CN104448841A - Method for improving hydrophilia and flexibility of poly peptide film through poly (lactic acid-glycolic acid) (PLGA) and polyacrylic acid - Google Patents
Method for improving hydrophilia and flexibility of poly peptide film through poly (lactic acid-glycolic acid) (PLGA) and polyacrylic acid Download PDFInfo
- Publication number
- CN104448841A CN104448841A CN201510004506.4A CN201510004506A CN104448841A CN 104448841 A CN104448841 A CN 104448841A CN 201510004506 A CN201510004506 A CN 201510004506A CN 104448841 A CN104448841 A CN 104448841A
- Authority
- CN
- China
- Prior art keywords
- poly
- acid
- lactic acid
- glycolic acid
- peptide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
The invention discloses a method for improving the hydrophilia and flexibility of a poly peptide film through poly (lactic acid-glycolic acid) (PLGA) and polyacrylic acid. The method includes the following steps that (1) carboxyl-terminated poly (lactic acid-glycolic acid) (PLGA)-monododecyl ether, solvents, condensing agents and poly peptide homopolymer are added to a dry reactor to be stirred and reacted for two to four days, and poly peptide-poly (lactic acid-glycolic acid) (PLGA) block copolymer is obtained; (2) amine-terminated poly (lactic acid-glycolic acid) (PLGA)-monododecyl ether, solvents, condensing agents and the polyacrylic acid are added to the dry reactor to be stirred and reacted for two to three days, and polyacrylic acid-poly (lactic acid-glycolic acid) (PLGA) graft copolymer is obtained; (3) the poly peptide-poly (lactic acid-glycolic acid) (PLGA) block copolymer, the polyacrylic acid-poly (lactic acid-glycolic acid) (PLGA) graft copolymer and solvents are added into the dry reactor to be stirred and mixed for 40 minutes to 50 minutes, then film formation through a tape casting method is conducted, drying is conducted, and the modified poly peptide film is obtained. The method is simple in process, and the hydrophilia and flexibility of the prepared modified poly peptide film are improved greatly.
Description
Technical field
The present invention relates to a kind of method that poly (lactic acid-glycolic acid) and polyacrylic acid improve poly-peptide film wetting ability and kindliness, belong to field of polymer film preparing technology.
Background technology
Poly-peptide a kind ofly has good biocompatibility and the biomaterial of biodegradability, and poly-peptide film can be used as artificial skin etc., but poly-peptide film more stiff, lack wetting ability, thus limit its application to a certain extent.Poly-(D, L) y has good biocompatibility and biodegradability, softer.Polyacrylic acid has good biocompatibility and biodegradability, and has excellent wetting ability.First poly (lactic acid-glycolic acid) segment is introduced respectively poly-peptide segment and polyacrylic acid segment forms poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer and poly acrylic acid-poly y graft copolymer, and then two kinds of multipolymers are mixed to form the blend with better consistency, obtained modification gathers peptide film, thus drastically increases wetting ability and the kindliness of poly-peptide film.There is not been reported to the research that poly-peptide film wetting ability and kindliness are improved for current poly (lactic acid-glycolic acid) and polyacrylic acid.
Summary of the invention
The object of the present invention is to provide a kind of simple to operate and effect preferably to the method that poly-peptide film wetting ability and kindliness are improved.Its technical scheme is:
A kind of poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: in modified membrane, the molecular weight of poly-peptide segment is 80000 ~ 90000, the molecular weight of poly (lactic acid-glycolic acid) segment is 3000 ~ 4000, and the molecular weight of polyacrylic acid segment is 5000 ~ 6000; Its method of modifying adopts following steps:
1) synthesis of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer: add the poly (lactic acid-glycolic acid) monododecyl ether of carboxy blocking, solvent, condensing agent and poly-peptide homopolymer in dry reactor, under inert atmosphere, in 25 ~ 30 DEG C of stirring reactions 2 ~ 4 days, termination reaction, by filtration, dialysis, drying, obtain target compound, wherein, poly-peptide homopolymer adopts poly-(r-phenmethyl-Pidolidone ester), poly-(r-ethyl-L-glutamate ester) or poly-(r-methyl-Pidolidone ester);
2) synthesis of poly acrylic acid-poly y graft copolymer: add amino-terminated poly (lactic acid-glycolic acid) monododecyl ether, solvent, condensing agent and polyacrylic acid in dry reactor, under inert atmosphere, in 25 ~ 35 DEG C of stirring reactions 2 ~ 3 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of poly (lactic acid-glycolic acid) and polyacrylic acid modified poly-peptide film: add poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer, poly acrylic acid-poly y graft copolymer and solvent in dry reactor, under inert atmosphere, after being uniformly mixed 40 ~ 50 minutes in 40 ~ 50 DEG C, also dry by casting method film forming, obtain target compound.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, in step 1), condensing agent adopts N, N '-dicyclohexylcarbodiimide, N, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, solvent adopts dimethyl formamide, and reactant solution concentration is 5 ~ 15 g:100 ml.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, in step 1), poly (lactic acid-glycolic acid) monododecyl ether adopts poly-(D, L) y monododecyl ether (lactic acid and oxyacetic acid mol ratio: 50/50), the mol ratio of poly (lactic acid-glycolic acid) monododecyl ether and poly-peptide homopolymer is 7 ~ 15:1; The mol ratio of condensing agent and poly-peptide homopolymer is 1.08 ~ 1.8:1.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, step 2) in, condensing agent adopts N, N '-dicyclohexylcarbodiimide, N, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, solvent adopts dimethyl sulfoxide (DMSO), and reactant solution concentration is 5 ~ 15 g:100 ml.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, step 2) in, poly (lactic acid-glycolic acid) monododecyl ether adopts poly-(D, L) y monododecyl ether (lactic acid and oxyacetic acid mol ratio: 50/50), poly (lactic acid-glycolic acid) monododecyl ether and polyacrylic mol ratio are 3 ~ 6:1; Condensing agent and polyacrylic mol ratio are 1.08 ~ 1.8:1.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, in step 3), the mass percent of poly acrylic acid-poly y graft copolymer in modified membrane is 2 ~ 4%, solvent adopts dimethyl sulfoxide (DMSO), and mixture solution concentration is 25 ~ 35 g:100 ml.
Compared with prior art, its advantage is in the present invention:
1. the poly (lactic acid-glycolic acid) described in and polyacrylic acid improve poly-peptide film wetting ability and the method for kindliness, adopt amidate action and blended two kinds of means, simple to operate, be easy to grasp;
2. the poly-peptide modified membrane wetting ability described in and kindliness are greatly improved.
Embodiment
embodiment 1
1) synthesis of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer
In dry reactor, add the poly (lactic acid-glycolic acid) monododecyl ether (molecular weight is 3000) of 16.1 grams of poly-(r-phenmethyl-Pidolidone ester) (molecular weight are 80000) and 7 grams of carboxy blockings, add 300 ml dimethyl formamides, then add 0.048 gram
n, N '-dicyclohexylcarbodiimide, under inert atmosphere, in 25 DEG C of stirring reactions 2 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
2) synthesis of poly acrylic acid-poly y graft copolymer
In dry reactor, add 3.5 grams of polyacrylic acid (molecular weight is 5000) and 9 grams of amino-terminated poly (lactic acid-glycolic acid) monododecyl ethers (molecular weight is 3000), add 160 ml dimethyl sulfoxide (DMSO), then add 0.165 gram
n, N '-dicyclohexylcarbodiimide, under inert atmosphere, in 25 DEG C of stirring reactions termination reaction after 2 days, by filtering, dialysis, dry, obtains target compound;
3) preparation of poly (lactic acid-glycolic acid) and polyacrylic acid modified poly-peptide film
12.5 grams of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymers and 45.8 ml dimethyl sulfoxide solvents are added in dry reactor, separately add the poly acrylic acid-poly y graft copolymer accounting for modified membrane gross weight 2%, under inert atmosphere, 40 minutes are uniformly mixed in 40 DEG C, use casting method film forming, dry in 50 DEG C of vacuum drying ovens, obtain target compound.
