CN105670007A - Method for preparing polyvinyl alcohol-poly trimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer micelle - Google Patents
Method for preparing polyvinyl alcohol-poly trimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer micelle Download PDFInfo
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- CN105670007A CN105670007A CN201610140620.4A CN201610140620A CN105670007A CN 105670007 A CN105670007 A CN 105670007A CN 201610140620 A CN201610140620 A CN 201610140620A CN 105670007 A CN105670007 A CN 105670007A
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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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- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
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- 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 invention discloses a method for preparing polyvinyl alcohol-poly trimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer micelle.The method comprises the following steps that firstly, polyvinyl alcohol, carboxyl-terminated poly trimethylene carbonate monododecyl ether, a solvent and a condensing agent are added in a reactor, and a polyvinyl alcohol-poly trimethylene carbonate grafted copolymer is obtained through a reaction; secondly, the grafted copolymer, carboxyl-terminated poly lactic acid-glycolic acid mono-tridecyl ether, a solvent and a condensing agent are added into the reactor, and a polyvinyl alcohol-poly trimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer is obtained through a reaction; thirdly, the double-grafted copolymer and a solvent are added in the reactor, and a double-grafted copolymer stock solution is obtained through dissolving; thirdly, the stock solution is added in a dialysis bag, the dialysis bag is put into a beaker with a selective solvent for 3-4 times of replacement, an obtained solution is poured into a volumetric flask with scales, adjustment is carried out to reach a scale, and the target object is obtained.The preparing process is simple and easy to grasp, and the obtained target object is a novel drug carrier.
Description
Technical field
The present invention relates to a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, belong to biodegradated polymer materal preparing technical field.
Background technology
Polyvinyl alcohol is a kind of biomaterial with good biocompatibility and biodegradability, has excellent hydrophilic, is widely used in medicine and pharmacology aspect. PTMC and poly-(D, Pfansteihl) glycolic (weight ratio of lactic acid and glycolic is 90/10) is the biomaterial with excellent biocompatibility and biodegradability, all there is good hydrophobicity, have a wide range of applications at medicine. First PTMC segment is grafted on polyvinyl alcohol molecule chain and obtains polyvinyl alcohol-PTMC graft copolymer, poly (lactic acid-glycolic acid) segment is grafted to polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer obtained in the polyvinyl alcohol segments in polyvinyl alcohol-PTMC graft copolymer again and has amphipathic, selective solvent can be self-assembly of micelle, it is a kind of novel pharmaceutical carrier, has broad application prospects in the difficult miscellaneous diseases such as treatment cancer.
Summary of the invention
It is an object of the invention to provide the method that a kind of simple to operate and effect prepares polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle preferably. Its technical scheme is:
A kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, it is characterized in that: in copolymer, the molecular weight of polyvinyl alcohol segments is 48000～52000, the molecular weight of PTMC segment is 2700～2900, and the molecular weight of poly (lactic acid-glycolic acid) segment is 2300～2400; Its preparation method adopts following steps:
1) preparation of polyvinyl alcohol-PTMC graft copolymer: add polyvinyl alcohol, the PTMC monododecyl ether of carboxy blocking, solvent and condensing agent in dry reactor, under inert atmosphere, in 28～33 DEG C of stirring reactions 2～4 days, terminate reaction, by filtering, dialyse, drying, obtain object;
2) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer: add polyvinyl alcohol-PTMC graft copolymer, the poly (lactic acid-glycolic acid) list tridecyl ether of carboxy blocking, solvent and condensing agent in dry reactor, under inert atmosphere, in 29～34 DEG C of stirring reactions 2～4 days, terminate reaction, by filtering, dialyse, drying, obtain object;
3) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution: add polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer and solvent in dry reactor, in 48～54 DEG C of stirring and dissolving 50～60 minutes, obtain object;
4) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle: under room temperature, stock solution is added in bag filter, put it in 500 ml beakers filling selective solvent, every displacement in 6 hours once, replace 3～4 times, solution display blue light in bag filter, be then poured in the graduated volumetric flask of band, it is adjusted to scale with selective solvent, obtains object.
A kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, in step 1), the mol ratio of PTMC monododecyl ether and polyvinyl alcohol is 15～25:1.
A kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, in step 1), condensing agent adoptsN,N’-dicyclohexylcarbodiimide,N,N’-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, the mol ratio of condensing agent and polyvinyl alcohol is 1.08～1.9:1, and solvent adopts dimethyl sulfoxide, and reactant solution concentration is 5～15g/100ml.
A kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, step 2) in, poly (lactic acid-glycolic acid) list tridecyl ether adopts poly-(D, Pfansteihl) glycolic list tridecyl ether, and the weight ratio of lactic acid and glycolic is 90/10, poly (lactic acid-glycolic acid) list tridecyl ether is 15～25:1 with the mol ratio of polyvinyl alcohol segments in polyvinyl alcohol-PTMC graft copolymer.
A kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, step 2) in, condensing agent adoptsN,N’-dicyclohexylcarbodiimide,N,N’-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, condensing agent is 1.07～1.9:1 with the mol ratio of polyvinyl alcohol segments in polyvinyl alcohol-PTMC graft copolymer, solvent adopts dimethyl sulfoxide, and reactant solution concentration is 5～15g/100ml.
A kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, in step 3), solvent adopts dimethyl sulfoxide, and original liquid concentration is 1～1.5mg/ml.
A kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, in step 4), bag filter capacity is 5～10ml, bag filter molecular cut off is 3500～4000, selective solvent adopts distilled water, and solution concentration is 0.1～0.3mg/ml.
Compared with prior art, its advantage is the present invention:
1, a kind of described method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, adopts the means that two step esterifications and dialysis combine, simple to operate, be prone to grasp;
2, described a kind of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle is a kind of novel pharmaceutical carrier.
Detailed description of the invention
Embodiment 1
1) preparation of polyvinyl alcohol-PTMC graft copolymer
In dry reactor, add the PTMC monododecyl ether (molecular weight is 2700) of 12.2 grams of polyvinyl alcohol (molecular weight is 48000), 12.8 grams of carboxy blockings, add 240 milliliters of dimethyl sulfoxide, add 0.069 gramN,N’-dicyclohexylcarbodiimide, under inert atmosphere, in 28 DEG C of stirring reactions 2 days, terminates reaction, by filtering, dialysis, dry, obtains object;
2) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer
In dry reactor, add the poly (lactic acid-glycolic acid) list tridecyl ether (molecular weight is 2300) of 10 grams of polyvinyl alcohol-PTMC graft copolymers, 8.7 grams of carboxy blockings, add 185 milliliters of dimethyl sulfoxide, add 0.056 gramN,N’-dicyclohexylcarbodiimide, under inert atmosphere, in 29 DEG C of stirring reactions 2 days, terminates reaction, by filtering, dialysis, dry, obtains object;
3) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution
In dry reactor, add 120 milligrams of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymers and 100 milliliters of dimethyl sulfoxide, in 48 DEG C of stirring and dissolving 50 minutes, obtain object;
4) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle
Under room temperature, 1 milliliter of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution is added in the bag filter of 5 milliliters of capacity (molecular cut off is 3500), put it in 500 ml beakers filling distilled water, every displacement in 6 hours once, replace 3 times, solution display blue light in bag filter, be then poured in the graduated 10 milliliters of volumetric flasks of band, it is adjusted to scale with distilled water, obtains object.
Embodiment 2
1) preparation of polyvinyl alcohol-PTMC graft copolymer
In dry reactor, add the PTMC monododecyl ether (molecular weight is 2800) of 12.3 grams of polyvinyl alcohol (molecular weight is 50000), 12.6 grams of carboxy blockings, add 238 milliliters of dimethyl sulfoxide, add 0.041 gramN,N’-DIC, under inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminates reaction, by filtering, dialysis, dry, obtains object;
2) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer
In dry reactor, add the poly (lactic acid-glycolic acid) list tridecyl ether (molecular weight is 2300) of 10.2 grams of polyvinyl alcohol-PTMC graft copolymers, 8.6 grams of carboxy blockings, add 182 milliliters of dimethyl sulfoxide, add 0.034 gramN,N’-DIC, under inert atmosphere, in 32 DEG C of stirring reactions 3 days, terminates reaction, by filtering, dialysis, dry, obtains object;
3) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution
In dry reactor, add 130 milligrams of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymers and 100 milliliters of dimethyl sulfoxide, in 52 DEG C of stirring and dissolving 55 minutes, obtain object;
4) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle
Under room temperature, 1 milliliter of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution is added in the bag filter of 6 milliliters of capacity (molecular cut off is 3700), put it in 500 ml beakers filling distilled water, every displacement in 6 hours once, replace 4 times, solution display blue light in bag filter, be then poured in the graduated 10 milliliters of volumetric flasks of band, it is adjusted to scale with distilled water, obtains object.
Embodiment 3
1) preparation of polyvinyl alcohol-PTMC graft copolymer
The PTMC monododecyl ether (molecular weight is 2900) of 12.4 grams of polyvinyl alcohol (molecular weight is 52000), 12.6 grams of carboxy blockings is added in dry reactor, add 239 milliliters of dimethyl sulfoxide, add 0.055 gram of 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, under inert atmosphere, in 33 DEG C of stirring reactions 4 days, terminate reaction, by filtering, dialyse, drying, obtain object;
2) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer
The poly (lactic acid-glycolic acid) list tridecyl ether (molecular weight is 2400) of 10.3 grams of polyvinyl alcohol-PTMC graft copolymers, 8.8 grams of carboxy blockings is added in dry reactor, add 185 milliliters of dimethyl sulfoxide, add 0.046 gram of 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, under inert atmosphere, in 34 DEG C of stirring reactions 4 days, terminate reaction, by filtering, dialyse, drying, obtain object;
3) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution
In dry reactor, add 140 milligrams of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymers and 100 milliliters of dimethyl sulfoxide, in 54 DEG C of stirring and dissolving 60 minutes, obtain object;
4) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle
Under room temperature, 1.2 milliliters of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution is added in the bag filter of 7 milliliters of capacity (molecular cut off is 4000), put it in 500 ml beakers filling distilled water, every displacement in 6 hours once, replace 4 times, solution display blue light in bag filter, be then poured in the graduated 12 milliliters of volumetric flasks of band, it is adjusted to scale with distilled water, obtains object.
Claims (7)
1. the method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle, it is characterized in that: in copolymer, the molecular weight of polyvinyl alcohol segments is 48000～52000, the molecular weight of PTMC segment is 2700～2900, and the molecular weight of poly (lactic acid-glycolic acid) segment is 2300～2400; Its preparation method adopts following steps:
1) preparation of polyvinyl alcohol-PTMC graft copolymer: add polyvinyl alcohol, the PTMC monododecyl ether of carboxy blocking, solvent and condensing agent in dry reactor, under inert atmosphere, in 28～33 DEG C of stirring reactions 2～4 days, terminate reaction, by filtering, dialyse, drying, obtain object;
2) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer: add polyvinyl alcohol-PTMC graft copolymer, the poly (lactic acid-glycolic acid) list tridecyl ether of carboxy blocking, solvent and condensing agent in dry reactor, under inert atmosphere, in 29～34 DEG C of stirring reactions 2～4 days, terminate reaction, by filtering, dialyse, drying, obtain object;
3) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer stock solution: add polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer and solvent in dry reactor, in 48～54 DEG C of stirring and dissolving 50～60 minutes, obtain object;
4) preparation of polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle: under room temperature, stock solution is added in bag filter, put it in 500 ml beakers filling selective solvent, every displacement in 6 hours once, replace 3～4 times, solution display blue light in bag filter, be then poured in the graduated volumetric flask of band, it is adjusted to scale with selective solvent, obtains object.
2. a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle according to claim 1, it is characterized in that: in step 1), the mol ratio of PTMC monododecyl ether and polyvinyl alcohol is 15～25:1.
3. a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle according to claim 1, it is characterised in that: in step 1), condensing agent adoptsN,N’-dicyclohexylcarbodiimide,N,N’-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, the mol ratio of condensing agent and polyvinyl alcohol is 1.08～1.9:1, and solvent adopts dimethyl sulfoxide, and reactant solution concentration is 5～15g/100ml.
4. a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle according to claim 1, it is characterized in that: step 2) in, poly (lactic acid-glycolic acid) list tridecyl ether adopts poly-(D, Pfansteihl) glycolic list tridecyl ether, and the weight ratio of lactic acid and glycolic is 90/10, poly (lactic acid-glycolic acid) list tridecyl ether is 15～25:1 with the mol ratio of polyvinyl alcohol segments in polyvinyl alcohol-PTMC graft copolymer.
5. a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle according to claim 1, it is characterised in that: step 2) in, condensing agent adoptsN,N’-dicyclohexylcarbodiimide,N,N’-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, condensing agent is 1.07～1.9:1 with the mol ratio of polyvinyl alcohol segments in polyvinyl alcohol-PTMC graft copolymer, solvent adopts dimethyl sulfoxide, and reactant solution concentration is 5～15g/100ml.
6. a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle according to claim 1, it is characterised in that: in step 3), solvent adopts dimethyl sulfoxide, and original liquid concentration is 1～1.5mg/ml.
7. a kind of method preparing polyvinyl alcohol-PTMC-poly (lactic acid-glycolic acid) dual graft copolymer micelle according to claim 1, it is characterized in that: in step 4), bag filter capacity is 5～10ml, bag filter molecular cut off is 3500～4000, selective solvent adopts distilled water, and solution concentration is 0.1～0.3mg/ml.
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Cited By (2)
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| CN107118364A (en) * | 2017-05-22 | 2017-09-01 | 山东理工大学 | A kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella |
| CN107118370A (en) * | 2017-05-25 | 2017-09-01 | 山东理工大学 | A kind of method for preparing polyacrylic acid PTMC polylactic acid poly propylene glycol copolymers micella |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107118364A (en) * | 2017-05-22 | 2017-09-01 | 山东理工大学 | A kind of preparation method of polyacrylic acid PTMC copolymer of poly lactic acid micella |
| CN107118370A (en) * | 2017-05-25 | 2017-09-01 | 山东理工大学 | A kind of method for preparing polyacrylic acid PTMC polylactic acid poly propylene glycol copolymers micella |
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