Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/51—Phosphorus bound to oxygen
  • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
  • C08K5/5377—Phosphinous compounds, e.g. R2=P—OR'
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/51—Phosphorus bound to oxygen
  • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
  • C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
  • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds

Definitions

• the present invention relates to a polyester elastomer composition containing a polyester elastomer derived and polymerized from polytetramethylene ether glycol (PTMG) derived from biomass resources, and in particular to a polyester elastomer composition containing a biomass resource-derived polyester elastomer that has excellent heat resistance, allows for mass production of pellet products without foaming during casting after polymerization of the polyester elastomer, and further has excellent reduced viscosity and color.
• PTMG polytetramethylene ether glycol
• Polyester elastomers have excellent injection and extrusion moldability, high mechanical strength, and rubber-like properties such as elastic recovery, impact resistance, and flexibility, as well as excellent heat and cold resistance. They are used in a wide range of applications, including automotive parts, electrical and electronic parts, fibers, films, and sports parts.
• biomass resources are used as the soft segment of polyester elastomers.
• biomass resources are renewable resources, they are thought to be an important design concept in future polymer development from the perspective of SDGs and carbon neutrality.
• PTMG derived from biomass resources is produced using a batch process with a fluorine-based catalyst, resulting in the inclusion of fluorine atoms in place of terminal hydroxyl groups.
• polyester elastomers are derived from PTMG containing these fluorine atoms and polymerized, the heat resistance of the polymer deteriorates.
• Patent Document 1 proposes using PTMG with a fluorine content of 100 ppm or less to address the problem of deterioration of heat resistance due to fluorine atoms. To produce PTMG with such a low fluorine content, it also proposes a method of using a strong acid catalyst other than a fluorine-based catalyst, and when a fluorine-based catalyst is used, removing fluorine-based impurities by washing with an alkaline aqueous solvent after polymerization.
• the former method cannot be used for PTMG derived from biomass resources, and the latter method also places a large burden on industrial wastewater, so it has not been adopted in the manufacturing process of PTMG derived from biomass resources.
• Patent Document 2 proposes adding a larger amount of oleum than is required for dehydration in order to obtain PTMG with a low fluorine content.
• this method also places a very large burden on the industrial wastewater and has low productivity, so it has not been adopted in the manufacturing process of PTMG derived from biomass resources.
• Patent Document 3 proposes incorporating 5 to 20 ppm of phosphoric acid into PTMG in order to reduce the tetrahydrofuran content in the polyester elastomer polymerized from PTMG and improve heat resistance.
• PTMG derived from fossil fuel resources can be successfully mass-produced using a continuous method without using a fluorine-based catalyst, and the above-mentioned problems caused by the inclusion of fluorine atoms have been resolved.
• the above-mentioned problems still exist because the PTMG contains approximately 20 to 200 ppm of fluorine atoms. Therefore, if PTMG derived from biomass resources is directly derived and polymerized into polyester elastomer, the heat resistance of the resulting polyester elastomer is low, and foaming occurs during casting to produce pellets due to heat retention in the reaction vessel after polymerization, making it extremely difficult to obtain a large amount of sample at once.
• the present invention was devised in consideration of the current state of the prior art, and its purpose is to provide a polyester elastomer composition containing a polyester elastomer derived from a biomass resource, which uses a polyester elastomer derived and polymerized from PTMG derived from a fluorine-containing biomass resource, has excellent heat resistance, allows for mass production of pellet products without foaming during casting after polymerization of the polyester elastomer, and has excellent reduced viscosity and color, and a method for producing the same.
• the inventors conducted extensive research into the cause of the decrease in heat resistance of polyester elastomers derived and polymerized from fluorine-atom-containing biomass resource-derived PTMG, particularly foaming during casting during the production of molded products, and discovered that the fluorine atoms in the PTMG promote the production of peroxides during casting, which causes the heat resistance to deteriorate and foaming to occur during casting. Based on this knowledge, they discovered that by adding a specific amount of a peroxide decomposer after polymerization to suppress the production of peroxides, it is possible to suppress the foaming that occurs during casting and prevent the deterioration of heat resistance.
• the polyester elastomer composition according to (1) wherein the aliphatic polyether contains 20 to 200 ppm of fluorine atoms.
