KR20070026142A - 실제적으로 직쇄형의 중합체 및 그의 제조방법 - Google Patents
실제적으로 직쇄형의 중합체 및 그의 제조방법 Download PDFInfo
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
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Abstract
Description
실시예 번호 | 성분 A | 성분 B | 성분 C | 생성물 수득량 |
18 | 실시예 1에 따라 제조된 고형분 생성물 (0.943 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.388 g) | 피리딘 (~0.2 ㎖) | 940 ㎎ |
19 | 실시예 2에 따라 제조된 고형분 생성물 (340 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (200 ㎎) | 피리딘 (~0.2 ㎖) | 440 ㎎ |
20 | 실시예 3에 따라 제조된 고형분 생성물 (79 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (50 ㎎) | 피리딘 (~0.2 ㎖) | 87 ㎎ |
21 | 실시예 4에 따라 제조된 고형분 생성물 (45 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (25 ㎎) | 피리딘 (~0.2 ㎖) | 33 ㎎ |
22 | 실시예 5에 따라 제조된 고형분 생성물 (44 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (25 ㎎) | 피리딘 (~0.2 ㎖) | 41 ㎎ |
23 | 실시예 8에 따라 제조된 고형분 생성물 (0.370 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.200 g) | 피리딘 (~0.2 ㎖) | 440 |
24 | 실시예 9에 따라 제조된 고형분 생성물 (0.640 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.350 g) | 피리딘 (~0.2 ㎖) | 700 |
25 | 실시예 11에 따라 제조된 고형분 생성물 (0.396 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.200 g) | 피리딘 (~0.2 ㎖) | 540 ㎎ |
26 | 실시예 12에 따라 제조된 고형분 생성물 (0.2272 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.100 g) | 피리딘 (~0.2 ㎖) | 320 ㎎ |
27 | 실시예 13에 따라 제조된 고형분 생성물 (210 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (150 ㎎) | 피리딘 (~0.2 ㎖) | 200 ㎎ |
28 | 실시예 14에 따라 제조된 고형분 생성물 (115 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (50 ㎎) | 피리딘 (~0.2 ㎖) | 78 ㎎ |
29 | 실시예 15에 따라 제조된 고형분 생성물 (83 ㎎) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (50 ㎎) | 피리딘 (~0.2 ㎖) | 5 ㎎ |
30 | 실시예 16에 따라 제조된 고형분 생성물 (0.135 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.086 g) | 없음 | 148 ㎎ |
31 | 실시예 17에 따라 제조된 고형분 생성물 (0.098 g) | 디메틸테트라메틸 에틸렌 디아민 팔라듐(II) (0.046 g) | 없음 | 780 ㎎ |
실시예 번호 | 단량체 성분 | 촉매 성분 | 랜덤 공중합체 생성물 수득량 |
35 | 부틸 아크릴레이트 (1.0 ㎖, 6.98 mmol) | 실시예 19의 생성물 (Pd 4.2 μmol) | 0.28 g |
36 | 부틸 아크릴레이트 (1.0 ㎖, 6.98 mmol) | 실시예 26의 생성물 (0.5㎖, Pd 8.0 μmol) | 0.1 g |
37 | 부틸 아크릴레이트 (1.0 ㎖, 6.98 mmol) | 실시예 30의 생성물 (0.5㎖, Pd 8.0 μmol) | 0.1 g |
38 | 스티렌 (1.0 ㎖, 8.73 mmol) | 실시예 26의 생성물 (0.5㎖, Pd 8.0 μmol) | 0.21 g |
39 | 스티렌 (1.0 ㎖, 8.73 mmol) | 실시예 30의 생성물 (0.5㎖, Pd 8.0 μmol) | 0.10 g |
40 | 스티렌 (1.0 ㎖, 8.73 mmol) | 실시예 25의 생성물 (0 5㎖, Pd 8.0 μmol) | 0.58 g |
41 | 이소보르닐 아크릴레이트 (1.0 ㎖, 4.73 mmol) | 실시예 19의 생성물 (0.5㎖, Pd 4.2 μmol) | 0.44 g |
42 | 이소보르닐 아크릴레이트 (1.0 ㎖, 4.73 mmol) | 실시예 26의 생성물 (0.5㎖, Pd 8.0 μmol) | 0.15 g |
반응기 셀 번호 | 반응온도 | 중합체 수득량 | 부틸아크릴레이트 배합률 | Mw(g/몰) | Mn(g/몰) | PDI |
1 | 90 ℃ | 0.65 g | 1.1 몰% | 108,000 | 72,000 | 1.5 |
2 | 110 ℃ | 0.48 g | 1.2 몰% | 68,000 | 40,000 | 1.7 |
3 | 120 ℃ | 0.30 g | 1.7 몰% | 43,000 | 25,000 | 1.7 |
Claims (10)
- 적어도 1개의 비환식 지방족 올레핀 단량체; 하기 식 [1]을 지닌 적어도 1개의 단량체; 및 하기 식 [2]에 따른 구조를 갖는 적어도 1개의 리간드와 착화된, 금속 중심 M을 지닌 촉매 조성물을 접촉시키는 것을 포함함을 특징으로 하고,수평균분자량이 21,200 이상이며,비환식 지방족 올레핀 단량체 단위를 1 내지 99.9 몰% 포함하는 공중합체를 제조하는 방법:식 중, Z는 할로겐, -CN, 방향족 하이드로카빌기, -COY 및 -CO2Y로부터 선택되고; Y는 수소 및 R19로부터 선택되며; R19는 하이드로카빌기, 방향족 하이드로카빌기 및 그의 유도체로부터 선택되고;J는 수소, 및 30개까지의 탄소를 지닌 지방족 하이드로카빌기로부터 선택되 며;금속 중심은 Ni 및 Pd로부터 선택되고;X1, X2 및 X3은 독립적으로 하이드로카빌기, 방향족 하이드로카빌기 및 그의 유도체로부터 선택되며;Q는 인, 비소, 질소 및 안티몬으로부터 선택되고;R15는 -SO3, SO2N(R18), -CO2, -PO3, -AsO3, -SiO2, -C(CF3)2O로부터 선택되며;R18은 수소, 할로겐, 하이드로카빌기, 방향족 하이드로카빌기 및 치환된 하이드로카빌기로부터 선택된다.
- 제 1항에 있어서, 상기 촉매 조성물은 금속원 M과 하기 식 [3]의 화합물을 배합하는 것을 포함하는 공정에 의해 형성되는 방법:[ X 2 X 3 O -- X 1 -- R 15 ] m [L] n ......[3]식 중, 각각의 L은 독립적으로 수소, 리튬, 나트륨, 칼륨, 탈륨, 칼슘 및 은으로부터 선택되고, m 및 n은 전하가 평형을 이루도록 선택된다.
- 제 1항에 있어서, 상기 비환식 지방족 올레핀 단량체로부터 유도된 공중합체의 부분의 분기쇄 함량은 분기쇄 함량 ≤ 15/1,000(분기쇄 수/탄소원자 수)을 나타내고, 상기 분기쇄 함량은 상기 공중합체의 탄소 13 NMR 및 융점에 의해 결정되는 방법.
- 제 1항에 있어서, M은 Pd인 방법.
- 제 1항에 있어서, 적어도 1개의 비환식 지방족 올레핀 단량체는 에틸렌인 방법.
- 제 1항에 있어서, 중합 온도는 0 내지 200℃인 방법.
