GB587467A - Manufacture of new azo-dyestuffs - Google Patents
Manufacture of new azo-dyestuffsInfo
- Publication number
- GB587467A GB587467A GB16834/44A GB1683444A GB587467A GB 587467 A GB587467 A GB 587467A GB 16834/44 A GB16834/44 A GB 16834/44A GB 1683444 A GB1683444 A GB 1683444A GB 587467 A GB587467 A GB 587467A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- pyrazolone
- dyestuffs
- group
- sulphone
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/447—Azo dyes
- C09B62/45—Monoazo dyes
Abstract
Azo dyestuffs of the general formula <FORM:0587467/IV/1> in which y is the residue of a polybasic acid bound in the form of an acid ester (e.g. the residue of sulphuric, oxalic, malonic, succinic, adipic, pimelic, suberic, maleic, phthalic, m-sulphobenzoic, sulphophthalic, sulphoacetic or chlorosulphoacetic acid). A is the residue of a yellow component, and R is an alkylene group which contains at least 2 but not more than 6 carbon atoms directly connected with one another, and may contain halogen atoms as substituents, and in which the benzene nucleus may contain further substituents, e.g. halogen atoms, alkyl, alkoxy or nitro groups, are manufactured by treating a dyestuff of the general formula <FORM:0587467/IV/2> (obtainable from, for example, aniline-o-, m- or p-(b -hydroxyethyl)-sulphone) with at least an equimolecular proportion of a polybasic acid or the anhydride or a halide or reactive ester thereof, or by diazotizing an aromatic amine of the general formula <FORM:0587467/IV/3> and coupling with a yellow component, e.g. a phenol such as phenol itself and especially a phenol coupling in o-position to the hydroxy group, such as p-cresol, resorcinol or a monoalkyl ether of hydroquinone, a dihydroxyquinoline, a -methylketol, an ester or amide of acetoacetic acid, or especially a pyrazolone such as 1 - phenyl - 3 - methyl - 5 - pyrazolone, a 1 - tolyl- or 1 - chlorophenyl - 3 - methyl - 5 - pyrazolone, a pyrazolone carboxylic or sulphonic acid, or 3-methyl-5-pyrazolone. The products, which are soluble in water, especially in the form of their salts, dye cellulose esters and ethers from aqueous solution in yellow shades, and are also suitable for dyeing artificial masses, e.g. nitrocellulose lacquers and artificial fibres composed of superpolyamides or superpolyurethanes, and in some cases for dyeing animal fibres, e.g. wool or silk. In examples: (1) aniline - p - (b - hydroxyethyl)- sulphone is diazotized and coupled with 1-(21-chloro)-phenyl - 3 - methyl - 5 - pyrazolone, and the product is treated with sulphuric acid and then neutralized with sodium carbonate; alternatively the diazo component is treated with sulphuric acid before diazotization; (2) the coupling component in (1) is replaced by p-cresol; (3) the initial dyestuff of (1) is heated with succinic anhydride in glacial acetic acid (or other solvent, e.g. toluene, benzene or xylene), and the product is neutralized with sodium carbonate; (4) cellulose acetate artificial silk yarn is dyed with the product of (1) from a bath containing sodium sulphate. Formul are given further dyestuffs, including one derived from aniline-p-(g -hydroxy-b -chloropropyl)-sulphone. Aminoaryl - b - hydroxyethyl - sulphones are obtainable by converting the corresponding acylaminoarylsulphohalide, e.g. an acetanilidesulphohalide, into the sulphinic acid, treating this with an ethylene halohydrin and then saponifying the acylamino group, or by treating the appropriate mercaptan of nitrobenzene with an ethylene halohydrin, oxidizing the thioether to the sulphone, and reducing the nitro group. Specification 516,929 is referred to. The Specification as open to inspection under Sect. 91 comprises also the manufacture of dyestuffs containing, instead of the -SO2-group in the general formula above, the grouping <FORM:0587467/IV/4> wherein Z is hydrogen or an alkyl or substituted alkyl group containing not more than 6 carbon atoms directly connected to one another. Additional diazo components specified are aniline-o-, -m- and -p-sulpho-N-(b -hydroxyethyl)-amides (obtainable by the action of ethanolamine on the corresponding sulphonic acid halide of nitrobenzene or acetanilide, followed by reduction or saponification), or their esters with polybasic acids, and formul are given of dyestuffs derived from these components, and also one from sulphanilic acid N - (b - sulphatoethyl)-N-phenylamide (sic). This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH587467X | 1943-09-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB587467A true GB587467A (en) | 1947-04-25 |
Family
ID=4521899
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16834/44A Expired GB587467A (en) | 1943-09-02 | 1944-09-04 | Manufacture of new azo-dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB587467A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE965902C (en) * | 1949-07-19 | 1957-09-19 | Hoechst Ag | Process for fixing water-soluble organic compounds on substrates with a fibrous structure |
US5106960A (en) * | 1980-03-28 | 1992-04-21 | Ciba-Geigy Corporation | Azo dyes and the production and use thereof |
-
1944
- 1944-09-04 GB GB16834/44A patent/GB587467A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE965902C (en) * | 1949-07-19 | 1957-09-19 | Hoechst Ag | Process for fixing water-soluble organic compounds on substrates with a fibrous structure |
US5106960A (en) * | 1980-03-28 | 1992-04-21 | Ciba-Geigy Corporation | Azo dyes and the production and use thereof |
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