CN107629310B - Supermolecule intercalation structure light stabilizer and preparation method thereof - Google Patents
Supermolecule intercalation structure light stabilizer and preparation method thereof Download PDFInfo
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Abstract
The invention provides a supermolecule intercalation structure light stabilizer and a preparation method thereof, wherein an ultraviolet absorbent and a free radical trapping agent are innovatively assembled between L DHs layers, ultraviolet absorption performance of the ultraviolet absorbent is utilized to block photodegradation of plastics, and active free radicals generated by photodegradation are captured by the free radical trapping agent to reduce photooxidation of the plastics.
Description
Field of the invention
The invention relates to a light stabilizer with a supermolecular intercalation structure and a preparation method thereof.
Background
The light stabilizer is a functional assistant capable of inhibiting the degradation of plastics induced by ultraviolet light, and the action principle of the light stabilizer is mainly to realize the purpose of light protection by absorbing and transferring ultraviolet light energy, shielding ultraviolet light or capturing free radicals. The light stabilizer is compounded with the plastic in a physical mixing mode and is highly dispersed in the plastic matrix to fully exert the protection effect of the light stabilizer, reduce the photooxidation degradation of the plastic and achieve the purpose of prolonging the service life of the plastic. However, most light stabilizers have the defects of easy volatilization, easy migration, poor thermal stability and the like, and limit the application range of the light stabilizers.
Hydrotalcite (L a Double Hydroxides, abbreviated as L DHs) is a compound formed by connecting metal hydroxide laminates with positive charges and interlayer anions with negative charges by weak chemical bonds, and the composition of metal elements of a host laminate, the charge density and distribution of the host laminates, the types and the quantity of the interlayer anions, the interaction between a host and a guest and the like of the hydrotalcite have adjustable characteristics, so that functional anions can be inserted between the layers of the hydrotalcite by utilizing the characteristics, and a functional material with special properties is prepared.
The references Chai H, Xu X, L in Y, et Al Synthesis and UV adsorption properties of2, 3-dihydroxynapthalene-6-sulfonated-intercaled Zn-Al layered double hydroxides [ J]Polymer Degradation and stability,2009,94(4):744-3L DH is a precursor, an ion exchange method is adopted to successfully intercalate and assemble 2-methylnaphthylamine-1, 5-disulfonic acid (NADA) as an ultraviolet absorbent between ZnAl-L DH layers to construct a ZnAl-NADA-L DH ultraviolet absorbent material with a supermolecular intercalation structure, ZnAl-NADA-L DH and polypropylene (PP) are compounded to prepare L DH/PP composite material, ultraviolet analysis shows that the ultraviolet absorption of L DH/PP composite film is obviously higher than that of PP film, and the light aging test result shows that the introduction of L DH improves the light stability of PP.
The document Chai H, L in Y, Evans D G, et Al, Synthesis and UV absorbance polymers of 2-naphtylamine-1, 5-disulfonic acid intercalated Zn-Al layered hydroxides [ J ]. Industral & Engineering Chemistry Research,2008,47(9): 2855-propanate 2860 takes ZnAl-L DH as a precursor, and adopts an ion exchange method to successfully intercalate and assemble a UV absorbent 2, 3-dihydroxynaphthalene-6-sulfonic acid (DNSA) between ZnAl-L DH layers to construct a supermolecular intercalation structure ZnAl-DNSA-L DH UV absorbent material, and a DH 63/PP composite material is prepared by compounding ZnAl-DNSA-L and PP to prepare the DH 63/PP composite material, and the UV analysis finds that the UV absorption of the L DH/PP composite film is obviously higher than that of a PP film, and the light aging test result shows that the light aging rate is slowed down by introducing the DH 78 into the PP film.
