GB543567A - Manufacture of azo-dyestuffs - Google Patents
Manufacture of azo-dyestuffsInfo
- Publication number
- GB543567A GB543567A GB8447/40A GB844740A GB543567A GB 543567 A GB543567 A GB 543567A GB 8447/40 A GB8447/40 A GB 8447/40A GB 844740 A GB844740 A GB 844740A GB 543567 A GB543567 A GB 543567A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aniline
- methyl
- chloro
- pyrazolone
- phenyl
- 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
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
- C09B29/34—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
Abstract
543,567. Dyes ; dyeing ; ; artificial filaments ; cellulose derivative compositions. SOC. OF CHEMICAL INDUSTRY IN BASLE. May 10, 1940, Nos. 8447 and 8448. Convention dates, May 11, 1939 and April 23, 1940. [Classes 2 (ii), 2 (iii) and 15 (ii)] Monoazo dyes readily soluble in organic solvents are produced in substance or on the material to be dyed by coupling a 1-aryl-3- methyl-5-pyrazolone in which the aryl group is of the benzene series with a diazotized amine of the general formula any further substituents in either of the benzene nuclei being non-ionogenic and other than nitro groups. Specified non-ionogenic substituents are methyl and O-alkyl groups and halogen atoms: Specified diazo components are aniline-2-, 3- and 4-#-hydroxyethylsulphonamides, aniline - 4 - chloro - 3 - # - hydroxyethylsulphonamide and aniline-2-methyl-5-#- hydroxyethylsulphonamide. Specified coupling components are the 1-pbenyl-, 1-(o- and pmethyl) phenyl-, 1-(o-, m- and p-chloro) phenyl- and 1-(o-methoxy) phenyl-derivatives of 3- methyl-5-pyrazolone.. The products obtained in substance are suitable for use as pigments, e.g. for colouring lacquers and masses from which cellulose acetate artificial silk is spun, and for dyeing cellulose acetate artificial silk. Example (1) relates to the production of the dyestuffs, aniline-3-#-hydroxyethylsulphon - amide or aniline-2-chloro-4-#-hydroxyethylsulphonamide # 1-(o-chloro) phenyl-3-methyl-5- pyrazolone, aniline-2-#-hydroxyethylsulphon - amide # 1-(o-methyl) phenyl-3-methyl-5-pyrazolone, and aniline-3-#-hydroxyethylsulphonamide # 1-phenyl-3-methyl-5-pyrazolone. Example (2) relates to the incorporation of the dyestuff, pasted with ethylene glycol monomethyl ether, in a nitrocellulose lacquer. Example (3) relates to the formation of a film from a solution made by stirring a solution of the dyestuff in ethylene glycol monomethyl ether into an acetone solution of acetylcellulose. Specification 12205/09, [Class 2 (iii)], is referred to. Aniline-#-hydroxyethylsulphonamides of the above general formula are obtained by reducing the nitro group in the products of reaction of the corresponding nitrobenzene sulphonic acid chlorides with ethanolamine. The Specification as open to inspection under Sect. 91 comprises also the production of azo dyestuffs by coupling a similar 1-aryl-3-methyl- 5-pyrazolone which may, however, be nitrosubstituted. with a similar diazotized amine of the general formula which may also however, be nitro-substituted, wherein R is any aliphatic residue containing 2 carbon atoms of which the α-carbon atom carries 2 hydrogen atoms and the #-carbon atom carries a hydroxyl group. Additional diazo components specified are aniline-2-, 3- or 4-#-hydroxyethylsulphone, aniline-2-chloro- or nitro-4-#-hydroxyethylsulphone, aniline - 4 - chloro-2-#-hydroxyethylsulphone, aniline-2-, 3- or 4 - sulphonic acid - # - hydroxyethyl ester, aniline - 2 - chloro - 4 - sulphonic acid - # - hydroxyethyl ester and aniline-3-N-methyl- or ethyl-N-#-hydroxyethylsulphonamide, and additional examples of the production of dyestuffs from various combinations of the components are given. Aniline-#-hydroxyethsulphones of the above general formula are obtained by reducing the nitro group (a) in the product of reaction with a #-halogenethanol of the sulphinic acid obtained by reduction of the corresponding nitrobenzenesulphonic acid chloride, (b) in the product, obtained by oxidizing the thioether obtained by reaction of #-chloroethanol with a nitrothiophenol obtainable by replacement of the halogen in a nitrohalogenbenzene by the thiol group. Aniline sulphonic acid-#-hydroxyethyl esters of the above general formula are obtained by reducing the nitro group in the product of reaction of the corresponding nitrobenzenesulphonic acid chloride with ethylene glycol. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH543567X | 1939-05-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB543567A true GB543567A (en) | 1942-03-04 |
Family
ID=4519219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8447/40A Expired GB543567A (en) | 1939-05-11 | 1940-05-10 | Manufacture of azo-dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB543567A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2424493A (en) * | 1943-09-02 | 1947-07-22 | Chem Ind Basel | Pyrazolone monoazo dyes containing polybasic acid esters of alkylene sulfones |
US3012843A (en) * | 1957-06-27 | 1961-12-12 | Cfmc | Process for the coloration of linear polyester fibres with new azo dyestuffs |
-
1940
- 1940-05-10 GB GB8447/40A patent/GB543567A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2424493A (en) * | 1943-09-02 | 1947-07-22 | Chem Ind Basel | Pyrazolone monoazo dyes containing polybasic acid esters of alkylene sulfones |
US3012843A (en) * | 1957-06-27 | 1961-12-12 | Cfmc | Process for the coloration of linear polyester fibres with new azo dyestuffs |
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