CN108912665A - A kind of flexible sensor and preparation method of near infrared light selfreparing - Google Patents
A kind of flexible sensor and preparation method of near infrared light selfreparing Download PDFInfo
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- CN108912665A CN108912665A CN201810533440.1A CN201810533440A CN108912665A CN 108912665 A CN108912665 A CN 108912665A CN 201810533440 A CN201810533440 A CN 201810533440A CN 108912665 A CN108912665 A CN 108912665A
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- RQAJBJDDNZLHQB-UHFFFAOYSA-N CC(N1N[O]=C(N)NC1=N1)=CC1=O Chemical compound CC(N1N[O]=C(N)NC1=N1)=CC1=O RQAJBJDDNZLHQB-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N CCCCCCCCCCN Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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Abstract
The present invention is to provide the flexible sensors and preparation method of a kind of near infrared light selfreparing.It is made of supermolecule polymer matrix and carbon nanotube, the supermolecule polymer matrix based on segment among 2- urea groups -4 [1H]-pyrimidone Quadrupolar hydrogen bond structure end group and polymer by being formed.The present invention develops a kind of supermolecule flexible polymer material that can be melted or soften under the stimulation of 808nm near infrared light, has widened self-healing flexible material field, the manufacture craft of material is simple, and cost is relatively low.Products obtained therefrom can be used for the more difficult field directly contacted, and being heated by indirect mode makes its spontaneous reparation damage.Replaced material recycles after can directly cleaning dissolves pouring molding again, effectively avoids the waste of raw material, saves use cost, increases economic efficiency.
Description
Technical field
The present invention relates to a kind of flexible sensor, the present invention also relates to be a kind of flexible sensor preparation side
Method.The flexible sensor and preparation method of specifically a kind of selfreparing.
Background technique
Flexible sensor refers to using sensor made of flexible material have good flexibility, ductility, even may be used
Free bend even folds, and structure type is versatile and flexible, can arbitrarily be arranged according to the requirement of measuring condition, can be very square
Just complexity is measured and is detected.Novel flexible sensor is in electronic skin, health care, electronics, electrician, locomotory apparatus
The fields such as material, textile, space flight and aviation, environmental monitoring are widely applied.Flexible sensor generally has two parts composition, and one
Dividing is flexible substrate, provides support part, and another part is the sensing element responded to a certain or a variety of stimulations.It is flexible
Matrix generally has the attributes such as soft, low modulus, easily-deformable.Common flexible material has：Polyvinyl alcohol (PVA), polyester
(PET), polyimides (PI), dimethyl silicone polymer (PDMS), paper, textile material etc..Traditional flexible substrate is flexible,
Deformation nature is excellent, but material is difficult to self-regeneration after scuffing or breakage, and senser element is caused to fail, increase use at
This.Therefore, it is novel can selfreparing flexible sensing device have become a hot topic of research.
Selfreparing (self-healing) refer to material under certain external condition effect, it is spontaneous that breakage is repaired
It is multiple, with before restoring breakage completely or partially a certain or a variety of property or (and) performance the phenomenon that, the phenomenon can occur
Material be referred to as self-healing material.Self-healing material can be applied to bionical device, intellectual material, packing container, medical equipment,
Film shell etc. is easy to the field of damaged and more difficult replacement, thus has obtained extensive concern and research.Traditional selfreparing material
Material mostly provides energy to system in a manner of through heating etc., brings it about crystallization, the effects of surface forms film or generates crosslinking
It realizes and repairs.Selfreparing flexible sensing device application field is extensive, this is but also in some special applications, it is difficult to directly
Heating operation processing is carried out to device, thus develops one kind the flexible sensor of contactless fever can occur as urgent need
It solves the problems, such as.
Summary of the invention
The purpose of the present invention is to provide a kind of near infrared lights that can be melted or soften under the excitation of 808nm near infrared light
The flexible sensor of selfreparing.The object of the invention is also to provide a kind of preparations of the flexible sensor of near infrared light selfreparing
Method.
The flexible sensor of near infrared light selfreparing of the invention is made of supermolecule polymer matrix and carbon nanotube, institute
Stating supermolecule polymer matrix is by based on segment among 2- urea groups -4 [1H]-pyrimidone Quadrupolar hydrogen bond structure end group and polymer
Composition.
The flexible sensor of near infrared light selfreparing of the invention can also include：
1,2- urea groups -4 [1H]-pyrimidone Quadrupolar hydrogen bond structure end group that is based on is such as one or more in flowering structure
It is a,
WhereinRepresent hydrogen bond, R1By one or two kinds of structure compositions as described below
1)C1-C10Direct-connected or branched alkyl；
2) comprising the C of 1-4 Carbamido substituted base1-C10Alkyl, the structure of the urea groups is
2, segment is one or more of such as flowering structure among the polymer,
1) polyether structure
Wherein R4、R5It is any one in following group with Y
a)H；
B) C1-C6 linear or branched alkyl group,
N is 1-6,
O is 10-100.
2) polyolefin structure
Wherein R6、R7It is any one in following group with Y
a)H；
B) C1-C6 linear or branched alkyl group；
C) C1-C6 linear chain or branched chain alkenyl,
P is 10-100.
3, it is for the mixture of following two polymer that the supermolecule polymer matrix, which is structure,：
Polymer 1：
Polymer 2：
Mixed proportion is weight ratio 3:1~9:1.
The preparation method of the flexible sensor of near infrared light selfreparing of the invention is：
(1) synthon is prepared
Methylisocytosine is reacted under protection of argon gas with hexamethylene diisocyanate, obtains white precipitate, is cooled to
N-hexane stirring is added after room temperature, filtering, with the washed washing of n-hexane, vacuum drying obtains white powder synthon, synthesizes
Son structure be
(2) polymer 1 is prepared
Synthon, chloroform and dibutyltin dilaurate catalyst is added after hydrogenated polybutadiene diol vacuum drying,
It is reacted under argon atmosphere, to which dry silica gel and dibutyl tin dilaurate are added after the reaction was completed, the reaction was continued, is cooled to room
Temperature filters to take filtrate concentration addition methanol and obtains colorless and transparent polymer 1, and the structure of polymer 1 is
(3) polymer 2 is prepared
Three-functionality-degree terminal hydroxy group polyethylene glycol oxide/propylene triol vacuum drying, is added synthon, chloroform and tin dilaurate two
Butyl tin catalyst reacts under argon atmosphere, to which the dibutyl tin dilaurate of dry silica gel sum is added after the reaction was completed
The reaction was continued, is cooled to room temperature, and filters to take filtrate concentration, and n-hexane is added and obtains colorless and transparent polymer 2, polymer
2 structure is
(4) carbon nanotube is sprayed
Polymer 1 is mixed into addition chloroform with polymer 2 and is tuned into paste, concentration after-pouring is dried to obtain oversubscription into mold
Sub- polymeric matrix；Chloroform, ultrasonic disperse, with spray gun even application in supermolecule polymer matrix surface is added in carbon nanotube.
The preparation method of the flexible sensor of near infrared light selfreparing of the invention can also include：
1, polymer 1, polymer 2, carbon nanotube proportion be：
1 180g of polymer
2 20g of polymer
Carbon nanotube chloroformic solution 10mL.
2, polymer 1, polymer 2, carbon nanotube proportion be：
1 170g of polymer
2 30g of polymer
Carbon nanotube chloroformic solution 10mL.
3, polymer 1, polymer 2, carbon nanotube proportion be：
1 150g of polymer
2 50g of polymer
Carbon nanotube chloroformic solution 10mL.
Supermolecule polymer is formed using non-covalent bond effect connection polymerized monomer with larger molecular weight polymer line
Property or network polymers, have certain mechanical strength guarantee its applicability.Simultaneously because the dynamic equilibrium of non-covalent bond is special
Property, supermolecule polymer may be implemented to carry out self-regeneration damage under a certain or a variety of specified conditions.Carbon nanotube is one
The kind higher black-materials of photo-thermal efficiency have stronger absorption to the near infrared light of 808nm and are converted into thermal response.It has simultaneously
Excellent conductivity, can be used as conductive coating, have preferable response to mechanical stimulation.By supermolecule polymer and carbon nanotube
Material combines, and can prepare the selfreparing flexibility mechanics senser element that can be absorbed 808nm near infrared light and generate heat.
