CN106589289A - Thermal reversible self-repairing polyurethane-imide film and preparation method thereof - Google Patents
Thermal reversible self-repairing polyurethane-imide film and preparation method thereof Download PDFInfo
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- CN106589289A CN106589289A CN201611159022.8A CN201611159022A CN106589289A CN 106589289 A CN106589289 A CN 106589289A CN 201611159022 A CN201611159022 A CN 201611159022A CN 106589289 A CN106589289 A CN 106589289A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/343—Polycarboxylic acids having at least three carboxylic acid groups
- C08G18/346—Polycarboxylic acids having at least three carboxylic acid groups having four carboxylic acid groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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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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- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
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- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
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- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
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Abstract
The invention discloses a thermal reversible self-repairing polyurethane-imide film and a preparation method thereof. The preparation method comprises the following steps: (1) dissolving diisocyanate in an organic solvent, dripping polyester polyol in a nitrogen environment, adding a catalyst, and performing stirring and a reaction at the temperature of 60-80 DEG C for 2-4 hours so as to obtain a polyurethane prepolymer; (2) dissolving dianhydride in the organic solvent, mixing the mixture with the polyurethane prepolymer obtained in the step (1), and performing stirring and a reaction at the temperature of 60-80 DEG C for 3-5 hours so as to obtain a polyurethane-imide prepolymer; and (3) cooling the prepolymer obtained in the step (2) to room temperature, dropwise adding 2-hydroxyethyl disulfides into the prepolymer obtained in the step (2), performing a reaction for 2-24 hours, and pouring the product into a polyfluortetraethylene plate for film-forming after the reaction is ended, thereby obtaining the thermal reversible self-repairing polyurethane-imide film. Thermal reversible self-repairing of the polyurethane-imide film is realized by utilizing a disulfide bond transposition exchange reaction, the defect that the existing polyurethane is poor in heat resistance and mechanical property is overcome, and the thermal reversible self-repairing polyurethane-imide film has the characteristics of simple preparation process, high practicality, wide application and the like.
Description
Technical field
The present invention relates to compound polyurethane material technical field, more particularly, to a kind of thermal reversion selfreparing polyurethane-
Acid imide film and preparation method thereof.
Background technology
As modern industry and social life quickly develop, polyurethane has excellent corrosion resistance, wearability because of it
And the performance such as good low temperature elasticity, biocompatibility so as to more and more important effect is played in the modern life,
It is widely used in fields such as coating, adhesive, elastomer, biomaterials.But polyurethane because the characteristics of its own in molding or
Certain defect is easily caused during person's use, surface defect may be easily observed, but internal flaw be difficult to it is timely
It was found that so that the mechanical property degradation of material, and shorten the service life of material.If these defects can be by
Find in time and repair, the performance of material can be made out, greatly reducing potential safety hazard, while reducing unnecessary
The wasting of resources and property loss.Therefore, the ability of mimic biology body self-healing wound, using polyurethane selfreparing is carried out
Research is just arisen at the historic moment.
It is well known that polyurethane heat resistant is poor, 80 DEG C are usually no more than using temperature, more than 80 DEG C materials will soften,
Even deform, cause mechanical property to be decreased obviously, serious limits applications of the PU in high-temperature field.And polyimides are materials
Resistant to elevated temperatures " gold " material in field, it is compound with polyurethane to improve the thermostability of polyurethane, while its machine can also be improved
Tool performance.
The content of the invention
For problems of the prior art, it is an object of the invention to provide a kind of thermal reversion selfreparing polyurethane-
Acid imide film and preparation method thereof, using cystine linkage transposition exchange reaction the thermal reversion selfreparing of polyurethane-imide film is realized,
The defect of existing polyurethane heat resistant and bad mechanical property is solved simultaneously.
For achieving the above object, the technical solution adopted in the present invention is:A kind of thermal reversion selfreparing polyurethane-imide
The preparation method of film, comprises the following steps:
Step (1):Diisocyanate is dissolved in organic solvent, and Deca PEPA in a nitrogen environment, and add
Enter catalyst, stirring reaction 2~4 hours, obtain base polyurethane prepolymer for use as at a temperature of 60~80 DEG C;
Step (2):Dianhydride is dissolved in organic solvent, and is mixed with gained base polyurethane prepolymer for use as in step (1), 60~
Stirring reaction 3~5 hours at a temperature of 80 DEG C, obtain polyurethane-imide performed polymer;
Step (3):Gained performed polymer is cooled to room temperature in step (2), and 2- HEDSs are added dropwise over into step
(2) in gained performed polymer, react 2~24 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion
Selfreparing polyurethane-imide film.
A kind of thermal reversion selfreparing polyurethane-imide film, by thermal reversion selfreparing polyurethane-imide described above
It is prepared by the preparation method of film.
The polyurethane-imide thermal reversion selfreparing mechanism of the present invention is as shown in Figure 1.
