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：US20160347976A1

公开(公告)日：2016-12-01

申请号：US15094705

申请日：2016-04-08

Applicant: Sirrus, Inc.

Inventor： Peter Rulon Stevenson ,  Aniruddha Sudhir Palsule ,  Jeffrey M. Sullivan

IPC: C09J135/02

CPC classification number: C09J135/02 ,  C08F222/14 ,  C08K3/01 ,  C08K5/0008 ,  C08K5/11 ,  C08L27/06 ,  C09J4/06

Abstract: A polymerizable system includes a curable composition and one or more encapsulated initiator particles. The curable composition can include one or more 1,1-disubstituted alkene compounds and the encapsulated initiator particles can include one or more polymerization initiators encapsulated by a cured composition. The cured composition includes one or more 1,1-disubstituted alkene compounds.

Abstract translation: 可聚合体系包括可固化组合物和一种或多种包封的引发剂颗粒。 可固化组合物可以包括一种或多种1,1-二取代烯烃化合物，并且包封的引发剂颗粒可以包括一种或多种由固化组合物包封的聚合引发剂。 固化的组合物包括一种或多种1,1-二取代烯烃化合物。

公开(公告)号：US09416091B1

公开(公告)日：2016-08-16

申请号：US14814961

申请日：2015-07-31

Applicant: Sirrus, Inc.

Inventor： Jeffrey M. Sullivan ,  Aniruddha Sudhir Palsule ,  Peter Rulon Stevenson ,  Kshitij Kishen Parab

IPC: C07C67/02 ,  C07C69/604 ,  C07C69/732

CPC classification number: C07C67/02 ,  C07C67/03 ,  C07C69/593 ,  C07C69/604 ,  C07C69/732 ,  C07C2601/14 ,  C07C2602/42

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.

Abstract translation: 公开了具有一个或多个酯基和在酯交换条件下反应的基团如1,1-二取代烯烃化合物与醇或酯的催化酯交换反应的方法和由其制备的新型组合物。 进一步公开的是作为所述方法的结果制备的新化合物和组合物。

公开(公告)号：US20160096906A1

公开(公告)日：2016-04-07

申请号：US14966247

申请日：2015-12-11

Applicant: Sirrus, Inc.

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

IPC: C08F2/06 ,  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.

Abstract translation: 本教导显示可以在溶液（例如使用一种或多种溶剂）中聚合1,1-二取代烯烃化合物。 与本体聚合相比，溶液中1,1-二取代烯烃化合物的聚合提供了更好地控制聚合的机会。 溶液聚合技术可用于制备均聚物，共聚物（例如无规共聚物）和嵌段共聚物。

公开(公告)号：US09279022B1

公开(公告)日：2016-03-08

申请号：US14810741

申请日：2015-07-28

Applicant: Sirrus, Inc.

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

IPC: C08F2/04 ,  C08F16/36 ,  C08F22/14 ,  C08F267/06 ,  C08F2/06 ,  C09J135/02 ,  C09J153/00

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.

Abstract translation: 本教导显示可以在溶液（例如使用一种或多种溶剂）中聚合1,1-二取代烯烃化合物。 与本体聚合相比，溶液中1,1-二取代烯烃化合物的聚合提供了更好地控制聚合的机会。 溶液聚合技术可用于制备均聚物，共聚物（例如无规共聚物）和嵌段共聚物。

公开(公告)号：US09221739B2

公开(公告)日：2015-12-29

申请号：US14352369

申请日：2012-10-18

Applicant: Sirrus, Inc.

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

IPC: C07C45/00 ,  C07C49/00 ,  C08L27/12 ,  B03D1/016 ,  C08F214/06 ,  C08L27/00 ,  C07C67/03 ,  C09J133/06 ,  C07C45/75 ,  C07C49/794 ,  C07C49/796 ,  C07C49/798 ,  C07C49/80 ,  C07D307/46 ,  C07D333/22 ,  C08F116/36 ,  C08F128/06 ,  C09D129/12 ,  C09D141/00 ,  C07C67/30 ,  C07C69/738 ,  C07D307/54 ,  C07D333/24 ,  C08F20/28 ,  C08F20/68 ,  C08F24/00 ,  C08F28/06 ,  C07C69/604 ,  C08F222/14 ,  C08F222/10

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 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 translation: 本发明提供亚甲基β-二酮单体，其制备方法，以及由其形成的组合物和产品。 在制备本发明的亚甲基β-二酮的方法中，β-二酮与改性的Knoevenagel反应中的甲醛源反应，任选地在酸性或碱性催化剂存在下，任选地在酸性或碱性 非酸性溶剂，形成反应络合物。 反应络合物可以是低聚物。 将反应复合物进行进一步处理，其可以通过与能量转移装置接触而汽化，​​以分离β-二酮单体。 本发明还包括由本发明的亚甲基β-二酮单体形成的组合物和产品，包括基于单体的产品（例如油墨，粘合剂，涂料，密封剂或反应性模塑）和基于聚合物的产品（例如纤维，薄膜，片材 ，医用聚合物，复合聚合物和表面活性剂）。

公开(公告)号：US09108914B1

公开(公告)日：2015-08-18

申请号：US14636402

申请日：2015-03-03

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: C07C67/327 ,  C07C67/31 ,  C07C69/593 ,  B01J29/40 ,  C07C67/56

CPC classification number: B01J19/245 ,  B01J8/067 ,  B01J29/40 ,  B01J2208/00168 ,  B01J2208/065 ,  B01J2219/00033 ,  B01J2219/0004 ,  B01J2219/00087 ,  B01J2219/00177 ,  B01J2219/24 ,  C07C67/31 ,  C07C67/327 ,  C07C67/333 ,  C07C67/56 ,  C07C69/593 ,  C08F222/14 ,  C09D4/00 ,  C09J4/00

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 translation: 获得二（羟甲基）丙二酸酯途径后亚甲基丙二酸酯和相关单体的方法。 随后将双（羟甲基）丙二酸酯中间体反应（即进行热解）以提供亚甲基丙二酸酯单体种类。 在碱性催化剂（如氢氧化钙）的存在下提供甲醛源（如福尔马林），在合适的反应条件下加入丙二酸酯（如丙二酸二乙酯），得到所需的中间体（如二烷基 双（羟甲基）丙二酸酯）。 在合适的条件下，在合适的催化剂（例如沸石）的存在下，使中间体反应（即进行热解），得到亚甲基丙二酸酯单体。 在一个示例性实施方案中，热解反应包括在加热的催化剂上加入双（羟甲基）丙二酸酯中间体。 收集并纯化反应产物。 所公开的方法可以在连续操作中执行。 离散步骤可以通过使用工厂内的模块化单元来执行。

公开(公告)号：US20150218081A1

公开(公告)日：2015-08-06

申请号：US14636402

申请日：2015-03-03

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: C07C67/327 ,  C07C67/56 ,  B01J29/40 ,  C07C67/31 ,  C07C69/593

CPC classification number: B01J19/245 ,  B01J8/067 ,  B01J29/40 ,  B01J2208/00168 ,  B01J2208/065 ,  B01J2219/00033 ,  B01J2219/0004 ,  B01J2219/00087 ,  B01J2219/00177 ,  B01J2219/24 ,  C07C67/31 ,  C07C67/327 ,  C07C67/333 ,  C07C67/56 ,  C07C69/593 ,  C08F222/14 ,  C09D4/00 ,  C09J4/00

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：US10428177B2

公开(公告)日：2019-10-01

申请号：US15610854

申请日：2017-06-01

Applicant: Sirrus, Inc.

Inventor： Jeffrey M. Sullivan ,  Ami Doshi

IPC: C08F267/06 ,  C08F122/20 ,  C08G63/52 ,  B32B27/36 ,  C12P7/62 ,  C09D151/08

Abstract: Disclosed are graft copolymers, compositions including graft copolymers, intermediate materials, and related methods, where the graft copolymer includes a first polymer component including a 1,1-disubstituted-1-alkene compound (preferably a methylene malonate compound) and is grafted to a second component. The resulting graft copolymer may be hydrophilic or water soluble. The second component preferably is a hydrophilic component.

公开(公告)号：US20190106522A1

公开(公告)日：2019-04-11

申请号：US16147859

申请日：2018-09-30

Applicant: Sirrus, Inc.

Inventor： Peter Rulon Stevenson ,  Aniruddha Sudhir Palsule ,  Jeffrey M. Sullivan

IPC: C08F222/14 ,  C08K9/10 ,  B01J13/18 ,  C08L27/06 ,  C09J135/02 ,  C08K5/11 ,  C08K3/01 ,  C08K5/00 ,  C09J4/06

Abstract: A polymerizable system includes a curable composition and one or more encapsulated initiator particles. The curable composition can include one or more 1,1-disubstituted alkene compounds and the encapsulated initiator particles can include one or more polymerization initiators encapsulated by a cured composition. The cured composition includes one or more 1,1-disubstituted alkene compounds.