CH511879A - Basic azo dyestuffs - Google Patents
Basic azo dyestuffsInfo
- Publication number
- CH511879A CH511879A CH474668A CH474668A CH511879A CH 511879 A CH511879 A CH 511879A CH 474668 A CH474668 A CH 474668A CH 474668 A CH474668 A CH 474668A CH 511879 A CH511879 A CH 511879A
- Authority
- CH
- Switzerland
- Prior art keywords
- series
- coupling
- alkyl
- cycloalkyl
- heterocyclic
- Prior art date
Links
- 230000008878 coupling Effects 0.000 claims abstract description 10
- 238000010168 coupling process Methods 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 150000005204 hydroxybenzenes Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical class S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 alkyl amides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- WLODWTPNUWYZKN-UHFFFAOYSA-N 1h-pyrrol-2-ol Chemical class OC1=CC=CN1 WLODWTPNUWYZKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Paper (AREA)
Abstract
Dyestuffs of formula (I) where X1 is the residue of a coupling component of the amino- or hydroxybenzene series, the heterocyclic series, the amino- or hydroxynaphthalene series or with a methylene group capable of coupling, Y is a direct bond or a divalent bridging group, p is 0-3 A is an anion and K1 is where R' and R" are (subst) alkyl or cycloalkyl or together form a heterocyclic group1 R3 and R4 are H, (substituted) alkyl, cycloalkyl or acyl, R8, R9 and R10 are (substituted) alkyl or cycloalkyl or can make a heterocyclic ring as can R' with R3 and/or R" with R4 are prepared by coupling an amine with a coupling component H-X1-Y-K1 circled positive. The dyestuff may be used for paper and polyacrylonitrile textile material.
Description
Verfahren zur Herstellung von Verbindungen der Dehydrothiotoluidinreihe
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Verbindungen der Dehydrothiotoluidinreihe der Formel
EMI1.1
worin X den Rest einer Kupplungskomponente, n 1 bis 6, und A den Säurerest eines Esters, vorzugsweise ein Halo genatom, bedeuten und die aromatischen Ringe B und/oder D weitersubstituiert sein können, dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2
nach an sich bekannten Methoden, mit Halogenmethyl abgebenden Verbindungen umsetzt, vorzugsweise chlor methyliert.
Die Ringe B und/oder D können vorteilhaft durch nicht wasserlöslich machende Substituenten substituiert sein.
Vorzugsweise enthalten sie Halogenatome, die Hydroxy-, Nitro- oder Cyangruppe, gegebenenfalls sub stituierte Alkyl- oder Alkoxygruppen oder Hydroxy aryl- oder Alkoxyarylgruppen. Die Verbindungen (I) können aber auch eine Sulfonsäure- oder Carbonsäure gruppe oder eine Sulfonsäureamid- oder Carbonsäure amidgruppe oder eine Alkyl- oder Arylsulfonylgruppe enthalten.
Die Kupplungskomponenten gehören beispielsweise der aromatischen Reihe an, z. B. der Benzol- oder
Naphthalinreihe, die einen die Kupplung ermöglichen
Substituenten tragen, z. B. Amino- oder Hydroxy azole, Amino- oder Hydroxynaphthaline; aber auch
Kupplungskomponenten der heterocyclischen Reihe, wie der Pyrazolon- oder Aminopyrazolreihe oder der Al kan-, Alken- oder Alkinreihe mit einer kupplungsfähigen Methylengruppe können eingesetzt werden, z. B.
l-Phenyl-3-methyl-pyrazolon-5 und Derivate davon oder Acylessigsäure-aryl- oder alkylamide, usw.
Die Verbindungen der Formel (I) können als Zwischenprodukte für die Herstellung von Farbstoffen verwendet werden. In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben.
Beispiel
24 Teile 2-(4'-Aminophenyl)-6-methylbenzthiazol werden in salzsaurer Lösung mit 7 Teilen Natriumnitrit diazotiert. Die Diazoniumlösung wird in essigsaurer Lösung mit 15 Teilen 2-Hydroxynaphthalin gekuppelt.
Die so erhaltene Monoazoverbindung wird in einem Gemisch, bestehend aus 100 Teilen Chlorsulfonsäure und 35 Teilen Schwefelsäure gelöst und mit 20 Teilen Paraformaldehyd versetzt. Man rührt 12 Stunden lang bei 60 und erhält das chlormethylierte Produkt.
