KR102239534B1 - 폴리올레핀 반응성 텔레켈릭 예비중합체를 제조하는 방법, 폴리올레핀 반응성 텔레켈릭 예비중합체 및 가교 엘라스토머 및 고분자량 엘라스토머 - Google Patents
폴리올레핀 반응성 텔레켈릭 예비중합체를 제조하는 방법, 폴리올레핀 반응성 텔레켈릭 예비중합체 및 가교 엘라스토머 및 고분자량 엘라스토머 Download PDFInfo
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- KR102239534B1 KR102239534B1 KR1020167007950A KR20167007950A KR102239534B1 KR 102239534 B1 KR102239534 B1 KR 102239534B1 KR 1020167007950 A KR1020167007950 A KR 1020167007950A KR 20167007950 A KR20167007950 A KR 20167007950A KR 102239534 B1 KR102239534 B1 KR 102239534B1
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- prepolymer
- reactive telechelic
- polyolefin
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 93
- 239000000806 elastomer Substances 0.000 title claims abstract description 93
- 229920000098 polyolefin Polymers 0.000 title claims description 111
- 238000000034 method Methods 0.000 title claims description 39
- 229920001730 Moisture cure polyurethane Polymers 0.000 title 2
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims abstract description 20
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 17
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 15
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 21
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 14
- 239000011976 maleic acid Substances 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- RCQYUWMJSHYZCA-XFXZXTDPSA-N (1Z)-3-hexylcyclooctene Chemical group C(CCCCC)C1\C=C/CCCCC1 RCQYUWMJSHYZCA-XFXZXTDPSA-N 0.000 claims description 10
- 239000011984 grubbs catalyst Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 125000000524 functional group Chemical group 0.000 description 41
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- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- 0 CC(C(*)(CCCC*)N)=C1NC1 Chemical compound CC(C(*)(CCCC*)N)=C1NC1 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- FCDPQMAOJARMTG-UHFFFAOYSA-M benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium;tricyclohexylphosphanium Chemical compound C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CC1=CC=CC=C1 FCDPQMAOJARMTG-UHFFFAOYSA-M 0.000 description 3
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- VFUYUMOOAYKNNO-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-(2-methylaziridin-1-yl)propanoic acid Chemical group CCC(CO)(CO)CO.CC1CN1CCC(O)=O.CC1CN1CCC(O)=O.CC1CN1CCC(O)=O VFUYUMOOAYKNNO-UHFFFAOYSA-N 0.000 description 2
- PFJYFNQRYAOFBV-UHFFFAOYSA-N CC1CN1CCC(=O)OCCCCOC(=O)CCN1CC1C Chemical group CC1CN1CCC(=O)OCCCCOC(=O)CCN1CC1C PFJYFNQRYAOFBV-UHFFFAOYSA-N 0.000 description 2
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- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000852 hydrogen donor Substances 0.000 description 2
- 229920001684 low density polyethylene Polymers 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000569 multi-angle light scattering Methods 0.000 description 2
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- VGMAAJKEQOXIML-ALCCZGGFSA-N (1z)-3-methylcyclooctene Chemical compound CC\1CCCCC\C=C/1 VGMAAJKEQOXIML-ALCCZGGFSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-M 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate Chemical compound OCC(C)(CO)C([O-])=O PTBDIHRZYDMNKB-UHFFFAOYSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
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- INYQDLQHEJDZHS-ARJAWSKDSA-N [(Z)-4-[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxybut-2-enyl] 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate Chemical compound OCC(C(=O)OC\C=C/COC(C(CO)(C)CO)=O)(C)CO INYQDLQHEJDZHS-ARJAWSKDSA-N 0.000 description 1
- VZUAUHWZIKOMFC-ARJAWSKDSA-N [(z)-4-acetyloxybut-2-enyl] acetate Chemical compound CC(=O)OC\C=C/COC(C)=O VZUAUHWZIKOMFC-ARJAWSKDSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
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- LKWHMUMFRUHFIR-UHFFFAOYSA-N but-2-ene-1,1,4,4-tetrol Chemical compound OC(O)C=CC(O)O LKWHMUMFRUHFIR-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000001939 cyclooctenes Chemical class 0.000 description 1
- BVPDPOIDPIKHHQ-UHFFFAOYSA-N dec-5-enedinitrile Chemical compound N#CCCCC=CCCCC#N BVPDPOIDPIKHHQ-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- CPSQPCGPYWRIPB-ONEGZZNKSA-N dimethyl (e)-hex-3-enedioate Chemical compound COC(=O)C\C=C\CC(=O)OC CPSQPCGPYWRIPB-ONEGZZNKSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
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- C—CHEMISTRY; METALLURGY
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
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- C08G2261/1412—Saturated aliphatic units
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
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- C08G2261/3322—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from cyclooctene
