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WO2025037568A1 - Résine de polycarbonate - Google Patents

Résine de polycarbonate Download PDF

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Publication number
WO2025037568A1
WO2025037568A1 PCT/JP2024/028358 JP2024028358W WO2025037568A1 WO 2025037568 A1 WO2025037568 A1 WO 2025037568A1 JP 2024028358 W JP2024028358 W JP 2024028358W WO 2025037568 A1 WO2025037568 A1 WO 2025037568A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
substituent
polycarbonate resin
group
bisphenol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2024/028358
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English (en)
Japanese (ja)
Inventor
駿 石川
大 小黒
豊 西林
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Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Publication of WO2025037568A1 publication Critical patent/WO2025037568A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • 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
    • 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
    • C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent

Definitions

  • the present invention relates to a novel terminally modified polycarbonate resin.
  • Polycarbonate resin compositions are very useful materials because they have high total light transmittance, high impact strength, and high molding retention stability. Polycarbonate resin compositions can be used in a variety of applications, including transparent substrates for optical materials, automotive parts, and coatings, and are particularly suitable for molding materials for outdoor use, such as camera lenses, eyeglass lenses, and sunglasses.
  • molded products of synthetic resins containing polycarbonate resins are prone to deterioration and yellowing due to long-term exposure to sunlight and ultraviolet rays, and therefore ultraviolet absorbers are sometimes blended to improve light resistance (Patent Documents 1 and 2). Polycarbonates having triazole or benzophenone-type ultraviolet absorbers at the end are also known (Patent Document 3). However, although these ultraviolet absorbers show excellent weather resistance, they have low activity as reactive groups, and are not suitable for use as raw materials for the production of block copolymers with other resins or as reactive resin modifiers.
  • terminally modified polycarbonate resins include a terminally modified polycarbonate oligomer terminated with a chalcone derivative (Patent Document 4) and a polycarbonate resin having a terminal group with a specific structure having a benzotriazole ring (Patent Document 5), but the development of further terminally modified polycarbonate resins is desired.
  • a terminal-modified polycarbonate resin comprising a terminal structure (A) derived from a hydroxy compound represented by general formula (1) and a structural unit (B) derived from a dihydric phenol compound.
  • R1 represents an alkyl group having 1 to 6 carbon atoms which may be branched
  • R2 represents a halogen, a hydroxyl group, or a phenylthio group which may have a substituent
  • n represents an integer of 0 to 4.
  • R 5 to R 8 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an
  • R 9 and R 10 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R 9 and R 10 are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer from 0 to 20; R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atom
  • ⁇ 4> The terminal-modified polycarbonate resin according to ⁇ 3>, wherein X is a divalent group represented by general formula (3).
  • ⁇ 5> The terminal-modified polycarbonate resin according to ⁇ 3>, wherein the dihydric phenol compound is a bisphenol compound.
  • ⁇ 6> The terminal-modified polycarbonate resin according to ⁇ 5>, wherein the bisphenol compound is selected from the group consisting of bisphenol A, bisphenol AP, bisphenol Z, bisphenol CD, bisphenol C, bisphenol IOTD, bisphenol IBTD and bisphenol MIBK.
  • ⁇ 7> The terminally modified polycarbonate resin according to ⁇ 6>, wherein the bisphenol compound is bisphenol A.
  • the terminally modified polycarbonate resin according to ⁇ 1> characterized in that the transmittance at 330 nm is 1% or less.
  • An optical material comprising the terminally modified polycarbonate resin according to ⁇ 1>.
  • An optical material comprising the terminally modified polycarbonate resin according to ⁇ 8>.
  • Terminally modified polycarbonate resin comprising a terminal structure (A) derived from a hydroxy compound represented by general formula (1) and a structural unit (B) derived from a dihydric phenol compound:
  • A represents an alkyl group having 1 to 6 carbon atoms which may be branched
  • B represents a halogen, a hydroxyl group, or a phenylthio group which may have a substituent
  • n represents an integer of 0 to 4.
  • the hydroxy compound represented by the general formula (1) may be a compound represented by any one of the following formulas (1-1), (1-2), or (1-3), or a combination of two or more of these compounds.
  • a terminally modified polycarbonate resin in which the hydroxy compound represented by the general formula (1) is a compound represented by any one of the following formulas (1-1), (1-2), or (1-3), or a combination of two or more of these compounds.
  • a terminally modified polycarbonate resin in which the hydroxy compound represented by the general formula (1) is a compound represented by the above formula (1-1). In one embodiment of the present invention, a terminally modified polycarbonate resin is provided in which the hydroxy compound represented by the general formula (1) is a compound represented by the above formula (1-2). In one embodiment of the present invention, a terminally modified polycarbonate resin is provided in which the hydroxy compound represented by the general formula (1) is a compound represented by the above formula (1-3). In one embodiment of the present invention, a terminally modified polycarbonate resin is provided in which the hydroxy compound represented by the general formula (1) is a combination of a compound represented by the above formula (1-1) and a compound represented by the above formula (1-2).
  • a terminally modified polycarbonate resin in which the hydroxy compound represented by the general formula (1) is a combination of a compound represented by the above formula (1-1) and a compound represented by the above formula (1-3).
  • a terminally modified polycarbonate resin is provided in which the hydroxy compound represented by the general formula (1) is a combination of a compound represented by the above formula (1-2) and a compound represented by the above formula (1-3).
  • a terminally modified polycarbonate resin is provided in which the hydroxy compound represented by the general formula (1) is a combination of a compound represented by the above formula (1-1), a compound represented by the above formula (1-2), and a compound represented by the above formula (1-3).
  • a terminal-modified polycarbonate resin wherein the dihydric phenol compound is a compound represented by the following general formula (2).
  • R 5 to R 8 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, X is —O—, —S—, —SO—, —SO 2 —, —CO—, or a divalent group represented by any one of the following general formulas (3) to (6).
  • R 9 and R 10 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R 9 and R 10 are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer from 0 to 20; R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atom
  • the terminally modified polycarbonate resin of the present invention may be a terminally modified polycarbonate resin having a constituent unit represented by the following general formula (I), the terminal group of which is represented by a terminal structure (A) derived from a hydroxy compound represented by the above general formula (1).
  • R 5 to R 8 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, X is —O—, —S—, —SO—, —SO 2 —, —CO—, or a divalent group represented by any one of the following general formulas (3) to (6).
  • R 9 and R 10 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or an alkenyl group having 2 to 15 carbon atoms which may have a substituent, or R 9 and R 10 are bonded to each other to form a carbocyclic ring having 3 to 20 carbon atoms or a heterocyclic ring having 1 to 20 carbon atoms; c represents an integer from 0 to 20; R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atom
  • X in the structural unit represented by the above general formula (I) may be a divalent group represented by general formula (3).
  • a terminally modified polycarbonate resin is provided in which X is a divalent group represented by general formula (3).
  • the dihydric phenol compound may be a bisphenol compound.
  • a terminally modified polycarbonate resin is provided in which the dihydric phenol compound is a bisphenol compound.
  • bisphenol compounds used as the dihydric phenol compound in the present invention include 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3-chlorophenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, and 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane.
  • Bisphenol A 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, ⁇ , ⁇ -bis[3-(O-hydroxyphenyl)propyl]polydimethylsiloxane, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A; BPA), 1,1-bis(4-hydroxyphenyl)-1-phenylethane (bisphenol AP), 2,2-bis(4-hydroxyphenyl)butane (bisphenol B; BPB), bis(4-hydroxyphenyl)diphenylmethane Bisphenol BP, Bisphenol CD, 2,2-bis(3-methyl-4-hydroxyphenyl)propane (Bisphenol C), 1,1-bis(4-hydroxyphenyl)ethane (Bisphenol E), Bis(4-hydroxyphenyl)methane (Bisphenol F), 2,2-bis(4-hydroxy-3-isopropylphenyl)propane (Bisphenol G
  • the bisphenol compound may be selected from the group consisting of bisphenol A, bisphenol AP, bisphenol Z, bisphenol CD, bisphenol C, bisphenol IOTD, bisphenol IBTD, and bisphenol MIBK.
