JP2015517604A - ブテン−1重合用触媒成分 - Google Patents
ブテン−1重合用触媒成分 Download PDFInfo
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- JP2015517604A JP2015517604A JP2015513226A JP2015513226A JP2015517604A JP 2015517604 A JP2015517604 A JP 2015517604A JP 2015513226 A JP2015513226 A JP 2015513226A JP 2015513226 A JP2015513226 A JP 2015513226A JP 2015517604 A JP2015517604 A JP 2015517604A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F4/52—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 selected from boron, aluminium, gallium, indium, thallium or rare earths
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/10—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of alkaline earth metals, zinc, cadmium, mercury, copper or silver
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/16—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of silicon, germanium, tin, lead, titanium, zirconium or hafnium
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/642—Component covered by group C08F4/64 with an organo-aluminium compound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/651—Pretreating with non-metals or metal-free compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/656—Pretreating with metals or metal-containing compounds with silicon or compounds thereof
- C08F4/6562—Pretreating with metals or metal-containing compounds with silicon or compounds thereof and metals of C08F4/64 or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/15—Isotactic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/17—Viscosity
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
で表される電子供与体化合物を含む固体触媒成分と、(b)アルミニウムアルキル共触媒と、(c)外部電子供与体とを含む、工程を提供することである。
Tiの判定
固体触媒成分のTi含有量は、「I.C.P Spectrometer ARL Accuris」を用いて、誘導結合プラズマ分光分析法(inductively coupled plasma emission spectroscopy)で判定することができる。
固体触媒化合物の内部供与体の含有量はガスクロマトグラフィーで判定した。固体成分を酸性水に溶解した。当該溶液を酢酸エチルで抽出し、内部標準液(internal standard)を添加し、有機相のサンプルをガスクロマトグラフィーで分析して、出発触媒物質に存在する供与体の量を判定した。
重合体2.5gとo−キシレン250mlを、冷却器と還流凝縮器(reflux condenser)を備えた丸底(round−bottomed)フラスコに入れて窒素下に置いた。結果物として得た混合物を135℃に加熱し、60分間攪拌した。最終溶液を攪拌し続けて0℃まで冷却し、不溶性重合体を0℃で濾過した。濾過水(filtrate)を窒素流(nitrogen flow)で140℃の温度で蒸発させ、恒量(constant weight)に到達した。当該キシレン可溶性分画の含有量は、本来の2.5gの百分率で示した後、X.I.%で示す。
キシレン不溶性分画(上述した「X.I.の判定」で得た物質)の測定において、C2Cl4D2に溶解した重合体の8重量%溶液を準備し、120℃におけるフーリエ変換方式で160.91MHzで作動し、クリオプローブ(cryoprobe)を備えたBruker AV−600 spectrometerで120℃でスペクトルを記録した。各スペクトルは90°パルスで得て、パルスとComposite Pulse Decoupling(CPD)との間に15秒の遅延をおいて、1H−13Cカップリングを除去した。9000Hzの分光窓を用いて64Kデータ点に約512過渡現象(transient)を保存した。
mmmm%=100(Immmm)/(Itot)
サンプルの加重量(weight amount)をテトラヒドロナフタレン(THN)に135℃の制御温度で溶解した。当該希釈液の流動時間(flow time)を、135℃に恒温化(thermostated)されたUbbelhode変形毛細管粘度計を備えたSematech Cineviscoシステムで測定した。Irganox 1010を抗酸化剤として添加して分子量の劣化現象を最小化した。IVをハギンズ式(Huggins’equation)を応用し、ハギンズ定数を0.35と仮定して計算した。溶媒及び溶液の流動時間は運動エネルギーによる分布を考慮して修正した。室温から135℃までのTHN容積変化を考慮して溶液の濃度を評価した。
