Bottlebrush polymers derived from poly(methylidenelactide)

Patent metadata

Field	Value
Publication number	US-10072121-B1
Application number	US-201715452996-A
Country	US
Kind code	B1
Filing date	Mar 8, 2017
Priority date	Mar 8, 2017
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

A process of forming a bottlebrush polymer includes forming a poly(methylidenelactide) (PML) material from an L-lactide molecule. The process also includes forming a lactide feedstock that includes a blend of a first amount of an L-lactide monomer and a second amount of the PML material. The process further includes polymerizing the lactide feedstock to form a bottlebrush polymer.

First claim

What is claimed is:

1. A process of forming a bottlebrush polymer, the process comprising:
forming a poly(methylidenelactide) (PML) material from an L-lactide molecule, the PML material having a polymeric repeat unit that includes a lactide group;
blending a first amount of an L-lactide monomer and a second amount of the PML material to form a lactide feedstock; and
polymerizing the lactide feedstock to form a bottlebrush polymer.

2. The process of claim 1 , wherein the bottlebrush polymer is a poly(lactic acid)-polyethylene (PLA-PE) material, the process further comprising adjusting a polyethylene portion of the PLA-PE material by varying the second amount of the PML material.

3. The process of claim 1 , wherein polymerizing the lactide feedstock includes initiating a ring-opening polymerization reaction.

4. The process of claim 3 , wherein the ring-opening polymerization reaction includes chemically reacting the lactide feedstock with a tin(II) octanoate material.

5. The process of claim 1 , wherein forming the PML material from the L-lactide molecule includes:
forming a methylidene lactide molecule from the L-lactide molecule; and
initiating a radical polymerization reaction using a radical initiator to form the PML material from the methylidene lactide molecule.

6. The process of claim 5 , wherein the radical initiator is azobisisobutyronitrile (AIBN).

7. A process of forming a bottlebrush polymer, the process comprising:
forming a mixture that includes a poly(methylidenelactide) (PML) material and a diol, the PML material having a polymeric repeat unit that includes a lactide group;
performing a ring-opening polymerization reaction on the mixture to form a PML-based polyester material; and
chemically reacting the PML-based polyester material with a lactone to form a bottlebrush polymer.

8. The process of claim 7 , wherein the ring-opening polymerization reaction includes a base-catalyzed ring-opening polymerization reaction of the PML material in the presence of the diol.

9. The process of claim 7 , wherein the ring-opening polymerization reaction includes an acid-catalyzed ring-opening polymerization reaction of the PML material in the presence of the diol.

10. The process of claim 7 , wherein the diol is ethylene glycol.

11. The process of claim 7 , wherein the diol is propylene glycol.

12. The process of claim 7 , wherein the lactone is β-propiolactone, γ-butyrolactone, δ-valerolactone, ε-caprolactone, or a combination thereof.

13. The process of claim 7 , wherein the lactone is a biorenewable lactone.

14. The process of claim 7 , further comprising:
forming a methylidene lactide molecule from a biorenewable L-lactide molecule; and
initiating a radical polymerization reaction using a radical initiator to form the PML material from the methylidene lactide molecule.

15. A process of forming a bottlebrush polymer, the process comprising:
initiating a radical polymerization reaction using a radical initiator to form a poly(methylidenelactide) (PML) material from a methylidene lactide molecule, the PML material having a polymeric repeat unit that includes a lactide group;
forming a mixture that includes the PML material or a PML-based polyester material derived from the PML material; and
polymerizing the mixture to form a bottlebrush polymer.

16. The process of claim 15 , wherein:
the radical initiator is azobisisobutyronitrile (AIBN);
the mixture includes a blend of an L-lactide monomer and the PML material;
polymerizing the mixture includes initiating a ring-opening polymerization reaction; and
wherein the bottlebrush polymer is a poly(lactic acid)-polyethylene (PLA-PE) material.

17. The process of claim 15 , further comprising forming the PML-based polyester material by performing a ring-opening polymerization reaction on the PML material in the presence of a diol.

18. The process of claim 17 , wherein the diol is ethylene glycol.

19. The process of claim 17 , wherein the mixture includes a lactone and the PML-based polyester material derived from the PML material.

20. The process of claim 19 , wherein the lactone is biorenewable ε-caprolactone.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Kuczynski Joseph
• Porter Jacob T
• Wertz Jason T

Classifications

• C08G63/08

  Lactones or lactides · CPC title

• C08G83/002 Primary

  Dendritic macromolecules · CPC title

• C08G63/912 Primary

  derived from hydroxycarboxylic acids · CPC title