TWI396700B - 過渡金屬化合物,烯烴聚合用觸媒及烯烴系聚合體之製造方法 - Google Patents
過渡金屬化合物,烯烴聚合用觸媒及烯烴系聚合體之製造方法 Download PDFInfo
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- TWI396700B TWI396700B TW095118610A TW95118610A TWI396700B TW I396700 B TWI396700 B TW I396700B TW 095118610 A TW095118610 A TW 095118610A TW 95118610 A TW95118610 A TW 95118610A TW I396700 B TWI396700 B TW I396700B
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- zirconium dichloride
- butyl
- fluorenyl
- tert
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- 238000000034 method Methods 0.000 title claims description 29
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- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- HPNURIVGONRLQI-UHFFFAOYSA-K trifluoroeuropium Chemical compound F[Eu](F)F HPNURIVGONRLQI-UHFFFAOYSA-K 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- OMQSJNWFFJOIMO-UHFFFAOYSA-J zirconium tetrafluoride Chemical class F[Zr](F)(F)F OMQSJNWFFJOIMO-UHFFFAOYSA-J 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- 229910006592 α-Sn Inorganic materials 0.000 description 1
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- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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Description
本發明關於一種可有效作為烯烴聚合用觸媒成分且具有新穎的特定構造之過渡金屬化合物,於該過渡金屬化合物之製造中有用之中間體,含有該過渡金屬化合物之烯烴聚合用觸媒,以及使用該聚合用觸媒的烯烴系聚合體之製造方法。
近年,作為烯烴聚合用之均勻系觸媒,可知有二茂金屬化合物。使用該二茂金屬化合物聚合烯烴之方法,特別是立體規則性地聚合α-烯烴之方法,自W.Kaminsky等人報告有整規聚合(Angew.Chem.Int.Ed.Engl.,24,507(1985))以來,已被廣為研究。
已知於使用該二茂金屬化合物之α-烯烴聚合中,將取代基導入至二茂金屬化合物之配位基之環戊二烯基環上,或者使2個環戊二烯基環交聯,藉此大幅改變所得之α-烯烴聚合體之立體規則性或分子量。
例如,揭示有於丙烯之聚合觸媒中使用具有環戊二烯基環與茀基環所交聯之配位基的二茂金屬化合物之情形時,由立體規則性之觀面而言,可藉二甲基亞甲基(環戊二烯基)(茀基)二氯化鋯獲得間規聚丙烯(J.Am.Chem.Soc.,110,6255(1988)),藉於環戊二烯基環之3位上導入有甲基之二甲基亞甲基(3-甲基環戊二烯基)(茀基)二氯化鋯獲得半整規(hemiisotactic)聚丙烯(日本專利特開平3-193796),同樣地藉導入了第三丁基之二甲基亞甲基(3-第三丁基-環戊二烯基)(茀基)二氯化鋯獲得整規聚丙烯(日本專利特開平6-122718)。又,揭示有經由二甲基亞甲基(3-第三丁基-5-甲基環戊二烯基)(茀基)二氯化鋯,於茀環之3,6位上導入第三丁基之二甲基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基茀基)二氯化鋯者,將得到整規立體規則性經提高的聚丙烯(WO01/27124)。
又,由分子量之觀點而言,已報告有:經由二甲基亞甲基(環戊二烯基)(茀基)二氯化鋯,將環戊二烯基環與茀環之交聯部改變為二苯基亞甲基交聯之二苯基亞甲基(環戊二烯基)(茀基)二氯化鋯者將獲得高分子量之間規聚丙烯(日本專利特開平2-274703);經由二甲基亞甲基(3-(2-金剛烷基)-環戊二烯基)(茀基)二氯化鋯,使交聯部改變為二苯基亞甲基交聯之二苯基亞甲基(3-(2-金剛烷基)-環戊二烯基)(茀基)二氯化鋯者,將獲得高分子量之整規-半整規聚丙烯(Organometallics,21,934(2002));經由二甲基亞甲基(3-第三丁基-環戊二烯基)(茀基)二氯化鋯,於環戊二烯基環之5位導入甲基之二甲基亞甲基(3-第三丁基-5-甲基環戊二烯基)(茀基)二氯化鋯者,將獲得高分子量之整規聚丙烯(日本專利特表2001-526730)。
進而,揭示有:藉於環戊二烯基環相鄰2個位置上導入取代基之二甲基亞甲基(3-第三丁基-2-甲基環戊二烯基)(茀基)二氯化鋯或二苯基亞甲基(3,4-二甲基環戊二烯基)(茀基)二氯化鋯,分別較二甲基亞甲基(3-第三丁基-5-甲基環戊二烯基)(茀基)二氯化鋯、二苯基亞甲基(3-甲基環戊二烯基)(茀基)二氯化鋯,獲得低分子量之聚丙烯(日本專利特表2001-526730、特開平10-226694)。
如此,關於含有環戊二烯基環與茀環所交聯之配位基的二茂金屬化合物已有許多報告例。另一方面,報告例對於茀環3,6位之取代基種類係極端地限定。具體而言,已知於茀環3,6位上取代第三丁基之二茂金屬化合物,或茀環之2,3-位、6,7-位形成飽和6員環之二茂金屬化合(WO01/27124),但均無任何具有於3,6-上取代不飽和鍵結之茀環的二茂金屬化合物之合成.聚合之報告例。此外,亦無關於在3,6位上取代碳-碳不飽和鍵結之茀衍生物的合成報告例。因此無法知曉此種二茂金屬化合物具有何等之性能。
一般而言,由聚合活性、立體規則性或分子量等之方面而言,業者期望進一步改良使用該等二茂金屬化合物之聚合用觸媒。
又,另一方面,茀化合物近年來亦使用於有機電致發光元件等中,製造於3,6-上取代不飽和鍵結之茀亦有助於該等領域。
專利文獻1:日本專利特開平3-193796號公報專利文獻2:日本專利特開平6-122718號公報專利文獻3:WO01/27124專利文獻4:日本專利特開平2-274703號公報專利文獻5:日本專利特表2001-526730號公報專利文獻6:日本專利特開平10-226694號公報
非專利文獻1:Angew.Chem.Int.Ed.Engl.,24,507(1985)非專利文獻2:J.Am.Chem.Soc.,110,6255(1988)非專利文獻3:Organometallics,21,934(2002)
本發明之目的在於提供一種可有效作為有機電致發光元件或烯烴聚合用過渡金屬化合物之中間體的新穎茀化合物,以及作為烯烴聚合用觸媒成分之具有該茀環作為部分結構之過渡金屬化合物,含該過渡金屬化合物之烯烴聚合用觸媒,以及使用該觸媒製造烯烴系聚合體的方法。
本發明係用於解決上述問題者,發現藉由在3,6位上取代不飽和鍵結之茀化合物、具有含該茀之配位基之有用且新穎的過渡金屬化合物、含有該過渡金屬化合物之烯烴聚合用觸媒、以及使用該聚合用觸媒之烯烴系聚合體的製造方法,將達成本發明目的,並基於此而完成本發明。本發明之茀、以及過渡金屬化合物係分別為下述通式[I]以及[Ⅱ]所表示之過渡金屬化合物。
[a]:一種茀衍生物,其特徵在於如下述通式[I]所示。
[b]:如[a]之茀衍生物,其中,上述通式[I]中,R1
、R2
為氫。
[c]:如[b]之茀衍生物,其中,上述通式[I]中,R1
、R2
、R3
、R8
、R9
、R1 4
為氫。
[d]:如[c]之茀衍生物,其中,上述通式[I]中,R1
、R2
、R3
、R8
、R9
、R1 4
為氫,R4
與R5
及/或R1 2
與R1 3
係相互鍵結形成環。
[e]:如[d]之茀衍生物,其中,上述通式[I]中,R1
、R2
、R3
、R8
、R9
、R1 4
為氫,R4
與R5
及/或R1 2
與R1 3
係相互鍵結形成5或6員環。
[f]:如[e]之茀衍生物,其如下述通式[Ⅱ]所示。
[g]:如[f]之茀衍生物,其中,上述通式[Ⅱ]中,R1 5
、R1 6
、R1 8
、R1 9
、R2 1
、R2 2
為甲基,R1 7
、R2 0
為氫原子。
[h]:一種過渡金屬化合物,其特徵為如下述通式[Ⅲ]所示。
[i]:如[h]之過渡金屬化合物,其中,上述通式[Ⅲ]中,R2 4
、R2 6
為氫。
[j]:一種烯烴聚合用觸媒,其特徵為含有[h]或[i]任一項之過渡金屬化合物。
[k]:一種烯烴聚合用觸媒,其特徵為至少含有一種自以下選擇之化合物:(A)[h]或[i]任一項之過渡金屬化合物、與(B)(B-1)有機金屬化合物、(B-2)有機鋁氧化物化合物、(B-3)與過渡金屬化合物(A)反應形成離子對之化合物。
[l]:一種烯烴系聚合體之製造方法,其係於[j]或[k]之烯烴聚合用觸媒存在下,使選自乙烯以及α-烯烴之1種以上之單體聚合的方法,其特徵為,至少1種單體為乙烯或丙烯。
[m]:如[l]之烯烴系聚合體之製造方法,其中,上述通式[Ⅱ]所表示之過渡金屬化合物係以載持於支持體上之形態使用。
本發明提供一種藉由使用新穎茀衍生物、以及含有該衍生物之過渡金屬化合物(二茂金屬化合物)、含有該過渡金屬化合物之烯烴聚合用觸媒,而依非常高之活性製造有用之烯烴系聚合體的方法。
以下,依序說明:上述通式[I]所表示之茀衍生物,上述通式[Ⅲ]所表示之過渡金屬化合物,較佳的茀衍生物之例示,較佳的過渡金屬化合物之例示,本發明之茀衍生物的製造方法,本發明之過渡金屬化合物的製造方法,將本發明之過渡金屬化合物供給於烯烴聚合用觸媒時之較佳形態,繼而最後於含有本發明之過渡金屬化合物的烯烴聚合用觸媒之存在下製造烯烴系聚合體之方法。
本發明之茀衍生物係以上述通式[I]表示。通式[I]中R1
、R2
、R3
、R5
、R6
、R7
、R8
、R9
、R1 0
、R1 1
、R1 2
、R1 4
係選自氫、烴基、含矽基、含硫基、含氧基、含氮基、含鹵素基,可分別相同亦可不同。作為上述烴基,可列舉甲基、乙基、正丙基、烯丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基等直鏈狀烴基;異丙基、第三丁基、戊基、3-甲基戊基、1,1-二乙基丙基、1,1-二甲基丁基、1-甲基-1-丙基丁基、1,1-丙基丁基、1,1-二甲基-2-甲基丙基、1-甲基-1-異丙基-2-甲基丙基等支鏈狀烴基;環戊基、環己基、環庚基、環辛基、降基、金剛烷基、甲基環己基、甲基金剛烷基等環狀飽和烴基;苯基、甲苯基、萘基、聯苯基、菲基、蒽基等環狀不飽和烴基;苄基、異丙苯基、1,1-二苯基乙基、三苯基甲基等環狀不飽和烴基所取代之飽和烴基等。作為含氧基可列舉甲氧基、乙氧基、苯氧基、呋喃基等。作為含氮基可列舉N-甲基胺基、N,N-二甲基胺基、N-苯基胺基、比林基(pyryl)等。作為含硫基可列舉甲硫基、噻吩基等。作為含矽基,可列舉三甲基矽烷基、三乙基矽烷基、二甲基苯基矽烷基、二苯基甲基矽烷基、三苯基矽烷基等。作為含鹵素基可列舉氟原子、三氟甲基、2,2,2-三氟乙基、氟苯基、二氟苯基、三氟苯基、五氟苯基、三氟甲基苯基、雙(三氟甲基)等含氟基,氯原子、三氯甲基、2,2,2-三氯乙基、氯苯基、二氯苯基、三氯苯基、五氯苯基、三氯甲基苯基、雙(三氯甲基)等含氯基,溴原子、溴化苯基等含溴基,碘原子、碘苯基等含碘基等。
通式[I]中,較佳的是R1
、R2
、R3
、R5
、R6
、R7
、R8
、R9
、R1 0
、R1 1
、R1 2
、R1 4
為氫、碳數1~20之烴基、含有碳數0~20之含矽基、含硫基、含氧基、含氮基、含鹵素基。作為碳數1~20之烴基、含有碳數0~20之含矽基、含硫基、含氧基、含氮基、含鹵素基,可例示上述之取代基。
又,R1
至R1 4
之相鄰接之取代基可相互鍵結形成環,亦可與接續該等之原子一同形成碳數1~20之亦可含有氧原子、氮原子、硫原子之環。又,R4
與R5
係可成為一體形成2價取代基之Ra,R1 2
與R1 3
亦可成為一體形成2價取代基之Rb。Ra、Rb為除了伸乙烯基以外之2價取代基,較佳為碳數1~20之烴基、含有碳數0~20之含矽基、含硫基、含氧基、含氮基、含鹵素基。作為上述2價烴基之例,可列舉亞甲基、伸乙基、亞乙基、伸丙基、亞異丙基、二甲基伸乙基、三甲基伸乙基、四甲基伸乙基、三亞甲基、三甲基三亞甲基、六甲基三亞甲基、四亞甲基、八甲基四亞甲基、伸丙烯基、亞乙烯基、亞環己基、1,2-伸環己烯基等。作為含矽基,可列舉亞矽烷基、二甲基亞矽烷基、二矽烯(disilene)基、四甲基二矽烯基、矽伸乙基(silaethylene) 、二甲基矽伸乙基(Dimethyl silaethylene)、四甲基矽伸乙基(tetramethyl silaethylene)等。作為含硫基,可列舉硫原子、硫伸乙基(thiaethylene)、二甲基硫伸乙基(Dimethyl thiaethylene)、硫酮基亞甲基(thioxomethylene)等。作為含氧基’可列舉氧原子、氧伸乙基(oxaethylene)、二甲基氧伸乙基(Dimethyl oxaethylene)、側氧基亞甲基(oxo methylene)等。作為含氮基可列舉亞胺基、甲基亞胺基,苯基亞胺基,氮雜伸乙基(azaethylene),N-甲基氮雜伸乙基,N-苯基氮雜伸乙基,三甲基氮雜伸乙基,亞胺基亞甲基,N-甲基亞胺基亞甲基等。作為含鹵素基,可列舉氟亞甲基、二氟亞甲基、(三氟甲基)亞甲基、雙(三氟甲基)亞甲基、四氟伸乙基、氯亞甲基、二氯亞甲基、二溴亞甲基、二碘亞甲基等。
作為此種鄰接之取代基形成環之茀衍生物之例,具體而言可列舉下式[Ⅱ]。
通式[Ⅱ]中R1 5
、R1 6
、R1 7
、R1 8
、R1 9
、R2 0
、R2 1
、R2 2
係選自氫、烴基、含矽基、含硫基、含氧基、含氮基、含鹵素基,可分別相同亦可不同。較佳係R1 5
、R1 6
、R1 7
、R1 8
、R1 9
、R2 0
、R2 1
、R2 2
為氫、碳數1~20之烴基、含碳數0~20之含矽基、含硫基、含氧基、含氮基。作為碳數1~20之烴基、含碳數0~20之含矽基、含硫基、含氧基、含氮基、含鹵素基,可例示上述之取代基。更佳為氫或碳數1~20之烴基,特佳為氫或甲基。
本發明之過渡金屬化合物以上述通式[Ⅲ]表示。通式[Ⅲ]中R2 3
、R2 4
、R2 5
、R2 6
、R2 7
、R2 8
係選自氫、烴基、含矽基、含硫基、含氧基、含氮基、含鹵素基,可分別相同亦可不同,R2 3
至R2 8
之相鄰接之取代基亦可相互鍵結形成環。M為第4族過渡金屬,Y為碳原子,Q為選自鹵素、烴基、陰離子配位基或可以孤立電子配位之中性配位基之相同或不同組合,j為1~4之整數。Z為含有上述茀衍生物之亞茀基。
作為上述烴基,可列舉甲基、乙基、正丙基、烯丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基等直鏈狀烴基;異丙基、第三丁基、戊基、3-甲基戊基、1,1-二乙基丙基、1,1-二甲基丁基、1-甲基-1-丙基丁基、1,1-丙基丁基、1,1-二甲基-2-甲基丙基、1-甲基-1-異丙基-2-甲基丙基等支鏈狀烴基;環戊基、環己基、環庚基、環辛基、降基、金剛烷基、甲基環己基、甲基金剛烷基等環狀飽和烴基;苯基、甲苯基、萘基、聯苯基、菲基、蒽基等環狀不飽和烴基;苄基,異丙苯基,1,1-二苯基乙基,三苯基甲基等環狀不飽和烴基所取代之飽和烴基等。作為含氧基可列舉甲氧基、乙氧基、苯氧基、呋喃基等。作為含氮基可列舉N-甲基胺基、N,N-二甲基胺基、N-苯基胺基、比林基(pyryl)等。作為含硫基可列舉甲硫基、噻吩基等。作為含矽基可列舉三甲基矽烷基、三乙基矽烷基、二甲基苯基矽烷基、二苯基甲基矽烷基、三苯基矽烷基等。作為含鹵素基,可列舉氟原子、三氟甲基、2,2,2-三氟乙基、氟苯基、二氟苯基、三氟苯基、五氟苯基、三氟甲基苯基、雙(三氟甲基)等含氟基,氯原子、三氯甲基、2,2,2-三氯乙基、氯苯基、二氯苯基、三氯苯基、五氯苯基、三氯甲基苯基、雙(三氯甲基)等含氯基,溴原子、溴苯基等含溴基,碘原子、碘苯基等含碘基等。
上述通式[Ⅲ]中,較佳係環戊二烯基環上取代之R2 3
、R2 4
、R2 5
、R2 6
為氫或碳數1~20之烴基。作為碳數1~20之烴基,可例示上述烴基。更佳係R2 4
、R2 6
為氫。特佳係R2 3
及/或R2 5
為碳數1~20之烴基。作為碳數1~20之烴基,可例示上述之烴基。
上述通式[I]中,使環戊二烯基環與茀環交聯之Y為碳原子。較佳係該Y上取代之R2 7
及R2 8
為氫、碳數1~20之烴基、碳數0~20之含矽基、含硫基、含氧基、含氮基、含鹵素基。作為碳數1~20之烴基、碳數0~20之含矽基、含硫基、含氧基、含氮基、含鹵素基,可例示上述取代基。該等可相互相同亦可不同,亦可相互鍵結形成環。作為R1 3
與R1 4
相互鍵結形成環之取代基,可列舉環亞戊基、環亞己基、環亞庚基、亞芴基、10-氫亞蒽基、二苄基亞環庚二烯基等。
上述通式[Ⅲ]中,M為第4族過渡金屬,具體而言可列舉Ti、Zr、Hf等。又,Q選自鹵素、烴基、陰離子配位基或可以孤立電子對配位之中性配位基之相同或不同之組合。j為1~4之整數,j為2以上時,Q既可相同亦可不同。作為鹵素之具體例,可列舉氟、氯、溴、碘;作為烴基之具體例,可列舉與上述相同者。作為陰離子配位基之具體例,可列舉甲氧基、第三丁氧基、苯氧基等烷氧基;醋酸酯、苯甲酸酯等羧酸酯基;甲磺酸酯、甲苯磺酸酯等磺酸酯基;二甲基醯胺基、二異丙基醯胺基、甲基苯胺基、二苯基醯胺基等醯胺基等。作為可以孤立電子對配位之中性配位基之具體例,可列舉三甲基膦、三乙基膦、三苯基膦、二苯基甲基膦等有機磷化合物,四氫呋喃、二乙醚、二烷、1,2-二甲氧基乙烷等醚類等。較佳係Q至少有1個為鹵素或烷基。
作為本發明較佳之茀衍生物,可列舉:1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀、1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀、1,3,6,
8-四甲基-1H,8H-二環戊[b,h]茀、3,6-二甲基-1H,8H-二環戊[b,h]茀、1H,8H-二環戊[b,h]茀、1,1,3-三甲基-1H-環戊[b]茀、1,3-二甲基-1H-環戊[b]茀、1,1-二甲基-1H-環戊[b]茀基茀、1-甲基-1H-環戊[b]茀、3-甲基-1H-環戊[b]茀、2,7-二甲基-1H,8H-二環戊[b,h]茀、2-甲基-1H,8H-二環戊[b,h]茀、1,1,2,3,6,7,8,8-八甲基-1H,8H-二環戊[b,h]茀、1,1,2,7,8,8-六甲基-1H,8H-二環戊[b,h]茀、3,6-二異丙基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀、3,6-二異丙基-1H,8H-二環戊[b,h]茀、3,6-二異丙基-1,3-二甲基-1H-環戊[b]茀、3-異丙基-1,1-二甲基-1H-環戊[b]茀基茀、3-異丙基-1-甲基-1H-環戊[b]茀、3,6-二異丙基-2,7-二甲基-1H,8H-二環戊[b,h]茀、3,6-二異丙基-2-甲基-1H,8H-二環戊[b,h]茀、3,6-二-第三丁基-1,1,2,7,8,8-六甲基-1H,8H-二環戊[b,h]茀、3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀、3,6-二-第三丁基-1H,8H-二環戊[b,h]茀、3,6-二-第三丁基-1,3-二甲基-1H-環戊[b]茀、3-第三丁基-1,1-二甲基-1H-環戊[b]茀基茀、3-第三丁基-1-甲基-1H-環戊[b]茀、3,6-二-第三丁基-2,7-二甲基-1H,8H-二環戊[b,h]茀、3,6-二-第三丁基-2-甲基-1H,8H-二環戊[b,h]茀、3,6-二-第三丁基-1,1,2,7,8,8-六甲基-1H,8H-二環戊[b,h]茀、1,2,9,10-四氫-二苯并[b,h]茀、1,1,10,10-四甲基-1,2,9,10-四氫-二苯并[h,h]氟、1,10-二甲基-1,2,9,10-四氫-二苯并[b,h]茀、4,7-二甲基-1,2,9,10-四氫-二苯并[b,h]茀、1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀、1H,2H-苯并[b]茀、1,1-二甲基-1H,2H-苯并[b]茀、1,1,4-三甲基-1H,2H-苯并[b]茀、1,4-二甲基-1H,2H-苯并[b]茀、4-甲基-1H,2H-苯并[b]茀、4,7-二-第三丁基-1,2,9,10-四氫-二苯并[b,h]茀、4,7-二-第三丁基-1,1,10,10-四甲基-1,2,9,10-四氫-二苯并[b,h]茀、4,7-二-第三丁基-1,10-二甲基-1,2,9,10-四氫-二苯并[b,h]茀、4-第三丁基-1,1-二甲基-1H,2H-苯并[b]茀、4-第三丁基-1-甲基-1H,2H-苯并[b]茀、3,6-二乙烯基茀、3-乙烯基茀、3,6-二-異丙烯基茀、3-異丙烯基茀、3,6-二丙烯基茀、3-丙烯基茀、3,6-二-(2-甲基異丙烯基)茀、3-(2-甲基異丙烯基)茀、3,6-二-(2-苯基異丙烯基)茀、3-(2-苯基異丙烯基)茀、3,6-二苯乙烯基茀、3-苯乙烯基氟、3,6-二-(2-苯基)丙烯基茀、3-(2-苯基)丙烯基茀、3,6-二-(1-甲基-2-苯基)丙烯基茀、3-(1-甲基-2-苯基)丙烯基茀等。其中,本發明之茀衍生物,並非受上述例示化合物任何限制者,為包含所有滿足申請專利範圍之要旨者。
作為本發明較佳的過渡金屬化合物,可列舉亞異丙基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3,5-二甲基環戊二烯)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對-第三丁基苯基)亞甲基(環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]氟基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三-丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[h,h]茀基)二氯化鋯、雙(對氯苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二丁基亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞環己基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苄基亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、苯基亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二苯基亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二-第三丁基-1,1,8,8-四甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯、亞異丙基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二丁基亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞環己基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苄基亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、苯基亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(甲基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(乙基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苯基亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二-對甲苯基亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氟苯基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氟苯基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氯苯基亞甲基)(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氯苯基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞異丙基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞環己基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、苯基亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞異丙基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞環己基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二-對甲苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三-丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞異丙基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞環己基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二-對甲苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氟苯基亞甲基)(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞異丙基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二丁基亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞環己基(3,5-二甲基環戊烷苯基)(3,6-二乙烯基茀基)二氯化鋯、二苄基亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、苯基亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、(苯基)(乙基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二苯基亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、二對甲苯基亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氟苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氟苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對氯苯基亞甲基)(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(間氯苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3,5-二甲基環戊二烯基)(3,6-二乙烯基茀基)二氯化鋯、亞異丙基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二丁基亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞環己基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苄基亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、苯基亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苯基亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]氟基)二氯化鋯、雙(對氟苯基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,1,0-四氫-二苯并[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯基[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-環戊二烯基)(1,1,4,7,
10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并(b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間三氟乙基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞異丙基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二丁基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞環己基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苄基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二-對甲苯基亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3-第三丁基-5-乙基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞異丙基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[h,h]茀基)二氯化鋯、二丁基亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、亞環己基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苄基亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(對甲苯基)(甲基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、(苯基)(乙基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、二對甲苯基亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間三氟甲基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氟苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氟苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對氯苯基亞甲基)(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(間氯苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯、雙(對第三丁基苯基)亞甲基(3,5-二甲基環戊二烯基)(1,1,4,7,10,10-六甲基-1,2,9,10-四氫-二苯并[b,h]茀基)二氯化鋯等。其中,本發明之過渡金屬化合物並非受上述例示化合物任何侷限,係包含所有滿足申請專利範圍之要旨者。
本發明中,將骨架中具有通式[I]所表示之茀衍生物之3位及/或6位取代基之碳-碳雙鍵,以公知之方法,進一步施加化學變化之衍生物,例如以過酸等將碳-碳雙鍵環氧化之衍生物,以含活性氫之化合物將該環氧衍生物進行開環之衍生物等,在可表現本發明之聚合活性之前提下,則可不受限制地使用。
本發明之茀衍生物可以公知之方法進行製造,製造法並無特別之限制。作為公知之方法,例如可列舉本申請人之WO01/27124號公報。首先,通式[I]之前驅體化合物(1)可以通式[A]之方法進行製造。
式中,R1
~R1 4
係與通式[I]相同。X1
、X2
可分別相同亦可不同,可列舉鹵素原子、三氟甲基磺酸基、磺酸基等。藉由以公知之方法使式(1)之化合物偶合,獲得通式[I]之化合物。該偶合反應,係例如使用一種或2種以上選自除了銅、鎂、鋅、鋰、鈉、鉀等金屬,或烷基鋰、鹵化烷基鎂、鹵化芳基鎂等有機金屬化合物等之外,於氯化鎳、硝酸鎳等鎳鹽或氯化鈀、乙酸鈀等鈀鹽中根據需要添加配位基所得之過渡金屬觸媒等,於無溶劑或有機溶劑中,以-80℃~300℃範圍之條件下進行。
又,通式[Ⅱ]之化合物可以如通式[B]之方法進行製造。
式中,R1 5
~R2 2
係與通式[Ⅱ]相同。屬於中間體之以式(2)表示之化合物,係將茀與公知之α,β-不飽和酮作為原料,於無溶劑或有機溶劑中,於-100℃~200℃下,根據需要於觸媒之存在下進行。成為原料之α,β-不飽和酮並無特別之限制,例如可列舉丁-3-烯-2-酮、戊-3-烯-2-酮、4-甲基-戊-3-烯-2-酮、4-苯基-丁-3-烯-2-酮、1-苯基丙烯酮、1,3-二苯基丙烯酮、2-甲基丙烯酮、2,4-二甲基-戊-3-烯-2-酮、4,4-二甲基-戊-1-烯-3-酮、2,2-二甲基-己-4-烯-3-酮、2,2,5-三甲基-己-4-烯-3-酮等。該等相對於茀可使用1~20當量,較佳1.8~10當量,更佳2~5當量。溶劑無特別之限制,可於無溶劑或二氯甲烷、氯仿、四氯化碳、氯苯、二氯苯、硝基苯、硝基甲烷、二硫化碳、己烷、庚烷、癸烷、環己烷等溶劑中進行。該反應可根據需要添加觸媒。作為觸媒,可使用1種或2種以上之鹽酸、氯化氫、硫酸、硝酸、磷酸、聚磷酸、五氧化二磷、三氟甲基磺酸、甲基磺酸、氫氟酸、氯化鋁、氯化錫、氯化鐵、氯化鋅、氟化硼、氯化銅、氯化水銀、四氯化鈦、四氯化鋯、四氯化鉿、溴化鋁、溴化鉄、氯化鈹、鋅、氯化鎵、或雜多酸、氧化鋁、沸石等固體酸等之公知之路易斯酸。
自式(2)所表示之中間體合成通式[Ⅱ]所表示之茀衍生物係可依與上述式(2)所表示之中間體之合成相同之方式進行。再者,中間體(2)可分離,亦可不分離而直接導入至通式[Ⅱ]所示之茀衍生物中。
本發明之過渡金屬化合物可以公知之方法進行製造,製造法並無特別之限制。作為公知之製造方法,例如可列舉本申請人之WO01/27124號公報。例如,通式[Ⅲ]之化合物可依如下之步驟進行製造。首先通式[Ⅲ]之前驅體化合物(9)可以通式[C]或[D]之方法進行製造。
式中,R3
~R2 6
、Y係與通式[I]相同,L為鹼金屬。G1
、G2
為鹵素或陰離子配位基,該等可相同,或者亦可為不同之組合。又,可認為(1)、(2)、(5)係存在僅於環戊二烯基環上之雙鍵位置不同之異構體,雖僅例示該等中之一種,但亦可為環戊二烯基環中僅雙鍵位置不同之其他異構體,或亦可為該等之混合物。
