CN109701463A - A kind of preparation method of the programmable release microcapsules of double responsiveness - Google Patents
A kind of preparation method of the programmable release microcapsules of double responsiveness Download PDFInfo
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- CN109701463A CN109701463A CN201910012648.3A CN201910012648A CN109701463A CN 109701463 A CN109701463 A CN 109701463A CN 201910012648 A CN201910012648 A CN 201910012648A CN 109701463 A CN109701463 A CN 109701463A
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Abstract
The invention discloses a kind of preparation method of the programmable release microcapsules of double responsiveness, the preparation method includes the following steps: that (1) prepares temperature sensitive type polymer nano-particle；(2) the temperature sensitive type polymer nano-particle of encapsulation guest molecule A is made；(3) microcapsules of the programmable release of double responsiveness are prepared；Encapsulation guest molecule A, the guest molecule B be respectively hydrophobic drug used in oil-soluble inhibitor, pharmaceutical carrier used in erosion shield, for the oil-soluble fluorescent dyestuff of fluorescence developing, for the curing agent or one of prepolymer in coatings.The present invention enables two kinds of guest molecules successively to release in a different order by imposing different stimulation sequences；The preparation method is applied widely and method is simple and easy, has a wide range of applications in fields such as drug delivery, gene delivery, corrosion-resistant material, catalysis and self-repair materials.
Description
Technical field
The present invention relates to programmable release microcapsules technology fields, pass through Pickering emulsion method more particularly, to one kind
The method for preparing the programmable release microcapsules of double responsiveness.
Background technique
Stimulating responsive microcapsules drug delivery, gene delivery, corrosion-resistant material, catalysis and self-repair material and its
He has sizable potentiality in applying.Usually extraneous stimulus mainly has pH, magnetic field, temperature, light, ionic strength etc.,
Single response type microcapsules can only respond a kind of environmental stimuli, cannot achieve the function of programmable release, limit the reality of microcapsules
Border application, needs to design multiple stimulation responsiveness microcapsules to meet actual demand.Although passed through it is various chemically and physically
Method has successfully prepared multiple stimulation response microcapsules, but most of can only encapsulate and discharge a kind of guest molecule
Son, but need to encapsulate two kinds of guest molecules so as to cooperate between guest molecule in drug delivery, anticorrosion and other field
It plays a role, it is therefore desirable to prepare multiple stimulation responsiveness microcapsules and encapsulate two kinds of guest molecules.
Although they usually exist currently, having synthesized some microcapsules for encapsulating two kinds of guest molecule
Two kinds of guest molecules are released simultaneously under a kind of stimulation, greatly hinder their practical application in certain fields.For example,
Gastrotherapy field releases ancillary drug later and drug effect is made to maximize and reduce it is generally desirable to release therapeutic agent first
Toxic side effect.So needing for multiple guest molecules to be encapsulated in multiple compartments and different compartments is to different environmental stimulis
With response in order to programming trelease, i.e., make the release of two kinds of guest molecules successive by changing the sequence of application environmental stimuli
Sequence changes, and a kind of release of guest molecule will not interfere the release of another guest molecule.Such microcapsules can not
It is prepared using traditional method, needs different and classification the designs of progress to the shell and inner space of microcapsules.
The method of common manufacture multiple response multicell microcapsules is using small porous particle and star-like nano particle as multiple
Miscellaneous template.One layer of stimulating responsive polymer is coated in microparticle surfaces, then in the smaller particle of polymer-coated (cladding
Another stimulating responsive polymer), multiple response multicell microcapsules are prepared after removing all template particles.But
It is that the multiple response multicell microcapsules of this method preparation are in irregular shape, and dispersibility is high, and yield is lower.Another kind preparation
The common method of multiple response multicell microcapsules is multithread microfluid.Come in fact from oily phase dissolved with different components in water phase
Individual loads in existing shell/core region.The composite construction prepared in this way includes mono-/multi- core-shell structure.Although microfluid
Technology can prepare a large amount of microcapsules in a short time, but the oil reservoir for bonding is usually on the surface of the microcapsules of preparation
On, this will affect the performance of microcapsules and further surface is modified.Further, since the size of microfluidic channel is larger, because
The capsule size that this can be manufactured is larger, and then reduces the long-time stability of microcapsules.The third method is with polymer nano
Meter Zai Ti prepares layering multicell structure (microcapsules, micro- container or particle) as main component, by noncovalent interaction.This
Method has unique advantage, and including the multi-selection of shell and it is multi-functional, encapsulation is multiple with heterogeneity, ingredient
With the ability of function loaded article.However, the nano-carrier as shell is that (electrostatic is mutual by weaker noncovalent interaction
Effect, hydrogen bond, hydrophobe effect) and formed, therefore microcapsule stability is lower.
Therefore, in conclusion still lacking a kind of not only simple and convenient but also efficient programmable release microcapsules of preparation at present
Method.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of programmable release of double responsiveness is micro-
The preparation method of capsule.The present invention enables two kinds of guest molecules first in a different order by imposing different stimulation sequences
After release；The preparation method is applied widely and method is simple and easy, drug delivery, gene delivery, corrosion-resistant material,
The fields such as catalysis and self-repair material have a wide range of applications.
Technical scheme is as follows:
A kind of preparation method of the programmable release microcapsules of double responsiveness, the preparation method include the following steps:
(1) by temperature sensitive type poly monomer adduct, N, N- methylene-bisacrylamide is added to the water with initiator, is in temperature
4~9h, isolated temperature sensitive type polymer nano-particle are reacted under conditions of 60~90 DEG C；
(2) temperature sensitive type polymer nano-particle made from step (1) is added to the water, 0.5~1.5h of ultrasonic disperse, high speed
It is added with stirring guest molecule A, continues 0.5~1.5h of high-speed stirred, is removed free guest molecule A by dialysing, it is dry
The temperature sensitive type polymer nano-particle of encapsulation guest molecule A is obtained afterwards；
(3) the temperature sensitive type polymer nano-particle of step (2) encapsulation guest molecule A obtained is dispersed in water as water
The oily phase containing pH responsive polymer monomer, crosslinking agent and guest molecule B is added in phase later, and high speed emulsifies 2-4min, is formed
The microcapsules of the programmable release of double responsiveness are made in stable lotion, lotion after solidifying；
The encapsulation guest molecule A, guest molecule B are respectively oil-soluble inhibitor, drug used in erosion shield
Hydrophobic drug used in carrier, for the oil-soluble dyes of fluorescence developing, for curing agent in coatings or pre-
One of polymers.
Temperature sensitive type poly monomer adduct described in step (1) and N,N methylene bis acrylamide mass ratio are 40:1~8:1；
The initiator is 1~4wt% of temperature sensitive type poly monomer adduct and N,N methylene bis acrylamide quality total amount；Temperature sensitive type poly
The concentration of monomer adduct is 10~30mg/mL.
Temperature sensitive polymer monomer described in step (1) is n-isopropyl acrylamide, poly glycol monomethyl ether, vinylpyridine
Pyrrolidone, poly lactide-glycolide acid, N- acryloyl group-glycine methyl ester, in N- acryloyl group-glycine ethyl ester
It is one or more；The initiator is one of cumyl hydroperoxide, potassium peroxydisulfate, ammonium persulfate, two valeric acid of peroxidating
Or it is a variety of.
The concentration of temperature sensitive type polymer nano-particle in water described in step (2) is 0.2~2mg/mL；The guest molecule
The mass ratio of sub- A and temperature sensitive type polymer nano-particle is 1:100~1:1000.
The condition of ultrasonic disperse described in step (2) are as follows: at room temperature, 0.5-1.5h；The revolving speed of the high-speed stirred is
15000-22000rpm。
The temperature sensitive type polymer nano-particle concentration in water that guest molecule A is encapsulated described in step (3) is 2~
32mg/mL；The mass ratio of the pH responsive polymer monomer and crosslinking agent is 0.25:1~1:4；Guest molecule B is responded in pH
Property polymer monomer in concentration be 0.2~2mg/mL；Oily is mutually 0.5:1~1:4 with the volume ratio of water phase.
The condition emulsified at a high speed described in step (3) is 15000-22000rpm；The cured mode be UV solidify or
Electronic beam curing.
The time of the UV or electronic beam curing are as follows: 5~15min.
PH responsive polymer monomer described in step (3) be 4-vinylpridine, dimethylaminoethyl methacrylate,
Acrylic acid, aziridine, chitosan, methacrylic acid, acrylamide, vinyl imidazole, styrene sulfonic acid, methacrylic acid-
One of 2- (N- morpholinyl) ethyl ester is a variety of；The crosslinking agent is three contracting four propylene glycol double methacrylates, 1,6-HD
The double first of double methacrylate, two contracting propylene glycol double methacrylates, bisphenol-A glycidol double methyl methacrylate, triethylene-glycol
Base acrylate, dipentaerythritol hexaacrylate, two propylene olefin(e) acid ester of diethylene glycol phthalate, neopentyl glycol diacrylate
Ester, pentaerythritol triacrylate, trimethylolpropane trimethacrylate, dipropylene glycol diacrylate, 1,3 butylene glycol two
One of acrylate is a variety of.
When the curing mode is that UV solidifies, use photoinitiator for 2- hydroxy-methyl phenyl-propane -1- ketone, 1- hydroxyl
Cyclohexyl phenyl ketone, 2- methyl-1-(4- methyl mercapto phenyl)-2- morpholinyl-1- acetone, benzoin dimethylether, 2,4,6- tri-
Methyl benzoyl diphenyl phosphine oxide, isopropyl thioxanthone, 4- (N, N- dimethylamino) ethyl benzoate, benzophenone,
4- chlorobenzophenone, methyl o-benzoylbenzoate, diphenyl iodnium hexafluorophosphate, N, N- dimethylaminobenzoic acid are different pungent
Ester, 4- methyl benzophenone, o-benzoyl yl benzoic acid methyl esters, 4- phenyl benzophenone, 2,4,6- trimethylbenzoyl-two
One of phenyl phosphine oxide, 2,4,6- trimethylbenzoyl phenyl phosphinic acid ethyl ester are a variety of.
The present invention is beneficial to be had the technical effect that
The programmable release microcapsules of double responsiveness are prepared the present invention provides a kind of Pickering emulsion method to be based on
The preparation of Pickering lotion.Pickering lotion is to stablize cream by being adsorbed on the solid nanoparticles at oil/water interface
Liquid, rather than organic surface active agent.It is empty that the particle emulsifying agents and inner emulsion of Pickering lotion provide different loads
Between can be used to prepare multiple stimulation responsiveness multicell microcapsules.Particle emulsifying agents and oily phase content can select extensively
The design selected, and can distinguished it assigns its different functionality, to prepare micro- glue of the programmable release of double response types
Capsule, the preparation method is applied widely and method is simple and easy, drug delivery, gene delivery, corrosion-resistant material, catalysis and from
The fields such as repair materials have a wide range of applications.
Guest molecule of the present invention is present in (i.e. monodisperse temperature sensitive type polymer nano-particle in two independent coating spaces
Inside interior and lotion after solidifying oily phase), two kinds of stimulating responsives will not interfere the independent release of two kinds of guest molecules；Two kinds
Different stimulations corresponds to different coating spaces, can be realized programmable release, applies the sequence of environmental stimuli by changing
The successive release sequence of adjustable two kinds of guest molecules.
The present invention can prepare w/o type and O/W type lotion, and oily phase range of choice is wide and functionalization side to particle emulsifying agents
Formula is more, and preparation method is simple.
Detailed description of the invention
Fig. 1 is the schematic diagram of programmable release microcapsules programming trelease the guest molecule A and B of the present invention.
Fig. 2 is the fluorescence photo that the programmable release microcapsules synthesized in embodiment 1 discharge guest molecule A at 50 DEG C.
Fig. 3 is fluorescence photo of the guest molecule B without release at synthesize 50 DEG C of programmable release microcapsules in embodiment 1.
Fig. 4 is the fluorescence photo that the programmable release microcapsules synthesized in embodiment 2 discharge guest molecule B in pH < 7.
Fig. 5 is that the programmable release microcapsules that the synthesize guest molecule A in pH < 7 shines without the fluorescence of release in embodiment 2
Piece, show the guest molecule A in microcapsules shell will not because of pH reduction and discharge.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1
A kind of preparation method of the programmable release microcapsules of double responsiveness, the preparation method include the following steps:
(1) monodisperse temperature sensitive type polymer nano-particle is prepared；
By 0.8g temperature sensitive type poly monomer adduct n-isopropyl acrylamide and 0.1g N, N- methylene-bisacrylamide,
0.009g initiator ammonium persulfate is added in 90mL water, and 4h, isolated monodisperse temperature sensitive type polymer nano are reacted at 60 DEG C
Rice corpuscles；
(2) Nile red is encapsulated in preparing monodisperse temperature sensitive type polymer nano-particle；
It weighs 0.02g temperature sensitive type polymer nano-particle to be distributed in 100mL water, single neck round bottom burning is poured into after ultrasonic 0.5h
In bottle, by 0.4mL Nile red/methanol (0.5mg mL under 1500rpm-1) solution is added dropwise in dispersion liquid, and continues to stir
0.5h；Finally above-mentioned mixing liquid is placed in the bag filter that molecular cut off is 14000, the sufficiently long time of dialysing will dissociate
Nile red removal；
(3) the programmable release microcapsules of double responsiveness are prepared；
It disperses the monodisperse temperature sensitive type polymer nano-particle of 0.2g enclosed inside Nile red in 100mL water, later
By 0.5g pH responsive polymer monomer dimethylaminoethyl methacrylate, 2g crosslinking agent neopentylglycol diacrylate,
0.5mg glucan-FITC mixing is added in 5mL water as oil, is obtained surely through mulser 15000rpm high speed emulsification 2min
Fixed lotion；By lotion electronic beam curing 5min, the microcapsules of programmable release are obtained after separation.
The programmable release microcapsules of the present embodiment discharge the fluorescence photo of guest molecule A as shown in Fig. 2, by scheming at 50 DEG C
2 as can be seen that show guest molecule A at high temperature as the red fluorescence of the extension shell of time gradually weakens final disappearance
It being capable of quick release.
Fluorescence photo of the guest molecule B without release is as shown in figure 3, by scheming at programmable 50 DEG C of microcapsules of the release of the present embodiment
3 it can be seen that microcapsules inside guest molecule B will not because of temperature raising and discharge.
Embodiment 2
A kind of preparation method of the programmable release microcapsules of double responsiveness, the preparation method include the following steps:
(1) monodisperse temperature sensitive type polymer nano-particle is prepared；
By 2g temperature sensitive type poly monomer adduct n-isopropyl acrylamide and 0.1g N, N- methylene-bisacrylamide,
0.053g initiator ammonium persulfate is added in 107mL water, and 6.5h, isolated monodisperse temperature sensitive type polymer are reacted at 75 DEG C
Nanoparticle；
(2) taxol is encapsulated in preparing monodisperse temperature sensitive type polymer nano-particle；
0.1g temperature sensitive type polymer nano-particle is weighed to be scattered in 100mL water, it will at 1900rpm after ultrasonic 1h
0.4mL taxol/methanol (0.5mg mL-1) solution is added dropwise in dispersion liquid, and continues to stir 1h；Finally by above-mentioned mixed liquor
Body is placed in the bag filter that molecular cut off is 14000, and the sufficiently long time of dialysing removes free taxol；
(3) the programmable release microcapsules of double responsiveness are prepared；
It disperses the monodisperse temperature sensitive type polymer nano-particle of 0.16g enclosed inside taxol in 10mL water, later
1g pH responsive polymer monomer 4-vinylpridine, 1g crosslinking agent 1,6-HD double methacrylate, 0.02g is light-initiated
Agent 1- hydroxy-cyclohexyl phenyl ketone, the mixing of 2mg adriamycin are added in 4mL water as oil, through mulser 19000rpm high
Speed emulsification 3min obtains stable lotion；Lotion UV is solidified into 10min, the microcapsules of programmable release are obtained after separation.
The programmable release microcapsules of the present embodiment discharge the fluorescence photo of guest molecule B in pH < 7 as shown in figure 4, by scheming
4 as can be seen that show guest molecule under low pH as the green fluorescence inside the extension microcapsules of time gradually weakens final disappearance
Sub- B being capable of quick release.
The programmable release microcapsules of the present embodiment in pH < 7 fluorescence photo of the guest molecule A without release as shown in figure 5, by
Fig. 5 can be seen that the guest molecule A in microcapsules shell will not because of pH reduction and discharge.
Embodiment 3
A kind of preparation method of the programmable release microcapsules of double responsiveness, the preparation method include the following steps:
(1) monodisperse temperature sensitive type polymer nano-particle is prepared；
By 4g temperature sensitive type poly monomer adduct n-isopropyl acrylamide and 0.1g N, N- methylene-bisacrylamide,
0.164g initiator ammonium persulfate is added in 137mL water, and 9h, isolated monodisperse temperature sensitive type polymer nano are reacted at 90 DEG C
Rice corpuscles；
(2) dodecenylsuccinic acid is encapsulated in preparing monodisperse temperature sensitive type polymer nano-particle；
0.2g temperature sensitive type polymer nano-particle is weighed to be scattered in 100mL water, it will at 2200rpm after ultrasonic 1.5h
0.4mL dodecenylsuccinic acid/methanol (0.5mg mL-1) solution is added dropwise in dispersion liquid, and continues to stir 1.5h；Finally will
Above-mentioned mixing liquid is placed in the bag filter that molecular cut off is 14000, the laurylene base that the sufficiently long time of dialysing will dissociate
The removal of succinic acid fluorescein；
(3) the programmable release microcapsules of double responsiveness are prepared；
10mL water is dispersed by the monodisperse temperature sensitive type polymer nano-particle of 0.32g enclosed inside dodecenylsuccinic acid
In, it is later that 1g pH responsive polymer monomeric acrylic, 4g crosslinking agent 1,3-BDO diacrylate, 0.03g is light-initiated
Agent benzophenone, the mixing of 10mg 9- hydroxyl-l0- phenyl stearic acid methyl esters are added in 20mL water as oil, through mulser
22000rpm high speed emulsification 4min obtains stable lotion；Lotion UV is solidified into 15min, programmable release is obtained after separation
Microcapsules.
Claims (10)
1. a kind of preparation method of the programmable release microcapsules of double responsiveness, which is characterized in that the preparation method includes as follows
Step:
(1) by temperature sensitive type poly monomer adduct, N, N- methylene-bisacrylamide is added to the water with initiator, temperature be 60~
4~9h, isolated temperature sensitive type polymer nano-particle are reacted under conditions of 90 DEG C；
(2) temperature sensitive type polymer nano-particle made from step (1) is added to the water, 0.5~1.5h of ultrasonic disperse, high-speed stirred
Lower addition guest molecule A continues 0.5~1.5h of high-speed stirred, removes free guest molecule A by dialysing, freezes later
It is dry, the temperature sensitive type polymer nano-particle of encapsulation guest molecule A is made；
(3) the temperature sensitive type polymer nano-particle of step (2) encapsulation guest molecule A obtained is dispersed in water as water phase,
The oily phase containing pH responsive polymer monomer, crosslinking agent and guest molecule B is added later, high speed emulsifies 2-4min, is formed steady
The microcapsules of the programmable release of double responsiveness are made in fixed lotion, lotion after solidifying；
The encapsulation guest molecule A, guest molecule B are respectively oil-soluble inhibitor, pharmaceutical carrier used in erosion shield
Used in hydrophobic drug, for the oil-soluble dyes of fluorescence developing, for the curing agent or prepolymer in coatings
One of.
2. preparation method according to claim 1, which is characterized in that temperature sensitive type poly monomer adduct described in step (1) with
N,N methylene bis acrylamide mass ratio is 40:1~8:1；The initiator is temperature sensitive type poly monomer adduct and N, N- methylene
1~4wt% of base bisacrylamide quality total amount；The concentration of temperature sensitive type poly monomer adduct is 10~30mg/mL.
3. preparation method according to claim 1, which is characterized in that temperature sensitive polymer monomer described in step (1) is N-
N-isopropylacrylamide, poly glycol monomethyl ether, vinyl pyrrolidone, poly lactide-glycolide acid, N- acryloyl
One of base-glycine methyl ester, N- acryloyl group-glycine ethyl ester are a variety of；The initiator be cumyl hydroperoxide,
One of potassium peroxydisulfate, ammonium persulfate, two valeric acid of peroxidating are a variety of.
4. preparation method according to claim 1, which is characterized in that temperature sensitive type polymer nanoparticle described in step (2)
The concentration of son in water is 0.2~2mg/mL；The mass ratio of the guest molecule A and temperature sensitive type polymer nano-particle is 1:
100~1:1000.
5. preparation method according to claim 1, which is characterized in that the condition of ultrasonic disperse described in step (2) are as follows: room
Under temperature, 0.5-1.5h；The revolving speed of the high-speed stirred is 15000-22000rpm.
6. preparation method according to claim 1, which is characterized in that encapsulate the temperature sensitive of guest molecule A described in step (3)
The concentration of type polymer nano-particle in water is 2~32mg/mL；The quality of the pH responsive polymer monomer and crosslinking agent
Than for 0.25:1~1:4；Concentration of the guest molecule B in pH responsive polymer monomer is 0.2~2mg/mL；Oily phase and water phase
Volume ratio be 0.5:1~1:4.
7. preparation method according to claim 1, which is characterized in that the condition emulsified at a high speed described in step (3) is
15000-22000rpm；The cured mode is UV solidification or electronic beam curing.
8. preparation method according to claim 7, which is characterized in that the time of the UV or electronic beam curing are as follows: 5~
15min。
9. preparation method according to claim 1, which is characterized in that pH responsive polymer monomer described in step (3)
For 4-vinylpridine, dimethylaminoethyl methacrylate, acrylic acid, aziridine, chitosan, methacrylic acid, propylene
One of amide, vinyl imidazole, styrene sulfonic acid, methacrylic acid -2- (N- morpholinyl) ethyl ester are a variety of；The crosslinking
Agent is three four propylene glycol double methacrylates of contracting, 1,6-HD double methacrylate, two contracting propylene glycol double methacrylates, bisphenol-A contracting
Water glycerol dimethacrylate, triethylene glycolbismethyl-acrylate, dipentaerythritol hexaacrylate, O-phthalic
Sour two propylene olefin(e) acid ester of diethylene glycol (DEG), neopentylglycol diacrylate, pentaerythritol triacrylate, trimethylolpropane tris propylene
One of acid esters, dipropylene glycol diacrylate, 1,3 butyleneglycol diacrylate are a variety of.
10. preparation method according to claim 7, which is characterized in that when the curing mode is that UV solidifies, drawn using light
Hair agent is 2- hydroxy-methyl phenyl-propane-1- ketone, 1- hydroxy-cyclohexyl phenyl ketone, 2- methyl-1-(4- methyl mercapto phenyl)-
2- morpholinyl -1- acetone, benzoin dimethylether, 2,4,6- trimethyl benzoyl diphenyl base phosphine oxide, isopropyl thioxanthone,
4- (N, N- dimethylamino) ethyl benzoate, benzophenone, 4- chlorobenzophenone, methyl o-benzoylbenzoate, diphenyl iodine
Hexafluorophosphate salt, N, the different monooctyl ester of N- dimethylaminobenzoic acid, 4- methyl benzophenone, o-benzoyl yl benzoic acid methyl esters,
4- phenyl benzophenone, 2,4,6- trimethylbenzoy-dipheny phosphine oxide, 2,4,6- trimethylbenzoyl phenyl phosphonic acids
One of ethyl ester is a variety of.
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| CN114790379A (en) * | 2022-04-24 | 2022-07-26 | 西南石油大学 | Double-chamber microcapsule for drilling fluid and preparation method and application thereof |
| CN115323823A (en) * | 2022-09-16 | 2022-11-11 | 广西大学 | Preparation method and application of intelligent antibacterial coating emulsion for packaging paper |
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| CN111558349A (en) * | 2020-05-19 | 2020-08-21 | 江南大学 | Double-chamber microcapsule with self-warning function and preparation method thereof |
| CN111558349B (en) * | 2020-05-19 | 2021-11-02 | 江南大学 | Double-chamber microcapsule with self-warning function and preparation method thereof |
| CN112546298A (en) * | 2020-12-08 | 2021-03-26 | 西安理工大学 | Preparation method of multi-stimulus cooperative response medicine-releasing bone cement |
| CN112546298B (en) * | 2020-12-08 | 2022-05-17 | 西安理工大学 | Preparation method of multi-stimulus cooperative response medicine-releasing bone cement |
| CN114790379A (en) * | 2022-04-24 | 2022-07-26 | 西南石油大学 | Double-chamber microcapsule for drilling fluid and preparation method and application thereof |
| CN115323823A (en) * | 2022-09-16 | 2022-11-11 | 广西大学 | Preparation method and application of intelligent antibacterial coating emulsion for packaging paper |
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