  • a terminal-modified polycarbonate resin is provided in which the bisphenol compound is selected from the group consisting of bisphenol A, bisphenol AP, bisphenol Z, bisphenol CD, bisphenol C, bisphenol IOTD, bisphenol IBTD, and bisphenol MIBK.
  • the bisphenol compound is bisphenol A.
  • a terminal-modified polycarbonate resin is provided in which the bisphenol compound is bisphenol A.
  • the dihydric phenol compound may be used alone or in combination of two or more.
  • a terminal-modified polycarbonate resin in which the bisphenol compound is bisphenol A, and the hydroxy compound represented by the general formula (1) is a compound represented by any one of the following formulas (1-1), (1-2), or (1-3), or a combination of two or more of these compounds:
  • a monohydric phenol (also referred to as "terminal terminator A"), which is a precursor of the structure represented by the terminal structure (A) derived from the hydroxy compound represented by the above general formula (1), can be easily obtained from the market as an ultraviolet absorber.
  • the monohydric phenol may be used alone or in combination of two or more types.
  • the terminal structure (A) derived from the hydroxy compound represented by the general formula (1) is contained in an amount of 0.5% by mass or more. In one embodiment of the present invention, it may be contained in an amount of preferably 0.5% by mass to 15% by mass relative to the structural unit (B) derived from the dihydric phenol compound.
  • the terminal structure (A) derived from the hydroxy compound represented by the general formula (1) may be contained in an amount of more preferably 1% by mass to 10% by mass, even more preferably 2% by mass to 10% by mass, and particularly preferably 3% by mass to 7% by mass relative to the structural unit (B) derived from the dihydric phenol compound.
  • the terminally modified polycarbonate resin may include any of a random copolymer structure, a block copolymer structure, and an alternating copolymer structure.
  • the terminally modified polycarbonate resin can be blended with other resins to form a terminally modified polycarbonate resin composition.
  • other resins include, but are not limited to, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyethylene terephthalate, polybutylene terephthalate, etc.
  • the terminally modified polycarbonate resin can be made into a terminally modified polycarbonate resin composition by adding an antioxidant and a release agent as additives.
  • Antioxidants include triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert -butyl-4-hydroxybenzyl)benzene, N,N-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-tert-butyl-4-hydroxy-benzylphosphonate-diethyl ester, tri
  • the content of the antioxidant in the terminally modified polycarbonate resin composition is preferably 0.50% by mass or less, more preferably 0.10 to 0.40% by mass, and particularly preferably 0.20 to 0.40% by mass.
  • the release agent is preferably one that is composed of 90% by mass 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 full ester of polyhydric alcohol and fatty acid.
  • the ester of monohydric alcohol and fatty acid is preferably an ester of monohydric alcohol having 1 to 20 carbon atoms and saturated fatty acid having 10 to 30 carbon atoms.
  • the partial or full ester of polyhydric alcohol and fatty acid is preferably a partial or full ester of polyhydric alcohol having 1 to 25 carbon atoms and saturated fatty acid having 10 to 30 carbon atoms.
  • esters of monohydric alcohols and saturated fatty acids include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, and isopropyl palmitate.
  • partial or full esters of polyhydric alcohols and saturated fatty acids include full or partial esters of dipentaerythritol, such as stearic acid monoglyceride, stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethyl
  • the content of the release agent in the terminally modified polycarbonate resin composition is preferably 0.50% by mass or less, more preferably 0.01 to 0.10% by mass, and particularly preferably 0.03 to 0.05% by mass.
  • additives such as processing stabilizers, UV absorbers, flow modifiers, crystal nucleating agents, reinforcing agents, dyes, antistatic agents, bluing agents, and antibacterial agents may be added to the terminally modified polycarbonate resin composition of the present invention.
