JP2014530922A5 - - Google Patents
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- Publication number
- JP2014530922A5 JP2014530922A5 JP2014534764A JP2014534764A JP2014530922A5 JP 2014530922 A5 JP2014530922 A5 JP 2014530922A5 JP 2014534764 A JP2014534764 A JP 2014534764A JP 2014534764 A JP2014534764 A JP 2014534764A JP 2014530922 A5 JP2014530922 A5 JP 2014530922A5
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- cocatalyst
- ticl
- tetrafluoropropene
- combinations
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 description 45
- 239000003054 catalyst Substances 0.000 description 18
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 13
- 239000003999 initiator Substances 0.000 description 13
- 229910007926 ZrCl Inorganic materials 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000178 monomer Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 5
- 229920000140 heteropolymer Polymers 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229940024548 aluminum oxide Drugs 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- CWINGZLCRSDKCL-UHFFFAOYSA-N ethoxycarbonyloxy ethyl carbonate Chemical compound CCOC(=O)OOC(=O)OCC CWINGZLCRSDKCL-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- IMFNMOWMVGGCDD-UHFFFAOYSA-N C(#N)C(CC(C(=O)O)N=N)(C)C(C)(CCC(=O)O)C#N Chemical compound C(#N)C(CC(C(=O)O)N=N)(C)C(C)(CCC(=O)O)C#N IMFNMOWMVGGCDD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QWJDFBFFYONKLC-UHFFFAOYSA-N 2-diazenylpentanoic acid Chemical compound N(=N)C(C(=O)O)CCC QWJDFBFFYONKLC-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 alkyl metal halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- IRVTWLLMYUSKJS-UHFFFAOYSA-N carboxyoxy propyl carbonate Chemical compound CCCOC(=O)OOC(O)=O IRVTWLLMYUSKJS-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161543714P | 2011-10-05 | 2011-10-05 | |
| US61/543,714 | 2011-10-05 | ||
| US13/645,444 US20130089671A1 (en) | 2011-10-05 | 2012-10-04 | Polymers formed from 2,3,3,3-tetrafluoropropene and articles and uses thereof |
| US13/645,437 US20130090439A1 (en) | 2011-10-05 | 2012-10-04 | Polymerization Of 2,3,3,3-Tetrafluoropropene And Polymers Formed From 2,3,3,3-Tetrafluoropropene |
| US13/645,437 | 2012-10-04 | ||
| US13/645,444 | 2012-10-04 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017130097A Division JP2017214588A (ja) | 2011-10-05 | 2017-07-03 | ２，３，３，３−テトラフルオロプロペンの重合、及び２，３，３，３−テトラフルオロプロペンから形成されるポリマー |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014530922A JP2014530922A (ja) | 2014-11-20 |
| JP2014530922A5 true JP2014530922A5 (https=) | 2015-07-30 |
Family
ID=48042478
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014534764A Pending JP2014530922A (ja) | 2011-10-05 | 2012-10-05 | ２，３，３，３−テトラフルオロプロペンの重合、及び２，３，３，３−テトラフルオロプロペンから形成されるポリマー |
| JP2017130097A Pending JP2017214588A (ja) | 2011-10-05 | 2017-07-03 | ２，３，３，３−テトラフルオロプロペンの重合、及び２，３，３，３−テトラフルオロプロペンから形成されるポリマー |
| JP2019012391A Pending JP2019108544A (ja) | 2011-10-05 | 2019-01-28 | ２，３，３，３−テトラフルオロプロペンの重合、及び２，３，３，３−テトラフルオロプロペンから形成されるポリマー |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017130097A Pending JP2017214588A (ja) | 2011-10-05 | 2017-07-03 | ２，３，３，３−テトラフルオロプロペンの重合、及び２，３，３，３−テトラフルオロプロペンから形成されるポリマー |