The documents Cui G-J, Xu X-Y, L in Y-J, et Al Synthesis and UV Absorption Properties of 5,5 '-Methyleneorganic Acid-Intercalated Zn-Al L layerddouble Hydroxides [ J ]. Industrial & Engineering Chemistry Research,2009,49(2):448-453 uses ZnAl-L DH as a precursor, and adopts an ion exchange method to successfully intercalate 5, 5' -methylenesalicylic Acid (MDSA) into the supermolecular layers of ZnAl-L DH to construct an Intercalated structure ZnAl-MDSA-L DH ultraviolet absorbing material, and the light aging test result shows that the introduction of L DH slows down the light aging rate of PP.
Although the above documents produce various light stabilizers with supramolecular intercalation structure, the light protection capability of the light stabilizers is limited, and PP can still be slowly degraded during the use process. In order to further improve the light stability of PP, a light stabilizer with more excellent performance is urgently needed.
Disclosure of Invention
The invention aims to provide a light stabilizer with a supermolecular intercalation structure and a preparation method thereof.
According to the ultraviolet absorbent and free radical trapping agent co-intercalated structure L DHs, the ultraviolet absorbent and the free radical trapping agent are innovatively assembled between L DHs layers, ultraviolet absorption performance of the ultraviolet absorbent is utilized to block ultraviolet light from degrading plastics, active free radicals generated by light degradation are trapped by the free radical trapping agent to reduce photooxidation of the plastics, and due to the synergistic anti-photoaging effect of the ultraviolet absorbent and the free radical trapping agent between L DHs layers, the photoaging resistance of the ultraviolet absorbent and free radical trapping agent co-intercalated structure L DHs is obviously superior to that of an ultraviolet absorbent single intercalated layer L DHs, and the defect that the existing ultraviolet absorbent single intercalated layer L DHs is poor in photoaging resistance is overcome.
The chemical general formula of the supermolecular intercalation structure light stabilizer prepared by the invention is as follows:
[M2+ 1-xM3+ x(OH)2](A-)y(B-)z·cH2O
wherein M is2+And M3+Respectively divalent and trivalent metal cations, M, located on the host laminate2+Is Mg2+、Zn2+、Ni2 +、Ca2+、Fe2+、Cu2+Either or both of them, preferably Mg2+、Zn2+One of (1), M3+Is Al3+、Co3+、Ti3+、Fe3 +、Cr3+One or two kinds of trivalent metal cations, preferably Al3+；A-Being an anion of a radical scavenger A, B-Is an ultraviolet absorber anion; x is M3+/(M2++M3+) Is prepared from (A) and (B)The ratio of x to y + z (0.2. ltoreq. x.ltoreq.0.4, 0.01<y<0.39，0.01<z<0.39); c is the number of interlayer water molecules, 0.4<c<1。
The free radical trapping agent is a tetramethylpiperidine compound, and the chemical formula of the free radical trapping agent is shown as the following formula:
in the formula R1Is H or CH3；R2Is O-R3-COONa、NH-R3-COONa、O-R3-SO3Na or NH-R3-SO3Na wherein R3Is [ CH ]2]m[C6H4]nM is an integer of 1 to 8, and n is 0 or 1.
The ultraviolet absorbent is one or more of sodium p-aminobenzoate, sodium p-methoxycinnamate, sodium salicylate, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, sodium coumarin-3-carboxylate, sodium cinnamate, sodium benzotriazole-4-hydroxy-benzenesulfonate, and sodium 2-phenylbenzimidazole-5-sulfonate.
The specific preparation steps of the supramolecular intercalation structure light stabilizer are as follows.
A. Weighing M2+、M3+Dissolving nitrate or chloride salt of (A) in deionized water to remove carbon dioxide to obtain mixed salt solution, wherein M2+And M3+In a molar ratio of2 to 4, M3+The molar concentration of (a) is 0.05-0.8 mol/L.
Said M2+Is Mg2+、Zn2+、Ni2+、Ca2+、Fe2+、Cu2+Either or both of them, preferably Mg2+、Zn2 +One of (1), M3+Is Al3+、Co3+、Ti3+、Fe3+、Cr3+One or two kinds of trivalent metal cations, preferably Al3 +；
B. Preparing an alkali solution with the molar concentration of 0.05-1 mol/L, wherein the alkali is NaOH, KOH or ammonia waterThe molar amount of the base is M in the solution of the step A2+And M3+1.8-2.5 times the sum of the molar amounts, i.e. nOH -＝1.8-2.5(nM 2++nM 3+)；
Dissolving the two raw materials into a solvent according to the ratio of the mole ratio of the ultraviolet absorbent to the free radical trapping agent of 0.025-39 to prepare a solution with the total mole concentration of 0.05-0.5 mol/L, and adding the solution into the alkali solution to form a mixed solution B, wherein the sum of the mole amounts of the ultraviolet absorbent and the free radical trapping agent and the M in the solution A3+The ratio of the sum of the molar amounts being 1 to 3, i.e. nA+nB＝1-3nM 3+(ii) a The solvent is deionized water for removing carbon dioxide or a mixed solvent of the deionized water and a polar solvent, the polar solvent is ethanol, glycol or glycerol, and the corresponding solvent is selected according to the ultraviolet absorbent and the free radical trapping agent which can be used for dissolving.
The free radical trapping agent is a tetramethylpiperidine compound, and the chemical formula of the free radical trapping agent is shown as the following formula:
in the formula R1Is H or CH3；R2Is O-R3-COONa、NH-R3-COONa、O-R3-SO3Na or NH-R3-SO3Na wherein R3Is [ CH ]2]m[C6H4]nM is an integer between 1 and 8, n is 0 or 1;
the ultraviolet absorbent is one or more of sodium p-aminobenzoate, sodium p-methoxycinnamate, sodium salicylate, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, sodium coumarin-3-carboxylate, sodium cinnamate, sodium benzotriazole-4-hydroxy-benzenesulfonate and sodium 2-phenylbenzimidazole-5-sulfonate;
C. mixing the mixed salt solution A and the mixed solution B under nitrogen protection and stirring, reacting to generate precipitate, centrifuging and washing the precipitate for 3 times, preparing slurry with water to obtain slurry with solid content of 1-100 g/L, and adding violetExternal absorbent and free radical trapping agent, wherein the addition amount of the ultraviolet absorbent and the free radical trapping agent are M in the slurry3+0.1-0.3 times of the molar weight, then stirring and reacting for 4-24 hours at 50-150 ℃, cooling, filtering the product and washing for 4-9 times, and drying the filter cake for 12-24 hours at 60-100 ℃ to obtain the supramolecular intercalation structure light stabilizer.
Fig. 1 is an XRD spectrum of the supramolecular intercalated structure light stabilizer prepared in example 1, which shows that it has a single crystalline phase structure and that the uv absorber and the radical scavenger are successfully assembled between L DHs layers.
FIG. 2 is the FT-IR spectrum of the supramolecular intercalated light stabilizer prepared in example 1, showing successful assembly of UV absorber and radical scavenger between layers L DHs.
Fig. 3 is a graph of the photoprotective effect of the supramolecular intercalation structure light stabilizer prepared in example 1 on PP, and it can be seen from fig. 3 that the photoprotective effect of uv absorber and radical scavenger co-intercalation L DH on PP is significantly better than that of uv absorber mono-intercalation L DH.
The invention has the advantages that: the supermolecule intercalation structure light stabilizer prepared by the invention has the advantages of simple preparation method, rich raw material sources and convenience for industrial production, and also has the advantages of high heat resistance, good migration resistance, excellent light protection performance and the like, and can be widely applied to the fields of plastics, coatings and the like.
Description of the drawings:
FIG. 1 is an XRD spectrum of co-intercalation layer L DH of the UV absorber and radical scavenger prepared in example 1.
FIG. 2 is a FT-IR spectrum of co-intercalation layer L DH of the UV absorber and radical scavenger prepared in example 1.
FIG. 3 is a graph showing the photoprotective effect of UV absorber and radical scavenger co-intercalation L DH on PP prepared in example 1, wherein a is polypropylene, b is 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid intercalation L DH/polypropylene complex, and c is 2,2,6, 6-tetramethylpiperidine-4-oxopropanoic acid co-intercalation L DH/polypropylene complex with 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid.
