CN106944016B - A kind of pH responsiveness water-oil separating foam and preparation method thereof - Google Patents
A kind of pH responsiveness water-oil separating foam and preparation method thereof Download PDFInfo
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- CN106944016B CN106944016B CN201710162751.7A CN201710162751A CN106944016B CN 106944016 B CN106944016 B CN 106944016B CN 201710162751 A CN201710162751 A CN 201710162751A CN 106944016 B CN106944016 B CN 106944016B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28042—Shaped bodies; Monolithic structures
- B01J20/28045—Honeycomb or cellular structures; Solid foams or sponges
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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
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/32—Hydrocarbons, e.g. oil
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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
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/08—Seawater, e.g. for desalination
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Water Treatment By Sorption (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
The invention discloses a kind of pH responsiveness water-oil separating foams and preparation method thereof.The water-oil separating foam is using melamine foams as carrier, and surface grafting pH responsive polymer poly 4 vinyl pyridine is, it can be achieved that pH responsiveness water-oil separating, and by changing pH value, water contact angle is adjustable within the scope of 0 ~ 135 °.Responsiveness water-oil separating foam of the present invention shows super hydrophilic/superoleophobic property in the lower solution of pH value, and high hydrophobic/super-oleophilic is presented as in the higher solution of pH；Meanwhile it can be not only used for water-oil separating, and the oil of quick release absorption is recycled, and sewage purification and fluid channel switch control can also be carried out.Preparation method of the present invention is simple, low in cost, is suitable for industrialized production.
Description
Technical field
The invention belongs to perforated foams fields, and in particular to a kind of pH responsiveness water-oil separating foam and its preparation side
Method.
Background technique
It is many effective for the generation of increasingly serious leaked offshore oil accident and industrial organic reagent leakage accident
Leakage processing is also come into being, such as method of chemical treatment, control combustion method, microbial degradation method and oil-absorption process.
Oil-absorption process has that clearance rate is high, low energy consumption, pollution is small and at low cost etc. for handling the petroleum of spillage over water
Advantage.Therefore, related scientific research worker mainly studies the preparation of oil absorption material, especially three-dimensional oil absorption material.Three-dimensional oil suction material
Material can directly carry out petroleum absorption in Oil spills place.It is recycled after petroleum absorbent, traditional way of recycling
It mainly distills and squeezes.However, distillation is higher for low boiling point light oil absorption efficiency, higher boiling heavy oil is difficult to back
It receives, while comparing energy consumption；Although squeezing oil recovery phase that can be fairly simple, but still there are many oil residuals on the sorbent
Result in secondary pollution (ACS Sustainable Chem. Eng. 2015,3,3012-3018).
The drawbacks of for above-mentioned oil recycling, the water-oil separating three-dimensional material of many responsiveness starts to occur.PH responsiveness material
Material also enters the scope of research.PH responsive polymer is commonplace, cheap and easy to get.Melamine foams are three-dimensional porous materials
Ideal template, surface is easy to chemical modification, and has excellent elasticity and anti-flammability.The present invention is by the way that pH responsiveness to polymerize
Object poly 4 vinyl pyridine, by graft polymerization in melamine base foam surface, has been obtained pH and rung in a manner of atom transferred free radical
The three-dimensional water-oil separating foam of answering property.
Summary of the invention
It is an object of that present invention to provide a kind of pH responsiveness water-oil separating foam, which is with melamine foams
Carrier, surface grafting poly 4 vinyl pyridine have pH quick response.
The object of the invention, which also resides in, provides a kind of pH responsiveness water-oil separating foam preparation processes.
The present invention is achieved through the following technical solutions.
A kind of pH responsiveness water-oil separating foam, using melamine foams as carrier, the poly- 4- of surface grafting pH responsive polymer
Vinylpyridine is, it can be achieved that pH responsiveness water-oil separating, and by changing pH value, water contact angle is adjustable within the scope of 0 ~ 135 °.
