Polyester ethers derived from asymmetrical monomers based upon bisanydrohexitols

Patent metadata

Field	Value
Publication number	US-9447230-B2
Application number	US-201113050684-A
Country	US
Kind code	B2
Filing date	Mar 17, 2011
Priority date	Mar 18, 2010
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

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.

First claim

We claim:

1. A process for producing a copolyester, comprising:
(a) producing isoidide 2-(4-carbomethoxyphenyl) ether by:
(i) protecting the 2-position of isosorbide with a protecting group;
(ii) functionalizing the 5-position of isosorbide with a leaving group to form a reactive ester;
(iii) 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
(iv) removing the protective moiety to create isoidide 2-(4-carbomethoxyphenyl) ether; and

(b) melting the isoidide 2-(4-carbomethoxyphenyl) ether produced in step (a) and a polyester, optionally with a catalyst.

2. The process of claim 1 , wherein the functionalizing the 5-position of isosorbide is through a mesylation reaction.

3. The process of claim 1 , wherein the polyester is polyethylene terephthalate.

Assignees

• Jaffe Michael
• Hammond Willis
• Feng Xianhong
• East Anthony
• New Jersey Inst Technology

Inventors

• Jaffe Michael
• Hammond Willis
• Feng Xianhong
• East Anthony

Classifications

• C08G63/66

  Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence) · CPC title

• C08G63/664 Primary

  derived from hydroxy carboxylic acids · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title