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Polyphosphorus polymer that is thiol-functionalised at the chain ends and production method thereof

A technology of polymers and polymer chains, applied in the field of polyphosphorus-based polymers, can solve the problems of polymer elastomer property degradation and performance degradation

Inactive Publication Date: 2016-09-21
MICHELIN & CO CIE GEN DES ESTAB MICHELIN +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This change in macrostructure generally results in a deterioration of the elastomeric properties of the polymer and thus in its performance in the intended application (eg in tires)

Method used

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  • Polyphosphorus polymer that is thiol-functionalised at the chain ends and production method thereof
  • Polyphosphorus polymer that is thiol-functionalised at the chain ends and production method thereof
  • Polyphosphorus polymer that is thiol-functionalised at the chain ends and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Example 1: Synthesis of xanthates with C4 cyanomethyl functional groups

[0112] - Reaction scheme

[0113]

[0114] Scheme 1. Synthesis of xanthates with C4 cyanomethyl functional groups

[0115] 6g (6.81x 10 -2mol) 3-methylbutanol was dissolved in 45ml THF. BuLi solution (1.6M in hexane) (46.5ml, 7.44x 10 -2 mol) was added dropwise to the reaction mixture at 0 °C. It was allowed to react with stirring for 30 minutes. Carbon disulfide (30ml, 4.96x 10 -1 mol) was added dropwise to the reaction medium at 0°C. The reaction mixture was then maintained at 0 °C for 30 minutes under magnetic stirring. Divide 11.6g (13.62x 10 -2 mol) bromoacetonitrile was added dropwise to the reaction mixture, and then the solution was kept under stirring for 15h. After evaporating THF, pass through CH 2 Cl 2 / water (1:1) to extract and purify the residue. Evaporate CH in vacuo 2 Cl 2 solution. After cleanup and evaporation on a chromatographic column (eluent: petroleum ethe...

Embodiment 2

[0118] Example 2: Synthesis of dimethyl vinyl phosphonate DMVP-C4 monoadduct

[0119] - Reaction scheme

[0120]

[0121] Scheme 2. Synthesis of DMVP-C4 monoadduct

[0122] C4 xanthate (2.76g, 13.59x 10 -2 mol), dimethyl vinyl phosphonate (1g, 7.35x 10 - 3 mol) and 1,2-dichloroethane solvent (6ml) were introduced into a 25ml round bottom flask covered with a reflux condenser. The mixture was degassed under argon for 15 minutes. The reaction mixture was then maintained at the reflux point of the solvent (95° C.) for 7 hours with magnetic stirring. 5 mole % dilauroyl peroxide was added every 60 minutes up to 25 mole %. After cleanup on a chromatography column (eluent: ethyl acetate) and evaporation, the final synthesis yield was 65%.

[0123] 1 H NMR (300MHz, CDCl 3 , δ=ppm): 5.58 (1H, m, O-CHCH 3 ), 4.35 (1H, m, NC-CH 2 -CH 2 -CH 1 -S-C=S), 3.82(3H, s, P=(OCH 3 ) 2 ), 2.62 (2H, m, NC-CH 2 -CH 2 -CH 1 -S-C=S), 2.45-2.21 (2H, m, NC-CH 2 -CH 2 -CH 1 -S-C=S)...

Embodiment 4

[0132] Example 4: Pyrolysis of DMVP-C4 monoadduct

[0133] - Reaction scheme

[0134]

[0135] Scheme 4. Pyrolysis of DMVP-C4 monoadduct

[0136] DMVP-C4 monoadduct (250mg, 7.37x 10 -4 mol) and 1,2-dichlorobenzene solvent (3ml) were introduced into a 25ml round bottom flask covered with a reflux condenser. The reaction mixture was degassed under argon for 15 minutes and then kept in the dark at the reflux point of the solvent (200° C.) for 5 minutes. The pyrolysis yield was 70%.

[0137] 31 P NMR (300MHz, CDCl 3 , δ=ppm): 26.3 (1P, s, P=(OCH 3 ) 2 ).

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Abstract

The invention relates to a novel polyphosphorus polymer that is thiol-functionalised at the chain ends, of which the polymer chain comprises units bearing at least one phosphonate pendant functional group and / or at least one phosphonic pendant functional group along the length of the chain. This novel polymer is particularly suitable for use in a thiol-ene coupling reaction. This provides the possibility of grafting the polyphosphorus polymers to diene polymers for example.

Description

technical field [0001] The present invention relates to a method for the synthesis of chain-end thiol-functionalized polymers with pendant phosphonate and / or phosphonic acid functions along the chain. The present invention also relates to said thiol-terminated polyphosphorus-based polymers. Background technique [0002] Various strategies are possible in order to modify the properties of the synthetic elastomers comprised in tire rubber compositions. Among these strategies, the introduction of new chemical functional groups at the polymer chain ends or along the polymer chain is one of the methods used. [0003] Within the scope of the present application, the applicant is particularly concerned with functionalization along the diene polymer chain. Various reactions on the unsaturation of functionalized diene polymers are known from the literature. Mention may be made between dienophiles (e.g. maleic anhydride) and diene copolymers with conjugated dienes along the chain b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F30/02C08F8/00C08F299/00
CPCC08F299/00C08F2438/03C08C19/24C08F8/00C08F2810/40C08F30/02
Inventor C·迪雷R·马特穆尔I·布利迪O·库特利耶M·德塔拉克
Owner MICHELIN & CO CIE GEN DES ESTAB MICHELIN
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