重合体の融解点(Tm)を示差走査熱測定法(D.S.C)を応用して事前にインジウムの融解点に矯正したPerkin Elmer DSC−1熱量計で測定した。DSCの炉内に置いた各サンプルの重量は6.0±0.5mgであった。FormIIの融解点を得るために、加重サンプルをアルミニウムパンに封入し、10℃/分の速度で180℃まで加熱した。サンプルを180℃で5分間放置して微小結晶を完全に融解した後、10℃/分の速度で20℃まで冷却した。20℃で2分間放置した後、サンプルを10℃/分の速度で180℃まで再度加熱した。2次加熱のピーク温度をForm IIの融解温度とみなす。
球形付加物の調製の手順
微細楕円形MgCl2・2.8C2H5OHの初期量をWO98/44009の実施例2に記載された方法に従って、ただし、より大きな規模で調製する。支持体の付加物は、約25ミクロンのP50を有し、エタノールの含有量は約56重量%であった。
500mlの4ッ口丸底フラスコを窒素でパージし、TiCl4250mlを0℃で導入した。攪拌しながら上述した方法で調製した球形付加物10gを添加した。フラスコを0℃に冷却し、所定のモル比Mg/IDを満たすように指定された内部電子供与体化合物を添加した。温度を指定値まで上昇させ、所定の指定チタン化(titanation)時間の間放置した。攪拌を停止し、固体生成物を沈殿させてから、上層の液体をサイフォンで吸い上げて除去した。
70℃の窒素流で1時間パージした4リットルのオートクレーブに、トリイソブチルアルミニウム3.5mmolを含有した無水ヘキサン12mlを30℃の窒素流に導入した。液状ブテン−1 1.35kgを供給し、温度を75℃まで昇温させ、水素(表2で指定された量)を添加した。重合を開始するために、無水ヘキサンに懸濁させた触媒懸濁液50mlを注入した。懸濁液は、トリイソブチルアルミニウム3.5mmol、固体触媒成分6mg及び表2で指定したタイプの外部供与体を同表で指定したMg/EDを満たす量で含有した。
上述した一般的な方式で固体触媒成分を調製した。各実施例ではチタン化条件を表1のように変化させた。他の実施例とは異なり、実施例3の固体は、ヘプタンで90℃で2回洗浄し、続いてヘキサンで60℃で4回洗浄した。
PDBPB ペンタン−2,4−ジイルビス(4−プロピルベンゾエート)
TMPDB 5−(tert−ブチル)−3−メチル−1,2−フェニレンジベンゾエート
EEOB エチル2−(3−エトキシ−3−オキソプロピル)ベンゾエート
上記固体触媒成分を上述した方法を用いて1−ブテンの単独重合に用いた。重合条件(水素と外部供与体の量、外部供与体の種類)を表2の記述に基づいて変化させた。
Claims (10)
- R基はC1−C5直鎖アルキル基から選択される、請求項1に記載の工程。
- nとmの合計は2である、請求項1に記載の工程。
- nとmは共に1である、請求項3に記載の工程。
- R1及びR2は水素及びC1−C5アルキル基から選択される、請求項1に記載の工程。
- R1及びR2は共にアルキル基であってはならない、請求項1に記載の工程。
- R1及びR2は水素である、請求項6に記載の工程。
- 前記アルキル−Al化合物(b)は、トリアルキルアルミニウム化合物の中から選択される、請求項1に記載の工程。
- 前記外部電子供与体は、式(R6)a(R7)bSi(OR8)cで表されるケイ素化合物から選択され、ここで、a及びbは0〜2の整数であり、cは1〜4の整数であり、合計(a+b+c)は4であり、
R6、R7、及びR8は、炭素数1−18のアルキル、シクロアルキルまたはアリールラジカル(aryl radical)であり、必要に応じてヘテロ原子を含有する、請求項1に記載の工程。 - R6及びR7のうち少なくとも一方は炭素数3−10の分枝アルキル(branch alkyl)またはシクロアルキルから選択され、
R8はC1−C10アルキル基である、請求項9に記載の工程。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261657058P | 2012-06-08 | 2012-06-08 | |
EP12171236.8 | 2012-06-08 | ||
US61/657,058 | 2012-06-08 | ||
EP12171236.8A EP2671894A1 (en) | 2012-06-08 | 2012-06-08 | Catalyst components for the polymerization of butene-1 |
PCT/EP2013/061158 WO2013182474A1 (en) | 2012-06-08 | 2013-05-30 | Catalyst components for the polymerization of butene-1 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2015517604A true JP2015517604A (ja) | 2015-06-22 |
JP2015517604A5 JP2015517604A5 (ja) | 2016-04-21 |
JP5976927B2 JP5976927B2 (ja) | 2016-08-24 |
Family
ID=46197182
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2015513226A Expired - Fee Related JP5976927B2 (ja) | 2012-06-08 | 2013-05-30 | ブテン−1重合用触媒成分 |
Country Status (8)
Country | Link |
---|---|
US (2) | US20150141595A1 (ja) |
EP (3) | EP2671894A1 (ja) |
JP (1) | JP5976927B2 (ja) |
KR (1) | KR20150027138A (ja) |
