JP2003525311A5 - - Google Patents
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- Publication number
- JP2003525311A5 JP2003525311A5 JP2000597337A JP2000597337A JP2003525311A5 JP 2003525311 A5 JP2003525311 A5 JP 2003525311A5 JP 2000597337 A JP2000597337 A JP 2000597337A JP 2000597337 A JP2000597337 A JP 2000597337A JP 2003525311 A5 JP2003525311 A5 JP 2003525311A5
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- solution
- filtered
- precipitated
- toluene
- 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
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- 229920000642 polymer Polymers 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 229920001429 chelating resin Polymers 0.000 description 34
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000003456 ion exchange resin Substances 0.000 description 12
- 229920003303 ion-exchange polymer Polymers 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 125000000565 sulfonamide group Chemical group 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 150000003949 imides Chemical class 0.000 description 8
- KJUJWQKOLRDCCH-UHFFFAOYSA-N n-(5-bicyclo[2.2.1]hept-2-enylmethyl)propane-1-sulfonamide Chemical compound C1C2C(CNS(=O)(=O)CCC)CC1C=C2 KJUJWQKOLRDCCH-UHFFFAOYSA-N 0.000 description 7
- -1 imide acetate Chemical class 0.000 description 6
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- FEALMIYDTDFJBH-UHFFFAOYSA-N n-(5-bicyclo[2.2.1]hept-2-enylmethyl)methanesulfonamide Chemical compound C1C2C(CNS(=O)(=O)C)CC1C=C2 FEALMIYDTDFJBH-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11893699P | 1999-02-05 | 1999-02-05 | |
| US60/118,936 | 1999-02-05 | ||
| US09/497,356 | 2000-02-03 | ||
| US09/497,356 US6235849B1 (en) | 1999-02-05 | 2000-02-03 | Method of preparing norbornene sulfonamide polymers |
| PCT/US2000/003060 WO2000046267A1 (en) | 1999-02-05 | 2000-02-04 | Method of preparing norbornene sulfonamide polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003525311A JP2003525311A (ja) | 2003-08-26 |
| JP2003525311A5 true JP2003525311A5 (https=) | 2011-02-03 |
Family
ID=22381647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000597337A Pending JP2003525311A (ja) | 1999-02-05 | 2000-02-04 | ノルボルネンスルホンアミドポリマーの製造法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6235849B1 (https=) |
| EP (1) | EP1157058B1 (https=) |
| JP (1) | JP2003525311A (https=) |
| KR (1) | KR100687963B1 (https=) |
| AT (1) | ATE243719T1 (https=) |
| AU (1) | AU2757300A (https=) |
| DE (1) | DE60003529T2 (https=) |
| WO (1) | WO2000046267A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6887956B2 (en) | 2000-10-12 | 2005-05-03 | Dow Global Technologies Inc. | Catalyst system for high-cis polybutadiene |
| KR20020056602A (ko) * | 2000-12-29 | 2002-07-10 | 노기호 | 황을 포함하는 고리형 올레핀 공중합체 및 그의 제조방법 |
| JP5013033B2 (ja) * | 2001-07-27 | 2012-08-29 | Ｊｓｒ株式会社 | 環状オレフィン付加重合体の製造方法 |
| JP4941621B2 (ja) * | 2001-07-27 | 2012-05-30 | Ｊｓｒ株式会社 | 環状オレフィン付加重合体の製造方法 |
| US6583307B2 (en) * | 2001-03-07 | 2003-06-24 | University Of New Orleans Research And Technology Foundation, Inc. | Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system |
| WO2004037866A2 (en) | 2002-10-21 | 2004-05-06 | Shipley Company L.L.C. | Photoresists containing sulfonamide component |
| US6677419B1 (en) | 2002-11-13 | 2004-01-13 | International Business Machines Corporation | Preparation of copolymers |
| EP1589055A4 (en) * | 2003-01-31 | 2010-06-02 | Zeon Corp | METHOD FOR THE PRODUCTION OF A CYCLOOLEFIN RESIN FILM AND METHOD FOR THE PRODUCTION OF A CYCLOOLEFIN RESIN FILM OR A CYCLOOLEFIN RESIN FILM |
| US6949325B2 (en) * | 2003-09-16 | 2005-09-27 | International Business Machines Corporation | Negative resist composition with fluorosulfonamide-containing polymer |
| JP2005171234A (ja) * | 2003-11-18 | 2005-06-30 | Jsr Corp | 新規な（共）重合体およびその製造方法並びにカルボキシル基含有（共）重合体の製造方法 |
