公开(公告)号：US09969822B2

公开(公告)日：2018-05-15

申请号：US15289300

申请日：2016-10-10

Applicant: SIRRUS INC.

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

IPC: C07C45/75 ,  C07C49/794 ,  C07C49/796 ,  C07C49/798 ,  C07C49/80 ,  C07C67/30 ,  C07C67/03 ,  C07C69/738 ,  C07D307/46 ,  C07D333/22 ,  C07D307/54 ,  C07D333/24 ,  C08F24/00 ,  C08F20/68 ,  C08F20/28 ,  C09J133/06 ,  C08F116/36 ,  C08F128/06 ,  C09D129/12 ,  C09D141/00 ,  C08F28/06 ,  C07C69/604 ,  C08F222/14 ,  C08F20/30 ,  C08F20/38 ,  C08F22/20 ,  C08K5/00 ,  C08L21/00 ,  C08L33/14 ,  C08L33/16 ,  C08L35/02 ,  C09D133/14 ,  C09D133/16 ,  C09D135/02 ,  C09J133/14 ,  C09J133/16 ,  C09J135/02 ,  C08F20/14 ,  C09D4/00 ,  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 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：US20190315892A1

公开(公告)日：2019-10-17

申请号：US16455040

申请日：2019-06-27

Applicant: Sirrus, Inc.

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

IPC: C08F20/28 ,  C08F24/00 ,  C07C67/333 ,  C07D333/24 ,  C09D129/12 ,  C08F128/06 ,  C08F116/36 ,  C07D333/22 ,  C09D141/00 ,  C07D307/46 ,  C09J133/06 ,  C08F20/68 ,  C07C67/343 ,  C08F20/14 ,  C09D4/00 ,  C09J4/00 ,  C08K3/013 ,  C08K5/00 ,  C07C67/30 ,  C07C49/80 ,  C09J133/16 ,  C09J135/02 ,  C09D135/02 ,  C09D133/16 ,  C09D133/14 ,  C08F20/30 ,  C07C69/738 ,  C08F28/06 ,  C08F222/14 ,  C08L35/02 ,  C08L33/16 ,  C08L33/14 ,  C08L21/00 ,  C08F22/20 ,  C08F20/38 ,  C07D307/54 ,  C09J133/14 ,  C07C45/75 ,  C07C49/798 ,  C07C49/796 ,  C07C49/794 ,  C07C67/03 ,  C07C69/604

Abstract: The present teachings are directed at 1,1-di substituted 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).

公开(公告)号：US20180346615A1

公开(公告)日：2018-12-06

申请号：US15978923

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

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：US10047192B2

公开(公告)日：2018-08-14

申请号：US14404870

申请日：2013-05-31

Applicant: Sirrus, Inc.

Inventor： Matthew McBrayer Ellison ,  Bernard Miles Malofsky ,  Adam Gregg Malofsky ,  Tanmoy Dey ,  Jeffrey M. Sullivan

IPC: B01F17/00 ,  C08G63/00 ,  C08F18/14 ,  G02B1/04 ,  C08F222/10 ,  C07C69/38 ,  C07C69/708 ,  C09J5/00 ,  C09J167/00 ,  G02B6/255

CPC classification number: C08G63/00 ,  C07C69/38 ,  C07C69/708 ,  C08F18/14 ,  C08F222/10 ,  C09J5/00 ,  C09J167/00 ,  G02B1/04 ,  G02B6/255 ,  C08L31/06

Abstract: Optical materials including polymerizable compositions and oligomeric and polymeric material formed therefrom. The oligomer or polymer material include structural repeat units. 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.

公开(公告)号：US20170355789A1

公开(公告)日：2017-12-14

申请号：US15661893

申请日：2017-07-27

Applicant: SIRRUS, INC.

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

IPC: C08F20/28 ,  C09D135/02 ,  C07C67/30 ,  C08L33/14 ,  C08F24/00 ,  C08F20/68 ,  C07C69/604 ,  C09J133/16 ,  C07C49/794 ,  C09D133/16 ,  C08F20/38 ,  C07C49/80 ,  C08F20/30 ,  C07D307/54 ,  C08K3/00 ,  C08K5/00 ,  C08F128/06 ,  C07C49/798 ,  C07D333/22 ,  C07C49/796 ,  C09J133/06 ,  C07C69/738 ,  C07C67/03 ,  C09J133/14 ,  C07C45/75 ,  C08F28/06 ,  C09D141/00 ,  C09D129/12 ,  C08F116/36 ,  C08L21/00 ,  C08F22/20 ,  C07D307/46 ,  C08L33/16 ,  C08L35/02 ,  C09J135/02 ,  C07D333/24 ,  C09D133/14 ,  C08F222/14 ,  C08F222/10

CPC classification number: C08F20/28 ,  C07C45/75 ,  C07C49/794 ,  C07C49/796 ,  C07C49/798 ,  C07C49/80 ,  C07C67/03 ,  C07C67/30 ,  C07C67/333 ,  C07C67/343 ,  C07C69/604 ,  C07C69/738 ,  C07C2601/02 ,  C07C2601/04 ,  C07C2601/08 ,  C07C2601/14 ,  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 ,  C08K5/005 ,  C08K5/08 ,  C08K5/13 ,  C08L21/00 ,  C08L33/14 ,  C08L33/16 ,  C08L35/02 ,  C09D4/00 ,  C09D129/12 ,  C09D133/14 ,  C09D133/16 ,  C09D135/02 ,  C09D141/00 ,  C09J4/00 ,  C09J133/06 ,  C09J133/14 ,  C09J133/16 ,  C09J135/02 ,  Y02P20/127 ,  C07C69/716

Abstract: 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).

公开(公告)号：US09828324B2

公开(公告)日：2017-11-28

申请号：US14868795

申请日：2015-09-29

Applicant: Sirrus, Inc.

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

IPC: C07C45/00 ,  C07C49/00 ,  C08L27/12 ,  B03D1/016 ,  C08F214/06 ,  C08L27/00 ,  C07C49/84 ,  C07C45/75 ,  C07C49/203 ,  C07C49/794 ,  C07C49/796 ,  C07D333/22 ,  C07C49/557 ,  C07C49/227 ,  C07D307/46 ,  C07C49/80

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

Abstract: The present teachings are directed at 1,1-disubstituted alkene monomers (e.g., methylene beta-diketone monomers), methods for producing the same, and compositions and products formed therefrom. In the method for producing the monomer, a beta-diketone is preferably 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 vaporization in order to isolate the monomer. 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：US09512058B2

公开(公告)日：2016-12-06

申请号：US14352356

申请日：2012-10-18

Applicant: Sirrus, Inc.

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

IPC: C07C67/03 ,  C09J133/06 ,  C07C45/75 ,  C07C49/794 ,  C07C49/798 ,  C07C49/80 ,  C07D307/46 ,  C07C69/604 ,  C07C49/796 ,  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 ,  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 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).

Abstract translation: 本发明提供多官能单体，包括但不限于多官能亚甲基丙二酸酯和亚甲基β-酮酯单体; 生产方法; 以及由其形成的组合物和产品。 本发明的多官能单体可以通过酯交换反应或通过直接合成由单官能亚甲基丙二酸酯单体或亚甲基β-酮酯单体制备。 本发明还包括由本发明的亚甲基β-酮酯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：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：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：US20170050914A1

公开(公告)日：2017-02-23

申请号：US15289300

申请日：2016-10-10

Applicant: SIRRUS INC.

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

IPC: C07C69/604

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).

Abstract translation: 本发明提供多官能单体，包括但不限于多官能亚甲基丙二酸酯和亚甲基β-酮酯单体; 生产方法; 以及由其形成的组合物和产品。 本发明的多官能单体可以通过酯交换反应或直接由单官能亚甲基丙二酸酯单体或亚甲基β-酮酯单体合成来制备。 本发明还包括由本发明的亚甲基β-酮酯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）。