CN107118364A - A kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella - Google Patents
A kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella Download PDFInfo
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Abstract
The present invention discloses a kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella, using following steps：1）Addition polymerization acrylic acid, hydroxy-end capped PTMC monododecyl ether, solvent and condensing agent in reactor, react to obtain polyacrylic acid PTMC graft copolymer；2）Adjunction graft copolymer, hydroxy-end capped PLA list tridecyl ether, solvent and condensing agent in reactor, react to obtain polyacrylic acid PTMC PLA dual graft copolymer；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 preparation method of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, 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.PTMC and PLA 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-
Trimethylene carbonate segment, which is grafted on polyacrylic acid strand, obtains poly acrylic acid-poly trimethylene carbonate graft copolymerization
Thing, then polylactic acid chain segment is grafted on the polyacrylic acid segment in poly acrylic acid-poly trimethylene carbonate graft copolymer
Resulting poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer have it is amphipathic, in selective solvent
Micella can be 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 trimethylene carbon is preferably prepared it is an object of the invention to provide a kind of simple to operate and effect
The method of acid esters-copolymer of poly lactic acid micella.Its technical scheme is：
A kind of preparation method of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, it is characterised in that：Copolymerization
The molecular weight of polyacrylic acid segment is 53000~62000 in thing, the molecular weight of PTMC segment for 2400~
2600, the molecular weight of polylactic acid chain segment is 2200~2300；Its preparation method uses following steps：
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer：Polyacrylic acid, hydroxyl are added in dry reactor
It is anti-in 27~35 DEG C of stirrings under PTMC monododecyl ether, solvent and the condensing agent of base end-blocking, inert atmosphere
Answer 2~3 days, terminating reaction, by filtering, dialysis, dry, obtain object；
2）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer：Added in dry reactor poly-
Acrylic acid-PTMC graft copolymer, hydroxy-end capped PLA list tridecyl ether, solvent and condensing agent,
Under inert atmosphere, in 28~35 DEG C of stirring reactions 2~3 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer stoste：Add in dry reactor
Enter poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer and solvent, in 47~52 DEG C of stirring and dissolvings 50~60
Minute, obtain object；
4）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA 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 6 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 preparation method of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, step 1）
In, the mol ratio of PTMC monododecyl ether and polyacrylic acid is 15~25:1.
A kind of preparation method of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, 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 1.07~1.8:1, solvent uses dimethyl sulfoxide (DMSO), reactant
Solution concentration is 5~15 g/100 ml.
A kind of preparation method of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, step 2）
In, PLA list tridecyl ether is using poly-（D, Pfansteihl）Single tridecyl ether, PLA list tridecyl ether and polypropylene
The mol ratio of polyacrylic acid segment is 15~25 in acid-PTMC graft copolymer:1.
A kind of preparation method of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, step 2）
In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- diformazan ammonia
Propyl group）Carbodiimide, mole of condensing agent and polyacrylic acid segment in poly acrylic acid-poly trimethylene carbonate graft copolymer
Than for 1.07~1.8:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g/100 ml.
A kind of preparation method of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, step 3）
In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
A kind of preparation method of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, 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, the preparation method of described a kind of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, using two steps
The means that esterification and dialysis are combined, it is simple to operate, be easy to grasp；
2nd, a kind of described poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella is that a kind of new medicine is carried
Body.
Embodiment
Embodiment 1
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer
14.1 grams of polyacrylic acid are added in dry reactor（Molecular weight is 53000）, 11.7 grams of hydroxy-end capped poly- three methylenes
Base carbonic ester monododecyl ether（Molecular weight is 2400）, 258 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.072 gram is addedN,N’-
Under dicyclohexylcarbodiimide, inert atmosphere, in 27 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtained
To object；
2）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer
Added in dry reactor 10 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 7.7 grams it is hydroxy-end capped
PLA list tridecyl ether（Molecular weight is 2200）, 177 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 trimethylene carbonate-PLA dual graft copolymer stoste
Added in dry reactor 120 milligrams of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymers and
100 milliliters of dimethyl sulfoxide (DMSO)s, in 47 DEG C of stirring and dissolvings 50 minutes, obtain object；
4）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly trimethylene carbonate-PLA 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 6 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 trimethylene carbonate graft copolymer
14.2 grams of polyacrylic acid are added in dry reactor（Molecular weight is 55000）, 12.1 grams of hydroxy-end capped poly- three methylenes
Base carbonic ester monododecyl ether（Molecular weight is 2500）, 263 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.042 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；
2）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer
Added in dry reactor 10.2 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 7.6 grams it is hydroxy-end capped
PLA list tridecyl ether（Molecular weight is 2200）, 178 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 trimethylene carbonate-PLA dual graft copolymer stoste
Added in dry reactor 130 milligrams of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymers and
100 milliliters of dimethyl sulfoxide (DMSO)s, in 50 DEG C of stirring and dissolvings 55 minutes, obtain object；
4）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly trimethylene carbonate-PLA 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 6 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 trimethylene carbonate graft copolymer
14.8 grams of polyacrylic acid are added in dry reactor（Molecular weight is 62000）, 11.5 grams of hydroxy-end capped poly- three methylenes
Base carbonic ester monododecyl ether（Molecular weight is 2600）, 263 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.059 gram of 3- second is added
Base -1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 35 DEG C of stirring reactions 2 days, terminating reaction, by filtering, thoroughly
Analyse, dry, obtain object；
2）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer
Added in dry reactor 10.1 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 7.6 grams it is hydroxy-end capped
PLA list tridecyl ether（Molecular weight is 2300）, 178 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.039 gram of 3- second is added
Base -1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 35 DEG C of stirring reactions 2 days, terminating reaction, by filtering, thoroughly
Analyse, dry, obtain object；
3）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer stoste
Added in dry reactor 140 milligrams of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymers and
100 milliliters of dimethyl sulfoxide (DMSO)s, in 52 DEG C of stirring and dissolvings 60 minutes, obtain object；
4）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly trimethylene carbonate-PLA 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 6 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 preparation method of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella, it is characterised in that：Altogether
The molecular weight of polyacrylic acid segment is 53000~62000 in polymers, the molecular weight of PTMC segment for 2400~
2600, the molecular weight of polylactic acid chain segment is 2200~2300；Its preparation method uses following steps：
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer：Polyacrylic acid, hydroxyl are added in dry reactor
It is anti-in 27~35 DEG C of stirrings under PTMC monododecyl ether, solvent and the condensing agent of base end-blocking, inert atmosphere
Answer 2~3 days, terminating reaction, by filtering, dialysis, dry, obtain object；
2）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer：Added in dry reactor poly-
Acrylic acid-PTMC graft copolymer, hydroxy-end capped PLA list tridecyl ether, solvent and condensing agent,
Under inert atmosphere, in 28~35 DEG C of stirring reactions 2~3 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer stoste：Add in dry reactor
Enter poly acrylic acid-poly trimethylene carbonate-PLA dual graft copolymer and solvent, in 47~52 DEG C of stirring and dissolvings 50~60
Minute, obtain object；
4）The preparation of poly acrylic acid-poly trimethylene carbonate-PLA 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 6 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 preparation of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella according to claim 1
Method, it is characterised in that：Step 1）In, the mol ratio of PTMC monododecyl ether and polyacrylic acid for 15~
25:1。
3. a kind of preparation of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella 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 1.07~1.8:1, it is molten
Agent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g/100 ml.
4. a kind of preparation of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella according to claim 1
Method, it is characterised in that：Step 2）In, PLA list tridecyl ether is using poly-（D, Pfansteihl）Single tridecyl ether, gathers breast
The mol ratio of sour list tridecyl ether and polyacrylic acid segment in poly acrylic acid-poly trimethylene carbonate graft copolymer is 15
~25:1.
5. a kind of preparation of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella 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 trimethylene carbonate graft copolymerization
The mol ratio of polyacrylic acid segment is 1.07~1.8 in thing:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~
15 g/100 ml。
6. a kind of preparation of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella according to claim 1
Method, it is characterised in that：Step 3）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
7. a kind of preparation of poly acrylic acid-poly trimethylene carbonate-copolymer of poly lactic acid micella 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.
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| CN201710362978.6A CN107118364A (en) | 2017-05-22 | 2017-05-22 | A kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542198A (en) * | 2016-03-09 | 2016-05-04 | 山东理工大学 | Preparation method of polyvinyl alcohol-poly(trimethylene carbonate)-poly(lactic acid-glycolic acid) dual-grafted copolymer micelle |
| CN105670007A (en) * | 2016-03-14 | 2016-06-15 | 山东理工大学 | Method for preparing polyvinyl alcohol-poly trimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer micelle |
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2017
- 2017-05-22 CN CN201710362978.6A patent/CN107118364A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542198A (en) * | 2016-03-09 | 2016-05-04 | 山东理工大学 | Preparation method of polyvinyl alcohol-poly(trimethylene carbonate)-poly(lactic acid-glycolic acid) dual-grafted copolymer micelle |
| CN105670007A (en) * | 2016-03-14 | 2016-06-15 | 山东理工大学 | Method for preparing polyvinyl alcohol-poly trimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer micelle |
Non-Patent Citations (1)
| Title |
|---|
| YANHUI MA等: ""Polymer Micelles from Poly(acrylic acid)-graft-polystyrene"", 《MACROMOLECULES》 * |
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