CN107011680A - A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance - Google Patents
A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance Download PDFInfo
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- CN107011680A CN107011680A CN201710376551.1A CN201710376551A CN107011680A CN 107011680 A CN107011680 A CN 107011680A CN 201710376551 A CN201710376551 A CN 201710376551A CN 107011680 A CN107011680 A CN 107011680A
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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
- C08L87/005—Block or graft polymers not provided for in groups C08L1/00 - C08L85/04
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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
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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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- 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
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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
- 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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Abstract
The present invention discloses a kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance, using following steps：1）Hydroxy-end capped PTMC monododecyl ether, solvent, condensing agent and polyacrylic acid is added in dry reactor, reacts 2~4 days, obtains polyacrylic acid PTMC graft copolymer；2）Graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensing agent are added in dry reactor, reacts 2~4 days, obtains polyacrylic acid polycaprolactone PTMC dual graft copolymer；3）Dual graft copolymer, polycaprolactone list tridecyl ether and solvent are added in dry reactor, after mixing 50~60 minutes, with the tape casting film forming and drying, object of the present invention is obtained.Preparation technology of the present invention is simple, be easy to grasp, and gained Modified Membrane water resistance and compliance are greatly improved.
Description
Technical field
The present invention relates to a kind of method improved to polypropylene sorrel water resistance and compliance, belong to thin polymer film
Preparing technical field.
Background technology
Polyacrylic acid is a kind of biomaterial with good biocompatibility and biodegradability, polypropylene sorrel
It can be used as artificial skin etc., but polypropylene sorrel hydrophily is too strong and more stiff, lacks preferable water resistance and compliance, so that
Its application is limited to a certain extent.Polycaprolactone and PTMC are with excellent biocompatibility and biology
The biomaterial of degradability, with good hydrophobicity and compliance.First PTMC segment is grafted to poly-
Poly acrylic acid-poly trimethylene carbonate graft copolymer is obtained on acrylic molecules chain, then polycaprolactone segment is grafted to
Poly acrylic acid-poly caprolactone-poly- is formed on polyacrylic acid segment in poly acrylic acid-poly trimethylene carbonate graft copolymer
Trimethylene carbonate dual graft copolymer, then adds poly acrylic acid-poly caprolactone-poly- three methylene by polycaprolactone segment again
Base carbonic ester dual graft copolymer formation blend, is made modified polypropene sorrel, so as to drastically increase polypropylene sorrel
Water resistance and compliance.
The content of the invention
It is preferable to polypropylene sorrel water resistance and submissive it is an object of the invention to provide a kind of simple to operate and effect
The method that property is improved.Its technical scheme is：
A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance, its
It is characterised by：The molecular weight of polyacrylic acid segment is 82000~93000 in Modified Membrane, point of PTMC segment
Son amount is 2500~2700, and the molecular weight of polycaprolactone segment is 2300~2400；Its method of modifying uses following steps：
1）The synthesis of poly acrylic acid-poly trimethylene carbonate graft copolymer：Added in dry reactor hydroxy-end capped
Under PTMC monododecyl ether, solvent, condensing agent and polyacrylic acid, inert atmosphere, in 27~34 DEG C of stirrings
Reaction 2~4 days, terminating reaction by filtering, dialysis, is dried, obtains object；
2）The synthesis of poly acrylic acid-poly caprolactone-PTMC dual graft copolymer：Added in dry reactor
Poly acrylic acid-poly trimethylene carbonate graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensation
Under agent, inert atmosphere, in 26~32 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, was dried, obtains target
Thing；
3）The preparation for the polypropylene sorrel that polycaprolactone is improved with PTMC：Poly- third is added in dry reactor
Olefin(e) acid-polycaprolactone-PTMC dual graft copolymer, polycaprolactone list tridecyl ether and solvent, indifferent gas
Under atmosphere, after 46~50 DEG C of stirrings are mixed 50~60 minutes, with the tape casting film forming and drying, object is obtained.
A kind of described polycaprolactone changes with PTMC to polypropylene sorrel water resistance and compliance
Good method, step 1）In, the mol ratio of PTMC monododecyl ether and polyacrylic acid is 15~25:1.
A kind of described polycaprolactone changes with PTMC to polypropylene sorrel water resistance and compliance
Good method, step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- second
Base -1-（3- dimethylaminopropyls）The mol ratio of carbodiimide, condensing agent and polyacrylic acid is 1.06~1.9:1, solvent uses two
Methyl sulfoxide, reactant solution concentration is 5~15 g:100 ml.
A kind of described polycaprolactone changes with PTMC to polypropylene sorrel water resistance and compliance
Good method, step 2）In, in polycaprolactone list tridecyl ether and poly acrylic acid-poly trimethylene carbonate graft copolymer
The mol ratio of polyacrylic acid segment is 15~25:1.
A kind of described polycaprolactone changes with PTMC to polypropylene sorrel water resistance and compliance
Good method, step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- second
Base -1-（3- dimethylaminopropyls）Carbodiimide, condensing agent and in poly acrylic acid-poly trimethylene carbonate graft copolymer poly- third
The mol ratio of olefin(e) acid segment 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 polycaprolactone changes with PTMC to polypropylene sorrel water resistance and compliance
Good method, step 3）In, mass percent of the polycaprolactone list tridecyl ether in Modified Membrane is 2~3%, and solvent is used
Dimethyl sulfoxide (DMSO), mixture solution concentration is 25~30 g:100 ml.
Compared with prior art, its advantage is the present invention：
1st, a kind of described polycaprolactone and PTMC are improved to polypropylene sorrel water resistance and compliance
Method, using esterification, amidation process and blending three kinds of means, it is simple to operate, be easy to grasp；
2nd, described polyacrylic acid improvement film water resistance and compliance are enhanced.
Embodiment
Embodiment 1
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer
15.7 grams of polyacrylic acid are added in dry reactor（Molecular weight is 82000）, 9.1 grams of hydroxy-end capped polytrimethylenes
Carbonic ester monododecyl ether（Molecular weight is 2500）, 248 ml dimethyl sulfoxide (DMSO)s are added, 0.049 gram is addedN,N’- two rings
Under hexyl carbodiimide, inert atmosphere, in 27 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 caprolactone-PTMC dual graft copolymer
Added in dry reactor 12 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 6.5 grams it is amino-terminated
Polycaprolactone list tridecyl ether（Molecular weight is 2300）, 186 ml dimethyl sulfoxide (DMSO)s are added, 0.035 gram is addedN,N’- two
Under carbodicyclo hexylimide, inert atmosphere, in 26 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried, obtained
Object；
3）The preparation for the polypropylene sorrel that polycaprolactone is improved with PTMC
10 grams of poly acrylic acid-poly caprolactone-PTMC dual graft copolymers and 37 are added in dry reactor
Ml dimethyl sulfoxide solvents, it is another to add the polycaprolactone list tridecyl ether for accounting for Modified Membrane gross weight 2%（Molecular weight is 2300）,
Under inert atmosphere, mixed 50 minutes in 46 DEG C of stirrings, use the tape casting film forming, target is dried to obtain in 50 DEG C of vacuum drying chambers
Thing.
After tested：The surface contact angle and its elongation at break of object and water of the present invention respectively than improving before modified
11.9 ° and 9.7%.
Embodiment 2
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer
15 grams of polyacrylic acid are added in dry reactor（Molecular weight is 87000）, 8.5 grams of hydroxy-end capped polytrimethylene carbon
Acid esters monododecyl ether（Molecular weight is 2600）, 235 ml dimethyl sulfoxide (DMSO)s are added, 0.028 gram is addedN,N’- diisopropyl
Under base carbodiimide, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtains target
Thing；
2）The preparation of poly acrylic acid-poly caprolactone-PTMC dual graft copolymer
Added in dry reactor 12.1 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 6.4 grams it is amino-terminated
Polycaprolactone list tridecyl ether（Molecular weight is 2400）, 185 ml dimethyl sulfoxide (DMSO)s are added, 0.021 gram is addedN,N’-
Under DIC, inert atmosphere, in 29 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtained
To object；
3）The preparation for the polypropylene sorrel that polycaprolactone is improved with PTMC
9.9 grams of poly acrylic acid-poly caprolactone-PTMC dual graft copolymers and 36 are added in dry reactor
Ml dimethyl sulfoxide solvents, it is another to add the polycaprolactone list tridecyl ether for accounting for Modified Membrane gross weight 3%（Molecular weight is 2400）,
Under inert atmosphere, mixed 55 minutes in 48 DEG C of stirrings, use the tape casting film forming, target is dried to obtain in 50 DEG C of vacuum drying chambers
Thing.
After tested：The surface contact angle and its elongation at break of object and water of the present invention respectively than improving before modified
12.4 ° and 10.3%.
Embodiment 3
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer
15.5 grams of polyacrylic acid are added in dry reactor（Molecular weight is 93000）, 8.3 grams of hydroxy-end capped polytrimethylenes
Carbonic ester monododecyl ether（Molecular weight is 2700）, 239 ml dimethyl sulfoxide (DMSO)s are added, 0.041 gram of 3- ethyls -1- is added
（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 34 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 caprolactone-PTMC dual graft copolymer
Added in dry reactor 11.5 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 5.6 grams it is amino-terminated
Polycaprolactone list tridecyl ether（Molecular weight is 2400）, 173 ml dimethyl sulfoxide (DMSO)s are added, 0.028 gram of 3- second is added
Base -1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 32 DEG C of stirring reactions 4 days, terminating reaction, by filtering, thoroughly
Analyse, dry, obtain object；
3）The preparation for the polypropylene sorrel that polycaprolactone is improved with PTMC
9.5 grams of poly acrylic acid-poly caprolactone-PTMC dual graft copolymers and 35 are added in dry reactor
Ml dimethyl sulfoxide solvents, it is another to add the polycaprolactone list tridecyl ether for accounting for Modified Membrane gross weight 2%（Molecular weight is 2400）,
Under inert atmosphere, mixed 60 minutes in 50 DEG C of stirrings, use the tape casting film forming, target is dried to obtain in 50 DEG C of vacuum drying chambers
Thing.
After tested：The surface contact angle and its elongation at break of object and water of the present invention respectively than improving before modified
13.2 ° and 10.9%.
Claims (6)
1. a kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance,
It is characterized in that：The molecular weight of polyacrylic acid segment is 82000~93000 in Modified Membrane, PTMC segment
Molecular weight is 2500~2700, and the molecular weight of polycaprolactone segment is 2300~2400；Its modification method uses following steps：
1）The synthesis of poly acrylic acid-poly trimethylene carbonate graft copolymer：Added in dry reactor hydroxy-end capped
Under PTMC monododecyl ether, solvent, condensing agent and polyacrylic acid, inert atmosphere, in 27~34 DEG C of stirrings
Reaction 2~4 days, terminating reaction by filtering, dialysis, is dried, obtains object；
2）The synthesis of poly acrylic acid-poly caprolactone-PTMC dual graft copolymer：Added in dry reactor
Poly acrylic acid-poly trimethylene carbonate graft copolymer, amino-terminated polycaprolactone list tridecyl ether, solvent and condensation
Under agent, inert atmosphere, in 26~32 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, was dried, obtains target
Thing；
3）The preparation for the polypropylene sorrel that polycaprolactone is improved with PTMC：Poly- third is added in dry reactor
Olefin(e) acid-polycaprolactone-PTMC dual graft copolymer, polycaprolactone list tridecyl ether and solvent, indifferent gas
Under atmosphere, after 46~50 DEG C of stirrings are mixed 50~60 minutes, with the tape casting film forming and drying, object is obtained.
2. a kind of polycaprolactone according to claim 1 and PTMC are to polypropylene sorrel water resistance and soft
The pliable method improved, it is characterised in that：Step 1）In, PTMC monododecyl ether and polyacrylic acid
Mol ratio be 15~25:1.
3. a kind of polycaprolactone according to claim 1 and PTMC to polypropylene sorrel water resistance and
The method that compliance is improved, it is characterised in that：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
For 1.06~1.9:1, solvent uses dimethyl sulfoxide (DMSO), and reactant solution concentration is 5~15 g:100 ml.
4. a kind of polycaprolactone according to claim 1 and PTMC are to polypropylene sorrel water resistance and soft
The pliable method improved, it is characterised in that：Step 2）In, polycaprolactone list tridecyl ether and poly acrylic acid-poly Sanya
The mol ratio of polyacrylic acid segment is 15~25 in methyl carbonic acid ester graft copolymer:1.
5. a kind of polycaprolactone according to claim 1 and PTMC to polypropylene sorrel water resistance and
The method that compliance is improved, it is characterised in that：Step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N, N’- DIC or 3- ethyls -1-（3- dimethylaminopropyls）Carbodiimide, condensing agent and poly acrylic acid-poly Sanya
The mol ratio of polyacrylic acid segment is 1.06~1.9 in methyl carbonic acid ester graft copolymer:1, solvent uses dimethyl sulfoxide (DMSO), instead
It is 5~15 g to answer thing solution concentration:100 ml.
6. a kind of polycaprolactone according to claim 1 and PTMC are to polypropylene sorrel water resistance and soft
The pliable method improved, it is characterised in that：Step 3）In, quality hundred of the polycaprolactone list tridecyl ether in Modified Membrane
Divide than being 2~3%, solvent uses dimethyl sulfoxide (DMSO), mixture solution concentration is 25~30 g:100 ml.
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| CN201710376551.1A CN107011680A (en) | 2017-05-25 | 2017-05-25 | A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance |
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| CN201710376551.1A CN107011680A (en) | 2017-05-25 | 2017-05-25 | A kind of method that polycaprolactone is improved with PTMC to polypropylene sorrel water resistance and compliance |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104559216A (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 polyacrylic acid |
| CN105542481A (en) * | 2016-03-16 | 2016-05-04 | 山东理工大学 | Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone |
| CN105647195A (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 polytrimethylene carbonate and polycaprolactone |
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- 2017-05-25 CN CN201710376551.1A patent/CN107011680A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104559216A (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 polyacrylic acid |
| CN105647195A (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 polytrimethylene carbonate and polycaprolactone |
| CN105542481A (en) * | 2016-03-16 | 2016-05-04 | 山东理工大学 | Method for modifying water resistance and flexibility of polyvinyl alcohol membrane through poly(trimethylene carbonate) and polycaprolactone |
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