CN115558270B - Regenerated modified plastic particles - Google Patents
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- CN115558270B CN115558270B CN202211130274.3A CN202211130274A CN115558270B CN 115558270 B CN115558270 B CN 115558270B CN 202211130274 A CN202211130274 A CN 202211130274A CN 115558270 B CN115558270 B CN 115558270B
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
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- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
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Abstract
The invention relates to the technical field of plastics, in particular to regenerated modified plastic particles. The modified plastic particles consist of the following components in parts by weight: 50-65 parts of polycarbonate waste; 20-30 parts of polypropylene; 10-20 parts of ABS resin; 10-15 parts of plasticizer; 8-12 parts of flame retardant; 5-10 parts of calcium carbonate; 0.2-1 part of dicumyl peroxide; the modified plastic particles have excellent fireproof and flame-retardant properties, good impact resistance, heat resistance and strength, and good toughness at low temperature.
Description
Technical Field
The invention relates to the technical field of plastics, in particular to regenerated modified plastic particles.
Background
Polycarbonate plastics are high molecular polymers containing carbonate groups in the molecular chain, and can be classified into various types such as aliphatic, aromatic, aliphatic-aromatic, and the like, depending on the structure of the ester groups. Wherein the application of aliphatic and aliphatic-aromatic polycarbonates in engineering plastics is limited due to their low mechanical properties. At present, only aromatic polycarbonates are industrially produced. The polycarbonate plastic has the advantages of outstanding impact strength, higher elastic modulus, higher dimensional stability, good colorability, better electrical insulation and the like, but the polycarbonate plastic products have poor impact resistance, which greatly limits the application of the polycarbonate plastic in certain fields. The polycarbonate plastic yield in China is increased more and more, the product types are various, and a large amount of waste is generated, and the waste comprises leftover materials in production and various aged and scrapped polycarbonate products, so that not only is the huge resource waste caused, but also the environment is polluted more seriously, and the recycling of the waste is a problem to be solved urgently.
The patent with application number 201310729146.5 provides a polystyrene and polycarbonate composite modified plastic, which is modified by using polystyrene and polycarbonate as main raw materials, and the prepared polystyrene and polycarbonate composite modified plastic has the effects of high temperature resistance, good stability, wear resistance, good toughness, stable performance and the like, but cannot realize recycling of polycarbonate waste. The patent with the application number of 2016610132194. X provides a low-expansion flame-retardant photodiffusion PC composite material for an LED lamp tube and a preparation method thereof, and reinforcing auxiliary agents, flame retardants, photodiffusion agents, antioxidants and the like are added for modification, wherein the flame retardants consist of phenyl silicone resin crystals and PC carrier polytetrafluoroethylene, and the prepared finished product has certain flame retardance but cannot realize recycling of polycarbonate waste. At present, the technology of the modified plastic of the polycarbonate waste is still immature, and the performance of the polycarbonate blending modified plastic commonly seen in the market is insufficient. Accordingly, the present invention provides a modified plastic prepared from waste plastics to solve the problems set forth in the background art described above.
Disclosure of Invention
The invention aims at overcoming the defects of the prior art and providing regenerated modified plastic particles which have good impact resistance, heat resistance and strength; the alloy still has better toughness at low temperature; but also has good fireproof and flame-retardant performance.
The technical scheme adopted by the invention for achieving the purpose is as follows:
the regenerated modified plastic particles comprise the following components in parts by weight:
50-65 parts of polycarbonate waste;
20-30 parts of polypropylene;
10-20 parts of ABS resin;
10-15 parts of plasticizer;
8-12 parts of flame retardant;
5-10 parts of calcium carbonate;
0.2-1 part of dicumyl peroxide;
wherein the plasticizer is diisobutyl phthalate, dimethyl phthalate or diethyl phthalate; the flame retardant is triphenyl phosphate derivative, and the preparation method comprises the following steps: the p-aminophenol is taken as an initial raw material, is sequentially substituted by propionyl chloride and a halogenated reagent, and finally is subjected to phosphorylation reaction with phosphorus oxychloride to generate a triphenyl phosphate derivative, and the structural general formula is as follows:
wherein X is a bromine atom or a chlorine atom; preferably, X is a bromine atom, and the chemical name is tris (4- (3-bromopropionamido) phenyl) phosphate, and the structural formula is as follows:
the invention provides regenerated modified plastic particles, wherein the preparation method of the triphenyl phosphate derivative comprises the following steps:
s1: adding p-aminophenol and triethylamine into an anhydrous dichloromethane solution, dropwise adding propionyl chloride under ice bath stirring, heating to 25 ℃, and reacting for 0.5h to generate an intermediate I, wherein the structural formula is as follows:
s2: adding the intermediate I into acetonitrile solution, protecting with nitrogen, heating to 55-65 ℃, adding azodiisobutyronitrile under stirring, and then adding N-bromosuccinimide or N-chlorosuccinimide to react for 0.5-1h to generate an intermediate II, wherein the structural formula is as follows:
wherein X is a bromine atom or a chlorine atom; preferably X is a bromine atom, in which case intermediate II is 3-bromo-N- (4-hydroxyphenyl) propionamide of formula:
among them, preferred is a reactionThe temperature was 65℃and the reaction time was 1h.
S3: sequentially adding the intermediate II, pyridine and phosphorus oxychloride into an anhydrous benzene solution, heating to 80 ℃, and reacting for 3-5 hours to obtain a target product triphenyl phosphate derivative, wherein the structural formula is as follows:
wherein X is a bromine atom or a chlorine atom; preferably, X is a bromine atom, and the target product is tris (4- (3-bromopropionamido) phenyl) phosphate, which has the structural formula:
among them, the reaction time of 4 hours is preferable.
The invention also provides a preparation method of the regenerated modified plastic particles, which comprises the following steps: collecting polycarbonate waste, cleaning, airing, and crushing into particles for later use; weighing the crushed polycarbonate waste, polypropylene, ABS resin, plasticizer, flame retardant, calcium carbonate and dicumyl peroxide according to the weight ratio, heating and mixing at a high speed, wherein the heating temperature is 70-90 ℃, the rotating speed is 90-110r/min, and the mixing time is 30-40min; continuously heating to 280 ℃ by using a granulator, melting, extruding the melted polymer, and granulating to obtain modified plastic particles; among them, the preferable heating temperature is 80℃and the rotation speed is 110r/min, and the mixing time is 40min.
According to the scheme, the triphenyl phosphate derivative is used as a flame retardant, and is obtained by carrying out structural modification on triphenyl phosphate serving as a phosphorus flame retardant, a core group phosphate group part is reserved, phosphoric anhydride or phosphoric acid can be generated in the combustion process, so that combustible materials are dehydrated and carbonized, combustible gas is prevented or reduced, meanwhile, glass-like melt is formed by phosphoric anhydride during pyrolysis and covers the surface of the combustible materials, and carbon dioxide is generated by oxidization of the phosphoric anhydride, so that the flame retardant effect is achieved; three halogens are introduced into the benzene ring, wherein the halogen is decomposed to generate hydrogen Halide (HX), the hydrogen halide reacts with a chain reaction active substance HO in flame to reduce the concentration of free radicals, so that the chain reaction of combustion is slowed down or stopped, residues after the hydrogen halide is decomposed can promote dehydration and carbonization of polymer materials to form a flame-retardant carbonized layer, the generation amount of low molecular weight cracking products is reduced, the introduction of the halogen enables the compound to have the dual flame-retardant effect of a phosphorus-halogen flame retardant, the evaporation temperature of the bromine-containing flame retardant is similar to the decomposition temperature of the polymer, when the polymer is heated and decomposed, the flame retardant is volatilized at the same time, and the flame-retardant is simultaneously in a gas-phase combustion zone with a thermal decomposition product, so that bromine has strong capability of capturing free radicals in the combustion reaction, and a better flame-retardant effect; simultaneously, three polar amide groups are introduced, so that the polymer has the processing lubrication function and the low-temperature anti-sticking function, on one hand, the polymer can be inserted into the polymer resin, the interaction among resin molecules is reduced, and the function of an internal lubricant is realized; on the other hand, the resin melt and processing equipment can be rubbed with each other, so that the resin melt is prevented from adhering to the metal surface, an external lubrication effect is achieved, the fluidity and the demolding property of molten plastics are improved, the processing yield of the plastics is improved, the energy consumption is reduced, and the product has extremely high surface smoothness; and the antistatic property of the plastic product can be improved, so that the plastic product is not easy to suck dust.
The invention has the following beneficial effects: the triphenyl phosphate derivative with dual flame retardant effect, lubrication, low-temperature anti-sticking and antistatic effects is obtained through structural modification, so that the components can be better fused with each other, and the fireproof flame retardant and mechanical properties of the modified plastic are improved; the regenerated modified plastic particles provided by the invention can effectively reduce waste pollution by recycling polycarbonate waste, and the plastic particles obtained through regeneration modification have good impact resistance, heat resistance and strength, excellent fireproof and flame-retardant properties, and still have good toughness at low temperature and wide application value.
Detailed Description
The following description of the technical solutions in the embodiments of the present application will be made clearly and completely in connection with the embodiments of the present application, and it is obvious that the described embodiments are only some embodiments of the present application, not all embodiments. All other embodiments, which can be made by one of ordinary skill in the art without undue burden from the present disclosure, are within the scope of the present disclosure.
P-aminophenol CAS number 123-30-8; propionyl chloride CAS number 79-03-8; n-bromosuccinimide CAS number 128-08-5; phosphorus oxychloride CAS number 10025-87-3; triethylamine CAS number 121-44-8; azodiisobutyronitrile CAS number 78-67-1; pyridine CAS number 110-86-1; triphenyl phosphate CAS No. 115-86-6; tris (2-chloroethyl) phosphate CAS number 115-96-8; dichloromethane CAS number 75-09-2; acetonitrile CAS number 75-05-8; benzene CAS number 71-43-2; all chemical reagents are commercially available.
Example 1
The embodiment provides a preparation method of triphenyl phosphate derivative, namely tris (4- (3-bromopropionamido) phenyl) phosphate, which comprises the following specific steps:
s1: adding 5.0g of p-aminophenol and 6.9g of triethylamine into 100mL of anhydrous dichloromethane solution, slowly dropwise adding 6.4g of propionyl chloride by using a dropping funnel under ice bath stirring, naturally heating to 25 ℃ after the addition is finished, stirring and reacting for 0.5h, and decompressing and steaming out the solvent after the reaction is finished to obtain an intermediate I (7.0 g); ESI-MS (m/z): 166[ M+H ]] + ； 1 HNMR(600MHz，DMSO-d 6 )δ：10.13(s，1H)，9.44(s，1H)，7.31(d，J＝8.5Hz，2H)，6.65(d，J＝8.2Hz，2H)，2.34～2.35(m，2H)，1.52(t，J＝6.0Hz，3H)。
The reaction formula is as follows:
s2: adding 7.0g of intermediate I into 80mL of acetonitrile solution, heating to 65 ℃ under nitrogen protection, adding 0.7g of azodiisobutyronitrile, adding 8.3. 8.3g N-bromosuccinimide, reacting for 1h, and evaporating solvent under reduced pressure after the reaction is finished to obtain 3-bromo-N- (4-hydroxyphenyl) propionamide (8.5 g); ESI-MS (m/z): 245[ M+H ]] + ； 1 HNMR(600MHz，DMSO-d 6 )δ：10.03(s，1H)，9.20(s，1H)，7.32(d，J＝8.4Hz，2H)，6.63(d，J＝8.0Hz，2H)，3.68(t，J＝6.5Hz，2H)，2.73(t，J＝6.2Hz，2H)。
The reaction formula is as follows:
s3: 8.0g of 3-bromo-N- (4-hydroxyphenyl) propionamide, 3.9g of pyridine and 2.5g of phosphorus oxychloride are sequentially added into 60mL of anhydrous benzene solution, the temperature is raised to 80 ℃ for reflux reaction for 4 hours, and after the reaction is finished, tris (4- (3-bromopropionamido) phenyl) phosphate (7.5 g) is obtained through reduced pressure distillation; ESI-MS (m/z): 777[ M+H ]] + ； 1 HNMR(600MHz，DMSO-d 6 )δ：10.10(s，3H)，7.56(d，J＝8.0Hz，6H)，7.38(d，J＝7.8Hz，6H)，3.68(t，J＝6.2Hz，6H)，2.73(t，J＝6.0Hz，6H)。
The reaction formula is as follows:
example 2
The embodiment provides a regenerated modified plastic particle and a preparation method thereof.
The regenerated modified plastic particles consist of the following components in parts by weight: 60 parts of polycarbonate waste, 30 parts of polypropylene, 20 parts of ABS resin, 14 parts of plasticizer, 10 parts of flame retardant, 10 parts of calcium carbonate and 0.5 part of dicumyl peroxide; wherein the flame retardant is tris (4- (3-bromopropionamido) phenyl) phosphate; the plasticizer is diisobutyl phthalate.
The preparation method of the modified plastic particles comprises the following steps: collecting polycarbonate waste, cleaning, airing, and crushing into particles for later use; weighing the crushed polycarbonate waste, polypropylene, ABS resin, plasticizer, flame retardant, calcium carbonate and dicumyl peroxide according to the weight ratio, heating and mixing at a high speed, wherein the heating temperature is 80 ℃, the rotating speed is 110r/min, and the mixing time is 40min; and continuously heating to 280 ℃ by using a granulator, melting, extruding the melted polymer, and granulating to obtain modified plastic particles.
Example 3
The embodiment provides a regenerated modified plastic particle and a preparation method thereof.
The regenerated modified plastic particles consist of the following components in parts by weight: 50 parts of polycarbonate waste, 25 parts of polypropylene, 15 parts of ABS resin, 10 parts of plasticizer, 8 parts of flame retardant, 10 parts of calcium carbonate and 0.5 part of dicumyl peroxide; wherein the flame retardant is tris (4- (3-bromopropionamido) phenyl) phosphate; the plasticizer is diisobutyl phthalate.
The preparation method of the modified plastic particles was the same as in example 2.
Example 4
The embodiment provides a regenerated modified plastic particle and a preparation method thereof.
The regenerated modified plastic particles consist of the following components in parts by weight: 65 parts of polycarbonate waste, 20 parts of polypropylene, 10 parts of ABS resin, 15 parts of plasticizer, 10 parts of flame retardant, 8 parts of calcium carbonate and 0.2 part of dicumyl peroxide; wherein the flame retardant is tris (4- (3-bromopropionamido) phenyl) phosphate; the plasticizer is diisobutyl phthalate.
The preparation method of the modified plastic particles was the same as in example 2.
Comparative example 1
The embodiment provides a regenerated modified plastic particle and a preparation method thereof.
This comparative example is compared to example 2, wherein no flame retardant was added, and the remainder is the same as example 2.
Comparative example 2
The embodiment provides a preparation method of regenerated modified plastic particles.
This comparative example is compared to example 2, wherein the added flame retardant is tris (4- (3-chloropropionamido) phenyl) phosphate, the remainder being the procedure of example 2; wherein the preparation method of tris (4- (3-chloropropionamido) phenyl) phosphate refers to example 1, N-bromosuccinimide is replaced by N-chlorosuccinimide.
Comparative example 3
The embodiment provides a regenerated modified plastic particle and a preparation method thereof.
This comparative example is compared with example 2 in which the flame retardant added is triphenyl phosphate, and the remainder is the same as example 2.
Comparative example 4
The embodiment provides a regenerated modified plastic particle and a preparation method thereof.
This comparative example is compared to example 2, wherein the flame retardant added is tris (2-chloroethyl) phosphate, with the remainder being the procedure of example 2.
Comparative example 5
A polycarbonate modified plastic particle sold in China is manufactured by Dongguan city plastics and plastics limited company, and the brand EXL4412.
Test example 1
The modified plastic particles prepared in examples 2 to 4 and comparative examples 1 to 2, respectively, were subjected to the relevant performance test in comparative example 3; tensile strength test method: GB/T1040-2006; notched impact strength test method: GB/T1043-2008; oxygen index test method: GB/T2406-2009; the Vicat softness testing method comprises the following steps: GB/T1633-2000; low temperature ball drop test conditions: placing the sample at the temperature of minus 30 ℃ for 5 hours, then carrying out ball falling test, and recording the ball falling height when the sample is cracked, wherein the ball falling is solid iron balls with the mass of 50 g; the test results are shown in Table 1.
Table 1 correlation performance test table
As can be seen from the comparison results of Table 1, the modified plastic particles prepared in examples 2 to 4 are superior to those prepared in comparative examples 1 to 5 in mechanical properties, flame retardance, low temperature resistance and heat resistance, wherein the modified plastic particles prepared in example 2 are excellent in mechanical properties, flame retardance and heat resistance, and still have good toughness at low temperature; by comparing the example 2 with the comparative example 1, the flame retardant tri (4- (3-bromopropionamido) phenyl) phosphate added in the example 2 has double flame retardant effect and better flame retardance, and the lubricating effect of the flame retardant can promote the components to be better fused with each other, so that the fireproof flame retardance and the mechanical property of the modified plastic are improved; the comparison of the example 2 and the comparative examples 2-4 shows that the triphenyl phosphate derivative of the flame retardant prepared by the invention has superior dual flame retardant effect compared with the triphenyl phosphate of the phosphorus flame retardant and the tri (2-chloroethyl) phosphate of the phosphorus halogen flame retardant, wherein the tri (4- (3-bromopropionamido) phenyl) phosphate is preferable, the flame retardant effect is the best, and meanwhile, the triphenyl phosphate derivative has lubricating effect, so that the components can be better fused with each other, and the comprehensive performance of the modified plastic is improved.
The regenerated modified plastic particles provided by the invention have good impact resistance, heat resistance and strength; the alloy still has better toughness at low temperature; but also has good fireproof and flame-retardant performance; the method is suitable for application in the fields of electronic devices, automobile components and the like, and can meet market demands.
Although embodiments of the present application have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the application, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. The regenerated modified plastic particles are characterized by comprising the following components in parts by weight:
50-65 parts of polycarbonate waste;
20-30 parts of polypropylene;
10-20 parts of ABS resin;
10-15 parts of plasticizer;
8-12 parts of flame retardant;
5-10 parts of calcium carbonate;
0.2-1 part of dicumyl peroxide;
the plasticizer is diisobutyl phthalate, dimethyl phthalate or diethyl phthalate; the flame retardant is triphenyl phosphate derivative, and the preparation method comprises the following steps: taking p-aminophenol as a starting material, and sequentially substituting the p-aminophenol by propionyl chloride and a halogenated reagent, wherein the halogenated reagent is N-bromosuccinimide or N-chlorosuccinimide; finally, the three-phosphorus oxychloride is subjected to phosphorylation reaction to generate a triphenyl phosphate derivative, and the structural formula is as follows:
the method comprises the steps of carrying out a first treatment on the surface of the Wherein X is a bromine atom or a chlorine atom.
2. The recycled modified plastic particle of claim 1, wherein the triphenyl phosphate derivative is prepared by the process of:
s1: adding p-aminophenol and triethylamine into an anhydrous dichloromethane solution, dropwise adding propionyl chloride under ice bath stirring, and then heating to react to generate an intermediate I, wherein the structural formula is as follows:
；
s2: adding the intermediate I into acetonitrile solution, protecting with nitrogen, heating and stirring, adding azodiisobutyronitrile, and then adding N-bromosuccinimide or N-chlorosuccinimide to react to generate an intermediate II, wherein the structural general formula is as follows:
；
s3: sequentially adding an intermediate II, pyridine and phosphorus oxychloride into an anhydrous benzene solution, and heating to react to generate a triphenyl phosphate derivative, wherein the structural general formula is as follows:
the method comprises the steps of carrying out a first treatment on the surface of the Wherein X is a bromine atom or a chlorine atom.
3. A recycled modified plastic particle as claimed in claim 2, wherein the reaction temperature in step S1 is 25 ℃ and the reaction time is 0.5h.
4. The recycled and modified plastic particles of claim 2, wherein the reaction temperature in step S2 is 55-65 ℃ and the reaction time is 0.5-1h.
5. A recycled modified plastic particle as claimed in claim 2, wherein the reaction temperature in step S3 is 80 ℃ and the reaction time is 3-5 hours.
6. A method for producing a reclaimed modified plastic granule as claimed in any one of claims 1 to 5, comprising the steps of: collecting polycarbonate waste, cleaning, airing, and crushing into particles for later use; weighing the crushed polycarbonate waste, polypropylene, ABS resin, plasticizer, flame retardant, calcium carbonate and dicumyl peroxide according to the weight ratio, heating and mixing at a high speed, wherein the heating temperature is 70-90 ℃, the rotating speed is 90-110r/min, and the mixing time is 30-40min; and continuously heating to 280 ℃ by using a granulator, melting, extruding the melted polymer, and granulating to obtain modified plastic particles.
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| CN114181246A (en) * | 2021-12-20 | 2022-03-15 | 江苏丹霞新材料有限公司 | Preparation method of liquid bisphenol A bis (diphenyl phosphate) flame retardant |
| WO2022111448A1 (en) * | 2020-11-25 | 2022-06-02 | 四川海思科制药有限公司 | Method for preparing btk degrading agent |
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| US4062909A (en) * | 1974-04-08 | 1977-12-13 | Monsanto Company | Phosphoroamidates |
| JPH10168227A (en) * | 1997-11-27 | 1998-06-23 | Asahi Chem Ind Co Ltd | Phosphoric ester flame retardant |
| JP2006069980A (en) * | 2004-09-03 | 2006-03-16 | Songwon Industrial Co Ltd | Functional organophosphorus compound and method for producing the same |
| CN109689759A (en) * | 2016-09-08 | 2019-04-26 | 溴化合物有限公司 | Fire-retardant transparent polycarbonate composition |
| CN106543659A (en) * | 2016-11-25 | 2017-03-29 | 广东国立科技股份有限公司 | A kind of recycled plastic granules and its preparation method |
| WO2022111448A1 (en) * | 2020-11-25 | 2022-06-02 | 四川海思科制药有限公司 | Method for preparing btk degrading agent |
| CN114181246A (en) * | 2021-12-20 | 2022-03-15 | 江苏丹霞新材料有限公司 | Preparation method of liquid bisphenol A bis (diphenyl phosphate) flame retardant |
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