CN115124766B - Preparation method of coated red phosphorus flame retardant - Google Patents
Preparation method of coated red phosphorus flame retardant Download PDFInfo
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- CN115124766B CN115124766B CN202210795430.1A CN202210795430A CN115124766B CN 115124766 B CN115124766 B CN 115124766B CN 202210795430 A CN202210795430 A CN 202210795430A CN 115124766 B CN115124766 B CN 115124766B
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- red phosphorus
- flame retardant
- phosphorus flame
- zinc
- coated red
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 78
- 239000003063 flame retardant Substances 0.000 title claims abstract description 47
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000013154 zeolitic imidazolate framework-8 Substances 0.000 claims abstract description 25
- MFLKDEMTKSVIBK-UHFFFAOYSA-N zinc;2-methylimidazol-3-ide Chemical compound [Zn+2].CC1=NC=C[N-]1.CC1=NC=C[N-]1 MFLKDEMTKSVIBK-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000011701 zinc Substances 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 21
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 20
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002775 capsule Substances 0.000 claims abstract description 17
- 239000002131 composite material Substances 0.000 claims abstract description 12
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003751 zinc Chemical class 0.000 claims abstract description 9
- 239000011787 zinc oxide Substances 0.000 claims abstract description 9
- 239000002244 precipitate Substances 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical group [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004246 zinc acetate Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229960001763 zinc sulfate Drugs 0.000 claims description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 abstract description 9
- 238000007254 oxidation reaction Methods 0.000 abstract description 9
- 238000012360 testing method Methods 0.000 description 8
- 239000002861 polymer material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 4
- 239000004640 Melamine resin Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- -1 zeolite imidazole ester Chemical class 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K2003/026—Phosphorus
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Fireproofing Substances (AREA)
Abstract
The invention provides a preparation method of a coated red phosphorus flame retardant, which comprises the following steps: (1) Dispersing red phosphorus and polyethylene glycol in water, adding cyanuric acid and zinc oxide, and reacting for 2-6 h; (2) Adding soluble zinc salt and 2-methylimidazole, adding ethylenediamine, reacting 5-20 h, dehydrating and drying the precipitate to obtain the coated red phosphorus flame retardant taking zinc cyanurate and ZIF-8 as composite capsule wall materials. The coated red phosphorus flame retardant provided by the invention has the characteristics of high whiteness, good oxidation resistance and high flame retardant efficiency.
Description
Technical Field
The invention relates to the field of flame retardant materials, in particular to a preparation method of a coated red phosphorus flame retardant.
Background
Compared with other halogen-free flame retardants, the red phosphorus flame retardant has the advantages of high flame retardant efficiency, small consumption and the like, and is widely applied to the fields of rubber, nylon, polyester, epoxy resin, polyurethane and the like. However, pure red phosphorus has the defects of easy moisture absorption, unstable property, poor compatibility with high polymer materials, easy coloring and the like. After the red phosphorus is coated, the stability is improved, and the compatibility with the high polymer material is better. In addition, after the mauve of the red phosphorus is covered by the capsule wall material, the prepared coated red phosphorus has lighter color and luster, and can be used for processing light-colored polymer material products. Therefore, the coated red phosphorus is added into the high polymer material as the flame retardant, so that the defect of direct use of the red phosphorus can be overcome, and a quite even better flame retardant effect can be achieved.
At present, a mature red phosphorus coated product in the market is melamine resin coated red phosphorus, and melamine resin is used as a capsule wall material, so that the red phosphorus coated red phosphorus has the characteristics of good oxidation resistance, low moisture absorption rate and good compatibility with high polymer materials, and is widely applied to processing of nylon, PET, PP and the like (Xiong Lianming, university of middle and south, doctor's paper, 2004). However, melamine resin is transparent polymer resin, has poor covering property on red phosphorus, has darker color, and cannot be used for processing light-colored polymer material products. In addition, the patent reports that the zeolite imidazole ester framework material coats the red phosphorus flame retardant and the preparation method thereof (CN 202011228743.6), and the ZIF-8 can be uniformly coated on the surface of the red phosphorus, and the prepared ZIF-8 coated red phosphorus has better whiteness, oxidation resistance and flame retardant property. However, compared with common inorganic coating materials such as melamine resin, aluminum hydroxide and the like, the ZIF-8 has higher raw material cost, and affects the large-scale application of the ZIF-8 coated red phosphorus. Therefore, the ZIF-8 and the cheap material are explored to cooperatively coat the red phosphorus so as to reduce the production cost, further improve the whiteness and the flame retardant property of the coated red phosphorus flame retardant, and have important significance for expanding the application range of the red phosphorus flame retardant.
Disclosure of Invention
The invention aims to provide a preparation method of a coated red phosphorus flame retardant, and the coated red phosphorus flame retardant obtained by the method has the advantages of high whiteness, good oxidation resistance, high flame retardant efficiency, lower cost and the like.
The invention provides a preparation method of a coated red phosphorus flame retardant, which comprises the following steps:
(1) Dispersing red phosphorus and polyethylene glycol in water, adding cyanuric acid and zinc oxide, and reacting for 2-6 h;
(2) Adding soluble zinc salt, 2-methylimidazole and ethylenediamine, reacting 5-20 h, dehydrating and drying the precipitate to obtain the coated red phosphorus flame retardant taking zinc cyanurate and ZIF-8 as composite capsule wall materials.
Further, the mass ratio of the polyethylene glycol to the red phosphorus is 1-6: 100.
Further, the reaction temperature is 70-100 ℃.
Further, the molar ratio of cyanuric acid to red phosphorus is 0.2-0.4: 1.
Further, the molar ratio of cyanuric acid to zinc oxide is 2-2.3: 3.
Further, the zinc salt is zinc acetate, zinc nitrate, zinc chloride or zinc sulfate.
Further, the molar ratio of Zn 2+ to red phosphorus in the zinc salt is 0.1-0.2: 1.
Further, the molar ratio of Zn 2+ to 2-methylimidazole in the zinc salt is 1:3 to 6.
Further, the molar ratio of ethylenediamine to 2-methylimidazole is 1:5 to 10.
The preparation method disclosed by the invention is simple in process, the surface of red phosphorus is coated by zinc cyanurate, and the ZIF-8 shell layer is self-assembled on the surface of the red phosphorus, so that the red phosphorus-coated flame retardant has the characteristics of good color coverage performance, high whiteness and good oxidation resistance, and can be applied to processing of light-colored polymer materials.
Zinc cyanurate is a flame retardant with good color coverage and low cost; ZIF-8 is a novel capsule wall material capable of continuously self-assembling on the solid surface, can be uniformly coated on the solid surface, and has good synergistic flame retardant property. The zinc cyanurate and the ZIF-8 are used as the composite capsule wall material for coating the red phosphorus, so that the advantages of the zinc cyanurate and the ZIF-8 can be effectively combined, and the whiteness and the flame retardant property of the prepared zinc cyanurate and ZIF-8 composite coated red phosphorus are superior to those of zinc cyanurate or ZIF-8 single coated red phosphorus. The zinc cyanurate and the ZIF-8 are used as composite capsule wall materials for coating red phosphorus, and have good synergistic effect.
Detailed Description
The following describes the present invention in further detail. The above and other objects, features and advantages of the present invention will be apparent to those skilled in the art from the detailed description of the present invention.
Example 1
Dispersing 17 g red phosphorus and 0.51 g polyethylene glycol in 500mL water, adding 21 g cyanuric acid and 18.5 g zinc oxide, and stirring at 85deg.C for reacting 3 h; adding 15 g zinc acetate, 26 g 2-methylimidazole and 2.5 g ethylenediamine, continuously stirring for reaction 10. 10 h, dehydrating and drying the precipitate obtained by the reaction to obtain the coated red phosphorus flame retardant taking zinc cyanurate and ZIF-8 as composite capsule wall materials, wherein the red phosphorus content is 26%.
Example 2
Dispersing 17 g red phosphorus and 0.25 g polyethylene glycol in 600 mL water, adding 14.5 g cyanuric acid and 11.5 g zinc oxide, and stirring at 70deg.C for reacting 6 h; then adding 20.5 g zinc nitrate, 52 g 2-methylimidazole and 6.5 g ethylenediamine, continuously stirring for reaction 20. 20 h, dehydrating and drying the precipitate obtained by the reaction to obtain the coated red phosphorus flame retardant taking zinc cyanurate and ZIF-8 as composite capsule wall materials, wherein the red phosphorus content is 29%.
Example 3
17 G red phosphorus and 0.9 g polyethylene glycol are dispersed in 700 mL water, 28 g cyanuric acid and 26 g zinc oxide, and stirred at 95 ℃ for reaction 2 h; then adding 9g zinc sulfate, 15 g 2-methylimidazole and 1.1 g ethylenediamine, continuously stirring for reaction 5.5 h, dehydrating and drying the precipitate obtained by the reaction to obtain the coated red phosphorus flame retardant taking zinc cyanurate and ZIF-8 as composite capsule wall materials, wherein the red phosphorus content is 23%.
Comparative example 1
17 G red phosphorus and 0.51 g polyethylene glycol are dispersed in 500mL water, 30.5 g cyanuric acid and 28.5 g zinc oxide are added, 13 h is reacted under stirring at 85 ℃, precipitate obtained by the reaction is dehydrated and dried, and the coated red phosphorus flame retardant taking zinc cyanurate as a single capsule wall material is obtained, wherein the red phosphorus content is 26%.
Comparative example 2
17 G red phosphorus and 0.17 g polyethylene glycol are dispersed in 500 mL water, 51 g zinc acetate, 92 g of 2-methylimidazole and 9 g ethylenediamine are added, 13 h is reacted under stirring at 85 ℃, precipitate obtained by the reaction is dehydrated and dried, and the coated red phosphorus flame retardant taking ZIF-8 as a single capsule wall material is obtained, wherein the red phosphorus content is 26%.
Performance test experiment:
the coated red phosphorus flame retardant samples prepared in examples 1 to 3, comparative example 1 and comparative example 2 were subjected to the following tests:
Whiteness test: weighing 10.00 g samples, tabletting, placing in a sample box, and testing on a digital display whiteness meter, wherein the results are shown in Table 1;
oxidation resistance test: respectively weighing 10.00 g samples into a three-neck flask containing 200 ml distilled water, boiling the solution for 1 h, filtering and removing an initial filtrate, adding 10.00 g analytically pure sodium chloride into 100 ml of the filtrate, titrating oxyacids formed by oxidation in the filtrate by using a standard sodium hydroxide solution after dissolution, and expressing oxidation resistance by using milligrams of sodium hydroxide consumed per gram of red phosphorus, wherein the result is shown in table 1;
Limiting oxygen index test: the test was carried out according to the method in GB/T2406.2-2009, the addition amount of the coated red phosphorus flame retardant is 12%, and the results are shown in Table 1.
From the test results of examples 1-3 in Table 1, it is known that the coated red phosphorus flame retardant using zinc cyanurate and ZIF-8 as composite capsule wall material has higher whiteness and flame retardant efficiency, and better oxidation resistance. According to the test results of example 1, comparative example 1 and comparative example 2, compared with the coated red phosphorus sample using zinc cyanurate or ZIF-8 as the single capsule wall material, the coated red phosphorus using zinc cyanurate and ZIF-8 as the composite capsule wall material has obviously better flame retardant property and whiteness under the condition of the same red phosphorus content. The result shows that the zinc cyanurate and the ZIF-8 are taken as the composite capsule wall material for coating the red phosphorus, so that the advantages of the zinc cyanurate and the ZIF-8 can be effectively combined, and the zinc cyanurate and the ZIF-8 have good synergistic effect.
It should be understood that while the present invention has been clearly described by way of the above embodiments, those skilled in the art will recognize that various changes and modifications can be made in accordance with the present invention without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (9)
1. The preparation method of the coated red phosphorus flame retardant is characterized by comprising the following steps:
(1) Dispersing red phosphorus and polyethylene glycol in water, adding cyanuric acid and zinc oxide, and reacting for 2-6 h;
(2) Adding soluble zinc salt, 2-methylimidazole and ethylenediamine, reacting 5-20 h, dehydrating and drying the precipitate to obtain the coated red phosphorus flame retardant taking zinc cyanurate and ZIF-8 as composite capsule wall materials.
2. The preparation method of the coated red phosphorus flame retardant according to claim 1, wherein the mass ratio of the polyethylene glycol to the red phosphorus is 1-6: 100.
3. The method for preparing the coated red phosphorus flame retardant according to claim 1, wherein the reaction temperature is 70-100 ℃.
4. The method for preparing the coated red phosphorus flame retardant according to claim 1, wherein the molar ratio of cyanuric acid to red phosphorus is 0.2-0.4: 1.
5. The method for preparing the coated red phosphorus flame retardant according to claim 1, wherein the molar ratio of cyanuric acid to zinc oxide is 2-2.3: 3.
6. The method for preparing the coated red phosphorus flame retardant according to claim 1, wherein the zinc salt is zinc acetate, zinc nitrate, zinc chloride or zinc sulfate.
7. The preparation method of the coated red phosphorus flame retardant according to claim 1, wherein the molar ratio of Zn 2+ to red phosphorus in the zinc salt is 0.1-0.2: 1.
8. The preparation method of the coated red phosphorus flame retardant according to claim 1, wherein the molar ratio of Zn 2+ to 2-methylimidazole in the zinc salt is 1:3 to 6.
9. The method for preparing the coated red phosphorus flame retardant according to claim 1, wherein the molar ratio of ethylenediamine to 2-methylimidazole is 1:5 to 10.
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| CN202210795430.1A CN115124766B (en) | 2022-07-07 | 2022-07-07 | Preparation method of coated red phosphorus flame retardant |
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| CN115124766B true CN115124766B (en) | 2024-04-26 |
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|---|---|---|---|---|
| WO2001090242A1 (en) * | 2000-05-25 | 2001-11-29 | Nippon Chemical Industrial Co., Ltd. | Red phosphorus-base flame retardant for epoxy resins, red phosphorus-base flame retardant compositions therefor, processes for the production of both, epoxy resin compositions for sealing semiconductor devices, sealants and semiconductor devices |
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| CN101343542A (en) * | 2008-08-25 | 2009-01-14 | 温州大学 | Method for preparing ultra-fine red phosphorus microcapsule |
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-
2022
- 2022-07-07 CN CN202210795430.1A patent/CN115124766B/en active Active
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