GB782322A - Halogenated salicylanilides and compositions containing the same - Google Patents
Halogenated salicylanilides and compositions containing the sameInfo
- Publication number
- GB782322A GB782322A GB25999/55A GB2599955A GB782322A GB 782322 A GB782322 A GB 782322A GB 25999/55 A GB25999/55 A GB 25999/55A GB 2599955 A GB2599955 A GB 2599955A GB 782322 A GB782322 A GB 782322A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- dichloro
- phenyl
- halogenated
- chlorine
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
An antiseptic detergent soap composition comprises a detergent soap and 0.1-10 per cent by weight, based on the weight of the soap, of a halogenated salicylanilide of the formula <FORM:0782322/III/1> wherein X1 is a chlorine or bromine atom, Y is a methyl or phenyl group and R1 is a halogenated aromatic hydrocarbon group containing one or more benzene nuclei and not more than 3 chlorine and/or bromine atoms, the orthopositions being free from halogen atoms when Y is a methyl group. Colours, water softeners, antioxidants, perfumes and emmolients may be added to the composition.ALSO:The invention comprises halogenated salicylanilides of the formula <FORM:0782322/IV (a)/1> wherein X is a halogen atom, Y is a methyl or phenyl group and R is a mono- or poly-halogenated aromatic hydrocarbon group containing one or more benzene nuclei, and their preparation by heating a compound of the formula <FORM:0782322/IV (a)/2> wherein -OZ is the residue of a phenol ZOH, with an amine RNH2, in an inert organic solvent. Values of R include phenyl, tolyl, ethylphenyl, cumenyl, tert.-butylphenyl, iso-amylphenyl, hexylphenyl, xylyl, cymyl and diphenylyl. The reaction is preferably carried out under reflux using a solvent which acts as an entraining agent for the phenol ZOH liberated, e.g. trichlorbenzene, diphenyl, diphenyl ether, phenylcyclohexane and dicyclohexyl. In examples: (1) 3-methylsalicylic acid is chlorinated in acetic acid giving 5-chloro-3-methylsalicylic acid, this is heated with phenol and POCl3 in dioxan to give phenyl 5-chloro-3-methylsalicylate and this is condensed with p-chloroaniline in 1,2,4-trichlorobenzene, giving 41,5-dichloro-3-methylsalicylanilide; (2)-(6) 31,5-dichloro-, 21,5-dichloro-, 21,41,5-trichloro- and 31,41,51,5-tetrachloro-3-methyl-salicylanilides and 31,5-dichloro - 21,3 - dimethyl - salicylanilide are prepared similarly; (7) 3-phenylsalicylic acid is chlorinated in acetic acid to give 5-chloro-3-phenylsalicylic acid, this is heated with phenol and POCl3 in dioxan, giving phenyl 5-chloro-3-phenylsalicylate and this condensed with p-chloroaniline in 1,2,4-trichlorobenzene, giving 41,5-dichloro-3-phenylsalicylanilide; (8) 31,5-dichloro-, 21,41,5 - trichloro-, 31,41,5 - trichloro-and 31,41,51,5 - tetrachloro - 3 - phenylsalicyl anilides are prepared similarly. A list of further compounds according to the invention, including bromine-containing and bromine- and chlorine-containing phenyl- and methyl-salicylanilides, is also given.ALSO:An antiseptic detergent soap composition comprises a detergent soap and from 0.1 to 10 per cent, by weight, based on the weight of the soap, of a halogenated salicylanilide of the formula <FORM:0782322/VI/1> wherein X1 is a chlorine or bromine atom, Y is a methyl or phenyl group and R1 is a halogenated aromatic hydrocarbon group containing one or more benzene nuclei and not more than 3 chlorine and/or bromine atoms, the ortho positions being free from halogen atoms when Y is a methyl group. Colours, antioxidants, perfumes, water softeners and emollients may be added to the composition. The term "detergent soap" is defined as a cleansing composition prepared from an alkaline reacting alkali metal compound such as potassium or sodium hydroxide and a saturated or unsaturated fat, fatty oil or fatty acid. "Ivory" (Registered Trade Mark) brand neutral, high grade, white tallow soaps containing halogenated salicylanilides according to the invention are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US782322XA | 1954-09-13 | 1954-09-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB782322A true GB782322A (en) | 1957-09-04 |
Family
ID=22142764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB25999/55A Expired GB782322A (en) | 1954-09-13 | 1955-09-12 | Halogenated salicylanilides and compositions containing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB782322A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1300926B (en) * | 1962-11-16 | 1969-08-14 | Monsanto Co | Process for the preparation of 5-chloro-3- (4-halophenyl) salicylic acid anilides |
US3489686A (en) * | 1965-07-30 | 1970-01-13 | Procter & Gamble | Detergent compositions containing particle deposition enhancing agents |
-
1955
- 1955-09-12 GB GB25999/55A patent/GB782322A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1300926B (en) * | 1962-11-16 | 1969-08-14 | Monsanto Co | Process for the preparation of 5-chloro-3- (4-halophenyl) salicylic acid anilides |
US3489686A (en) * | 1965-07-30 | 1970-01-13 | Procter & Gamble | Detergent compositions containing particle deposition enhancing agents |
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