DE1544544A1 - Azofarbstoffe und Verfahren zu deren Darstellung - Google Patents
Azofarbstoffe und Verfahren zu deren DarstellungInfo
- Publication number
- DE1544544A1 DE1544544A1 DE19651544544 DE1544544A DE1544544A1 DE 1544544 A1 DE1544544 A1 DE 1544544A1 DE 19651544544 DE19651544544 DE 19651544544 DE 1544544 A DE1544544 A DE 1544544A DE 1544544 A1 DE1544544 A1 DE 1544544A1
- Authority
- DE
- Germany
- Prior art keywords
- azo
- radical
- group
- compounds
- azo dyes
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000000987 azo dye Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 22
- -1 hydrazine compound Chemical class 0.000 claims description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- 239000004743 Polypropylene Substances 0.000 claims description 13
- 229920001155 polypropylene Polymers 0.000 claims description 13
- 150000002429 hydrazines Chemical class 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical compound NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 claims description 4
- GULVDPYLWVXKGC-UHFFFAOYSA-N quinoxalin-2-ylhydrazine Chemical class C1=CC=CC2=NC(NN)=CN=C21 GULVDPYLWVXKGC-UHFFFAOYSA-N 0.000 claims description 4
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 claims description 3
- 150000004782 1-naphthols Chemical class 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 150000003252 quinoxalines Chemical class 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 150000000181 1,2-naphthoquinones Chemical class 0.000 claims description 2
- 150000004786 2-naphthols Chemical class 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical group 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- 150000004055 1,2-benzoquinones Chemical class 0.000 description 2
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RODNZCIFRICALV-UHFFFAOYSA-N (3-chloroquinoxalin-2-yl)hydrazine Chemical compound C1=CC=C2N=C(Cl)C(NN)=NC2=C1 RODNZCIFRICALV-UHFFFAOYSA-N 0.000 description 1
- PHTHKSNCQCCOHM-UHFFFAOYSA-N (4,6-dimethylpyrimidin-2-yl)hydrazine Chemical compound CC1=CC(C)=NC(NN)=N1 PHTHKSNCQCCOHM-UHFFFAOYSA-N 0.000 description 1
- PCHXNQBTDCVAIT-UHFFFAOYSA-N (4-methoxy-6-methylpyrimidin-2-yl)hydrazine Chemical compound COC1=CC(C)=NC(NN)=N1 PCHXNQBTDCVAIT-UHFFFAOYSA-N 0.000 description 1
- HXQPYFMXCAIHAB-UHFFFAOYSA-N (4-methoxypyrimidin-2-yl)hydrazine Chemical compound COC1=CC=NC(NN)=N1 HXQPYFMXCAIHAB-UHFFFAOYSA-N 0.000 description 1
- WUKBRNKMQNEPAW-UHFFFAOYSA-N (4-methylpyrimidin-2-yl)hydrazine Chemical compound CC1=CC=NC(NN)=N1 WUKBRNKMQNEPAW-UHFFFAOYSA-N 0.000 description 1
- FLDYBLAUDDQRAB-UHFFFAOYSA-N (4-methylquinolin-2-yl)hydrazine Chemical compound C1=CC=C2C(C)=CC(NN)=NC2=C1 FLDYBLAUDDQRAB-UHFFFAOYSA-N 0.000 description 1
- BJYYJTBSIMBZTC-UHFFFAOYSA-N (4-phenylpyrimidin-2-yl)hydrazine Chemical compound NNC1=NC=CC(C=2C=CC=CC=2)=N1 BJYYJTBSIMBZTC-UHFFFAOYSA-N 0.000 description 1
- JUOYVELUZXXEGE-UHFFFAOYSA-N (5-bromopyrimidin-2-yl)hydrazine Chemical compound NNC1=NC=C(Br)C=N1 JUOYVELUZXXEGE-UHFFFAOYSA-N 0.000 description 1
- WUDNSGDMTFEQIF-UHFFFAOYSA-N (5-chloropyrimidin-2-yl)hydrazine Chemical compound NNC1=NC=C(Cl)C=N1 WUDNSGDMTFEQIF-UHFFFAOYSA-N 0.000 description 1
- FTYUJXNPXVDGLD-UHFFFAOYSA-N (5-methoxypyrimidin-2-yl)hydrazine Chemical compound COC1=CN=C(NN)N=C1 FTYUJXNPXVDGLD-UHFFFAOYSA-N 0.000 description 1
