Graft polymer to which combined nitrogen molecules are grafted

A technology for polymers and compounds, applied in organic chemistry and other directions, can solve problems such as reducing hysteresis

Active Publication Date: 2013-03-20
MICHELIN & CO CIE GEN DES ESTAB MICHELIN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Unexpectedly, the applicants have found that it is possible to obtain polymers modified with groups other than thiazolines and oxazolines mentioned in the above patents which are hardly susceptible to attack by nucleophiles, Modified polymers with reduced hysteresis

Method used

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  • Graft polymer to which combined nitrogen molecules are grafted
  • Graft polymer to which combined nitrogen molecules are grafted
  • Graft polymer to which combined nitrogen molecules are grafted

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Example 1: By grafting 2,4,6-trimethyl-3-(2-(2-oxyimidazolidin-1-yl)ethoxy) Nitrile Oxide Modified SBR

[0106] 1.1- Preparation of Modifier:

[0107] a) Preparation of 1-(2-(3'-nitrileoxytrimethylphenyl-1'-oxyl)ethyl)imidazolidin-2-one

[0108]

[0109] This compound can be prepared from hydroxyethylimidazolidinone tricresylphenol according to the following synthetic scheme.

[0110]

[0111] b) Preparation of 3-hydroxy-2,4,6-trimethylbenzaldehyde

[0112]

[0113] This compound can be obtained according to the procedures described in the following articles: Yakubov, A.P.; Tsyganov, D.V.; Belen'kii, L.I.; Krayushkin, M.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation) ; vol.40; nb.7.2; (1991); pp. 1427-1432; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb.7;

[0114] c) Preparation of 1-(2-chloroethyl)imidazolidin-2-one:

[0115]

[0116] This product is described in the article Naga...

Embodiment 2

[0174] Example 2: By grafting 2,4,6-trimethyl-3-(2-(2-oxoimidazolidin-1-yl)ethoxy) Bulk Modified Polyisoprene

[0175] 2.1- Modifier grafted to polyisoprene Natsyn2200 (Goodyear)

[0176] The same modifier as that obtained in Example 1 before was used.

[0177] 2.85 g of 2,4,6-trimethyl-3-(2-(2-oxoimidazolidin-1-yl ) ethoxy) nitrile oxide doped with 30 g of polyisoprene Natsyn 2200 ([ML(1+4) 100°C=79, unit 3,4=0.5%, unit trans 1,4=1.9%, unit cis 1,4=97.6%, Mw=1044.10 3 g / mol, Vp=3.6]). The mixture was homogenized 15 times.

[0178] This mixing stage was followed by a heat treatment in a press at a pressure of 10 bar.

[0179] The duration and temperature of this second phase are adjusted.

[0180] 1 H NMR analysis made it possible to determine the molar amount of grafting and the molar yield of grafting, which are reported in the table below:

[0181] Table 6

[0182]

[0183]

Embodiment 3

[0184] Example 3: By grafting 3-methoxy-4-[2-(2-oxyimidazolidin-1-yl)ethoxy]benzyl Nitrile Oxide Modified SBR

[0185] 1.1- Preparation of Modifier:

[0186] a) Preparation of 3-methoxy-4-[2-(2-oxyimidazolidin-1-yl)ethoxy]benzonitrile oxide

[0187]

[0188] This compound can be prepared from vanillin and 2-chloroethyl imidazolidinone according to the following synthetic scheme:

[0189]

[0190] b) Preparation of 3-methoxy-4-[2-(2-oxyimidazolidin-1-yl)ethoxy]benzaldehyde

[0191]

[0192] Route A

[0193] Vanillin (30.0g, 0.197mol) and K 2 CO 3 (95.4 g, 0.690 mol) in DMF (200 mL) was heated at 50°С for 15 min. To this suspension was added 1-(2-chloroethyl)imidazolidinone-2-one (44.0 g, 0.296 mol, purity >90%) in DMF (30 mL), 1-(2-chloroethyl The preparation of the imidazolidinone-2-one has been described in Example 1. The reaction medium is heated to 90°C (T 浴 ), the temperature is maintained for about 4 hours. The reaction medium was allowed to come...

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Abstract

The present invention relates to a modified polymer produced by grafting a compound thereto, said compound including at least one group Q and at least one group A bonded together by at least one, and preferably only one, spacer group Sp, where: Q includes a dipole containing at least one, and preferably only one, nitrogen atom capable of being grafted onto the polymer chain by [l,3]-dipolar cycloaddition; A includes a combined group that includes at least one nitrogen atom; and Sp is an atom or a group of atoms forming a bond between Q and A.

Description

technical field [0001] The present invention relates to a polymer modified by grafting nitrogen-containing associative molecules comprising at least one unit enabling their association with each other or with fillers via non-covalent bonds. Background technique [0002] Since the need to save fuel and protect the environment has become a priority, it is advantageous to prepare mixtures with good mechanical properties and as low hysteresis as possible, in order to be able to use said mixtures in the form of rubber compositions which Can be used for the manufacture of various semi-finished products that are introduced into the composition of the tire casing (eg undertread, sidewalls, tread) and in order to obtain tires with reduced rolling resistance. [0003] Reduction of the hysteresis of the mixture is a long-term goal which must however be achieved while maintaining the processability of the mixture to be used. [0004] To achieve the goal of reducing lag, many workaround...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08C19/28C08F8/30C08F10/06
CPCC07D233/36C08C19/22C08C19/28C07D233/00C08F36/04C07D233/34C08F8/30C08F10/06C08F210/16
Inventor J·阿劳若达西尔瓦J-M·法夫罗A-F·萨利特N·西博特
Owner MICHELIN & CO CIE GEN DES ESTAB MICHELIN
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