CN112266541A - Nitrogen-phosphorus flame-retardant polypropylene material and preparation method thereof - Google Patents
Nitrogen-phosphorus flame-retardant polypropylene material and preparation method thereof Download PDFInfo
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- CN112266541A CN112266541A CN202011112629.7A CN202011112629A CN112266541A CN 112266541 A CN112266541 A CN 112266541A CN 202011112629 A CN202011112629 A CN 202011112629A CN 112266541 A CN112266541 A CN 112266541A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/32—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing phosphorus or sulfur
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Abstract
The invention discloses a nitrogen-phosphorus flame-retardant polypropylene material and a preparation method thereof; the nitrogen-phosphorus flame-retardant polypropylene material comprises the following components: 60-100 parts by mass of polypropylene grafted nitrogen-phosphorus flame retardant, 5-20 parts by mass of toughening agent, 1-3 parts by mass of composite antioxidant and 2-5 parts by mass of other auxiliary agents; according to the invention, the flame retardant is grafted on the polypropylene molecular chain, and the flame retardant molecules and the polypropylene are combined in a covalent bond mode, so that the problems that the flame retardant is added into the polypropylene base material by a physical mixing method, the compatibility of the flame retardant and the polymer is poor, and the flame retardant is easy to lose are solved.
Description
Technical Field
The invention belongs to the field of polymer chemical synthesis, and particularly relates to a nitrogen-phosphorus flame-retardant polypropylene material and a preparation method thereof.
Background
The polypropylene is a polymer obtained by addition polymerization of propylene, is a white wax-like material, has a transparent and light appearance, and has a density of 0.89 to 0.91g/cm3Is inflammable, has a melting point of 165 ℃, is softened at about 155 ℃, has a use temperature range of-30-140 ℃, and can resist acid, alkali and salt solution below 80 DEG CAnd corrosion of various organic solvents, can be decomposed under the action of high temperature and oxidation, and the polypropylene is widely applied to the production of fiber products such as clothes, blankets and the like, medical instruments, automobiles, bicycles, parts, conveying pipelines, chemical containers and the like, and is also used for packaging foods and medicines. The polypropylene molecular chain is composed of hydrocarbon elements, is easy to burn and has no flame retardance, and a flame retardant is usually added in the preparation of a polypropylene material, for example, Chinese patent CN102199804B discloses a polypropylene fiber for wig of a composite nitrogen-phosphorus flame retardant and a production method thereof, wherein at least one or more of the combination of ammonium phosphate, diammonium pyrophosphate, ammonium hypophosphite, urea ammonium phosphate and ammonium metaphosphate and melamine or melamine polyphosphate or melamine phosphate or melamine borate are added in the polypropylene material; the polypropylene material with the characteristics of no toxicity, smoke suppression, environmental friendliness and the like is obtained.
The invention patent adds the flame retardant into the polypropylene base material by a physical mixing method, and because the bonding effect between the flame retardant molecules and the polypropylene base material is weaker, the dispersion uniformity of the flame retardant is not easy to ensure, and in addition, the loss problem of the flame retardant components is difficult to avoid, thus directly influencing the long-term flame retardant property of the product. Based on the statement, the invention provides a nitrogen-phosphorus flame-retardant polypropylene material and a preparation method thereof.
Disclosure of Invention
In order to solve the defects of the prior art, the invention provides a nitrogen-phosphorus flame-retardant polypropylene material and a preparation method thereof, wherein small molecules with a flame-retardant effect are grafted on a polypropylene molecular chain, so that the polypropylene material has flame retardancy, and the flame-retardant molecules and covalent bonds are combined with polypropylene, so that the problems of poor compatibility of a flame retardant and a polymer and easy loss of the flame retardant are solved.
The invention aims to provide a nitrogen-phosphorus flame-retardant polypropylene material.
The invention also aims to provide a preparation method of the nitrogen-phosphorus flame-retardant polypropylene material.