- 적어도 1개의 비환식 지방족 올레핀 단량체; 적어도 1개의 노르보르넨 혹은 치환된 노르보르넨 단량체; 하기 식 [1]을 지닌 적어도 1개의 단량체; 및 하기 식 [2]에 따른 구조를 갖는 적어도 1개의 리간드와 착화된, 금속 중심 M을 지닌 촉매 조성물을 접촉시키는 것을 포함하는 것을 특징으로 하며,노르보르넨 또는 치환된 노르보르넨 유래 단위를 0.1 내지 50 몰% 포함하는 삼원 공중합체를 제조하는 방법:식 중, Z는 할로겐, -CN, 방향족 하이드로카빌기, -COY 및 -CO2Y로부터 선택되고; Y는 수소 및 R19로부터 선택되며; R19는 하이드로카빌기, 방향족 하이드로카빌기 및 그의 유도체로부터 선택되고;J는 수소, 및 30개까지의 탄소를 지닌 지방족 하이드로카빌기로부터 선택되며;M은 Ni 및 Pd로부터 선택되고;X1, X2 및 X3은 독립적으로 하이드로카빌기, 방향족 하이드로카빌기 및 그의 유도체로부터 선택되며;Q는 인, 비소, 질소 및 안티몬으로부터 선택되고;R15는 -SO3, SO2N(R18), -CO2, -PO3, -AsO3, -SiO2, -C(CF3)2O로부터 선택되며;R18은 수소, 할로겐, 하이드로카빌기, 방향족 하이드로카빌기 및 치환된 하이드로카빌기로부터 선택된다.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US71286605P | 2005-08-31 | 2005-08-31 | |
US60/712,866 | 2005-08-31 | ||
US11/457,982 US7635739B2 (en) | 2005-08-31 | 2006-07-17 | Substantially linear polymers and methods of making and using same |
US11/457,982 | 2006-07-17 |
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KR1020070097520A KR100881446B1 (ko) | 2005-08-31 | 2007-09-27 | 실제적으로 직쇄형의 중합체 및 그의 제조방법 |
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US (1) | US7635739B2 (ko) |
EP (1) | EP1760097B1 (ko) |
JP (1) | JP4799322B2 (ko) |
KR (2) | KR100856692B1 (ko) |
CN (1) | CN1923866B (ko) |
CA (1) | CA2556347C (ko) |
TW (1) | TWI331613B (ko) |
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CA2620852A1 (en) | 2007-02-28 | 2008-08-28 | Rohm And Haas Company | A porous linear polymer composition and method of making same |
JP5111145B2 (ja) * | 2007-02-28 | 2012-12-26 | ローム アンド ハース カンパニー | 非環式脂肪族オレフィンの重合 |
CA2620884C (en) * | 2007-02-28 | 2011-07-12 | Rohm And Haas Company | Composition and method for preparing copolymers of polar and non-polar olefins substantially free of free radical intiated polymer |
JP5292059B2 (ja) * | 2007-10-30 | 2013-09-18 | 日本ポリプロ株式会社 | α−オレフィン・(メタ)アクリル酸エステル共重合体の製造方法ならびにα−オレフィン・(メタ)アクリル酸エステル共重合体 |
CN102066392B (zh) * | 2008-06-19 | 2015-01-14 | 加利福尼亚大学董事会 | Pd(ii)和ni(ii)络合物的粘土活化 |
FR2937643B1 (fr) * | 2008-10-27 | 2011-10-14 | Arkema France | Nouveaux copolymeres a blocs d'olefines polaires et apolaires |
JP4524335B2 (ja) * | 2008-10-30 | 2010-08-18 | 日本ポリプロ株式会社 | 新規な金属錯体ならびにそれを用いたα−オレフィン重合体の製造方法およびα−オレフィンと(メタ)アクリル酸エステル共重合体の製造方法 |
CN102292344B (zh) * | 2008-11-20 | 2014-12-10 | 日本聚乙烯株式会社 | 新三芳基膦或三芳基胂化合物及α-烯烃聚合催化剂、三元共聚物和α-烯烃/(甲基)丙烯酸系共聚物的制法 |
JP5666808B2 (ja) * | 2009-02-05 | 2015-02-12 | 日本ポリエチレン株式会社 | 新規なトリアリールホスフィン又はトリアリールアルシン化合物及びそれらを使用するα−オレフィン系重合触媒並びにα−オレフィン系共重合体の製造方法。 |
EP2470575B9 (en) * | 2009-08-28 | 2014-01-15 | The University of Tokyo | Production method of copolymer of allyl monomer containing polar group |
JP5622376B2 (ja) * | 2009-10-20 | 2014-11-12 | 日本ポリプロ株式会社 | 新規な金属錯体ならびにそれを用いたα−オレフィン重合体の製造方法およびα−オレフィンとプロペン酸誘導体エステル共重合体の製造方法 |
JP5945449B2 (ja) * | 2011-04-27 | 2016-07-05 | 日本ポリエチレン株式会社 | 新規なトリアリールホスフィン又はトリアリールアルシン化合物及びそれらによるオレフィン系重合触媒並びにオレフィン系共重合体の製法 |
