CN106832172A - A kind of light heat response at different level shape-memory polymer and its preparation method and application - Google Patents
A kind of light heat response at different level shape-memory polymer and its preparation method and application Download PDFInfo
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- CN106832172A CN106832172A CN201611234855.6A CN201611234855A CN106832172A CN 106832172 A CN106832172 A CN 106832172A CN 201611234855 A CN201611234855 A CN 201611234855A CN 106832172 A CN106832172 A CN 106832172A
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- shape
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3836—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing azo groups
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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
- C08G2280/00—Compositions for creating shape memory
Abstract
The present invention is applied to intelligent macromolecule material field, there is provided a kind of light heat response at different level shape-memory polymer and its preparation method and application.The light heat response at different level shape-memory polymer is polymerized by monomer A, monomer B and monomer C；Wherein, the structural formula of monomer A isMonomer B is hexamethylene diisocyanate, and monomer C is N methyl diethanolamines.The light heat response at different level shape-memory polymer that the present invention is provided has unique light heat response at different level SME, has independent DEFORMATION RESPONSE to ultraviolet light and thermostimulation respectively.
Description
Technical field
The invention belongs to intelligent macromolecule material field, more particularly to a kind of light heat response at different level shape-memory polymer
And its preparation method and application.
Background technology
In research of the nearest decades to shape-memory polymer (SMPs), thermo-stimulative shape memory polymer material
(TSMPs) research is developed on a large scale very much with application.But TSMPs is difficult to realize remote control, need directly to be lured by heating
Lead material phase transformation to realize deformation, this causes that applications of the TSMPs in shielding system and noncontact system is very limited.Separately
On the one hand, because light stimulus has the excellent characteristic such as the feature of environmental protection, remote controllability, instantaneity, photic SMPs is subject to researcher
Great attention.It is unique excellent that there is photic SMPs noncontact to regulate and control deformation, fixed point regulation and control deformation and quick, cleaning regulation and control deformation etc.
Gesture, and luminous energy can be directly translated into mechanical energy, improve the utilization ratio of light.However, the SMPs of common light stimulus to light according to
Lai Xingqiang, deforms when having illumination, and deformation recovers during no light, it is impossible to fixed temporary shapes.In addition, in order to further open up
Open up the multifunction and practical ranges of SMPs, the research of SMPs is increasingly biased toward both at home and abroad realize multiple response and
Multiple shape memory effect.However, current multiple shape memory effect is all can anti-phase or use by temperature control multiple
The Glass Transition of wide scope realizes triple or multiple shape memory as reversible equivalent way, and this is limited to by temperature.
It is by electrically or optically acting on lower produced heat come the triple shape-memory properties realized, still falling within after all to have some researchs
The triple SMEs of single thermic.
Therefore, the prior art is defective, it is necessary to improve.
The content of the invention
In order to solve the above technical problems, the invention provides a kind of light heat response at different level shape-memory polymer and its system
Preparation Method and application, it is intended to improve the fixed effect of the temporary shapes of existing shape-memory polymer, develop the fixation of its shape
Controllability, so as to realize the development and application of multifunction SMPs.
The present invention is achieved in that a kind of light heat response at different level shape-memory polymer, the light heat response at different level
Shape-memory polymer is polymerized by monomer A, monomer B and monomer C；
Wherein, the structural formula of monomer A isMonomer B is the isocyanide of hexa-methylene two
Acid esters, monomer C is N methyldiethanol amine.
Present invention also offers the preparation method of above-mentioned light heat response at different level shape-memory polymer, comprise the following steps：
Monomer A and monomer B are carried out into polymerisation, the shape-memory polymer pre-polymerization containing azobenzene structure unit is obtained
Body；
Monomer C and monomer B are added in the shape-memory polymer performed polymer, the shape of the HMW is obtained
Memory polymer.