  • the terminally modified polycarbonate resin can be produced in the same manner as in the production method for conventional polycarbonate resins, except that a terminal terminator is used.
  • the interfacial polymerization method involves reacting a dihydric phenol compound with phosgene in the presence of an inert organic solvent or an aqueous alkali solution, and then polymerizing by adding a terminal terminator and a polymerization catalyst such as a tertiary amine or a quaternary ammonium salt;
  • the pyridine method involves dissolving a dihydric phenol compound and a terminal terminator in pyridine or a mixed solution of pyridine and an inert solvent, and then blowing in phosgene to directly obtain a polycarbonate oligomer.
  • the interfacial polymerization method may also involve adding the terminal terminator during the reaction of the dihydric phenol compound with phosgene.
  • Terminally Modified Polycarbonate Resin The terminally modified polycarbonate resin of the present invention was evaluated for the following physical properties.
  • the viscosity average molecular weight (Mv) of the terminally modified polycarbonate resin may be preferably 10,000 to 60,000.
  • a terminally modified polycarbonate resin having a viscosity average molecular weight of 10,000 to 60,000 is provided.
  • the viscosity average molecular weight (Mv) of the terminally modified polycarbonate is more preferably 13,000 to 50,000, further preferably 15,000 to 40,000, further more preferably 20,000 to 35,000, and particularly preferably 25,300 to 33,500.
  • the viscosity average molecular weight (Mv) of the polycarbonate is within the above range, it is possible to prevent the molded body from becoming brittle, to prevent the melt viscosity from becoming excessively high, to facilitate removal of the resin after production, and to improve the fluidity and facilitate injection molding in a molten state.
  • a high wavelength at which the transmittance is 0% means that the transmittance is high in a wide range of wavelengths.
  • a high transmittance in a wide range of wavelengths is more beneficial.
  • the transmittance at wavelengths from 850 nm to 200 nm was measured, and the wavelength at which the transmittance is 0% was detected.
  • the terminally modified polycarbonate resin may have a transmittance at 330 nm of 1% or less.
  • a terminally modified polycarbonate resin is provided, characterized in that the transmittance at 330 nm is 1% or less.
  • the transmittance at 330 nm of the terminally modified polycarbonate resin of the present invention may be preferably 0.5% or less, more preferably 0.1 or less. If the transmittance at 330 nm is within the above range, the terminally modified polycarbonate resin can be used in practice as a terminally modified polycarbonate resin having both excellent ultraviolet absorbing ability and stability to light.
  • the transmittance was obtained by measuring the transmittance of a resin solution under the following conditions. ⁇ Measuring equipment: Shimadzu Corporation UV-1280 ultraviolet-visible spectrophotometer Solvent: dichloromethane Resin solution concentration: 10 w/w% Cell: 1 cm quartz cell Photometric mode Zero point correction at 330 nm performed with dichloromethane solvent Measurement wavelength range: 850 nm to 200 nm
  • the weight loss temperature range (°C) was calculated as follows. A smaller weight loss temperature range (°C) means that thermal decomposition occurs rapidly, and it can be said that the thermal decomposition behavior is stable. When the weight loss temperature range (°C) is small, the transparency of the molded product is sufficiently high and satisfies the conditions required for optical materials, making it easier to determine the application and to respond to the thermal decomposition of the molded product.
  • the obtained laminate was subjected to an adhesion test in accordance with JIS K5600-5-6, using a 24 mm wide Cellophane Tape (registered trademark) (adhesive strength 4.01 N x 10 mm) manufactured by Nichiban Co., Ltd., in accordance with the cross-cut test method (1 mm intervals).
  • the adhesion was evaluated by classifying it into a number from 0 (no peeling) to 5 (almost complete peeling) based on the JIS classification index. The less peeling there is, the higher the adhesion. The less peeling there is, the more suitable it is for applications such as coatings.
  • the terminally modified polycarbonate resin of the present invention can be used in a variety of applications, such as transparent substrate applications for optical materials, applications for automobile parts, and coating films, and is particularly suitable for molding materials for outdoor use, such as lenses for camera lenses, eyeglass lenses, and sunglasses.
  • an optical material comprising a terminal-modified polycarbonate resin that includes a terminal structure (A) derived from a hydroxy compound represented by general formula (1) and a structural unit (B) derived from a dihydric phenol compound.
  • A represents an alkyl group having 1 to 6 carbon atoms which may be branched
  • B represents a halogen, a hydroxyl group, or a phenylthio group which may have a substituent
  • n represents an integer of 0 to 4.
  • an optical material comprising a terminally modified polycarbonate resin, in which the bisphenol compound is bisphenol A, and the hydroxy compound represented by the general formula (1) is a compound represented by any one of the following formulas (1-1), (1-2), or (1-3), or a combination of two or more of these compounds:
  • a terminally modified polycarbonate resin was produced according to the method described below, and the viscosity average molecular weight (Mv), 330 nm transmittance, and infrared absorption (IR) spectrum of the resulting resin were analyzed.
  • Compound (1-2) can be obtained by referring to a general synthesis method of benzotriazole (for example, the method described in JP-A-2004-509877). That is, 4-methyl-2-(2-nitro-4-chloro-phenylazo)-phenol is stirred together with N,N-dimethylacetamide and sodium azide, or 4-methyl-6-(2,5-dichlorophenylazo)-phenol is stirred together with dimethylformamide, sodium azide, triethylamine and copper bromide (I), and after the reaction is completed, the mixture is extracted with toluene, washed with water and dried to obtain compound (1-2) of the following formula.
  • benzotriazole for example, the method described in JP-A-2004-509877. That is, 4-methyl-2-(2-nitro-4-chloro-phenylazo)-phenol is stirred together with N,N-dimethylacetamide and sodium azide, or 4-methyl-6-(2,5-dichlorophenylazo)
  • UVA326 (24.3 g, 76.9 mmol, 1.00 eq)
  • bis(pinacolato)diboron (25.4 g, 100 mmol, 1.30 eq)
  • potassium acetate (22.6 g, 231 mmol, 3.00 eq)
  • toluene (485 mL)
  • UVA326-BPin (25.5 g, 62.6 mmol, 1.00 eq) was dissolved in THF (250 mL) in a 1 L eggplant flask and cooled on ice.
  • 2.5 M aqueous sodium hydroxide solution 50 mL, 125 mmol, 2.00 eq
  • 30% aqueous hydrogen peroxide 75.0 mL, 748 mmol, 11.9 eq was added dropwise over 15 minutes. After warming to room temperature and stirring for 1.5 hours, the reaction solution was separated with chloroform (250 mL).
  • the aqueous layer was extracted with chloroform (100 mL), and all the organic layers were combined, dehydrated with sodium sulfate, filtered, and concentrated to about 1/3 of the solvent.
  • Water (200 mL) was added thereto, and the organic layer was distilled off under reduced pressure.
  • Ethyl acetate (200 mL) was added to the remaining aqueous layer and separated, and the organic layer was washed with water (200 mL), dehydrated with sodium sulfate, filtered, and concentrated.
  • a crude product of 18.1 g was obtained as a yellow-green amorphous substance.
  • Example 1 100 g of bisphenol A (BPA: manufactured by Mitsubishi Chemical Corporation) and 0.5 g of hydrosulfite were added and dissolved in 620 ml of a 9 w/w % aqueous sodium hydroxide solution. 300 ml of dichloromethane was added to this solution, and while stirring, the solution temperature was set to 20° C., and 60.7 g of phosgene was further blown in over 30 minutes.
  • the polymerization liquid was separated into an aqueous layer and an organic layer, and the organic layer was neutralized with phosphoric acid and repeatedly washed with pure water until the pH of the washings reached pH 7.0.
  • the organic solvent was evaporated from this purified polycarbonate resin to obtain a polycarbonate resin powder.
