CN110183600A - A kind of paramagnetism novolac polymer complex microsphere and preparation method thereof - Google Patents
A kind of paramagnetism novolac polymer complex microsphere and preparation method thereof Download PDFInfo
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- CN110183600A CN110183600A CN201910470049.6A CN201910470049A CN110183600A CN 110183600 A CN110183600 A CN 110183600A CN 201910470049 A CN201910470049 A CN 201910470049A CN 110183600 A CN110183600 A CN 110183600A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
- C08G8/22—Resorcinol
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2265—Oxides; Hydroxides of metals of iron
- C08K2003/2275—Ferroso-ferric oxide (Fe3O4)
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/01—Magnetic additives
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Abstract
The present invention provides a kind of preparation methods of paramagnetism novolac polymer complex microsphere, comprising: water-soluble phenols, aldehydes solution, catalyst, water-based magnetic fluid and aqueous phase solvent mixing obtain water phase；Surfactant and oil phase solvent are mixed, above-mentioned water phase is added dropwise, emulsifies, obtains lotion；Lotion carries out polymerization reaction, obtains paramagnetism novolac polymer complex microsphere.The present invention passes through water-soluble phenols, aldehydes and water-soluble magnetic fluid mixed solution under the conditions of basic catalyst, carries out inverse emulsion polymerization, step preparation size is controllable, size is distributed uniform paramagnetism novolac polymer microballoon.Using water-soluble material, the compatibility between raw material and high magnetic nanoparticle is improved, the phenolic hydroxyl group that especially phenols in raw material contains forms stronger hydrogen bond with magnetic nanoparticle, makes it combine stronger.Method of the invention prepares magnetic core simple process, and prepared magnetic core has the characteristics that size controllably and narrow size distribution, magnetic response is fast, structural modification is easy.
Description
Technical field
The present invention relates to magnetic catalyst preparation field, more particularly, to a kind of paramagnetism novolac polymer complex microsphere and
Preparation method.
Background technique
Immunomagnetic beads are a kind of Magnetic polymer composite materials, are widely used in immune detection, cell separation, big point of biology
The fields such as son purifying and molecular biology.The structure of immunomagnetic beads can be divided into three parts: the magnetic core of internal layer, middle layer from the inside to surface
Three parts of confining bed and outermost functional layer etc..Wherein, important component of the magnetic core as immunomagnetic beads, direct shadow
Ring the performances such as size and its distribution, the Magneto separate of immunomagnetic beads.Meanwhile the superiority and inferiority of performance is also to obtain high-performance to exempt from
The technological difficulties and emphasis of epidemic disease magnetic bead.
Currently, the immunomagnetic beads of commercialization have the immunomagnetic beads such as Dyna series and JSR series.The preparation magnetic core that they are provided
In, mainly using phenylethylene micro ball as template, on the surface of the microsphere by iron ion absorption, hydrolysis, deposition process or magnetic fluid
Coating procedure, to construct corresponding construction magnetic core；In addition, there are also patent CN106040309A with hydrophobicity magnetic fluid with polymerize singly
Body (styrene or acrylic acid derivative) mixture is polymerize, and magnetic core is directly obtained.
But technical solution that Dyna magnetic bead and JSR magnetic bead provide, building magnetic core there are techniques relative complex, size Control
Hardly possible is difficult the disadvantages of obtaining high magnetic content magnetic bead；In addition, magnetic fluid uniformly mixes with polymerized monomer, polymerize, magnetic can be directly obtained
Core.But this method leads to the poor compatibility of polymerization system component due to the polarity difference between magnetic fluid and polymerized monomer.?
In polymerization process, the mutually separation of magnetic fluid and polymerized monomer can be caused, be not easy to obtain the magnetic core of size uniformity, high magnetic content.
Summary of the invention
In view of this, the technical problem to be solved in the present invention is that providing a kind of paramagnetism novolac polymer complex microsphere
Preparation method, the paramagnetism novolac polymer complex microsphere size that the present invention is prepared is controllable, size distribution is uniform, and magnetic
Fast response time.
The present invention provides a kind of preparation methods of paramagnetism novolac polymer complex microsphere, comprising:
Water-soluble phenols, aldehydes solution, catalyst, water-based magnetic fluid and aqueous phase solvent mixing, obtain water phase；
Surfactant and oil phase solvent are mixed, above-mentioned water phase is added dropwise, emulsifies, obtains lotion；Lotion polymerize anti-
It answers, obtains paramagnetism novolac polymer complex microsphere.
Preferably, the water-soluble phenols is selected from one of phenol and its derivatives, diphenol and its derivative or a variety of.
Preferably, the aldehydes includes one of benzaldehyde and its derivative, formalin and paraformaldehyde or more
Kind.
Preferably, the amount ratio of the phenols and aldehydes solution mass is 1:0.8~1:3；
The weight ratio ratio of the aqueous phase solvent and water-soluble phenols is 1~10:1；
The weight ratio of the catalyst and water-soluble phenols is 1:(100~10000).
Preferably, the water-based magnetic fluid dosage accounts for water-soluble phenols weight percent 10%~50%；The water base magnetic
Fluid is Fe3O4Water-based magnetic fluid.
Preferably, the catalyst is selected from one or more of carbonate, bicarbonate salts and alkalescent inorganic salts；
The aqueous phase solvent is selected from one or more of water and alcoholic solution.
Preferably, the surfactant be selected from Span-20, Span-40, Span-60, Span-80, Tween20,
One or more of Tween 40, Tween 60 and Tween 8；The concentration of the surfactant is 0.001~0.1g/
mL。
The oil phase solvent alkane solvents and aromatic hydrocarbon solvent；
The weight ratio of the surfactant and oil phase solvent is (1~10): (100~1000)；
The weight ratio of the aqueous phase solvent and oil phase solvent: (1~40): 100.
Preferably, the reaction temperature is 40~100 DEG C；Reaction time be 1~for 24 hours.
It preferably, further include by solid component cleaning, centrifuge separation, vacuum drying after the reaction；The cleaning is to adopt
It is cleaned by ultrasonic with water and ethyl alcohol；The centrifugal rotational speed is 1000~4000r/min；The vacuum drying temperature be 40~
80℃。
The present invention provides a kind of paramagnetism novolac polymer complex microspheres, as described in above-mentioned technical proposal any one
Preparation method is prepared.
Compared with prior art, the present invention provides a kind of preparation method of paramagnetism novolac polymer complex microsphere, packets
Include: water-soluble phenols, aldehydes solution, catalyst, water-based magnetic fluid and aqueous phase solvent mixing obtain water phase；By surfactant
It is mixed with oil phase solvent, above-mentioned water phase is added dropwise, emulsified, obtain lotion；Lotion carries out polymerization reaction, obtains the polymerization of paramagnetism phenolic aldehyde
Object complex microsphere.The present invention passes through water-soluble phenols, aldehydes and water-soluble magnetic fluid mixed solution under the conditions of basic catalyst,
Inverse emulsion polymerization is carried out, step preparation size is controllable, size is distributed uniform paramagnetism novolac polymer microballoon.Using water-soluble
Property raw material, be conducive to improve the compatibility between raw material and high magnetic nanoparticle, the especially phenol contained by the phenols in raw material
Hydroxyl can form stronger hydrogen bond with magnetic nanoparticle, make it combine stronger.Meanwhile polymer generated is height
Cross-linking type, porous polymer are conducive to coat more magnetic nanoparticles, can effectively improve the performances such as magnetic core response.This hair
Bright method prepares magnetic core simple process, and prepared magnetic core has size controllable and narrow size distribution, magnetic response are fast, structure is repaired
The features such as decorations are easy.
Detailed description of the invention
Fig. 1 is the SEM figure for the paramagnetism novolac polymer complex microsphere 1 that the embodiment of the present invention 1 is prepared.
Specific embodiment
The present invention provides a kind of paramagnetism novolac polymer complex microspheres and preparation method thereof, and those skilled in the art can
To use for reference present disclosure, it is suitably modified realization of process parameters.In particular, it should be pointed out that all similar substitutions and modifications are to this
It is for the technical staff of field it will be apparent that they shall fall within the protection scope of the present invention.Method and application of the invention is
Through being described by preferred embodiment, related personnel obviously can not depart from the content of present invention, in spirit and scope to this
The methods and applications of text are modified or appropriate changes and combinations, carry out implementation and application the technology of the present invention.
The present invention provides a kind of preparation methods of paramagnetism novolac polymer complex microsphere, comprising:
Water-soluble phenols, aldehydes solution, catalyst, water-based magnetic fluid and aqueous phase solvent mixing, obtain water phase；
Surfactant and oil phase solvent are mixed, above-mentioned water phase is added dropwise, emulsifies, obtains lotion；Lotion polymerize anti-
It answers, obtains paramagnetism novolac polymer complex microsphere.
The present invention first mixes water-soluble phenols, aldehydes solution, catalyst, water-based magnetic fluid and aqueous phase solvent, obtains
Water phase.
According to the present invention, the water solubility phenols is preferably selected from one in phenol and its derivatives, diphenol and its derivative
Kind is a variety of；More preferably phenol and resorcinol；
The aldehydes preferably includes one of benzaldehyde and its derivative, formalin and paraformaldehyde or a variety of；
More preferably formaldehyde；It can be formalin.
In the present invention, the amount of the phenols and aldehydes solution mass is than being preferably 1:0.8~1:3；More preferably 1:0.9
~1:2.
Wherein, the catalyst is preferably selected from one or more of carbonate, bicarbonate salts and alkalescent inorganic salts；
More preferably one or more of sodium carbonate, potassium carbonate, sodium bicarbonate and saleratus；
The aqueous phase solvent is selected from one or more of water and alcoholic solution.It as can be aqueous solution or water and ethyl alcohol
Mixed solution；Wherein one or more of the preferred methanol of the alcohols, ethyl alcohol, propyl alcohol and isopropanol.
According to the present invention, the weight ratio of the aqueous phase solvent and water-soluble phenols is preferably 1~10:1；More preferably 2~
9:1；Most preferably 3~8:1；
The weight ratio of the catalyst and water-soluble phenols is preferably 1:(100~10000)；More preferably 1:(150~
9000)；Most preferably 1:(200~8000).
Water-based magnetic fluid of the present invention includes but is not limited to Fe3O4Water-based magnetic fluid；Water-based magnetic fluid of the present invention is used
Amount is to account for water-soluble phenols weight percent preferably 10%~50%；More preferably 15%~45%.
After obtaining water phase, surfactant and oil phase solvent are mixed.
Wherein, the surfactant is selected from Span-20, Span-40, Span-60, Span-80, Tween20, Tween
40, one or more of Tween 60 and Tween 8；The concentration of the surfactant is preferably 0.001~0.1g/mL；
More preferably 0.01~0.09g/mL；Most preferably 0.02~0.08g/mL；The oil phase solvent be preferably alkane solvents and
Aromatic hydrocarbon solvent；More preferably petroleum ether, n-hexane, hexamethylene, normal heptane, normal octane, n -nonane, n-decane, positive 12
One or more of alkane, toluene and benzene.
According to the present invention, the weight ratio of the surfactant and oil phase solvent is preferably (1~10): (100~1000)；
More preferably (2~9): (150~900)；Most preferably (3~8): (200~800)；
After mixing, above-mentioned water phase is added dropwise, emulsifies, obtains lotion.
According to the present invention, the weight ratio of the aqueous phase solvent and oil phase solvent is preferably (1~40): 100；More preferably (5
~35): 100.
The present invention for the dropwise addition speed without limit, preferably can be 5~20mL/min；More preferably
10mL/min。
It is emulsified, is added dropwise using high-shear emulsion machine, continue 2~5min of emulsification, prepare lotion.
Lotion carries out polymerization reaction, obtains paramagnetism novolac polymer complex microsphere.
Lotion is transferred in reaction flask, mechanical stirring, carries out polymerization reaction；The reaction temperature is preferably 40~100
℃；More preferably 50~90 DEG C；Most preferably 60~80 DEG C；The reaction time is preferably 1~for 24 hours；More preferably 2~20h；
Most preferably 5~10h.
According to the present invention, after reaction, reaction solution is cooled to room temperature, and is centrifuged.The present invention is for cooling mode
Without limiting, natural cooling；The present invention for the centrifugation mode without limiting, those skilled in the art are known
?.
Obtained solid component, by solid component cleaning, centrifuge separation, vacuum drying；The cleaning is using water and second
Alcohol is successively cleaned by ultrasonic；
The centrifugal rotational speed is preferably 1000~4000r/min；More preferably 2000r/min；The vacuum drying temperature
Preferably 40~80 DEG C of degree；More preferably 60 DEG C.
Preparation paramagnetism novolac polymer complex microsphere method provided by the invention is simpler, and size Control is easy.It is made
Standby porous polymer microsphere has high magnetic response speed, while microsphere surface contains phenolic hydroxyl group, be conducive to further to close and
Functionalization.
The present invention provides a kind of paramagnetism novolac polymer complex microspheres, as described in above-mentioned technical proposal any one
Preparation method is prepared.
The present invention provides a kind of preparation methods of paramagnetism novolac polymer complex microsphere, comprising: water-soluble phenols, aldehyde
Class solution, catalyst, water-based magnetic fluid and aqueous phase solvent mixing, obtain water phase；Surfactant and oil phase solvent are mixed, drop
In addition stating water phase, emulsifies, obtain lotion；Lotion carries out polymerization reaction, obtains paramagnetism novolac polymer complex microsphere.The present invention
Through water-soluble phenols, aldehydes and water-soluble magnetic fluid mixed solution under the conditions of basic catalyst, inverse emulsion polymerization is carried out,
One step preparation size is controllable, size is distributed uniform paramagnetism novolac polymer microballoon.Using water-soluble material, be conducive to improve
Compatibility between raw material and high magnetic nanoparticle, the especially phenolic hydroxyl group contained by the phenols in raw material can be with magnetic Nanos
Particle forms stronger hydrogen bond, makes it combine stronger.Meanwhile polymer generated be high cross-linking type, porous polymer,
Be conducive to coat more magnetic nanoparticles, the performances such as magnetic core response can be effectively improved.Method of the invention prepares magnetic core work
Skill is simple, and prepared magnetic core has the characteristics that size controllable and narrow size distribution, magnetic response is fast, structural modification is easy.
In order to further illustrate the present invention, with reference to embodiments to a kind of paramagnetism novolac polymer provided by the invention
Complex microsphere and preparation method thereof is described in detail.
Embodiment 1
Resorcinol (1.04g), 37% formalin (1.07g), sodium carbonate (0.05g), water-based magnetic fluid is molten
Liquid (1.07g) and water (2.8g) mixing, dissolution preparation water phase.The drop into the hexane solution (0.02g/mL, 50mL) of Span-20
In addition stating the water phase of preparation, while being emulsified, be added dropwise using high-shear emulsion machine, continued to emulsify 2min, prepare lotion.
Then lotion is transferred in reaction flask, mechanical stirring 5 hours at 60 DEG C.End of reaction, reaction solution are cooled to room temperature, carry out from
Heart separation.Obtained solid component carries out ultrasonic cleaning with acetone, water and ethyl alcohol respectively and centrifuge separation is purified.Finally,
Vacuum drying is carried out at 60 DEG C can be obtained paramagnetism novolac polymer complex microsphere, and Fig. 1 is that the embodiment of the present invention 1 is prepared into
The SEM of the paramagnetism novolac polymer complex microsphere 1 arrived schemes.As seen from Figure 1, average-size 150nm, Fe3O4Content is
21%, saturated magnetization rate is 13emu/g.
Embodiment 2
Resorcinol (1.04g), 37% formalin (1.07g), sodium carbonate (0.05g), water-based magnetic fluid is molten
Liquid (1.07g) and water (5.8g) mixing, dissolution preparation water phase.The drop into the hexane solution (0.02g/mL, 50mL) of Span-20
In addition stating the water phase of preparation, while being emulsified, be added dropwise using high-shear emulsion machine, continued to emulsify 2min, prepare lotion.
Then lotion is transferred in reaction flask, mechanical stirring 5 hours at 60 DEG C.End of reaction, reaction solution are cooled to room temperature, carry out from
Heart separation.Obtained solid component carries out ultrasonic cleaning with acetone, water and ethyl alcohol respectively and centrifuge separation is purified.Finally,
Vacuum drying is carried out at 60 DEG C can be obtained paramagnetism novolac polymer complex microsphere, average-size 100nm, and Fe3O4 contains
Amount is 23%, and saturated magnetization rate is 14emu/g.
Embodiment 3
Resorcinol (1.04g), 37% formalin (1.07g), sodium carbonate (0.05g), water-based magnetic fluid is molten
Liquid (1.07g) and water (2.8g) mixing, dissolution preparation water phase.The drop into the hexane solution (0.02g/mL, 50mL) of Span-20
In addition stating the water phase of preparation, while being emulsified, be added dropwise using high-shear emulsion machine, continued to emulsify 2min, prepare lotion.
Then lotion is transferred in reaction flask, mechanical stirring 5 hours at 60 DEG C.End of reaction, reaction solution are cooled to room temperature, carry out from
Heart separation.Obtained solid component carries out ultrasonic cleaning with acetone, water and ethyl alcohol respectively and centrifuge separation is purified.Finally,
Vacuum drying is carried out at 60 DEG C can be obtained paramagnetism novolac polymer complex microsphere, average-size 80um, Fe3O4 content
It is 18%, saturated magnetization rate is 10emu/g.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of paramagnetism novolac polymer complex microsphere characterized by comprising
Water-soluble phenols, aldehydes solution, catalyst, water-based magnetic fluid and aqueous phase solvent mixing, obtain water phase；
Surfactant and oil phase solvent are mixed, above-mentioned water phase is added dropwise, emulsifies, obtains lotion；Lotion carries out polymerization reaction, obtains
To paramagnetism novolac polymer complex microsphere.
2. preparation method according to claim 1, which is characterized in that the water solubility phenols is raw selected from phenol derivmives blend
One of object, diphenol and its derivative are a variety of.
3. preparation method according to claim 2, which is characterized in that the aldehydes includes benzaldehyde and its derivative, first
One of aldehyde aqueous solution and paraformaldehyde are a variety of.
4. preparation method according to claim 3, which is characterized in that the amount ratio of the phenols and aldehydes solution mass is 1:
0.8~1:3；
The weight ratio ratio of the aqueous phase solvent and water-soluble phenols is 1~10:1；
The weight ratio of the catalyst and water-soluble phenols is 1:(100~10000).
5. preparation method according to claim 1, which is characterized in that the water-based magnetic fluid dosage accounts for water-soluble phenols weight
Measure percentage 10%~50%；The water-based magnetic fluid is Fe3O4Water-based magnetic fluid.
6. preparation method according to claim 1, which is characterized in that the catalyst is selected from carbonate, bicarbonate salts
One or more of with alkalescent inorganic salts；
The aqueous phase solvent is selected from one or more of water and alcoholic solution.
7. preparation method according to claim 1, which is characterized in that the surfactant is selected from Span-20, Span-
40, one or more of Span-60, Span-80, Tween20, Tween40, Tween60 and Tween8；The surface-active
The concentration of agent is 0.001~0.1g/mL；
The oil phase solvent alkane solvents and aromatic hydrocarbon solvent；
The weight ratio of the surfactant and oil phase solvent is (1~10): (100~1000)；
The weight ratio of the aqueous phase solvent and oil phase solvent: (1~40): 100.
8. preparation method according to claim 1, which is characterized in that the reaction temperature is 40~100 DEG C；Reaction time
For 1~for 24 hours.
9. preparation method according to claim 1, which is characterized in that further include after the reaction by solid component cleaning,
Centrifuge separation, vacuum drying；The cleaning is to be cleaned by ultrasonic using water and ethyl alcohol；The centrifugal rotational speed be 1000~
4000r/min；The vacuum drying temperature is 40~80 DEG C.
10. a kind of paramagnetism novolac polymer complex microsphere, which is characterized in that by system described in any one of claim 1 to 9
Preparation Method is prepared.
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| CN103657546A (en) * | 2012-09-20 | 2014-03-26 | 复旦大学 | Method for preparing nuclear shell type magnetic composite resin microballoons |
| CN104387712A (en) * | 2014-11-03 | 2015-03-04 | 遵义医学院 | Nano composite carrier with superparamagnetism and preparation method thereof |
| CN109293860A (en) * | 2018-10-25 | 2019-02-01 | 齐鲁工业大学 | A kind of preparation method of magnetism yolk structure phenolic aldehyde resin microsphere |
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2019
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|---|---|---|---|---|
| CN103657546A (en) * | 2012-09-20 | 2014-03-26 | 复旦大学 | Method for preparing nuclear shell type magnetic composite resin microballoons |
| CN104387712A (en) * | 2014-11-03 | 2015-03-04 | 遵义医学院 | Nano composite carrier with superparamagnetism and preparation method thereof |
| CN109293860A (en) * | 2018-10-25 | 2019-02-01 | 齐鲁工业大学 | A kind of preparation method of magnetism yolk structure phenolic aldehyde resin microsphere |
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