Patent GB-1072118-A (GB)
Title: Amides of aminopropionic acid
Inventor: HOFFER KURT
IPC: C07C237/00
Filed: 1963-11-27
Abstract: Novel basic amides are prepared by first reacting 1 to 2 mol of an ester of acrylic acid with a volatile alcohol, at a temperature below 100 DEG  C. at which no substantial amidation occurs, with one mol. of primary, secondary or tertiary amine of the formula <FORM:1072118/C2/1> to form an ester-amine which is then further heated with 1 to 2 mol. of a primary, secondary or tertiary amine of the formula <FORM:1072118/C2/2> to form an amide-amine with simultaneous splitting off of an alcohol, said amide-amine being subsequently alkylated, alkoxylated and/or quaternated and/or acylated if desired, one of R1, R2 and R3 representing C12- 24 alkyl or alkenyl, each of the remaining five of R1 to R6 representing hydrogen or C1- 6 alkyl or hydroxyalkyl, A1 and A2 each representing a C2- 6 alkylene radical and each of m and n representing 0 or an integer of from 1 to 6 inclusive provided that at least one represents an integer. Examples describe the preparation of (1) a 1 :2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1,6-hexamethylene-diamine and either ethoxylation and quaternization, methylation, or propionylation and methylation of the resulting stearylamino-dipropionic acid di-1-aminohexyl-6-amide; (2) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1,3-propylenediamine and either ethoxylation and quaternization, methylation or acetylation and methylation of the resulting stearylamino-propionic acid 1-aminopropyl-3-amide; (3) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1,2-ethylenediamine and either methylation or methylation and acetylation of the resulting stearylamino-propionic acid 1-aminoethyl-2-amide; (4) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of 1,6-hexamethylenediamine and either methylation, alkoxylation or alkoxylation and quaternization (with monochloracetic acid) of the resulting stearylamino-propionic acid 1-aminohexyl-6-amide; (5) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of 1-amino-3-dimethylaminopropane and either methylation or carbamidomethylation (with chloroacetamide) of the resulting stearylaminopropionic acid 1-dimethylaminopropane 3-amide; (6) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of diethylene-triamine and methylation of the resulting monostearylamino-propionic acid amide of diethylene-triamine; (7) a 1:2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1,3-propylene-diamine and methylation of the resulting stearylamino-dipropionic acid di-1-aminopropane-3-amide; and (8) a 1:2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1-amino-3-dimethylaminopropane and quaternization of the resulting stearylamino-dipropionic acid di-3-dimethylamino-propane-1- amide with either methyl sulphate or chloroacetamide.ALSO:Novel amino-amides containing a C1- 24 alkyl or alkenyl group in addition to C1- 6 alkyl or hydroxyalkyl groups (see Division C2) are alkoxylated and, if desired, further quaternated or acylated.  The amino-amides and their quaternary derivatives may be used as polymerization emulsifiers.  In examples a stearylamine - dipropionic acid di - 1 - aminohexyl-6-amide is ethoxylated with up to 75 mols. of ethylene oxide and subsequently quaternized with dimethyl sulphate and alternatively with chloroacetic acid; a stearylamine-propionic acid 1-aminopropyl-3-amide is ethoxylated with up to 30 mols. of ethylene oxide and subsequently quaternized with monochloroacetic acid or alternatively dimethyl sulphate, benzyl chloride, chloroacetamide, glycolchlorohydrin or epichlorohydrin; a stearylaminopropionic acid 1-aminohexyl-6-amide is propoxylated with 2.4 mols. of propylene oxide and subsequently quaternized with chloroacetic acid; a stearylamine-propionic acid 1-aminohexyl-6-amide quaternized with 2 mols. of dimethyl sulphate is added to an emulsion polymerization system containing aqueous sodium bisulphite, vinyl acetate, ferrous sulphate and hydrogen peroxide; and a stearylamine-propionic acid 1-aminopropyl-3-amide methylated with two mols. of dimethyl sulphate is added to an emulsion polymerization system containing aqueous sodium bisulphite, ethyl acrylate, butyl acrylate, acrylonitrile, ferrous sulphate and hydrogen peroxide; the polymer emulsions may be used for treating textiles or paper.ALSO:Novel amino-amides containing a C12-24 alkyl or alkenyl group in addition to C1-6 alkyl or hydroxyalkyl groups (see Division C2) and their quarternary or alkoxylated derivatives are used as levelling agents in dyeing baths or as emulsifying agents in emulsion polymerization systems, to which they impart improved paper sizing properties.  In examples the products are used in a dyebath containing 2:1 metal complex dyes, ammonium sulphate, and formic acid to obtain a level dyeing effect on striped dyeing nylon woven material, and in an emulsion polymerization system containing aqueous sodium bisulphite, ferrous sulphate, hydrogen peroxide, ethylacrylate, butyl acrylate and acrylonitrile, this being used to size bleached sulphite cellulose in conjunction with rosin size, aluminium sulphate, kaolin and an optical brightening agent.