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Functionalized polymers and methods for their manufacture

a technology of functionalized polymers and polymers, applied in the direction of transportation and packaging, tyre parts, special tyres, etc., can solve the problems of polymer high cold flow due to polymer hysteresis and unpredictable whether a reactive polymer can be functionalized by treatment with a particular functionalizing agen

Inactive Publication Date: 2011-03-31
BRIDGESTONE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a method for making a functionalized polymer by polymerizing a monomer with a coordination catalyst to form a reactive polymer, and then reacting the reactive polymer with a carboxylic or thiocarboxylic ester containing a silylated amino group. This method can produce a functionalized polymer with improved properties, such as increased strength and flexibility. The invention also provides a functionalized polymer made by polymerizing a conjugated diene monomer with a coordination catalyst to form a reactive cis-1,4-polydiene, and then reacting the reactive polydiene with a carboxylic or thiocarboxylic ester containing a silylated amino group. This functionalized polymer has a high cis-1,4-linkage content and improved properties.

Problems solved by technology

Nevertheless, whether a particular functional group imparted to a polymer can reduce hysteresis is often unpredictable.
However, whether a reactive polymer can be functionalized by treatment with a particular functionalizing agent can be unpredictable.
However, one disadvantage of the cis-1,4-polydienes prepared with lanthanide-based catalysts is that the polymers exhibit high cold flow due to their linear backbone structure.
The high cold flow causes problems during storage and transport of the polymers and also hinders the use of automatic feeding equipment in rubber compound mixing facilities.

Method used

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  • Functionalized polymers and methods for their manufacture
  • Functionalized polymers and methods for their manufacture
  • Functionalized polymers and methods for their manufacture

Examples

Experimental program
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example 1

Synthesis of Ethyl N,N-Bis(trimethylsilyl)glycinate (BTMSEG)

[0190]About 6.02 g of ethyl glycinate hydrochloride, 14.39 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 21.1 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was stirred at room temperature for 19 hours to give a biphasic mixture. The top layer was transferred to another flask, and the bottom layer was extracted with 40 ml of toluene. The combined toluene solution was evaporated under vacuum. The residue was extracted with 100 ml of hexane, and the hexane layer was evaporated under vacuum, yielding ethyl [bis(trimethylsilyl)amino]acetate, also known as ethyl N,N-bis(trimethylsilyl)glycinate (BTMSEG), as a colorless liquid (9.23 g, 87% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 3.89 (quartet...

example 2

Synthesis of Ethyl 3-[Bis(trimethylsilyl)amino]propionate (3-BTMSAEP)

[0191]About 7.23 g of ethyl 3-aminopropionate hydrochloride, 15.71 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 23.00 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was stirred at room temperature for 39 hours to give a biphasic mixture. The top layer was transferred to another flask, and the bottom layer was extracted with 40 ml of toluene. The combined toluene solution was evaporated under vacuum. The residue was extracted with 100 ml of hexane, and the hexane layer was evaporated under vacuum, yielding ethyl 3-[bis(trimethylsilyl)amino]propionate (3-BTMSAEP) as a colorless oil (11.03 g, 90% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 3.91 (quartet, 2H, OCH2 protons), 3.21 (mult...

example 3

Synthesis of Ethyl 3-[Bis(trimethylsilyl)amino]benzoate (3-BTMSAEBz)

[0192]About 8.37 g of ethyl 3-aminobenzoate, 11.80 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 25.91 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was heated to reflux for 30 hours to give a biphasic mixture. The top layer was transferred to another flask, and the bottom layer was extracted with 40 ml of toluene. The combined toluene solution was evaporated under vacuum. The residue was extracted with 100 ml of hexane, and the hexane layer was evaporated under vacuum, yielding ethyl 3-[bis(trimethylsilyl)amino]benzoate (3-BTMSAEBz) as a yellow oil (14.50 g, 92% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 7.95 (multiplet, 1H, aromatic proton), 7.91 (multiplet, 1H, aromatic proton)...

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Abstract

A method for preparing a functionalized polymer, the method comprising the steps of (i) polymerizing monomer with a coordination catalyst to form a reactive polymer; and (ii) reacting the reactive polymer with a carboxylic or thiocarboxylic ester containing a silylated amino group.

Description

FIELD OF THE INVENTION[0001]One or more embodiments of the present invention relate to functionalized polymers and methods for their manufacture.BACKGROUND OF THE INVENTION[0002]In the art of manufacturing tires, it is desirable to employ rubber vulcanizates that demonstrate reduced hysteresis, i.e., less loss of mechanical energy to heat. For example, rubber vulcanizates that show reduced hysteresis are advantageously employed in tire components, such as sidewalls and treads, to yield tires having desirably low rolling resistance. The hysteresis of a rubber vulcanizate is often attributed to the free polymer chain ends within the crosslinked rubber network, as well as the dissociation of filler agglomerates.[0003]Functionalized polymers have been employed to reduce the hysteresis of rubber vulcanizates. The functional group of the functionalized polymer may reduce the number of free polymer chain ends via interaction with filler particles. Also, the functional group may reduce fill...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08J5/14C08F8/30
CPCC08C19/44C08F136/06C08F236/06C08F4/545B60C1/00C08C19/00C08C19/25C08L15/00
Inventor LUO, STEVEN
Owner BRIDGESTONE CORP
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