CN101817937A - Supermolecular structural 5,5'-sulfenyl disalicylic acid intercalation ultraviolet absorbing material and preparation method thereof - Google Patents
Supermolecular structural 5,5'-sulfenyl disalicylic acid intercalation ultraviolet absorbing material and preparation method thereof Download PDFInfo
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Abstract
The invention provides a supermolecular structural 5,5'-sulfenyl disalicylic acid intercalation ultraviolet absorbing material and a preparation method thereof. The supermolecular structural 5,5'-sulfenyl disalicylic acid intercalation material is abbreviated as ZnAl-TDSA-LDHs and has the molecular formula of [Zn2+1-xAl3+x(OH)2]x+(C14H8O6S)2-x/2.mH2O. The preparation method of the ultraviolet absorbing material comprises the following steps of: intercalating 5,5'-sulfenyl disalicylic acid among ZnAl-NO3-LDHs layers by using houghite ZnAl-NO3-LDHs as a precursor and adopting an ion exchange method, and assembling to obtain the ZnAl-TDSA-LDHs with good crystalline phase structure and excellent performance. The ZnAl-TDSA-LDHs material has the ultraviolet absorptivity of over 80 percent within the wave band range of 250-400 nm, has excellent ultraviolet absorbing capacity, and is a good ultraviolet absorbing material. The material begins the combustion decomposition of anions among layers at the temperature of 330 DEG C, reaches the peak temperature of an exothermic peak at the temperature of 430 DEG C, has high thermal stability performance, and is an excellent photo-thermal stabilizing agent. The capability of resisting ultraviolet degradation can be greatly improved by adding the ZnAl-TDSA-LDHs into polymeric materials such as polypropylene and the like.
Description
Technical field
The present invention relates to a kind of supramolecular structure 5,5 '-sulfenyl salicyl salicylic acid diplosal intercalation ultraviolet absorption material and preparation method thereof.
Background technology
Environmental pollution brings ultraviolet increasing considerably, because of photochemical effect and biological effect that ultraviolet ray produced very remarkable, cause that other high molecular polymers of Polyolefin and are aging, cause its performance to reduce, material becomes fragile, finally lose physical strength, therefore be necessary to study uvioresistant additive efficiently.5,5 '-English name of sulfenyl salicyl salicylic acid diplosal is 5,5 '-Thiodisalicylic acid, be abbreviated as TDSA, have the good absorption performance at 250～370nm wave band, outward appearance is a buff powder, be slightly soluble in water under the room temperature, soluble in water behind the one-tenth sodium salt, generate colored complex with the metal ion reaction, therefore be used for the ion check more.TDSA high temperature easily decomposes down, and resistant to extraction and water-wash resistance are all relatively poor in matrix material, make its range of application and result of use be subjected to great restriction.
Hydrotalcite (Layered Double Hydroxides is abbreviated as LDHs) is the important novel inorganic functional materials of a class, and particularly in recent years, hydrotalcite is having new application aspect plastics additive, the auxiliary agent.Intercalation assembling performance and the favorable photo-thermal stability of utilizing hydrotalcite to have have very high using value with it as plastics additive or carrier.Therefore, utilize the ion exchange property of hydrotalcite, TDSA is inserted into the thermostability that hydrotalcite layers can increase substantially TDSA,, can prepare the compound uv-absorbing agent of organic/inorganic of good heat stability in conjunction with the uv absorption property of TDSA itself.After the TDSA negatively charged ion enters the LDHs interlayer, LDHs plays the effect of " molecule container ", TDSA ion and laminate interact make the carboxylic acid group can not be directly and metal or plastics have an effect, the uv absorption property that the ultraviolet shielded and TDSA self structure of combination water talcum laminate itself is determined, show that by experiment this kind novel material can be used as photostabilizer and is applied in the polyolefine.
Document [1] Dianqing Li, Zhenjun Tuo, David G.Evans, Xue Duan*.Preparation of5-benzotriazolyl-4-hydroxy-3-sec-butylbenzenesulfonate anion-pillared layered doublehydroxide and its photostabilizing effect on polypropylene.Journal of Solid State Chemistry, 2006,179, among the 3114-3120 5-benzotriazole base-4-hydroxyl-3-isobutyl-benzene sulfonic acid is successfully inserted hydrotalcite layers, pass through electrostatic force, covalent linkage and hydrogen bond etc. interact between main body laminate and object organic ion, under the prerequisite that original UV absorbing properties does not influence, inorganic laminate performance intercepts action of ultraviolet radiation, has improved its thermostability greatly.
Document [2] Chai, H.; Lin, Y.J.; Evans, D.G.; Li, D.Q.Synthesis and UV AbsorptionProperties of 2-Naphthylamine-1.5-disulfonic Acid Intercalated Zn-Al Layered DoubleHydroxide.Ind.Eng.Chem.Res.2008,47, among the 2855-1860 with 2-naphthylamines-1,5-disulfonic acid intercalation ZnAl-LDHs, obtain have the intercalation product of excellent uv absorption property and thermal stability, and be successfully applied in the polypropylene, obtain good anti-photooxidation resistance effect.
Document [3] Hao Chai, Xiangyu Xu, Yanjun Lin, David G.Evans, Dianqing Li*.Synthesisand UV absorption properties of 2,3-dihydroxynaphthalene-6-sulfonate anion-intercalatedZn-Al layered double hydroxides.Polym.Degrad.Stab.2009,94, prepared 2 among the 744-749,3-dihydroxyl-6-sulfonic acid intercalation hydrotalcite, the uv absorption property and the thermal stability of product are significantly improved.
Document [4] Cui, G.J.; Xu, X.Y.; Lin, Y.J.; Evans, D.G.; Li, D.Q.Synthesis and UVAbsorption Properties of 5,5 '-Methylenedisalicylic Acid-Intercalated Zn-Al LayeredDouble Hydroxides Ind.Eng.Chem.Res.2010,49, be precursor with zinc-aluminium nitrate radical hydrotalcite among the 448-453, to remove CO
2Deionized water be dispersion medium, prepare collection shielding and absorb the novel inorganic functional materials of dual-use function with ion-exchange techniques.
Summary of the invention
The purpose of this invention is to provide a kind of supramolecular structure 5,5 '-sulfenyl salicyl salicylic acid diplosal intercalation ultraviolet absorption material; Another object of the present invention provide this kind supramolecular structure 5,5 '-preparation method of sulfenyl salicyl salicylic acid diplosal intercalation ultraviolet absorption material.
The interlayer anion of ZnAl-TDSA-LDHs begins to decompose when temperature is 330 ℃, reaches the peak temperature of exothermic peak in the time of 430 ℃; Its uv-absorbing rate to 250～330nm wave band surpasses 80%, and the maximal ultraviolet absorption peak appears at 320～400nm place, specific absorption 85～90%.
A. with hydrotalcite LDHs precursor and except that CO
2Deionized water add in the reactor that band stirs and fully mix the suspension that compound concentration is 0.05～0.1mol/L;
The structural formula of used LDHs precursor is [Zn
2+ 1-xAl
3+ x(OH)
2]
X+(NO
3 -)
xMH
2O, wherein Zn
2+/ Al
3+Mol ratio is 2～3: 1; The value of x changes with mole number, 0≤x≤1, and m is an interlayer crystal water molecule number, 0.65≤m≤0.90.
B. with 5,5 '-sulfenyl salicyl salicylic acid diplosal (TDSA), be dissolved in except that CO
2Deionized water in be mixed with the aqueous solution that concentration is 0.025～0.2mol/L, adjusting the pH value of solution value with NaOH is 4～10, dissolves fully to TDSA;
C. in the ratio of negatively charged ion mole number in the described hydrotalcite precursor of TDSA negatively charged ion mole number and steps A 1～6: 1 ratio; TDSA solution is joined short mix in the reactor of steps A; under nitrogen protection; stir fast; crystallization is 6～18 hours under 60～100 ℃ of temperature; filter, washing, drying obtains the hydrotalcite of ZnAl-TDSA-LDHs intercalation.
The intercalated houghite that obtains has been carried out following sign:, show that the TDSA negatively charged ion has been assembled into hydrotalcite layers by X-ray powder diffraction (XRD), infrared (IR), elemental analysis.To its thermogravimetric differential thermal analysis (TG-DTA) of carrying out the results are shown in Figure 1, Fig. 2, the result shows that the temperature of initial decomposition of its intercalation product is 330 ℃, has improved 115 ℃ for 245 ℃ than the temperature of initial decomposition of TDSA.See Fig. 3 with the ultraviolet absorption curve that the UV, visible light analytical procedure is measured, by Fig. 3 find out its to the uv-absorbing rate of 250～400nm wave band all above 80%.
Reaching this uv-absorbing material not, the TDSA of intercalation is well-dispersed in the polypropylene (PP) by mixing, and make TDSA/PP, ZnAl-TDSA-LDHs/PP and pure PP sample film, be the ultraviolet ageing contrast experiment, by measuring three's infrared spectrum, compared hydroxyl peak (see figure 4) and the carbonyl peak (see figure 5) of representing polypropylene photooxidation droping degree, found that TDSA intercalated houghite uv-absorbing material can obviously improve polyacrylic ageing resistance by ultraviolet light performance.
The invention has the beneficial effects as follows:
First intercalation prepared interlayer anion be 5,5 of divalence '-hydrotalcite material of sulfenyl salicyl salicylic acid diplosal radical ion;
2. this kind intercalation ultraviolet absorption material all above 80%, has good uv absorption property to the uv-absorbing rate of 250～400nm wave band, has expanded the scope of UV light absorber.
3. the Heat stability is good of this kind intercalation material, temperature of initial decomposition has been brought up to 330 ℃, and very strong thermal stability is arranged.
4. as polyacrylic additive the photodegradative ability of its uvioresistant is increased substantially with ZnAl-TDSA-LDHs.
Description of drawings
Fig. 1 is the TG-DTA curve of embodiment TDSA.
Fig. 2 is the TG-DTA curve of ZnAl-TDSA-LDHs.
Fig. 3 is the ultraviolet absorption curve of sample, and wherein: a is ZnAl-NO
3The ultraviolet absorption curve of-LDHs, b are the ultraviolet absorption curves of TDSA, and c is the ultraviolet absorption curve of ZnAl-TDSA-LDHs.
Fig. 4 is that the hydroxyl peak intensity of the PP film of the PP film that added TDSA, ZnAl-TDSA-LDHs and pure PP film is with the ultra violet lamp time variation diagram.
Fig. 5 is that the carbonyl peak intensity of the PP film of the PP film that added TDSA, ZnAl-TDSA-LDHs and pure PP film is with the ultra violet lamp time variation diagram.
Annotate: specimen and interpolation sample used among Fig. 1-5 are all taken from embodiment 1.
Embodiment
Embodiment 1
Steps A: with the solid Al (NO of 45.00g (0.12mol)
3)
39H
2Solid Zn (the NO of O and 71.39g (0.24mol)
3)
26H
2O is dissolved in except that CO
2Deionized water in, be mixed with the 300mL mixing salt solution; Take by weighing the NaOH of 28.8g (0.72mol), be dissolved in except that CO
2Deionized water in, be mixed with the 300mL alkaline solution; Under the room temperature two kinds of solution are added quick nucleation in the rotation liquid film reactor with identical flow velocity, the slurries that obtain are moved to 100 ℃ of crystallization 6h of 1000mL flask, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to the pH of washing water, obtain ZnAl-NO
3-LDHs, its Zn
2+/ Al
3+=2: 1.
Getting above-mentioned filter cake 6.21g (0.005mol) uses except that CO in four-hole boiling flask
2The deionized water ultra-sonic dispersion, be mixed with 75mL suspension.
Step B: take by weighing 0.54g (0.0018mol) TDSA and 0.144g NaOH (0.0036mol), make NO
3 -With object TDSA ion ratio be 1: 1, be dissolved in 75mL and remove CO
2Deionized water in, fast agitation condition adds appropriate amount of NaOH down to adjust pH value is 7.01, prepares the aqueous solution of TDSA.
Step C: under nitrogen protection, the solution with step B preparation joins in the precursor slurry of steps A preparation rapidly, and at 100 ℃ of following crystallization 6h, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to pH, obtain TDSA intercalation configuration uv-absorbing material ZnAl-TDSA-LDHs.
The intercalated houghite that obtains is carried out signs such as XRD, IR, ultimate analysis, and to draw its chemical formula be Zn
0.65Al
0.35(OH)
2(TDSA)
0.180.67H
2O.
The initial decomposition temperature of ZnAl-TDSA-LDHs is 330 ℃, and its strongest ultraviolet absorption peak appears at 320～400nm place, specific absorption 85～90%.
Embodiment 2
Steps A: preparation ZnAl-NO
3-LDHs precursor slurry, method is identical with steps A among the embodiment 1.
Step B: take by weighing 1.92g (0.0072mo1) TDSA and 0.56g NaOH (0.014mol), make NO
3 -With object TDSA ion ratio be 1: 4, be dissolved in 75mL and remove CO
2Deionized water in, fast agitation condition adds appropriate amount of NaOH down to adjust pH value is 10.03, prepares the aqueous solution of TDSA.
Step C: under nitrogen protection, the solution with step B preparation joins in the precursor slurry of steps A preparation rapidly, and at 80 ℃ of following crystallization 12h, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to pH, obtain TDSA intercalation configuration uv-absorbing material ZnAl-TDSA-LDHs.
The intercalated houghite that obtains is carried out signs such as XRD, IR, ultimate analysis, and to draw its chemical formula be Zn
0.65Al
0.35(OH)
2(TDSA)
0.150.75H
2O.
The initial decomposition temperature of ZnAl-TDSA-LDHs is 335 ℃, and its strongest ultraviolet absorption peak appears at 335～390nm place, specific absorption 85～90%.
Embodiment 3
Steps A: preparation ZnAl-NO
3-LDHs precursor slurry, method is identical with steps A among the embodiment 1.
Step B: take by weighing 3.24g (0.011mol) TDSA and 0.88g NaOH (0.022mol), make NO
3 -With object TDSA ion ratio be 1: 6, be dissolved in 75mL and remove CO
2Deionized water in, fast agitation condition adds appropriate amount of NaOH down to adjust pH value is 4.12, prepares the aqueous solution of TDSA.
Step C: under nitrogen protection, the solution with step B preparation joins in the precursor slurry of steps A preparation rapidly, and at 90 ℃ of following crystallization 10h, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to pH, obtain TDSA intercalation configuration uv-absorbing material ZnAl-TDSA-LDHs.
The intercalated houghite that obtains is carried out signs such as XRD, IR, ultimate analysis, and to draw its chemical formula be Zn
0.65Al
0.35(OH)
2(TDSA)
0.160.68H
2O.
The initial decomposition temperature of ZnAl-TDSA-LDHs is 332 ℃, and its strongest ultraviolet absorption peak appears at 330～385nm place, specific absorption 85～90%.
Embodiment 4
Steps A: with the solid Al (NO of 30.01g (0.08mol)
3)
39H
2Solid Zn (the NO of O and 71.39g (0.24mol)
3)
26H
2O is dissolved in except that CO
2Deionized water in, be mixed with the 300mL mixing salt solution; Take by weighing the NaOH of 20.48g (0.51mol), be dissolved in except that CO
2Deionized water in, be mixed with the 300mL alkaline solution; Under the room temperature two kinds of solution are added quick nucleation in the rotation liquid film reactor with identical flow velocity, the slurries that obtain are moved to 100 ℃ of crystallization 6h of 1000mL flask, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to the pH of washing water, obtain ZnAl-NO
3-LDHs, wherein Zn
2+/ Al
3+=3: 1.
Getting above-mentioned filter cake 8.88g (0.0072mol) uses except that CO in four-hole boiling flask
2The deionized water ultra-sonic dispersion, be mixed with 75mL suspension.
Step B: take by weighing 1.10g (0.0036mol) TDSA and 0.288g NaOH (0.0072mol), make NO
3 -With object TDSA ion ratio be 1: 2, be dissolved in 75mL and remove CO
2Deionized water in, fast agitation condition adds appropriate amount of NaOH down to adjust pH value is 7.10, prepares the aqueous solution of TDSA.
Step C: under nitrogen protection, the solution with step B preparation joins in the precursor slurry of steps A preparation rapidly, and at 60 ℃ of following crystallization 18h, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to pH, obtain TDSA intercalation configuration uv-absorbing material ZnAl-TDSA-LDHs.
The intercalated houghite that obtains is carried out signs such as XRD, IR, ultimate analysis, and to draw its chemical formula be Zn
0.75Al
0.25(OH)
2(TDSA)
0.130.83H
2O.
The initial decomposition temperature of ZnAl-TDSA-LDHs is 330 ℃, and its strongest ultraviolet absorption peak appears at 320～400nm place, specific absorption 85～90%.
Steps A: preparation ZnAl-NO
3-LDHs precursor slurry, method is identical with steps A among the embodiment 4.
Step B: take by weighing 1.65g (0.0054mol) TDSA and 0.44g NaOH (0.011mol), make NO
3 -With object TDSA ion ratio be 1: 3, be dissolved in 75mL and remove CO
2Deionized water in, fast agitation condition adds appropriate amount of NaOH down to adjust pH value is 9.98, prepares the aqueous solution of TDSA.
Step C: under nitrogen protection, the solution with step B preparation joins in the precursor slurry of steps A preparation rapidly, and at 80 ℃ of following crystallization 12h, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to pH, obtain TDSA intercalation configuration uv-absorbing material ZnAl-TDSA-LDHs.
The intercalated houghite that obtains is carried out signs such as XRD, IR, ultimate analysis, and to draw its chemical formula be Zn
0.75Al
0.25(OH)
2(TDSA)
0.130.85H
2O.
The initial decomposition temperature of ZnAl-TDSA-LDHs is 330 ℃, and its strongest ultraviolet absorption peak appears at 330～400nm place, specific absorption 85～90%.
Embodiment 6
Steps A: preparation ZnAl-NO
3-LDHs precursor slurry, method is identical with steps A among the embodiment 4.
Step B: take by weighing 2.75g (0.009mol) TDSA and 0.72g NaOH (0.018mol), make NO
3 -With object TDSA ion ratio be 1: 5, be dissolved in 75mL and remove CO
2Deionized water in, fast agitation condition adds appropriate amount of NaOH down to adjust pH value is 4.45, prepares the aqueous solution of TDSA.
Step C: under nitrogen protection, the solution with step B preparation joins in the precursor slurry of steps A preparation rapidly, and at 90 ℃ of following crystallization 10h, centrifugation is with removing CO
2Deionized water wash be about 7,70 ℃ of dry 24h to pH, obtain TDSA intercalation configuration uv-absorbing material ZnAl-TDSA-LDHs.
The intercalated houghite that obtains is carried out signs such as XRD, IR, ultimate analysis, and to draw its chemical formula be Zn
0.75Al
0.25(OH)
2(TDSA)
0.130.83H
2O.
The initial decomposition temperature of ZnAl-TDSA-LDHs is 370 ℃, and its strongest ultraviolet absorption peak appears at 350～370nm place, specific absorption 85～90%.
Claims (3)
- A supramolecular structure 5,5 '-sulfenyl salicyl salicylic acid diplosal intercalation ultraviolet absorption material, be called for short ZnAl-TDSA-LDHs, its molecular formula is [Zn 2+ 1-xAl 3+ x(OH) 2] X+(C 14H 8O 6S) 2- X/2MH 2O, wherein Zn 2+/ Al 3+Mol ratio is 2～3: 1, and the value of x changes with mole number, 0≤x≤1, and m is an interlayer crystal water molecule number, 0.65≤m≤0.90.
- 2. supramolecular structure 5,5 according to claim 1 '-sulfenyl salicyl salicylic acid diplosal intercalation ultraviolet absorption material, it is characterized in that the interlayer anion of ZnAl-TDSA-LDHs begins to decompose when temperature is 330 ℃, reach the peak temperature of exothermic peak in the time of 430 ℃; All above 80%, the maximal ultraviolet absorption peak appears at 320～400nm place to the uv-absorbing rate of 250～400nm wave band for it, and specific absorption is 85～90%.
- A preparation supramolecular structure 5,5 as claimed in claim 1 '-method of sulfenyl salicyl salicylic acid diplosal intercalation ultraviolet absorption material, concrete preparation process is as follows:A. with the hydrotalcite precursor and except that CO 2Deionized water add in the reactor that band stirs and fully mix the suspension that compound concentration is 0.05～0.1mol/L;The structural formula of used hydrotalcite precursor is [Zn 2+ 1-xAl 3+ x(OH) 2] X+(NO 3 -) xMH 2O, wherein Zn 2+/ Al 3+Mol ratio is 2～3: 1; The value of x changes with mole number, 0≤x≤1, and m is an interlayer crystal water molecule number, 0.65≤m≤0.90.B. with 5,5 '-sulfenyl salicyl salicylic acid diplosal TDSA, be dissolved in except that CO 2Deionized water in be mixed with the aqueous solution that concentration is 0.025～0.2mol/L, adjusting the pH value of solution value with NaOH is 4～10, dissolves fully to TDSA;C. in the ratio of negatively charged ion mole number in the described hydrotalcite precursor of TDSA negatively charged ion mole number and steps A 1～6: 1 ratio; TDSA solution is joined short mix in the reactor of steps A; under nitrogen protection; stir fast; crystallization is 6～18 hours under 60～100 ℃ of temperature; filter, washing, drying obtains ZnAl-TDSA-LDHs.
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Cited By (2)
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|---|---|---|---|---|
| CN104761750A (en) * | 2015-03-24 | 2015-07-08 | 北京化工大学 | Supermolecular structure p-nitrophenol or isomer intercalation ultraviolet barrier material thereof and preparation method thereof |
| CN108193552A (en) * | 2017-12-07 | 2018-06-22 | 常州市沃兰特电子有限公司 | A kind of preparation method of water solubility paper fibre light stabilizer |
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| CN101173118A (en) * | 2007-11-09 | 2008-05-07 | 北京化工大学 | Supramolecular structured 2-naphthylamine-1,5-disulfonic acid intercalation ultraviolet absorption material and method for producing the same |
| CN101544782A (en) * | 2009-05-15 | 2009-09-30 | 北京化工大学 | Supermolecular structural 5,5'-methylene disalicylic acid intercalation ultraviolet absorption material and preparation method thereof |
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2010
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| CN1318595A (en) * | 2000-04-17 | 2001-10-24 | 北京化工大学 | Composite oganic-inorganic selective ultraviolet blocking material and its preparation |
| CN101173118A (en) * | 2007-11-09 | 2008-05-07 | 北京化工大学 | Supramolecular structured 2-naphthylamine-1,5-disulfonic acid intercalation ultraviolet absorption material and method for producing the same |
| CN101544782A (en) * | 2009-05-15 | 2009-09-30 | 北京化工大学 | Supermolecular structural 5,5'-methylene disalicylic acid intercalation ultraviolet absorption material and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104761750A (en) * | 2015-03-24 | 2015-07-08 | 北京化工大学 | Supermolecular structure p-nitrophenol or isomer intercalation ultraviolet barrier material thereof and preparation method thereof |
| CN104761750B (en) * | 2015-03-24 | 2017-07-04 | 北京化工大学 | A kind of supramolecular structure p-nitrophenol or its isomers intercalation ultraviolet blocking material and preparation method thereof |
| CN108193552A (en) * | 2017-12-07 | 2018-06-22 | 常州市沃兰特电子有限公司 | A kind of preparation method of water solubility paper fibre light stabilizer |
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