WO2025013399A1 - ポリカーボネート共重合体およびそれからなる成形品 - Google Patents
ポリカーボネート共重合体およびそれからなる成形品 Download PDFInfo
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- WO2025013399A1 WO2025013399A1 PCT/JP2024/017729 JP2024017729W WO2025013399A1 WO 2025013399 A1 WO2025013399 A1 WO 2025013399A1 JP 2024017729 W JP2024017729 W JP 2024017729W WO 2025013399 A1 WO2025013399 A1 WO 2025013399A1
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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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
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- the present invention relates to a polycarbonate copolymer that exhibits minimal dimensional change due to heat or water absorption and has excellent heat resistance, and to a molded article made from the copolymer.
- Polycarbonate resin has excellent transparency and impact resistance, and is used as an engineering plastic in a wide range of fields, including housings for electrical and electronic equipment, interior and exterior parts for automobiles, building materials, furniture, musical instruments, and miscellaneous goods.
- Polycarbonate resins that have 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane as a structural unit are known to have excellent heat resistance (see, for example, Patent Documents 1 and 2). Although this polycarbonate resin has excellent heat resistance, it has a high linear expansion coefficient, which means that its dimensions change significantly due to heat.
- the object of the present invention is to provide polycarbonate resins that have little dimensional change due to heat or water absorption and excellent heat resistance, and molded articles made from them.
- the present invention provides the following items 1 to 8.
- the polycarbonate copolymers of the present invention and the molded articles made from them are particularly suitable for use in electrical and electronic parts because they undergo minimal dimensional change due to heat or water absorption and have excellent heat resistance. Therefore, the industrial effects they provide are exceptional.
- the polycarbonate copolymer of the present invention is a polycarbonate copolymer containing a structural unit (A) represented by the following formula (1) and a structural unit (B) represented by the following formula (2).
- the polycarbonate copolymer contains 70 mol % or more of the structural units (A) and (B) based on the total structural units, preferably 80 mol % or more, and more preferably 90 mol % or more.
- R 1 , R 2 and R 3 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms;
- R 4 represents an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl-substituted alkyl group having 7 to 13 carbon atoms; and
- n and m each independently represent an integer of 1 to 4.
- X represents a group that bonds with a carbon atom to form an alicyclic hydrocarbon having 6 to 12 carbon atoms which may have a substituent.
- R 1 , R 2 and R 3 are each independently a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.
- R 4 is an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl-substituted alkyl group having 7 to 13 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and most preferably a phenyl group.
- the content (molar fraction) of the structural unit (A) is 10 to 90 mol % relative to all structural units of the polycarbonate copolymer, preferably 20 to 90 mol %, more preferably 30 to 90 mol %, and even more preferably 30 to 80 mol %. If it is below the lower limit, the glass transition temperature may be low or the linear expansion coefficient may be high. Also, if it exceeds the upper limit, the water absorption rate may be high.
- X is a group that bonds with a carbon atom to form an alicyclic hydrocarbon having 6 to 12 carbon atoms (including the carbon atoms in formula (2)) that may have a substituent, and is preferably a cyclohexyl group substituted with a methyl group, and most preferably a 3,3,5-trimethylcyclohexyl group.
- the content (molar fraction) of the structural unit (B) is preferably 10 to 90 mol%, more preferably 10 to 80 mol%, even more preferably 10 to 70 mol%, and particularly preferably 20 to 70 mol%. If it is below the lower limit, the water absorption rate may be high. If it exceeds the upper limit, the glass transition temperature may be low or the linear expansion coefficient may be high.
- the polycarbonate copolymer of the present invention may further contain the structural unit (C) represented by the following formula (3) or other copolymerization units in an amount of 30 mol % or less, preferably 20 mol % or less, and more preferably 10 mol % or less of all structural units.
- C structural unit represented by the following formula (3) or other copolymerization units in an amount of 30 mol % or less, preferably 20 mol % or less, and more preferably 10 mol % or less of all structural units.