For the demand of body temperature self-healing flexible material, this hair provide one kind can 808nm near infrared light excitation under energy
Enough supermolecule flexible conductive polymer based composites melted or soften, can be used for preparing selfreparing flexible sensor.This hair
Bright middle material prescription is using raw materials such as synthetic resin, carbon nanotubes.
Technical way of the invention is：Near infrared light selfreparing flexible sensor, by supermolecule polymer matrix and
Carbon nanotube composition.Its preparation process includes the synthesis of matrix resin, pours, the dispersion and solution in the solution of carbon nanotube
The processes such as spraying.Supermolecule polymer matrix is based on 2- urea groups -4 [1H]-pyrimidone Quadrupolar hydrogen bond structure, selects different polymer
As intermediate segment, the supermolecule flexible polymer material that can be melted or soften under a certain specific temperature is prepared to realize certainly
Healing.
It is poly- that the present invention develops a kind of supermolecule flexibility that can be melted or soften under the stimulation of 808nm near infrared light
Object material is closed, has widened self-healing flexible material field, the manufacture craft of material is simple, and cost is relatively low.Products obtained therefrom can be used for
The more difficult field directly contacted, being heated by indirect mode makes its spontaneous reparation damage.Replaced material can be cleaned directly
After recycle and dissolve pouring molding again, effectively avoid the waste of raw material, save use cost, increase economic efficiency.
Specific embodiment
The supermolecule polymer matrix of the flexible sensor of near infrared light selfreparing is based on Quadrupolar hydrogen bond structure as end group
And select different polymer as intermediate segment, further, the Quadrupolar hydrogen bond system according to electron donor (D) and electronics by
The position arrangement of body (A) is different, and Quadrupolar hydrogen bond is such as one or more in flowering structure there are two kinds of association modes of DADA and AADD
It is a,
WhereinRepresent hydrogen bond, R1By one or two kinds of structure compositions as described below
1)C1-C10Direct-connected or branched alkyl；
2) comprising the C of 1-4 Carbamido substituted base1-C10Alkyl, urea groups is shown below structure
Meanwhile Quadrupolar hydrogen bond group passes through R1It is connected with segment among polymer as supermolecule polymer main chain.
There is 10-100 Quadrupolar hydrogen bond group in the supermolecule polymer matrix of the flexible sensor of near infrared light selfreparing
It is connected with segment among polymer.
The supermolecule polymer matrix of the flexible sensor of near infrared light selfreparing is based on Quadrupolar hydrogen bond structure as end group,
And select different polymer as intermediate segment, and further, the flexible sensor of the near infrared light selfreparing, described in
Among polymer segment be such as one or more of flowering structure,
1) polyether structure
Polyether structure is as follows
Wherein R4、R5It is any one in following group with Y
a)H；
B) C1-C6 linear or branched alkyl group.
N is 1-6.
O is 10-100.
2) polyolefin structure
Polyolefin structure is following one of which
Wherein R6、R7It is any one in following group with Y
c)H；
D) C1-C6 linear or branched alkyl group；
E) C1-C6 linear chain or branched chain alkenyl；
P is 10-100.
The supermolecule polymer matrix resin of the flexible sensor of near infrared light selfreparing can be above-mentioned Quadrupolar hydrogen bond oversubscription
One in sub- polymer constitutes or multiple compounds.
- 4 [1H]-pyrimidone Quadrupolar hydrogen bond structure of 2- urea groups is artificial composite structure, the tree of segment among polymer
Rouge can be natural resin, be also possible to synthetic resin.The solvent of supermolecule polymer matrix preparation process can be alkanes,
Or mixtures thereof alkyl halide hydro carbons, alcohols, esters, ethers, ketone, aromatic organic solvent, such as use hexamethylene, trichlorine
Methane, ethyl alcohol, ethyl acetate, tetrahydrofuran, butanone, toluene etc..
The carbon nanotube of the flexible sensor of near infrared light selfreparing is near-infrared optical Response material, while having both conduction
Property with power/electrical response performance.Carbon nanotube used be commercial single-walled carbon nanotube (SWCNT) or (and) multi-walled carbon nanotube
(MWCNT).Carbon nanotube, which is scattered in organic solvent, is sprayed on above-mentioned flexible supermolecule polymer surface, obtains uniform carbon
Layer, to prepare the flexible sensor composite material of near infrared light selfreparing.
It illustrates below and the present invention is described in more detail.
Dry chloroform is evaporated under reduced pressure after overnight by calcium hydride reflux and is obtained.Dry tetrahydrofuran and toluene passes through sodium
Silk is refluxed overnight rear distillation under pressure with benzophenone and obtains.Dry butanone is evaporated under reduced pressure after being refluxed overnight by natrium carbonicum calcinatum
It obtains.Dry ethyl alcohol and dimethylformamide is obtained by being evaporated under reduced pressure after 4A molecular sieve soaked overnight.
(1) preparation of synthon
Methylisocytosine (65g) and hexamethylene diisocyanate (HDI, 650g) 100 DEG C of stirrings under protection of argon gas
16h is reacted, obtains white precipitate after the reaction was completed.1L n-hexane and high degree of agitation 1h, filtering, with just are added after being cooled to room temperature
The washed washing of hexane, vacuum drying obtain white powder.
1H NMR(500MHz,CDCl3):δ13.1(1H),11.8(1H),10.1(1H),5.8(1H),3.3(4H),2.1
(3H), 1.6(4H),1.4(4H).
FT-IR:ν(cm-1)2935,2281,1698,1668,1582,1524,1256.
(2) preparation of polymer
Polymer 1
(Cray Valley company of the U.S., linear hydroxyl-terminated hydrogenation are poly- by 22.4g hydrogenated polybutadiene diol HLBH-P3000
Butadiene, 3.2kD) 1h is dried in vacuo at 100 DEG C, and (temperature cannot be excessively high, and the time cannot be too long to prevent long-time heating point
Solution), it is cooling under dry environment, 4.3g synthon, 500mL chloroform and micro dibutyltin dilaurate catalyst is added,
72h is stirred to react for 60 DEG C of constant temperature under argon atmosphere.To which dry silica gel and micro two fourth of tin dilaurate after the reaction was completed, is added
Ji Xi, the reaction was continued for 24 hours.It is cooled to room temperature, filters to take filtrate, be concentrated into 100mL, methanol is added and obtains white precipitate.Use first
Alcohol washing, vacuum drying obtain colorless and transparent elastomeric material.
1H NMR(500MHz,CDCl3):δ5.8,4.1,3.3-3.0,2.9-2.8,2.2,1.6-1.0,0.8.
FT-IR(neat):ν(cm-1)3457,3336,3216,2959,2925,2855,1700,1664,1590,1525,
1461,1379,1252,761.
Tm:65.6℃
Polymer 2
24.8g TEP330N (U.S. Dow chemistry, three-functionality-degree terminal hydroxy group polyethylene glycol oxide/propylene triol, 5.1kD) exists
It is dried in vacuo 1h (temperature cannot be excessively high, and the time cannot be too long to prevent long-time heating from decomposing) at 100 DEG C, under dry environment
It is cooling, 4.36g synthon, 500mL chloroform and micro dibutyltin dilaurate catalyst, the constant temperature under argon atmosphere is added
60 DEG C are stirred to react 72h.To which dry silica gel and micro dibutyl tin dilaurate after the reaction was completed, is added, the reaction was continued
24h.It is cooled to room temperature, filters to take filtrate, be concentrated into 100mL, n-hexane is added and obtains white precipitate.It is washed with n-hexane, very
Sky is dry, obtains colorless and transparent elastomeric material.
1H NMR(500MHz,CDCl3):δ13.1,11.8,10.2,8.0,4.2,3.8-3.1,2.3,1.7-1.0.
FT-IR(neat):ν(cm-1)3341,3216,2971,2931,2869,1722,1700,1667,1588,1527,
1454,1374,1256,1108,1015,931.
Tm:23.8℃
(3) dispersion and spraying of carbon nanotube
0.06g multi-walled carbon nanotube is added in 20mL chloroform, ultrasonic disperse 4h, with spray gun even application in 25*50mm's
Supermolecule polymer surface.Spray pressure 0.5MPa, spray gun height 10cm.
Embodiment 1
1 presses following component proportion
1 180g of polymer
2 20g of polymer
Carbon nanotube chloroformic solution 10mL
2 preparation methods
Polymer 1 and polymer 2 are added dissolution in 2000mL chloroform and are tuned into paste after mixing, be concentrated into 500mL, pour to
Mould
Supermolecule polymer sill is obtained after drying in tool.After supermolecule polymer matrix is dry, even application carbon is received
Mitron chlorine
Imitative solution, the flexible sensor of drying to obtain near infrared light selfreparing.
The material can soften self-healing at 45 DEG C, melt at 60 DEG C.
Embodiment 2
1 presses following component proportion
1 170g of polymer
2 30g of polymer
Carbon nanotube chloroformic solution 10mL
2 preparation methods
Polymer 1 and polymer 2 are added dissolution in 2000mL chloroform and are tuned into paste after mixing, be concentrated into 500mL, pour to
Mould
Supermolecule polymer sill is obtained after drying in tool.After supermolecule polymer matrix is dry, even application carbon is received
Mitron chlorine
Imitative solution, the flexible sensor of drying to obtain near infrared light selfreparing.
The material can soften self-healing at 40 DEG C, melt at 55 DEG C.
Embodiment 3
1 presses following component proportion
1 150g of polymer
2 50g of polymer
Carbon nanotube chloroformic solution 10mL
2 preparation methods
Polymer 1 and polymer 2 are added dissolution in 2000mL chloroform and are tuned into paste after mixing, be concentrated into 500mL, pour to
Supermolecule polymer sill is obtained after drying in mold.After supermolecule polymer matrix is dry, even application carbon
Nanotube
Chloroformic solution, the flexible sensor of drying to obtain near infrared light selfreparing.
The material can soften self-healing at 40 DEG C, melt at 53 DEG C.
Claims (9)
1. a kind of flexible sensor of near infrared light selfreparing, it is characterized in that：By supermolecule polymer matrix and carbon nanotube group
At the supermolecule polymer matrix is by based in 2- urea groups -4 [1H]-pyrimidone Quadrupolar hydrogen bond structure end group and polymer
Between segment form.
2. the flexible sensor of near infrared light selfreparing according to claim 1, it is characterized in that：It is described to be based on 2- urea groups -4
[1H]-pyrimidone Quadrupolar hydrogen bond structure end group be such as one or more of flowering structure,
WhereinRepresent hydrogen bond, R1By one or two kinds of structure compositions as described below
1)C1-C10Direct-connected or branched alkyl；
2) comprising the C of 1-4 Carbamido substituted base1-C10Alkyl, the structure of the urea groups is
3. the flexible sensor of near infrared light selfreparing according to claim 1 or 2, it is characterized in that：In the polymer
Between segment be one or more of such as flowering structure,
1) polyether structure
Wherein R4、R5It is any one in following group with Y
a)H；
B) C1-C6 linear or branched alkyl group,
N is 1-6,
O is 10-100.
2) polyolefin structure
Wherein R6、R7It is any one in following group with Y
a)H；
B) C1-C6 linear or branched alkyl group；
C) C1-C6 linear chain or branched chain alkenyl,
P is 10-100.
4. the flexible sensor of near infrared light selfreparing according to claim 1 or 2, it is characterized in that：The supermolecule is poly-
It is for the mixture of following two polymer that conjunction object matrix, which is structure,：
Polymer 1：
Polymer 2：
Mixed proportion is weight ratio 3:1~9:1.
5. the flexible sensor of near infrared light selfreparing according to claim 3, it is characterized in that：The supermolecule polymer
Matrix is that structure is for the mixture of following two polymer：
Polymer 1：
Polymer 2：
Mixed proportion is weight ratio 3:1~9:1.
6. a kind of preparation method of the flexible sensor of near infrared light selfreparing described in claim 1, it is characterized in that：
(1) synthon is prepared
Methylisocytosine is reacted under protection of argon gas with hexamethylene diisocyanate, obtains white precipitate, is cooled to room temperature
N-hexane stirring is added afterwards, filtering, with the washed washing of n-hexane, vacuum drying obtains white powder synthon, synthon
Structure is
(2) polymer 1 is prepared
Synthon, chloroform and dibutyltin dilaurate catalyst is added after hydrogenated polybutadiene diol vacuum drying, in argon gas
It is reacted under atmosphere, to which dry silica gel and dibutyl tin dilaurate are added after the reaction was completed, the reaction was continued, is cooled to room temperature, mistake
The concentration of leaching filtrate is added methanol and obtains colorless and transparent polymer 1, and the structure of polymer 1 is
(3) polymer 2 is prepared
Three-functionality-degree terminal hydroxy group polyethylene glycol oxide/propylene triol vacuum drying, is added synthon, chloroform and di lauric dibutyl
Tin catalyst reacts under argon atmosphere, and the dibutyl tin dilaurate to which dry silica gel sum is added after the reaction was completed continues
Reaction, is cooled to room temperature, and filters to take filtrate concentration, and n-hexane is added and obtains colorless and transparent polymer 2, polymer 2
Structure is
(4) carbon nanotube is sprayed
Polymer 1 is mixed into addition chloroform with polymer 2 and is tuned into paste, it is poly- that concentration after-pouring is dried to obtain supermolecule into mold
Close object matrix；Chloroform, ultrasonic disperse, with spray gun even application in supermolecule polymer matrix surface is added in carbon nanotube.
7. the preparation method of the flexible sensor of near infrared light selfreparing according to claim 6, it is characterized in that polymer
1, polymer 2, carbon nanotube proportion be：
1 180g of polymer
2 20g of polymer
Carbon nanotube chloroformic solution 10mL.
8. the preparation method of the flexible sensor of near infrared light selfreparing according to claim 6, it is characterized in that polymer
1, polymer 2, carbon nanotube proportion be：
1 170g of polymer
2 30g of polymer
Carbon nanotube chloroformic solution 10mL.
9. the preparation method of the flexible sensor of near infrared light selfreparing according to claim 6, it is characterized in that polymer
1, polymer 2, carbon nanotube proportion be：
1 150g of polymer
2 50g of polymer
Carbon nanotube chloroformic solution 10mL.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110423337A (en) * | 2019-07-08 | 2019-11-08 | 浙江大学衢州研究院 | A kind of Thermo-sensitive supermolecule polymer and preparation method thereof of multiple hydrogen bonding regulation |
| CN111286075A (en) * | 2019-12-02 | 2020-06-16 | 哈尔滨工程大学 | Recyclable supramolecular polymer foam material and preparation method thereof |
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| CN106221100A (en) * | 2016-07-21 | 2016-12-14 | 天津大学 | A kind of preparation method of optical drive selfreparing thin film based on ethylene-butylene copolymer |
| CN107216643A (en) * | 2017-08-03 | 2017-09-29 | 四川大学 | A kind of selfreparing polyurethane nano composite material and its production and use |
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| CN104833376A (en) * | 2015-04-24 | 2015-08-12 | 中国人民大学 | Self-repairing sensing chip and preparation method thereof |
| CN104892871A (en) * | 2015-06-16 | 2015-09-09 | 厦门大学 | Hydrogel with self-repairing function and preparation method of hydrogel |
| CN106221100A (en) * | 2016-07-21 | 2016-12-14 | 天津大学 | A kind of preparation method of optical drive selfreparing thin film based on ethylene-butylene copolymer |
| CN107216643A (en) * | 2017-08-03 | 2017-09-29 | 四川大学 | A kind of selfreparing polyurethane nano composite material and its production and use |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110423337A (en) * | 2019-07-08 | 2019-11-08 | 浙江大学衢州研究院 | A kind of Thermo-sensitive supermolecule polymer and preparation method thereof of multiple hydrogen bonding regulation |
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| CN111286075A (en) * | 2019-12-02 | 2020-06-16 | 哈尔滨工程大学 | Recyclable supramolecular polymer foam material and preparation method thereof |
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