CN110003087B - Fullerene pyrrolidine aniline derivative and preparation method and application thereof - Google Patents
Fullerene pyrrolidine aniline derivative and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a compound shown in formula (I)The fullerene pyrrolidine aniline derivative is prepared through the reaction of amino acid and p-aminobenzaldehyde to produce methyl imine ylide, and the subsequent reaction with fullerene [1,3 ]]And performing cycloaddition reaction to obtain the fullerene pyrrolidine aniline derivative. When the fullerene derivative is used as a light stabilizer for polystyrene products, the light stabilizing effect of the fullerene derivative is obviously superior to that of fullerene C 60 。
In the formula: r 1 ＝‑CH 3 ,‑C 2 H 5 ，R 2 ＝‑H,‑CH 2 ‑C 6 H 5 ,‑CH 2 ‑C 6 H 5 ‑OCH 3 。
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and relates to a light stabilizer for plastic products, in particular to a fullerene pyrrolidine aniline derivative and a preparation technology thereof.
Technical Field
With the popularization and expansion of polymer material application, the requirements on the strength and weather resistance of polymer products are continuously improved, and high-performance and multifunctional polymer additives become a hot problem of research. The light stabilizer is one of indispensable components for regulating the light aging resistance of the polymer product and prolonging the service life of the polymer product, and is a very key functional material in the formula of the polymer product. The search for light stabilizers with excellent properties has been a major direction to improve the light stability and prolong the service life of polymer products under the existing circumstances.
Polystyrene is one of the most widely used polymer materials, and is often used as a packaging material, a building material and an insulating material, and products thereof are mainly applied outdoors, so that a light stabilizer needs to be added to prolong the service life of the polystyrene, but the conventional light stabilizers (such as TiO2, UV-0, nickel dibutyldithiocarbamate and the like) used conventionally have the defects of poor light stabilization effect, low efficiency, environmental pollution, single action mechanism, poor compatibility with polystyrene and the like.
Fullerene C 60 Is carbon allotrope, has good ultraviolet absorption capacity and free radical capture capacity, and thus, the carbon allotrope is used as a light stabilizer to be directly added into polystyrene products, and the technical effect is obviously superior to that of the traditional light stabilizer. However, is this the best solution? The applicant has intensively studied and found that there are better solutions, which will be shown below.
Disclosure of Invention
The invention aims to provide a polystyrene product light stabilizer which is more excellent than the prior art and a preparation method thereof, and the specific technical scheme is as follows:
a fullerene pyrrolidine aniline derivative has a structure shown in the following formula (I):
in the formula: r 1 ＝-CH 3 ,-C 2 H 5 ，
R 2 ＝-H,-CH 2 -C 6 H 5 ,-CH 2 -C 6 H 5 -OCH 3 。
The fullerene pyrrolidine aniline derivative is used as a light stabilizer for polystyrene products.
The preparation method of the fullerene pyrrolidine aniline derivative comprises the following steps: and (2) adding fullerene C into the mixture according to the molar ratio of 1 60 Dissolving p-aminobenzaldehyde and amino acid in organic solvent, and ultrasonic treating to obtain fullerene C 60 Dissolving p-aminobenzaldehyde completely, mixing with amino acid, magnetically stirring under heating in oil bath to react amino acid with p-aminobenzaldehyde to obtain ylide, and reacting with fullerene [1,3 ]]Performing cycloaddition reaction to obtain fullerene pyrrolidine aniline derivatives, stopping heating after the reaction is complete, and cooling the reactor to room temperature; removing the solvent by rotary evaporation, and dissolving the residual solid with a small amount of carbon disulfideSeparating by column chromatography, washing with organic solvent, and washing off brown product band to obtain the final product.
The p-aminobenzaldehyde is one of p-dimethylaminobenzaldehyde and p-diethylaminobenzaldehyde; the amino acid is one of glycine, N-benzylglycine and N- (4-methoxy-benzyl) -glycine; the organic solvent is one of toluene, chlorobenzene, o-dichlorobenzene, dichloromethane, dimethyl sulfoxide, petroleum ether and trichloromethane or a mixture of any number of the toluene, the chlorobenzene, the o-dichlorobenzene, the dichloromethane, the dimethyl sulfoxide, the petroleum ether and the trichloromethane.
Compared with the prior art, the invention has the following characteristics and beneficial effects:
(1) The fullerene pyrrolidine aniline derivative has remarkable light stabilizing effect compared with fullerene C 60 Better, can obviously improve the light stability of the polystyrene product and prolong the service life.
(2) The fullerene pyrrolidine derivative has good compatibility with polystyrene and unique physical and chemical properties, can further optimize the use performance of polystyrene products, obtains the polystyrene products with high strength and excellent weather resistance, and has great significance for improving the product quality and enhancing the product grade.
(3) The synthesis method of the fullerene pyrrolidine derivative is simple and convenient, has mild conditions, high yield and good economy, and is suitable for industrial mass production.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of N-benzyl-2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene of example 1
FIG. 2 is a nuclear magnetic hydrogen spectrum of 2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene of example 2
FIG. 3 is a nuclear magnetic hydrogen spectrum of N- (4-methoxy-benzyl) -2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene of example 3
FIG. 4 is a graph of the change in molecular weight for a series of polystyrene materials, wherein:
(a) Pure polystyrene; (ii) a
(b) Containing 0.5% of C 60 The polystyrene of (4);
(c) Polystyrene containing 0.5% of N-benzyl-2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene;
(d) Polystyrene containing 0.5% N- (4-methoxy-benzyl) -2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene.
Detailed Description
The following examples are intended to illustrate the invention further, but should not be construed as limiting the scope of the invention, and many insubstantial modifications and adaptations of the invention by those skilled in the art based on the teachings set forth herein should be made without departing from the scope of the invention.
Example 1:
the preparation method of the N-benzyl-2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene comprises the following steps:
accurately 36mg (0.05 mmol) of C 60 Adding 30mg (0.20 mmol) of 4-N, N-dimethylaminobenzaldehyde and 50mg (0.30 mmol) of N-benzylglycine into a 100mL thick-walled eggplant-shaped bottle, measuring and adding 10mL of chlorobenzene, and ultrasonically oscillating for 15min to enable C to be in contact with the mixed solution 60 And the aldehyde were completely dissolved and mixed with glycine uniformly, the oil bath was heated to 130 ℃ and stirred magnetically for 5h, after which the heating was stopped and the reactor was cooled to room temperature. The solvent was removed by rotary evaporation and the residual solid was dissolved well with a small amount of carbon disulphide and separated by column chromatography, washed with carbon disulphide and washed off a brown product band. The solution was rotary evaporated to give a brownish black solid as the product, which was weighed after 10h of vacuum drying at a yield of 61%. The structure is characterized as follows: 1 H NMR(600MHz,CS 2 /CDCl 3 ＝1/3)δ7.61(d,J＝7.5Hz,4H,Ph-H),7.41(t,J＝7.5Hz,2H,Ph-H),7.30(t,J＝7.3Hz,1H,Ph-H),6.70(d,J＝7.5Hz,2H,Ph-H),5.07(s,1H,C 60 -CH(NH)-Ph),4.79(d,J＝9.4Hz,1H,C 60 -CH 2 -N),4.54(d,J＝13.4Hz,1H,Ph-CH 2 -N),4.08(d,J＝9.4Hz,1H,C 60 -CH 2 -N),3.57(d,J＝13.4Hz,1H,Ph-CH 2 -N),2.95(s,6H,N-(CH 3 ) 2 ) The nuclear magnetic hydrogen spectrum is shown in figure 1. 13 C NMR(150MHz,CS 2 /CDCl 3 ＝1/3)δ156.66,154.21,154.11,153.97,150.24,147.33,147.30,147.05,146.76,146.59,146.35,146.30,146.25,146.20,146.16,146.12,145.97,145.96,145.87,145.61,145.58,145.55,145.53,145.44,145.32,145.30,145.29,145.28,145.15,144.76,144.45,144.44,143.20,143.03,142.71,142.65,142.62,142.59,142.43,142.34,142.21,142.20,142.18,142.08,141.90,141.70,141.63,140.22,140.17,140.04,139.71,138.20,136.82,136.69,135.89,135.85,128.91,128.79,127.56,124.02,81.40(sp 3 -C of C 60 ),77.21(sp 3 -C of C 60 ),68.64,66.68,56.83,40.40。UV-Vis(toluene)λ/(nm):287,332,433。HRMS(MALDI-TOF)m/z calcd[M+H] + 972.1626,found 972.1628。
Example 2:
the preparation method of the 2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene comprises the following steps:
accurately 36mg (0.05 mmol) of C 60 Adding 30mg (0.20 mmol) of 4-N, N-dimethylaminobenzaldehyde and 23mg (0.30 mmol) of glycine into a 100mL thick-walled eggplant-shaped bottle, measuring and adding 25mL of toluene, and ultrasonically oscillating for 15min to enable C to be in a state of being in contact with the liquid 60 And the aldehyde are completely dissolved and uniformly mixed with the glycine, the oil bath is heated to 130 ℃ and the mixture is magnetically stirred for 8 hours at a constant temperature, then the heating is stopped and the reactor is cooled to the room temperature. The solvent was removed by rotary evaporation and the residual solid was dissolved thoroughly with a small amount of carbon disulphide and separated by column chromatography, washed with toluene and washed with a brown band of product. The solution was rotary evaporated to give a brownish black solid as the product, which was weighed after 10h of vacuum drying with a yield of 44%. The structure is characterized as follows: 1 H NMR(600MHz,CS 2 /CDCl 3 ＝1/3)δ7.63(d,J＝8.8Hz,2H,Ph-H),6.75(d,J＝8.8Hz,2H,Ph-H),5.74(s,1H,C 60 -CH(NH)-Ph),5.10(d,J＝10.5Hz,1H,C 60 -CH 2 -NH),4.89(d,J＝10.5Hz,1H,C 60 -CH 2 -NH),3.00(s,6H,N-(CH 3 ) 2 ) The nuclear magnetic hydrogen spectrum is shown in FIG. 2. 13 C NMR(150MHz,CS 2 /CDCl 3 ＝1/3)δ156.07,153.80,153.70,153.28,149.86,146.90,146.85,146.70,146.43,146.29,146.04,145.97,145.93,145.84,145.78,145.66,145.65,145.52,145.28,145.19,145.13,145.11,145.05,145.02,144.98,144.96,144.89,144.38,144.33,144.14,144.06,142.93,142.76,142.45,142.39,142.36,142.33,142.17,142.14,141.99,141.93,141.91,141.85,141.81,141.79,141.66,141.48,141.34,139.93,139.90,139.78,139.48,136.25,135.98,135.74,135.47,128.78,128.09,125.19,112.15,78.14(sp 3 -C of C 60 ),77.11(sp 3 -C of C 60 ),72.59,61.53,40.08。UV-Vis(toluene)λ/(nm):287,332,433。HRMS(MALDI-TOF)m/z calcd[M+H] + 882.1162,found 882.1166。
Example 3:
the preparation method of the N- (4-methoxy-benzyl) -2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene comprises the following steps:
accurately 36mg (0.05 mmol) of C 60 30mg (0.20 mmol) of 4-N, N-dimethylaminobenzaldehyde and 59mg (0.30 mmol) of N- (4-methoxy-benzyl) -glycine are added into a 100mL thick-walled eggplant-shaped bottle, 10mL of o-dichlorobenzene is measured and added, and ultrasonic oscillation is carried out for 15min to ensure that C is saturated 60 And the aldehyde were dissolved completely and glycine was mixed well, the oil bath was heated to 110 ℃ and magnetic stirring was carried out for 20min at constant temperature, then heating was stopped and the reactor was cooled to room temperature. The solvent was removed by rotary evaporation and the residual solid was fully dissolved with a small amount of carbon disulfide and separated by column chromatography, washed with a mixed solvent of n-hexane: carbon disulfide =1 and washed off a brown product band. The solution was rotary evaporated to give a dark brown solid as the product, which was weighed after 10h of vacuum drying to a yield of 54%. The structure is characterized as follows: 1 H NMR(600MHz,CS 2 /CDCl 3 ＝1/3)δ7.76(d,J＝11.2Hz,2H,Ph-H),7.56(d,J＝8.1Hz,2H,Ph-H),7.00(d,J＝8.1Hz,2H,Ph-H),6.81(s,2H,Ph-H),5.11(s,1H,C 60 -CH(NH)-Ph),4.85(d J＝9.4Hz,1H,C 60 -CH 2 -N),4.53(d,J＝13.1Hz,1H,Ph-CH 2 -N),4.15(d J＝9.2Hz,1H,C 60 -CH 2 -N),3.89(s,3H,N-(CH 2 C 6 H 4 )-OCH 3 ),3.63(d J＝13.6Hz,1H,Ph-CH 2 -N),3.03(s,6H,Ph-N(CH 3 ) 2 ) The nuclear magnetic hydrogen spectrum is shown in FIG. 3. 13 C NMR(150MHz,CS 2 /CDCl 3 ＝1/3)δ159.06,156.70,154.26,154.13,153.99,150.16,147.32,147.29,147.04,146.76,146.58,146.35,146.30,146.24,146.19,146.16,146.12,145.96,145.95,145.86,145.60,145.57,145.54,145.52,145.43,145.32,145.29,145.28,145.27,145.15,144.76,144.45,144.44,143.19,143.03,142.71,142.65,142.61,142.59,142.42,142.34,142.20,142.17,142.07,142.06,141.90,141.70,141.63,140.22,140.17,140.03,139.70,136.82,136.69,135.88,135.83,130.13,129.75,128.72,114.14,81.14(sp 3 -C of C 60 ),77.24(sp 3 -C of C 60 ),68.56,66.55,56.07,55.11,40.43。UV-Vis(toluene)λ/(nm):287,332,433。
Example 4:
the preparation method of the N- (4-methoxy-benzyl) -2- (4-N, N-diethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene comprises the following steps:
accurately 36mg (0.05 mmol) of C 60 35mg (0.20 mmol) of 4-N, N-diethylaminobenzaldehyde and 59mg (0.30 mmol) of N- (4-methoxy-benzyl) -glycine are added to a 250mL round-bottomed flask, 80mL of dimethyl sulfoxide are metered in and added thereto, and the mixture is shaken ultrasonically for 15min to convert C 60 And the aldehyde were dissolved completely and glycine was mixed well, the oil bath was heated to 110 ℃ and magnetic stirring was carried out for 20min at constant temperature, then heating was stopped and the reactor was cooled to room temperature. The solvent was removed by distillation under reduced pressure, and the residual solid was sufficiently dissolved with a small amount of carbon disulfide and separated by column chromatography, washed with a mixed solvent of n-hexane: carbon disulfide =1, and washed to remove a brown product band. The solution was rotary evaporated to give a brownish black solid as the product, which was weighed after 10h of vacuum drying with a yield of 45%. The structure is characterized as follows: 1 H NMR(600MHz,CS 2 /CDCl 3 ＝1/3)δ7.83-7.45(m,4H,Ph-H),6.93(d,J＝8.5Hz,2H,Ph-H),6.70-6.55(m,2H,Ph-H),5.02(s,1H,C 60 -CH(NH)-Ph),4.76(d,J＝9.3Hz,1H,C 60 -CH 2 -N),4.46(d,J＝13.2Hz,1H,Ph-CH 2 -N),4.06(d,J＝9.3Hz,1H,C 60 -CH 2 -N),3.82(s,3H,N-(CH 2 C 6 H 4 )-OCH 3 ),3.53(d,J＝13.1Hz,1H,Ph-CH 2 -N),3.33(q,J＝6.7Hz,4H,Ph-N-(CH 2 ) 2 ),1.16(t,J＝7.0Hz,6H,N-(CH 2 ) 2 -(CH 3 ) 2 )。 13 C NMR(150MHz,CS 2 /CDCl 3 ＝1/3)δ159.02,156.79,154.33,154.28,154.13,147.83,147.32,147.29,147.10,146.91,146.60,146.34,146.29,146.24,146.19,146.15,146.11,145.96,145.95,145.86,145.59,145.57,145.50,145.42,145.31,145.29,145.28,145.27,145.14,144.76,144.46,144.43,143.18,143.02,142.70,142.64,142.60,142.58,142.42,142.34,142.21,142.17,142.07,141.90,141.69,141.63,140.20,140.15,140.04,139.69,136.80,136.70,135.88,135.81,81.27(sp 3 -C of C 60 ),68.59(sp 3 -C of C 60 ),66.57,60.37,56.09,55.13,44.60,13.09。UV-Vis(toluene)λ/(nm):287,332,433。
the raw materials, aminobenzaldehyde, amino acid and organic solvent, used according to the present invention, can be any one of the respective categories, and are not limited by the above examples, so that many examples can be written, but are not limited to space and are not enumerated one by one.
Example 5:
the preparation and the photoaging behavior of the polystyrene material added with the novel fullerene pyrrolidine multifunctional light stabilizer are as follows:
weighing 995mg of polystyrene, ultrasonically dissolving the polystyrene in 20mL of toluene, accurately weighing 5mg of N-benzyl-2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene and N- (4-methoxy-benzyl) -2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene respectively, adding the obtained mixture into a toluene solution of polystyrene, and ultrasonically dissolving for 2 hours to uniformly mix the obtained mixture to obtain a solution system with the fullerene pyrrolidine derivative content of 0.5%. Transferring the solution to a culture dish with the diameter of 7.5cm, standing and volatilizing, obtaining the polystyrene material containing the fullerene pyrrolidine derivative after the solution is completely volatilized, and respectively preparing the polystyrene material containing 0.5 percent of fullerene and pure polystyrene according to the same method. The prepared material is placed in an ultraviolet aging test box, an ultraviolet accelerated aging test is carried out in the air atmosphere, the test temperature is 35-39 ℃, and the light source is six PHILIPS TL60W/10R mercury lamp tubes (the peak wavelength is 365 nm). The molecular weight of the series of polystyrene materials before and after aging was determined using gel chromatography (see FIG. 4), the data for polystyrene after aging was as high as 39% with 25% reduction in the number average molecular weight of polystyrene containing 0.5% C60, while the polystyrene containing 0.5% N-benzyl-2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene was only 14% reduction in the number average molecular weight of polystyrene containing 0.5% N- (4-methoxy-benzyl) -2- (4-N, N-dimethylaminophenyl) pyrrolidine [3',4',1,2] [60] fullerene was only 11% reduction. Test results show that the addition of the fullerene and the pyrrolidine derivative thereof can improve the photostability of the polystyrene, and the photostability of the fullerene pyrrolidine derivative is more remarkable.
Claims (3)
1. A fullerene pyrrolidine aniline derivative is characterized in that the structure of the fullerene pyrrolidine aniline derivative is shown as the following formula (I):
in the formula: r 1 ＝-CH 3 ，
R 2 ＝-CH 2 -C 6 H 5 ，-CH 2 -C 6 H 5 -OCH 3 。
2. The use of a fullerene pyrrolidine aniline derivative according to claim 1, wherein the fullerene pyrrolidine aniline derivative is used as a light stabilizer for polystyrene products.
3. The process for producing a fullerene pyrrolidine aniline derivative according to claim 1, comprising the steps of: according to the mol ratio of 1:4:6 fullerene C 60 Dissolving p-aminobenzaldehyde and amino acid in organic solvent, and ultrasonic treating to obtain fullerene C 60 Dissolving p-aminobenzaldehyde completely, mixing with amino acid, magnetically stirring under heating in oil bath to react amino acid with p-aminobenzaldehyde to obtain ylide, and reacting with fullerene [1,3 ]]Performing cycloaddition reaction to obtain fullerene pyrrolidine aniline derivative, stopping heating after the reaction is sufficient, and cooling the reactor to room temperature; removing solvent by rotary evaporation, dissolving the residual solid with small amount of carbon disulfide, and performing column chromatographySeparating, washing with organic solvent, and washing off brown product band to obtain product;
the p-aminobenzaldehyde is p-dimethylaminobenzaldehyde; the amino acid is one of N-benzyl glycine and N- (4-methoxy-benzyl) -glycine; the organic solvent is one of toluene, chlorobenzene, o-dichlorobenzene, dichloromethane, dimethyl sulfoxide, petroleum ether and trichloromethane or a mixture of any number of the toluene, the chlorobenzene, the o-dichlorobenzene, the dichloromethane, the dimethyl sulfoxide, the petroleum ether and the trichloromethane.
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