CN105542481A - Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone - Google Patents
Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone Download PDFInfo
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- CN105542481A CN105542481A CN201610148911.8A CN201610148911A CN105542481A CN 105542481 A CN105542481 A CN 105542481A CN 201610148911 A CN201610148911 A CN 201610148911A CN 105542481 A CN105542481 A CN 105542481A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L87/00—Compositions of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
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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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- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2230/00—Compositions for preparing biodegradable polymers
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- 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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- 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
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2467/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L2201/06—Biodegradable
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
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Abstract
The invention discloses a method for modifying the water resistance and flexibility of a polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone. The method includes the following steps of firstly, synthesizing polyvinyl alcohol, poly(trimethylene carbonate) and polycaprolactone double-draft copolymers, wherein poly(trimethylene carbonate) monododecyl ether with the end sealed by a carboxyl group, polycaprolactone monotridecyl ether with the end sealed by a carboxyl group, solvent, condensing agent and polyvinyl alcohol are added into a drying reactor to react for 2-3 days at a temperature of 30-35 DEG C to obtain the target object; secondly, preparing the polyvinyl alcohol membrane modified by the poly(trimethylene carbonate) and polycaprolactone, wherein the polyvinyl alcohol, poly(trimethylene carbonate) and polycaprolactone double-draft copolymers, polycaprolactone monotridecyl ether and solvent are added into the drying reactor to be mixed for 50-60 minutes at a temperature of 47-52 DEG C, and the membrane is formed and dried to obtain the target object. The method is simple in preparation process and easy to grasp, and the water resistance and flexibility of the modified membrane 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.PTMC and polycaprolactone have excellent biocompatibility and the biomaterial of biodegradability, has good hydrophobicity and kindliness.First PTMC segment and polycaprolactone segment are introduced polyvinyl alcohol segments simultaneously and form polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer, and then polycaprolactone segment is added polyvinyl alcohol-PTMC-polycaprolactone 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 PTMC and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, it is characterized in that: in modified membrane, the molecular weight of polyvinyl alcohol segments is 86000 ~ 92000, the molecular weight of PTMC segment is 2600 ~ 2900, and the molecular weight of polycaprolactone segment is 2600 ~ 2900; Its method of modifying adopts following steps:
1) synthesis of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer: add the PTMC monododecyl ether of carboxy blocking, the polycaprolactone list tridecyl ether of carboxy blocking, solvent, condensing agent and polyvinyl alcohol in dry reactor, under inert atmosphere, in 30 ~ 35 DEG C of stirring reactions 2 ~ 3 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
2) preparation of PTMC and Polycaprolactone modified polyvinyl alcohol film: add polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer, polycaprolactone list tridecyl ether and solvent in dry reactor, under inert atmosphere, after being uniformly mixed 50 ~ 60 minutes in 47 ~ 52 DEG C, also dry by casting method film forming, obtain target compound.
Described a kind of PTMC and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, in step 1), the mol ratio of PTMC monododecyl ether and polyvinyl alcohol is 15 ~ 25:1, and the mol ratio of polycaprolactone list tridecyl ether and polyvinyl alcohol is 15 ~ 25:1.
Described a kind of PTMC and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, and 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.
Described a kind of PTMC and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, step 2) in, the mass percent of polycaprolactone list tridecyl 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, described a kind of PTMC and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, adopt a kind of polymkeric substance polymeric monomer different from two kinds to carry out the reaction of esterification and blended two kinds of means simultaneously, 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-polycaprolactone dual graft multipolymer
18 grams of polyvinyl alcohol (molecular weight is 86000), the PTMC monododecyl ether (molecular weight is 2600) of 10.2 grams of carboxy blockings and the polycaprolactone list tridecyl ether (molecular weight is 2600) of 10.2 grams of carboxy blockings is added at dry reactor, add 350ml dimethyl sulfoxide (DMSO), then add 0.055 gram
n, N '-dicyclohexylcarbodiimide, under inert atmosphere, in 30 DEG C of stirring reactions 2 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
2) preparation of PTMC and Polycaprolactone modified polyvinyl alcohol film
10 grams of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymers and 37ml dimethyl sulfoxide solvent is added in dry reactor, separately add the polycaprolactone list tridecyl ether (molecular weight is 2600) 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 12.3 ° and 12.6% before modified.
