CN104667888A - Photosensitive polymer modified adsorbing material and preparation method and application of photosensitive polymer modified adsorbing material - Google Patents
Photosensitive polymer modified adsorbing material and preparation method and application of photosensitive polymer modified adsorbing material Download PDFInfo
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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Abstract
The invention discloses a photosensitive polymer modified adsorbing material and a preparation method and application of the photosensitive polymer modified adsorbing material. Particularly, the preparation method of the photosensitive polymer modified adsorbing material comprises the following steps: (1) synthesizing a spiropyrane photosensitive monomer; (2) performing silane coupling agent modification to a substrate material; and (3) copolymerizing the photosensitive monomer and the modified substrate material. According to the photosensitive polymer modified adsorbing material, the oil-water selectivity and the oil-keeping performance of the original substrate material are enhanced, the adsorbing material has the characteristics of light-operated adsorption/desorption of oils and organic solvents, and compared with the method for extruding for deoiling by use of mechanical pressure, the method has the advantages that the intelligentized function is achieved, the space and the time are almost not limited, and the operation is easy.
Description
Technical field
The invention belongs to technical field of polymer composite materials, be specifically related to a kind of spiro-pyrans type photosensitive polymer-melamine foamed plastic composite adsorbing material, its preparation method with ultraviolet light response, and as the purposes of oil absorption material.
Background technology
In the last few years, the oil of frequent generation and organic solvent were revealed event and were not only brought serious harm to natural environment, also brought tremendous influence to social economy, were unfavorable for the circulation sustainable development of society.At present, the oils utilizing oil absorption material process to reveal and organic solvent are one of most economical effective methods.But traditional oil absorption material (as diatomite, oil sucting pad, fabric etc.) is although still there is obvious deficiency compared with low in cost: (1) adsorbance is little; (2) oil-water selectivity is poor; (3) Oil keeping is poor, organic efficiency is low.Therefore, how to prepare that oil suction multiplying power is high, oil-water selectivity is high, Oil keeping is good and reusable novel absorption material has become current study hotspot.
Many researchers obtain inspiration from occurring in nature " super-hydrophobic (superhydrophobicity) " this phenomenon, utilize all multi-methods to prepare a series of novel absorption material with super-hydrophobic oleophilic properties.Wherein, the substrate of sorbing material selects polyurethane sponge, melamine foamed plastic, graphene oxide foam etc. both to have more functional group of modifying usually, has again the porous material of good mechanical properties.Method of modifying for these porous materials then has nano-precipitation method, Small molecular finishing and polymer copolymerization etc.
Spiro-pyrans (spiropyran) and derivative thereof are the important photaesthesia compounds of a class, because it can realize the transformation of open/close under ultraviolet/visible light is irradiated, and open/close makes it have the heterogeneity of hydrophilic/lipophilic, thus receive the concern of many researchers in sorbing material field.Spiro-pyrans Small molecular is modified substrate material surface by methods such as dehydrating condensations by existing bibliographical information, and obtaining is hydrophilic functional material under visible light under ultraviolet light in hydrophobicity, but the method also exists, and reaction efficiency is lower waits deficiency.Therefore, if spiro-pyrans function monomer and base material are carried out initiated polymerization, then not only can improve raw material availability, also be expected to obtain the oil absorption material that can carry out hydrophobic/hydrophilic character qualitative change simultaneously.
Summary of the invention
For above-mentioned situation, the object of the invention is to obtain the photosensitive sorbing material of spiro-pyrans type intelligence by a kind of preparation method of novelty, carry out adsorbing to realize this sorbing material under visible/ultraviolet is irradiated/desorption oils and organic effect.
General principle of the present invention is as follows: first utilize silane coupler (as vinyl trichlorosilane) can carry out the carbon-carbon double bond of polymerisation in the upper introducing of base material (as melamine foamed plastic), then under the initiation of initator, carry out free-radical polymerized with the same spiropyran derivatives containing carbon-carbon double bond, finally obtain novel absorption material base material totally being modified out one deck photosensitive polymer.Under visible light, the sorbing material obtained is hydrophobic material, can be used for the oils and the organic matter that adsorb leakage.After absorption, utilize UV-irradiation, can make above-mentioned is that hydrophobic sorbing material is transformed into hydrophilic material, utilizes profit to repel automatic desorption oils and organic matter, thus realizes the recovery of adsorbate and reusing of sorbing material.
In order to achieve the above object, the present invention adopts following concrete technical scheme:
A preparation method for the sorbing material that spiro-pyrans type photosensitive polymer is modified, it comprises the steps:
1) synthesis of photaesthesia monomer: under inert gas shielding; spiro-pyrans (SP-OH) is dissolved in anhydrous solvent; after dripping unsaturated acylating reagent, react 10 ~ 20 hours under condition of ice bath, after reaction terminates; removal of solvent under reduced pressure; through chromatography purification, vacuum drying, obtains photaesthesia monomer; the mol ratio of wherein said spiro-pyrans and unsaturated acylating reagent is 1:1.1 ~ 3, and the structural formula of described spiro-pyrans is as follows:
；
2) modification of base material: according to the bath raio of 1:400 ~ 500, by base material submergence 5 ~ 20 minutes in decorating liquid, take out and extract decorating liquid, then organic solvent washing is used, in 100 DEG C of oven dry, obtain modificationization base material, wherein said decorating liquid is that silane coupler is at toluene or N, solution in dinethylformamide, in described decorating liquid, the percentage by weight of silane coupler is 0.5 ~ 2%;
3) copolymerization of photaesthesia monomer and modificationization base material: according to the bath raio of 1:300 ~ 500, by step 2) in the modification base material that obtains be immersed in copolymer fluid, repeatedly after extruding, in 65 ~ 75 DEG C of reactions 12 ~ 24 hours under inert gas shielding, take out and extract copolymer fluid, then wash with low polar solvent, in 100 DEG C of oven dry, obtain the sorbing material that spiro-pyrans type photosensitive polymer is modified, wherein said copolymer fluid is that the photaesthesia monomer and polymerization initiator that obtain in step 1) are at cyclohexanone or N, solution in dinethylformamide, in described copolymer fluid, the percentage by weight of photaesthesia monomer is 2 ~ 6%, the mol ratio of polymerization initiator and photaesthesia monomer is 1:70 ~ 100.
Preferably, inert gas described in step 1) be selected from nitrogen, helium, neon any one, preferred nitrogen.
Preferably, solvent described in step 1) be selected from carrene, chloroform, toluene any one, preferred carrene.
Preferably, described in step 1), unsaturated acylating reagent is selected from any one in 2-methacrylic chloride, acryloyl chloride, methacrylic anhydride, preferred 2-methacrylic chloride.
Preferably, the time of reacting described in step 1) is 12 hours.
Preferably, step 2) described in bath raio be 1:400.
Preferably, step 2) described in base material be selected from polyurethane sponge, melamine foamed plastic, graphene oxide foam any one, preferred melamine foamed plastic.
Preferably, step 2) described in time of submergence be 20 minutes.
Preferably, step 2) described in organic solvent be ethanol or toluene, preferred alcohol.
Preferably, step 2) described in silane coupler be selected from vinyl trichlorosilane, γ-(2-methacryloxy) propyl trimethoxy silicane, β-(2-methacryloxy) ethyltriacetoxysilane, γ-(iso-amylene acyloxy) propyl-triethoxysilicane any one, preferred vinyl trichlorosilane, molecular formula is CH
2=CHSiCl
3.
Preferably, step 2) described in decorating liquid the percentage by weight of silane coupler be 1%.
Preferably, bath raio described in step 3) is 1:300.
Preferably, inert gas described in step 3) be selected from nitrogen, helium, argon gas any one, preferred argon gas.
Preferably, the temperature of reacting described in step 3) is 70 DEG C, and the time is 12 hours.
Preferably, low polar solvent described in step 3) is n-hexane or ether, preferred n-hexane.
Preferably, in copolymer fluid described in step 3), the percentage by weight of photaesthesia monomer is 5%, and the mol ratio of polymerization initiator and photaesthesia monomer is 1:70.
On the other hand, the invention provides the sorbing material of the spiro-pyrans type photosensitive polymer modification prepared according to above-mentioned preparation method.
Finally, the invention provides the purposes of sorbing material as oil absorption material of above-mentioned spiro-pyrans type photosensitive polymer modification.
