CN106117531A - The synthetic method of a kind of novel optical copolyesters and performance - Google Patents

The synthetic method of a kind of novel optical copolyesters and performance Download PDF

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CN106117531A
CN106117531A CN201610439564.4A CN201610439564A CN106117531A CN 106117531 A CN106117531 A CN 106117531A CN 201610439564 A CN201610439564 A CN 201610439564A CN 106117531 A CN106117531 A CN 106117531A
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quantum dot
carbon quantum
copolyesters
end hydroxy
water
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CN106117531B (en
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贾坤
何小红
周雪飞
张大伟
徐明珍
刘孝波
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University of Electronic Science and Technology of China
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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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Nanotechnology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

The invention belongs to polymer luminescent material field, be specifically related to synthetic method and the luminescent properties research thereof of the optics polyester copolymer that a class possesses blue emission characteristic and the good end hydroxy polyether of toughness is modified.Such novel optical polyester is obtained by the copolyreaction of end hydroxy polyether with ethylene glycol terephthalate, the introducing of end hydroxy polyether, on the one hand can improve the toughness of polyester as soft section of copolymer molecule chain；On the other hand can be pyrolyzed generation carbon quantum dot in situ, give the fluorescence emitting characteristics that copolyesters is special, under solution and solid fabric state, all present strong blue fluorescent emissions characteristic.Synthetic method of the present invention is the most effective, it is thus achieved that novel optical copolyesters in fields such as bio-imaging, fluorescence sense, photodiode, photocatalysis, there is potential application prospect.

