CH653696A5 - Verfahren zur herstellung von disazofarbstoffen. - Google Patents
Verfahren zur herstellung von disazofarbstoffen. Download PDFInfo
- Publication number
- CH653696A5 CH653696A5 CH512/83A CH51283A CH653696A5 CH 653696 A5 CH653696 A5 CH 653696A5 CH 512/83 A CH512/83 A CH 512/83A CH 51283 A CH51283 A CH 51283A CH 653696 A5 CH653696 A5 CH 653696A5
- Authority
- CH
- Switzerland
- Prior art keywords
- navy blue
- formula
- disazo
- compound
- purity
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 35
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 description 33
- 238000005859 coupling reaction Methods 0.000 description 25
- 230000008878 coupling Effects 0.000 description 24
- 238000010168 coupling process Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 238000004043 dyeing Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 229920000728 polyester Polymers 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 11
- -1 alkoxycarbamoyl Chemical group 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JDFLQGBQDBFMGH-UHFFFAOYSA-N 2-amino-5-[(4-nitrophenyl)diazenyl]thiophene-3-carbonitrile Chemical compound N#CC1=C(N)SC(N=NC=2C=CC(=CC=2)[N+]([O-])=O)=C1 JDFLQGBQDBFMGH-UHFFFAOYSA-N 0.000 description 1
- LOGPMRUTGLEHIV-UHFFFAOYSA-N 2-amino-5-phenyl-2-(thiophen-2-yldiazenyl)-3H-thiophene-3-carbonitrile Chemical compound NC1(SC(=CC1C#N)C1=CC=CC=C1)N=NC=1SC=CC1 LOGPMRUTGLEHIV-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920006239 diacetate fiber Polymers 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Photoreceptors In Electrophotography (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57012083A JPS58129059A (ja) | 1982-01-28 | 1982-01-28 | ジスアゾ染料の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH653696A5 true CH653696A5 (de) | 1986-01-15 |
Family
ID=11795686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH512/83A CH653696A5 (de) | 1982-01-28 | 1983-01-28 | Verfahren zur herstellung von disazofarbstoffen. |
Country Status (5)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2122633B (en) * | 1982-05-18 | 1986-01-08 | Mitsubishi Chem Ind | Thiophene disazo dyes for dyeing cellulose-containing fibers |
| DE3622297A1 (de) * | 1986-07-03 | 1988-01-07 | Basf Ag | Disazothiophenfarbstoffe |
| GB8704727D0 (en) * | 1987-02-27 | 1987-08-05 | Ici Plc | Aromatic disazo compound |
| JP2002516621A (ja) | 1996-11-27 | 2002-06-04 | イーストマン ケミカル カンパニー | 光吸収性ポリマー組成物の製造方法 |
| DE10039701A1 (de) | 2000-08-14 | 2002-02-28 | Basf Ag | Triarylmethanfarbstoffe |
| EP3470390B1 (en) | 2013-01-30 | 2023-06-07 | Ecolab USA Inc. | Hydrogen sulfide scavengers |
| US10308886B2 (en) | 2015-04-22 | 2019-06-04 | Ecolab Usa Inc. | Development of a novel high temperature stable scavenger for removal of hydrogen sulfide |
| US10584286B2 (en) | 2015-09-08 | 2020-03-10 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
| WO2017044250A1 (en) | 2015-09-08 | 2017-03-16 | Ecolab Usa Inc. | Hydrocarbon soluble/dispersible hemiformals as hydrogen sulfide scavengers |
| CA3031535A1 (en) | 2016-07-29 | 2018-02-01 | Ecolab Usa Inc. | Antifouling and hydrogen sulfide scavenging compositions |
| US10538710B2 (en) | 2017-07-13 | 2020-01-21 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
| CA3127439A1 (en) | 2019-01-23 | 2020-07-30 | Championx Usa Inc. | Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a michael acceptor |
| CN116515317A (zh) * | 2023-04-25 | 2023-08-01 | 宁夏保隆科技有限公司 | 一种分散蓝的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US989953A (en) * | 1910-10-04 | 1911-04-18 | Farbenfab Vorm Bayer F & Co | Dye. |
| DE2438496A1 (de) * | 1974-08-10 | 1976-02-26 | Bayer Ag | Disazofarbstoffe |
| DE2443485C2 (de) * | 1974-09-11 | 1983-04-07 | Bayer Ag, 5090 Leverkusen | Disazofarbstoffe und deren Verwendung |
| DE2640542A1 (de) * | 1976-09-09 | 1978-03-23 | Basf Ag | Azofarbstoffe |
| GB2093056B (en) * | 1980-12-26 | 1985-06-12 | Mitsubishi Chem Ind | Disazo dyestuffs and dyeing process |
| JPS57177059A (en) * | 1981-04-23 | 1982-10-30 | Mitsubishi Chem Ind Ltd | Disazo compound |
-
1982
- 1982-01-28 JP JP57012083A patent/JPS58129059A/ja active Granted
-
1983
- 1983-01-14 US US06/457,872 patent/US4760133A/en not_active Expired - Fee Related
- 1983-01-20 DE DE19833301822 patent/DE3301822A1/de active Granted
- 1983-01-28 CH CH512/83A patent/CH653696A5/de not_active IP Right Cessation
- 1983-01-28 GB GB08302437A patent/GB2114144B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0313265B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-02-22 |
| US4760133A (en) | 1988-07-26 |
| GB2114144A (en) | 1983-08-17 |
| GB2114144B (en) | 1985-07-24 |
| DE3301822A1 (de) | 1983-08-04 |
| DE3301822C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-02-28 |
| GB8302437D0 (en) | 1983-03-02 |
| JPS58129059A (ja) | 1983-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: RESEARCH ASSOCIATION OF SYNTHETIC DYESTUFFS -DANN |
|
| PL | Patent ceased |