Due to the utilization of technique scheme, the present invention compared with prior art has following advantages:
(1) amphipathic base material foam originally can be made to become pure hydrophobic foam by the modification of polymer, thus make material possess good oil-water selectivity;
(2) the spiro-pyrans component in the photosensitive polymer modified can in open loop under UV-irradiation, thus make foamed material be transformed into hydrophily by hydrophobicity, the oils utilizing the automatic desorption of profit repellency to adsorb and organic solvent, make foamed material to reuse;
(3) base material selected by is cheap and easy to get, and its porous network structure had is conducive to oils and organic absorption, can improve the oil suction multiplying power of material;
(4) polymer-modified method is comparatively easy, utilizes light as the controller of suction/de-oiling then not by the restriction of Time and place, handled easily.
Accompanying drawing explanation
Fig. 1 is the ESEM comparison diagram of melamine foamed plastic in polymer-modified front and back.
Fig. 2 is the infrared spectrum comparison diagram of melamine foamed plastic in polymer-modified front and back.
Fig. 3 is the contact angle test comparison figure of melamine foamed plastic in polymer-modified front and back.
Fig. 4 is the procedure chart that polymer-modified melamine foamed plastic carries out the water surface and the absorption of water-bed oils under visible light respectively.
Fig. 5 is the procedure chart that polymer-modified melamine foamed plastic carries out oils desorption respectively under visible ray and UV-irradiation.
Detailed description of the invention
Below in conjunction with the drawings and specific embodiments, further description is made to the present invention.
Embodiment one: the synthesis of photaesthesia monomer spiro-pyrans 2-methacrylate.
Under nitrogen protection; by 1g(2.83mmol) spiro-pyrans (SP-OH) is dissolved in 15mL anhydrous methylene chloride; drip 300 μ l(3.1mmol) after 2-methacrylic chloride; react 12 hours under condition of ice bath; after reaction terminates, steam removing carrene by revolving, gained crude on silica gel column chromatography purifies (solvent is benzinum: carrene=1:2); 0.4g yellow solid is obtained, i.e. spiro-pyrans 2-methacrylate (SPMA) after vacuum drying.
1H-NMR (400MHz, CDCl
3), δ (ppm): 7.97-8.05 (m, 2H), 7.17-7.24 (m, 1H), 7.09 (d, 1H), 6.89 (dd, 2H), 6.74 (dd, 2H), 6.07 (d, 1H), 5.87 (d, 1H), 5.56 (d, 1H), 4.3 (t, 2H), 3.37-3.62 (m, 2H), 1.92 (s, 3H), 1.28 (s, 3H), 1.16 (s, 3H)。
Embodiment two: the vinyl trichlorosilane of melamine foamed plastic is modified.
Measure 1g vinyl trichlorosilane to be dissolved in 99g toluene, obtain the vinyl trichlorosilane toluene solution that percentage by weight is 1%, stand-by.
Melamine foamed plastic (purchased from Ming Jie sponge product Co., Ltd of Zhangjagang City) is cut into the square (weight is 65mg) of 2cm × 2cm × 2cm, be immersed in the above-mentioned vinyl trichlorosilane toluene solution of 26g, after 20 minutes, foam is taken out, extract wherein solution of silane, then 50mL ethanol cyclic washing foam 3 times are used, dry in 100 DEG C of baking ovens, obtain the melamine foamed plastic (weight is 66.5mg) that vinyl trichlorosilane is modified.
Embodiment three: the copolymerization of the melamine foamed plastic that spiro-pyrans monomer SPMA and vinyl trichlorosilane are modified.
The inventory of reactant various in embodiment one is amplified on year-on-year basis, prepares 1g SPMA according to same step.Take 840mg(2.1mmol) SPMA, 5mg(0.03mmol) AIBN is dissolved in 28.5g DMF, obtains 29.345g copolymer fluid, stand-by.
Be immersed in above-mentioned copolymer fluid by the melamine foamed plastic (2cm × 2cm × 2cm, 65.5mg) that the vinyl trichlorosilane obtained in embodiment two is modified, extruding makes copolymer fluid fully contact with foam repeatedly, then reacts 12 hours in 70 DEG C under argon shield.Reaction terminates rear taking-up foam, extrudes solution wherein, then uses 50mL n-hexane foam 3 times, finally dry in 100 DEG C of baking ovens, obtains the melamine foam material that SPMA photosensitive polymer is modified.
