DE3034576C2 - Asymmetrische 1:2-Chromazokomplexe, Verfahren zur Herstellung und Verwendung - Google Patents
Asymmetrische 1:2-Chromazokomplexe, Verfahren zur Herstellung und VerwendungInfo
- Publication number
- DE3034576C2 DE3034576C2 DE3034576A DE3034576A DE3034576C2 DE 3034576 C2 DE3034576 C2 DE 3034576C2 DE 3034576 A DE3034576 A DE 3034576A DE 3034576 A DE3034576 A DE 3034576A DE 3034576 C2 DE3034576 C2 DE 3034576C2
- Authority
- DE
- Germany
- Prior art keywords
- udf54
- udf53
- hydrogen
- formula
- chlorine
- 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
- 238000002360 preparation method Methods 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052804 chromium Inorganic materials 0.000 claims description 15
- 150000001844 chromium Chemical class 0.000 claims description 14
- 239000011651 chromium Substances 0.000 claims description 14
- 238000004043 dyeing Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 238000004040 coloring Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 239000000975 dye Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 150000002431 hydrogen Chemical group 0.000 description 16
- 150000001768 cations Chemical class 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- -1 nitro, methyl Chemical group 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 101150018444 sub2 gene Proteins 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 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 description 1
- 238000003801 milling Methods 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000375 suspending agent Substances 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
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000001238 wet grinding 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/04—Azo compounds in general
- C09B45/10—Cobalt compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8600/79A CH649773A5 (de) | 1979-09-24 | 1979-09-24 | Asymmetrische 1:2-chromkomplexe aromatischer azoverbindungen, verfahren zu ihrer herstellung und diese enthaltende praeparate. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3034576A1 DE3034576A1 (de) | 1981-04-09 |
| DE3034576C2 true DE3034576C2 (de) | 1987-04-09 |
Family
ID=4342473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3034576A Expired DE3034576C2 (de) | 1979-09-24 | 1980-09-13 | Asymmetrische 1:2-Chromazokomplexe, Verfahren zur Herstellung und Verwendung |
Country Status (12)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4502860A (en) * | 1982-07-02 | 1985-03-05 | Ciba-Geigy Corporation | Bis-1:2-chromium complexes of disazo dyes, and their preparation and use |
| CH658252A5 (de) * | 1984-03-08 | 1986-10-31 | Ciba Geigy Ag | Verfahren zur herstellung von 1:2-chromkomplexfarbstoffen. |
| CH658065A5 (de) * | 1984-03-08 | 1986-10-15 | Ciba Geigy Ag | Verfahren zur herstellung von 1:2-chromkomplexazofarbstoffen. |
| CH664763A5 (de) * | 1985-01-24 | 1988-03-31 | Ciba Geigy Ag | Unsymmetrische chromkomplexfarbstoffe. |
| CH688281A5 (de) * | 1987-12-04 | 1997-07-15 | Ciba Geigy Ag | Verfahren zur Herstellung von 1:2-Metallkomplexazofarbstoffen. |
| DK1361074T3 (da) * | 2002-04-26 | 2005-08-29 | Okt Kunststofftechnik Gmbh | Fremgangsmåde til forbedring af metaleffekterne, videreforarbejdningskriterierne samt fleksibiliteten af harpikscoatede dekorpapirer |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906746A (en) * | 1959-09-29 | Metalliferous azo dyestuffs | ||
| US3005813A (en) * | 1953-05-22 | 1961-10-24 | Ciba Ltd | Metalliferous azo-dyestuffs |
| DE1012007B (de) * | 1953-06-08 | 1957-07-11 | Ciba Geigy | Verfahren zur Herstellung chromhaltiger Azofarbstoffe |
| US2806760A (en) * | 1953-06-10 | 1957-09-17 | Ciba Ltd | Process for dyeing nitrogenous fibers with metalliferous monoazo dyestuffs |
| DE1262478B (de) * | 1961-12-21 | 1968-03-07 | Wolfen Filmfab Veb | Verfahren zur Herstellung eines chromhaltigen Mischkomplexfarbstoffes aus Monoazofarbstoffen |
| CH427095A (de) * | 1965-10-01 | 1966-12-31 | Sandoz Ag | Verfahren zur Herstellung von Mischkomplexverbindungen |
| GB1163713A (en) | 1966-02-10 | 1969-09-10 | Ici Ltd | Chromium-Containing Azo Dyestuffs |
