Color stabilization of monomers and other reactants for forming bio-based polymers

Patent metadata

Field	Value
Publication number	US-12258325-B2
Application number	US-201917252964-A
Country	US
Kind code	B2
Filing date	Jun 18, 2019
Priority date	Jun 18, 2018
Publication date	Mar 25, 2025
Grant date	Mar 25, 2025

Abstract

Compositions and methods are provided for the production of bio-based polymers (e.g., polymers made from glucose), including polyesters, as well as end products resulting from such production, in which one or more color stabilizing additive compounds is utilized. The additive(s) may be used in the stabilization of a monomer or prepolymer that is reacted in such production methods, prior to obtaining the polymer. Particular bio-based polymers are those having furandicarboxylate moieties or residues in their backbone structure, with poly(alkylene furan dicarboxylate) polymers, such as polyethylene furan dicarboxylate) (PEF) and poly(trimethylene furan dicarboxylate) (PTF) being representative.

First claim

The invention claimed is:

1. A monomer composition, consisting essentially of:
2,5-furan dicarboxylic acid (FDCA) or an esterified derivative thereof and a color stabilizing additive compound, wherein the esterified derivative is formed by the esterification of FDCA with methanol, ethanol, or phenol.

2. The monomer composition of claim 1 , wherein the color stabilizing additive compound is a substituted phenol;
wherein the substituted phenol is a methoxy-substituted phenol or a tert-butyl-substituted phenol.

3. The monomer composition of claim 1 , wherein the color stabilizing additive compound is selected from the group consisting of butylated hydroxyanisole (BHA); 2,6-dimethoxyphenol (DMP); 2,6-di-tert-butyl-4-methoxylphenol (DTMP); pentaerythritol tetrakis[3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionate (PETC); 2-tert-butylhydroquinone (TBHQ); 4,4′-bis(α,α-dimethylbenzyl) diphenylamine (XDPA); ethylenebis (oxyethylene) bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)-propionate); tris(2,4-di-tert-butylphenyl)phosphite; octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate, ascorbic acid, and mixtures thereof.

4. The monomer composition of claim 1 , wherein the monomer composition consists essentially of, as the esterified derivative of FDCA, a dialkyl ester derivative formed by esterification of FDCA with methanol, ethanol, or phenol.

5. The monomer composition of claim 4 , wherein the monomer composition consists essentially of, as the dialkyl ester derivative of FDCA, a dimethyl ester derivative that is 2,5-furan dicarboxylic acid dimethyl ester (FDME).

6. The monomer composition of claim 5 , wherein the color stabilizing additive compound is present in the monomer composition in an amount from about 50 to about 2000 parts per million by weight (wt-ppm).

7. The monomer composition of claim 5 , wherein the monomer composition exhibits an American Public Health Association (APHA) color of less than 10 and a chromaticity coordinate b* in the L* a* b* color space of less than 0.5 after accelerated degradation testing at 120° C. in an isolated air environment for 15 hours.

8. The monomer composition of claim 5 , wherein the monomer composition exhibits an American Public Health Association (APHA) color of less than 10 and a chromaticity coordinate b* in the L* a* b* color space of less than 0.5 after accelerated degradation testing at 150° C. in an isolated air environment for 6 hours.

9. The monomer composition of claim 1 , wherein the monomer composition consists essentially of FDCA.

10. The monomer composition of claim 9 , wherein a solution of the monomer composition, formed by dissolution in a colorless solvent at a dissolution level of 1-3% by weight of FDCA, exhibits a chromaticity coordinate b* in the L* a* b* color space of less than 0.5 after accelerated degradation testing at 100° C. in an isolated air environment for 2 hours.

11. The monomer composition of claim 10 ,
wherein the solution of the monomer composition, formed by dissolution in the colorless solvent which is a propylene glycol, at a dissolution level of 1% by weight of FDCA, exhibits a chromaticity coordinate b* in the L* a* b* color space of less than 0.5 after accelerated degradation testing at 100° C. in an isolated air environment for 2 hours.

12. The monomer composition of claim 10 ,
wherein the solution of the monomer composition, formed by dissolution in the colorless solvent which is triethylene glycol monomethyl ether, at a dissolution level of 3% by weight of FDCA, exhibits a chromaticity coordinate b* in the L* a* b* color space of less than 0.5 after accelerated degradation testing at 100° C. in an isolated air environment for 2 hours.

13. The monomer composition of claim 10 , wherein, in the solution of the monomer composition, the color stabilizing additive compound is present in an amount from about 50 to about 2000 parts per million by weight (wt-ppm).

14. The monomer composition according to claim 1 , wherein the color stabilizing additive compound is added prior to administration of an esterification/transesterification catalyst.

Assignees

• Archer Daniels Midland Co
• Dupont Ind Biosciences Usa Llc

Inventors

• Hagberg Erik
• Ma Chi Cheng
• Stensrud Kenneth F

Classifications

• C08G63/78

  Preparation processes · CPC title

• C08G63/66

  Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence) · CPC title

• C07D307/68 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• C08K5/14 Primary

  Peroxides · CPC title

• A61K31/341 Primary

  not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine · CPC title