- Y is a single bond or at least one group selected from the group consisting of the following formula (4):
- R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 each independently represent at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 14 carbon atoms and an aralkyl group having 7 to 20 carbon atoms;
- R 13 and R Each of 14 independently represents at least one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkoxy group having 6 to 20 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms
- the raw material monomers used for the polycarbonate copolymer in the present invention include dihydric phenols represented by the following formula (5) and the following formula (6).
- R 1 , R 2 and R 3 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms;
- R 4 represents an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl-substituted alkyl group having 7 to 13 carbon atoms; and
- n and m each independently represent an integer of 1 to 4.
- X represents a group that bonds with a carbon atom to form an alicyclic hydrocarbon having 6 to 12 carbon atoms which may have a substituent.
- PPPBP 2-phenyl-3,3-bis(p-hydroxyphenyl)phthalimidine
- TMC 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane
- the raw material monomers used in the polycarbonate copolymer of the present invention include the above formula (5) and formula (6), and may further include a monomer represented by the following formula (7) other than the monomers represented by formula (5) and formula (6).
- Y is a single bond or at least one group selected from the group consisting of the following formula (4):
- R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 each independently represent at least one group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 14 carbon atoms and an aralkyl group having 7 to 20 carbon atoms;
- R 13 and R Each of 14 independently represents at least one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 6 to 20 carbon atoms, a cycloalkoxy group having 6 to 20 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms
- 2,2-bis(4-hydroxyphenyl)propane 2,2-bis(4-hydroxy-3-methylphenyl)propane, or ⁇ , ⁇ '-bis(4-hydroxyphenyl)-1,3-diisopropylbenzene are preferred, with 2,2-bis(4-hydroxyphenyl)propane (hereinafter sometimes abbreviated as BPA) being more preferred.
- BPA 2,2-bis(4-hydroxyphenyl)propane
- the polycarbonate copolymer of the present invention may further be copolymerized with other dihydroxy compounds or diol compounds to the extent that the properties of the polycarbonate copolymer are not impaired.
- dihydroxy compounds include hydroquinone, resorcinol, orcinol, 2,2-bis(4-hydroxyphenyl)norbornene, 1,3-bis(4-hydroxyphenyl)adamantane; 2,2-bis(4-hydroxyphenyl)adamantane; 1,3-bis(4-hydroxyphenyl)-5,7-dimethyladamantane, 10,10-bis(4-hydroxyphenyl)-9-anthrone, 1,5-bis(4-hydroxyphenylthio)-2,3-dioxapentaenebisphenoxyethanolfluorene, etc.
- diol compounds include isosorbide:1,4:3,6-dianhydro-D-sorbitol, tricyclodecane dimethanol (TCDDM), 4,8-bis(hydroxymethyl)tricyclodecane, tetramethylcyclobutanediol (TMCBD), 2,2,4,4-tetramethylcyclobutane-1,3-diol, mixed isomers, cis/trans-1,4-cyclohexanedimethanol (CHDM), cis/trans-1,4-bis(hydroxymethyl)cyclohexane, cyclohex-1,4-ylenedimethane, These include cyclohexanedimethanol, trans-1,4-cyclohexanedimethanol (tCHDM), trans-1,4-bis(hydroxymethyl)cyclohexane, cis-1,4-cyclohexanedimethanol (cCHDM), cis-1,4-bis(hydroxymethyl)cyclohexane, cis-1
- the polycarbonate copolymer in the present invention is obtained by reacting the dihydric phenol compound with a carbonate precursor.
- Reaction methods include interfacial polycondensation, melt transesterification, solid-phase transesterification of carbonate prepolymers, and ring-opening polymerization of cyclic carbonate compounds.
- interfacial polycondensation a monohydric phenol end-terminator is usually used.
- the polycarbonate copolymer includes polyester carbonates copolymerized with aromatic or aliphatic (including alicyclic) bifunctional carboxylic acids.
- the aliphatic bifunctional carboxylic acids are preferably ⁇ , ⁇ -dicarboxylic acids.
