11-03 | 1973-10-30 | Schwer loesliche naphthochinonverbindungen, ihre herstellung und verwendung als farbstoffe |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US3931163A (enExample) |
| JP (1) | JPS4977942A (enExample) |
| DE (2) | DE2365361A1 (enExample) |
| GB (2) | GB1451493A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2365361A1 (de) * | 1972-11-03 | 1974-08-15 | Sandoz Ag | Triazinylverbindungen, ihre herstellung und verwendung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1392872A (fr) | 1963-04-11 | 1965-03-19 | Ciba Geigy | Procédé de préparation des phtaloylpyrrocolines |
| US3413302A (en) * | 1965-05-17 | 1968-11-26 | Allied Allied Chemical Corp | Phthaloylpyrrocoline compounds |
| DE2365361A1 (de) * | 1972-11-03 | 1974-08-15 | Sandoz Ag | Triazinylverbindungen, ihre herstellung und verwendung |
-
1973
- 1973-10-30 DE DE2365361*A patent/DE2365361A1/de not_active Withdrawn
- 1973-10-30 GB GB5030573A patent/GB1451493A/en not_active Expired
- 1973-10-30 DE DE19732354198 patent/DE2354198A1/de not_active Withdrawn
- 1973-10-30 US US05/411,086 patent/US3931163A/en not_active Expired - Lifetime
- 1973-10-30 GB GB1585276A patent/GB1451494A/en not_active Expired
- 1973-11-01 JP JP48122278A patent/JPS4977942A/ja active Pending
-
1975
- 1975-09-15 US US05/613,336 patent/US4033963A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3931163A (en) | 1976-01-06 |
| US4033963A (en) | 1977-07-05 |
| GB1451494A (en) | 1976-10-06 |
| DE2354198A1 (de) | 1974-07-18 |
| GB1451493A (en) | 1976-10-06 |
| JPS4977942A (enExample) | 1974-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1235466B (de) | Verfahren zur Herstellung von organischen Farbstoffen | |
| EP0038296B1 (de) | Disazoverbindungen | |
| DE1069313B (enExample) | ||
| EP0714955A1 (de) | Azofarbstoffe, Verfahren zu deren Herstellung und deren Verwendung | |
| DE1070313B (de) | Verfahren zur Herstellung von 1-Amino-4- phenylamino- anthrachinon- 2- sulfonsäuren | |
| DE2365361A1 (de) | Triazinylverbindungen, ihre herstellung und verwendung | |
| EP0051563A1 (de) | Monoazoverbindungen | |
| DE2852037A1 (de) | Neue verbindungen, verfahren zu deren herstellung und deren verwendung | |
| DE3501199A1 (de) | Azo-pigmentfarbstoffe | |
| DE2445932C2 (de) | Azofarbstoffe, ihre Herstellung und Verwendung | |
| EP0026414B1 (de) | Wasserlösliche Monoazoverbindungen, deren Herstellung und deren Verwendung als Farbstoffe zum Färben und Bedrucken von Textilmaterialien sowie die Amine an sich | |
| EP0000737B1 (de) | Monoazopigmente der Acetoacetylaminobenzimidazolonreihe, Verfahren zu deren Herstellung, und deren Verwendung zum Pigmentieren von hochmolekularem organischem Material | |
| CH574944A5 (en) | Triazinyl cpds used as dye inters - prepd from halogen-substd triazinyl cpd and acetoacetylamines | |
| DE2922227A1 (de) | Verfahren zur herstellung von azofarbstoffen | |
| DE548680C (de) | Verfahren zur Herstellung von kupferhaltigen Azofarbstoffen | |
| DE1644093A1 (de) | Verfahren zur Herstellung von wasserloeslichen basischen Azofarbstoffen | |
| DE2935011A1 (de) | Disperse monoazofarbstoffe und verfahren zu ihrer herstellung sowie ihre verwendung zum faerben von synthetischen textilmaterialien | |
| DE2429524C2 (de) | Chromhaltige Azofarbstoffe, deren Herstellung und Verwendung | |
| DE2631669A1 (de) | Azo-benzothiazoliumfarbstoffe, verfahren zu ihrer herstellung und deren verwendung | |
| DE1113772B (de) | Verfahren zur Herstellung von Monoazofarbstoffen der Benzothiazolreihe | |
| CH625539A5 (en) | Process for preparing azo pigments | |
| CH346309A (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1111317B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE1117234B (de) | Verfahren zur Herstellung von wasserunloeslichen metallhaltigen Azofarbstoffen | |
| CH605849A5 (en) | Heterocyclic coupling components for pigment mfr. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |