CN106947085A - A kind of polyacrylic acid PPDO gathers（Lactide glycolide）The preparation method of copolymer micelle - Google Patents
A kind of polyacrylic acid PPDO gathers（Lactide glycolide）The preparation method of copolymer micelle Download PDFInfo
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- CN106947085A CN106947085A CN201710362976.7A CN201710362976A CN106947085A CN 106947085 A CN106947085 A CN 106947085A CN 201710362976 A CN201710362976 A CN 201710362976A CN 106947085 A CN106947085 A CN 106947085A
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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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- 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
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- 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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2230/00—Compositions for preparing biodegradable polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The present invention discloses a kind of polyacrylic acid PPDO and gathered（Lactide glycolide）The preparation method of 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）It is adjunction graft copolymer in reactor, hydroxy-end capped poly-（Lactide glycolide）Single tridecyl ether, solvent and condensing agent, react polyacrylic acid PPDO gather（Lactide glycolide）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 poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The system of copolymer micelle
Preparation 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 terms of being widely used in medicine and pharmacology.PPDO and poly-（Lactide coglycolide）（Lactide is handed over second
The weight ratio of ester is 90/10）It is the biomaterial with excellent biocompatibility and biodegradability, all with good
Hydrophobicity, has a wide range of applications in medicine.PPDO segment is first grafted to polyacrylic acid strand
On obtain poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer, then will be poly-（Lactide coglycolide）Segment is grafted to polypropylene
On polyacrylic acid segment in acid-PPDO graft copolymer obtained by poly acrylic acid-poly Lanthanum Isopropoxide-
It is poly-（Lactide coglycolide）Dual graft copolymer has amphipathic, and micella can be self-assembly of in selective solvent, is one
New pharmaceutical carrier is planted, is had broad application prospects in medicine.
The content of the invention
Poly acrylic acid-poly is preferably prepared to dioxocyclohex it is an object of the invention to provide a kind of simple to operate and effect
Ketone-poly-（Lactide coglycolide）The method of copolymer micelle.Its technical scheme is：
A kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation method of copolymer micelle, its feature
It is：The molecular weight of polyacrylic acid segment is 53000~65000 in copolymer, and the molecular weight of PPDO segment is
2600~2800, gather（Lactide coglycolide）The molecular weight of segment is 2200~2500；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 27~31 DEG C of stirring reactions 2
~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer：In dry reaction
Poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer is added in device, it is hydroxy-end capped poly-（Lactide coglycolide）Single tridecane
Under base ether, solvent and condensing agent, inert atmosphere, in 28~31 DEG C of stirring reactions 2~4 days, terminating reaction, by filtering, dialysis,
Dry, obtain object；
3）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer stoste：In drying
The interior addition poly acrylic acid-poly Lanthanum Isopropoxide of reactor-poly-（Lactide coglycolide）Dual graft copolymer and solvent, in 47
~53 DEG C of stirring and dissolvings 50~60 minutes, obtain object；
4）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of 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, is put
Change 3~4 times, solution shows blue light in bag filter, is then poured into in graduated volumetric flask, is adjusted to selective solvent
Scale, obtains object.
Described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, step 1）In, the mol ratio of PPDO monododecyl ether and polyacrylic acid is 15~25:1.
Described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-
（3- dimethylaminopropyls）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.07~1.8:1, solvent is sub- using dimethyl
Sulfone, reactant solution concentration is 5~15 g/100 ml.
Described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, step 2）In, gather（Lactide coglycolide）Single tridecyl ether is using poly-（D, L- lactide coglycolide）Single tridecyl
Ether（The weight ratio of lactide and glycolide is 90/10）, gather（Lactide coglycolide）Single tridecyl ether and poly acrylic acid-poly
The mol ratio of polyacrylic acid segment is 15~25 in Lanthanum Isopropoxide graft copolymer:1.
Described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-
（3- dimethylaminopropyls）Carbodiimide, condensing agent and polyacrylic acid chain in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
The mol ratio of section is 1.07~1.8:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g/100 ml.
Described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, step 3）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
Described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, step 4）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4000, and selective solvent is used
Distilled water, solution concentration is 0.1~0.3 mg/ml.
Compared with prior art, its advantage is the present invention：
1st, described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation side of copolymer micelle
Method, the means being combined using two step esterifications and dialysis, it is simple to operate, be easy to grasp；
2nd, described a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）Copolymer micelle is a kind of new
Pharmaceutical carrier.
Embodiment
Embodiment 1
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
14 grams of polyacrylic acid are added in dry reactor（Molecular weight is 53000）, 12.7 grams it is hydroxy-end capped poly- to dioxy ring
Hexanone monododecyl ether（Molecular weight is 2600）, 267 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.072 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）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer
Added in dry reactor 10 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.6 grams it is hydroxy-end capped poly-
（Lactide coglycolide）Single tridecyl ether（Molecular weight is 2200）, 176 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.048 is added
GramN,N’Under-dicyclohexylcarbodiimide, inert atmosphere, in 28 DEG C of stirring reactions 2 days, terminating reaction, by filtering, dialysis,
Dry, obtain object；
3）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer stoste
120 milligrams of poly acrylic acid-poly Lanthanum Isopropoxides-poly- are added in dry reactor（Lactide coglycolide）Dual graft
Copolymer and 100 milliliters of dimethyl sulfoxide (DMSO)s, in 47 DEG C of stirring and dissolvings 50 minutes, obtain object；
4）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer micelle
At room temperature, by 1 milliliter of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）Dual graft copolymer stoste adds
In the bag filter for entering 5 milliliters of capacity（Molecular cut off is 3500）, put it into 500 milliliters of beakers for filling distilled water, often
Every displacement in 7 hours once, replace 3 times, solution shows blue light in bag filter, is then poured into graduated 10 milliliters of capacity
In bottle, scale is adjusted to distilled water, object is obtained.
Embodiment 2
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
14.2 grams of polyacrylic acid are added in dry reactor（Molecular weight is 55000）, 13.1 grams it is hydroxy-end capped poly- to dioxy
Cyclohexanone monododecyl ether（Molecular weight is 2700）, 273 milliliters of dimethyl sulfoxide (DMSO)s are added, 0.042 gram is addedN,N’- two
Under diisopropylcarbodiimide, inert atmosphere, in 29 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtained
Object；
2）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer
Added in dry reactor 10.2 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.7 grams it is hydroxy-end capped
It is poly-（Lactide coglycolide）Single tridecyl ether（Molecular weight is 2300）, 179 milliliters of dimethyl sulfoxide (DMSO)s are added, are added
0.029 gramN,N’Under-DIC, inert atmosphere, in 29 DEG C of stirring reactions 3 days, terminating reaction, by filtering,
Dialyse, dry, obtain object；
3）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer stoste
130 milligrams of poly acrylic acid-poly Lanthanum Isopropoxides-poly- are added in dry reactor（Lactide coglycolide）Dual graft
Copolymer and 100 milliliters of dimethyl sulfoxide (DMSO)s, in 50 DEG C of stirring and dissolvings 55 minutes, obtain object；
4）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer micelle
At room temperature, by 1 milliliter of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）Dual graft copolymer stoste adds
In the bag filter for entering 6 milliliters of capacity（Molecular cut off is 3700）, put it into 500 milliliters of beakers for filling distilled water, often
Every displacement in 7 hours once, replace 4 times, solution shows blue light in bag filter, is then poured into graduated 10 milliliters of capacity
In bottle, scale is adjusted to distilled water, object is obtained.
Embodiment 3
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
15.5 grams of polyacrylic acid are added in dry reactor（Molecular weight is 65000）, 12.4 grams it is hydroxy-end capped poly- to dioxy
Cyclohexanone monododecyl ether（Molecular weight is 2800）, add 279 milliliters of dimethyl sulfoxide (DMSO)s, add 0.059 gram of 3- ethyl-
1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 31 DEG C of stirring reactions 4 days, terminating reaction, by filtering, dialysis,
Dry, obtain object；
2）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer
Added in dry reactor 10.3 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.6 grams it is hydroxy-end capped
It is poly-（Lactide coglycolide）Single tridecyl ether（Molecular weight is 2500）, 179 milliliters of dimethyl sulfoxide (DMSO)s are added, are added
0.039 gram of 3- ethyls -1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 31 DEG C of stirring reactions 4 days, terminating reaction,
By filtering, dialysis, dry, obtain object；
3）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer stoste
140 milligrams of poly acrylic acid-poly Lanthanum Isopropoxides-poly- are added in dry reactor（Lactide coglycolide）Dual graft
Copolymer and 100 milliliters of dimethyl sulfoxide (DMSO)s, in 53 DEG C of stirring and dissolvings 60 minutes, obtain object；
4）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer micelle
At room temperature, by 1 milliliter of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）Dual graft copolymer stoste adds
In the bag filter for entering 7 milliliters of capacity（Molecular cut off is 4000）, put it into 500 milliliters of beakers for filling distilled water, often
Every displacement in 7 hours once, replace 4 times, solution shows blue light in bag filter, is then poured into graduated 10 milliliters of capacity
In bottle, scale is adjusted to distilled water, object is obtained.
Claims (7)
1. a kind of poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation method of copolymer micelle, it is special
Levy and be：The molecular weight of polyacrylic acid segment is 53000~65000, the molecular weight of PPDO segment in copolymer
For 2600~2800, gather（Lactide coglycolide）The molecular weight of segment is 2200~2500；Its preparation method uses following step
Suddenly：
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 27~31 DEG C of stirring reactions 2
~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer：In dry reaction
Poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer is added in device, it is hydroxy-end capped poly-（Lactide coglycolide）Single tridecane
Under base ether, solvent and condensing agent, inert atmosphere, in 28~31 DEG C of stirring reactions 2~4 days, terminating reaction, by filtering, dialysis,
Dry, obtain object；
3）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of dual graft copolymer stoste：In drying
The interior addition poly acrylic acid-poly Lanthanum Isopropoxide of reactor-poly-（Lactide coglycolide）Dual graft copolymer and solvent, in 47
~53 DEG C of stirring and dissolvings 50~60 minutes, obtain object；
4）Poly acrylic acid-poly Lanthanum Isopropoxide-poly-（Lactide coglycolide）The preparation of 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, is put
Change 3~4 times, solution shows blue light in bag filter, is then poured into in graduated volumetric flask, is adjusted to selective solvent
Scale, obtains object.
2. a kind of poly acrylic acid-poly Lanthanum Isopropoxide according to claim 1-poly-（Lactide coglycolide）Copolymer
The preparation method of micella, it is characterised in that：Step 1）In, mole of PPDO monododecyl ether and polyacrylic acid
Than for 15~25:1.
3. a kind of poly acrylic acid-poly Lanthanum Isopropoxide according to claim 1-poly-（Lactide coglycolide）Copolymer
The preparation method of micella, it is characterised in that：Step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- two is different
Propyl group carbodiimide or 3- ethyls -1-（3- dimethylaminopropyls）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.07
~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 Lanthanum Isopropoxide according to claim 1-poly-（Lactide coglycolide）Copolymer
The preparation method of micella, it is characterised in that：Step 2）In, gather（Lactide coglycolide）Single tridecyl ether is using poly-（D, L- third
Lactide-co-glycolides）Single tridecyl ether（The weight ratio of lactide and glycolide is 90/10）, gather（Lactide coglycolide）Single ten
Trialkyl ether is 15~25 with the mol ratio of polyacrylic acid segment in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer:1.
5. a kind of poly acrylic acid-poly Lanthanum Isopropoxide according to claim 1-poly-（Lactide coglycolide）Copolymer
The preparation method of micella, it is characterised in that：Step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- two is different
Propyl group carbodiimide or 3- ethyls -1-（3- dimethylaminopropyls）Carbodiimide, condensing agent and poly acrylic acid-poly Lanthanum Isopropoxide
The mol ratio of polyacrylic acid segment is 1.07~1.8 in graft copolymer:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution is dense
Spend for 5~15 g/100 ml.
6. a kind of poly acrylic acid-poly Lanthanum Isopropoxide according to claim 1-poly-（Lactide coglycolide）Copolymer
The preparation method of micella, 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 poly acrylic acid-poly Lanthanum Isopropoxide according to claim 1-poly-（Lactide coglycolide）Copolymer
The preparation method of micella, it is characterised in that：Step 4）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is
3500~4000, selective solvent uses distilled water, and solution concentration is 0.1~0.3 mg/ml.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710362976.7A CN106947085A (en) | 2017-05-22 | 2017-05-22 | A kind of polyacrylic acid PPDO gathers（Lactide glycolide）The preparation method of copolymer micelle |
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| CN201710362976.7A CN106947085A (en) | 2017-05-22 | 2017-05-22 | A kind of polyacrylic acid PPDO gathers（Lactide glycolide）The preparation method of copolymer micelle |
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Application publication date: 20170714 |