ES2544711T3 - Procedimiento para la preparación de polímeros de dieno o copolímeros de vinilareno-dieno estadísticos - Google Patents
Procedimiento para la preparación de polímeros de dieno o copolímeros de vinilareno-dieno estadísticos Download PDFInfo
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- ES2544711T3 ES2544711T3 ES11781615.7T ES11781615T ES2544711T3 ES 2544711 T3 ES2544711 T3 ES 2544711T3 ES 11781615 T ES11781615 T ES 11781615T ES 2544711 T3 ES2544711 T3 ES 2544711T3
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- diene
- statistical
- preparation
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- polymers
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- 229920000642 polymer Polymers 0.000 title abstract description 8
- 229920001577 copolymer Polymers 0.000 title abstract 2
- 150000001993 dienes Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title 1
- 229920002554 vinyl polymer Polymers 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 229910052744 lithium Inorganic materials 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 alkyl lithium Chemical compound 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- CSYYEIXEPOTLMO-UHFFFAOYSA-N 2-(2-methoxyethyl)oxolane Chemical compound COCCC1CCCO1 CSYYEIXEPOTLMO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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
- 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
- C08F4/46—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 alkali metals
- C08F4/48—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 alkali metals selected from lithium, rubidium, caesium or francium
-
- 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
- C08F36/06—Butadiene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/60—Polymerisation by the diene synthesis
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—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
- C08F236/04—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
- C08F236/10—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 with vinyl-aromatic monomers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Un procedimiento para la preparación de polímeros de dieno o copolímeros de vinilareno-dieno estadísticos (aleatorios) que comprende la (co)polimerización aniónica, en disolventes hidrocarbonados, de al menos un monómero de un dieno conjugado, opcionalmente en presencia de un monómero de vinilarilo, y usando un compuesto que pertenece al grupo de alquilos de litio como iniciador, caracterizado porque el iniciador de alquil-litio es modificado in situ por medio de una reacción con un compuesto que tiene la fórmula general (I) : Rm - ( X - H ) n (I) en donde R es un (ciclo)alquilo C2-C20 o un radical aromático C6-C20, X es un heteroátomo que pertenece al grupo V A o grupo VI A del sistema periódico de elementos, n es un número entero superior o igual a 1, m es un número entero >= 1 que depende de la valencia del heteroátomo X.
Description
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E11781615
05-08-2015
Ejemplo 4
Se cargaron en el siguiente orden 600 gramos de ciclohexano anhidro y 27 gramos de butadieno anhidro recién destilado, en un reactor de depósito agitado de 1 litro provisto de una camisa para la circulación de un fluido termostático. A continuación, se introdujo 1 mmol de alcohol t-butílico.
Se reguló la temperatura de la mezcla de reacción a 120°C por medio de un termostato y se mantuvo constante a ± 4°C durante todo el experimento. A continuación, se alimentaron 1,5 mmoles de n-butil litio con el fin de obtener una relación en moles entre el alcoholato de litio, resultante de la reacción entre n-butil litio y alcohol t-butílico, y el n-butil litio activo para la polimerización, de aproximadamente 2:1. Las condiciones de reacción se mantuvieron constantes durante 60 minutos, tras lo cual se alimentó una cantidad de alcohol etílico, que era equimolecular con respecto a la cantidad de n-butil litio activo. Los resultados se indican en la Tabla 1.
Tabla 1
- Ejemplos
- Temperatura (ºC) [RO-Li+] / [n-butLi] Δ abs [%] HMW [%]
- Ejemplo comparativo 1
- 80 0 1,08 0
- Ejemplo comparativo 2
- 120 0 1,23 28,0
- Ejemplo 3
- 120 1,1 1,19 17,1
- Ejemplo 4
- 120 1,9 1,14 12,2
La columna “altos pesos moleculares (HMW, del inglés high molecular weights) " de la Tabla 1 indica el contenido, expresado en porcentaje en peso, de las múltiples fracciones de pesos moleculares con respecto a las del precursor del polímero. Estas familias de macromoléculas se originan a partir de la presencia de reacciones de extremo de cadena mediante metalación de la cadena, lo que lleva a la formación de ramificaciones estadísticas (aleatorias). El experimento que se llevó a cabo a 80°C muestra que, en ausencia de un modificador, esta temperatura es muy baja para producir la reacción de extremo de cadena y que el polímero está completamente libre de fracciones de alto peso molecular.
Ejemplo comparativo 5
Se cargaron en el siguiente orden 600 gramos de ciclohexano anhidro, 27 gramos de butadieno anhidro recién destilado y 100 ppm de 2-metoxi-etil-tetrahidrofurano (etil-THFA), en un reactor de depósito agitado de 1 litro provisto de una camisa para la circulación de un fluido termostático. El reactor estaba provisto de un sistema para medir de manera constante el espectro de absorción UV-Vis de la disolución polimérica. Este sistema consistía en una celda de flujo de cuarzo, que tenía un paso óptico de 2 mm, conectada al reactor por medio de un circuito en el que una bomba HPLC retiraba la disolución polimérica, la hacía pasar a través de la celda de flujo y la enviaba de regreso al reactor. Esto permitió medir de manera constante la concentración del extremo de cadena viviente de butadienilo, aplicando la ley de Lambert-Beer:
A =1 ε c
en donde A es la absorbancia, 1 es el paso óptico de la celda de medición, ε es el coeficiente de extinción en moles (el cual para butadienilo en presencia de 2-metoxi-etil-tetrahidrofurano, es de aproximadamente 6.500 l·cm-1·mol-1) y c es la concentración en moles. El espectro de UV-Vis se midió usando un espectrómetro Lambda 25 de Perkin Elmer dentro del intervalo de 260 a 400 nm, a intervalos de 2 minutos entre una medición y otra ,con el fin de medir la extensión de la reacción de extremo de cadena.
Se reguló la temperatura de la mezcla de reacción a 70°C por medio de un termostato y se mantuvo constante a ± 4°C durante todo el experimento. A continuación, se alimentó 1 mmol de n-butil litio para comenzar la reacción de polimerización de butadieno. Las condiciones de reacción se mantuvieron constantes durante 30 minutos, tras lo cual se recogió y coaguló el polímero y luego se estabilizó con un antioxidante y se sometió a ensayo para determinar la distribución de pesos moleculares a través de GPC. Los resultados se indican en la Tabla 2.
Ejemplo 6
Se cargaron en el siguiente orden 600 gramos de ciclohexano anhidro, 27 gramos de butadieno anhidro y 100 ppm de etil-THFA, en un reactor de depósito agitado de 1 litro provisto de una camisa para la circulación de un fluido termostático. A continuación, se introdujo 1 mmol de alcohol t-butílico. El reactor estaba provisto de un sistema para medir de manera constante el espectro de absorción UV-Vis de la disolución polimérica, como se describe en el ejemplo previo.
7
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2010A001826A IT1402007B1 (it) | 2010-10-06 | 2010-10-06 | Procedimento per la preparazione di polimeri dienici o copolimeri statistici vinilarene-diene |
| ITMI20101826 | 2010-10-06 | ||
| PCT/IB2011/054282 WO2012046167A1 (en) | 2010-10-06 | 2011-09-29 | Process for the preparation of diene polymers or statistical vinylarene-diene copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2544711T3 true ES2544711T3 (es) | 2015-09-03 |
Family
ID=43479661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11781615.7T Active ES2544711T3 (es) | 2010-10-06 | 2011-09-29 | Procedimiento para la preparación de polímeros de dieno o copolímeros de vinilareno-dieno estadísticos |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8710164B2 (es) |
| EP (1) | EP2625209B1 (es) |
| KR (1) | KR101831475B1 (es) |
| CN (1) | CN103228683A (es) |
| BR (1) | BR112013008218B1 (es) |
| CA (1) | CA2813485C (es) |
| ES (1) | ES2544711T3 (es) |
| IT (1) | IT1402007B1 (es) |
| MX (1) | MX340561B (es) |
| RU (1) | RU2569308C2 (es) |
| WO (1) | WO2012046167A1 (es) |
| ZA (1) | ZA201301957B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3183280T3 (pl) * | 2014-08-20 | 2018-12-31 | Versalis S.P.A. | Sposób wytwarzania polimerów dienu lub bezładnych kopolimerów winyloaren-dien |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764572A (en) * | 1985-07-23 | 1988-08-16 | Shell Oil Company | Anionic polymerization process |
