CN106700121A - Efficient oil-water separated chitosan sponge and preparation method thereof - Google Patents
Efficient oil-water separated chitosan sponge and preparation method thereof Download PDFInfo
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/40—Devices for separating or removing fatty or oily substances or similar floating material
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/40—Impregnation
- C08J9/405—Impregnation with polymerisable compounds
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/40—Impregnation
- C08J9/42—Impregnation with macromolecular compounds
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- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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Abstract
The invention belongs to the field of chitosan materials, and discloses an efficientoil-water separated chitosan sponge and a preparation method thereof. The preparation method comprises the following steps of (1) dissolving chitosan into acid liquor to obtain a chitosan solution, and freeze-drying to obtain chitosan porous sponge; (2) through polymerization reaction of an in-situ silicone monomer, coating organo-siloxane on the surface of the chitosan porous sponge, and drying to obtain the efficient oil-water separated chitosan sponge. According to the efficient oil-water separated chitosan sponge and the preparation method thereof provided by the invention, the chitosan porous sponge is obtained through freeze drying, a layer of organo-siloxane coating is applied on the surface of a framework of the chitosan sponge through polymerization reaction of the in-situ silicone monomer, and an oleophylic hydrophobic material with organo silicone on the surface is formed, so that the efficient oil-water separated chitosan sponge with super-hydrophobic and super-oleophilic characteristics is prepared, has a good mechanical property, and can meet the practical application requirement. The efficient oil-water separated chitosan sponge has higher oil absorption times on multiple oil, can be used for preparing a large-volume hydrophobic oleophylic sponge, is high in oil retaining ability, and is applied in oil-water separation.
Description
Technical field
The invention belongs to chitosan material field, more particularly to a kind of high efficiency oil-water separates chitosan sponge and its preparation side
Method.
Background technology
Increasing environmental problem in recent years, water pollution that such as Oil spills is caused, industrial discharge contain organic dyestuff
Or effluent containing heavy metal ions etc. are as important global problems, cause economic loss hundreds billion of every year, result in the life of difficult reparation
State is destroyed, and grave danger is brought to marine organisms and human health.Substantial amounts of manpower has been put into for wastewater treatments such as greasy dirts
Material resources, but effect is not ideal.The material for being now used for greasy dirt absorption is mostly not biodegradable, and substantial amounts of use can be caused
White pollution.New, efficient, safe, environment-friendly, abundance the natural porous polymer sponge of research and development, protects for environment
Shield and pollution control are very necessary and very urgent.
1966, U.S.'s Dow Chemical synthesized the first oil suction macromolecule divinylbenzene crosslink alkyl vinyl.It is Japanese afterwards
Three wells, the big, catalyst in east etc. have also carried out the research of oil-absorbing resin, and realize commercialization.In recent years, various structures novelties is more
Porous materials are used for the absorption of greasy dirt, including polyurethane, polyvinyl formal and carbon nanomaterial and inorganic porous material.But inhale
Oil is adsorbed in material capillary by physical action more than light wood material, oil absorbing effect is undesirable, such as 1. oil absorption is little, oil suction
Multiplying power is smaller；2. oil-water selectivity is low, is also absorbed water while oil suction；3. Oil keeping is poor after oil suction, and slightly pressure will oil leak；4. grind
Hair and manufacturing cost are huge, it is impossible to recycle or be difficult to degrade in nature.Which has limited it in oil mixing with water system
Practical application, it is impossible to meet waste oil reclaim, environmental improvement and the requirement of Green Development.It would therefore be highly desirable to development quality is light, high thin
Aqueous, oil suction efficiency high, speed is fast, it is repeatable utilize, can natural degradation new oil absorption material.
Ocean renewable resource shitosan is the extremely abundant natural resources of storage on the earth, is unique positively charged moving
Fibres element.Shitosan carries amino cation group, has strong absorption complexing to negatively charged harmful substance, in material
The field such as material, chemistry, environment, food, medicine, biology, medical science has a wide range of applications.Because it is complete biogenetic derivation, from
Body again can whole natural degradations, it obtains, using, the link such as reclaim and be substantially not present any environmental hazard, therefore develop its
Application tool in terms of hydrophobic oleophilic oil is of great significance.But chitosan sponge prepared by freeze-drying is hydrophilic
Surface nature, many water suctions in oil water mixture, the adsorbance to oil is little, does not have any oil-water selectivity to adsorb.So far
There is no suitable technical method quickly to prepare the chitosan sponge material with oleophilic drainage for water-oil separating.
The content of the invention
In order to overcome the shortcomings and deficiencies of the prior art described above, primary and foremost purpose of the invention is to provide a kind of high efficiency oil-water
Separate the preparation method of chitosan sponge.
Another object of the present invention is to provide high efficiency oil-water separation chitosan sponge prepared by the above method.
Still a further object of the present invention is to provide above-mentioned high efficiency oil-water to separate application of the chitosan sponge in water-oil separating.
The purpose of the present invention is realized by following proposal：
A kind of high efficiency oil-water separates the preparation method of chitosan sponge, comprises the following steps：
(1) shitosan is dissolved in acid solution and obtains chitosan solution, freezed, obtain chitosan multi-porous sponge；
(2) by the polymerisation of siloxanyl monomers in situ, organosiloxane is coated in chitosan multi-porous sponge surface
High efficiency oil-water is obtained after drying and separates chitosan sponge.
Wherein in one embodiment, the shitosan described in step (1) is the powdered shitosan of 80~400 purposes.
Wherein in one embodiment, acid solution described in step (1) can for formic acid, acetic acid (acetic acid), oxalic acid, lactic acid and
One or more in hydrochloric acid of mixture aqueous solution.
Wherein in one embodiment, the mass concentration of the chitosan solution described in step (1) is 0.1~5%, sour
Mass concentration is 0.1~5%.
Wherein in one embodiment, the operation in step (1) is to be dissolved in acid solution shitosan under mechanical stirring.
Described mechanical agitation is preferably 30~1200min of stirring under the speed of 50~1500rpm.
Wherein in one embodiment, the condition freezed described in step (1) is 4~24h of freezing at -10~-80 DEG C, then
At -56 DEG C~-80 DEG C, 12~48h is dried.
Wherein in one embodiment, the siloxanyl monomers described in step (2) can be dimethyl siloxane, trimethoxy
Silane, tetraethoxysilane, tetramethoxy-silicane, MTMS, propyl trimethoxy silicane, methyl triethoxy
Silane, propyl-triethoxysilicane, vinyltrimethoxy silane, VTES, 3- aminopropyl trimethoxies
Silane, gamma-aminopropyl-triethoxy-silane, n-octytriethoxysilane, hexadecyl trimethoxy silane and octadecyl
At least one in triethoxysilicane.
Wherein in one embodiment, the medium of polymerisation described in step (2) is the mixture of ethanol and ammoniacal liquor.
Wherein in one embodiment, the medium of polymerisation described in step (2) is that mass ratio is 100:1~5:1
The mixture of ethanol and ammoniacal liquor.
Wherein in a preferred embodiment, the medium of polymerisation described in step (2) is that mass ratio is 9:1 ethanol
With the mixture of ammoniacal liquor.
Wherein in one embodiment, the mass ratio of polymerisation used medium described in step (2) and siloxanyl monomers
It is 100:1~10:1.
Wherein in one embodiment, the condition of polymerisation is 25~80 DEG C described in step (2), and the reaction time is
0.5~24h.
Wherein in one embodiment, the polymerisation described in step (2) concretely soaks chitosan multi-porous sea
Carried out in the medium of silicone-containing monomer.
Wherein in one embodiment, chitosan multi-porous sponge used is with the mass ratio of siloxanyl monomers in step (2)
0.1:10~5:1.
Wherein in one embodiment, dry temperature described in step (2) be 30~100 DEG C, drying time be 0.5~
48h。
The present invention provides the high efficiency oil-water separation chitosan sponge that the above method is prepared, and specially surface is organosilicon
Oleophilic drainage material, with super-hydrophobic and super oil-wet behavior, in can be applied to water-oil separating.
Described oil includes monochloro methane, dichloromethane, chloroform, carbon tetrachloride, petroleum crude oil, gasoline, diesel oil, sunflower
Oil, peanut oil, soybean oil, n-hexane, normal octane, acetone, benzene,toluene,xylene, ethylbenzene and styrene etc..
The present invention obtains chitosan solution by the way that shitosan is dissolved under mechanical stirring in acidic aqueous solution, then by shell
Glycan solution freeze-drying, obtains chitosan multi-porous sponge；It is poly- in shell afterwards by the polymerisation of siloxanyl monomers in situ
The framework surface of sugared sponge coats one layer of organosiloxanes coatings, is the oleophilic drainage material of organosilicon as surface, so as to make
It is standby to go out to separate chitosan sponge with the super-hydrophobic high efficiency oil-water with super oil-wet behavior.The inventive method is cheap, operation is simple
Single, energy consumption is low, preparation efficiency is high, environmentally safe.The complete biogenetic derivation of shitosan, it is cheap, it is nontoxic, can be whole
Natural degradation.The hydrophobic sponge of shitosan, mechanical property is good, can meet application request.All have to various oil higher
Oil suction multiple, can prepare the hydrophobic oleophilic oil sponge of large volume, and oil-retaining is strong, is applied in water-oil separating.
The present invention has the following advantages and beneficial effect relative to prior art：
1st, the present invention proposes a kind of method for preparing shitosan hydrophobic oleophilic oil sponge, cheap, simple to operate, energy consumption
Low, preparation efficiency is high, environmentally safe, and the chitosan sponge of preparation can be used for actual water-oil separating operation.
2nd, the present invention uses the complete biogenetic derivation of shitosan, cheap, nontoxic, environment-friendly, can be all natural
Degraded, its obtain, using, reclaim etc. link environmental hazard it is small, be it is a kind of green macromolecular material.
3rd, the hydrophobic sponge of shitosan prepared by the present invention, mechanical property is good, can meet application request.To various oil
All there is oil suction multiple higher, the hydrophobic oleophilic oil sponge of large volume can be prepared, oil-retaining is strong.
Brief description of the drawings
Fig. 1 is the loose structure scanning electron microscope diagram of the chitosan sponge of preparation in embodiment 1.
Fig. 2 is the chitosan sponge prepared in embodiment 2, polysilane before modified after suspension situation in water.
Fig. 3 is the oily oil absorbing effect of the hydrophobic chitosan sponge to different types of preparation in embodiment 3.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
The reagent used in the following example can be obtained from commercial channel.
Embodiment 1
By 2g shitosans, 2mL hydrochloric acid, 100mL deionized waters, (400r/min stirs 120min) is abundant under mechanical stirring
Dissolving obtains transparent chitosan solution；The chitosan solution that will be obtained freezes 4h at -20 DEG C and is frozen into ice, then is carried out at -56 DEG C
Freeze-drying, obtains chitosan multi-porous sponge；By above-mentioned 1cm3Sponge be dipped into and contain 0.2g tetramethoxy-silicanes and 0.5g
In the ethanol ammonia water mixture of hexadecyl trimethoxy silane (ethanol 9mL+ ammoniacal liquor 1mL), polymerisation 4h is carried out at 50 DEG C,
Sponge is dried into 12h at 40 DEG C, shitosan oleophilic drainage sponge is obtained.
Accompanying drawing 1 is the scanning electron microscope (SEM) photograph of the chitosan multi-porous sponge that embodiment 1 is prepared.As can be seen from Figure 1 hole
Structure-rich, pore size is suitable for water-oil separating between 250~500 μm.
The oil suction multiple that the shitosan oleophilic drainage sponge of gained carries out toluene is determined, sponge is immersed in toluene,
The weight after the dry weight and adsorption equilibrium of contrast sponge is weighed, is found to the absorption multiple of toluene up to 7.5 times.
Embodiment 2
By 1g shitosans, 1.5mL glacial acetic acids, 100mL deionized waters under mechanical stirring (600r/min stirs 240min)
Fully dissolving obtains transparent chitosan solution；The chitosan solution that will be obtained freezes 6h at -40 DEG C and is frozen into ice, then at -80 DEG C
Freeze-drying is carried out, chitosan multi-porous sponge is obtained；By above-mentioned 1cm3Sponge be dipped into containing 0.4g dimethyl siloxanes and
In the ethanol ammonia water mixture of 0.6g vinyltrimethoxy silanes (ethanol 8mL+ ammoniacal liquor 2mL), polymerisation is carried out at 60 DEG C
10h, 8h is dried by sponge at 60 DEG C, obtains shitosan oleophilic drainage sponge.
