GB859770A - Improvements in or relating to quaternary ammonium compounds - Google Patents
Improvements in or relating to quaternary ammonium compoundsInfo
- Publication number
- GB859770A GB859770A GB1655056A GB1655056A GB859770A GB 859770 A GB859770 A GB 859770A GB 1655056 A GB1655056 A GB 1655056A GB 1655056 A GB1655056 A GB 1655056A GB 859770 A GB859770 A GB 859770A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyethyl
- dimethyl
- ammonium
- thioglycollate
- dodecyl
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
- A61Q9/04—Depilatories
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Abstract
The invention comprises quaternary ammonium thioglycollates, having the general formula R1R2R3R4N+ -OOC,CH2,SH wherein R1R R2, R3 and R4 are the same or different and each is an alkyl or hydroxy-alkyl group, the total number of carbon atoms in the four groups being at least 10. Preferably R1 contains at least 8 carbons in a straight chain. R2 may be a hydroxy alkyl group and each of R2, R3 and R4 preferably contains not more than 4 carbons. The quaternary salts may be prepared by reacting the corresponding quaternary ammonium hydroxides with thioglycollic acid. Those containing a hydroxy alkyl group may also be prepared by forming the thioglycollate of an appropriate tertiary amine R1R2R3N and thereafter reacting the p thioglycollate with a 1 : 2-alkylene oxide, preferably at 60-70 DEG C. in a closed reactor. The quaternary salts may be used as bactericidal agents, textile modifying agents and as hair-waving agents (see Group IV(c)) and depilatory agents. They react with ferric compounds, molybdates and iodine. In Examples: (1) hexadecyl trimethyl ammonium thioglycollate is prepared by treating a methanolic solution of the corresponding quarternary ammonium chloride with KOH in methanol, filtering off precipitated potassium chloride, neutralising the solution to pH7,0 with thioglycollic acid and then evaporating off the methanol; (2) hexadecyl dimethyl b -hydroxyethyl ammonium thioglycollate is prepared by reacting dimethyl hexadecylamine with ethylene oxide in aqueous ethanol at 60 DEG -80 DEG C. under pressure and neutralising the resultant quaternary ammonium hydroxide to pH7,0 with thioglycollic acid; (3) dibutyl b -hydroxy ethyl octadecyl ammonium thioglycollate is prepared from dibutyl octadecyl amine by the method of (2); (4) dodecyl dimethyl b -hydroxyethyl ammonium thioglycollate is prepared by adding aqueous thioglycollic acid to an ethanolic solution of dimethyl dodecylamine, adding thereto ethylene oxide at 0,5 DEG C. and then heating in a closed vessel at 60-70 DEG C. Other ammonium thioglycollates obtainable by the methods of the examples are the tributyl-b -hydroxyethyl-, dodecyl di- (b -hydroxyethyl)-methyl-, trimethyl-octyl-, dodecyl-b -hydroxypropyl-dimethyl-, and hexyl-b -hydroxy ethyl-dimethyl-ammonium thioglycollates.ALSO:Hair and other keratinous fibres are treated, e.g. waved, by a process comprising applying an aqueous solution of a quaternary ammonium thioglycollate of the general formula: R1R2R3R4+OOC,CH2SH wherein the Rs are the same or different and represent alkyl or hydroxyalkyl groups, the total number of carbon atoms in the four groups being at least 10; the solution is applied to the hair or other keratinous fibres at a pH of 7-10 and at a solution concentration not exceeding 25% by weight to relax the fibres, which are deformed whilst they are relaxed, and thereafter, if desired, treated with a mild oxidising solution, e.g. of sodium bromate. Specified quaternary ammonium thioglycollates are the hexadecyl trimethyl, hexadecyl dimethyl b - hydroxyethyl, dibutyl b - hydroxyethyl octadecyl, dodecyl dimethyl b - hydroxyethyl, tributyl b - hydroxyethyl, dodecyl methyl di(b - hydroxyethyl), trimethyl octyl, dodecyl b - hydroxyethyl dimethyl and hexyl-b - hydroxyethyl dimethyl ammonium thioglycollates. Their preparation is described (see Group IV(b)).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1655056A GB859770A (en) | 1956-05-29 | 1956-05-29 | Improvements in or relating to quaternary ammonium compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1655056A GB859770A (en) | 1956-05-29 | 1956-05-29 | Improvements in or relating to quaternary ammonium compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB859770A true GB859770A (en) | 1961-01-25 |
Family
ID=10079339
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1655056A Expired GB859770A (en) | 1956-05-29 | 1956-05-29 | Improvements in or relating to quaternary ammonium compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB859770A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3311625A (en) * | 1964-03-17 | 1967-03-28 | Millmaster Onyx Corp | Quaternary ammonium salts of sulfur bearing anions |
GB2312444A (en) * | 1996-04-27 | 1997-10-29 | R & C Products Pty Ltd | Keratin fibre modification using quaternary ammonium compounds |
-
1956
- 1956-05-29 GB GB1655056A patent/GB859770A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3311625A (en) * | 1964-03-17 | 1967-03-28 | Millmaster Onyx Corp | Quaternary ammonium salts of sulfur bearing anions |
GB2312444A (en) * | 1996-04-27 | 1997-10-29 | R & C Products Pty Ltd | Keratin fibre modification using quaternary ammonium compounds |
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