Polypropiolactones and methods of preparation

Patent metadata

Field	Value
Publication number	US-12338318-B2
Application number	US-202218286264-A
Country	US
Kind code	B2
Filing date	Apr 12, 2022
Priority date	Apr 16, 2021
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

Disclosed are methods of efficiently making poly(3-hydroxypropionate) and related copolymers from beta propiolactone utilizing carboxylate salts of an onium cation. In another aspect, the present invention provides polymerization systems comprising combinations of initiators and monomers that together enable the efficient production of poly(3-hydroxypropionate) and related copolymers. Disclosed are novel polymer compositions having structures and/or compositional characteristics that differentiate them from previously produced polymers and polymer compositions.

First claim

We claim:

1. A polymer comprising one or more polymer chains having ring opened beta propiolactone and/or substituted betapropiolactone units and having on one end of the chains a residue of a carboxylate anion covalently bonded to the one end of the polymer chains;
wherein the polymer comprises chains according to the formula:

wherein: A is separately in each occurrence a polymer chain having ring opened beta propiolactone and/or substituted betapropiolactone units;
R 20 is separately in each occurrence a hydrocarbyl group which is optionally substituted; and
w is separately in each occurrence a number of 1 or greater:

wherein the polymer exhibits one or more of the polymer is polymorphic having DSC peaks at from 73 to 83° C. and from 110 to 125° C. or the polymers are crosslinked by one or more polyepoxides or polylactones.

2. The polymer according to claim 1 , wherein the polymer contains a comonomer which polymerizes with ring opened beta propiolactone and/or substituted betapropiolactone.

3. The polymer according claim 2 , wherein the comonomers are one or more of caprolactones, lactides, epoxides, oxetanes, cyclic anhydrides, cyclic ethers, lactams, episulfides, aziridines, (meth)acrylates, valerolactones, butyrolactone, glycolides and substituted glycolides.

4. The polymer according to claim 1 wherein the polymer has polydispersity of 2.5 or less calculated from gel permeation chromatography data.

5. The polymer according to claim 1 , wherein the polymer exhibits a polydispersity of 3.5 or less.

6. A polymer according to claim 1 , wherein the polymer is polymorphic having DSC peaks at from 73 to 83° C., from 89 to 95° C. and from 110 to 125° C.

7. A polymer comprising one or more polymer chains having ring opened beta propiolactone and/or substituted betapropiolactone units and having on one end of the chains a residue of a carboxylate anion covalently bonded to the one end of the polymer chains; wherein the polymer comprises chains according to the formula:

wherein A is separately in each occurrence a polymer chain having ring opened beta propiolactone and/or substituted betapropiolactone units, w is 2 and R 20 is a propyl group having a hydroxyl group on the middle carbon, 2 carbon.

8. A polymer comprising one or more polymer chains having ring opened beta propiolactone and/or substituted betapropiolactone units and having on one end of the chains a residue of a carboxylate anion covalently bonded to the one end of the polymer chains; wherein the polymer comprises chains according to the formula:

wherein A is separately in each occurrence a polymer chain having ring opened beta propiolactone and/or substituted betapropiolactone units; w is 3 and R 20 is an ethyl group.

9. A polymer according to claim 7 , wherein the polymer is polymorphic having DSC peaks at from 73 to 83° C. and from 110 to 125° C. or the polymers are crosslinked by one or more polyepoxides or polylactones.

10. A polymer according to claim 8 , wherein the polymer is polymorphic having DSC peaks at from 73 to 83° C. and from 110 to 125° C. or the polymers are crosslinked by one or more polyepoxides or polylactones.

Assignees

• Novomer Inc

Inventors

• Derosa Christopher A
• Stoutenburg Eric
• Todd Lisa B
• Falkner Catherine A

Classifications

• C08G63/81

  using solvents (C08G63/79 takes precedence) · CPC title

• C08G63/08 Primary

  Lactones or lactides · CPC title

• C08G63/6852 Primary

  derived from hydroxy carboxylic acids · CPC title