DE751343C - Verfahren zur Herstellung von Disazofarbstoffen - Google Patents
Verfahren zur Herstellung von DisazofarbstoffenInfo
- Publication number
- DE751343C DE751343C DEG104868D DEG0104868D DE751343C DE 751343 C DE751343 C DE 751343C DE G104868 D DEG104868 D DE G104868D DE G0104868 D DEG0104868 D DE G0104868D DE 751343 C DE751343 C DE 751343C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- coupling
- water
- dye
- dioxy
- 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 41
- 238000000034 method Methods 0.000 title claims description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 15
- 230000008878 coupling Effects 0.000 claims description 34
- 238000010168 coupling process Methods 0.000 claims description 34
- 238000005859 coupling reaction Methods 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000002790 naphthalenes Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 23
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 239000000835 fiber Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
- 150000001879 copper Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 244000172533 Viola sororia Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 235000011116 calcium hydroxide Nutrition 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AIOLRLMFOWGSPL-UHFFFAOYSA-N chembl1337820 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=CC2=C1 AIOLRLMFOWGSPL-UHFFFAOYSA-N 0.000 description 2
- -1 copper complex compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 description 1
- KPXVZOAGGSFZEX-UHFFFAOYSA-N 5-methyl-4-phenylpyrazol-3-one Chemical compound O=C1N=NC(C)=C1C1=CC=CC=C1 KPXVZOAGGSFZEX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical class [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- RSJOBNMOMQFPKQ-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate Chemical class [Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O RSJOBNMOMQFPKQ-UHFFFAOYSA-L 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 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
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/18—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from heterocyclic compounds
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/16—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy-amines
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH232505T | 1941-02-18 | ||
| CH609299X | 1942-02-03 | ||
| CH616155X | 1942-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE751343C true DE751343C (de) | 1953-05-04 |
Family
ID=27177968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG104868D Expired DE751343C (de) | 1941-02-18 | 1942-02-14 | Verfahren zur Herstellung von Disazofarbstoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US2427537A (en, 2012) |
| BE (3) | BE444535A (en, 2012) |
| CH (38) | CH229184A (en, 2012) |
| DE (1) | DE751343C (en, 2012) |
| FR (3) | FR888245A (en, 2012) |
| GB (4) | GB609299A (en, 2012) |
| NL (4) | NL61608C (en, 2012) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2637723A (en) * | 1953-05-05 | Disazo dyestuffs contalgmd | ||
| US2820783A (en) * | 1958-01-21 | Foreign | ||
| US2557057A (en) * | 1943-12-20 | 1951-06-12 | Ciba Ltd | Disazo dyestuff |
| NL74670C (en, 2012) * | 1946-03-08 | |||
| US2476260A (en) * | 1946-04-11 | 1949-07-12 | Ciba Ltd | Process for the manufacture of disazo-dyestuffs |
| US2476261A (en) * | 1946-04-11 | 1949-07-12 | Ciba Ltd | Process for the manufacture of asymmetrical polyazo-dyestuffs |
| US2475265A (en) * | 1946-04-23 | 1949-07-05 | Ciba Ltd | Process for carrying out coupling reactions |
| US2536957A (en) * | 1946-10-17 | 1951-01-02 | Ciba Ltd | Process of making metalliferous azo dyestuffs |
