CA2396050A1 - Preparation of conjugated diene polymers by using an iron-based catalyst system - Google Patents

Preparation of conjugated diene polymers by using an iron-based catalyst system Download PDF

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Publication number
CA2396050A1
CA2396050A1 CA002396050A CA2396050A CA2396050A1 CA 2396050 A1 CA2396050 A1 CA 2396050A1 CA 002396050 A CA002396050 A CA 002396050A CA 2396050 A CA2396050 A CA 2396050A CA 2396050 A1 CA2396050 A1 CA 2396050A1
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Prior art keywords
compound
iron
conjugated diene
group
substituted
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CA002396050A
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French (fr)
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CA2396050C (en
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Steven Luo
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Bridgestone Corp
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Priority to CA2569632A priority Critical patent/CA2569632C/en
Publication of CA2396050A1 publication Critical patent/CA2396050A1/en
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Publication of CA2396050C publication Critical patent/CA2396050C/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • 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
    • C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F136/02—Homopolymers 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
    • C08F136/04—Homopolymers 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 conjugated
    • 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
    • C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F136/02—Homopolymers 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
    • C08F136/04—Homopolymers 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 conjugated
    • C08F136/06—Butadiene
    • 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
    • C08F4/70—Iron group metals, platinum group metals or compounds thereof

Abstract

A process for preparing conjugated diene polymers by polymerizingconjugated diene monomers in the presence of a catalyst composition that is formed by combining an iron-containing compound, a hydrogen phosphite, and an organoaluminum compound.

Claims (10)

1. A process for preparing conjugated diene polymers comprising the step of polymerizing conjugated diene monomers in the presence of a catalytically effective amount of a catalyst composition that is formed by combining:
(a) an iron-containing compound;
(b) a hydrogen phosphite; and (c) an organoaluminum compound comprising (1) at least one compound defined by the formula AlR n X3-n, where each R, which may be the same or different, is a mono-valent organic group, each X, which may be the same or different, is a hydrogen atom, a carboxylate group, en alkoxide group, or an aryloxide group, and n is an integer including 1, 2 or 3, or (2) at least one compound defined by one of the following formulas:

where x is as integer of 1 to 100, y is an integer of 2 to 100, and each R4, which may be the same or different, is a mono-valent organic group, said catalyst composition comprising from 0.01 to 1.0 mmol iron-containing compound per 100 grains monomer.
2. A process for preparing conjugated diene polymers comprising the step of homopolymerizing 1,3-butadiene monomer in the presence of a catalytically effective amount of a catalyst composition formed by combining:
(a) an iron-containing compound;
(b) a hydrogen phosphite; and (c) an organoaluminum compound, in the presence of conjugated diene monomer so as to provide syndiotactic 1,2-polybutadiene, with the proviso that the molar ratio of said organoaluminum compound to said iron-combining compound is from 11:1 to 100:1.
3. A process for preparing conjugated diene polymers comprising the step of homopolymerizing 1,3-butadiene monomer in the presence of a catalytically effective amount of a catalyst composition that is formed by combining:
(a) an iron-containing compound;
(b) a hydrogen phosphite; and (c) an organoaluminum compound in the presence of conjugated diene monomer so as to provide amorphous high-vinyl polybutadiene, with the proviso that the molar ratio of said organoaluminum compound to said iron-containing compound is from 1:1 to 9:1.
4. The process of any of claims 1 to 3 where the molar ratio of said hydrogen phosphite to said iron-containing compound is from 0.5:1 to 50:1.
5. The process of claims 1 to 3 where the conjugated diene monomers are 1,3-butadiene monomers.
6. The process of claim 3 where they molar ratio of the organoaluminurn compound to the iron-containing compound is from 1:1 to about 7:1.
7. The process of any of claims 1 to 3 where the hydrogen phosphite is an acycl\ic hydrogen phosphite defined by the keto-enol tautomeric structures or a cyclic hydrogen phosphate defined by the keto-enol tautomeric structures or a mixture thereof, where R1 and R2, which may be the same or different, are mono-valent organic groups and where R3 is a divalent organic group.
8. The process of claim 7, where R1 and R2 are alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, cycloalkenyl, substituted alkenyl, aryl, allyl, substituted aryl, aralkyl, alkaryl, or alkynyl groups, with each group containing up to about 20 carbon atoms, and where R3 is an alkylene, cycloalkylene, substituted alkylene, substituted cycloalkylene, alkenylene, cycloalkenylene, substituted alkenylene, substituted cycloalkenylene, arylene, or substituted arylene group, with each group containing up to about 20 carbon atoms.
9. The process of any of claims 2 and 3 where the organoaluminum compound comprises at least one compound defined by the formula AlR n X3-n where each R, which may be the same or different, is a mono-valent organic group;
each X, which may be the same or different, is s hydrogen atom, a carboxylate group, an alkoxide group, or an aryloxide group; and n is an integer including 1, 2 or 3.
10. The process of claim 1, where the (a), (b) and (c) are combined in the presence of conjugated diene monomer.
CA2396050A 1999-12-30 2000-12-29 Preparation of conjugated diene polymers by using an iron-based catalyst system Expired - Fee Related CA2396050C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2569632A CA2569632C (en) 1999-12-30 2000-12-29 Preparation of conjugated diene polymers by using an iron-based catalyst system

