Phosphorus-containing polymers, and methods of producing thereof

Patent metadata

Field	Value
Publication number	US-11685809-B2
Application number	US-201916981437-A
Country	US
Kind code	B2
Filing date	Mar 20, 2019
Priority date	Mar 22, 2018
Publication date	Jun 27, 2023
Grant date	Jun 27, 2023

Abstract

Provided are methods of producing sulfur- and phosphorus-containing polymers from beta-lactones. The sulfur- and phosphorus-containing polymers include bio-based sulfur- and phosphorus-containing polymers that may be obtained from renewable sources.

First claim

What is claimed is:

1. A method, comprising:
combining a beta-lactone with a diol compound to produce an alkanoate compound having two terminal hydroxy groups; and
combining the alkanoate compound with a phosphanediamine compound or a phosphanetriamine compound to produce a phosphorus-containing polyester.

2. The method of claim 1 , wherein the beta-lactone is beta-propiolactone, beta-butyrolactone, or beta-valerolactone, and wherein the diol is ethylene glycol.

3. A method according to claim 1 , wherein
the beta-lactone corresponds to formula (1)

wherein the diol corresponds to formula (4) HO—R 4 —OH, wherein R 4 is -alkyl-, -cycloalkyl-, -aryl-, -heteroaryl-, -ether-, or -arylalkyl-; and
wherein the alkanoate compound having two terminal hydroxy groups corresponds to formula (7)

wherein R 1a , R 1b , R 1c , and R 1d is as defined for formula (1), and wherein R 4 is as defined above for formula (4);
wherein the phosphanediamine compound corresponds to the formula (C-1)

and
wherein the phosphanetriamine compound is a compound of formula (C-2)

wherein R y is alkyl or OR y1 , and wherein R y1 is alkyl; and
wherein the polymer comprises repeating units of formula

wherein each R 1a , R 1b , R 1c and R 1d is independently H or alkyl, R 4 is independently in each occurrence-alkyl-, -cycloalkyl-, -aryl-, -heteroaryl-, -ether-, or -arylalkyl-, each R z1 , R z2 , R z3 , R z4 , R z5 and R z6 is independently in each occurrence alkyl, R y is independently in each occurrence alkyl or —OR y1 ; and R y1 is alkyl.

4. The method of claim 3 , wherein R 1a is H or alkyl, R 1b , R 1c , and R 1d are all H, and R 4 is -alkyl.

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

Assignees

• Novomer Inc

Inventors

• Lee Han
• Tseitlin Alexander
• Sookraj Sadesh H

Classifications

• C08K5/5399

  Phosphorus bound to nitrogen · CPC title

• C08G63/08 Primary

  Lactones or lactides · CPC title

• C08K2003/3009

  Sulfides · CPC title

• C08K3/30

  Sulfur-, selenium- or tellurium-containing compounds · CPC title

• C08K2003/309

  Sulfur containing acids · CPC title