Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
  • C07C31/18—Polyhydroxylic acyclic alcohols
  • C07C31/20—Dihydroxylic alcohols
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C47/00—Compounds having —CHO groups
  • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
  • C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
• • 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/44—Polycarbonates

Definitions

• the present invention relates to a 1,6-hexanediol composition and a polymer using the 1,6-hexanediol composition as a reaction raw material.
• 1,6-Hexanediol (1,6-HDO) compositions are useful intermediates for the production of polymers such as polyesters and polyurethanes.
• Polymers such as polyesters and polyurethanes obtained by reacting 1,6-hexanediol compositions are widely used in artificial leathers and the like.
• There is a constant demand for improving the quality of these polymers such as polyesters and polyurethanes.
• methods are known for obtaining a 1,6-hexanediol (1,6-HDO) composition derived from a biomass resource by utilizing microorganisms such as Corynebacterium and Escherichia coli from the biomass resource (see, for example, Patent Documents 1 and 2).
• JP 2020-114227 A Special table number 2016-533162
• a 1,6-hexanediol composition derived from a biomass resource which is obtained by the production method described in the above-mentioned Patent Document 1
• the hydrogen ion concentration (pH) of the fermentation liquid is usually adjusted by a neutralizing agent in order to efficiently proceed with the fermentation.
• the neutralizing agent and culture liquid contain many alkali metal elements and alkaline earth metals.
• the upper limit of the acid value of the 1,6-hexanediol composition of the present invention is 0.5 mgKOH/g or less, preferably 0.3 mgKOH/g or less, and more preferably 0.1 mgKOH/g or less.
• the lower limit of the acid value is 0.001 mgKOH/g or more, and preferably 0.01 mgKOH/g or more. Any combination of these upper and lower limits can be used.
• the acid value of the 1,6-hexanediol composition of the present invention is from 0.001 to 0.5 mgKOH/g, preferably from 0.001 to 0.3 mgKOH/g, and more preferably from 0.01 to 0.3 mgKOH/g.
• the acid value is within the above range, when the 1,6-hexanediol composition is used to prepare a polymer (eg, polycarbonate polyol, polyurethane, etc.), the performance of the polymer is expected to be improved.
• the acid value is a value measured in accordance with JIS K 0070-1992.
• Organic acid contains an organic acid as described above.
• organic acids include acetic acid, succinic acid, propionic acid, adipic acid, valeric acid, pivalic acid, catechol, phenol, glycine, alanine, valine, leucine, isoleucine, serine, cysteine, methionine, aspartic acid, asparagine, glutamic acid, glutamine, arginine, lysine, histidine, phenylalanine, tyrosine, tryptophan, proline, etc.
• acetic acid and succinic acid it is preferable to contain acetic acid.
• the content of the organic acid may be such that the acid value of the composition of the present invention falls within the above-mentioned numerical range.
• the upper limit of the organic acid content is preferably 2000 ppm by mass or less, and more preferably 1000 ppm by mass or less.
• the lower limit of the content is preferably 0.001 ppm by mass or more, and more preferably 0.01 ppm by mass or more. Any combination of these upper and lower limits can be used.
• the organic acid content in the 1,6-hexanediol composition is preferably 1 to 2000 ppm by mass, more preferably 10 to 1000 ppm by mass, for reasons of economic efficiency in the purification process.
• the content of organic acid means the total content when a plurality of organic acids are contained. The same applies to the contents of other components.
• the content of organic acid in the 1,6-hexanediol composition means the content of free organic acid in principle, but may also include the content of organic acid in the form of a salt.
• the content of organic acid is a value measured by high performance liquid chromatography mass spectrometry (LC/MS).
• composition of the present invention may contain 6-hydroxyhexanal.
• 6-Hydroxyhexanal is produced as an intermediate in a metabolic pathway that produces 1,6-hexanediol using biomass resources.
• the upper limit of the 6-hydroxyhexanal content is preferably 300 ppm by mass or less, more preferably 150 ppm by mass or less, and even more preferably 100 ppm by mass or less.
• the lower limit of the content is preferably 10 ppm by mass or more, and more preferably 20 ppm by mass or more. Any combination of these upper and lower limits can be used.
• the content of 6-hydroxyhexanal is preferably from 10 to 300 ppm by mass, more preferably from 20 to 150 ppm by mass. In this specification, the content of 6-hydroxyhexanal is measured by high performance liquid chromatography mass spectrometry (LC/MS).
• the composition of the present invention may contain an alkali metal element.
• the upper limit of the total content of the alkali metal elements relative to the total amount of the composition is preferably 200 mass ppm or less, more preferably 100 mass ppm or less, and even more preferably 50 mass ppm or less.
• the lower limit of the total content is preferably 0.1 mass ppm or more, and more preferably 1 mass ppm or more. Any combination of these upper and lower limits can be used.
• the total content of the alkali metal elements is preferably from 0.1 to 100 ppm by mass, and more preferably from 0.1 to 50 ppm by mass.
• the alkali metal element When the alkali metal element is contained at 200 ppm by mass, the APHA color number value in the PCD and the storage stability of the NCO-terminated prepolymer did not result in good results, as shown in Example 10 below, so the content of the alkali metal element is preferably 100 ppm by mass or less. However, even when the alkali metal element of Example 10 is contained at 200 ppm by mass, when polyurethane (PU) is produced using such an NCO-terminated prepolymer, the PU sheet can show good results in each evaluation item of tensile strength, breaking elongation, and hydrolysis resistance (see the results in Table 1 below).
• PU polyurethane
• the alkali metal element is not particularly limited, and examples thereof include lithium, sodium, potassium, rubidium, and cesium. These elements may be contained alone or in combination of two or more. Of these, it is preferable that sodium and potassium are contained.
• the state of the alkali metal element contained in the composition of the present invention is not particularly limited, and may be an alkali metal element, an alkali metal compound, an alkali metal ion, or the like.
• the alkali metal compound for example, the above-mentioned alkali metal elements are present in the composition of the present invention as alkali metal salts by reacting with the above-mentioned organic acids.
• the total content of alkali metal elements is preferably 100 mass ppm or less as described above, and the lower limit of the total content is preferably 0.1 mass ppm or more.
• the total content of alkali metal elements is preferably 0.1 to 100 ppm by mass, more preferably 1 to 50 ppm by mass. In this specification, the total content of alkali metal elements is measured by inductively coupled plasma mass spectrometry (ICP-MS).
• the polycarbonate polyol of the present invention is a polyol obtained by reacting the 1,6-hexanediol composition of the present invention with a carbonate. Therefore, the polycarbonate polyol of the present invention has at least structural units derived from the 1,6-hexanediol composition of the present invention and structural units derived from carbonate, and also contains 6-hydroxyhexanal, organic acid, alkali metal element, and the like contained in the 1,6-hexanediol composition of the present invention.
• Examples of carbonates that can be used as raw materials for the polycarbonate polyol of the present invention include dialkyl carbonates (dimethyl carbonate, diethyl carbonate, etc.), ethylene carbonate, and diphenyl carbonate, among which dialkyl carbonates are preferred, and diethyl carbonate is particularly preferred.
• the polycarbonate polyol of the present invention is particularly preferably a polycarbonate diol.
• the method of production there are no particular limitations on the method of production, and it can be synthesized by various known methods, for example, by reacting the 1,6-hexanediol composition of the present invention with carbonate in the presence of an ester exchange catalyst.
• the content of the structural unit derived from the 1,6-hexanediol composition of the present invention in 100% by mass of the polycarbonate polyol of the present invention is preferably 10 to 95% by mass, more preferably 30 to 90% by mass. This tends to make it possible to obtain the desired effect.
• the content of each structural unit in the polycarbonate polyol is measured by NMR.
• the total content of alkali metal elements is preferably 0.05 to 90 mass ppm, more preferably 0.05 to 45 mass ppm. This tends to make it possible to more suitably obtain the effects of the present invention.
• the content of 6-hydroxyhexanal, including the amount consumed during the synthesis of the polycarbonate polyol is preferably 5 to 270 ppm by mass, and more preferably 15 to 135 ppm by mass. This tends to make it possible to more suitably obtain the effects of the present invention.
• the polycarbonate polyol of the present invention contains an acid
• the number average molecular weight (Mn) of the polycarbonate polyol of the present invention is preferably from 300 to 1,000,000, more preferably from 500 to 10,000, and even more preferably from 1,000 to 5,000.
• the number average molecular weight (Mn) of a polymer is a value measured by gel permeation chromatography (GPC).
• the polyurethane of the present invention is a reaction product obtained by reacting the polycarbonate polyol of the present invention with a polyisocyanate. If necessary, a polyol other than the polycarbonate polyol of the present invention, a chain extender, a chain terminator, a crosslinking agent, etc. may be used in combination as a reaction raw material for the polyurethane of the present invention.
• the polyurethane of the present invention has structural units derived from a polyol and structural units derived from a polyisocyanate, and has at least structural units derived from the 1,6-hexanediol composition of the present invention, and also contains 6-hydroxyhexanal, an organic acid, an alkali metal element, and the like contained in the 1,6-hexanediol composition of the present invention.
• Polyols other than the polycarbonate polyol of the present invention include polyols such as polycarbonate polyols, polyether polyols, and polyester polyols that do not use the 1,6-hexanediol composition of the present invention as a raw material. These polyols may or may not use the 1,6-hexanediol composition as a reaction raw material, and the polyurethane of the present invention may use at least a polyol that uses the 1,6-hexanediol composition as a reaction raw material as a reaction raw material.
• a polyol obtained by a reaction between a known glycol and a carbonate may be used as the polycarbonate polyol not using the 1,6-hexanediol composition of the present invention as a raw material.
• the glycol include various saturated or unsaturated glycols such as diethylene glycol, ethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, pentanediol, 3-methyl-1,5-pentanediol, octanediol, 1,4-butynediol, dipropylene glycol, tripropylene glycol, polytetramethylene ether glycol, 2-methyl-1,3-propanediol, and 2-ethyl-2-butyl-1,3-propanediol, alicycl
• Polyether polyols are, for example, polyether polyols obtained by addition polymerization of alkylene oxides using various glycols as initiators.
• alkylene oxides include ethylene oxide, propylene oxide, butylene oxide, and tetrahydrofuran.
• examples of various glycols include those similar to those of the polycarbonate diols mentioned above.
• polyester polyols include condensation polyester polyols, lactone polyester polyols, etc.
• Condensation polyester polyols are, for example, reaction products of low molecular weight polyhydric alcohols (ethylene glycol (EG), diethylene glycol, propylene glycol (PG), dipropylene glycol, (1,3- or 1,4-)butanediol, pentanediol, neopentyl glycol, cyclohexanedimethanol, glycerin, 1,1,1-trimethylolpropane (TMP), 1,2,5-hexanetriol, pentaerythritol, 1,4-cyclohexanedimethanol, and other low molecular weight polyols, sorbitol, and other sugars) and polybasic carboxylic acids (glutaric acid, adipic acid, azelaic acid, fumaric acid, maleic acid, pimelic acid, suberic acid, sebacic acid,
• At least the polycarbonate polyol of the present invention is used as the polyol, and the content of the polycarbonate polyol made from the composition of the present invention in 100% by mass of polyol is preferably 10 to 100% by mass, more preferably 50 to 100% by mass.
• polyisocyanates examples include 1,3- and 1,4-phenylene diisocyanate, 1-methyl-2,4-phenylene diisocyanate, 1-methyl-2,6-phenylene diisocyanate, 1-methyl-2,5-phenylene diisocyanate, 1-methyl-2,6-phenylene diisocyanate, 1-methyl-3,5-phenylene diisocyanate, 1-ethyl-2,4-phenylene diisocyanate, 1-isopropyl-2,4-phenylene diisocyanate, 1,3-dimethyl-2,4-phenylene diisocyanate, and 1,3-dimethyl-4,6-phenylene diisocyanate.
• 1,4-dimethyl-2,5-phenylene diisocyanate diethylbenzene diisocyanate, diisopropylbenzene diisocyanate, 1-methyl-3,5-diethylbenzene diisocyanate, 3-methyl-1,5-diethylbenzene-2,4-diisocyanate, 1,3,5-triethylbenzene-2,4-diisocyanate, naphthalene-1,4-diisocyanate, naphthalene-1,5-diisocyanate, 1-methyl-naphthalene-1,5-diisocyanate, naphthalene-2,6-diisocyanate, naphthalene-2,7-diisocyanate, 1,1-dinaphthyl-2,2 aromatic polyisocyanates such as 1,3-dimethyl-2,4-diisocyanate, 4,4'-diphenylmethane diisocyanate,
• polyisocyanates can also be derived from biomass resources. These may be used alone or in combination of two or more. Among them, aromatic polyisocyanates are preferred, and 4,4'-diphenylmethane diisocyanate and toluene diisocyanate are more preferred.
• Chain extenders include, for example, aliphatic polyol compounds such as ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, hexamethylene glycol, saccharose, methylene glycol, glycerin, sorbitol, and neopentyl glycol; aromatic polyols such as bisphenol A, 4,4'-dihydroxydiphenyl, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxydiphenyl sulfone, hydrogenated bisphenol A, and hydroquinone.
• aromatic polyols such as bisphenol A, 4,4'-dihydroxydiphenyl, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxydiphenyl sulfone, hydrogenated bisphenol A, and hydroquinone.
• amine compounds such as ethylenediamine, 1,2-propanediamine, 1,6-hexamethylenediamine, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, isophoronediamine, 4,4'-dicyclohexylmethanediamine, 3,3'-dimethyl-4,4'-dicyclohexylmethanediamine, 1,2-cyclohexanediamine, 1,4-cyclohexanediamine, aminoethylethanolamine, hydrazine, diethylenetriamine, triethylenetetramine, isophoronediamine, and 4,4'-methylenebis(2-chloroaniline) can be used.
• chain extenders can also be derived from biomass resources.
• chain extenders can be used alone or in combination of two or more.
• neopentyl glycol, 1,4-butanediol (1,4-butylene glycol), trimethylolpropane, isophoronediamine, and 4,4'-methylenebis(2-chloroaniline) are more preferred.
• a chain terminator having one active hydrogen group can be used as necessary.
• chain terminators include aliphatic monohydroxy compounds having a hydroxyl group, such as methanol, ethanol, propanol, butanol, and hexanol, and aliphatic monoamines having an amino group, such as morpholine, diethylamine, dibutylamine, monoethanolamine, and diethanolamine. These may be used alone or in combination of two or more.
• a crosslinking agent with three or more active hydrogen groups or isocyanate groups can be used to increase the heat resistance and strength of the resulting polyurethane.
• the polyurethane of the present invention can be obtained by a known polyurethane manufacturing method. Specific examples include a manufacturing method in which the polyol, the polyisocyanate, and the chain extender are charged and reacted, and a method in which the polyol and the polyisocyanate are reacted to synthesize a prepolymer, and then the prepolymer is reacted with the chain extender. These reactions are preferably carried out at a temperature of 50 to 100°C for 3 to 10 hours. The reaction may also be carried out in an organic solvent.
• organic solvents examples include ketone solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, methyl ethyl ketone, methyl-n-propyl ketone, acetone, and methyl isobutyl ketone; ester solvents such as methyl formate, ethyl formate, propyl formate, methyl acetate, ethyl acetate, isopropyl acetate, isobutyl acetate, isobutyl acetate, and sec-butyl acetate; and alcohol solvents such as methanol, ethanol, isopropyl alcohol, and butanol. These organic solvents may also be derived from biomass resources. These organic solvents may be used alone or in combination of two or more.
• the polyurethane is made from the polycarbonate polyol of the present invention as a raw material, and the content of structural units derived from the polycarbonate polyol of the present invention in 100% by mass of the polyurethane is preferably 10 to 90% by mass, more preferably 20 to 90% by mass. This tends to make it possible to more suitably obtain the effects of the present invention.
• the content of the structural units derived from the 1,6-hexanediol composition of the present invention in 100% by mass of the polyurethane of the present invention is preferably 1 to 63% by mass, and more preferably 2 to 63% by mass, which tends to more suitably obtain the effects of the present invention.
• the content of each structural unit in the polyurethane is measured by NMR.
• the total content of alkali metal elements is preferably 0.01 to 75 mass ppm, and more preferably 0.01 to 36 mass ppm. This tends to make it possible to more suitably obtain the effects of the present invention.
• the organic acid content is preferably 0.5 to 1500 ppm by mass, more preferably 0.5 to 750 ppm by mass, and even more preferably 3 to 360 ppm by mass. This tends to make it possible to more suitably obtain the effects of the present invention.
• the content of 6-hydroxyhexanal is preferably 5 to 240 ppm by mass, and more preferably 10 to 110 ppm by mass. This tends to make it easier to obtain the effects of the present invention.
• the number average molecular weight (Mn) of the polyurethane of the present invention is preferably 5,000 to 1,000,000, and more preferably 10,000 to 500,000. This tends to make it possible to more suitably obtain the effects of the present invention.
• the number average molecular weight (Mn) of the polyurethane is a value measured by gel permeation chromatography (GPC).
• polyurethane can be produced through the following steps (i) to (iii).
• PCD polycarbonate diol
• MDI 4,4'-diphenylmethane diisocyanate
• 1,4-butylene glycol (1,4BG)/trimethylolpropane (TMP) 1,4-butylene glycol
• TMP trimethylolpropane
• each polymer is obtained stepwise from PCD to NCO-terminated prepolymer to PU sheet.
• an alkali metal element remains in the form of a salt with an organic acid.
• the organic acid that does not form a salt with an alkali metal element reacts with 1,6-HDO to form an ester, which is then incorporated into the polymer.
• 6-Hydroxyhexanal is incorporated into the polymer as an end-capping structure during the synthesis of PCD. That is, in the following examples, the physical properties of polymers containing alkali metal salts, organic acids (carboxylic acids), and 6-hydroxyhexanal are evaluated.
• the polycarbonate diol (PCD) obtained in the step (i) preferably has a color number APHA value of less than 50, more preferably 20 or less.
• the color number APHA value can be measured in accordance with JIS K0071-2017 using, for example, a petroleum product color tester OME2000 manufactured by Nippon Denshoku Kogyo Co., Ltd.
• the isocyanate (NCO)-terminated prepolymer obtained in step (ii) preferably has a storage stability (viscosity change rate) value of less than 4, and more preferably less than 3.
• the storage stability (viscosity change rate) value of the NCO-terminated prepolymer is more preferably 2 or more and less than 3, and even more preferably 1 or more and less than 2.
• the viscosity change rate can be determined as follows.
• the polyurethane elastomer obtained in step (iii) preferably has a tensile strength of 25 MPa or more, and more preferably 30 MPa or more.
• the breaking elongation of the polyurethane elastomer is preferably 300% or more, and more preferably 320% or more.
• the tensile strength and elongation at break can be determined as follows.
• a polyurethane (PU) sheet is measured in accordance with JIS K7312 using a No. 3 test piece at a grip distance of 60 mm, a gauge distance of 20 mm, a head speed of 500 mm/min, and a measurement temperature of 23°C to measure the tensile strength and elongation at break (break elongation).
• an Autograph AGX-V model manufactured by Shimadzu Corporation can be used.
• the hydrolysis resistance (strength retention) of the polyurethane elastomer is preferably 70% or more, and more preferably 80% or more.
• the polymer of the present invention can be used for a wide variety of applications. Specifically, it can be used in a wide range of applications, including artificial leather, synthetic leather, shoes, thermoplastic resins, foamed resins, thermosetting resins, paints, laminating adhesives, elastic fibers, urethane raw materials, automobile parts, sporting goods, vibration-proofing materials, vibration-damping materials, fiber treatment agents, and binders.
• the polyurethane of the present invention can be used in a wide variety of applications. Specifically, it can be used in a wide range of applications, including the surface layer, intermediate layer, foam layer, and adhesive layer of artificial leather and synthetic leather; various coating agents such as paints, metal surface treatment agents, and film primers; binders for inkjet printing, ink, textile printing, and glass fiber bundling agents; adhesives such as shoes, thermoplastic resins, foam resins, thermosetting resins, and laminating adhesives, vibration-proofing materials, vibration-damping materials, automobile parts, sporting goods, and fiber treatment agents.
• various coating agents such as paints, metal surface treatment agents, and film primers
• binders for inkjet printing, ink, textile printing, and glass fiber bundling agents binders for inkjet printing, ink, textile printing, and glass fiber bundling agents
• adhesives such as shoes, thermoplastic resins, foam resins, thermosetting resins, and laminating adhesives, vibration-proofing materials, vibration-damping materials, automobile
• the recombinant E. coli for producing 1,6-hexanediol was prepared by referring to the method for producing the recombinant E. coli described in JP-A-2022-530467.
• the culture solution was centrifuged at 4° C. for 20 minutes, and the supernatant was collected and filtered using a membrane filter with an appropriate pore size of 0.2 to 0.4 ⁇ m to obtain a 1,6-hexanediol composition as the filtrate.
• step (a) cation exchange was performed in a batch manner. The temperature for contact with the cation exchange resin was set to 40°C, and DIAION SK1BH manufactured by Mitsubishi Chemical Corporation was added as a cation exchange resin to the 1,6-hexanediol composition, followed by stirring for 3 hours. After stirring, filtration was performed to obtain 1,6-hexanediol composition A as the filtrate.
• anion exchange was carried out in a batch manner. The temperature for contact with the anion exchange resin was set to 40° C., and DIAION SA10AOH manufactured by Mitsubishi Chemical Corporation was added as an anion exchange resin to the 1,6-hexanediol composition, followed by stirring for 3 hours. After stirring, filtration was carried out to obtain a 1,6-hexanediol composition B as a filtrate.
• the 6-hydroxyhexanal content changes depending on the species of origin of 6-hydroxyhexanal 1-reductase used in the production of recombinant Escherichia coli or the strength of the expression promoter. Taking such points into consideration, the 6-hydroxyhexanal content was adjusted.
• the content of alkali metal changes by changing the amount of cation exchange resin described in the above ⁇ Step (a): Ion exchange for removing cations>. Therefore, the content of alkali metal was adjusted taking this into consideration.
• Example 3 similarly to Example 2, the 1,6-hexanediol composition-1 (1,6HDO-1) in Example 1 was changed to the 1,6-hexanediol composition-3 (1,6HDO-3), and the same procedure as in Example 1 was carried out to obtain polycarbonate diol-3 in Example 3.
• Example 4 and subsequent examples were conducted in the same manner as Examples 2 and 3, and the example numbers correspond to the reference numbers of the polycarbonate diols. The same applies to Comparative Examples 1 and 2.
• PU polyurethane
• the polyurethane (PU) sheet was measured in accordance with JIS K7312 using a No. 3 test piece at a grip distance of 60 mm, a gauge distance of 20 mm, a head speed of 500 mm/min, and a measurement temperature of 23°C to measure the tensile strength and elongation at break (break elongation).
• the measurement equipment used was an Autograph AGX-V model manufactured by Shimadzu Corporation. The tensile strength was evaluated based on the following criteria.

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