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Polymers functionalized with lactones or thiolactones containing a protected amino group

A thiolactone, polymer technology, used in transportation and packaging, special tires, tire parts, etc.

Active Publication Date: 2014-06-11
BRIDGESTONE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polymers made using anionic initiators may also exhibit high cold flow problems without introducing any coupling or branching structures

Method used

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  • Polymers functionalized with lactones or thiolactones containing a protected amino group
  • Polymers functionalized with lactones or thiolactones containing a protected amino group
  • Polymers functionalized with lactones or thiolactones containing a protected amino group

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preparation example Construction

[0097] The preparation of reactive polymers according to the invention can be achieved by polymerizing conjugated diolefins, optionally together with monomers copolymerizable with conjugated diene monomers, in the presence of a catalytically effective amount of a catalyst or initiator. vinyl monomers. The introduction of catalyst or initiator, conjugated diene monomer, optional comonomer, and any solvent (if used) forms the polymerization mixture in which the reactive polymer is formed. The amount of catalyst or initiator to be used can depend on the interplay of various factors, such as the type of catalyst or initiator used, the purity of the ingredients, the polymerization temperature, the desired rate and conversion of polymerization, the desired molecular weight and many other factors. Accordingly, no specific amount of catalyst or initiator can be definitively described other than to indicate that a catalytically effective amount of catalyst or initiator may be used.

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example 1

[0212] Example 1. α-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-γ-butyrolactone (lactone-NSi 2 )Synthesis

[0213] α-Amino-γ-butyrolactone hydrobromide (9.01 g, 0.050 mmol) and dichloromethane (30 mL) were mixed in an ice-bath cooled round bottom flask. To this mixture was added triethylamine (16.70 g, 0.165 mmol), and a solution of 1,2-bis(chlorodimethylsilyl)ethane (10.76 g, 0.050 mmol) in dichloromethane (50 ml) . The resulting mixture was stirred at room temperature for 47 hours, then evaporated under vacuum. The residue was extracted with 500 ml cyclohexane and filtered through frit. The filtrate was evaporated under vacuum to yield α-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-γ-butyrolene as a white solid Esters (abbreviated as Lactone-NSi 2 ) (11.8 g, 97% yield). product of 1 H NMR data (C 6 D. 6 , 25°C, referring to tetramethylsilane) as follows: δ3.50 (multiplet, 1H), 3.33 (multiplet, 1H), 3.22 (multiplet, 1H), 1.64 (multiplet, 1H), 1.50 ( ...

example 2

[0215] Example 2. α-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-γ-thiobutyrolactone (thiolactone -NSi 2 )Synthesis

[0216] DL-homocysteine ​​thiolactone hydrochloride (7.68 g, 0.050 mmol) and dichloromethane (30 mL) were mixed in a round bottom flask cooled with an ice bath. To this mixture was added triethylamine (16.70 g, 0.165 mmol), and a solution of 1,2-bis(chlorodimethylsilyl)ethane (10.76 g, 0.050 mmol) in 50 ml of dichloromethane. The resulting mixture was stirred at room temperature for 47 hours, then evaporated under vacuum. The residue was extracted with 500 ml cyclohexane and filtered through fritted glass. The filtrate was evaporated under vacuum to yield α-(2,2,5,5-tetramethyl-1-aza-2,5-disila-1-cyclopentyl)-γ-thioxo as a white solid Butyrolactone (abbreviated as Thiolactone-NSi 2 ) (11.8 g, 97% yield). product of 1 H NMR data (C 6 D. 6 , 25°C, referring to tetramethylsilane) are listed as follows: δ3.24 (multiplet, 1H), 2.34 (multiplet, 1H), 2...

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Abstract

A method for preparing a functionalized polymer, the method comprising the steps of: (i) polymerizing monomers to form a reactive polymer, and (ii) reacting the reactive polymer with a lactone or thiolactone that contains a protected amino group.

Description

[0001] This application claims the benefit of US Provisional Patent Application Serial No. 61 / 529,541, filed August 31, 2011, which is incorporated herein by reference. technical field [0002] One or more embodiments of the invention relate to polymers functionalized with lactones or thiolactones containing protected amino groups. Background technique [0003] In the field of tire manufacture, it is desirable to use vulcanizates which exhibit reduced hysteresis, ie less loss of mechanical energy to heat. For example, vulcanizates exhibiting reduced hysteresis are advantageously used in tire components such as sidewalls and treads to produce tires with the desired low rolling resistance. The hysteresis of vulcanizates is generally attributed to free polymer chain ends within the crosslinked rubber network, and dissociation of filler agglomerates. [0004] Functionalized polymers have been used to reduce the hysteresis of vulcanizates. The functional groups of the functiona...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08C19/26C08C19/44
CPCC08F8/34C08C19/44B60C1/00C08L21/00C08F136/06
Inventor 史蒂文·骆秦增全
Owner BRIDGESTONE CORP
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