Abstract: Disclosed are methods for the catalytic transesterification of compounds having one or more ester groups and groups reactive under transesterification conditions, such as 1,1-disubstituted alkene compounds, with alcohols or esters and novel compositions prepared therefrom. Further disclosed are novel compounds and compositions prepared as a result of the methods.
Type:
Grant
Filed:
July 31, 2015
Date of Patent:
August 16, 2016
Assignee:
SIRRUS, INC.
Inventors:
Jeffrey M. Sullivan, Aniruddha Sudhir Palsule, Peter Rulon Stevenson, Kshitij Kishen Parab
Abstract: An encapsulated initiator particle includes one or more polymerization initiators encapsulated by a cured composition. The cured composition includes one or more 1,1-disubstituted alkene compounds. Polymerizable systems can include one or more encapsulated initiator particles and a polymerizable composition. The polymerizable composition can include one or more 1,1-disubstituted alkene compounds. Methods for forming an encapsulated initiator particle are also described herein.
Type:
Grant
Filed:
May 29, 2015
Date of Patent:
May 10, 2016
Assignee:
Sirrus, Inc.
Inventors:
Peter Rulon Stevenson, Aniruddha Sudhir Palsule, Jeffrey M. Sullivan
Abstract: The disclosure relates to compositions containing 1,1-disubstituted alkene compounds capable of preparing polymers having glass transition temperatures above room temperature. The present teaching also relates to polymers prepared 1,1-disubstituted alkene compounds which exhibit glass transition temperatures of 60° C. The disclosure also relate to methods for enhancing the glass transition temperatures of polymers prepared from 1,1-disubstituted alkene compounds.
Type:
Grant
Filed:
September 21, 2015
Date of Patent:
April 19, 2016
Assignee:
SIRRUS, INC.
Inventors:
Jeffrey M. Sullivan, Aniruddha Palsule, Alexander R. Holzer, Kshitij K. Parab, Ami Doshi
Abstract: The present teachings show that it is possible to polymerize 1,1-disubstituted alkene compounds in a solution (for example using one or more solvents). Polymerization of 1,1-disubstituted alkene compounds in an solution provides opportunities to better control the polymerization compared with bulk polymerization. The solution polymerization techniques can be employed for preparing homopolymers, copolymers (e.g., random copolymers), and block copolymers.
Type:
Grant
Filed:
July 28, 2015
Date of Patent:
March 8, 2016
Assignee:
SIRRUS, INC.
Inventors:
Aniruddha Palsule, Alexander R. Holzer, Peter Rulon Stevenson, Kshitij Kishen Parab, Jeffrey M. Sullivan
Abstract: The present teachings show that it is possible to polymerize 1,1-disubstituted alkene compounds in an emulsion (for example using a water based carrier liquid), despite the possible reactions between the monomer and water. Polymerization of 1,1-disubstituted alkene compounds in an emulsion provides opportunities to better control the polymerization compared with bulk polymerization. The emulsion polymerization techniques can be employed for preparing homopolymers, copolymers (e.g., random copolymers), and block copolymers.
Type:
Grant
Filed:
July 1, 2015
Date of Patent:
February 2, 2016
Assignee:
SIRRUS, INC.
Inventors:
Peter Rulon Stevenson, Alexander R. Holzer, Aniruddha Sudhir Palsule
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 ?-ketoesters, methylene ?-diketones, dialkyl disubstituted vinyls, and dihaloalkyl disubstituted vinyls. Exemplary compositions are polymerizable at ambient temperatures.
Type:
Grant
Filed:
March 29, 2013
Date of Patent:
January 12, 2016
Assignee:
Sirrus, Inc.
Inventors:
Bernard M. Malofsky, Adam G. Malofsky, Matthew M. Ellison
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).
Type:
Grant
Filed:
October 18, 2012
Date of Patent:
December 29, 2015
Assignee:
SIRRUS, INC.
Inventors:
Adam G. Malofsky, Jeffrey M. Sullivan, Tanmoy Dey, Bernard M. Malofsky
Abstract: A method of initiating polymerization of a composition formed of a 1,1-disubstituted alkene compound includes contacting the composition with a substrate and passing an electrical charge through the composition. The composition can also be electrografted to the substrate or include conductive synergists.
Type:
Grant
Filed:
June 1, 2015
Date of Patent:
December 22, 2015
Assignee:
Sirrus, Inc.
Inventors:
Peter Rulon Stevenson, Jeffrey M. Sullivan
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.
Type:
Grant
Filed:
March 29, 2013
Date of Patent:
November 10, 2015
Assignee:
SIRRUS, INC.
Inventors:
Bernard M. Malofsky, Adam G. Malofsky, Matthew M. Ellison, Stanley C. Wojciak
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.
Type:
Grant
Filed:
March 3, 2015
Date of Patent:
August 18, 2015
Assignee:
SIRRUS, INC.
Inventors:
Bernard Miles Malofsky, Adam Gregg Malofsky, Jeffrey M. Sullivan, Philip B Kisanga, John Joseph Anderson, Michael Charles Milner Cockrem, Philip Jay Carlberg
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 ?-ketoesters, methylene ?-diketones, dialkyl disubstituted vinyls, and dihaloalkyl disubstituted vinyls. Exemplary compositions are polymerizable at ambient temperatures.
Type:
Application
Filed:
March 29, 2013
Publication date:
April 16, 2015
Applicant:
Sirrus, Inc.
Inventors:
Bernard M. Malofsky, Adam G. Malofsky, Matthew M. Ellison