IP Library Granted Patent US 8,268,954
Granted Patent B2
US 8,268,954 · App. 12/669,598 · Granted Sep 18, 2012

Method for making copolymers of lactide and a 1:4-3:6 dianhydrohexitol

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Quick Facts
Patent No.
US 8,268,954
App. No.
12/669,598
Granted
Sep 18, 2012
Kind
B2
Abstract

Polyester-carbonate copolymers are prepared by copolymerizing lactide with a 1:4-3:6 dianhydrohexitol in the presence of a carbonate precursor and a polymerization catalyst. The copolymers have an elevated glass transition temperature, relative to polylactide resins.

Claims (12)

1. A process comprising polymerizing a 1:4-3:6-dianhydrohexitol, lactide and a carbonate precursor in one step by forming a mixture of the 1:4-3:6-dianhydrohexitol, lactide, carbonate precursor, and at least one polymerization catalyst, and subjecting the mixture to polymerization conditions including an elevated temperature and a subatmospheric pressure to form a polyester-carbonate containing randomly distributed dianhydrohexitol carbonate repeating units and lactide repeating units.

2. The process of claim 1 , wherein the molar ratio of the lactide to the 1:4-3:6-dianhydrohexitol is from 5:1 to 1:2.

3. The process of claim 2 , wherein the polyester-carbonate has a T g of 75° C. to 110° C.

4. The process of claim 3 , wherein the 1:4-3:6-dianhydrohexitol is isosorbide.

5. The process of claim 4 , wherein the molar ratio of the lactide to the 1:4-3:6-dianhydrohexitol is from 5:1 to 1:1.

6. The process of claim 1 wherein the carbonate precursor has the structure

wherein each X is independently halogen or an alkoxy or aryloxy group having up to 12 carbon atoms.

7. The process of claim 6 , wherein the carbonate precursor is diphenylcarbonate.

8. The process of claim 1 , wherein the polyester-carbonate has an M n of from 10,000 to 100,000.

9. The process of claim 1 , further comprising coupling the polyester-carbonate with a difunctional coupling agent.

10. The process of claim 9 , wherein the coupled polyester-carbonate has an M n of from 50,000 to 150,000.

11. The process of claim 9 , wherein the difunctional coupling agent is a diisocyanate compound, a diepoxide, a dicarboxylic acid, a dianhydride of a tetracarboxylic acid, or a compound having two primary or secondary amino groups.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Aug 11, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: NATUREWORKS, LLC
Reel/Frame 072412/0844 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Oct 20, 2021
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: NATUREWORKS LLC
Reel/Frame 057873/0985 →
SECURITY INTEREST Recorded Oct 20, 2021
From: NATUREWORKS LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 057879/0338 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jan 16, 2018
From: NATUREWORKS LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045075/0556 →