WO2017003123A1 - Résine de copolycarbonate et son procédé de préparation - Google Patents

Résine de copolycarbonate et son procédé de préparation Download PDF

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Publication number
WO2017003123A1
WO2017003123A1 PCT/KR2016/006590 KR2016006590W WO2017003123A1 WO 2017003123 A1 WO2017003123 A1 WO 2017003123A1 KR 2016006590 W KR2016006590 W KR 2016006590W WO 2017003123 A1 WO2017003123 A1 WO 2017003123A1
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WO
WIPO (PCT)
Prior art keywords
bis
copolycarbonate resin
weight
hydroxyphenyl
bisphenol
Prior art date
Application number
PCT/KR2016/006590
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English (en)
Korean (ko)
Inventor
고운
반형민
전병규
박정준
이기재
손영욱
홍무호
황영영
김민정
Original Assignee
(주) 엘지화학
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
Priority claimed from KR1020160072892A external-priority patent/KR101856329B1/ko
Application filed by (주) 엘지화학 filed Critical (주) 엘지화학
Priority to US15/508,449 priority Critical patent/US10030096B2/en
Priority to PL16818156T priority patent/PL3170852T3/pl
Priority to CN201680002461.XA priority patent/CN106715527B/zh
Priority to JP2017509757A priority patent/JP6474141B2/ja
Priority to EP16818156.8A priority patent/EP3170852B1/fr
Publication of WO2017003123A1 publication Critical patent/WO2017003123A1/fr

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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
    • C08G64/18—Block or graft polymers
    • 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
    • C08G64/20—General preparatory processes
    • C08G64/22—General preparatory processes using carbonyl halides
    • C08G64/24—General preparatory processes using carbonyl halides and phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances

Definitions

  • the present disclosure relates to a copolycarbonate resin and a method for producing the same, and more particularly, to a copolycarbonate resin having a superior chemical resistance and abrasion resistance by applying a predetermined comonomer and a method for producing the same.
  • Polycarbonate resins are prepared by condensation polymerization of aromatic diols such as bisphenol A and carbonate precursors such as phosgene. It is applied to a wide range of fields.
  • the polycarbonate resin has a problem that it is difficult to apply to a product that requires high chemical resistance and wear resistance because of poor chemical resistance and wear resistance.
  • an object of this invention is to provide the molded article manufactured from the said copolycarbonate resin.
  • the present disclosure provides a polymerized copolycarbonate resin including a bisphenol-based monomer, a comonomer represented by the following formula (1), and a carbonate precursor.
  • R 1 and R 2 are independently alkylene having 1 to 10 carbon atoms, n is an integer of 1 to 50)
  • the present disclosure provides a method for producing a copolycarbonate resin, comprising the step of interfacial polymerization including a bisphenol-based monomer, a comonomer represented by Formula 1, and a carbonate precursor.
  • the present invention also provides a molded article prepared from the copolycarbonate resin.
  • the present inventors have found that when a modified poly (alkylene dicarboxylate) in which both ends of a poly (alkylene dicarboxylate) are modified with 4-hydroxybenzoic acid is used as a comonomer of a polycarbonate resin, It was confirmed that the chemical resistance and the wear resistance of the carbonate resin were greatly improved, and based on this, the present disclosure was completed.
  • the copolycarbonate resin of the present disclosure is characterized by including a bisphenol-based monomer, a comonomer represented by the following formula (1) and a carbonate precursor.
  • R 1 and R 2 are independently alkylene having 1 to 10 carbon atoms, n is an integer of 1 to 50)
  • R 1 and R 2 are independently alkylene having 2 to 6 carbon atoms or alkylene group having 3 to 5 carbon atoms, and have excellent effects of chemical resistance and wear resistance within this range.
  • N is an integer of 5-40 or an integer of 10-30, for example, and there exists an effect excellent in chemical resistance and abrasion resistance within this range.
  • the comonomer represented by Chemical Formula 1 is, for example, as shown in Scheme 1 below, 1) polycondensation reaction of alkanediol and dicarboxylic acid to synthesize poly (alkylene dicarboxylate), 2) thus synthesized It can be prepared by esterifying poly (alkylene dicarboxylate) and 4-hydroxybenzoic acid.
  • the esterification reaction of 2) is another reaction of poly (alkylene dicarboxylate) and 4-acetoxybenzoyl chloride and then hydrolyzing the product under a base catalyst to convert acetoxy groups to hydroxy groups.
  • a base catalyst to convert acetoxy groups to hydroxy groups.
  • the 4-acetoxybenzoyl chloride can be prepared by, for example, chlorination of 4-acetoxybenzoic acid, and the cloning is not particularly limited in the case of the method of normally cloning carboxylic acid. .
  • Catalysts, solvents and other reaction conditions used in the polycondensation reaction and esterification reaction are generally limited in the case of catalysts, solvents and other reaction conditions used in the condensation polymerization reaction or esterification reaction of diol compounds and dicarboxylic acids. Instead, it can select and use suitably as needed.
  • the comonomer may be included in an amount of 0.1 to 19% by weight, 0.1 to 15% by weight, 0.5 to 10% by weight, or 0.5 to 5% by weight based on the total weight of the bisphenol-based monomer and the comonomer. It is effective in chemical resistance and wear resistance.
  • the comonomer represented by Chemical Formula 1 has a tin content of 10 mass ppm or less (as an element) or 5 mass ppm (as an element), and in this case, the thermal stability of the copolycarbonate resin produced, particularly at high temperatures Stability is excellent effect.
  • the tin content may be achieved by, for example, treating a reaction mixture including the compound represented by Chemical Formula 1 with an aqueous solution of phosphoric acid or a solid adsorbent, but is not limited thereto.
  • an organic solvent such as methylene chloride may be used as the organic phase or the diluent when treating the aqueous phosphoric acid solution or the solid adsorbent.
  • the aqueous solution of phosphoric acid may be, for example, 0.5 to 40% by mass, 1.0 to 10% by mass, or 2 to 5% by mass. Within this range, the extraction efficiency and economic efficiency of the tin compound are excellent, and the effect of minimizing environmental damage is excellent. have.
  • the solid adsorbent is not particularly limited in the case of a solid adsorbent capable of adsorbing tin compounds, for example, activated clay; Acidic clay; Ion exchange resins; Chelate resins; Activated carbon; Composite adsorbents composed of silica, magnesia, alumina and the like; And the like.
  • the comonomer represented by Formula 1 has a hydroxybenzoic acid content of 500 mass ppm or less, or 100 mass ppm or less, and in this case, the thermal stability of the manufactured copolycarbonate resin is excellent, particularly at high temperature. In addition, there is an effect that separation of the aqueous phase and the organic phase in the washing step during the interfacial polymerization of the copolycarbonate resin.
  • the comonomer represented by Formula 1 has a hydroxybenzoic acid alkyl ester content of 1.0% by mass or less, or 0.5% by mass or less, in which case the thermal stability of the copolycarbonate resin prepared, in particular, the thermal stability at high temperature This is excellent, and there is an effect of minimizing the molecular weight fluctuation by the hydroxybenzoic acid alkyl ester that can act as an end terminator during interfacial polymerization of the copolycarbonate resin.
  • the tin content may be measured using, for example, an inductively coupled plasma optical emission spectrometry (ICP-OES) device, and may be measured according to JIS K0116 using ICP-OES SPS-5100 manufactured by SII NanoTechnology.
  • ICP-OES inductively coupled plasma optical emission spectrometry
  • the hydroxybenzoic acid and the hydroxybenzoic acid alkyl ester content may be measured using, for example, a high-performance liquid chromatography (HPLC) apparatus.
  • HPLC high-performance liquid chromatography
  • a GL science ODS-3 column may be used, and the column temperature is 40 ° C.
  • bisphenol monomers examples include bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) sulfoxide and bis ( 4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) ketone, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane (bisphenol A), 2,2-bis (4-hydroxyphenyl) butane, 1,1-bis (4-hydroxyphenyl) cyclohexane (bisphenol Z), 2,2-bis (4-hydroxy-3,5-dibro Mophenyl) 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, 2,2-bis (4-hydroxy-3,5-di
  • the bisphenol-based monomer is, for example, 81 to 99.9% by weight, 85 to 99.9% by weight, 90 to 99.5% by weight, or 95 to 99.5% by weight relative to the total weight of the bisphenol-based monomers and comonomers, within this range Intrinsic properties of the carbonate resin has an excellent effect.
  • the carbonate precursor may be, for example, a compound represented by the following Chemical Formula 2, and has an effect of imparting essential properties of the polycarbonate resin within this range.
  • X 1 , X 2 are independently halogen, haloalkyl group, halocycloalkyl group, haloaryl group, alkoxy group or haloalkoxy group.
  • the carbonate precursor is dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, diphenyl carbonate, ditoryl carbonate, bis (chlorophenyl) carbonate, di-m-cresyl carbonate, dinaphthyl Carbonate, bis (diphenyl) carbonate, phosgene, triphosgene, diphosgene, bromophosgene and bishaloformate, and may be at least one selected from the group consisting of triphosgene or phosgene, in which case polycarbonate There is an effect of imparting essential properties of the resin.
  • the carbonate precursor may be, for example, 10 to 150 parts by weight, 30 to 100 parts by weight, or 40 to 70 parts by weight based on 100 parts by weight of the total weight of the bisphenol-based monomer and comonomer, and within this range, a polycarbonate resin
  • the intrinsic properties of have excellent effects.
  • the copolycarbonate may be polymerized by further including, for example, a molecular weight regulator.
  • the molecular weight modifier may be, for example, mono-alkylphenol.
  • the mono-alkylphenols are, for example, p-tert-butylphenol, p-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, hexadecylphenol, octadecylphenol, ecosylphenol, docosylphenol and triacontyl. It is 1 or more types chosen from the group which consists of phenols, Preferably it is para-tert- butylphenol, In this case, a molecular weight control effect is large.
  • the molecular weight modifier may be, for example, 0.1 to 10 parts by weight, 0.1 to 6 parts by weight, or 1 to 5 parts by weight based on 100 parts by weight of the total weight of the bisphenol-based monomer and the comonomer, and may be a target within this range. ) Molecular weight can be obtained.
  • the copolycarbonate resin may have a weight average molecular weight of 10,000 to 50,000 g / mol, 25,000 to 45,000 g / mol, or 20,000 to 40,000 g / mol, and has excellent chemical resistance and wear resistance within this range. .
  • the copolycarbonate resin for example, has a weight loss amount of 10% by weight after contact with an aqueous 20 wt% HCl solution according to ASTM D543 method for 168 hours, and has excellent chemical resistance within this range.
  • the copolycarbonate resin is, for example, 10% by weight, preferably 3% by weight or less, after contact with methanol for 168 hours based on ASTM D543 method, and has excellent chemical resistance within this range.
  • % Weight reduction of the present description means ((weight before contact-weight after contact) / weight before contact) X 100.
  • the copolycarbonate resin is, for example, wear resistance according to the ASTM D3363 method is 1B or more, preferably HB or more, there is an effect that can be applied to products that require high wear resistance within this range.
  • the copolycarbonate resin composition of the present disclosure is characterized in that it comprises 100 parts by weight of the copolycarbonate resin, 0.005 to 0.5 parts by weight of the diphosphite compound, 0.001 to 0.5 parts by weight of alicyclic epoxy compound and 0.01 to 1 part by weight of modified silicone. .
  • the diphosphite compound is, for example, bis (2,4-dicumylphenyl) pentaerythritol diphosphite, and, for example, may be Doverphos S-9228PC manufactured by Dover Chemical, having a residual sodium component of 1 mass ppm or less, in this case, high temperature. It has an excellent thermal stability during molding and excellent light transmittance, brightness and weather resistance.
  • the alicyclic epoxy compound is, for example, 1,2 of 3,4-epoxycyclohexenylmethyl-3 ', 4'-epoxycyclohexenecarboxylate and 2,2-bis (idoxymethyl) -1-butanol.
  • the modified silicone is, for example, a functional group-containing modified silicone compound in which at least one group of methoxy group, vinyl group and phenyl group is introduced into the silicone compound, preferably organopolysiloxane having a phenyl group, methoxy group and vinyl group. It may be KR511 of Shin-Etsu Chemical Co., Ltd., in which case there is an effect of improving the thermal stability during molding.
  • Method for producing a copolycarbonate resin of the present substrate is characterized in that it comprises a step of interfacial polymerization including a bisphenol-based monomer, a comonomer represented by the formula (1) and a carbonate precursor.
  • R 1 and R 2 are independently alkylene having 1 to 10 carbon atoms, n is an integer of 1 to 50)
  • R 1 and R 2 are independently an alkylene having 2 to 6 carbon atoms or an alkylene group having 3 to 5 carbon atoms, and have excellent effects of chemical resistance and wear resistance within this range.
  • N is an integer of 5-40 or an integer of 10-30, for example, and there exists an effect excellent in chemical resistance and abrasion resistance within this range.
  • the interfacial polymerization can be polymerized at atmospheric pressure and low temperature, for example, and has an effect of easily controlling the molecular weight.
  • the interfacial polymerization may be carried out by further including at least one of an acid binder, an organic solvent and a reaction accelerator.
  • the interfacial polymerization may include a step of prepolymerization, a coupling agent, and then polymerization again.
  • a high molecular weight copolycarbonate resin may be obtained.
  • the other materials used for the interfacial polymerization are not particularly limited when the materials can be used for the polymerization of polycarbonate, and the amount of the materials used may be adjusted as necessary.
  • the acid binder may be, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or an amine compound such as pyridine.
  • the organic solvent is not particularly limited in the case of a solvent usually used for polymerization of polycarbonate, and may be, for example, a halogenated hydrocarbon such as methylene chloride and chlorobenzene.
  • the interfacial polymerization is, for example, reactions such as tertiary amine compounds such as triethylamine, tetra-n-butylammonium bromide, tetra-n-butylphosphonium bromide, quaternary ammonium compounds, and quaternary phosphonium compounds to promote reaction. Accelerators may be used further.
  • tertiary amine compounds such as triethylamine, tetra-n-butylammonium bromide, tetra-n-butylphosphonium bromide, quaternary ammonium compounds, and quaternary phosphonium compounds to promote reaction. Accelerators may be used further.
  • the reaction temperature of the interfacial polymerization is, for example, 0 to 40 °C
  • the reaction time is for example 10 minutes to 5 hours
  • the pH of the reaction may be preferably maintained at 9 or more or 11 or more, for example.
  • the interfacial polymerization may be carried out by further including, for example, a molecular weight regulator, which may be added before the start of the polymerization, during the start of the polymerization or after the start of the polymerization.
  • a molecular weight regulator which may be added before the start of the polymerization, during the start of the polymerization or after the start of the polymerization.
  • the molded article of the present disclosure is characterized by containing the copolycarbonate resin of the present disclosure.
  • the molded article may be, for example, an injection molded article.
  • the molded article may further include one or more selected from the group consisting of, for example, antioxidants, heat stabilizers, light stabilizers, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, fluorescent brighteners, ultraviolet absorbers, pigments and dyes. Can be.
  • the method for producing the molded article is, for example, after mixing the copolycarbonate resin and the additives, such as antioxidants of the present invention well using a mixer, the mixture is extruded into an extruder to produce a pellet, and then dried It may include the step of injection into an injection molding machine.
  • the reaction was carried out for 1 hour, and after 10 minutes, 46 g of TEA (triethylamine) was added for a coupling reaction. After 1 hour and 20 minutes of total reaction time, the pH was lowered to 4 to remove TEA, and the resulting polymer was washed three times with distilled water to adjust the pH of the produced polymer to 6-7 neutral.
  • the polymer thus obtained was obtained by reprecipitation in a mixed solution of methanol and hexane and then dried at 120 ° C. to obtain a final copolycarbonate resin.
  • the obtained copolycarbonate resin measured molecular weight by GPC using PC standard (Standard) to confirm that the weight average molecular weight is 29,700 g / mol.
  • Example 1 Except for using comonomer 11.6 g (corresponding to 5% by weight) and bisphenol A in 220.4 g (corresponding to 95% by weight) in Example 1, copolycarbonate and its Injection specimens were prepared.
  • the obtained copolycarbonate resin measured molecular weight by GPC using PC standard (Standard) to confirm that the weight average molecular weight is 29,800 g / mol.
  • the obtained copolycarbonate resin was measured by GPC using PC standard (Standard) to determine the weight average molecular weight of 29,600 g / mol.
  • Example 1 Except not using a comonomer in Example 1, polycarbonate and an injection specimen thereof was prepared in the same manner as in Example 1.
  • the obtained copolycarbonate resin measured molecular weight by GPC using PC standard (Standard) to confirm that the weight average molecular weight is 29,700 g / mol.
  • Example 1 except that 46.4g (corresponding to 20% by weight) of the comonomer and 185.6g (corresponding to 80% by weight) of bisphenol A, the copolycarbonate and the same method as in Example 1 Injection specimens were prepared.
  • the obtained copolycarbonate resin measured molecular weight by GPC using PC standard (Standard) to confirm that the weight average molecular weight is 29,900 g / mol.
  • the copolycarbonate resins (Examples 1 to 3) of the present disclosure are conventional copolycarbonate resins (Comparative Example 1) or copolycarbonate resins in which an excessive amount of the comonomer of Formula 1 is used (compared to Compared with Example 2) it was confirmed that the chemical resistance and wear resistance is improved without reducing the impact strength.
  • copolycarbonate resin obtained in Example 1 100 parts by weight of copolycarbonate resin obtained in Example 1, 0.02 parts by weight of bis (2,4-dicumylphenyl) pentaerythritol diphosphite (Doverphos S-9228PC), 3,4-epoxy Organopolysiloxane (Shin-Etsu Chemical Co., Ltd. product) which has 0.02 weight part of cyclohexenyl methyl-3 ', 4'- epoxycyclohexene carboxylate (made by Daicel Chemical Industry Co., Ltd., 2021P) and a phenyl group, a methoxy group, and a vinyl group.

