CH499586A - Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen - Google Patents
Verfahren zur Herstellung von wasserunlöslichen AzofarbstoffenInfo
- Publication number
- CH499586A CH499586A CH158765A CH158765A CH499586A CH 499586 A CH499586 A CH 499586A CH 158765 A CH158765 A CH 158765A CH 158765 A CH158765 A CH 158765A CH 499586 A CH499586 A CH 499586A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- water
- formula
- nitrobenzene
- amino
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- ZZQFDAZNUQAIRZ-UHFFFAOYSA-N methyl 3-[N-(2-methoxyethyl)anilino]propanoate Chemical compound COC(=O)CCN(CCOC)C1=CC=CC=C1 ZZQFDAZNUQAIRZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 13
- 230000008878 coupling Effects 0.000 abstract description 10
- 238000010168 coupling process Methods 0.000 abstract description 10
- 238000005859 coupling reaction Methods 0.000 abstract description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 8
- 229940081735 acetylcellulose Drugs 0.000 abstract description 3
- 229920002301 cellulose acetate Polymers 0.000 abstract description 3
- 238000004043 dyeing Methods 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 239000004753 textile Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 3
- 239000010979 ruby Substances 0.000 description 5
- 229910001750 ruby Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- HOTZLWVITTVZGY-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F HOTZLWVITTVZGY-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- PITMSNMLUXCPLM-UHFFFAOYSA-N methyl 3-(3-aminophenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC(N)=C1 PITMSNMLUXCPLM-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YMZIFDLWYUSZCC-UHFFFAOYSA-N 2,6-dibromo-4-nitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1Br YMZIFDLWYUSZCC-UHFFFAOYSA-N 0.000 description 1
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- KIMXIMWZIRTKCQ-UHFFFAOYSA-N 2-methylsulfonyl-4-nitroaniline Chemical compound CS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1N KIMXIMWZIRTKCQ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- -1 alkylsulfone Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YOLHRXMBXDEAFS-UHFFFAOYSA-N methyl 3-(ethylamino)-5-methylbenzoate Chemical compound CCNC1=CC(C)=CC(C(=O)OC)=C1 YOLHRXMBXDEAFS-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75369A DE1283986B (de) | 1964-02-10 | 1964-02-10 | Verfahren zur Herstellung wasserunloeslicher Azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH499586A true CH499586A (de) | 1970-11-30 |
Family
ID=6978629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH158765A CH499586A (de) | 1964-02-10 | 1965-02-05 | Verfahren zur Herstellung von wasserunlöslichen Azofarbstoffen |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT248574B (en]) |
| BE (1) | BE659465A (en]) |
| CH (1) | CH499586A (en]) |
| DE (1) | DE1283986B (en]) |
| GB (1) | GB1090768A (en]) |
| NL (1) | NL6501591A (en]) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1135595B (de) * | 1959-03-04 | 1962-08-30 | Ici Ltd | Verfahren zur Herstellung von Azofarbstoffen |
-
1964
- 1964-02-10 DE DEB75369A patent/DE1283986B/de active Pending
-
1965
- 1965-02-05 CH CH158765A patent/CH499586A/de not_active IP Right Cessation
- 1965-02-09 GB GB552765A patent/GB1090768A/en not_active Expired
- 1965-02-09 NL NL6501591A patent/NL6501591A/xx unknown
- 1965-02-09 BE BE659465D patent/BE659465A/xx unknown
- 1965-02-10 AT AT118565A patent/AT248574B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1090768A (en) | 1967-11-15 |
| AT248574B (de) | 1966-08-10 |
| DE1283986B (de) | 1968-11-28 |
| NL6501591A (en]) | 1965-08-11 |
| BE659465A (en]) | 1965-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |