公开(公告)号：US11958841B2

公开(公告)日：2024-04-16

申请号：US18189286

申请日：2023-03-24

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America, as represented by The Secretary of the Army

Inventor： Giuseppe R. Palmese ,  Santosh K. Yadav ,  John J. LaScala

IPC: C07D413/06 ,  C07D307/52 ,  C07D413/14 ,  C08G73/02

CPC classification number: C07D413/06 ,  C07D307/52 ,  C07D413/14 ,  C08G73/024 ,  C08G73/0273

Abstract: Benzoxazine compounds, methods of making them, polymers made therefrom and methods of polymerizing the benzoxazines. These renewable benzoxazine monomers and polymers that utilize the variety of building blocks found in renewable plant biomass, demonstrate excellent processability and large temperature windows for processing of resin systems.

公开(公告)号：US20220259220A1

公开(公告)日：2022-08-18

申请号：US17530089

申请日：2021-11-18

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America as Represented by the Secretary of the Army

Inventor： Joshua Matthew Sadler ,  John Joseph La Scala ,  Giuseppe R. Palmese

IPC: C07D493/04 ,  C08G59/42 ,  C08L63/00 ,  C08G59/17

Abstract: This invention outlines a method for synthesizing a blended resin system in a one pot reaction that may utilize, for example, bio-based anhydrosugars such as isosorbide as a principle component to produce isosorbide dimethacrylate and other monomeric materials for thermosetting applications. This invention establishes a one-pot procedure for reacting a hydroxy group containing compound with methacrylic anhydride in the first step and using the by-product methacrylic acid to react with glycidyl ethers to form additional methacrylate compounds in the second step. This methodology can be formulated to produce a wide array of resin systems that have controlled ratios of hydroxy group containing compound/cross-linker/reactive diluent. Additionally, the novel resin systems may be partially to fully bio-based, promoting global sustainability and reducing costs, and when free radically polymerized have properties that meet or exceed their petroleum derived counterparts.

公开(公告)号：US11208420B2

公开(公告)日：2021-12-28

申请号：US16462741

申请日：2017-11-16

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America as Represented by the Secretary of the Army

Inventor： Joshua Matthew Sadler ,  John Joseph La Scala ,  Giuseppe R. Palmese

IPC: C07D493/04 ,  C08G59/42 ,  C08L63/00 ,  C08G59/16 ,  C08L33/08 ,  C08L33/10 ,  C08G59/17

Abstract: This invention outlines a method for synthesizing a blended resin system in a one pot reaction that may utilize, for example, bio-based anhydrosugars such as isosorbide as a principle component to produce isosorbide dimethacrylate and other monomeric materials for thermosetting applications. This invention establishes a one-pot procedure for reacting a hydroxy group containing compound with methacrylic anhydride in the first step and using the by-product methacrylic acid to react with glycidyl ethers to form additional methacrylate compounds in the second step. This methodology can be formulated to produce a wide array of resin systems that have controlled ratios of hydroxy group containing compound/crosslinker/reactive diluent. Additionally, the novel resin systems may be partially to fully biobased, promoting global sustainability and reducing costs, and when free radically polymerized have properties that meet or exceed their petroleum derived counterparts.

公开(公告)号：US20190315763A1

公开(公告)日：2019-10-17

申请号：US16462741

申请日：2017-11-16

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America as Represented by the Secretary of the Army

Inventor： Joshua Matthew Sadler ,  John Joseph La Scala ,  Giuseppe R. Palmese

IPC: C07D493/04 ,  C08L63/00 ,  C08G59/42

Abstract: This invention outlines a method for synthesizing a blended resin system in a one pot reaction that may utilize, for example, bio-based anhydrosugars such as isosorbide as a principle component to produce isosorbide dimethacrylate and other monomeric materials for thermosetting applications. This invention establishes a one-pot procedure for reacting a hydroxy group containing compound with methacrylic anhydride in the first step and using the by-product methacrylic acid to react with glycidyl ethers to form additional methacrylate compounds in the second step. This methodology can be formulated to produce a wide array of resin systems that have controlled ratios of hydroxy group containing compound/crosslinker/reactive diluent. Additionally, the novel resin systems may be partially to fully biobased, promoting global sustainability and reducing costs, and when free radically polymerized have properties that meet or exceed their petroleum derived counterparts.

公开(公告)号：US20240092767A1

公开(公告)日：2024-03-21

申请号：US18189286

申请日：2023-03-24

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America, as represented by The Secretary of the Army

Inventor： Giuseppe R. Palmese ,  Santosh K. Yadav ,  John J. LaScala

IPC: C07D413/06 ,  C07D307/52 ,  C07D413/14 ,  C08G73/02

CPC classification number: C07D413/06 ,  C07D307/52 ,  C07D413/14 ,  C08G73/024 ,  C08G73/0273

Abstract: Benzoxazine compounds, methods of making them, polymers made therefrom and methods of polymerizing the benzoxazines. These renewable benzoxazine monomers and polymers that utilize the variety of building blocks found in renewable plant biomass, demonstrate excellent processability and large temperature windows for processing of resin systems.

公开(公告)号：US20200216429A1

公开(公告)日：2020-07-09

申请号：US16637551

申请日：2018-08-21

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America, as represented by The Secretary of the Army

Inventor： Giuseppe R. Palmese ,  Santosh K. Yadav ,  John J. LaScala

IPC: C07D413/06 ,  C07D413/14 ,  C08G73/02

Abstract: Benzoxazine compounds, methods of making them, polymers made therefrom and methods of polymerizing the benzoxazines. These renewable benzoxazine monomers and polymers that utilize the variety of building blocks found in renewable plant biomass, demonstrate excellent processability and large temperature windows for processing of resin systems.

公开(公告)号：US20170182152A1

公开(公告)日：2017-06-29

申请号：US15127081

申请日：2015-03-25

Applicant: The Government of the United States of America as Represented by the Secretary of the Army

Inventor： Carl R. ALVING ,  Zoltan BECK

IPC: A61K39/21 ,  C12N7/00 ,  A61K39/39

CPC classification number: A61K39/21 ,  A61K9/127 ,  A61K39/12 ,  A61K39/39 ,  A61K2039/55555 ,  A61K2039/55572 ,  A61K2039/55577 ,  C12N7/00 ,  C12N2740/16034 ,  C12N2740/16134 ,  C12N2740/16171

Abstract: Provided herein is an adjuvant formulation comprising a monophosphoryl lipid A (MPLA)-containing liposome composition to saponin (e.g., QS-21), wherein the liposome composition comprises i) a lipid bilayer comprising phospholipids in which the hydrocarbon chains have a melting temperature in water of ≧23° C. and ii) cholesterol at a mole percent concentration of greater than about 50% (mol/mol), preferably about 55% to about 71% (mol/mol), or more preferably about 55% (mol/mol). The adjuvant formulation displays minimal toxicity of either lipid A or saponin.

公开(公告)号：US20200181329A1

公开(公告)日：2020-06-11

申请号：US16637568

申请日：2018-08-21

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America, as represented by The Secretary of the Army

Inventor： Giuseppe R. Palmese ,  Santosh K. Yadav ,  John J. LaScala

IPC: C08G73/10 ,  C08K7/14

Abstract: A renewable polyimide or polyamic acid formed from a reaction comprising one or more furfurylamine compounds of Formula (I) or Formula (II) and one or more dianhydride or diacid compounds and heating to a temperature of up to 350° C., as well as methods of forming thereof, and polymers comprising the polyimide or polyamic acid compounds. The renewable furan based polyimides which demonstrate excellent processability, large temperature windows for processing of resin systems, and are less toxic.

公开(公告)号：US20230278942A1

公开(公告)日：2023-09-07

申请号：US18053589

申请日：2022-11-08

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America, as represented by The Secretary of the Army

Inventor： Giuseppe R. Palmese ,  Emre Kinaci ,  John J. LaScala

IPC: C07C39/19 ,  C08F222/20

CPC classification number: C07C39/19 ,  C08F222/20

Abstract: A polymerizable monomer prepared by reacting at least one epoxidized cardanol with (meth)acrylic anhydride or (meth)acryloyl chloride in the presence of one or more of triethylamine, tertiary amines, pyridines and pyridine derivatives; wherein the epoxidized cardanol is formed by epoxidation of an unsaturation site of a cardanol having the formula:




wherein R is selected from hydrogen and an alkyl, or alkenyl group having 1-6 carbon atoms, and n is 7, 10, or 13, a polymer and resin made form the polymerizable monomer, and a method of preparing such a polymer. The resin created from this monomer is suitable for moderate temperature composites and coatings applications.

公开(公告)号：US11629220B2

公开(公告)日：2023-04-18

申请号：US16640155

申请日：2018-08-21

Applicant: DREXEL UNIVERSITY ,  The Government of the United States of America, as represented by The Secretary of the Army

Inventor： Giuseppe R. Palmese ,  Santosh K. Yadav ,  John Vergara ,  John J. LaScala

IPC: C08G59/50 ,  C07D307/52 ,  C07D407/06 ,  C07D407/14 ,  C08G59/24 ,  C08G59/32 ,  C08G18/32 ,  C08G18/73 ,  C08G18/75 ,  C08G18/76 ,  C08G18/77 ,  C08G69/26

Abstract: The present invention relates novel furan based amine cross-linkers with improved thermomechanical and water barrier properties. The novelty of this invention is the use of aromatic, and hydrophobic aliphatic aldehydes to bridge two furfuryl amines, which yields a diamine or tetra amines with a significantly enhanced hydrophobic character. These diamine cross-linkers exhibit enhanced water barrier properties and thermomechanical properties when cured with both commercial and synthetic epoxies.