KR102648571B1 - 폴리로탁산의 제조 방법 및 폴리로탁산 - Google Patents
폴리로탁산의 제조 방법 및 폴리로탁산 Download PDFInfo
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- KR102648571B1 KR102648571B1 KR1020187001295A KR20187001295A KR102648571B1 KR 102648571 B1 KR102648571 B1 KR 102648571B1 KR 1020187001295 A KR1020187001295 A KR 1020187001295A KR 20187001295 A KR20187001295 A KR 20187001295A KR 102648571 B1 KR102648571 B1 KR 102648571B1
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- polyrotaxane
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- 238000000034 method Methods 0.000 claims abstract description 117
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 65
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- 229920000858 Cyclodextrin Polymers 0.000 claims description 139
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 117
- 239000003999 initiator Substances 0.000 claims description 69
- -1 poly(ethylene glycol) Polymers 0.000 claims description 63
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 38
- 229920001223 polyethylene glycol Polymers 0.000 claims description 38
- 230000002209 hydrophobic effect Effects 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 31
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 22
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- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical group C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 claims description 10
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
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- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 3
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- 150000003254 radicals Chemical class 0.000 description 61
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- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 19
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- 125000000524 functional group Chemical group 0.000 description 18
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- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 239000000047 product Substances 0.000 description 15
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- DUDCYUDPBRJVLG-UHFFFAOYSA-N ethoxyethane methyl 2-methylprop-2-enoate Chemical compound CCOCC.COC(=O)C(C)=C DUDCYUDPBRJVLG-UHFFFAOYSA-N 0.000 description 14
- 238000000111 isothermal titration calorimetry Methods 0.000 description 14
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 12
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- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 description 11
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- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 1
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- RNVFBWLVCITLPA-UHFFFAOYSA-N tert-butyl 7-(tert-butyldiazenyl)-7-methyloctaneperoxoate Chemical compound CC(CCCCCC(=O)OOC(C)(C)C)(C)N=NC(C)(C)C RNVFBWLVCITLPA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/007—Polyrotaxanes; Polycatenanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/08—Isoprene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- C08G85/00—General processes for preparing compounds provided for in this subclass
- C08G85/002—Post-polymerisation treatment
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/246—Intercrosslinking of at least two polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
-
- 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
- C08J2300/00—Characterised by the use of unspecified polymers
- C08J2300/20—Polymers characterized by their physical structure
- C08J2300/21—Polyrotaxanes; Polycatenanes
-
- 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
- C08J2347/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Derivatives of such polymers
-
- 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
