Polyesters From Assymetrical Monomers Based Upon Bisanhydrohexitols
AssigneeIowa Corn Promotion Board
InventorsAnthony East, Willis Hammond, Michael Jaffe, Xianhong Feng
Life of this patent
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Abstract
Asymmetrically substituted compounds of bisanhydrohexitols are described, including the bisanhydrohexitol isosorbide. The compounds are useful as AB monomers. The synthesis of polymers from the monomers is also described.
Claims23
An AB monomer comprising bisanhydrohexitol derivatives capable of self-polymerization directly to form stereoregular or regioregular condensation polymer of the general type
- A-X—C—Y—B
- where A is a carboxylic acid or ester or reactive carbonyl derivative such as an acid chloride, Y is a bisanhydrohexitol unit derived from isosorbide, isoidide or isomannide and X is selected from the group consisting of aromatic rings, including 1,4-phenylene, 1,3-phenylene, 2,6-naphthalene or 2,7-naphthalene (or substituted derivatives thereof), and suitable heterocyclic variants, including 2,5-furan and 2,5-thiophene, both saturated and unsaturated aliphatic chains and acyclic compounds, and B is —OH and C is an ester carbonyl link with the carbon attached to X and the oxygen attached to Y.
A process for producing an AB monomer, comprising the steps of:
- (a) reacting a substituted derivative of an bisanhydrohexitol with a protective moiety to protect one of the —OH groups of the substituted derivative of an bisanhydrohexitol;
- (b) reacting the protected substituted derivative of an bisanhydrohexitol with a compound selected from the group consisting of substituted and unsubstituted aromatic, or heterocyclic or aliphatic unsaturated and alicyclic acids and their derivatives to attach the compound to the protected bisanhydrohexitol at the unprotected —OH group via an ester, thioester or amide linkage;
- and
- (c) removing the protective moiety to create an AB monomer.
A method of introducing bisanhydrohexitol moieties into a condensation polymer, comprising adding an oligomer or polymer of claim 15 as an initial reaction material to the condensation polymer initial reaction mixture.
Dependencies are inferred from the claim text.