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WO2022065690A1 - Polyester comprenant un composant issu d'une biomasse et son procédé de préparation - Google Patents

Polyester comprenant un composant issu d'une biomasse et son procédé de préparation Download PDF

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Publication number
WO2022065690A1
WO2022065690A1 PCT/KR2021/010762 KR2021010762W WO2022065690A1 WO 2022065690 A1 WO2022065690 A1 WO 2022065690A1 KR 2021010762 W KR2021010762 W KR 2021010762W WO 2022065690 A1 WO2022065690 A1 WO 2022065690A1
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Prior art keywords
triol
diol
methyl
group
polyester
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English (en)
Korean (ko)
Inventor
정미혜
김준영
하지민
용다경
박근영
김은지
최민호
박기현
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Kolon Industries Inc
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Kolon Industries Inc
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Priority claimed from KR1020210097219A external-priority patent/KR20220039559A/ko
Application filed by Kolon Industries Inc filed Critical Kolon Industries Inc
Publication of WO2022065690A1 publication Critical patent/WO2022065690A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof

Definitions

  • One embodiment has a carbon reduction effect including a bio-derivative monomer, and has excellent transparency, impact resistance, flexibility, and elasticity compared to conventional polyethyleneterephthalate (PET), so that packaging ( Polyester that can be used as a new biomass PET for packaging) is provided.
  • PET polyethyleneterephthalate
  • the trihydric or higher polyhydric alcohol is propane-1,2,3-triol (propane-1,2,3-triol), 1-methyl-propane-1,2,3-triol (1-methyl-propane- 1,2,3-triol), 2-methyl-propane-1,2,3-triol (2-methyl-propane-1,2,3-triol), butane-1,2,4-triol ( butane-1,2,4-triol), 1-methyl-butane-1,2,4-triol (1-methyl-butane-1,2,4-triol), 2-methyl-butane-1,2 ,4-triol (2-methyl-butane-1,2,4-triol), pentane-1,2,5-triol (pentane-1,2,5-triol), pentane-1,3,5 -triol (pentane-1,3,5-triol), 1-methyl-pentane-1,2,5-triol (1-methyl-pentane-1,2,5-triol), 2-methyl-pentane
  • the esterification reaction may be performed at a pressure of 0 kg/cm 2 to 10.0 kg/cm 2 and a temperature of 150° C. to 270° C.
  • the polycondensation may be performed at a pressure of 600 mmHg to 0.01 mmHg and a temperature of 150° C. to 290° C. for 0.5 hours to 2.75 hours.
  • alkyl refers to saturated monovalent aliphatic hydrocarbon radicals, including straight and branched chains, having the specified number of carbon atoms.
  • Alkyl groups typically have 1 to 20 carbon atoms ("C 1 -C 20 alkyl”), preferably 1 to 12 carbon atoms (“C 1 -C 12 alkyl”), more preferably 1 to 8 carbon atoms (“C 1 -C 8 alkyl”), or 1 to 6 carbon atoms (“C 1 -C 6 alkyl”), or 1 to 4 carbon atoms (“C 1 -C 4 alkyl”) ) contains Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-oc
  • Alkyl groups described herein as being optionally substituted may be substituted with one or more substituents, which substituents are independently selected unless otherwise stated.
  • the total number of substituents is equal to the total number of hydrogen atoms on the alkyl moiety to the extent that such substitutions satisfy the chemical sense.
  • Optionally substituted alkyl groups typically have 1 to 6 optional substituents, often 1 to 5 optional substituents, preferably 1 to 4 optional substituents, more preferably 1 to 3 optional substituents It may contain substituents.
  • Optional substituents suitable for the above alkyl groups include, but are not limited to, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl, 3 to 12 membered heterocycle.
  • Alkylene groups are unsubstituted or substituted by the same groups as described herein as suitable for alkyl.
  • halo or halogen refers to fluorine (F), chlorine (Cl), bromine (Br) or iodine (I), unless otherwise specified.
  • hydroxy refers to the group —OH.
  • alkoxy refers to a monovalent -O-alkyl group in which the alkyl moiety has the specified number of carbon atoms.
