Patent GB-989495-A (GB)
Title: Organic sulfonates and methods for their preparation
IPC: C07D233/14
Filed: 1962-01-03
Abstract: The invention comprises a surface-active organic sulphonate of the general formula <FORM:0989495/C2/1> whereinA is an organic-amino radical joined to the remainder of the molecule through a nitrogen atom and having at least one substituent consisting of a hydrocarbon radical of 6-24 carbon atoms and M is a cation, the self internal salts and the self or mixed external salts thereof. A is preferably one of the following radicals <FORM:0989495/C2/2> or <FORM:0989495/C2/3> , in which R and Ra are (C6-C24) hydrocarbon radicals, R2 is (a) hydrogen, (b) a (C1-C6) alkyl radical, (c) a (C2 -C6) hydroxyalkyl radical, or (d) 1-15 mole alkylene oxide adduct of said hydroxyalkyl radical; R3 is a C2-C6 alkylene group, C2-C6 hydroxy alkylene group or a 1-15 mole alkylene oxide adduct of said hydroxy alkylene group; Q1 is (b), (c) or (d) as defined for R2; Q2 is (a), (b), (c) (d) as defined for R2, (e) an aromatic, aromatic-aliphatic or aliphatic-aromatic hydrocarbon radical of 6-12 carbon atoms of (f) <FORM:0989495/C2/4> each Y is (b), (v), (d) as defined for R2 or (e) as defined for Q2; with each alkylene oxide group being of 2-4 carbon atoms.  The (C6-C24) hydrocarbon radical Ra may be aliphatic (saturated or unsaturated), cylo-aliphatic, or aliphatic-aromatic with the aliphatic portion having at least 3 carbon atoms; while R may be aliphatic (saturated or unsaturated), cycloaliphatic, aromatic, aliphatic-aromatic or aromatic-aliphatic; M can be hydrogen, Na, K or other alkali metals or other equivalent cations. The internal salts may be obtained by heating a sultone of the formula <FORM:0989495/C2/5> with an amine having at least one substituent which is a C6-C24 hydrocarbon radical, in an aqueous medium with pH less than 7, which yields the internal salt of the sulphonate. The internal salts are converted to external salts (or amphoteric salts in their simple form) by heating to and maintaining at 65-90 DEG  C. under alkaline conditions.  The alkaline agent employed is suitably NaOH or KCH.  The amphoteric salts in their simple form may either alone or in combinations of two or more of them be reacted with each other in the presence of an acidic agent, such as hydrochloric, acetic, hydroxy acetic or phosphoric acid, to provide external self or mixed salts, such as <FORM:0989495/C2/6> Amines preferred for use in the above reaction are amines IA IB, IC and ID having respectively the following formulae <FORM:0989495/C2/7> wherein R1, Ra, R2, R3, Q1 and Q2 are as hereinbefore defined, and such amines are exemplified by the following <FORM:0989495/C2/8> an amine of the above formula where the -CH2-CH2-OH group is replaced by a -C3H7 group, amines of the above formula where the C11H23-radical is replaced by C9,H19, C17H35 and C17H33 radicals, the amines of the following structures <FORM:0989495/C2/9> amines of the last given formula except that the C11-H23 radical is replaced by the C13H27 and C17H31 radicals, amines of the last given formula except that the C2H4OH radical is replaced by C2H5, C2H4-O-C2H4OH and C2H4-O-(C2 H4-O)3-H radicals, an amine of the same type formula except that CH3 is substituted for the H on the amide nitrogen and C2H4-O-(C3H6 -O)5H is substituted for the C2H4OH radical; lauryl amine, octyl methylamine, capryl-phenyl ethanolamine, an amine of the formula C10H21-NH-C2H4O-(C2H40) 3-H lauryl hexyl ethanolamine, capryl-phenyl ethyl methylamine and an amine of the formula C10H21-N(CH3)-C2H4O-(C2 H4O)5-H The products of the general formula may be used as general purpose detergents, textile treating agents, foaming agents, emulsifying agents and in shampoo and cosmetic formulations.  Amines having the first type of Formula IA may be obtained by reacting an appropriate diamine with a C7-C25 monocarboxylic acid until about 2 moles of water have been eliminated. Alkyleneoxylation of the alkanol radical if present may be effected by treating with an alkylene oxide to give a 1-15 mole alkylene oxide adduct per hydroxy group of said alkanol radical.  Amines of the second type Formula IB may be obtained by reacting an appropriate diamine with a monocarboxylic acid until 1 mole of water has been eliminated.  Alkyleneoxylation of the alkanol radicals if present may be effected by treating with an alkylene oxide to give a 1-15 mole alkylene oxide adduct per hydroxy group.  Suitable diamines which may be used to prepare reactants of Formula IA and IB include NH2C2H4NHC2H4OH, NH2C2H4NHC2H5 and NH2C2H4NHC4H9. Suitable diamines which may be used to prepare the IB type reactants include CH3NHC3H6NHC3H6OH, NH2C4H8NHC4H8OH, NH2C3H5OHNHC3H5(OH)2, C2H4OHNHC2H4NHC2H4OH and NH2C3H5OHNHC2H5OH. Suitable carboxylic acids including the equivalent anhydrides and esters thereof include saturated or unsaturated aliphatic fatty acids which may contain substituents, e.g. aryl radicals, cyclo-aliphatic carboxylic acids, aromatic, aliphatic-aromatic and aromatic-aliphatic carboxylic acids.  The carboxylic acids may be derived from oils or fats of marine, animal or vegetable origin or they may be synthetic acids derived by oxidation of paraffin wax and similar hydrocarbons. The acid may also be one of the resinic acids, a naphthenic acid or a long-chain fatty acid having an aromatic hydrocarbon radical connected directly to the aliphatic chain.  Amines of the type IC and ID include hexyl phenylene methyl tributoxy butanolamine.  The sultone of the formula <FORM:0989495/C2/100> is obtained by heating a mixture of sodium metabisulphite with an aqueous solution of sodium hydroxide at 90 DEG  C. for 15 minutes, cooling to 28 DEG  C., adding epichlorohydrin slowly, maintaining the temperature at 47-50 DEG  C. for about 3 hours, boiling the mass for 1 hour and then cooling to room temperature to give an aqueous solution of the required sultone. Specifications 853,440 and 853,441 are referred to.