- Preferred examples of the aliphatic bifunctional carboxylic acids include linear saturated aliphatic dicarboxylic acids such as sebacic acid (decanedioic acid), dodecanedioic acid, tetradecanedioic acid, octadecanedioic acid, and icosane diacid, as well as alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid.
- carboxylic acids may be copolymerized to the extent that the purpose is not hindered.
- the polycarbonate copolymer may be copolymerized with a structural unit containing a polyorganosiloxane unit, if necessary.
- polycarbonate copolymers can be made into branched polycarbonates by copolymerizing structural units containing trifunctional or higher polyfunctional aromatic compounds.
- trifunctional or higher polyfunctional aromatic compounds used in branched polycarbonates include trisphenols such as 4,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)heptene-2, 2,4,6-trimethyl-2,4,6-tris(4-hydroxyphenyl)heptane, 1,3,5-tris(4-hydroxyphenyl)benzene, 1,1,1-tris(4-hydroxyphenyl)ethane, 1,1,1-tris(3,5-dimethyl-4-hydroxyphenyl)ethane, 2,6-bis(2-hydroxy-5-methylbenzyl)-4-methylphenol, and 4- ⁇ 4-[1,1-bis(4-hydroxyphenyl)ethyl]benzene ⁇ - ⁇ , ⁇ -dimethylbenzylphenol.
- trisphenols such as 4,6-dimethyl-2,4,6-tris(4-hydroxyphenyl)heptene-2, 2,4,6-trimethyl-2,4,6-tris(4-hydroxyphenyl)heptan
- 1,1,1-tris(4-hydroxyphenyl)ethane is preferred.
- the constituent units derived from such polyfunctional aromatic compounds preferably account for 0.03 to 1.5 mol%, more preferably 0.1 to 1.2 mol%, and particularly preferably 0.2 to 1.0 mol%, of a total of 100 mol% including the constituent units from other dihydric phenol components.
- the branched structural unit may be derived not only from a polyfunctional aromatic compound, but also from a side reaction occurring during a polymerization reaction by a melt transesterification method without using a polyfunctional aromatic compound.
- the proportion of such branched structures can be calculated by 1H -NMR measurement.
- the reaction is usually carried out in the presence of an acid binder and a solvent.
- an acid binder for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or an amine compound such as pyridine, is used.
- the solvent for example, a halogenated hydrocarbon such as methylene chloride or chlorobenzene is used.
- a catalyst such as a tertiary amine or a quaternary ammonium salt can be used to promote the reaction.
- the reaction temperature is usually 0 to 40°C, and the reaction time is several minutes to 5 hours.
- Transesterification using, for example, a carbonic acid diester as a carbonate precursor is carried out by heating and stirring a predetermined proportion of aromatic dihydroxy components with the carbonic acid diester under an inert gas atmosphere, and distilling off the resulting alcohol or phenol.
- the reaction temperature varies depending on the boiling point of the resulting alcohol or phenol, but is usually in the range of 120 to 300°C.
- the reaction is completed by reducing the pressure from the beginning and distilling off the resulting alcohol or phenol.
- a catalyst usually used in transesterification can be used.
- carbonic acid diesters used in the transesterification reaction include diphenyl carbonate, dinaphthyl carbonate, bis(diphenyl)carbonate, dimethyl carbonate, diethyl carbonate, and dibutyl carbonate. Of these, diphenyl carbonate is particularly preferred.
- Monofunctional phenols that are commonly used as end terminators can be used.
- monofunctional phenols are commonly used as end terminators to adjust molecular weight, and the resulting polycarbonate copolymer has excellent thermal stability compared to those that are not, since the ends are blocked with groups based on monofunctional phenols.
- Specific examples of the monofunctional phenols include phenol, m-methylphenol, p-methylphenol, m-propylphenol, p-propylphenol, 1-phenylphenol, 2-phenylphenol, p-tert-butylphenol, p-cumylphenol, isooctylphenol, and p-long-chain alkylphenol.
- the polycarbonate copolymer of the present invention may contain various additives to give various properties to the resin composition within a range that does not impair the object of the present invention.