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/475,343 1999-12-30
US09/475,343 US6399732B2 (en) 1998-10-14 1999-12-30 Preparation of conjugated diene polymers by using an iron-based catalayst system
PCT/US2000/035564 WO2001049753A1 (en) 1999-12-30 2000-12-29 Preparation of conjugated diene polymers by using an iron-based catalyst system

Related Child Applications (1)

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CA2569632A Division CA2569632C (en) 1999-12-30 2000-12-29 Preparation of conjugated diene polymers by using an iron-based catalyst system

Publications (2)

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CA2396050A1 true CA2396050A1 (en) 2001-07-12
CA2396050C CA2396050C (en) 2011-05-10

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CA2396050A Expired - Fee Related CA2396050C (en) 1999-12-30 2000-12-29 Preparation of conjugated diene polymers by using an iron-based catalyst system

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US (2) US6399732B2 (en)
EP (1) EP1242481A1 (en)
JP (1) JP2003519256A (en)
CA (1) CA2396050C (en)
WO (1) WO2001049753A1 (en)

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US6576725B1 (en) 2002-01-18 2003-06-10 Bridgestone Corporation Iron-based catalyst for producing high-vinyl polybutadiene
US6720397B2 (en) 2002-02-20 2004-04-13 Bridgestone Corporation Polymerization process for preparing syndiotactic 1,2-polybutadiene
CN1557847A (en) * 2002-12-27 2004-12-29 中国科学院长春应用化学研究所 Process for preparing high vinyl polybutadiene rubber
US7807763B2 (en) * 2008-04-07 2010-10-05 Bridgestone Corporation Method for bulk polymerization
KR101762461B1 (en) 2009-10-14 2017-07-27 가부시키가이샤 브리지스톤 Processes for preparation of cyclic acyclic diene copolymer and rubber composition
US20120202910A1 (en) * 2009-10-14 2012-08-09 Nippon Soda Co., Ltd. Method for producing polybutadiene
US8389433B2 (en) * 2009-11-24 2013-03-05 Chevron U.S.A. Hydroprocessing bulk catalyst and methods of making thereof
US8372776B2 (en) * 2009-11-24 2013-02-12 Chevron U.S.A. Inc. Hydroprocessing bulk catalyst and methods of making thereof
WO2016078023A1 (en) * 2014-11-19 2016-05-26 中国科学院长春应用化学研究所 Random-syndiotactic block polybutadiene and preparation method thereof
KR101936668B1 (en) * 2017-06-19 2019-01-10 금호석유화학 주식회사 A method for manufacturing a rubber composition comprising a syndiotactic 1,2-polybutadiene

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Also Published As

Publication number Publication date
CA2396050C (en) 2011-05-10
US20010012878A1 (en) 2001-08-09
JP2003519256A (en) 2003-06-17
WO2001049753A1 (en) 2001-07-12
US6399732B2 (en) 2002-06-04
EP1242481A1 (en) 2002-09-25
US20020137862A1 (en) 2002-09-26

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