JP2007063409A5 - - Google Patents
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- JP2007063409A5 JP2007063409A5 JP2005251303A JP2005251303A JP2007063409A5 JP 2007063409 A5 JP2007063409 A5 JP 2007063409A5 JP 2005251303 A JP2005251303 A JP 2005251303A JP 2005251303 A JP2005251303 A JP 2005251303A JP 2007063409 A5 JP2007063409 A5 JP 2007063409A5
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- Prior art keywords
- cyclic olefin
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- producing
- compound
- halogen
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- -1 cyclic olefin compound Chemical class 0.000 claims description 13
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 9
- 239000004713 Cyclic olefin copolymer Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- JFNLZVQOOSMTJK-UHFFFAOYSA-N Norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000003623 transition metal compounds Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N Cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N Cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000001639 boron compounds Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- URYYVOIYTNXXBN-UHFFFAOYSA-N cyclooctene Chemical compound [CH]1[CH]CCCCCC1 URYYVOIYTNXXBN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004913 cyclooctene Substances 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002829 nitrogen Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 230000000737 periodic Effects 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 239000004711 α-olefin Substances 0.000 claims description 2
- SIHWESHIQGPCBP-UHFFFAOYSA-N hexadec-4-ene Chemical compound CCCCCCCCCCCC=CCCC SIHWESHIQGPCBP-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- SDTYFWAQLSIEBH-UHFFFAOYSA-N undec-3-ene Chemical compound CCCCCCCC=CCC SDTYFWAQLSIEBH-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
Description
（１）下記一般式（１）で表される遷移金属化合物（Ａ）及び有機アルミニウムオキシ化合物又は有機ホウ素化合物から選ばれる１種以上の活性化剤（Ｂ）からなる重合触媒の存在下、エチレン及び／又は炭素数３〜２０のα−オレフィンと、シクロペンテン、シクロヘプテン、シクロオクテン及び二重結合を形成する炭素原子とそれに隣接する炭素原子との結合角が１２０°よりも小さいか、又は１２０°よりも大きい下記一般式（３）で表される化合物からなる群より選ばれる少なくとも１種類の環状オレフィン化合物の環を構成する二重結合との共重合を行うことにより、環状オレフィンの含有量が１２．７ｍｏｌ％以上のランダム共重合体を製造することを特徴とする環状オレフィン系共重合体の製造方法。 (1) Ethylene in the presence of a polymerization catalyst comprising a transition metal compound (A) represented by the following general formula (1) and one or more activators (B) selected from organic aluminum oxy compounds or organic boron compounds And / or the bond angle between the C3-C20 α-olefin and the carbon atom forming the cyclopentene, cycloheptene, cyclooctene and double bond and the adjacent carbon atom is smaller than 120 ° or 120 ° By performing copolymerization with a double bond constituting a ring of at least one cyclic olefin compound selected from the group consisting of compounds represented by the following general formula (3) , the cyclic olefin content is increased. A method for producing a cyclic olefin copolymer, comprising producing a random copolymer of 12.7 mol% or more .
（式中、Ｍは周期律表４族の遷移金属を表す。Ｘは水素、ハロゲン又は炭素数１〜２０のアルキル基、アルコキシ基、アリール基、アリロキシ基、アラルキル基を表す。Ｌ又はＸは、各々独立に、同一であっても良いし異なっていても良い。ｍは１〜３の整数を表す。Ｒ１〜Ｒ５は各々同じでも異なっていても良く、水素、ハロゲン又は炭素数１〜２０のアルキル基、アルコキシ基、アリール基、アリロキシ基からなり、任意の２つ又は３つが縮合し環を形成していても良い。環には共役２重結合を含んだ芳香族性を有するものも含む。） (In the formula, M represents a transition metal of Group 4 of the periodic table. X represents hydrogen, halogen, or an alkyl group having 1 to 20 carbon atoms, an alkoxy group, an aryl group, an allyloxy group, or an aralkyl group. L or X represents Each independently may be the same or different, m represents an integer of 1 to 3. R 1 to R 5 may be the same or different and each may be hydrogen, halogen or carbon number 1 It consists of ˜20 alkyl groups, alkoxy groups, aryl groups, and aryloxy groups, and any two or three may be condensed to form a ring, which has aromaticity including a conjugated double bond. Including things.)
