KR101944143B1 - 폴리카보네이트-폴리오르가노실록산 공중합체 및 그 제조 방법 - Google Patents
폴리카보네이트-폴리오르가노실록산 공중합체 및 그 제조 방법 Download PDFInfo
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- KR101944143B1 KR101944143B1 KR1020147010226A KR20147010226A KR101944143B1 KR 101944143 B1 KR101944143 B1 KR 101944143B1 KR 1020147010226 A KR1020147010226 A KR 1020147010226A KR 20147010226 A KR20147010226 A KR 20147010226A KR 101944143 B1 KR101944143 B1 KR 101944143B1
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- polycarbonate
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- polyorganosiloxane
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 44
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 239000004417 polycarbonate Substances 0.000 claims description 69
- 229920000515 polycarbonate Polymers 0.000 claims description 60
- -1 phenol compound Chemical class 0.000 claims description 56
- 239000000243 solution Substances 0.000 claims description 48
- 239000007864 aqueous solution Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 24
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- 125000003118 aryl group Chemical group 0.000 claims description 22
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- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 13
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- 239000012295 chemical reaction liquid Substances 0.000 claims description 8
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- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
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- 125000005375 organosiloxane group Chemical group 0.000 description 5
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
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- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
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- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
- NTFMNNZPXYHYNY-UHFFFAOYSA-N 1,2-bis(4-hydroxyphenyl)-10h-anthracen-9-one Chemical compound C1=CC(O)=CC=C1C1=CC=C(CC=2C(=CC=CC=2)C2=O)C2=C1C1=CC=C(O)C=C1 NTFMNNZPXYHYNY-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
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Images
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- 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
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
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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
- C08G64/18—Block or graft polymers
- C08G64/186—Block or graft polymers containing polysiloxane sequences
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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
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
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| JP6007058B2 (ja) * | 2012-10-12 | 2016-10-12 | 出光興産株式会社 | ポリカーボネート−ポリオルガノシロキサン共重合体の連続的な製造方法 |
| CN104837895B (zh) * | 2013-07-01 | 2017-06-06 | Lg化学株式会社 | 聚硅氧烷化合物及其制备方法以及包含它的共聚碳酸酯树脂 |
| JP6283264B2 (ja) * | 2014-05-30 | 2018-02-21 | 出光興産株式会社 | ポリカーボネートの製造方法 |
| KR101687683B1 (ko) | 2014-09-05 | 2016-12-19 | 주식회사 엘지화학 | 코폴리카보네이트 및 이를 포함하는 조성물 |
| JP2016088974A (ja) * | 2014-10-30 | 2016-05-23 | 出光興産株式会社 | ポリカーボネート−ポリオルガノシロキサン共重合体の製造方法 |
| JP2016098292A (ja) * | 2014-11-20 | 2016-05-30 | 出光興産株式会社 | ポリカーボネート−ポリオルガノシロキサン共重合体の製造方法 |
| KR101685665B1 (ko) | 2014-12-04 | 2016-12-12 | 주식회사 엘지화학 | 코폴리카보네이트 및 이를 포함하는 조성물 |
| KR20160067714A (ko) | 2014-12-04 | 2016-06-14 | 주식회사 엘지화학 | 코폴리카보네이트 및 이를 포함하는 물품 |
| JP2016108439A (ja) * | 2014-12-05 | 2016-06-20 | 出光興産株式会社 | ポリカーボネート−ポリオルガノシロキサン共重合体の製造方法 |
| US10059800B2 (en) * | 2014-12-12 | 2018-08-28 | Idemitsu Kosan Co., Ltd. | Process for producing polycarbonate |
| WO2017034040A1 (ja) * | 2015-08-27 | 2017-03-02 | 出光興産株式会社 | ポリカーボネート－ポリオルガノシロキサン共重合体の製造方法 |
| KR101825652B1 (ko) | 2015-11-06 | 2018-02-05 | 주식회사 엘지화학 | 코폴리카보네이트 및 이를 포함하는 조성물 |
| US9598577B1 (en) * | 2015-11-17 | 2017-03-21 | Sabic Global Technologies B.V. | Polycarbonate-polysiloxane copolymer compositions, articles formed therefrom, and methods of manufacture thereof |
| JP2018059028A (ja) | 2016-10-07 | 2018-04-12 | 出光興産株式会社 | ポリカーボネート系樹脂組成物及び成形体 |