The above purpose of the invention is realized by the following technical scheme:
the preparation method of the nitrogen-phosphorus flame-retardant polypropylene material comprises the following steps:
the components by weight portion are as follows: 60-100 parts by mass of polypropylene grafted nitrogen-phosphorus flame retardant, 5-20 parts by mass of toughening agent, 1-3 parts by mass of composite antioxidant and 2-5 parts by mass of other additives are subjected to normal-temperature mixing extrusion, cooling and granulation in a high-speed mixer to prepare the nitrogen-phosphorus flame-retardant polypropylene material.
The nitrogen-phosphorus flame retardant grafted with the polypropylene has a structural formula shown as the following formula (I):
in the formula (I), the compound is shown in the specification,
the value of n is 15-50.
The reaction process and the preparation method of the nitrogen-phosphorus flame retardant grafted with the nitrogen-phosphorus flame retardant are as follows:
the preparation method of the polypropylene grafted nitrogen-phosphorus flame retardant comprises the following steps:
1. adding triethylamine and glycine into a branched flask, adding chloroform, adding a phenylphosphonyl dichloride chloroform solution at a low temperature after the glycine is completely dissolved, heating to 60-70 ℃, reacting for 4-6 hours, carrying out reduced pressure distillation, suction filtration, extraction, and silica gel column chromatography purification to obtain the aliphatic carboxylic acid containing phosphorus and nitrogen.
Wherein the feeding molar ratio of the phenylphosphonic dichloride to the triethylamine to the glycine is 1:1: 1.5.
2. Adding aliphatic carboxylic acid containing phosphorus and nitrogen into a flask with a branch mouth, adding tetrahydrofuran for dissolving, heating to 70-80 ℃, and dropwise adding SOCl2Carrying out acyl chlorination reaction; n is a radical of2Under protection, pyridine is used as an acid-binding agent, toluene is used as a solvent, and the hydroxyl-terminated polypropylene and the solvent are subjected to esterification reaction to obtain the polypropylene grafted nitrogen-phosphorus flame retardant.
Wherein, hydroxyl-terminated polypropylene and SOCl2The molar ratio of the aliphatic carboxylic acid to the phosphorus-nitrogen-containing aliphatic carboxylic acid is 1:1:1.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the invention provides a nitrogen-phosphorus flame-retardant polypropylene material, which leads polypropylene molecules to have flame retardance by grafting a flame retardant on a polypropylene molecular chain.
(2) The invention provides a nitrogen-phosphorus flame-retardant polypropylene material, wherein flame-retardant molecules and covalent bonds are combined with polypropylene, so that the problems of poor compatibility of a flame retardant and a polymer and easy loss of the flame retardant are solved by adding the flame retardant into a polypropylene substrate by a physical mixing method.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum diagram of a polypropylene grafted nitrogen phosphorus flame retardant.
Detailed Description
The present invention will be described in further detail with reference to specific examples, which are not intended to limit the present invention in any manner. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
Example 1
Glycine (7.5mmoL), triethylamine (5mmoL) and 25mL of dry chloroform were added to a 150mL flask with a small mouth, and stirred to be sufficiently dissolved and mixed; weighing phenylphosphonic dichloride (5mmoL) and dissolving in 25mL chloroform, dripping into a reaction bottle in ice bath within 1h, slowly heating to 70 ℃ after dripping, refluxing for 6h, adding 10mL distilled water to stop the reaction, distilling under reduced pressure to remove the solvent, cooling to room temperature, performing suction filtration, dissolving the filtrate with dichloromethane with twice volume, extracting for 3 times with distilled water, taking an organic layer, and using anhydrous Na2SO3Drying, filtering and distilling off dichloromethane to obtain a crude product, (dichloromethane)/(petroleum ether) ═ 10:1 is eluent, and purifying by silica gel column chromatography to obtain the phosphorus-nitrogen-containing aliphatic carboxylic acid with the yield of 73.4%.
