CN110358759A - A kind of Pickering lotion and preparation method thereof for encapsulating lipase - Google Patents
A kind of Pickering lotion and preparation method thereof for encapsulating lipase Download PDFInfo
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- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
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- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
- C12Y301/01003—Triacylglycerol lipase (3.1.1.3)
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Abstract
The invention belongs to lotion preparation technical fields, disclose a kind of Pickering lotion and preparation method thereof for encapsulating lipase.Lotion of the present invention carries out esterification modification to the starch after gelatinization using modified starch as particle stabilizers, especially by esterifying agent, is granulated, and obtains esterification nano particle；Then coupling reaction is carried out with methoxy silane, carries out hydrophobically modified；After being scattered in organic solution again as oily phase, is mixed with the water phase of lipase solution, stir to get stable Pickering lotion.The present invention is by being esterified starch and silylating reagent, wherein the esterifying agents such as benzoic anhydride and its derivative make particle have very high interfacial activity due to the presence of carboxyl；And alcoholic extract hydroxyl group can generate hydrogen bond with hydroxyl in starch after methoxy silane hydrolysis more than 8 carbochains, assign its unique hydrophobicity, modified starch granules can form stable Pickering lotion with lipase solution, realize the encapsulating of lipase.
Description
Technical field
The invention belongs to lotion preparation technical field, in particular to a kind of Pickering lotion for encapsulating lipase and its
Preparation method.
Background technique
In recent years, the research and development for constructing zymophore by Water-In-Oil Pickering lotion is rapid.But in order to meet
Fine dispersion of the particle in oily phase generally requires modified to particulate surface hydrophobic.In addition, the biocompatibility of particle and enzyme is
Another factor that must be taken into consideration.Therefore, in Pickering interfacial enzymes catalytic process, particle stabilizers all have passed through complexity
Modification, such as hydridization micella, polymer and surface-functionalized inorganic particle.
Starch base nano particle has that the processing is simple, renewable, good biocompatibility, nontoxic compared with inorganic nanoparticles
The advantages that.Significantly, since having well-regulated spherical structure, there is good tolerance in organic phase and water phase, it
Obtained extensive research as Pickering emulsion stabilizer.In addition, hydroxyl abundant imparts starch reaction activity,
By hydroxyl derivatization reaction, hydrophobic chain alkyl chain and polymer chain can be easily introduced on starch chain.By this
Method, starch base nanoparticle are easily achieved functionalization.Alcoholic extract hydroxyl group energy and starch after methoxy silane hydrolysis more than 8 carbochains
Middle hydroxyl generates hydrogen bond, can be effectively reduced starch nanometer granule surface can, assign its unique hydrophobicity, so as to
There is good dispersibility in the organic solvents such as acetone, normal heptane, ethyl acetate.And benzoic anhydride and its derivative are as a kind of ester
Agent realizes high interfacial activity there are the wetability of adjustable starch particle surface due to carboxyl.Therefore, pass through optimization
Silane-modified and esterification process can make modified starch nanoparticle become the reason that Water-In-Oil Pickering lotion encapsulates enzyme
Think material.
Summary of the invention
In order to overcome the shortcomings and deficiencies of the prior art described above, the primary purpose of the present invention is that providing a kind of encapsulating fat
The Pickering lotion of enzyme.
The present invention is by being used as particle stabilizers after being modified to starch, to obtain encapsulating lipase
Pickering lotion.
Another object of the present invention is to provide a kind of preparation method of the Pickering lotion of above-mentioned encapsulating lipase.
The purpose of the present invention is realized by following proposal:
A kind of Pickering lotion for encapsulating lipase, using modified starch as particle stabilizers, especially by esterification
Agent carries out esterification modification to the starch after gelatinization, is granulated, and obtains esterification nano particle；Then it carries out being coupled with methoxy silane anti-
It answers, carries out hydrophobically modified；After being scattered in organic solution again as oily phase, mixes, stir with the water phase of lipase solution
To stable Pickering lotion.