The specific implementation mode is as follows:
example 1:
step A: 1.5g (5.0mmol) Mg (NO) are weighed3)2 .6H2O、0.938g(2.5mmol)Al(NO3)3 .9H2O, dissolving in 30ml to remove CO2Preparing a salt solution in the deionized water.
And B: weighing 0.6g of NaOH, dissolving in 30ml of deionized water without carbon dioxide to prepare an alkali solution; 0.5925g (2.5mmol) of sodium 2,2,6, 6-tetramethylpiperidine-4-oxopropionate and 0.825g (2.5mmol) of sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate were weighed out and dissolved in 40ml of a mixed solvent of deionized water with carbon dioxide removed and ethylene glycol, and the solution was added to an alkali solution to obtain a mixed solution.
And C: under the protection of nitrogen and stirring, the solution prepared in the step A, B is mixed and reacted to generate sediment, the generated sediment is centrifuged and washed for 3 times, then 120ml of deionized water without carbon dioxide is added to prepare slurry, 0.0593g (0.25mmol) of sodium 2,2,6, 6-tetramethylpiperidine-4-oxopropanoate and 0.0825g (0.25mmol) of sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate are respectively weighed and added into the slurry, then the sediment is placed in a water bath at 100 ℃ to be stirred and reacted for 6 hours, after the reaction is finished, the reaction product is centrifuged and washed for 6 times, the product obtained by centrifuging is placed in a baking oven at 100 ℃ to be dried for 24 hours, and the light stabilizer [ Mg ] with the supermolecule intercalation structure is obtained0.66Al0.34(OH)2](C12H22O3N)0.17(C14H11O6S)0.17·0.6H2O。
Example 2:
step A: 2.25g (7.5mmol) Mg (NO) are weighed3)2 .6H2O、0.938g(2.5mmol)Al(NO3)3 .9H2O, dissolved in 40ml to remove CO2Preparing a salt solution in the deionized water.
And B: weighing 0.8g of NaOH, dissolving in 45ml of deionized water without carbon dioxide to prepare an alkali solution; 0.5925g (2.5mmol) of sodium 1,2,2,6, 6-pentamethylpiperidine-4-oxoacetate and 0.8g (5mmol) of sodium salicylate were weighed out and dissolved in deionized water except carbon dioxide, and added to the alkali solution to form a mixed solution.
And C: under the protection of nitrogen and stirring, the solution prepared in the step A, B is mixed and reacted to generate sediment, the generated sediment is centrifuged and washed for 3 times, then 120ml of deionized water without carbon dioxide is added to prepare slurry, 0.0593g (0.25mmol) of 1,2,2,6, 6-pentamethylpiperidine-4-oxyl sodium acetate and 0.04g (0.25mmol) of sodium salicylate are respectively weighed and added into the slurry, then the sediment is placed in a water bath at 95 ℃ to react for 15 hours, the reaction product is centrifuged and washed for 6 times after the reaction is finished, the product obtained by centrifugation is placed in an oven at 80 ℃ to be dried for 22 hours, and the light stabilizer [ Mg with the supermolecular intercalation structure ] is obtained0.66Al0.34(OH)2](C12H22O3N)0.11(C7H5O3)0.23·0.6H2O。
Example 3:
step A: 3g (10.0mmol) Mg (NO) are weighed3)2 .6H2O、0.938g(2.5mmol)Al(NO3)3 .9H2O, dissolving in 45ml to remove CO2Preparing a salt solution in the deionized water.
And B: 1g NaOH is weighed and dissolved in 25ml deionized water without carbon dioxide to prepare an alkali solution. 1.175g (5mmol) of sodium 2,2,6, 6-tetramethylpiperidine-4-aminopropionate and 0.3978g (2.5mmol) of sodium p-aminobenzoate were weighed out and dissolved in a mixed solvent of deionized water and ethylene glycol except for carbon dioxide, and added to an alkali solution to form a mixed solution.
And C: under the protection of nitrogen and stirring, the solution prepared in the step A, B is mixed and reacted to generate sediment, the generated sediment is centrifugally washed for 3 times, then 120ml of deionized water without carbon dioxide is added to prepare serous fluid, 0.0588g (0.25mmol) of2, 2,6, 6-tetramethylpiperidine-4-aminopropionic acid sodium and 0.0398g (0.25mmol) of sodium p-aminobenzoate are respectively weighed and added into the serous fluid, then the sediment is placed in a water bath at 100 ℃ to react for 12 hours, after the reaction is finished, the reaction product is centrifuged and washed for 6 times, the product obtained by centrifugation is placed in a drying oven at 90 ℃ to be dried for 18 hours, and the light stabilizer [ Mg with the supermolecular intercalation structure ] is obtained0.66Al0.34(OH)2](C12H23O2N2)0.23(C7H6O2N)0.11·0.6H2O。
Example 4:
step A: 1.5g (5.0mmol) Mg (NO) are weighed3)2 .6H2O、0.938g(2.5mmol)Al(NO3)3 .9H2Dissolving the mixture in 30ml of deionized water for removing carbon dioxide to prepare a salt solution.
And B: weighing 0.6g of NaOH, dissolving in 35ml of deionized water without carbon dioxide to prepare an alkali solution; 1.7625g (7.5mmol) of 1,2,2,6, 6-pentamethylpiperidine-4-aminoacetic acid sodium and 0.465g (2.5mmol) of potassium cinnamate were weighed out and dissolved in a mixed solvent of deionized water and ethylene glycol except for carbon dioxide, and added to an alkali solution to form a mixed solution.
And C: under the protection of nitrogen and stirring, the solution prepared in the step A, B is mixed and reacted to generate sediment, the generated sediment is centrifuged and washed for 3 times, then 120ml of deionized water without carbon dioxide is added to prepare slurry, 0.0588g (0.25mmol) of 1,2,2,6, 6-pentamethylpiperidine-4-aminoacetic acetate and 0.0465g (0.25mmol) of potassium cinnamate are respectively weighed and added into the slurry, then the sediment is placed in a water bath at 90 ℃ to react for 10 hours, after the reaction is finished, the reaction product is centrifuged and washed for 6 times, the product obtained by centrifugation is placed in a drying oven at 100 ℃ to be dried for 20 hours, and the light stabilizer [ Mg with the supermolecular intercalation structure ] is obtained0.66Al0.34(OH)2](C12H23O2N2)0.25(C9H7O2)0.09·0.6H2O。
Example 5:
step A: 2.25g (7.5mmol) Mg (NO) are weighed3)2 .6H2O、0.938g(2.5mmol)Al(NO3)3 .9H2Dissolving the mixture in 30ml of deionized water for removing carbon dioxide to prepare a salt solution.
And B: weighing 0.8g (20mmol) of NaOH and dissolving in 40ml of deionized water without carbon dioxide to prepare an alkali solution; 0.6805g (2.5mmol) of sodium 2,2,6, 6-tetramethylpiperidine-4-propoxysulfonate and 0.8258g (2.5mmol) of sodium phenylbenzimidazole sulfonate were weighed out and dissolved in deionized water with carbon dioxide removed, and added to an alkali solution to form a mixed solution.
And C: under the protection of nitrogen and stirring, the solution prepared in the step A, B is mixed and reacted to generate precipitate, the generated precipitate is centrifuged and washed for 3 times, then 120ml of deionized water with carbon dioxide removed is added to prepare slurry, 0.0681g (0.25mmol) of2, 2,6, 6-tetramethylpiperidine-4-propoxysulfonate and 0.0826g (0.25mmol) of phenylbenzimidazole sodium sulfonate are respectively weighed and added into the slurry, then the precipitate is placed in a water bath at 95 ℃ to react for 9 hours, after the reaction is finished, the reaction product is centrifuged and washed for 6 times, the product obtained by centrifugation is placed in a drying oven at 90 ℃ to be dried for 24 hours, and the light stabilizer [ Mg with the supermolecular intercalation structure ] is obtained0.66Al0.34(OH)2](C12H24O4NS)0.17(C13H9N2O3S)0.17·0.6H2O。
Claims (2)
1. A preparation method of a supramolecular intercalation structure light stabilizer comprises the following specific steps:
A. weighing M2+、M3+Dissolving nitrate or chloride in deionized water to obtain mixed salt solution A, wherein M is2+And M3+In a molar ratio of2 to 4, M3+The molar concentration of (A) is 0.05-0.8 mol/L;
wherein M is2+Is Mg2+、Zn2+、Ni2+、Ca2+、Fe2+、Cu2+Either one or both of; m3+Is Al3+、Co3+、Ti3+、Fe3 +、Cr3+One or two of trivalent metal cations;
B. preparing an alkali solution with the molar concentration of 0.05-1 mol/L, wherein the alkali is NaOH, KOH or ammonia water, and the molar amount of the alkali is M in the solution in the step A2+And M3+1.8-2.5 times of the sum of the molar weight;
according to the mole ratio of 0.025-39 of ultraviolet absorbent and free radical trapping agent, the two raw materials are dissolved in solvent to prepare the total mole concentration of0.05-0.5 mol/L solution is added into the alkali solution to form a mixed solution B, wherein the sum of the molar weight of the ultraviolet absorbent and the free radical trapping agent and the M in the solution A3+The ratio of the sum of the molar weights is 1 to 3; the solvent is deionized water without carbon dioxide or a mixed solvent of the deionized water and a polar solvent, the polar solvent is ethanol, glycol or glycerol, and the corresponding solvent is selected according to the ultraviolet absorbent and the free radical trapping agent which can be used for dissolving;
the free radical trapping agent is a tetramethylpiperidine compound, and the chemical formula of the free radical trapping agent is shown as the following formula:
in the formula R1Is H or CH3；R2Is O-R3-COONa、NH-R3-COONa、O-R3-SO3Na or NH-R3-SO3Na wherein R3Is [ CH ]2]m[C6H4]nM is an integer between 1 and 8, n is 0 or 1;
the ultraviolet absorbent is one or more of sodium p-aminobenzoate, sodium p-methoxycinnamate, sodium salicylate, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, sodium coumarin-3-carboxylate, sodium cinnamate, sodium benzotriazole-4-hydroxy-benzenesulfonate and sodium 2-phenylbenzimidazole-5-sulfonate;
C. under the protection of nitrogen and stirring, mixing the mixed salt solution A and the mixed solution B to react to generate precipitate, centrifugally washing the generated precipitate for 3 times, preparing slurry with solid content of 1-100 g/L by using water, and adding an ultraviolet absorbent and a free radical trapping agent, wherein the addition amount of the ultraviolet absorbent and the free radical trapping agent is M in the slurry3+0.1-0.3 times of the molar weight, then stirring and reacting for 4-24 hours at 50-150 ℃, cooling, filtering the product and washing for 4-9 times, drying the filter cake for 12-24 hours at 60-100 ℃ to obtain the supermolecular intercalation structure light stabilizer, wherein the chemical general formula is as follows:
[M2+ 1-xM3+ x(OH)2](A-)y(B-)z·cH2O
wherein x is y + z, x is more than or equal to 0.2 and less than or equal to 0.4, y is more than 0.01 and less than 0.39, z is more than 0.01 and less than 0.39, c is the number of interlayer water molecules, and c is more than 0.4 and less than 1;
M2+is Mg2+、Zn2+、Ni2+、Ca2+、Fe2+、Cu2+Either one or both of; m3+Is Al3+、Co3+、Ti3+、Fe3+、Cr3+One or two of them; a. the-Being an anion of a radical scavenger, B-Is an ultraviolet absorber anion.
2. The method for preparing supramolecular intercalated structure light stabilizer according to claim 1, wherein M is selected from the group consisting of2+Is Mg2+、Zn2+One of (1), M3+Is Al3+。
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