The photosensitive polymer of melamine foamed plastic modifies whether success can be verified by multiple spectrogram.Obviously can find out from scanning electron microscope (SEM) photograph (SEM) as shown in Figure 1, the foam framework (right side) after copolymerization has wrapped up polymer.As can be seen from infrared spectrogram as shown in Figure 2, there is spiro-pyrans signal peak in the spectrogram (solid line) after copolymerization, the successful modification of polymer can be described equally.
The oil-water selectivity of sorbing material can be tested by contact angle and be determined.As can be seen from contact angle test comparison figure as shown in Figure 3, because foam before copolyreaction is amphipathic, so when carrying out contact angle test with water, acquired results is 0 °; And after modification completes, contact angle is increased to 155.5 °, reach super-hydrophobic standard, sorbing material is possessed good oil-water selectivity.
Embodiment four: the oil absorbency test carrying out the water surface and the bottom with the hydrophobic foam obtained in embodiment three under visible light respectively.
As shown in Figure 4, in water surface oil suction test, the toluene being dissolved with dyestuff is dropped on the water surface, within 2 seconds, observe absorption situation afterwards with tweezers gripping foam contacting; In water-bed oil suction test, then the chloroform being dissolved with dyestuff is dropped in the bottom, within 2 seconds, observe absorption situation afterwards with tweezers gripping foam contacting.As can be seen from the figure, no matter organic matter is at the water surface or the bottom, hydrophobic foam prepared by the present invention can be adsorbed soon, and not adsorbed water in whole process, illustrate polymer-modified after melamine foamed plastic not only there is the very fast rate of adsorption, also there is good oil-water selectivity.
Embodiment five: the desorption that the foam of absorption chloroform carries out respectively under visible ray and UV-irradiation is tested.
As shown in Figure 5, with tweezers gripping foam, immerse in the chloroform held in culture dish, be immersed in again in water after taking-up, irradiate with under visible ray and ultraviolet light respectively, observe de-oiling situation.Can find from figure, under visible light illumination, almost not observe the desorption of chloroform, this illustrates that foam is hydrophobic under visible light, and has good Oil keeping energy.And under ultraviolet light, obviously can see that chloroform starts to ooze from foam, this is because under ultraviolet irradiation, foam starts to be transformed into hydrophily, utilizes profit repulsive interaction by adsorbed chloroform exruded foams, reaches the object of light-operated de-oiling.
Claims (10)
1. a preparation method for the sorbing material of spiro-pyrans type photosensitive polymer modification, it comprises the steps:
1) synthesis of photaesthesia monomer: under inert gas shielding, is dissolved in spiro-pyrans in anhydrous solvent, after dripping unsaturated acylating reagent, react 10 ~ 20 hours under condition of ice bath, after reaction terminates, removal of solvent under reduced pressure, through chromatography purification, vacuum drying, obtains photaesthesia monomer;
Wherein: the mol ratio of described spiro-pyrans and unsaturated acylating reagent is 1:1.1 ~ 3, and the structural formula of described spiro-pyrans is as follows:
；
2) modification of base material: according to the bath raio of 1:400 ~ 500, by base material submergence 5 ~ 20 minutes in decorating liquid, takes out and extracts decorating liquid, then using organic solvent washing, in 100 DEG C of oven dry, obtaining modificationization base material;
Wherein: described decorating liquid is the solution of silane coupler in toluene or DMF, in described decorating liquid, the percentage by weight of silane coupler is 0.5 ~ 2%;
3) copolymerization of photaesthesia monomer and modificationization base material: according to the bath raio of 1:300 ~ 500, by step 2) in the modification base material that obtains be immersed in copolymer fluid, repeatedly after extruding, in 65 ~ 75 DEG C of reactions 12 ~ 24 hours under inert gas shielding, take out and extract copolymer fluid, then with low polar solvent washing, in 100 DEG C of oven dry, the sorbing material that spiro-pyrans type photosensitive polymer is modified is obtained;
Wherein: described copolymer fluid is that the photaesthesia monomer and polymerization initiator that obtain in step 1) are at cyclohexanone or N, solution in dinethylformamide, in described copolymer fluid, the percentage by weight of photaesthesia monomer is 2 ~ 6%, and the mol ratio of polymerization initiator and photaesthesia monomer is 1:70 ~ 100.
