CN114213759B - Preparation method and application of polyphosphonate grafted graphene flame-retardant modified polypropylene - Google Patents
Preparation method and application of polyphosphonate grafted graphene flame-retardant modified polypropylene Download PDFInfo
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- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
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- C08G83/001—Macromolecular compounds containing organic and inorganic sequences, e.g. organic polymers grafted onto silica
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Abstract
The invention relates to the technical field of flame-retardant polypropylene, and discloses a polyphosphate grafted graphene flame-retardant modified polypropylene, which is prepared by chemically bonding polyphosphate containing diphenyl sulfone and phosphabicyclo structure to the surface of graphene to realize organic functional modification of graphene, and modifying polypropylene by taking the polyphosphate phosphabicyclo grafted graphene as a flame-retardant functional filler and taking the polyphosphate of the diphenyl sulfone and phosphabicyclo structure as a flame-retardant component.
Description
Technical Field
The invention relates to the technical field of flame-retardant polypropylene, in particular to a preparation method and application of flame-retardant modified polypropylene of polyphosphate grafted graphene.
Background
Polypropylene has good acid and alkali resistance, chemical resistance, electrical insulation, good processability and the like, and is widely applied to a plurality of fields such as mechanical manufacture, electronic and electric appliances, textile industry, packaging materials and the like as one of four general thermoplastic resins, but the traditional polypropylene has poor flame retardance and is easy to burn, so that flame retardant modification is needed to be carried out on the polypropylene, and the polypropylene is modified at present mainly by copolymerization modification, grafting modification, nucleating agent addition and other methods.
The traditional flame retardant mainly comprises a phosphate flame retardant, an organosilicon flame retardant, a halogen-containing flame retardant and the like, wherein the phosphate flame retardant has the advantages of low smoke, no toxicity, flame retardance and the like, is a flame retardant with very wide application, is prepared from graphene serving as an inorganic nano filler, is widely applied to high polymer materials such as polypropylene, polyimide and the like, and is introduced into flame retardant molecules through chemical modification in the graphene, and is a research hotspot in recent years, so that the phosphate flame retardant can be grafted to the surface of the graphene to obtain flame-retardant functional graphene for flame-retardant modification of polypropylene.
(one) solving the technical problems
Aiming at the defects of the prior art, the invention provides a preparation method and application of flame-retardant modified polypropylene of polyphosphate grafted graphene, and solves the problem of poor flame retardance of polypropylene.
(II) technical scheme
In order to achieve the above purpose, the present invention provides the following technical solutions: the preparation method of the polyphosphoric acid ester grafted graphene flame-retardant modified polypropylene comprises the following steps:
(1) Adding N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction, filtering the solvent, and washing the precipitate by using N-methylpyrrolidone and ethanol in sequence to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 5-7h at 75-85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine, performing in-situ polymerization reaction, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene in a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the polyphosphate grafted graphene flame-retardant modified polypropylene.
Preferably, the mass ratio of the carboxylated graphene, the 4,4' -diamino diphenyl sulfone, the 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and the 4-dimethylaminopyridine in the step (1) is 100:350-600:18-35:6-12.
Preferably, the amidation reaction in the step (1) is carried out at a temperature of 20-50 ℃ for 24-48 hours.
Preferably, the mass ratio of the phosphabicyclo-phosphoryl chloride intermediate, 4' -diaminodiphenyl sulfone, amino diphenyl sulfone grafted graphene and triethylamine in the step (3) is 300-450:240-370:420-640:100:80-125.
Preferably, the temperature of the in-situ polymerization reaction in the step (3) is 75-90 ℃ and the reaction time is 12-24h.
Preferably, the mass ratio of the polyphosphate grafted graphene to the polypropylene in the step (4) is 0.5-2:100.
(III) beneficial technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
according to the flame-retardant modified polypropylene of the polyphosphate grafted graphene, under the catalysis of 1-ethyl-3-dimethylaminopropyl carbonyl diimine hydrochloride and 4-dimethylaminopyridine, the carboxyl of the graphene and one amino group of 4,4 '-diaminodiphenyl sulfone are subjected to amidation reaction to obtain amino diphenyl sulfone grafted graphene, a phosphadicyclophosphamide intermediate formed by 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride, and 4,4' -diaminodiphenyl sulfone are used as polymerization monomers, and the amino diphenyl sulfone grafted by the graphene is used as a polymerization reaction site to perform in-situ polymerization reaction to obtain the polyphosphate phosphadicyclo grafted graphene, so that the polyphosphate containing diphenyl sulfone and phosphadicyclo structure is chemically bonded to the surface of the graphene, and the organic functional modification of the graphene is realized.
According to the flame-retardant modified polypropylene with the polyphosphate grafted graphene, the polyphosphate phosphabicyclo-grafted graphene is used as a flame-retardant functional filler, and the grafted polyphosphate containing diphenyl sulfone and phosphabicyclo structures is used as a flame-retardant component to modify the polypropylene, so that the flame-retardant modified polypropylene has excellent carbonization promoting, smoke suppressing and flame retarding effects, the flame retarding effects of the polypropylene are remarkably enhanced, and the mechanical strength of the polypropylene is not influenced while the flame retarding effects are achieved by controlling the dosage of the polyphosphate phosphabicyclo-grafted graphene.
Drawings
FIG. 1 is a schematic diagram of the synthesis of aminodiphenyl sulfone grafted graphene;
FIG. 2 is a schematic diagram of the synthesis of polyphosphonate phosphabicyclo grafted graphene.
Detailed Description
In order to achieve the above object, the present invention provides the following specific embodiments and examples: the preparation method of the polyphosphonate grafted graphene flame-retardant modified polypropylene comprises the following steps:
(1) Adding N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, performing amidation reaction for 24-48h at 20-50 ℃ according to the mass ratio of 100:350-600:18-35:6-12, filtering the solvent, and washing and precipitating by sequentially using N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 5-7h at 75-85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 300-450:240-370:420-640:100:80-125, performing in-situ polymerization at 75-90 ℃ for 12-24h, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene with the mass ratio of 0.5-2:100 into a double screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
Example 1
(1) Adding an N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction for 24 hours at 20 ℃ according to the mass ratio of 100:350:18:6, filtering the solvent, and washing and precipitating by sequentially using the N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 5 hours at 75 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 300:240:420:100:80, performing in-situ polymerization for 12 hours at 75 ℃, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene with the mass ratio of 0.5:100 into a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
Example 2
(1) Adding an N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction for 24 hours at 50 ℃, filtering the solvent, and washing and precipitating by sequentially using the N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 5 hours at 85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 350:280:480:100:95, performing in-situ polymerization for 18 hours at 80 ℃, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene in a mass ratio of 1:100 into a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
Example 3
(1) Adding an N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction for 36h at 30 ℃ with the mass ratio of 100:500:30:10, filtering the solvent, and washing and precipitating by sequentially using the N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 6 hours at 80 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 400:320:570:100:110, performing in-situ polymerization for 18 hours at 80 ℃, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene with the mass ratio of 1.5:100 into a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
Example 4
(1) Adding an N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction for 48 hours at 50 ℃, filtering the solvent, and washing and precipitating by sequentially using the N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 7 hours at 85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 450:370:640:100:125, performing in-situ polymerization for 24 hours at 90 ℃, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene in a mass ratio of 2:100 into a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
Comparative example 1
(1) Adding an N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction for 24 hours at 40 ℃, filtering the solvent, and washing and precipitating by sequentially using the N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 6 hours at 85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 250:180:350:100:65, performing in-situ polymerization for 12 hours at 90 ℃, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene with the mass ratio of 0.2:100 into a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
Comparative example 2
(1) Adding an N-methylpyrrolidone solvent, carboxylated graphene and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction for 36h at 40 ℃, filtering the solvent, and washing and precipitating by sequentially using the N-methylpyrrolidone and ethanol to obtain the amino diphenyl sulfone grafted graphene.
(2) 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane and phosphorus oxychloride react to obtain a phosphabicyclo-phosphoryl chloride intermediate.
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4' -diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 7h at 85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine according to the mass ratio of 500:420:700:100:140, performing in-situ polymerization for 24h at 80 ℃, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain the polyphosphate phosphabicyclo-grafted graphene.
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene with the mass ratio of 2.5:100 into a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the flame-retardant modified polypropylene of the polyphosphate grafted graphene.
The flame retardant property of the polyphosphonate grafted graphene flame retardant modified polypropylene is tested by a TTech-cone calorimeter.
And testing the tensile strength of the polyphosphoric acid ester grafted graphene flame-retardant modified polypropylene by using a WAW-C universal testing machine.
Claims (3)
1. The flame-retardant modified polypropylene of the polyphosphate grafted graphene is characterized in that: the preparation method of the polyphosphonate grafted graphene flame-retardant modified polypropylene comprises the following steps:
(1) Adding N-methylpyrrolidone solvent, carboxylated graphene and 4,4 '-diaminodiphenyl sulfone into a three-necked bottle, adding 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride and 4-dimethylaminopyridine after ultrasonic dispersion, carrying out amidation reaction, filtering the solvent, and washing the precipitate by using N-methylpyrrolidone and ethanol in sequence to obtain amino diphenyl sulfone grafted graphene, wherein the mass ratio of carboxylated graphene to 4,4' -diaminodiphenyl sulfone to 1-ethyl-3-dimethylaminopropyl carbodiimide hydrochloride to 4-dimethylaminopyridine is 100:350-600:18-35:6-12;
(2) Reacting 1-oxo-4-hydroxymethyl-2, 6, 7-trioxa-1-phosphabicyclo- [2.2.2] octane with phosphorus oxychloride to obtain a phosphabicyclo-phosphoryl chloride intermediate;
(3) Adding acetonitrile solvent, phosphabicyclo-phosphoryl chloride intermediate and 4,4 '-diaminodiphenyl sulfone into a three-necked bottle, introducing nitrogen, reacting for 5-7h at 75-85 ℃, adding amino diphenyl sulfone grafted graphene and triethylamine, performing in-situ polymerization reaction, filtering the solvent, and washing and precipitating with N, N-dimethylformamide and ethanol to obtain polyphosphoric acid ester phosphabicyclo-grafted graphene, wherein the mass ratio of acetonitrile solvent to phosphabicyclo-phosphoryl chloride intermediate to 4,4' -diaminodiphenyl sulfone to amino diphenyl sulfone grafted graphene to triethylamine is 300-450:240-370:420-640:100:80-125;
(4) Placing the polyphosphate phosphabicyclo-grafted graphene and polypropylene in a double-screw extruder, adding a plasticizer, an antioxidant and a lubricant, extruding master batch after blending uniformly, and then performing injection molding by an injection molding machine to obtain the polyphosphate phosphabicyclo-grafted graphene flame-retardant modified polypropylene, wherein the mass ratio of the polyphosphate phosphabicyclo-grafted graphene to the polypropylene is 0.5-2:100.
2. The polyphosphate grafted graphene flame retardant modified polypropylene according to claim 1, wherein: the amidation reaction temperature in the step (1) is 20-50 ℃ and the reaction time is 24-48h.
3. The polyphosphate grafted graphene flame retardant modified polypropylene according to claim 1, wherein: the temperature of the in-situ polymerization reaction in the step (3) is 75-90 ℃ and the reaction time is 12-24h.
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