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GB436725A - The manufacture of new quaternary ammonium compounds - Google Patents

The manufacture of new quaternary ammonium compounds

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Publication number
GB436725A
GB436725A GB11238/34A GB1123834A GB436725A GB 436725 A GB436725 A GB 436725A GB 11238/34 A GB11238/34 A GB 11238/34A GB 1123834 A GB1123834 A GB 1123834A GB 436725 A GB436725 A GB 436725A
Authority
GB
United Kingdom
Prior art keywords
chloride
ammonium
dodecylthiomethyl
saturated
prepared
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
GB11238/34A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB436725A publication Critical patent/GB436725A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Quaternary ammonium compounds containing attached to nitrogen at least one high-molecular saturated aliphatic radicle of at least 8 carbon atoms which is interrupted by a sulphur or nitrogen atom, the remaining organic radicles attached to the nitrogen being saturated radicles, are prepared by (1) reacting upon a suitable amine with a reactive ester, e.g. a halide or benzene sulphonyl ester, of the high-molecular aliphatic alcohol containing sulphur or nitrogen in the chain; (2) treating an amine containing the high-molecular substituent with a reactive ester of a saturated alcohol, (3) reacting an appropriate thioalcohol or amine with a saturated amine containing a radicle with a replaceable substituent such as chlorine, and (4) treating a saturated amine having a radicle containing an amino or sulphydryl group with a reactive ester of a saturated alcohol; in each case the product is converted, if necessary, into the quaternary form. The compounds possess bactericidal and fungicidal properties and may be incorporated with inert dispersing agents. The samples furnished under Sect. 2 (5) comprise (1) trimethyl - dodecyl - thiomethyl - ammonium chloride, prepared by heating dodecylthiomethyl chloride, obtained by introducing hydrogen chloride into a mixture of dodecylmercaptan and formaldehyde, with trimethylamine; (2) dimethyl-dodecyl-dodecyl-thiomethyl-ammonium chloride, formed by heating dodecylthiomethyl chloride with dimethyldodecylamine; (3) dimethyl - hydroxyethyl - dodecylthiomethyl - ammonium chloride, obtained by stirring dodecylthiomethyl chloride with dimethylaminoethanol; (4) methyl-diethyl - dodecylthioethyl - ammonium iodide, prepared by heating methyl iodide with diethyl - dodecylthioethylamine, which results from the interaction of sodium dodecylmercaptan with diethylaminoethyl chloride; (5) trimethyl - decylmethylaminoethyl - ammonium bromide, which is produced by heating trimethylamine with methyldecylaminoethyl bromide, the latter being formed when the reaction product of methyldecylamine and ethylene bromhydrin is treated with hydrogen bromide; (6) trimethyl - dodecylmethylaminoethyl-ammonium iodide, prepared by heating methyldodecylamine with dimethylaminoethyl chloride and treating the resulting dodecyl-trimethyl-ethylenediamine with methyl iodide. The Specification as open to inspection under Sect. 91 describes the high-molecular aliphatic radicle as preferably containing 8--20 carbon atoms and states that substituents, such as hydroxyl, alkoxy and amino groups and halogen atoms, may be present therein. It further states that the other saturated organic radicles are preferably lower alkyl groups, but may also comprise alkyl groups of 8--18 carbon atoms or cyclo-aliphatic groups, e.g. cyclopentyl and cyclohexyl groups. The preparation of the following compounds is also described: (1) tributyldodecylthiomethyl - ammonium chloride from dodecylthiomethyl chloride and tributylamine; (2) trihydroxyethyl - dodecylthiomethyl - ammonium chloride from dodecylthiomethyl chloride and triethanolamine; (3) methyl-diethyl-octylthioethyl-ammonium iodide from diethyl - octylthioethylamine, prepared by reacting octylthioethyl chloride with diethylamine, and methyl iodide. Finally, it is stated that the quaternary ammonium products in the form of their hydrohalides may be converted into salts with nitric, sulphuric, alkyl- and phenyl-sulphonic, phosphoric, formic, acetic, lactic, citric, tartaric, benzoic and salicylic acids, or may be treated with caustic alkali to give the free bases. This subject-matter does not appear in the Specification as accepted.
GB11238/34A 1933-04-13 1934-04-13 The manufacture of new quaternary ammonium compounds Expired GB436725A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE436725X 1933-04-13

Publications (1)

Publication Number Publication Date
GB436725A true GB436725A (en) 1935-10-14

Family

ID=6506944

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11238/34A Expired GB436725A (en) 1933-04-13 1934-04-13 The manufacture of new quaternary ammonium compounds

Country Status (1)

Country Link
GB (1) GB436725A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2689790A (en) * 1951-09-26 1954-09-21 Monsanto Chemicals Nitrogenous compound herbicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2689790A (en) * 1951-09-26 1954-09-21 Monsanto Chemicals Nitrogenous compound herbicides

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