DE1644192A1 - Chrom-Mischkomplex-Azofarbstoffe - Google Patents
Chrom-Mischkomplex-AzofarbstoffeInfo
- Publication number
- DE1644192A1 DE1644192A1 DE19671644192 DE1644192A DE1644192A1 DE 1644192 A1 DE1644192 A1 DE 1644192A1 DE 19671644192 DE19671644192 DE 19671644192 DE 1644192 A DE1644192 A DE 1644192A DE 1644192 A1 DE1644192 A1 DE 1644192A1
- Authority
- DE
- Germany
- Prior art keywords
- chromium
- dyes
- dye
- aminobenzene
- complex
- 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.)
- Pending
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 21
- 229910052804 chromium Inorganic materials 0.000 title claims description 21
- 239000011651 chromium Substances 0.000 title claims description 19
- 239000000987 azo dye Substances 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 41
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 150000003931 anilides Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- LSDJWPOITYCHHU-UHFFFAOYSA-N 2-amino-4-sulfamoylbenzoic acid Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1C(O)=O LSDJWPOITYCHHU-UHFFFAOYSA-N 0.000 description 3
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 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
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- ITUBXYGHGAJZAX-UHFFFAOYSA-N 5-ethyl-2-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC(CC)=NN1C1=CC=CC=C1 ITUBXYGHGAJZAX-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 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 |
|---|---|---|---|
| DEF0051352 | 1967-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1644192A1 true DE1644192A1 (de) | 1971-07-15 |
Family
ID=7104535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671644192 Pending DE1644192A1 (de) | 1967-01-26 | 1967-01-26 | Chrom-Mischkomplex-Azofarbstoffe |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3625937A (en, 2012) |
| BE (1) | BE709915A (en, 2012) |
| CH (3) | CH487985A (en, 2012) |
| DE (1) | DE1644192A1 (en, 2012) |
| FR (1) | FR1558605A (en, 2012) |
| GB (1) | GB1162084A (en, 2012) |
| NL (1) | NL6800947A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3939140A (en) * | 1971-04-23 | 1976-02-17 | Hoechst Aktiengesellschaft | Process for the preparation of a dyestuff consisting substantially of only unsymmetrical 1:2-chromium complex azo dyestuffs |
| US3880797A (en) * | 1973-08-10 | 1975-04-29 | Hodogaya Chemical Co Ltd | Process for preparing colored polyurethane |
| IT1031222B (it) * | 1974-01-30 | 1979-04-30 | Bayer Ag | Coloranti complessi metallici |
| US4340536A (en) * | 1979-05-23 | 1982-07-20 | Ciba-Geigy Corporation | Chrome-complex dyes and the production and use thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3221003A (en) * | 1965-11-30 | Chrgmium cqmplex mixed azo dyestuffs | ||
| US3067191A (en) * | 1962-12-04 | chschohchaoh | ||
| US3213079A (en) * | 1963-01-18 | 1965-10-19 | Sandoz Ltd | Metallized pyrazolone azo dyes |
| 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 |
| CH405549A (de) * | 1961-08-22 | 1966-01-15 | Sandoz Ag | Verfahren zur Herstellung von Azofarbstoffen |
| DE1444655C3 (de) * | 1963-02-19 | 1974-08-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2:1-Chrommischkomplex-Azofarbstoffen |
-
1967
- 1967-01-26 DE DE19671644192 patent/DE1644192A1/de active Pending
- 1967-12-22 CH CH1804067A patent/CH487985A/de not_active IP Right Cessation
- 1967-12-22 CH CH95070A patent/CH519052A/de not_active IP Right Cessation
- 1967-12-22 CH CH95070D patent/CH95070A4/xx unknown
-
1968
- 1968-01-19 US US699021A patent/US3625937A/en not_active Expired - Lifetime
- 1968-01-22 NL NL6800947A patent/NL6800947A/xx unknown
- 1968-01-23 GB GB3438/68A patent/GB1162084A/en not_active Expired
- 1968-01-26 FR FR1558605D patent/FR1558605A/fr not_active Expired
- 1968-01-26 BE BE709915D patent/BE709915A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH519052A (de) | 1972-02-15 |
| US3625937A (en) | 1971-12-07 |
| BE709915A (en, 2012) | 1968-05-30 |
| CH95070A4 (en, 2012) | 1971-10-29 |
| CH487985A (de) | 1970-03-31 |
| FR1558605A (en, 2012) | 1969-02-28 |
| GB1162084A (en) | 1969-08-20 |
| NL6800947A (en, 2012) | 1968-07-29 |
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