GB429176A - Manufacture of dyestuffs - Google Patents
Manufacture of dyestuffsInfo
- Publication number
- GB429176A GB429176A GB32341/33A GB3234133A GB429176A GB 429176 A GB429176 A GB 429176A GB 32341/33 A GB32341/33 A GB 32341/33A GB 3234133 A GB3234133 A GB 3234133A GB 429176 A GB429176 A GB 429176A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- anhydride
- sulphonated
- acid
- hydroxy
- 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
- C09B25/00—Quinophthalones
Abstract
Dyestuffs of the quinoline series are manufactured by condensing a quinaldine, containing in the 3-position a hydroxy group, with the anhydride or imide of an unsubstituted or substituted dicarboxylic acid, the product being, if required, sulphonated or, if desired, halogenated, or both sulphonated and halogenated in either order. The sulphonation may be effected in known manner, e.g. by the action of fuming sulphuric acid below 15 DEG C. Suitable quinaldines are 3-hydroxy-2-methylquinoline or its substitution products containing, for instance, a sulphonic group, or containing, e.g. in the 4-position, an amino-group, which may be acylated or arylated. Suitable dicarboxylic acid anhydrides are phthalic anhydride and its substitution products, e.g. 3-chloro- or 3 : 6-dichlorophthalic anhydride, also polycarboxylic acid anhydrides, such as tetracarboxylic acid anhydrides, e.g. pyromellitic acid anhydride, also naphthalene-1 : 2 : 5 : 6-tetracarboxylic acid anhydride or mellitic acid anhydride. The products are acid wool dyestuffs, whilst those from polycarboxylic acid anhydrides, when sulphonated, also dye cotton. In examples: (1) 2 - methyl - 3 - hydroxyquinoline is fused with phthalic anhydride to produce 3-hydroxyquinophthalone, which is sulphonated; the product dyes wool yellow tints; (2) the condensation of (1) is effected at a lower temperature in the presence of zinc chloride; (3) 3-hydroxyquinophthalone is brominated in boiling acetic acid solution, yielding a monobromocompound which is sulphonated; the product dyes wool yellow tints; (4) phthalic anhydride is fused with 3-hydroxyquinaldinesulphonic acid (obtainable by sulphonating 3-hydroxyquinaldine); the product dyes wool light yellow tints; (5) 4-benzoylamino-3-hydroxy-2-methylquinoline (obtainable by coupling 3-hydroxyquinaldine with diazotized aniline, reducing and splitting the azo-dyestuff and reacting the product with benzoyl chloride) is fused with phthalic anhydride and the product is sulphonated; the product dyes wool greenish-yellow tints; if the benzoyl chloride is replaced by 1 - hydroxy - 2 - carboxy - benzene - 4 - sulphonic acid chloride the dyestuff contains groups capable of being chromed; (6) b -hydroxyquinaldine is fused with 3-chlorophthalic anhydride and the product is sulphonated; the product dyes wool yellow tints; (7) the 3-chlorophthalic anhydride of (6) is replaced by 3 : 6-dichlorophthalic anhydride; the product dyes wool yellow tints; (8) pyromellitic acid anhydride is boiled with 3-hydroxyquinaldine and trichlorobenzene and the product is sulphonated; the product dyes wool and cotton yellow tints; (9) aliphatic or alicyclic dicarboxylic acid anhydrides may be employed in the foregoing examples. Samples have been furnished under Sect. 2 (5) of products prepared as follows: (a) 2-methyl-3-hydroxyquinoline-4-carboxylic acid is heated with phthalic anhydride, yielding a product identical with the unsulphonated product of (1); it may be used as a pigment dyestuff or for colouring lakes and benzine; (b) the product of (a) is sulphonated to yield a product identical with the sulphonated product of (1); (c) 4-acetylamino - 3 - hydroxy - 2 - methylquinoline (obtainable by coupling 3-hydroxy-2-methylquinoline with diazotized sulphanilic acd reducing and splitting the azo-dyestuff and boiling the product with acetic anhydride in chlorobenzene) is heated with phthalic anhydride; (d) the product of (c) is sulphonated, yielding a dyestuff which dyes wool yellow tints.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE429176X | 1932-11-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB429176A true GB429176A (en) | 1935-05-20 |
Family
ID=6477577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32341/33A Expired GB429176A (en) | 1932-11-18 | 1933-11-20 | Manufacture of dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB429176A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036876A (en) * | 1958-08-02 | 1962-05-29 | Basf Ag | Linear polyesters dyed with 3'-hydroxy-quinophthalone dyestuffs |
-
1933
- 1933-11-20 GB GB32341/33A patent/GB429176A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036876A (en) * | 1958-08-02 | 1962-05-29 | Basf Ag | Linear polyesters dyed with 3'-hydroxy-quinophthalone dyestuffs |
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