- the additives may include a mold release agent, a heat stabilizer, an ultraviolet absorber, a bluing agent, an antistatic agent, a flame retardant, a heat shielding agent, a fluorescent dye (including a fluorescent brightener), a pigment, a light diffusing agent, a reinforcing filler, other resins, elastomers, etc.
- the release agent is preferably one that is composed of 90% by weight or more of an ester of alcohol and fatty acid.
- Specific examples of the ester of alcohol and fatty acid include ester of monohydric alcohol and fatty acid, and partial or complete ester of polyhydric alcohol and fatty acid.
- Specific examples of the ester of monohydric alcohol and saturated fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate, etc. Stearyl stearate is preferred.
- esters of polyhydric alcohols and saturated fatty acids include stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, dipentaerythritol hexastearate, and other complete or partial esters of dipentaerythritol.
- esters stearic acid monoglyceride, stearic acid triglyceride, pentaerythritol tetrastearate, and mixtures of stearic acid triglyceride and stearyl stearate are preferred, and stearic acid monoglyceride and pentaerythritol tetrastearate are more preferred.
- the amount of release agent to be added is preferably in the range of 0.05 to 0.5 parts by weight, more preferably in the range of 0.1 to 0.4 parts by weight, and even more preferably in the range of 0.12 to 0.3 parts by weight, per 100 parts by weight of the polycarbonate copolymer.
- Heat stabilizers include phosphorus-based heat stabilizers, sulfur-based heat stabilizers, and hindered phenol-based heat stabilizers.
- Phosphorus-based heat stabilizers include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, and esters thereof.
- bis(2,4-dicumylphenyl)pentaerythritol diphosphite tris(2,4-di-tert-butylphenyl)phosphite, tris(2,6-di-tert-butylphenyl)phosphite, 3-(3,5-di-tert-butyl-4-hydroxyphenyl)stearyl propionate, [1,1-biphenyl]-4,4-diylbis[bis(2,4-di-tert-butylphenoxy)phosphine], 3,9-bis(2,6-di-tert-butylphenyl)phosphite, 3,5-di-tert-butyl-4-hydroxyphenyl)stearyl propionate, [1,1-biphenyl]-4,4-diylbis[bis(2,4-di-tert-butylphenoxy)phosphine], 3,9-bis(2,6-di-di
- butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane is preferred, and tris(2,4-di-tert-butylphenyl)phosphite, 3-(3,5-di-tert-butyl-4-hydroxyphenyl)stearyl propionate, and 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane are more preferred.
- the amount of heat stabilizer to be added is preferably in the range of 0.001 to 0.5 parts by weight, more preferably in the range of 0.005 to 0.4 parts by weight, and even more preferably in the range of 0.01 to 0.3 parts by weight, per 100 parts by weight of polycarbonate copolymer.
- the viscosity average molecular weight of the polycarbonate copolymer in the present invention is preferably 6,000 to 30,000, more preferably 7,000 to 28,000, and even more preferably 8,000 to 25,000. Within the above range, mechanical properties, productivity, and processability are excellent, which is preferable.
- the viscosity average molecular weight of the polycarbonate copolymer in the present invention can be calculated by the following formula : [ t0 is the number of seconds that methylene chloride falls, and t is the number of seconds that the sample solution falls]
- the glass transition temperature (Tg) of the polycarbonate copolymer in the present invention is preferably in the range of 200 to 280° C., more preferably 220 to 280° C., and even more preferably 240 to 275° C. If the Tg is within the above range, the heat resistance is excellent, which is preferable.
- the glass transition temperature (Tg) is measured using a 2910 DSC manufactured by TA Instruments Japan Ltd. at a heating rate of 20° C./min.
- the coefficient of linear expansion (CTE) of the polycarbonate copolymer in the present invention is preferably in the range of 40 to 60 ppm/°C, more preferably 43 to 58 ppm/°C, and even more preferably 45 to 56 ppm/°C. If the CTE is within the above range, dimensional change due to heat is small, which is preferable.
