Patent GB-930668-A (GB)
Title: Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams
IPC: C07D207/27
Filed: 1959-08-19
Abstract: The invention comprises polymers and copolymers of compounds of formula <FORM:0930668/IV(a)/1> where A is C2-10 alkylene with 2 to 4 carbon atoms in the lactam ring, x is an integer from 1 to 4, n is an integer from 1 to 4 when x is 1 and from 2 to 4 when x is greater than 1, R0 is hydrogen or C1-6 alkyl and R is acryloyl or methacryloyl, the CnH2nO groups present when x is greater than 1 being the same or different.  In In examples polymers are prepared from N-(methacryloxyethoxyethyl) pyrrolidinone and N-(methacryloxyethoxyethoxyethyl) - pyrrolidinone by heating with azodiisobutyronitrile.  The addition of 2-10% of such a polymer or copolymer to a monomer such as methyl methacrylate or a mixture of methyl methacrylate and ethyl acrylate in an organic solvent, either before or after polymerization of said monomer improves adhesion to metals and may be used in lacquers.  The monomers of Formula I may be used in polyvinyl chloride plastisol compositions, e.g. a composition containing polyvinyl chloride, dioctyl phthalate, methacryloxyethyl pyrrolidinone and t-butyl perbenzoate is prepared by mixing on rollers, and then moulded, fluxed at 350 DEG F. and cooled.ALSO:The invention comprises compounds of formula <FORM:0930668/IV(a)/1> where A is an alkylene group of 2 to 10 carbon atoms with 2 to 4 carbon atoms in the heterocyclic ring, x is an integer from 1-4, n is an integer from 1-4 when x is one and from 2-4 when x is greater than 1, R DEG  is hydrogen or C1-6 alkyl, and R is acryloyl or methacryloyl, the CnH2nO groups present when x is greater than one being the same or different.  They are prepared from the corresponding hydroxy compounds of formula <FORM:0930668/IV(a)/2> by (1) alcoholysis with an acrylic or methocrylic ester containing up to 10 carbon atoms or (2) reaction with an acryloyl or methacryloyl halide in the presence of a hydrogen halide acceptor.  Catalysts for method (1) include alkali metal and quaternary ammonium alkoxides including alkali metal derivatives of compounds of formula II, aromatic and aliphatic sulphonic acids and tetralkyl titanates, amounts of catalyst of 0.1-5% of the weight of compound II being mentioned; reflux temperatures, e.g. 65-140 DEG C., are mentioned; reduced pressure may be used.  For method (2), temperatures of 0 to about 60 DEG C. are mentioned; an organic solvent may be present.  Polymerization inhibitors may be included in the reaction mixtures or added subsequently.  The starting materials of formula II in which both n and x are 1 may be prepared by reacting the corresponding lactams with formaldehyde using an alkaline catalyst; N-methylol-E-caprolactam and -piperidinone are thus prepared in Example 8.  Other compounds in which x is 1 may be prepared by heating lactones with aminoalkanols; specific compounds thus prepared are: N-(3-hydroxypropyl)-, N - (3-hydroxybutyl), N - 2 - (1-hydroxy-2-methylpropyl)-, and N-2-(hydroxybutyl)-pyrrolidinone. Alternatively the corresponding pyrollinones, obtained by the hydrolysis by heating with water of pyrrolines, may be hydrogenated. Compounds with other sizes of lactam ring may be prepared by analagous methods.  The compounds in which x is greater than one may be obtained by reacting N-hydroxyalkylactams with one or more alkylene oxides in one or more stages.  Specified compounds thus prepared areN-hydroxy-ethoxyethyl, N-hydroxyethoxyethoxyethyl and N-hydroxyethoxyethoxyethoxy-, ethyl pyrrolidinones and a mixture of N-hydroxy-ethoxyethyl- and N- hydroxyethoxyethoxyethyl-3-methyl-3, 5-diisobutylpyrrolidinones.  Many other compounds of formula II are mentioned,