  • An alkoxy group typically has 1 to 8 carbon atoms (“C 1 -C 8 alkoxy”), or 1 to 6 carbon atoms (“C 1 -C 6 alkoxy”), or 1 to 4 carbon atoms ( “C 1 -C 4 alkoxy”).
  • C 1 -C 4 alkoxy is methoxy (-OCH 3 ), ethoxy (-OCH 2 CH 3 ), isopropoxy (-OCH(CH 3 ) 2 ), tert-butyloxy (-OC( CH 3 ) 3 ) and the like.
  • a fluorinated alkyl group is a fluoroalkoxy group, typically substituted with 1, 2 or 3 fluoro atoms, such as C 1 -C 6 , C 1 -C 4 or C 1 -C 2 fluoroalkoxy may be specifically referred to as a group.
  • the terms “optionally substituted” and “substituted or unsubstituted” mean that the particular group being described may have no non-hydrogen substituents (ie, unsubstituted), or that the group may have one or more non- Used interchangeably to indicate that it may have a hydrogen substituent (ie, substituted).
  • the total number of substituents that may be present is equal to the number of H atoms present on the unsubstituted form of the group being described.
  • the group occupies the available valence, reducing the total number of other substituents included by two.
  • optional substituents are independently selected from a list of substitutes, the selected groups are the same or different. Throughout this specification, it will be understood that the number and nature of optional substituents will be limited to the extent that such substitutions satisfy chemistry.
  • the combination of the divalent aliphatic hydrocarbon group and the ketone group means that one of the ketone groups is connected to one of the divalent aliphatic hydrocarbon groups, and the other of the ketone group and the other of the divalent aliphatic hydrocarbon group are in the formula 1 means that it is connected to tetrahydrofuran and oxygen, respectively.
  • a 13 may be a divalent aliphatic hydrocarbon group having 1 to 15 carbon atoms including a hydroxyl group or an alkoxy group.
  • a 13 is -CH 2 CH(OH)CH 2 -, -CH 2 CH(OH)CH 2 CH 2 -, -CH 2 CH(OH)CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH(OH)CH 2 CH 2 -, -CH 2 CH(OR')CH 2 -, -CH(OR')CH 2 CH 2 -, or -CH 2 C(OR')(OR")CH 2 -.
  • Each of R' and R" may independently be an alkyl group (eg, a methyl group, an ethyl group, a propyl group, a butyl group, or a pentyl group).
  • a 13 may be a divalent aliphatic hydrocarbon group having 2 to 15 carbon atoms, which further includes a hydroxy group or an alkoxy group and a branched chain having 1 to 5 carbon atoms.
  • a 13 is -CHR'CH(OH)CH 2 -, -CH 2 C(OH)R'CH 2 -, -CHR'CH(OH)CH 2 CH 2 -, -CH 2 C( OH)R'CH 2 CH 2 -, -CHR'CH(OH)CH 2 CH 2 CH 2 -, -CH 2 CH(OH)CHR'CH 2 CH 2 -, -CHR'CH 2 CH(OH)CH 2 CH 2 -, -CH 2 CHR'CH(OH)CH 2 CH 2 -, -CH 2 CH 2 C(OH)R'CH 2 CH 2 -, -CH 2 C(OR')R"CH 2 - , -C(OR')R"CH 2 CH 2 -, or -CHR
  • a 13 and the oxygen groups positioned on both sides of A 13 may be derived from trihydric or higher polyhydric alcohols.
  • the trihydric or higher polyhydric alcohol is propanetriol, alkylpropanetriol, butanetriol, alkylbutanetriol, pentanetriol, alkylpentanetriol, (hydroxyalkyl)propanediol, (hydroxyalkyl ) alkylpropanediol, or pentaerythritol.
  • R 11 represents a substituent of the tetrahydrofuran group, and may be, for example, a halogen group, a hydroxyl group, an alkoxy group, or an alkyl group, and n 12 may be an integer of 0 to 6. When n 12 is 0, the tetrahydrofuran is substituted with only hydrogen.
  • n 11 represents the number of repetitions of the repeating unit, and n 11 may be appropriately adjusted according to the weight average molecular weight of the polyester, for example, 1 or more, 100 to 200, or 30 to 80, but the present invention is not limited thereto.