CN (2) | CN104540858A (ja) |
BR (2) | BR112014029395A2 (ja) |
ES (2) | ES2634138T3 (ja) |
WO (2) | WO2013182474A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6216634B2 (ja) * | 2013-12-17 | 2017-10-18 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分、オレフィン類重合用触媒及びオレフィン類重合体の製造方法 |
CN103897080B (zh) * | 2014-04-19 | 2016-05-04 | 山东东方宏业化工有限公司 | 高等规聚丁烯的工业化生产方法及实施该方法的装置 |
US9738736B2 (en) * | 2014-08-12 | 2017-08-22 | W. R. Grace & Co.-Conn | Combined internal donor system for Ziegler-Natta polyolefin catalysts and methods of making and using same |
WO2017204811A1 (en) * | 2016-05-23 | 2017-11-30 | W.R. Grace & Co. -Conn. | Non-phthalate donor for polyolefin catalysts |
CN112649464A (zh) * | 2019-10-10 | 2021-04-13 | 中国石油化工股份有限公司 | 一种聚丁烯-1可溶物含量的检测方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59117509A (ja) * | 1982-12-24 | 1984-07-06 | Mitsui Petrochem Ind Ltd | オレフインの重合方法 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
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DK133012C (da) | 1968-11-21 | 1976-08-09 | Montedison Spa | Katalysator til polymerisation af alkener |
YU35844B (en) | 1968-11-25 | 1981-08-31 | Montedison Spa | Process for obtaining catalysts for the polymerization of olefines |
GB1603724A (en) | 1977-05-25 | 1981-11-25 | Montedison Spa | Components and catalysts for the polymerisation of alpha-olefins |
IT1096661B (it) | 1978-06-13 | 1985-08-26 | Montedison Spa | Procedimento per la preparazione di prodotti in forma sferoidale solidi a temperatura ambiente |
IT1098272B (it) | 1978-08-22 | 1985-09-07 | Montedison Spa | Componenti,di catalizzatori e catalizzatori per la polimerizzazione delle alfa-olefine |
IT1190683B (it) | 1982-02-12 | 1988-02-24 | Montedison Spa | Componenti e catalizzatori per la polimerizzazione di olefine |
ATE38044T1 (de) | 1984-08-30 | 1988-11-15 | Mitsui Petrochemical Ind | Buten-1-polymer und seine verwendung. |
IT1230134B (it) | 1989-04-28 | 1991-10-14 | Himont Inc | Componenti e catalizzatori per la polimerizzazione di olefine. |
IT1262934B (it) | 1992-01-31 | 1996-07-22 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione di olefine |
IT1262935B (it) | 1992-01-31 | 1996-07-22 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione di olefine |
IT1256648B (it) | 1992-12-11 | 1995-12-12 | Montecatini Tecnologie Srl | Componenti e catalizzatori per la polimerizzazione delle olefine |
AUPO591797A0 (en) | 1997-03-27 | 1997-04-24 | Commonwealth Scientific And Industrial Research Organisation | High avidity polyvalent and polyspecific reagents |
HUP0001557A3 (en) | 1997-03-29 | 2010-01-28 | Montell Technology Company Bv | Magnesium dichloride-alcohol adducts, process for their preparation and catalyst components obtained therefrom |
DE69910511T2 (de) | 1998-03-05 | 2004-06-17 | Basell Poliolefine Italia S.P.A. | Polybutene-1 (co)polymere und verfahren zu ihrer herstellung |
CN1169845C (zh) | 2002-02-07 | 2004-10-06 | 中国石油化工股份有限公司 | 用于烯烃聚合的固体催化剂组分和含该催化剂组分的催化剂及其应用 |
RU2315063C2 (ru) | 2002-05-29 | 2008-01-20 | Базелль Полиолефин Италия С.П.А. | (co)полимеры бутена-1, трубы, полученные из них, и способ получения (со)полимеров бутена-1 |
ES2672069T3 (es) | 2008-12-31 | 2018-06-12 | W.R. Grace & Co.-Conn. | Composición de procatalizador con donador interno de diéster aromático de 1,2-fenileno sustituido y método |
KR20120077684A (ko) * | 2010-12-31 | 2012-07-10 | 주식회사 효성 | 올레핀 중합 또는 공중합용 촉매, 이의 제조방법 및 이를 이용한 올레핀의 중합 또는 공중합 방법 |
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2012
- 2012-06-08 EP EP12171236.8A patent/EP2671894A1/en not_active Withdrawn
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2013
- 2013-05-13 US US14/406,390 patent/US20150141595A1/en not_active Abandoned
- 2013-05-30 JP JP2015513226A patent/JP5976927B2/ja not_active Expired - Fee Related
- 2013-05-30 ES ES13725706.9T patent/ES2634138T3/es active Active
- 2013-05-30 CN CN201380026497.8A patent/CN104540858A/zh active Pending
- 2013-05-30 EP EP13725706.9A patent/EP2859026B1/en not_active Not-in-force
- 2013-05-30 BR BR112014029395A patent/BR112014029395A2/pt not_active Application Discontinuation
- 2013-05-30 KR KR1020147036575A patent/KR20150027138A/ko active Search and Examination
- 2013-05-30 WO PCT/EP2013/061158 patent/WO2013182474A1/en active Application Filing
- 2013-06-05 WO PCT/EP2013/061546 patent/WO2013182585A1/en active Application Filing
- 2013-06-05 ES ES13726562.5T patent/ES2573516T3/es active Active
- 2013-06-05 BR BR112014029728A patent/BR112014029728A2/pt not_active Application Discontinuation
- 2013-06-05 EP EP13726562.5A patent/EP2859024B1/en active Active
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JPS59117509A (ja) * | 1982-12-24 | 1984-07-06 | Mitsui Petrochem Ind Ltd | オレフインの重合方法 |
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CN104854141A (zh) | 2015-08-19 |
EP2859024B1 (en) | 2016-04-27 |
ES2573516T3 (es) | 2016-06-08 |
BR112014029395A2 (pt) | 2017-06-27 |
WO2013182585A1 (en) | 2013-12-12 |
US20150141595A1 (en) | 2015-05-21 |
BR112014029728A2 (pt) | 2017-06-27 |
EP2859024A1 (en) | 2015-04-15 |
US20150141594A1 (en) | 2015-05-21 |
CN104854141B (zh) | 2020-03-10 |
EP2859026A1 (en) | 2015-04-15 |
ES2634138T3 (es) | 2017-09-26 |
CN104540858A (zh) | 2015-04-22 |
KR20150027138A (ko) | 2015-03-11 |
EP2859026B1 (en) | 2017-06-28 |
JP5976927B2 (ja) | 2016-08-24 |
WO2013182474A1 (en) | 2013-12-12 |
EP2671894A1 (en) | 2013-12-11 |
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