（式中、Ｒ(Wherein R ６6 〜Ｒ~ R １７17 は各々独立して互いに同一でも異なっていてもよく、水素原子、ハロゲン原子、ハロゲンで置換されていてもよい炭化水素基、酸素を含む置換基または窒素原子を含む置換基を示し、ＲEach independently may be the same as or different from each other, and each represents a hydrogen atom, a halogen atom, a hydrocarbon group optionally substituted with a halogen, a substituent containing oxygen or a substituent containing a nitrogen atom; １４14 〜Ｒ~ R １７17 は互いに結合して単環又は多環を形成していてよく、かつその単環または多環が二重結合を有していてもよく、またＲMay be bonded to each other to form a monocyclic or polycyclic ring, and the monocyclic or polycyclic ring may have a double bond, and R １４14 とＲAnd R １５15 とでアルキリデン基を形成していてもよい。ｎは０〜２の整数を表す。）And an alkylidene group may be formed. n represents an integer of 0 to 2. )
（２）前記環状オレフィン化合物がノルボルネンであることを特徴とする上記（１）に記載の環状オレフィン系共重合体の製造方法。
（３）前記環状オレフィン化合物が、トリシクロ［４．４．０．１ ２．５ ］−３−ウンデセンであることを特徴とする上記（１）に記載の環状オレフィン系共重合体の製造方法。
（４）前記環状オレフィン化合物が、ペンタシクロ［６．６．１．１ ３．６ ．０ ２．７ ．０ ９．１４ ］−４−ヘキサデセンであることを特徴とする上記（１）に記載の環状オレフィン系共重合体の製造方法。
（５）前記遷移金属化合物（Ａ）の一般式（１）におけるＲ １ 〜Ｒ ５ が水素、ＭがＴｉ、Ｘが塩素、ｍ＝１であり、前記環状オレフィン化合物がノルボルネンであることを特徴とする上記（１）に記載の環状オレフィン系共重合体の製造方法。
(2) The method for producing a cyclic olefin copolymer according to (1), wherein the cyclic olefin compound is norbornene.
(3) The method for producing a cyclic olefin copolymer as described in (1) above , wherein the cyclic olefin compound is tricyclo [4.4.0.1 2.5 ] -3-undecene.
(4) The cyclic olefin compound is pentacyclo [6.6.1.1 3.6 . 0 2.7 . 0 9.14 ] -4-hexadecene, The method for producing a cyclic olefin copolymer according to (1) above.
(5) R 1 to R 5 in the general formula (1) of the transition metal compound (A) are hydrogen, M is Ti, X is chlorine, m = 1, and the cyclic olefin compound is norbornene. The manufacturing method of the cyclic olefin type copolymer as described in said (1).
Claims (5)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005251303A JP2007063409A (en) | 2005-08-31 | 2005-08-31 | Process for producing cycloolefin copolymer |
| PCT/JP2006/317063 WO2007026743A1 (en) | 2005-08-31 | 2006-08-30 | Process for production of cycloolefin copolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005251303A JP2007063409A (en) | 2005-08-31 | 2005-08-31 | Process for producing cycloolefin copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007063409A JP2007063409A (en) | 2007-03-15 |
| JP2007063409A5 true JP2007063409A5 (en) | 2008-08-28 |
Family
ID=37808828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005251303A Pending JP2007063409A (en) | 2005-08-31 | 2005-08-31 | Process for producing cycloolefin copolymer |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP2007063409A (en) |
| WO (1) | WO2007026743A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7558658B2 (en) | 2019-01-25 | 2024-10-01 | 三井化学株式会社 | Olefin Polymerization Catalysts |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6358852B2 (en) * | 2014-05-23 | 2018-07-18 | ポリプラスチックス株式会社 | Method for producing cyclic olefin copolymer |
| JP6847719B2 (en) * | 2017-03-13 | 2021-03-24 | 三井化学株式会社 | Methods for Producing Transition Metal Compounds, Catalysts for Olefin Polymerization, and Olefin Polymers |
| CN110272526B (en) * | 2018-03-16 | 2021-10-19 | 中国石油化工股份有限公司 | Catalyst composition for ethylene polymerization and application thereof |
| JP7175426B2 (en) * | 2020-07-31 | 2022-11-18 | ポリプラスチックス株式会社 | Method for producing cyclic olefin copolymer |
| JP6997887B2 (en) * | 2021-01-18 | 2022-01-18 | 三井化学株式会社 | Methods for Producing Transition Metal Compounds, Catalysts for Olefin Polymerization, and Olefin Polymers |
| CN118660917A (en) | 2022-03-11 | 2024-09-17 | 三井化学株式会社 | Cyclic olefin copolymer, cyclic olefin copolymer composition, molded article, and optical part |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2215444C (en) * | 1997-09-15 | 2005-08-02 | Stephen John Brown | Catalyst having a ketimide ligand |
| CA2311068C (en) * | 2000-06-08 | 2010-03-09 | Nova Chemicals Corporation | Process to prepare ethylene propylene elastomer |
| EP2261269B1 (en) * | 2003-07-09 | 2016-11-09 | Arlanxeo Netherlands B.V. | Process for the production of a polymer comprising monomeric units of ethylene, an alpha-olefin and a vinyl norbornene |
| EP1730205B1 (en) * | 2004-03-17 | 2012-09-26 | Lanxess Elastomers B.V. | Polimerization catalyst comprising an amidine ligand |
-
2005
- 2005-08-31 JP JP2005251303A patent/JP2007063409A/en active Pending
-
2006
- 2006-08-30 WO PCT/JP2006/317063 patent/WO2007026743A1/en active Application Filing
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7558658B2 (en) | 2019-01-25 | 2024-10-01 | 三井化学株式会社 | Olefin Polymerization Catalysts |
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