GB1086994A - Monazo heterocyclic dyes, cationic derivatives thereof, and their use - Google Patents
Monazo heterocyclic dyes, cationic derivatives thereof, and their useInfo
- Publication number
- GB1086994A GB1086994A GB2916865A GB2916865A GB1086994A GB 1086994 A GB1086994 A GB 1086994A GB 2916865 A GB2916865 A GB 2916865A GB 2916865 A GB2916865 A GB 2916865A GB 1086994 A GB1086994 A GB 1086994A
- Authority
- GB
- United Kingdom
- Prior art keywords
- unsubstituted
- acid
- substituted
- groups
- alkyl
- 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 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 2
- 125000002091 cationic group Chemical group 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- -1 5-amino-pyrazole compound Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 abstract 1
- 150000003842 bromide salts Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 125000003010 ionic group Chemical group 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
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/14—1,2-Diazoles or hydrogenated 1,2-diazoles ; Pyrazolium; Indazolium
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
Pyrazole monoazo dyes are obtained by diazotizing a 5-amino-pyrazole compound of tautomeric formulae <FORM:1086994/C4-C5/1> with nitrosyl sulphuric acid and coupling with an aromatic amine in para-position to the amino group to form a dye of formula <FORM:1086994/C4-C5/2> and reacting this with the ester of an unsubstituted or non-ionogenically substituted alkanol with an inorganic or organic acid to form a cyclammonium compound of formula <FORM:1086994/C4-C5/3> In the above formula R1 is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical which contains no groups which dissociate acid in neutral water, R2 is an alkyl, carbalkoxy, or an N-substituted or N-unsubstituted carboxylic acid amide radical, each of R3 and R4 is hydrogen or an unsubstituted or substituted alkyl, cycloalkyl or aryl radical containing no groups which dissociate acid in neutral water or R3 and R4 together with the nitrogen atom represent a non-aromatic heterocycle, Ar is an unsubstituted or substituted p-arylene radical of the benzene or naphthalene series containing no groups which dissociate acid in water whilst any substituent of Ar in a position adjacent the -NR3R4 group can take part with R3 and R4 in forming a heterocycle, R5 is an alkyl group which may contain non-ionic groups and X- is an anion of an inorganic or organic acid. The reaction of the monoazo dye with the alkanol ester is preferably performed by heating in an inert organic solvent, e.g. halogenated or nitrated hydrocarbons, the cyclammonium compounds being produced as salts, especially chlorides, bromides, iodides, metho- and etho-sulphates, bisulphates, benzene sulphonates or p-toluene sulphonates. The dyes give orange-red shades on polyacrylonitrile fibres.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH904564A CH442569A (en) | 1964-07-10 | 1964-07-10 | Process for the preparation of cationic azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1086994A true GB1086994A (en) | 1967-10-11 |
Family
ID=4347715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2916865A Expired GB1086994A (en) | 1964-07-10 | 1965-07-09 | Monazo heterocyclic dyes, cationic derivatives thereof, and their use |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH442569A (en) |
| DE (1) | DE1544579B1 (en) |
| GB (1) | GB1086994A (en) |
| NL (1) | NL130779C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119622A (en) * | 1975-12-20 | 1978-10-10 | Basf Aktiengesellschaft | Pyrazolonylazoaniline or aminonaphtyl compounds for copying processes |
| US4308205A (en) * | 1976-11-17 | 1981-12-29 | Montedison S.P.A. | Water-soluble monoazo cationic dyestuffs derived from 1-phenyl-3-aminopyrazoles |
| GB2168713A (en) * | 1984-12-20 | 1986-06-25 | Ciba Geigy Ag | Cationic pyrazole-azo dyestuffs |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101540A (en) * | 1975-09-30 | 1978-07-18 | Produits Chimiques Ugine Kuhlmann | 3-Trifluoromethyl-4-phenyl-pyrazolium azo dyestuffs |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT555665B (en) * | 1955-01-28 | |||
| FR1151304A (en) * | 1955-06-14 | 1958-01-29 | Basf Ag | Process for the production of basic azo dyes |
| FR1274223A (en) * | 1960-11-25 | 1961-10-20 | American Cyanamid Co | Dyes which are azo compounds of quaternary imidazolium salts |
-
0
- NL NL130779D patent/NL130779C/xx active
-
1964
- 1964-07-10 CH CH904564A patent/CH442569A/en unknown
-
1965
- 1965-07-09 DE DE19651544579 patent/DE1544579B1/en not_active Withdrawn
- 1965-07-09 GB GB2916865A patent/GB1086994A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119622A (en) * | 1975-12-20 | 1978-10-10 | Basf Aktiengesellschaft | Pyrazolonylazoaniline or aminonaphtyl compounds for copying processes |
| US4308205A (en) * | 1976-11-17 | 1981-12-29 | Montedison S.P.A. | Water-soluble monoazo cationic dyestuffs derived from 1-phenyl-3-aminopyrazoles |
| GB2168713A (en) * | 1984-12-20 | 1986-06-25 | Ciba Geigy Ag | Cationic pyrazole-azo dyestuffs |
| FR2575169A1 (en) * | 1984-12-20 | 1986-06-27 | Ciba Geigy Ag | AZOPYRAZOL CATIONIC COMPOUNDS |
| DE3544574A1 (en) * | 1984-12-20 | 1986-07-10 | Ciba-Geigy Ag, Basel | Cationic pyrazole azo compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1544579B1 (en) | 1970-08-27 |
| NL130779C (en) | |
| CH442569A (en) | 1967-08-31 |
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