The reaction condition of the esterification modification is preferably in 80-90 DEG C of reaction 2-3h.
The mass parts of starch and esterifying agent used are preferably respectively 1-3 mass parts and 1.5-4.5 mass parts.
Esterification starch nano particle used and the mass ratio of methoxy silane are 1:1-3:1.
The esterifying agent preferably includes at least one of benzoic anhydride, phthalic anhydride, 3- hydroxyl phthalate anhydride.
The methoxy silane may include positive decyl trimethoxy silane, dodecyltrimethoxysilane, hexadecane
At least one of base trimethoxy silane, octadecyl trimethoxysilane.
The type of the starch may include in cornstarch, rice starch, sorghum starch, wheaten starch and potato starch
At least one.
The esterification modification is specially that starch and the esterifying agent esterification under initiator initiation after gelatinization are obtained ester
Change nano particle.
The dosage of the initiator is preferably 0.05-0.2 mass parts.
The initiator is conventional esterification initiator, such as can be selected from pyridine, 4-dimethylaminopyridine, 2-
At least one of aminopyridine, 3- aminopyridine, 2,6- dimethyl -4-aminopyridine.
The concrete operations of the gelatinization can be heated to 40-60 DEG C of gelatinization 10-40min for starch to be added in organic solvent.
The solvent can be dimethyl sulfoxide (DMSO), dimethyl acetamide (DMAC), N-Methyl pyrrolidone (NMP), N, N- dimethyl
At least one of organic solvents such as formamide (DMF).
The granulation, which refers to, is added to the water system after reaction, and stirring is precipitated, separation, obtains esterification nano particle.More
Body is that system solution volume ratio 1:10-1:20 will be added to the water after reacting, and stirs, separation, obtains esterification nano particle.
The hydrophobically modified is specially that esterification starch nano particle and methoxy silane are added in ethanol/water solution
100-300rpm stirs 1-3h and carries out coupling reaction.
Ethanol/water volume ratio is 2:1-4:1 in the ethanol/water solution.
In reaction system, the concentration of the methoxy silane is preferably 1-4mg/mL,
It, can be by being centrifuged, being dried to obtain hydrophobization nano-starch particle after the coupling reaction.The drying can be first
Then the heated-air drying at 45 DEG C continues under nitrogen atmosphere with 120 DEG C of dry 2h.
In Pickering lotion of the invention, the oil is preferably mutually 1:1 with the volume ratio of water phase.
In the oil phase, the concentration of hydrophobic esterification nano particle is preferably 20-40mg/mL organic solvent.The dispersion is excellent
Select ultrasonic disperse 10-15min.
The lipase solution is preferably the volume diluted with the Tris-HCl buffer that 10mmol/L, pH are 7.2
Concentration is the solution of 2-3%.
The mixing preferably uses high-speed shearing machine to be vigorously stirred 1-3min with the speed of 12000-20000rpm.
The organic solvent may include at least one of n-hexane, normal heptane, pentane, iso-heptanol, isooctanol etc..
The lipase may be from least one of aspergillus niger, candida albicans, aspergillus oryzae, Candida etc..
The present invention also provides a kind of preparation methods of the Pickering lotion of above-mentioned encapsulating lipase, including in detail below
Step:
(1) starch is added in solvent and is heated to 40-60 DEG C of gelatinization 10-40min；It is warming up to 80-90 DEG C, esterification is added
Agent and initiator stir lower insulation reaction 2-3h；
(2) system after reaction in step (1) is added drop-wise in water, stirring, separation, drying obtain esterification nano particle；
(3) the obtained esterification nano particle in step (2) is added in ethanol/water solution with methoxy silane with 100-
300rpm stirs 1-3h and carries out coupling reaction, obtains hydrophobization nano-starch particle；
(4) hydrophobization nano-starch particle ultrasonic disperse is used as to oily phase in organic solvent, with Tris-HCl buffer
Diluted lipase solution is water phase, and two-phase mixtures stirring obtains the Pickering lotion of encapsulating lipase.
The present invention, which is esterified starch, and silylating reagent is to be prepared can stablize encapsulating lipase
Pickering lotion, wherein the esterifying agents such as benzoic anhydride and its derivative change starch using it due to the presence of carboxyl
Property adjustable starch particle surface wetability, make particle that there is very high interfacial activity；And methoxy silane more than 8 carbochains
Alcoholic extract hydroxyl group can generate hydrogen bond with hydroxyl in starch after hydrolysis, can be effectively reduced the surface energy of starch nanometer granule, assign it solely
Special hydrophobicity, so as to have good dispersibility in the organic solvents such as acetone, normal heptane, ethyl acetate；It is modified
Starch have excellent performance stable Pickering lotion can be formed with lipase solution, realize the encapsulating of lipase.
The present invention compared with the existing technology, have the following advantages and the utility model has the advantages that
(1) substrate for preparing natural products starch as Pickering emulsion particle stabilizer, raw material environmental protection are easy to get.
(2) it carries out surface chemical property to starch by esterification and Silanization reaction to be modified, mild condition is easy to operate.
(3) Water-In-Oil Pickering lotion can make the mutually convenient recycling of oil, be conducive to the circulation of enzymic catalytic reaction.
Detailed description of the invention
Fig. 1 is the laser co-focusing figure that encapsulating lipase Pickering lotion is made in embodiment 1.Wherein, lipase is with different
Thiocyanic acid fluorescent staining.
Fig. 2 is that encapsulating lipase Pickering lotion is made in the optics of different cycle period stable emulsions in embodiment 1
Microphoto.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto.
Material involved in the following example can be obtained from commercial channel.Dosage of each component in terms of quality parts by volume, g,
mL。
Embodiment 1
(1) cornstarch of 3 mass parts is added in 30 parts by volume DMSO, temperature is then increased to 60 DEG C, starts to paste
Change process.After 15min, the starch being gelatinized completely is continued to be heated to 90 DEG C, while 4.5 mass parts benzoic anhydrides and 0.2 matter is added
It measures part pyridine and starts esterification.Reaction carries out 3h at 200 rpm.
(2) gelatinized corn starch after esterification in 10 parts by volume steps (1) is instilled in 200 parts by volume water with the rate of 1mL/min.
Obtained suspension stirs 20min at 600 rpm, finally passes through water washing/centrifugation 3 times, and be dried in vacuum overnight to obtain ester
Change nano particle.
The positive decyl trimethoxy silicon of the nano-starch particle and 0.1 mass parts that are prepared in (3) 0.1 mass parts steps (2)
Alkane is dissolved in the solution that 100 parts of ethanol/water volume ratios are 4:1, and after stirring 3h at room temperature with 300rpm, it is heavy that lower layer is collected by centrifugation
It forms sediment.It will be deposited in heated-air drying at 45 DEG C, then continued under nitrogen atmosphere with 120 DEG C of dry 2h.
(4) the hydrophobic esterification starch nanometer granule prepared in 0.02 mass parts step (3) is added in 2 parts by volume n-hexanes
Middle ultrasonic disperse 15min, as oily phase.Stoste by 0.06 parts by volume lipase (derive from aspergillus niger) is with concentration
The Tris-HCl buffer that 10mmol/L, pH are 7.2 is diluted to 2 parts by volume, and mixing shakes up 3min as water phase.Use high speed shear
Machine carries out 1min to mixing liquid with the speed of 15000rpm and is vigorously stirred, to obtain uniform Pickering lotion.
Embodiment 2
(1) rice starch of 1 mass parts is added in 30 parts by volume DMAC, temperature is then increased to 40 DEG C, starts to paste
Change process.After 15min, the starch being gelatinized completely is continued to be heated to 80 DEG C, while 1.5 mass parts phthalic anhydrides and 0.05 mass is added
Part 4-dimethylaminopyridine starts esterification.Reaction carries out 3h at 200 rpm.
