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US 2011/0257346 A1Published application
Polyester Ethers Derived From Asymmetrical Monomers Based Upon Bisanydrohexitols
AssigneeIowa Corn Promotion Board
InventorsMichael Jaffe, Willis Hammond, Xianhong Feng, Anthony East
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Abstract
Asymmetrically substituted compounds of bisanhydrohexitols are described, including the bisanhydrohexitol isosorbide. The compounds are useful as monomers. The synthesis of polymers from the monomers is also described.
Claims31
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
- wherein A is selected from the group consisting of carboxylic acids, ester derivatives of carboxylic acids, and reactive carbonyl derivatives of carboxylic acids such as an acid chloride;
- 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 and 2,7-naphthalene, and substituted derivatives thereof, and suitable heterocyclic variants, including 2,5-furan and 2,5-thiophene, and both saturated and unsaturated aliphatic chains and acyclic compounds;
- B is —OH;
- and C is selected from the group consisting of ether oxygen, a sulfide sulfur, and an amine, and NH or NR wherein R is C1 to C6, attaching X to Y.
3 more elements
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) converting the unprotected —OH group to a derivative susceptible to nucleophilic substitution;
- (c) reacting the protected substituted derivative of an bisanhydrohexitol with a compound selected from the group consisting of substituted and unsubstituted aromatic phenols and thiophenols, substituted and unsubstituted aromatic primary and secondary amines, aliphatic unsaturated and alicyclic alcohols, and aliphatic unsaturated and alicyclic primary and secondary amines, and their derivatives, to attach the compound to the protected bisanhydrohexitol at the derivatized —OH group via an ether linkage;
- and
- (d) removing the protective moiety.
2 more elements
Dependencies are inferred from the claim text.