Description

The synthetic method of a kind of novel optical copolyesters and performance
Technical field
The invention belongs to polymer luminescent material field, relate to synthetic method and the performance thereof of a class novel optical copolyesters Research.
Background technology
Polyethylene terephthalate (PET) is a kind of typical thermoplastic resin, owing to containing fragrance on its main chain Ring, is allowed to have higher fusing point and more rich physicochemical property compared with aliphatic polyester.Nineteen forty-one, Englishman J.R.Whenfield P-phthalic acid and ethylene glycol is used to be that raw material has synthesized PET polyester first, has been made for polyester fiber Shen with J.D.Dickson Please patent, completed pilot scale in 1949 in Britain subsequently.Owing to the spinning effect of PET is good, the fibre property prepared is excellent, Du pont company founds the factory first after purchase patent and realizes the industrialized production of PET polyester fiber.PET is as one synthesis fibre Tie up and be just widely applied once coming out, be made that tremendous contribution for human lives and production and be sure to occupy first of synthetic fibers. And there is the feature such as Heat stability is good, hygroscopicity is little, hardness is big, easy to process, resistance to chemical attack due to PET simultaneously, therefore 80 Since age, PET also has breakthrough development as engineering plastics, in industries such as organic electro-optic device, packaging, automobile, buildings Tool is widely used, it has also become one of five large-engineering plastics.More crisp yet with PET quality, limit the most to a certain extent Some require higher applications to toughness of material, and PET polyester should in the major part of optical material with devices field simultaneously With being all based on its high transparent at visible light wave range, thus it is necessary PET to carry out suitable modification to improve its toughness also The further optical property of abundant polyester, thus expand the polyester application model at engineering plastics and optical material with devices field Enclose.
Carbon quantum dot (CDs) is the fluorescent carbon nano-particle with torispherical structure of a kind of 10nm of being smaller in size than.2004 Year, Xu etc., during utilizing Purified in electrophoresis to be prepared SWCN by arc discharge, is found that the carbon of luminescence is received first Rice corpuscles, referred to as carbon quantum dot.Subsequently, the Sun Ya equality people of Clemson University was at first time laser etching method in 2006 It is prepared for carbon quantum dot.Thereafter, researcher uses electrochemical oxidation, pyrolysis, microwave cracking, hydro-thermal method to be prepared the most successively. Owing to carbon quantum dot has higher biocompatibility, hypotoxicity, stability of photoluminescence compared with conventional semiconductors quantum dot and organic dyestuff, Thus since self-discovery, the most of great interest, at present at bio-imaging, fluorescence sense, organic photovoltaic, light emitting diode Potential using value is shown with catalytic field.But, current majority system relates to multiple step or passivation for the method for CDs Process, therefore develop a class and simplify the method for synthesis carbon quantum dot and be a need for.
Summary of the invention
The present invention provides synthetic method and the photoluminescence property thereof of the novel high tenacity optics copolyesters of a class.Thered is provided There is fluorescent emission character and the good novel optical copolyesters of toughness, synthetic method is simple, by single step reaction by end hydroxyl Base polyethers introduces in polyester molecule chain, on the one hand enhances the toughness of copolyesters, on the other hand gives copolyesters good photic The characteristics of luminescence, shows as its solid fabric and solution and is provided with strong blue emission characteristic under ultraviolet excitation.
The technical scheme is that:
(1) structure of novel copolymerized ester.
Novel copolymerized ester is obtained by oligomer and the end hydroxy polyether generation polycondensation reaction of ethylene glycol terephthalate, its Structural formula is as follows:
(2) blue emission copolyesters and the synthetic method of water-solubility fluorescent carbon quantum dot.
A kind of have blue emission and the novel copolymerized ester of good toughness and the synthetic method of water-solubility fluorescent carbon quantum dot, bag Include following steps:
(1) in reactor, it is sequentially added into 20 parts of p-phthalic acids, 0.5-2.5 part M-phthalic acid and 13 parts of ethylene glycol.
(2) gained mixture in step (1) is forced into 2-3bars under nitrogen protection, stirs back at 220-240 DEG C Flow 2～4 hours.
(3) reactor pressure is down to normal pressure, and the water and the unnecessary ethylene glycol that step (2) reaction are generated are discharged.
(4) temperature of reaction kettle rises to 265～285 DEG C, adds 3-5 part true through 120 DEG C in the reactant liquor of step (3) gained Empty dried end hydroxy polyether, adds 0.2-0.3 part Sb2O3Making catalyst, increase to melt viscosity, reaction about 2～4 is little Time.
(5) step (4) gained fused mass is injected quick cooling in flowing water and obtains novel fluorescence copolyesters.
(6) in the reaction vessel with stirring and heater, add 10～30mmol end hydroxy polyethers, be passed through nitrogen, It is stirred at reflux at 260～280 DEG C 3～4 hours, obtains the carbon quantum dot being dispersed in alcohol.
Reaction mechanism of the present invention can be described as follows:
The novel copolymerized ester of tool blue emission provided by the present invention and good toughness is by a class PET oligomer and end hydroxyl Base polyethers generation polycondensation reaction and formed block copolymer method synthesis.Higher temperature in preparation process makes part end hydroxyl Base polyethers has been decomposed thermally to form carbon quantum dot to be disperseed in the copolymer, thus obtains the fluorescence copolymerization with blue emission characteristic Thing.Additionally, due to the embedding that end hydroxy polyether soft segment is in PET skeleton makes copolymer have higher toughness.
In sum, the technical characterstic of the present invention be following some:
1, synthesized and possess high tenacity and there is the novel copolymerized ester of blue emission characteristic, its simple synthetic method, efficiently, It is easily achieved industrialization, aqueous solution and solid fabric all show blue emission characteristic.
2, the fluorescent characteristic of synthesized novel copolymerized ester comes from the carbon quantum dot that building-up process situ produces.
3, being prepared for the adjustable carbon quantum dot of fluorescence emission wavelengths by one-step synthesis, its preparation method is easy, do not make With strong acid and strong base and passivator, and there is good water solublity.
4, by the time of the carbon quantum dot prepared by control, the size of carbon quantum dot can be adjusted.
Accompanying drawing explanation
Fig. 1 is that the aqueous solution of the fluorescence quantum that the present invention provides is inhaled at the ultraviolet-visible corresponding to the differential responses time Receive spectrum and fluorescence emission spectrum.
Fig. 2 be the novel copolymerized ester that the present invention provides synthetic route and with tradition pet polymer differential scanning amount Hot instrument and thermogravimetric analysis data.
Fig. 3 is the novel copolymerized ester that provides of the present invention and the resonance offset effect of tradition pet polymer and X-ray diffraction spectrum Figure.
Fig. 4 is the novel copolymerized ester that provides of present invention fluorescence excitation in the solution and emission spectrum and solid fabric thereof Emission spectrum.
Detailed description of the invention
Below by way of the description of detailed description of the invention, the present invention will be further described, but this not limit to the present invention System, those skilled in the art, according to the basic thought of the present invention, can make various modification, basic without departing from the present invention Thought, the most within the scope of the present invention.
Embodiment 1: the synthesis of the novel copolymerized ester of blue emission of the present invention
(1) in reactor, it is sequentially added into 20 parts of p-phthalic acids, 2 parts of M-phthalic acids and 13 parts of ethylene glycol.
(2) gained mixture in step (1) is forced into 2.7bars under nitrogen protection, is stirred at reflux at 230 DEG C 2.5 hour.
(3) reactor pressure is down to normal pressure, and the water and the unnecessary ethylene glycol that step (2) reaction are generated are discharged.
(4) temperature of reaction kettle rises to 280 DEG C, adds 4.2 parts and do through 120 DEG C of vacuum in the reactant liquor of step (3) gained End hydroxy polyether after dry, adds 0.26 part of Sb2O3Make catalyst, increase to melt viscosity, react 3.5 hours.
(5) step (4) gained fused mass is injected quick cooling in flowing water and obtains fluorescence copolyesters.
Embodiment 2: the optical property of fluorescent carbon quantum dot of the present invention
(1) in the reaction vessel with stirring and heater, add 30mmol end hydroxy polyether, be passed through nitrogen, It is stirred at reflux at 280 DEG C 3.5 hours, the carbon quantum dot with polyethers must be disperseed.
(2) with pure water as solvent, the response time of configuration low concentration is respectively 0.5h, 1.5h, 2.0h, 2.5h, 3.0h The carbon quantum dot solution being dispersed in PEG obtained with 3.5h, carries out uv-visible absorption spectra scanning respectively.
(3) with pure water as solvent, the carbon quantum dot solution obtained under the configuration 0.25g/mL differential responses time.
(4) using spectrofluorophotometer, arranging wavelength of transmitted light is 450nm, and slit width is 10nm, and PMT voltage is 400V, response time 0.1s, obtain the excitation spectrum of each solution in (2) by length scanning, thus determine excitation wavelength range.
(5) use spectrofluorophotometer, arrange excitation wavelength be respectively 300nm, 330nm, 365nm, 420nm and 420nm, slit width is 10nm, and PMT voltage is 400V, response time 0.1s, obtains by scanning under different excitation wavelengths (2) fluorescence emission spectrum of each solution in.
Thus obtain uv-visible absorption spectra and the fluorescence emission of the carbon quantum dot of acquisition under the differential responses time Spectrum is as it is shown in figure 1, present the characteristic absorption peak of 245nm in ultra-violet absorption spectrum；In fluorescence emission spectrum it can be seen that with The increase maximum emission peak in response time occurs in that red shift, and after the longer response time, emission band broadens, maximum excitation ripple Long it be positioned at 365nm and be basically unchanged, and the increase of transmitted wave personal attendant's excitation wavelength and red shift, show the carbon amounts having obtained in the present invention Sub-point.
Embodiment 3: the crystallinity of the novel copolymerized ester of the present invention and thermal stability
(1) the temperature control program arranging differential scanning calorimeter (DSC) is that the speed with 50 DEG C/min rises to 280 DEG C from 25 DEG C Rear holding 10min, to eliminate thermal history, is down to 40 DEG C with the speed of 15 DEG C/min subsequently, then with the speed falling-rising of 15 DEG C/min extremely 320 DEG C, respectively PET polyester and novel copolymerized ester are tested, obtain its differential scanning (DSC) curve.
(2) the temperature control program arranging thermogravimetric analyzer is to rise to 600 DEG C with the speed of 20 DEG C/min, divides under nitrogen atmosphere Other pet polymer and novel copolymerized ester are carried out thermogravimetric analysis, obtain its thermogravimetric analysis (TGA) curve.
(3) with PLM with heating stage, pet polymer and novel copolymerized ester are carried out respectively the sight of nonisothermal crystallization behavior Examine, obtain its polarized light microscopy picture.
(4) it is a length of with transmitted wave that X-ray diffractometer working voltage 40kV, electric current 30mA are setTo pet polymer Carry out X-ray diffraction (XRD) scanning with novel copolymerized ester, obtain its XRD spectra.
Thus obtaining PET and the DSC of novel copolymerized ester, TGA, polarized light microscopy and XRD figure to compose as shown in Figure 2,3, Fig. 2 presents The route map of the novel copolymerized ester going out synthesis shows that end hydroxy polyether segment is embedded in PET skeleton, thus shows higher Toughness；And novel copolymerized ester reduces by 20 DEG C, degree of supercooling increase and cold crystallization peak relative to pet polymer fusing point in DSC curve Appearance all prove novel copolymerized ester crystallize imperfection, i.e. the introducing of PEG flexible chain reduce PET strand regularity and then Affect its crystallinity.Simultaneously from the figure 3, it may be seen that relative to PET, synthesizing new copolyesters owes regular spherocrystal pattern and wider XRD diffraction maximum has proved this viewpoint further；Fig. 2 also embodies crystallization imperfection and result in novel copolymerized ester heat stability simultaneously Decline.
Embodiment 4: the photoluminescent property of the novel copolymerized ester of the present invention
(1) making solvent with sym-tetrachloroethane and phenol volume ratio 1:1, configuration concentration is the copolyesters solution of 0.5g/mL.
(2) using spectrofluorophotometer, arranging fluorescence emission wavelengths is 450nm, and slit width is 10nm, PMT voltage For 400V, response time 0.1s, obtain the excitation spectrum of solution in (1) by length scanning.
(3) using spectrofluorophotometer, arranging fluorescence exciting wavelength is 385nm, and slit width is 10nm, PMT voltage For 400V, response time 0.1s, obtain the emission spectrum of solution in (1) by length scanning.
(4) use 405nm laser instrument that sample microcell is excited, it is thus achieved that the fluorescent emission of novel copolymerized ester solid fabric Spectrum.
The copolyesters fluorescence excitation obtained and emission spectrum as shown in Figure 4, can be seen that the transmitting light of copolyesters from spectrum Compose close with the emission spectrum of carbon quantum dot in the present invention, show fluorescent light source end hydroxy polyether in building-up process of copolyesters The thermal decomposition of segment and the carbon quantum dot that formed, solid-state emission spectrum relatively solution emission spectrum has obvious red shift simultaneously.

Claims (3)

1. the method that a class prepares novel optical copolyesters and water-solubility fluorescent carbon quantum dot, it is characterised in that include walking as follows Rapid:
(1) in reactor, it is sequentially added into 20 parts of p-phthalic acids, 0.5-2.5 part M-phthalic acid and 13 parts of ethylene glycol.
(2) gained mixture in step (1) is forced into 2-3bars under nitrogen protection, at 220-240 DEG C, is stirred at reflux 2 ～4 hours.
(3) reactor pressure is down to normal pressure, and the water and the unnecessary ethylene glycol that step (2) reaction are generated are discharged.
(4) temperature of reaction kettle rises to 265～285 DEG C, adds 3-5 part and do through 120 DEG C of vacuum in the reactant liquor of step (3) gained End hydroxy polyether after dry, adds 0.2-0.3 part Sb2O3Make catalyst, increase to melt viscosity, react about 2～4 hours.
(5) step (4) gained fused mass is injected quick cooling in flowing water and obtains novel fluorescence copolyesters.
(6) in the reaction vessel with stirring and heater, add 10～30mmol end hydroxy polyethers, be passed through nitrogen, It is stirred at reflux at 260～280 DEG C 3～4 hours, obtains the carbon quantum dot being dispersed in alcoholic solvent.
The most according to claim 1, the novel copolymerized ester of blue emission and the method for water-solubility fluorescent carbon quantum dot, its feature exists In: step (4) adds flexible ends hydroxy polyethers to improve the toughness of tradition PET polyester；Step (6) uses one-step synthesis Thermally decomposing to yield fluorescent carbon quantum dot by end hydroxy polyether, synthetic method is simple, does not uses strong acid and strong base or passivator.
3. having preferable toughness and fluorescent characteristic according to the novel copolymerized ester of blue emission described in claim 1,2, it is luminous special Property come from building-up process situ formed carbon quantum dot；Described water-solubility fluorescent carbon quantum dot has flexible adjustable fluorescence and sends out Penetrating characteristic and preferable ultraviolet-visible spectrum absorbability, water solublity is good, and can adjust carbon by the control in response time Quantum point grain diameter.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115851269A (en) * 2022-12-01 2023-03-28 南京工业大学 Method for preparing fluorescent carbon quantum dots by using waste PET and application of fluorescent carbon quantum dots in LED

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103087302A (en) * 2013-01-22 2013-05-08 金发科技股份有限公司 Copolyester, preparation method and application thereof
CN103387831A (en) * 2013-07-24 2013-11-13 中国科学院长春光学精密机械与物理研究所 Carbon nano point with high fluorescence quantum efficiency and preparation method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103087302A (en) * 2013-01-22 2013-05-08 金发科技股份有限公司 Copolyester, preparation method and application thereof
CN103387831A (en) * 2013-07-24 2013-11-13 中国科学院长春光学精密机械与物理研究所 Carbon nano point with high fluorescence quantum efficiency and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RUI-JUN FAN等: ""Photoluminescent carbon dots directly derived from polyethylene glycol and their application for cellular imaging"", 《CARBON》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115851269A (en) * 2022-12-01 2023-03-28 南京工业大学 Method for preparing fluorescent carbon quantum dots by using waste PET and application of fluorescent carbon quantum dots in LED
CN115851269B (en) * 2022-12-01 2024-03-29 南京工业大学 Method for preparing fluorescent carbon quantum dots by using waste PET and application of fluorescent carbon quantum dots in LED

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