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[Bis (trihydrocarbyl silyl) amino silyl] functionalized styrene and preparation method thereof

A technology of styrene derivatives and alkyl groups, which is applied in chemical instruments and methods, organic chemistry, compounds of group 4/14 elements of the periodic table, etc., can solve problems such as hydrolytic instability of aniline derivatives

Active Publication Date: 2020-02-11
SYNTHOS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under typical processing conditions, the compound according to EP 2772515A1 and the N,N-bis(SiMe 3 ) 2 more hydrolytically unstable than aniline derivatives
[0008] The prior art only deals with the preparation of N-functionalized polydienes with varying amounts of N-functional groups that can interact with commonly used fillers (i.e. silica and carbon black) through non-covalent interactions

Method used

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  • [Bis (trihydrocarbyl silyl) amino silyl] functionalized styrene and preparation method thereof
  • [Bis (trihydrocarbyl silyl) amino silyl] functionalized styrene and preparation method thereof
  • [Bis (trihydrocarbyl silyl) amino silyl] functionalized styrene and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Magnesium metal (13.37 g, 0.55 mol) was loaded into a 1 L volumetric reactor equipped with a magnetic stirrer, dropping funnel and reflux condenser with gas introduction accessory and oil valve (Zaitsev gasket) under an argon atmosphere, followed by addition of Dry and deoxygenated tetrahydrofuran (THF, 200 mL) and iodine (I 2 , 0.69g, 2.75mmol). Next, it was heated to 50° C. with stirring the contents of the reactor. Magnesium activation was performed until the brown color disappeared, then the reactor contents were allowed to cool to room temperature. Then, 1-[{N,N-bis(trimethylsilylamino)}(dimethylsilyl)]-2-{chloro-dimethylsilyl}ethane (170.10 g, 0.50 mol) and the remainder of the solvent (300 mL) were added to the prepared activated magnesium. The dropping funnel was filled with 1-bromo-4-vinylbenzene (99 g, 0.53 mol). In the initial step of the reaction, 9.90 mL of 1-bromo-4-vinylbenzene was added dropwise to the mixture without stirring the reactor contents. ...

Embodiment 2

[0085] A 20 L volume reactor equipped with a magnetic stirrer, dropping funnel and reflux condenser with gas introduction accessories and oil valve (Zaitsev gasket) was loaded with magnesium metal (153.73 g, 6.2232 mol) in an argon atmosphere, followed by addition of Dry and deoxygenated tetrahydrofuran (THF, 1.00L) and iodine (I 2 , 7.97g, 31.62mmol). Next, it was heated to 50° C. with stirring the contents of the reactor. Magnesium activation was performed until the brown color disappeared, then the reactor contents were allowed to cool to room temperature. Then, 1-[{N,N-bis(trimethylsilylamino)}(dimethylsilyl)]-2-{chlorodimethylsilyl}ethane (1956.20 g, 5.75 mol) was mixed with The remaining portion (9.00 L) of solvent was added to the prepared activated magnesium. The dropping funnel was filled with 1-bromo-4-vinylbenzene (1,105 g, 6.04 mol). In the initial step of the reaction, 100 mL of 1-bromo-4-ethylbenzene was added dropwise into the reaction system without stirrin...

Embodiment 3

[0087] In the same manner as in Example 1, in 6.19g (0.26mol) with I 2(0.38 g, 1.16 mmol) in the presence of activated Mg to make 1-[{N,N-bis(trimethylsilylamino)}(dimethylsilyl)]-2-{chlorodimethylsilyl } Ethane (78.82 g, 0.23 mol) was reacted with 1-(chloromethyl)-4-vinylbenzene (37.13 g, 0.24 mol). 91.03 g of 1-[{N,N-bis(trimethylsilylamino)}(dimethylsilyl)]-2-{(4-vinylphenylmethyl)dimethylsilyl} were obtained Ethane, the yield is 93%. The product was subjected to spectroscopic analysis.

[0088] GC-MS:

[0089] 393.2(0.9); 260.2(3.4); 237.4(2.0); 236.4(10.3); 234.5(41.4); 223.5(2.6); 222.5(12.7); 221.6(19.1); 188.8(1.4);186.8(1.5);177.8(1.7);176.9(2.3);175.9(14.8);1517(7.5);117.7(3.9);100.5(2.6);73.3(2.8).

[0090] NMR:

[0091] 1 H NMR (300MHz, CDCl 3 , 300K) δ (ppm) = 7.28 (d, 2H, -C 6 h 4 -); 6.97(d, 2H, -C 6 h 4 -); 6.67 (dd, 1H, -CH=); 5.68 (d, 1H, =CH 2 ); 5.68 (d, 1H, =CH 2 ); 5.16 (d, 1H, =CH 2 ); 2.11(s, 2H, -CH 2 -); 0.51, 0.43 (m, 4H, -CH 2 CH 2 ...

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Abstract

The present invention relates to [bis(trihydrocarbylsilyl)aminosilyl] functionalized styrenes and processes for their preparation. The present invention also relates to the use of the styrene derivative in the preparation of its copolymer.

Description

technical field [0001] The present invention relates to [bis(trihydrocarbylsilyl)aminosilyl] functionalized styrenes and processes for their preparation. The styrene derivative can be especially applied to the production of styrene-butadiene rubber with unique physical and chemical properties. These rubbers are used to make compound rubbers used in the manufacture of passenger car tires. Background technique [0002] An important parameter that determines whether styrene-butadiene rubber can be used in the manufacture of tires and other elastomeric goods is the compatibility of the rubber with commonly used fillers such as carbon black and silica. An increase in the interaction of styrene-butadiene rubber with inorganic fillers can be achieved by introducing polymer segments containing appropriate functional groups that enhance the affinity of the polymer with the fillers used. [0003] US 4,935,471 B discloses that the introduction of nitrogen-containing functional groups...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F236/10C08F12/26C07F7/10C08F230/08C08F212/14
CPCC07F7/10C08F12/26C08F212/14C08F230/08C08F236/10C08F212/26C07C15/46
Inventor 希罗姆·马切耶夫斯基伊雷纽斯·科恩纳基波格丹·马辛尼斯
Owner SYNTHOS