2. preparation method according to claim 1, is characterized in that, solvent described in step 1) be selected from carrene, chloroform, toluene any one.
3. preparation method according to claim 1, is characterized in that, described in step 1), unsaturated acylating reagent is selected from any one in 2-methacrylic chloride, acryloyl chloride, methacrylic anhydride.
4. preparation method according to claim 1, is characterized in that, step 2) described in base material be selected from polyurethane sponge, melamine foamed plastic, graphene oxide foam any one.
5. preparation method according to claim 1, it is characterized in that, step 2) described in silane coupler be selected from vinyl trichlorosilane, γ-(2-methacryloxy) propyl trimethoxy silicane, β-(2-methacryloxy) ethyltriacetoxysilane, γ-(iso-amylene acyloxy) propyl-triethoxysilicane any one.
6. preparation method according to claim 1, is characterized in that, step 2) described in decorating liquid the percentage by weight of silane coupler be 1%.
7. preparation method according to claim 1, is characterized in that, the temperature of reacting described in step 3) is 70 DEG C, and the time is 12 hours.
8. preparation method according to claim 1, is characterized in that, in copolymer fluid described in step 3), the percentage by weight of photaesthesia monomer is 5%, and the mol ratio of polymerization initiator and photaesthesia monomer is 1:70.
9. the sorbing material that the spiro-pyrans type photosensitive polymer that prepared by preparation method according to any one of claim 1 to 8 is modified.
10. the sorbing material modified of spiro-pyrans type photosensitive polymer according to claim 9 is as the purposes of oil absorption material.
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| CN105175393A (en) * | 2015-08-07 | 2015-12-23 | 中海石油环保服务（天津）有限公司 | Compound, preparation method thereof, oil absorbing resin and synthesis method thereof |
| CN107805294A (en) * | 2017-11-29 | 2018-03-16 | 杭州电子科技大学 | The preparation method and applications of Photosensitive magnetic nano-particle |
| CN109942603A (en) * | 2019-05-06 | 2019-06-28 | 湖南科技大学 | Photoswitch spiro-pyrans-imide compound preparation and its application |
| CN114752024A (en) * | 2022-03-29 | 2022-07-15 | 吉林大学 | Preparation method of copolymerization modified intelligent magnetic nano material |
| CN115193268A (en) * | 2022-06-28 | 2022-10-18 | 南京林业大学 | Photoresponse type intelligent wood film and preparation method and application thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105175393A (en) * | 2015-08-07 | 2015-12-23 | 中海石油环保服务（天津）有限公司 | Compound, preparation method thereof, oil absorbing resin and synthesis method thereof |
| CN105175393B (en) * | 2015-08-07 | 2019-04-19 | 中海石油环保服务（天津）有限公司 | A kind of compound, preparation method, a kind of oil-absorbing resin and its synthetic method |
| CN107805294A (en) * | 2017-11-29 | 2018-03-16 | 杭州电子科技大学 | The preparation method and applications of Photosensitive magnetic nano-particle |
| CN109942603A (en) * | 2019-05-06 | 2019-06-28 | 湖南科技大学 | Photoswitch spiro-pyrans-imide compound preparation and its application |
| CN109942603B (en) * | 2019-05-06 | 2021-08-10 | 湖南科技大学 | Preparation and application of optical switch spiropyran-perylene bisimide compound |
| CN114752024A (en) * | 2022-03-29 | 2022-07-15 | 吉林大学 | Preparation method of copolymerization modified intelligent magnetic nano material |
| CN114752024B (en) * | 2022-03-29 | 2024-01-30 | 吉林大学 | Preparation method of copolymerization-modified intelligent magnetic nano material |
| CN115193268A (en) * | 2022-06-28 | 2022-10-18 | 南京林业大学 | Photoresponse type intelligent wood film and preparation method and application thereof |
| CN115193268B (en) * | 2022-06-28 | 2023-11-03 | 南京林业大学 | Light response type intelligent wood film and preparation method and application thereof |
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