Example 2
Phosphorus and nitrogen-containing aliphatic carboxylic acid (4.0mmol) and 20ml of anhydrous tetrahydrofuran THF were charged into a reactorIn the reaction, after the reaction temperature is raised to 70 ℃, slowly dropwise adding SOCl2(4.0mmol) and after the dropwise addition, the reaction was carried out for 2 hours, after the completion of the reaction, SOCl was removed by distillation under reduced pressure2And THF to obtain the acyl chloride product of aliphatic carboxylic acid containing phosphorus and nitrogen, and adding proper amount of toluene to dissolve.
The hydroxyl-terminated polypropylene (4.0mmol) was charged into a 50ml Schlenk flask and, after purging with nitrogen three times, N2Under protection, 30ml of anhydrous toluene is added into a disposable injector, the temperature is raised to 70 ℃, 1ml of pyridine is injected after the hydroxyl-terminated polypropylene is completely dissolved, the mixture is stirred for 30min, the phosphorus-nitrogen-containing aliphatic carboxylic acid acyl chloride product is dropwise added, the temperature is raised to 80 ℃, the reaction is continued for 2.5h, the product is cooled to room temperature, and after two times of continuous dissolution/precipitation circulation of toluene/methanol, the product is dried to constant weight under vacuum at 45 ℃, so that the polypropylene grafted nitrogen-phosphorus flame retardant is obtained, and the yield is 74.2%.
Example 3
100 parts by mass of a polypropylene grafted nitrogen-phosphorus flame retardant, 10 parts by mass of an ethylene-vinyl acetate copolymer, 1 part by mass of an antioxidant 1010, 1 part by mass of an antioxidant 168, and 3 parts by mass of talcum powder are subjected to normal-temperature mixing extrusion, cooling and granulation in a high-speed mixer to prepare a nitrogen-phosphorus flame-retardant polypropylene material; and (2) carrying out vacuum drying on the obtained nitrogen-phosphorus flame-retardant polypropylene material at 80 ℃ for 12h, adding the nitrogen-phosphorus flame-retardant polypropylene material on an open type heat mixer with a double-roller temperature of 155 ℃, carrying out melting and roll wrapping, mixing for 10min, uniformly taking out the sheet, carrying out hot pressing on a flat vulcanizing machine at 160 ℃ for 10min, carrying out cold pressing at room temperature for 8min, taking out the sheet, preparing various standard sample strips on a universal sampling machine, and carrying out flame retardant property testing.
Example 4
80 parts by mass of polypropylene grafted nitrogen-phosphorus flame retardant, 10 parts by mass of ethylene-vinyl acetate copolymer, 1 part by mass of antioxidant 1010, 1 part by mass of antioxidant 168 and 3 parts by mass of talcum powder are subjected to normal-temperature mixing extrusion, cooling and granulation in a high-speed mixer to prepare a nitrogen-phosphorus flame-retardant polypropylene material; and (2) carrying out vacuum drying on the obtained nitrogen-phosphorus flame-retardant polypropylene material at 80 ℃ for 12h, adding the nitrogen-phosphorus flame-retardant polypropylene material on an open type heat mixer with a double-roller temperature of 155 ℃, carrying out melting and roll wrapping, mixing for 10min, uniformly taking out the sheet, carrying out hot pressing on a flat vulcanizing machine at 160 ℃ for 10min, carrying out cold pressing at room temperature for 8min, taking out the sheet, preparing various standard sample strips on a universal sampling machine, and carrying out flame retardant property testing.
Example 5
60 parts by mass of a polypropylene grafted nitrogen-phosphorus flame retardant, 10 parts by mass of an ethylene-vinyl acetate copolymer, 1 part by mass of an antioxidant 1010, 1 part by mass of an antioxidant 168, and 3 parts by mass of talcum powder are subjected to normal-temperature mixing extrusion, cooling and granulation in a high-speed mixer to prepare a nitrogen-phosphorus flame-retardant polypropylene material; and (2) carrying out vacuum drying on the obtained nitrogen-phosphorus flame-retardant polypropylene material at 80 ℃ for 12h, adding the nitrogen-phosphorus flame-retardant polypropylene material on an open type heat mixer with a double-roller temperature of 155 ℃, carrying out melting and roll wrapping, mixing for 10min, uniformly taking out the sheet, carrying out hot pressing on a flat vulcanizing machine at 160 ℃ for 10min, carrying out cold pressing at room temperature for 8min, taking out the sheet, preparing various standard sample strips on a universal sampling machine, and carrying out flame retardant property testing.