embodiment 2
1) preparation of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer
21.6 grams of polyvinyl alcohol (molecular weight is 89000), the PTMC monododecyl ether (molecular weight is 2700) of 11.7 grams of carboxy blockings and the polycaprolactone list tridecyl ether (molecular weight is 2700) of 11.7 grams of carboxy blockings is added at dry reactor, add 445ml dimethyl sulfoxide (DMSO), then add 0.037 gram
n, N '-DIC, under inert atmosphere, in 32 DEG C of stirring reactions 3 days, termination reaction, by filtering, dialysis, dry, obtains target compound;
2) preparation of PTMC and Polycaprolactone modified polyvinyl alcohol film
10 grams of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymers and 36ml dimethyl sulfoxide solvent is added in dry reactor, separately add the polycaprolactone list tridecyl ether (molecular weight is 2700) 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 13.1 ° and 13.5% before modified.
embodiment 3
1) preparation of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer
22 grams of polyvinyl alcohol (molecular weight is 92000), the PTMC monododecyl ether (molecular weight is 2900) of 12.5 grams of carboxy blockings and the polycaprolactone list tridecyl ether (molecular weight is 2900) of 12.5 grams of carboxy blockings is added at dry reactor, add 456ml dimethyl sulfoxide (DMSO), add 0.059 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, obtain target compound;
2) preparation of PTMC and Polycaprolactone modified polyvinyl alcohol film
9.5 grams of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymers and 35ml dimethyl sulfoxide solvent is added in dry reactor, separately add the polycaprolactone list tridecyl ether (molecular weight is 2900) accounting for modified membrane gross weight 4%, under inert atmosphere, 60 minutes are uniformly mixed in 52 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 13.6 ° and 14.4% before modified.
Claims (4)
1. a PTMC and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, it is characterized in that: in modified membrane, the molecular weight of polyvinyl alcohol segments is 86000 ~ 92000, the molecular weight of PTMC segment is 2600 ~ 2900, and the molecular weight of polycaprolactone segment is 2600 ~ 2900; Its method of modifying adopts following steps:
1) synthesis of polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer: add the PTMC monododecyl ether of carboxy blocking, the polycaprolactone list tridecyl ether of carboxy blocking, solvent, condensing agent and polyvinyl alcohol in dry reactor, under inert atmosphere, in 30 ~ 35 DEG C of stirring reactions 2 ~ 3 days, termination reaction, by filtration, dialysis, drying, obtain target compound;
2) preparation of PTMC and Polycaprolactone modified polyvinyl alcohol film: add polyvinyl alcohol-PTMC-polycaprolactone dual graft multipolymer, polycaprolactone list tridecyl ether and solvent in dry reactor, under inert atmosphere, after being uniformly mixed 50 ~ 60 minutes in 47 ~ 52 DEG C, also dry by casting method film forming, obtain target compound.
2. a kind of PTMC according to claim 1 and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, it is characterized in that: in step 1), the mol ratio of PTMC monododecyl ether and polyvinyl alcohol is 15 ~ 25:1, and the mol ratio of polycaprolactone list tridecyl ether and polyvinyl alcohol is 15 ~ 25:1.
3. a kind of PTMC according to claim 1 and polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, it 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 polycaprolactone improve the method for polyvinyl alcohol film water tolerance and kindliness, it is characterized in that: step 2) in, the mass percent of polycaprolactone list tridecyl ether in modified membrane is 2 ~ 4%, solvent adopts dimethyl sulfoxide (DMSO), and mixture solution concentration is 25 ~ 30g:100ml.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610148911.8A CN105542481A (en) | 2016-03-16 | 2016-03-16 | Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone |
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| CN201610148911.8A CN105542481A (en) | 2016-03-16 | 2016-03-16 | Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106947261A (en) * | 2017-05-22 | 2017-07-14 | 山东理工大学 | A kind of method that PTMC improves polypropylene sorrel water resistance and compliance with polypropylene glycol |
| CN106947259A (en) * | 2017-05-22 | 2017-07-14 | 山东理工大学 | A kind of method being improved with MPEGPLA and PTMC to polypropylene sorrel water resistance and compliance |
| CN106977947A (en) * | 2017-05-25 | 2017-07-25 | 山东理工大学 | A kind of method that polycaprolactone improves polypropylene sorrel water resistance and compliance with PTMC |
| CN106987125A (en) * | 2017-05-22 | 2017-07-28 | 山东理工大学 | A kind of method that PTMC improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN106987130A (en) * | 2017-05-22 | 2017-07-28 | 山东理工大学 | A kind of method being improved with PTMC and polycaprolactone to polypropylene sorrel water resistance and compliance |
| CN107011665A (en) * | 2017-05-22 | 2017-08-04 | 山东理工大学 | A kind of method that PTMC improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN107011678A (en) * | 2017-05-25 | 2017-08-04 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN107011680A (en) * | 2017-05-25 | 2017-08-04 | 山东理工大学 | A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance |
| CN107011672A (en) * | 2017-05-22 | 2017-08-04 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN107011668A (en) * | 2017-05-22 | 2017-08-04 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with PTMC |
| CN107118570A (en) * | 2017-05-25 | 2017-09-01 | 山东理工大学 | A kind of method that PLA improves polypropylene sorrel water resistance and compliance with polycaprolactone |
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| CN103865091A (en) * | 2014-03-24 | 2014-06-18 | 山东理工大学 | Method for improving water resisting performance of polyvinyl alcohol film from polycaprolactone and polylactic acid |
| 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) |
| CN104479157A (en) * | 2015-01-06 | 2015-04-01 | 山东理工大学 | Method for improving hydrophilia and flexibility of polypeptide membrane through polycaprolactone and polyethylene glycol |
| CN104559213A (en) * | 2015-01-06 | 2015-04-29 | 山东理工大学 | Method for improving hydrophily and flexibility of polypeptide membrane by poly(trimethylene carbonate) and polyethylene glycol |
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2016
- 2016-03-16 CN CN201610148911.8A patent/CN105542481A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103865091A (en) * | 2014-03-24 | 2014-06-18 | 山东理工大学 | Method for improving water resisting performance of polyvinyl alcohol film from polycaprolactone and polylactic acid |
| 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) |
| CN104479157A (en) * | 2015-01-06 | 2015-04-01 | 山东理工大学 | Method for improving hydrophilia and flexibility of polypeptide membrane through polycaprolactone and polyethylene glycol |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106947261A (en) * | 2017-05-22 | 2017-07-14 | 山东理工大学 | A kind of method that PTMC improves polypropylene sorrel water resistance and compliance with polypropylene glycol |
| CN106947259A (en) * | 2017-05-22 | 2017-07-14 | 山东理工大学 | A kind of method being improved with MPEGPLA and PTMC to polypropylene sorrel water resistance and compliance |
| CN106987125A (en) * | 2017-05-22 | 2017-07-28 | 山东理工大学 | A kind of method that PTMC improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN106987130A (en) * | 2017-05-22 | 2017-07-28 | 山东理工大学 | A kind of method being improved with PTMC and polycaprolactone to polypropylene sorrel water resistance and compliance |
| CN107011665A (en) * | 2017-05-22 | 2017-08-04 | 山东理工大学 | A kind of method that PTMC improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN107011672A (en) * | 2017-05-22 | 2017-08-04 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN107011668A (en) * | 2017-05-22 | 2017-08-04 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with PTMC |
| CN106977947A (en) * | 2017-05-25 | 2017-07-25 | 山东理工大学 | A kind of method that polycaprolactone improves polypropylene sorrel water resistance and compliance with PTMC |
| CN107011678A (en) * | 2017-05-25 | 2017-08-04 | 山东理工大学 | A kind of method that MPEGPLA improves polypropylene sorrel water resistance and compliance with polycaprolactone |
| CN107011680A (en) * | 2017-05-25 | 2017-08-04 | 山东理工大学 | A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance |
| CN107118570A (en) * | 2017-05-25 | 2017-09-01 | 山东理工大学 | A kind of method that PLA improves polypropylene sorrel water resistance and compliance with polycaprolactone |
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