| CH499585A (de) * | 1967-03-08 | 1970-11-30 | Sandoz Ag | Verfahren zur Herstellung von Monoazofarbstoffen und ihren Metallkomplexen |
| US4159983A (en) * | 1975-07-25 | 1979-07-03 | Sandoz Ltd. | Pure and substantially pure asymmetric 1:2 cobalt complexes of monoazo compounds |
| CH616444A5 (en) * | 1975-07-25 | 1980-03-31 | Sandoz Ag | Process for the preparation of asymmetric 1:2 cobalt complex azo compounds |
-
1979
- 1979-09-24 CH CH8600/79A patent/CH649773A5/de not_active IP Right Cessation
-
1980
- 1980-09-13 DE DE3034576A patent/DE3034576C2/de not_active Expired
- 1980-09-19 US US06/188,624 patent/US4396544A/en not_active Expired - Lifetime
- 1980-09-22 GB GB8030516A patent/GB2059431B/en not_active Expired
- 1980-09-22 AU AU62583/80A patent/AU541681B2/en not_active Ceased
- 1980-09-22 ES ES495246A patent/ES495246A0/es active Granted
- 1980-09-22 JP JP13088380A patent/JPS5655457A/ja active Granted
- 1980-09-23 SU SU802980104A patent/SU1168098A3/ru active
- 1980-09-23 BR BR8006083A patent/BR8006083A/pt unknown
- 1980-09-23 IT IT49724/80A patent/IT1128567B/it active
- 1980-09-24 FR FR8020475A patent/FR2465768A1/fr active Granted
-
1986
- 1986-08-14 HK HK597/86A patent/HK59786A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES8200135A1 (es) | 1981-10-16 |
| US4396544A (en) | 1983-08-02 |
| AU541681B2 (en) | 1985-01-17 |
| IT1128567B (it) | 1986-05-28 |
| FR2465768B1 (US07582779-20090901-C00044.png) | 1984-11-09 |
| CH649773A5 (de) | 1985-06-14 |
| IT8049724A0 (it) | 1980-09-23 |
| AU6258380A (en) | 1981-04-09 |
| HK59786A (en) | 1986-08-22 |
| FR2465768A1 (fr) | 1981-03-27 |
| ES495246A0 (es) | 1981-10-16 |
| DE3034576A1 (de) | 1981-04-09 |
| GB2059431A (en) | 1981-04-23 |
| JPS6123948B2 (US07582779-20090901-C00044.png) | 1986-06-09 |
| SU1168098A3 (ru) | 1985-07-15 |
| GB2059431B (en) | 1983-05-25 |
| BR8006083A (pt) | 1981-04-07 |
| JPS5655457A (en) | 1981-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2409433A1 (de) | Monoazo-chromkomplexfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zur faerbung oder zum druck von natuerlichen oder synthetischen polyamiden | |
| DE1544341A1 (de) | Kunststoffloesliche Farbstoffe und Verfahren zu deren Herstellung und Durchfuehrung des Faerbeverfahrens | |
| DE3034576C2 (de) | Asymmetrische 1:2-Chromazokomplexe, Verfahren zur Herstellung und Verwendung | |
| DE3029699C2 (US07582779-20090901-C00044.png) | ||
| DE2704364C2 (US07582779-20090901-C00044.png) | ||
| DE2636798C2 (de) | Asymmetrische 1:2-Chromkomplex-azoverbindungen, deren Herstellung und Verwendung | |
| EP0718374B1 (de) | 1:2-Chromkomplexfarbstoffe enthaltende Farbstoffmischungen und 1:2 Chromkomplexfarbstoffe | |
| DE2729915C2 (de) | Gemische von 1 zu 2-Kobaltkomplexazoverbindungen, deren Herstellung und Verwendung | |
| DE2451219B2 (de) | Verfahren zur herstellung konzentrierter loesungen von farbstoffen und farbstoffzwischenprodukten und verwendung der loesungen | |
| EP0532994B1 (de) | Unsymmetrische 1:2-chrom-komplexfarbstoffe | |
| EP0024677A1 (de) | Wasserlösliche Phthalocyaninverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| DE2631830C2 (de) | Reine asymmetrische 1:2-Kobaltkomplexazoverbindungen und Gemische dieser Komplexe, Verfahren zu deren Herstellung sowie ihre Verwendung | |
| EP0265828A1 (de) | Wasserlösliche Disazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| DE2849995C3 (de) | Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| CH624978A5 (en) | Process for the preparation of chromium or cobalt complex dyes | |
| CH667278A5 (de) | Reaktive formazanverbindungen. | |
| DE3427806C2 (US07582779-20090901-C00044.png) | ||
| DE3923483A1 (de) | Faserreaktive disazofarbstoffe | |
| DE3332212C2 (US07582779-20090901-C00044.png) | ||
| DE2413169A1 (de) | Monoazo-saeurefarbstoffe fuer polyamide | |
| DE3223018A1 (de) | Gemische von symmetrischen und asymmetrischen 1:2-kobaltkomplexen, verfahren zur herstellung und verwendung | |
| DE2637883A1 (de) | Organische verbindungen | |
| DE2608535A1 (de) | Neue chromkomplexfarbstoffe, ihre herstellung und verwendung | |
| DE2656345A1 (de) | Asymmetrische 1 zu 2-chromkomplexazofarbstoffe | |
| CH635608A5 (en) | Asymmetric 1:2 chromium complex azo compounds and preparation and use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |