公开(公告)号：US20220153932A1

公开(公告)日：2022-05-19

申请号：US17405554

申请日：2021-08-18

Applicant: Sirrus, Inc.

Inventor： J. Taylor Goodrich ,  Alexander Y. Polykarpov

IPC: C08G75/045 ,  C07C323/52 ,  C07C319/18

Abstract: A liquid 1,1-dicarbonyl substituted 1-alkene prepolymer is formed by reacting a multifunctional 1,1-dicarbonyl substituted-1-alkene and a polythiol or monothiol at a ratio of thiols/carbon-carbon double bonds of 0.001 to 0.5 in the presence of 0.1 parts per million (ppm) to 100 ppm by weight of strong acid, polythiol/monothiol and 1,1-dicarbonyl substituted-1-alkene. Further ingredients, such as other monomers, fillers, and rheological modifiers may be added to form polymerizable compositions. The prepolymer or polymerizable compositions may be addition polymerized to form polymer articles.

公开(公告)号：US20210309780A1

公开(公告)日：2021-10-07

申请号：US17223793

申请日：2021-04-06

Applicant: Sirrus, Inc.

Inventor： Deenadayalu Chundury ,  Aniruddha Palsule

IPC: C08F283/06 ,  C08F283/02

Abstract: Disclosed are compositions which include a polymer with a nucleophilic group and a 1,1-disubstituted alkene disposed on the polymer. Disclosed is a composition containing a polymer which includes a nucleophilic group. In addition, also disclosed are methods of making a composition including a polymer with a nucleophilic group and a 1,1-disubstituted alkene disposed on the polymer, methods of chain extending or cross linking a polymer with a nucleophilic group with a 1,1-disubstituted alkene and methods of polymerizing a 1,1-disubstituted alkene.

公开(公告)号：US20190202947A1

公开(公告)日：2019-07-04

申请号：US15857808

申请日：2017-12-29

Applicant: SIRRUS, INC.

Inventor： Jeffrey M. Sullivan ,  Aniruddha Palsule ,  Alexander R. Holzer ,  Kshitij K. Parab ,  Ami Doshi

IPC: C08F22/10 ,  C07C69/593 ,  C08F2/06 ,  C09J135/02 ,  C08F222/14

CPC classification number: C08F22/10 ,  C07C69/593 ,  C08F2/06 ,  C08F222/14 ,  C09J135/02

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.

公开(公告)号：US10150886B2

公开(公告)日：2018-12-11

申请号：US15638290

申请日：2017-06-29

Applicant: SIRRUS, INC.

Inventor： Aniruddha S. Palsule ,  Jeffrey M. Sullivan ,  Katherine E. Vanderpool ,  Alexander R. Holzer ,  Anushree Deshpande ,  John Klier

IPC: C09D167/06 ,  C08L67/06 ,  C08L33/14 ,  C09D133/06 ,  C08G63/00 ,  C08G63/78 ,  C12P7/62 ,  C08G63/553 ,  C08G63/676 ,  C09D167/02

Abstract: Compositions comprising a) one or more polyester macromers containing one or more chains of the residue of one or more diols and one or more diesters wherein the residue of the one or more diols and the one or more diesters alternate along the chain and a portion of the diesters are 1,1-diester-1-alkenes and at least one terminal end comprises the residue of one of the 1,1-diester-1 alkenes and wherein one or more terminal ends may comprise the residue of one or more diols; and b) one or more polymers having pendant Michael Addition donor groups. Disclosed are coating prepared from these compositions.

公开(公告)号：US20180327525A1

公开(公告)日：2018-11-15

申请号：US15978974

申请日：2018-05-14

Applicant: Sirrus, Inc.

Inventor： Bernard M. Malofsky ,  Adam G. Malofsky ,  Tanmoy Dey ,  Matthew M. Ellison ,  Larry Hines

IPC: C08F20/28 ,  C07C69/604 ,  C07D307/54 ,  C09D4/00 ,  C08F20/14 ,  C09J133/14 ,  C08F20/30 ,  C08F20/38 ,  C08F22/20 ,  C08K5/00 ,  C08L21/00 ,  C08L33/14 ,  C08L33/16 ,  C08L35/02 ,  C09D133/14 ,  C09D133/16 ,  C09D135/02 ,  C09J135/02 ,  C09J133/16 ,  C07C49/80 ,  C08K3/013 ,  C07C67/03

CPC classification number: C08F20/28 ,  C07C45/75 ,  C07C49/794 ,  C07C49/796 ,  C07C49/798 ,  C07C49/80 ,  C07C67/03 ,  C07C67/30 ,  C07C69/604 ,  C07C69/738 ,  C07D307/46 ,  C07D307/54 ,  C07D333/22 ,  C07D333/24 ,  C08F20/14 ,  C08F20/30 ,  C08F20/38 ,  C08F20/68 ,  C08F22/20 ,  C08F24/00 ,  C08F28/06 ,  C08F116/36 ,  C08F128/06 ,  C08F222/1006 ,  C08F222/14 ,  C08K3/013 ,  C08K5/0008 ,  C08L21/00 ,  C08L33/14 ,  C08L33/16 ,  C08L35/02 ,  C09D4/00 ,  C09D129/12 ,  C09D133/14 ,  C09D133/16 ,  C09D135/02 ,  C09D141/00 ,  C09J133/06 ,  C09J133/14 ,  C09J133/16 ,  C09J135/02 ,  Y02P20/127

Abstract: The present invention provides multifunctional monomers, including, but not limited to include multifunctional methylene malonate and methylene beta-ketoester monomers; methods for producing the same; and compositions and products formed therefrom. The multifunctional monomers of the invention may be produced by transesterification or by direct synthesis from monofunctional methylene malonate monomers or methylene beta-ketoester monomers. The present invention further compositions and products formed from methylene beta-ketoester 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).