Comparative example 1
Mixing 100 parts by mass of polypropylene, 10 parts by mass of ethylene-vinyl acetate copolymer, 1 part by mass of antioxidant 1010, 1 part by mass of antioxidant 168 and 3 parts by mass of talcum powder in a high-speed mixer at normal temperature, extruding, cooling and granulating to prepare a polypropylene material; and (2) drying the obtained polypropylene material in vacuum at 80 ℃ for 12h, adding the polypropylene material to an open type heat mixing machine with a double-roller temperature of 155 ℃, uniformly taking out the polypropylene material after the polypropylene material is melted and coated on the roller, mixing for 10min, hot-pressing the polypropylene material on a flat vulcanizing machine at 160 ℃ for 10min, cold-pressing the polypropylene material at room temperature for 8min, taking out the polypropylene material, preparing various standard sample strips on a universal sampling machine, and testing the flame retardant property.
Comparative example 2
Mixing 80 parts by mass of polypropylene, 10 parts by mass of ethylene-vinyl acetate copolymer, 1 part by mass of antioxidant 1010, 1 part by mass of antioxidant 168 and 3 parts by mass of talcum powder in a high-speed mixer at normal temperature, extruding, cooling and granulating to prepare a polypropylene material; and (2) drying the obtained polypropylene material in vacuum at 80 ℃ for 12h, adding the polypropylene material to an open type heat mixing machine with a double-roller temperature of 155 ℃, uniformly taking out the polypropylene material after the polypropylene material is melted and coated on the roller, mixing for 10min, hot-pressing the polypropylene material on a flat vulcanizing machine at 160 ℃ for 10min, cold-pressing the polypropylene material at room temperature for 8min, taking out the polypropylene material, preparing various standard sample strips on a universal sampling machine, and testing the flame retardant property.
Comparative example 3
60 parts by mass of polypropylene grafted nitrogen-phosphorus flame retardant, 10 parts by mass of ethylene-vinyl acetate copolymer, 1 part by mass of antioxidant 1010, 1 part by mass of antioxidant 168 and 3 parts by mass of talcum powder are subjected to normal-temperature mixing extrusion, cooling and granulation in a high-speed mixer to prepare a polypropylene material; and (2) drying the obtained polypropylene material in vacuum at 80 ℃ for 12h, adding the polypropylene material to an open type heat mixing machine with a double-roller temperature of 155 ℃, uniformly taking out the polypropylene material after the polypropylene material is melted and coated on the roller, mixing for 10min, hot-pressing the polypropylene material on a flat vulcanizing machine at 160 ℃ for 10min, cold-pressing the polypropylene material at room temperature for 8min, taking out the polypropylene material, preparing various standard sample strips on a universal sampling machine, and testing the flame retardant property.
Limiting oxygen index test: the instrument is FTAII (1600) type limit oxygen index instrument of RS company in UK, test standard GB/T2406.2-2009, spline specification 100mm x 6mm x 3mm, and a group of 5-10, before test, the spline is placed in an environment with temperature 23 + -2 deg.C and humidity 50 + -5% and adjusted for more than 88 h.
UL-94 vertical burning test: the instrument is an CZF-5A horizontal vertical combustion tester of Jiangning analytical instruments factory for carrying out UL-94 vertical combustion test, the specification of the sample bar is 125mm multiplied by 13mm multiplied by 3.2mm, and the test standard is UL94ISBN 0-7629 and 0082-2. Before testing, the sample is put in an environment with the temperature of 23 +/-2 ℃ and the humidity of 50 +/-5% and is adjusted for more than 48 h.
