CA1050014A - Azo dyes - Google Patents
Azo dyesInfo
- Publication number
- CA1050014A CA1050014A CA220,917A CA220917A CA1050014A CA 1050014 A CA1050014 A CA 1050014A CA 220917 A CA220917 A CA 220917A CA 1050014 A CA1050014 A CA 1050014A
- Authority
- CA
- Canada
- Prior art keywords
- signifies
- hydrogen
- formula
- halogen atom
- sulpho group
- 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
- 239000000987 azo dye Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- -1 sulpho group Chemical group 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 150000001768 cations Chemical class 0.000 claims abstract description 13
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 9
- 239000011651 chromium Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 11
- 238000004043 dyeing Methods 0.000 claims description 9
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000010000 carbonizing Methods 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical group C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 238000010026 decatizing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 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 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH282774A CH594035A5 (en, 2012) | 1974-02-28 | 1974-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050014A true CA1050014A (en) | 1979-03-06 |
Family
ID=4242485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,917A Expired CA1050014A (en) | 1974-02-28 | 1975-02-27 | Azo dyes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4058514A (en, 2012) |
| JP (1) | JPS5835228B2 (en, 2012) |
| BE (1) | BE876430Q (en, 2012) |
| BR (1) | BR7501159A (en, 2012) |
| CA (1) | CA1050014A (en, 2012) |
| CH (1) | CH594035A5 (en, 2012) |
| DE (1) | DE2507120C2 (en, 2012) |
| FR (1) | FR2262687B1 (en, 2012) |
| GB (1) | GB1494023A (en, 2012) |
| HK (1) | HK46579A (en, 2012) |
| IT (1) | IT1029888B (en, 2012) |
| PL (1) | PL96885B1 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5285230A (en) * | 1976-01-09 | 1977-07-15 | Sandoz Ag | Unsymmetrical 1 22chrome complex compounds and process for producing same and dyeing or textile printing method |
| FR2508472A1 (fr) * | 1981-06-25 | 1982-12-31 | Sandoz Sa | Melanges de complexes metalliferes, leur preparation et leur application comme colorants |
| DE3631751A1 (de) * | 1986-09-18 | 1988-03-31 | Bayer Ag | Asymmetrische 1:2-chromkomplexfarbstoffe |
| DE3631752A1 (de) * | 1986-09-18 | 1988-03-31 | Bayer Ag | Asymmetrische 1:2-chromkomplexfarbstoffe |
| EP0384893B1 (de) * | 1989-02-23 | 1994-09-07 | Ciba-Geigy Ag | Verfahren zur Herstellung von asymmetrischen 1:2-Metallkomplexfarbstoffen |
| TW200634100A (en) * | 2005-02-04 | 2006-10-01 | Clariant Int Ltd | Cationic antipyrine based azo metal complex dyes for use in optical layers for optical data recording |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2832760A (en) * | 1958-04-29 | Cooh i | ||
| US2767166A (en) * | 1952-01-31 | 1956-10-16 | Gen Aniline & Film Corp | Process for the preparation of chromed azo dyes derived from an anisidine |
| US3005813A (en) * | 1953-05-22 | 1961-10-24 | Ciba Ltd | Metalliferous azo-dyestuffs |
| US2806760A (en) * | 1953-06-10 | 1957-09-17 | Ciba Ltd | Process for dyeing nitrogenous fibers with metalliferous monoazo dyestuffs |
| US2826573A (en) * | 1953-10-02 | 1958-03-11 | Gen Aniline & Film Corp | Monoacid salts of aralkyl polyamines and metallized monoazo dyestuffs |
| FR1197010A (fr) * | 1956-12-15 | 1959-11-27 | Basf Ag | Procédé pour la production de colorants azoïques chromifères |
| US3144437A (en) * | 1957-03-15 | 1964-08-11 | Sandoz Ag | Chromium and cobalt complex compounds of monoazo dyestuffs |
| CH355238A (fr) * | 1958-07-04 | 1961-06-30 | Matieres Colorantes S A Comp F | Procédé de préparation de colorants monoazoïques |
| DE1271857B (de) * | 1962-10-17 | 1968-07-04 | Ciba Geigy | Verfahren zur Herstellung chromhaltiger Azofarbstoffe |
| US3356671A (en) * | 1965-03-17 | 1967-12-05 | Ici Ltd | Process of preparing unsymmetrical 1:2-cobalt complexed azo compounds |
| CH476812A (de) * | 1966-05-06 | 1969-08-15 | Geigy Ag J R | Verfahren zur Herstellung schwermetallhaltiger Azofarbstoffe |
| FR1518833A (fr) * | 1967-02-10 | 1968-03-29 | Ugine Kuhlmann | Nouveaux complexes métallifères mixtes |
| DE2408224A1 (de) * | 1974-02-21 | 1975-10-02 | Bayer Ag | Azochrommischkomplex-farbstoffe |
-
1974
- 1974-02-28 CH CH282774A patent/CH594035A5/xx not_active IP Right Cessation
-
1975
- 1975-02-19 DE DE2507120A patent/DE2507120C2/de not_active Expired
- 1975-02-24 GB GB7710/75A patent/GB1494023A/en not_active Expired
- 1975-02-24 US US05/552,241 patent/US4058514A/en not_active Expired - Lifetime
- 1975-02-26 BR BR1159/75A patent/BR7501159A/pt unknown
- 1975-02-26 JP JP50022976A patent/JPS5835228B2/ja not_active Expired
- 1975-02-27 CA CA220,917A patent/CA1050014A/en not_active Expired
- 1975-02-27 IT IT48377/75A patent/IT1029888B/it active
- 1975-02-27 PL PL1975178368A patent/PL96885B1/pl unknown
- 1975-02-27 FR FR7506109A patent/FR2262687B1/fr not_active Expired
-
1979
- 1979-05-21 BE BE0/195304A patent/BE876430Q/xx not_active IP Right Cessation
- 1979-07-12 HK HK465/79A patent/HK46579A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1494023A (en) | 1977-12-07 |
| JPS50119831A (en, 2012) | 1975-09-19 |
| FR2262687B1 (en, 2012) | 1978-09-29 |
| IT1029888B (it) | 1979-03-20 |
| US4058514A (en) | 1977-11-15 |
| BR7501159A (pt) | 1975-12-02 |
| HK46579A (en) | 1979-07-20 |
| FR2262687A1 (en, 2012) | 1975-09-26 |
| DE2507120C2 (de) | 1983-10-27 |
| DE2507120A1 (de) | 1975-09-04 |
| CH594035A5 (en, 2012) | 1977-12-30 |
| PL96885B1 (pl) | 1978-01-31 |
| JPS5835228B2 (ja) | 1983-08-01 |
| BE876430Q (fr) | 1979-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0051041B1 (en) | Basic or cationic sulphonic acid group-containing azo compounds, their synthesis and their use in dyeing substrates containing paper or cotton as well as dyestuff preparations thereof | |
| JPH04252270A (ja) | アゾ染料 | |
| JPS6014045B2 (ja) | 反応性染料およびその製法 | |
| JPH0251565A (ja) | アゾ染料 | |
| CA1050014A (en) | Azo dyes | |
| US4502866A (en) | Symmetrical unsubstituted and substituted 2-halo-4-(4'-(trisulfonaphthylazo)phenylamino)-1,3,5-triazin-6-ylamino compounds | |
| US3426008A (en) | Water-soluble monoazo dyestuffs and their metal complex compounds | |
| JPS6131743B2 (en, 2012) | ||
| CA1052374A (en) | Trisazo dyes | |
| DE2349709A1 (de) | Azoverbindungen, deren herstellung und verwendung | |
| US2804454A (en) | Complex heavy metal compounds of monoazo dyestuffs | |
| US2839521A (en) | Azo dyestuffs containing heavy metal | |
| EP0188473A1 (en) | Azo compounds containing a vinylsulphonyl group and at least one basic group and metal complexes thereof. | |
| US5698683A (en) | Mixed aluminium-heavy metal dyestuff complexes and a process for their preparation | |
| CA1070297A (en) | Azo dyestuffs | |
| US3578653A (en) | Monoazonaphthotriazostilbene dyestuffs | |
| US4051116A (en) | Assymmetrical 1:2 cobalt complexes of metallizable monoazo compounds having one sulfo group per complex | |
| US2741655A (en) | Cupriferous azo-dyestuffs | |
| GB2027734A (en) | Chromium complex dyestuffs | |
| US3970615A (en) | Unsymmetrical mono-sulfo containing chromium complexes of azo dyes | |
| JPH06212083A (ja) | アゾ染料類、それらの製造方法及びその用途 | |
| JPS63112661A (ja) | 水溶性ジスアゾ化合物、その製法及び該化合物を染料として使用する方法 | |
| JPS60112860A (ja) | 反応性染料 | |
| US4101547A (en) | 1,4-Diaminoanthraquinones | |
| JPS61133269A (ja) | モノアゾ染料 |