CN105542178A - Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(trimethylene carbonate) and polypeptide - Google Patents
Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(trimethylene carbonate) and polypeptide Download PDFInfo
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- CN105542178A CN105542178A CN201610125105.9A CN201610125105A CN105542178A CN 105542178 A CN105542178 A CN 105542178A CN 201610125105 A CN201610125105 A CN 201610125105A CN 105542178 A CN105542178 A CN 105542178A
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- polyvinyl alcohol
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- ptmc
- peptide
- kindliness
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- 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
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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
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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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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- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- 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
Abstract
The invention discloses a method for improving water resistance and flexibility of a polyvinyl alcohol film through poly(trimethylene carbonate) and polypeptide. The method comprises steps as follows: 1), carboxyl terminated poly(trimethylene carbonate) monododecyl ether, a solvent, a condensing agent and polyvinyl alcohol are added to a dry reactor and have a reaction, and a polyvinyl alcohol-poly(trimethylene carbonate) grafted copolymer is obtained; (2), the polyvinyl alcohol-poly(trimethylene carbonate) grafted copolymer, a carboxyl terminated polypeptide homopolymer, a solvent and a condensing agent are added to the reactor and have a reaction, and a polyvinyl alcohol-poly(trimethylene carbonate)-polypeptide double-grafted copolymer is obtained; 3), the polyvinyl alcohol-poly(trimethylene carbonate)-polypeptide double-grafted copolymer, the poly(trimethylene carbonate) monododecyl ether and a solvent are added to the reactor and mixed, then a film is formed, and a target product is obtained. The preparation process is simple and easy to master, and the water resistance and the flexibility of the modified film are greatly improved.
Description
Technical field
The present invention relates to a kind of method that polyvinyl alcohol film water tolerance and kindliness are improved, belong to field of polymer film preparing technology.
Background technology
Polyvinyl alcohol a kind ofly has good biocompatibility and the biomaterial of biodegradability, polyvinyl alcohol film can be used as artificial skin etc., but polyvinyl alcohol film wetting ability too by force and more stiff, lacks good water tolerance and kindliness, thus limit its application to a certain extent.Poly-peptide has excellent biocompatibility and the biomaterial of biodegradability, has excellent hydrophobicity.PTMC has excellent biocompatibility and the biomaterial of biodegradability, has good hydrophobicity and kindliness.First PTMC segment is introduced polyvinyl alcohol segments and form polyvinyl alcohol-PTMC graft copolymer, again poly-peptide segment is introduced in the polyvinyl alcohol segments in polyvinyl alcohol-PTMC graft copolymer and obtain polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer, and then PTMC segment is added polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer formation blend, obtained modified PVA membrane, thus drastically increase water tolerance and the kindliness of polyvinyl alcohol film.
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 polyvinyl alcohol film water tolerance and kindliness are improved.Its technical scheme is:
A kind of method that PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, it is characterized in that: in modified membrane, the molecular weight of polyvinyl alcohol segments is 84000 ~ 90000, the molecular weight of PTMC segment is 2500 ~ 2700, and the molecular weight of poly-peptide segment is 2000 ~ 2200; Its method of modifying adopts following steps:
1) preparation of polyvinyl alcohol-PTMC graft copolymer: add the PTMC monododecyl ether of carboxy blocking, solvent, condensing agent and polyvinyl alcohol 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;
2) preparation of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer: add polyvinyl alcohol-PTMC graft copolymer, the poly-peptide homopolymer of carboxy blocking, solvent and condensing agent in dry reactor, under inert atmosphere, in 26 ~ 34 DEG C of stirring reactions 2 ~ 4 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the polyvinyl alcohol film of PTMC and poly-peptide modification: add polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer, PTMC monododecyl ether and solvent in dry reactor, under inert atmosphere, after being uniformly mixed 50 ~ 60 minutes in 47 ~ 50 DEG C, also dry by casting method film forming, obtain target compound.
The method that described a kind of PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, in step 1), the mol ratio of PTMC monododecyl ether and polyvinyl alcohol is 15 ~ 25:1.
The method that described a kind of PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, in step 1), condensing agent adopts
n, N '-dicyclohexylcarbodiimide,
n, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, the mol ratio of condensing agent and polyvinyl alcohol is 1.07 ~ 1.8:1, and solvent adopts dimethyl sulfoxide (DMSO), and reactant solution concentration is 5 ~ 15g:100ml.
The method that described a kind of PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, step 2) in, gather peptide homopolymer and adopt poly-(r-phenmethyl-Pidolidone ester), poly-(r-ethyl-L-glutamate ester) or poly-(r-methyl-Pidolidone ester), the mol ratio of gathering the polyvinyl alcohol segments in peptide homopolymer and polyvinyl alcohol-PTMC graft copolymer is 15 ~ 25:1.
The method that described a kind of PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, step 2) in, condensing agent adopts
n, N '-dicyclohexylcarbodiimide,
n, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, the mol ratio of the polyvinyl alcohol segments in condensing agent and polyvinyl alcohol-PTMC graft copolymer is 1.07 ~ 1.8:1, solvent adopts dimethyl sulfoxide (DMSO), and reactant solution concentration is 5 ~ 15g:100ml.
The method that described a kind of PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, in step 3), the mass percent of PTMC monododecyl ether in modified membrane is 2 ~ 4%, solvent adopts dimethyl sulfoxide (DMSO), and mixture solution concentration is 25 ~ 30g:100ml.
Compared with prior art, its advantage is in the present invention:
1, the method that described a kind of PTMC and poly-peptide improve polyvinyl alcohol film water tolerance and kindliness, adopts two step esterifications and blended three kinds of means, simple to operate, be easy to grasp;
2, described polyvinyl alcohol modification film water tolerance and kindliness are enhanced.
Embodiment
embodiment 1
1) preparation of polyvinyl alcohol-PTMC graft copolymer
Add the PTMC monododecyl ether (molecular weight is 2500) of 18 grams of polyvinyl alcohol (molecular weight is 84000) and 9.5 grams of carboxy blockings at dry reactor, add 260ml dimethyl sulfoxide (DMSO), then add 0.056 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) preparation of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer
Add poly-(r-phenmethyl-Pidolidone ester) (molecular weight is 2000) of 10 grams of polyvinyl alcohol-PTMC graft copolymer and 4.5 grams of carboxy blockings at dry reactor, add 144ml dimethyl sulfoxide (DMSO), then add 0.031 gram
n, N '-dicyclohexylcarbodiimide, under inert atmosphere, in 26 DEG C of stirring reactions 2 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
3) preparation of the polyvinyl alcohol film of PTMC and poly-peptide modification
10 grams of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer and 37ml dimethyl sulfoxide solvent is added in dry reactor, separately add the PTMC monododecyl ether (molecular weight is 2500) accounting for modified membrane gross weight 2%, under inert atmosphere, 50 minutes are uniformly mixed in 47 DEG C, use casting method film forming, in 50 DEG C of vacuum drying ovens, drying obtains target compound.
After tested: the surface contact angle of target compound of the present invention and water and elongation at break thereof are respectively than improve 12.4 ° and 12.6% before modified.
embodiment 2
1) preparation of polyvinyl alcohol-PTMC graft copolymer
Add the PTMC monododecyl ether (molecular weight is 2600) of 18.2 grams of polyvinyl alcohol (molecular weight is 88000) and 9.6 grams of carboxy blockings at dry reactor, add 262ml dimethyl sulfoxide (DMSO), then add 0.034 gram
n, N '-DIC, under inert atmosphere, in 30 DEG C of stirring reactions 3 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
2) preparation of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer
Add poly-(r-ethyl-L-glutamate ester) (molecular weight is 2100) of 10.3 grams of polyvinyl alcohol-PTMC graft copolymer and 4.4 grams of carboxy blockings at dry reactor, add 145ml dimethyl sulfoxide (DMSO), then add 0.019 gram
n, N '-DIC, under inert atmosphere, in 30 DEG C of stirring reactions 3 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
3) preparation of the polyvinyl alcohol film of PTMC and poly-peptide modification
9.8 grams of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer and 36ml dimethyl sulfoxide solvent is added in dry reactor, separately add the PTMC monododecyl ether (molecular weight is 2600) accounting for modified membrane gross weight 3%, under inert atmosphere, 55 minutes are uniformly mixed in 49 DEG C, use casting method film forming, in 50 DEG C of vacuum drying ovens, drying obtains target compound.
After tested: the surface contact angle of target compound of the present invention and water and elongation at break thereof are respectively than improve 12.7 ° and 13.1% before modified.
embodiment 3
1) preparation of polyvinyl alcohol-PTMC graft copolymer
The PTMC monododecyl ether (molecular weight is 2700) of 18.3 grams of polyvinyl alcohol (molecular weight is 90000) and 10.2 grams of carboxy blockings is added at dry reactor, add 264ml dimethyl sulfoxide (DMSO), add 0.053 gram of 3-ethyl-1-(3-dimethylaminopropyl again) carbodiimide, under inert atmosphere, in 35 DEG C of stirring reactions 2 days, termination reaction, by filtration, dialysis, drying, obtains target compound;
2) preparation of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer
Poly-(r-methyl-Pidolidone ester) (molecular weight is 2200) of 10 grams of polyvinyl alcohol-PTMC graft copolymer and 4.6 grams of carboxy blockings is added at dry reactor, add 143ml dimethyl sulfoxide (DMSO), add 0.028 gram of 3-ethyl-1-(3-dimethylaminopropyl again) carbodiimide, under inert atmosphere, in 34 DEG C of stirring reactions 4 days, termination reaction, by filtration, dialysis, drying, obtains target compound;
3) preparation of the polyvinyl alcohol film of PTMC and poly-peptide modification
9.5 grams of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer and 35ml dimethyl sulfoxide solvent is added in dry reactor, separately add the PTMC monododecyl ether (molecular weight is 2700) accounting for modified membrane gross weight 4%, under inert atmosphere, 60 minutes are uniformly mixed in 50 DEG C, use casting method film forming, in 50 DEG C of vacuum drying ovens, drying obtains target compound.
After tested: the surface contact angle of target compound of the present invention and water and elongation at break thereof are respectively than improve 13.1 ° and 13.5% before modified.
Claims (6)
1. method polyvinyl alcohol film water tolerance and kindliness improved with PTMC and poly-peptide, it is characterized in that: in modified membrane, the molecular weight of polyvinyl alcohol segments is 84000 ~ 90000, the molecular weight of PTMC segment is 2500 ~ 2700, and the molecular weight of poly-peptide segment is 2000 ~ 2200; Its method of modifying adopts following steps:
1) preparation of polyvinyl alcohol-PTMC graft copolymer: add the PTMC monododecyl ether of carboxy blocking, solvent, condensing agent and polyvinyl alcohol 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;
2) preparation of polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer: add polyvinyl alcohol-PTMC graft copolymer, the poly-peptide homopolymer of carboxy blocking, solvent and condensing agent in dry reactor, under inert atmosphere, in 26 ~ 34 DEG C of stirring reactions 2 ~ 4 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
3) preparation of the polyvinyl alcohol film of PTMC and poly-peptide modification: add polyvinyl alcohol-PTMC-poly-peptide dual graft multipolymer, PTMC monododecyl ether and solvent in dry reactor, under inert atmosphere, after being uniformly mixed 50 ~ 60 minutes in 47 ~ 50 DEG C, also dry by casting method film forming, obtain target compound.
2. a kind of PTMC according to claim 1 and poly-peptide method that polyvinyl alcohol film water tolerance and kindliness are improved, it is characterized in that: in step 1), the mol ratio of PTMC monododecyl ether and polyvinyl alcohol is 15 ~ 25:1.
3. the method improved polyvinyl alcohol film water tolerance and kindliness of a kind of PTMC according to claim 1 and poly-peptide, is characterized in that: in step 1), and condensing agent adopts
n, N '-dicyclohexylcarbodiimide,
n, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, the mol ratio of condensing agent and polyvinyl alcohol is 1.07 ~ 1.8:1, and solvent adopts dimethyl sulfoxide (DMSO), and reactant solution concentration is 5 ~ 15g:100ml.
4. a kind of PTMC according to claim 1 and poly-peptide method that polyvinyl alcohol film water tolerance and kindliness are improved, it is characterized in that: step 2) in, gather peptide homopolymer and adopt poly-(r-phenmethyl-Pidolidone ester), poly-(r-ethyl-L-glutamate ester) or poly-(r-methyl-Pidolidone ester), the mol ratio of gathering the polyvinyl alcohol segments in peptide homopolymer and polyvinyl alcohol-PTMC graft copolymer is 15 ~ 25:1.
5. the method improved polyvinyl alcohol film water tolerance and kindliness of a kind of PTMC according to claim 1 and poly-peptide, is characterized in that: step 2) in, condensing agent adopts
n, N '-dicyclohexylcarbodiimide,
n, N '-DIC or 3-ethyl-1-(3-dimethylaminopropyl) carbodiimide, the mol ratio of the polyvinyl alcohol segments in condensing agent and polyvinyl alcohol-PTMC graft copolymer is 1.07 ~ 1.8:1, solvent adopts dimethyl sulfoxide (DMSO), and reactant solution concentration is 5 ~ 15g:100ml.
6. a kind of PTMC according to claim 1 and poly-peptide method that polyvinyl alcohol film water tolerance and kindliness are improved, it is characterized in that: in step 3), the mass percent of PTMC monododecyl ether in modified membrane is 2 ~ 4%, solvent adopts dimethyl sulfoxide (DMSO), and mixture solution concentration is 25 ~ 30g:100ml.
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| CN201610125105.9A CN105542178A (en) | 2016-03-07 | 2016-03-07 | Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(trimethylene carbonate) and polypeptide |
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| CN201610125105.9A CN105542178A (en) | 2016-03-07 | 2016-03-07 | Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(trimethylene carbonate) and polypeptide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106947265A (en) * | 2017-05-25 | 2017-07-14 | 山东理工大学 | A kind of method that PPDO is improved with PTMC to polypropylene sorrel water resistance and compliance |
| CN106987136A (en) * | 2017-05-25 | 2017-07-28 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with PTMC |
| CN107118571A (en) * | 2017-05-25 | 2017-09-01 | 山东理工大学 | A kind of method that PLA is improved with PTMC to polypropylene sorrel water resistance and compliance |
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| CN103819907A (en) * | 2014-03-10 | 2014-05-28 | 山东理工大学 | Method for improving polypeptide membrane hydrophilicity by adopting polypropylene glycol and polyvinyl alcohol |
| CN103881398A (en) * | 2014-03-24 | 2014-06-25 | 山东理工大学 | Method for improving water resistance of polyvinyl alcohol film by using poly(trimethylene carbonate) and poly(p-dioxanone) |
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| CN104530721A (en) * | 2015-01-05 | 2015-04-22 | 山东理工大学 | Method for improving hydrophilia and flexibility of polypeptide film through polyurethane and polyvinyl alcohol |
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| CN102181060A (en) * | 2011-03-20 | 2011-09-14 | 山东理工大学 | Polyvinyl alcohol-polypeptide-polyethylene glycol graft copolymer and preparation method thereof |
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| CN106947265A (en) * | 2017-05-25 | 2017-07-14 | 山东理工大学 | A kind of method that PPDO is improved with PTMC to polypropylene sorrel water resistance and compliance |
| CN106987136A (en) * | 2017-05-25 | 2017-07-28 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with PTMC |
| CN107118571A (en) * | 2017-05-25 | 2017-09-01 | 山东理工大学 | A kind of method that PLA is improved with PTMC to polypropylene sorrel water resistance and compliance |
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Application publication date: 20160504 |