IP Library Patent Application 17135562
Patent Application
App. No. 17/135,562

PROCESS FOR PREPARING POLY(TRIMETHYLENE FURAN DICARBOXYLATE)

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Patent No.
US None
App. No.
17/135,562
Abstract

A process is disclosed herein, the process comprising: a) contacting a mixture comprising furandicarboxylic acid dialkyl ester, 1,3-propanediol, and a metal catalyst at a temperature in the range of from 160° C. to 220° C. to form a prepolymer, wherein the mole ratio of the furandicarboxylic acid dialkyl ester to the 1,3-propanediol is in the range of from 1:1.3 to 1:2.2 and the concentration of metal catalyst is in the range of from 20 ppm to 400 ppm, based on the total weight of the mixture; b) removing at least a portion of the unreacted 1,3-propanediol; and c) heating the prepolymer to a temperature in the range of from 230° C. to 260° C. under reduced pressure to form poly(trimethylene furandicarboxylate) polymer while removing 1,3-propanediol. The poly(trimethylene furandicarboxylate) polymer

Claims (53)

1 . A composition comprising:

poly(trimethylene furandicarboxylate) polymer comprising:

ix) 95 to 99.9% by weight of trimethylene furandicarboxylate repeat units;

x) less than or equal to 1% by weight of di-PDO repeat units in the polymer backbone;

xi) less than or equal to 20 milliequivalents of allyl end group per kilogram of polymer;

xii) less than or equal to 15 milliequivalents of carboxylic acid end groups per kilogram of polymer;

xiii) less than or equal to 10 milliequivalents of alkyl ester end groups per kilogram of polymer;

xiv) less than or equal to 1% by weight of cyclic dimer oligoester;

xv) less than or equal to 10 milliequivalents of di-PDO end groups per kilogram of polymer; and

xvi) an intrinsic viscosity in the range of from 0.70 to 1.2 dL/g;

wherein the percentages by weight are based on the total weight of the poly(trimethylene furandicarboxylate) polymer in the composition.

2 . The composition of claim 1 , wherein the composition has a b* color value of less than 15, as determined by spectrocolorimetry.

3 . The composition of claim 1 , wherein the composition has a b* color value of less than 10, as determined by spectrocolorimetry.

4 . The composition of claim 1 , wherein the composition has an L color value greater than or equal to 60, as determined by spectrocolorimetry.

5 . The composition of claim 1 , further comprising one or more additives comprising a thermal stabilizer, a UV absorber, an antioxidant, a nucleating agent, a process aid, a toner/optical brightener, an oxygen barrier additive, a chain extender, a chain terminator, a reheat agent, or a light blocking agent.

6 . The composition of claim 1 , wherein the furandicarboxylic acid dialkyl ester is 2,5-furandicarboxylate dimethyl ester.

7 . A process comprising:

a) contacting a mixture comprising furandicarboxylic acid dialkyl ester, 1,3-propanediol, and a metal catalyst at a temperature in the range of from 160° C. to 220° C. to form a prepolymer,

wherein the mole ratio of the furandicarboxylic acid dialkyl ester to the 1,3-propanediol is in the range of from 1:1.3 to 1:2.2 and

the concentration of metal catalyst is in the range of from 20 ppm to 400 ppm, based on the total weight of the mixture;

b) removing at least a portion of the unreacted 1,3-propanediol; and

c) heating the prepolymer to a temperature in the range of from 230° C. to 260° C. under reduced pressure to form poly(trimethylene furandicarboxylate) polymer while removing 1,3-propanediol.

8 . The process of claim 7 , wherein the poly(trimethylene furandicarboxylate) polymer has a b* color value of less than 15, as determined by spectrocolorimetry.

9 . The process of claim 7 , wherein the poly(trimethylene furandicarboxylate) polymer has an intrinsic viscosity in the range of from 0.70 to 1.2 dL/g.

10 . The process of claim 7 , wherein the process is batch, semi-continuous, or continuous.

11 . The process of claim 7 , wherein at least 50% by weight of the excess 1,3-propanediol is removed in step b).

12 . The process of claim 7 , wherein at least 90% by weight of the excess 1,3-propanediol is removed in step b).

13 . The process of claim 7 , wherein the furandicarboxylic acid dialkyl ester is 2,5-furandicarboxylate dimethyl ester.

14 . The process of claim 7 , wherein the poly(trimethylene furandicarboxylate) polymer has a crystallization half time measured at 120° C. is less than or equal to 100 minutes.

15 . The process of claim 7 , wherein step a) further comprises concurrently removing at least a portion of the alkyl alcohol formed.

16 . The process of claim 7 , further comprising step d) crystallizing the poly(trimethylene furandicarboxylate) polymer at a temperature in the range of from about 110° C. to about 130° C. to obtain crystallized poly(trimethylene furandicarboxylate) polymer.

17 . Poly(trimethylene furandicarboxylate) polymer obtained by the process of claim 7 .

18 . The poly(trimethylene furandicarboxylate) polymer of claim 17 , wherein the polymer comprises:

xvii) 95 to 99.9% by weight of trimethylene furandicarboxylate repeat units;

xviii) less than or equal to 20 milliequivalents of allyl end group per kilogram of polymer;

xix) less than or equal to 15 milliequivalents of carboxylic acid end groups per kilogram of polymer;

xx) less than or equal to 1% by weight of di-PDO repeat units in the polymer backbone;

xxi) less than or equal to 10 milliequivalents of alkyl ester end groups per kilogram of polymer;

xxii) less than or equal to 1% by weight of cyclic dimer oligoester;

xxiii) less than or equal to 10 milliequivalents of di-PDO end groups per kilogram of polymer; and

xxiv) an intrinsic viscosity in the range of from 0.70 to 1.20 dL/g;

wherein the percentages by weight are based on the total weight of the poly(trimethylene furandicarboxylate) polymer.

19 . A composition comprising:

poly(trimethylene furandicarboxylate) polymer comprising:

ix) 95 to 99.9% by weight of trimethylene furandicarboxylate repeat units;

x) less than or equal to 1% by weight of di-PDO repeat units in the polymer backbone;

xi) less than or equal to 20 milliequivalents of allyl end group per kilogram of polymer;

xii) less than or equal to 21 milliequivalents of carboxylic acid end groups per kilogram of polymer;

xiii) less than or equal to 15 milliequivalents of alkyl ester end groups per kilogram of polymer;

xiv) less than or equal to 1% by weight of cyclic dimer oligoester;

xv) less than or equal to 10 milliequivalents of di-PDO end groups per kilogram of polymer; and

xvi) an intrinsic viscosity in the range of from 0.60 to 1.2 dL/g;

wherein the percentages by weight are based on the total weight of the poly(trimethylene furandicarboxylate) polymer in the composition.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2024
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: COVATION INC.
Reel/Frame 066208/0565 →