| US5625017A (en) * | 1992-10-19 | 1997-04-29 | Bridgestone Corporation | Process for preparing a polymer using lithium initiator prepared by in situ preparation |
| FR2698630B1 (fr) * | 1992-11-27 | 1995-01-06 | Atochem Elf Sa | Procédé de préparation de copolymères séquences élastomères thermoplastiques dérivés de diènes conjugués et de méthacrylate de méthyle, à tenue à la chaleur améliorée et produits obtenus. |
| US5416168A (en) * | 1994-03-31 | 1995-05-16 | Shell Oil Company | Protected functional initiators for making terminally functionalized polymers |
| JP3625919B2 (ja) * | 1995-10-16 | 2005-03-02 | 株式会社ブリヂストン | 重合体の製造方法 |
| IT1289605B1 (it) | 1997-01-30 | 1998-10-15 | Enichem Spa | Copolimerizzazione anionica di dieni coniugati e vinil areni in presenza di alchil eteri del tetraidropiranil metanolo |
| DE19806775A1 (de) * | 1998-02-18 | 1999-08-19 | Basf Ag | Verfahren zur retardierten anionischen Polymerisation |
| IT1318479B1 (it) | 2000-04-20 | 2003-08-25 | Enichem Spa | Procedimento per la preparazione di gomme sbr con miglioratalavorabilita' e minore resistenza al rotolamento. |
| US6451935B1 (en) * | 2000-05-10 | 2002-09-17 | Bridgestone Corporation | Highly functionalized polymers and a process for making the same |
| DE10053324A1 (de) * | 2000-10-27 | 2002-05-08 | Basf Ag | Verfahren zum Kettenabbruch bei der anionischen Polymerisation |
| US6515087B2 (en) * | 2000-12-14 | 2003-02-04 | The Goodyear Tire & Rubber Company | Synthesis of elastomers having low hysteresis |
| RU2175330C1 (ru) * | 2001-01-25 | 2001-10-27 | Федеральное государственное унитарное предприятие "Научно-исследовательский институт синтетического каучука им. академика С.В. Лебедева" | Способ получения диеновых (со)полимеров, содержащих функциональные группы |
| US7074869B2 (en) * | 2002-12-27 | 2006-07-11 | The Goodyear Tire & Rubber Company | Synthesis of functionalized high vinyl rubber |
| ITMI20060385A1 (it) | 2006-03-03 | 2007-09-04 | Polimeri Europa Spa | Procedimento in continuo per la preparazione di copolimeri randon dieni coniugati-vinil areni |
| WO2009032154A2 (en) * | 2007-08-31 | 2009-03-12 | Bridgestone Corporation | Synthesis of a liquid polymer and a functionalized polymer |
-
2010
- 2010-10-06 IT ITMI2010A001826A patent/IT1402007B1/it active
-
2011
- 2011-09-29 EP EP11781615.7A patent/EP2625209B1/en active Active
- 2011-09-29 MX MX2013003738A patent/MX340561B/es active IP Right Grant
- 2011-09-29 RU RU2013120309/04A patent/RU2569308C2/ru active
- 2011-09-29 CA CA2813485A patent/CA2813485C/en not_active Expired - Fee Related
- 2011-09-29 CN CN2011800484112A patent/CN103228683A/zh active Pending
- 2011-09-29 KR KR1020137011404A patent/KR101831475B1/ko not_active Application Discontinuation
- 2011-09-29 US US13/877,438 patent/US8710164B2/en active Active
- 2011-09-29 BR BR112013008218-6A patent/BR112013008218B1/pt active IP Right Grant
- 2011-09-29 ES ES11781615.7T patent/ES2544711T3/es active Active
- 2011-09-29 WO PCT/IB2011/054282 patent/WO2012046167A1/en active Application Filing
-
2013
- 2013-03-15 ZA ZA2013/01957A patent/ZA201301957B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112013008218A2 (pt) | 2016-06-21 |
| ZA201301957B (en) | 2013-11-27 |
| EP2625209A1 (en) | 2013-08-14 |
| US20130245217A1 (en) | 2013-09-19 |
| IT1402007B1 (it) | 2013-08-28 |
| RU2569308C2 (ru) | 2015-11-20 |
| CA2813485C (en) | 2018-10-16 |
| BR112013008218B1 (pt) | 2020-10-13 |
| WO2012046167A1 (en) | 2012-04-12 |
| CN103228683A (zh) | 2013-07-31 |
| RU2013120309A (ru) | 2014-11-20 |
| ITMI20101826A1 (it) | 2012-04-07 |
| EP2625209B1 (en) | 2015-06-03 |
| KR101831475B1 (ko) | 2018-02-22 |
| MX2013003738A (es) | 2013-10-03 |
| CA2813485A1 (en) | 2012-04-12 |
| US8710164B2 (en) | 2014-04-29 |
| MX340561B (es) | 2016-07-14 |
| KR20130141509A (ko) | 2013-12-26 |
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