| JP2019012391A Pending JP2019108544A (ja) | 2011-10-05 | 2019-01-28 | ２，３，３，３−テトラフルオロプロペンの重合、及び２，３，３，３−テトラフルオロプロペンから形成されるポリマー |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20130090439A1 (https=) |
| EP (2) | EP3243850A1 (https=) |
| JP (3) | JP2014530922A (https=) |
| CN (2) | CN108285504A (https=) |
| WO (1) | WO2013052790A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9624325B2 (en) | 2011-10-05 | 2017-04-18 | Honeywell Intenational Inc. | Curable fluorocopolymer formed from tetrafluoropropene |
| CN103360524A (zh) * | 2012-04-09 | 2013-10-23 | 纳幕尔杜邦公司 | 两相反应介质中的氟化乙烯基单体的聚合 |
| US8927666B2 (en) * | 2012-11-08 | 2015-01-06 | Honeywell International Inc. | Polymerization of monomers using fluorinated propylene solvents |
| EP3060590B1 (en) | 2013-10-22 | 2020-03-04 | Honeywell International Inc. | Curable fluorocopolymer formed from tetrafluoropropene |
| WO2016040525A1 (en) * | 2014-09-09 | 2016-03-17 | Honeywell International Inc. | Low voc and high solid fluoropolymer for coating applications |
| CN105111038B (zh) | 2015-08-18 | 2017-11-21 | 巨化集团技术中心 | 一种用甲基氯化镁制备2,3,3,3‑四氟丙烯的方法 |
| US11015005B2 (en) * | 2015-11-20 | 2021-05-25 | Honeywell International Inc. | Fluorocopolymers for coating applications |
| CN109311911B (zh) | 2016-06-20 | 2021-11-16 | 盐野义制药株式会社 | 用于制备取代多环吡啶酮衍生物及其晶体的方法 |
| CN109477673B (zh) * | 2016-06-27 | 2021-07-06 | 联合工艺公司 | 电热传热系统 |
| CN110536939B (zh) | 2017-04-18 | 2021-08-03 | Ａｇｃ株式会社 | 氟系涂料、氟系涂料的制造方法、涂装物品及其制造方法 |
| JP2020105234A (ja) | 2017-04-18 | 2020-07-09 | Ａｇｃ株式会社 | 粉体塗料 |
| JP7083681B2 (ja) * | 2018-04-05 | 2022-06-13 | 株式会社クレハ | フッ化ビニリデン共重合体の製造方法 |
| CN109810213B (zh) * | 2018-12-26 | 2021-05-04 | 乳源东阳光氟树脂有限公司 | 一种水/超临界二氧化碳混合体系下含氟聚合物及制备方法 |
| US11340528B2 (en) * | 2019-12-11 | 2022-05-24 | Jsr Corporation | Production method of composition for resist top coat layer, method of forming resist pattern, production method of fluorine-containing resin, and method of improving water repellency of resist top coat layer |
| JP7415778B2 (ja) * | 2020-05-08 | 2024-01-17 | Ａｇｃ株式会社 | 含フッ素重合体および含フッ素重合体の製造方法 |
| US20230373887A1 (en) * | 2020-10-15 | 2023-11-23 | Resonac Corporation | Method for storing fluorobutene |
| KR102924118B1 (ko) * | 2020-10-15 | 2026-02-09 | 가부시끼가이샤 레조낙 | 플루오로부텐의 보관 방법 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2599640A (en) | 1944-08-04 | 1952-06-10 | Du Pont | Copolymers of chlorotrifluoroethylene, an olefinic hydrocarbon and a vinyl carboxylate |
| US2919263A (en) | 1954-07-14 | 1959-12-29 | Hoechst Ag | Process for the preparation of high molecular weight fluorine compounds |
| US2970988A (en) * | 1955-10-14 | 1961-02-07 | Minnesota Mining & Mfg | New fluorine-containing polymers and preparation thereof |
| US3085996A (en) | 1955-10-14 | 1963-04-16 | Minnesota Mining & Mfg | Copolymer of 2, 3, 3, 3-tetrafluoropropene and fluorinated conjugated diolefins and the preparation thereof |
| US3053818A (en) | 1956-07-31 | 1962-09-11 | Minnesota Mining & Mfg | Trifluorochloroethylene interpolymers |