The flame retardant performance of the nitrogen-phosphorus flame retardant polypropylene material is evaluated through the limit oxygen index and the UL-94 vertical combustion test, and the result is shown in Table 1.
Table 1 shows the flame retardant properties of the nitrogen-phosphorus flame retardant polypropylene material.
| Sample (I) | Example 3 | Example 4 | Example 5 | Comparative example 1 | Comparative example 2 | Comparative example 3 |
| LOI(％) | 31.2 | 30.7 | 29.1 | 17.2 | 17.5 | 17.9 |
| UL-94 | V-1 | V-1 | V-1 | N.R | N.R | N.R |
As can be seen from Table 1, the flame retardant property of polypropylene can be obviously improved by grafting the organic micromolecules with flame retardant effect on the polypropylene polymer chain, and the comparison of the data of the examples 3-5 and the comparative examples 1-3 shows that the LOI of pure PP is about 17%, when the organic micromolecules with flame retardant effect are grafted on the polypropylene molecular chain to modify the polypropylene, the LOI can reach 31.2%, and the flame retardant property of the polypropylene can be effectively improved.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (5)
1. The nitrogen-phosphorus flame-retardant polypropylene material is characterized by comprising the following components in parts by weight: 60-100 parts by mass of polypropylene grafted nitrogen-phosphorus flame retardant, 5-20 parts by mass of toughening agent, 1-3 parts by mass of composite antioxidant and 2-5 parts by mass of other auxiliary agents, wherein the polypropylene grafted nitrogen-phosphorus flame retardant has a structure shown in a formula (I):
in the formula (I), the compound is shown in the specification,
the value of n is 15-50.
2. The preparation method of the nitrogen-phosphorus flame-retardant polypropylene material according to claim 1, which is characterized by comprising the following steps:
60-100 parts by mass of polypropylene grafted nitrogen-phosphorus flame retardant, 5-20 parts by mass of toughening agent, 1-3 parts by mass of composite antioxidant and 2-5 parts by mass of other additives are subjected to normal-temperature mixing extrusion, cooling and granulation in a high-speed mixer to prepare the nitrogen-phosphorus flame-retardant polypropylene material.
3. The nitrogen-phosphorus flame-retardant polypropylene material according to claim 1, wherein the preparation method of the polypropylene grafted nitrogen-phosphorus flame retardant comprises the following steps:
(1) adding triethylamine and glycine into a branched flask, adding chloroform, completely dissolving the glycine, adding a phenylphosphonyl dichloride chloroform solution at a low temperature, heating to 60-70 ℃, reacting for 4-6 hours, carrying out reduced pressure distillation, suction filtration, extraction and silica gel column chromatography purification to obtain the aliphatic carboxylic acid containing phosphorus and nitrogen;
(2)adding aliphatic carboxylic acid containing phosphorus and nitrogen into a flask with a branch mouth, adding tetrahydrofuran for dissolving, heating to 70-80 ℃, and dropwise adding SOCl2Carrying out acyl chlorination reaction; n is a radical of2Under protection, pyridine is used as an acid-binding agent, toluene is used as a solvent, and the hydroxyl-terminated polypropylene and the solvent are subjected to esterification reaction to obtain the polypropylene grafted nitrogen-phosphorus flame retardant.
4. The nitrogen-phosphorus flame-retardant polypropylene material according to claim 3, wherein in the step (1), the feeding molar ratio of the phenylphosphonic dichloride, the triethylamine and the glycine is 1:1: 1.5.
5. The nitrogen-phosphorus flame-retardant polypropylene material according to claim 3, wherein the preparation method of the polypropylene grafted nitrogen-phosphorus flame retardant comprises the step (2) of hydroxyl-terminated polypropylene and SOCl2The molar ratio of the aliphatic carboxylic acid to the phosphorus-nitrogen-containing aliphatic carboxylic acid is 1:1:1.
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| CN115029946A (en) * | 2022-06-29 | 2022-09-09 | 界首市宏利塑料股份有限公司 | Wear-resistant PE plastic rope and production process thereof |
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