# US 11,028,221 B2 · PET polymer with an anti-crystallization comonomer that can be bio-sourced

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- Number: US 11,028,221 B2
- Document ID: US11028221B2
- Status: Granted
- Kind: B2
- Application number: 16/060,525
- Filed: 2015-12-11
- Published: 2018-12-13
- Granted: 2021-06-08
- Earliest claimed: 2015-12-11
- Assignees: SociéTé Anonyme Des Eaux MinéRales D'Evian Et En AbréGé “S.A.E.M.E”
- Applicants: Societe Anonyme Des Eaux Minerales D'Evian Et En AbréGé “S.A.E.M.E”
- Inventors: Françoise Poulat; Philippe Reutenauer
- Web page: https://patentgrep.com/patent/US11028221B2

## CPC

- C08G 63/183: Terephthalic acids
- C08G 63/181: Acids containing aromatic rings
- C08G 63/42: Cyclic ethers (C08G59/00 takes precedence); Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
- C08G 63/78: Preparation processes
- C08G 63/80: Solid-state polycondensation
- C08G 2390/00: Containers
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A polyethylene terephthalate (PET) polymer having diacid units derived from diacid compounds, said diacid units comprising: a) from 92.50 mol % to 97.75 mol % of terephthalic units derived from terephthalic acid (TA) or an ester thereof, and b) from 2.25 mol % to 7.50 mol % of 2,5-FDCA units derived from 2,5- furandicarboxylic acid (2,5-FDCA) or an ester thereof, and-diol units derived from diol compound(s), the diol units having monoethylene glycol units derived from monoethylene glycol (MEG), as well as to a method to prepare a PET polymer. The use of a 2,5-FDCA compound selected from 2,5- furandicarboxylic acid (2,5-FDCA) and esters thereof as an anti-crystallization comonomer in a PET polymer and a bio-based PET polymer in which the anti-crystallisation comonomer is bio-based.

## Claims

### Claim 1

A method to prepare a PET polymer comprising:
diacid units derived from diacid compounds, said diacid units comprising:
a) from 96.14 mol % to 97.15 mol % of said diacid units being terephthalic acid (TA) units or an ester thereof, and
b) from 2.85 mol % to 3.86 mol % of said diacid units being 2,5-furandicarboxylic acid (2,5-FDCA) units or an ester thereof, based on 100 mol % of all diacid units, and
diol units derived from diol compound(s), said diol units comprising monoethylene glycol units in an amount of at least 95.00 mol % of the diol units and optionally diethylene glycol units in an amount of less than 5.00 mol % of the diol units, based on 100 mol % of all diol units, comprising copolymerizing a mixture of:
the diacid compounds comprising terephthalic acid (TA) or an ester thereof, and 2,5-furandicarboxylic acid (2,5-FDCA) or an ester thereof, and
the diol compound(s), wherein the diol compound(s) comprise at least 95.00 mol % of monoethylene glycol of said diol compound(s) based on 100 mol % of all diol compound(s),
wherein copolymerizing comprises a first step of melt polymerization and a second step of solid state polymerization,
wherein the melt polymerization comprises a first sub-step of esterification or transesterification and a second sub-step of polycondensation,
wherein the polycondensation is performed at a temperature of 285° C. in the presence of Sb2O3 as a catalyst.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the diol units comprise diethylene glycol units in an amount of less than 5.00 mol % of the diol units.

### Claim 3 (depends on 1)

The method according to claim 1, wherein at least one of the diacid and diol compounds is obtained from at least one bio-material.

### Claim 4 (depends on 1)

The method according to claim 1, wherein:
the diacid compounds comprise:
a) from 96.14 mol % to 97.00 mol % of said diacid compounds being terephthalic acid or dimethyl therephthalate, and
b) from 3.00 mol % to 3.86 mol % of said diacid compounds being 2,5-furandicarboxylic acid or dimethyl 2,5-furandicarboxylate.