Rohm and Haas Company

Jerome F Levy

Sheldon N Lewis

William D Emmons

Napoleon L Horton

A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.

Method of preparing sulfonic acid salts of acyloxyalkylamines and

Method of preparing novel sulfonic acid salts of acyloxyalkylamines and

Sulfonic acid salts of acyloxyalkylamines

This invention concerns novel ester isocyanates derived from acyloxyalkylamine hydrochlorides. The novel compounds may contain a hetero atom in either the acid or alkanolamine moiety and may contain oxalic acid as the acyl moiety.

Novel ester isocyanates

The present invention is concerned with novel oxazolidines, polyoxazolidines, and particularly polymers of both condensation and addition type containing 1,3-oxazolidine groups linked to the polymer through an aliphatic ester linkage. They are the products of reaction between (1) 3-glycidyl-1,3-oxazolidines which may be substituted in the 2-position with an alkyl or aralkyl group and (2) a monocarboxylic acid, a polycarboxylic acid, or a polymer (of addition or condensation type) containing at least one carboxyl group. The polymeric products have improved adhesion when employed as adhesive or coating materials. The oxazolidine in such polymeric substances improves the usefulness of the polymers in regard to adhesiveness or cohesiveness when such polymers are used as coating compositions, adhesive compositions and for the molding of plastic articles. The non-polymeric products serve as intermediates which can be used as reactive components to react with carboxyl groups of addition or condensation polymers to introduce oxazolidine groups into such polymers to modify their adhesiveness. This application also covers methods of producing the new oxazolidine products and moisture-curable mixtures of a polyisocyanate and a reaction product of (1) and (2) above.

Oxazolidine, oxazolidine-containing condensation and addition polymers

Novel acyl-containing amine hydrochlorides are produced by first converting the amino group or groups of an amino acid to an acid salt by reaction with hydrochloric acid and the resulting product is reacted with an alkanolamine or diol in an inert liquid medium while passing a stream of hydrogen chloride gas therethrough. The amine hydrochlorides produced in this manner may be converted to the corresponding isocyanates by reaction with phosgene or other carbonyl dihalide.

Aliphatic acyl-containing amine hydrochlorides

New products and methods for their preparation; principally, 3-(glycidyl)-1,3-oxazolidines and derivatives thereof obtained via the reaction of a 3-(glycidyl)-1,3-oxazolidine with an amine, alcohol, sulfonate, mercaptan, azide or cyanide. Also covered are oxazolidines containing a carboxy function which are obtained by treating a 3-(glycidyl)-1,3-oxazolidine with a mono-or poly-carboxylic acid. The products are useful in improving the adhesiveness of polymers and in promoting the room temperature cure of isocyanate and anhydride polymers to afford new plastic, adhesive and coating materials.

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Dresher, PA, United States of America

Jerome F Levy