Exxon Research and Engineering Company

Daniel N Hall

Alexis A Oswald

Wolfgang H Mueller

Phosphorylsulfenyl halides are added to monoolefins, multiolefins, conjugated multiolefins and acetylenic compounds. 1,2-Markownikov oriented adducts are the principle products when conjugated diolefins are employed as the starting feedstock. Anti-Markownikov adducts are obtained as major products when unsymmetrical monoolefins and nonconjugated multiolefins are used as the starting material. The addition reactions are conducted at low temperatures. The materials which are obtained are of interest as pesticides and as intermediates in the synthesis of pesticides.

Phosphoryl sulfenyl chloride olefin adducts

Acylthiosulfenyl halides, phosphorylsulfenyl halides, and thiophosphorylsulfenyl halides are added to monoolefins, multiolefins and acetylenic compounds. 1,2-Markownikov oriented adducts are the principal products when conjugated diolefins are employed as the starting feedstock. Anti-Markownikov adducts are obtained as major products when unsymmetrical monoolefins and nonconjugated multiolefins are used as the starting material. The addition reactions are conducted at low temperatures.

Addition of sulfenyl halides to olefins and acetylenes

Polythiols having more than two terminal and/or pendant thiol groups per polymer molecule are formed by the free radical catalyzed addition of a monomer system made up of either hydrogen sulfide or a dithiol alone or in combination with an acetylenic compound to a polyolefin having at least three olefin sites. The polyolefin is preferably a tri-terminal olefin. The polythiol products are liquid, essentially gel-free materials having number average molecular weights varying from 200 to 30000. The polyfunctional prepolymers of the invention can be cured to stable three-dimensional networks with inexpensive bi-functional oxidants such as lead dioxide. Additionally, prepolymer compositions having 3 or more pendant or terminal thiol groups per molecule when combined with polyfunctional organic reagents, such as diepoxides, form stable, high-tenacity adhesive systems.

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Daniel N Hall