JP2014530940A5 - - Google Patents
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- JP2014530940A5 JP2014530940A5 JP2014537332A JP2014537332A JP2014530940A5 JP 2014530940 A5 JP2014530940 A5 JP 2014530940A5 JP 2014537332 A JP2014537332 A JP 2014537332A JP 2014537332 A JP2014537332 A JP 2014537332A JP 2014530940 A5 JP2014530940 A5 JP 2014530940A5
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- present
- optionally substituted
- heterocycle
- heteroatom
- 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.)
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- 238000000034 method Methods 0.000 claims description 91
- 239000000178 monomer Substances 0.000 claims description 56
- 238000006116 polymerization reaction Methods 0.000 claims description 31
- 239000007800 oxidant agent Substances 0.000 claims description 28
- 230000001590 oxidative effect Effects 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 229920000547 conjugated polymer Polymers 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 238000010791 quenching Methods 0.000 claims description 16
- 230000000171 quenching effect Effects 0.000 claims description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000002841 Lewis acid Substances 0.000 claims description 14
- 150000007517 lewis acids Chemical class 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- 239000007848 Bronsted acid Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000003577 thiophenes Chemical class 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 150000004053 quinones Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical group ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 7
- -1 3-substituted thiophene Chemical group 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000004059 quinone derivatives Chemical class 0.000 description 3
- 125000004151 quinonyl group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- MPKAOMIFYFZQFF-UHFFFAOYSA-N 3-(2,2,2-trifluoroethoxy)thiophene Chemical compound FC(F)(F)COC=1C=CSC=1 MPKAOMIFYFZQFF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 150000004060 quinone imines Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161550332P | 2011-10-21 | 2011-10-21 | |
| US61/550,332 | 2011-10-21 | ||
| PCT/US2012/061179 WO2013059712A1 (en) | 2011-10-21 | 2012-10-19 | Improved synthesis of conjugated polymers via oxidative polymerization and related compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014530940A JP2014530940A (ja) | 2014-11-20 |
| JP2014530940A5 true JP2014530940A5 (https=) | 2015-12-03 |
| JP6252480B2 JP6252480B2 (ja) | 2017-12-27 |
Family
ID=47116492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014537332A Active JP6252480B2 (ja) | 2011-10-21 | 2012-10-19 | 酸化重合による共役ポリマーの改善された合成方法および関連する組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US8859718B2 (https=) |
| EP (1) | EP2768868B1 (https=) |
| JP (1) | JP6252480B2 (https=) |
| KR (1) | KR101938922B1 (https=) |
| CN (1) | CN103987735B (https=) |
| TW (1) | TWI555772B (https=) |
| WO (2) | WO2013059714A1 (https=) |
Families Citing this family (71)
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| EP2992825B1 (en) | 2007-11-26 | 2017-11-01 | C.R. Bard Inc. | Integrated system for intravascular placement of a catheter |
| US8781555B2 (en) | 2007-11-26 | 2014-07-15 | C. R. Bard, Inc. | System for placement of a catheter including a signal-generating stylet |
| US9521961B2 (en) | 2007-11-26 | 2016-12-20 | C. R. Bard, Inc. | Systems and methods for guiding a medical instrument |
| US9532724B2 (en) | 2009-06-12 | 2017-01-03 | Bard Access Systems, Inc. | Apparatus and method for catheter navigation using endovascular energy mapping |
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| CN102711642B (zh) | 2009-09-22 | 2015-04-29 | 麦迪尼治疗公司 | 用于控制一类不同治疗装置的使用和操作的系统和方法 |
| WO2011150376A1 (en) | 2010-05-28 | 2011-12-01 | C.R. Bard, Inc. | Apparatus for use with needle insertion guidance system |
| JP6252480B2 (ja) | 2011-10-21 | 2017-12-27 | 日産化学工業株式会社 | 酸化重合による共役ポリマーの改善された合成方法および関連する組成物 |
| US9330809B2 (en) * | 2013-12-17 | 2016-05-03 | Dow Global Technologies Llc | Electrically conducting composites, methods of manufacture thereof and articles comprising the same |
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| CN107849376B (zh) * | 2015-07-17 | 2021-11-30 | 日产化学工业株式会社 | 适用于有机电子的包含金属纳米颗粒的非水性油墨组合物 |
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| JP6640917B2 (ja) * | 2018-06-04 | 2020-02-05 | キヤノンメディカルシステムズ株式会社 | 医用画像診断装置及び医用画像診断装置における穿刺針の管理装置 |
| CN112867443B (zh) | 2018-10-16 | 2024-04-26 | 巴德阿克塞斯系统股份有限公司 | 用于建立电连接的安全装备连接系统及其方法 |
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| CN114159098B (zh) | 2020-09-10 | 2026-01-02 | 巴德阿克塞斯系统股份有限公司 | 具有压力测量能力的超声探测器 |
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2012
- 2012-10-19 JP JP2014537332A patent/JP6252480B2/ja active Active
- 2012-10-19 KR KR1020147012813A patent/KR101938922B1/ko active Active
- 2012-10-19 TW TW101138791A patent/TWI555772B/zh active
- 2012-10-19 US US13/656,561 patent/US8859718B2/en not_active Expired - Fee Related
- 2012-10-19 US US13/656,563 patent/US9949720B2/en active Active
- 2012-10-19 CN CN201280061750.9A patent/CN103987735B/zh active Active
- 2012-10-19 WO PCT/US2012/061182 patent/WO2013059714A1/en not_active Ceased
- 2012-10-19 WO PCT/US2012/061179 patent/WO2013059712A1/en not_active Ceased
- 2012-10-19 EP EP12780380.7A patent/EP2768868B1/en not_active Not-in-force
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2014
- 2014-09-09 US US14/481,692 patent/US20150105534A1/en not_active Abandoned
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2018
- 2018-04-12 US US15/951,903 patent/US11413015B2/en active Active
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