Ring-opening polymerization of cyclic esters, polyesters formed thereby, and articles comprising the polyesters

a technology of cyclic esters and polyesters, applied in the preparation of carboxylic acid esters, chemistry apparatus and processes, organic chemistry, etc., can solve the problems of limiting the use of polymers and polyyl alcohol, and polyyl alcohol has relatively low molecular weigh

Inactive Publication Date: 2010-03-18
ASANDEI ALEXANDRU DRAGOS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0014]Another embodiment is a method of depolymerizing a polymer comprising ester linkages, comprising: mixing the polymer comprising ester linkages with a catalytic amount of a Group 4 transition metal hydride to form a mixture; and maintaining the mixture at a temperature and for a time effective to depolymerize the polymer comprising ester linkages.

Problems solved by technology

However, known ring-opening polymerization methods typically produce polyesters having relatively low molecular weights.
This molecular weight limitation is manifested as a limitation on the mechanical properties of the polymers (including storage modulus, loss modulus, Young's modulus, tensile elongation at break, and melt viscosity), which in turn limits the uses of the polymers.

Method used

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  • Ring-opening polymerization of cyclic esters, polyesters formed thereby, and articles comprising the polyesters
  • Ring-opening polymerization of cyclic esters, polyesters formed thereby, and articles comprising the polyesters
  • Ring-opening polymerization of cyclic esters, polyesters formed thereby, and articles comprising the polyesters

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0063]This example describes the ring-opening polymerization of ε-caprolactone using Schwartz's reagent. Catalyst (Cp2ZrHCl, 23.27 milligrams (mg), 0.09 millimoles (mmol)), CL (1 milliliter (mL), 9.02 mmol) and toluene (1 mL) were added to a to a 25-milliliter Schlenk tube. The tube was degassed, filled with argon (Ar), and heated to 90° C. and maintained at the temperature for 2.5 hours. A colorless homogeneous solution was formed after less than one minute at 90° C. Periodically, samples were taken under Ar using an airtight syringe, divided into two parts. The first part was used for determination of percent conversion by 1H NMR, which indicated 93 percent conversion of monomer. The second part was used for molecular weight determination by GPC, which indicated a number average molecular weight of 36,577 and a polydispersity index of 1.2.

example 2

[0064]This example describes the synthesis of a high molecular weight polycaprolactone using Schwartz's reagent. 0.14 mL of Cp2ZrHCl stock solution in toluene (Cp2ZrHCl, 15 mg, 0.058 mmol in 3 mL toluene), CL (6 mL, 54.1 mmol), and toluene (18 mL) were added to a to a 250-mL Schlenk tube. The tube was degassed, filled with Ar, and refluxed at 150° C. under Ar. A colorless homogeneous solution was formed in less than one minute. Periodically, samples were taken under Ar using an airtight syringe and divided into two parts for percent conversion and molecular weight determination. These analyses indicated a 93% conversion of monomer, a number average molecular weight of 327,617 atomic mass units, and a polydispersity index of 1.13.

example 3

[0065]This example describes synthesis of a high molecular weight polycaprolactone using bis(cyclopentadienyl)zirconium dihydride. Cp2ZrH2 (10.0 mg, 0.045 mmol), CL (50 microliters (μL), 0.451 mmol) and toluene (4 mL) were combined in a Schlenk tube inside a glove box and heated to 90° C. A homogeneous dispersion (a cloudy mixture in which the cloudiness did not settle) was formed after 15 minutes. 162 μL, of the solution was added into a 250 mL Schlenk tube containing a pre-degassed mixture of CL (4 mL, 36.1 mmol) and toluene (16 mL). The tube was re-degassed, filled with Ar and was heated to 130° C. under Ar. A colorless homogeneous solution was formed. Periodically, samples were taken under Ar using an airtight syringe and divided into two parts for percent conversion and molecular weight determination. These analyses indicated a 66 percent conversion of monomer after 26 hours, a number average molecular weight of 278,778 atomic mass units, and a polydispersity index of 1.42.

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Abstract

Cyclic esters are polymerized in the presence of a catalytic amount of a Group 4 transition metal hydride. The method is capable of producing high molecular weight polyesters with low polydispersities. These high molecular weight polyesters exhibit improved mechanical properties and are useful in a variety of product applications.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]This application is a division of U.S. Nonprovisional patent application Ser. No. 12 / 061,909, filed Apr. 3, 2008, which claims the benefit of U.S. Provisional Patent Application Ser. No. 60 / 910,675 filed Apr. 9, 2007. These priority applications are fully incorporated herein by reference.STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH & DEVELOPMENT[0002]The U.S. Government has certain rights in this invention pursuant to National Science Foundation CHEMISTRY—Organic Synthesis: Methodology and Organometallic, Grant No. CHEM-0518247.BACKGROUND OF THE INVENTION[0003]Polyesters represent a commercially important class of polymers. One route to polyesters is via ring-opening polymerization of cyclic esters. For example, ε-caprolactone can by polymerized to polycaprolactone, which is widely used as a biocompatible material for the fabrication of implantable devices. However, known ring-opening polymerization methods typically produce polyesters...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G63/08C08G79/00C07C67/00
CPCC08G63/08C08G2261/126C08G63/823C08G63/81
Inventor ASANDEI, ALEXANDRU DRAGOS
Owner ASANDEI ALEXANDRU DRAGOS
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