公开(公告)号：US10647878B2

公开(公告)日：2020-05-12

申请号：US15576399

申请日：2016-06-01

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Teluka Galhenage

IPC: C09D175/08 ,  C08G18/62 ,  C08G18/72 ,  C08G18/75 ,  C08G18/79 ,  C08G18/80 ,  C08G18/28 ,  C09D175/04 ,  C09D5/16

Abstract: The invention is directed to curable polyurethane coating compositions which may be used to form fouling release coatings, e.g., for use in protecting boat hulls. The curable polyurethane coating compositions of the invention comprise (a) a prepolymer made by reacting at least one polyisocyanate with (i) at least one monocarbinol-terminated poly(dimethylsiloxane), (ii) at least one methoxy-terminated poly(ethylene glycol), or (iii) mixtures thereof, (b) at least one polyol, and (c) at least one polyisocyanate crosslinker. The invention also relates to the prepolymer used in the curable coating compositions. The invention further relates to methods for reducing or preventing biofouling of a surface exposed to an aqueous environment comprising the steps of coating the surface with a curable coating composition of the invention to form a coated surface, and curing the coating coating composition on the coated surface.

公开(公告)号：US10072178B2

公开(公告)日：2018-09-11

申请号：US15133813

申请日：2016-04-20

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  James A. Docken, Jr. ,  Satyabrata Samanta ,  James A. Bahr

IPC: C08G73/10 ,  C09D175/12 ,  C08G59/02 ,  C08K5/17 ,  C08K5/00 ,  C08K5/3462

CPC classification number: C09D175/12 ,  C08G59/027 ,  C08G71/04 ,  C08K5/0025 ,  C08K5/17 ,  C08K5/3462 ,  C08L69/00

Abstract: The invention relates to a resin having a plurality of cyclic carbonate groups comprising the reaction product of: a) an epoxidized sucrose fatty acid ester resin, and b) carbon dioxide where a) and b) are reacted under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent. In one embodiment the epoxidized sucrose fatty acid ester resin is epoxidized sucrose soyate. The invention also relates to methods for producing a resin having a plurality of cyclic carbonate groups. In a method of the invention, an epoxidized sucrose fatty acid ester resin is contacted with carbon dioxide under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent. Other embodiments of the invention relate to curable composition containing a) a resin having a plurality of cyclic carbonate groups; b) an alkyl amine curing agent having two or more reactive amine groups; and c) optionally, a catalyst; and cured compositions and articles.

公开(公告)号：US12252590B2

公开(公告)日：2025-03-18

申请号：US17106866

申请日：2020-11-30

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Eric M. Krall ,  Kelly M. Sutko ,  Alexander T. Hart ,  Karan Bansal ,  Mohiuddin Quadir

IPC: C08H7/00 ,  C08J9/14 ,  C08L97/00

Abstract: The invention relates to acetoacetylated lignin resin compositions comprising the reaction product of lignin and an acetoacetate ester. The invention also relates to (meth)acrylated lignin resin compositions comprising the reaction product of lignin and a (meth)acrylic compound. The invention also relates to methods of making the acetoacetylated and (meth)acrylated lignin resin compositions. The invention also relates to curable coating compositions comprising the acetoacetylated and (meth)acrylated lignin resin compositions. The invention also relates to methods of making the curable coating compositions of the invention. The invention also relates to methods of applying curable coating compositions of the invention to substrates. The invention also relates to articles of manufacture comprising a curable coating composition of the invention and a method of making such article. The invention also relates to foam materials comprising the reaction product of an acetoacetylated resin composition, a polyamine compound, and a physical blowing agent and/or a polysiloxane compound.