- LMFJCTVBDCMPAI-UHFFFAOYSA-N (5-phenylpyrimidin-2-yl)hydrazine Chemical compound C1=NC(NN)=NC=C1C1=CC=CC=C1 LMFJCTVBDCMPAI-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical class C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- DEKREBCFNLUULC-UHFFFAOYSA-N 1-aminonaphthalen-2-ol;hydron;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])=C(O)C=CC2=C1 DEKREBCFNLUULC-UHFFFAOYSA-N 0.000 description 1
- NMSRYZBDOYDJBJ-UHFFFAOYSA-N 4-anilinonaphthalene-1,2-dione Chemical compound C12=CC=CC=C2C(=O)C(=O)C=C1NC1=CC=CC=C1 NMSRYZBDOYDJBJ-UHFFFAOYSA-N 0.000 description 1
- FZPFRAHWZGGZMO-UHFFFAOYSA-N 4-methoxynaphthalene-1,2-dione Chemical compound C1=CC=C2C(OC)=CC(=O)C(=O)C2=C1 FZPFRAHWZGGZMO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QTOJRHLRJFVPJN-UHFFFAOYSA-L nickel(2+);diphenoxide Chemical class C=1C=CC=CC=1O[Ni]OC1=CC=CC=C1 QTOJRHLRJFVPJN-UHFFFAOYSA-L 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- MDNAGNNHVHHNDQ-UHFFFAOYSA-M potassium;n-oxosulfamate Chemical compound [K+].[O-]S(=O)(=O)N=O MDNAGNNHVHHNDQ-UHFFFAOYSA-M 0.000 description 1
- IVRLZJDPKUSDCF-UHFFFAOYSA-N pyrazin-2-ylhydrazine Chemical compound NNC1=CN=CC=N1 IVRLZJDPKUSDCF-UHFFFAOYSA-N 0.000 description 1
- YTRGNBTVTHPFJM-UHFFFAOYSA-N pyridazin-3-ylhydrazine Chemical compound NNC1=CC=CN=N1 YTRGNBTVTHPFJM-UHFFFAOYSA-N 0.000 description 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
- QIEQDFYXVYQLLU-UHFFFAOYSA-N pyrimidin-4-ylhydrazine Chemical compound NNC1=CC=NC=N1 QIEQDFYXVYQLLU-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- SGMABXRSPZLOPP-UHFFFAOYSA-N quinazolin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=NC=C21 SGMABXRSPZLOPP-UHFFFAOYSA-N 0.000 description 1
- QVKNQXCOGYNFPC-UHFFFAOYSA-N quinazolin-4-ylhydrazine Chemical compound C1=CC=C2C(NN)=NC=NC2=C1 QVKNQXCOGYNFPC-UHFFFAOYSA-N 0.000 description 1
- QMVCLSHKMIGEFN-UHFFFAOYSA-N quinolin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=CC=C21 QMVCLSHKMIGEFN-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 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
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/928—Polyolefin fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0047226 | 1965-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1544544A1 true DE1544544A1 (de) | 1970-04-16 |
Family
ID=7101507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651544544 Pending DE1544544A1 (de) | 1965-09-17 | 1965-09-17 | Azofarbstoffe und Verfahren zu deren Darstellung |
Country Status (6)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147544A (en) * | 1977-09-12 | 1979-04-03 | Eastman Kodak Company | Photographic products and processes employing novel nondiffusible pyridylazonaphthol dye-releasing compounds |
| US4148642A (en) * | 1978-03-07 | 1979-04-10 | Eastman Kodak Company | Photographic products and processes employing nondiffusible 1-arylazo-4-isoquinolinol dye-releasing compounds |
| EP0357554A3 (de) * | 1988-08-31 | 1990-09-12 | Ciba-Geigy Ag | Metallkomplexverbindungen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3152112A (en) * | 1964-10-06 | Phenylazo- and phenylhydrazo- | ||
| US3116278A (en) * | 1960-04-30 | 1963-12-31 | Hoechst Ag | Water-insoluble azo-dyestuffs |
| FR1270940A (fr) * | 1960-10-17 | 1961-09-01 | Hoechst Ag | Complexes de métaux de colorants azoïques et leur préparation |
