CN106986997A - A kind of method for preparing polyacrylic acid polycaprolactone copolymer of poly lactic acid micella - Google Patents
A kind of method for preparing polyacrylic acid polycaprolactone copolymer of poly lactic acid micella Download PDFInfo
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- CN106986997A CN106986997A CN201710362709.XA CN201710362709A CN106986997A CN 106986997 A CN106986997 A CN 106986997A CN 201710362709 A CN201710362709 A CN 201710362709A CN 106986997 A CN106986997 A CN 106986997A
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- 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
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Abstract
The present invention discloses a kind of method for preparing polyacrylic acid polycaprolactone copolymer of poly lactic acid micella, using following steps：1）Addition polymerization acrylic acid, hydroxy-end capped PLA monododecyl ether, solvent and condensing agent, react to obtain polyacrylic acid polylactic acid graft copolymer in reactor；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-copolymer of poly lactic acid micella, belong to biological drop
Solve field of polymer material preparing technology.
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 PLA are can with excellent biocompatibility and biology
The biomaterial of degradability, all with good hydrophobicity, has a wide range of applications in medicine.First by polylactic acid chain segment
It is grafted on polyacrylic acid strand and obtains poly acrylic acid-poly lactic acid graft copolymer, then polycaprolactone segment is grafted to poly-
Poly acrylic acid-poly caprolactone-PLA pair obtained by polyacrylic acid segment in acrylic acid-polylactic acid graft copolymer connects
Graft copolymer has amphipathic, and micella can be self-assembly of in selective solvent, is a kind of new pharmaceutical carrier, in doctor
Pharmaceutical field has broad application prospects.
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 lactic acid copolymer micella.Its technical scheme is：
A kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, it is characterised in that：Poly- third in copolymer
The molecular weight of olefin(e) acid segment is 52000~62000, and the molecular weight of polylactic acid chain segment is 2500~2600, polycaprolactone segment
Molecular weight is 2200~2400；Its preparation method uses following steps：
1）The preparation of poly acrylic acid-poly lactic acid graft copolymer：Polyacrylic acid is added in dry reactor, it is hydroxy-end capped poly-
Under lactic acid monododecyl ether, solvent and condensing agent, inert atmosphere, in 28~33 DEG C of stirring reactions 2~4 days, terminating reaction was led to
Filter, dialyse, dry, obtain object；
2）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer：In dry reactor add polyacrylic acid-
Under polylactic acid graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensing agent, inert atmosphere, in 29
~34 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, is dried, obtains object；
3）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste：Polypropylene is added in dry reactor
Acid-polycaprolactone-PLA dual graft copolymer and solvent, in 47~52 DEG C of stirring and dissolvings 50~60 minutes, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer micelle：At room temperature, stoste is added into bag filter
In, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 7 hours once, replace 3~4 times, bag filter
Middle solution shows blue light, is then poured into in graduated volumetric flask, scale is adjusted to selective solvent, obtain target
Thing.
A kind of described method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, step 1）In, gather breast
Sour monododecyl ether is using poly-（D, Pfansteihl）Mole of monododecyl ether, PLA monododecyl ether and polyacrylic acid
Than for 15~25:1.
A kind of described method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, step 1）In, condensation
Agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- dimethylaminopropyls）Carbon
The mol ratio of diimine, condensing agent and polyacrylic acid is 1.07~1.9:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution is dense
Spend for 5~15 g/100 ml.
A kind of described method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, step 2）In, gather oneself
The mol ratio of lactone list tridecyl ether and polyacrylic acid segment in poly acrylic acid-poly lactic acid graft copolymer is 15~25:1.
A kind of described method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, step 2）In, condensation
Agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- dimethylaminopropyls）Carbon
The mol ratio of diimine, condensing agent and polyacrylic acid segment in poly acrylic acid-poly lactic acid graft copolymer is 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-copolymer of poly lactic acid micella, step 3）In, solvent
Using dimethyl sulfoxide (DMSO), original liquid concentration is 1~1.5 mg/ml.
A kind of described method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, step 4）In, dialysis
Bag capacity is 5~10 ml, and bag filter molecular cut off is 3500~4000, and selective solvent uses distilled water, and solution 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-copolymer of poly lactic acid micella, using esterification, acyl
The means that aminating reaction and dialysis are combined, it is simple to operate, be easy to grasp；
2nd, a kind of described poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella is a kind of new pharmaceutical carrier.
Embodiment
Embodiment 1
1）The preparation of poly acrylic acid-poly lactic acid graft copolymer
13.7 grams of polyacrylic acid are added in dry reactor（Molecular weight is 52000）, 12.1 grams of hydroxy-end capped PLA lists
Lauryl ether（Molecular weight is 2500）, 258 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.073 gram is addedN,N’- dicyclohexyl carbon
Under diimine, inert atmosphere, in 28 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer
10 grams of poly acrylic acid-poly lactic acid graft copolymers, 7.7 grams of amino-terminated polycaprolactone lists are added in dry reactor
Tridecyl ether（Molecular weight is 2200）, 177 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.048 gram is addedN,N’- dicyclohexyl carbon
Under diimine, inert atmosphere, in 29 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste
130 milligrams of poly acrylic acid-poly caprolactone-PLA dual graft copolymers and 100 milliliter two are added in dry reactor
Methyl sulfoxide, in 47 DEG C of stirring and dissolvings 50 minutes, obtains object；
4）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste is added to the dialysis of 5 milliliters of capacity
In bag（Molecular cut off is 3500）, put it into 500 milliliters of beakers for filling distilled water, every displacement in 7 hours once, put
Change 3 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, is adjusted to distilled water
Scale, obtains object.
Embodiment 2
1）The preparation of poly acrylic acid-poly lactic acid graft copolymer
14.1 grams of polyacrylic acid are added in dry reactor（Molecular weight is 55000）, 12.2 grams of hydroxy-end capped PLA lists
Lauryl ether（Molecular weight is 2500）, 263 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.041 gram is addedN,N’- diisopropyl carbon
Under diimine, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer
10.2 grams of poly acrylic acid-poly lactic acid graft copolymers, 7.6 grams of amino-terminated polycaprolactones are added in dry reactor
Single tridecyl ether（Molecular weight is 2300）, 178 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.028 gram is addedN,N’- diisopropyl carbon
Under diimine, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste
135 milligrams of poly acrylic acid-poly caprolactone-PLA dual graft copolymers and 100 milliliter two are added in dry reactor
Methyl sulfoxide, in 50 DEG C of stirring and dissolvings 55 minutes, obtains object；
4）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste is added to the dialysis of 6 milliliters of capacity
In bag（Molecular cut off is 3700）, put it into 500 milliliters of beakers for filling distilled water, every displacement in 7 hours once, put
Change 4 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, is adjusted to distilled water
Scale, obtains object.
Embodiment 3
1）The preparation of poly acrylic acid-poly lactic acid graft copolymer
14.9 grams of polyacrylic acid are added in dry reactor（Molecular weight is 62000）, 11.5 grams of hydroxy-end capped PLA lists
Lauryl ether（Molecular weight is 2600）, 264 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.059 gram of 3- ethyls -1- is added（3- diformazans
Aminopropyl）Under carbodiimide, inert atmosphere, in 33 DEG C of stirring reactions 4 days, terminating reaction by filtering, dialysis, was dried, obtained
Object；
2）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer
10.3 grams of poly acrylic acid-poly lactic acid graft copolymers, 7.5 grams of amino-terminated polycaprolactones are added in dry reactor
Single tridecyl ether（Molecular weight is 2400）, 177 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.039 gram of 3- ethyls -1- is added（3- bis-
First aminopropyl）Under carbodiimide, inert atmosphere, in 34 DEG C of stirring reactions 4 days, terminating reaction by filtering, dialysis, was dried, obtained
To object；
3）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste
140 milligrams of poly acrylic acid-poly caprolactone-PLA dual graft copolymers and 100 milliliter two are added in dry reactor
Methyl sulfoxide, in 52 DEG C of stirring and dissolvings 60 minutes, obtains object；
4）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste is added to the dialysis of 7 milliliters of capacity
In bag（Molecular cut off is 4000）, put it into 500 milliliters of beakers for filling distilled water, every displacement in 7 hours once, put
Change 4 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, is adjusted to distilled water
Scale, obtains object.
Claims (7)
1. a kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella, it is characterised in that：Gather in copolymer
The molecular weight of acrylate is 52000~62000, and the molecular weight of polylactic acid chain segment is 2500~2600, polycaprolactone segment
Molecular weight be 2200~2400；Its preparation method uses following steps：
1）The preparation of poly acrylic acid-poly lactic acid graft copolymer：Polyacrylic acid is added in dry reactor, it is hydroxy-end capped poly-
Under lactic acid monododecyl ether, solvent and condensing agent, inert atmosphere, in 28~33 DEG C of stirring reactions 2~4 days, terminating reaction was led to
Filter, dialyse, dry, obtain object；
2）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer：In dry reactor add polyacrylic acid-
Under polylactic acid graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensing agent, inert atmosphere, in 29
~34 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, is dried, obtains object；
3）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer stoste：Polypropylene is added in dry reactor
Acid-polycaprolactone-PLA dual graft copolymer and solvent, in 47~52 DEG C of stirring and dissolvings 50~60 minutes, obtain object；
4）The preparation of poly acrylic acid-poly caprolactone-PLA dual graft copolymer micelle：At room temperature, stoste is added into bag filter
In, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 7 hours once, replace 3~4 times, bag filter
Middle solution shows blue light, is then poured into in graduated volumetric flask, scale is adjusted to selective solvent, obtain target
Thing.
2. a kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella according to claim 1, its
It is characterised by：Step 1）In, PLA monododecyl ether is using poly-（D, Pfansteihl）Monododecyl ether, PLA list 12
The mol ratio of alkyl ether and polyacrylic acid is 15~25:1.
3. a kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella according to claim 1, its
It is characterised by：Step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- second
Base -1-（3- dimethylaminopropyls）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.07~1.9:1, solvent uses two
Methyl sulfoxide, reactant solution concentration is 5~15 g/100 ml.
4. a kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella according to claim 1, its
It is characterised by：Step 2）In, polycaprolactone list tridecyl ether and polyacrylic acid chain in poly acrylic acid-poly lactic acid graft copolymer
The mol ratio of section is 15~25:1.
5. a kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella according to claim 1, its
It is characterised by：Step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- second
Base -1-（3- dimethylaminopropyls）Carbodiimide, condensing agent and polyacrylic acid segment in poly acrylic acid-poly lactic acid graft copolymer
Mol ratio 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 method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella according to claim 1, its
It is characterised by：Step 3）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
7. a kind of method for preparing poly acrylic acid-poly caprolactone-copolymer of poly lactic acid micella according to claim 1, its
It is characterised by：Step 4）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4000, and selectivity is molten
Agent uses distilled water, and solution concentration is 0.1~0.3 mg/ml.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105694067A (en) * | 2016-03-14 | 2016-06-22 | 山东理工大学 | Method for preparing polyvinyl alcohol-poly (lactic acid-glycolic acid)-polycaprolactone bi-grafted copolymer micelle |
| CN105754110A (en) * | 2016-03-09 | 2016-07-13 | 山东理工大学 | Preparation method of a polyvinyl alcohol-polycaprolactone-poly lactic acid-glycolic acid dual-grafted copolymer micelle |
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- 2017-05-22 CN CN201710362709.XA patent/CN106986997A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105754110A (en) * | 2016-03-09 | 2016-07-13 | 山东理工大学 | Preparation method of a polyvinyl alcohol-polycaprolactone-poly lactic acid-glycolic acid dual-grafted copolymer micelle |
| CN105694067A (en) * | 2016-03-14 | 2016-06-22 | 山东理工大学 | Method for preparing polyvinyl alcohol-poly (lactic acid-glycolic acid)-polycaprolactone bi-grafted copolymer micelle |
Non-Patent Citations (1)
| Title |
|---|
| YANHUI MA等: ""Polymer Micelles from Poly(acrylic acid)-graft-polystyrene"", 《MACROMOLECULES》 * |
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Application publication date: 20170728 |