公开(公告)号：US11859099B2

公开(公告)日：2024-01-02

申请号：US17191035

申请日：2021-03-03

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Alireza Rahimi

IPC: C09D175/08 ,  C08G18/62 ,  C08G18/72 ,  C08G18/75 ,  C08G18/79 ,  C08G18/80 ,  C08G18/28 ,  C09D175/04 ,  C09D5/16

CPC classification number: C09D175/08 ,  C08G18/283 ,  C08G18/289 ,  C08G18/6229 ,  C08G18/725 ,  C08G18/755 ,  C08G18/792 ,  C08G18/8064 ,  C09D5/1637 ,  C09D175/04

Abstract: The invention is directed to curable polyurethane coating compositions which may be used to form fouling release coatings, e.g., for use in protecting boat hulls. A curable coating composition of the invention comprises a) at least one amphiphilic additive; b) at least one polyisocyanate; c) at least one polyol; and d) optionally, at least one amphiphilic PEG-PDMS isocyanate prepolymer. Another curable coating composition of the invention comprises the at least one polyisocyanate, b), the at least one polyol, c), and the at least one amphiphilic PEG-PDMS isocyanate prepolymer, d). The invention further relates to methods for reducing or preventing biofouling of a surface exposed to an aqueous environment comprising the steps of coating the surface with the curable coating compositions of the invention to form a coated surface, and curing the coating composition on the coated surface.

公开(公告)号：US10759950B2

公开(公告)日：2020-09-01

申请号：US16076395

申请日：2017-02-28

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Madhura Pade

IPC: C09D5/16 ,  C09D183/10 ,  C08G77/455 ,  C08G77/08 ,  C08G77/388 ,  C09D183/08 ,  C08G77/00

Abstract: This invention relates to novel non-isocyanate siloxane-modified glycidol carbamate (GC) resins and coating compositions containing them. The non-isocyanate siloxane modified GC resins of the invention comprise the reaction product of at least one organic polyisocyanate, glycidol, and at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane. The coating compositions of the invention comprise at least one non-isocyanate siloxane modified GC resin of the invention and at least one curing agent. The invention also relates to methods of making the resins of the invention and coatings containing them. The invention also relates to a fouling-release (FR) coating system comprising the coating compositions of the invention and methods of applying said FR coating systems to substrates. The invention also relates to articles of manufacture comprising a coating composition of the invention and a method of making such articles.

公开(公告)号：US10323119B2

公开(公告)日：2019-06-18

申请号：US15034312

申请日：2014-11-07

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Lindsey Bultema ,  Jingling Yan

IPC: C09D147/00 ,  C08G59/17 ,  C08F290/06 ,  C08G65/22 ,  C08G65/26 ,  C08F290/04 ,  C08G59/32

Abstract: The invention provides poiyfunctionai bio-based methacrylate oligomers, which are synthesized via the ring-opening reaction between at least one ethyienicaliy unsaturated acid selected from methacrylic acid, acrylic acid, and crotonic acid, and a poiyfunctionai bio-based epoxy resin, such as epoxidized sucrose soyate. The extent of reaction may be varied to generate a family of methacrylate oligomers with differing degrees of methacryiation. These methacrylate oligomers can optionally be mixed with a reactive diluent, such as styrene, and cured using, for example, a thermally-activated free radical initiator to form a thermoset polymer with high modulus. The thermosets can be used to form composites, adhesives, coatings, and dental restorative materials. Methods of making the methacrylate oligomers are disclosed as are coating compositions and coated objects, such as dental restorative materials, using the methacrylate oligomers.

公开(公告)号：US09765233B2

公开(公告)日：2017-09-19

申请号：US15135144

申请日：2016-04-21

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Arvin Yu

IPC: C09D175/12 ,  C08G59/02 ,  C09D133/10 ,  C07C69/67 ,  C09D133/06 ,  C09D133/08

CPC classification number: C09D133/10 ,  C07C69/67 ,  C09D133/06 ,  C09D133/08 ,  C08L67/00

