DE1218637B - Verfahren zur Herstellung von wasserunloeslichen Disazofarbstoffen - Google Patents
Verfahren zur Herstellung von wasserunloeslichen DisazofarbstoffenInfo
- Publication number
- DE1218637B DE1218637B DES83110A DES0083110A DE1218637B DE 1218637 B DE1218637 B DE 1218637B DE S83110 A DES83110 A DE S83110A DE S0083110 A DES0083110 A DE S0083110A DE 1218637 B DE1218637 B DE 1218637B
- Authority
- DE
- Germany
- Prior art keywords
- water
- parts
- preparation
- disazo dyes
- insoluble disazo
- 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
- 239000000975 dye Substances 0.000 title claims description 11
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- -1 aromatic radical Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000013589 supplement Substances 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSYKHFLOFLPSGY-UHFFFAOYSA-N 1-(4-amino-6-ethoxy-1,3-benzothiazol-2-yl)butane-1,3-dione Chemical compound CCOC1=CC(N)=C2N=C(C(=O)CC(C)=O)SC2=C1 OSYKHFLOFLPSGY-UHFFFAOYSA-N 0.000 description 1
- ZSSLZLKDKSRTDR-UHFFFAOYSA-N C(CC(=O)C)(=O)NC=1SC2=C(N1)C(=CC=C2)OC Chemical compound C(CC(=O)C)(=O)NC=1SC2=C(N1)C(=CC=C2)OC ZSSLZLKDKSRTDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- UBSFWQHUDZXPLU-UHFFFAOYSA-N aniline;1,3-benzothiazole Chemical compound NC1=CC=CC=C1.C1=CC=C2SC=NC2=C1 UBSFWQHUDZXPLU-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- KRVAVIMTIIEASB-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical compound C1=CC=C2SC(NC(=O)CC(=O)C)=NC2=C1 KRVAVIMTIIEASB-UHFFFAOYSA-N 0.000 description 1
- NHICDHRWQLIKIS-UHFFFAOYSA-N n-(6-acetamido-1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical compound C1=C(NC(C)=O)C=C2SC(NC(=O)CC(=O)C)=NC2=C1 NHICDHRWQLIKIS-UHFFFAOYSA-N 0.000 description 1
- KZNSYVINVBDMMP-UHFFFAOYSA-N n-(6-methoxy-1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical compound COC1=CC=C2N=C(NC(=O)CC(C)=O)SC2=C1 KZNSYVINVBDMMP-UHFFFAOYSA-N 0.000 description 1
- WQXHRCVELMMXNV-UHFFFAOYSA-N n-(6-methyl-1,3-benzothiazol-2-yl)-3-oxobutanamide Chemical compound C1=C(C)C=C2SC(NC(=O)CC(=O)C)=NC2=C1 WQXHRCVELMMXNV-UHFFFAOYSA-N 0.000 description 1
- YFFMOTYYWNEBHP-UHFFFAOYSA-N n-[2-(3-oxobutanoylamino)-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(NC(=O)CC(=O)C)=NC2=CC=C1NC(=O)C1=CC=CC=C1 YFFMOTYYWNEBHP-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing 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
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1218637X | 1962-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1218637B true DE1218637B (de) | 1966-06-08 |
Family
ID=4563585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES83110A Pending DE1218637B (de) | 1962-01-19 | 1962-12-29 | Verfahren zur Herstellung von wasserunloeslichen Disazofarbstoffen |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE626371A (enrdf_load_stackoverflow) |
| DE (1) | DE1218637B (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1088634B (de) * | 1958-05-23 | 1960-09-08 | Hoechst Ag | Verfahren zur Herstellung eines wasserunloeslichen Disazofarbstoffes |
-
0
- BE BE626371D patent/BE626371A/xx unknown
-
1962
- 1962-12-29 DE DES83110A patent/DE1218637B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1088634B (de) * | 1958-05-23 | 1960-09-08 | Hoechst Ag | Verfahren zur Herstellung eines wasserunloeslichen Disazofarbstoffes |
Also Published As
| Publication number | Publication date |
|---|---|
| BE626371A (enrdf_load_stackoverflow) |
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