作為上述通式[C]、[D]反應中所使用之鹼金屬,可列舉鋰、鈉或鉀,作為鹼土類金屬可列舉鎂、鈣。又,作為鹵素,可列舉氟、氯、溴、碘。作為陰離子配位基之具體例,可列舉甲氧基、第三丁氧基、苯氧基等烷氧基;醋酸酯、苯甲酸酯等羧酸酯基;甲磺酸酯、甲苯磺酸酯等磺酸酯基等。
繼而,以下表示自通式(9)之前驅體化合物製造過渡金屬化合物之例,但其並非為限制發明範圍者,亦可以公知之任一方法進行製造。以通式[C]、[D]之反應所得之通式(9)之前驅體化合物,係於有機溶劑中於反應溫度為-80℃~200℃之範圍與鹼金屬、氫化驗金屬或有機鹼金屬相接觸,而作成二鹼金屬鹽。作為上述反應中所使用之有機溶劑,可列舉戊烷、己烷、庚烷、環己烷、癸烷等脂肪族烴;或苯、甲苯、二甲苯等芳香族烴;或四氫呋喃、二乙基醚、二烷、1,2-二甲氧基乙烷、第三丁基甲基醚、環戊基甲基醚等醚;或二氯甲烷、氯仿等鹵化烴等。又,作為上述反應中所使用之鹼金屬,可列舉鋰、鈉、鉀等;作為氫化驗金屬,可列舉氫化鈉、氫化鉀等;作為有機鹼金屬可列舉甲基鋰、丁基鋰、苯基鋰等。
繼而可使上述所得之二鹼金屬鹽,與以通式(13)MJk………(13)(式中,M為選自週期表第4族之金屬,J為選自鹵素、陰離子配位基或可以孤立電子對配位之中性配位基之相同或不同之組合,k為3~6之整數。)所表示之化合物於有機溶煤中進行反應,合成通式[Ⅲ]表示之二茂金屬化合物。作為通式(13)所表示之化合物的較佳具體例,可列舉三價或四價鈦氟化物、氯化物、溴化物以及碘化物,四價鋯氟化物、氯化物、溴化物以及碘化物,四價鉿氟化物、氯化物、溴化物以及碘化物,或該等之四氫呋喃、二乙基醚、二烷或與1,2-二甲氧基乙烷等醚類之錯合物。又,作為可使用之有機溶劑可列舉與上述相同者。上述所得之二鹼金屬鹽與通式(13)所表示之化合物的反應,較佳係可依等莫耳反應進行,於上述有機溶劑中,於反應溫度為-80℃~200℃之範圍進行。反應所得之二茂金屬化合物可藉萃取、再結晶、昇華等方法,進行分離.精製。以如此之方法所得之本發明之過渡金屬化合物係以質子核磁共振光譜、1 3
C核磁共振光譜、質量分析、以及元素分析等分析方法進行鑒定。
繼而對使用本發明之過渡金屬化合物作為烯烴聚合觸媒之情形時之較佳形態進行說明。於使用本發明之過渡金屬化合物作為烯烴聚合用觸媒之情形時,較佳係觸媒成分含有:(A)上述過渡金屬化合物;(B)選自與(B-1)有機金屬化合物、(B-2)有機鋁氧化物化合物、以及(B-3)與過渡金屬化合物(A)反應而形成離子對之化合物之至少一種化合物;進而根據需要含有(C)粒子狀載體。
以下,對各成分加以具體說明。
作為本發明所使用之有機金屬化合物(B-1),具體而言係使用下述第1、2族以及第12、13族之有機金屬化合物。
(B-1a)通式:Ra
mAl(ORb
)nHpEq(式中,Ra以及Rb相互可相同亦可不同,表示碳數為1~15、較佳1~4之烴基,E表示鹵素原子,m為0<m≦3、n為0≦n<3、p為0≦p<3、q為0≦q<3之數,且m+n+p+q=3)所表示之有機鋁化合物。作為此種化合物之具體例,可列舉三甲基鋁、三乙基鋁、三異丁基鋁、二異丁基氫化鋁等。
(B-1b)通式:M2
A1Ra 4
(式中,M2
表示Li、Na或K,Ra
表示碳數為1~15、較佳1~4之烴基)所表示之第1族金屬與鋁之錯合烷基化物。作為此種化合物,可例示LiAl(C2
H5
)5
、LiAl(C7
H1 5
)4
等。
(B-1c)通式:Ra
Rb
M3
(式中,Ra
以及Rb
相互可相同亦可不同,表示碳數為1~15、較佳1~4之烴基,M3
為Mg、Zn或Cd)所表示之第2族或第12族金屬之二烷基化合物。上述有機金屬化合物(B-1)中,較佳為有機鋁化合物。又,此種有機金屬化合物(B-1)可單獨使用亦可將2種以上組合使用。
於本發明中使用之有機鋁氧化物化合物(B-2),可為習知公知之鋁氧烷,又,亦可為日本專利持開平2-78687號公報中例示之苯不溶性有機鋁氧化物化合物。
習知公知之鋁氧烷係例如可以下述之方法進行製造,通常為獲得碳氫化合物溶劑之溶液。
(1)於含吸著水之化合物或含結晶水之鹽類,例如氯化鎂水合物、硫酸銅水合物、硫酸鋁水合物、硫酸鎳水合物、氯化亞鈰水合物等碳氫化合物媒介懸濁液中,添加三烷基鋁等有機鋁化合物,使吸著水或結晶水與有機鋁化合物反應之方法。
(2)於苯、甲苯、二乙基醚、四氫呋喃等媒介中,使水、冰或水蒸氣直接作用於三烷基鋁等之有機鋁化合物上之方法。
(3)於癸烷、苯、甲苯等媒介中使三烷基鋁等有機鋁化合物,與氧化二甲基錫、氧化二丁基錫等之有機錫氧化物反應之方法。
再者,上述鋁氧烷亦可含有少量有機金屬成分。又,可自回收之上述鋁氧烷溶液中蒸餾去除溶劑或未反應之有機鋁化合物後,使其再溶解於溶劑中或者懸濁於鋁氧烷之貧溶劑中。作為製備鋁氧烷時所使用之有機鋁化合物,具體而言可列舉與例示為屬於上述(B-1a)之有機鋁化合物者相同之有機鋁化合物。該等中,較佳為三烷基鋁、三環烷基鋁,特佳為三甲基鋁。上述之有機鋁化合物可單獨使用1種或將2種組合使用。
又,本發明中所使用之苯基不溶性之有機鋁氧化物化合物係溶解於60℃苯中之Al成分以Al原子予以換算,通常為10%以下,較佳5%以下,特佳2%以下者,即,較佳係對於苯而言屬不溶性或難溶性者。該等之有機鋁氧化物化合物(B-2)可單獨使用1種或將2種以上組合使用。
作為與本發明中所使用之過渡金屬化合物(A)反應而形成離子對之化合物(B-3)(以下,稱為「離子化離子性化合物」)可列舉日本專利特開平1-501950號公報、日本專利特開平1-502036號公報、日本專利特開平3-179005號公報、日本專利特開平3-179006號公報、日本專利特開平3-207703號公報、日本專利特開平3-207704號公報、USP-5321106號等中所揭示之路易斯酸、離子性化合物、硼烷化合物以及碳硼烷化合物等。進而,亦可列舉雜多化合物以及異多化合物。此種離子化離子性化合物(B-3)可單獨使用或將2種以上組合使用。使用本發明之過渡金屬化合物作為烯烴聚合用觸媒之情形時,若併用作為助觸媒成分之甲基鋁氧烷等有機鋁氧化物化合物(B-2),則對烯烴化合物表現出特別高之聚合活性。
又,本發明相關之烯烴聚合用觸媒可使用上述過渡金屬化合物(A)、選自有機金屬化合物(B-1)、有機鋁氧化物化合物(B-2)、以及離子化離子性化合物(B-3)之至少1種之化合物(B),同時亦可根據需要使用載體(C)。
於本發明中使用之載體(C)為無機或有機化合物,為顆粒狀至微粒子狀之固體。作為無機化合物,較佳的為多孔質氧化物、無機氯化物、黏土、黏土礦物或離子交換性層狀化合物。
作為多孔質氧化物,具體而言係使用SiO2
、Al2
O3
、MgO、ZrO2
、TiO2
、B2
O3
、CaO、ZnO、BaO、ThO2
等,或含有該等之複合物或混合物,例如可使用天然或合成沸石、SiO2
-MgO、SiO2
-Al2
O3
、SiO2
-TiO2
、SiO2
-V2
O5
、SiO2
-Cr2
O3
、SiO2
-TiO2
-MgO等。該等中,較佳為以SiO2
及/或Al2
O3
為主成分者。此種多孔質氧化物因種類以及製法而其性狀不同,但本發明中適合使用之載體係粒徑為5~300 μ m,更佳10~100 μ m,比表面積為50~1000 m2
/g,更佳200~900 m2
/g之範圍,細孔容積為0.3~3.0 cm3
/g之範圍。此種載體根據需要於100~1000℃,較佳於150~700℃下進行燒成而使用。
作為無機氯化物可使用MgCl2
、MgBr2
、MnCl2
、MnBr2
等。無機氯化物可直接使用,亦可使用球磨機、振動磨碎機予以粉碎後使用。又,將無機氯化物溶解於醇等溶劑中之後,亦可使用藉由析出劑使之析出為微粒子狀者。
於本發明中使用之黏土係通常以黏土礦物作為主成分而構成。又,於本發明中使用之離子交換性層狀化合物為具有經由離子鍵所構成之面以相互較弱之鍵結力平行堆積之結晶結構的化合物,係可交換所含有之離子者。大部分黏土礦物為離子交換性層狀化合物。又,作為該等之黏土、黏土礦物、離子交換性層狀化合物,不限於天然產者,亦可使用人工合成物。又,作為黏土、黏土礦物或離子交換性層狀化合物,可例示黏土、黏土礦物、又、具有六方最密堆積型、銻型、CdCl2
型、CdI2
型等層狀結晶構造之離子結晶性化合物等。作為此種黏土、黏土礦物、可列舉高嶺土、膨潤土、木節土、蛙目黏土、鋁英石、矽鐵土、葉蠟石、雲母群、蒙脫石群、蛭石、綠泥石群、坡縷石、高嶺石、珍珠石、狄克石、多水高嶺土等,作為離子交換性層狀化合物,可列舉α-Zr(HAsO4
)2
.H2
O、α-Zr(HPO4
)2
、α-Zr(KPO4
)2
.3H2
O、α-Ti(HPO4
)2
、α-Ti(HAsO4
)2
.H2
O、α-Sn(HPO4
)2
.H2
O、γ-Zr(HPO4
)2
、γ-Ti(HPO4
)2
、γ-Ti(NH4
PO4
)2
.H2
O等多價金屬之結晶性酸性鹽等。最好對於本發明中使用之黏土、黏土礦物實施化學處理。作為化學處理,可使用去除附著於表面之雜質之表面處理、對黏土結晶結構造成影響之處理等任意者。作為化學處理,具體而言可列舉酸處理、鹼處理、鹽類處理、有機物處理等。