  • the polyester may further include a repeating unit derived from an aromatic dicarboxylic acid, an aliphatic dicarboxylic acid, an aromatic diol, an aliphatic diol, or a mixture thereof. These will be described later in the method for producing the polyester.
  • the polyester may have a glass transition temperature (Tg) of 40 °C to 100 °C, for example, 40 °C to 60 °C, or 60 °C to 80 °C.
  • Tg glass transition temperature
  • the polyester may have a weight average molecular weight of 6000 g/mol to 50000 g/mol, for example, 6000 g/mol to 20000 g/mol, or 25000 g/mol to 50000 g/mol. If the weight average molecular weight is less than 6000 g / mol, film processing for use as a packaging material may be difficult and may not achieve a desired modulus, and if it exceeds 50000 g / mol, the viscosity may increase and productivity may decrease.
  • the polyester including the repeating unit has a lower glass transition temperature (Tg) than conventional PET, and has an excellent Young's modulus, so it can be used for food containers or toys.
  • Tg glass transition temperature
  • the tetrahydrofuran derivative represented by Formula 3 may be, for example, biomass-derived dihydroxyalkyl tetrahydrofuran or tetrahydrofuran dicarboxylic acid.
  • the dihydroxyalkyl tetrahydrofuran can be obtained directly from hexoses such as glucose or fructose according to Scheme 1 below.
  • polyester is produced using the tetrahydrofuran derivative obtained from the biomass, the effect of reducing carbon can be obtained.
  • the trihydric or higher polyhydric alcohol represented by Formula 4 is, for example, propanetriol, butanetriol, pentanetriol, (hydroxyalkyl)propanediol, (hydroxyalkyl)alkylpropanediol, or pentaerythritolyl can
  • the trihydric or higher polyhydric alcohol may be a trihydric or higher polyhydric alcohol substituted with at least one or more C1 to C5 alkyl groups.
  • the trihydric or higher polyhydric alcohol may be alkylpropanetriol, alkylbutanetriol, alkylpentanetriol, or (hydroxyalkyl)alkylpropanediol.
  • the trihydric or higher polyhydric alcohol is propane-1,2,3-triol (propane-1,2,3-triol), 1-alkyl-propane-1,2,3-triol (1- alkyl-propane-1,2,3-triol), 2-alkyl-propane-1,2,3-triol (2-alkyl-propane-1,2,3-triol), butane-1,2,4 -triol (butane-1,2,4-triol), 1-alkyl-butane-1,2,4-triol (1-alkyl-butane-1,2,4-triol), 2-alkyl-butane -1,2,4-triol (2-alkyl-butane-1,2,4-triol), pentane-1,2,5-triol (pentane-1,2,5-triol), pentane-1 ,3,5-triol (pentane-1,3,5-triol), 1-alkyl-pentane-1,2,5-triol (1-alkyl-
  • the trihydric or higher polyhydric alcohol is propane-1,2,3-triol (propane-1,2,3-triol), 1-methyl-propane-1,2,3-triol (1-methyl -propane-1,2,3-triol), 2-methyl-propane-1,2,3-triol (2-methyl-propane-1,2,3-triol), butane-1,2,4- Triol (butane-1,2,4-triol), 1-methyl-butane-1,2,4-triol (1-methyl-butane-1,2,4-triol), 2-methyl-butane- 1,2,4-triol (2-methyl-butane-1,2,4-triol), pentane-1,2,5-triol (pentane-1,2,5-triol), pentane-1, 3,5-triol (pentane-1,3,5-triol), 1-methyl-pentane-1,2,5-triol (1-methyl-pentane-1,2,5-triol), 2- Methyl-pentan
  • the polyester includes a repeating unit derived from a trihydric or higher polyhydric alcohol having the branched chain
  • the branched chain causes steric hindrance during polyester polymerization, thereby lowering the crystallinity of the polyester, thereby increasing the transparency of the polymer can do it
  • the polyester including the repeating unit has a lower glass transition temperature (Tg) than conventional PET and has an excellent Young's modulus, so it can be used for food containers or toys.
  • Tg glass transition temperature
  • the mixture may further include an aromatic diol or an aliphatic diol as an additional diol component in addition to the monomer represented by Chemical Formula 3 or Chemical Formula 4.
  • the aromatic diol may include an aromatic diol compound having 8 to 40 carbon atoms, for example, 8 to 33 carbon atoms.
