Patent GB-860655-A (GB)
Title: Amides of aminoalkyl pyrrolidones
IPC: B03D1/01
Filed: 1959-06-03
Abstract: The invention comprises compounds of the formula <FORM:0860655/IV (b)/1> (wherein R is an aliphatic group of 5 to 22 carbon atoms or a mixture of such groups or is an alkaryl, aralkyl, phenoxyalkyl or dichlorophenoxyalkyl group, R1 is hydrogen or an alkyl or hydroxyalkyl group of at most 5 carbon atoms, m is zero, 1, 2, 3, and n is 1, 2 or 3 and the group-(CH2)n-may be substituted by a hydroxyl radical).  They may be prepared by heating, at reduced pressure, equimolecular proportions of the appropriate acid or mixture of acids RCOOH with the appropriate amino-alkyl-pyrrolidone, prepared from an alkylene diamine or polyamine and gamma-butyrolactone.  In examples aminoethylaminoethyl-pyrrolidone is reacted with lauric, pelargonic, oleic, iso-octanoic, palmitic and stearic acids and with a mixture consisting of 50% oleic, 40% linoleic, 4% linolenic and 6% rosin acids; aminoethyl pyrrolidone is reacted with lauric, oleic, pelargonic, iso-octanoic, myristic, palmitic, capric, 2:4-dichlorophenoxybutyric, coconut fatty and stripped coconut fatty acids and with the mixture detailed above; N-(3-amino-2-hydroxypropyl)-pyrrolidone with lauric and oleic acids; and b -hydroxyethyl-aminoethyl-pyrrolidone with lauric acid. Reference is also made to the use of caproic and capryllic acids and acids from tall oil, hydrogenated tall oil, oxo alcohols and aldehydes, oxidized petroleum fractions, olive, tallow, palm, castor, peanut, soybean, cottonseed, ucuhuba, linseed, cod, herring, menhaden, neat's-foot, sperm, corn, butter, babassu, kapok, hempseed, mustard, rape, safflower and sesame oils and dimer and trimer acids; and to the use of other amino-alkyl pyrrolidones.ALSO:<FORM:0860655/IV(c)/1> (wherein R is an aliphatic group of 5-22 carbon atoms or a mixture of such groups, or is an alkaryl, aralkyl, phenoxyalkyl or dichlorophenoxyalkyl group, R1 is hydrogen or an alkyl or hydroxyalkyl group of at most 5 carbon atoms, m is zero, 1, 2 or 3, n is 1, 2 or 3 and the group-(CH2)nmay be substituted by a hydroxyl radical) are stated to be useful as antistatic agents and in the preparation of hair-wave sets.  Specific anides of the above formula wherein RCO is variously polargonoyl, iso-octanoyl, a mixture of oleoyl, linoleoyl, linolenoyl and acyl groups of rosin acids, lauroyl, oleoyl, acyl groups of coconut fatty acids and stripped coconut fatty acids, myristoyl, palmitoyl, and capryl, R1 is hydrogen or hydroxyethyl, m is zero or 1 and n is 2 or 3 are stated to be effective as antistatic agents when tested on nylon, Orlon, Dacron and Acrilan ("Orlon", "Dacron", and "Acrilan" are Registered Trade Marks) and some are stated to be useful as wetting agents, e.g. in 1% aqueous solution.ALSO:Amides of the formula <FORM:0860655/III/1> (wherein R is an aliphatic group of 5 to 22 carbon atoms or a mixture of such groups, or is an alkaryl aralkyl, phenoxyalkyl or dichlorophenoxy alkyl group, R1 is hydrogen or an alkyl or hydroxyalkyl group of at most 5 carbon atoms, m is zero, 1, 2 or 3, and n is 1, 2 or 3 and the group -(CH2)nmay be substituted by a hydroxyl radical) are used as emulsifiers and foam-building agents.  In specified amides used as foam-building agents, particularly when formulated with alkylarylsulphonates or other surfactants, the group RCO is variously palmitoyl, stearoyl, acyl groups of coconut and stripped coconut fatty acids, myristoyl, capryl, oleoyl, and a mixture of oleoyl, linoleoyl, linolenoyl and acyl groups of rosin acids, R1 is hydrogen or hydroxyethyl, m is zero or 1 and n is 2 or 3.  The amide from oleic acid and aminoethylaminoethyl pyrrolidone is stated to be an effective lime soap dispersing agent, and the amide from this acid and aminoethyl pyrrolidone forms good emulsions with mineral oil.  It is also stated that the amide from iso-octanoic acid and p  aminoethyl pyrrolidone may be used as a defoaming agent.