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Aged lanthanide-based catalyst systems and their use in the preparation of cis-1,4-polydienes

a technology of lanthanide-based catalysts and cis-1,4-polydienes, which is applied in the field of preformed lanthanide-based catalyst systems and their use in the synthesis of cis1, 4polydienes, can solve the problems of high catalyst loading of lanthanide catalysts, high cost of lanthanide compounds, and high cost of cis-1,4-polydienes prepared with lanthanide-based catalysts

Inactive Publication Date: 2020-12-31
BRIDGESTONE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method reduces catalyst and co-catalyst loadings while maintaining high cis-1,4 linkage content and low 1,2 content, achieving cost-effective production of cis-1,4-polydienes with improved polymer properties.

Problems solved by technology

However, one disadvantage of the cis-1,4-polydienes prepared with lanthanide-based catalysts is the relatively high cost of the lanthanide compounds.
Furthermore, high catalyst loadings of the lanthanide catalysts and high loadings of Al co-catalysts are often needed to obtain polymers with good processability.
Still, the aluminoxane co-catalysts are also expensive and typically a large excess is required.

Method used

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  • Aged lanthanide-based catalyst systems and their use in the preparation of cis-1,4-polydienes
  • Aged lanthanide-based catalyst systems and their use in the preparation of cis-1,4-polydienes
  • Aged lanthanide-based catalyst systems and their use in the preparation of cis-1,4-polydienes

Examples

Experimental program
Comparison scheme
Effect test

example i (

Samples 1-8)

[0138]In order to demonstrate the beneficial properties observed when aged catalyst compositions are employed to prepare cis-1,4-polydienes, the following catalyst compositions were prepared and employed to synthesize polydienes.

[0139]Unless otherwise specified, the Mooney viscosities (ML1+4) of the polymer samples were determined at 100° C. by using a Monsanto Mooney viscometer with a large rotor, a one-minute warm-up time, and a four-minute running time. The number average (Mn) and weight average (M) molecular weights of the polymer samples were determined by gel permeation chromatography (GPC). The GPC instrument was equipped with a differential refractive index (RI) detector and an ultraviolet (UV) absorption detector. The cis-1,4-linkage, trans-1,4-linkage, and 1,2-linkage contents of the polymer samples were determined by infrared spectroscopy. The GPC UV / RI ratio, which is the ratio of the UV detector signal to the RI detector signal, was used to calculate the % f...

example ii (

Samples 8-14)

[0150]In order to demonstrate the beneficial properties observed when aged catalyst compositions are treated with additional alkylating agent, the following catalyst compositions were prepared and employed to synthesize polydienes.

[0151]A preformed catalyst solution was prepared by sequentially mixing 11.76 mL of a 20.1 wt. % solution of butadiene in hexanes, 2.69 mL of a 0.54 M neodymium versatate solution in cyclohexanes, and 13.38 mL of a 1.08 M diisobutylaluminum hydride solution in hexanes. The mixture was allowed to stand at room temperature for 3 minutes and then 2.17 mL of a 1.00 M ethylaluminum dichloride solution in hexanes was added. After an additional 10 minutes of aging at room temperature the catalyst mixture was diluted with 4.00 mL of hexanes.

Sample 8

[0152]A nitrogen purged sealed glass vessel was charged with 84.6 g of anhydrous hexanes and 248.8 g of a 20.1 wt. % solution of butadiene in hexanes. To this solution was added 2.00 mL of the preformed cat...

example iii (

Samples 15-20)

[0160]In order to demonstrate the beneficial properties observed when aged catalyst compositions are treated with additional alkylating agent, the following catalyst compositions were prepared and employed to synthesize polydienes.

CatalystAA (No Catalyst Aging):

[0161]A catalyst solution was prepared by sequentially mixing 8.50 mL of a 0.11 M neodymium versatate solution in cyclohexanes, 10.79 mL of a 21.3 wt. % solution of butadiene in hexanes, 10.89 mL of a 1.03 M diisobutylaluminum hydride solution in hexanes, 2.46 mL of a 0.43 M ethylaluminum sesquichloride solution in hexanes, and 4.75 mL of hexanes. After addition of each individual chemical component to the catalyst mixture, the mixture was allowed to stand for 10 minutes.

Catalyst BB (Aged 7 Days):

[0162]A catalyst solution was prepared by sequentially mixing 8.50 mL of a 0.11 M neodymium versatate solution in cyclohexanes, 10.79 mL of a 21.3 wt. % solution of butadiene in hexanes, 10.89 mL of a 1.03 M diisobutyla...

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Abstract

A method for preparing cis-1,4-polydienes, the method comprising the steps of preparing a preformed, active lanthanide-based catalyst, aging the active lanthanide-based catalyst for more than 5 days to thereby formed an aged catalyst, and introducing the aged catalyst and conjugated diene monomer to be polymerized to thereby form an active polymerization mixture in which the conjugated diene monomer is polymerized to form a polydiene having a reactive chain end.

Description

[0001]This application claims the benefit of U.S. Provisional Application Ser. No. 62 / 108,761, filed Jan. 28, 2015, U.S. Provisional Application Ser. No. 62 / 108,781, filed Jan. 28, 2015, and U.S. Provisional Application Ser. No. 62 / 108,899, filed Jan. 28, 2015, which are incorporated herein by reference.FIELD OF THE INVENTION[0002]Embodiments of the invention relate to preformed lanthanide-based catalyst systems and their use in the synthesis of cis-1,4-polydienes.BACKGROUND OF THE INVENTION[0003]Lanthanide-based catalyst systems are known to be useful for polymerizing conjugated diene monomers to form polydienes having high cis-1,4-linkage contents, low 1,2-linkages, narrow molecular weight distributions, and linear backbones. These cis-1,4-polydienes containing a linear backbone are believed to provide better tensile properties, higher abrasion resistance, lower hysteresis, and better fatigue resistance as compared to the cis-1,4-polydienes prepared with other catalyst systems suc...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F136/06C08F136/08C08F2/02C08F2/60C08F4/42
CPCC08F136/08C08F2/02C08F136/06C08F2/60C08L9/00C08L2205/02C08F4/42C08L21/00C08F36/04C08F4/52C08F4/545
Inventor DICKSTEIN, JOSHUA S.LUO, STEVENABELL, JOSHUAKOCSIS, LAURA S.MCCAULEY, KEVIN
Owner BRIDGESTONE CORP
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