Virginia Tech Intellectual Properties, Inc.

Purdue Research Foundation

Vtip Intellectual Properties, Inc.

Kevin Edgar

Junyi Chen

Charles E Frazier

John Matson

Brittany L B Nichols

Xiangtao Meng

Ann Walstrom Norris

Lynne S Taylor

Daiqiang Xu

Yifan Dong

Xueyan Zheng

Laura I Mosquera-Giraldo

Ann Norris

Nilanjana Kar

Kyle Arrington

A method for the synthesis of alkyl ω-carboxy(hydroxyethyl) polysaccharides is described. The method includes methylating or ethylating a polysaccharide or providing a methylated or ethylated polysaccharide, hydroxyethylating the methylated or ethylated polysaccharide, and oxidizing the hydroxyethylated polysaccharide to form the ω-carboxy(hydroxyethyl) polysaccharide. A method for the synthesis of oxidized polysaccharides is also described. The method includes hydroxypropylating a polysaccharide and oxidizing the hydroxypropylated polysaccharides. A method for the production of a solid capable of forming a hydrogel is also described. The method includes combining a first solution comprising an oxidized oligo(hydroxypropyl) polysaccharide bearing one or more ketone groups with a second solution comprising an amine substituted polysaccharide to form a third solution, and removing solvent from the third solution to form the solid, or adding an additional solvent to the third solution to precipitate the solid. Novel polysaccharides and hydrogels prepared according to these methods are also described.

Amphiphilic polysaccharides, polysaccharide-based hydrogels, and methods of manufacture

Described herein are block copolymers that can be used as compatibilizers. The block copolymers can be graft block or triblock copolymers. The block copolymers can include a polysaccharide or a polyester and a polyolefin. Also described herein are polymer blends that can include and be made using the block copolymers described herein.

Copolymer compatibilizers and uses thereof

A method for the synthesis of alkyl &#x3c9;-carboxy(hydroxyethyl) polysaccharides is described. The method includes methylating or ethylating a polysaccharide or providing a methylated or ethylated polysaccharide, hydroxyethylating the methylated or ethylated polysaccharide, and oxidizing the hydroxyethylated polysaccharide to form the &#x3c9;-carboxy(hydroxyethyl) polysaccharide. A method for the synthesis of oxidized polysaccharides is also described. The method includes hydroxypropylating a polysaccharide and oxidizing the hydroxypropylated polysaccharides. A method for the production of a solid capable of forming a hydrogel is also described. The method includes combining a first solution comprising an oxidized oligo(hydroxypropyl) polysaccharide bearing one or more ketone groups with a second solution comprising an amine substituted polysaccharide to form a third solution, and removing solvent from the third solution to form the solid, or adding an additional solvent to the third solution to precipitate the solid. Novel polysaccharides and hydrogels prepared according to these methods are also described.

Methods for the cross-metathesis of polysaccharides with one or more olefin-terminated side chains and cross-metathesized products are described. In an exemplary embodiment, a method for the synthesis of cellulose &#x3c9;-carboxyesters via olefin cross-metathesis with acrylates is described. Conditions of the reactions were relatively mild and the olefin-substituted polysaccharides and the appropriate acrylate partners appear to follow Grubbs rules as summarized herein. Additionally, a method of hydrogenation of the cross-metathesized product is described. The compounds and methods may be useful for waterborne coating applications, adhesives, lubricants, or any product in need of dispersion in an aqueous media.

Polysaccharide derivatives and cross-metathesis processes for preparing them

Methods for the cross-metathesis of polysaccharides with one or more olefin-terminated side chains and cross-metathesized products are described. In an exemplary embodiment, a method for the synthesis of cellulose &#x3c9;-carboxyesters via olefin cross-metathesis is described. Conditions of the reactions were relatively mild and the olefin-substituted polysaccharides and the appropriate monomeric olefin partners appear to follow Grubbs rules as summarized herein. The compounds and methods may be useful for structure-property studies, particularly those aimed at developing polymers for drug delivery, such as for controlled-release drug delivery systems, controlled-release coatings, increasing bioavailability of drugs, and maintaining drug supersaturation in the GI tract.

Cross-metathesized polysaccharide derivatives and processes for preparing them

The present invention relates to esters of diacids and cellulosic materials and methods for making thereof. The ester has the chemical composition of Formula (I) Formula I where R1, R2, and R3 can be the same or different, and each of which is selected from &#x2014;H, &#x2014;COR', &#x2014;R&#x2032;&#x2033;, or &#x2014;COR&#x2033; COOH, with the proviso that at least one of the R1, R2, or R3 is &#x2014;COR&#x2033; COOH; R&#x2032; is an alkyl, alkenyl, alkynyl, or aromatic group; R&#x2033; is an alkyl, alkenyl, or alkynyl group having 4 or more carbon atoms (&#x2267;C); and R&#x2032;&#x2033; is an alkyl, alkenyl, alkynyl, polyol, or aromatic group.

Esters of cellulosic materials and diacids and method of making thereof

Embodiments of the invention provide regioselectively substituted carbohydrate and polysaccharide derivatives, such as cellulose esters, and methods for preparing them. Particular methods of the invention include deacylation of esters using tetrabutylammonium fluoride to obtain selective substitution at desired hydroxyl position(s) of the ester. Preferred is deacylation of an ester, which shows selectivity for removal of acyl groups from the ester of the secondary alcohols at C-2 and C-3, and which affords cellulose-6-O-esters with high regioselectivity by a simple one-step process employing no protective groups. Inventive regioselectively substituted cellulose esters can be prepared by such methods to obtain esters with the following anhydroglucose repeating units: 

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Blacksburg, VA, United States of America

Kevin Edgar