CN107629310A - A kind of supermolecular intercalation structure light stabilizer and preparation method thereof - Google Patents
A kind of supermolecular intercalation structure light stabilizer and preparation method thereof Download PDFInfo
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Abstract
The invention provides a kind of supermolecular intercalation structure light stabilizer and preparation method thereof.Ultraviolet absorber and radical scavenger are innovatively assembled to LDHs interlayers by the present invention jointly, using light degradation of the uv absorption property barrier ultraviolet of ultraviolet absorber to plastics, the photooxidation of plastics is reduced using living radical caused by radical scavenger capture light degradation.Because collaboration anti-light aging effect be present in the ultraviolet absorber and radical scavenger of LDHs interlayers, the anti-light aging performance of ultraviolet absorber and the common intercalation configuration LDHs of radical scavenger is substantially better than ultraviolet absorber list intercalation LDHs, overcomes the shortcomings that current ultraviolet absorber list intercalation LDHs anti-light agings are ineffective.Preparation method of the present invention is simple, raw material sources enrich, is easy to the advantages of industrialized production.Prepared supermolecular intercalation structure light stabilizer has the advantages that heat resistance is high, resistance to migration is good, light-protection energy is excellent, can be widely applied to the fields such as plastics, coating.
Description
Art
The present invention relates to a kind of supermolecular intercalation structure light stabilizer and preparation method thereof.
Background technology
Light stabilizer is that one kind can suppress the UV light-induced function additive for causing plastic degradation, and its action principle is mainly
The purpose of light protection is realized by absorbing and shifting UV energy, shielding ultraviolet light or capture free radical.Light stabilizer one
As it is compound with plastics in a manner of physical mixed, and be highly dispersed in plastic substrate with give full play to the protection of light stabilizer effect
Fruit, the photooxidative degradation of plastics is reduced, reach the purpose for extending plastics service life.But most of light stabilizer, which exists, easily to be waved
The shortcomings of sending out, be easy to migrate, heat endurance is poor, limits its application.
Hydrotalcite (Layered Double Hydroxides, be abbreviated as LDHs) is by positively charged metal hydroxide
Nitride layer plate is connected the compound formed with negatively charged interlayer anion with weak chemical bond, its main layer board metallic element
Composition, main layer board charge density and distribution, interlayer object anion species and quantity, host-guest interaction etc. all have can
The characteristic of modulation, therefore the characteristic can be utilized in hydrotalcite layers insertions function anion, so as to be prepared with special
The functional material of property.
Document Chai H, Xu X, Lin Y, et al.Synthesis and UV absorption properties of
2, 3-dihydroxynaphthalene-6-sulfonate anion-intercalated Zn–Al layered double
hydroxides[J]. Polymer Degradation and stability,2009,94(4):744-749 is with ZnAl-
NO3- LDH is presoma, using ion-exchange by ultraviolet absorber 2- alpha naphthylamines -1,5- disulfonic acid (NADA) success intercalation group
ZnAl-LDH interlayers are attached to, construct supermolecular intercalation structure ZnAl-NADA-LDH UV absorbing materials；By ZnAl-NADA-LDH
With the compound preparation LDH/PP composites of polypropylene (PP), ultra-violet analysis finds that the UV absorption of LDH/PP laminated films is substantially high
In PP films, light aging test result shows, LDH introducing improves PP photostability.
Document Chai H, Lin Y, Evans D G, et al.Synthesis and UV absorption
properties of 2-naphthylamine-1,5-disulfonic acid intercalated Zn-Al layered
double hydroxides[J].Industrial& Engineering Chemistry Research,2008,47(9):
2855-2860 is using ZnAl-LDH as presoma, using ion-exchange by ultraviolet absorber 2,3- dihydroxy naphthlene -6- sulfonic acid
(DNSA) success intercalation is assembled into ZnAl-LDH interlayers, constructs supermolecular intercalation structure ZnAl-DNSA-LDH UV absorbing materials；
By ZnAl-DNSA-LDH and the compound preparation LDH/PP composites of PP, ultra-violet analysis finds the ultraviolet suction of LDH/PP laminated films
Receipts show that LDH introducing slow down PP light aging speed apparently higher than PP films, light aging test result.
Document Cui G-J, Xu X-Y, Lin Y-J, et al.Synthesis and UV Absorption
Properties of 5, 5′-Methylenedisalicylic Acid-Intercalated Zn-Al Layered
Double Hydroxides[J].Industrial& Engineering Chemistry Research,2009,49(2):
448-453 is assembled 5,5 '-methylenesalicylic (MDSA) success intercalation using ZnAl-LDH as presoma, using ion-exchange
To ZnAl-LDH interlayers, supermolecular intercalation structure ZnAl-MDSA-LDH UV absorbing materials, light aging test result table are constructed
Bright, LDH introducing slow down PP light aging speed.
Although above-mentioned document is prepared for a variety of supermolecular intercalation structure light stabilizers, its light protective capability to PP has
Limit, PP still can slowly degrade in use.For further lifting PP light stability, it is badly in need of a kind of performance more
Excellent light stabilizer.
The content of the invention
It is an object of the invention to provide a kind of supermolecular intercalation structure light stabilizer and preparation method thereof.
Ultraviolet absorber and radical scavenger are innovatively assembled to LDHs interlayers by the present invention jointly, utilize ultraviolet suction
Light degradation of the uv absorption property barrier ultraviolet of agent to plastics is received, is lived using caused by radical scavenger capture light degradation
Free love base reduces the photooxidation of plastics.Because the ultraviolet absorber and radical scavenger of LDHs interlayers are anti-light old in the presence of cooperateing with
Change acts on, and the anti-light aging performance of ultraviolet absorber and the common intercalation configuration LDHs of radical scavenger is substantially better than ultraviolet absorber
Single intercalation LDHs, overcome the shortcomings that current ultraviolet absorber list intercalation LDHs anti-light agings are ineffective.
The chemical general formula of supermolecular intercalation structure light stabilizer prepared by the present invention is：
[M2+ 1-xM3+ x(OH)2](A-)y(B-)z·cH2O
Wherein M2+And M3+Divalence and trivalent metal cation respectively in main layer board, M2+For Mg2+、Zn2+、
Ni2+、Ca2+、Fe2+、Cu2+In any one or two kinds, preferably Mg2+、Zn2+In one kind, M3+For Al3+、Co3+、 Ti3 +、Fe3+、Cr3+Deng one or both of trivalent metal cation, preferably Al3+；A-For radical scavenger A it is cloudy from
Son, B-For ultraviolet absorber anion；X is M3+/(M2++M3+) molar ratio, x=y+z (0.2≤x≤0.4,0.01<y <
0.39,0.01<z<0.39)；C is intermediary water Molecules, 0.4<c<1.
Described radical scavenger is tetramethyl piperidine class compound, and its chemical formula is shown below：
R in formula1For H or CH3；R2For O-R3-COONa、N-R3-COONa、O-R3-SO3Na or O-R3-SO3Na, wherein R3For
[CH2]m[C6H6]n, integers of the m between 1-8, n=0 or 1.
Described ultraviolet absorber is para aminobenzoic acid sodium salt, p- methoxy cinnamic acid sodium, sodium salicylate, 2- hydroxyls -4-
Methoxy benzophenone -5- sodium sulfonates, coumarin-3-carboxy acid's sodium, sodium cinnamate, BTA -4- hydroxyls-benzene sulfonic acid sodium salt, 2-
One or more in phenylbenzimidazol -5- sodium sulfonates.
Supermolecular intercalation structure light stabilizer of the present invention, specific preparation process are as described below.
A. M is weighed2+、M3+Nitrate or chlorate be dissolved in the deionized water of removing carbon dioxide that to be configured to salt-mixture molten
Liquid, wherein M2+With M3+Mol ratio be 2-4, M3+Molar concentration be 0.05-0.8mol/L.
Described M2+For Mg2+、Zn2+、Ni2+、Ca2+、Fe2+、Cu2+In any one or two kinds, preferably Mg2+、
Zn2+In one kind, M3+For Al3+、Co3+、Ti3+、Fe3+、Cr3+Deng one or both of trivalent metal cation, preferably
Al3+；
B. the aqueous slkali that molar concentration is 0.05-1mol/L is prepared, described alkali is NaOH, KOH or ammoniacal liquor；Wherein alkali
Mole is M in step solution A2+With M3+1.8-2.5 times of mole sum, i.e. nOH -=1.8-2.5 (nM 2++nM 3+)；
It is according to the ratio that the molar ratio of ultraviolet absorber and radical scavenger is 0.025-39, both raw materials are molten
The solution that total mol concentration is 0.05-0.5mol/L is made into solvent, is added in above-mentioned aqueous slkali and forms mixed solution B；
Wherein the mole sum of ultraviolet absorber and radical scavenger and M in solution A3+The ratio of mole sum is 1-3, i.e. nA
+nB=1-3 nM 3+；Described solvent is the deionized water or its mixed solvent with polar solvent of removing carbon dioxide, described
Polar solvent be ethanol, ethylene glycol or glycerine, selected according to ultraviolet absorber used and radical scavenger can be dissolved
With corresponding solvent.
Described radical scavenger is tetramethyl piperidine class compound, and its chemical formula is shown below：
R in formula1For H or CH3；R2For O-R3-COONa、N-R3-COONa、O-R3-SO3Na or N-R3-SO3Na, wherein R3For
[CH2]m[C6H6]n, integers of the m between 1-8, n=0 or 1；
Described ultraviolet absorber is para aminobenzoic acid sodium salt, p- methoxy cinnamic acid sodium, sodium salicylate, 2- hydroxyls -4-
Methoxy benzophenone -5- sodium sulfonates, coumarin-3-carboxy acid's sodium, sodium cinnamate, BTA -4- hydroxyls-benzene sulfonic acid sodium salt, 2-
One or more in phenylbenzimidazol -5- sodium sulfonates；
C. in the case where nitrogen is protected and is stirred, mixing salt solution A and mixed solution B is all mixed, reaction generation precipitation will
The pelleting centrifugation of generation washs 3 times, is then configured to the slurries that solid content is 1-100g/L with water；Add ultraviolet absorber with
Radical scavenger, wherein ultraviolet absorber, radical scavenger addition are M in slurries3+0.1-0.3 times of mole,
Then the stirring reaction 4-24 hours at 50-150 DEG C, cooling, filtration product are simultaneously washed 4-9 times, and filter cake is in 60-100 DEG C of drying
12-24 hours obtain a kind of supermolecular intercalation structure light stabilizer.
Fig. 1 and Fig. 2 is the XRD spectra of the supermolecular intercalation structure light stabilizer prepared by embodiment 1, and it is single to show that it has
One crystal phase structure and ultraviolet absorber and radical scavenger has successfully been assembled into LDHs interlayers.
Fig. 2 is the FT-IR spectrograms of the supermolecular intercalation structure light stabilizer prepared by embodiment 1, as a result shows ultraviolet suction
Receive agent and radical scavenger has successfully been assembled into LDHs interlayers.
Fig. 3 is light protecting effect figure of the supermolecular intercalation structure light stabilizer prepared by embodiment 1 to PP, can by Fig. 3
Know that intercalation LDH is substantially better than ultraviolet absorber list intercalation to PP light protecting effect altogether for ultraviolet absorber and radical scavenger
LDH。
Advantages of the present invention：Supermolecular intercalation structure light stabilizer prepared by the present invention has preparation method simple, former
Material abundance, it is easy to the advantages of industrialized production, while also with heat resistance is high, resistance to migration is good, light-protection energy is excellent
The advantages that, it can be widely applied to the fields such as plastics, coating.
Brief description of the drawings:
Fig. 1 is ultraviolet absorber prepared by embodiment 1 and the common intercalation LDH of radical scavenger XRD spectra.
Fig. 2 is ultraviolet absorber prepared by embodiment 1 and the common intercalation LDH of radical scavenger FT-IR spectrograms.
Fig. 3 is ultraviolet absorber prepared by embodiment 1 and radical scavenger light protecting effects of the intercalation LDH to PP altogether
Figure.A is polypropylene in figure, and b is BP-4 intercalation LDH/ polypropylene composites, c 2,
2,6,6- tetramethyl piperidines -4- epoxides propionic acid and the common intercalation LDH/ polypropylene of BP-4
Compound.
Embodiment：
Embodiment 1：
Step A：Weigh 1.5g (5.0mmol) Mg (NO3)2·6H2O、0.938g(2.5mmol)Al(NO3)3·9H2O, it is molten
CO is removed in 30ml2Deionized water in be made into salting liquid.
Step B：Weigh 0.6g NaOH and be dissolved in the deionized water of 30ml removing carbon dioxides and be made into aqueous slkali；Weigh
0.5925g (2.5mmol) 2,2,6,6- tetramethyl piperidines -4- epoxides sodium propionate and 0.825g (2.5mmol) 2- hydroxyl -4- first
Epoxide benzophenone -5- sodium sulfonates are dissolved in the deionized water of 40ml removing carbon dioxides and the in the mixed solvent of ethylene glycol composition, add
Enter and mixed solution is formed into aqueous slkali.
Step C：In the case where nitrogen is protected and is stirred, the solution hybrid reaction that step A, B is prepared generates precipitation, by generation
Pelleting centrifugation washs 3 times, then adds the deionized water of 120ml removing carbon dioxides to be configured to slurries, weighs 0.0593g respectively
(0.25 mmol) 2,2,6,6- tetramethyl piperidines -4- epoxides sodium propionate and 0.0825g (0.25mmol) 2- hydroxyl -4- methoxyl groups
Benzophenone -5- sulphur sodium is added in slurries, and precipitation then is placed in into 100 DEG C of stirred in water bath reaction 6h, and reaction will after terminating
Reaction product centrifugation, washing 6 times, the product for centrifuging acquisition is placed in 100 DEG C of baking ovens and dries 24h, a kind of supermolecule is obtained and inserts
Rotating fields light stabilizer [Mg0.66Al0.34(OH)2](C12H22O3N)0.17(C14H11O6S)0.17·0.6H2O。
Embodiment 2：
Step A：Weigh 2.25g (7.5mmol) Mg (NO3)2·6H2O、0.938g(2.5mmol)Al(NO3)3·9H2O, it is molten
CO is removed in 40ml2Deionized water in be made into salting liquid.
Step B：Weigh 0.8g NaOH and be dissolved in the deionized water of 45ml removing carbon dioxides and be made into aqueous slkali；Weigh
0.5925 g (2.5mmol) 1,2,2,6,6- pentamethvls -4- ethoxyacetic acids sodium and 0.8g (5mmol) sodium salicylate are dissolved in and removed
In the deionized water of carbon dioxide, it is added in aqueous slkali and forms mixed solution.
Step C：In the case where nitrogen is protected and is stirred, the solution hybrid reaction that step A, B is prepared generates precipitation, by generation
Pelleting centrifugation washs 3 times, then adds the deionized water of 120ml removing carbon dioxides to be configured to slurries, weighs 0.0593g respectively
(0.25 mmol) 1,2,2,6,6- pentamethvls -4- ethoxyacetic acids sodium and 0.04g (0.25mmol) sodium salicylate are added to slurry
In liquid, then precipitation is placed in 95 DEG C of water-baths and reacts 15h, reaction product is centrifuged, washed 6 times by reaction after terminating, and will be centrifuged
The product of acquisition, which is placed in 80 DEG C of baking ovens, dries 22h, obtains a kind of supermolecular intercalation structure light stabilizer [Mg0.66Al0.34
(OH)2] (C12H22O3N)0.11(C7H5O3)0.23·0.6H2O。
Embodiment 3：
Step A：Weigh 3g (10.0mmol) Mg (NO3)2·6H2O、0.938g(2.5mmol)Al(NO3)3·9H2O, it is dissolved in
45ml removes CO2Deionized water in be made into salting liquid.
Step B：Weigh 1g NaOH and be dissolved in the deionized water of 25ml removing carbon dioxides and be made into aqueous slkali.Weigh 1.175g
(5mmol) 2,2,6,6- tetramethyl piperidines -4- amidos sodium propionate and 0.3978g (2.5mmol) para aminobenzoic acid sodium salt are dissolved in and removed
The deionized water of carbon dioxide and the in the mixed solvent of ethylene glycol, are added in aqueous slkali and form mixed solution.
Step C：In the case where nitrogen is protected and is stirred, the solution hybrid reaction that step A, B is prepared generates precipitation, by generation
Pelleting centrifugation washs 3 times, then adds the deionized water of 120ml removing carbon dioxides to be configured to slurries, weighs 0.0588g respectively
(0.25 mmol) 2,2,6,6- tetramethyl piperidines -4- amidos sodium propionate and 0.0398g (0.25mmol) para aminobenzoic acid sodium salt add
Entering into slurries, then precipitation is placed in 100 DEG C of water-baths and reacts 12h, reaction product is centrifuged, washed 6 times by reaction after terminating,
The product for centrifuging acquisition is placed in 90 DEG C of baking ovens and dries 18h, obtains a kind of supermolecular intercalation structure light stabilizer
[Mg0.66Al0.34(OH)2](C12H22O2N2)0.23(C7H6NO2)0.11·0.6H2O。
Embodiment 4：
Step A：Weigh 1.5g (5.0mmol) Mg (NO3)2·6H2O、0.938g(2.5mmol)Al(NO3)3·9H2O, it is molten
Salting liquid is made into the deionized water of 30ml removing carbon dioxides.
Step B：Weigh 0.6g NaOH and be dissolved in the deionized water of 35ml removing carbon dioxides and be made into aqueous slkali；Weigh
1.7625 g (7.5mmol) 1,2,2,6,6- pentamethvls -4- glycines sodium and 0.465g (2.5mmol) potassium cinnamate are molten
In the deionized water of removing carbon dioxide and the in the mixed solvent of ethylene glycol, it is added in aqueous slkali and forms mixed solution.
Step C：In the case where nitrogen is protected and is stirred, the solution hybrid reaction that step A, B is prepared generates precipitation, by generation
Pelleting centrifugation washs 3 times, then adds the deionized water of 120ml removing carbon dioxides to be configured to slurries, weighs 0.0588g respectively
(0.25 mmol) 1,2,2,6,6- pentamethvls -4- glycines sodium and 0.0465g (0.25mmol) potassium cinnamate are added to
In slurries, then precipitation is placed in 90 DEG C of water-baths and reacts 10h, reaction product is centrifuged, washed 6 times after terminating by reaction, will be from
The product that the heart obtains, which is placed in 100 DEG C of baking ovens, dries 20h, obtains a kind of supermolecular intercalation structure light stabilizer [Mg0.66Al0.34
(OH)2] (C12H22O2N2)0.25(C10H9O3)0.09·0.6H2O。
Embodiment 5：
Step A：Weigh 2.25g (7.5mmol) Mg (NO3)2·6H2O、0.938g(2.5mmol)Al(NO3)3·9H2O, it is molten
Salting liquid is made into the deionized water of 30ml removing carbon dioxides.
Step B：Weigh 0.8g (20mmol) NaOH and be dissolved in the deionized water of 40ml removing carbon dioxides and be made into aqueous slkali；Claim
Take 0.6805g (2.5mmol) 2,2,6,6- tetramethyl piperidines -4- propoxyl group sodium sulfonate and 0.8258g (2.5mmol) phenyl benzo
Imidazole sulfonic acid sodium is dissolved in the deionized water of removing carbon dioxide, is added in aqueous slkali and is formed mixed solution.
Step C：In the case where nitrogen is protected and is stirred, the solution hybrid reaction that step A, B is prepared generates precipitation, by generation
Pelleting centrifugation washs 3 times, then adds the deionized water of 120ml removing carbon dioxides to be configured to slurries, weighs 0.0681g respectively
(0.25 mmol) 2,2,6,6- tetramethyl piperidines -4- propoxyl group sodium sulfonate and 0.0826g (0.25mmol) phenylbenzimidazol sulphur
Sour sodium is added in slurries, and then precipitation is placed in 95 DEG C of water-baths and reacts 9h, and reaction product is centrifuged, washed by reaction after terminating
6 times, the product for centrifuging acquisition is placed in 90 DEG C of baking ovens and dries 24h, obtains a kind of supermolecular intercalation structure light stabilizer
[Mg0.66Al0.34(OH)2](C11H22O4NS)0.17(C13H9N2O3S)0.17·0.6H2O。
Claims (4)
1. a kind of supermolecular intercalation structure light stabilizer, its chemical general formula are：
[M2+ 1-xM3+ x(OH)2](A-)y(B-)z·cH2O
Wherein x=y+z, 0.2≤x≤0.4,0.01<y<0.39,0.01<z<0.39, c is intermediary water molecular number, 0.4<c<1；
M2+For Mg2+、Zn2+、Ni2+、Ca2+、Fe2+、Cu2+In any one or two kinds；M3+For Al3+、Co3+、Ti3+、Fe3+、Cr3+
One or both of；A-For radical scavenger A anion, B-For ultraviolet absorber anion；
Described radical scavenger A is tetramethyl piperidine class compound, and its chemical formula is shown below：
R in formula1For H or CH3；R2For O-R3-COONa、N-R3-COONa、O-R3-SO3Na or O-R3-SO3Na, wherein R3For
[CH2]m[C6H6]n, integers of the m between 1-8, n=0 or 1；
Described ultraviolet absorber B is para aminobenzoic acid sodium salt, p- methoxy cinnamic acid sodium, sodium salicylate, 2- hydroxyl -4- first
Epoxide benzophenone -5- sodium sulfonates, coumarin-3-carboxy acid's sodium, sodium cinnamate, BTA -4- hydroxyls-benzene sulfonic acid sodium salt, 2- benzene
One or more in base benzimidazole -5- sodium sulfonates.
2. supermolecular intercalation structure light stabilizer according to claim 1, it is characterized in that described M2+It is Mg2+、Zn2+In
One kind, M3+It is Al3+。
3. a kind of method of the supermolecular intercalation structure light stabilizer prepared described in claim 1, is comprised the following steps that：
A. M is weighed2+、M3+Nitrate or chlorate be dissolved in the deionized water of removing carbon dioxide and be configured to mixing salt solution A, its
Middle M2+With M3+Mol ratio be 2-4, M3+Molar concentration be 0.05-0.8mol/L；
Wherein M2+For Mg2+、Zn2+、Ni2+、Ca2+、Fe2+、Cu2+In any one or two kinds；M3+For Al3+、Co3+、Ti3+、Fe3 +、Cr3+Deng one or both of trivalent metal cation；
B. the aqueous slkali that molar concentration is 0.05-1mol/L is prepared, described alkali is NaOH, KOH or ammoniacal liquor；Wherein mole of alkali
Measure as M in step solution A2+With M3+1.8-2.5 times of mole sum；
According to the ratio that the molar ratio of ultraviolet absorber and radical scavenger is 0.025-39, both raw materials are dissolved in molten
The solution that total mol concentration is 0.05-0.5mol/L is made into agent, is added in above-mentioned aqueous slkali and forms mixed solution B；Wherein
The mole sum of ultraviolet absorber and radical scavenger and M in solution A3+The ratio of mole sum is 1-3；Described is molten
Agent is the deionized water or its mixed solvent with polar solvent of removing carbon dioxide, and described polar solvent is ethanol, second two
Alcohol or glycerine, corresponding solvent is selected according to ultraviolet absorber used and radical scavenger can be dissolved；
Described radical scavenger is tetramethyl piperidine class compound, and its chemical formula is shown below：
R in formula1For H or CH3；R2For O-R3-COONa、N-R3-COONa、O-R3-SO3Na or N-R3-SO3Na, wherein R3For
[CH2]m[C6H6]n, integers of the m between 1-8, n=0 or 1；
Described ultraviolet absorber is para aminobenzoic acid sodium salt, p- methoxy cinnamic acid sodium, sodium salicylate, 2- hydroxyl -4- methoxies
Base benzophenone -5- sodium sulfonates, coumarin-3-carboxy acid's sodium, sodium cinnamate, BTA -4- hydroxyls-benzene sulfonic acid sodium salt, 2- phenyl
One or more in benzimidazole -5- sodium sulfonates；
C. in the case where nitrogen is protected and is stirred, mixing salt solution A and the generation of mixed solution B hybrid reactions are precipitated, by the heavy of generation
Shallow lake centrifuge washing 3 times, then it is configured to the slurries that solid content is 1-100g/L with water；Ultraviolet absorber is added to catch with free radical
Agent is obtained, wherein ultraviolet absorber, radical scavenger addition is M in slurries3+0.1-0.3 times of mole, then in 50-
Stirring reaction 4-24 hours at 150 DEG C, cooling, filtration product are simultaneously washed 4-9 times, and filter cake is in 60-100 DEG C of dry 12-24 hour
Obtain supermolecular intercalation structure light stabilizer.
4. the preparation method of supermolecular intercalation structure light stabilizer according to claim 2, it is characterized in that described M2+It is
Mg2+、Zn2+In one kind, M3+It is Al3+。
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| CN108794803A (en) * | 2018-05-15 | 2018-11-13 | 北京化工大学 | A kind of supermolecule is total to the preparation method of intercalation configuration anti-light aging material |
| CN110862613A (en) * | 2019-12-03 | 2020-03-06 | 江苏林辉塑料制品有限公司 | Anti-aging garbage can and preparation process thereof |
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| CN113956883A (en) * | 2021-11-25 | 2022-01-21 | 北京化工大学 | Monoatomic/magnesium-aluminum hydrotalcite material and preparation method and application thereof |
| CN114892297A (en) * | 2022-04-22 | 2022-08-12 | 南通大学 | Anti-aging polypropylene fiber based on novel light stabilizer intercalation and preparation method thereof |
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