RU2001104876A - The method of polymerization of conjugated diolefins (dienes) With rare earth catalysts in the presence of vinyl aromatic solvent - Google Patents

The method of polymerization of conjugated diolefins (dienes) With rare earth catalysts in the presence of vinyl aromatic solvent Download PDF

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RU2001104876A
RU2001104876A RU2001104876/04A RU2001104876A RU2001104876A RU 2001104876 A RU2001104876 A RU 2001104876A RU 2001104876/04 A RU2001104876/04 A RU 2001104876/04A RU 2001104876 A RU2001104876 A RU 2001104876A RU 2001104876 A RU2001104876 A RU 2001104876A
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compounds
rare earth
conjugated
carbon atoms
conjugated diolefins
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RU2001104876/04A
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Хайке ВИНДИШ (DE)
Хайке ВИНДИШ
Вернер ОБРЕХТ (DE)
Вернер ОБРЕХТ
Гисберт МИХЕЛЬС (DE)
Гисберт МИХЕЛЬС
Норберт ШТАЙНХАУЗЕР (DE)
Норберт ШТАЙНХАУЗЕР
Томас ШНИДЕР (DE)
Томас ШНИДЕР
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Байер Акциенгезельшафт (De)
Байер Акциенгезельшафт
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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
    • 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
    • C08F36/04—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 conjugated

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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
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  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Claims (9)

1. Способ сополимеризации сопряженных диолефинов с винилароматическими соединениями, отличающийся тем, что полимеризацию сопряженных диолефинов проводят в присутствии катализаторов, состоящих из: а) по меньшей мере, одного соединения редкоземельного металла, б) по меньшей мере, одного циклопентадиенильного соединения и в) по меньшей мере, одного органоалюминиевого соединения, либо состоящих из: а) по меньшей мере, одного соединения редкоземельного металла, и в) по меньшей мере, одного органоалюминиевого соединения, а также в присутствии винилароматических соединений при температуре от -30°С до +100°С, причем молярное соотношение компонентов (а):(б):(в) находится в пределах 1:0,01-1,99:0,1-1000, либо молярное соотношение компонентов (а):(в) находится в пределах 1:0,1-1000, компонент (а) катализатора используют в количестве от 1 мкмол до 10 ммол в расчете на 100 г используемых сопряженных диолефинов, а винилароматическое соединение используют в количестве от 50 г до 2000 г в расчете на 100 г используемых сопряженных диолефинов.1. The method of copolymerization of conjugated diolefins with vinyl aromatic compounds, characterized in that the polymerization of conjugated diolefins is carried out in the presence of catalysts consisting of: a) at least one rare earth metal compound, b) at least one cyclopentadienyl compound and c) at least at least one organoaluminum compound, or consisting of: a) at least one rare earth metal compound, and c) at least one organoaluminum compound, as well as in the presence of of aromatic compounds at a temperature of from -30 ° C to + 100 ° C, and the molar ratio of components (a): (b) :( c) is in the range 1: 0.01-1.99: 0.1-1000, or the molar ratio of components (a) :( c) is in the range 1: 0.1-1000, component (a) of the catalyst is used in an amount of 1 μmol to 10 mmol per 100 g of conjugated diolefins used, and the vinyl aromatic compound is used in an amount from 50 g to 2000 g per 100 g of conjugated diolefins used. 2. Способ по п.1, отличающийся тем, что в качестве сопряженных диоле-финов используют 1,3-бутадиен, 1,3-изопрен, 2,3-диметилбутадиен, 2,4-гексадиен, 1,3-пентадиен и/или 2-метил-1,3-пентадиен.2. The method according to claim 1, characterized in that 1,3-butadiene, 1,3-isoprene, 2,3-dimethylbutadiene, 2,4-hexadiene, 1,3-pentadiene and / are used as conjugated diolefins or 2-methyl-1,3-pentadiene. 3. Способ по п.1 или 2, отличающийся тем, что в качестве соединений редкоземельных металлов используют их алкоголяты, фосфонаты, фосфинаты, фосфаты и карбоксилаты, а также комплексные соединения редкоземельных металлов с дикетонами и/или аддитивные соединения галогенидов редкоземельных металлов с соединениями - донорами кислорода или азота.3. The method according to claim 1 or 2, characterized in that the compounds of rare earth metals use their alcoholates, phosphonates, phosphinates, phosphates and carboxylates, as well as complex compounds of rare earth metals with diketones and / or additive compounds of rare earth halides with compounds - donors of oxygen or nitrogen. 4. Способ по пп.1-3, отличающийся тем, что в качестве соединений редкоземельных металлов используют неодимферзатат, неодимоктанат и/или неодимнафтенат.4. The method according to claims 1 to 3, characterized in that as compounds of rare-earth metals, neodymphrosate, neodymium octane and / or neodymium naphthenate are used. 5. Способ по пп.1-4, отличающийся тем, что в качестве циклопентадиена используют соединения формул (I), (II) или (III)5. The method according to claims 1 to 4, characterized in that the compounds of formulas (I), (II) or (III) are used as cyclopentadiene
Figure 00000001
Figure 00000001
 где R1 - R9 являются одинаковыми или различными либо, возможно, связанными друг с другом либо конденсированными с циклопентадиеном формулы (I), (II) или (III) и могут означать водород, алкильную группу с 1-30 атомами углерода, арильную группу с 6-10 атомами углерода, алкиларильную группу с 7-40 атомами углерода, силильную группу с 3-30 атомами углерода, причем алкильная группа может быть насыщенной или может содержать одну или несколько ненасыщенных связей и гетероатомы.where R 1 - R 9 are the same or different or possibly connected to each other or condensed with a cyclopentadiene of the formula (I), (II) or (III) and may mean hydrogen, an alkyl group with 1-30 carbon atoms, an aryl group with 6-10 carbon atoms, an alkylaryl group with 7-40 carbon atoms, a silyl group with 3-30 carbon atoms, the alkyl group may be saturated or may contain one or more unsaturated bonds and heteroatoms. 6. Способ по пп.1-5, отличающийся тем, что в качестве органоалюминиевых соединений используют алюмоксан и/или органилалюминиевые соединения.6. The method according to claims 1-5, characterized in that as organoaluminum compounds use aluminoxane and / or organoaluminum compounds. 7. Способ по пп.1-6, отличающийся тем, что в качестве дополнительного компонента (г) используют сопряженный диолефин в количестве 1-1000 мол в расчете на 1 мол компонента (а).7. The method according to claims 1-6, characterized in that as an additional component (g) use a conjugated diolefin in an amount of 1-1000 mol per 1 mol of component (a). 8. Способ по пп.1-7, отличающийся тем, что в качестве ароматических винильных соединений используют стирол, α-метилстирол, димер α-метилстирола, п-метилстирол, дивинилбензол и/или алкилстирол с 2-6 атомами углерода в алкильном остатке.8. The method according to claims 1 to 7, characterized in that styrene, α-methylstyrene, dimer of α-methylstyrene, p-methylstyrene, divinylbenzene and / or alkylstyrene with 2-6 carbon atoms in the alkyl residue are used as aromatic vinyl compounds. 9. Способ по пп.1-8, отличающийся тем, что кроме сопряженных диенов используют еще и другие ненасыщенные соединения, которые могут быть сополимеризованы с названными диолефинами, а именно, в количестве 0,1-80 мол.% в расчете на сопряженный диен.9. The method according to claims 1-8, characterized in that in addition to the conjugated dienes, other unsaturated compounds are also used, which can be copolymerized with the said diolefins, namely, in an amount of 0.1-80 mol.% Calculated on the conjugated diene .
RU2001104876/04A 1998-07-18 1999-07-07 The method of polymerization of conjugated diolefins (dienes) With rare earth catalysts in the presence of vinyl aromatic solvent RU2001104876A (en)

