Rubber composition, tire, bisphenyldiamine compound and antiaging agent
A technology of bisphenyldiamine compound and rubber composition is applied in the field of rubber composition of tread rubber or sidewall rubber, and can solve the problems of crack propagation, rupture of rubber products and the like
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preparation example 1
[0124] Preparation Example 1: Preparation of N,N'-bis[4-(isopropylamino)phenyl]-N,N'-dimethylethane-1,2-diamine (Compound I-1)
[0125] (1) Preparation of N,N'-bis(4-nitrophenyl)ethane-1,2-diamine
[0126] After adding 4.79 g of ethylenediamine and 73.3 g of potassium carbonate to a solution of 25.0 g of 4-fluoronitrobenzene in 150 mL of N,N-dimethylformamide, it was stirred at 100° C. overnight. The resulting reaction solution was filtered through Celite, and 500 mL of water and 300 mL of ethyl acetate were added to the filtrate, followed by liquid separation to obtain an organic layer. The organic layer was concentrated under reduced pressure to obtain a solid residue, which was subsequently washed with a mixture of isopropanol and diisopropyl ether, and dried under reduced pressure to obtain 21.3 g (88% yield) of N,N' - bis(4-nitrophenyl)ethane-1,2-diamine.
[0127] (2) Preparation of N,N'-bis(4-nitrophenyl)-N,N'-dimethylethane-1,2-diamine.
[0128] A solution of 100 g o...
preparation example 2
[0137] Preparation Example 2: Preparation of N,N'-diisopropyl-N,N'-bis[4-(isopropylamino)phenyl]ethane-1,2-diamine (Compound I-2)
[0138] (1) Preparation of N,N'-bis(4-nitrophenyl)ethane-1,2-diamine
[0139] After adding 4.79 g of ethylenediamine and 73.3 g of potassium carbonate to a solution of 25.0 g of 4-fluoronitrobenzene in 150 mL of N,N-dimethylformamide, it was stirred at 100° C. overnight. The resulting reaction liquid was filtered with celite, and after adding 500 mL of water and 300 mL of ethyl acetate to the filtrate, liquid separation was performed to obtain an organic layer. The organic layer was concentrated under reduced pressure to obtain a solid residue which was subsequently washed with a mixture of isopropanol and diisopropyl ether and dried under reduced pressure to obtain 21.3 g (88% yield) of N,N' - bis(4-nitrophenyl)ethane-1,2-diamine.
[0140] (2) Preparation of N,N'-bis(4-aminophenyl)ethane-1,2-diamine
[0141] After adding 400 mg of 5% palladium ...
preparation example 3
[0148] Preparation Example 3: Preparation of N,N'-diisopropyl-N,N'-bis[4-(pent-3-ylamino)phenyl]ethane-1,2-diamine (Compound I-3) preparation
[0149] (1) Preparation of N,N'-bis[4-(pent-3-ylamino)phenyl]ethane-1,2-diamine
[0150]After adding 23.5 g of diethyl ketone to a solution of 30.0 g of N,N'-bis(4-aminophenyl)ethane-1,2-diamine in 300 mL of methanol, under ice cooling, 17.1 g of cyanide sodium borohydride, then 12 mL of acetic acid was added in two portions. Stirring was carried out for 1.5 hours under ice-cooling and overnight at room temperature. Then, 250 mL of 1N aqueous sodium hydroxide solution was added to the reaction liquid, and stirring was performed for 30 min. Thereafter, extraction was performed with chloroform, and the resulting organic layer was washed once with water. The organic layer was concentrated under reduced pressure to obtain a residue, which was then dissolved in chloroform, treated by silica gel column chromatography (hexane:ethyl acetate...
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