# US 11,898,031 B2 · Biodegradable polyester resin composition and biodegradable polyester molded article including the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,898,031 B2 - Document ID: US11898031B2 - Status: Granted - Kind: B2 - Application number: 18/320,826 - Filed: 2023-05-19 - Published: 2023-11-23 - Granted: 2024-02-13 - Earliest claimed: 2022-05-21 - Assignees: Ecovance Co. Ltd. - Applicants: Ecovance Co. Ltd. - Inventors: Kyung Youn Kim; Seong Dong Kim; Hoon Kim; Jun Su Byeon; Joo Young Jung; Ji Yeon Ryu - Web page: https://patentgrep.com/patent/US11898031B2 ## CPC - C08G 63/183: Terephthalic acids - C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) - C08G 18/4216: {from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols} - C08G 18/7657: {containing two or more aromatic rings} - C08G 63/6856: {Dicarboxylic acids and dihydroxy compounds} - C08G 63/916: {Dicarboxylic acids and dihydroxy compounds} - C08J 5/18: Manufacture of films or sheets - C08K 5/12: of cyclic polycarboxylic acids - C08G 2230/00: Compositions for preparing biodegradable polymers - C08J 2300/16: Biodegradable polymers - C08J 2367/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence) - C08L 2201/06: Biodegradable - C08L 2203/16: used for films - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract An eco-friendly biodegradable polyester resin composition includes: a polyester resin including a diol, an aromatic dicarboxylic acid and an aliphatic dicarboxylic acid; and 5000 ppm to 20000 ppm of a hydrophilic regulator having a molecular weight of 400 to 1300. ## Claims ### Claim 1 A biodegradable polyester resin composition, comprising: a polyester resin comprising a diol, an aromatic dicarboxylic acid and an aliphatic dicarboxylic acid; and a hydrophilic regulator, wherein a content of the hydrophilic regulator ranges from 5000 ppm to 20000 ppm based on a total amount of the biodegradable polyester resin composition, and wherein the hydrophilic regulator has a molecular weight of 400 to 1300, wherein the hydrophilic regulator comprises: a first oligomer having a molecular weight ranging from 415 to 425; a second oligomer having a molecular weight ranging from 620 to 630; a third oligomer having a molecular weight ranging from 640 to 650; and a fourth oligomer having a molecular weight ranging from 840 to 850. ### Claim 2 (depends on 1) The biodegradable polyester resin composition according to claim 1, wherein the hydrophilic regulator comprises an oligomer formed by reaction of at least two of the diol, the aromatic dicarboxylic acid and the aliphatic dicarboxylic acid. ### Claim 3 (depends on 1) The biodegradable polyester resin composition according to claim 1, wherein a hydrolysis degree after one week is 35% to 60%, and a hydrolysis degree after three weeks is 85% or more, wherein the hydrolysis degree after one week and the hydrolysis degree after three weeks are measured by a measurement method below: wherein in the measurement method, the hydrolysis degree after one week is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester film, of the biodegradable polyester film placed for one week under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%, and the hydrolysis degree after three weeks is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester film, of the biodegradable polyester film placed for three weeks under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%. ### Claim 4 (depends on 1) The biodegradable polyester resin composition according to claim 1 wherein a content of the first oligomer ranges from 3000 to 5000 ppm based on the polyester resin, a content of the second oligomer ranging from 2000 ppm to 4000 ppm based on the biodegradable polyester resin, a content of the third oligomer ranging from 500 ppm to 2000 ppm based on the biodegradable polyester resin, and a content of the fourth oligomer ranging from 700 ppm to 2500p ppm based on the biodegradable polyester resin. ### Claim 5 (depends on 1) The biodegradable polyester resin composition according to claim 1, wherein the hydrophilic regulator comprises a first oligomer, wherein the first oligomer comprises one first unit represented by Formula 6 below and one second unit represented by Formula 7 below: ### Claim 6 (depends on 5) The biodegradable polyester resin composition according to claim 5 wherein the hydrophilic regulator comprises a second oligomer; and a third oligomer, wherein the second oligomer comprises one first unit denoted above and two second units denoted above, the third oligomer comprises two first units denoted above and one second unit denoted above, and the second oligomer is comprised in the hydrophilic regulator in a higher content than the third oligomer. ### Claim 7 (depends on 6) The biodegradable polyester resin composition according to claim 6 wherein the hydrophilic regulator further comprises a fourth oligomer, wherein the fourth oligomer comprises two first units denoted above and two second units denoted above. ### Claim 8 (depends on 1) The biodegradable polyester resin composition according to claim 1, wherein a water contact angle of the biodegradable polyester resin composition measured by a measurement method below is 65° to 90°, and a polarity of the biodegradable polyester resin composition measured by a measurement method below is 4 mN/m to 7 mN/m: wherein in the measurement method the biodegradable polyester resin composition is dried at 80° C., placed in a stainless steel mold, and compressed at 210° C. under a pressure of 10 MPa for 3 minutes to produce a polyester sheet having a thickness of 300 μm, and the water contact angle and the polarity are measured on a surface of the polyester sheet. ### Claim 9 (depends on 1) The biodegradable polyester resin composition according to claim 1, wherein a biodegradability of the biodegradable polyester resin composition after one week is 45% to 65%, a biodegradability of the biodegradable polyester resin composition after nine weeks is 85% or more, wherein the biodegradability after one week and the biodegradability after nine weeks are measured by a measurement method below: wherein in the measurement method the biodegradability after one week is a molecular weight reduction rate, compared to an initial molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed at 60° C. and a relative humidity of 90% for one week under composting conditions, and the biodegradability after nine weeks is a molecular weight reduction rate, compared to an initial molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed at 60° C. and a relative humidity of 90% for nine weeks under composting conditions. ### Claim 10 A biodegradable polyester resin composition, comprising a polyester resin comprising a diol, an aromatic dicarboxylic acid and an aliphatic dicarboxylic acid, a hydrolysis degree after one week is 35% to 60%, and a hydrolysis degree after three weeks is 85% or more, wherein the hydrolysis degree after one week and the hydrolysis degree after three weeks are measured by a measurement method below: wherein in the measurement method the hydrolysis degree after one week is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed for one week under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%, and the hydrolysis degree after three weeks is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed for three weeks under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%. ### Claim 11 (depends on 10) The biodegradable polyester resin composition according to claim 10, wherein a biodegradability after nine weeks is 85% or more, wherein the biodegradability after nine weeks is a molecular weight reduction rate, compared to an initial molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed at 60° C. and a relative humidity of 90% for nine weeks under composting conditions. ### Claim 12 (depends on 10) The biodegradable polyester resin composition according to claim 10, wherein a biodegradability after one week is 45% to 75%, wherein the biodegradability after one week is a molecular weight reduction rate, compared to an initial molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed at 60° C. and a relative humidity of 90% for one week under composting conditions. ### Claim 13 (depends on 10) The biodegradable polyester resin composition according to claim 10, wherein a hydrolysis degree after two weeks is 80% to 95%, wherein the hydrolysis degree after two weeks is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed for two weeks under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%. ### Claim 14 (depends on 13) The biodegradable polyester resin composition according to claim 13, wherein a hydrolysis degree after four weeks is 85% or more, wherein the hydrolysis degree after four weeks is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed for four weeks under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%, and a hydrolysis degree increase rate from one week to two weeks is 29%/week to 50%/week, and a hydrolysis degree increase rate from three weeks to four weeks is 0.01%/week to 3%/week. ### Claim 15 (depends on 12) The biodegradable polyester resin composition according to claim 12, wherein a biodegradability after four weeks is 73% to 85%, wherein the biodegradability after four weeks is a number average molecular weight reduction rate, compared to an initial number average molecular weight of the biodegradable polyester resin composition, of the biodegradable polyester resin composition placed for four weeks under high-temperature and high-humidity conditions of 80° C. and a relative humidity of 100%, and a biodegradability increase rate from one week to four weeks is 3.5%/week to 8%/week. ### Claim 16 (depends on 10) The biodegradable polyester resin composition according to claim 10, wherein an acid value of the biodegradable polyester resin composition is 2.0 mg KOH/g or less. ### Claim 17 (depends on 16) The biodegradable polyester resin composition according to claim 16, wherein an oligomer having a molecular weight ranging from 400 to 1300 is comprised in an amount ranging from 5000 ppm to 20000 ppm based on a total amount of the biodegradable polyester resin composition. ### Claim 18 (depends on 17) The biodegradable polyester resin composition according to claim 17, wherein the oligomer comprises the diol, the aromatic dicarboxylic acid and the aliphatic dicarboxylic acid. ### Claim 19 A biodegradable molded article, comprising a biodegradable resin composition, wherein the biodegradable resin composition comprises a polyester resin comprising a diol, an aromatic dicarboxylic acid and an aliphatic dicarboxylic acid; and a hydrophilic regulator, wherein a content of the hydrophilic regular ranges from 5000 ppm to 20000 ppm based on a total amount of the biodegradable polyester resin composition, and wherein the hydrophilic regulator has a molecular weight of 400 to 1300 wherein the hydrophilic regulator comprises: a first oligomer having a molecular weight ranging from 415 to 425; a second oligomer having a molecular weight ranging from 620 to 630; a third oligomer having a molecular weight ranging from 640 to 650; and a fourth oligomer having a molecular weight ranging from 840 to 850.