WO1994012547A3 - Polymerisation de monomeres fonctionnalises a l'aide de catalyseurs de ziegler-natta - Google Patents

Polymerisation de monomeres fonctionnalises a l'aide de catalyseurs de ziegler-natta Download PDF

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Publication number
WO1994012547A3
WO1994012547A3 PCT/US1993/011186 US9311186W WO9412547A3 WO 1994012547 A3 WO1994012547 A3 WO 1994012547A3 US 9311186 W US9311186 W US 9311186W WO 9412547 A3 WO9412547 A3 WO 9412547A3
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WO
WIPO (PCT)
Prior art keywords
catalysts
pentene
ebthi
zrme
polymerization
Prior art date
Application number
PCT/US1993/011186
Other languages
English (en)
Other versions
WO1994012547A2 (fr
Inventor
Robert M Waymouth
Michael R Kesti
Geoffrey W Coates
Original Assignee
Univ Leland Stanford Junior
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Leland Stanford Junior filed Critical Univ Leland Stanford Junior
Priority to EP94902289A priority Critical patent/EP0623149A4/en
Priority to JP6513242A priority patent/JPH07507095A/ja
Publication of WO1994012547A2 publication Critical patent/WO1994012547A2/fr
Publication of WO1994012547A3 publication Critical patent/WO1994012547A3/fr

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Classifications

    • 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
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/20—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds unconjugated
    • 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
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/14—Monomers containing five or more carbon atoms
    • 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
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
    • C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
    • C08F4/65925—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually non-bridged
    • 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
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
    • C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
    • C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Catalyseurs dérivés de la réaction de Cp*2ZrMe2 avec B(B6F5)3 ou [N,N-diméthylanilinium] [B(C6F5)4] (indiqué sous forme de [Cp*ZrMe]+X-, Cp* = pentaméthylcyclopentadiényle, X = B(C¿6?F5)4 ou CH3B(C6F5)3) sont actifs pour l'homopolymérisation de diènes et d'alpha-oléfines fonctionnalisées telles que 4-TMSO-1,6-heptadiène (TMSO = triméthylsiloxy), 5-TBDMSO-1-pentène (TBDMSO = tertbutyldiméthylsiloxy), 5-N,N-diisopropylamino-1-pentène, 5-diphénylphosphino-1-pentène et N-(1-pentène-4-yle)carbazole. D'autres catalyseurs organométalliques tels que [rac (EBTHI)ZrMe]?+X-¿ et [EBIZrMe¿2]?+X- (EBTHI = éthylène-1,2-bis(n5-4,5,6,7-tétrahydro-1-indényle, EBI = éthylène-1,2-bis(1-indényle)) sont des catalyesurs de polymérisation actifs pour la polymérisation d'oléfines fonctionnalisées, bien qu'ils soient plus facilement empoisonnés par les éthers de silyle; les catalyseurs [rac-(EBTHI)ZrMe]+X- polymérisent 4-TBDMSO-1,6-heptadiène et 5-N,N-diisopropylamino-1-pntène. Une série d'autres éthers de silyle ont été polymérisés. Des analyses 13C NMR préliminaires de polymères obtenus à partir des alpha-oléfines fonctionnalisées avec des catalyseurs [(EBTHI)ZrMe]+X- sont compatibles avec des microstructures hautement isotactiques. Des polymères surtout syndiotactiques sont produits à -25° en présence de catalyserus [Cp*¿2?ZrMe]?+X-¿, ce qui est compatible avec le contrôle de fin de chaîne. Le traitement d'éthers de polysilyle avec HCl permet d'obtenir de nouveaux polyalcools. L'ajout de HCl au poly(5-N,N-diisopropylamino-1-pentène) produit le polyélectrolyte correspondant. Les catalyseurs organométalliques/méthylaluminoxane sont actifs pour la polymérisation d'alpha-oléfines contenant des groupes éther de silyle.
PCT/US1993/011186 1992-11-25 1993-11-17 Polymerisation de monomeres fonctionnalises a l'aide de catalyseurs de ziegler-natta WO1994012547A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94902289A EP0623149A4 (en) 1992-11-25 1993-11-17 Polymerization of functionalized monomers with ziegler-natta catalysts.
JP6513242A JPH07507095A (ja) 1992-11-25 1993-11-17 チーグラー・ナッタ触媒で官能化した単量体の重合

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US98169692A 1992-11-25 1992-11-25
US07/981,696 1992-11-25

Publications (2)

Publication Number Publication Date
WO1994012547A2 WO1994012547A2 (fr) 1994-06-09
WO1994012547A3 true WO1994012547A3 (fr) 1994-07-21

Family

ID=25528582

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/011186 WO1994012547A2 (fr) 1992-11-25 1993-11-17 Polymerisation de monomeres fonctionnalises a l'aide de catalyseurs de ziegler-natta

Country Status (4)

Country Link
EP (1) EP0623149A4 (fr)
JP (1) JPH07507095A (fr)
CA (1) CA2128691A1 (fr)
WO (1) WO1994012547A2 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3357961A (en) * 1965-05-24 1967-12-12 Exxon Research Engineering Co Copolymers of ethylene and hexadiene 1, 5
US4734472A (en) * 1986-12-24 1988-03-29 Exxon Research And Engineering Company Method for preparing functional alpha-olefin polymers and copolymers
US4794096A (en) * 1987-04-03 1988-12-27 Fina Technology, Inc. Hafnium metallocene catalyst for the polymerization of olefins
US4841004A (en) * 1986-11-29 1989-06-20 Hoechst Aktiengesellschaft Process for the preparation of a 1-olefin stereoblock polymer
US4892851A (en) * 1988-07-15 1990-01-09 Fina Technology, Inc. Process and catalyst for producing syndiotactic polyolefins
US4975403A (en) * 1987-09-11 1990-12-04 Fina Technology, Inc. Catalyst systems for producing polyolefins having a broad molecular weight distribution

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755279A (en) * 1965-06-25 1973-08-28 Exxon Research Engineering Co Copolymerization of alpha olefins with sterically hindered alkenyl amines using ziegler catalysts
GB1094557A (en) * 1965-11-29 1967-12-13 Montedison Spa Polymers of unsaturated tertiary amines

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3357961A (en) * 1965-05-24 1967-12-12 Exxon Research Engineering Co Copolymers of ethylene and hexadiene 1, 5
US4841004A (en) * 1986-11-29 1989-06-20 Hoechst Aktiengesellschaft Process for the preparation of a 1-olefin stereoblock polymer
US4734472A (en) * 1986-12-24 1988-03-29 Exxon Research And Engineering Company Method for preparing functional alpha-olefin polymers and copolymers
US4794096A (en) * 1987-04-03 1988-12-27 Fina Technology, Inc. Hafnium metallocene catalyst for the polymerization of olefins
US4975403A (en) * 1987-09-11 1990-12-04 Fina Technology, Inc. Catalyst systems for producing polyolefins having a broad molecular weight distribution
US4892851A (en) * 1988-07-15 1990-01-09 Fina Technology, Inc. Process and catalyst for producing syndiotactic polyolefins

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Journal of Applied Polymer Science, Vol. 35, "C-NMR Characterization of Poly (1,5-hexadiene)", pages 825-829 (1988), (CHENG): see page 825, Synopsis; page 827, first paragraph. *
See also references of EP0623149A4 *

Also Published As

Publication number Publication date
JPH07507095A (ja) 1995-08-03
WO1994012547A2 (fr) 1994-06-09
EP0623149A4 (en) 1995-09-27
CA2128691A1 (fr) 1994-06-09
EP0623149A1 (fr) 1994-11-09

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