CN115895039A - Triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant and preparation method thereof - Google Patents
Triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant and preparation method thereof Download PDFInfo
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- CN115895039A CN115895039A CN202211462228.3A CN202211462228A CN115895039A CN 115895039 A CN115895039 A CN 115895039A CN 202211462228 A CN202211462228 A CN 202211462228A CN 115895039 A CN115895039 A CN 115895039A
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical class [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 title claims abstract description 34
- 239000003063 flame retardant Substances 0.000 title claims abstract description 32
- 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 28
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000002002 slurry Substances 0.000 claims abstract description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229960001545 hydrotalcite Drugs 0.000 abstract description 21
- 229910001701 hydrotalcite Inorganic materials 0.000 abstract description 21
- 239000002131 composite material Substances 0.000 abstract description 13
- 239000011159 matrix material Substances 0.000 abstract description 6
- 238000005054 agglomeration Methods 0.000 abstract description 5
- 230000002776 aggregation Effects 0.000 abstract description 5
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 239000004743 Polypropylene Substances 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 238000005303 weighing Methods 0.000 description 7
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 6
- -1 biomedicines Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical class [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920006113 non-polar polymer Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 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
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- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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Abstract
The invention discloses a triazine-based organic covalent skeleton modified hydrotalcite-based flame retardant and a preparation method thereof, wherein melamine and MgAl-LDH are placed in DMF, and are ultrasonically stirred to obtain slurry A; putting trichloro hydrogen in DMF, and ultrasonically stirring to obtain slurry B; slowly dripping the slurry B into the slurry A under the stirring condition, and then adding triethylamine to obtain slurry C; and heating the slurry C for reaction to obtain the triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant. According to the invention, the triazine-based organic covalent skeleton is generated through in-situ polymerization reaction on the MgAl-LDH surface, so that the stability and the hydrophobicity of the hydrotalcite are improved, the agglomeration performance of the hydrotalcite and the compatibility between the hydrotalcite and a polymer matrix are improved, and the mechanical property and the flame retardant property of the composite material are obviously improved.
Description
Technical Field
The invention belongs to the technical field of hydrotalcite flame retardance, and particularly relates to a triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant and a preparation method thereof.
Background
Layered Double Hydroxides (LDHs) are a layered anionic clay consisting of positively charged metal cation platelets and negatively charged interlayer anions. Due to its unique structure and properties, LDHs are widely used in the fields of catalysts, adsorbents, biomedicines, flame retardants, and the like. Wherein, the magnesium aluminum hydrotalcite (MgAl-LDH) is used as the most typical layered double hydroxide and is used for various high molecular flame retardants due to the characteristics of no halogen, low smoke, easy preparation, low price and the like.
However, as a halogen-free flame retardant, the MgAl-LDH laminate contains a large number of hydroxyl groups, which easily causes hydrogen bonds to form to cause agglomeration of the MgAl-LDH. In addition, mgAl-LDH as an inorganic clay material has the problem of poor compatibility with a nonpolar polymer matrix, thereby easily causing the mechanical properties of the composite material to be damaged.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide a triazine-based organic covalent skeleton modified hydrotalcite-based flame retardant and a preparation method thereof.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a preparation method of a triazine-based organic covalent skeleton modified hydrotalcite-based flame retardant comprises the following steps:
(1) Putting melamine and MgAl-LDH into DMF, and ultrasonically stirring to obtain slurry A; putting trichloro hydrogen in DMF, and ultrasonically stirring to obtain slurry B;
(2) Slowly dripping the slurry B into the slurry A under the stirring condition, and then adding triethylamine to obtain slurry C; and heating the slurry C for reaction to obtain the triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant.
According to the invention, a triazine-based organic covalent skeleton is generated through in-situ polymerization reaction on the surface of MgAl-LDH, and the surface morphology of MgAl-LDH is obviously changed while nitrogen is introduced, so that the stability and hydrophobicity of hydrotalcite are improved, and the agglomeration performance of hydrotalcite and the compatibility between hydrotalcite and a polymer matrix are improved. Moreover, the inventor also unexpectedly finds that in the reaction process, the addition sequence and the mixing process of the raw materials can generate obvious influence on the surface appearance and the performance of the finally generated triazine-based organic covalent skeleton modified hydrotalcite-based flame retardant. Only when the addition sequence and the mixing mode of firstly mixing the MgAl-LDH with the melamine and then adding the trichloro hydrogen are adopted, the MgAl-LDH is easier to modify on the surface, and the self-stacking condition of the MgAl-LDH is obviously improved. The other method is that the melamine and the cyanuric chloride hydrogen are mixed firstly, and then the MgAl-LDH is added; or directly mixing the three, the obtained hydrotalcite-based flame retardant has relatively smooth surface and self-stacking is not improved. This is also apparent in the mechanical and flame retardant properties of the flame retardant composite material finally obtained.
Further, in the step (1), the mass ratio of MgAl-LDH to melamine is 2-3:1; in the slurry A, the concentration of MgAl-LDH is 10-20g/L; the concentration of the trichloro hydrogen in the slurry B is 20-30g/L.
Further, in the step (2), the mass ratio of MgAl-LDH to hydrogen trichloride in the slurry C is 3-5:1, the mass-to-volume ratio of MgAl-LDH to triethylamine is 0.3-0.6g:1ml.
Further, in the step (2), the heating reaction temperature is 70-90 ℃ and the time is 8-12h.
The invention also provides the triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant prepared by the preparation method.
The invention has the advantages that:
according to the invention, the triazine-based organic covalent skeleton is generated on the surface of MgAl-LDH through in-situ polymerization reaction by strictly controlling the adding sequence and the mixing process of the reaction raw materials, and the surface morphology of MgAl-LDH is obviously changed while introducing nitrogen, so that the stability and the hydrophobicity of hydrotalcite are improved, the agglomeration performance of hydrotalcite per se and the compatibility between hydrotalcite and a polymer matrix are improved, and the mechanical performance and the flame retardant property of the composite material are obviously improved.
Drawings
FIG. 1 is an XRD pattern of LDH @ TOF obtained in example 1 of the present invention;
FIG. 2 is an FTIR plot of an LDH @ TOF made in example 1 of the present invention;
FIG. 3 is an SEM photograph of LDH @ TOF and LDH (MgAl-LDH) produced in example 1 of the present invention;
FIG. 4 is SEM images of LDH @ TOF obtained in example 1 of the present invention, D1 obtained in comparative example 1, and D2 obtained in comparative example 2.
Detailed Description
The invention is further described below with reference to the drawings and examples.
In the invention, mgAl-LDH is conventional magnesium-aluminum hydrotalcite and is prepared by the prior method, for example:
firstly, according to the molar ratio of magnesium cations to aluminum cations of 3:1 weighing 0.03mol of Mg (NO) 3 ) 2 ·6H 2 O and 0.01mol of Al (NO) 3 ) 3 ·6H 2 And O, dissolving the two into 200ml of deionized water, and carrying out ultrasonic treatment to form a mixed salt solution for later use. Accurately weighing urea with 3.3 times of the total molar number of the metal cations, placing the urea in 200ml of deionized water, and carrying out ultrasonic dissolution for later use. The two are transferred into a 500ml hydrothermal reaction kettle with a polytetrafluoroethylene liningAnd after fully mixing, transferring the mixture into an electric heating constant-temperature drying oven to react for 24 hours at the temperature of 110 ℃. And finally, carrying out suction filtration, washing, drying and grinding on the obtained product to obtain the product, namely the magnesium-aluminum hydrotalcite (MgAl-LDH).
Example 1
(1) Weighing 3g of magnesium aluminum hydrotalcite (MgAl-LDH) and 1.11g of melamine, ultrasonically dispersing the mixture in 200ml of DMF to obtain slurry A, and transferring the slurry A into a 500ml three-neck flask;
(3) Weighing 0.75g of trichloropolyhydrogen, ultrasonically dispersing in 30ml of DMF to obtain slurry B, slowly dropwise adding into a three-neck flask, finally dropwise adding 6ml of triethylamine to obtain slurry C, reacting at 90 ℃ for 12 hours, keeping stirring in the reaction process, and after the reaction is finished, carrying out suction filtration, washing, drying and grinding on the obtained target product to obtain the triazine-based organic covalent skeleton modified magnesium-aluminum hydrotalcite-based flame retardant, which is recorded as LDH @ TOF.
As shown in fig. 1, LDH @ tof shows the characteristic diffraction peaks (003), (006), (009), (015), (018) unique to hydrotalcite materials, suggesting that it still retains the layered structure of LDH. Compared with the diffraction peak of LDH, the LDH @ TOF has several new diffraction peaks, all characteristic diffraction peaks of the LDH @ TOF can correspond to the diffraction peaks of the LDH and TOF (triazine-based organic covalent framework), and the peak shape is still sharp and strong, which indicates that the LDH still maintains a good crystal form after modification.
As shown in FIG. 2, not only the peak of LDH oscillation but also 1664cm was observed in the FT-IR spectrum of LDH @ TOF -1 And 1536cm -1 An oscillation peak of the TOF triazine ring appears nearby, and further proves the successful synthesis of the LDH @ TOF.
As shown in fig. 3, both LDH (upper) and LDH @ tof (lower) show sheet structures, which are typical of magnesium aluminum hydrotalcite structures. The LDH surface is smooth, the particle size is uniform, the edge is smooth, the surface of the LDH @ TOF is rough and is covered by a layer of substance, and the successful modification of the triazine-based organic covalent skeleton generated by the in-situ reaction of melamine and cyanuric chloride on the LDH surface is shown.
Comparative example 1
(1) Weighing 3g of magnesium aluminum hydrotalcite (MgAl-LDH), ultrasonically dispersing in 200ml of DMF, and transferring into a 500ml three-neck flask;
(2) Weighing 1.11g of melamine and 0.75g of trichlorohydrine, ultrasonically dispersing the melamine and the trichlorohydrine together in 30ml of DMF (dimethyl formamide), slowly dropwise adding the mixture into a three-necked flask, finally dropwise adding 6ml of triethylamine, reacting at 90 ℃ for 12 hours, keeping stirring in the reaction process, and after the reaction is finished, carrying out suction filtration, washing, drying and grinding on the obtained target product to obtain the triazine-based organic covalent skeleton modified magnesium-aluminum hydrotalcite-based flame retardant, which is marked as D1.
Comparative example 2
(1) Weighing 3g of magnesium aluminum hydrotalcite (MgAl-LDH), 1.11g of melamine and 0.75g of trichlorohydric chloride, ultrasonically dispersing the mixture in 200ml of DMF, and transferring the mixture into a 500ml three-neck flask;
(2) Measuring 6ml of triethylamine, dripping the triethylamine into a three-neck flask, reacting for 12 hours at 90 ℃, keeping stirring in the reaction process, and after the reaction is finished, carrying out suction filtration, washing, drying and grinding on the obtained target product to obtain the triazine-based organic covalent skeleton modified magnesium-aluminum hydrotalcite-based flame retardant, which is marked as D2.
As shown in FIG. 4, from the morphology, the surface modification rate of LDH @ TOF obtained in example 1 is significantly higher than that of D1 obtained in comparative example 1 and that of D2 obtained in comparative example 2, and the surface morphologies of D1 and D2 are smooth and self-stacking is severe.
LDH, LDH @ TOF prepared in example 1, D1 prepared in comparative example 1 and D2 prepared in comparative example 2 are respectively melt-blended with polypropylene (PP) by a melt blending method with the mass fraction of the flame retardant being 20wt% to prepare PP composite materials, and the flame retardance and mechanical property tests are carried out on the PP composite materials, and the results are shown in Table 1:
TABLE 1 flame retardance and mechanical Property test results for different PP composites
As can be seen from Table 1, after the flame retardants LDH and LDH @ TOF are added, the tensile strength and the elongation at break of the PP/LDH composite material and the PP/LDH @ TOF composite material are reduced, and compared with the situation that pure LDH has an agglomeration phenomenon in a PP matrix, after the LDH @ TOF is added, the compatibility of the LDH @ TOF and the PP matrix is greatly improved, and the reduction of mechanical performance parameters is obviously relieved. Pure PP is a material which is easy to burn, after the flame retardant is added, the LOI value and the UL-94 grade of the PP composite material show a trend of rising, and the peak heat release rate and the total heat release rate are correspondingly reduced. Under the same load capacity, the LOI value and UL-94 grade of PP/LDH @ TOF are both obviously superior to those of PP/LDH, and the flame retardant property of LDH @ TOF is shown to be obviously stronger than that of LDH, namely the flame retardant property of LDH is obviously improved after triazine-based organic covalent skeleton modification.
Further, as can be seen from the comparison of the flame retardant performance and mechanical performance of the PP composite materials obtained by adding the LDH @ tof prepared in example 1, the D1 prepared in comparative example 1 and the D2 prepared in comparative example 2 as the flame retardant, the PP composite materials obtained by adding the LDH @ tof prepared in example 1 as the flame retardant are significantly better than the PP composite materials obtained by adding MgAl-LDH and melamine in the same order and mixing manner (such as mixing melamine and trichloro and then adding MgAl-LDH or mixing them directly at the same time) in comparative example 1 and comparative example 2 in the same order and mixing manner.
Claims (5)
1. A preparation method of a triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant is characterized by comprising the following steps:
(1) Putting melamine and MgAl-LDH into DMF, and ultrasonically stirring to obtain slurry A; putting trichloro hydrogen in DMF, and ultrasonically stirring to obtain slurry B;
(2) Slowly dripping the slurry B into the slurry A under the stirring condition, and then adding triethylamine to obtain slurry C; and heating the slurry C for reaction to obtain the triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant.
2. The preparation method according to claim 1, wherein in the step (1), the mass ratio of MgAl-LDH to melamine is 2-3:1; in the slurry A, the concentration of MgAl-LDH is 10-20g/L; the concentration of the trichloro hydrogen in the slurry B is 20-30g/L.
3. The method according to claim 1, wherein in the step (2), the mass ratio of MgAl-LDH to hydrogen trichloride in the slurry C is 3-5:1, the mass-to-volume ratio of MgAl-LDH to triethylamine is 0.3-0.6g:1ml.
4. The method according to claim 1, wherein in the step (2), the heating reaction is carried out at a temperature of 70 to 90 ℃ for 8 to 12 hours.
5. The triazine-based organic covalent skeleton-modified hydrotalcite-based flame retardant prepared by the preparation method of any one of claims 1 to 4.
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- 2022-11-22 CN CN202211462228.3A patent/CN115895039B/en active Active
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