CN107343960A - Biotechnology gear division desensitizer and preparation method thereof - Google Patents
Biotechnology gear division desensitizer and preparation method thereof Download PDFInfo
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- CN107343960A CN107343960A CN201710402436.7A CN201710402436A CN107343960A CN 107343960 A CN107343960 A CN 107343960A CN 201710402436 A CN201710402436 A CN 201710402436A CN 107343960 A CN107343960 A CN 107343960A
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- Prior art keywords
- desensitizer
- nano particle
- silane coupler
- gear division
- acrylic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/42—Phosphorus; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/16—Fluorine compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
Abstract
Biotechnology gear division desensitizer and preparation method thereof, it is related to a kind of new gear division desensitizer, more particularly to a kind of biotechnology gear division desensitizer and preparation method thereof gear division desensitizer of the present invention is prepared by high-molecular copolymer Encapsulation nanoparticle, wherein high-molecular copolymer is acrylic acid(Ester)Copolymer, nano particle are the nano particle of silane coupler processing.The advantage of the invention for combining high-molecular copolymer and nano particle well, prepares the desensitizer with slowly releasing effect.The present invention is using high-molecular copolymer as carrier, Encapsulation nanoparticle, has given full play to the special efficacy of the parcel of high-molecular copolymer, slow releasing function and nano particle, can not only remove sensitivity of tooth can also play good daily nursing preventing decayed tooth and prevention effect.
Description
Technical field
The present invention relates to a kind of new gear division desensitizer, more particularly to a kind of biotechnology gear division desensitizer and preparation method thereof.
Background technology
Nanometer technology (nanotechnology), also referred to as nanotechnology is research structure size at 1 nanometer to 100 nanometers
In the range of the property of material and a kind of technology of application.Currently, many researchers formed by analyzing existing zoic life,
Eucaryotic cell structure and microstructure etc., pass through nanometer technology artificial synthesized biomimetic material and biomaterial with specific function.It is high
Molecule copolymer refers to the HMW for repeating to be formed by connecting by covalent bond by many identicals, simple construction unit(Generally
Up to 10~106)Compound.High-molecular copolymer is due to macromolecular chain, multilayered structure and the special fortune of macromolecular chain
The features such as flowing mode, therefore it has the advantages that high elastic deformation, viscoplasticity, wear-resisting, heat-resisting.
High-molecular copolymer and nano material are combined, the high-molecular copolymer nanometer material with property can be prepared
Material, the nano-macromolecule material such as obtained by microemulsion polymerization method have huge specific surface area.Nano-particle it is special
Performance makes it comply with demand of the macromolecule polymeric material to high-performance filler in the evolution in this field, occurs some
The new property and New function that common micro level material does not have.The blending mutual assistance of nanometer technology and high-molecular copolymer is even more to open
Having created some has the biomaterial of property.
Bio-nanotechnology is forward position and the hot issue in International Biotechnology field, in medicine, life science and health
Field has a wide range of applications and clear and definite industrialization prospect, particularly nano biological sensor, nano-medicament carrier and nanometer
Imaging technique and intelligent miniature medicine equipment etc..Currently, bio-nanotechnology prevention, medical diagnosis on disease, treatment and
Health care etc. plays a significant role.
The advantage of the invention for combining high-molecular copolymer and nano particle well, prepare de- with slowly releasing effect
Quick dose.The present invention Encapsulation nanoparticle, has given full play to wrapping up, delaying for high-molecular copolymer using high-molecular copolymer as carrier
Release the special efficacy of effect and nano particle.The present invention desensitizer can not only remove sensitivity of tooth can also play well it is daily
Nurse preventing decayed tooth and prevention effect.
The content of the invention
The purpose of the present invention aims to provide a kind of new gear division desensitizer, especially provides a kind of biotechnology gear division desensitizer
And preparation method thereof
Gear division desensitizer of the present invention is prepared by high-molecular copolymer Encapsulation nanoparticle, wherein high-molecular copolymer
For acrylic acid(Ester)Copolymer, nano particle are the nano particle of silane coupler processing.
Gear division desensitizer component of the present invention includes:It is acrylic acid, acrylic acid amides, acrylic acid -2- hydroxyl ethyl esters, hydrophilic
At property polymer, initiator, crosslinking agent, nertralizer, organic dispersion medium, dispersant, ethanol, deionized water and silane coupler
The nano particle of reason.
Count according to the mass fraction, it is as follows relative to 10 parts of calculating of acrylic acid, the specific dosage of component:
Acrylic acid 10;Acrylamide 3-7;Acrylic acid -2- hydroxyl ethyl esters 1-2;Hydrophilic polymer 1-3;Initiator 0.01-0.15;
Crosslinking agent 0.006-0.2;Right 50%-90% in nertralizer control;Organic dispersion medium 50-70;Dispersant 0.2-0.6;Second
Alcohol 30-100;Deionized water 30-60;The nano particle 0.5-10 of silane coupler processing.
The hydrophilic polymer is one or both of polyvinyl alcohol, polyethylene glycol, polyvinylpyrrolidone.
The initiator is potassium peroxydisulfate or ammonium persulfate.
The crosslinking agent is acrylic acid propylene, glycol diacrylate or N, N '-methylene-bisacrylamide.
The nertralizer is sodium carbonate, sodium acid carbonate, sodium hydroxide, potassium hydroxide or ammonium hydrogencarbonate.
The organic dispersion medium is n-hexane or hexamethylene.
The dispersant is one kind or one kind in Span20, Span40, Span60, Span80, Tween20, Tween40
More than.
The nano particle of the silane coupler processing is to handle tricalcium phosphate, potassium nitrate, fluorination using silane coupler
One or more kinds of nano particles in sodium, strontium fluoride.Its preparation method is as follows:
(1)Under stirring, silane coupler is added in nano particle, stirs 1-3 hours;Silane coupler and nanometer
The quality parts ratio of particle is:0.5:10-3:10;
(2)By mixture in 50-70 DEG C of baking oven, dry 4-6 hours, grinding, obtain the nano particle of silane coupler processing.
Above-mentioned silane coupler be gamma-aminopropyl-triethoxy-silane, γ-(2,3- the third oxygen of epoxy)Propyl trimethoxy silicon
Alkane, γ-(Methacryloxypropyl)One or more in propyl trimethoxy silicane, γ-mercaptopropyl trimethoxysilane.
Its specific preparation method of gear division desensitizer of the present invention comprises the following steps.
(1)Nertralizer deionized water dissolving is taken, is then slowly added in ice-water bath in acrylic acid, stirring is to having reacted
Entirely;
(2)It is water-soluble that acrylamide, acrylic acid -2- hydroxyl ethyl esters, ethanol, hydrophilic polymer are added in the solution obtained by step 1
Liquid, the nano particle of silane coupler processing, ultrasonic oscillation are scattered 2~8 hours;
(3)Initiator and crosslinking agent are dissolved in deionized water, are well mixed with step 2 gained mixed liquor, it is stand-by;
(4)Take dispersant to be dissolved in organic dispersion medium, then add step 3 gained mixed liquor, stir under nitrogen protection
Uniformly, 60-80 DEG C is then heated to, isothermal reaction 3~8 hours,
(5)Ethanol is added dropwise in the reaction system obtained by step 4, is sufficiently stirred;It is kept stirring for dropping to room temperature, produces final production
Product.
Gear division desensitizer of the present invention, there is desensitization to take effect, can persistently desensitize, while there is anticaries action, grasp
Make the advantages that simple and convenient, its feature is as follows:
(1)Nano particle is handled using silane coupler, nano particle is disperseed in high-molecular copolymer more equal
It is even, the effect of desensitization can be effectively improved;
(2)Using situ aggregation method, the hydrophilic polymer of line style is added in main body exchanges body, desensitizer is improved and oral cavity sticks
Film and the combination of saliva, be advantageous to further improve desensitization effect;
(3)Hydrophile copolymers are used in high-molecular copolymer, the nano particle of parcel can delay in the presence of hydrophilic radical
On The Drug Release, effectively extend desensitizing anticarious effect.
Embodiment
With embodiment, the present invention will be further described below.
Embodiment 1
(1)With 20g deionized water dissolving 4.44g sodium hydroxides, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
Mix it is complete to reaction, in it is right be 80%.
(2)In step(1)3g acrylamides, 1.5g acrylic acid -2- hydroxyl ethyl esters are added in resulting solution, 30g ethanol, is contained admittedly
The nano particle of polyvinyl alcohol water solution and 4g the silane couplers processing for 1g is measured, is disperseed 3 hours with ultrasonic vibration.
(3)By 0.06g ammonium persulfates and 0.01gN, N '-methylene-bisacrylamide is dissolved in 10g deionized waters, with
Step(2)Gained mixed liquor is well mixed, stand-by.
(4)Take 0.1gSpan20 and 0.2gSpan60 to be dissolved in 60g hexamethylene, then add step(3)Gained mixes
Close in liquid, nitrogen charging gas shielded, stir, then heat to 75 DEG C, isothermal reaction 4 hours.
(5)In step(4)15g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. weigh 0.5g gamma-aminopropyl-triethoxy-silanes and 0.5g γ-(2,3- the third oxygen of epoxy)Propyl trimethoxy silicane
It is added in 10g sodium fluorides, stirs 1.5 hours under stirring;
2. by mixture in 50 DEG C of baking oven, dry 6 hours, grinding, obtain the nano particle of silane coupler processing.
Embodiment 2
(1)With 25g deionized water dissolving 4.47g potassium hydroxide, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
Mix it is complete to reaction, in it is right be 70%.
(2)In step(1)5g acrylamides, 1g acrylic acid -2- hydroxyl ethyl esters, 35g ethanol, solid content are added in resulting solution
The nano particle of polyvinyl alcohol water solution and the processing of 0.5g silane couplers for 1.5g, is disperseed 2 hours with ultrasonic vibration.
(3)0.08g ammonium persulfates and 0.006g acrylic acid propylenes are dissolved in 20g deionized waters, with step(2)Institute
Mixed liquor is obtained to be well mixed, it is stand-by.
(4)Take 0.25g Span20 and 0.1g Span30 to be dissolved in 50g hexamethylene, then add step(3)Gained
In mixed liquor, nitrogen charging gas shielded, stir, then heat to 80 DEG C, isothermal reaction 3 hours.
(5)In step(4)20g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. weighing 1.5g γ-(2,3- the third oxygen of epoxy)Propyl trimethoxy silicane is added to 3g tricalcium phosphates under stirring
In 7g potassium nitrate, stir 2 hours;
2. by mixture in 55 DEG C of baking oven, dry 6 hours, grinding, obtain the nano particle of silane coupler processing.
Embodiment 3
(1)With 30g deionized water dissolving 9.87g ammonium hydrogen carbonate, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
Mix it is complete to reaction, in it is right be 90%.
(2)In step(1)3.5g acrylamides, 2g acrylic acid -2- hydroxyl ethyl esters are added in resulting solution, 20g ethanol, is contained admittedly
Measure what the Aqueous Solutions of Polyethylene Glycol for 0.5g, the aqueous solution for the polyvinyl alcohol that solid content is 0.5g and 10g silane couplers were handled
Nano particle, disperseed 8 hours with ultrasonic vibration.
(3)0.1g ammonium persulfates and 0.08g N, N '-methylene-bisacrylamide are dissolved in 30g deionized waters, with
Step(2)Gained mixed liquor is well mixed, stand-by.
(4)Take 0.3g Span60 to be dissolved in 70g hexamethylene, then add step(3)In gained mixed liquor, nitrogen charging
Gas shielded, stir, then heat to 60 DEG C, isothermal reaction 3 hours.
(5)In step(4)30g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. weighing 3g gamma-aminopropyl-triethoxy-silanes to be added under stirring in 2g potassium nitrate and 8g strontium fluorides, stir
1.5 hour;
2. by mixture in 50 DEG C of baking oven, dry 6 hours, grinding, obtain the nano particle of silane coupler processing.
Embodiment 4
(1)With 35g deionized water dissolving 10.31g sodium carbonate, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
To reaction completely, right in is 70%.
(2)In step(1)7g acrylamides, 1.5g acrylic acid -2- hydroxyl ethyl esters are added in resulting solution, 55g ethanol, is contained admittedly
Measure what the Aqueous Solutions of Polyethylene Glycol for 1.5g, the aqueous solution for the polyvinyl alcohol that solid content is 0.5g and 10g silane couplers were handled
Nano particle, disperseed 4 hours with ultrasonic vibration.
(3)0.01g potassium peroxydisulfates and 0.2g N, N '-methylene-bisacrylamide are dissolved in 20g deionized waters, with
Step(2)Gained mixed liquor is well mixed, stand-by.
(4)Take 0.3g Span60,0.2g Span40 and 0.1gSpan 80 to be dissolved in 70g hexamethylene, then add
Step(3)In gained mixed liquor, nitrogen charging gas shielded, stir, then heat to 65 DEG C, isothermal reaction 5 hours.
(5)In step(4)45g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. weigh 2g gamma-aminopropyl-triethoxy-silanes and 1g γ-(Methacryloxypropyl)Propyl trimethoxy silicane is stirring
Mix and be added under state in 4g potassium nitrate and 6g sodium fluorides, stirred 2.5 hours;
2. by mixture in 50 DEG C of baking oven, dry 6 hours, grinding, obtain the nano particle of silane coupler processing.
Embodiment 5
(1)With 30g deionized water dissolving 3.89g potassium hydroxide, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
Mix it is complete to reaction, in it is right be 50%.
(2)In step(1)5g acrylamides, 1.6g acrylic acid -2- hydroxyl ethyl esters are added in resulting solution, 47g ethanol, is contained admittedly
The nano particle of Aqueous Solutions of Polyethylene Glycol and 6g the silane couplers processing for 3g is measured, is disperseed 6 hours with ultrasonic vibration.
(3)0.08g ammonium persulfates and 0.06 glycol diacrylate are dissolved in 15g deionized waters, with step(2)
Gained mixed liquor is well mixed, stand-by.
(4)Take 0.2g Span60 to be dissolved in 50g hexamethylene, then add step(3)In gained mixed liquor, nitrogen charging
Gas shielded, stir, then heat to 65 DEG C, isothermal reaction 3.5 hours.
(5)In step(4)25g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. weigh 1.5g gamma-aminopropyl-triethoxy-silanes and 1g γ-mercaptopropyl trimethoxysilane adds under stirring
Into 3g potassium nitrate and 7g tricalcium phosphates, stir 2.5 hours;
2. by mixture in 60 DEG C of baking oven, dry 4 hours, grinding, obtain the nano particle of silane coupler processing.
Embodiment 6
(1)With 30g deionized water dissolving 9.33g ammonium hydrogen carbonate, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
Mix it is complete to reaction, in it is right be 80%.
(2)In step(1)3g acrylamides, 1g acrylic acid -2- hydroxyl ethyl esters, 14g ethanol, solid content are added in resulting solution
The nanometer of the aqueous solution and 5.5g the silane couplers processing for the polyvinyl alcohol for being 2g for 1g Aqueous Solutions of Polyethylene Glycol, solid content
Grain, is disperseed 7 hours with ultrasonic vibration.
(3)0.15g ammonium persulfates and 0.06g N, N '-methylene-bisacrylamide are dissolved in 15g deionized waters, with
Step(2)Gained mixed liquor is well mixed, stand-by.
(4)Take 0.6g Span20 to be dissolved in 70g hexamethylene, then add step(3)In gained mixed liquor, nitrogen charging
Gas shielded, stir, then heat to 70 DEG C, isothermal reaction 6 hours.
(5)In step(4)16g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. weighing 2g gamma-aminopropyl-triethoxy-silanes to be added under stirring in 6g sodium fluorides and 4g potassium nitrate, stir
2.5 hour;
2. by mixture in 60 DEG C of baking oven, dry 5 hours, grinding, obtain the nano particle of silane coupler processing.
Embodiment 7
(1)With 35g deionized water dissolving 4.44g sodium hydroxides, then it is slowly added into 10g acrylic acid, stirs in ice-water bath
Mix it is complete to reaction, in it is right be 80%.
(2)In step(1)6g acrylamides, 2g acrylic acid -2- hydroxyl ethyl esters, 54g ethanol, solid content are added in resulting solution
The nanometer of the aqueous solution and 5g the silane couplers processing for the polyvinyl alcohol for being 1.5g for 0.5g Aqueous Solutions of Polyethylene Glycol, solid content
Particle, disperseed 5 hours with ultrasonic vibration.
(3)0.07g ammonium persulfates and 0.08g N, N '-methylene-bisacrylamide are dissolved in 25g deionized waters, with
Step(2)Gained mixed liquor is well mixed, stand-by.
(4)Take 0.3g Span60 to be dissolved in 55g hexamethylene, then add step(3)In gained mixed liquor, nitrogen charging
Gas shielded, stir, then heat to 60 DEG C, isothermal reaction 3 hours.
(5)In step(4)20g ethanol is added dropwise in the reaction system of gained, continues to be stirred until homogeneous.It is kept stirring for dropping to
Room temperature, produce final products.
Step(2)The nano particle preparation process of middle silane coupler processing is as follows:
1. 1.6g gamma-aminopropyl-triethoxy-silanes are weighed to be added under stirring in 7g potassium nitrate and 3g tricalcium phosphates,
Stirring 2.5 hours;
2. by mixture in 55 DEG C of baking oven, dry 6 hours, grinding, obtain the nano particle of silane coupler processing.
Claims (10)
1. a kind of gear division desensitizer is prepared by high-molecular copolymer Encapsulation nanoparticle, wherein high-molecular copolymer is propylene
Acid(Ester)Copolymer, nano particle are the nano particle of silane coupler processing;Described gear division desensitizer component includes:Propylene
Acid, acrylic acid amides, acrylic acid -2- hydroxyl ethyl esters, hydrophilic polymer, initiator, crosslinking agent, nertralizer, organic dispersion medium,
Dispersant, ethanol, deionized water and the nano particle of silane coupler processing;
Count according to the mass fraction, it is as follows relative to 10 parts of calculating of acrylic acid, the specific dosage of component:
Acrylic acid 10;Acrylamide 3-7;Acrylic acid -2- hydroxyl ethyl esters 1-2;Hydrophilic polymer 1-3;Initiator 0.01-0.15;
Crosslinking agent 0.006-0.2;Right 50%-90% in nertralizer control;Organic dispersion medium 50-70;Dispersant 0.2-0.6;Second
Alcohol 30-100;Deionized water 30-60;The nano particle 0.5-10 of silane coupler processing.
2. gear division desensitizer as claimed in claim 1, it is characterised in that the hydrophilic polymer is polyvinyl alcohol, poly- second two
One or both of alcohol, polyvinylpyrrolidone.
3. gear division desensitizer as claimed in claim 1, it is characterised in that the initiator is potassium peroxydisulfate or ammonium persulfate.
4. gear division desensitizer as claimed in claim 1, it is characterised in that the crosslinking agent is acrylic acid propylene, ethylene glycol two
Acrylate or N, N '-methylene-bisacrylamide.
5. gear division desensitizer as claimed in claim 1, it is characterised in that the nertralizer is sodium carbonate, sodium acid carbonate, hydrogen-oxygen
Change sodium, potassium hydroxide or ammonium hydrogencarbonate.
6. gear division desensitizer as claimed in claim 1, it is characterised in that the organic dispersion medium is n-hexane or hexamethylene.
7. gear division desensitizer as claimed in claim 1, it is characterised in that the dispersant be Span20, Span40, Span60,
One or more in Span80, Tween20, Tween40.
8. gear division desensitizer as claimed in claim 1, it is characterised in that the nano particle of the silane coupler processing is to adopt
With one or more kinds of nano particles in silane coupler processing tricalcium phosphate, potassium nitrate, sodium fluoride, strontium fluoride;It is described
Silane coupler processing nano particle, it is characterised in that the silane coupler be gamma-aminopropyl-triethoxy-silane,
γ-(2,3- the third oxygen of epoxy)Propyl trimethoxy silicane, γ-(Methacryloxypropyl)Propyl trimethoxy silicane, γ-mercapto propyl group
One or more in trimethoxy silane.
9. the nano particle of silane coupler processing as claimed in claim 8, its preparation method are as follows:
Under stirring, silane coupler is added in nano particle, stirs 1-3 hours;Silane coupler and nanometer
Grain quality parts ratio be:0.5:10-3:10;
By mixture in 50-70 DEG C of baking oven, dry 4-6 hours, grinding, obtain the nano particle of silane coupler processing.
10. gear division desensitizer as claimed in claim 1, it is characterised in that specific preparation method comprises the following steps:
Nertralizer deionized water dissolving is taken, is then slowly added in ice-water bath in acrylic acid, stirring is complete to reaction;
(2)It is water-soluble that acrylamide, acrylic acid -2- hydroxyl ethyl esters, ethanol, hydrophilic polymer are added in the solution obtained by step 1
Liquid, the nano particle of silane coupler processing, ultrasonic oscillation are scattered 2~8 hours;
(3)Initiator and crosslinking agent are dissolved in deionized water, are well mixed with step 2 gained mixed liquor, it is stand-by;
(4)Take dispersant to be dissolved in organic dispersion medium, then add step 3 gained mixed liquor, stir under nitrogen protection
Uniformly, 60-80 DEG C is then heated to, isothermal reaction 3~8 hours;
(5)Ethanol is added dropwise in the reaction system obtained by step 4, is sufficiently stirred;It is kept stirring for dropping to room temperature, produces final production
Product.
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Citations (4)
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CN101240052A (en) * | 2008-02-29 | 2008-08-13 | 厦门大学 | Method for preparing acrylic acid series semi-interpenetration network composite high water absorption resin |
WO2008140476A2 (en) * | 2006-10-31 | 2008-11-20 | Oroscience, Inc. | Process to form nano-sized materials, the compositions and uses thereof |
CN102245153A (en) * | 2008-10-08 | 2011-11-16 | 生物薄膜有限公司 | Tooth remineralisation |
US20170112949A1 (en) * | 2015-10-21 | 2017-04-27 | The Regents Of The University Of Michigan | Detection and treatment of caries and microcavities with nanoparticles |
-
2017
- 2017-06-01 CN CN201710402436.7A patent/CN107343960A/en active Pending
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2008140476A2 (en) * | 2006-10-31 | 2008-11-20 | Oroscience, Inc. | Process to form nano-sized materials, the compositions and uses thereof |
CN101240052A (en) * | 2008-02-29 | 2008-08-13 | 厦门大学 | Method for preparing acrylic acid series semi-interpenetration network composite high water absorption resin |
CN102245153A (en) * | 2008-10-08 | 2011-11-16 | 生物薄膜有限公司 | Tooth remineralisation |
US20170112949A1 (en) * | 2015-10-21 | 2017-04-27 | The Regents Of The University Of Michigan | Detection and treatment of caries and microcavities with nanoparticles |
Non-Patent Citations (1)
Title |
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Application publication date: 20171114 |