Accompanying drawing 2 be the polysilane of chitosan multi-porous sponge for preparing of embodiment 2 before modified after the suspension in water
Situation photo.It can be seen that before modified, shitosan is hydrophilic, submerged.Modified chitosan sponge swims in water completely
On face, show its hydrophobic character.
The oil suction multiple that the shitosan oleophilic drainage sponge of gained carries out dichloroethanes is determined, sponge is immersed in dichloro
In ethane, the weight after the dry weight and adsorption equilibrium of contrast sponge is weighed, found to the absorption multiple of dichloroethanes up to 10 times.
Embodiment 3
By 0.5g shitosans, 1.5mL lactic acid, 100mL deionized waters, (1000r/min is stirred under mechanical stirring
480min) fully dissolving obtains transparent chitosan solution；The chitosan solution that will be obtained freezes 8h at -60 DEG C and is frozen into ice, then
Freeze-drying is carried out at -80 DEG C, chitosan multi-porous sponge is obtained；By above-mentioned 1cm3Sponge be dipped into and contain 0.5g propyl group front threes
In the ethanol ammonia water mixture of TMOS and 0.5g tetramethoxy-silicanes (ethanol 9.5mL+ ammoniacal liquor 0.5mL), carried out at 80 DEG C
Polymerisation 5h, 4h is dried by sponge at 80 DEG C, obtains shitosan oleophilic drainage sponge.
The shitosan oleophilic drainage sponge of gained is carried out into toluene, sunflower oil, dichloromethane, n-hexane, chloroform, acetone
Oil suction multiple is determined, and sponge is immersed in aforesaid liquid, weighs the weight after the dry weight and adsorption equilibrium of contrast sponge.
Accompanying drawing 3 is that the chitosan multi-porous sponge that embodiment 3 is prepared is compared the oily oil absorbing effect of different types.
Embodiment 4
By 4g shitosans, 4mL formic acid, 100mL deionized waters, (500r/min stirs 600min) is abundant under mechanical stirring
Transparent chitosan solution is obtained in dissolving；The chitosan solution that will be obtained freezes 8h at -80 DEG C and is frozen into ice, then enters at -80 DEG C
Row freeze-drying, obtains chitosan multi-porous sponge；By above-mentioned 1cm3Sponge be dipped into containing 0.6g trimethoxy silanes and
In the ethanol ammonia water mixture of 0.1g gamma-aminopropyl-triethoxy-silanes (ethanol 10mL+ ammoniacal liquor 2mL), it is polymerized at 30 DEG C
Reaction 20h, 2h is dried by sponge at 100 DEG C, obtains shitosan oleophilic drainage sponge.
The oil suction multiple that the shitosan oleophilic drainage sponge of gained carries out sunflower oil is determined, sponge is immersed in sunflower oil
In, the weight after the dry weight and adsorption equilibrium of contrast sponge is weighed, find to the absorption multiple of sunflower oil up to 7.8 times.
Embodiment 5
By 0.5g shitosans, 0.5mL oxalic acid, 100mL deionized waters under mechanical stirring (1500r/min stirs 60min)
Fully transparent chitosan solution is obtained in dissolving；The chitosan solution that will be obtained freezes 8h at -80 DEG C and is frozen into ice, then -80
DEG C freeze-drying is carried out, obtain chitosan multi-porous sponge；By above-mentioned 1cm3Sponge be dipped into and contain 0.3g tetraethoxysilanes
With (ethanol 20mL+ ammoniacal liquor 1mL) in the ethanol ammonia water mixture of 0.1g propyl-triethoxysilicanes, polymerisation is carried out at 70 DEG C
10h, 24h is dried by sponge at 30 DEG C, obtains shitosan oleophilic drainage sponge.
The oil suction multiple that the shitosan oleophilic drainage sponge of gained carries out n-hexane is determined, sponge is immersed in n-hexane
In, the weight after the dry weight and adsorption equilibrium of contrast sponge is weighed, find to the absorption multiple of n-hexane up to 6.4 times.
Embodiment 6
By 5g shitosans, 5mL hydrochloric acid, 100mL deionized waters, (700r/min stirs 180min) is abundant under mechanical stirring
Transparent chitosan solution is obtained in dissolving；The chitosan solution that will be obtained freezes 24h at -15 DEG C and is frozen into ice, then enters at -56 DEG C
Row freeze-drying, obtains chitosan multi-porous sponge；By above-mentioned 1cm3Sponge be dipped into and contain 0.4g vinyl trimethoxy silicon
In the ethanol ammonia water mixture of alkane (ethanol 10mL+ ammoniacal liquor 0.05mL), polymerisation 24h is carried out at 25 DEG C, by sponge at 90 DEG C
3h is dried, shitosan oleophilic drainage sponge is obtained.