• the peroxide decomposer is at least one selected from the group consisting of phosphonites, phosphites, and hindered amine stabilizers.
• the polyester elastomer composition according to (1) characterized in that the reduced viscosity of the polyester elastomer composition is 1.2 dl/g or more.
• polyester elastomer composition of the present invention a polyester elastomer derived from PTMG derived from biomass resources containing fluorine atoms is used, but the generation of peroxides due to fluorine atoms during casting is suppressed by the incorporation of a peroxide decomposer, so that the heat resistance is high, there is no foaming during casting after polymerization of the polyester elastomer, and mass production of pellet products is possible.
• the polyester elastomer composition of the present invention although PTMG derived from biomass resources is used as the raw material for the polyester elastomer, the reduced viscosity and color are excellent. Therefore, since the polyester elastomer composition of the present invention can be effectively used with PTMG derived from biomass resources as a raw material, it will greatly contribute to solving global environmental problems such as the depletion of fossil fuel resources.
• the polyester elastomer composition of the present invention contains a polyester elastomer in which a hard segment made of a polyester whose constituent components are an aromatic dicarboxylic acid derived from a fossil fuel resource and an aliphatic and/or alicyclic diol derived from a fossil fuel resource is bonded to a soft segment made of PTMG derived from a biomass resource containing fluorine atoms, and is characterized in that a peroxide decomposer is contained in a ratio of 0.01 to 1 part by mass per 100 parts by mass of the polyester elastomer.
• Normal aromatic dicarboxylic acids are widely used as the aromatic dicarboxylic acid constituting the polyester of the hard segment of the polyester elastomer, and the main aromatic dicarboxylic acid is preferably terephthalic acid or naphthalenedicarboxylic acid (among the isomers, 2,6-naphthalenedicarboxylic acid is preferred).
• the content of these aromatic dicarboxylic acids in the total dicarboxylic acids constituting the polyester of the hard segment is preferably 70 mol% or more, more preferably 80 mol% or more, and even more preferably 90 mol% or more, and may be 100 mol%.
• Dicarboxylic acid components other than terephthalic acid and naphthalenedicarboxylic acid include aromatic dicarboxylic acids such as diphenyldicarboxylic acid, isophthalic acid, and 5-sodium sulfoisophthalic acid, alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid and tetrahydrophthalic anhydride, and aliphatic dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, dodecanedioic acid, dimer acid, and hydrogenated dimer acid.
• aromatic dicarboxylic acids such as diphenyldicarboxylic acid, isophthalic acid, and 5-sodium sulfoisophthalic acid
• alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid and tetrahydrophthalic anhydride
• these dicarboxylic acids can be used in a range that does not significantly lower the melting point of the resin, and the amount is preferably 30 mol% or less of the total acid components, more preferably 20 mol% or less, and even more preferably 10 mol% or less, and may be 0 mol%.
• these dicarboxylic acids may be in the form of esters of the dicarboxylic acids.
• terephthalic acid and dimethyl terephthalate can also be used as raw materials.
• aliphatic or alicyclic diol constituting the polyester of the hard segment general aliphatic or alicyclic diols are widely used, and although there is no particular limitation, it is preferable that they are mainly alkylene glycols having 2 to 8 carbon atoms. Specific examples include ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, and 1,4-cyclohexanedimethanol. Of these, either ethylene glycol or 1,4-butanediol is preferable.
• the components constituting the polyester of the hard segments are preferably made of butylene terephthalate units (units consisting of terephthalic acid and 1,4-butanediol) or butylene naphthalate units (units consisting of 2,6-naphthalenedicarboxylic acid and 1,4-butanediol) in terms of physical properties, moldability, and cost performance.
• the aromatic polyester when an aromatic polyester suitable as the polyester constituting the hard segment of the polyester elastomer is produced in advance and then copolymerized with a soft segment component, the aromatic polyester can be easily obtained according to a normal polyester production method.
• such a polyester preferably has a number average molecular weight of 10,000 to 40,000.
• the aromatic dicarboxylic acid and the aliphatic and/or alicyclic diol constituting the hard segment are derived from fossil fuel resources.
• PTMG is used as the aliphatic polyether that constitutes the soft segment of the polyester elastomer.