於本發明中使用之離子交換性層狀化合物,亦可為藉由利用離子交換性,將層間交換性離子與其他大體積離子進行交換,而擴大層間狀態之層狀化合物。此種大體積離子係擔負支持層狀構造之功效,通常稱之為柱(pillar)。又,將於此種層狀化合物之層間導入其他物質者稱之為嵌入(intercalation)。作為嵌入之客體化合物,可列舉TiCl4
、ZrCl4
等陽離子性無機化合物;Ti(OR)4
、Zr(OR)4
、PO(OR)3
、B(OR)3
等烷氧基金屬(R為烴基等);[Al1 3
O4
(OH)2 4
]7 +
、[Zr4
(OH)1 4
]2 +
、[Fe3
O(OCOCH3
)6
]+
等金屬氫氧化物離子等。該等化合物可單獨使用亦可將2種以上組合使用。又,嵌入該等化合物時,亦可使將Si(OR)4
、Al(OR)3
、Ge(OR)4
等烷氧基金屬(R為烴基等)等加水分解所獲得之聚合物、SiO2
等膠體狀無機化合物共存。又,作為柱,可列舉藉由將上述金屬氫氧化物離子嵌入層間後進行加熱脫水所生成之氧化物等。該等中,較佳者為黏土或黏土礦物,特佳為蒙脫石、蛭石、針鈉鈣石、鋰鎂雲母以及合成雲母。
作為有機化合物,可列舉粒徑為5~300 μ m範圍中之顆粒狀至微粒子狀固體。具體而言,可例示以乙烯、丙烯、1-丁烯、4-甲基-1-戊烯等碳數為2~14之α-烯烴作為主成分所生成之(共)聚合體,以乙烯環己烷、苯乙烯作為主成分所生成之(共)聚合體,以及該等之變形體。
本發明相關之烯烴聚合用觸媒係含有本發明之過渡金屬化合物(A)、選自有機金屬化合物(B-1)、有機鋁氧化物化合物(B-2)、以及離子化離子性化合物(B-3)中之至少1種之化合物(B),根據需要再含有載體(C),同時亦根據需要可含有下述之特定有機化合物成分(D)。
本發明中,有機化合物成分(D)可根據需要,以提高聚合性能以及生成聚合物之物性為目的而使用。作為此種有機化合物,可列舉醇類、苯酚性化合物、羧酸、磷化合物以及磺酸鹽等,但並非侷限於此。
聚合時,可任意選擇各成分之使用法、添加順序,可例示如下之方法。
(1)將成分(A)單獨加入至聚合器中之方法。
(2)將成分(A)以及成分(B)以任意順序加入至聚合器中之方法。
(3)將於載體(C)上承載有成分(A)之觸媒成分、成分(B)以任意順序加入至聚合器中之方法。
(4)將於載體(C)上承載有成分(B)之觸媒成分、成分(A)以任意順序加入至聚合器中之方法。
(5)將於載體(C)上承載有成分(A)與成分(B)之觸媒成分加入至聚合器中之方法。
上述(2)~(5)各方法中,亦可使各觸媒成分中至少2種以上預先接觸。承載有成分(B)之上述(4)、(5)各方法中,可根據需要以任意順序添加未承載之成分(B)。該情形時成分(B)可相同亦可不同。又,上述於成分(C)上承載有成分(A)之固體觸媒成分、於成分(C)上承載有成分(A)以及成分(B)之固體觸媒成分,係可預先聚合烯烴,亦可於預備聚合之固體觸媒成分上,進而承載觸媒成分。
本發明相關之烯烴系聚合體之製造方法中,係於上述烯烴聚合用觸媒之存在下,使烯烴聚合或共聚合而獲得烯烴系聚合體。於本發明中,聚合可以溶液聚合、懸濁聚合等液相聚合法或氣相聚合法之任一者實施。作為液相聚合法中使用之惰性碳氫化合物媒介,具體可列舉丙烷、丁烷、戊烷、己烷、庚烷、辛烷、癸烷、十二烷、燈油等脂肪族烴;環戊烷、環己烷、甲基環戊烷等脂環族烴;苯、甲苯、二甲苯等芳香族烴;氯化乙烯、氯苯、二氯甲烷等鹵化烴或該等之混合物等,烯烴自身亦可作為溶劑使用。
使用如上述之烯烴聚合用觸媒,進行烯烴聚合時,成分(A)通常以每1公升反應容積,使用10- 8
~10- 2
莫耳、較佳10- 7
~10- 3
莫耳之量。成分(B-1)通常以成分(B-1)與成分(A)中全過渡金屬原子(M)之莫耳比[(B-1)/M]為0.01~5,000、較佳0.05~2,000之量使用。成分(B-2)通常以成分(B-2)中鋁原子與成分(A)中全過渡金屬(M)之莫耳比[(B-2)/M]為10~5,000、較佳20~2,000之量使用。成分(B-3)通常以成分(B-3)與成分(A)中過渡金屬原子(M)之莫耳比[(B-3)/M]為1~10、較佳1~5之量使用。
成分(D)係於成分(B)為成分(B-1)之情形時,通常以莫耳比[(D)/(B-1)]為0.01~10、較佳0.1~5之量使用;於成分(B)為成分(B-2)之情形時,通常以莫耳比[(D)/(B-2)]為0.01~2、較佳0.005~1之量使用;於成分(B)為成分(B-3)之情形時,通常以莫耳比[(D)/(B-3)]為0.01~10、較佳0.1~5之量使用。
又,使用此種烯烴聚合用觸媒之烯烴聚合溫度,通常為-50~+200℃,較佳0~170℃之範圍。聚合壓力通常為常壓~10MPa之計示壓力,較佳常壓~5MPa計示壓力之條件,聚合反應可以分批式、半連續式、連續式任一之方法進行。進而亦可分為反應條件不同之二階段以上而進行聚合。所得之烯烴系聚合體之分子量,可藉由使氫存在於聚合系中,或使聚合溫度變化而進行調節。進而,亦可藉由使用之成分(B)之量而進行調節。添加氫之情形時,其量較適合為每1 kg烯烴為0.001~100 NL左右。
於本發明中,供給於聚合反應中之烯烴,為選自乙烯以及α-烯烴之1種以上之單體,較佳為至少1種單體為乙烯或丙烯。作為α-烯烴,可為碳原子數為3~20、較佳3~10之直鏈狀或支鏈狀α-烯烴,例如可列舉:丙烯、1-丁烯、2-丁烯、1-戊烯、3-甲基-1-丁烯、1-己烯、4-甲基-1-戊烯、3-甲基-1-戊烯、1-辛烯、1-癸烯、1-十二烯、1-十四烯、1-十六烯、1-十八烯、1-二十烯等。又,亦可為碳原子數為3~30、較佳3~20之環狀烯烴,例如可列舉:環戊烯、環庚烯、降烯、5-甲基-2-降烯、四環十二烯、2-甲基-1,4,5,8-二甲橋-1,2,3,4,4a,5,8,8a-八氫化萘;極性單體,例如可列舉丙烯酸、甲基丙烯酸、反丁烯二酸、順丁烯二酸酐、衣康酸、衣康酸酐、雙環(2,2,1)-5-庚基-2,3-二羧酸酐等α,β-不飽和羧酸,以及該等之鈉鹽、鉀鹽、鋰鹽、鋅鹽、鎂鹽、鈣鹽、鋁鹽等金屬鹽;丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丙酯、丙烯酸異丙酯、丙烯酸正丁酯、丙烯酸異丁酯、丙烯酸第三丁酯、丙烯酸2-乙基己酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丙酯、甲基丙烯酸異丙酯、甲基丙烯酸正丁酯、甲基丙烯酸異丁酯等之α,β-不飽和羧酸酯;乙酸乙烯酯、丙酸乙烯酯、己酸乙烯酯、癸酸乙烯酯、十二烷酸乙烯酯、硬脂酸乙烯酯、三氟乙酸乙烯酯等乙烯酯類;丙烯酸環氧丙酯、甲基丙烯酸環氧丙酯、衣康酸單環氧丙酯等不飽和環氧丙酯等。又,亦可使乙烯環己烷、二烯或多烯等芳香族乙烯化合物,例如可列舉苯乙烯、鄰甲基苯乙烯、間甲基苯乙烯、對甲基苯乙烯、鄰,對二甲基苯乙烯、鄰乙基苯乙烯、間乙基苯乙烯、對乙基苯乙烯等單或多烷基苯乙烯;甲氧基苯乙烯、乙氧基苯乙烯、乙烯基苯甲酸、乙烯基苯甲酸甲酯、乙烯基苄基乙酸酯、羥基苯乙烯、鄰氯苯乙烯、對氯苯乙烯、二乙烯苯等含有官能基之苯乙烯衍生物;以及3-苯基丙烯,4-苯基丙烯,α-甲基苯乙烯等共存於反應系中進行聚合。
於本發明之烯烴系聚合體之製造方法中,至少1種單體為乙烯或丙烯。單體為二種以上之情形時,較佳係乙烯、丙烯或乙烯+丙烯為全體單體量之50莫耳%以上,具體而言可較佳地用於乙烯/丙烯共聚體(EPR)、丙烯/乙烯共聚體(PER)、丙烯/乙烯無規共聚體(無規PP)、丙烯/乙烯嵌段共聚體(嵌段PP)、丙烯/丁烯共聚體(PBR)、丙烯/乙烯/丁烯共聚體(PEBR)等之製造中。
以下,根據實施例對本發明加以詳細說明。
使用日本分光公司製造之傅立葉變換紅外分光光度計FT/IR-610,求取基於丙烯之甲基之橫向搖擺振動1155cm- 1
附近之面積與C-H伸縮振動之諧波吸收4325 cm- 1
附近之吸光度,由該比以檢量線(使用以1 3
C-NMR標定之標準試料製成)算出。
使用離合公司製造之自動動黏度測定裝置VMR-053PC以及改良尤伯落德型毛細管黏度計,求得十氫萘、135℃下之比黏度η sp,並以下式算出極限黏度。
[η]=η sp/{C(1+K.η sp)}<C:溶液濃度[g/dl],K:常數>
使用Waters公司製造之Alliance GPC2000,以流量1.0 ml/分鐘移動500 μ l之濃度為0.1 wt%之試料溶液,並進行測定。標準聚苯乙烯使用Tosoh公司製造,作為換算為各聚合體之分子量而算出。
分離管柱:TSKgel GMH6-HT以及TSKgel GMH6-HTL(各內徑7.5 mm,長度300 mm各2根)管柱溫度:140℃移動相:鄰二氯苯檢出器:示差折射器
以下,根據實施例對本發明加以更詳細之說明,但本發明並非限定於該等實施例者。
再者,以合成例所得之化合物之結構,係使用270 MHz1
H-NMR(日本電子GSH-270),FD-質量分析(日本電子SX-102A)等而測定。
於氮氣環境下,於300 ml之三口燒瓶中加入25.8 g無水氯化鋁、5.18 g茀、200 ml二硫化碳。於水浴下,以15分鐘滴下6.18 g氧化三甲苯,於迴流下攪拌10小時。放置冷卻後,添加100 ml水,分離有機層。以300 ml己烷萃取水層,與先前之有機層合併,以水、飽和氯化鈉水溶液洗淨,以硫酸鎂乾燥後,餾去溶劑。以管柱層析法進行精製,以乙醇/己烷混合溶劑進行再結晶。收量為1.14 g。以1
H-NMR光譜進行鑒定。以下表示該測定結果。
1
H-NMR(270 MHz,CDCl3
,TMS基準):δ 7.62(s,2H),δ 7.43(s,2H),δ 6.03(s,2H),δ 3.89(s,2H),δ 2.19(s,6H),δ 1.33(s,12H)
(1)3-第三丁基-6-苯基-1,6-二甲基-芙之合成於氮氣環境下,於100 ml之三口燒瓶中加入1.50 g以缽粉碎之氫氧化鉀、0.91 g 18-冠-6-醚、45 ml之THF。於水浴下,以10分鐘滴下2.70 g第三丁基-甲基環戊二烯,攪拌3小時。以10分鐘滴下11.33 g苯乙酮,攪拌22小時。將反應溶液注入至100 ml之2N鹽酸中。分離有機層,以200 ml己烷萃取水層,與先前之有機層合併,以飽和碳酸氫鈉水溶液、水、飽和氯化鈉水溶液洗淨。以硫酸鎂乾燥後,餾去溶劑,以管柱層析法進行精製。收量為1.98 g。以1
H-NMR光譜進行鑒定。以下表示該測定結果。根據1
H-NMR之結果為異構體混合物。
1
H-NMR(270 MHz,CDCl3
,TMS基準):δ 7.37-7.30(m,4H),7.24-7.20(m,1H),6.33+5.56(m+m,1H),6.17+6.11(d+d,1H),2.50+2.41(s+s,3H),2.34+1.36(s+s,3H),1.19+1.01(s+s,9H)
(2)(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀)之合成於氮氣環境下,於100 ml三口燒瓶中加入1.71 g之1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀、40 ml二乙基醚。冰/丙酮浴下,經3分鐘滴下3.5 ml(5.4 mmol)1.54M之正丁基鋰己烷溶液。一面緩慢升溫至室溫一面攪拌21小時。以10分鐘添加1.41 g(5.92 mmol)3-第三丁基-6-苯基-1,6-二甲基芙之二乙醚溶液。於迴流下攪拌7天後,將反應溶液注入100 ml之1 N鹽酸中。分離有機層,以75 ml己烷萃取水層2次。合併所得之有機層,以飽和碳酸氫鈉水溶液洗淨1次、以水洗淨2次、以飽和食鹽水洗淨1次。以硫酸鎂乾燥,餾去溶劑。所得之固體以管柱層析法精製,以甲醇洗淨。收量為0.70 g。以FD-MS光譜進行鑒定。以下表示其結果。
FD-MS:m/Z=564(M+
)
(3)(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯之合成於氮氣環境下,在30 ml Schlenk管中加入0.691 g(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯基)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)、15 ml醚。於醚/丙酮浴下,添加1.75 ml(2.70 mmol)之1.54Mn-BuLi己烷溶液攪拌10分鐘。於室溫下攪拌24小時後,以冰/丙酮浴冷卻後,添加0.439 g(1.88 mmol)四氯化鋯。一面緩慢恢復至室溫一面攪拌19小時。餾去溶劑,以己烷萃取可溶分。餾去溶劑,以醚進行再結晶。將所得之結晶以戊烷洗淨。收量為52 mg。以1
H-NMR光譜、FD-MS進行鑒定。以下表示該測定結果。
1
H-NMR(270 MHz,CDCl3
,TMS基準):δ 7.94-7.90(m,1H),7.87(s,1H),7.85(s,1H),7.82(s,1H),7.76-7.73(m,1H),7.65-7.50(m,1H),7.45-4.38(m,2H),6.09(d,1H),6.03(d,1H),5.90(d,1H),5.90(d,1H,),5.87(d,1H),5.54(d,1H),2.78(s,3H),2.42(s,3H),2.20(d,3H),2.16(d,3H),1.53(s,3H),1.35(s,6H),1.21(s,1H),1.01(s,9H),0.96(s,3H),0.86(s,3H)
FD-MS:m/Z=724(M+
)
於經充分氮氣置換之100 ml之三口燒瓶中安裝攪拌棒,於其中添加1.00 g二氧化矽承載甲基鋁氧烷(Al=14.6 wt%)。在此於室溫下添加10 ml脫水甲苯,一面攪拌一面添加20 ml之於上述實施例2中合成之(苯基)(甲基)亞甲基(3-第三丁基-5-甲基環戊二烯)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯21.0mg之甲苯溶液作為過渡金屬化合物,攪拌1小時。以過濾器過濾所得之漿料,並將過濾器上之粉體以10 ml脫水甲苯洗淨1次,繼而以10 ml脫水己烷洗淨3次。將洗淨後之粉體減壓乾燥2小時獲得0.934 g粉體,故將其與8.41 g礦物油相混合而製成10.0 wt%漿料。
於經充分氮氣置換之內容量為2000 ml之SUS製高壓釜中加入300 g液體丙烯,一面充分攪拌一面加溫至55℃,此處以乙烯氣體進行加壓將高壓釜內壓升為30 kg/Cm2
G。繼而,於安裝於高壓釜上、並經充分氮氣置換之內容量30 ml之觸媒插入用壺中添加4 ml脫水己烷與1 ml三異丁基鋁之己烷溶液(Al=1.0 M)之混合溶液,以氮加壓插入至高壓釜中。繼而於觸媒插入用壺中,添加344 mg上述實施例3中所製備之承載觸媒之漿料與1.0 mmol三異丁基鋁之己烷溶液(Al=1.0 M)之混合物,以氮加壓插入至高壓釜中開始聚合。聚合進行3分鐘後,添加少量甲醇停止聚合。於添加有鹽酸之大過量甲醇中添加聚合物並脫灰,過濾聚合物後,於80℃下減壓乾燥10小時。所得之聚合物為16.7 g,聚合活性為342 kg-Polymer/mmol-Zr.hr。聚合物分析之結果為:聚合物中之乙烯含量=30 mol%、[η]=2.22 dl/g、Mw=238,000、Mw/Mn=2.0。
除了使用347 mg上述實施例3中製備之承載觸媒之漿料,以乙烯氣體進行加壓將高壓釜內壓上升至35 kg/cm2
G,聚合4分鐘以外,其他與上述實施例4相同進行聚合。所得之聚合物為50.9 g,聚合活性為773 kg-Polymer/mmol-Zr.hr。聚合物分析之結果為:聚合物中之乙烯含量=47 mol%、[η]=2.55 dl/g、Mw=250,000、Mw/Mn=2.0。
除了使用199 mg上述實施例3中所製備之承載觸媒之漿料,以乙烯氣體進行加壓將高壓釜內壓上升至40 kg/cm2
G,進行4分鐘聚合以外,其他與上述實施例4相同進行聚合。所得之聚合物為24.3 g,聚合活性為734 kg-Polymer/mmol-Zr.hr。聚合物分析之結果為:聚合物中之乙烯含量=60 mol%、[η]=3.04 dl/g、Mw=305,000、Mw/Mn=2.1。
於經充分氮氣置換之50 ml之側臂燒瓶(side arm flask)中加入磁性攪拌子,於其中添加1.02 g上述實施例3中製備之承載觸媒之漿料與1.0 mmol三異丁基鋁之己烷溶液(Al=1.0 M)以及5.0 ml脫水己烷,並導入至經充分氮氣置換之內容量為2,000 ml之SUS製高壓釜中。其後,加入500 g液體丙烯,於70℃進行40分鐘聚合後,冷卻高壓釜並淨化(purge)丙烯以停止聚合,於80℃下減壓乾燥聚合物10小時。所得之聚合物為248.9 g整規聚丙烯,聚合活性為128.6 kg-PP/mmol-Zr.hr。聚合物分析之結果為:[η]=3.77 dl/g、Mw=606,000、Mw/Mn=2.9、Tm=147.4℃。
除了使用0.340 g上述實施例3中製備之承載觸媒之漿料,加入500 g液體丙烯後,添加0.30 N1氫以外,其他與實施例7同樣進行聚合。所得之聚合物為328.9 g整規聚丙烯,聚合活性為510.0 kg-PP/mmol-Zr.hr。聚合物分析之結果為:[η]=2.18 dl/g、Mw=261,000、Mw/Mn=2.7、Tm=150.1℃。
除了使用0.201 g上述實施例3中製備之承載觸媒之漿料,加入500 g液體丙烯後,添加0.60 N1氫以外,其他與實施例7相同進行聚合。所得之聚合物為255.0 g整規聚丙烯,聚合活性為670.2 kg-PP/mmol-Zr.hr。聚合物分析之結果為:[η]=1.16 dl/g、Mw=121,000、Mw/Mn=2.3、Tm=150.3℃。
(1)6,6-二-對甲苯基芙之合成於氮氣環境下,於具有磁性攪拌子以及三通旋塞之200 ml二口燒瓶中加入6.72 g(31.9 mmol)4,4’-二甲基二苯甲酮、30 ml四氫呋喃。一面以冰水浴冷卻一面緩慢添加19 ml(38 mmol)之2.0 mol/l環戊二烯基鈉/四氫呋喃溶液後,於室溫下攪拌6天。一面以冰水浴冷卻一面緩慢添加100ml 1N之鹽酸,繼而添加100 ml二乙基醚。分離有機層,以100 ml水洗淨2次,以100 ml飽和食鹽水洗淨1次。以硫酸鎂乾燥後,餾去溶劑,以管柱層析法進行精製。收量為6.15 g,收率為74.5%。以1
H-NMR光譜進行鑒定。以下表示該測定結果。
1