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- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
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- C08G2261/70—Post-treatment
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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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
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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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyamides (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
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| US201361884594P | 2013-09-30 | 2013-09-30 | |
| US61/884,594 | 2013-09-30 | ||
| PCT/US2014/056195 WO2015047840A1 (en) | 2013-09-30 | 2014-09-18 | A process to produce a polyolefin reactive telechelic pre-polymer, polyolefin reactive telechelic pre-polymers and crosslinked elastomers and high molecular weight elastomers |
Publications (2)
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| KR20160065833A KR20160065833A (ko) | 2016-06-09 |
| KR102239534B1 true KR102239534B1 (ko) | 2021-04-14 |
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| EP (1) | EP3052542B1 (enExample) |
| JP (2) | JP6385445B2 (enExample) |
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| CN (1) | CN105873977B (enExample) |
| BR (1) | BR112016004686B1 (enExample) |
| SG (2) | SG10201801789YA (enExample) |
| TW (1) | TWI558727B (enExample) |
| WO (1) | WO2015047840A1 (enExample) |
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| TWI735442B (zh) * | 2015-05-28 | 2021-08-11 | 美商陶氏全球科技有限責任公司 | 聚烯烴反應性遙爪預聚合物 |
| TWI719981B (zh) * | 2015-05-28 | 2021-03-01 | 美商陶氏全球科技有限責任公司 | 製備聚烯烴反應性遙爪預聚合物之方法 |
| JP7124702B2 (ja) * | 2016-10-31 | 2022-08-24 | 日本ゼオン株式会社 | 架橋性組成物および架橋体 |
| CN107602867B (zh) * | 2017-09-06 | 2020-07-07 | 济南大学 | 一种含氟和／或硅的聚烯烃-聚芳酯共聚物及制备方法和应用 |
| JP7610511B2 (ja) | 2018-12-28 | 2025-01-08 | ダウ グローバル テクノロジーズ エルエルシー | テレケリックポリオレフィンおよびこれを調製するための方法 |
| BR112021012845A2 (pt) | 2018-12-28 | 2021-09-28 | Dow Global Technologies Llc | Composição curável, e, artigo |
| JP7609783B2 (ja) | 2018-12-28 | 2025-01-07 | ダウ グローバル テクノロジーズ エルエルシー | 不飽和ポリオレフィンを含む硬化性組成物 |
| WO2020140064A1 (en) | 2018-12-28 | 2020-07-02 | Dow Global Technologies Llc | Organometallic chain transfer agents |
| WO2020205992A1 (en) | 2019-04-01 | 2020-10-08 | Regents, Of The University Of Minnesota | Multiblock copolymers of polyolefins and polyesters |
| KR102267775B1 (ko) | 2020-06-02 | 2021-06-21 | 고려대학교 산학협력단 | 기계적 힘에 의한 화학구조 변화가 가능한 아지리딘 고분자 |
| US20240317932A1 (en) * | 2021-05-27 | 2024-09-26 | Korea University Research And Business Foundation | Mechanical force selectively responsive aziridine polymer |
| CN114031944B (zh) * | 2021-12-01 | 2023-03-24 | 深圳先进电子材料国际创新研究院 | 一种低迟滞导热凝胶及其制备方法 |
| WO2023205392A1 (en) * | 2022-04-21 | 2023-10-26 | Regents Of The University Of Minnesota | Reactive additives for recycling mixed plastic waste |
| CN115960288B (zh) * | 2022-12-27 | 2024-01-05 | 中国科学技术大学 | 交联增强的复分解聚烯烃及其制备方法 |
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2014
- 2014-08-26 TW TW103129330A patent/TWI558727B/zh active
- 2014-09-18 SG SG10201801789YA patent/SG10201801789YA/en unknown
- 2014-09-18 WO PCT/US2014/056195 patent/WO2015047840A1/en not_active Ceased
- 2014-09-18 EP EP14780973.5A patent/EP3052542B1/en active Active
- 2014-09-18 JP JP2016545759A patent/JP6385445B2/ja active Active
- 2014-09-18 SG SG11201602058VA patent/SG11201602058VA/en unknown
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- 2014-09-18 US US15/024,948 patent/US10005878B2/en active Active
- 2014-09-18 KR KR1020167007950A patent/KR102239534B1/ko active Active
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| JP2009287042A (ja) | 1999-05-31 | 2009-12-10 | Nippon Zeon Co Ltd | 開環オレフィン重合体およびその水素化物の製造方法 |
| JP2004533424A (ja) | 2001-03-30 | 2004-11-04 | カリフォルニア インスティチュート オブ テクノロジー | シクロオレフィンの選択的開環クロス−メタセシス |
| WO2005012427A1 (ja) * | 2003-08-04 | 2005-02-10 | Zeon Corporation | 重合性組成物及びそれを用いてなる成形体 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20160065833A (ko) | 2016-06-09 |
| US20160237203A1 (en) | 2016-08-18 |
| CN105873977A (zh) | 2016-08-17 |
| JP2016535812A (ja) | 2016-11-17 |
| SG11201602058VA (en) | 2016-04-28 |
| US10005878B2 (en) | 2018-06-26 |
| JP6802223B2 (ja) | 2020-12-16 |
| BR112016004686B1 (pt) | 2022-05-31 |
| SG10201801789YA (en) | 2018-04-27 |
| TWI558727B (zh) | 2016-11-21 |
| CN105873977B (zh) | 2019-05-10 |
| WO2015047840A1 (en) | 2015-04-02 |
| JP6802223B6 (ja) | 2021-01-20 |
| JP6385445B2 (ja) | 2018-09-05 |
| JP2018197349A (ja) | 2018-12-13 |
| BR112016004686A2 (enExample) | 2017-08-01 |
| EP3052542A1 (en) | 2016-08-10 |
| TW201522382A (zh) | 2015-06-16 |
| EP3052542B1 (en) | 2021-12-22 |
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