  • This polycarbonate resin powder was dried at 120°C for 24 hours to completely evaporate off the solvent.
  • Example 2 A polycarbonate resin powder was obtained in the same manner as in Example 1, except that the compound represented by formula (1-1) was replaced with 7.09 g of the compound represented by formula (1-2).
  • Example 3 A polycarbonate resin powder was obtained in the same manner as in Example 1, except that the compound represented by formula (1-1) was replaced with 3.95 g of the compound represented by formula (1-3).
  • Example 1 A polycarbonate resin powder was obtained in the same manner as in Example 1, except that the compound represented by formula (1-1) was replaced with 6.17 g of a compound represented by the following formula (SEESORB 701, manufactured by Shipro Kasei Co., Ltd.).
  • the terminally modified polycarbonate resin of the present invention not only has high transmittance over a wide wavelength range, good adhesion, and high heat resistance, but also has stable thermal decomposition behavior, produces little gas during molding, and can suppress mold deposits.
  • the terminally modified polycarbonate resin of the present invention which has such properties, can be used in a variety of applications, such as transparent substrates for optical materials, automotive parts, and coatings, and is particularly suitable for molding materials used outdoors, such as sunglasses lenses.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne une résine de polycarbonate à extrémité modifiée ayant une capacité d'absorption des ultraviolets. Plus spécifiquement, l'invention concerne une résine de polycarbonate à extrémité modifiée comprenant une structure terminale (A) dérivée d'un composé hydroxy représenté par la formule générale (1) et une unité constitutive (B) dérivée d'un composé phénol dihydrique. (Dans la formule générale (1), R1 représente un groupe alkyle en C1-C6 éventuellement ramifié, R2 représente un atome d'halogène, un groupe hydroxy, ou un groupe phénylthio éventuellement substitué, et n est un nombre entier de 0 à 4.)
PCT/JP2024/028358 2023-08-15 2024-08-08 Résine de polycarbonate Pending WO2025037568A1 (fr)

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JP2023-132337 2023-08-15
JP2023132337 2023-08-15

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4999596A (fr) * 1973-01-25 1974-09-20
JPH01201330A (ja) * 1988-02-08 1989-08-14 Mitsubishi Gas Chem Co Inc 耐候性ポリカーボネート樹脂の製法
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JPS4999596A (fr) * 1973-01-25 1974-09-20
JPH01201330A (ja) * 1988-02-08 1989-08-14 Mitsubishi Gas Chem Co Inc 耐候性ポリカーボネート樹脂の製法
JPH06145330A (ja) * 1992-11-04 1994-05-24 Idemitsu Petrochem Co Ltd ポリカーボネートの製造方法
JPH07145247A (ja) * 1993-11-25 1995-06-06 Takiron Co Ltd 紫外線吸収剤含有樹脂成形品及びその製造方法
JPH08169946A (ja) * 1994-05-20 1996-07-02 Bayer Ag 公知の芳香族ポリカーボネート類と任意に混合されたｕｖ安定性ポリカーボネート類、それらの製造およびそれらの使用
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US20170313815A1 (en) * 2014-11-19 2017-11-02 Sabic Global Technologies B.V. A method of polymerizing end-capped polycarbonate and end-capped polycarbonates derived therefrom
WO2020114936A1 (fr) * 2018-12-06 2020-06-11 Basf Se Nouvelle procédure pour la formation de corps 2h-benzotriazole et de congénères
WO2020137819A1 (fr) * 2018-12-26 2020-07-02 ミヨシ油脂株式会社 Absorbant d'uv résistant à la lumière, résistant à la chaleur et durable
WO2020175474A1 (fr) * 2019-02-26 2020-09-03 ミヨシ油脂株式会社 Matériau de moulage en résine, son procédé de production et procédé de production d'un élément en résine ou similaire
WO2020203958A1 (fr) * 2019-04-02 2020-10-08 三菱瓦斯化学株式会社 Résine de polycarbonate

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