| CN109836565B (zh) * | 2017-11-29 | 2022-01-07 | 万华化学集团股份有限公司 | 一种硅氧烷共聚碳酸酯及其制备方法 |
| KR102802951B1 (ko) * | 2017-12-28 | 2025-04-30 | 이데미쓰 고산 가부시키가이샤 | 폴리카보네이트-폴리오가노실록세인 공중합체 |
| CN109585502B (zh) * | 2018-10-25 | 2020-09-08 | 深圳市华星光电技术有限公司 | 用于喷墨打印的基板及其制作方法 |
| US12018122B2 (en) * | 2018-11-07 | 2024-06-25 | Merz+Benteli Ag | Method for producing silane-modified polymers |
| CN111187403B (zh) * | 2018-11-14 | 2022-08-02 | 万华化学集团股份有限公司 | 一种硅氧烷共聚碳酸酯及其制备方法 |
| CN113272362B (zh) | 2018-12-21 | 2022-06-17 | 美国陶氏有机硅公司 | 硅酮-聚酯共聚物、包括硅酮-聚酯共聚物的密封剂和相关方法 |
| US11760841B2 (en) | 2018-12-21 | 2023-09-19 | Dow Silicones Corporation | Silicone-polycarbonate copolymer, sealants comprising same, and related methods |
| KR102811805B1 (ko) | 2018-12-21 | 2025-05-27 | 다우 실리콘즈 코포레이션 | 실리콘-유기 공중합체, 이를 포함하는 밀봉제 및 관련된 방법 |
| KR102813023B1 (ko) | 2018-12-21 | 2025-05-28 | 다우 실리콘즈 코포레이션 | 실리콘-폴리아크릴레이트 공중합체, 이를 포함하는 밀봉제 및 관련된 방법 |
| JP7629412B2 (ja) | 2019-12-06 | 2025-02-13 | 出光興産株式会社 | ポリカーボネート－ポリオルガノシロキサン共重合体及び該共重合体を含む樹脂組成物 |
| EP4071195A4 (en) * | 2019-12-06 | 2023-12-06 | Idemitsu Kosan Co., Ltd | POLYCARBONATE/POLYORGANOSILOXANE COPOLYMER AND RESIN COMPOSITION INCLUDING THIS COPOLYMER |
| JP7608367B2 (ja) | 2019-12-27 | 2025-01-06 | 出光興産株式会社 | ポリカーボネート－ポリオルガノシロキサン共重合体 |
| CN111560117B (zh) * | 2020-06-08 | 2022-08-05 | 万华化学集团股份有限公司 | 一种硅氧烷共聚碳酸酯的制备方法 |
| EP3957672A1 (en) * | 2020-08-20 | 2022-02-23 | Idemitsu Kosan Co.,Ltd. | Polycarbonate-polyorganosiloxane copolymer, method for producing the same, and resin composition comprising the copolymer |
| EP3957674A1 (en) * | 2020-08-20 | 2022-02-23 | Idemitsu Kosan Co.,Ltd. | Polycarbonate-polyorganosiloxane copolymer, method for producing the same, and resin composition comprising the copolymer |
| KR20220128500A (ko) * | 2021-03-11 | 2022-09-21 | 삼성디스플레이 주식회사 | 발광 소자 및 발광 소자용 아민 화합물 |
| CN113201127B (zh) * | 2021-06-21 | 2022-09-16 | 万华化学集团股份有限公司 | 聚硅氧烷-聚碳酸酯共聚物、制造方法及聚碳酸酯树脂 |
| CN114196001B (zh) * | 2022-01-11 | 2023-09-19 | 万华化学集团股份有限公司 | 一种聚碳酸酯-聚有机硅氧烷共聚物、制造方法及包含该共聚物的树脂组合物 |
| CN114989407B (zh) * | 2022-06-10 | 2024-05-03 | 万华化学集团股份有限公司 | 聚碳酸酯-聚硅氧烷共聚物、制造方法及含其的聚碳酸酯树脂组合物 |
| CN114957673B (zh) * | 2022-06-30 | 2023-10-17 | 万华化学集团股份有限公司 | 聚硅氧烷-聚碳酸酯共聚物、制造方法及含其的聚碳酸酯树脂组合物 |
| CN117645782B (zh) * | 2023-11-29 | 2025-01-28 | 新兴际华(北京)材料技术研究院有限公司 | 一种低温增韧改性的pc复合材料及其制备方法 |
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| JP2005060599A (ja) | 2003-08-19 | 2005-03-10 | Idemitsu Petrochem Co Ltd | ポリカーボネート系樹脂の製造方法 |
| WO2011013846A1 (ja) | 2009-07-29 | 2011-02-03 | 帝人化成株式会社 | ポリカーボネート−ポリジオルガノシロキサン共重合体 |
| JP2011046913A (ja) * | 2009-07-29 | 2011-03-10 | Teijin Chem Ltd | ポリカーボネート−ポリジオルガノシロキサン共重合体 |
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| JP3037588B2 (ja) | 1994-07-15 | 2000-04-24 | 出光石油化学株式会社 | ポリカーボネート樹脂組成物 |
| US5530083A (en) | 1994-07-21 | 1996-06-25 | General Electric Company | Silicone-polycarbonate block copolymers and polycarbonate blends having reduced haze, and method for making |
| JPH10245711A (ja) | 1997-02-27 | 1998-09-14 | Idemitsu Petrochem Co Ltd | 透明バイザー付きヘルメット |
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| WO2004076512A2 (en) | 2003-02-21 | 2004-09-10 | General Electric Company | Transparent and high-heat polycarbonate-polysiloxane copolymers and transparent blends with polycarbonate and a process for preparing same |
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| JP5305645B2 (ja) * | 2007-11-29 | 2013-10-02 | 出光興産株式会社 | ポリカーボネート樹脂組成物、ポリカーボネート樹脂成形品及びその製造方法 |
| JP5684588B2 (ja) | 2011-01-27 | 2015-03-11 | 帝人株式会社 | ポリカーボネート樹脂組成物および成形品 |
| JP6007058B2 (ja) | 2012-10-12 | 2016-10-12 | 出光興産株式会社 | ポリカーボネート−ポリオルガノシロキサン共重合体の連続的な製造方法 |
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| JP2005060599A (ja) | 2003-08-19 | 2005-03-10 | Idemitsu Petrochem Co Ltd | ポリカーボネート系樹脂の製造方法 |
| WO2011013846A1 (ja) | 2009-07-29 | 2011-02-03 | 帝人化成株式会社 | ポリカーボネート−ポリジオルガノシロキサン共重合体 |
| JP2011046913A (ja) * | 2009-07-29 | 2011-03-10 | Teijin Chem Ltd | ポリカーボネート−ポリジオルガノシロキサン共重合体 |
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| US9080021B2 (en) | 2015-07-14 |
| US20140256888A1 (en) | 2014-09-11 |
| KR20140078670A (ko) | 2014-06-25 |
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