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DE19832446A DE19832446A1 (en) 1998-07-18 1998-07-18 Copolymerization of conjugated diene with vinyl-aromatic compound is carried out with a catalyst comprising rare earth metal, organoaluminum and possibly cyclopentadiene compounds
DE19832446.4 1998-07-18

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CN1518561A (en) * 2001-05-04 2004-08-04 Random or block co-or terpolymers produced by using of metal complex catalysts
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WO2009061499A1 (en) * 2007-11-09 2009-05-14 University Of Maryland, College Park Process for preparation of polyolefins via living coordinative chain transfer polymerization
JP5251744B2 (en) * 2009-06-12 2013-07-31 宇部興産株式会社 Process for producing conjugated diene polymer
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CN103965410B (en) * 2014-04-26 2017-01-04 大连理工大学 With rare earth integrated rubber for the toughener method that substance law prepares ABS resin in situ
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JP6630138B2 (en) * 2015-12-01 2020-01-15 株式会社ブリヂストン Method for producing copolymer, copolymer, rubber composition, and rubber product
JP6202182B2 (en) 2016-02-23 2017-09-27 横浜ゴム株式会社 Aromatic vinyl-diene copolymer, method for producing aromatic vinyl-diene copolymer, and rubber composition
WO2017145799A1 (en) * 2016-02-23 2017-08-31 横浜ゴム株式会社 Aromatic vinyl-diene copolymer, method for producing aromatic vinyl-diene copolymer, and rubber composition
KR102106806B1 (en) * 2018-02-09 2020-05-06 주식회사 엘지화학 Method for preparing conjugated diene based polymer and apparatus for preparing conjugated diene based polymer
CN109467661B (en) * 2018-11-05 2020-06-16 大连理工大学 Functionalized styrene thermoplastic elastomer and preparation method thereof
CN109824811A (en) * 2018-12-08 2019-05-31 濮阳班德路化学有限公司 A kind of preparation method of Alpha-Methyl benzene second dilute liquid resin
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RU2607813C2 (en) * 2012-07-12 2017-01-20 Бриджстоун Корпорейшн Method of producing polymer composition and polymer composition
US9714338B2 (en) 2012-07-12 2017-07-25 Bridgestone Corporation Method for manufacturing polymer composition and the polymer composition

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