Compared with prior art, beneficial effect is the present invention：Light heat response at different level shape provided in an embodiment of the present invention
Memory polymer, the polymer of shape memory and alteration of form is constructed using the photic configurational isomerization change of azobenzene molecule
Macromolecular material.Thus obtained light heat response at different level shape-memory polymer has unique light heat response at different level shape note
Recall effect, there is independent DEFORMATION RESPONSE to ultraviolet light and thermostimulation respectively.Under ultraviolet light, the shape-memory polymer
Can actively deform；After ultraviolet light revocation, under normal temperature and visible light environment, deformation keeps constant, obtains temporary shapes；When
Using thermostimulation, rise when more than high-temperature to the glass transition temperature of shape-memory polymer, the shape-memory polymer can be led
It is dynamic to recover deformation, return to original shape from temporary shapes.
Brief description of the drawings
Fig. 1 be the LHSMPU prepared by the embodiment of the present invention 2 light heat response at different level change in shape and recovery process in show
It is intended to；
Fig. 2 is the azobenzene knot of LHSMPU prepared by the embodiment of the present invention 3 under the ultraviolet Photic Stimulation of different time
Structure cellular construction change schematic diagram.
Specific embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, it is right below in conjunction with drawings and Examples
The present invention is further elaborated.It should be appreciated that specific embodiment described herein is only used to explain the present invention, not
For limiting the present invention.
First embodiment of the invention provides a kind of light heat response at different level shape-memory polymer, and the light heat classification rings
Shape-memory polymer is answered to be polymerized by monomer A, monomer B and monomer C；
Wherein, the structural formula of monomer A isMonomer B is the isocyanide of hexa-methylene two
Acid esters, monomer C is N methyldiethanol amine.
The light heat response at different level shape-memory polymer that first embodiment of the invention is provided, with azoaromatic diacid, six Asias
Methyl diisocyanate and N methyldiethanol amine are polymerized.It is first different with part hexa-methylene two by azoaromatic diacid respectively
There is sudden reaction in cyanate, construct azobenzene soft section chain under catalyst action；It is sub- with remaining six by N methyldiethanol amine
There is sudden reaction in methyl diisocyanate, construct N methyldiethanol amine hard section phase under catalyst action；Then, azobenzene
Soft section chain is connected with N methyldiethanol amine hard section by chemical bond, and the photic configurational isomerization using azobenzene molecule changes
To construct the polymeric material of shape memory and alteration of form.Thus obtained light heat response at different level shape memory gathers
Compound has unique light heat response at different level SME, and there is independent deformation to ring to ultraviolet light and thermostimulation respectively
Should.
Referring to Fig. 1, under ultraviolet light, the shape-memory polymer can actively deform；After ultraviolet light revocation,
Under normal temperature and visible light environment, deformation keeps constant, obtains temporary shapes；When thermostimulation is used, high-temperature to shape memory is risen
When more than the glass transition temperature of polymer, the shape-memory polymer can actively recover deformation, be returned to just from temporary shapes
Beginning shape.
Specifically, the structural formula of the shape-memory polymer is as follows：
Wherein, n >=10, m >=10.The light heat response at different level shape-memory polymer that first embodiment of the invention is provided,
Azobenzene structure unit introduces polyurethane backbone, with photoresponse function.Segmented polyurethane recovers to provide physical crosslinking for thermic
Point, under thermal stimulation effect, recurring structure change causes backbone motion to azobenzene structure, elasticity occurs and recovers, and returns to initial
State.
Specifically, the mass ratio of the monomer A, monomer B and monomer C is (10~20):(30~40):(40~60).It is logical
Regulation and control monomer A, the consumption of monomer B and monomer C are crossed, the weight/mass percentage composition for making monomer A in the shape-memory polymer is
The weight/mass percentage composition of 10wt%~20wt%, monomer C is 30wt%~40wt%, and the weight/mass percentage composition of monomer B is
40wt%~60wt%.So as to deflection of the content realization to the photoresponse of the shape-memory polymer by regulating and controlling monomer A
Control；By regulating and controlling B, C content realizes the control of the temperature-responsive scope of the thermal response of the shape-memory polymer.
Specifically, monomer B includes at least one in aliphatic diisocyanate.The monomer C includes N- methyl diethyls
Hydramine, at least one in N- methyl dimethoxy hydramine.
Specifically, in the NCO molal quantity b and monomer C in carboxyl molal quantity a, the monomer B in the monomer A
Hydroxyl moles c meets following relation：
The span of r=b/ (a+c), r is 0.95~1.05.
By limiting the NCO molal quantity b in carboxyl molal quantity a, monomer B in monomer A and the hydroxyl in monomer C
The quantitative relation of base molal quantity c, makes the number-average molecular weight of the shape-memory polymer being polymerized more than 5000, so that the shape
Shape memory polymer has preferable moulding property.
Specifically, the glass transition temperature of the light heat response at different level shape-memory polymer is 30~90 DEG C.By adjusting
The content of monomer A, B, C in the shape-memory polymer is controlled, polyurethane glass conversion temperature is maintained at 30~90 DEG C.
Second embodiment of the invention provides a kind of preparation method of above-mentioned light heat response at different level shape-memory polymer,
Comprise the following steps：
Monomer A and monomer B are carried out into polymerisation, the shape-memory polymer pre-polymerization containing azobenzene structure unit is obtained
Body；
Monomer C and monomer B are added in the shape-memory polymer performed polymer, the shape of the HMW is obtained
Memory polymer.
The preparation method of the light heat response at different level shape-memory polymer that second embodiment of the invention is provided, with azobenzene
Dicarboxylic acids, diisocyanate and N methyldiethanol amine are raw material, carry out polymerization synthesis.Azoaromatic diacid and part two first
Isocyanates alternating copolymerization, constructs azobenzene soft section chain, and the azoaromatic diacid is with the catalyst of di-isocyanate reaction
Dibutyl tin laurate；N methyldiethanol amine and remaining diisocyanate alternating copolymerization again, construct azobenzene hard section phase,
Azobenzene soft section chain is connected with azobenzene hard section by chemical bond, using azobenzene molecule photic configurational isomerization change come
Construct the polymeric material of shape memory and alteration of form.
Specifically, the chemical structural formula of the shape-memory polymer performed polymer is as follows：
Wherein n >=10.
The preparation method of the light heat response at different level shape-memory polymer that second embodiment of the invention is provided, is derived from
The chemical structural formula of light heat response at different level shape-memory polymer be：The preparation method process letter
It is single, it is adapted to large-scale production.
Third embodiment of the invention provides a kind of application of above-mentioned light heat response at different level shape-memory polymer, described
Using for by the light heat response at different level shape-memory polymer be used for prepare intelligent nano device, intellectual drug controlled release agent or
Intelligence sensor.
Third embodiment of the invention is applied azobenzene compound as the group of photoresponse in luminous energy conversion machinery fortune
In dynamic device or preparation, it is with a wide range of applications.
Technical scheme is described further below in conjunction with specific embodiment.
Embodiment 1
0.37g 4,4'- azoaromatic diacids, the dissolving of 10.0g N, N'- dimethylformamide are added in there-necked flask；
1.5g hexamethylene diisocyanates, 0.6mL dibutyl tin laurates, 80 DEG C of reaction 30min are then added dropwise；It is subsequently adding
1.96g N methyldiethanol amines, 1.5g hexamethylene diisocyanates, 80 DEG C are reacted 30min again；After question response terminates, will be molten
Liquid is poured into Teflon mould, and it is to obtain light heat response at different level shape memory to gather that 24h is dried in 80 DEG C of air dry ovens
Urethane (LHSMPU).Azobenzene structure unit introduces polyurethane backbone, with photoresponse function.Segmented polyurethane recovers for thermic
Physical crosslinking point is provided, azobenzene structure under thermal stimulation effect, also can recurring structure change, cause backbone motion, there is bullet
Property recover, return to original state.
Embodiment 2
0.54g 4,4'- azoaromatic diacids, the dissolving of 12.0g N, N'- dimethylformamide are added in there-necked flask；
1.5g hexamethylene diisocyanates, 0.6mL dibutyl tin laurates, 80 DEG C of reaction 30min are then added dropwise；It is subsequently adding
1.89g N methyldiethanol amines, 1.5g hexamethylene diisocyanates, 80 DEG C are reacted 30min again；After question response terminates, treat by
Solution is poured into Teflon mould, and it is to obtain light heat response at different level shape memory that 24h is dried in 80 DEG C of air dry ovens
Polyurethane (LHSMPU).Fig. 1 be prepared LHSMPU light heat response at different level change in shape and recovery process in schematic diagram.
It will be noted from fig. 1 that under ultraviolet light, polyurethane backbone is crimped, with photic shape distortion；Ultraviolet light stops
Afterwards, curly form keeps stabilization at room temperature, with excellent in shape fixing function.In temperature-rise period, no light stimulates, curl shape
Shape progressively returns to original planar condition, realizes that thermic shape is recovered.
Embodiment 3
0.96g 4,4'- azoaromatic diacids, the dissolving of 15.0g N, N'- dimethylformamide are added in there-necked flask；
1.5g hexamethylene diisocyanates, 0.6mL dibutyl tin laurates, 80 DEG C of reaction 30min are then added dropwise；It is subsequently adding
1.69g N methyldiethanol amines, 1.5g hexamethylene diisocyanates, 80 DEG C are reacted 30min again；After question response terminates, treat by
Solution is poured into Teflon mould, and it is to obtain light heat response at different level shape memory that 24h is dried in 80 DEG C of air dry ovens
Polyurethane (LHSMPU).Fig. 2 has been tracked under the ultraviolet Photic Stimulation of different time using ultra-violet absorption spectrum, prepared
The change of azobenzene structure cellular construction in LHSMPU.As shown in Fig. 2 under ultraviolet Photic Stimulation, as ultraviolet light stimulus is made
With the increase of time, the π-π * electron transitions (transisomer) of nitrogen nitrogen double bond (- N=N-) inhales in azobenzene group at 362nm
Receiving peak intensity gradually reduces, and shows that azobenzene group is gradually changed into cis-isomer from transisomer；Pass through ultraviolet light
Stimulation, molecular structure there occurs change, and macroscopically material cashes out the deformation of curling.
Presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, it is all in essence of the invention
Any modification, equivalent and improvement made within god and principle etc., should be included within the scope of the present invention.
Claims (10)
1. a kind of light heat response at different level shape-memory polymer, it is characterised in that the light heat response at different level shape memory gathers
Compound is polymerized by monomer A, monomer B and monomer C；
Wherein, the structural formula of monomer A isMonomer B is hexamethylene diisocyanate,
Monomer C is N methyldiethanol amine.
2. light heat response at different level shape-memory polymer as claimed in claim 1, it is characterised in that the shape memory gathers
The structural formula of compound is as follows：
Wherein, n >=10, m >=10.
3. light heat response at different level shape-memory polymer as claimed in claim 1, it is characterised in that the monomer A, monomer B
And the mass ratio of monomer C is (10~20):(30~40):(40~60).
4. light heat response at different level shape-memory polymer as claimed in claim 1, it is characterised in that monomer B includes aliphatic
At least one in diisocyanate.
5. light heat response at different level shape-memory polymer as claimed in claim 1, it is characterised in that the monomer C includes N-
Methyl diethanolamine, at least one in N- methyl dimethoxy hydramine.
6. light heat response at different level shape-memory polymer as claimed in claim 1, it is characterised in that the carboxylic in the monomer A
The hydroxyl moles c in NCO molal quantity b and monomer C in base molal quantity a, monomer B meets following relation：
The span of r=b/ (a+c), r is 0.95~1.05.
7. light heat response at different level shape-memory polymer as claimed in claim 1, it is characterised in that the light heat classification rings
The glass transition temperature for answering shape-memory polymer is 30~90 DEG C.
8. the preparation method of the light heat response at different level shape-memory polymer as described in claim 1 to 7 any one, it is special
Levy and be, comprise the following steps：
Monomer A and monomer B are carried out into polymerisation, the shape-memory polymer performed polymer containing azobenzene structure unit is obtained；
Monomer C and monomer B are added in the shape-memory polymer performed polymer, the shape memory of the HMW is obtained
Polymer.
9. the preparation method of light heat response at different level shape-memory polymer as claimed in claim 8, it is characterised in that described
The catalyst that monomer A and monomer B carries out polymerisation is dibutyl tin laurate.
10. the application of the light heat response at different level shape-memory polymer as described in claim 1 to 7 any one, its feature exists
In the application is to be used to the light heat response at different level shape-memory polymer prepare intelligent nano device, intellectual drug control
Release agent or intelligence sensor.
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| CN107317041A (en) * | 2017-07-12 | 2017-11-03 | 中国石油大学(北京) | A kind of catalyst layer and metal-air battery for metal air battery cathodes |
| CN107337780A (en) * | 2017-07-20 | 2017-11-10 | 深圳大学 | A kind of preparation method for the shape memory elastic body that light heat double-bang firecracker is answered |
| CN110922561A (en) * | 2019-12-13 | 2020-03-27 | 广东石油化工学院 | Light/heat triple shape memory star polymer and preparation method thereof |
| CN111269386A (en) * | 2020-03-26 | 2020-06-12 | 深圳大学 | Ionic shape memory polyurethane, crystal form A, preparation method and application thereof |
| CN111875765A (en) * | 2020-07-16 | 2020-11-03 | 复旦大学 | Linear azobenzene polymer containing hydrogen bond and preparation method and application thereof |
| CN116694066A (en) * | 2023-08-07 | 2023-09-05 | 苏州易昇光学材料股份有限公司 | GPU (graphic processing unit) optical film and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107317041A (en) * | 2017-07-12 | 2017-11-03 | 中国石油大学(北京) | A kind of catalyst layer and metal-air battery for metal air battery cathodes |
| CN107337780A (en) * | 2017-07-20 | 2017-11-10 | 深圳大学 | A kind of preparation method for the shape memory elastic body that light heat double-bang firecracker is answered |
| CN110922561A (en) * | 2019-12-13 | 2020-03-27 | 广东石油化工学院 | Light/heat triple shape memory star polymer and preparation method thereof |
| CN110922561B (en) * | 2019-12-13 | 2022-01-04 | 广东石油化工学院 | Light/heat triple shape memory star polymer and preparation method thereof |
| CN111269386A (en) * | 2020-03-26 | 2020-06-12 | 深圳大学 | Ionic shape memory polyurethane, crystal form A, preparation method and application thereof |
| CN111269386B (en) * | 2020-03-26 | 2021-09-28 | 深圳大学 | Ionic shape memory polyurethane, crystal form A, preparation method and application thereof |
| CN111875765A (en) * | 2020-07-16 | 2020-11-03 | 复旦大学 | Linear azobenzene polymer containing hydrogen bond and preparation method and application thereof |
| CN116694066A (en) * | 2023-08-07 | 2023-09-05 | 苏州易昇光学材料股份有限公司 | GPU (graphic processing unit) optical film and preparation method thereof |
| CN116694066B (en) * | 2023-08-07 | 2023-09-29 | 苏州易昇光学材料股份有限公司 | GPU (graphic processing unit) optical film and preparation method thereof |
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