- CTE coefficient of linear expansion
- the saturated water absorption of the polycarbonate copolymer in the present invention is measured in accordance with JIS K7209:2000 and is preferably 2.40% or less, more preferably 2.38% or less, and even more preferably 2.35% or less. If the saturated water absorption is within the above range, the dimensional change due to water absorption is small, which is preferable.
- the lower limit of the saturated water absorption is not particularly limited, but 0.10% or more is sufficient.
- a general method for molding a polycarbonate copolymer can be used, such as injection molding, extrusion molding, compression molding, solution casting, etc.
- a method for molding a molded product by injection molding or a method for molding a sheet or film by extrusion molding is preferably used.
- the polycarbonate copolymer of the present invention has excellent transparency, dimensional stability and heat resistance, and can be used for a variety of molded products, and is particularly suitable for electrical and electronic parts such as connectors, switches, sockets, sensor cases and flexible films that are used in high-temperature environments.
- composition Ratio 40 mg of a sample was dissolved in 0.6 mL of deuterated chloroform, and the polymer composition ratio (molar ratio) was calculated from the integral ratio of each structural unit using proton NMR on a JEOL JNM-AL400.
- Viscosity average molecular weight Specific viscosity ( ⁇ SP) (t-t 0 )/t 0 [ t0 is the number of seconds that methylene chloride falls, and t is the number of seconds that the sample solution falls]
- the specific viscosity ( ⁇ SP) calculated by the above formula was determined by using an Ostwald viscometer to dissolve 0.7 g of the sample in 100 ml of methylene chloride at 20° C., and the viscosity average was calculated from the specific viscosity ( ⁇ SP) by the following formula:
- the molecular weight Mv was calculated.
- CTE Coefficient of linear expansion
- Example 1 In a reactor equipped with a thermometer, a stirrer, and a reflux condenser, 98.69 parts by weight of ion-exchanged water and 59.04 parts by weight of 25% aqueous sodium hydroxide solution were placed under a nitrogen atmosphere, and 33.15 parts by weight of 2-phenyl-3,3-bis(p-hydroxyphenyl)phthalimidine (manufactured by Sansei Ryusei Pharmaceutical Co., Ltd., hereinafter referred to as PPPBP) as a dihydric phenol, 6.54 parts by weight of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (manufactured by Honshu Chemical Co., Ltd., hereinafter referred to as TMC), and 0.079 parts by weight of hydrosulfite (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) were dissolved therein, and then 116.5 parts by weight of methylene chloride was added,
- Example 2 In a reactor equipped with a thermometer, a stirrer, and a reflux condenser, 94.80 parts by weight of ion-exchanged water and 56.70 parts by weight of 25% aqueous sodium hydroxide solution were placed under a nitrogen atmosphere, and 7.96 parts by weight of PPPBP, 25.11 parts by weight of TMC, and 0.066 parts by weight of hydrosulfite were dissolved as dihydric phenols. Then, 116.5 parts by weight of methylene chloride was added, and 13.03 parts by weight of phosgene was blown in over 60 minutes at 18 to 20°C while stirring.
- Example 3 In a reactor equipped with a thermometer, a stirrer, and a reflux condenser, 94.76 parts by weight of ion-exchanged water and 56.70 parts by weight of 25% aqueous sodium hydroxide solution were placed under a nitrogen atmosphere, and 19.89 parts by weight of PPPBP, 15.71 parts by weight of TMC, and 0.071 parts by weight of hydrosulfite were dissolved as dihydric phenols, and then 111.9 parts by weight of methylene chloride was added, and 13.03 parts by weight of phosgene was blown in over 60 minutes at 18 to 20°C while stirring.