| US2590346A (en) * | 1947-06-26 | 1952-03-25 | Ciba Ltd | Cupriferous disazo-dyestuffs |
| BE488200A (en, 2012) * | 1948-04-02 | |||
| US2612496A (en) * | 1948-04-02 | 1952-09-30 | Gaspar | Acid azo dyes |
| US2584935A (en) * | 1949-02-04 | 1952-02-05 | Gen Aniline & Film Corp | Unsymmetrical disazo dyestuffs |
| US2644814A (en) * | 1950-01-20 | 1953-07-07 | Hoechst Ag | Water-insoluble monoazodyestuffs |
| US2630431A (en) * | 1951-02-24 | 1953-03-03 | Du Pont | Metallized disazo dyes |
| NL177467B (nl) * | 1952-04-10 | Hoechst Ag | Werkwijze voor de bereiding van een katalysator voor het reduceren van stikstofoxyden in afvalgas. | |
| US2769806A (en) * | 1952-04-10 | 1956-11-06 | Ciba Ltd | Disazo-dyestuffs |
| US2793205A (en) * | 1952-11-28 | 1957-05-21 | Ciba Ltd | Disazo-dyestuffs |
| US2816102A (en) * | 1953-02-12 | 1957-12-10 | Ciba Ltd | Metalliferous azo dyestuffs |
| US2809963A (en) * | 1954-10-26 | 1957-10-15 | Ciba Ltd | Azo-dyestuffs |
| US2886562A (en) * | 1955-08-11 | 1959-05-12 | Bayer Ag | Disazo dyestuffs |
| BE559762A (en, 2012) * | 1956-08-02 | |||
| CH437589A (de) * | 1963-11-08 | 1967-06-15 | Durand & Huguenin Ag | Verfahren zur Herstellung von wasserlöslichen metallisierbaren Disazofarbstoffen |
| DE2451257C3 (de) * | 1974-10-29 | 1979-05-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von konzentrierten Farbstofflösungen und Verfahren zum Färben |
| CH663027A5 (de) * | 1985-01-08 | 1987-11-13 | Ciba Geigy Ag | Verfahren zur herstellung von metallisierbaren azofarbstoffen. |
| BR0116593A (pt) * | 2000-12-28 | 2003-12-23 | Ciba Sc Holding Ag | Corantes de disazo e seus complexos de cobre para tingir papel |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR481190A (fr) * | 1915-06-19 | 1916-11-08 | Soc Ind Chimique Bale | Production de colorants orthooxyazoiques substantifs et leur transformation en combinaisons cuivrées en substance ou sur la fibre |
| GB102881A (en) * | 1916-05-13 | 1917-01-04 | Oliver Imray | Manufacture of New, Direct-dyeing Ortho-oxy-azo-dyestuffs. |
| FR20186E (fr) * | 1915-06-19 | 1917-01-25 | Soc Ind Chimique Bale | Production de colorants orthooxyazoiques substantifs et leur transformation en combinaisons cuivrées en substance ou sur la fibre |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2036159A (en) * | 1936-03-31 | Manufacture of new azo dye stuff | ||
| GB190916092A (en) * | 1907-10-10 | 1910-08-09 | Antoine Miltiade Mille | Improvements in Automatic Lubricators. |
| US1210751A (en) * | 1915-10-08 | 1917-01-02 | Chem Ind Basel | Substantive orthooxyazo dyestuffs and a process of making same. |
| US1889732A (en) * | 1930-03-11 | 1932-11-29 | Gen Aniline Works Inc | Copper containing disazodyestuffs |
| GB352956A (en) * | 1930-04-14 | 1931-07-14 | Ig Farbenindustrie Ag | Process for the manufacture of substantive dyeing disazo dyestuffs containing copper |
| US1921337A (en) * | 1931-09-21 | 1933-08-08 | Gen Aniline Works Inc | Copper-containing azodyestuff |
| CH163896A (de) * | 1931-11-13 | 1933-09-15 | Ig Farbenindustrie Ag | Verfahren zur Herstellung eines o-Oxyazofarbstoffes. |
| GB410192A (en) * | 1931-11-13 | 1934-05-14 | Ig Farbenindustrie Ag | Process for the manufacture of azo-dyestuffs |
| FR842972A (fr) * | 1937-09-07 | 1939-06-22 | Ig Farbenindustrie Ag | Colorants azoïques et leur procédé de production |
| US2241796A (en) * | 1938-05-30 | 1941-05-13 | Gen Aniline & Film Corp | Azo dyestuffs |
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0
- BE BE453075D patent/BE453075A/xx unknown
-
1941
- 1941-02-18 CH CH229184D patent/CH229184A/de unknown
- 1941-02-18 CH CH232505D patent/CH232505A/de unknown
- 1941-02-18 CH CH232506D patent/CH232506A/de unknown
