CN106986998A - A kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle - Google Patents
A kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle Download PDFInfo
- Publication number
- CN106986998A CN106986998A CN201710362718.9A CN201710362718A CN106986998A CN 106986998 A CN106986998 A CN 106986998A CN 201710362718 A CN201710362718 A CN 201710362718A CN 106986998 A CN106986998 A CN 106986998A
- Authority
- CN
- China
- Prior art keywords
- poly
- ppdo
- acrylic acid
- graft copolymer
- caprolactone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- C08J3/097—Sulfur containing compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/027—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyester or polycarbonate sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2230/00—Compositions for preparing biodegradable polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2387/00—Characterised by the use of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Polyamides (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
The present invention discloses a kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle, using following steps：1）Addition polymerization acrylic acid, hydroxy-end capped PPDO monododecyl ether, solvent and condensing agent in reactor, react to obtain polyacrylic acid PPDO graft copolymer；2）Adjunction graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensing agent, react to obtain dual graft copolymer in reactor；3）Add dual graft copolymer and solvent in reactor, dissolve to obtain dual graft copolymer stoste；4）Stoste is added into bag filter, the beaker for filling selective solvent is put into, is replaced 3~4 times, is poured into graduated volumetric flask, be adjusted to scale, obtain object of the present invention.Preparation technology of the present invention is simple, be easy to grasp, and gained object is a kind of new pharmaceutical carrier.
Description
Technical field
The present invention relates to a kind of method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, category
In biodegradated polymer materal preparing technical field.
Background technology
Polyacrylic acid is a kind of biomaterial with good biocompatibility and biodegradability, with excellent
Hydrophily, in terms of being widely used in medicine and pharmacology.Polycaprolactone and PPDO are with excellent biocompatibility
With the biomaterial of biodegradability, all with good hydrophobicity, had a wide range of applications in medicine.First will be poly-
Lanthanum Isopropoxide segment, which is grafted on polyacrylic acid strand, obtains poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer,
Polycaprolactone segment is grafted to gained on the polyacrylic acid segment in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer again
To poly acrylic acid-poly caprolactone-PPDO dual graft copolymer have it is amphipathic, can in selective solvent
Micella is self-assembly of, is a kind of new pharmaceutical carrier, is had broad application prospects in medicine.
The content of the invention
Poly acrylic acid-poly caprolactone-poly- is preferably prepared it is an object of the invention to provide a kind of simple to operate and effect
The method of Lanthanum Isopropoxide copolymer micelle.Its technical scheme is：
A kind of method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, it is characterised in that：Copolymerization
The molecular weight of polyacrylic acid segment is 52000~61000 in thing, the molecular weight of PPDO segment for 2400~
2600, the molecular weight of polycaprolactone segment is 2200~2300；Its preparation method uses following steps：
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer：Polyacrylic acid, hydroxyl are added in dry reactor
Under PPDO monododecyl ether, solvent and the condensing agent of end-blocking, inert atmosphere, in 27~33 DEG C of stirring reactions 2
~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer：Added in dry reactor poly-
Acrylic acid-PPDO graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensing agent,
Under inert atmosphere, in 28~34 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste：Add in dry reactor
Enter poly acrylic acid-poly caprolactone-PPDO dual graft copolymer and solvent, in 46~51 DEG C of stirring and dissolvings 50~60
Minute, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer micelle：At room temperature, by stoste plus
Enter in bag filter, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 7 hours once, displacement 3~4
Secondary, solution shows blue light in bag filter, is then poured into in graduated volumetric flask, scale is adjusted to selective solvent,
Obtain object.
A kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, step 1）
In, the mol ratio of PPDO monododecyl ether and polyacrylic acid is 15~25:1.
A kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, step 1）
In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- diformazan ammonia
Propyl group）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.07~1.9:1, solvent uses dimethyl sulfoxide (DMSO), reactant
Solution concentration is 5~15 g/100 ml.
A kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, step 2）
In, polycaprolactone list tridecyl ether rubs with polyacrylic acid segment in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
You are than being 15~25:1.
A kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, step 2）
In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- diformazan ammonia
Propyl group）Carbodiimide, the mol ratio of condensing agent and polyacrylic acid segment in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
For 1.07~1.9:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g/100 ml.
A kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, step 3）
In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.6 mg/ml.
A kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, step 4）
In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4000, and selective solvent uses distilled water, molten
Liquid concentration is 0.1~0.3 mg/ml.
Compared with prior art, its advantage is the present invention：
1st, a kind of described method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, using esterification
Reaction, the means that are combined of amidation process and dialysis, it is simple to operate, be easy to grasp；
2nd, a kind of described poly acrylic acid-poly caprolactone-PPDO copolymer micelle is that a kind of new medicine is carried
Body.
Embodiment
Embodiment 1
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
13.7 grams of polyacrylic acid are added in dry reactor（Molecular weight is 52000）, 11.6 grams it is hydroxy-end capped poly- to dioxy
Cyclohexanone monododecyl ether（Molecular weight is 2400）, 253 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.07 gram is addedN,N’- two rings
Under hexyl carbodiimide, inert atmosphere, in 27 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtains mesh
Mark thing；
2）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer
Added in dry reactor 10 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.5 grams it is amino-terminated poly-
Caprolactone list tridecyl ether（Molecular weight is 2200）, 175 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.048 gram is addedN,N’- two
Under carbodicyclo hexylimide, inert atmosphere, in 28 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtained
Object；
3）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste
Added in dry reactor 130 milligrams of poly acrylic acid-poly caprolactone-PPDO dual graft copolymers and
100 milliliters of dimethyl sulfoxide (DMSO)s, in 46 DEG C of stirring and dissolvings 50 minutes, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste is added into 5 milliliters of appearances
In the bag filter of amount（Molecular cut off is 3500）, put it into 500 milliliters of beakers for filling distilled water, put every 7 hours
Change once, replace 3 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, with steaming
Distilled water is adjusted to scale, obtains object.
Embodiment 2
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
14.1 grams of polyacrylic acid are added in dry reactor（Molecular weight is 55000）, 12.1 grams it is hydroxy-end capped poly- to dioxy
Cyclohexanone monododecyl ether（Molecular weight is 2500）, 262 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.041 gram is addedN,N’- two
Under diisopropylcarbodiimide, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtained
Object；
2）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer
Added in dry reactor 10.2 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.6 grams it is amino-terminated
Polycaprolactone list tridecyl ether（Molecular weight is 2200）, 177 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.028 gram is addedN,N’-
Under DIC, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtained
To object；
3）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste
Added in dry reactor 140 milligrams of poly acrylic acid-poly caprolactone-PPDO dual graft copolymers and
100 milliliters of dimethyl sulfoxide (DMSO)s, in 48 DEG C of stirring and dissolvings 55 minutes, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste is added into 6 milliliters of appearances
In the bag filter of amount（Molecular cut off is 3700）, put it into 500 milliliters of beakers for filling distilled water, put every 7 hours
Change once, replace 4 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, with steaming
Distilled water is adjusted to scale, obtains object.
Embodiment 3
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
14.7 grams of polyacrylic acid are added in dry reactor（Molecular weight is 61000）, 11.5 grams it is hydroxy-end capped poly- to dioxy
Cyclohexanone monododecyl ether（Molecular weight is 2600）, add 262 milliliters of dimethyl sulfoxide (DMSO)s, add 0.059 gram of 3- ethyl-
1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 33 DEG C of stirring reactions 4 days, terminating reaction, by filtering, dialysis,
Dry, obtain object；
2）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer
Added in dry reactor 10.3 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.4 grams it is amino-terminated
Polycaprolactone list tridecyl ether（Molecular weight is 2300）, 175 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.038 gram of 3- second is added
Base -1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 34 DEG C of stirring reactions 4 days, terminating reaction, by filtering, thoroughly
Analyse, dry, obtain object；
3）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste
Added in dry reactor 150 milligrams of poly acrylic acid-poly caprolactone-PPDO dual graft copolymers and
100 milliliters of dimethyl sulfoxide (DMSO)s, in 51 DEG C of stirring and dissolvings 60 minutes, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste is added into 7 milliliters of appearances
In the bag filter of amount（Molecular cut off is 4000）, put it into 500 milliliters of beakers for filling distilled water, put every 7 hours
Change once, replace 4 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, with steaming
Distilled water is adjusted to scale, obtains object.
Claims (7)
1. a kind of method for preparing poly acrylic acid-poly caprolactone-PPDO copolymer micelle, it is characterised in that：Altogether
The molecular weight of polyacrylic acid segment is 52000~61000 in polymers, the molecular weight of PPDO segment for 2400~
2600, the molecular weight of polycaprolactone segment is 2200~2300；Its preparation method uses following steps：
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer：Polyacrylic acid, hydroxyl are added in dry reactor
Under PPDO monododecyl ether, solvent and the condensing agent of end-blocking, inert atmosphere, in 27~33 DEG C of stirring reactions 2
~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer：Added in dry reactor poly-
Acrylic acid-PPDO graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensing agent,
Under inert atmosphere, in 28~34 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer stoste：Add in dry reactor
Enter poly acrylic acid-poly caprolactone-PPDO dual graft copolymer and solvent, in 46~51 DEG C of stirring and dissolvings 50~60
Minute, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PPDO dual graft copolymer micelle：At room temperature, by stoste plus
Enter in bag filter, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 7 hours once, displacement 3~4
Secondary, solution shows blue light in bag filter, is then poured into in graduated volumetric flask, scale is adjusted to selective solvent,
Obtain object.
2. a kind of poly acrylic acid-poly caprolactone-PPDO copolymer micelle of preparing according to claim 1
Method, it is characterised in that：Step 1）In, the mol ratio of PPDO monododecyl ether and polyacrylic acid for 15~
25:1。
3. a kind of poly acrylic acid-poly caprolactone-PPDO copolymer micelle of preparing according to claim 1
Method, it is characterised in that：Step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- diisopropyl carbon two is sub-
Amine or 3- ethyls -1-（3- dimethylaminopropyls）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.07~1.9:1, it is molten
Agent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g/100 ml.
4. a kind of poly acrylic acid-poly caprolactone-PPDO copolymer micelle of preparing according to claim 1
Method, it is characterised in that：Step 2）In, polycaprolactone list tridecyl ether and the grafting of poly acrylic acid-poly Lanthanum Isopropoxide are common
The mol ratio of polyacrylic acid segment is 15~25 in polymers:1.
5. a kind of poly acrylic acid-poly caprolactone-PPDO copolymer micelle of preparing according to claim 1
Method, it is characterised in that：Step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- diisopropyl carbon two is sub-
Amine or 3- ethyls -1-（3- dimethylaminopropyls）Carbodiimide, condensing agent and poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
The mol ratio of middle polyacrylic acid segment is 1.07~1.9:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15
g/100 ml。
6. a kind of poly acrylic acid-poly caprolactone-PPDO copolymer micelle of preparing according to claim 1
Method, it is characterised in that：Step 3）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.6 mg/ml.
7. a kind of poly acrylic acid-poly caprolactone-PPDO copolymer micelle of preparing according to claim 1
Method, it is characterised in that：Step 4）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4000, choosing
Selecting property solvent uses distilled water, and solution concentration is 0.1~0.3 mg/ml.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710362718.9A CN106986998A (en) | 2017-05-22 | 2017-05-22 | A kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710362718.9A CN106986998A (en) | 2017-05-22 | 2017-05-22 | A kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106986998A true CN106986998A (en) | 2017-07-28 |
Family
ID=59420462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710362718.9A Withdrawn CN106986998A (en) | 2017-05-22 | 2017-05-22 | A kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106986998A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542185A (en) * | 2016-03-14 | 2016-05-04 | 山东理工大学 | Method for preparing polyvinyl alcohol-polycaprolactone-poly(p-dioxanone) dual-grafted copolymer micelle |
| CN105754109A (en) * | 2016-03-09 | 2016-07-13 | 山东理工大学 | Preparation method of polyvinyl alcohol-polycaprolactone-poly-p-dioxanone dual-grafted copolymer micelle |
-
2017
- 2017-05-22 CN CN201710362718.9A patent/CN106986998A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105754109A (en) * | 2016-03-09 | 2016-07-13 | 山东理工大学 | Preparation method of polyvinyl alcohol-polycaprolactone-poly-p-dioxanone dual-grafted copolymer micelle |
| CN105542185A (en) * | 2016-03-14 | 2016-05-04 | 山东理工大学 | Method for preparing polyvinyl alcohol-polycaprolactone-poly(p-dioxanone) dual-grafted copolymer micelle |
Non-Patent Citations (1)
| Title |
|---|
| YANHUI MA等: ""Polymer Micelles from Poly(acrylic acid)-graft-polystyrene"", 《MACROMOLECULES》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106986998A (en) | A kind of method for preparing polyacrylic acid polycaprolactone PPDO copolymer micelle | |
| CN107118362A (en) | A kind of preparation method of polyacrylic acid polycaprolactone MPEGPLA copolymer micelles | |
| CN106987000A (en) | A kind of preparation method of polyacrylic acid polycaprolactone PPDO copolymer micelle | |
| CN106977729A (en) | A kind of method for preparing polyacrylic acid PPDO MPEGPLA copolymer micelles | |
| CN106977732A (en) | A kind of preparation method of polyacrylic acid PPDO MPEGPLA copolymer micelles | |
| CN106987001A (en) | A kind of preparation method of polyacrylic acid MPEGPLA graft copolymer micellas | |
| CN107118364A (en) | A kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella | |
| CN106986995A (en) | A kind of preparation method of polyacrylic acid PPDO copolymer of poly lactic acid micella | |
| CN106977733A (en) | A kind of method for preparing polyacrylic acid PTMC copolymer of poly lactic acid micella | |
| CN107033362A (en) | A kind of method for preparing polyacrylic acid polycaprolactone PTMC copolymer micelle | |
| CN107057073A (en) | A kind of method for preparing polyacrylic acid PPDO copolymer of poly lactic acid micella | |
| CN106977736A (en) | A kind of method for preparing polyacrylic acid PPDO polycaprolactone polypropylene glycol copolymers micella | |
| CN106986999A (en) | A kind of method for preparing polyacrylic acid PTMC MPEGPLA copolymer micelles | |
| CN107118367A (en) | A kind of method for preparing polyacrylic acid PPDO polycaprolactone PLGA micella | |
| CN106986996A (en) | A kind of polyacrylic acid polycaprolactone gathers（Lactide glycolide）The preparation method of copolymer micelle | |
| CN107043458A (en) | A kind of preparation method of polyacrylic acid polylactic acid poly caprolactone dual graft copolymer micelle | |
| CN106986997A (en) | A kind of method for preparing polyacrylic acid polycaprolactone copolymer of poly lactic acid micella | |
| CN106987007A (en) | A kind of method for preparing polyacrylic acid PPDO polycaprolactone PTMC copolymer micelle | |
| CN106987010A (en) | A kind of method for preparing polyacrylic acid PPDO PTMC copolymer of poly lactic acid micella | |
| CN106947086A (en) | A kind of preparation method of polyacrylic acid PTMC MPEGPLA copolymer micelles | |
| CN106977734A (en) | One kind prepares polyacrylic acid polycaprolactone and gathered（Lactide glycolide）The method of copolymer micelle | |
| CN106977740A (en) | A kind of preparation method of polyacrylic acid polylactic acid graft copolymer micella | |
| CN107011520A (en) | A kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle | |
| CN107118365A (en) | A kind of preparation method of polyacrylic acid polycaprolactone PTMC copolymer micelle | |
| CN107011521A (en) | A kind of preparation method of polyacrylic acid PPDO polycaprolactone copolymer of poly lactic acid micella |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20170728 |
|
| WW01 | Invention patent application withdrawn after publication |