Air Products and Chemicals, Inc.

Walter L Renz

Robert K Pinschmidt, Jr

Ning Chen

William Eamon Carroll

David A Cornforth

Andrew Francis Nordquist

Chung-Ling Mao

Richard A Bafford

Jeffrey A Kuphal

Lori A Vratsanos

W Eamon Carroll

Dawn Fowler

Dawn Howell

N-vinyl compositions comprising 3-(N-vinylformamido)propionamides and 2-methyl-3-(N-vinylformamido)propionamides containing terminal amino, hydroxyl or a second N-vinyl group are obtained by amidation of the corresponding propionate ester with appropriate alkylamines. The invention also describes a process for preparing these compounds. The subject materials are useful as monomers in free radical polymerization as well as precursors in the preparation of unsaturated resins.

Functional N-vinylformamides

A process is provided for the synthesis of N-vinylformamidopropionates by the reaction of NVF with acrylic and methacrylic acid esters in the presence of a metal hydride catalyst. This process allows for the improved production of mono-functional monomers and also for the synthesis of new multi-functional monomers which are useful as crosslinkers and chain extenders in photo-cure applications.

N-vinylformamidopropionates and process for their synthesis

This invention pertains to aqueous emulsions containing water insoluble, vinyl polymer particles containing polymerized Michael adduct units of N-vinylformamide and to emulsions of vinyl acetate polymers containing said Michael adducts. These latex dispersions are prepared by the emulsion polymerization of a Michael adduct of N-vinylformamide, optionally with other ethylenically unsaturated monomers, e.g., vinyl acetate. The Michael adducts of N-vinylformamide are represented by the formula: ##STR1## where R is H or CH.sub.3, X=CN, O=CR.sub.1, O=COR.sub.1 or other electron withdrawing group such as SO.sub.3 M, SO.sub.3 R.sub.1 and NO.sub.2 wherein R.sub.1 is a linear or branched alkyl, cycloalkyl, heterocyclic, arylalkyl, alkyloxy or aryl group containing between 1 and about 20 carbon atoms and substituted derivatives thereof and M is an ion. The preferred Michael adduct N-vinyl amide monomers are unsaturated monomers consisting of the alkl 3-N-vinylformamidopropionates and alkyl 2-methyl-3-N-vinylformamidopropionates and represented by the formula: ##STR2## where R is hydrogen or methyl, and R.sup.1 is a linear or branched alkyl, cycloalkyl, heterocyclic, arylalkyl, alkyloxy or aryl group containing between 1 and about 20 carbon atoms.

Aqueous polymeric emulsions incorporating polymerized units of michael

Novel unsaturated compounds comprising the 3-(N-vinylformamido)propionates and 2-methyl-3-(N-vinylformamido)propionates, or the corresponding propionamides, are obtained by the Michael addition reaction of N-vinylformamide with an acrylic or methacrylic acid ester. These compounds are useful as monomers in free radical polymerizations, particularly as components of photocurable coatings.

N-vinylformamide/alkyl acrylate Michael adducts

A class of unsaturated resins which are suitable for use in radiation curable coatings has been developed. The resins comprise N-vinyl-N-acyl oligomers made by reacting a secondary N-vinylamide with a polyisocyanate monomer which is reacted with at least one mono- or polyhydric alcohol to form a urethane linkage.

N-vinyl-n-acyl urea resins

A composite structure which comprises, in intimate jointed lamination, a substrate layer, and intermediate adhesion layer, and a tightly adhered polymeric film, the adhesion layer comprising an aqueous emulsion polymer containing a vinylamine homopolymer or copolymer, preferably polyvinyl alcohol/polyvinylamine copolymer.

Use of vinylamine homopolymers and copolymers in film lamination

Novel unsaturated compounds comprising the 3-(N-vinylformamido)propionates and 2-methyl-3-(N-vinylformamido)propionates are obtained by the Michael addition reaction of N-vinylformamide with an acrylic or methacrylic acid ester. These compounds are useful as monomers in free radical polymerizations, particularly as components of photocurable coatings.

Michael adducts of N-vinylformamide and acrylic and methacrylic esters

A process is provided whereby radiation curable compositions comprising N-vinylformamide and an oligomer selected from the group consisting of epoxy-acrylate resins, polyester acrylate resins, polyurethane acrylate resins, acrylic acrylate resins, silicone acrylate resins, unsaturated polyester resins, maleate ester resins, vinyl ether resins and mixtures thereof are applied to the surface of a substrate and subsequently exposed to a radiation source until an adherent dry polymerized film is formed on the substrate. These compositions are useful for a wide range of applications including pigmented and unpigmented coatings, printing inks, adhesives and the like.

Coating process using radiation curable compositions

Improved radiation curable compositions are provided which comprises N-vinylformamide and an oligomer selected from the group consisting of epoxy-acrylate resins, polyester acrylate resins, polyurethane acrylate resins and mixtures thereof. A photoinitiator is also added to the composition. A process is also provided whereby the composition is applied to the surface of a substrate and subsequently exposed to a radiation source until an adherent dry polymerized film is formed on the substrate. These compositions are useful as pigmented and unpigmented coatings, printing inks, adhesives and the like.

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Macungie, PA, United States of America

Walter L Renz