H-NMR光譜(270 MHz,CDCl3
,TMS基準):d2.39(s,6H),6.2-6.3(m,2H),6.5-6.6(m,2H),7.1-7,2(m,2H)
(2)(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)(環戊二烯基)二-對甲苯基甲烷之合成於氮氣環境下,於具有磁性攪拌子、三通旋塞以及50 ml滴下漏斗之200 ml二口燒瓶中,裝入749 mg(2.29 mmol)1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀、30 ml四氫呋喃。一面以冰水浴冷卻一面緩慢添加1.56 ml(2.43 mmol)1.56mol/l之正丁基鋰/己烷溶液後,於室溫下攪拌6.5小時後。一面以甲醇/乾冰浴冷卻,一面使用滴下漏斗以20分鐘緩慢添預先溶解於30 ml四氫呋喃中之6,6-二-對甲苯基芙718 mg(2.78 mmol)。此後緩慢升溫至室溫,於室溫下攪拌20小時。緩慢添加50 ml之1 N鹽酸,繼而添加50 ml二乙基醚。分離有機層,以50 ml水洗淨2次,以50 ml飽和食鹽水洗淨1次,以硫酸鎂乾燥後,餾去溶劑,以管柱層析法進行精製。收量為397 mg(0.679 mmol),收率為29.6%。以1
H-NMR光譜以及FD-MS光譜進行鑒定。以下表示該測定結果。
1
H-NMR光譜(270 MHz,CDCl3
,TMS基準):0.8-1.4(m,12H),1.8-2.2(m,6H),2.2-2.3(m,6H),2.8-3.1(br,1H),5.33(s,1H),5.9-6.0(m,2H),6.0-6.6(br,4H),6.7-7.5(br,12H)
FD-MS:M/z 584(M+
)
(3)二-對甲苯基亞甲基(環戊二烯基(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯之合成於氮氣環境下,於具有磁性攪拌子之100 ml克而達(kjeldahl)燒瓶中,添加376 mg(0.643 mmol)之1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)(環戊二烯基)二-對甲苯基甲烷、40 ml二乙醚。一面以冰水浴冷卻,一面緩慢添加0.86 ml(1.3 mmol)之1.56mol/l正丁基鋰/己烷溶液後,於氮氣環境下以室溫攪拌20小時。一面以甲醇/乾冰浴冷卻一面添加0.260 g(0.688 mmol)四氯化鋯.四氫呋喃錯合物(1:2)後,緩慢升溫至室溫,於室溫下攪拌17小時。於減壓條件下餾去溶劑並以己烷萃取所得之固體,於減壓條件下餾去所得之溶液溶劑。將其以戊烷洗淨後,以二氯甲烷萃取,於減壓條件下餾去所得之溶液溶劑並獲得目標化合物。收量為149 mg(0.200 mmol),收率為31.1%。以1
H-NMR光譜以及FD-MS光譜進行鑒定。以下表示該測定結果。
1
H-NMR光譜(270 MHz,CDCl3
,TMS基準):0.94(s,6H),1.04(s,6H),2.17(d,6H),2.35(s,6H),5.68(t,2H),5.95(d,2H),6.10(s,Ar(Flu),2H),6.28(t,2H),7.1-7.3(m,4H),7.8-7.9(m,4H),7.91(s,2H)
FD-MS:M/z 744(M+
)
於經充分氮氣置換之100 ml之三口燒瓶中安裝攪拌棒,於其中添加0.989 g二氧化矽承載甲基鋁氧烷(Al=19.3wt%)以及42 ml甲苯。緩慢添加於8.0 ml甲苯中溶解有20.2 mg(0.0271 mmol)作為過渡金屬化合物之上述實施例10中合成之二-對甲苯基亞甲基(環戊二烯基(1,1,3,6,8,8-六甲基-1H,8H-二環戊[b,h]茀基)二氯化鋯之溶液,其後於室溫下攪拌1小時。停止攪拌靜置後,傾析去除上清液。其後,進行3次添加45 ml庚烷、攪拌、靜置、傾析去除上清液之操作。進而添加庚烷,製成全量為50 ml之漿料。一面攪拌一面添加2.0 ml(Al=2.0 mmol)之三異丁基鋁之正癸烷溶液後,將乙烯吹入漿料中,於20℃下進行34分鐘聚合。停止供給乙烯以及攪拌並靜置後,傾析去除上清液。其後,進行3次添加45 ml庚烷、攪拌、靜置、傾析去除上清液之操作。繼而添加庚烷製成全量為100 ml之漿料,獲得前聚合承載觸媒之庚烷漿料。
於經充分氮氣置換之內容積1公升之SUS製高壓釜中加入500 ml精製庚烷,流通乙烯,以乙烯使液相以及氣相飽和。繼而,使用氫-乙烯混合氣體(氫濃度:0.99 vol%),置換系內氣體後,順次添加0.25 mmol三異丁基鋁、5.0 ml以實施例11製備之承載觸媒漿料。升溫至80℃,以0.78 MPa.G聚合1小時。將所得之聚合物真空乾燥10小時,獲得56.7 g乙烯聚合體。聚合活性為1120 g-PE/g-cat.h。又,所得之乙烯聚合體之[η]為0.88 dl/g。
於經充分氮氣置換之內容積1公升之SUS製高壓釜中添加500 mL精製庚烷,流通乙烯,以乙烯使液相以及氣相飽和。繼而,順次加入0.25 mmol三異丁基鋁、3.0 ml 1-己烯、1.4 ml以實施例11製備之承載觸媒漿料。升溫至80℃,於0.78MPa.G下進行45分鐘聚合。將所得之聚合物真空乾燥10小時,獲得74.7 g乙烯/1-己烯共聚體。聚合活性為7060 g-PE/g-cat.h。又,所得之乙烯聚合體之密度為0.946 g/cm3
。
於經充分氮氣置換之100 ml之三口燒瓶中安裝攪拌棒,並於其中加入1.01 g二氧化矽承載甲基鋁氧烷(Al=14.6 wt%)。此時於室溫下添加10 ml脫水甲苯,一面攪拌一面添加20 ml作為過渡金屬化合物之依據WO01/27124合成之20.6 mg亞異丙基(3-第三丁基-5-甲基環戊二烯基)(茀基)二氯化鋯之甲苯溶液,攪拌1小時。使用過濾器過濾所得之漿料,將過濾器上之粉體以10 ml脫水甲苯洗淨1次,繼而以10 ml脫水己烷洗淨3次。減壓乾燥洗淨後之粉體2小時獲得0.929 g粉體,並將其與8.36 g礦物油相混合製成10.0 wt%漿料。
於經充分氮氣置換之內容量2000 ml之SUS製高壓釜中加入300 g液體丙烯,一面充分攪拌一面升溫至55℃,此時以乙烯氣體進行加壓將高壓釜內壓上升至35 kg/cm2
G。繼而,於安裝於高壓釜上並經充分氮氣置換之內容量30 ml之觸媒插入用壺中加入4 ml脫水己烷與1 ml三異丁基鋁之己烷溶液(Al=1.0 M)之混合溶液,以氮加壓插入高壓釜中。繼而於觸媒插入用壺中加入170 mg上述比較例1中製備之承載觸媒漿料與1.0 mmol三異丁基鋁之己烷溶液(Al=1.0 M)之混合物,以氮加壓插入至高壓釜中並開始聚合。進而聚合5分鐘後,添加少量甲醇停止聚合。於添加鹽酸之大過量甲醇中添加聚合物並脫灰,過濾聚合物後,以80℃進行減壓乾燥10小時。所得之聚合物為19.6 g,聚合活性為174 kg-Polymer/mmol-Zr.hr。聚合物分析之結果為:聚合物中乙烯含量=39 mol%、[η]=1.00 dl/g、Mw=74,000、Mw/Mn=2.0。
於經充分氮氣置換之50 ml側臂燒瓶中加入磁性攪拌子,並於其中加入0.262 g上述比較例1中製備之承載觸媒漿料與1.0 mmol三異丁基鋁之己烷溶液(Al=1.0 M)以及5.0 ml脫水己烷,導入經充分氮氣置換之內容量2,000 ml之SUS製高壓釜中。此後,加入500 g液體丙烯後,添加0.30 Nl氫原子,於70℃下聚合40分鐘後,冷卻高壓釜並淨化丙烯以停止聚合。於80℃下減壓乾燥聚合物10小時。所得之聚合物為171.1 g整規聚丙烯,聚合活性為246 kg-PP/mmol-Zr.hr。聚合物分析之結果為:[η]=1.67 dl/g、Mw=198000、Mw/Mn=2.2、Tm=242.3℃。
本發明之在3,6位上取代碳-碳不飽和鍵結之茀化合物、具有含對應於該茀化合物之茀基之配位基的有用且新穎的過渡金屬化合物,係可作為新穎具有用之烯烴聚合用觸媒成分。含有該過渡金屬化合物之烯烴聚合用觸媒為非常高活性,而提供一種更經濟地製造烯烴系共聚體的方法。
Claims (6)
- 一種過渡金屬化合物,其特徵為,係以下述通式[Ⅲ]所示:
- 如申請專利範圍第1項之過渡金屬化合物,其中,上述通式[Ⅲ]中,R24 、R26 為氫。
- 一種烯烴聚合用觸媒,其特徵為,含有申請專利範圍第1或2項之過渡金屬化合物。
- 一種烯烴聚合用觸媒,其特徵為,至少含有一種自以下選擇之化合物: (A)申請專利範圍第1或2項之過渡金屬化合物;與(B)(B-1)有機金屬化合物;(B-2)有機鋁氧化物化合物;(B-3)與過渡金屬化合物(A)反應而形成離子對之化合物。
- 一種烯烴系聚合體之製造方法,其係於申請專利範圍第3或4項之烯烴聚合用觸媒存在下,使選自乙烯以及α-烯烴之1種以上單體進行聚合的方法,其中,至少1種單體為乙烯或丙烯。
- 如申請專利範圍第5項之烯烴系聚合體之製造方法,其中,上述通式[Ⅲ]所表示之過渡金屬化合物係以支持於支持體上之形態而使用。
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