GB607222A - Manufacture and use of new phenoxyethyl-ammonium compounds - Google Patents

Manufacture and use of new phenoxyethyl-ammonium compounds

Info

Publication number
GB607222A
GB607222A GB29502/45A GB2950245A GB607222A GB 607222 A GB607222 A GB 607222A GB 29502/45 A GB29502/45 A GB 29502/45A GB 2950245 A GB2950245 A GB 2950245A GB 607222 A GB607222 A GB 607222A
Authority
GB
United Kingdom
Prior art keywords
bromide
carbon atoms
phenoxy
dodecyl
nitrogen atom
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
Application number
GB29502/45A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB607222A publication Critical patent/GB607222A/en
Expired legal-status Critical Current

Links

Landscapes

  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Phenoxyethylammonium compounds, useful as disinfectants and preserving agents, are manufactured by (a) quaternating phenoxy-ethyldimethylamine with a quaternating agent which introduces an alkyl residue having at least 8 carbon atoms, or (b) treating phenoxy-ethylamine, containing, at the nitrogen atom, an alkyl residue having at least 8 carbon atoms and a hydrogen atom or a methyl group, with a methylating agent, or (c) treating a hydroxy-ethyldimethylammonium compound, containing, at the quaternary nitrogen atom, an alkyl residue having at least 8 carbon atoms, or a reactive derivative thereof, with phenol or a reactive derivative thereof, or (d) treating a reactive ester (especially a halide) of phenoxy-ethanol (obtainable from phenol and a reactive ester of ethylene glycol) with a dimethylamine containing, as a substituent at the nitrogen atom, an alkyl residue having at least 8 carbon atoms. As quaternating agent in method (a) or (b) may be used a reactive ester of an alcohol having at least 8 carbon atoms or of methanol, e.g. an ester of a hydrohalic acid or of an aliphatic, aromatic or araliphatic sulphonic acid. Method (c) may be carried out by reacting a halogenethylammonium compound with phenol or a hydroxyethylammonium compound with a halogenbenzene. In examples: (1) b -phenoxy-ethyldimethyldodecylammonium bromide is made by heating b -phenoxyethyldimethylamine with dodecyl bromide or by methylacting b -phenoxyethyldodecylamine with formaldehyde and formic acid and then quaternating with methyl bromide; the corresponding chloride is obtained by treating the bromide with silver chloride in alcohol or by replacing the dodecyl bromide by dodecyl chloride, and the corresponding p-toluenesulphonate by replacing the methyl bromide by p-toluenesulphonic acid methyl ester; (2) the dodecyl bromide in (1) is replaced by hexadecyl or octyl bromide. Samples have been furnished under Sect. 2 (5) of b - phenoxyethyldimethyldodecylammonium bromide prepared by refluxing phenoxyethyl bromide with dodecyldimethylamine in (I) ethyl acetate, (II) acetone and (III) water. The Specification as open to inspection under Sect. 91 comprises also the manufacture of other phenoxyethyldimethylammonium compounds derived from monohydric phenols in which the phenyl nucleus may be substituted, e.g. by halogen atoms or alkyl groups, and containing at the quaternary nitrogen atom a hydrocarbon residue having at least 8 carbon atoms, e.g. b -(p-chlorophenoxy)-ethyldimethyl-dodecylammonium bromide (from b -(p-chloro-phenoxy) - ethyldimethylamine and dodecyl bromide, or from dimethyldodecylamine and b -(p-chlorophenoxy)-ethyl bromide (obtained in turn by reacting potassium p-chlorophenolate with ethylene chlorhydrin and then replacing the hydroxy group by bromine), or from potassium p-chlorophenolate and b -bromoethyl-dimethyldodecylammonium bromide), b -(p- and o-methylphenoxy)-ethyldimethyldodecylammonium bromide (from b -(p- or o-methylphenoxy)-ethyldimethylamine and dodecyl bromide), b -(p-tert.-butyl-, -iso-octyl-and-hexyl-phenoxy)-ethyldimethyldodecylammonium bromide (similarly from the appropriate starting materials, obtainable in turn from the appropriate phenols and b - chloroethyldimethylamine), b - (p-tert.-butylphenoxy) - ethyldimethyloctylammonium bromide (from b -(p-tert.-butylphenoxy)-ethyl-dimethylamine and octyl bromide) and b -(p-tert. - octylphenoxy) - ethyldimethyldodecylammonium bromide. Reference is also made to the preparation of b -phenoxyethyldimethyl-(ethylhexyl)-ammonium bromide. This subject-matter does not appear in the Specification as accepted.ALSO:Disinfectants consist of phenoxyethyldimethylammonium compounds containing at the quaternary nitrogen atom an alkyl residue having at least 8 carbon atoms, which compounds may be used in the form of solutions or emulsion or with inert or other active substances, e.g. in salves or dry powders. In examples: (1) b - phenoxyethyldimethyldodecylammonium bromide is pressed into tablets with starch, and, if desired, substances which accelerate dissolution in water; (2) b - phenoxyethyldimethylhexadecylammonium bromide is mixed with a finely pulverized diluent such as bole, boric acid, urea or cork meal, to produce a dusting powder. The Specification as open to inspection under Sect. 91 comprises also the use of similar compounds in which the phenyl group may be substituted by halogen atoms or alkyl groups. In further examples: (4) b - (p-methylphenoxy)-is dissolved in water, and colouring and odoriferous substances may be added; (6) b - (p-iso-octylphenoxy) - ethyldimethyl - dodecylammonium bromide is dissolved in a salve base consisting of white petroleum jelly, paraffin oil, wool fat and a little water. This subject-matter does not appear in the Specification as accepted.
GB29502/45A 1944-11-24 1945-11-06 Manufacture and use of new phenoxyethyl-ammonium compounds Expired GB607222A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH607222X 1944-11-24

Publications (1)

Publication Number Publication Date
GB607222A true GB607222A (en) 1948-08-27

Family

ID=4523152

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29502/45A Expired GB607222A (en) 1944-11-24 1945-11-06 Manufacture and use of new phenoxyethyl-ammonium compounds

Country Status (1)

Country Link
GB (1) GB607222A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5165918A (en) * 1988-06-28 1992-11-24 Ciba-Geigy Corporation Antimicrobial ophthalmic solutions containing dodecyl-dimethyl-(2 phenoxyethyl)-ammonium bromide and methods of using the same
CN115477597A (en) * 2022-09-23 2022-12-16 山东科洗新材料有限公司 Preparation method and application of surfactant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5165918A (en) * 1988-06-28 1992-11-24 Ciba-Geigy Corporation Antimicrobial ophthalmic solutions containing dodecyl-dimethyl-(2 phenoxyethyl)-ammonium bromide and methods of using the same
CN115477597A (en) * 2022-09-23 2022-12-16 山东科洗新材料有限公司 Preparation method and application of surfactant

Similar Documents

Publication Publication Date Title
Adler et al. Investigation of the acid-catalysed alkylation of lignins by means of NMR spectroscopic methods
GB607222A (en) Manufacture and use of new phenoxyethyl-ammonium compounds
GB504378A (en) Improvements in sensitive photographic films
US2232053A (en) Foaming composition
ES246512A1 (en) New aminobenzoic acid deriatives and compositions containing same
US2218569A (en) Glycosides of pentose ethers
ES402326A1 (en) Liquid detergent compositions and laundering process
GB853442A (en) Polyester compositions
US2158958A (en) Hydroxy-alkyl ethers of 4-tertiaryalkyl phenols
US1882200A (en) Production of perfumes
GB1313479A (en) Monocarboxylic acid esters of polyethylene glycol ethers
GB586493A (en) New synthetic oestrogenic agents
GB832430A (en) Dichloroxylenol acetate and antifungal formulations containing it
Purchase et al. The acute and chronic toxicity of sterigmatocystin
ES360570A1 (en) Procedure for the preparation of perfume compositions. (Machine-translation by Google Translate, not legally binding)
US2728683A (en) Laundry starch composition
ES311092A1 (en) Procedure for preparing hydroxyethylchellulose. (Machine-translation by Google Translate, not legally binding)
ES429193A1 (en) Herbicidal composition
Hayashi et al. Determination of Threonine in Lipid of Animal Brain.
ES304427A1 (en) A procedure to prepare the dispersion of a cellulose matter. (Machine-translation by Google Translate, not legally binding)
GB892260A (en) Improved water-soluble thermoplastic cellulose ether compositions and films preparedtherefrom
GB835832A (en) Process for the preparation of compositions for use in liquid heat-exchange media
GB996309A (en) New 19-nor steroids
JPS5589299A (en) Novel estradiol derivative, its preparation, and antitumor agent
ES360705A1 (en) A procedure for preparing an emulsifying agent (Machine-translation by Google Translate, not legally binding)