Polymers including a methylene beta-ketoester and products formed therefrom
The present teachings are directed at 1,1-disubstituted alkene monomers (e.g., methylene beta-ketoester monomers), methods for producing the same, polymerizable compositions including a methylene beta-ketoester monomer, and polymers, compositions and products formed therefrom. The monomer preferably is a high purity monomer. In the method for producing the methylene beta-ketoesters of the invention, a beta-ketoester may be reacted with a source of formaldehyde. The methylene beta-ketoester monomers may be used in monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).
1. A polymer prepared from a polymerizable composition comprising:
at least one methylene beta-ketoester monomer having the structural formula:
wherein R 1 and R 2 are independently C 1 -C 15 alkyl, C 2 -C 15 alkenyl, halo-(C 1 -C 15 alkyl), C 3 -C 6 cycloalkyl, halo-(C 3 -C 6 cycloalkyl), heterocyclyl, heterocyclyl-(C 1 -C 15 alkyl), aryl, aryl-(C 1 -C 15 alkyl), heteroaryl or heteroaryl-(C 1 -C 15 alkyl), each of which may be optionally substituted by C 1 -C 15 alkyl, halo-(C 1 -C 15 alkyl), C 3 -C 6 cycloalkyl, halo-(C 3 -C 6 cycloalkyl), heterocyclyl, heterocyclyl-(C 1 -C 15 alkyl), aryl, aryl □(C 1 -C 15 alkyl), heteroaryl, C 1 -C 15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester;
or
wherein R 1 and R 2 are taken together with the atoms to which they are bound to form a 5-7membered heterocyclic ring which may be optionally substituted by C 1 -C 15 alkyl, halo-(C 1 -C 15 alkyl), C 3 -C 6 cycloalkyl, halo-(C 3 -C 6 cycloalkyl), heterocyclyl, heterocyclyl-( C 1 -C 15 alkyl), aryl, aryl □(C 1 -C 15 alkyl), heteroaryl, C 1 -C 15 alkoxy, C 1 -C 15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester; and
wherein the amount of ketals in the polymerizable composition is less than about 100 ppm and/or the amount of latent acid-forming impurities in the polymerizable composition is less than about 100 ppm.
2. The polymer prepared from the polymerizable composition of claim 1 , wherein the polymer includes a difunctional monomeric cross-linking agent.
3. The polymer prepared from the polymerizable composition of claim 1 ,
wherein R 1 and R 2 are independently C 1 -C 6 alkyl or aryl.
4. The polymer prepared from the polymerizable composition of claim 1 , wherein the methylene beta-ketoester monomer has the structure:
5. The polymer prepared from the polymerizable composition of claim 1 , wherein the methylene beta-ketoester monomer has the structure:
6. The polymer prepared from the polymerizable composition of claim 1 further comprising one or more components which include tougheners, plasticizers, thixotropic agents, rubbers or reinforcing agents.
7. The polymer prepared from the polymerizable composition of claim 1 , wherein the polymer is a fiber, a film, a sheet, a medical polymer, a composite polymer or a surfactant.