DE2305071C2 - Wasserunlösliche Disazomethinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Wasserunlösliche Disazomethinfarbstoffe, Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE2305071C2 DE2305071C2 DE2305071A DE2305071A DE2305071C2 DE 2305071 C2 DE2305071 C2 DE 2305071C2 DE 2305071 A DE2305071 A DE 2305071A DE 2305071 A DE2305071 A DE 2305071A DE 2305071 C2 DE2305071 C2 DE 2305071C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dyes
- formula
- water
- dye
- 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
- 239000000975 dye Substances 0.000 title claims description 28
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000007639 printing Methods 0.000 description 15
- 239000000976 ink Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical group NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 6
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 150000004985 diamines Chemical class 0.000 description 6
- 229940018564 m-phenylenediamine Drugs 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000001052 yellow pigment Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- -1 heterocyclic amine Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical class C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000004988 m-phenylenediamines Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral 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
- 230000000485 pigmenting effect Effects 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
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 150000004003 1-naphthaldehydes Chemical class 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- OTNKCGQLSHSABI-UHFFFAOYSA-N 2-hydroxy-6-methoxynaphthalene-1-carbaldehyde Chemical compound O=CC1=C(O)C=CC2=CC(OC)=CC=C21 OTNKCGQLSHSABI-UHFFFAOYSA-N 0.000 description 1
- ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
- HQDCQNCMUSAKQU-UHFFFAOYSA-N 4-bromobenzene-1,3-diamine Chemical compound NC1=CC=C(Br)C(N)=C1 HQDCQNCMUSAKQU-UHFFFAOYSA-N 0.000 description 1
- NQHVJMJEWQQXBS-UHFFFAOYSA-N 4-ethoxybenzene-1,3-diamine Chemical compound CCOC1=CC=C(N)C=C1N NQHVJMJEWQQXBS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000000020 Nitrocellulose Substances 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
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 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
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004002 naphthaldehydes Chemical class 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 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
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001043 yellow dye 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
- C09B55/00—Azomethine dyes
- C09B55/005—Disazomethine dyes
- C09B55/007—Disazomethine dyes containing only carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2305071A DE2305071C2 (de) | 1973-02-02 | 1973-02-02 | Wasserunlösliche Disazomethinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| AR252153A AR208279A1 (es) | 1973-02-02 | 1974-01-01 | Colorantes insolubles en agua de compuestos de m-fenilen-diamino-disazometino naftol procedimiento para su preparacion y composiciones que los contienen |
| NL7401120A NL7401120A (cg-RX-API-DMAC7.html) | 1973-02-02 | 1974-01-28 | |
| IN199/CAL/74A IN141043B (cg-RX-API-DMAC7.html) | 1973-02-02 | 1974-01-30 | |
| CH129174A CH587894A5 (cg-RX-API-DMAC7.html) | 1973-02-02 | 1974-01-30 | |
| JP49012320A JPS49110718A (cg-RX-API-DMAC7.html) | 1973-02-02 | 1974-01-31 | |
| IT20046/74A IT1007190B (it) | 1973-02-02 | 1974-01-31 | Coloranti bisazometinici idroinso lubili processo per la loro prepa razione e loro impiego |
| AU65026/74A AU481852B2 (en) | 1973-02-02 | 1974-01-31 | Water-insoluble disazomethine dyestuffs and process for their preparation |
| BR709/74A BR7400709D0 (pt) | 1973-02-02 | 1974-01-31 | Processo para a preparacao de corantes disazometina insoluveis na agua |
| GB469074A GB1413264A (en) | 1973-02-02 | 1974-02-01 | Waterinsoluble disazomethine dyestuffs and process for their preparation |
| DK55074A DK136080C (da) | 1973-02-02 | 1974-02-01 | Vanduoploselige disazomethinfarvestoffer til anvendelse ved pigmentering |
| CA191,601A CA1025476A (en) | 1973-02-02 | 1974-02-01 | Water-insoluble disazomethine pigments, process for their preparation and use |
| BE140520A BE810568A (fr) | 1973-02-02 | 1974-02-04 | Colorants bis-azomethiniques insolubles dans l'eau |
| FR7403594A FR2216328B1 (cg-RX-API-DMAC7.html) | 1973-02-02 | 1974-02-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2305071A DE2305071C2 (de) | 1973-02-02 | 1973-02-02 | Wasserunlösliche Disazomethinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2305071B1 DE2305071B1 (de) | 1974-08-15 |
| DE2305071C2 true DE2305071C2 (de) | 1975-04-17 |
Family
ID=5870719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2305071A Expired DE2305071C2 (de) | 1973-02-02 | 1973-02-02 | Wasserunlösliche Disazomethinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS49110718A (cg-RX-API-DMAC7.html) |
| AR (1) | AR208279A1 (cg-RX-API-DMAC7.html) |
| BE (1) | BE810568A (cg-RX-API-DMAC7.html) |
| BR (1) | BR7400709D0 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1025476A (cg-RX-API-DMAC7.html) |
| CH (1) | CH587894A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2305071C2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK136080C (cg-RX-API-DMAC7.html) |
| FR (1) | FR2216328B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1413264A (cg-RX-API-DMAC7.html) |
| IN (1) | IN141043B (cg-RX-API-DMAC7.html) |
| IT (1) | IT1007190B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7401120A (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2533947A1 (de) * | 1975-07-30 | 1977-02-17 | Hoechst Ag | Metallhaltige disazomethinverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel |
| DE2610308A1 (de) * | 1976-03-12 | 1977-09-15 | Hoechst Ag | Wasserunloesliche disazomethin-mischkomplexe, verfahren zu ihrer herstellung und ihre verwendung als farbmittel |
-
1973
- 1973-02-02 DE DE2305071A patent/DE2305071C2/de not_active Expired
-
1974
- 1974-01-01 AR AR252153A patent/AR208279A1/es active
- 1974-01-28 NL NL7401120A patent/NL7401120A/xx not_active Application Discontinuation
- 1974-01-30 CH CH129174A patent/CH587894A5/xx not_active IP Right Cessation
- 1974-01-30 IN IN199/CAL/74A patent/IN141043B/en unknown
- 1974-01-31 IT IT20046/74A patent/IT1007190B/it active
- 1974-01-31 BR BR709/74A patent/BR7400709D0/pt unknown
- 1974-01-31 JP JP49012320A patent/JPS49110718A/ja active Pending
- 1974-02-01 CA CA191,601A patent/CA1025476A/en not_active Expired
- 1974-02-01 GB GB469074A patent/GB1413264A/en not_active Expired
- 1974-02-01 DK DK55074A patent/DK136080C/da active
- 1974-02-04 BE BE140520A patent/BE810568A/xx unknown
- 1974-02-04 FR FR7403594A patent/FR2216328B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2305071B1 (de) | 1974-08-15 |
| DK136080B (da) | 1977-08-08 |
| CA1025476A (en) | 1978-01-31 |
| DK136080C (da) | 1978-02-06 |
| NL7401120A (cg-RX-API-DMAC7.html) | 1974-08-06 |
| AU6502674A (en) | 1975-07-31 |
| IN141043B (cg-RX-API-DMAC7.html) | 1977-01-15 |
| BR7400709D0 (pt) | 1974-09-10 |
| GB1413264A (en) | 1975-11-12 |
| AR208279A1 (es) | 1976-12-20 |
| FR2216328B1 (cg-RX-API-DMAC7.html) | 1977-09-16 |
| CH587894A5 (cg-RX-API-DMAC7.html) | 1977-05-13 |
| FR2216328A1 (cg-RX-API-DMAC7.html) | 1974-08-30 |
| BE810568A (fr) | 1974-08-05 |
| JPS49110718A (cg-RX-API-DMAC7.html) | 1974-10-22 |
| IT1007190B (it) | 1976-10-30 |
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|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |