CN111057349A - Environment-friendly flame-retardant plastic, preparation method and application - Google Patents
Environment-friendly flame-retardant plastic, preparation method and application Download PDFInfo
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- CN111057349A CN111057349A CN201911375663.0A CN201911375663A CN111057349A CN 111057349 A CN111057349 A CN 111057349A CN 201911375663 A CN201911375663 A CN 201911375663A CN 111057349 A CN111057349 A CN 111057349A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5353—Esters of phosphonic acids containing also nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
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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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Abstract
The invention discloses an environment-friendly flame-retardant plastic, a preparation method and application thereof. The environment-friendly flame-retardant plastic is prepared from the following raw materials in parts by weight: 90-110 parts of polyester, 5-15 parts of flame retardant, 2-5 parts of plasticizer, 1-3 parts of antioxidant and 0.5-1 part of uvioresistant agent. The flame retardant is prepared by compounding an N-phosphorus compound substituted phosphinimine flame retardant and a phosphonate flame retardant. The flame retardant has good performance, has small influence on the mechanical property of the material, and well widens the application scene of plastics.
Description
Technical Field
The invention relates to the technical field of plastics, in particular to an environment-friendly flame-retardant plastic, a preparation method and application thereof.
Background
The polyester plastic is a heterochain polymer which is prepared by one or more polyols and polybasic acid (or anhydride) in a polycondensation mode and contains ester group on the main chain of the molecule. Polyester plastics have the advantages of excellent mechanical property, electrical insulation property, corrosion resistance, heat resistance, low cost, easy processing and forming and the like, so the polyester plastics are generally used for preparing various textiles, packaging materials, mechanical parts, agricultural films, biological medicines and other products.
The molecular backbone of polyester is composed mainly of carbon and hydrogen-combustible elements, is a combustible material, will melt in the presence of fire, releases a large amount of heat, and produces harmful smoke particles. The heat and smoke released by the burning of polyester can harm life and pollute environment, and the defect greatly limits the application field of polyester plastics. Therefore, the research on how to improve the flame retardant property of the polyester plastic has great research significance.
The research on the flame retardant property by adding the efficient and environment-friendly flame retardant into the polyester plastic becomes the key for expanding the application of the polyester plastic field. The phosphorus flame retardant is a halogen-free flame retardant with low smoke, low toxicity and environmental friendliness, and has been a popular subject in the field of research on halogen-free flame retardants at present. At present, phosphorus flame retardants are applied to polyester plastics, and generally a single phosphorus flame retardant is added into the polyester plastics.
For example, the phosphonate compound is one of the most important phosphorus-containing flame retardants, has better hydrolysis resistance and thermal stability than common phosphorus-containing flame retardants, and has the advantages of less addition amount, good compatibility with polyester plastics, small influence on the mechanical properties of materials after flame retardant modification, and the like. However, the phosphonate compound has general flame retardant performance, has no good effect of other phosphorus-containing flame retardants, and has great limitation on application and development.
For another example, the phosphinimine compound is a relatively few phosphorus-containing flame retardant, the molecular chain of the compound contains a-P ═ N-structure, phosphorus and nitrogen atoms can be substituted by different functional groups, the phosphinimine flame retardant has good flame retardant performance, but the filling of the phosphinimine compound can adversely affect the mechanical properties of polyester plastics, and the imine structure in the compound is easy to hydrolyze, so that a large amount of the phosphinimine flame retardant needs to be added to continuously maintain good flame retardant effect.
Therefore, the existing single phosphorus flame retardant is difficult to simultaneously achieve the effects of small influence on the mechanical property of polyester, good flame retardance and good compatibility of plastic materials.
Disclosure of Invention
In view of the above defects in the prior art, the technical problem to be solved by the present invention is to add a flame retardant compounded by a phosphonate compound and a phosphinimine compound into a polyester plastic, so as to solve the problem of poor flame retardant effect of the existing polyester plastic, and have small influence on the mechanical properties of the polyester plastic.
In order to realize the aim, the invention provides a preparation method of environment-friendly flame-retardant plastic, which comprises the following steps:
(1) placing the polyester in an oven for drying;
(2) preheating a screw cylinder and an injection mold of an injection molding machine;
(3) feeding the dried polyester into a screw cylinder of an injection molding machine, and heating to a molten state;
(4) adding a flame retardant, a plasticizer, an antioxidant and an anti-ultraviolet agent into polyester in a molten state, fully and uniformly mixing, spraying into a mold, and cooling the mold after completion;
(5) opening the mold and taking out the product in the mold.
The drying temperature in the step (1) is 100-120 ℃, and the drying time is 3-5 h.
The temperature of the screw cylinder in the step (2) is 250-270 ℃.
The temperature of the mould in the step (2) is 60-100 ℃.
The cooling temperature of the die in the step (4) is 25-30 ℃.
The weight parts of the raw materials are as follows: 90-110 parts of polyester, 5-15 parts of flame retardant, 2-5 parts of plasticizer, 1-3 parts of antioxidant and 0.5-1 part of uvioresistant agent.
The flame retardant consists of a compound of a formula (1) and/or a compound of a formula (2),
for convenience of explanation, the compound flame retardant of formula (1) is referred to as flame retardant A, and the compound flame retardant of formula (2) is referred to as flame retardant B.
Preferably, the flame retardant consists of a flame retardant A and a flame retardant B in a mass ratio of 1: (5-10).
The plasticizer is any one of di (2-ethylhexyl) phthalate, di-n-octyl phthalate and dibutyl phthalate.
The antioxidant is any one of hydroquinone, p-phenylenediamine and 2, 6-di-tert-butylphenol.
The uvioresistant agent is any one of 2-hydroxy-4-n-octoxy benzophenone, 3, 5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester and 2- (2 '-hydroxy-5' -methylphenyl) benzotriazole.
The invention also provides an environment-friendly flame-retardant plastic which is prepared from the following raw materials in parts by weight: 90-110 parts of polyester, 5-15 parts of flame retardant, 2-5 parts of plasticizer, 1-3 parts of antioxidant and 0.5-1 part of uvioresistant agent;
preferably, the plasticizer is any one of di (2-ethylhexyl) phthalate, di-n-octyl phthalate and dibutyl phthalate;
preferably, the antioxidant is any one of hydroquinone, p-phenylenediamine and 2, 6-di-tert-butylphenol;
preferably, the uvioresistant agent is any one of 2-hydroxy-4-n-octoxy benzophenone, 3, 5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester and 2- (2 '-hydroxy-5' -methylphenyl) benzotriazole;
the flame retardant consists of a compound of a formula (1) and/or a compound of a formula (2);
furthermore, the invention also provides the application of the composite material in the industries of electronic appliances, household appliances, communication tools and automobile manufacturing.
The invention has the beneficial effects that:
(1) the environment-friendly flame-retardant plastic provided by the invention takes the phosphonate flame retardant A and the phosphinimine flame retardant B as flame retardants, so that the defect of the single flame retardant is overcome; the flame retardant A has poor flame retardant effect, and the flame retardant B has great influence on the mechanical property of the polyester plastic. After compounding, the advantages of the components are fully exerted; the flame retardant A has little influence on the mechanical property of the polyester plastic, the flame retardant B has good flame retardant effect, the flame retardant property of the polyester plastic is greatly improved, and meanwhile, the flame retardant A has little influence on the mechanical property of the polyester plastic.
(2) The flame retardant A has the characteristics of high content of a plurality of aromatic rings and phosphorus, can form a hydrogen bond and a pi-pi bond conjugation effect with a polyester matrix and a flame retardant B, and has a stable imine structure in the flame retardant B due to the interaction force between the molecules of the flame retardant A and the flame retardant B, and is not easy to hydrolyze, so that the problems that the flame retardant B is unstable in property and affects the flame retardant effect are solved. When the hydrogen bonds and the pi-pi bonds in the whole system formed by the flame retardants A and B and the polyester matrix act simultaneously, larger binding energy is generated, so that higher mechanical properties are endowed to the material. When the material is acted by external force, the hydrogen bond and the pi-pi bond are firstly broken to dissipate energy, so that the toughness and the mechanical strength of the material are improved.
(3) Compared with the prior art, the environment-friendly flame-retardant plastic prepared by the invention has the advantages of less total flame retardant addition amount, good flame-retardant effect and small influence on the mechanical property of the material, so that the polyester plastic has good application prospect in many fields.
Detailed Description
The sources of the raw materials in the examples and comparative examples are:
the synthesis method of the flame retardant A is obtained by referring to the synthesis method of example 4 in patent CN 110283359A.
The synthesis method of the flame retardant B is obtained by referring to the synthesis method of example 5 in patent CN 110372745A.
Comparative examples 4-5, in which flame retardant C was dimethyl styrylphosphonate as a compound of formula (3), were obtained by the synthesis method in the reference (fantagenci, Zhang Zhou, Liwenyuan, etc.. Synthesis and characterization of styrylphosphonate flame retardant [ J ]. coating industry, 2019, 42(3):29-31.),
polyester Polyethylene terephthalate (PET) belongs to a high molecular compound. Polyethylene terephthalate (PET) is produced by Polycondensation of Terephthalic Acid (PTA) and Ethylene Glycol (EG).
The polyester used in the invention is selected from copolyester with the trademark of ULTRADUR PBT B4030G6 produced by BASF.
Example 1
The environment-friendly flame-retardant plastic is prepared from the following raw materials in parts by weight: 100 parts of polyester, 10 parts of flame retardant, 2 parts of plasticizer, 2 parts of antioxidant and 0.8 part of uvioresistant agent.
The flame retardant consists of a flame retardant A and a flame retardant B.
The flame retardant is prepared from a flame retardant A and a flame retardant B in a mass ratio of 1: 5.
The plasticizer is di-n-octyl phthalate.
The antioxidant is 2, 6-di-tert-butyl phenol.
The uvioresistant agent is 2-hydroxy-4-n-octoxy benzophenone.
The preparation method of the environment-friendly flame-retardant plastic comprises the following steps:
(1) drying the polyester in an oven at the drying temperature of 110 ℃ for 4 h;
(2) preheating a screw cylinder and an injection mold of an injection molding machine, wherein the temperature of the screw cylinder is 260 ℃ and the temperature of the mold is 80 ℃;
(3) feeding the dried polyester into a screw cylinder of an injection molding machine, and heating to a molten state;
(4) adding a flame retardant, a plasticizer, an antioxidant and an anti-ultraviolet agent into polyester in a molten state, fully and uniformly mixing, spraying into a mold, and cooling the mold after the mold is cooled to 28 ℃;
(5) opening the mold and taking out the product in the mold.
Example 2
Essentially the same as example 1, except that:
the flame retardant is prepared from a flame retardant A and a flame retardant B in a mass ratio of 1: 6.
Example 3
Essentially the same as example 1, except that:
the flame retardant is prepared from a flame retardant A and a flame retardant B in a mass ratio of 1: 7.
Example 4
Essentially the same as example 1, except that:
the flame retardant is prepared from a flame retardant A and a flame retardant B in a mass ratio of 1: 8.
Example 5
Essentially the same as example 1, except that:
the flame retardant is prepared from a flame retardant A and a flame retardant B in a mass ratio of 1: 9.
Example 6
Essentially the same as example 1, except that:
the flame retardant is prepared from a flame retardant A and a flame retardant B in a mass ratio of 1: 10.
Comparative example 1
Essentially the same as example 1, except that:
the environment-friendly flame-retardant plastic is prepared from the following raw materials in parts by weight: 100 parts of polyester, 10 parts of flame retardant, 3 parts of plasticizer, 2 parts of antioxidant and 0.8 part of uvioresistant agent.
Comparative example 2
Essentially the same as example 1, except that:
the flame retardant is a flame retardant A.
Comparative example 3
Essentially the same as example 1, except that:
the flame retardant is a flame retardant B.
Comparative example 4
Essentially the same as example 1, except that:
the flame retardant is a flame retardant C.
Comparative example 5
Essentially the same as example 1, except that:
the flame retardant is prepared from a flame retardant C and a flame retardant B in a mass ratio of 1: 8.
Test example 1
Flame retardant property of polyester
And (3) oxygen index test: an oxygen index test was performed using a hap electric technology, llc model HC-2 oxygen index tester, according to ASTM D2863 standard. The length of the sample is 100mm, the width (10. + -. 0.5) mm and the thickness (4. + -. 0.25) mm.
The test method comprises the following steps: under the specified test conditions, the sample was vertically clamped in a transparent glass combustion cylinder, in which an oxygen-nitrogen stream was uniformly mixed and flowed upward. The upper end of the sample is ignited, and when the continuous burning time of the sample is less than 3 minutes or the destruction length after ignition is less than 50mm, the critical oxygen concentration in the oxygen-nitrogen mixture is required, that is, the Oxygen Index (OI) of the sample.
The environmental-friendly flame retardant plastics prepared in examples 1-6 of the invention and comparative examples 1-5 were subjected to flame retardant property tests, and the results are shown in Table 1.
Table 1:
| examples/comparative examples | Oxygen index (%) |
| Example 1 | 31.8 |
| Example 2 | 32.3 |
| Example 3 | 32.8 |
| Example 4 | 34.2 |
| Example 5 | 32.9 |
| Example 6 | 31.4 |
| Comparative example 1 | 22.2 |
| Comparative example 2 | 25.0 |
| Comparative example 3 | 30.8 |
| Comparative example 4 | 23.6 |
| Comparative example 5 | 28.8 |
As can be seen from the data in Table 1, when the composite flame retardants in examples 1 to 6 are prepared by compounding the flame retardant A and the flame retardant B according to a specific mass ratio, only the flame retardant A is added in comparative example 2, and only the flame retardant B is added in comparative example 3. The flame retardant effects of examples 1-6 were all superior to those of comparative examples 2-3. The reason for this is probably that after the flame retardant A and the flame retardant B are compounded, the flame retardant A and the flame retardant B form a hydrogen bond and a pi-pi bond conjugate effect, and due to the existence of an interaction force between the molecules of the flame retardant A and the flame retardant B, the imine structure in the flame retardant B becomes stable, hydrolysis is not easy to occur, the unstable property of the flame retardant B is improved, and thus the flame retardant performance of the polyester is synergistically improved.
Example 4 the composite flame retardant is prepared by mixing a flame retardant a and a flame retardant B in a mass ratio of 1: 8, the flame retardant effect is optimal. The reason for this may be that the mass ratio of the flame retardant a to the flame retardant B is 1: 8 after the mixture is compounded, the best mass ratio enables the most effective acting force to be formed between the A molecules and the B molecules, so that most of the flame retardant A molecules and most of the flame retardant B molecules can form hydrogen bonds and pi-pi bond conjugate effects, the whole system is promoted to be more stable, and the flame retardant effect is best.
Test example 2
Tensile Strength test
The test method comprises the following steps:
tensile strength: the tests according to ISO 527-1/-2 were carried out on an Instron model 5569A universal materials tester from the Instron company.
The test method is as follows:
(1) the test speed (50 +/-5) mm/min;
(2) the experimental environment, the experimental temperature (25 +/-2) DEG C and the relative humidity (65 +/-5)%;
(3) sample pretreatment, namely placing the sample in a standard environment to expose the surface of the sample in the environment as much as possible;
(4) measuring the thickness (4.00 +/-0.05) mm and the width (10.00 +/-0.05) mm of the sample;
(5) when a sample is clamped by a clamp, the center of the longitudinal axis direction of the sample is coincided with the connecting line of the centers of the upper clamp and the lower clamp, the tightness is proper, and the sample cannot slip or be clamped too tightly at a clamping opening to damage the sample when stressed;
(6) starting the machine at the selected speed to perform a tensile test;
(7) reading the load and the extension between gauge distances after the sample is broken, or reading the load when the sample is yielded; if the sample is broken at a position outside the gauge length, the test is abandoned, and the sample is taken for supplement.
The environmental-friendly flame retardant plastic prepared in the example 4 of the invention and the comparative examples 1 to 3 were subjected to tensile strength tests, and the results are shown in Table 2.
Table 2:
| examples/comparative examples | Tensile strength MPa |
| Example 4 | 136 |
| Comparative example 1 | 140 |
| Comparative example 2 | 128 |
| Comparative example 3 | 102 |
As can be seen from the data in table 2, the composite flame retardant in example 4 is prepared by mixing the flame retardant a and the flame retardant B in a mass ratio of 1: 8, compared with the comparative example 1 without adding a flame retardant, the mechanical property of the polyester material is basically not changed. The reason for this is probably that when the hydrogen bond and pi-pi bond act simultaneously in the whole system, a larger binding energy is generated, thereby giving the material higher mechanical properties. When the material is acted by external force, the hydrogen bond and the pi-pi bond are firstly broken to dissipate energy, so that the toughness and the mechanical strength of the material are improved.
The foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.
Claims (10)
1. A preparation method of environment-friendly flame-retardant plastic comprises the following steps:
(1) placing the polyester in an oven for drying;
(2) preheating a screw cylinder and an injection mold of an injection molding machine;
(3) feeding the dried polyester into a screw cylinder of an injection molding machine, and heating to a molten state;
(4) adding a flame retardant, a plasticizer, an antioxidant and an anti-ultraviolet agent into polyester in a molten state, fully and uniformly mixing, spraying into a mold, and cooling the mold after completion;
(5) opening the mold and taking out the product in the mold.
2. The method for preparing environment-friendly flame retardant plastic as claimed in claim 1, wherein the drying temperature is 100-120 ℃, and the drying time is 3-5 h; the temperature of the screw cylinder is 250-270 ℃, and the temperature of the mould is 60-100 ℃; the cooling temperature of the mould is 25-30 ℃.
3. The preparation method of the environment-friendly flame-retardant plastic as claimed in claim 1, which is characterized by comprising the following raw materials in parts by weight: 90-110 parts of polyester, 5-15 parts of flame retardant, 2-5 parts of plasticizer, 1-3 parts of antioxidant and 0.5-1 part of uvioresistant agent.
4. The preparation method of the environment-friendly flame retardant plastic as claimed in claim 3, characterized in that: the plasticizer is any one of di (2-ethylhexyl) phthalate, di-n-octyl phthalate and dibutyl phthalate.
5. The preparation method of the environment-friendly flame retardant plastic as claimed in claim 3, characterized in that: the antioxidant is any one of hydroquinone, p-phenylenediamine and 2, 6-di-tert-butylphenol.
6. The preparation method of the environment-friendly flame retardant plastic as claimed in claim 3, characterized in that: the uvioresistant agent is any one of 2-hydroxy-4-n-octoxy benzophenone, 3, 5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester and 2- (2 '-hydroxy-5' -methylphenyl) benzotriazole.
7. The method for preparing environment-friendly flame retardant plastic according to claim 3, wherein the flame retardant consists of the compound of formula (1) and/or the compound of formula (2),
8. the preparation method of the environment-friendly flame retardant plastic as claimed in claim 7, wherein the flame retardant is prepared from the compound of formula (1) and the compound of formula (2) in a mass ratio of 1: (5-10).
9. The environment-friendly flame-retardant plastic is characterized by comprising the following raw materials in parts by weight: 90-110 parts of polyester, 5-15 parts of flame retardant, 2-5 parts of plasticizer, 1-3 parts of antioxidant and 0.5-1 part of uvioresistant agent;
preferably, the plasticizer is any one of di (2-ethylhexyl) phthalate, di-n-octyl phthalate and dibutyl phthalate;
preferably, the antioxidant is any one of hydroquinone, p-phenylenediamine and 2, 6-di-tert-butylphenol;
preferably, the uvioresistant agent is any one of 2-hydroxy-4-n-octoxy benzophenone, 3, 5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester and 2- (2 '-hydroxy-5' -methylphenyl) benzotriazole;
the flame retardant consists of a compound of a formula (1) and/or a compound of a formula (2),
10. use of the environmentally friendly flame retardant plastic according to claim 9 in the industries of electronic appliances, household appliances, communication tools, and automobile manufacturing.
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| CN201911375663.0A CN111057349A (en) | 2019-12-27 | 2019-12-27 | Environment-friendly flame-retardant plastic, preparation method and application |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000212412A (en) * | 1999-01-22 | 2000-08-02 | Kanegafuchi Chem Ind Co Ltd | Reinforced flame retarded polyester resin composition |
| CN102317373A (en) * | 2008-12-30 | 2012-01-11 | 沙伯基础创新塑料知识产权有限公司 | Reinforced polyester compositions, method of manufacture, and articles thereof |
| CN103102658A (en) * | 2013-03-08 | 2013-05-15 | 天津然跃环保创新科技有限公司 | Halogen-free environment-friendly flame-retardant modified thermoplastic polyester resin |
| JP2014224096A (en) * | 2013-04-17 | 2014-12-04 | キヤノン株式会社 | Novel compound and resin composition containing the same |
| CN110283359A (en) * | 2019-07-30 | 2019-09-27 | 中国科学技术大学 | A kind of N- phosphorus compound replaces phosphinimine type fire retardant and preparation method thereof |
| CN110372745A (en) * | 2019-08-07 | 2019-10-25 | 吕梁学院 | A kind of flame-retardant compound and its preparation method and application |
-
2019
- 2019-12-27 CN CN201911375663.0A patent/CN111057349A/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000212412A (en) * | 1999-01-22 | 2000-08-02 | Kanegafuchi Chem Ind Co Ltd | Reinforced flame retarded polyester resin composition |
| CN102317373A (en) * | 2008-12-30 | 2012-01-11 | 沙伯基础创新塑料知识产权有限公司 | Reinforced polyester compositions, method of manufacture, and articles thereof |
| CN103102658A (en) * | 2013-03-08 | 2013-05-15 | 天津然跃环保创新科技有限公司 | Halogen-free environment-friendly flame-retardant modified thermoplastic polyester resin |
| JP2014224096A (en) * | 2013-04-17 | 2014-12-04 | キヤノン株式会社 | Novel compound and resin composition containing the same |
| CN110283359A (en) * | 2019-07-30 | 2019-09-27 | 中国科学技术大学 | A kind of N- phosphorus compound replaces phosphinimine type fire retardant and preparation method thereof |
| CN110372745A (en) * | 2019-08-07 | 2019-10-25 | 吕梁学院 | A kind of flame-retardant compound and its preparation method and application |
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