| US7063931B2 (en) * | 2004-01-08 | 2006-06-20 | International Business Machines Corporation | Positive photoresist composition with a polymer including a fluorosulfonamide group and process for its use |
| CA2462011A1 (en) * | 2004-02-23 | 2005-08-23 | Bayer Inc. | Process for the preparation of low molecular weight nitrile rubber |
| ATE414118T1 (de) * | 2004-07-07 | 2008-11-15 | Promerus Llc | Lichtempfindliche dielektrische harzzusammensetzungen und ihre verwendungen |
| JP4494161B2 (ja) * | 2004-10-14 | 2010-06-30 | 東京応化工業株式会社 | 高分子化合物、ポジ型レジスト組成物およびレジストパターン形成方法 |
| EP2033978A1 (en) * | 2004-12-15 | 2009-03-11 | Nihon University | Method for producing norbornene based addition (co)polymer |
| ATE517370T1 (de) * | 2005-02-22 | 2011-08-15 | Promerus Llc | Norbornenpolymere und deren herstellungsverfahren |
| US7799883B2 (en) * | 2005-02-22 | 2010-09-21 | Promerus Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP4887710B2 (ja) * | 2005-09-28 | 2012-02-29 | セントラル硝子株式会社 | α−置換アクリル酸ノルボルナニル類の製造方法 |
| CN100344656C (zh) * | 2006-05-11 | 2007-10-24 | 复旦大学 | 聚降冰片烯的制备方法 |
| US20080027246A1 (en) * | 2006-07-26 | 2008-01-31 | Andrew Bell | Process for forming perfluorinated-alkyl sulfonamide substituted norbornene-type monomers |
| JP5076682B2 (ja) * | 2006-07-26 | 2012-11-21 | セントラル硝子株式会社 | Ｎ−（ビシクロ［２，２，１］ヘプト−５−エン−２−イルメチル）−１，１，１−トリフルオロメタンスルホンアミドの製造方法 |
| JP5314882B2 (ja) | 2007-02-15 | 2013-10-16 | 東京応化工業株式会社 | 高分子化合物、レジスト組成物及びレジストパターン形成方法 |
| WO2008099725A1 (ja) * | 2007-02-15 | 2008-08-21 | Tokyo Ohka Kogyo Co., Ltd. | 高分子化合物、レジスト組成物及びレジストパターン形成方法 |
| JP5236246B2 (ja) * | 2007-10-18 | 2013-07-17 | 株式会社クラレ | スルホニルハライド誘導体の製造方法 |
| KR101610315B1 (ko) * | 2008-09-02 | 2016-04-07 | 주식회사 쿠라레 | 설톤 유도체의 제조방법 |
| JP5117484B2 (ja) * | 2009-12-28 | 2013-01-16 | 東京応化工業株式会社 | 新規な化合物、及びその製造方法 |
| US8541523B2 (en) * | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| CN102702432B (zh) * | 2012-05-30 | 2014-06-18 | 宁波工程学院 | 用于降冰片烯、马来酸酐与环己烯三元共聚的催化剂以及三元共聚方法 |
| CN105218821A (zh) * | 2015-10-19 | 2016-01-06 | 昆明理工大学 | 一种聚合单体与二氧化硫共聚物的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970133A (en) * | 1974-12-16 | 1976-07-20 | The Goodyear Tire & Rubber Company | Chlorothio-sulfonamide-modified rubbery terpolymers and their blends |
| DE3720760A1 (de) | 1987-06-24 | 1989-01-05 | Bayer Ag | Norbornan- und norbornensulfonamide, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel |
| JP3221636B2 (ja) * | 1993-03-15 | 2001-10-22 | 株式会社クラレ | ３−フェニルスルホニルアミノ−ビシクロ［２，２，１］ヘプタン−２−カルボン酸アルキルエステルの製造方法 |
| US5656412A (en) * | 1995-03-07 | 1997-08-12 | Lucent Technologies Inc. | Energy-sensitive resist material and a process for device fabrication using an energy-sensitive resist material |
| CA2154862A1 (en) * | 1995-03-20 | 1996-09-21 | Roger John Hopper | Process for preparation of n-halothiosulfonamide modified terpolymers |
| JPH09124588A (ja) * | 1995-11-07 | 1997-05-13 | Mitsubishi Materials Corp | 不飽和スルホン酸誘導体とその製造方法 |
| WO1997033198A1 (en) | 1996-03-07 | 1997-09-12 | The B.F. Goodrich Company | Photoresist compositions comprising polycyclic polymers with acid labile pendant groups |
| JPH11184090A (ja) * | 1997-10-13 | 1999-07-09 | Fuji Photo Film Co Ltd | 遠紫外線露光用ポジ型フォトレジスト組成物 |
| JP3720970B2 (ja) * | 1998-01-13 | 2005-11-30 | 株式会社東芝 | 感光性組成物、およびこれを用いたパターン形成方法、半導体装置の製造方法 |
-
2000
- 2000-02-03 US US09/497,356 patent/US6235849B1/en not_active Expired - Lifetime
- 2000-02-04 WO PCT/US2000/003060 patent/WO2000046267A1/en not_active Ceased
- 2000-02-04 AT AT00905995T patent/ATE243719T1/de not_active IP Right Cessation
- 2000-02-04 AU AU27573/00A patent/AU2757300A/en not_active Abandoned
- 2000-02-04 KR KR1020017009927A patent/KR100687963B1/ko not_active Expired - Fee Related
- 2000-02-04 EP EP00905995A patent/EP1157058B1/en not_active Expired - Lifetime
- 2000-02-04 JP JP2000597337A patent/JP2003525311A/ja active Pending
- 2000-02-04 DE DE60003529T patent/DE60003529T2/de not_active Expired - Lifetime
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