CN106977736A - A kind of method for preparing polyacrylic acid PPDO polycaprolactone polypropylene glycol copolymers micella - Google Patents

A kind of method for preparing polyacrylic acid PPDO polycaprolactone polypropylene glycol copolymers micella Download PDF

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CN106977736A
CN106977736A CN201710376578.0A CN201710376578A CN106977736A CN 106977736 A CN106977736 A CN 106977736A CN 201710376578 A CN201710376578 A CN 201710376578A CN 106977736 A CN106977736 A CN 106977736A
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polycaprolactone
polypropylene glycol
acrylic acid
lanthanum isopropoxide
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朱国全
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Shandong University of Technology
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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • 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
    • 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
    • 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
    • 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
    • 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
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
    • 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
    • C08G2230/00—Compositions for preparing biodegradable polymers
    • 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 method for preparing polyacrylic acid PPDO polycaprolactone polypropylene glycol copolymers micella, using following methods：1）Polyacrylic acid, PPDO, solvent and condensing agent are added in dry reactor, reaction obtains the copolymer of the two；2）Above-mentioned copolymer, polycaprolactone, polypropylene glycol, solvent and condensing agent are added in dry reactor, reaction obtains polyacrylic acid PPDO polycaprolactone polypropylene glycol copolymers；3）Above-mentioned copolymer and solvent are added in drying receptacle, dissolving obtains copolymer stoste；4）Stoste is added in bag filter, put it into the beaker for filling selective solvent, is replaced 3~4 times, is 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

It is common that one kind prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers micella
Technical field
Poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella is prepared the present invention relates to one kind Method, belong 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.PPDO, polycaprolactone and polypropylene glycol（Molecular weight 2000 More than）It is the biomaterial with excellent biocompatibility and biodegradability, with hydrophobicity, has in medicine Extensive use.First PPDO segment is grafted on polyacrylic acid strand and obtains poly acrylic acid-poly to dioxy ring Hexanone graft copolymer, is then grafted to poly acrylic acid-poly to dioxy simultaneously by polycaprolactone segment and polypropylene glycol segment again On polyacrylic acid segment in cyclohexanone graft copolymer, resulting poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone- Polypropylene glycol copolymers have amphipathic, and micella can be self-assembly of in selective solvent, are that a kind of new medicine is carried Body, has a wide range of applications in medicine.
The content of the invention
It is an object of the invention to provide a kind of preferable poly acrylic acid-poly Lanthanum Isopropoxide of simple to operate and effect- The preparation method of polycaprolactone-polypropylene glycol copolymers micella.Its technical scheme is：
A kind of method for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella, its feature It is：The molecular weight of polyacrylic acid segment is 51000~62000 in copolymer, and the molecular weight of PPDO segment is 2400~2500, the molecular weight of polycaprolactone segment is 2200~2300, and the molecular weight of polypropylene glycol segment is 2200~2300； Its preparation method is as follows：
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer：Polyacrylic acid, hydroxyl are added in dry reactor Under PPDO list tridecyl ether, solvent and the condensing agent of end-blocking, inert atmosphere, in 28~32 DEG C of stirring reactions 2 ~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers：Add in dry reactor Enter poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer, it is amino-terminated polycaprolactone monododecyl ether, amino-terminated Under polypropylene glycol monobutyl ether, solvent and condensing agent, inert atmosphere, in 27~32 DEG C of stirring reactions 2~4 days, terminating reaction passed through Filter, dialyse, dry, obtain object；
3）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste：In dry reactor Interior addition poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers and solvent, it is molten in 46~52 DEG C of stirrings Solution 40~60 minutes, obtains object；
4）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella：At room temperature, by stoste Add in bag filter, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 8 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 described side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella Method, step 1）In, the mol ratio of PPDO list tridecyl ether and polyacrylic acid is 15~25:1.
A kind of described side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella 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 1.06~1.9:1, solvent is sub- using dimethyl Sulfone, reactant solution concentration is 5~15 g:100 ml.
A kind of described side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella Method, step 2）In, polycaprolactone monododecyl ether and polyacrylic acid in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer The mol ratio of segment is 15~25:1, polypropylene glycol monobutyl ether in poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer with gathering The mol ratio of acrylate is 15~25:1.
A kind of described side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella 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 1.06~1.9:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g:100 ml.
A kind of described side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella Method, step 3）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
A kind of described side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella Method, step 4）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4500, 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 side for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella Method, the means being combined using esterification, amidation process and dialysis, it is simple to operate, be easy to grasp；
2nd, a kind of described poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella is a kind of new Pharmaceutical carrier.
Embodiment
Embodiment 1
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 51000）, 12.3 grams it is hydroxy-end capped poly- to dioxy Cyclohexanone list tridecyl ether（Molecular weight is 2400）, 267 ml dimethyl sulfoxide (DMSO)s are added, 0.073 gram is addedN,N’- two rings Under hexyl carbodiimide, inert atmosphere, in 28 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtains mesh Mark thing；
2）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers
Added in dry reactor 10.1 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.5 grams it is amino-terminated Polycaprolactone monododecyl ether（Molecular weight is 2200）With 7.5 grams of amino-terminated polypropylene glycol monobutyl ethers（Molecular weight is 2200）, 251 ml dimethyl sulfoxide (DMSO)s are added, 0.049 gram is addedN,N’Under-dicyclohexylcarbodiimide, inert atmosphere, in 27 DEG C stirring reaction 2 days, terminating reaction by filtering, dialysis, is dried, obtains object；
3）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste
Added in dry reactor 120 milligrams of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers, 100 milliliters of dimethyl sulfoxide (DMSO)s, in 46 DEG C of stirring and dissolvings 40 minutes, obtain object；
4）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella
At room temperature, 1 milliliter of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste is added into 5 millis In the bag filter for rising capacity（Molecular cut off is 3500）, put it into 500 milliliters of beakers for filling distilled water, it is small every 8 When displacement once, replace 3 times, solution shows blue light in bag filter, be then poured into in graduated 10 milliliters of volumetric flasks, Scale is adjusted to distilled water, object is obtained.
Embodiment 2
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
15.1 grams of polyacrylic acid are added in dry reactor（Molecular weight is 55000）, 12.4 grams it is hydroxy-end capped poly- to dioxy Cyclohexanone list tridecyl ether（Molecular weight is 2400）, 272 ml dimethyl sulfoxide (DMSO)s are added, 0.044 gram is addedN,N’- two is different Under propyl group carbodiimide, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtains mesh Mark thing；
2）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers
Added in dry reactor 10.2 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7.4 grams it is amino-terminated Polycaprolactone monododecyl ether（Molecular weight is 2200）With 7.4 grams of amino-terminated polypropylene glycol monobutyl ethers（Molecular weight is 2200）, 247 ml dimethyl sulfoxide (DMSO)s are added, 0.028 gram is addedN,N’Under-DIC, inert atmosphere, in 30 DEG C stirring reaction 3 days, terminating reaction by filtering, dialysis, is dried, obtains object；
3）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste
Added in dry reactor 130 milligrams of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers, 100 milliliters of dimethyl sulfoxide (DMSO)s, in 49 DEG C of stirring and dissolvings 50 minutes, obtain object；
4）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella
At room temperature, 1 milliliter of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste is added into 7 millis In the bag filter for rising capacity（Molecular cut off is 4000）, put it into 500 milliliters of beakers for filling distilled water, it is small every 8 When displacement once, replace 4 times, solution shows blue light in bag filter, be then poured into in graduated 10 milliliters of volumetric flasks, Scale is adjusted to distilled water, object is obtained.
Embodiment 3
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer
16.2 grams of polyacrylic acid are added in dry reactor（Molecular weight is 62000）, 12.7 grams it is hydroxy-end capped poly- to dioxy Cyclohexanone list tridecyl ether（Molecular weight is 2500）, 288 ml dimethyl sulfoxide (DMSO)s are added, 0.062 gram of 3- ethyls -1- is added （3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 32 DEG C of stirring reactions 4 days, terminating reaction, by filtering, dialysis, dry It is dry, obtain object；
2）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers
Added in dry reactor 10.2 grams of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymers, 7 grams it is amino-terminated poly- Caprolactone monododecyl ether（Molecular weight is 2300）With 7 grams of amino-terminated polypropylene glycol monobutyl ethers（Molecular weight is 2300）, 242 ml dimethyl sulfoxide (DMSO)s are added, 0.038 gram of 3- ethyls -1- is added（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, In 32 DEG C of stirring reactions 4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
3）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste
Added in dry reactor 140 milligrams of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers, 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 Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella
At room temperature, 1 milliliter of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste is added into 8 millis In the bag filter for rising capacity（Molecular cut off is 4500）, put it into 500 milliliters of beakers for filling distilled water, it is small every 8 When displacement once, replace 3 times, solution shows blue light in bag filter, be then poured into in graduated 10 milliliters of volumetric flasks, Scale is adjusted to distilled water, object is obtained.

Claims (7)

1. a kind of method for preparing poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella, it is special Levy and be：The molecular weight of polyacrylic acid segment is 51000~62000, the molecular weight of PPDO segment in copolymer For 2400~2500, the molecular weight of polycaprolactone segment is 2200~2300, the molecular weight of polypropylene glycol segment for 2200~ 2300；Its preparation method is as follows：
1）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer：Polyacrylic acid, hydroxyl are added in dry reactor Under PPDO list tridecyl ether, solvent and the condensing agent of end-blocking, inert atmosphere, in 28~32 DEG C of stirring reactions 2 ~4 days, terminating reaction by filtering, dialysis, was dried, obtains object；
2）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers：Add in dry reactor Enter poly acrylic acid-poly Lanthanum Isopropoxide graft copolymer, it is amino-terminated polycaprolactone monododecyl ether, amino-terminated Under polypropylene glycol monobutyl ether, solvent and condensing agent, inert atmosphere, in 27~32 DEG C of stirring reactions 2~4 days, terminating reaction passed through Filter, dialyse, dry, obtain object；
3）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers stoste：In dry reactor Interior addition poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers and solvent, it is molten in 46~52 DEG C of stirrings Solution 40~60 minutes, obtains object；
4）The preparation of poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol copolymers micella：At room temperature, by stoste Add in bag filter, put it into 500 milliliters of beakers for filling selective solvent, every displacement in 8 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.
It is common that 2. one kind according to claim 1 prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers micella, it is characterised in that：Step 1）In, mole of PPDO list tridecyl ether and polyacrylic acid Than for 15~25:1.
It is common that 3. one kind according to claim 1 prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers 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 1.06 ~1.9:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g:100 ml.
It is common that 4. one kind according to claim 1 prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers micella, it is characterised in that：Step 2）In, polycaprolactone monododecyl ether is with poly acrylic acid-poly to dioxy ring The mol ratio of polyacrylic acid segment is 15~25 in hexanone graft copolymer:1, polypropylene glycol monobutyl ether and poly acrylic acid-poly pair The mol ratio of polyacrylic acid segment is 15~25 in dioxanone graft copolymer:1.
It is common that 5. one kind according to claim 1 prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers 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 1.06~1.9 in graft copolymer:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution is dense Spend for 5~15 g:100 ml.
It is common that 6. one kind according to claim 1 prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers micella, it is characterised in that：Step 3）In, solvent uses dimethyl sulfoxide (DMSO), and original liquid concentration is 1~1.5 mg/ml.
It is common that 7. one kind according to claim 1 prepares poly acrylic acid-poly Lanthanum Isopropoxide-polycaprolactone-polypropylene glycol The method of polymers micella, it is characterised in that：Step 4）In, bag filter capacity is 5~10 ml, and bag filter molecular cut off is 3500~4500, selective solvent uses distilled water, and solution concentration is 0.1~0.3 mg/ml.
CN201710376578.0A 2017-05-25 2017-05-25 A kind of method for preparing polyacrylic acid PPDO polycaprolactone polypropylene glycol copolymers micella Withdrawn CN106977736A (en)

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