A kind of method of preparation pH responsiveness water-oil separating foam, includes the following steps:
(1) melamine foams are placed in the toluene solution of 3- TSL 8330, carry out back flow reaction；Reaction
After take out, toluene washs repeatedly, nitrogen drying；
(2) foam impregnation for obtaining step (1) under ice-water bath, is added dropwise dropwise in the dichloromethane solution of pyridine
2- bromine isobutyl acylbromide continues to be reacted in ice-water bath after being added dropwise, react again under room temperature 10 ~ 15 hours；After reaction
It takes out, is successively washed repeatedly with methylene chloride and acetone, it is dry under nitrogen atmosphere；
(3) under nitrogen atmosphere, the foam that step (2) obtains is placed in butanone and isopropyl containing monomer 4-vinylpridine
Alcohol in the mixed solvent is added catalyst CuBr and complexant pentamethyldivinyltriamine, is reacted；It takes after reaction
Out, deionized water is cleaned, dry under nitrogen atmosphere, obtains the pH responsiveness water-oil separating foam.
Further, in step (1), the mass concentration of the toluene solution of the 3- TSL 8330 is 1 ~
10 %。
Further, in step (1), the temperature of the back flow reaction is 110 ~ 115 DEG C, and the time of reaction is 1 ~ 10 small
When.
Further, in step (1), the number that the toluene washs repeatedly is 3 times.
Further, in step (2), in the dichloromethane solution of the pyridine, the mass concentration of pyridine is 3.0%.
Further, in step (2), mass ratio 2:1 ~ 20:1 of the 2- bromine isobutyl acylbromide and melamine foams.
Further, in step (2), after dripping 2- bromine isobutyl acylbromide, continuing the time reacted under ice-water bath is 1 small
When.
Further, in step (2), the number that the methylene chloride and acetone wash repeatedly is 5 times.
Further, in step (3), in the butanone and isopropyl alcohol mixed solvent containing monomer 4-vinylpridine,
The volume ratio of butanone and isopropanol is 1:1, and the concentration of monomer 4-vinylpridine is 6.4-64 mg/mL.
Further, in step (3), mass ratio 10:1 ~ 30:1 of the monomer 4-vinylpridine and melamine foams.
Further, in step (3), the quality of the catalyst CuBr is the 2 ~ 6% of 4-vinylpridine quality.
Further, in step (3), the quality of the complexant pentamethyldivinyltriamine is 4-vinylpridine matter
The 15 ~ 25% of amount.
Further, in step (3), the temperature of the reaction is 40 ~ 60 DEG C, and the time of reaction is 2 ~ 20 hours.
Compared with prior art, the invention has the advantages that and the utility model has the advantages that
(1) preparation method of the present invention is simple, low in cost, is suitable for industrialized production；
(2) responsiveness water-oil separating foam of the present invention shows super hydrophilic/super in the solution of pH value lower (pH < 4.5)
Oleophobic property is presented as high hydrophobic/super-oleophilic in the solution of (pH > 4.5) pH higher；
(3) responsiveness water-oil separating foam of the present invention can be not only used for water-oil separating, and the oil of quick release absorption into
Row recycling, can also carry out sewage purification and fluid channel switch control.
Detailed description of the invention
Fig. 1 is the scanning electron microscope (SEM) photograph of pH responsiveness melamine base foam prepared by embodiment 1.
Specific embodiment
Present invention will now be described in further detail with reference to the embodiments and the accompanying drawings, but embodiments of the present invention are unlimited
In this.Other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Embodiment 1
(1) 16mg melamine foams are placed in the 20mL toluene solution containing 200 μ L 3- TSL 8330s
In, back flow reaction 1h at 115 DEG C is cleaned three times repeatedly with toluene, drying in nitrogen atmosphere；
(2) foam obtained is placed in 15mL anhydrous methylene chloride (anhydrous pyridine containing 3.0wt%), under the conditions of 0 DEG C, by
86 μ L 2- bromine isobutyl acylbromide initiators are added dropwise in drop, continue to react 1h under ice-water bath after being added dropwise, then be placed in normal-temperature reaction 12
h；Foam is taken out, is cleaned repeatedly 5 times with methylene chloride and acetone, it is dry in nitrogen atmosphere；
(3) under nitrogen atmosphere, which is placed in 5mL butanone and isopropanol containing 0.32g monomer 4-vinylpridine
In (butanone: isopropanol volume ratio is 1:1) solution, catalyst 15mg CuBr and complexant 60mg pentamethyl divinyl is added
Triamine takes out foam after 50 DEG C of reaction 2h, cleans by deionized water, dry under nitrogen atmosphere, has obtained the close of pH responsiveness
Amido foam.
The scanning electron microscope (SEM) photograph of the melamine base foam of obtained pH responsiveness is as shown in Figure 1, as shown in Figure 1, melamine foams light
Sliding surface is capped a large amount of poly 4 vinyl pyridine, forms coarse surface, shows that pH responsive polymer is good
It is fixed on melamine foams surface and forms the foam with responsiveness.
Embodiment 2
(1) 16mg melamine foams are placed in the 20mL toluene solution containing 450 μ L 3- TSL 8330s
In, back flow reaction 6h at 115 DEG C is cleaned three times repeatedly with toluene solvant, drying in nitrogen atmosphere；
(2) foam obtained is placed in anhydrous 15mL methylene chloride (anhydrous pyridine containing 3.0wt%), under the conditions of 0 DEG C, by
17 μ L 2- bromine isobutyl acylbromide initiators are added dropwise in drop, continue to react 1h under ice-water bath after being added dropwise, then be placed in normal-temperature reaction
12h；Foam is taken out, is cleaned repeatedly 5 times with methylene chloride and acetone, it is dry in nitrogen atmosphere；
(3) under nitrogen atmosphere, which is placed in 10mL butanone and isopropanol containing 0.16g monomer 4-vinylpridine
In (butanone: isopropanol volume ratio is 1:1) solution, catalyst 6mg CuBr and complexant 48mg pentamethyl divinyl three is added
Amine takes out the product after 40 DEG C of reaction 20h, cleans by deionized water, dry under nitrogen atmosphere, has obtained the close of pH responsiveness
Amido foam.
The melamine base foam surface of obtained pH responsiveness can be found in Fig. 1.
Embodiment 3
(1) 16mg melamine foams are placed in the 20mL toluene solution containing 900 μ L 3- TSL 8330s
In, back flow reaction 4h at 115 DEG C is cleaned three times repeatedly with toluene solvant, drying in nitrogen atmosphere；
(2) foam obtained is placed in anhydrous 15mL methylene chloride (anhydrous pyridine containing 3.0wt%), under the conditions of 0 DEG C, by
172 μ L 2- bromine isobutyl acylbromide initiators are added dropwise in drop, continue to react 1h under ice-water bath after being added dropwise, then be placed in normal-temperature reaction
12h；Foam is taken out, is cleaned repeatedly 5 times with methylene chloride and acetone, it is dry in nitrogen atmosphere；
(3) under nitrogen atmosphere, which is placed in 10mL butanone and isopropanol containing 0.32g monomer 4-vinylpridine
In (butanone: isopropanol volume ratio is 1:1) solution, catalyst 19mg CuBr and complexant 80mg pentamethyl divinyl is added
Triamine takes out the product after 50 DEG C of reaction 10h, cleans by deionized water, dry under nitrogen atmosphere, has obtained pH responsiveness
Melamine base foam.
The melamine base foam surface of obtained pH responsiveness can be found in Fig. 1.
Embodiment 4
(1) 16mg melamine foams are placed in the 20mL toluene solution containing 1.5 mL 3- TSL 8330s
In, back flow reaction 8h at 115 DEG C is cleaned three times repeatedly with toluene solvant, drying in nitrogen atmosphere；
(2) foam obtained is placed in anhydrous 15mL methylene chloride (anhydrous pyridine containing 3.0wt%), under the conditions of 0 DEG C, by
86 μ L 2- bromine isobutyl acylbromide initiators are added dropwise in drop, continue to react 1h under ice-water bath after being added dropwise, then be placed in normal-temperature reaction
10h；Foam is taken out, is cleaned repeatedly 5 times with methylene chloride and acetone, it is dry in nitrogen atmosphere；
(3) under nitrogen atmosphere, which is placed in 15mL butanone and isopropanol containing 0.48g monomer 4-vinylpridine
In (butanone: isopropanol volume ratio is 1:1) solution, catalyst 19mg CuBr and complexant 80mg pentamethyl divinyl is added
Triamine takes out the product after 60 DEG C of reaction 15h, cleans by deionized water, dry under nitrogen atmosphere, has obtained pH responsiveness
Melamine base foam.
The melamine base foam surface of obtained pH responsiveness can be found in Fig. 1.
Embodiment 5
(1) 16mg melamine foams are placed in the 20mL toluene solution containing 2 mL 3- TSL 8330s,
Back flow reaction 10h at 115 DEG C is cleaned three times repeatedly with toluene solvant, drying in nitrogen atmosphere；
(2) foam obtained is placed in anhydrous 15mL methylene chloride (anhydrous pyridine containing 3.0wt%), under the conditions of 0 DEG C, by
86 μ L 2- bromine isobutyl acylbromide initiators are added dropwise in drop, continue to react 1h under ice-water bath after being added dropwise, then be placed in normal-temperature reaction
15h.Foam is taken out, is cleaned repeatedly 5 times with methylene chloride and acetone, it is dry in nitrogen atmosphere；
(3) under nitrogen atmosphere, which is placed in 50mL butanone and isopropanol containing 0.32g monomer 4-vinylpridine
In (butanone: isopropanol volume ratio is 1:1) solution, catalyst 15mg CuBr and complexant 60mg pentamethyl divinyl is added
Triamine takes out the product after 50 DEG C of reaction 20h, cleans by deionized water, dry under nitrogen atmosphere, has obtained pH responsiveness
Melamine base foam.
The melamine base foam surface of obtained pH responsiveness can be found in Fig. 1.
The performance of 1 ~ 5 gained pH responsiveness melamine base foam of embodiment: as pH=1.0, the foam is hydrophilic and oleophobic
State (water contact angle in its air is 0 °)；As pH=7.0, which is in the state (water in its air of oleophilic drainage
Contact angle is 135 °)；When pH value of solution > 4.5, which is in the state of oleophilic drainage, can be with oil insoluble in adsorbent solution
Or organic matter, as pH < 4.5, which is in hydrophilic and oleophobic state, the oil of absorption or organic matter can quickly be discharged
Out.The way of recycling of this water-oil separating and oil will not only damage the structure of adsorbent, but also avoid the two of air
Secondary pollution.
Claims (6)
1. a kind of preparation method of pH responsiveness water-oil separating foam, which comprises the steps of:
(1) melamine foams are placed in the toluene solution of 3- TSL 8330, carry out back flow reaction；Reaction terminates
After take out, toluene washs repeatedly, nitrogen drying；The mass concentration of the toluene solution of the 3- TSL 8330 is
1~10 %；The temperature of the back flow reaction is 110 ~ 115 DEG C, and the time of reaction is 1 ~ 10 hour；
(2) foam impregnation for obtaining step (1) is in the dichloromethane solution of pyridine, and under ice-water bath, 2- bromine is added dropwise dropwise
Isobutyl acylbromide continues to be reacted under ice-water bath after being added dropwise to complete, react again under room temperature 10 ~ 15 hours；It takes after reaction
Out, it is successively washed repeatedly with methylene chloride and acetone, it is dry under nitrogen atmosphere；
(3) under nitrogen atmosphere, the foam that step (2) obtains is placed in the butanone containing monomer 4-vinylpridine and isopropanol is mixed
In bonding solvent, catalyst CuBr and complexant pentamethyldivinyltriamine is added, is reacted；It takes out, goes after reaction
Ionized water cleans, dry under nitrogen atmosphere, obtains the pH responsiveness water-oil separating foam；The quality of the catalyst CuBr is 4-
The 2 ~ 6% of vinylpyridine quality；The quality of the complexant pentamethyldivinyltriamine is the 15 of 4-vinylpridine quality
~25%；The temperature of the reaction is 40 ~ 60 DEG C, and the time of reaction is 2 ~ 20 hours.
2. a kind of preparation method of pH responsiveness water-oil separating foam according to claim 1, which is characterized in that step
(1) in, the number that the toluene washs repeatedly is 3 times.
3. a kind of preparation method of pH responsiveness water-oil separating foam according to claim 1, which is characterized in that step
(2) in, in the dichloromethane solution of the pyridine, the mass concentration of pyridine is 3.0%；The 2- bromine isobutyl acylbromide and melamine steep
Mass ratio 2:1 ~ 20:1 of foam.
4. a kind of preparation method of pH responsiveness water-oil separating foam according to claim 1, which is characterized in that step
(2) in, after dripping 2- bromine isobutyl acylbromide, continuing the time reacted under ice-water bath is 1 hour；The methylene chloride and acetone
The number washed repeatedly is 5 times.
5. a kind of preparation method of pH responsiveness water-oil separating foam according to claim 1, which is characterized in that step
(3) in, in the butanone and isopropyl alcohol mixed solvent containing monomer 4-vinylpridine, the volume ratio of butanone and isopropanol is
1:1, the concentration of monomer 4-vinylpridine are 6.4-64 mg/mL；The quality of the monomer 4-vinylpridine and melamine foams
Than 10:1 ~ 30:1.
6. a kind of pH responsiveness water-oil separating foam made from the preparation method as described in claim 1, which is characterized in that with melamine
Foam is carrier, and surface grafting pH responsive polymer poly 4 vinyl pyridine is, it can be achieved that pH responsiveness water-oil separating, by changing
Change pH values, water contact angle are adjustable within the scope of 0 ~ 135 °.
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| CN110947360A (en) * | 2018-09-26 | 2020-04-03 | 中国石油天然气股份有限公司 | pH-responsive ultra-light porous carbon material and preparation method and application thereof |
| CN111013199A (en) * | 2019-12-31 | 2020-04-17 | 常州大学 | Preparation method of intelligent pH response type melamine foam oil-water separation material |
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| CN105170110A (en) * | 2015-05-18 | 2015-12-23 | 西北大学 | Magnetic composite nanoparticle and preparation method thereof |
| CN105693940A (en) * | 2016-04-07 | 2016-06-22 | 咸阳师范学院 | 4-vinylpyridine resin and preparation method and application thereof |
| CN106215904A (en) * | 2016-09-27 | 2016-12-14 | 郑州峰泰纳米材料有限公司 | A kind of method obtaining oil absorption material for substrate with melamine resin foam |
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| TWI402277B (en) * | 2007-12-31 | 2013-07-21 | Ind Tech Res Inst | Method of forming an adsorptive ion-exchange material |
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Patent Citations (3)
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|---|---|---|---|---|
| CN105170110A (en) * | 2015-05-18 | 2015-12-23 | 西北大学 | Magnetic composite nanoparticle and preparation method thereof |
| CN105693940A (en) * | 2016-04-07 | 2016-06-22 | 咸阳师范学院 | 4-vinylpyridine resin and preparation method and application thereof |
| CN106215904A (en) * | 2016-09-27 | 2016-12-14 | 郑州峰泰纳米材料有限公司 | A kind of method obtaining oil absorption material for substrate with melamine resin foam |
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| Smart Fiber Membrane for pH-Induced Oil/Water Separation;Jin-Jin Li et al.;《ACS Appl. Mater. Interfaces》;20150821;第7卷;19643？19650 * |
| Superhydrophobic Silanized Melamine Sponges as High Efficiency Oil Absorbent Materials;Viet Hung Pham et al.;《ACS Appl. Mater. Interfaces》;20140721;第6卷;14181？14188 * |
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