JPS5943500B2 - 非対称型１：２クロム錯塩染料 - Google Patents
非対称型１：２クロム錯塩染料Info
- Publication number
- JPS5943500B2 JPS5943500B2 JP51100706A JP10070676A JPS5943500B2 JP S5943500 B2 JPS5943500 B2 JP S5943500B2 JP 51100706 A JP51100706 A JP 51100706A JP 10070676 A JP10070676 A JP 10070676A JP S5943500 B2 JPS5943500 B2 JP S5943500B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chlorine
- group
- hydrogen
- dye according
- 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 16
- 229910052804 chromium Inorganic materials 0.000 title claims description 16
- 239000011651 chromium Substances 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000011734 sodium 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 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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 1
- 239000000975 dye Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000004043 dyeing Methods 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 8
- -1 di-substituted phenyl Chemical group 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920002647 polyamide Polymers 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001844 chromium Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4h-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 1
- YCTAOQGPWNTYJE-UHFFFAOYSA-N 3-amino-5-chloro-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC(S(O)(=O)=O)=C1O YCTAOQGPWNTYJE-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 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
- 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
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229960004042 diazoxide Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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 |
|---|---|---|---|
| CH1109975A CH616953A5 (en, 2012) | 1975-08-27 | 1975-08-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5228522A JPS5228522A (en) | 1977-03-03 |
| JPS5943500B2 true JPS5943500B2 (ja) | 1984-10-22 |
Family
ID=4370043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51100706A Expired JPS5943500B2 (ja) | 1975-08-27 | 1976-08-25 | 非対称型１：２クロム錯塩染料 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4618673A (en, 2012) |
| JP (1) | JPS5943500B2 (en, 2012) |
| AR (1) | AR210896A1 (en, 2012) |
| AU (1) | AU504714B2 (en, 2012) |
| BE (1) | BE845508A (en, 2012) |
| BR (1) | BR7605627A (en, 2012) |
| CA (1) | CA1070297A (en, 2012) |
| CH (1) | CH616953A5 (en, 2012) |
| DE (1) | DE2636798C2 (en, 2012) |
| ES (1) | ES451017A1 (en, 2012) |
| FR (1) | FR2322179A1 (en, 2012) |
| GB (1) | GB1551799A (en, 2012) |
| HK (1) | HK30380A (en, 2012) |
| IT (1) | IT1065824B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000331B1 (de) * | 1977-06-23 | 1983-12-28 | Ciba-Geigy Ag | Verfahren zum Färben linearer Polyamide in der Masse mit Salzen von 1:2 Chromkomplex-monoazofarbstoffen; die damit erzeugten Fasern |
| FR2525226A1 (fr) * | 1982-04-16 | 1983-10-21 | Ici Francolor | Nouveaux complexes de chrome de colorants, leur preparation et leur utilisation |
| DE4130806A1 (de) * | 1991-09-17 | 1993-03-18 | Bayer Ag | Unsymmetrische 1:2-chromkomplexfarbstoffe |
| AU762999B2 (en) | 1998-08-14 | 2003-07-10 | Clariant Finance (Bvi) Limited | 1:2 chromium complex dyes, their production and use |
| US6235100B1 (en) * | 1999-06-24 | 2001-05-22 | Engelhard Corporation | Metallized azo yellow pigments |
| GB0123150D0 (en) | 2001-09-27 | 2001-11-21 | Clariant Int Ltd | Organic compounds |
| WO2007009966A2 (en) * | 2005-07-21 | 2007-01-25 | Clariant International Ltd | Chromium complex dyes |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2673201A (en) * | 1954-03-23 | Cobaltiferous azo-dyestuffs | ||
| US2906746A (en) * | 1959-09-29 | Metalliferous azo dyestuffs | ||
| US3041327A (en) * | 1962-06-26 | Chj sojh | ||
| 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 |
| DE2500550C2 (de) * | 1974-01-10 | 1983-11-03 | CIBA-GEIGY AG, 4002 Basel | Neue Chromkomplexfarbstoffe, deren Herstellung und Verwendung |
| US3062806A (en) * | 1959-08-07 | 1962-11-06 | Geigy Ag J R | 1:2-metal complexes of monoazo dyes containing a 1, 2-diphenyl-3, 5-diketopyrazolidine coupling component |
| DE1151078B (de) * | 1960-01-13 | 1963-07-04 | Wolfen Filmfab Veb | Verfahren zur Herstellung chromhaltiger Azofarbstoffkomplex-verbindungen |
| DE1271857B (de) * | 1962-10-17 | 1968-07-04 | Ciba Geigy | Verfahren zur Herstellung chromhaltiger Azofarbstoffe |
| BE638749A (en, 2012) * | 1963-10-11 | |||
| FR1518833A (fr) * | 1967-02-10 | 1968-03-29 | Ugine Kuhlmann | Nouveaux complexes métallifères mixtes |
| JPS4952219A (en, 2012) * | 1972-09-18 | 1974-05-21 | ||
| CH583285A5 (en, 2012) * | 1974-01-15 | 1976-12-31 | Ciba Geigy Ag | |
| US4083839A (en) * | 1974-01-15 | 1978-04-11 | Ciba-Geigy Corporation | Unsymmetrical mono sulfo containing 1:2 azo, azo chromium complex dyes |
| CH589126A5 (en, 2012) * | 1974-01-17 | 1977-06-30 | Ciba Geigy Ag | |
| CH593323A5 (en, 2012) * | 1974-01-30 | 1977-11-30 | Ciba Geigy Ag | |
| IT1031222B (it) * | 1974-01-30 | 1979-04-30 | Bayer Ag | Coloranti complessi metallici |
| FR2271267B1 (en, 2012) * | 1974-02-06 | 1976-10-08 | Ugine Kuhlmann | |
| DE2408224A1 (de) * | 1974-02-21 | 1975-10-02 | Bayer Ag | Azochrommischkomplex-farbstoffe |
| FR2300779A1 (fr) * | 1975-02-13 | 1976-09-10 | Ugine Kuhlmann | Procede pour l |
-
1975
- 1975-08-27 CH CH1109975A patent/CH616953A5/de not_active IP Right Cessation
-
1976
- 1976-08-12 FR FR7624658A patent/FR2322179A1/fr active Granted
- 1976-08-16 DE DE2636798A patent/DE2636798C2/de not_active Expired
- 1976-08-25 AR AR264455A patent/AR210896A1/es active
- 1976-08-25 JP JP51100706A patent/JPS5943500B2/ja not_active Expired
- 1976-08-25 BE BE170068A patent/BE845508A/xx not_active IP Right Cessation
- 1976-08-25 CA CA259,829A patent/CA1070297A/en not_active Expired
- 1976-08-26 ES ES451017A patent/ES451017A1/es not_active Expired
- 1976-08-26 GB GB35514/76A patent/GB1551799A/en not_active Expired
- 1976-08-26 AU AU17206/76A patent/AU504714B2/en not_active Expired
- 1976-08-26 BR BR7605627A patent/BR7605627A/pt unknown
- 1976-08-27 IT IT26636/76A patent/IT1065824B/it active
-
1980
- 1980-06-05 HK HK303/80A patent/HK30380A/xx unknown
-
1981
- 1981-09-22 US US06/304,621 patent/US4618673A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK30380A (en) | 1980-06-13 |
| DE2636798A1 (de) | 1977-03-03 |
| AR210896A1 (es) | 1977-09-30 |
| BE845508A (fr) | 1977-02-25 |
| JPS5228522A (en) | 1977-03-03 |
| ES451017A1 (es) | 1978-10-16 |
| AU504714B2 (en) | 1979-10-25 |
| CH616953A5 (en, 2012) | 1980-04-30 |
| CA1070297A (en) | 1980-01-22 |
| AU1720676A (en) | 1978-03-02 |
| BR7605627A (pt) | 1977-08-09 |
| FR2322179A1 (fr) | 1977-03-25 |
| FR2322179B1 (en, 2012) | 1980-05-09 |
| IT1065824B (it) | 1985-03-04 |
| DE2636798C2 (de) | 1984-07-12 |
| US4618673A (en) | 1986-10-21 |
| GB1551799A (en) | 1979-08-30 |
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