• the PTMG used in the present invention is derived from biomass resources. Such PTMG can be obtained commercially and used; for example, BioPTMG1000 and BioPTMG2000 manufactured by Mitsubishi Chemical are preferably used.
• PTMG derived from biomass resources is produced in a batch process using a fluorine-based catalyst, and therefore contains fluorine atoms instead of terminal hydroxyl groups. Therefore, the PTMG used in the present invention also contains fluorine atoms.
• the content is generally 20 to 200 ppm, more preferably 40 to 180 ppm, and particularly 50 to 160 ppm.
• the number average molecular weight of PTMG is preferably 500 to 4000, more preferably 700 to 3000, and even more preferably 800 to 2500. If the number average molecular weight is below the above range, it may be difficult to develop elastomeric properties. On the other hand, if the number average molecular weight exceeds the above range, compatibility with the hard segment component decreases, and copolymerization in a block form may become difficult.
• the polyester elastomer is preferably a copolymer whose main components are terephthalic acid, 1,4-butanediol, and PTMG.
• terephthalic acid is preferably 40 mol% or more, more preferably 70 mol% or more, even more preferably 80 mol% or more, and particularly preferably 90 mol% or more.
• the glycol components constituting the polyester elastomer the sum of 1,4-butanediol and PTMG is preferably 40 mol% or more, more preferably 70 mol% or more, even more preferably 80 mol% or more, and particularly preferably 90 mol% or more.
• the mass of the hard segment refers to the mass of the component consisting of aromatic dicarboxylic acid and aliphatic and/or alicyclic diol
• the mass of the soft segment refers to the mass of the component consisting of aromatic dicarboxylic acid and aliphatic polyether.
• the mass of the hard segment is the mass of butylene terephthalate units (condensation units of terephthalic acid and 1,4-butanediol)
• the mass of the soft segment is the mass of the condensation units of terephthalic acid and PTMG.
• the mass ratio of hard segments to soft segments in the polyester elastomer is preferably 5/95 to 90/10, more preferably 10/90 to 85/15, and even more preferably 15/85 to 80/20. If the amount of hard segments is small (the amount of PTMG is large), the polyester elastomer may not have satisfactory heat aging resistance and moldability (crystallinity). Conversely, if the amount of hard segments is large (the amount of PTMG is small), the compatibility between the hard segment components and the soft segment components may decrease, making it difficult to copolymerize them into blocks.
• the polyester elastomer preferably has a melting point of 150 to 230°C. If the melting point is less than 150°C, it may not be possible to obtain a polyester elastomer that satisfies the heat aging resistance and moldability (crystallinity) functions required for the polyester elastomer. Conversely, if the melting point exceeds 230°C, it will contain a large amount of hard segments, and the glass transition temperature (Tg) will be accordingly high, and it may not be possible to obtain a polyester elastomer that satisfies the impact resilience, flexibility, and low-temperature mechanical properties functions required for the polyester elastomer.
• Tg glass transition temperature
• the polyester elastomer composition of the present invention contains 0.01 to 1 part by mass, preferably 0.02 to 0.8 parts by mass, more preferably 0.03 to 0.7 parts by mass of a peroxide decomposer per 100 parts by mass of polyester elastomer.
• the peroxide decomposer is a compound capable of decomposing peroxide into alcohol, and is different from a simple stabilizer. In the present invention, even if peroxide that causes foaming is generated during casting to produce a pellet product due to fluorine atoms contained in PTMG derived from biomass resources, which is the raw material of the polyester elastomer, the peroxide decomposer decomposes the generated peroxide.
• the peroxide decomposer is preferably a phosphonite (a compound having one carbon-phosphorus bond and two phosphorus-oxygen bonds, R-P-(O-R) 2 ), a phosphite (a compound having three phosphorus-oxygen bonds, P-(O-R) 3 ), or a hindered amine stabilizer (HALS).
• the peroxide decomposer is more preferably at least one of a phosphonite and a phosphite, since they have a large effect of suppressing foaming during casting.
• R is a hydrocarbon group, which may be the same or different, and may have a structure in which the groups are linked to each other.
• the hydrocarbon group may have a structure in which a substituent such as a hydroxyl group or a halogen group is linked to a hydrocarbon.
• a substituent such as a hydroxyl group or a halogen group
• R has at least one aromatic structure, alicyclic structure, or ring structure linked to each other. More preferably, R is a phosphonite having an aromatic structure or R is a phosphite having an alkyl cyclic structure. This makes it possible to obtain the desired effect with a smaller amount of addition, and to more highly achieve both the foaming suppression effect during casting and pellet quality such as color.
• the polyester elastomer composition preferably has a Co-b value of 7 or less, more preferably 6 or less, and even more preferably 5.5 or less. If the Co-b value exceeds the upper limit, the prepared pellets will turn yellow, significantly impairing the appearance of the molded product, and a satisfactory product may not be obtained.
• composition and composition ratio of the polyester elastomer composition of the present invention can be determined by calculating from the proton integral ratio of 1 H-NMR measured by dissolving a sample in a solvent such as deuterated chloroform.
• the polyester elastomer composition of the present invention is produced by polymerizing a polyester elastomer using a catalyst such as tetrabutyl titanate according to a conventional method, and then adding a peroxide decomposer.
• the peroxide decomposer must be added after the polymerization of the polyester elastomer is complete and before casting to produce a molded product. If it is added before the polymerization is complete, the above-mentioned effects of the peroxide decomposer cannot be fully exerted. Furthermore, since peroxides that cause foaming are generated during casting to produce a molded product, it is necessary to add the peroxide decomposer before casting.
• Fluorine Content The fluorine content in PTMG was measured by combustion ion chromatography using an automatic sample combustion apparatus (manufactured by Mitsubishi Chemical Analytech Co., Ltd.).
• the Co-b value of the polyester elastomer composition was measured using an automatic color difference meter (manufactured by Toyorika Kogyo Co., Ltd.) The larger the Co-b value, the greater the yellowness.
• Example 1 Dimethyl terephthalate (DMT, manufactured by SK Petrochemical) was charged in a reactor with 56 parts by mass, 1,4-butanediol (1,4-BDO, manufactured by Mitsubishi Chemical) in 36 parts by mass, and polytetramethylene ether glycol (BioPTMG1000, manufactured by Mitsubishi Chemical, molecular weight 1000 g/mol) derived from biomass resources in 8 parts by mass. Furthermore, a solution of tetrabutyl titanate (TBT, manufactured by Nacalai Tesque) as a catalyst diluted to a concentration of 1% by mass with 1-butanol was charged in the reactor at a ratio of 0.08 parts by mass per 100 parts by mass of the polymer to be purified.
• DMT dimethyl terephthalate
• 1,4-BDO 1,4-butanediol
• BioPTMG1000 polytetramethylene ether glycol
• TBT tetrabutyl titanate
• Examples 2 and 3 The final polyester elastomer compositions of Examples 2 and 3 were obtained in the same manner as in Example 1, except that the addition ratio of peroxide decomposer A was changed to 0.5 parts by mass and 0.15 parts by mass, respectively, per 100 parts by mass of the purified polymer.
• Example 4 The final polyester elastomer composition of Example 4 was obtained in the same manner as in Example 1, except that in Example 1, the blending ratios of dimethyl terephthalate and 1,4-butanediol were changed as shown in Table 1, and BioPTMG2000 (manufactured by Mitsubishi Chemical Corporation, molecular weight 2000 g/mol) was used as the biomass resource-derived polytetramethylene ether glycol in the blending ratio shown in Table 1.
• Example 5 The final polyester elastomer composition of Example 5 was obtained in the same manner as in Example 2, except that the blending ratios of dimethyl terephthalate and 1,4-butanediol in Example 2 were changed as shown in Table 1, and BioPTMG2000 (manufactured by Mitsubishi Chemical Corporation, molecular weight 2000 g/mol) was used as the biomass resource-derived polytetramethylene ether glycol in the blending ratio shown in Table 1.
• Example 6 The final polyester elastomer composition of Example 6 was obtained in the same manner as in Example 1, except that dimethyl 2,6-naphthalenedicarboxylate (NDC, manufactured by SK Petrochemical) was used in place of dimethyl terephthalate in the blending ratio shown in Table 1, and the blending ratios of 1,4-butanediol and biomass resource-derived polytetramethylene ether glycol were changed to those shown in Table 1.
• NDC dimethyl 2,6-naphthalenedicarboxylate
• Example 7 The final polyester elastomer composition of Example 7 was obtained in the same manner as in Example 2, except that dimethyl 2,6-naphthalenedicarboxylate (NDC, manufactured by SK Petrochemical) was used in place of dimethyl terephthalate in the blending ratio shown in Table 1, and the blending ratios of 1,4-butanediol and biomass resource-derived polytetramethylene ether glycol were changed to those shown in Table 1.
• NDC dimethyl 2,6-naphthalenedicarboxylate
• Example 8 The final polyester elastomer composition of Example 8 was obtained in the same manner as in Example 6, except that the blending ratios of dimethyl 2,6-naphthalenedicarboxylate, 1,4-butanediol, and biomass resource-derived polytetramethylene ether glycol in Example 6 were changed as shown in Table 1.
• Example 9 The final polyester elastomer composition of Example 9 was obtained in the same manner as in Example 7, except that the blending ratios of dimethyl 2,6-naphthalenedicarboxylate, 1,4-butanediol, and biomass resource-derived polytetramethylene ether glycol in Example 7 were changed as shown in Table 1.
• Example 10 The final polyester elastomer composition of Example 10 was obtained in the same manner as in Example 3, except that peroxide decomposer B (phosphorus-based antioxidant (phosphonite), HOSTANOX P-EPQ, manufactured by Clariant Japan) was used instead of peroxide decomposer A in Example 3.
• peroxide decomposer B phosphorus-based antioxidant (phosphonite), HOSTANOX P-EPQ, manufactured by Clariant Japan
• Example 11 The final polyester elastomer composition of Example 11 was obtained in the same manner as in Example 10, except that the blending ratios of dimethyl terephthalate and 1,4-butanediol in Example 10 were changed as shown in Table 1, and BioPTMG2000 (manufactured by Mitsubishi Chemical Corporation, molecular weight 2000 g/mol) was used as the biomass resource-derived polytetramethylene ether glycol in the blending ratio shown in Table 1.
• Example 12 The final polyester elastomer composition of Example 12 was obtained in the same manner as in Example 10, except that dimethyl 2,6-naphthalenedicarboxylate (NDC, manufactured by SK Petrochemical) was used in place of dimethyl terephthalate in the blending ratio shown in Table 1, and the blending ratios of 1,4-butanediol and biomass resource-derived polytetramethylene ether glycol were changed to those shown in Table 1.
• NDC dimethyl 2,6-naphthalenedicarboxylate
• Example 13 The final polyester elastomer composition of Example 13 was obtained in the same manner as in Example 10, except that dimethyl 2,6-naphthalenedicarboxylate (NDC, manufactured by SK Petrochemical) was used in place of dimethyl terephthalate in the blending ratio shown in Table 1, and the blending ratios of 1,4-butanediol and biomass resource-derived polytetramethylene ether glycol were changed to those shown in Table 1.
• NDC dimethyl 2,6-naphthalenedicarboxylate
• Example 14 The final polyester elastomer composition of Example 14 was obtained in the same manner as in Example 3, except that peroxide decomposer C (hindered amine-based HALS, Chimassorb 944 FDL, manufactured by BASF Japan) was used instead of peroxide decomposer A.
• peroxide decomposer C hindered amine-based HALS, Chimassorb 944 FDL, manufactured by BASF Japan
• Example 15 The final polyester elastomer composition of Example 15 was obtained in the same manner as in Example 14, except that in Example 14, the blending ratios of dimethyl terephthalate and 1,4-butanediol were changed as shown in Table 1, and BioPTMG2000 (manufactured by Mitsubishi Chemical Corporation, molecular weight 2000 g/mol) was used as the biomass resource-derived polytetramethylene ether glycol in the blending ratio shown in Table 1.
• Example 16 The final polyester elastomer composition of Example 16 was obtained in the same manner as in Example 14, except that dimethyl 2,6-naphthalenedicarboxylate (NDC, manufactured by SK Petrochemical) was used in place of dimethyl terephthalate in the blending ratio shown in Table 1, and the blending ratios of 1,4-butanediol and biomass resource-derived polytetramethylene ether glycol were changed to those shown in Table 1.
• NDC dimethyl 2,6-naphthalenedicarboxylate
• Example 17 The final polyester elastomer composition of Example 17 was obtained in the same manner as in Example 14, except that dimethyl 2,6-naphthalenedicarboxylate (NDC, manufactured by SK Petrochemical) was used in place of dimethyl terephthalate in the blending ratio shown in Table 1, and the blending ratios of 1,4-butanediol and biomass resource-derived polytetramethylene ether glycol were changed to those shown in Table 1.
• NDC dimethyl 2,6-naphthalenedicarboxylate
• Comparative Example 1 The final polyester elastomer composition of Comparative Example 1 was obtained in the same manner as in Example 1, except that the peroxide decomposer A was not added after completion of the polymerization reaction.
• Comparative Example 2 The final polyester elastomer composition of Comparative Example 2 was obtained in the same manner as in Example 1, except that the blending ratio of the peroxide decomposer A in Example 1 was changed as shown in Table 1.
• Comparative Example 3 The final polyester elastomer composition of Comparative Example 3 was obtained in the same manner as in Example 1, except that the blending ratio of the peroxide decomposer A in Example 1 was changed as shown in Table 1.
• Comparative Example 4 The final polyester elastomer composition of Comparative Example 4 was obtained in the same manner as in Example 1, except that a stabilizer A not having peroxide decomposition ability (hindered phenol-based antioxidant, Irganox 1098, manufactured by BASF Japan) was used in place of the peroxide decomposer A in the blending ratio shown in Table 1.
• a stabilizer A not having peroxide decomposition ability hindered phenol-based antioxidant, Irganox 1098, manufactured by BASF Japan
• Comparative Example 5 The final polyester elastomer composition of Comparative Example 5 was obtained in the same manner as in Example 1, except that a stabilizer B having no peroxide decomposition ability (semi-hindered phenol-based antioxidant, Adeka STAB AO-80, manufactured by ADEKA Corporation) was used in place of the peroxide decomposer A in the blending ratio shown in Table 1.
• a stabilizer B having no peroxide decomposition ability si-hindered phenol-based antioxidant, Adeka STAB AO-80, manufactured by ADEKA Corporation
• Comparative Example 6 The final polyester elastomer composition of Comparative Example 6 was obtained in the same manner as in Example 1, except that a stabilizer C (sulfur-based antioxidant, Lasmit LG, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) not having peroxide decomposing ability was used in place of the peroxide decomposing agent A in the blending ratio shown in Table 1.
• a stabilizer C sulfur-based antioxidant, Lasmit LG, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.
• Comparative Example 7 The final polyester elastomer composition of Comparative Example 7 was obtained in the same manner as in Example 1, except that a stabilizer D (amine-based antioxidant, Nonflex DCD, manufactured by Seiko Chemical Industry Co., Ltd.) not having peroxide decomposition ability was used in place of the peroxide decomposer A in the blending ratio shown in Table 1.
• a stabilizer D amine-based antioxidant, Nonflex DCD, manufactured by Seiko Chemical Industry Co., Ltd.
• Comparative Example 1 which did not contain any peroxide decomposer, and Comparative Example 2, which contained too little peroxide decomposer, both had poor heat resistance and foamed during casting, making it impossible to sample.
• Comparative Example 3 which contained too much oxide decomposer, had sufficient heat resistance, but had a high Co-b value and poor color.
• polyester elastomer composition of the present invention a polyester elastomer derived from PTMG derived from biomass resources containing fluorine atoms is used, but the generation of peroxides during casting due to fluorine atoms is suppressed by the incorporation of a peroxide decomposer, so that the heat resistance is high, foaming does not occur during casting after polymerization of the polyester elastomer, and mass production of pellet products is possible.
• the polyester elastomer composition of the present invention although PTMG derived from biomass resources is used as the raw material for the polyester elastomer, the reduced viscosity and color are excellent. Therefore, since the polyester elastomer composition of the present invention can be effectively used with PTMG derived from biomass resources as a raw material, it contributes greatly to solving global environmental problems such as the depletion of fossil fuel resources and is extremely useful in this industry.

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  • 2024-07-01 JP JP2025535667A patent/JPWO2025022936A1/ja active Pending
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