- 1941-02-18 CH CH232504D patent/CH232504A/de unknown
- 1941-02-18 CH CH232508D patent/CH232508A/de unknown
- 1941-02-18 CH CH232503D patent/CH232503A/de unknown
- 1941-02-18 CH CH233083D patent/CH233083A/de unknown
- 1941-02-18 CH CH231843D patent/CH231843A/de unknown
- 1941-02-18 CH CH232509D patent/CH232509A/de unknown
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1942
- 1942-02-02 CH CH257015D patent/CH257015A/de unknown
- 1942-02-02 CH CH257016D patent/CH257016A/de unknown
- 1942-02-02 CH CH246422D patent/CH246422A/de unknown
- 1942-02-03 CH CH236925D patent/CH236925A/de unknown
- 1942-02-03 CH CH241346D patent/CH241346A/de unknown
- 1942-02-03 CH CH238264D patent/CH238264A/de unknown
- 1942-02-05 CH CH257009D patent/CH257009A/de unknown
- 1942-02-05 CH CH257020D patent/CH257020A/de unknown
- 1942-02-05 CH CH257012D patent/CH257012A/de unknown
- 1942-02-05 CH CH257010D patent/CH257010A/de unknown
- 1942-02-05 CH CH257014D patent/CH257014A/de unknown
- 1942-02-05 CH CH246423D patent/CH246423A/de unknown
- 1942-02-05 CH CH257019D patent/CH257019A/de unknown
- 1942-02-05 CH CH257013D patent/CH257013A/de unknown
- 1942-02-05 CH CH257011D patent/CH257011A/de unknown
- 1942-02-14 DE DEG104868D patent/DE751343C/de not_active Expired
- 1942-02-14 FR FR888245D patent/FR888245A/fr not_active Expired
- 1942-02-16 FR FR888249D patent/FR888249A/fr not_active Expired
- 1942-02-18 GB GB2155/42A patent/GB609299A/en not_active Expired
- 1942-02-18 BE BE444535D patent/BE444535A/xx unknown
- 1942-02-18 BE BE444536D patent/BE444536A/xx unknown
- 1942-02-23 GB GB2370/42A patent/GB609300A/en not_active Expired
- 1942-02-24 GB GB2438/42A patent/GB609302A/en not_active Expired
- 1942-03-17 NL NL105166A patent/NL61608C/xx active
- 1942-03-17 NL NL105168A patent/NL61609C/xx active
- 1942-03-17 NL NL105167A patent/NL61326C/xx active
- 1942-10-30 CH CH236926D patent/CH236926A/de unknown
- 1942-10-30 CH CH236935D patent/CH236935A/de unknown
- 1942-10-30 CH CH236928D patent/CH236928A/de unknown
- 1942-10-30 CH CH241347D patent/CH241347A/de unknown
- 1942-10-30 CH CH236927D patent/CH236927A/de unknown
- 1942-10-30 CH CH236929D patent/CH236929A/de unknown
- 1942-10-30 CH CH236938D patent/CH236938A/de unknown
- 1942-10-30 CH CH236933D patent/CH236933A/de unknown
- 1942-10-30 CH CH236934D patent/CH236934A/de unknown
- 1942-10-30 CH CH236931D patent/CH236931A/de unknown
- 1942-10-30 CH CH236937D patent/CH236937A/de unknown
- 1942-10-30 CH CH236936D patent/CH236936A/de unknown
- 1942-10-30 CH CH236930D patent/CH236930A/de unknown
- 1942-10-30 CH CH236932D patent/CH236932A/de unknown
-
1943
- 1943-08-16 US US498883A patent/US2427537A/en not_active Expired - Lifetime
- 1943-08-16 US US498884A patent/US2426977A/en not_active Expired - Lifetime
- 1943-08-16 US US498885A patent/US2439153A/en not_active Expired - Lifetime
- 1943-08-16 US US498886A patent/US2424066A/en not_active Expired - Lifetime
- 1943-10-27 GB GB17711/43A patent/GB616155A/en not_active Expired
- 1943-10-28 FR FR899230D patent/FR899230A/fr not_active Expired
- 1943-10-28 NL NL113722A patent/NL62314C/xx active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR481190A (fr) * | 1915-06-19 | 1916-11-08 | Soc Ind Chimique Bale | Production de colorants orthooxyazoiques substantifs et leur transformation en combinaisons cuivrées en substance ou sur la fibre |
| FR20186E (fr) * | 1915-06-19 | 1917-01-25 | Soc Ind Chimique Bale | Production de colorants orthooxyazoiques substantifs et leur transformation en combinaisons cuivrées en substance ou sur la fibre |
| GB102881A (en) * | 1916-05-13 | 1917-01-04 | Oliver Imray | Manufacture of New, Direct-dyeing Ortho-oxy-azo-dyestuffs. |
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