- C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2353/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
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| LU92744 | 2015-06-17 | ||
| LU92744 | 2015-06-17 | ||
| PCT/EP2016/063838 WO2016202906A1 (en) | 2015-06-17 | 2016-06-16 | Method of preparing a polyrotaxane and polyrotaxane |
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| KR20180019172A KR20180019172A (ko) | 2018-02-23 |
| KR102648571B1 true KR102648571B1 (ko) | 2024-03-18 |
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| WO2018115238A1 (en) * | 2016-12-21 | 2018-06-28 | Universitaet Des Saarlandes | Method of preparing a polyrotaxane and polyrotaxane |
| WO2019067786A1 (en) | 2017-09-29 | 2019-04-04 | The Regents Of The University Of California | MULTI-ARM POLYROTAXANE PLATFORM FOR PROTECTED ADMINISTRATION OF NUCLEIC ACIDS |
| CN108192554B (zh) * | 2017-12-28 | 2020-07-28 | 宁波凯耀电器制造有限公司 | 一种耐高温透明胶及其制备方法 |
| CN108383960B (zh) * | 2018-03-23 | 2020-02-14 | 西南大学 | 一种基于Cy5的近红外荧光聚合物的制备方法 |
| DE102018107702A1 (de) | 2018-03-29 | 2019-10-02 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gmbh | Nanostrukturierte Kompositmaterialien mit selbstheilenden Eigenschaften |
| CN111808217B (zh) * | 2020-06-01 | 2022-06-14 | 上海大学 | 温敏环糊精聚轮烷、凝胶及其制备方法 |
| CN112266432B (zh) * | 2020-10-27 | 2022-10-28 | 中国科学院青岛生物能源与过程研究所 | 一种具有高3,4-结构含量的高分子量聚月桂烯的高效制备方法 |
| KR102904621B1 (ko) * | 2020-11-27 | 2025-12-29 | 주식회사 엘지화학 | 디엔계 고무질 중합체 복합체의 제조방법 및 이를 포함하는 그라프트 중합체의 제조방법 |
| CN112748484B (zh) * | 2020-12-30 | 2022-04-29 | 西北工业大学 | 一种双功能超表面 |
| JP2023124226A (ja) * | 2022-02-25 | 2023-09-06 | 横浜ゴム株式会社 | ロタキサン及びその製造方法、並びに、架橋ポリマー、高分子微粒子及び高分子樹脂部材 |
| CN115882061A (zh) * | 2022-12-29 | 2023-03-31 | 北京工业大学 | 一种聚轮烷基聚合物电解质的制备及其应用 |
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| KR100389098B1 (ko) | 1994-10-28 | 2003-12-31 | 롬 앤드 하스 캄파니 | 개선된중합체제조방법 |
| WO2014080981A1 (ja) | 2012-11-22 | 2014-05-30 | 国立大学法人 東京大学 | 新規ポリロタキサン及びその製造方法 |
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| US4265964A (en) * | 1979-12-26 | 1981-05-05 | Arco Polymers, Inc. | Lightweight frothed gypsum structural units |
| JPS6014877A (ja) * | 1983-07-06 | 1985-01-25 | 住友ゴム工業株式会社 | ソリッドゴルフボール |
| DE19533269A1 (de) | 1995-09-08 | 1997-03-13 | Basf Ag | Verfahren zur Herstellung von Polymerisaten in wäßrigem Medium |
| DE19956326A1 (de) * | 1999-11-23 | 2001-05-31 | Bayer Ag | Verfahren zur Herstellung von Polymeren auf Basis von 1,3-Dienen |
| KR100586726B1 (ko) * | 2004-06-18 | 2006-06-08 | 한국타이어 주식회사 | 타이어 트레드용 고무 조성물 |
| JPWO2006090819A1 (ja) | 2005-02-24 | 2008-07-24 | 国立大学法人 東京大学 | ポリロタキサン及びポリマー並びにイオン性液体を有する材料、及びその製造方法 |
| JP2007063398A (ja) | 2005-08-31 | 2007-03-15 | Nissan Motor Co Ltd | 疎水性直鎖状分子ポリロタキサン及び架橋ポリロタキサン |
| JP4521875B2 (ja) | 2005-08-31 | 2010-08-11 | 日産自動車株式会社 | 疎水性修飾ポリロタキサン |
| KR101593717B1 (ko) * | 2008-05-07 | 2016-02-12 | 아도반스토 소후토 마테리아루즈 가부시키가이샤 | 폴리로탁산, 및 폴리로탁산과 중합체의 가교체, 및 이들의 제조 방법 |
| JP5854342B2 (ja) | 2009-02-16 | 2016-02-09 | 日産自動車株式会社 | 微粒子−ポリロタキサン含有塗料、微粒子−ポリロタキサン含有塗膜及び塗装物品 |
| JP5907646B2 (ja) | 2009-02-16 | 2016-04-26 | 日産自動車株式会社 | 微粒子−ポリロタキサン含有塗料、微粒子−ポリロタキサン含有塗膜及び塗装物品 |
| WO2014196636A1 (ja) * | 2013-06-07 | 2014-12-11 | アドバンスト・ソフトマテリアルズ株式会社 | ポリロタキサン、並びにオキシラン基及び／又はオキセタン基を２以上有する化合物を有する架橋用組成物 |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100389098B1 (ko) | 1994-10-28 | 2003-12-31 | 롬 앤드 하스 캄파니 | 개선된중합체제조방법 |
| WO2014080981A1 (ja) | 2012-11-22 | 2014-05-30 | 国立大学法人 東京大学 | 新規ポリロタキサン及びその製造方法 |
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| JP2018522973A (ja) | 2018-08-16 |
| KR20180019172A (ko) | 2018-02-23 |
| EP3310847A1 (en) | 2018-04-25 |
| US20180362691A1 (en) | 2018-12-20 |
| US10954331B2 (en) | 2021-03-23 |
| WO2016202906A1 (en) | 2016-12-22 |
| JP6830256B2 (ja) | 2021-02-17 |
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