JP6750936B2 (ja) * | 2014-10-15 | 2020-09-02 | 日本ポリエチレン株式会社 | エチレン系アイオノマーの製造方法及びエチレン系アイオノマー |
US11066545B2 (en) * | 2016-08-25 | 2021-07-20 | University Of Florida Research Foundation, Inc. | Lubricious structures, methods of making them, and methods of use |
CN109694435A (zh) * | 2017-10-24 | 2019-04-30 | 中国石油化工股份有限公司 | 一种烯烃-不饱和羧酸聚合物及其制备方法 |
EP3733725A4 (en) * | 2017-12-25 | 2021-03-31 | Japan Polyethylene Corporation | MULTINARY POLAR GROUP OLEFIN COPOLYMER |
US11739171B2 (en) | 2018-03-28 | 2023-08-29 | Japan Polyethylene Corporation | Method for producing α-olefin/(meth)acrylic acid ester copolymer |
EP3936535B1 (en) * | 2019-03-04 | 2022-12-28 | Japan Polyethylene Corporation | Multi-component ionomer |
JP2022159228A (ja) | 2021-03-31 | 2022-10-17 | 日本ポリケム株式会社 | オレフィン系重合体の重合触媒 |
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EP0589527B1 (en) | 1992-09-21 | 1999-07-28 | Montell Technology Company bv | Polymerization process |
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FR2752237B1 (fr) * | 1996-08-12 | 1998-09-18 | Atochem Elf Sa | Procede de polymerisation ou copolymerisation radicalaire controlee de monomeres (meth)acryliques et vinyliques et (co)polymeres obtenus |
WO1998030610A1 (en) | 1997-01-14 | 1998-07-16 | E.I. Du Pont De Nemours And Company | Polymerization of ethylene |
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EP1290043A2 (en) * | 2000-05-31 | 2003-03-12 | E.I. Du Pont De Nemours And Company | Polymerization of olefins |
EP1292623A2 (en) * | 2000-05-31 | 2003-03-19 | E. I. du Pont de Nemours and Company | Polymerization of olefins |
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US20030130452A1 (en) * | 2001-10-12 | 2003-07-10 | Johnson Lynda Kaye | Copolymers of ethylene with various norbornene derivatives |
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CN1563111A (zh) * | 2004-03-19 | 2005-01-12 | 中国科学院上海有机化学研究所 | 催化烯烃聚合的方法 |
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US7833927B2 (en) * | 2005-08-31 | 2010-11-16 | Rohm And Haas Company | Single site palladium catalyst complexes |
CA2620884C (en) * | 2007-02-28 | 2011-07-12 | Rohm And Haas Company | Composition and method for preparing copolymers of polar and non-polar olefins substantially free of free radical intiated polymer |
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KR20070111412A (ko) | 2007-11-21 |
JP2007077395A (ja) | 2007-03-29 |
CA2556347C (en) | 2011-07-05 |
EP1760097B1 (en) | 2015-03-25 |
EP1760097A2 (en) | 2007-03-07 |
CN1923866B (zh) | 2010-10-06 |
US7635739B2 (en) | 2009-12-22 |
TW200718717A (en) | 2007-05-16 |
CA2556347A1 (en) | 2007-02-28 |
EP1760097A3 (en) | 2007-06-13 |
KR100856692B1 (ko) | 2008-09-04 |
CN1923866A (zh) | 2007-03-07 |
US20070049712A1 (en) | 2007-03-01 |
JP4799322B2 (ja) | 2011-10-26 |
KR100881446B1 (ko) | 2009-02-06 |
TWI331613B (en) | 2010-10-11 |
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