CH643873A5 - Kupferhaltige monoazoverbindungen, verfahren zur herstellung und ihre verwendung. - Google Patents
Kupferhaltige monoazoverbindungen, verfahren zur herstellung und ihre verwendung. Download PDFInfo
- Publication number
- CH643873A5 CH643873A5 CH1132179A CH1132179A CH643873A5 CH 643873 A5 CH643873 A5 CH 643873A5 CH 1132179 A CH1132179 A CH 1132179A CH 1132179 A CH1132179 A CH 1132179A CH 643873 A5 CH643873 A5 CH 643873A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- hydrogen
- alkyl
- compound
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 10
- 229910052802 copper Inorganic materials 0.000 title claims description 10
- 239000010949 copper Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical class [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 description 2
- 239000000460 chlorine Substances 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- -1 sulfo, carboxy Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000004043 dyeing Methods 0.000 claims description 10
- 241000251730 Chondrichthyes Species 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 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 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- VNMGVBPCESRCOG-UHFFFAOYSA-N OC(=O)ClS(O)(=O)=O Chemical compound OC(=O)ClS(O)(=O)=O VNMGVBPCESRCOG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229960001922 sodium perborate Drugs 0.000 description 2
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- TZBROGJRQUABOK-UHFFFAOYSA-N 4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 TZBROGJRQUABOK-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 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
- 238000004045 reactive dyeing Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
- 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/095—Metal complex azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1132179A CH643873A5 (de) | 1979-12-20 | 1979-12-20 | Kupferhaltige monoazoverbindungen, verfahren zur herstellung und ihre verwendung. |
| IT50316/80A IT1142199B (it) | 1979-12-20 | 1980-12-05 | Coloranti ramiferi e loro preparazione |
| DE19803046451 DE3046451A1 (de) | 1979-12-20 | 1980-12-10 | "halo-triazinyl-verbindungen, deren herstellung und verwendung" |
| GB8040437A GB2066283B (en) | 1979-12-20 | 1980-12-17 | Fibre-reactive dyestuffs |
| JP17814680A JPS56100860A (en) | 1979-12-20 | 1980-12-18 | Halo triazinyl containing compound |
| BR8008409A BR8008409A (pt) | 1979-12-20 | 1980-12-19 | Processo para a producao de um composto e processo para tingimento ou estampagem de substratos organicos contendo nitrogenio ou grupo hidroxi |
| FR8027047A FR2472002B1 (fr) | 1979-12-20 | 1980-12-19 | Nouveaux colorants cupriferes et leur preparation |
| ES498022A ES498022A0 (es) | 1979-12-20 | 1980-12-19 | Un procedimiento para la preparacion de derivados de halogeno triacinilo. |
| HK318/84A HK31884A (en) | 1979-12-20 | 1984-04-12 | Chloro-triazinyl-containing mono azo compounds |
| BE1/011452A BE904409Q (fr) | 1979-12-20 | 1986-03-13 | Nouveaux colorants cupriferes et leur preparation. |
| KE3635A KE3635A (en) | 1979-12-20 | 1986-05-05 | Chloro-triazinyl-containing mono azo compounds |
| MY696/86A MY8600696A (en) | 1979-12-20 | 1986-12-30 | Chloro-trianzinyl-containing monoazo compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1132179A CH643873A5 (de) | 1979-12-20 | 1979-12-20 | Kupferhaltige monoazoverbindungen, verfahren zur herstellung und ihre verwendung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643873A5 true CH643873A5 (de) | 1984-06-29 |