Abstract: The invention relates to a polyfunctional bio-based oligomer which is the reaction product of a) at least one epoxidized sucrose fatty acid ester resin; b) at least one ethylenically unsaturated acid selected from methacrylic acid, acrylic acid, crotonic acid, and mixtures thereof; c) at least one acid anhydride selected from acetic acid anhydride, acrylic acid anhydride, methacrylic acid anhydride, crotonic acid anhydride, and mixtures thereof; d) optionally, at least one catalyst; and e) optionally, at least one inhibitor. In a polyfunctional bio-based oligomer of the invention, the ratio of ethylenically unsaturated acid to acid anhydride ranges from 90:1 to 1:90; at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one ethylenically unsaturated acid; and at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one acid anhydride. Other embodiments of the invention relate to methods of making the polyfunctional bio-based oligomers of the invention and to curable coating compositions containing them.

公开(公告)号：US20210347990A1

公开(公告)日：2021-11-11

申请号：US17313653

申请日：2021-05-06

Applicant: NDSU Research Foundation

Inventor： Todd Sirotiak ,  Dean C. Webster ,  Samantha Silbert Uzelac

IPC: C08L75/14 ,  C09D175/14 ,  C08J9/35 ,  C08J3/11 ,  C03C17/00 ,  C03C17/32

Abstract: An aerogel hybrid and a method for preparing the aerogel hybrid. The aerogel hybrid includes a resin composition and a plurality of aerogel particles. The resin composition may fill the interstitial space between the plurality of aerogel particles. The aerogel hybrid may be produced by preparing the aerogel and preparing the resin composition, blending the aerogel and the resin composition together to form an aerogel hybrid and curing the aerogel hybrid for providing an aerogel hybrid containing resin mixture with the ability to fit large amounts of aerogel into the resin to enhance the aerogel's physical properties.

公开(公告)号：US10730998B2

公开(公告)日：2020-08-04

申请号：US15758181

申请日：2016-09-15

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Songqi Ma

IPC: C08G59/34 ,  C08G59/42 ,  C08G59/32 ,  C08G65/26 ,  C08G59/04

Abstract: The invention relates to novel curable bio-based thermosetting compositions of a) at least one highly-functional bio-based epoxy resin; and b) at least one carboxylic acid crosslinker selected from the group consisting of a water-soluble multifunctional carboxylic acid, a dicarboxylic acid oligomer from a melt reaction between a diol and a dicarboxylic acid or its anhydride, and mixtures thereof and which are curable with water, an alcohol or a water and alcohol mixture. The bio-based thermosets of the invention may be free of VOCs and/or organic solvents. The bio-based thermosets of the invention can be used to form coatings, composites, adhesives, and films. Methods of making the bio-based thermosets of the invention are disclosed as are coating compositions and coated objects, such as coatings, composites, adhesives, and films, using the bio-based thermosets of the invention.

公开(公告)号：US10329377B2

公开(公告)日：2019-06-25

申请号：US14801306

申请日：2015-07-16

Applicant: NDSU RESEARCH FOUNDATION

Inventor： Dean C. Webster ,  Partha Pratim Sengupta ,  Zhigang Chen ,  Xiao Pan ,  Adlina Paramarta

IPC: C08G59/02 ,  C08G59/34 ,  C08G59/42 ,  C08L63/00 ,  C08L63/10 ,  C08G59/14 ,  C08G59/16 ,  C08G59/17 ,  C09D163/00 ,  C07D303/16 ,  C09D163/08 ,  C09D175/08

Abstract: The invention provides highly functional epoxy resins that may be used themselves in coating formulations and applications but which may be further functionalized via ring-opening reactions of the epoxy groups yielding derivative resins with other useful functionalities. The highly functional epoxy resins are synthesized from the epoxidation of vegetable or seed oil esters of polyols having 4 or more hydroxyl groups/molecule. In one embodiment, the polyol is sucrose and the vegetable or seed oil is selected from corn oil, castor oil, soybean oil, safflower oil, sunflower oil, linseed oil, tall oil fatty acid, tung oil, vernonia oil, and mixtures thereof. Methods of making of the epoxy resin and each of its derivative resins are disclosed as are coating compositions and coated objects using each of the resins.