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Highly functionalized polymers and a process for making the same

Inactive Publication Date: 2002-09-12
BRIDGESTONE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010] Advantageously, the process of the present invention overcomes many shortcomings of the prior art by end-functionalizing anionically-polymerized polymers in the presence of at least one stabilizer compound. As a result, the monomer concentration of a polymerization medium can be increased and highly functionalized polymers are obtained. Also, the amount of solvent needed to run anionic polymerizations in solution is reduced, thereby increasing the efficacy of continuous polymerization processes.

Problems solved by technology

Also, living polymers can spontaneously terminate because their carbanion centers decay with time.
These high monomer concentrations, however, produce very exothermic reactions that result in very high reaction temperatures.

Method used

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  • Highly functionalized polymers and a process for making the same
  • Highly functionalized polymers and a process for making the same
  • Highly functionalized polymers and a process for making the same

Examples

Experimental program
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Effect test

example i

[0055] Living polybutadiene polymers were prepared at low polymerization temperatures. These polymers were then divided into nine samples and each sample was subjected to different conditions. The polymers were then ultimately analyzed to determine whether the addition of lithium t-butoxide improved coupling with tin tetrachloride.

[0056] Specifically, polybutadienyllithium was prepared by admixing 3.21 Kg (7.07 lbs.) of a 25% by weight solution of 1,3-butadiene in hexane, 0.64 ml. of a 0.5 M solution of 2,2'-di (tetrahydrofuryl) propane in hexane, 5.75 ml. of a 1.0 M hexamethyleneimine in hexane, 3.90 ml. of a 1.63 M solution of n-butyllithium in hexane, and 1.71 Kg (3.76 lbs.) of dry hexane. This mixture was heated to about 49.degree. C. (120.degree. F.) for about 4 hours with agitation.

[0057] The resulting solution of polybutadienyllithium was divided and placed under pressure into nine capped and nitrogen-purged bottles. Three bottles were selected and subjected to three separate...

example ii

[0062] Two batches of polybutadiene polymers were prepared at high polymerization temperatures, subsequently subjected to heat treatment for various time intervals, and then coupled with tin tetrachloride. Lithium t-butoxide was added to one batch prior to the attainment of a peak polymerization temperature. The resulting polymers were analyzed for percent polymer conversion and percent coupling.

[0063] Specifically, the first batch was prepared by reacting 3.18 Kg (7.01 lbs.) of a 25 percent solution of 1,3-butadiene monomer in hexane, 0.43 ml of a 0.5 M 2,2'- di (tetrahydrofuryl) propane in hexane, 5.75 ml. of a 1.0 M hexamethyleneimine in hexane, 3.90 ml. of a 1.63 M solution of n-butyllithium in hexane, and 1.67 Kg (3.68 lbs.) of dry hexane. The reaction mixture was heated to 55.degree. C. (131.degree. F.) and a peak polymerization temperature of 90.5.degree. C. (195.degree. F.) was observed. Following this peak temperature, the reaction mixture was maintained at higher temperatu...

example iii

[0066] Two batches of styrene-butadiene copolymer were prepared at high polymerization temperatures. Lithium t-butoxide was added to the reaction mixtures at initial mixing. The polymers were coupled with tin tetrachloride and the percent polymer coupling was determined.

[0067] Specifically, a first batch of styrene-butadiene copolymer was prepared by charging the reactor with 549 grams (1.21 lbs.) of a 33.0% styrene solution in hexane, 2.12 Kg (4.67 lbs.) of 25.7% 1,3-butadiene solution in hexane, 7.8 ml. of 0.5 M 2,2'- di (tetrahydrofuryl) propane in hexane, 3.08 ml. of 1.95 M hexamethyleneimine in hexane, 3.80 ml. of 1.72 M solution of n-butyllithium in hexane, 6.4 ml. of 1.03 M solution of lithium t-butoxide in hexane, and an additional 1.75 Kg (3.85 lbs.) of dry hexane. This reaction mixture was heated by increasing the jacket temperature to about 117.degree. C. (242.degree. F.) until the batch temperature reached about 74.degree. C. (165.degree. F.). The mixture was then jacket...

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Abstract

A process for preparing highly functionalized polymers comprising the steps of admixing anionically-polymerizable monomers and at least one anionic-polymerization initiator to form an admixture of living polymers, adding at least one lithium alkoxide stabilizer to the admixture of living polymers to form a stabilized admixture, and adding a functionalizing agent to the stabilized admixture.

Description

FIELD OF THE INVENTION[0001] The present invention generally relates to highly functionalized polymers and processes for making the same. More particularly, the highly functionalized polymers of this invention are prepared by using anionic polymerization techniques and then the polymers are end-functionalized in the presence of stabilization compounds. More specifically, the highly functionalized polymers prepared according to this invention are end-functionalized in the presence of at least one lithium alkoxide compound.BACKGROUND OF THE INVENTION[0002] It is known to use organolithium initiators to polymerize conjugated diene, triene, and monovinyl aromatic monomers. These polymerizations proceed according to anionic polymerization mechanisms. That is, these polymerization reactions generally include the reaction of monomers by nucleophilic initiation to form and propagate a polymeric structure. Throughout the formation and propagation of this polymer, the polymeric structure is i...

Claims

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Application Information

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IPC IPC(8): C08C19/44C08F6/00C08F8/00C08F8/42
CPCC08C19/44
Inventor SCHREFFLER, JOHN R.STAYER, MARK L. JR.ANTKOWIAK, THOMAS A.
Owner BRIDGESTONE CORP
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