CN109053960A - A kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle - Google Patents
A kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle Download PDFInfo
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- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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Abstract
The invention belongs to field of nanometer material technology, more particularly to a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle: preparing maleic anhydride modified beta-cyclodextrin, pass through emulsion polymerization again, using maleic anhydride modified beta-cyclodextrin, styrene and n-isopropyl acrylamide as monomer, the beta-cyclodextrin nanoparticle of preparation temperature sensitivity.The maleic anhydride modified beta-cyclodextrin of the present invention, again with styrene and n-isopropyl acrylamide and maleic anhydride modified beta-cyclodextrin alternating copolymerization, the introducing of styrene is easy to that alternating copolymerization occurs with MAH- β-CD, is conducive to NIPAM and MAH- β-CD and all preferably participates in copolyreaction；The partial size of temperature sensitive beta-cyclodextrin nanoparticle is between 60-100nm prepared by the present invention, and monodispersity is preferable, good sphericity；Prepared beta-cyclodextrin nanoparticle has apparent temperature sensitivity, can perceive the variation of ambient temperature, generate the swelling and contraction of volume.
Description
Technical field
The invention belongs to field of nanometer material technology, and in particular to a kind of preparation side of temperature sensitive beta-cyclodextrin nanoparticle
Method.
Background technique
Beta-cyclodextrin (β-CD) is a hollow and annular oligosaccharide compound, has intracavitary hydrophobic, chamber external hydrophilicity amphiphilic
Property feature, and can with various guest compounds formed super molecule inclusion compound.Special structure impart cyclic dextrin clathrate, sustained release,
The ability of catalysis, Cyclodextrin Polymer can be effectively applied to drug release as pharmaceutical carrier.
In recent years, stimulating responsive nano structural material is because the potential application in drug delivery and biology obtains
It is widely applied research.Since temperature signal is widely present in environmental signal, and it is easiest to one of the signal of control, therefore
Thermo-sensitive material has received widespread attention in numerous stimulating responsive nano structural materials.
When beta-cyclodextrin is used for field of medicine release at present, it is faced with and has a single function the problem excessive with partial size.Utilize β-
The unique molecule inclusion of CD, slow-release capability and poly(N-isopropylacrylamide) (PNIPAM) are in lowest critical solution temperature
(LCST) swelling and Shrinkage behavior nearby shown can by n-isopropyl acrylamide and beta-cyclodextrin with Covalent bonding together
Assign beta-cyclodextrin new function.The beta-cyclodextrin nanoparticle of size tunable is prepared using the method for emulsion polymerization simultaneously.
Summary of the invention
The invention discloses a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle, the temperature of size tunable is quick
The preparation method of the beta-cyclodextrin nanoparticle of sense,
It solves the above problems, the invention discloses a kind of Ni-based extraordinary welding wire of high-performance stainless steel built-up welding and its preparation sides
Method, the welding wire have the gas of resistance to activity, resistance to caustic medium, the superperformance of reducing resistance acid medium corrosion, in welding process
In, arc stability and slag removing are excellent, can obtain excellent welding bead construction, obtain with intensity height, good toughness, resistance to defect
Property, high-temperature cracking resistance, the welding metal of corrosion resistance.
To achieve the goals above, the present invention adopts the following technical scheme:
A kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle, it is characterised in that: the preparation method is that, system
Standby maleic anhydride modified beta-cyclodextrin, then by emulsion polymerization, with maleic anhydride modified beta-cyclodextrin, styrene and N- isopropyl
Base acrylamide is monomer, the beta-cyclodextrin nanoparticle of preparation temperature sensitivity.
Specifically, the preparation method of above-mentioned temperature sensitive beta-cyclodextrin nanoparticle, comprises the following specific steps that:
(1) preparation of maleic anhydride modified beta-cyclodextrin: maleic anhydride and beta-cyclodextrin are added in DMF, 80
Reaction solution is poured slowly into the chloroform soln being stirred continuously after cooling and is settled out product by DEG C reaction 8-10h, then with third
Ketone washs sediment to white, drains to obtain white solid, dry, obtains maleic anhydride modified beta-cyclodextrin, is placed in drying
It is spare in device；
(2) preparation of temperature sensitive beta-cyclodextrin nanoparticle: by styrene, n-isopropyl acrylamide, crosslinking agent,
Maleic anhydride modified beta-cyclodextrin prepared by emulsifier, deionized water and step (1) is uniformly mixed, and is passed through nitrogen under stirring
It is bubbled 15-30min deoxygenation, initiator is then added, is warming up to 70 DEG C under nitrogen protection, Na is used in reaction process2CO3Solution
PH value is adjusted, so that pH value in reaction process is remained at 7-8, stops heating after reaction 6-8 hours, cooled to room temperature,
Obtain temperature sensitive beta-cyclodextrin nanoparticle.
The reaction process of step (1) are as follows:
The reaction process of step (2) are as follows:
Specifically, the molar ratio of beta-cyclodextrin and maleic anhydride is 1:7-12 in above-mentioned steps (1).
Specifically, in above-mentioned steps (2) maleic anhydride modified beta-cyclodextrin, styrene and n-isopropyl acrylamide matter
Amount is than being 1-4:4:16.The present invention has found that when styrene-content is too low, MAH- β-CD and NIPAM can not be very by a large number of experiments
It participates in polymerizeing well, low yield, and when styrene-content is excessively high, although particle size is smaller, Thermo-sensitive is poor, the above dosage
Than that can guarantee that prepared beta-cyclodextrin nanoparticle has more regular spherical structure, lesser partial size and preferable temperature
Quick property.
Specifically, the crosslinking agent in above-mentioned steps (2) is N, N '-methylene-bisacrylamide, the N, N '-di-2-ethylhexylphosphine oxide
The additional amount of acrylamide is the 2-4% of monomer gross mass.Contain and temperature in N, N '-methylene-bisacrylamide (MBA) molecule
The identical acrylamide group of quick monomer n-isopropyl acrylamide can be reduced pair using MBA as crosslinking agent to the maximum extent
The influence of temperature sensitive performance, N is worked as in test discovery, when the additional amount of N '-methylene-bisacrylamide is more than 4%, prepared nanoparticle
Crosslinking can be generated between son.
Specifically, mentioned emulsifier is lauryl sodium sulfate, and the additional amount of the lauryl sodium sulfate is that monomer is total
The 3-5% of quality.Lauryl sodium sulfate (SDS) is anion emulsifier, and emulsifying capacity is very strong, can be the formation of micella
Enough charges are provided, test discovery is when the additional amount of lauryl sodium sulfate is lower than 3%, the partial size of prepared nanoparticle
It is bigger.
Specifically, the initiator in above-mentioned steps (2) is one or both of potassium peroxydisulfate and ammonium persulfate.
Specifically, the initiator additional amount in above-mentioned steps (2) is the 3-5% of monomer gross mass.When initiator amount mistake
It is unobvious to the initiation effect of polymerization when few, and too high levels will lead to implode phenomenon, by test, finally determine initiator
Additional amount is that the 3-5% of monomer gross mass is more appropriate.
Specifically, the structural formula of the temperature sensitive beta-cyclodextrin nanoparticle of above-mentioned steps (2) preparation are as follows:
Specifically, the partial size of the temperature sensitive beta-cyclodextrin nanoparticle of above-mentioned steps (2) preparation is 60-100nm.
The present invention have it is following the utility model has the advantages that the maleic anhydride modified beta-cyclodextrin of the present invention, then with styrene and N-
N-isopropylacrylamide and maleic anhydride modified beta-cyclodextrin alternating copolymerization, the introducing of styrene are easy to hand over MAH- β-CD
For copolymerization, is conducive to NIPAM and MAH- β-CD and all preferably participates in copolyreaction；Temperature sensitive β prepared by the present invention-ring paste
For the partial size of smart nanoparticle between 60-100nm, monodispersity is preferable, good sphericity；Prepared beta-cyclodextrin nanoparticle
With apparent temperature sensitivity, the variation of ambient temperature can be perceived, generates the swelling and contraction of volume.
Detailed description of the invention
Fig. 1 is β-CD (A), MAH- β-CD (B) and temperature sensitive beta-cyclodextrin nanoparticle (Poly (NIPAM-co-
St-co-MAH- β-CD)) infrared spectrum of (C).As shown in Figure 1, compared with spectrogram A, spectrogram B is in 1719cm-1There is carboxylic in place
The symmetrical stretching vibration absorption peak of acid esters illustrates that β-CD is successfully modified by maleic anhydride；Compared with spectrogram B, spectrogram C exists
696cm-1There is the cyclosubstituted peak C-H of benzene in styrene, 1646cm in place-1And 1554cm-1There is NIPAM structural unit in place
Amide characteristic absorption peak, 1458cm-1And 1388cm-1There is the isopropyl characteristic absorption peak of NIPAM structural unit in place, says
It is bright to be successfully prepared temperature sensitive beta-cyclodextrin nanoparticle.
Fig. 2 is the curve graph that beta-cyclodextrin nano particle diameter prepared by embodiment 1 and comparative example 2 varies with temperature.From
Fig. 2 can be seen that in temperature from during being raised to 45 DEG C for 25 DEG C, under beta-cyclodextrin nano particle diameter prepared by embodiment 1
Drop is obvious, and Thermo-sensitive is good, and the change of size of comparative example 1 is little, although illustrating beta-cyclodextrin nanoparticle prepared by comparative example 1
Partial size is smaller, but Thermo-sensitive is poor.
Fig. 3 is the scanning electron microscope (SEM) photograph of beta-cyclodextrin nanoparticle prepared by embodiment 4.As seen from Figure 3, prepared β-
Cyclodextrin nano particle size distribution is uniform, good dispersion.
Fig. 4 is the scanning electron microscope (SEM) photograph of beta-cyclodextrin nanoparticle prepared by comparative example 4.As seen from Figure 4, prepared
Occurs intergranular crosslinking phenomena between beta-cyclodextrin nanoparticle.
Specific embodiment
Presently in connection with embodiment, the present invention is described in further detail.
Embodiment 1
(1) 4.9g maleic anhydride and 5.68g beta-cyclodextrin the preparation of maleic anhydride modified beta-cyclodextrin: are added to 30mL
It in DMF, reacts 10 hours at 80 DEG C, after cooling, reaction solution is poured slowly into the 100mL chloroform soln being stirred continuously
It is settled out product, then is in three times washed sediment to white with enough acetone solns, drains to obtain white solid, by product
Drying in 80 DEG C of vacuum ovens is placed in for 24 hours, to obtain maleic anhydride modified beta-cyclodextrin, be placed in spare in drier；
(2) preparation of temperature sensitive beta-cyclodextrin nanoparticle: by 2g styrene, 8g n-isopropyl acrylamide,
0.33gN, N '-methylene-bisacrylamide, 0.33g lauryl sodium sulfate, 400mL deionized water and 1g step (1) are made
Standby maleic anhydride modified beta-cyclodextrin is uniformly mixed, and nitrogen is passed through under stirring and is bubbled 20min deoxygenation, 0.44g mistake is then added
Potassium sulfate is warming up to 70 DEG C under nitrogen protection, Na is used in reaction process2CO3Solution adjusts pH value, makes pH value in reaction process
7-8 is remained at, stops heating after reaction 7 hours, cooled to room temperature obtains temperature sensitive beta-cyclodextrin nanoparticle
The dispersion liquid of son, the partial size of beta-cyclodextrin nanoparticle is 75nm or so after drying.
Embodiment 2
(1) 4.9g maleic anhydride and 8.11g beta-cyclodextrin the preparation of maleic anhydride modified beta-cyclodextrin: are added to 30mL
It in DMF, reacts 8 hours at 80 DEG C, after cooling, reaction solution is poured slowly into the 100mL chloroform soln being stirred continuously
It is settled out product, then is in three times washed sediment to white with enough acetone solns, drains to obtain white solid, by product
Drying in 80 DEG C of vacuum ovens is placed in for 24 hours, to obtain maleic anhydride modified beta-cyclodextrin, be placed in spare in drier；
(2) preparation of temperature sensitive beta-cyclodextrin nanoparticle: by 2g styrene, 8g n-isopropyl acrylamide,
0.21gN, N '-methylene-bisacrylamide, 0.42g lauryl sodium sulfate, 400mL deionized water and 0.5g step (1) institute
The maleic anhydride modified beta-cyclodextrin of preparation is uniformly mixed, and nitrogen is passed through under stirring and is bubbled 20min deoxygenation, 0.32g is then added
Potassium peroxydisulfate is warming up to 70 DEG C under nitrogen protection, Na is used in reaction process2CO3Solution adjusts pH value, makes pH in reaction process
Value remains at 7-8, stops heating after reaction 6 hours, cooled to room temperature obtains temperature sensitive beta-cyclodextrin nanometer
The dispersion liquid of particle, the partial size of beta-cyclodextrin nanoparticle is 60nm or so after drying.
Embodiment 3
(1) 4.9g maleic anhydride and 4.73g beta-cyclodextrin the preparation of maleic anhydride modified beta-cyclodextrin: are added to 30mL
It in DMF, reacts 9 hours at 80 DEG C, after cooling, reaction solution is poured slowly into the 100mL chloroform soln being stirred continuously
It is settled out product, then is in three times washed sediment to white with enough acetone solns, drains to obtain white solid, by product
Drying in 80 DEG C of vacuum ovens is placed in for 24 hours, to obtain maleic anhydride modified beta-cyclodextrin, be placed in spare in drier；
(2) preparation of temperature sensitive beta-cyclodextrin nanoparticle: by 2g styrene, 8g n-isopropyl acrylamide,
0.48gN, N '-methylene-bisacrylamide, 0.6g lauryl sodium sulfate, 400mL deionized water and 2g step (1) are made
Standby maleic anhydride modified beta-cyclodextrin is uniformly mixed, and nitrogen is passed through under stirring and is bubbled 20min deoxygenation, 0.3g over cure is then added
Sour potassium and 0.3g ammonium persulfate, are warming up to 70 DEG C under nitrogen protection, Na are used in reaction process2CO3Solution adjusts pH value, makes anti-
PH value remains at 7-8 during answering, and stops heating after reaction 8 hours, cooled to room temperature obtains temperature sensitive β-
The dispersion liquid of cyclodextrin nano particle, the partial size of beta-cyclodextrin nanoparticle is 100nm or so after drying.
Embodiment 4
(1) 4.9g maleic anhydride and 6.31g beta-cyclodextrin the preparation of maleic anhydride modified beta-cyclodextrin: are added to 30mL
It in DMF, reacts 10 hours at 80 DEG C, after cooling, reaction solution is poured slowly into the 100mL chloroform soln being stirred continuously
It is settled out product, then is in three times washed sediment to white with enough acetone solns, drains to obtain white solid, by product
Drying in 80 DEG C of vacuum ovens is placed in for 24 hours, to obtain maleic anhydride modified beta-cyclodextrin, be placed in spare in drier；
(2) preparation of temperature sensitive beta-cyclodextrin nanoparticle: by 2g styrene, 8g n-isopropyl acrylamide,
0.34gN, N '-methylene-bisacrylamide, 0.36g lauryl sodium sulfate, 400mL deionized water and 1.2g step (1) institute
The maleic anhydride modified beta-cyclodextrin of preparation is uniformly mixed, and nitrogen is passed through under stirring and is bubbled 20min deoxygenation, 0.45g is then added
Ammonium persulfate is warming up to 70 DEG C under nitrogen protection, Na is used in reaction process2CO3Solution adjusts pH value, makes pH in reaction process
Value remains at 7-8, stops heating after reaction 7 hours, cooled to room temperature obtains temperature sensitive beta-cyclodextrin nanometer
The dispersion liquid of particle, the partial size of beta-cyclodextrin nanoparticle is 88nm or so after drying.
Compared with Example 1, the additional amount of maleic anhydride modified beta-cyclodextrin is that 2.5g is (maleic anhydride modified to comparative example 1
The mass ratio of beta-cyclodextrin and styrene is 5:4, the 1-4:4 limited more than claim), other are the same as embodiment 1.Experimentation
Middle discovery, step (2) generate a large amount of precipitatings, reaction failure.
Compared with Example 1, the additional amount of styrene is the 3g (matter of styrene and n-isopropyl acrylamide to comparative example 2
Amount is than being 6:16, the 4:16 limited more than claim), other are the same as embodiment 1.As shown in Figure 2,2 particle size of comparative example with
The variation of temperature is unobvious, and Thermo-sensitive is poor.
Comparative example 3 compared with Example 1, is not added with styrene, other are the same as embodiment 1.At the end of reaction, embodiment 1 is
Milky white liquid, and occur partly precipitated in comparative example 3, this may be due to being not added with styrene in the case where, maleic anhydride
It cannot be copolymerized well between modified beta-cyclodextrin and n-isopropyl acrylamide, but depositing due to emulsifier and initiator
Autohemagglutination can occur in, n-isopropyl acrylamide monomer, generation mutually separates, to there is partly precipitated precipitation.
Compared with Example 1, the additional amount of N, N '-methylene-bisacrylamide is 0.55g (N, N '-methylene to comparative example 4
Bisacrylamide dosage reaches the 5% of monomer mass), other are the same as embodiment 1.From fig. 4, it can be seen that being handed between particle
Connection.
Comparative example 5 compared with Example 1, uses hectorite as crosslinking agent, other are the same as embodiment 1.With 1 phase of embodiment
Than the LCST higher of 5 product of comparative example, this may be since hectorite is Physical crosslinking agent, by molecule in a manner of hydrogen bond
Together, the formation of a large amount of hydrogen bonds causes the LCST of temperature-sensitive nano particle to rise to chain link, has an impact to Thermo-sensitive.
Comparative example 6 compared with Example 1, adds stearic acid sodium salt as emulsifier, other are the same as embodiment 1.It is prepared
Beta-cyclodextrin particle it is dry after partial size reach 300nm or so.
Taking the above-mentioned ideal embodiment according to the present invention as inspiration, through the above description, relevant staff is complete
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property range is not limited to the contents of the specification, it is necessary to which the technical scope thereof is determined according to the scope of the claim.
Claims (10)
1. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle, it is characterised in that: the preparation method is that, preparation
Maleic anhydride modified beta-cyclodextrin, then by emulsion polymerization, with maleic anhydride modified beta-cyclodextrin, styrene and N- isopropyl
Acrylamide is monomer, the beta-cyclodextrin nanoparticle of preparation temperature sensitivity.
2. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as described in claim 1, it is characterised in that: packet
Include following specific steps:
(1) preparation of maleic anhydride modified beta-cyclodextrin: maleic anhydride and beta-cyclodextrin are added in DMF, anti-at 80 DEG C
Answer 8-10h that reaction solution is poured slowly into the chloroform soln being stirred continuously and is settled out product after cooling, then will with acetone
Sediment is washed to white, drains to obtain white solid, dry, is obtained maleic anhydride modified beta-cyclodextrin, is placed in drier
It is spare；
(2) preparation of temperature sensitive beta-cyclodextrin nanoparticle: by styrene, n-isopropyl acrylamide, crosslinking agent, emulsification
Maleic anhydride modified beta-cyclodextrin prepared by agent, deionized water and step (1) is uniformly mixed, and nitrogen bubbling is passed through under stirring
15-30min deoxygenation, is then added initiator, is warming up to 70 DEG C under nitrogen protection, Na is used in reaction process2CO3Solution is adjusted
PH value makes pH value in reaction process remain at 7-8, stops heating after reaction 6-8 hours, cooled to room temperature is made
Obtain temperature sensitive beta-cyclodextrin nanoparticle.
3. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as claimed in claim 2, it is characterised in that: institute
Stating the molar ratio of beta-cyclodextrin and maleic anhydride in step (1) is 1:7-12.
4. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as claimed in claim 2, it is characterised in that: institute
The mass ratio for stating maleic anhydride modified beta-cyclodextrin, styrene and n-isopropyl acrylamide in step (2) is 1-4:4:16.
5. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as claimed in claim 2, it is characterised in that: institute
Stating the crosslinking agent in step (2) is N, N '-methylene-bisacrylamide, the N, the additional amount of N '-methylene-bisacrylamide
For the 2-4% of monomer gross mass.
6. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as claimed in claim 2, it is characterised in that: institute
Stating emulsifier is lauryl sodium sulfate, and the additional amount of the lauryl sodium sulfate is the 3-5% of monomer gross mass.
7. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as claimed in claim 2, it is characterised in that: institute
Stating the initiator in step (2) is one or both of potassium peroxydisulfate and ammonium persulfate.
8. a kind of preparation method of temperature sensitive beta-cyclodextrin nanoparticle as claimed in claim 7, it is characterised in that: institute
State the 3-5% that the initiator additional amount in step (2) is monomer gross mass.
9. special such as a kind of described in any item preparation methods of temperature sensitive beta-cyclodextrin nanoparticle of claim 1-8
Sign is: the structural formula of the temperature sensitive beta-cyclodextrin nanoparticle of step (2) preparation are as follows:
10. special such as a kind of described in any item preparation methods of temperature sensitive beta-cyclodextrin nanoparticle of claim 1-8
Sign is that the partial size of the temperature sensitive beta-cyclodextrin nanoparticle of step (2) preparation is 60-100nm.
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| CN110951091A (en) * | 2019-12-10 | 2020-04-03 | 常州大学 | Preparation method of double-sensitive slow-release β -cyclodextrin hydrogel |
| CN112079961A (en) * | 2020-09-22 | 2020-12-15 | 清华大学 | Crosslinked polymer, preparation method thereof, drug loading body and biomedical implant material |
| CN114100606A (en) * | 2021-11-12 | 2022-03-01 | 扬州工业职业技术学院 | Temperature-sensitive nano noble metal palladium catalyst and preparation method thereof |
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