Preparation of methacrylamides
AssigneeThe Goodyear Tire & Rubber Company
InventorRoger W. Spoerke
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Abstract
An improved process for the preparation of methacrylamides from primary amines, methacrylic esters, and base catalysts such as alkoxides and amides. Some products are obtained in the form useful as comonomers in the preparation of elastomers.
Claims12
A process for the production of a polymer containing a bound methacrylamide antioxidant comprising (a) reacting a methacrylic ester with an amine in an organic solvent having a boiling point above 100.degree. C. in the presence of a basic metallic catalyst to yield an intermediate metallic salt, (b) removing the salt from solution, (c) washing the salt with an organic solvent, (d) at least partially drying the salt, and (e) adding the salt as a comonomer to an aqueous polymerization system wherein an in situ hydrolysis occurs during the polymerization reaction and wherein the methacrylic ester has the general structure (I) ##EQU2## the amine has the general structure (II) ##SPC5##
- and the basic metallic catalyst is selected from the group consisting of alkoxy metal halide bases having the formula R.sup.5 OZX, alkali metals, alkaline earth metals and amides, hydrides, hydroxides and alkoxides of alkali metals and alkaline earth metals, and wherein R.sup.1 is a radical selected from the group consisting of alkyl radicals having from 1 to 10 carbon atoms, aryl radicals having from 6 to 12 carbon atoms, cycloalkyl radicals having from 5 to 12 carbon atoms, A is selected from the group consisting of HO-- and R.sup.2 NH wherein R.sup.2 is selected from the group consisting of hydrogen, alkyl radicals having from 1 to 20 carbon atoms, cycloalkyl radicals having from 5 to 12 carbon atoms, aryl radicals having from 6 to 12 carbon atoms, aralkyl radicals having from 7 to 13 carbon atoms and wherein R.sup.3 and R.sup.4 are the same or different radicals selected from the group consisting of hydrogen and tert. alkyl radicals having from 4 to 8 carbon atoms and wherein R.sup.5 is an alkyl radical, Z is an alkaline earth metal selected from the group consisting of magnesium and calcium, and X is a halide selected from the group consisting of chlorine and bromine.
Dependencies are inferred from the claim text.