公开(公告)号：US10086355B2

公开(公告)日：2018-10-02

申请号：US15345976

申请日：2016-11-08

Applicant: SIRRUS, INC.

Inventor： Bernard Miles Malofsky ,  Adam Gregg Malofsky ,  Jeffrey M. Sullivan ,  Philip B. Kisanga ,  John Joseph Anderson ,  Michael Charles Milner Cockrem ,  Philip Jay Carlberg

IPC: B01J8/06 ,  B01J19/24 ,  B01J29/40 ,  C07C67/31 ,  C07C67/327 ,  C07C67/333 ,  C07C67/56 ,  C07C69/593 ,  C09J4/00 ,  C09D4/00 ,  C08F222/14

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.

公开(公告)号：US09969819B2

公开(公告)日：2018-05-15

申请号：US15589364

申请日：2017-05-08

Applicant: Sirrus, Inc.

Inventor： Aniruddha Palsule ,  Alexander R. Holzer ,  Peter Rulon Stevenson ,  Kshitij Kishen Parab ,  Jeffrey M. Sullivan

IPC: C09J7/38 ,  C08F2/06 ,  C08F222/14 ,  C09J153/00 ,  C09J135/02

CPC classification number: C08F2/06 ,  B05D3/007 ,  C08F2/26 ,  C08F222/14 ,  C08F297/02 ,  C09D135/02 ,  C09D153/00 ,  C09J135/02 ,  C09J153/00

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.

公开(公告)号：US20170349781A1

公开(公告)日：2017-12-07

申请号：US15638290

申请日：2017-06-29

Applicant: SIRRUS, INC.

Inventor： Aniruddha S. Palsule ,  Jeffrey M. Sullivan ,  Katherine E. Vanderpool ,  Alexander R. Holzer ,  Anushree Deshpande ,  John Klier

IPC: C09D167/06 ,  C08L67/06 ,  C08G63/78 ,  C12P7/62 ,  C08G63/00

CPC classification number: C09D167/06 ,  C08G63/00 ,  C08G63/553 ,  C08G63/676 ,  C08G63/78 ,  C08L67/06 ,  C09D133/06 ,  C09D167/02 ,  C12P7/625 ,  C08L83/04 ,  C08L79/02

Abstract: Compositions comprising a) one or more polyester macromers containing one or more chains of the residue of one or more diols and one or more diesters wherein the residue of the one or more diols and the one or more diesters alternate along the chain and a portion of the diesters are 1,1-diester-1-alkenes and at least one terminal end comprises the residue of one of the 1,1-diester-1 alkenes and wherein one or more terminal ends may comprise the residue of one or more diols; and b) one or more polymers having pendant Michael Addition donor groups. Disclosed are coating prepared from these compositions.

公开(公告)号：US20170342011A1

公开(公告)日：2017-11-30

申请号：US15678533

申请日：2017-08-16

Applicant: Sirrus, Inc.

Inventor： Jeffrey M. Sullivan ,  Adam G. Malofsky ,  Bernard M. Malofsky ,  Tanmoy Dey

IPC: C07C49/84 ,  C07D307/46 ,  C07C49/80 ,  C07C49/796 ,  C07C49/557 ,  C07C49/227 ,  C07C49/203 ,  C07C45/75 ,  C07D333/22 ,  C07C49/794 ,  C07C2601/14

Abstract: The present teachings are directed at polymers, polymeric compositions, polymerizable compositions, and articles including a 1,1-disubstituted alkene monomers (e.g., methylene beta-diketone monomers) and one or more formulation materials. The monomer preferably is a high purity monomer. Preferably, the amount of ketals (e.g., in the polymerizable composition) is less than about 100 ppm and/or the amount of latent acid-forming impurities (e.g., in the polymerizable composition) is less than about 100 ppm (e.g., based on the total weight of the monomer). Preferably, the methylene beta-diketone monomer is a high purity monomer having a purity of about 95 weight percent or more. The monomer(s) may be employed in compositions and products, 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).

公开(公告)号：US20170275446A1

公开(公告)日：2017-09-28

申请号：US15509403

申请日：2015-09-09

Applicant: Sirrus, Inc.

Inventor： Jeffrey M. SULLIVAN ,  Aniruddha Sudhir PALSULE ,  Alexander R. HOLZER ,  Peter R. STEVENSON ,  Kshitij K. PARAB

IPC: C08L33/04 ,  C08F222/10 ,  C07C69/38

Abstract: The disclosure relates to polymers including one or more 1,1-disubstituted alkene monomers. By employing a plurality of monomers and/or tailored chain structure, polymers having improved combinations of properties are achieved. The polymer may be a copolymer, preferably including two or more 1,1-disubstituted alkene monomers. The polymer may be a homopolymer having a tailored chain structure.