Patent GB-499130-A (GB)
Title: Improvements in the manufacture and production of wetting agents
IPC: D06M13/402
Filed: 1937-04-09
Abstract: Compounds of the general formula <FORM:0499130/IV/1> where Me is hydrogen, an alkali metal, an ammonium radicle or the radicle of an organic base, X is a sulpho group linked to carbon, oxygen or sulphur, R is an aliphatic residue containing at the most 8 carbon atoms, R1, R2, R3 and R4 are hydrogen or aliphatic radicles, at least two of which are aliphatic radicles containing more than 3 carbon atoms each and more than 11 carbon atoms together, and m and n are 1 or 2, are manufactured by treating amides of the formula <FORM:0499130/IV/2> (where R is an aliphatic residue containing at the most 8 carbon atoms and at least one double linkage, hydroxy or esterified hydroxy group, hydrogen atom in a -position to a CO or COOH group, or halogen atom, and the remaining symbols are as above) with sulphonating agents if hydroxy or esterified hydroxy groups, double linkages or hydrogen atoms in a -position to a CO or COOH group are present, or with sulphites if double linkages are present, or with sulphites or thiosulphates if halogen is present in the acyl radicle of the amides, the amounts of the sulphonating agents or sulphites or thiosulphates being so selected that one or two sulphonic groups are introduced into the acyl radicle.  The starting materials are obtainable by reacting the appropriate di- or tri-carboxylic acids, e.g. maleic, racemic, malonic, succinic or citric acid, or their anhydrides, halides or esters, with suitable amines (which may be in the form of their salts, in which case the presence of an acid-binding agent is desirable), e.g. with amines obtainable from alcohols contained in the higher fractions obtained in the synthesis of methanol or isobutyl alcohol, from alcohols from the oxidation of paraffin waxes, from alcohols obtainable by the condensation of aldehydes and ketones followed by hydrogenation, from mixtures of isohexyl and isoheptyl alcohols, from isodecylcarboxylic acid and other acids from the oxidation of mineral oil, also mono- or diisooctylamine, or ethylhexylamine (obtainable by condensation of butyraldehyde and p  hydrogenation in the presence of ammonia).  In a modification of the process, products containing the sulpho group attached to carbon are manufactured by starting with sulphonated aliphatic di- or tri-carboxylic acids, e.g. sulphomalonic or sulphosuccinic acid, and converting them into the amides.  The products may be used as wetting-agents in the textile industry, alone or with other wetting or cleansing agents, the wetting power in many cases being improved by the presence of constituents of limited water-solubility.  In an example, malonic acid di-(isooctyl)-amide (prepared by heating malonic acid diethyl ester with two molecular proportions of isooctylamine), or the corresponding amide methylated on both amide nitrogen atoms, is treated in carbon tetrachloride solution with sulphur trioxide, and the product is neutralized with caustic soda.  Samples have been furnished under Sect. 2 (5) of products prepared as follows: (A) tartaric acid is heated with diisooctylamine, the resulting amide is treated with chlorsulphonic acid in ether and the product is neutralized with caustic soda; (B) citric acid is heated with isooctylamine, the resulting amide is heated with chlorsulphonic acid and the product is neutralized with caustic soda; (C) adipic acid is heated with a mixture of primary alkyl amines in which the alkyl radicle contains 7-9 carbon atoms (obtainable by converting fatty acids from the oxidation of paraffin wax into nitriles and hydrogenating these in the presence of a cobalt catalyst, e.g. as described in Specification 438,793), the resulting amide mixture is treated in carbon tetrachloride solution with sulphur trioxide and the product is neutralized with ammonia; (D) the sulphonation product of (C) is neutralized with diethylamine. Reference has been directed by the Comptroller to Specification 382,718.