# US 2023/0265239 A1 · Process for preparing poly(alkylene furandicarboxylate) > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2023/0265239 A1 - Document ID: US20230265239A1 - Status: Published application - Kind: A1 - Application number: 18/141,613 - Filed: 2023-05-01 - Published: 2023-08-24 - Earliest claimed: 2017-02-24 - Applicants: Covation Inc. - Inventors: Hari Babu SUNKARA; Paul J. Pigliacampi - Web page: https://patentgrep.com/patent/US20230265239A1 ## CPC - C08G 63/672: Dicarboxylic acids and dihydroxy compounds - C08G 63/181: Acids containing aromatic rings - C08G 63/668: derived from polycarboxylic acids and polyhydroxy compounds - C08G 63/85: Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} - C08K 5/18: with aromatically bound amino groups - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A process to prepare poly(alkylene furandicarboxylate) polymer is disclosed herein. In one embodiment, the process comprises a) contacting a mixture comprising furandicarboxylic acid dialkyl ester, a diol comprising ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,4-cyclohexanedimethanol, or mixtures thereof, and a metal catalyst at a temperature in the range of from about 140° C. to about 220° C. to form prepolymer, wherein the mole ratio of the furandicarboxylic acid dialkyl ester to the diol is in the range of from 1:1.3 to 1:2.2; b) performing polycondensation by heating the prepolymer under reduced pressure to a temperature in the range of from about 220° C. to about 260° C. to form poly(alkylene furandicarboxylate) polymer; wherein the rate of polycondensation in step c) is faster with the anthraquinone compound present than without; and c) adding at least one anthraquinone compound as disclosed herein; and ## Claims ### Claim 1 A process comprising the steps: a) contacting a mixture comprising furandicarboxylic acid dialkyl ester, a diol comprising ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,4-cyclohexanedimethanol, or mixtures thereof, and a metal catalyst at a temperature in the range of from about 140° C. to about 220° C. to form prepolymer, wherein the mole ratio of the furandicarboxylic acid dialkyl ester to the diol is in the range of from 1:1.3 to 1:2.2; b) performing polycondensation by heating the prepolymer under reduced pressure to a temperature in the range of from about 220° C. to about 260° C. to form poly(alkylene furandicarboxylate) polymer; wherein the rate of polycondensation in step c) is faster with the anthraquinone compound present than without; and c) independently adding to step a) and/or step b) at least one anthraquinone compound represented by Structure A wherein each R is independently selected from the group consisting of H, OH, C1-C6 alkyl, NHCOCH3, SO2NHC6H11, and each Q, Y, and Z is independently selected from H, OH, NH2, and NHR′, wherein R′ is cyclohexyl or substituted aryl. ### Claim 2 (depends on 1) The process of claim 1, wherein the furandicarboxylic acid dialkyl ester is 2,5-furandicarboxylate dimethyl ester. ### Claim 3 (depends on 1) The process of claim 1, wherein the diol is 1,3-propanediol and the poly(alkylene furandicarboxylate) polymer is poly(trimethylene furandicarboxylate). ### Claim 4 (depends on 1) The process of claim 1, wherein the diol is ethylene glycol and the poly(alkylene furandicarboxylate) polymer is poly(ethylene furandicarboxylate). ### Claim 5 (depends on 1) The process of claim 1, wherein the diol is 1,4-butanediol and the poly(alkylene furandicarboxylate) polymer is poly(butylene furandicarboxylate). ### Claim 6 (depends on 1) The process of claim 1, wherein the metal catalyst comprises at least one titanium, bismuth, zirconium, tin, antimony, germanium, aluminum, cobalt, magnesium, or manganese compound. ### Claim 7 (depends on 1) The process of claim 1, wherein the metal catalyst is present in the mixture in a concentration in the range of from about 20 ppm to about 300 ppm, based on the total weight of the polymer. ### Claim 8 (depends on 1) The process of claim 1, wherein the anthraquinone compound is present in the mixture in a concentration in the range of from about 1 ppm to about 20 ppm, based on the total weight of the polymer. ### Claim 9 (depends on 1) The process of claim 1, wherein the anthraquinone compound is present in the prepolymer in a concentration in the range of from about 1 ppm to about 20 ppm, based on the total weight of the polymer. ### Claim 10 (depends on 1) The process of claim 1, wherein the anthraquinone compound is 1,4-bis[(2,4,6-trimethylphenyl)amino]anthracene-9,10-dione. ### Claim 11 (depends on 1) The process of claim 1, further comprising the step: d) crystallizing the poly(alkylene furandicarboxylate) polymer obtained from step c) at a temperature in the range of from about 100° C. to about 150° C. to obtain crystallized poly(alkylene furandicarboxylate) polymer. ### Claim 12 (depends on 11) The process of claim 11, further comprising the step: e) polymerizing the crystallized poly(alkylene furandicarboxylate) polymer in the solid state at a temperature 5-25° C. below the melting point of the polymer. ### Claim 13 (depends on 12) The process of claim 12, wherein an anthraquinone compound of Structure A is added in step e) polymerizing in the solid state. ### Claim 14 (depends on 13) The process of claim 13, wherein the solid state polymerization rate in step e) is faster with the anthraquinone compound present than without. ### Claim 15 (depends on 1) The process of claim 1, wherein the process is batch, semi-continuous, or continuous. ### Claim 16 (depends on 3) A poly(trimethylene furandicarboxylate) obtained by the process of claim 3. ### Claim 17 (depends on 4) A poly(ethylene furandicarboxylate) obtained by the process of claim 4. ### Claim 18 (depends on 5) A poly(butylene furandicarboxylate) obtained by the process of claim 5.