Family
ID=4372345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1132179A CH643873A5 (de) | 1979-12-20 | 1979-12-20 | Kupferhaltige monoazoverbindungen, verfahren zur herstellung und ihre verwendung. |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS56100860A (pt) |
| BE (1) | BE904409Q (pt) |
| BR (1) | BR8008409A (pt) |
| CH (1) | CH643873A5 (pt) |
| DE (1) | DE3046451A1 (pt) |
| ES (1) | ES498022A0 (pt) |
| FR (1) | FR2472002B1 (pt) |
| GB (1) | GB2066283B (pt) |
| HK (1) | HK31884A (pt) |
| IT (1) | IT1142199B (pt) |
| KE (1) | KE3635A (pt) |
| MY (1) | MY8600696A (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2270923B (en) * | 1992-09-24 | 1995-11-08 | Sandoz Ltd | Fibre-reactive monoazo copper complexes |
| FR2779872B1 (fr) * | 1998-06-11 | 2000-08-04 | Alsthom Cge Alcatel | Batterie monobloc comportant un dispositif d'echange thermique par circulation d'un fluide |
| CN108640883A (zh) * | 2018-04-11 | 2018-10-12 | 江苏安诺其化工有限公司 | 一种偶氮类化合物、其制备方法及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569115A (pt) * | 1957-07-05 | |||
| DE1098098B (de) * | 1958-09-17 | 1961-01-26 | Telefunken Gmbh | Wickelmaschine zur Herstellung von Wicklungen der Elektrotechnik nach dem Saegezahnschrittverfahren |
| DE1139932B (de) * | 1959-04-07 | 1962-11-22 | Ici Ltd | Verfahren zur Herstellung von wasserloeslichen, metallhaltigen Monoazofarbstoffen |
| FR78104E (fr) * | 1960-05-04 | 1962-06-08 | Sandoz Sa | Colorants réactifs métallifères, leurs procédés de fabrication et leurs applications |
| DE1215842B (de) * | 1961-04-21 | 1966-05-05 | Sandoz Ag | Verfahren zur Herstellung wasserloeslicher Reaktivfarbstoffe |
| CH499603A (de) * | 1967-04-07 | 1970-11-30 | Bayer Ag | Verfahren zur Herstellung von Azo-Reaktivfarbstoffen |
| DE1644208C3 (de) * | 1967-04-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe |
| US3732218A (en) * | 1968-11-12 | 1973-05-08 | Ciba Geigy Ag | Quaternary substituted triazines |
| DE2037543A1 (en) * | 1970-07-29 | 1972-02-03 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Monochlorotriazine metal complex dyes -for wool, polyamide, polyureth - and esp cellulosic fibres |
-
1979
- 1979-12-20 CH CH1132179A patent/CH643873A5/de not_active IP Right Cessation
-
1980
- 1980-12-05 IT IT50316/80A patent/IT1142199B/it active
- 1980-12-10 DE DE19803046451 patent/DE3046451A1/de not_active Withdrawn
- 1980-12-17 GB GB8040437A patent/GB2066283B/en not_active Expired
- 1980-12-18 JP JP17814680A patent/JPS56100860A/ja active Pending
- 1980-12-19 BR BR8008409A patent/BR8008409A/pt unknown
- 1980-12-19 FR FR8027047A patent/FR2472002B1/fr not_active Expired
- 1980-12-19 ES ES498022A patent/ES498022A0/es active Granted
-
1984
- 1984-04-12 HK HK318/84A patent/HK31884A/xx unknown
-
1986
- 1986-03-13 BE BE1/011452A patent/BE904409Q/fr not_active IP Right Cessation
- 1986-05-05 KE KE3635A patent/KE3635A/xx unknown
- 1986-12-30 MY MY696/86A patent/MY8600696A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3046451A1 (de) | 1981-08-27 |
| BR8008409A (pt) | 1981-07-14 |
| GB2066283A (en) | 1981-07-08 |
| ES8303501A1 (es) | 1983-02-01 |
| GB2066283B (en) | 1983-06-22 |
| JPS56100860A (en) | 1981-08-13 |
| IT1142199B (it) | 1986-10-08 |
| FR2472002A1 (fr) | 1981-06-26 |
| FR2472002B1 (fr) | 1986-05-09 |
| IT8050316A0 (it) | 1980-12-05 |
| KE3635A (en) | 1986-05-30 |
| MY8600696A (en) | 1986-12-31 |
| HK31884A (en) | 1984-04-19 |
| BE904409Q (fr) | 1986-06-30 |
| ES498022A0 (es) | 1983-02-01 |
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