GB815226A - Manufacture of water-soluble organic iso thiouronium salts - Google Patents

Abstract

Emulsions are formed from chlorinated hydrocarbons, e.g tetrachloroalkanes of the formula bl(CH2)nCbl3, and isothiouronium salts containing a trihalogeno-alkyl group or a dihalogeno-alkenyl group and prepared by reacting a tetrahalogeno-alkane of the formula (halogen)3C-(CH2-CH2)n-halogen or a trihalogeno-alkene of the formula (halogen)2 C = CH-CH2-(CH2-CH2)n-1-halogen (wherein the halogen is chlorine or bromine and n is an integer from 1 to 10) with thiourea or a substituted thiourea, e.g. N-alkyl-, N : N1-dialkyl- or N : N-dialkylthioureas wherein the alkyl groups may be wholly or partially replaced by aryl groups, or N : N-alkylenethioureas.ALSO:Polyvinyl chloride is emulsified with isothiouronium salts containing a trihalogenoalkyl group or a dihalogeno-alkenyl group and prepared by reacting a tetrahalogeno-alkane of the formula (halogen)3C-(CH2-CH2)n-halogen or a trihalogeno-alkene of the formula (halogen)2C = CH-CH2-(CH2-CH2)n-1 - halogen (wherein the halogen is chlorine or bromine and n is an integer from 1 to 10) with thiourea or a substituted thiourea, e.g. N-alkyl-, N:N1-dialkyl- or N:N-dialkyl-thioureas wherein the alkyl groups may be wholly or partially replaced by aryl groups, or N:N-alkylene thioureas.ALSO:Isothiouronium salts containing a trihalogenoalkyl group or a dihalogenoalkenyl group are prepared by reacting a tetrahalogeno-alkane of the formula (halogen)3C-(CH2-CH2)n-halogen or a trihalogeno-alkene of the formula (hal)2C=CH-CH2-(CH2-CH2)n-1-hal (wherein the halogen is chlorine or bromine and n is an integer from 1 to 10) with thiourea or a substituted thiourea, e.g. N-alkyl-, N : N1-dialkyl- or N : N-dialkyl-thioureas wherein the alkyl groups may be wholly or partially replaced by aryl groups, or N : N-alkylene-thioureas. The reaction is advantageously conducted in an organic solvent, e.g. ethanol, acetone, methyl ethyl ketone or methanol, with or without the addition of water. The salts may be converted into the free bases by addition of weak bases such as ammonium hydroxide and the free bases may then be converted to other salts. Alternatively, other salts may be formed by double decomposition, e.g. trichloropentyl-isothiouronium thiocyanate from the chloride and potassium thiocyanate. In examples: (1) 1 : 1 : 1 : 5-tetrachloropentane and thiourea are refluxed in ethanol to give 1 : 1 : 1 - trichloropentyl - (5) - isothiouronium chloride; (2) 1 : 1 : 1 - trichloroheptyl - (7) - isothiouronium chloride is similarly prepared; (3) a mixture of 1 : 1 : 1 : o -tetrachloralkanes having the average constitution cl(CH2)16Ccl3 is reacted with thiourea as in (1) to give an o : o : o -trichloralkyl-(1)-isothiouronium chloride mixture; (4) ethylene thiourea and 1 : 1 : 1 : 5-tetrachloropentane similarly yield 2-(5 : 5 : 5-trichloropentyl) - mercapto - imidazoline hydrochloride; (5) 1 : 1 : 5-trichloropentene-(1) and thiourea similarly yield 1 : 1-dichloropenten-(1) yl-(5)-isothiouronium chloride; and (6) the process of (1) is performed in the absence of a solvent.