Patent GB-816617-A (GB)
Title: Quaternary ammonium polyoxyalkylenated amino diamide corrosion inhibitors
IPC: C23F11/14
Filed: 1956-08-03
Abstract: Quaternary salts of polyoxyalkylated aminodiamides having a formula such as <FORM:0816617/III/1> where R is a C8-22 unsaturated aliphatic radical, R1 is alkyl, allyl, hydroxyalkyl or aralkyl, R1 is alkyl, allyl, hydroxyalkyl or aralkyl, R2 is H or C1-2 alkyl, X is an anion and n, n2 and n3 each have a value of at least 1 and a total value ranging from 4 to 20, and similar compounds based on polyalkylene polyamines generally (see Group IV (b) for preparation), alone or in admixture with the glycerol formed as a by-product during their preparation from triglycerides, are added to mineral waxes and are also used to break petroleum oil emulsions.ALSO:Quaternary salts of polyoxyalkylated aminodiamides having a formula such as <FORM:0816617/IV (a)/1> where R is a C8-22 unsaturated aliphatic radical, R1 is alkyl, allyl, hydroxyalkyl or aralkyl, R2 is H or C1-2 alkyl, X is an anion and n1, n2 and n3 each have a value of at least 1 and a total value ranging from 4 to 20, and similar compounds based on polyalkylene polyamines generally (see Group IV (b) for preparation), alone or in admixture with the glycerol formed as a by-product during their preparation from triglycerides, are used as plasticisers and modifiers for alkyd and phenolformaldehyde resins.ALSO:Quaternary salts of polyoxyalkylated aminodiamides having formul  such as <FORM:0816617/IV (b)/1> where R is a C8-22 unsaturated aliphatic radical R1 is alkyl, allyl, hydroxyalkyl or aralkyl, R2 is H or C1-2 alkyl, X is an anion and n1, n2 and n3 each have a value of at least 1 and a total value ranging from 4 to 20, are prepared by (A) reacting at a temperature of 130 DEG  to 200 DEG C. one mole. of a polyalkylene polyamine with at least two molecular equivalents of a fatty acid containing a C8-22 unsaturated aliphatic radical or a C1-3 alkyl ester thereof, to produce an amino-diamide, (B) reacting the amino-diamide with more than sufficient C2-4 alkylene oxide to condense with all the remaining replaceable N-hydrogen atoms therein and produce at least one N-polyoxyalkylene radical, and (C) reacting one mole. of the N-polyoxyalkylated product with sufficient alkylating, alkenylating or aralkylating agent to quaternate one N atom per molecule.  Exemplified polyalkylene polyamines are triethylene tetramine, diethylene triamine, tetraethylene pentamine, pentaethylene hexamine and mixtures thereof such as are derived by reacting ammonia with ethylene dichloride. Exemplified fatty acids are oleic, ricinoleic, erucic, linolenic, elaeostearic, licanic, arachidonic, clupanodonic, lauroleic, myristoleic, palmitoleic and gadoleic acids.  Methyl, ethyl and isopropyl esters of the foregoing acids may also be used, as well as glycerides such as soybean, sperm, safflower, salmon, sardine, sesame, sunflower, teaseed, tung, ucuhuba, walnut, whale, babassu, castor, coconut, cod, corn, cottonseed, dogfish, hempseed, herring, kapok, linseed, menhaden, mustard, neat's-foot, oiticica, olive, ouri-curi, palm, peanut, palm-kernal, perilla, pilchard, poppyseed, rape and rubberseed oils, mutton and beef tallow, and cooking fat. The alkylene oxide treatment may be carried out with or without an alkaline catalyst, or with such a catalyst during the latter stages of the treatment.  The use of ethylene, propylene and butylene oxides is specified.  Between 4 and 20 moles. of alkylene oxide are employed per mole. of amino-diamide. Quaternation may be effected with benzyl, methyl or allyl chlorides, methyl bromide, dimethyl and diethyl sulphates, ethylene chlorhydrin, glycerol monochlorohydrin, epichlorohydrin, bis - (chloromethyl) naphthalene, 1-chloro-1-phenylethane, ethylene oxide, propylene oxide and allyl, alkyl and aralkyl phosphates, acetates and stearates. Quaternation with the alkylene oxides is preferably preceded by converting the tertiary amine to its hydrochloric, oxalic or para-toluenesulphonic acid salt.  In examples: (1) 1 mole. of diethylenetriamine is heated with 0.66 mole. of soybean oil, 0.91 mole. of the amide product is condensed with 5.07 moles. of ethylene oxide and 0.54 moles. of the polyoxyethylated product is quaternated with 0.7 mole. of benzyl chloride; (2) 1 mole. of soybean oil is heated with 1.3 moles. of diethylene triamine, 1 mole. of the amide product is condensed with 4.75 moles. of ethylene oxide and 0.45 mole. of the polyoxyethylated product is quaternated with 0.626 mole. of benzyl chloride; (3) to provide a product derived from a saturated fatty acid for comparison, 2 moles. of stearic acid are heated with 1 mole. of diethylene triamine, the amide product is condensed with 5.1 moles. of ethylene oxide and the polyoxyethylated product quaternated with 1 mole. of benzylchloride; (4) 2 moles. of soybean oil fatty acid are heated with 1 mole. of diethylene triamine and the amide product is treated as in (1); and (5) to provide a quaternary polyoxyethylated monoamide for comparison, 1 mole. of soybean oil is heated with 3 moles. of diethylenetriamine, the amide product is condensed with 4.6 moles. of ethylene oxide and the polyoxyethylated product is quaternated with 2 moles. of benzyl chloride.ALSO:Quaternary salts of polyoxyalkylated amino-diamides having a formula such as <FORM:0816617/II/1> where R is a C8-22 unsaturated aliphatic radical, R1 is alkyl, allyl, hydroxyalkyl, or aralkyl, R2 is H or C1-2 alkyl, X is an anion and n1, n2 and n3 each have a value of at least 1 and a total value ranging from 4 to 20, and similar compounds based on polyalkylene polyamines generally (see Group IV (b) for preparation), alone or in admixture with the glycerol formed as a by-product during their preparation from triglycerides, are used as inhibitors in acid pickling baths or are employed as from flotation agents.ALSO:Quaternary salts of polyoxyalkylated aminodiamides having a formula such as <FORM:0816617/VI/1> where R is a C8-22 unsaturated aliphatic radical, R1 is alkyl, allyl, hydroxyalkyl or aralkyl, R2 is H or C1-2 alkyl, X is an anion and n1, n2 and n3 each have a value of at least 1 and a total value ranging from 4 to 20, and similar compounds based on polyalkylene polyamines generally (see Group IV (b) for preparation), alone or in admixture with the glycerol formed as a by-product during their preparation from triglycerides, are used in emulsifier systems of insecticide compositions and agricultural sprays such as D.D.T., 2 : 4-D, toxaphene, chlordane, dormant or mineral oil sprays, nicotine sulphate, Dieldrin, Aldrin, Lindane, sulphur, B.H.C., Heptachlor, I.P.C., Chloro I.P.C., and Methoxychlor.