IP Library Granted Patent US 11,773,215
Granted Patent B2
US 11,773,215 · App. 16/970,736 · Granted Oct 3, 2023

Polypropiolactone films, and methods of producing thereof

Inventor: Utpal Mahendra Vakil (Evansville, IN)
Assignee: Novomer, Inc.
C08G63/08B29C48/0018B29C48/288C08J5/18C08J11/12B29K2067/04B29K2995/004B29K2995/006B29K2995/0077B29K2995/0088C08J2367/04
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Quick Facts
Patent No.
US 11,773,215
App. No.
16/970,736
Granted
Oct 3, 2023
Kind
B2
Abstract

Provided is a method of producing a film by cryogenically grinding polypropiolactone to form a powder, and extruding the powder to form the film. Provided herein are also polypropiolactone films having certain biocontent and compostability, as well as certain mechanical and physical properties. Such films may also be suitable for use as packaging materials.

Claims (31)

1. A method of producing a film, comprising:

blending a mixture of polypropiolactone polymers having different average molecular weights; and

blowing the mixture to form the film.

2. The method of claim 1 , wherein at least one of the polypropiolactone polymers in the mixture of the polypropiolactone polymers has an average molecular weight (M w ) between about 100,000 g/mol and about 200,000 g/mol.

3. The method of claim 1 , wherein at least one of the polypropiolactone polymers in the mixture of the polypropiolactone polymers has an average molecular weight (M w ) between about 800,000 g/mol to about 1,000,000 g/mol.

4. The method of claim 1 , wherein the film is multilayered.

5. A film produced according to the method of claim 1 .

6. A film, comprising extruded polypropiolactone, wherein the film:

(a) has a biocontent of at least about 60% (w/w);

(b) is compostable up to 100%;

(c) has a tensile modulus range between about 800 MPa and about 1100 MPa;

(d) has a tensile strength at break range between about 25 MPa to about 35 MPa; or

(e) has an elongation at break range of about 440% to about 660%, or any combination of (a)-(e).

7. The film of claim 6 , wherein the polypropiolactone has an average molecular weight (M w ) between about 100,000 g/mol to about 200,000 g/mol.

8. The film of claim 6 , wherein the polypropiolactone has an average molecular weight (M w ) between about 800,000 g/mol to about 1,000,000 g/mol.

9. The film of claim 5 for use as packaging material.

10. A method of producing acrylic acid from a bio-based and compostable film, comprising:

providing a polypropiolactone film; and

thermolyzing at least a portion of the polypropiolactone film to produce acrylic acid.

11. The method of claim 1 , further comprising three or more polypropiolactone polymers having differing average molecular weight (M w ).

12. The method of claim 1 , wherein the polypropiolactone polymers have a form of particles, and wherein the polypropiolactone polymers have a size of about 300 ppm to about 3,000 ppm so that the polypropiolactone polymers feed easily into an extruder.

13. The method of claim 1 , wherein the step of blowing the mixture to form the film occurs at a temperature below 160 degrees Celsius so that the film is free of acrylic acid.

14. The method of claim 1 , further comprising:

thermolyzing at least a portion of the film at a temperature above 160 degrees Celsius to produce acrylic acid.

15. The method of claim 11 , further comprising:

producing polypropiolactone polymers from ethylene oxide and carbon monoxide, wherein the ethylene oxide and the carbon monoxide have a biocontent that is greater than 0% (w/w).

16. The film of claim 6 , wherein the polypropiolactone has an average molecular weight (M w ) between about 120,000 g/mol and about 150,000 g/mol.

17. The film of claim 6 , wherein the film has up to about 50% crystallinity.

18. The film of claim 6 , wherein the film is substantially free of acrylic acid.

19. The method of claim 10 , wherein the polypropiolactone film has a tensile modulus range between about 800 MPa and about 1000 MPa or has a tensile strength break range between about 25 MPa to about 35 MPa.

20. The method of claim 10 , wherein the polypropiolactone film has an elongation at break between about 0.1% and about 1000%.

Assignments (4)
CHANGE OF NAME Recorded Mar 24, 2026
From: NMER WINDDOWN, INC.
To: NOVOMER LLC
Reel/Frame 075187/0876 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2022
From: TRUIST BANK
To: NOVOMER, INC.
Reel/Frame 061088/0116 →
SECURITY INTEREST Recorded Feb 1, 2022
From: NOVOMER, INC.
To: TRUIST BANK
Reel/Frame 058922/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2021
From: VAKIL, UTPAL MAHENDRA
To: NOVOMER, INC.
Reel/Frame 056127/0152 →
Continuity (2)
Provisional Application 62654197 · Apr 6, 2018
Related Publication 20200369825A1 · Nov 26, 2020