Abstract: The present invention provides a method of making a methylene malonate monomer that includes the steps of reacting a malonic acid ester with a source of formaldehyde optionally in the presence of an acidic or basic catalyst and optionally in the presence of an acidic or non-acidic solvent to form reaction complex. The reaction is optionally performed in the presence of or contacted with an energy transfer means such as a heat transfer agent, a heat transfer surface, a source of radiation or a laser such that reaction complex is substantially vaporized to produce a vapor phase comprising methylene malonate monomer which may be isolated. The present invention further provides methylene malonate monomers prepared by the method of the invention, as well as compositions and products formed from the methylene malonate monomers, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g.
Type:
Grant
Filed:
October 19, 2011
Date of Patent:
November 11, 2014
Assignee:
Bioformix Inc.
Inventors:
Bernard M. Malofsky, Adam G. Malofsky, Tanmoy Dey, Jeffrey M. Sullivan, Yangbin Chen, Stanley C. Wojciak, Michael C. Cockrem
Abstract: The present invention provides improved methods for the chemical synthesis of methylene malonates using the Knovenagel synthesis reaction. The method of the invention provides for improved methylene malonates by significantly reducing or eliminating the formation of alternative and/or deleterious side products, significantly reducing or eliminating unwanted consumption of methylene malonates, and significantly reducing or eliminating the degradation of methylene malonates. These advantages result in methylene malonates, which upon recovery, are of higher quality, greater purity, improved yield and possess overall improved performance characteristics (e.g., improved cure speed, retention of cure speed, improved shelf-life and/or stability).
Type:
Application
Filed:
November 8, 2013
Publication date:
September 4, 2014
Applicant:
Bioformix Inc.
Inventors:
Bernard M. Malofsky, Adam G. Malofsky, Tanmoy Dey, Jeffrey M. Sullivan, Yangbin Chen, Stanley C. Wojciak
Abstract: The present invention provides improved methods for the chemical synthesis of methylene malonates using the Knovenagel synthesis reaction. The method of the invention provides for improved methylene malonates by significantly reducing or eliminating the formation of alternative and/or deleterious side products, significantly reducing or eliminating unwanted consumption of methylene malonates, and significantly reducing or eliminating the degradation of methylene malonates. These advantages result in methylene malonates, which upon recovery, are of higher quality, greater purity, improved yield and possess overall improved performance characteristics (e.g., improved cure speed, retention of cure speed, improved shelf-life and/or stability).
Type:
Grant
Filed:
October 19, 2011
Date of Patent:
December 17, 2013
Assignee:
Bioformix Inc.
Inventors:
Adam G. Malofsky, Tanmoy Dey, Jeffrey M. Sullivan, Yangbin Chen, Stanley C. Wojciak, Bernard M. Malofsky
Abstract: The present invention provides a method of making a methylene malonate monomer that includes the steps of reacting a malonic acid ester with a source of formaldehyde optionally in the presence of an acidic or basic catalyst and optionally in the presence of an acidic or non-acidic solvent to form reaction complex. The reaction is optionally performed in the presence of or contacted with an energy transfer means such as a heat transfer agent, a heat transfer surface, a source of radiation or a laser such that reaction complex is substantially vaporized to produce a vapor phase comprising methylene malonate monomer which may be isolated. The present invention further provides methylene malonate monomers prepared by the method of the invention, as well as compositions and products formed from the methylene malonate monomers, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g.
Type:
Application
Filed:
October 19, 2011
Publication date:
October 24, 2013
Applicant:
BIOFORMIX INC.
Inventors:
Bernard M. Malofsky, Adam G. Malofsky, Tanmoy Dey, Jeffrey M. Sullivan, Yangbin Chen, Stanley C. Wojciak, Michael C. Cockrem