The beneficial effects of the present invention is:The present invention reaches thermal reversion selfreparing using cystine linkage transposition exchange reaction, solves
Polyurethane determine when internal factor or external damage is suffered, selfreparing has been carried out in time, played its excellent properties, reduced safety
Hidden danger, reduces the wasting of resources and property loss, meanwhile, imide ring structure is introduced in polyurethane, make in polyurethane molecular chain
Not only contain flexible polyurethane hard section but also have rigid imide ring structure, the significant thermostability and mechanical performance for improving polyurethane,
And preparation process is simple, it is practical.
Description of the drawings
Fig. 1 is polyurethane-imide thermal reversion selfreparing mechanism figure.
Specific embodiment
Describe the present invention with reference to specific embodiment, the description of this part is only exemplary and explains
Property, there should not be any restriction effect to protection scope of the present invention.
The preparation method of the thermal reversion selfreparing polyurethane-imide film of the present invention, comprises the following steps:
Step (1):Diisocyanate is dissolved in organic solvent, and Deca PEPA in a nitrogen environment, and add
Enter catalyst, stirring reaction 2~4 hours, obtain base polyurethane prepolymer for use as at a temperature of 60~80 DEG C;
Step (2):Dianhydride is dissolved in organic solvent, and is mixed with gained base polyurethane prepolymer for use as in step (1), 60~
Stirring reaction 3~5 hours at a temperature of 80 DEG C, obtain polyurethane-imide performed polymer;
Step (3):Gained performed polymer is cooled to room temperature in step (2), and 2- HEDSs are added dropwise over into step
(2) in gained performed polymer, react 2~24 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion
Selfreparing polyurethane-imide film.
In above-mentioned technical proposal, in the step (1), first by PEPA vacuum dehydration at a temperature of 120~130 DEG C
1~2 hour, and be cooled to after room temperature, add in reaction system and reacted.
Preferably, in the diisocyanate in-NCO and PEPA-ratio of the amount of the material of OH is 2.1:1;
The dianhydride added in the step (2) is 7 with the ratio of the amount of the material of 2- HEDSs in step (3):3~3:7.
Preferably, 2- HEDSs are added dropwise in the step (3), and are reacted at room temperature.
Preferably, the diisocyanate is that toluene di-isocyanate(TDI), isophorone diisocyanate, diphenyl methane two are different
The mixture of one kind or many persons in cyanate, hexamethylene diisocyanate.
Preferably, the PEPA is in PCDL, polybutylene glyool adipate, polypropylene glycol
The mixture of one or both.
Preferably, described dianhydride be 3,3', 4,4'--- benzophenone tetracarboxylic dianhydrides, pyromellitic dianhydride in one kind or
Two kinds.
Preferably, the catalyst is dibutyl tin laurate, the amount that the catalyst is added for gross mass 0.1~
0.2%.
Preferably, the organic solvent is DMF, N,N-dimethylacetamide, N- methyl -2- pyrroles
One kind in alkanone, dimethyl sulfoxide, tetrahydrofuran.
A kind of thermal reversion selfreparing polyurethane-imide film, by thermal reversion selfreparing polyurethane-imide described above
It is prepared by the preparation method of film.
Embodiment 1:
(1) 8.1 parts of isoflurane chalcone diisocyanates are dissolved in 30 parts of DMF solvents, and in nitrogen ring
17.4 parts of PEPAs of Deca under border, and 0.01 part of dibutyl tin laurate is added, stirring reaction 2 is little at a temperature of 80 DEG C
When, obtain base polyurethane prepolymer for use as;
(2) by 3.9 part 3,3', 4,4'--- benzophenone tetracarboxylic dianhydrides are dissolved in 39.6 parts of DMF solvents,
And mix with gained base polyurethane prepolymer for use as in step (1), stirring reaction 3 hours, obtain polyurethane-imide at a temperature of 80 DEG C
Performed polymer;
(3) gained performed polymer is cooled to room temperature in step (2), and 0.8 part of 2- HEDS is added dropwise over into step
(2) in gained performed polymer, react 2 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion and review one's lessons by oneself
Multiple polyurethane-imide film.
Embodiment 2:
(1) 8.2 parts of isoflurane chalcone diisocyanates are dissolved in 35 parts of DMF solvents, and in nitrogen ring
17.5 parts of PEPAs of Deca under border, and 0.01 part of dibutyl tin laurate is added, stirring reaction 3 is little at a temperature of 70 DEG C
When, obtain base polyurethane prepolymer for use as;
(2) by 2.8 part 3,3', 4,4'--- benzophenone tetracarboxylic dianhydrides are dissolved in 35 parts of DMF solvents, and
Mix with gained base polyurethane prepolymer for use as in step (1), stirring reaction 3 hours, obtain polyurethane-imide pre- at a temperature of 70 DEG C
Aggressiveness;
(3) gained performed polymer is cooled to room temperature in step (2), and 1.4 parts of 2- HEDSs are added dropwise over into step
(2) in gained performed polymer, react 3 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion and review one's lessons by oneself
Multiple polyurethane-imide film.