After tested: the hydrophilic rate of target compound of the present invention and elongation at break are respectively than improve 12.9% and 13.8% before modified.
embodiment 2
1) synthesis of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer
The poly (lactic acid-glycolic acid) monododecyl ether (molecular weight is 3500) of 16.3 grams of poly-(r-ethyl-L-glutamate ester) (molecular weight are 85000) and 7 grams of carboxy blockings is added in dry reactor, add 305 ml dimethyl formamides, add 0.031 gram of N again, N '-DIC, under inert atmosphere, in 27 DEG C of stirring reactions 3 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
2) synthesis of poly acrylic acid-poly y graft copolymer
In dry reactor, add 3 grams of polyacrylic acid (molecular weight is 5500) and 9 grams of amino-terminated poly (lactic acid-glycolic acid) monododecyl ethers (molecular weight is 3500), add 155 ml dimethyl sulfoxide (DMSO), then add 0.08 gram
n, N '-DIC, under inert atmosphere, in 28 DEG C of stirring reactions termination reaction after 3 days, by filtering, dialysis, dry, obtains target compound;
3) preparation of poly (lactic acid-glycolic acid) and polyacrylic acid modified poly-peptide film
12.6 grams of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymers and 45.5 ml dimethyl sulfoxide solvents are added in dry reactor, separately add the poly acrylic acid-poly y graft copolymer accounting for modified membrane gross weight 3%, under inert atmosphere, 45 minutes are uniformly mixed in 45 DEG C, use casting method film forming, dry in 50 DEG C of vacuum drying ovens, obtain target compound.
After tested: the hydrophilic rate of target compound of the present invention and elongation at break are respectively than improve 13.4% and 14.6% before modified.
embodiment 3
1) synthesis of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer
The poly (lactic acid-glycolic acid) monododecyl ether (molecular weight is 4000) of 16.5 grams of poly-(r-methyl-Pidolidone ester) (molecular weight are 90000) and 7 grams of carboxy blockings is added in dry reactor, add 310 ml dimethyl formamides, add 0.046 gram of 3-ethyl-1-(3-dimethylaminopropyl again) carbodiimide, under inert atmosphere, in 30 DEG C of stirring reactions 4 days, termination reaction, by filtration, dialysis, drying, obtains target compound;
2) synthesis of poly acrylic acid-poly y graft copolymer
3.1 grams of polyacrylic acid (molecular weight is 6000) and 9.2 grams of amino-terminated poly (lactic acid-glycolic acid) monododecyl ethers (molecular weight is 4000) are added in dry reactor, add 158 ml dimethyl sulfoxide (DMSO), add 0.141 gram of 3-ethyl-1-(3-dimethylaminopropyl again) carbodiimide, under inert atmosphere, in 35 DEG C of stirring reactions termination reaction after 2 days, by filtration, dialysis, drying, obtain target compound;
3) preparation of poly (lactic acid-glycolic acid) and polyacrylic acid modified poly-peptide film
12.8 grams of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymers and 45.4 ml dimethyl sulfoxide solvents are added in dry reactor, separately add the poly acrylic acid-poly y graft copolymer accounting for modified membrane gross weight 4%, under inert atmosphere, 50 minutes are uniformly mixed in 50 DEG C, use casting method film forming, dry in 50 DEG C of vacuum drying ovens, obtain target compound.
After tested: the hydrophilic rate of target compound of the present invention and elongation at break are respectively than improve 14.3% and 15.1% before modified.
Claims (6)
1. a poly (lactic acid-glycolic acid) and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: in modified membrane, the molecular weight of poly-peptide segment is 80000 ~ 90000, the molecular weight of poly (lactic acid-glycolic acid) segment is 3000 ~ 4000, and the molecular weight of polyacrylic acid segment is 5000 ~ 6000; Its method of modifying adopts following steps:
1) synthesis of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer: add the poly (lactic acid-glycolic acid) monododecyl ether of carboxy blocking, solvent, condensing agent and poly-peptide homopolymer in dry reactor, under inert atmosphere, in 25 ~ 30 DEG C of stirring reactions 2 ~ 4 days, termination reaction, by filtration, dialysis, drying, obtain target compound, wherein, poly-peptide homopolymer adopts poly-(r-phenmethyl-Pidolidone ester), poly-(r-ethyl-L-glutamate ester) or poly-(r-methyl-Pidolidone ester);
2) synthesis of poly acrylic acid-poly y graft copolymer: add amino-terminated poly (lactic acid-glycolic acid) monododecyl ether, solvent, condensing agent and polyacrylic acid in dry reactor, under inert atmosphere, in 25 ~ 35 DEG C of stirring reactions 2 ~ 3 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of poly (lactic acid-glycolic acid) and polyacrylic acid modified poly-peptide film: add poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer, poly acrylic acid-poly y graft copolymer and solvent in dry reactor, under inert atmosphere, after being uniformly mixed 40 ~ 50 minutes in 40 ~ 50 DEG C, also dry by casting method film forming, obtain target compound.
2. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: in step 1), condensing agent adopts N, N '-dicyclohexylcarbodiimide, N, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, solvent adopts dimethyl formamide, and reactant solution concentration is 5 ~ 15 g:100 ml.
3. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: in step 1), poly (lactic acid-glycolic acid) monododecyl ether adopts poly-(D, L) y monododecyl ether (lactic acid and oxyacetic acid mol ratio: 50/50), the mol ratio of poly (lactic acid-glycolic acid) monododecyl ether and poly-peptide homopolymer is 7 ~ 15:1; The mol ratio of condensing agent and poly-peptide homopolymer is 1.08 ~ 1.8:1.
4. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: step 2) in, condensing agent adopts N, N '-dicyclohexylcarbodiimide, N, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, solvent adopts dimethyl sulfoxide (DMSO), and reactant solution concentration is 5 ~ 15 g:100 ml.
5. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: step 2) in, poly (lactic acid-glycolic acid) monododecyl ether adopts poly-(D, L) y monododecyl ether (lactic acid and oxyacetic acid mol ratio: 50/50), poly (lactic acid-glycolic acid) monododecyl ether and polyacrylic mol ratio are 3 ~ 6:1; Condensing agent and polyacrylic mol ratio are 1.08 ~ 1.8:1.
6. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylic acid improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: in step 3), the mass percent of poly acrylic acid-poly y graft copolymer in modified membrane is 2 ~ 4%, solvent adopts dimethyl sulfoxide (DMSO), and mixture solution concentration is 25 ~ 35 g:100 ml.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510004506.4A CN104448841B (en) | 2015-01-06 | 2015-01-06 | A kind of method that poly (lactic acid-glycolic acid) improves poly-peptide film hydrophilic and compliance with polyacrylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510004506.4A CN104448841B (en) | 2015-01-06 | 2015-01-06 | A kind of method that poly (lactic acid-glycolic acid) improves poly-peptide film hydrophilic and compliance with polyacrylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104448841A true CN104448841A (en) | 2015-03-25 |
| CN104448841B CN104448841B (en) | 2016-08-31 |
Family
ID=52895627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510004506.4A Expired - Fee Related CN104448841B (en) | 2015-01-06 | 2015-01-06 | A kind of method that poly (lactic acid-glycolic acid) improves poly-peptide film hydrophilic and compliance with polyacrylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104448841B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105504303A (en) * | 2016-03-03 | 2016-04-20 | 山东理工大学 | Polyvinyl alcohol-polypeptide-polycaprolactone-poly lactic acid-glycolic acid triple-graft copolymer preparation method |
| CN105622950A (en) * | 2016-02-29 | 2016-06-01 | 山东理工大学 | Preparation method of polyvinyl alcohol-poly(trimethylene carbonate)-poly(lactic acid-glycolic acid) dual-grafted copolymer |
| CN105647193A (en) * | 2016-03-07 | 2016-06-08 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film by polylactic acid-glycolic acid and polypeptide |
| CN105647197A (en) * | 2016-03-16 | 2016-06-08 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film by polypeptide and poly(lactic acid-glycolic acid) |
| CN105694059A (en) * | 2016-03-03 | 2016-06-22 | 山东理工大学 | Method for preparing polyvinyl alcohol-poly lactic acid-glycolic acid-polycaprolactone dual-grafted copolymer |
| CN105694474A (en) * | 2016-03-07 | 2016-06-22 | 山东理工大学 | Method for improving water resisting property and flexibility of polyvinyl alcohol film by means of poly trimethylene carbonate and poly lactic acid-glycolic acid |
| CN105694476A (en) * | 2016-03-16 | 2016-06-22 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol membrane through poly trimethylene carbonate and poly lactic acid-glycolic acid |
| CN105732994A (en) * | 2016-03-03 | 2016-07-06 | 山东理工大学 | Method for preparing polyvinyl alcohol-polytrimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer |
| CN106987139A (en) * | 2017-05-25 | 2017-07-28 | 山东理工大学 | A kind of method that MPEGPLA lifts polypropylene sorrel water resistance and compliance with polylactide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012255066B2 (en) * | 2011-05-18 | 2016-06-02 | Takeda Pharmaceutical Company Limited | Modification-dependent activity assays |
| CN103242536B (en) * | 2013-05-09 | 2014-12-10 | 山东理工大学 | Method for preparing polypeptide-polylactic acid-polyethyleneglycol dual-graft copolymer |
-
2015
- 2015-01-06 CN CN201510004506.4A patent/CN104448841B/en not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622950A (en) * | 2016-02-29 | 2016-06-01 | 山东理工大学 | Preparation method of polyvinyl alcohol-poly(trimethylene carbonate)-poly(lactic acid-glycolic acid) dual-grafted copolymer |
| CN105504303A (en) * | 2016-03-03 | 2016-04-20 | 山东理工大学 | Polyvinyl alcohol-polypeptide-polycaprolactone-poly lactic acid-glycolic acid triple-graft copolymer preparation method |
| CN105694059A (en) * | 2016-03-03 | 2016-06-22 | 山东理工大学 | Method for preparing polyvinyl alcohol-poly lactic acid-glycolic acid-polycaprolactone dual-grafted copolymer |
| CN105732994A (en) * | 2016-03-03 | 2016-07-06 | 山东理工大学 | Method for preparing polyvinyl alcohol-polytrimethylene carbonate-poly lactic acid-glycolic acid double-grafted copolymer |
| CN105647193A (en) * | 2016-03-07 | 2016-06-08 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film by polylactic acid-glycolic acid and polypeptide |
| CN105694474A (en) * | 2016-03-07 | 2016-06-22 | 山东理工大学 | Method for improving water resisting property and flexibility of polyvinyl alcohol film by means of poly trimethylene carbonate and poly lactic acid-glycolic acid |
| CN105694474B (en) * | 2016-03-07 | 2018-07-10 | 山东理工大学 | A kind of method being improved with polytrimethylene carbonate and poly (lactic acid-glycolic acid) to polyvinyl alcohol film water resistance and compliance |
| CN105647197A (en) * | 2016-03-16 | 2016-06-08 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film by polypeptide and poly(lactic acid-glycolic acid) |
| CN105694476A (en) * | 2016-03-16 | 2016-06-22 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol membrane through poly trimethylene carbonate and poly lactic acid-glycolic acid |
| CN105694476B (en) * | 2016-03-16 | 2018-07-13 | 山东理工大学 | A kind of method that polytrimethylene carbonate improves polyvinyl alcohol film water resistance and compliance with poly (lactic acid-glycolic acid) |
| CN106987139A (en) * | 2017-05-25 | 2017-07-28 | 山东理工大学 | A kind of method that MPEGPLA lifts polypropylene sorrel water resistance and compliance with polylactide |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104448841B (en) | 2016-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104448841A (en) | Method for improving hydrophilia and flexibility of poly peptide film through poly (lactic acid-glycolic acid) (PLGA) and polyacrylic acid | |
| CN104479158A (en) | Method for improving hydrophilia and flexibility of polypeptide membrane through polydioxanone and polyethylene glycol | |
| CN104479157A (en) | Method for improving hydrophilia and flexibility of polypeptide membrane through polycaprolactone and polyethylene glycol | |
| CN104559213A (en) | Method for improving hydrophily and flexibility of polypeptide membrane by poly(trimethylene carbonate) and polyethylene glycol | |
| CN103865087B (en) | A kind of method that poly-peptide film kindliness is improved by poly(lactic acid) and PPDO | |
| CN103834180B (en) | A kind of method that polycaprolactone and polypropylene glycol improve poly-peptide film kindliness | |
| CN105542479A (en) | Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(p-dioxanone) and poly lactic acid-glycolic acid | |
| CN105542482A (en) | Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(p-dioxanone) and poly(lactic acid-glycolic acid) | |
| CN103819905B (en) | A kind of method that PTMC and polyvinylpyrrolidone improve poly-peptide film wetting ability | |
| CN104559212A (en) | Method for improving hydrophily and flexibility of polypeptide membrane by poly(lactic acid-glycolic acid) and polyethylene glycol | |
| CN105542208A (en) | Method for improving water resistance and flexibility of polyvinyl alcohol film through polycaprolactone and poly(p-dioxanone) | |
| CN105647200A (en) | Method for improving water resistance and flexibility of polyvinyl alcohol film by polycaprolactone and poly(lactic acid-glycolic acid) | |
| CN103865090B (en) | A kind of method that polycaprolactone and polyoxyethylene glycol improve poly-peptide film wetting ability | |
| CN104559214A (en) | Method for improving hydrophily and flexibility of polypeptide membrane by polypropylene glycol and polyacrylic acid | |
| CN104559208A (en) | Method for improving hydrophilic property and flexibility of polypeptide film by adopting poly (lactic acid-glycolic acid) and polyacrylamide | |
| CN104559210A (en) | Method for improving hydrophily and flexibility of polypeptide film by polypropylene glycol and polyethylene glycol | |
| CN103819907B (en) | A kind of method that polypropylene glycol and polyvinyl alcohol improve poly-peptide film wetting ability | |
| CN104448843A (en) | Method for improving hydrophilia and flexibility of poly peptide film through polycaprolactone and polyacrylic acid | |
| CN104559218A (en) | Method for improving hydrophilicity and flexibility of polypeptide film by poly(p-dioxanone) and carboxymethyl chitosan | |
| CN104559216A (en) | Method for improving hydrophily and flexibility of polypeptide membrane by poly(trimethylene carbonate) and polyacrylic acid | |
| CN104559206A (en) | Method for improving hydrophilic property and flexibility of polypeptide film by adopting poly trimethylene carbonate and polyacrylamide | |
| CN104559211A (en) | Method for improving hydrophily and flexibility of polypeptide membrane by poly(p-dioxanone) and polyacrylic acid | |
| CN103819701B (en) | A kind of method that PTMC and PTMG are improved poly-peptide film kindliness | |
| CN104559222A (en) | Method for improving hydrophilicity and flexibility of polypeptide film by polycaprolactone and carboxymethyl chitosan | |
| CN104559215A (en) | Method for improving hydrophily and flexibility of polypeptide membrane by polylactic acid and polyethylene glycol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160831 Termination date: 20180106 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |