CN107011520A - A kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle - Google Patents
A kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle Download PDFInfo
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- CN107011520A CN107011520A CN201710376601.6A CN201710376601A CN107011520A CN 107011520 A CN107011520 A CN 107011520A CN 201710376601 A CN201710376601 A CN 201710376601A CN 107011520 A CN107011520 A CN 107011520A
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- 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
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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
- 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
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- 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
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Abstract
The present invention discloses a kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle, using following methods：1）Polyacrylic acid, hydroxy-end capped PLA monododecyl ether, hydroxy-end capped PPDO list undecyl ether, solvent and condensing agent are added in dry reactor, reaction obtains polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer；2）Dual graft copolymer and solvent are added in dry reactor, dissolving obtains copolymer stoste；3）Stoste is added in bag filter, put it into the beaker for filling selective solvent, every displacement in 7 hours once, replaces 3~4 times, is then poured into in graduated volumetric flask, scale is adjusted to selective solvent, 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 side of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle
Method, belongs to biodegradated polymer materal preparing technical field.
Background technology
Polyacrylic acid is a kind of biomaterial with good biocompatibility and biodegradability, with excellent
Hydrophily, in medicine extensive application.PLA and PPDO are with excellent biocompatibility
With the biomaterial of biodegradability, there is preferable hydrophobicity, be widely used in medicine.By polylactic acid chain segment,
PPDO segment be grafted to simultaneously on polyacrylic acid strand obtained by poly acrylic acid-poly lactic acid-poly- to dioxy
Cyclohexanone dual graft copolymer has amphipathic, and micella can be self-assembly of in selective solvent, is a kind of new medicine
Thing carrier, has broad application prospects in medicine.
The content of the invention
It is an object of the invention to provide a kind of preferable poly acrylic acid-poly lactic acid of simple to operate and effect-poly- to dioxy
The preparation method of cyclohexanone dual graft copolymer micelle.Its technical scheme is：
A kind of preparation method of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle, it is characterised in that：
The molecular weight of polyacrylic acid segment is 51000~64000 in copolymer, and the molecular weight of polylactic acid chain segment is 2100~2300, is gathered
The molecular weight of Lanthanum Isopropoxide segment is 2100~2300；Its preparation method is as follows：
1）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer：Poly- third is added in dry reactor
Olefin(e) acid, hydroxy-end capped PLA monododecyl ether, hydroxy-end capped PPDO list undecyl ether, solvent and
Under condensing agent, inert atmosphere, in 26~32 DEG C of stirring reactions 2~3 days, terminating reaction by filtering, dialysis, was dried, obtains mesh
Mark thing；
2）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste：Added in dry reactor
Poly acrylic acid-poly lactic acid-PPDO dual graft copolymer and solvent, in 46~52 DEG C of 50~60 points of stirring and dissolvings
Clock, obtains object；
3）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle：At room temperature, stoste is added
In bag filter, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 7 hours once, replace 3~4 times,
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 lactic acid-PPDO dual graft copolymer micelle, step
Rapid 1）In, PLA monododecyl ether is using poly-（D, Pfansteihl）Monododecyl ether, PLA monododecyl ether is with gathering
The mol ratio of acrylic acid is 15~25:1, the mol ratio of PPDO list undecyl ether and polyacrylic acid for 15~
25:1。
A kind of preparation method of described poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle, step
Rapid 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- bis-
First aminopropyl）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.06~1.8:1, solvent uses dimethyl sulfoxide (DMSO), instead
It is 5~15 g/100 ml to answer thing solution concentration.
A kind of preparation method of described poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle, step
Rapid 2）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 lactic acid-PPDO dual graft copolymer micelle, step
Rapid 3）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4500, and selective solvent is using distillation
Water, solution concentration is 0.1~0.4 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 lactic acid-PPDO dual graft copolymer micelle, is used
The means that a kind of polymer is combined with the esterification and dialysis that two kinds of different polymeric monomers are carried out simultaneously are simple to operate, easy
In grasp；
2nd, a kind of described poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle is a kind of new medicine
Thing carrier.
Embodiment
Embodiment 1
1）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer
14.6 grams of polyacrylic acid are added in dry reactor（Molecular weight is 51000）, 11.2 grams of hydroxy-end capped PLA lists
Lauryl ether（Molecular weight is 2100）With 11.2 grams of hydroxy-end capped PPDO list undecyl ethers（Molecular weight is
2100）, 371 ml dimethyl sulfoxide (DMSO)s are added, 0.075 gram is addedN,N’Under-dicyclohexylcarbodiimide, inert atmosphere, in 26
DEG C stirring reaction 2 days, terminating reaction by filtering, dialysis, is dried, obtains object；
2）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste
130 milligrams of poly acrylic acid-poly lactic acid-PPDO dual graft copolymers, 100 millis are added in dry reactor
Dimethyl sulfoxide (DMSO) is risen, in 46 DEG C of stirring and dissolvings 50 minutes, object is obtained；
3）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste is added into 6 milliliters of capacity
Bag filter in（Molecular cut off is 3500）, put it into 500 milliliters of beakers for filling distilled water, replaced every 7 hours
Once, replace 3 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, with distillation
Water is adjusted to scale, obtains object.
Embodiment 2
1）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer
15.4 grams of polyacrylic acid are added in dry reactor（Molecular weight is 55000）, 11.6 grams of hydroxy-end capped PLA lists
Lauryl ether（Molecular weight is 2200）With 11.6 grams of hydroxy-end capped PPDO list undecyl ethers（Molecular weight is
2200）, 386 ml dimethyl sulfoxide (DMSO)s are added, 0.044 gram is addedN,N’Under-DIC, inert atmosphere, in 30
DEG C stirring reaction 2 days, terminating reaction by filtering, dialysis, is dried, obtains object；
2）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste
140 milligrams of poly acrylic acid-poly lactic acid-PPDO dual graft copolymers, 100 millis are added in dry reactor
Dimethyl sulfoxide (DMSO) is risen, in 50 DEG C of stirring and dissolvings 55 minutes, object is obtained；
3）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste is added into 7 milliliters of capacity
Bag filter in（Molecular cut off is 4000）, put it into 500 milliliters of beakers for filling distilled water, replaced every 7 hours
Once, replace 4 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, with distillation
Water is adjusted to scale, obtains object.
Embodiment 3
1）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer
17.8 grams of polyacrylic acid are added in dry reactor（Molecular weight is 64000）, 12.2 grams of hydroxy-end capped PLA lists
Lauryl ether（Molecular weight is 2300）With 12.2 grams of hydroxy-end capped PPDO list undecyl ethers（Molecular weight is
2300）, 421 ml dimethyl sulfoxide (DMSO)s are added, 0.066 gram of 3- ethyls -1- is added（3- dimethylaminopropyls）Carbodiimide, inertia
Under atmosphere, in 32 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste
145 milligrams of poly acrylic acid-poly lactic acid-PPDO dual graft copolymers, 100 millis are added in dry reactor
Dimethyl sulfoxide (DMSO) is risen, in 52 DEG C of stirring and dissolvings 60 minutes, object is obtained；
3）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle
At room temperature, 1 milliliter of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste is added into 8 milliliters of capacity
Bag filter in（Molecular cut off is 4500）, put it into 500 milliliters of beakers for filling distilled water, replaced every 7 hours
Once, replace 3 times, solution shows blue light in bag filter, is then poured into in graduated 10 milliliters of volumetric flasks, with distillation
Water is adjusted to scale, obtains object.
Claims (5)
1. a kind of preparation method of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle, its feature exists
In：The molecular weight of polyacrylic acid segment is 51000~64000 in copolymer, and the molecular weight of polylactic acid chain segment is 2100~2300,
The molecular weight of PPDO segment is 2100~2300；Its preparation method is as follows：
1）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer：Poly- third is added in dry reactor
Olefin(e) acid, hydroxy-end capped PLA monododecyl ether, hydroxy-end capped PPDO list undecyl ether, solvent and
Under condensing agent, inert atmosphere, in 26~32 DEG C of stirring reactions 2~3 days, terminating reaction by filtering, dialysis, was dried, obtains mesh
Mark thing；
2）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer stoste：Added in dry reactor
Poly acrylic acid-poly lactic acid-PPDO dual graft copolymer and solvent, in 46~52 DEG C of 50~60 points of stirring and dissolvings
Clock, obtains object；
3）The preparation of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle：At room temperature, stoste is added
In bag filter, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 7 hours once, replace 3~4 times,
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 lactic acid-PPDO dual graft copolymer micelle according to claim 1
Preparation method, it is characterised in that：Step 1）In, PLA monododecyl ether is using poly-（D, Pfansteihl）Monododecyl ether,
The mol ratio of PLA monododecyl ether and polyacrylic acid is 15~25:1, PPDO list undecyl ether is with gathering
The mol ratio of acrylic acid is 15~25:1.
3. a kind of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle according to claim 1
Preparation method, it is characterised in that：Step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- diisopropyl
Carbodiimide or 3- ethyls -1-（3- dimethylaminopropyls）The mol ratio of carbodiimide, condensing agent and polyacrylic acid be 1.06~
1.8:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g/100 ml.
4. a kind of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle according to claim 1
Preparation method, it is characterised in that：Step 2）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
5. a kind of poly acrylic acid-poly lactic acid-PPDO dual graft copolymer micelle according to claim 1
Preparation method, it is characterised in that：Step 3）In, bag filter capacity be 5~10 ml, bag filter molecular cut off be 3500~
4500, selective solvent uses distilled water, and solution concentration is 0.1~0.4 mg/ml.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710376601.6A CN107011520A (en) | 2017-05-25 | 2017-05-25 | A kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710376601.6A CN107011520A (en) | 2017-05-25 | 2017-05-25 | A kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle |
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| CN107011520A true CN107011520A (en) | 2017-08-04 |
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| CN201710376601.6A Withdrawn CN107011520A (en) | 2017-05-25 | 2017-05-25 | A kind of preparation method of polyacrylic acid polylactic acid poly Lanthanum Isopropoxide dual graft copolymer micelle |
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Application publication date: 20170804 |