CA1049001A - Chromium complex dyes, their manufacture and use - Google Patents
Chromium complex dyes, their manufacture and useInfo
- Publication number
- CA1049001A CA1049001A CA75217945A CA217945A CA1049001A CA 1049001 A CA1049001 A CA 1049001A CA 75217945 A CA75217945 A CA 75217945A CA 217945 A CA217945 A CA 217945A CA 1049001 A CA1049001 A CA 1049001A
- Authority
- CA
- Canada
- Prior art keywords
- nitro
- formula
- methyl
- chromium complex
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 34
- 239000011651 chromium Substances 0.000 title claims abstract description 27
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- -1 1-(2'ethylphenyl)-3-methyl-5-pyrazolone 1-(4'-bromophenyl)-3-methyl-5-pyrazolone 1-(2'-chloro-6'-methylphenyl)-3-methyl-5-pyrazolone 1-(3'-nitrophenyl)-3-methyl-5-pyrazolone Chemical compound 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 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 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- KCEIVWKDBLAQKL-UHFFFAOYSA-N 2,5-dichloro-4-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl KCEIVWKDBLAQKL-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- MHAFRUMLQZZSIN-UHFFFAOYSA-N 2-amino-4-chloro-6-nitrophenol Chemical compound NC1=CC(Cl)=CC([N+]([O-])=O)=C1O MHAFRUMLQZZSIN-UHFFFAOYSA-N 0.000 description 1
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GDBFSJLHQMUHPQ-UHFFFAOYSA-N COC1=CC=C(C=C1)N1N=C(CC1=O)C.ClC1=C(C(=CC(=C1)Cl)Cl)N1N=C(CC1=O)C.BrC1=C(C=C(C=C1)Br)N1N=C(CC1=O)C Chemical compound COC1=CC=C(C=C1)N1N=C(CC1=O)C.ClC1=C(C(=CC(=C1)Cl)Cl)N1N=C(CC1=O)C.BrC1=C(C=C(C=C1)Br)N1N=C(CC1=O)C GDBFSJLHQMUHPQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method 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
- 238000001914 filtration Methods 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004552 water soluble powder Substances 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 |
|---|---|---|---|
| CH61774A CH589126A5 (en, 2012) | 1974-01-17 | 1974-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049001A true CA1049001A (en) | 1979-02-20 |
Family
ID=4191170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75217945A Expired CA1049001A (en) | 1974-01-17 | 1975-01-15 | Chromium complex dyes, their manufacture and use |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5837341B2 (en, 2012) |
| AR (1) | AR207461A1 (en, 2012) |
| AU (1) | AU7736275A (en, 2012) |
| BR (1) | BR7500264A (en, 2012) |
| CA (1) | CA1049001A (en, 2012) |
| CH (1) | CH589126A5 (en, 2012) |
| DE (1) | DE2501449C2 (en, 2012) |
| ES (1) | ES433862A1 (en, 2012) |
| FR (1) | FR2258431B1 (en, 2012) |
| GB (1) | GB1493474A (en, 2012) |
| IT (1) | IT1026342B (en, 2012) |
| NL (1) | NL7500077A (en, 2012) |
| ZA (1) | ZA75315B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH616953A5 (en, 2012) * | 1975-08-27 | 1980-04-30 | Sandoz Ag | |
| DE2840651A1 (de) * | 1978-09-19 | 1980-03-27 | Bayer Ag | Chromkomplexfarbstoffe |
| DE3049552A1 (de) * | 1980-12-31 | 1982-07-29 | Basf Ag, 6700 Ludwigshafen | Komplexfarbstoff-gemische |
| JPH03169971A (ja) * | 1989-11-29 | 1991-07-23 | Matsushita Electric Works Ltd | 直敷床材とその製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB765355A (en) * | 1953-06-08 | 1957-01-09 | Ciba Ltd | Mixed complexes of metalliferous mono-azo-dyestuffs and process for making them |
| FR1209088A (fr) * | 1958-04-30 | 1960-02-29 | Cfmc | Nouveau procédé de chromage de colorants azoïques et nouveaux colorants chromifères en résultant |
| FR1518833A (fr) * | 1967-02-10 | 1968-03-29 | Ugine Kuhlmann | Nouveaux complexes métallifères mixtes |
-
1974