  • aromatic diol compound examples include polyoxyethylene-(2.0)-2,2-bis(4-hydroxyphenyl)propane, polyoxypropylene-(2.0)-2,2-bis(4-hydroxyphenyl) Propane, polyoxypropylene-(2.2)-polyoxyethylene-(2.0)-2,2-bis(4-hydroxyphenyl)propane, polyoxyethylene-(2.3)-2,2-bis(4-hydroxyl Phenyl) propane, polyoxypropylene-(6)-2,2-bis(4-hydroxyphenyl)propane, polyoxypropylene-(2.3)-2,2-bis(4-hydroxyphenyl)propane, polyoxy Propylene-(2.4)-2,2-bis(4-hydroxyphenyl)propane, polyoxypropylene-(3.3)-2,2-bis(4-hydroxyphenyl)propane, polyoxyethylene-(3.0)-
  • the aliphatic diol may include an aliphatic diol compound having 2 to 20 carbon atoms, for example, an aliphatic diol compound having 2 to 12 carbon atoms.
  • an aliphatic diol compound include ethylene glycol, diethylene glycol, triethylene glycol, propanediol (1,2-propanediol, 1,3-propanediol, etc.), 1,4-butanediol, pentanediol, hexanediol ( 1,6-hexanediol, etc.), neopentyl glycol (2,2-dimethyl-1,3-propanediol), 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexanediol and linear, branched or cyclic aliphatic diol components such as methanol, 1,3-cyclohexanedimethanol,
  • the mixture may further include an aromatic dicarboxylic acid or an aliphatic dicarboxylic acid as an additional dicarboxylic acid component in addition to the monomer represented by Chemical Formula 3 or Chemical Formula 4.
  • the aromatic dicarboxylic acid may be an aromatic dicarboxylic acid having 8 to 20 carbon atoms, preferably 8 to 14 carbon atoms, or a mixture thereof.
  • the aromatic dicarboxylic acid is, for example, isophthalic acid, naphthalenedicarboxylic acid such as 2,6-naphthalenedicarboxylic acid, diphenyl dicarboxylic acid, 4,4'-stilbenedicarboxylic acid, 2, 5-furandicarboxylic acid, or 2,5-thiophenedicarboxylic acid, and the like.
  • the aromatic dicarboxylic acid may include terephthalic acid
  • the terephthalic acid is a dicarboxylic acid such as terephthalic acid or an alkyl ester thereof (monomethyl, monoethyl, dimethyl, diethyl or dibutyl ester, etc. having 1 to 4 carbon atoms). of a lower alkyl ester) and/or an acid anhydride thereof, and may react with a diol component to form a dicarboxylic acid moiety such as a terephthaloyl moiety.
  • the aliphatic dicarboxylic acid is malonic acid, succinic acid, glutaric acid, 2-methylglutaric acid, 3-methylglutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, fumaric acid, 2,2-dimethylglutaric acid, suberic acid, maleic acid, itaconic acid, or maleic acid.
  • the mixture may include the additional dicarboxylic acid or diol component in an amount of 10 mol% to 90 mol%, or 40 mol% to 85 mol% based on the total amount of the mixture.
  • additional dicarboxylic acid or diol component is further included, mechanical properties and heat resistance of the polyester may be further improved.
  • the esterification step may be performed by reacting the diol component and the dicarboxylic acid component at a pressure of 0 kg/cm 2 to 10.0 kg/cm 2 and a temperature of 150° C. to 270° C.
  • the esterification reaction conditions may be appropriately adjusted according to the specific characteristics of the polyester to be prepared, the molar ratio of the dicarboxylic acid component to the diol, or process conditions.
  • a preferred example of the esterification reaction conditions may include a temperature of 200 °C to 270 °C, or 220 °C to 260 °C.
  • the reaction yield may be low or a sufficient reaction may not occur, so that the physical properties of the finally prepared polyester may be reduced. If the temperature of the esterification reaction is too high, the possibility that the appearance of the polyester to be produced will be yellow is increased or the depolymerization reaction may proceed so that the polyester resin may not be synthesized in the production method.
