# US 2019/0375890 A1 · 2, 5-furandicarboxylic acid-based polyesters

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- Number: US 2019/0375890 A1
- Document ID: US20190375890A1
- Status: Published application
- Kind: A1
- Application number: 16/479,258
- Filed: 2018-01-22
- Published: 2019-12-12
- Earliest claimed: 2017-01-26
- Applicants: Synvina C.V.; Roquette Frères
- Inventors: Nicolas Jacquel; Gabriel Degand; René Saint-Loup; Matheus Adrianus Dam; Bing Wang
- Web page: https://patentgrep.com/patent/US20190375890A1

## CPC

- C08G 63/672: Dicarboxylic acids and dihydroxy compounds
- C08G 63/199: Acids or hydroxy compounds containing cycloaliphatic rings
- C08G 63/85: Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The invention is directed to a polyester comprising 5-furandicarboxylic acid moieties (A); ethylene glycol moieties (B); 1,4:3,6-dianhydrohexitol moieties (C); alicyclic diol moieties other than the 1,4:3,6-dianhydrohexitol moieties (D); wherein the molar ratio (B)/[(B)+(C)+(D)] is greater than 0.2. The invention aloes relates to a process of preparing the polyester and to its use.

## Claims

### Claim 1

A polyester comprising:
2,5-furandicarboxylic acid moieties (A);
ethylene glycol moieties (B);
1,4:3,6-dianhydrohexitol moieties (C); and
alicyclic diol moieties other than the 1,4:3,6-dianhydrohexitol moieties (D);
wherein the molar ratio (B)/[(B)+(C)+(D)] is greater than 0.2.

### Claim 2 (depends on 1)

The polyester according to claim 1, wherein the 1,4:3,6-dianhydrohexitol (C) is selected from isosorbide, isomannide, isoidide or mixtures thereof.

### Claim 3 (depends on 2)

The polyester according to claim 2, wherein the 1,4:3,6-dianhydrohexitol (C) is isosorbide.

### Claim 4 (depends on 1)

The polyester according to claim 1, wherein the alicyclic diol other than 1,4:3,6-dianhydrohexitol (D) is selected from 1,4-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol or a mixture thereof.

### Claim 5 (depends on 4)

The polyester according to claim 4, wherein the wherein the alicyclic diol other than 1,4:3,6-dianhydrohexitol (D) is 1,4-cyclohexanedimethanol.

### Claim 6 (depends on 1)

The polyester according to claim 1, wherein the molar ratio [(B)/[(B)+(C)+(D)] does not exceed 0.8, preferably the molar ratio (B)/[(B)+(C)+(D)] is from 0.35 to 0.75.

### Claim 7 (depends on 1)

The polyester according to claim 1, wherein the molar ratio (A)/[(B)+(C)+(D)] is 0.8 to 1.2.

### Claim 8 (depends on 1)

The polyester according to claim 1 having a glass transition temperature of at least 80° C., preferably at least 85° C.

### Claim 9 (depends on 1)

A process of preparation of the polyester according to claim 1 comprising the following steps:
introducing into a reactor monomers comprising 2,5-furandicarboxylic acid or a diester, preferably C1-C2 alkyl diester, thereof (A), ethylene glycol (B), at least one 1,4:3,6-dianhydrohexitol (C), and at least one alicyclic diol other than the 1,4:3,6-dianhydrohexitol (D), and a catalyst, the molar ratio (B)/[(B)+(C)+(D)] being greater than 0.2 and the monomers not comprising aliphatic dicarboxylic acid or a diester thereof and/or terephthalic acid or a diester thereof;
polymerizing the monomers, said step comprising:
oligomerization of the monomers by esterification or transesterification during which the reaction mixture is stirred under inert atmosphere at a temperature of 140° C. to 230° C., preferably 160° C. to 220° C. to produce oligomers;
polycondensation of the oligomers during which the oligomers are stirred under vacuum at a temperature of 230° C. to 300° C., preferably 240° C. to 280° C.; and
collecting the resulting polyester.

### Claim 10 (depends on 1)

A composition comprising the polyester according to claim 1, the composition optionally comprising at least one additive and/or at least one additional polymer.

### Claim 11 (depends on 1)

A plastic article comprising the polyester according to claim 1.