The oil suction multiple that the shitosan oleophilic drainage sponge of gained carries out petroleum crude oil is determined, sponge is immersed in oil
In crude oil, the weight after the dry weight and adsorption equilibrium of contrast sponge is weighed, found to the absorption multiple of petroleum crude oil up to 10 times.
Above-described embodiment is the present invention preferably implementation method, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from Spirit Essence of the invention and the change, modification, replacement made under principle, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (10)
1. a kind of high efficiency oil-water separates the preparation method of chitosan sponge, it is characterised in that comprise the following steps：
(1) shitosan is dissolved in acid solution and obtains chitosan solution, freezed, obtain chitosan multi-porous sponge；
(2) by the polymerisation of siloxanyl monomers in situ, dried in chitosan multi-porous sponge surface cladding organosiloxane
After obtain high efficiency oil-water separate chitosan sponge.
2. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
Described in siloxanyl monomers be dimethyl siloxane, trimethoxy silane, tetraethoxysilane, tetramethoxy-silicane, methyl
Trimethoxy silane, propyl trimethoxy silicane, MTES, propyl-triethoxysilicane, vinyl trimethoxy
Base silane, VTES, 3- aminopropyl trimethoxysilanes, gamma-aminopropyl-triethoxy-silane, n-octyl three
At least one in Ethoxysilane, hexadecyl trimethoxy silane and octadecyl triethoxysilicane.
3. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
Described in the medium of polymerisation be the mixture of ethanol and ammoniacal liquor.
4. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
Described in the mass ratio of polymerisation used medium and siloxanyl monomers be 100:1~10:1.
5. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
Described in the condition of polymerisation be 25~80 DEG C, the reaction time is 0.5~24h.
6. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
Described in polymerisation be specially to be immersed in chitosan multi-porous sea in the medium of silicone-containing monomer and carry out.
7. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
In the mass ratio of chitosan multi-porous sponge used and siloxanyl monomers be 0.1:10~5:1.
8. high efficiency oil-water according to claim 1 separates the preparation method of chitosan sponge, it is characterised in that：Step (2)
Described in dry temperature be 30~100 DEG C, drying time be 0.5~48h.
9. a kind of high efficiency oil-water separates chitosan sponge, it is characterised in that the preparation side according to any one of claim 1~8
Method is obtained.
10. the high efficiency oil-water described in claim 9 separates application of the chitosan sponge in water-oil separating.
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| CN107987311A (en) * | 2017-12-27 | 2018-05-04 | 淮阴工学院 | A kind of preparation method of hydrophobicity melamine sponge enhancing polysilsesquioxane composite aerogel |
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| CN107987311A (en) * | 2017-12-27 | 2018-05-04 | 淮阴工学院 | A kind of preparation method of hydrophobicity melamine sponge enhancing polysilsesquioxane composite aerogel |
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| CN109364896A (en) * | 2018-12-20 | 2019-02-22 | 南京林业大学 | A kind of preparation method of the strong oil absorption material of organic-silicon-modified lignin-base |
| CN109364896B (en) * | 2018-12-20 | 2021-10-29 | 南京林业大学 | Preparation method of organic silicon modified lignin-based strong oil absorption material |
| CN110606992A (en) * | 2019-08-13 | 2019-12-24 | 浙江跃维新材料科技有限公司 | Preparation method and application of porous foam material based on biomass nano material |
| CN110497492A (en) * | 2019-08-30 | 2019-11-26 | 北京林业大学 | A kind of preparation method of the super-hydrophobic wooden sponge |
| CN113563634A (en) * | 2021-07-27 | 2021-10-29 | 王宇昕 | Hydrophobic modification method of hydrophilic porous material |
| CN114369191A (en) * | 2022-01-24 | 2022-04-19 | 西南石油大学 | Preparation method of super-hydrophobic polystyrene porous material |
| CN114369191B (en) * | 2022-01-24 | 2023-09-19 | 西南石油大学 | Preparation method of super-hydrophobic polystyrene porous material |
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