DE1569638B2 - Verfahren zur herstellung chromhaltiger azomethinfarbstoffe - Google Patents
Verfahren zur herstellung chromhaltiger azomethinfarbstoffeInfo
- Publication number
- DE1569638B2 DE1569638B2 DE19511569638 DE1569638A DE1569638B2 DE 1569638 B2 DE1569638 B2 DE 1569638B2 DE 19511569638 DE19511569638 DE 19511569638 DE 1569638 A DE1569638 A DE 1569638A DE 1569638 B2 DE1569638 B2 DE 1569638B2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- aldehyde
- chromium
- hydroxy
- 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.)
- Granted
Links
- 239000000975 dye Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229910052804 chromium Inorganic materials 0.000 claims description 17
- 239000011651 chromium Substances 0.000 claims description 17
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 15
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
- -1 3-sulfophenyl Chemical group 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 210000002268 wool Anatomy 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000000909 amidinium group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 150000005840 aryl radicals Chemical class 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000004043 dyeing Methods 0.000 claims 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 3
- 150000001805 chlorine compounds Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002790 naphthalenes Chemical class 0.000 claims 2
- 150000003142 primary aromatic amines Chemical class 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical class O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000004532 chromating Methods 0.000 claims 1
- 150000001844 chromium Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000004675 formic acid derivatives Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- BVSPJPNNLDIUFE-UHFFFAOYSA-N n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC=C1 BVSPJPNNLDIUFE-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims 1
- 150000003870 salicylic acids Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims 1
- 229960004546 thiabendazole Drugs 0.000 claims 1
- 150000003673 urethanes Chemical class 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- WAPRMAKDPQYODC-UHFFFAOYSA-N 2-amino-3-hydroxybenzenesulfonic acid Chemical compound NC1=C(O)C=CC=C1S(O)(=O)=O WAPRMAKDPQYODC-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
-
- 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
- C09B55/00—Azomethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511569638 DE1569638B2 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur herstellung chromhaltiger azomethinfarbstoffe |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511569638 DE1569638B2 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur herstellung chromhaltiger azomethinfarbstoffe |
| DEB83129A DE1260471B (de) | 1965-08-04 | 1965-08-04 | Verfahren zur Herstellung von Sulfobetainen der Pyrazolonreihe |
| DEB0083156 | 1965-08-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1569638A1 DE1569638A1 (de) | 1970-04-30 |
| DE1569638B2 true DE1569638B2 (de) | 1973-09-06 |
| DE1569638C3 DE1569638C3 (enrdf_load_stackoverflow) | 1974-05-09 |
Family
ID=27180815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19511569638 Granted DE1569638B2 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur herstellung chromhaltiger azomethinfarbstoffe |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1569638B2 (enrdf_load_stackoverflow) |
-
1951
- 1951-01-28 DE DE19511569638 patent/DE1569638B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE1569638A1 (de) | 1970-04-30 |
| DE1569638C3 (enrdf_load_stackoverflow) | 1974-05-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |