GB955520A - Improvements relating to monoazo aminopyrazole dyestuffs and their use - Google Patents
Improvements relating to monoazo aminopyrazole dyestuffs and their useInfo
- Publication number
- GB955520A GB955520A GB239962D GB239962D GB955520A GB 955520 A GB955520 A GB 955520A GB 239962 D GB239962 D GB 239962D GB 239962 D GB239962 D GB 239962D GB 955520 A GB955520 A GB 955520A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- diazonium compounds
- water
- group
- diazonium
- 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
- -1 monoazo aminopyrazole Chemical compound 0.000 title abstract 2
- 239000000975 dye Substances 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 3
- 150000001989 diazonium salts Chemical class 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 230000003381 solubilizing effect Effects 0.000 abstract 2
- WFVVYUPKAADCGR-UHFFFAOYSA-N 1h-indazole-3-diazonium Chemical class C1=CC=C2C([N+]#N)=NNC2=C1 WFVVYUPKAADCGR-UHFFFAOYSA-N 0.000 abstract 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract 1
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 abstract 1
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 abstract 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 abstract 1
- QPYWEQFKRCJSAD-UHFFFAOYSA-N CS(=O)(=O)OC1=CC=CC2=CC=CC=C12.[Na].[Na] Chemical compound CS(=O)(=O)OC1=CC=CC2=CC=CC=C12.[Na].[Na] QPYWEQFKRCJSAD-UHFFFAOYSA-N 0.000 abstract 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical group N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- LPTIRUACFKQDHZ-UHFFFAOYSA-N hexadecyl sulfate;hydron Chemical compound CCCCCCCCCCCCCCCCOS(O)(=O)=O LPTIRUACFKQDHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 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 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 235000010292 orthophenyl phenol Nutrition 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 abstract 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003536 tetrazoles Chemical class 0.000 abstract 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
Abstract
1 - (b - hydroxy - b - phenylethyl) - 3 - methyl-5-aminopyrazole, for use in the production of azo dyes (see Division C4) is obtained by reacting styrene oxide with hydrazine in a molar ratio of about 1:1 followed by condensation of the b -hydroxy-b -phenylethyl-hydrazine formed with cyanacetone imine.ALSO:The invention comprises a monoazo dye of the formula <FORM:0955520/C3/1> wherein A represents the radical of an isocyclic or heterocyclic diazo component which contains no metallizable group in o-position to the azo group, which dyestuff is free from water solubilizing groups which dissociate acid in water. In particular A represents a benzene radical which contains no metallizable group in o-position to the azo group but contains at least one electrophilic substituent in o- or p-position to the azo group. The dyes are obtained by reacting an appropriate diazonium compound with a 5-amino pyrazole which couples in the 4-position, the components being chosen so that the product contains no water solubilizing groups which dissociate acid in water. Diazonium compounds specified include benzene diazonium compounds substituted with halogen, trifluoromethyl, nitro, cyano, alkyl sulphonyl, sulphamyl groups optionally substituted at the nitrogen atom and such heterocyclic compounds as thiazole, benzthiazole, thiadiazole, triazole, tetrazole and indazole diazonium compounds. The diazonium compounds used in examples are prepared from 2,4-dinitro-; 2-nitro-4-ethyl-sulphonyl-; 4-nitro-; 2-nitro-4-sulphonamide-; 2 - chloro - 4 - nitro - and - 2,6 - dichloro - 4 - nitro - 1 - aminobenzenes, 2 - amino - 5 - nitro-thiazole and 2-aminobenzthiazole. The products milled with such dispersing agents as disodium naphthyl methane sulphonate, sodium dodecylbenzene sulphonate, sodium diisobutyl naphthalene sulphonate or hexadecyl sulphate and are employed in aqueous dispersions with the addition of carriers such as o-phenylphenol to dye terephthalic polyester fibres.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH239961A CH454305A (en) | 1959-09-11 | 1961-02-28 | Process for the production of water-dispersible, sparingly soluble azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB955520A true GB955520A (en) | 1964-04-15 |
Family
ID=4232860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB239962D Expired GB955520A (en) | 1961-02-28 | 1962-02-27 | Improvements relating to monoazo aminopyrazole dyestuffs and their use |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE614461R (en) |
| DE (1) | DE1444674A1 (en) |
| ES (1) | ES275193A2 (en) |
| GB (1) | GB955520A (en) |
-
1962
- 1962-02-27 GB GB239962D patent/GB955520A/en not_active Expired
- 1962-02-27 BE BE614461A patent/BE614461R/en active
- 1962-02-27 DE DE19621444674 patent/DE1444674A1/en active Pending
- 1962-02-27 ES ES0275193A patent/ES275193A2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES275193A2 (en) | 1962-10-16 |
| BE614461R (en) | 1962-09-28 |
| DE1444674A1 (en) | 1968-11-07 |
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