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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)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention concerne une résine de polycarbonate et un procédé de préparation de celle-ci, qui permet d'obtenir une résine de polycarbonate présentant une excellente résistance chimique et une excellente résistance à l'abrasion, par application d'un comonomère prédéfini; et un procédé de préparation associé.
PCT/KR2016/006590 2015-07-01 2016-06-22 Résine de copolycarbonate et son procédé de préparation WO2017003123A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US15/508,449 US10030096B2 (en) 2015-07-01 2016-06-22 Copolycarbonate resin and method for preparing the same
PL16818156T PL3170852T3 (pl) 2015-07-01 2016-06-22 Żywica kopoliwęglanowa i sposób jej wytwarzania
CN201680002461.XA CN106715527B (zh) 2015-07-01 2016-06-22 共聚碳酸酯树脂及其制备方法
JP2017509757A JP6474141B2 (ja) 2015-07-01 2016-06-22 コポリカーボネート樹脂及びその製造方法
EP16818156.8A EP3170852B1 (fr) 2015-07-01 2016-06-22 Résine de copolycarbonate et son procédé de préparation

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20150094030 2015-07-01
KR10-2015-0094030 2015-07-01
KR10-2016-0072892 2016-06-13
KR1020160072892A KR101856329B1 (ko) 2015-07-01 2016-06-13 코폴리카보네이트 수지 및 이의 제조방법

Publications (1)

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WO2017003123A1 true WO2017003123A1 (fr) 2017-01-05

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005232252A (ja) * 2004-02-18 2005-09-02 Teijin Chem Ltd 改質ポリカーボネート樹脂
KR20070012346A (ko) * 2004-02-19 2007-01-25 이데미쓰 고산 가부시키가이샤 폴리카보네이트 공중합체의 제조방법
KR20080071992A (ko) * 2005-11-18 2008-08-05 제네럴 일렉트릭 컴퍼니 전리 방사선 안정화 열가소성 조성물, 제조 방법, 및그로부터 제조된 물품
KR20090087081A (ko) * 2006-11-22 2009-08-14 사빅 이노베이티브 플라스틱스 아이피 비.브이. 열가소성 조성물, 이의 제조방법, 및 이로부터 유도된 물품
KR20150037663A (ko) * 2013-09-30 2015-04-08 주식회사 엘지화학 높은 유동성을 갖는 폴리카보네이트 및 그의 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005232252A (ja) * 2004-02-18 2005-09-02 Teijin Chem Ltd 改質ポリカーボネート樹脂
KR20070012346A (ko) * 2004-02-19 2007-01-25 이데미쓰 고산 가부시키가이샤 폴리카보네이트 공중합체의 제조방법
KR20080071992A (ko) * 2005-11-18 2008-08-05 제네럴 일렉트릭 컴퍼니 전리 방사선 안정화 열가소성 조성물, 제조 방법, 및그로부터 제조된 물품
KR20090087081A (ko) * 2006-11-22 2009-08-14 사빅 이노베이티브 플라스틱스 아이피 비.브이. 열가소성 조성물, 이의 제조방법, 및 이로부터 유도된 물품
KR20150037663A (ko) * 2013-09-30 2015-04-08 주식회사 엘지화학 높은 유동성을 갖는 폴리카보네이트 및 그의 제조방법

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