| US3240757A (en) | 1961-04-26 | 1966-03-15 | Dow Chemical Co | Copolymers of 3, 3, 3-trifluoro-2-trifluoromethyl propene and vinyl monomers |
| US3240825A (en) | 1963-01-14 | 1966-03-15 | Pennsalt Chemicals Corp | Homotelomers of 2,3,3,3-tetrafluoropropene-1 and method for making same |
| US3893987A (en) | 1974-05-20 | 1975-07-08 | Allied Chem | Modified hexa fluoroisobutylene/vinylidene fluoride copolymers having improved processing characteristics |
| JPH07119261B2 (ja) | 1990-06-20 | 1995-12-20 | セントラル硝子株式会社 | 含フッ素共重合体 |
| BE1005693A3 (fr) | 1992-02-05 | 1993-12-21 | Solvay | Nouveaux materiaux plastiques formes de copolymeres heterogenes de fluorure de vinylidene et de chlortrifluorethylene, utilisation et procede de fabrication. |
| DE69633024T2 (de) * | 1995-02-06 | 2005-08-04 | E.I. Du Pont De Nemours And Co., Wilmington | Amorphe HFP/TFE Copolymere |
| EP0911347B1 (en) * | 1997-10-15 | 2006-08-23 | E.I. Du Pont De Nemours And Company | Copolymers of maleic anhydride or acid and fluorinated olefins |
| IT1301451B1 (it) | 1998-06-04 | 2000-06-13 | Ausimont Spa | Copolimeri del clorotrifluoroetilene |
| EP1242486B1 (fr) * | 1999-12-29 | 2004-11-17 | Hydro-Québec | Elastomeres flouorosulfones a faible tg a base d'hexafloropropene et ne contenant ni du tetrafluoroethylene, ni de groupement siloxane |
| US8557938B2 (en) * | 2005-11-10 | 2013-10-15 | Arkema Inc. | Branched fluoropolymers |
| US7803890B2 (en) * | 2006-12-20 | 2010-09-28 | Honeywell International Inc. | Fluorocopolymers |
| US8063149B2 (en) * | 2006-12-20 | 2011-11-22 | Honeywell International Inc. | Fluorocopolymers blends |
| EP2592108A1 (en) * | 2006-12-20 | 2013-05-15 | Honeywell International Inc. | Copolymers for barriers |
| CN105669891A (zh) * | 2008-07-07 | 2016-06-15 | 阿科玛股份有限公司 | 偏二氟乙烯/2,3,3,3-四氟丙烯共聚物 |
| JP2010095576A (ja) * | 2008-10-14 | 2010-04-30 | Daikin Ind Ltd | 部分結晶性フッ素樹脂及び積層体 |
| EP2597106B1 (en) * | 2009-03-05 | 2014-04-30 | Daikin Industries, Ltd. | Fluoroelastomer, curable composition and cured rubber article |
| WO2011122661A1 (ja) | 2010-03-30 | 2011-10-06 | ダイキン工業株式会社 | ２，３，３，３－テトラフルオロプロペンの単独重合体 |
| EP2686355B1 (en) * | 2011-03-16 | 2018-06-27 | Arkema, Inc. | Copolymers of vdf and 2,3,3,3-tetrafluoropropene |
| EP2686354A4 (en) | 2011-03-16 | 2014-10-15 | Arkema Inc | SYNTHESIS 2,3,3,3-TETRAFLUORPROPHIC FLUOROPOLYMERS |
-
2012
- 2012-10-04 US US13/645,437 patent/US20130090439A1/en not_active Abandoned
- 2012-10-05 CN CN201810179859.1A patent/CN108285504A/zh active Pending
- 2012-10-05 EP EP17163688.9A patent/EP3243850A1/en not_active Withdrawn
- 2012-10-05 CN CN201280059491.6A patent/CN103958553B/zh not_active Expired - Fee Related
- 2012-10-05 EP EP12837790.0A patent/EP2751147A4/en not_active Withdrawn
- 2012-10-05 WO PCT/US2012/058938 patent/WO2013052790A2/en not_active Ceased
- 2012-10-05 JP JP2014534764A patent/JP2014530922A/ja active Pending
-
2017
- 2017-05-01 US US15/583,448 patent/US20170240666A1/en not_active Abandoned
- 2017-07-03 JP JP2017130097A patent/JP2017214588A/ja active Pending
-
2019
- 2019-01-28 JP JP2019012391A patent/JP2019108544A/ja active Pending
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