Process for the preparation of compounds of the dehydrothiotoluidine series
The invention relates to a process for the preparation of compounds of the dehydrothiotoluidine series of the formula
EMI1.1
wherein X is the radical of a coupling component, n 1 to 6, and A is the acid radical of an ester, preferably a halogen atom, and the aromatic rings B and / or D can be further substituted, characterized in that a compound of the formula
EMI1.2
by methods known per se, reacted with halogenomethyl-releasing compounds, preferably chloromethylated.
The rings B and / or D can advantageously be substituted by non-water-solubilizing substituents.
They preferably contain halogen atoms, the hydroxyl, nitro or cyano group, optionally substituted alkyl or alkoxy groups or hydroxy aryl or alkoxyaryl groups. The compounds (I) can, however, also contain a sulfonic acid or carboxylic acid group or a sulfonic acid amide or carboxylic acid amide group or an alkyl or arylsulfonyl group.
The coupling components belong, for example, to the aromatic series, e.g. B. the benzene or
Naphthalene series that enable a coupling
Carry substituents, e.g. B. amino or hydroxy azoles, amino or hydroxynaphthalenes; but also
Coupling components of the heterocyclic series, such as the pyrazolone or aminopyrazole series or the alkane, alkene or alkyne series with a methylene group capable of coupling can be used, for. B.
l-phenyl-3-methyl-pyrazolone-5 and derivatives thereof or acyl acetic acid aryl or alkyl amides, etc.
The compounds of the formula (I) can be used as intermediates for the preparation of dyes. In the following examples, the parts are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius.
example
24 parts of 2- (4'-aminophenyl) -6-methylbenzthiazole are diazotized in hydrochloric acid solution with 7 parts of sodium nitrite. The diazonium solution is coupled with 15 parts of 2-hydroxynaphthalene in acetic acid solution.
The monoazo compound thus obtained is dissolved in a mixture consisting of 100 parts of chlorosulfonic acid and 35 parts of sulfuric acid, and 20 parts of paraformaldehyde are added. The mixture is stirred for 12 hours at 60 and the chloromethylated product is obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH474668A CH511879A (en) | 1968-01-24 | 1968-01-24 | Basic azo dyestuffs |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH474668A CH511879A (en) | 1968-01-24 | 1968-01-24 | Basic azo dyestuffs |
| CH102368A CH513953A (en) | 1968-01-24 | 1968-01-24 | Prepn of azo dyes - for textile materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH511879A true CH511879A (en) | 1971-08-31 |
Family
ID=4200639
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH474668A CH511879A (en) | 1968-01-24 | 1968-01-24 | Basic azo dyestuffs |
| CH1177470A CH511880A (en) | 1968-01-24 | 1968-01-24 | Basic azo dyestuffs |
| CH1189270A CH528577A (en) | 1968-01-24 | 1968-01-24 | Prepn of azo dyes - for textile materials |
| CH102368A CH513953A (en) | 1968-01-24 | 1968-01-24 | Prepn of azo dyes - for textile materials |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1177470A CH511880A (en) | 1968-01-24 | 1968-01-24 | Basic azo dyestuffs |
| CH1189270A CH528577A (en) | 1968-01-24 | 1968-01-24 | Prepn of azo dyes - for textile materials |
| CH102368A CH513953A (en) | 1968-01-24 | 1968-01-24 | Prepn of azo dyes - for textile materials |
Country Status (1)
| Country | Link |
|---|---|
| CH (4) | CH511879A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015233B1 (en) * | 1979-02-02 | 1984-03-07 | Ciba-Geigy Ag | Process for dyeing cellulose-containing fibrous materials |
-
1968
- 1968-01-24 CH CH474668A patent/CH511879A/en not_active IP Right Cessation
- 1968-01-24 CH CH1177470A patent/CH511880A/en not_active IP Right Cessation
- 1968-01-24 CH CH1189270A patent/CH528577A/en not_active IP Right Cessation
- 1968-01-24 CH CH102368A patent/CH513953A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH511880A (en) | 1971-08-31 |
| CH528577A (en) | 1972-09-30 |
| CH513953A (en) | 1971-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |