CN109160995A - A kind of column [5] aromatic hydrocarbons self assembly elastomeric material and preparation method thereof - Google Patents
A kind of column [5] aromatic hydrocarbons self assembly elastomeric material and preparation method thereof Download PDFInfo
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- CN109160995A CN109160995A CN201810944931.5A CN201810944931A CN109160995A CN 109160995 A CN109160995 A CN 109160995A CN 201810944931 A CN201810944931 A CN 201810944931A CN 109160995 A CN109160995 A CN 109160995A
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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
- C08G18/65—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
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
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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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone 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
- 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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a kind of column [5] aromatic hydrocarbons self assembly elastomeric materials and preparation method thereof, belong to polymeric material field.Chloroform solvent polymeric is added at a certain temperature and obtains for the propylene glycol that the material is blocked by 1- (3- aminopropyl) imidazoles, diisocyanate terminated polypropylene glycol and three headpins [5] aromatic hydrocarbons.The preparation method of material mainly includes the following steps: for diisocyanate terminated polypropylene glycol to be dissolved in chloroform solvent, then 1- (3- aminopropyl) imidazoles is dissolved in chloroform solvent and is added dropwise in above-mentioned solution, the propylene glycol that three headpin aromatic hydrocarbons block is added after return stirring reaction, and the reaction was continued, product is poured into polytetrafluoroethylene (PTFE) grinding tool after the reaction was completed, obtains that there is certain mechanical strength and toughness polymer composite material after 50 DEG C of forced air dryings.Compared with prior art, preparation process of the invention is simple, and preparation efficiency is high, is suitble to industrial mass production.
Description
Technical field
The invention belongs to polymeric material fields, and in particular to a kind of to be self-assembly of elasticity with column [5] aromatic hydrocarbons Subjective and Objective
Composite material and preparation method thereof.
Background technique
Traditional high molecular material is formed and being covalently keyed by small molecule monomer, by dexterously designing me
Can assign their good optics, electricity and mechanical properties to meet the needs of social development is for material.But by
In the irreversibility of covalent bond, there are also disadvantages for traditional high molecular material, such as are difficult to degrade, and are not easy to recycle, very
Hardly possible adapt to external environment stimulation, drug wrap up and control release in terms of using very limited etc..However non-covalent bond is for example
Multiple hydrogen bonding, pi-pi accumulation, metal coordinate bond, hydrophobe effect, Host-guest Recognition etc., are dynamic keys, they have invertibity and
Stimulating responsive.If non-covalent bond and conventional polymer material combined, not only can solve existing for traditional high sub- material
Some problems, and type, quantity, the chemical structure of functional group etc. by changing non-covalent bond, can also prepare has
The supramolecular polymer material of different chemically or physically performances.
In numerous supermolecular mechanism power, it is based on the master of macrocyclic host (such as crown ether, cyclodextrin, calixarenes, Cucurbituril)
Object identification has been widely used for preparing various functional supramolecular polymer materials, and it is past that this is mainly due to Host-guest Recognitions
Toward the synergistic effect from a variety of non-covalent bond effect power, so that not only there is good binding ability between Subjective and Objective, but also
The host-guest complex of formation has certain space conformation and directionality.In addition, Host-guest Recognition also has stimulation abundant
Responsiveness, such as the response to soda acid, light, anion, cation, temperature and solvent etc..Therefore, super based on Host-guest Recognition
Molecularly Imprinted Polymer material is with important application prospects.
Column aromatic hydrocarbons is some unique excellent compared to having for other supermolecule main blocks as a new class of macrocyclic host
Point: the cavity of electron rich makes column aromatic hydrocarbons have the ability in conjunction with molecule even neutral with electron deficient well, including
Alkyl chain, pyridine, viologen, imidazoles, alkylammonium salt and neutral imdazole derivatives etc.；The structure of high degree of symmetry and easy function dough
The characteristics of make column aromatic hydrocarbons have very strong Host-guest Recognition ability.Therefore, column aromatic hydrocarbons is largely used to construct various functional super
Molecular system, including the polymerization of mechanical interlock (rotaxane and catenne etc.), liquid crystal, supermolecular gel, chemical sensor, supermolecule
Object, pharmaceutical carrier, cell be bionical, transdermal delivery channel and cell mucous membrane etc..
Summary of the invention
To solve the deficiencies in the prior art, column [5] aromatic hydrocarbons Subjective and Objective self assembly is used the object of the present invention is to provide a kind of
Form elastic composite and preparation method thereof.
To achieve the goals above, the present invention adopts the following technical scheme:
A kind of column aromatic hydrocarbons Subjective and Objective self assembly elastic composite provided by the invention by 1- (3- aminopropyl) imidazoles,
Propylene glycol polycondensation, master in chloroform solvent of diisocyanate terminated polypropylene glycol and three headpins [5] aromatic hydrocarbons sealing end
Drying and forming-film obtains after object self assembly；The polymer point for propylene glycol and the imidazoles sealing end that three headpin aromatic hydrocarbons block in composite material
It is connected between subchain by the binding force between Subjective and Objective；There is also some dynamics between different polymer molecular chains in material simultaneously
Hydrogen bond, therefore the elastic composite also has certain intensity and toughness.
In the propylene glycol structure of three headpins [5] aromatic hydrocarbons sealing end, each molecule is containing there are three column [5] aromatic hydrocarbons.Presoma imidazoles
Imidazole ring and column aromatic hydrocarbons cavity in the polypropylene glycol of sealing end can carry out host-guest interaction, have very strong combination energy
Power, this is conducive to polymer and forms spacial framework, enhances the intensity and toughness of elastomer.
Diisocyanate terminated polypropylene glycol structural formula is as follows:
Wherein, diisocyanate terminated polypropylene glycols amount is preferably 2300.
The present invention also provides the preparation methods of the room temperature Self-repair Composites, comprising the following steps:
Step 1: under an inert atmosphere, the diisocyanate terminated polypropylene glycol stirring of 2.3g being dissolved in the three of 25 DEG C of 20mL
In chloromethane alkane solvents；
Step 2: 1- (3- aminopropyl) imidazoles being dissolved in chloroform solvent, step is then added dropwise in proportion
(1) it in solution, is stirred at reflux reaction 2h and obtains prepolymer, 1- (3- aminopropyl) imidazoles and diisocyanate terminated poly-
The molar ratio of propylene glycol is 2:1；
Step 3: the propylene glycol that three headpins [5] aromatic hydrocarbons of preparation blocks being dissolved in chloroform, then to step (2)
It is proportionally added into solution, the reaction was continued 30min；
Step 4: the product that step (3) obtains being transferred in the mold of polytetrafluoroethylene (PTFE), 50 DEG C in air dry oven
Obtain having both the self assembly elastomeric material of high-intensity and high-tenacity after drying.
Compared with prior art, the present invention its remarkable advantage is:
(1) elastomer prepared by the present invention is the effect and traditional elasticity for the space crosslinking played by host-guest interaction
Body, which is compared, to be easy to explain, and can be recycled.
(2) elastomer prepared by the present invention is due to containing host-guest interaction, therefore the elastomer also has thorn abundant
Swash responsiveness, such as the response to soda acid, light, anion, cation, temperature and solvent etc..
(3) there are host-guest interactions between imidazole ring and column aromatic hydrocarbons in the present invention, so that the elastomer has extensively
Application prospect.
(4) preparation process of the present invention is easy to operate, reproducible, and operation is easy, is suitable for marketing.
(5) composite material of the invention can be hot-forming, and polymer network is crosslinked by non-covalent bond in composite material, can
With recycling.
Detailed description of the invention
Fig. 1 is the preparation flow schematic diagram of composite material of the present invention.
Fig. 2 is the nuclear magnetic spectrogram of the hydrogen of 1- (4- bromine butoxy) -4- methoxybenzene that in the present invention prepared by step 1.
Fig. 3 is the nuclear magnetic spectrogram of bromo column [5] aromatic hydrocarbons hydrogen that in the present invention prepared by step 2.
Fig. 4 is the nuclear magnetic spectrogram of the propylene glycol hydrogen of three headpins [5] the aromatic hydrocarbons sealing end prepared in the present invention.
Fig. 5 is presoma material object photo prepared by the embodiment of the present invention 1.
Fig. 6 is self assembly elastomer material object photo prepared by the embodiment of the present invention 1.
Fig. 7 is the nuclear magnetic spectrogram present invention demonstrates that host-guest interaction.
Fig. 8 is the nuclear magnetic spectrogram present invention demonstrates that host-guest interaction.
Specific embodiment
The invention will be further described below in conjunction with the accompanying drawings.Following embodiment is only used for clearly illustrating the present invention
Technical solution, and not intended to limit the protection scope of the present invention.
The preparation of bromo column [5] aromatic hydrocarbons
Step 1: preparing 1- (4- bromine butoxy) -4- methoxybenzene for p-hydroxyanisole 12.4g (0.1mol), potassium carbonate
Then 22g (0.16mol) is added 200mL acetonitrile, 30min is stirred at room temperature, adds potassium iodide 0.2g in three neck round bottom flask
(10mmol), Isosorbide-5-Nitrae-dibromobutane 14.2mL (0.12mol), 80 DEG C of back flow reaction 16h.It filters after reaction, filtrate is true
Crude product is obtained after sky is dry, with column Chromatographic purification (petroleum ether: ethyl acetate=10:1).1H NMR, 300MHz, CDCl3, such as scheme
Shown in 2.
Step 2: by 4.14g (30mmol) Isosorbide-5-Nitrae-dimethoxy benzene, product 1- (the 4- bromine fourth of 1.56g (6mmol) step 1
Oxygroup) -4- methoxybenzene, 1.635g paraformaldehyde is placed in three-necked flask, and 150mL 1,2- dichloroethanes is added；Ultrasound
30min is then stirred at room temperature in 30min, adds boron trifluoride ether 4.29mL, reacts at room temperature 3h.75mL methanol is added to be quenched
Reaction is extracted with water (2*150mL), takes organic phase, be dried overnight with anhydrous sodium sulfate, filters, filtrate is spin-dried for obtain thick mesh
Product is marked, obtains target product with column Chromatographic purification (methylene chloride: n-hexane=2:1).1H NMR, 300MHz, CDCl3, such as Fig. 3
It is shown.
The propylene glycol preparation of three headpins [5] aromatic hydrocarbons sealing end
As shown in Figure 1, a kind of preparation method of room temperature Self-repair Composites, comprising the following steps:
Weigh three polypropylene glycol ether of trimethylol propane (amino-terminated) 90mg (0.20mmol), potassium carbonate 83mg
Then (0.6mmol) is added 30mL acetonitrile, 30min is stirred at room temperature, adds potassium iodide 100g in three neck round bottom flask
(5mmol), bromo column [5] aromatic hydrocarbons 500mg (0.6mmol), 80 DEG C of back flow reactions are for 24 hours.After reaction, add in phase reaction system
Enter distilled water, (extraction is three times) is then extracted with dichloromethane, takes organic phase；Crude product is rotated to obtain, it is then molten with chloroform
Agent dialysis removes impurity, rotates to obtain target product, 1H NMR, 300MHz, CDCl3, as shown in Figure 4.
Embodiment 1 prepares elastic composite by self assembly
As shown in Figure 1, a kind of preparation method of room temperature Self-repair Composites, comprising the following steps:
Step 1: in a nitrogen atmosphere, the diisocyanate terminated polypropylene glycol stirring of 1.54g being dissolved in 20mL chloroform
In solvent；
Step 2: 0.167g1- (3- aminopropyl) imidazoles being dissolved in 10mL chloroform solvent, step is then added dropwise
In rapid 1 solution, it is stirred to react 2h；
Step 3: the propylene glycol of tri- headpin of 0.6g [5] aromatic hydrocarbons sealing end being added into the solution of step 2, continues to stir 60min
Carry out self assembly；
Step 4: the product that step 3 is obtained is transferred in the mold of polytetrafluoroethylene (PTFE), is done for 50 DEG C in air dry oven
Elastic composite is obtained after dry.
Embodiment 2 prepares elastic composite by self assembly
As shown in Figure 1, a kind of preparation method of room temperature Self-repair Composites, comprising the following steps:
Step 1: in a nitrogen atmosphere, the diisocyanate terminated polypropylene glycol stirring of 1.54g being dissolved in 20mL chloroform
In solvent；
Step 2: 0.167g1- (3- aminopropyl) imidazoles being dissolved in 10mL chloroform solvent, step is then added dropwise
In rapid 1 solution, it is stirred to react 2h；
Step 3: the propylene glycol of tri- headpin of 1.2g [5] aromatic hydrocarbons sealing end being added into the solution of step 2, continues to stir 30min
Carry out self assembly；
Step 4: the product that step 3 is obtained is transferred in the mold of polytetrafluoroethylene (PTFE), is done for 50 DEG C in air dry oven
Elastic composite is obtained after dry.
Embodiment 3 prepares elastic composite by self assembly
As shown in Figure 1, a kind of preparation method of room temperature Self-repair Composites, comprising the following steps:
Step 1: in a nitrogen atmosphere, the diisocyanate terminated polypropylene glycol stirring of 1.54g being dissolved in 20mL chloroform
In solvent；
Step 2: 0.167g1- (3- aminopropyl) imidazoles being dissolved in 10mL chloroform solvent, step is then added dropwise
In rapid 1 solution, it is stirred to react 2h；
Step 3: the propylene glycol of tri- headpin of 2.4g [5] aromatic hydrocarbons sealing end being added into the solution of step 2, continues to stir 15min
Carry out self assembly；
Step 4: the product that step 3 is obtained is transferred in the mold of polytetrafluoroethylene (PTFE), is done for 50 DEG C in air dry oven
Elastic composite is obtained after dry.
Elastomer preparation process of the present invention by the product that the first two steps of case study on implementation 3 obtain as shown in Figure 1, removed
Remove the polypropylene glycol of available presoma imidazoles sealing end after solvent, it is sticky fluid, it is in kind as shown in Figure 5；When forward
It drives after the propylene glycol of three headpins [5] aromatic hydrocarbons sealing end is added in the chloroform soln of body, due to imidazole ring and column aromatic hydrocarbons Subjective and Objective
Effect carries out self assembly, eventually forms elastomer, as shown in Figure 6.The glycol material of three headpins [5] aromatic hydrocarbons sealing end is added in comparison
The variation of fore/aft properties becomes this variation of elastomer by the thick liquid before in addition, it can be seen that host-guest interaction is in the bullet
Effect played in property body formation process.
In order to confirm that imidazole ring and the cavity of column [5] aromatic hydrocarbons have carried out self assembly, simple experiment has been carried out first, by butyl
Imidazoles and column [5] aromatic hydrocarbons are dissolved in deuterated chloroform and survey nucleus magnetic hydrogen spectrum (300M), and the nuclear magnetic spectrogram of itself and pure butyl imidazole is compared,
It was found that chemical shift has occurred in the hydrogen of imidazole ring, as shown in Figure 7,8, it is possible thereby to prove that imidazole ring has occurred with column [5] aromatic hydrocarbons
Inclusion.Then it will be surveyed after the mixed with propylene glycol of the polypropylene glycol of the imidazoles sealing end in the present invention and three headpins [5] aromatic hydrocarbons sealing end
Hydrogen composes (300M), it is again seen that chemical shift has occurred in the hydrogen of imidazole ring, therefore equally also illustrates that imidazole ring and column [5] aromatic hydrocarbons occur
Autonomous dress has occurred in inclusion, i.e. this process.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the technical principles of the invention, several improvement and deformations can also be made, these improvement and deformations
Also it should be regarded as protection scope of the present invention.
Claims (9)
1. a kind of column [5] aromatic hydrocarbons self assembly elastomeric material, which is characterized in that composite material by 1- (3- aminopropyl) imidazoles,
Propylene glycol polycondensation, master in chloroform solvent of diisocyanate terminated polypropylene glycol and three headpins [5] aromatic hydrocarbons sealing end
Drying and forming-film obtains after object self assembly；The propylene glycol and imidazoles envelope that the composite material is blocked by three headpins [5] aromatic hydrocarbons
It is connected between the polymer molecular chain at end by the binding force between Subjective and Objective.
2. composite material according to claim 1, which is characterized in that the diisocyanate terminated polypropylene glycol knot
Structure formula is as follows:
Wherein, diisocyanate terminated polypropylene glycols amount is 2300.
3. composite material according to claim 1, which is characterized in that the propylene glycol of three headpins [5] the aromatic hydrocarbons sealing end
In structure, each molecule is containing there are three column [5] aromatic hydrocarbons.
4. composite material according to claim 3, which is characterized in that the propylene glycol is trimethylol propane trimerization the third two
Alcohol ether (amino-terminated).
5. a kind of preparation method of composite material according to claim 1-4, which is characterized in that including following step
It is rapid:
(1) under an inert atmosphere, the stirring of diisocyanate terminated polypropylene glycol is dissolved in chloroform solvent；
(2) 1- (3- aminopropyl) imidazoles is dissolved in chloroform solvent, the solution of step (1) is then added dropwise in proportion
In, it is stirred at reflux reaction at least 4h and obtains prepolymer；
(3) chloroform soln of the propylene glycol of three headpins [5] aromatic hydrocarbons sealing end is proportionally added into the solution of step (2), after
Continuous reaction at least 30min；
(4) product that step (3) obtains is transferred in the mold of polytetrafluoroethylene (PTFE), obtains self assembly elastomer material after dry
Material.
6. the preparation method of composite material according to claim 5, which is characterized in that the inert atmosphere is nitrogen.
7. the preparation method of composite material according to claim 5, which is characterized in that described 1- (3- aminopropyl) miaow
The mass ratio of the material of azoles and diisocyanate terminated polypropylene glycol is 1:1~3:1.
8. the preparation method of composite material according to claim 5, which is characterized in that the prepolymer presoma and three
The mass ratio of the material of the propylene glycol of headpin [5] aromatic hydrocarbons sealing end is 3:1~3:4.
9. the preparation method of composite material according to claim 5, which is characterized in that in step (4), the dry tool
Body are as follows: 50 DEG C of dryings in air dry oven.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111393370A (en) * | 2020-03-30 | 2020-07-10 | 山西大学 | AB monomer based on column [5] arene and imidazole derivative and construction and application of supramolecular polymer network |
| CN112048073A (en) * | 2020-08-11 | 2020-12-08 | 太原理工大学 | Liquid crystal material based on columnar aromatic hydrocarbon and preparation method thereof |
| WO2021017319A1 (en) * | 2019-07-26 | 2021-02-04 | Tcl华星光电技术有限公司 | Liquid crystal alignment material and display panel |
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