Embodiment 3:
(1) 8.2 parts of isoflurane chalcone diisocyanates are dissolved in 35 parts of DMF solvents, and in nitrogen ring
17.6 parts of PEPAs of Deca under border, and 0.01 part of dibutyl tin laurate is added, stirring reaction 3 is little at a temperature of 60 DEG C
When, obtain base polyurethane prepolymer for use as;
(2) by 2.7 part 3,3', 4,4'--- benzophenone tetracarboxylic dianhydrides are dissolved in 35 parts of DMF solvents, and
Mix with gained base polyurethane prepolymer for use as in step (1), stirring reaction 3 hours, obtain polyurethane-imide pre- at a temperature of 70 DEG C
Aggressiveness;
(3) gained performed polymer is cooled to room temperature in step (2), and 2.3 parts of 2- HEDSs are added dropwise over into step
(2) in gained performed polymer, react 4 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion and review one's lessons by oneself
Multiple polyurethane-imide film.
Embodiment 4:
(1) 8.2 parts of isoflurane chalcone diisocyanates are dissolved in 35 parts of DMF solvents, and in nitrogen ring
17.6 parts of PEPAs of Deca under border, and 0.01 part of dibutyl tin laurate is added, stirring reaction 3 is little at a temperature of 80 DEG C
When, obtain base polyurethane prepolymer for use as;
(2) by 1.7 part 3,3', 4,4'--- benzophenone tetracarboxylic dianhydrides are dissolved in 35 parts of DMF solvents, and
Mix with gained base polyurethane prepolymer for use as in step (1), stirring reaction 3 hours, obtain polyurethane-imide pre- at a temperature of 60 DEG C
Aggressiveness;
(3) gained performed polymer is cooled to room temperature in step (2), and 1.9 parts of 2- HEDSs are added dropwise over into step
(2) in gained performed polymer, react 2 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion and review one's lessons by oneself
Multiple polyurethane-imide film.
Thermal reversion selfreparing polyurethane-imide prepared by the present invention is mainly used in membrane material, while can be used for
Coating, adhesive etc..
The above, is only presently preferred embodiments of the present invention, not makes any restriction to the technical scope of the present invention, therefore
Any trickle amendment, equivalent variations and modification that every technical spirit according to the present invention is made to above example, still belong to
In the range of technical scheme.
Claims (10)
1. a kind of preparation method of thermal reversion selfreparing polyurethane-imide film, it is characterised in that comprise the following steps:
Step (1):Diisocyanate is dissolved in organic solvent, and Deca PEPA in a nitrogen environment, and add and urge
Agent, stirring reaction 2~4 hours, obtain base polyurethane prepolymer for use as at a temperature of 60~80 DEG C;
Step (2):Dianhydride is dissolved in organic solvent, and is mixed with gained base polyurethane prepolymer for use as in step (1), at 60~80 DEG C
At a temperature of stirring reaction 3~5 hours, obtain polyurethane-imide performed polymer.
Step (3):Gained performed polymer is cooled to room temperature in step (2), and 2- HEDSs are added dropwise in step (2)
In gained performed polymer, react 2~24 hours, reaction pours film forming in polyfluortetraethylene plate into after terminating, that is, obtain thermal reversion and review one's lessons by oneself
Multiple polyurethane-imide film.
2. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
In step (1), first by PEPA at a temperature of 120~130 DEG C vacuum dehydration 1~2 hour, and be cooled to after room temperature, then
Add and reacted in reaction system.
3. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
In diisocyanate-NCO and PEPA in-ratio of the amount of the material of OH is 2.1:1;Add in the step (2)
Dianhydride is 7 with the ratio of the amount of the material of 2- HEDSs in step (3):3~3:7.
4. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
2- HEDSs are added dropwise in step (3), and are reacted at room temperature.
5. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
Diisocyanate is that toluene di-isocyanate(TDI), isophorone diisocyanate, methyl diphenylene diisocyanate, hexa-methylene two are different
The mixture of one kind or many persons in cyanate.
6. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
PEPA is the mixture of one or both of PCDL, polybutylene glyool adipate, polypropylene glycol.
7. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
Dianhydride is 3,3', one or two in 4,4'--- benzophenone tetracarboxylic dianhydrides, pyromellitic dianhydride.
8. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
Catalyst is dibutyl tin laurate, and the amount that it is added is 0.1~0.2% of reactant gross mass in the step (1).
9. the preparation method of thermal reversion selfreparing polyurethane-imide film as claimed in claim 1, it is characterised in that:It is described
Organic solvent is N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, METHYLPYRROLIDONE, dimethyl sulfoxide, tetrahydrochysene
One kind in furan.
10. a kind of thermal reversion selfreparing polyurethane-imide film, it is characterised in that:By described in claim 1~9 any one
Thermal reversion selfreparing polyurethane-imide film preparation method prepare.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109988281A (en) * | 2019-04-24 | 2019-07-09 | 陕西科技大学 | A kind of preparation method of the hydrophobic performance containing disulfide bond and the dual selfreparing no-solvent polyurethane of mechanical property |
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