  • the molar ratio of the dicarboxylic acid component and the diol component participating in the esterification reaction may be 1:1.05 to 1:3.0. If the molar ratio of the dicarboxylic acid component to the diol component is less than 1.05, unreacted dicarboxylic acid component may remain during the polymerization reaction, thereby reducing the transparency of the polymer, and if the molar ratio exceeds 3.0, the polymerization reaction rate may decrease may be lowered or the productivity of the polymer may be reduced.
  • the esterification reaction may be performed in the presence of an esterification reaction catalyst including a zinc-based compound.
  • the zinc-based compound may be, for example, zinc acetate, zinc acetate dihydrate, zinc chloride, zinc sulfate, zinc sulfide, zinc carbonate, zinc citrate, zinc gluconate, or a mixture thereof.
  • the esterification reaction catalyst may be used in an amount of 1 ppm to 100 ppm based on a central metal atom in the synthesized polyester. If the content of the esterification reaction catalyst is too small, it may be difficult to greatly improve the efficiency of the esterification reaction, and the amount of reactants not participating in the reaction may be greatly increased. In addition, if the content of the esterification reaction catalyst is too large, the physical properties of the polyester to be produced may be deteriorated.
  • Polycondensation of the resultant of the esterification reaction may be performed in the presence of a polycondensation catalyst at a pressure of 600 mmHg to 0.01 mmHg and a temperature of 150° C. to 290° C. for 0.5 hours to 2.75 hours.
  • glycol a by-product of the polycondensation reaction
  • the intrinsic viscosity of the final reaction product is low, thereby reducing the physical properties of the polyester produced.
  • the polycondensation reaction proceeds in excess of 290 °C, the possibility that the appearance of the prepared polyester becomes yellow is increased or the depolymerization reaction proceeds so that the polyester may not be synthesized.
  • the polycondensation catalyst may be added to the product of the esterification reaction before the start of the polycondensation reaction, and may be added to a mixture including the diol component and the dicarboxylic acid component before the esterification reaction, and the ester It may be added during the reaction step.
  • a titanium-based compound As the polycondensation catalyst, a titanium-based compound, a germanium-based compound, an antimony-based compound, an aluminum-based compound, a tin-based compound, or a mixture thereof may be used.
  • titanium-based compound examples include tetraethyl titanate, acetyl tripropyl titanate, tetrapropyl titanate, tetrabutyl titanate, polybutyl titanate, 2-ethylhexyl titanate, octylene glycol titanate, and lactate titanate. , triethanolamine titanate, acetylacetonate titanate, ethylacetoacetic ester titanate, isostearyl titanate, titanium dioxide, titanium dioxide/silicon dioxide copolymer, titanium dioxide/zirconium dioxide copolymer, and the like.
  • germanium-based compound germanium dioxide (GeO2), germanium tetrachloride (GeCl 4 ), germanium ethyleneglycoxide (germanium ethyleneglycoxide), germanium acetate (germanium acetate), copolymers using them, and their mixtures, and the like.
  • a stabilizer or a colorant may be optionally added further.
  • the stabilizer may be selected in consideration of the physical properties of the finally manufactured polyester, for example, a phosphorus-based stabilizer may be used.
  • a phosphorus-based stabilizer include phosphoric acid, trimethyl phosphate, triethyl phosphate, triphenyl phosphate, triethyl phosphono acetate, or a mixture of two or more thereof.
  • the stabilizer may be used in an amount of 10 ppm to 300 ppm, or 20 ppm to 200 ppm, based on the total weight of the polymer to be synthesized.
  • the colorant may be a cobald compound such as cobalt acetate or an organic colorant.
  • the organic colorant may include an anthraquinone-based compound, an azo-based compound, a perinone-based compound, a methine-based compound, a phthalocyanine-based compound, an anthrapyridone-based compound, a perimidine-based compound, or a mixture of two or more thereof.
  • the colorant may be used in an amount of 1 ppm to 100 ppm based on the total weight of the resin to be prepared.
  • the slurry was filled in the reactor by bubbling nitrogen up to 1.5 bar at room temperature, and then the process of lowering the slurry to atmospheric pressure was repeated for 5 minutes (repeated 5 times). Then, after the above process, the inside of the reactor was depressurized to 10 torr to 100 torr, and a vacuum pump was connected to remove dissolved oxygen in the slurry for 5 minutes. This process was repeated 3 times.