- Example 4 In a reactor equipped with a thermometer, a stirrer, and a reflux condenser, 94.76 parts by weight of ion-exchanged water and 56.70 parts by weight of 25% aqueous sodium hydroxide solution were placed under a nitrogen atmosphere, and 15.92 parts by weight of PPPBP, 15.71 parts by weight of TMC, 2.31 parts by weight of 2,2-bis(4-hydroxyphenyl)propane (manufactured by Nippon Steel Chemical & Material, hereinafter referred to as BPA) and 0.063 parts by weight of hydrosulfite were dissolved as dihydric phenols, and then 111.87 parts by weight of methylene chloride was added, and 13.03 parts by weight of phosgene was blown in over 60 minutes at 18 to 20°C while stirring.
- BPA 2,2-bis(4-hydroxyphenyl)propane
- Example 5 In a reactor equipped with a thermometer, a stirrer, and a reflux condenser, 109.45 parts by weight of ion-exchanged water and 65.49 parts by weight of a 25% aqueous sodium hydroxide solution were placed under a nitrogen atmosphere, and 41.36 parts by weight of PPPBP, 3.63 parts by weight of TMC, and 0.090 parts by weight of hydrosulfite were dissolved as dihydric phenols. Then, 129.22 parts by weight of methylene chloride was added, and 15.05 parts by weight of phosgene was blown in over 60 minutes at 18 to 20°C under stirring.
- the organic phase was repeatedly washed with ion-exchanged water.
- the aqueous phase was dropped into warm water kept at 50 to 80°C to evaporate and remove the solvent, and a flaky solid was obtained.
- the obtained solid was filtered and dried at 120°C for 24 hours to obtain a white flaky polycarbonate copolymer.
- the obtained polycarbonate copolymer was used to carry out various evaluations using the above-mentioned methods, and the results are shown in Table 1.
- the polycarbonate copolymer of the present invention has excellent heat resistance and undergoes minimal dimensional change due to heat or water absorption, making it suitable for use in electrical and electronic components such as connectors, switches, sockets, sensor cases, and flexible films that are used in high-temperature environments.
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| US20200172664A1 (en) * | 2018-11-30 | 2020-06-04 | Sabic Global Technologies B.V. | Endcapped polycarbonates, methods of manufacture, and articles formed therefrom |
| US20200339745A1 (en) * | 2017-11-01 | 2020-10-29 | Sabic Global Technologies B.V. | Phthalimidine copolycarbonate optical articles, articles formed therefrom, and methods of manufacture |
| WO2021171262A1 (en) * | 2020-02-28 | 2021-09-02 | Shpp Global Technologies B.V. | High heat polycarbonate copolymer formulations |
| WO2022112943A1 (en) * | 2020-11-26 | 2022-06-02 | Shpp Global Technologies B.V. | Polycarbonate and compositions and articles comprising the polycarbonate |
| WO2024090157A1 (ja) * | 2022-10-28 | 2024-05-02 | 帝人株式会社 | ポリカーボネート樹脂およびそれからなる成形品 |
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- 2024-06-03 TW TW113120459A patent/TW202511355A/zh unknown
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| US20190135977A1 (en) * | 2016-04-28 | 2019-05-09 | Sabic Global Technologies B.V. | Phthalimidine copolycarbonates, articles formed therefrom, and methods of manufacture |
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| US20200339745A1 (en) * | 2017-11-01 | 2020-10-29 | Sabic Global Technologies B.V. | Phthalimidine copolycarbonate optical articles, articles formed therefrom, and methods of manufacture |
| US20200172664A1 (en) * | 2018-11-30 | 2020-06-04 | Sabic Global Technologies B.V. | Endcapped polycarbonates, methods of manufacture, and articles formed therefrom |
| WO2021171262A1 (en) * | 2020-02-28 | 2021-09-02 | Shpp Global Technologies B.V. | High heat polycarbonate copolymer formulations |
| WO2022112943A1 (en) * | 2020-11-26 | 2022-06-02 | Shpp Global Technologies B.V. | Polycarbonate and compositions and articles comprising the polycarbonate |
| WO2024090157A1 (ja) * | 2022-10-28 | 2024-05-02 | 帝人株式会社 | ポリカーボネート樹脂およびそれからなる成形品 |
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| JPWO2025013399A1 (https=) | 2025-01-16 |
| TW202511355A (zh) | 2025-03-16 |
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