DE2155866C3 - Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Verwendung - Google Patents
Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und VerwendungInfo
- Publication number
- DE2155866C3 DE2155866C3 DE19712155866 DE2155866A DE2155866C3 DE 2155866 C3 DE2155866 C3 DE 2155866C3 DE 19712155866 DE19712155866 DE 19712155866 DE 2155866 A DE2155866 A DE 2155866A DE 2155866 C3 DE2155866 C3 DE 2155866C3
- Authority
- DE
- Germany
- Prior art keywords
- water
- dyes
- dye
- preparation
- monoazo 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 5
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 description 15
- 238000004043 dyeing Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 10
- 239000000835 fiber Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 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 4
- 239000004952 Polyamide Substances 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- -1 polyhexamethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006304 triacetate fiber Polymers 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- YMNDTPFVRMWDQK-UHFFFAOYSA-N [O-][N+](CC(O)OC(C=C1)=CC=C1[N+]([O-])=O)=O Chemical compound [O-][N+](CC(O)OC(C=C1)=CC=C1[N+]([O-])=O)=O YMNDTPFVRMWDQK-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE791261D BE791261A (fr) | 1971-11-10 | Colorants monoazoiques insolubles dans l'eau | |
| DE19712155866 DE2155866C3 (de) | 1971-11-10 | 1971-11-10 | Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Verwendung |
| ES408277A ES408277A1 (es) | 1971-11-10 | 1972-11-04 | Procedimiento para la preparacion de colorantes monoazoicosinsolubles en agua. |
| CH1621872A CH564579A5 (enrdf_load_stackoverflow) | 1971-11-10 | 1972-11-07 | |
| JP11132272A JPS4858026A (enrdf_load_stackoverflow) | 1971-11-10 | 1972-11-08 | |
| BR782472A BR7207824D0 (pt) | 1971-11-10 | 1972-11-08 | Processo para obtencao de corantes monoazoicos insoluveis em agua |
| IT3143072A IT970319B (it) | 1971-11-10 | 1972-11-08 | Monocazocoloranti idroinsolubili e procedimento per la loro prepa razione |
| CA156,069A CA962669A (en) | 1971-11-10 | 1972-11-09 | Water-insoluble monoazo dyestuffs and process for preparing them |
| FR7239899A FR2159454B1 (enrdf_load_stackoverflow) | 1971-11-10 | 1972-11-10 | |
| GB5205272A GB1409254A (en) | 1971-11-10 | 1972-11-10 | Water-insoluble monoazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712155866 DE2155866C3 (de) | 1971-11-10 | 1971-11-10 | Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2155866A1 DE2155866A1 (de) | 1973-05-24 |
| DE2155866B2 DE2155866B2 (de) | 1974-02-28 |
| DE2155866C3 true DE2155866C3 (de) | 1974-10-10 |
Family
ID=5824734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712155866 Expired DE2155866C3 (de) | 1971-11-10 | 1971-11-10 | Wasserunlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und Verwendung |
Country Status (10)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1261580A (fr) * | 1960-06-29 | 1961-05-19 | Sandoz Ag | Nouveaux colorants azoïques nitrés convenant pour la teinture, le foulardage et l'impression des fibres de polyester et préparation de ces colorants |
| FR1494489A (fr) * | 1965-09-24 | 1967-09-08 | Geigy Ag J R | Colorants mono-azoïques et leur préparation |
-
0
- BE BE791261D patent/BE791261A/xx unknown
-
1971
- 1971-11-10 DE DE19712155866 patent/DE2155866C3/de not_active Expired
-
1972
- 1972-11-04 ES ES408277A patent/ES408277A1/es not_active Expired
- 1972-11-07 CH CH1621872A patent/CH564579A5/xx not_active IP Right Cessation
- 1972-11-08 BR BR782472A patent/BR7207824D0/pt unknown
- 1972-11-08 IT IT3143072A patent/IT970319B/it active
- 1972-11-08 JP JP11132272A patent/JPS4858026A/ja active Pending
- 1972-11-09 CA CA156,069A patent/CA962669A/en not_active Expired
- 1972-11-10 FR FR7239899A patent/FR2159454B1/fr not_active Expired
- 1972-11-10 GB GB5205272A patent/GB1409254A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2159454A1 (enrdf_load_stackoverflow) | 1973-06-22 |
| DE2155866A1 (de) | 1973-05-24 |
| CA962669A (en) | 1975-02-11 |
| CH564579A5 (enrdf_load_stackoverflow) | 1975-07-31 |
| DE2155866B2 (de) | 1974-02-28 |
| BE791261A (fr) | 1973-05-10 |
| FR2159454B1 (enrdf_load_stackoverflow) | 1976-06-04 |
| ES408277A1 (es) | 1976-03-01 |
| JPS4858026A (enrdf_load_stackoverflow) | 1973-08-15 |
| GB1409254A (en) | 1975-10-08 |
| IT970319B (it) | 1974-04-10 |
| BR7207824D0 (pt) | 1973-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |