WO2016003132A1 - Copolymère de polysiloxane-polycarbonate ayant une transparence et une résistance au choc à basses températures améliorées et son procédé de préparation - Google Patents

Copolymère de polysiloxane-polycarbonate ayant une transparence et une résistance au choc à basses températures améliorées et son procédé de préparation Download PDF

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Publication number
WO2016003132A1
WO2016003132A1 PCT/KR2015/006625 KR2015006625W WO2016003132A1 WO 2016003132 A1 WO2016003132 A1 WO 2016003132A1 KR 2015006625 W KR2015006625 W KR 2015006625W WO 2016003132 A1 WO2016003132 A1 WO 2016003132A1
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WO
WIPO (PCT)
Prior art keywords
group
polysiloxane
carbon atoms
ppm
polycarbonate copolymer
Prior art date
Application number
PCT/KR2015/006625
Other languages
English (en)
Korean (ko)
Inventor
김미란
권영도
손소리
신경무
윤원규
박주현
강효일
Original Assignee
주식회사 삼양사
희성금속 주식회사
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 주식회사 삼양사, 희성금속 주식회사 filed Critical 주식회사 삼양사
Publication of WO2016003132A1 publication Critical patent/WO2016003132A1/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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
    • C08G77/448—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences containing polycarbonate sequences
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers

Definitions

  • the present invention is to solve the problems of the prior art as described above, and to provide a novel polysiloxane-polycarbonate copolymer having excellent low temperature impact resistance and excellent transparency, and a method of manufacturing the same.
  • the preferred content of the hydroxy-terminated polysiloxane in the polysiloxane-polycarbonate copolymer of the present invention is 1 to 40% by weight, more preferably 2 to 30% by weight, based on the total weight of the copolymer. If the content of hydroxy-terminated polysiloxane in the copolymer is less than 1% by weight, the low-temperature impact resistance of the resulting copolymer may be insufficient, and if the content exceeds 40% by weight, physical properties such as fluidity and heat resistance transparency may be deteriorated. The increase in manufacturing costs is undesirable from an economic point of view.
  • X is a linear, branched or cyclic alkylene containing an alkylene group, a straight, branched or cyclic alkylene group having no functional group, or a functional group such as sulfide, ether, sulfoxide, sulfone, ketone, naphthyl, isobutylphenyl Group.
  • X may be a linear, branched or cyclic alkylene group having 3 to 6 carbon atoms.
  • 2,2-bis (4-hydroxyphenyl) propane bisphenol A
  • Other functional dihydric phenols may refer to US Pat. Nos. 2,999,835, 3,028,365, 3,153,008, 3,334,154, and the like. The dihydric phenols may be used alone or in combination of two or more. Can be used.
  • carbonyl chloride phosphene
  • carbonyl bromide bis halo formate
  • diphenyl carbonate or dimethyl carbonate may be used as another monomer of the polycarbonate resin.
  • the phase transfer catalyst is, for example, [CH 3 (CH 2 ) 3 ] 4 NY, [CH 3 (CH 2 ) 3 ] 4 PY, [CH 3 (CH 2 ) 5 ] 4 NY, [CH 3 (CH 2 ) 6 ] 4 NY, [CH 3 (CH 2 ) 4 ] 4 NY, CH 3 [CH 3 (CH 2 ) 3 ] 3 NY, CH 3 [CH 3 (CH 2 ) 2 ] 3 NY have.
  • Y represents Cl, Br or -OR 8 , wherein R 8 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 18 carbon atoms.
  • the content thereof is preferably 0.01% by weight or more in terms of transparency of the resulting copolymer, but is not limited thereto.
  • the assembly time may be very long, and if the temperature of the pure water exceeds 100 °C it may be difficult to obtain the shape of the polycarbonate with a certain size.
  • the viscosity average molecular weight (Mv) of the polysiloxane-polycarbonate copolymer according to the present invention may be, for example, 10,000 to 100,000, more specifically 15,000 to 80,000.
  • Bisphenol A in aqueous solution and phosgene gas were interfacially reacted in the presence of methylene chloride to prepare 400 mL of an oligomeric polycarbonate mixture having a viscosity average molecular weight of about 1,000.
  • 4.5% by weight of hydroxy-terminated polysiloxane of formula E1 of Example 1 and tetrabutyl ammonium chloride (TBACl) dissolved in methylene chloride in the obtained oligomeric polycarbonate mixture 1.8 mL of p-tert-butylphenol (PTBP) 2.68g, triethylamine (triethylamine, TEA, 15wt% aqueous solution) was mixed and reacted for 30 minutes after mixing.
  • PTBP p-tert-butylphenol
  • a 100 mL three-necked flask was equipped with a condenser, and 0.03 mol of 2-allylphenol and 0.015 mol of hydrogen-terminated polydimethylsiloxane of formula E1-1 were completely dissolved in 50 mL of chlorobenzene in a nitrogen atmosphere, and then a platinum catalyst (platinum (0) -1 , 3-divinyl-1,1,3,3-tetramethyldisiloxane complex) was added to 0.00364 mmol and refluxed for 24 hours. After removing the solvent of the reaction solution was washed with distilled water, to prepare a hydroxy-terminated polysiloxane of the formula CE2-1.
  • the hydroxy-terminated siloxanes prepared according to the Examples of the present invention showed overall excellent yields compared to those prepared according to the Comparative Examples. Also, as can be seen from Table 2, the polysiloxane-polycarbonate copolymers prepared according to the examples of the present invention showed excellent low temperature impact resistance and transparency compared to those prepared according to the comparative example.
  • Viscosity Average Molecular Weight (c) The viscosity of the methylene chloride solution was measured at 20 ° C. using an Ubbelohde Viscometer, from which the ultimate viscosity [ ⁇ ] was calculated by the following equation.
  • Impact strength was measured at room temperature and low temperature (-60 °C) using an impact tester (RESIL IMPACTOR, CEAST). Low temperature impact resistance was evaluated as follows.

