Patent GB-883994-A (GB)
Title: Improvements in or relating to the production of oxazolidone products
IPC: C08G59/40
Filed: 1958-12-10
Abstract: Resinous products are prepared by heating a di-epoxide with an organic di-isocyanate in the presence of an addition catalyst which is a trialkylamine, an alkali metal halide or an ammonium compound of the general formula NR1R2R3R4.X wherein X is a halide ion and each R represents hydrogen or an alkyl, alkenyl, cyclo alkyl, aryl, aralkyl or alkaryl radical, numerous amines and quaternary ammonium halides being mentioned.  It is stated that addition of an isocyanate group to an epoxide group occurs with resulting formation of an oxazolidonyl group.  Reaction may be effected at above 100 DEG  C. in the presence of an inert solvent, and if desired under pressure.  In Examples: (6) vinyl cyclohexene dioxide is heated with 2,4-toluene di-isocyanate in dimethyl formamide using a minor amount of tetra ethyl ammonium bromide as catalyst yielding a high M.P. resin; (9) the di-epoxide obtained from epichlorhydrin and bis(4-hydroxy phenyl) dimethyl methane is heated with toluene di-isocyanate using N(CH3)4.I as catalyst.  The use of di-epoxides of the general formula <FORM:0883994/IV (a)/1> wherein R11, R111 and R1111 represent hydrogen or alkyl, alkenyl, cycloalkyl, aryl, aralkyl or alkaryl radicals and R1 is the group <FORM:0883994/IV (a)/2> is referred to.ALSO:Oxazolidones are prepared by heating an organic isocyanate with an oxirane in the presence of an addition catalyst which is a trialkylamine, an alkali metal halide or an ammonium compound NR1R2R3R4.X wherein X is a fluoride, chloride, bromide or iodide ion and each R represents hydrogen or an alkyl, alkenyl, cycloalkyl, aryl, aralkyl or alkaryl radical and numerour trialkylamines and quaternary ammonium halides are mentioned.  The isocyanates may be of the type R.NCO wherein R represents an alkyl, cycloalkyl, aryl, alkaryl or aralkyl radical which may bear another isocyanate group. The oxiranes may be mono- or di-epoxides and include those of the general formula <FORM:0883994/IV (b)/1> wherein R11, R111 and R1111 may be hydroge or an alkyl, alkenyl, cycloalkyl, aryl, aralkyl or alkaryl radical and R1 may have the same meaning or represent another oxirane group.  Reaction is generally effected at about 100 DEG C. in a sealed vessel, if desired, in the presence of an inert solvent. The oxazolidone formation results from addition of an isocyanate group to the epoxide group.  Reaction of a di-isocyanate with a diepoxide yields a resin (see Group IV(a)).  Examples describe the preparation of (1) 3-phenyl-2-oxazolidone from ethylene oxide and phenylisocyanate; (2) 3-phenyl-5-methyl-2-oxazolidone from propylene oxide and phenyl isocyanate; (3) 2,4-bis (3-oxazolidonyl) toluene from ethylene oxide and toluene di-isocyanate; (4) 3-ethyl-2-oxazolidone from ethylene oxide and ethyl isocyanate; and (5) 3-phenyl-5-n-decyl-2-oxazolidone from 1,2-dodecylene oxide and phenyl isocyanate, reaction being effected in a solvent with tetra ethyl ammonium bromide, triethylamine or KI as catalyst.  Numerous other reactants are specified including vinyl-cyclohexene di-oxide, the di-epoxide obtained by reacting epichlorhydrin with bis-(4-hydroxy phenyl) dimethyl methane, methyl isocyanate and benzyl isocyanate.