CN106977944A - A kind of method that poly (lactic acid-glycolic acid) is improved with PTMC to polypropylene sorrel water resistance and compliance - Google Patents
A kind of method that poly (lactic acid-glycolic acid) is improved with PTMC to polypropylene sorrel water resistance and compliance Download PDFInfo
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- CN106977944A CN106977944A CN201710376534.8A CN201710376534A CN106977944A CN 106977944 A CN106977944 A CN 106977944A CN 201710376534 A CN201710376534 A CN 201710376534A CN 106977944 A CN106977944 A CN 106977944A
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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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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- 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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- 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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- 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 poly (lactic acid-glycolic acid) 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 poly (lactic acid-glycolic acid) list tridecyl ether, solvent and condensing agent are added in dry reactor, reacts 2~4 days, obtains polyacrylic acid poly (lactic acid-glycolic acid) PTMC dual graft copolymer；3）Dual graft copolymer, poly (lactic acid-glycolic acid) 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.It is poly-（D,L）Y（Lactic acid is 90/10 with glycolic mol ratio）With poly- three methylene
Base carbonic ester is the biomaterial with excellent biocompatibility and biodegradability, with good hydrophobicity and submissive
Property.First PTMC segment is grafted on polyacrylic acid strand and obtains poly acrylic acid-poly trimethylene carbonic acid
Ester graft copolymer, then poly (lactic acid-glycolic acid) segment is grafted in poly acrylic acid-poly trimethylene carbonate graft copolymer
Polyacrylic acid segment on form poly acrylic acid-poly y-PTMC dual graft copolymer, Ran Houzai
Poly (lactic acid-glycolic acid) segment is added into poly acrylic acid-poly y-PTMC dual graft copolymer to be formed
Blend, is made modified polypropene sorrel, so as to drastically increase the water resistance and compliance of polypropylene sorrel.
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：
The side that a kind of poly (lactic acid-glycolic acid) is improved with PTMC to polypropylene sorrel water resistance and compliance
Method, it is characterised in that：The molecular weight of polyacrylic acid segment is 82000~93000, PTMC segment in Modified Membrane
Molecular weight be 2600~2800, the molecular weight of poly (lactic acid-glycolic acid) segment is 2300~2400；Its method of modifying is using following
Step：
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 28~33 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 y-PTMC dual graft copolymer：In dry reactor
Add poly acrylic acid-poly trimethylene carbonate graft copolymer, it is amino-terminated poly (lactic acid-glycolic acid) list tridecyl ether, molten
Under agent and condensing agent, inert atmosphere, in 27~31 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, was dried, obtained
To object；
3）The preparation for the polypropylene sorrel that poly (lactic acid-glycolic acid) is improved with PTMC：Added in dry reactor
Poly acrylic acid-poly y-PTMC dual graft copolymer, poly (lactic acid-glycolic acid) list tridecyl ether and
Under solvent, inert atmosphere, after 48~51 DEG C of stirrings are mixed 50~60 minutes, with the tape casting film forming and drying, object is obtained.
A kind of described poly (lactic acid-glycolic acid) enters with PTMC to polypropylene sorrel water resistance and compliance
The method of row improvement, step 1）In, the mol ratio of PTMC monododecyl ether and polyacrylic acid is 15~25:
1。
A kind of described poly (lactic acid-glycolic acid) enters with PTMC to polypropylene sorrel water resistance and compliance
The method of row improvement, 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 is 1.06~1.9:1, solvent is adopted
With dimethyl sulfoxide (DMSO), reactant solution concentration is 5~15 g:100 ml.
A kind of described poly (lactic acid-glycolic acid) enters with PTMC to polypropylene sorrel water resistance and compliance
The method of row improvement, step 2）In, poly (lactic acid-glycolic acid) list tridecyl ether is using poly-（D,L）Y list tridecyl
Ether (lactic acid is 90/10 with glycolic mol ratio), poly (lactic acid-glycolic acid) list tridecyl ether and poly acrylic acid-poly trimethylene carbon
The mol ratio of polyacrylic acid segment is 15~25 in acid esters graft copolymer:1.
A kind of described poly (lactic acid-glycolic acid) enters with PTMC to polypropylene sorrel water resistance and compliance
The method of row improvement, step 2）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or
3- ethyls -1-（3- dimethylaminopropyls）In carbodiimide, condensing agent and poly acrylic acid-poly trimethylene carbonate graft copolymer
The mol ratio of polyacrylic 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 poly (lactic acid-glycolic acid) enters with PTMC to polypropylene sorrel water resistance and compliance
The method of row improvement, step 3）In, poly (lactic acid-glycolic acid) list tridecyl ether is using poly-（D,L）Y list tridecyl
Ether (lactic acid is 90/10 with glycolic mol ratio), mass percent of the poly (lactic acid-glycolic acid) list tridecyl ether in Modified Membrane
For 2~3%, solvent uses dimethyl sulfoxide (DMSO), and mixture solution concentration is 25~30 g:100 ml.
Compared with prior art, its advantage is the present invention：
1st, a kind of described poly (lactic acid-glycolic acid) and PTMC are carried out to polypropylene sorrel water resistance and compliance
The method of improvement, 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）, 9.2 grams of hydroxy-end capped polytrimethylenes
Carbonic ester monododecyl ether（Molecular weight is 2600）, 249 ml dimethyl sulfoxide (DMSO)s are added, 0.049 gram is addedN,N’- two rings
Under hexyl carbodiimide, inert atmosphere, in 28 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 y-PTMC dual graft copolymer
Added in dry reactor 12.1 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 6.5 grams it is amino-terminated
Poly (lactic acid-glycolic acid) list tridecyl ether（Molecular weight is 2300）, 186 ml dimethyl sulfoxide (DMSO)s are added, 0.036 gram is addedN, N’Under-dicyclohexylcarbodiimide, inert atmosphere, in 27 DEG C of stirring reactions 2 days, terminating reaction by filtering, dialysis, was dried,
Obtain object；
3）The preparation for the polypropylene sorrel that poly (lactic acid-glycolic acid) is improved with PTMC
10 grams of poly acrylic acid-poly y-PTMC dual graft copolymers are added in dry reactor
With 37 ml dimethyl sulfoxide solvents, another addition accounts for the poly (lactic acid-glycolic acid) list tridecyl ether of Modified Membrane gross weight 2%（Molecular weight
For 2300）, under inert atmosphere, in 48 DEG C of stirring mixing 50 minutes, the tape casting film forming is used, it is dry in 50 DEG C of vacuum drying chambers
To object.
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 9.3%.
Embodiment 2
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer
15.1 grams of polyacrylic acid are added in dry reactor（Molecular weight is 87000）, 8.8 grams of hydroxy-end capped polytrimethylenes
Carbonic ester monododecyl ether（Molecular weight is 2700）, 239 ml dimethyl sulfoxide (DMSO)s are added, 0.028 gram is addedN,N’- two is different
Under propyl group carbodiimide, inert atmosphere, in 30 DEG C of stirring reactions 3 days, terminating reaction by filtering, dialysis, was dried, obtains mesh
Mark thing；
2）The preparation of poly acrylic acid-poly y-PTMC dual graft copolymer
Added in dry reactor 12.2 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 6.4 grams it is amino-terminated
Poly (lactic acid-glycolic acid) 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,
Obtain object；
3）The preparation for the polypropylene sorrel that poly (lactic acid-glycolic acid) is improved with PTMC
9.9 grams of poly acrylic acid-poly y-PTMC dual graft copolymers are added in dry reactor
With 36 ml dimethyl sulfoxide solvents, another addition accounts for the poly (lactic acid-glycolic acid) list tridecyl ether of Modified Membrane gross weight 3%（Molecular weight
For 2400）, under inert atmosphere, in 49 DEG C of stirring mixing 55 minutes, the tape casting film forming is used, it is dry in 50 DEG C of vacuum drying chambers
To object.
After tested：The surface contact angle and its elongation at break of object and water of the present invention respectively than improving before modified
12.9 ° and 10.3%.
Embodiment 3
1）The preparation of poly acrylic acid-poly trimethylene carbonate graft copolymer
15.8 grams of polyacrylic acid are added in dry reactor（Molecular weight is 93000）, 8.5 grams of hydroxy-end capped polytrimethylenes
Carbonic ester monododecyl ether（Molecular weight is 2800）, 243 ml dimethyl sulfoxide (DMSO)s are added, 0.041 gram of 3- ethyls -1- is added
（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 33 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 y-PTMC dual graft copolymer
Added in dry reactor 11.6 grams of poly acrylic acid-poly trimethylene carbonate graft copolymers, 5.6 grams it is amino-terminated
Poly (lactic acid-glycolic acid) list tridecyl ether（Molecular weight is 2400）, 173 ml dimethyl sulfoxide (DMSO)s are added, 0.028 gram of 3- is added
Ethyl -1-（3- dimethylaminopropyls）Under carbodiimide, inert atmosphere, in 31 DEG C of stirring reactions 4 days, terminating reaction, by filtering,
Dialyse, dry, obtain object；
3）The preparation for the polypropylene sorrel that poly (lactic acid-glycolic acid) is improved with PTMC
9.5 grams of poly acrylic acid-poly y-PTMC dual graft copolymers are added in dry reactor
With 35 ml dimethyl sulfoxide solvents, another addition accounts for the poly (lactic acid-glycolic acid) list tridecyl ether of Modified Membrane gross weight 2%（Molecular weight
For 2400）, under inert atmosphere, in 51 DEG C of stirring mixing 60 minutes, the tape casting film forming is used, it is dry in 50 DEG C of vacuum drying chambers
To object.
After tested：The surface contact angle and its elongation at break of object and water of the present invention respectively than improving before modified
13.6 ° and 11.5%.
Claims (6)
- What 1. a kind of poly (lactic acid-glycolic acid) was improved with PTMC to polypropylene sorrel water resistance and compliance Method, it is characterised in that：The molecular weight of polyacrylic acid segment is 82000~93000, PTMC chain in Modified Membrane The molecular weight of section is 2600~2800, and the molecular weight of poly (lactic acid-glycolic acid) segment is 2300~2400；Its modification method use with Lower step：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 28~33 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 y-PTMC dual graft copolymer：In dry reactor Add poly acrylic acid-poly trimethylene carbonate graft copolymer, it is amino-terminated poly (lactic acid-glycolic acid) list tridecyl ether, molten Under agent and condensing agent, inert atmosphere, in 27~31 DEG C of stirring reactions 2~4 days, terminating reaction by filtering, dialysis, was dried, obtained To object；3）The preparation for the polypropylene sorrel that poly (lactic acid-glycolic acid) is improved with PTMC：Added in dry reactor Poly acrylic acid-poly y-PTMC dual graft copolymer, poly (lactic acid-glycolic acid) list tridecyl ether and Under solvent, inert atmosphere, after 48~51 DEG C of stirrings are mixed 50~60 minutes, with the tape casting film forming and drying, object is obtained.
- 2. a kind of poly (lactic acid-glycolic acid) according to claim 1 is with PTMC to polypropylene sorrel water resistance And the method that compliance is improved, it is characterised in that：Step 1）In, PTMC monododecyl ether and poly- third The mol ratio of olefin(e) acid is 15~25:1.
- 3. a kind of poly (lactic acid-glycolic acid) according to claim 1 and PTMC are water-fast to polypropylene sorrel The method that property and compliance are improved, it is characterised in that：Step 1）In, condensing agent is usedN,N’- dicyclohexylcarbodiimide,N,N’- DIC or 3- ethyls -1-（3- dimethylaminopropyls）Mole of carbodiimide, condensing agent and polyacrylic acid Than 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 poly (lactic acid-glycolic acid) according to claim 1 is with PTMC to polypropylene sorrel water resistance And the method that compliance is improved, it is characterised in that：Step 2）In, poly (lactic acid-glycolic acid) list tridecyl ether is using poly-（D, L）Y list tridecyl ether (lactic acid is 90/10 with glycolic mol ratio), poly (lactic acid-glycolic acid) list tridecyl ether Mol ratio with polyacrylic acid segment in poly acrylic acid-poly trimethylene carbonate graft copolymer is 15~25:1.
- 5. a kind of poly (lactic acid-glycolic acid) according to claim 1 and PTMC are water-fast to polypropylene sorrel The method that property and compliance are 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 three The mol ratio of polyacrylic acid segment is 1.06~1.9 in carbonate graft copolymer:1, solvent uses dimethyl sulfoxide (DMSO), Reactant solution concentration is 5~15 g:100 ml.
- 6. a kind of poly (lactic acid-glycolic acid) according to claim 1 is with PTMC to polypropylene sorrel water resistance And the method that compliance is improved, it is characterised in that：Step 3）In, poly (lactic acid-glycolic acid) list tridecyl ether is using poly-（D, L）Y list tridecyl ether (lactic acid is 90/10 with glycolic mol ratio), poly (lactic acid-glycolic acid) list tridecyl ether Mass percent in Modified Membrane is 2~3%, and solvent uses dimethyl sulfoxide (DMSO), and mixture solution concentration is 25~30 g:100 ml。
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| CN201710376534.8A CN106977944A (en) | 2017-05-25 | 2017-05-25 | A kind of method that poly (lactic acid-glycolic acid) 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 |
|---|---|---|---|---|
| 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) |
| CN105542479A (en) * | 2016-03-07 | 2016-05-04 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(p-dioxanone) and poly lactic acid-glycolic acid |
| 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 |
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- 2017-05-25 CN CN201710376534.8A patent/CN106977944A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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) |
| CN105542479A (en) * | 2016-03-07 | 2016-05-04 | 山东理工大学 | Method for improving water resistance and flexibility of polyvinyl alcohol film through poly(p-dioxanone) and poly lactic acid-glycolic acid |
| 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 |
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Application publication date: 20170725 |