Patent GB-786927-A (GB)
Title: N-vinyloxyalkyl-alkanecarboxamides
IPC: C08F16/28
Filed: 1955-12-07
Abstract: The invention comprises compounds of the formula CH2:CH.O.A.NR.CO.R1, where A is C2 or C3 alkylene with at least 2 carbon atoms between the O and N, R is H or methyl and R1 is C11-C17 alkyl.  These are made by acylating the corresponding aminoalkyl vinyl ethers with the fatty acid ester or chloride.  Examples show the production of N-(b -vinyloxyethyl)-stearamide, N - (b  - vinyloxyethyl) - lauramide, N-(g  - vinyloxypropyl) - palmitamide and N-methyl - N - (g  - vinyloxypropyl) - palmitamide.  Other amines that may be acylated are N-methyl - b  - vinyloxyethylamine, b  - vinyloxypropylamine, b  - vinyloxy - isopropylamine and the N-methyl derivatives of the last two.ALSO:Surface-active polymers useful in the sizing, conditioning and dressing of textiles (e.g. mercerization of cotton and rayon) are obtained by copolymerizing a compound of the formula CH2 : CH.O.A.NR.CO.R1 with either (a) a water-soluble monomer such as acrylamide, ureidoethyl vinyl ether, formamidoethyl vinyl ether, vinylpyrrolidone or hydroxyethyl acrylate or methacrylate; or (b) a vinyl ester with subsequent hydrolysis of the ester group.  The polymers are useful in preparing dispersions of other coating materials since they have film-forming properties themselves.  In the formula above A is C2-C3 alkylene with at least 2 carbon atoms between the O and N, R is H or methyl and R1 is C11-C17 alkyl.  In an example the copolymer from N-(b -vinyloxyethyl)-lauramide and ureidoethyl vinyl ether is added to aqueous sodium hydroxide for the mercerization of cotton.  It is also stated that the monomer N - methyl - N - (g  - vinyloxypropyl)-palmitamide and polymeric N-(b -vinyloxyethyl)-lauramide are useful as lubricants for yarns and threads.ALSO:Polymers of compounds of the formula CH2:CH.O.A.NR.CO.R1, where A is C2-C3 alkylene with at least 2 carbon atoms between the O and N, R is H or methyl and R1 is C11-C17 alkyl are useful as components of waxes and as gelling agents for hydrocarbons, such as gasoline, for use in flame-throwers.  Those in which R is methyl improve the viscosity index of lubricating mineral oils when present in 2-6 per cent by weight of the oil.  A particular substance for this latter purpose is the copolymer of N-methyl- N - (b  - vinyloxyethyl) - lauramide and N - (b  - vinyloxyethyl)-stearamide.  It is also stated that the copolymer of N-(b -vinyloxyethyl)-lauramide and ureidoethyl vinyl ether is surface-active can be used in conjunction with soap to form a built soap detergents.ALSO:The invention comprises polymers and copolymers of compounds of the formula CH2:CH.O.A.NR.CO.R1 where A is C2 or C3 alkylene with at least 2 carbon atoms between the O and N, R is H or methyl and R1 is C11-C17 alkyl.  The compounds may be copolymerized with vinyl and vinylidene halides; isobutylene, butadiene and its halogen derivatives, styrene; esters, amides and nitriles of acrylic, haloacrylic and methacrylic acids; vinyl ethers and esters; unsaturated aldehydes and ketones; N-vinyl imides, -lactams and -pyridines; tetrafluorethylene; diethyl fumarate and maleate; many compounds of the above types are specified.  Polymerization may be effected in bulk, in solution or in emulsion, using a catalyst of the acyclic azo type.  Surface-active compounds are obtained by copolymerizing 1-25 per cent of the monomers with 99-75 per cent of water-soluble monomers such as acrylamide, ureidoethyl vinyl ether, formamidoethyl vinyl ether, vinylpyrrolidone, or hydroxyethyl acrylate or methacrylate. Alternatively a vinyl ester such as the acetate or propionate can be used and the polymer subjected to alkaline hydrolysis to split the ester group without affecting the amide group.  Examples show the polymerization of N-(b -vinyloxyethyl)-lauramide and N-(b -vinyloxyethyl)-stearamide, and the preparation of copolymers from (1) N-methyl-N-(g -vinyl-oxypropyl)-palmitamide and methyl methacrylate; (2) N - (b  - vinyloxyethyl) - lauramide and ureidoethyl vinyl ether; and (3) N-(b -vinyloxyethyl) - stearamide and N - methyl - N - (b  - vinyloxyethyl) - lauramide.  Other suitable monomers are mentioned.