New Jersey Institute of Technology

Xianhong Feng

Michael L Jaffe

Willis Hammond

Anthony East

An AB monomer, useful for the production of condensation polymers, wherein the AB monomer has the structure: A-X-C-Y-B; wherein A is reactive carbonyl derivative of carboxylic acids; Y is a bisanhydrohexitol unit derived from the group consisting of isosorbide, isoidide and isomannide; X is selected from the group consisting of: aromatic rings, including 1,4-phenylene, 1,3-phenylene, 2,6-naphthalene 2,7-naphthalene, and substituted derivatives thereof; heterocycles including, 2,5-furan, 2,5-thiophene, substituted 2,5-furan and substituted 2,5-thiophene; and saturated or unsaturated aliphatic chains; B is OH; and C is selected from the group consisting of ether oxygen, a sulfide, and an amine, wherein the amine is NH or NR wherein R is C1 to C6, attaching X to Y.

Polyester ethers derived from asymmetrical monomers based upon bisanhydrohexitols

An AB monomer, useful for the production of condensation polymers, wherein the AB monomer has the structure: A&#x2014;X&#x2014;C&#x2014;Y&#x2014;B; wherein A is a carboxylic acid or ester or reactive carbonyl derivative, Y is a bisanhydrohexitol unit derived from isosorbide, isoidide or isomannide; X is selected from the group consisting of aromatic rings, substituted or unsubstituted heterocycles, and saturated or unsaturated aliphatic chains; and B is OH and C is an ester carbonyl link with the carbon attached to X and the oxygen attached to Y, and wherein the AB monomer is at least about 98% pure endo-substituted bisanhydrohexitol derivative or an at least about 98% pure exo-substituted bisanhydrohexitol derivative.

Polyesters from assymetrical monomers based upon bisanhydrohexitols

Isosorbide-derived epoxies and methods of making same are disclosed. Isosorbide and its isomers are attached to glycidyl ether to make crosslinkable epoxy resin monomers. Adding the hydrophobic functional group into the backbone of isosorbide epoxy or adjusting the amount and type of crosslinker is operable to modify the mechanical properties and water uptake ratio (from &#x3c;1 wt % to &#x3e;50 wt %) of the isosorbide-derived epoxies for different uses. High water uptake epoxies with controllable biodegradation rate are suitable for drug delivery systems or extracellular matrices for biomedical applications, while low water uptake epoxies with strong mechanical properties may be used for can coatings, bone cements and other industrial additives and adhesives.

Isosorbide-derived epoxy resins and methods of making same

A process for producing copolymers of a polymer and asymmetrically substituted compounds of bisanhydrohexitols, including the bisanhydrohexitol isosorbide. In a specific example, the AB monomer isosorbide 2-(4-carbomethoxybenzoate) is synthesized and copolymerized with polyester to form a copolyester. The asymmetrically substituted compounds provide a way of incorporating bisanydrohexitols that may be derived from natural sources into polymers.

Polyesters from asymetrical monomers based upon bisanhydrohexitols

A process for producing a copolyester through the production of an AB monomer of isoidide - Isodide 2-(4-carbomethoxyphenyl) ether. In certain aspects, the AB monomer is produced by performing the steps of: protecting the 2-position of isosorbide with a protecting group; functionalizing the 5-position of isosorbide with a suitable leaving group to form a reactive ester; nucleophilicly displacing the leaving group in a reaction with an alkali metal alkoxide or phenoxide to give an isoidide ether through a stereochemical inversion of the 5-position; and removing the protective moiety to create the AB monomer. In certain embodiments, the copolyester is produced by melting the AB monomer and a polyester, optionally with a catalyst.

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Kearny, NJ, United States of America

Xianhong Feng