  • tetrahydrofurandimethanol THFDM 3737.5 g (53.5 mol%) and 1-methyl-propane-1,2,3-triol (1-methyl-propane-1,2,3-triol) ) 3250 g (46.5 mol%) were mixed to form a slurry.
  • the slurry was filled in the reactor by bubbling nitrogen up to 1.5 bar at room temperature, and then the process of lowering the slurry to atmospheric pressure was repeated for 5 minutes (repeated 5 times). Then, after the above process, the inside of the reactor was depressurized to 10 torr to 100 torr, and a vacuum pump was connected to remove dissolved oxygen in the slurry for 5 minutes. This process was repeated 3 times.
  • PET polyethylene terephthalate
  • FIG. 1 is a HOMO electron cloud distribution diagram of the three-dimensional structural formula of Chemical Formula 5
  • FIG. 2 is a LUMO electron cloud distribution diagram of the three-dimensional structural formula of Chemical Formula 5
  • FIG. 3 is a HOMO electron cloud distribution diagram of the three-dimensional structural formula of Chemical Formula 7
  • FIG. 4 is Chemical Formula 7 LUMO electron cloud distribution diagram of the three-dimensional structure of
  • the glass transition temperature was measured using a differential scanning calorimeter (DSC) after sampling a portion of the polymer polymer. Specifically, the analysis conditions were 25 °C to 200 °C, and a temperature increase rate of 10 °C/min under a nitrogen stream. It was decided.
  • DSC differential scanning calorimeter

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  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

La présente invention concerne un polyester et un procédé de préparation de celui-ci, ledit polyester comprenant une unité de répétition issue d'un dérivé de tétrahydrofurane obtenue à partir d'une biomasse et une unité de répétition dérivée de l'alcool polyhydrique (trihydrique ou à plus de trois groupes hydroxyle) et ayant ainsi un effet de réduction du carbone, et pouvant être utilisé pour des récipients alimentaires et des jouets grâce à un excellent module de Young en comparaison avec le polyéthylène téréphtalate (PET) existant.
PCT/KR2021/010762 2020-09-22 2021-08-12 Polyester comprenant un composant issu d'une biomasse et son procédé de préparation Ceased WO2022065690A1 (fr)

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KR20200122490 2020-09-22
KR10-2020-0122490 2020-09-22
KR1020210097219A KR20220039559A (ko) 2020-09-22 2021-07-23 바이오매스 유래 성분을 포함하는 폴리에스테르 및 이의 제조 방법
KR10-2021-0097219 2021-07-23

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130118221A (ko) * 2010-05-24 2013-10-29 노바몬트 에스.피.에이. 지방족-방향족 코폴리에스테르 및 이의 혼합물
KR20160059287A (ko) * 2014-11-18 2016-05-26 롯데케미칼 주식회사 폴리에스테르 수지의 제조 방법
KR20170078832A (ko) * 2014-11-03 2017-07-07 바스프 에스이 재생가능한 원료를 기반으로 한 신규한 폴리우레탄 분산액
US20170306087A1 (en) * 2014-09-12 2017-10-26 Arkema France Specific method for preparing biobased polyesters
KR101891179B1 (ko) * 2017-05-25 2018-08-24 주식회사 삼양사 다가 알코올을 이용하여 제조된 폴리에스테르 수지 및 그 제조방법, 및 그 수지를 포함하는 분체 도료 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130118221A (ko) * 2010-05-24 2013-10-29 노바몬트 에스.피.에이. 지방족-방향족 코폴리에스테르 및 이의 혼합물
US20170306087A1 (en) * 2014-09-12 2017-10-26 Arkema France Specific method for preparing biobased polyesters
KR20170078832A (ko) * 2014-11-03 2017-07-07 바스프 에스이 재생가능한 원료를 기반으로 한 신규한 폴리우레탄 분산액
KR20160059287A (ko) * 2014-11-18 2016-05-26 롯데케미칼 주식회사 폴리에스테르 수지의 제조 방법
KR101891179B1 (ko) * 2017-05-25 2018-08-24 주식회사 삼양사 다가 알코올을 이용하여 제조된 폴리에스테르 수지 및 그 제조방법, 및 그 수지를 포함하는 분체 도료 조성물

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