- 1974-01-17 CH CH61774A patent/CH589126A5/xx not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR257306A patent/AR207461A1/es active
- 1975-01-03 NL NL7500077A patent/NL7500077A/xx not_active Application Discontinuation
- 1975-01-14 FR FR7500958A patent/FR2258431B1/fr not_active Expired
- 1975-01-15 DE DE2501449A patent/DE2501449C2/de not_active Expired
- 1975-01-15 BR BR264/75A patent/BR7500264A/pt unknown
- 1975-01-15 IT IT47680/75A patent/IT1026342B/it active
- 1975-01-15 CA CA75217945A patent/CA1049001A/en not_active Expired
- 1975-01-16 ZA ZA00750315A patent/ZA75315B/xx unknown
- 1975-01-16 GB GB1935/75A patent/GB1493474A/en not_active Expired
- 1975-01-16 ES ES433862A patent/ES433862A1/es not_active Expired
- 1975-01-16 AU AU77362/75A patent/AU7736275A/en not_active Expired
- 1975-01-17 JP JP50007197A patent/JPS5837341B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2501449A1 (de) | 1975-07-24 |
| JPS5837341B2 (ja) | 1983-08-16 |
| IT1026342B (it) | 1978-09-20 |
| GB1493474A (en) | 1977-11-30 |
| ZA75315B (en) | 1976-01-28 |
| ES433862A1 (es) | 1976-12-01 |
| BR7500264A (pt) | 1975-11-04 |
| AR207461A1 (es) | 1976-10-08 |
| FR2258431B1 (en, 2012) | 1977-07-01 |
| NL7500077A (nl) | 1975-07-21 |
| CH589126A5 (en, 2012) | 1977-06-30 |
| JPS50102623A (en, 2012) | 1975-08-14 |
| AU7736275A (en) | 1976-07-22 |
| FR2258431A1 (en, 2012) | 1975-08-18 |
| DE2501449C2 (de) | 1983-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1059997A (en) | Chromium complex dyes, their manufacture and use | |
| US4234479A (en) | Chromium mixed complex dyestuffs of phenyl-azo-pyrazole components | |
| CA1049001A (en) | Chromium complex dyes, their manufacture and use | |
| US5008379A (en) | Chromium complexes of sulfo group containing disazo compounds having a resorcinol biscoupling component radical | |
| US3468871A (en) | Metal-containing monoazo dyestuffs | |
| US4083839A (en) | Unsymmetrical mono sulfo containing 1:2 azo, azo chromium complex dyes | |
| US3970615A (en) | Unsymmetrical mono-sulfo containing chromium complexes of azo dyes | |
| CA1049000A (en) | Chromium complex dyes, their manufacture and use | |
| US4053462A (en) | Unsymmetrical phenyl azo naphthyl chromium complex dyes | |
| US4248773A (en) | Acetoacetamide diazo dyestuffs | |
| US4996303A (en) | Preparation of 1:2 metal complex dyes by coupling in the presence of a metal donor in an inert gas atmosphere | |
| DE2835493C2 (de) | Chromkomplexfarbstoffe | |
| US4499015A (en) | Chromium complex azo dyestuffs and mixtures of chromium complex azo dyestuffs derivated from 1-amino-2-hydroxynaphtalene-4-sulphonic acids or aminophenols | |
| US3925346A (en) | Mixed chromium-containing azo dyestuffs containing, per atom of chromium, one molecule of an o,o'-dihydroxy-sulphophenylene-azo-naphthalene and one molecule of an -o-hydroxyphenylene-azo-acetoacetamide | |
| US4113719A (en) | 1:2-Cobalt-complex azo dyestuffs having an acetoacetylamino diphenylamino coupler | |
| US3511827A (en) | Metallized monoazo dye for nylon | |
| US3502642A (en) | Reactive copper-containing benzeneazonaphthalene dyes containing a trichloropyrimidine group | |
| CA1047486A (en) | Chromium complex dye, its manufacture and use | |
| US4443370A (en) | Chrome-complex dyes | |
| CA1159051A (en) | Fibre-reactive chromium complex dyes, process for their production and use thereof | |
| US3169951A (en) | Chromhjm-containing azo dyestuffs | |
| US3163634A (en) | Dyestuffs containing metal in complex combination | |
| US4013630A (en) | Chromium complex disazo dyes | |
| US2709698A (en) | Azo dyes derived from hydroquinone mono-ethers | |
| US4029643A (en) | Chromium containing azo dyes |