CN104559208A - Method for improving hydrophilic property and flexibility of polypeptide film by adopting poly (lactic acid-glycolic acid) and polyacrylamide - Google Patents
Method for improving hydrophilic property and flexibility of polypeptide film by adopting poly (lactic acid-glycolic acid) and polyacrylamide Download PDFInfo
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- CN104559208A CN104559208A CN201510001625.4A CN201510001625A CN104559208A CN 104559208 A CN104559208 A CN 104559208A CN 201510001625 A CN201510001625 A CN 201510001625A CN 104559208 A CN104559208 A CN 104559208A
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Abstract
The invention discloses a method for improving the hydrophilic property and flexibility of a polypeptide film by adopting poly (lactic acid-glycolic acid) and polyacrylamide. The method comprises the following steps: 1) adding carboxyl-terminated poly (lactic acid-glycolic acid) monododecyl ether, a solvent, a condensing agent and a polypeptide homopolymer into a drying reactor, and stirring for reaction for 3-4 days, so as to obtain a polypeptide- poly (lactic acid-glycolic acid) segmented copolymer; 2) adding isocyanate-terminated poly (lactic acid-glycolic acid) monododecyl ether, a solvent, a catalyst and the polyacrylamide into the drying reactor, and stirring for reaction for 50-60 minutes, so as to obtain a polyacrylamide-poly (lactic acid-glycolic acid) grafted copolymer; 3) adding the polypeptide-poly (lactic acid-glycolic acid) segmented copolymer, the polyacrylamide-poly (lactic acid-glycolic acid) grafted copolymer and a solvent into the drying reactor, stirring and mixing for 40-50 minutes, performing film formation by adopting a tape-casting method, and drying, so as to obtain the target object. According to the invention, the preparation technology is simple, and the hydrophilic property and flexibility of the obtained modified film are greatly improved.
Description
Technical field
The present invention relates to a kind of method that poly (lactic acid-glycolic acid) and polyacrylamide 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, soft.Polyacrylamide has good biocompatibility and biodegradability, and has good wetting ability.First poly (lactic acid-glycolic acid) segment is introduced respectively poly-peptide segment and polyacrylamide segment forms poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer and polyacrylamide-poly (lactic acid-glycolic acid) 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 polyacrylamide.
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 polyacrylamide 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 polyacrylamide 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 20 ~ 30 DEG C of stirring reactions 3 ~ 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 polyacrylamide-poly (lactic acid-glycolic acid) graft copolymer: add the poly (lactic acid-glycolic acid) monododecyl ether of isocyano end-blocking, solvent, catalyzer and polyacrylamide in dry reactor, under inert atmosphere, in 60 ~ 65 DEG C of stirring reactions 50 ~ 60 minutes, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the poly-peptide film of poly (lactic acid-glycolic acid) and polyacrylamide modification: add poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer, polyacrylamide-poly (lactic acid-glycolic acid) 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 polyacrylamide 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 polyacrylamide 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 polyacrylamide improve the method for poly-peptide film wetting ability and kindliness, step 2) in, solvent adopts dimethyl formamide, catalyzer adopts dibutyl tin laurate, catalyst charge is 3 ~ 5 ‰ of poly (lactic acid-glycolic acid) monododecyl ether and polyacrylamide gross weight, and reactant solution concentration is 5 ~ 15 g:100 ml.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylamide 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) (lactic acid and oxyacetic acid mol ratio: 50/50), the mol ratio of poly (lactic acid-glycolic acid) monododecyl ether and polyacrylamide is 3 ~ 7:1 to y monododecyl ether.
Described a kind of poly (lactic acid-glycolic acid) and polyacrylamide improve the method for poly-peptide film wetting ability and kindliness, in step 3), polyacrylamide-the mass percent of poly (lactic acid-glycolic acid) graft copolymer in modified membrane is 2 ~ 4%, solvent adopts dimethyl formamide, 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 polyacrylamide improve poly-peptide film wetting ability and the method for kindliness, adopt amidate action, addition reaction and blended three 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 20 DEG C of stirring reactions 3 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
2) synthesis of polyacrylamide-poly (lactic acid-glycolic acid) graft copolymer
Poly (lactic acid-glycolic acid) monododecyl ether (molecular weight is 3000) and the 160 ml dimethyl formamides of 3.5 grams of polyacrylamides (molecular weight is 5000) and 9 grams of isocyano end-blockings are added in dry reactor, add the dibutyl tin laurate of above-mentioned reactant gross weight 3 ‰ again, under inert atmosphere, in 60 DEG C of stirring reactions 50 minutes, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the poly-peptide film of poly (lactic acid-glycolic acid) and polyacrylamide modification
12.5 grams of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymers and 45.8 ml solvent dimethylformamides are added in dry reactor, separately add the polyacrylamide-poly (lactic acid-glycolic acid) 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 13.3% 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 25 DEG C of stirring reactions 4 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
2) synthesis of polyacrylamide-poly (lactic acid-glycolic acid) graft copolymer
Poly (lactic acid-glycolic acid) monododecyl ether (molecular weight is 3500) and the 160 ml dimethyl formamides of 3.5 grams of polyacrylamides (molecular weight is 5500) and 9 grams of isocyano end-blockings are added in dry reactor, add the dibutyl tin laurate of above-mentioned reactant gross weight 4 ‰ again, under inert atmosphere, in 62 DEG C of stirring reactions 55 minutes, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the poly-peptide film of poly (lactic acid-glycolic acid) and polyacrylamide modification
12.6 grams of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymers and 45.5 ml solvent dimethylformamides are added in dry reactor, separately add the polyacrylamide-poly (lactic acid-glycolic acid) 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 13.8% and 14.2% 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 3 days, termination reaction, by filtration, dialysis, drying, obtains target compound;
2) synthesis of polyacrylamide-poly (lactic acid-glycolic acid) graft copolymer
Poly (lactic acid-glycolic acid) monododecyl ether (molecular weight is 4000) and the 160 ml dimethyl formamides of 3.5 grams of polyacrylamides (molecular weight is 6000) and 9 grams of isocyano end-blockings are added in dry reactor, add the dibutyl tin laurate of above-mentioned reactant gross weight 5 ‰ again, under inert atmosphere, in 65 DEG C of stirring reactions 60 minutes, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the poly-peptide film of poly (lactic acid-glycolic acid) and polyacrylamide modification
12.8 grams of poly-peptide-poly (lactic acid-glycolic acid) segmented copolymers and 45.4 ml solvent dimethylformamides are added in dry reactor, separately add the polyacrylamide-poly (lactic acid-glycolic acid) 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 14.5% and 15.7% before modified.
Claims (6)
1. a poly (lactic acid-glycolic acid) and polyacrylamide 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 polyacrylamide 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 20 ~ 30 DEG C of stirring reactions 3 ~ 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 polyacrylamide-poly (lactic acid-glycolic acid) graft copolymer: add the poly (lactic acid-glycolic acid) monododecyl ether of isocyano end-blocking, solvent, catalyzer and polyacrylamide in dry reactor, under inert atmosphere, in 60 ~ 65 DEG C of stirring reactions 50 ~ 60 minutes, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the poly-peptide film of poly (lactic acid-glycolic acid) and polyacrylamide modification: add poly-peptide-poly (lactic acid-glycolic acid) segmented copolymer, polyacrylamide-poly (lactic acid-glycolic acid) 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 polyacrylamide 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 polyacrylamide 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 polyacrylamide improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: step 2) in, solvent adopts dimethyl formamide, catalyzer adopts dibutyl tin laurate, catalyst charge is 3 ~ 5 ‰ of poly (lactic acid-glycolic acid) monododecyl ether and polyacrylamide gross weight, and reactant solution concentration is 5 ~ 15 g:100 ml.
5. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylamide 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) (lactic acid and oxyacetic acid mol ratio: 50/50), the mol ratio of poly (lactic acid-glycolic acid) monododecyl ether and polyacrylamide is 3 ~ 7:1 to y monododecyl ether.
6. a kind of poly (lactic acid-glycolic acid) according to claim 1 and polyacrylamide improve the method for poly-peptide film wetting ability and kindliness, it is characterized in that: in step 3), polyacrylamide-the mass percent of poly (lactic acid-glycolic acid) graft copolymer in modified membrane is 2 ~ 4%, solvent adopts dimethyl formamide, and mixture solution concentration is 25 ~ 35 g:100 ml.
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Cited By (5)
| 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 |
| 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 |
| CN105694058A (en) * | 2016-02-29 | 2016-06-22 | 山东理工大学 | Method for preparing polyving akohol-poly(lactic acid-glycolic acid)-polypeptide double graft copolymer |
| CN105754110A (en) * | 2016-03-09 | 2016-07-13 | 山东理工大学 | Preparation method of a polyvinyl alcohol-polycaprolactone-poly lactic acid-glycolic acid dual-grafted copolymer micelle |
| CN112592587A (en) * | 2021-03-04 | 2021-04-02 | 旗众科技有限公司 | Preparation method of polylactic acid biological composite material |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103224627A (en) * | 2013-05-09 | 2013-07-31 | 山东理工大学 | Preparation method of polylactic acid glycollic acid-polypeptide-polyethylene glycol diblock-grafted copolymer |
| CN103804916A (en) * | 2014-03-14 | 2014-05-21 | 山东理工大学 | Method for improving hydrophilicity of polypeptide membrane by using polylactic acid and polyacrylic acid |
| CN103865274A (en) * | 2014-03-14 | 2014-06-18 | 山东理工大学 | Method for improving flexibility of polypeptide film by poly(lactic acid-glycolic acid) and poly(caprolactone-lactide) |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103224627A (en) * | 2013-05-09 | 2013-07-31 | 山东理工大学 | Preparation method of polylactic acid glycollic acid-polypeptide-polyethylene glycol diblock-grafted copolymer |
| CN103804916A (en) * | 2014-03-14 | 2014-05-21 | 山东理工大学 | Method for improving hydrophilicity of polypeptide membrane by using polylactic acid and polyacrylic acid |
| CN103865274A (en) * | 2014-03-14 | 2014-06-18 | 山东理工大学 | Method for improving flexibility of polypeptide film by poly(lactic acid-glycolic acid) and poly(caprolactone-lactide) |
Cited By (5)
| 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 |
| CN105694058A (en) * | 2016-02-29 | 2016-06-22 | 山东理工大学 | Method for preparing polyving akohol-poly(lactic acid-glycolic acid)-polypeptide double graft copolymer |
| 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 |
| CN105754110A (en) * | 2016-03-09 | 2016-07-13 | 山东理工大学 | Preparation method of a polyvinyl alcohol-polycaprolactone-poly lactic acid-glycolic acid dual-grafted copolymer micelle |
| CN112592587A (en) * | 2021-03-04 | 2021-04-02 | 旗众科技有限公司 | Preparation method of polylactic acid biological composite material |
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