Verfahren zur Herstellung von Oxazolidinonderivaten

摘要

12 gms. of phenylisocyanate was mixed with 41.5 gms. of isopropylidene bis[1-(p-phenyleneoxy)-3-chloro-2-propanol], methylene chloride and stannous octoate (catalyst) and allowed to stand for sixteen hours at room temperature. The resulting product was dehydrohalogenated to the epoxyoxazolidinone by adding NaOH in dioxan at 70-75 DEG C. The mixture was cooled, neutralized with CO2, filtered and dried, to obtain a viscous yellow syrup.ALSO:Poly - (beta - haloalkylurethano) halohydrin compounds are prepared by reacting an organic polyisocyanate with a poly-(halohydrin) in quantities providing 1.1-4.0 halohydrin groups per -NCO group. The term "beta-haloalkylurethano" refers to the radical where X is a halogen, the term "poly-(beta - haloalkylurethano) halohydrin" means compounds containing two or more halohydrin groups where X is a halogen and two or more beta-haloalkylurethano radicals. The isocyanate may be a compound containing two or more -NCO or -NCS radicals. The poly-(halohydrin) may be of formula where m is an integer between 2 and 5, X is a halogen and Z1 is a polyvalent organic radical or a covalent bond directly connecting two halohydrin moieties. The polyisocyanate is preferably tolylene diisocyanate and the poly-(halohydrin) is poly-(epichlorhydrin) or isopropylidene bis - [1 - (p - phenyleneoxy) - 3 - chloro - 2 - propanol]. The polyisocyanate may be the reaction product of tolylene diisocyanate and polypropylene glycol and the poly-(halohydrin), the adduct of epichlorohydrin with polyethylene glycol or trimethylolpropane. In a typical Example (6) an adduct of tolylene diisocyanate and polypropylene glycol was reacted with an adduct of epichlorhydrin and polypropylene glycol. The product was dehydrohalogenated with sodium hydroxide to yield an epoxyoxazolidinone which was dissolved in acetone and used as a plasticizer for a 1/1 ethyl acrylate/methyl methacrylate polymer dissolved in toluene. Epoxy oxazolidinones may also be used as plasticizers for polyvinyl chloride. In Example (3) an epoxy resin was prepared by dihydrohalogenating the reaction product of tolylene diisocyanate (17 gms.) and isopropylidene bis - [1 - (p - phenyleneoxy) - 3 - chloro - 2 - propanol] (85 gms.) with aqueous NaOH. The polyepoxides obtained by dehydrohalogenation of the halohydrins with alkali are cured with conventional curing agents for epoxy resins.