Landscapes

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

Abstract

Cette invention concerne un copolymère de polysiloxane-polycarbonate ayant une transparence et une résistance au choc à basses températures améliorées, et son procédé de préparation et, plus spécifiquement : un copolymère de polysiloxane-polycarbonate comprenant, à titre de motif de répétition, un polysiloxane ayant une structure spécifique, dont un groupe hydroxyphényle à ses deux extrémités, et une séquence polycarbonate, ledit copolymère ayant simultanément une excellente résistance au choc à basses températures et une excellente transparence ; et son procédé de préparation.
PCT/KR2015/006625 2014-06-30 2015-06-29 Copolymère de polysiloxane-polycarbonate ayant une transparence et une résistance au choc à basses températures améliorées et son procédé de préparation WO2016003132A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2014-0080786 2014-06-30
KR1020140080786A KR20160002485A (ko) 2014-06-30 2014-06-30 투명성 및 저온 내충격성이 향상된 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법

Publications (1)

Publication Number Publication Date
WO2016003132A1 true WO2016003132A1 (fr) 2016-01-07

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PCT/KR2015/006625 WO2016003132A1 (fr) 2014-06-30 2015-06-29 Copolymère de polysiloxane-polycarbonate ayant une transparence et une résistance au choc à basses températures améliorées et son procédé de préparation

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KR (1) KR20160002485A (fr)
TW (1) TW201615699A (fr)
WO (1) WO2016003132A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101948823B1 (ko) 2015-09-04 2019-02-15 주식회사 엘지화학 신규한 폴리오르가노실록산 및 이를 사용하여 제조되는 코폴리카보네이트
KR102383997B1 (ko) * 2020-04-24 2022-04-08 주식회사 삼양사 히드록시 말단 폴리실록산 혼합물을 이용한 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258398A (ja) * 1994-02-07 1995-10-09 Mitsubishi Gas Chem Co Inc 新規ポリカーボネート重合体およびその製造法
KR20100040946A (ko) * 2007-07-31 2010-04-21 사빅 이노베이티브 플라스틱스 아이피 비.브이. 개선된 몰딩 능력을 갖는 폴리카보네이트 조성물
JP2011088377A (ja) * 2009-10-23 2011-05-06 Mitsubishi Gas Chemical Co Inc 積層成形部材、及びシロキサン共重合ポリカーボネート
KR20110108610A (ko) * 2010-03-29 2011-10-06 주식회사 삼양사 에스테르 결합을 갖는 히드록시 말단 실록산, 폴리실록산-폴리카보네이트 공중합체 및 그 제조 방법
KR20130047612A (ko) * 2011-10-31 2013-05-08 주식회사 삼양사 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258398A (ja) * 1994-02-07 1995-10-09 Mitsubishi Gas Chem Co Inc 新規ポリカーボネート重合体およびその製造法
KR20100040946A (ko) * 2007-07-31 2010-04-21 사빅 이노베이티브 플라스틱스 아이피 비.브이. 개선된 몰딩 능력을 갖는 폴리카보네이트 조성물
JP2011088377A (ja) * 2009-10-23 2011-05-06 Mitsubishi Gas Chemical Co Inc 積層成形部材、及びシロキサン共重合ポリカーボネート
KR20110108610A (ko) * 2010-03-29 2011-10-06 주식회사 삼양사 에스테르 결합을 갖는 히드록시 말단 실록산, 폴리실록산-폴리카보네이트 공중합체 및 그 제조 방법
KR20130047612A (ko) * 2011-10-31 2013-05-08 주식회사 삼양사 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법

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TW201615699A (zh) 2016-05-01
KR20160002485A (ko) 2016-01-08

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