(2) gelatinized corn starch after esterification in 10 parts by volume steps (1) is instilled into 100 parts by volume water with the rate of 0.5mL/min
In.Obtained suspension stirs 20min at 600 rpm, finally passes through water washing/centrifugation 3 times, and be dried in vacuum overnight
To esterification nano particle.
The hexadecyl trimethoxy of the nano-starch particle and 0.4 mass parts that are prepared in (3) 1.2 mass parts steps (2)
Silane is dissolved in the solution that 100 parts of ethanol/water volume ratios are 4:1, and after stirring 1h at room temperature with 100rpm, lower layer is collected by centrifugation
Precipitating.It will be deposited in heated-air drying at 45 DEG C, then continued under nitrogen atmosphere with 120 DEG C of dry 2h.
(4) the hydrophobic esterification starch nanometer granule prepared in 0.02 mass parts step (3) is added in 2 parts by volume normal heptanes
Ultrasonic disperse 10min, as oily phase.It with concentration is 10mmol/ by the stoste of 0.04 parts by volume lipase (derive from aspergillus oryzae)
The Tris-HCl buffer that L, pH are 7.2 is diluted to 2 parts by volume, and mixing shakes up 3min as water phase.With high-speed shearing machine with
The speed of 15000rpm carries out 1min to mixing liquid and is vigorously stirred, to obtain uniform Pickering lotion.
Embodiment 3
(1) sorghum starch of 1 mass parts is added in 30 parts by volume NMP, temperature is then increased to 50 DEG C, starts to be gelatinized
Process.After 15min, the starch being gelatinized completely is continued to be heated to 80 DEG C, at the same be added 3 mass parts 3- hydroxyl phthalate anhydrides and
0.1 mass parts 2-aminopyridine starts esterification.Reaction carries out 3h at 200 rpm.
(2) gelatinized corn starch in 10 parts by volume steps (1) after esterification is taken to instill in 200 parts by volume water with the rate of 1mL/min.
Obtained suspension stirs 20min at 600 rpm, finally passes through water washing/centrifugation 3 times, and be dried in vacuum overnight to obtain ester
Change nano particle.
The octadecyl of the nano-starch particle and 0.3 mass parts that are prepared in (3) 0.6 mass parts steps (2)
Silane is dissolved in the solution that 100 parts of ethanol/water volume ratios are 4:1, and after stirring 2h at room temperature with 100rpm, lower layer is collected by centrifugation
Precipitating.It will be deposited in heated-air drying at 45 DEG C, then continued under nitrogen atmosphere with 120 DEG C of dry 2h.
(4) the hydrophobic esterification starch nanometer granule prepared in 0.02 mass parts step (3) is added in 2 parts by volume pentanes
Ultrasonic disperse 15min, as oily phase.It with concentration is 10mol/ by the stoste of 0.06 parts by volume lipase (derive from Candida)
The Tris-HCl buffer that L, pH are 7.2 is diluted to 2 parts by volume, and mixing shakes up 3min as water phase.With high-speed shearing machine with
The speed of 15000rpm carries out 1min to mixing liquid and is vigorously stirred, to obtain uniform Pickering lotion.
Embodiment 4
(1) wheaten starch of 1 mass parts is added in 30 parts by volume DMF, temperature is then increased to 60 DEG C, starts to be gelatinized
Process.After 15min, the starch being gelatinized completely is continued to be heated to 80 DEG C, while 4.5 mass parts benzoic anhydrides and 0.1 mass is added
Part 2,6- dimethyl -4-aminopyridine starts esterification.Reaction carries out 3h at 200 rpm.
(2) gelatinized corn starch in 10 parts by volume steps (1) after esterification is taken to instill in 100 parts by volume water with the rate of 1mL/min.
Obtained suspension stirs 20min at 600 rpm, finally passes through water washing/centrifugation 3 times, and be dried in vacuum overnight to obtain ester
Change nano particle.
The dodecyl trimethoxy of the nano-starch particle and 0.4 mass parts that are prepared in (3) 0.8 mass parts steps (2)
Silane is dissolved in the solution that 100 parts of ethanol/water volume ratios are 4:1, and after stirring 2h at room temperature with 100rpm, lower layer is collected by centrifugation
Precipitating.It will be deposited in heated-air drying at 45 DEG C, then continued under nitrogen atmosphere with 120 DEG C of dry 2h.
(4) the hydrophobic esterification starch nanometer granule prepared in 0.02 mass parts step (3) is added in 2 parts by volume n-hexanes
Ultrasonic disperse 15min, as oily phase.It with concentration is 10mmol/ by the stoste of 0.06 parts by volume lipase (derive from candida albicans)
The Tris-HCl buffer that L, pH are 7.2 is diluted to 2 parts by volume, and mixing shakes up 3min as water phase.With high-speed shearing machine with
The speed of 15000rpm carries out 1min to mixing liquid and is vigorously stirred, to obtain uniform Pickering lotion.
Catalytic efficiency measurement
Using the transesterification of n-butanol and vinyl acetate as model, the catalytic performance of lipase is measured.Contained with 2mL
The organic phase of 150mmol/L n-butanol and 150mmol/L vinyl acetate is oily phase, after homogeneous forms Pickering lotion,
200rpm mixes slowly initiation catalysis reaction.After reacting 20h, stop stirring, is mutually taken out by decantation by oily, and pass through1H
NMR carries out product analysis.
In next reaction cycle, it will be added in remaining water phase, be slowly stirred again dissolved with the green oil of substrate
Starting catalysis reaction.Subsequent cyclic program is identical as first set reaction circulation.It the results are shown in Table 1 and Fig. 1-Fig. 2.
Fig. 1 is the laser co-focusing figure that encapsulating lipase Pickering lotion is made in embodiment 1.Wherein, lipase is with different
Thiocyanic acid fluorescent staining.Fig. 2 is that the obtained encapsulating lipase Pickering lotion of embodiment 1 is stablized in different cycle periods
The light micrograph of lotion.
By table 1 it can be found that the Pickering emulsion interface catalyst prepared in the embodiment of the present invention can be efficiently real
Existing transesterification, yield up to 96% or more, and be catalyzed reaction still kept after 10 reaction times 94% or more it is excellent
Different catalytic effect.
The catalytic efficiency of 1 Pickering lotion of table
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, 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.
Claims (10)
1. a kind of Pickering lotion for encapsulating lipase, it is characterised in that using modified starch as particle stabilizers, specifically
Esterification modification is carried out to the starch after gelatinization by esterifying agent, is granulated, esterification nano particle is obtained；Then with methoxy silane into
Row coupling reaction carries out hydrophobically modified；It is mixed with the water phase of lipase solution after being scattered in organic solution again as oily phase
It closes, stirs to get stable Pickering lotion.
2. the Pickering lotion of encapsulating lipase according to claim 1, it is characterised in that: the esterification modification
Reaction condition is in 80-90 DEG C of reaction 2-3h.
3. the Pickering lotion of encapsulating lipase according to claim 1, it is characterised in that: starch used and esterification
The mass parts of agent are respectively 1-3 mass parts and 1.5-4.5 mass parts；The matter of esterification starch nano particle and methoxy silane used
Amount is than being 1:1-3:1.
4. the Pickering lotion of encapsulating lipase according to claim 1, it is characterised in that: the esterifying agent packet
Include at least one of benzoic anhydride, phthalic anhydride, 3- hydroxyl phthalate anhydride；The methoxy silane includes positive decyl trimethoxy
Silane, dodecyltrimethoxysilane, hexadecyl trimethoxy silane, at least one in octadecyl trimethoxysilane
Kind.
5. the Pickering lotion of encapsulating lipase according to claim 1, it is characterised in that: the esterification modification tool
Body is starch and the esterifying agent esterification under initiator initiation after being gelatinized, and obtains esterification nano particle；The initiator
Dosage be 0.05-0.2 mass parts；The initiator is selected from pyridine, 4-dimethylaminopyridine, 2-aminopyridine, 3- amino
At least one of pyridine, 2,6- dimethyl -4-aminopyridine.
6. it is according to claim 1 encapsulating lipase Pickering lotion, it is characterised in that: the gelatinization it is specific
Operation is heated to 40-60 DEG C of gelatinization 10-40min for starch to be added in organic solvent.
7. it is according to claim 1 encapsulating lipase Pickering lotion, it is characterised in that: the granulation refer to by
System volume ratio 1:10-1:20 is added to the water after reaction, and stirring is precipitated, separation, obtains esterification nano particle.
8. the Pickering lotion of encapsulating lipase according to claim 1, it is characterised in that: the hydrophobically modified
100-300rpm stirring 1-3h in ethanol/water solution specially is added in esterification starch nano particle and methoxy silane to carry out occasionally
Connection reaction.
9. the Pickering lotion of encapsulating lipase according to claim 1, it is characterised in that: the oil phase and water phase
Volume ratio be 1:1；In the oil phase, the concentration of hydrophobic esterification nano particle is 20-40mg/mL organic solvent；The fat
Enzyme solutions be 7.2 with 10mmol/L, pH the volumetric concentration that dilutes of Tris-HCl buffer for 2-3% solution.
10. a kind of preparation method of the Pickering lotion of the described in any item encapsulating lipase of claim 1-9, feature
Be comprising the following specific steps
(1) starch is added in solvent and is heated to 40-60 DEG C of gelatinization 10-40min；Be warming up to 80-90 DEG C, be added esterifying agent and
Initiator stirs lower insulation reaction 2-3h；
(2) system after reaction in step (1) is added drop-wise in water, stirring, separation, drying obtain esterification nano particle；
(3) the obtained esterification nano particle in step (2) is added in ethanol/water solution with methoxy silane with 100-
300rpm stirs 1-3h and carries out coupling reaction, obtains hydrophobization nano-starch particle；
(4) hydrophobization nano-starch particle ultrasonic disperse is used as to oily phase in organic solvent, with the dilution of Tris-HCl buffer
Lipase solution be water phase, two-phase mixtures stirring, obtain encapsulating lipase Pickering lotion.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111808839A (en) * | 2020-06-10 | 2020-10-23 | 广东省测试分析研究所（中国广州分析测试中心） | Lipase interface immobilization method based on hydrophobic modified gelatin microspheres |
| CN113151244A (en) * | 2021-04-14 | 2021-07-23 | 华南理工大学 | pH-responsive enzyme-loaded starch granule with controllable enzyme distribution position and preparation method thereof |
| CN113605121A (en) * | 2021-08-10 | 2021-11-05 | 浙江金龙再生资源科技股份有限公司 | Preparation method of high-strength biochemical mechanical pulp |
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| CN111808839A (en) * | 2020-06-10 | 2020-10-23 | 广东省测试分析研究所（中国广州分析测试中心） | Lipase interface immobilization method based on hydrophobic modified gelatin microspheres |
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| CN113151244B (en) * | 2021-04-14 | 2023-02-17 | 华南理工大学 | pH-responsive enzyme-loaded starch granule with controllable enzyme distribution position and preparation method thereof |
| CN113605121A (en) * | 2021-08-10 | 2021-11-05 | 浙江金龙再生资源科技股份有限公司 | Preparation method of high-strength biochemical mechanical pulp |
| CN113605121B (en) * | 2021-08-10 | 2023-10-13 | 浙江金龙再生资源科技股份有限公司 | Preparation method of high-strength biochemical slurry |
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