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Novel compound, and modified conjugated diene-based polymer containing functional group derived from compound

A compound and selected technology, applied in the fields of organic chemistry, rolling resistance optimization, road transportation emission reduction, etc., can solve the problems of low end modification ratio, insignificant improvement effect of tire physical properties, etc., and achieve excellent affinity. Effect

Active Publication Date: 2019-07-23
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, BR or SBR modified by the above method has a low terminal modification ratio, and the effect of improving the physical properties of tires manufactured using it is not significant

Method used

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  • Novel compound, and modified conjugated diene-based polymer containing functional group derived from compound
  • Novel compound, and modified conjugated diene-based polymer containing functional group derived from compound
  • Novel compound, and modified conjugated diene-based polymer containing functional group derived from compound

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preparation example Construction

[0084] The method for preparing a compound according to one embodiment of the present invention is characterized in that it includes: performing a first reaction of a compound represented by the following formula 2 with a compound represented by the following formula 3 to prepare a compound represented by the following formula 4 (step a ); and carrying out the second reaction (step b) of the compound represented by the formula 4 with the compound represented by the following formula 5:

[0085] [Formula 2]

[0086]

[0087] [Formula 3]

[0088]

[0089] [Formula 4]

[0090]

[0091] [Formula 5]

[0092]

[0093] [Formula 1]

[0094]

[0095] In Formula 1 to Formula 5, R 1 to R 4 Same as described above.

[0096]The first reaction in step a is a step for preparing the compound represented by Formula 4, and may be performed by reacting the compound represented by Formula 2 with the compound represented by Formula 3.

[0097] In addition, the second reaction...

preparation Embodiment 1

[0220] Preparation Example 1: Preparation of butyl 1-(6-(cyclohexylideneamino)hexyl)-5-oxopyrrolidine-3-carboxylate (i)

[0221] 1) Preparation of 6-(cyclohexylideneamino)hexane-1-amine

[0222] In the round bottom flask of 250ml, add the 1,6-hexamethylenediamine of 9.0g (77.45mmol), and add the cyclohexanone of 24.08ml (232.34mmol), then, use Dean-Stark apparatus to remove Water is produced and the temperature is raised to 150°C. Then, the reaction was performed for 12 hours, the reaction was terminated, distillation was performed to remove the remaining cyclohexanone, and 14.64 g (yield 96.3%) of 6-(cyclohexylideneamino)hexan-1-amine was obtained. 6-(Cyclohexylideneamino)hexan-1-amine 1 H NMR spectral data are as follows.

[0223] 1 H-NMR (500MHz, CDCl 3 )δ3.26-3.24(t,2H),2.67-2.64(t,2H),2.25-2.23(t,4H),1.70-1.68(m,2H),1.61-1.56(m,6H),1.43- 1.39(t,2H),1.33-1.31(m,4H),1.11-0.95(br,2H).

[0224] 2) Preparation of butyl 1-(6-(cyclohexylideneamino)hexyl)-5-oxopyrrolidine-...

preparation Embodiment 2

[0228] Preparation Example 2: Preparation of 1-(6-(cyclohexylideneamino)hexyl)-5-oxopyrrolidine-3-carboxylic acid methyl ester (ii)

[0229] 1) Preparation of 6-(cyclohexylideneamino)hexane-1-amine

[0230] In the round bottom flask of 250ml, add the 1,6-hexamethylenediamine of 9.0g (77.45mmol), and add the cyclohexanone of 24.08ml (232.34mmol), then, use Dean-Stark apparatus to remove Water is produced and the temperature is raised to 150°C. Then, the reaction was performed for 12 hours, the reaction was terminated, distillation was performed to remove remaining cyclohexanone, and 14.64 g (yield: 96.3%) of 6-(cyclohexylideneamino)hexan-1-amine was obtained. The preparation process was repeated twice to give a total of 29.28 g. 6-(Cyclohexylideneamino)hexan-1-amine 1 H NMR spectral data are as follows.

[0231] 1 H-NMR (500MHz, CDCl 3 )δ3.26-3.24(t,2H),2.67-2.64(t,2H),2.25-2.23(t,4H),1.70-1.68(m,2H),1.61-1.56(m,6H),1.43- 1.39(t,2H),1.33-1.31(m,4H),1.11-0.95(br,2H).

[...

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Abstract

The present invention relates to a compound represented by chemical formula 1, a preparation method therefor, and a modified conjugated diene-based polymer having a high modification ratio, containinga functional group derived from the compound.

Description

technical field [0001] [Cross Reference to Related Application] [0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0124413 filed on September 26, 2017 and Korean Patent Application No. 10-2018-0093812 filed on August 10, 2018, both of which The entire content of the application is incorporated into this specification by reference. [0003] [technical field] [0004] The present invention relates to a novel compound for modifying polymers, a preparation method thereof, and a modified conjugated diene-based polymer comprising a functional group derived from the compound. Background technique [0005] According to the recent demand for automobiles with low fuel consumption, conjugated diene-based polymers having modulation stability represented by wet skid resistance and low rolling resistance and excellent abrasion resistance and tensile properties are required as tires Made of rubber material. [0006] In order to reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/267C08K5/3415C08F36/04C08F8/30
CPCC08F8/30C08F36/04C08K5/3415C07D207/277C07D207/267C08C19/22C08F136/06
Inventor 崔承镐金智恩崔源文赵大濬
Owner LG CHEM LTD
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