DE2656781C2 - Verfahren zur Herstellung aminogruppenhaltiger Azometallkomplexfarbstoffe - Google Patents
Verfahren zur Herstellung aminogruppenhaltiger AzometallkomplexfarbstoffeInfo
- Publication number
- DE2656781C2 DE2656781C2 DE19762656781 DE2656781A DE2656781C2 DE 2656781 C2 DE2656781 C2 DE 2656781C2 DE 19762656781 DE19762656781 DE 19762656781 DE 2656781 A DE2656781 A DE 2656781A DE 2656781 C2 DE2656781 C2 DE 2656781C2
- Authority
- DE
- Germany
- Prior art keywords
- dye
- metal complex
- complex dyes
- preparation
- amino groups
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 239000000434 metal complex dye Substances 0.000 title claims description 6
- 125000003277 amino group Chemical group 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 26
- 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 claims description 11
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 229910001385 heavy metal Inorganic materials 0.000 claims description 6
- 150000002736 metal compounds Chemical class 0.000 claims description 6
- 239000003463 adsorbent Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910052804 chromium Inorganic materials 0.000 description 8
- 239000011651 chromium Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000987 azo dye Substances 0.000 description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- ZFRBZRZEKIOGQI-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=CC(O)=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 ZFRBZRZEKIOGQI-UHFFFAOYSA-N 0.000 description 3
- HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 description 3
- 229910002480 Cu-O Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 2
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 2
- WKWVTNARZXNZQY-UHFFFAOYSA-N azanide;copper(1+) Chemical compound [Cu]N WKWVTNARZXNZQY-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- BJUKBQYOYJOPDS-UHFFFAOYSA-N [O-][N+]([Cu])=O Chemical compound [O-][N+]([Cu])=O BJUKBQYOYJOPDS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010626 work up procedure 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
- C09B45/48—Preparation from other complex metal compounds of azo dyes
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
-
- 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
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762656781 DE2656781C2 (de) | 1976-12-15 | 1976-12-15 | Verfahren zur Herstellung aminogruppenhaltiger Azometallkomplexfarbstoffe |
| IN385/DEL/77A IN147252B (en:Method) | 1976-12-15 | 1977-11-11 | |
| GB5160277A GB1554088A (en) | 1976-12-15 | 1977-12-12 | Process for the preparation of azo metal complex dyestuffs containing amino groups |
| CH1532477A CH626111A5 (en) | 1976-12-15 | 1977-12-13 | Process for preparing amino-containing azo metal complex dyes |
| JP14892477A JPS5374529A (en) | 1976-12-15 | 1977-12-13 | Method of making azo metal complex dye containing amino group |
| ES465042A ES465042A1 (es) | 1976-12-15 | 1977-12-14 | Procedimiento para la obtencion de colorantes azoicos de me-tal complejos conteniendo grupos amino. |
| FR7737740A FR2374383A1 (fr) | 1976-12-15 | 1977-12-14 | Procede de preparation de colorants consistant en complexes metalliques de composes azoiques portant des groupes amines |
| BR7708297A BR7708297A (pt) | 1976-12-15 | 1977-12-14 | Processo para preparacao de corantes complexos de metal azoicos contendo grupos amino |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762656781 DE2656781C2 (de) | 1976-12-15 | 1976-12-15 | Verfahren zur Herstellung aminogruppenhaltiger Azometallkomplexfarbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2656781A1 DE2656781A1 (de) | 1978-06-22 |
| DE2656781C2 true DE2656781C2 (de) | 1985-02-21 |
Family
ID=5995592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762656781 Expired DE2656781C2 (de) | 1976-12-15 | 1976-12-15 | Verfahren zur Herstellung aminogruppenhaltiger Azometallkomplexfarbstoffe |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5374529A (en:Method) |
| BR (1) | BR7708297A (en:Method) |
| CH (1) | CH626111A5 (en:Method) |
| DE (1) | DE2656781C2 (en:Method) |
| ES (1) | ES465042A1 (en:Method) |
| FR (1) | FR2374383A1 (en:Method) |
| GB (1) | GB1554088A (en:Method) |
| IN (1) | IN147252B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19806744A1 (de) * | 1998-02-18 | 1999-08-19 | Bayer Ag | Verfahren zur Herstellung von Aminodiarylazoverbindungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1514670A (en) * | 1975-11-28 | 1978-06-21 | Bayer Ag | Removing 4-coupled products from azo dyestuffs derived from 1-naphthol series coupling components |
-
1976
- 1976-12-15 DE DE19762656781 patent/DE2656781C2/de not_active Expired
-
1977
- 1977-11-11 IN IN385/DEL/77A patent/IN147252B/en unknown
- 1977-12-12 GB GB5160277A patent/GB1554088A/en not_active Expired
- 1977-12-13 JP JP14892477A patent/JPS5374529A/ja active Pending
- 1977-12-13 CH CH1532477A patent/CH626111A5/de not_active IP Right Cessation
- 1977-12-14 ES ES465042A patent/ES465042A1/es not_active Expired
- 1977-12-14 BR BR7708297A patent/BR7708297A/pt unknown
- 1977-12-14 FR FR7737740A patent/FR2374383A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CH626111A5 (en) | 1981-10-30 |
| ES465042A1 (es) | 1978-09-01 |
| FR2374383B1 (en:Method) | 1981-12-24 |
| GB1554088A (en) | 1979-10-17 |
| FR2374383A1 (fr) | 1978-07-13 |
| IN147252B (en:Method) | 1980-01-05 |
| BR7708297A (pt) | 1978-08-15 |
| DE2656781A1 (de) | 1978-06-22 |
| JPS5374529A (en) | 1978-07-03 |
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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 |