Abstract:
Ink and coating compositions, printing and coating processes, and printed and coated substrates utilizing a polymerizable composition comprising one or more di-activated vinyl compounds, with the proviso that said a di-activated vinyl compound is not a cyanoacrylate. Exemplary compositions include methylene malonates, methylene β-ketoesters, methylene β-diketones, dialkyl disubstituted vinyls, and dihaloalkyl disubstituted vinyls. Exemplary compositions are polymerizable at ambient temperatures.
Abstract:
A composite material comprises a reinforcing material carried in a polymer matrix material which is the polymerization product of a polymerizable composition comprising a di-activated vinyl compound, with the proviso that the di-activated vinyl compound is not a cyanoacrylate. The reinforcing materials may be a wide variety of substrates including thermally sensitive materials. Exemplary composites can be molded and cured at ambient temperatures. Also disclosed are laminate materials having layered materials adhered by curing a di-activated vinyl polymerizable composition.
Abstract:
Method to obtain methylene malonate and related monomers following a bis(hydroxymethyl) malonate pathway. A bis(hydroxymethyl) malonate intermediary is subsequently reacted (i.e., subjected to thermolysis) to provide a methylene malonate monomer species. A source of formaldehyde (e.g., formalin) is provided in the presence of a basic catalyst (e.g., calcium hydroxide), to which a malonate (e.g., diethyl malonate) is added under suitable reaction conditions to obtain the desired intermediary (e.g., dialkyl bis(hydroxymethyl) malonate). The intermediary is reacted (i.e., subjected to thermolysis) under suitable conditions in the presence of a suitable catalyst (e.g., a zeolite) to obtain a methylene malonate monomer. In an exemplary embodiment, the thermolysis reaction includes the addition of the bis(hydroxymethyl) malonate intermediary onto a heated catalyst. The reaction product is collected and purified. The disclosed methods may be performed in a continuous operation. Discrete steps may be performed by using modular units within a plant.
Abstract:
The exemplary embodiments disclosed herein relate to activating methods for initiation polymerization of methylene malonates and other polymerizable compositions. The polymerization may be activated by anionic or free radical mechanisms. Because the polymerization may occur very quickly upon contact between the activating agent and the polymerizable composition, methods are provide herein for separating or otherwise rendering the activating agent ineffective to initiate polymerization, until such a reaction is desired. The separation may be physical (separate packaging, separate application steps, encapsulation) or it may be based on latent- activation methods (activation precursors, UV activation). Products formed from the methods disclosed herein may include inks, adhesives, coatings, sealants, reactive moldings, fibers, films, sheets, medical polymers, composites, laminates and the like. Exemplary polymerizable compositions and products formed therefrom are environmentally sustainable, environmentally benign and/or biologically benign.
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. 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 and polymer-based products.
Abstract:
The present invention provides methylene beta-diketone monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-diketones of the invention, a beta-diketone is reacted with a source of formaldehyde in a modified Knoevenagel reaction 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 complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-diketone monomer. The present invention further compositions and products formed from methylene beta-diketone monomers of the invention, including 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).
Abstract:
An electronics composition includes a curable matrix material and, optionally, a filler material disposed within the matrix material. The cured matrix material includes an oligomer or polymer material derived from a compound selected from a methylene malonate monomer, a multifunctional methylene monomer, a methylene beta ketoester monomer, a methylene beta diketone monomer, or a mixture thereof.
Abstract:
Reactive composition includes a reactive component able to form an adhesive bond between two substrates, at least one of which comprises a plastic material. The substrate may include an initiator on or near the surface thereof. The initiator may be present in the plastic material inherently, by blending in an additive package, through injection molding, or other process. The reactive component may comprise a methylene malonate, a reactive multifunctional methylene, a methylene beta ketoester, a methylene beta diketone. A carrier component for the reactive component may be selected to interact with the plastic substrate to soften and/or penetrate the surface to be bonded. The surface of the plastic may be abraded or otherwise treated to expose the initiator. The reactive component, upon contact with a suitable initiator, is able to polymerize to form an interpenetrating polymer weld.
Abstract:
Optical materials including polymerizable compositions and oligomeric and polymeric material formed therefrom. The oligomer or polymer material include structural repeat units represented by any of the formulas selected from (II), (III) and (IV). The optical material has low or substantially no absorbance of wavelengths in at least one of the spectral regions of interest. Optical components include adhesives, waveguides, spherical or non-spherical optical lenses, architectural articles, automotive components, laminated structures and composites.
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).