| GB1090045A (en) * | 1964-04-17 | 1967-11-08 | Sumitomo Chemical Co | Monoazo dyestuffs containing a quinoline residue and suitable for dyeing metal-modified polyolefin materials, and processes for producing and using them |
| US3337290A (en) * | 1964-04-28 | 1967-08-22 | American Aniline Prod | Polyolefin dyeing |
-
1965
- 1965-09-17 DE DE19651544544 patent/DE1544544A1/de active Pending
-
1966
- 1966-07-05 CH CH973166A patent/CH471198A/de not_active IP Right Cessation
- 1966-09-08 US US577805A patent/US3492287A/en not_active Expired - Lifetime
- 1966-09-12 NL NL6612822A patent/NL6612822A/xx unknown
- 1966-09-12 BE BE686734D patent/BE686734A/xx unknown
- 1966-09-16 GB GB41446/66A patent/GB1132638A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1132638A (en) | 1968-11-06 |
| CH471198A (de) | 1969-04-15 |
| BE686734A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-02-15 |
| US3492287A (en) | 1970-01-27 |
| NL6612822A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1544544A1 (de) | Azofarbstoffe und Verfahren zu deren Darstellung | |
| DE1544464B1 (de) | Verfahren zur Herstellung von wasserloeslichen,metallisierbaren Dis- und Trisazofarbstoffen und deren Schwermetallkomplexen | |
| DE2236269C2 (de) | Azoverbindungen, deren Herstellung und Verwendung | |
| DE1544480A1 (de) | Metallhaltige Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE942104C (de) | Verfahren zur Herstellung metallhaltiger Azofarbstoffe | |
| DE937367C (de) | Verfahren zur Herstellung chrom- oder kobalthaltiger Azofarbstoffe | |
| DE1001438C2 (de) | Verfahren zur Herstellung metallhaltiger Monoazofarbstoffe | |
| DE963898C (de) | Verfahren zur Herstellung von metallhaltigen Azofarbstoffen | |
| DE852724C (de) | Verfahren zur Herstellung neuer Disazofarbstoffe | |
| DE1003374C2 (de) | Verfahren zur Herstellung von metallhaltigen Azofarbstoffen | |
| DE1249814B (de) | Verfahren zum Färben metallhaltiger synthetischer Fasern | |
| DE913458C (de) | Verfahren zur Herstellung komplexer Chromverbindungen von Monoazofarbstoffen | |
| DE1109809B (de) | Verfahren zur Herstellung von Monoazofarbstoffen und ihren Metallkomplexverbindungen | |
| DE2022453C3 (de) | Azofarbstoffe und ihre 1 zu 1 Metallkomplexe, deren Herstellung und Verwendung | |
| DE1644356C3 (de) | 1 zu 2-Chrom- oder Kobalt-Mischkomplexfarbstoffe, ihre Herstellung und Verwendung zum Färben, Klotzen oder Bedrucken von natürlichen und synthetischen Polyamiden oder Leder | |
| AT162618B (de) | Verfahren zur Herstellung neuer Tetrakisazofarbstoffe | |
| DE932815C (de) | Verfahren zur Herstellung metallhaltiger Azofarbstoffe | |
| DE1007902B (de) | Verfahren zur Herstellung metallhaltiger Monoazofarbstoffe | |
| AT165077B (de) | Verfahren zur Herstellung neuer Trisazofarbstoffe | |
| AT163181B (de) | Verfahren zur Herstellung neuer Monoazofarbstoffe | |
| DE952200C (de) | Verfahren zur Herstellung von o,o-Dioxyazofarbstoffen und deren Metallkomplexverbindungen | |
| DE956864C (de) | Verfahren zur Herstellung metallhaltiger Azofarbstoffe | |
| DE1419837A1 (de) | Verfahren zur Herstellung von reaktiven Farbstoffen | |
| DE2450911A1 (de) | Neue azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| CH615210A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |