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

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...

Examples

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).

[...

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...

Examples

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).

[...

Images