CN106589382A - Preparation method of fluorescent polyhedral oligomeric silsesquioxane/polymethyl methacrylate - Google Patents
Preparation method of fluorescent polyhedral oligomeric silsesquioxane/polymethyl methacrylate Download PDFInfo
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- CN106589382A CN106589382A CN201610916978.1A CN201610916978A CN106589382A CN 106589382 A CN106589382 A CN 106589382A CN 201610916978 A CN201610916978 A CN 201610916978A CN 106589382 A CN106589382 A CN 106589382A
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- fluorescence
- oligomeric silsesquioxane
- polyhedral oligomeric
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
- C08L33/12—Homopolymers or copolymers of methyl methacrylate
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- 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
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1491—Heterocyclic containing other combinations of heteroatoms
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention relates to a preparation method of novel fluorescent polyhedral oligomeric silsesquioxane/polymethyl methacrylate (POSS/PMMA). The method comprises the following steps: introducing a long-conjugate fluorine derivative EMOF with high fluorescence quantum yield to POSS by using an addition reaction of a Si-H bond and end alkyne through molecular design to prepare a dendritic organic/inorganic hybrid luminescent material EMOF-POSS with the POSS as a core and a fluorescence chromophore as an arm; and preparing an inorganic/organic composite nanomaterial from the EMOF-POSS and the PMMA through a solution blending technology. Combination of the POSS and the EMOF effectively reduces aggregation of the fluorescence chromophore in the PMMA matrix, so the luminescence properties of the material are obviously improved, and the composite material has good heat stability.
Description
Technical field
The present invention relates to a kind of new fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate (POSS/
PMMA preparation method), belongs to plastics modification technology field.
Background technology
In recent years, luminous organic material was widely used in electroluminescent and display device field, and main target is to improve
The efficiency of luminescent device.Most of luminescent materials have higher fluorescence quantum yield in the solution, and in the collected state then
Fluorescent weakening or even the phenomenon being quenched can occur.In addition, the heat stability of luminescent material is poor, equally easily send out when temperature is higher
Raw quenching effect.And in actual life application, people generally require luminescent material to be made with certain contour structures
Solid, therefore, how effectively eliminating the aggregation quenching effect of luminescent material and improving its heat stability just becomes organic light emission
Materials problem demanding prompt solution.
Polyhedral oligomeric silsesquioxane (POSS) is that a class has nanoscale (0.5～3nm), has cage structure
Si-O organic inorganic hybridization molecules.As organic and inorganic component is effectively combined by POSS on a molecular scale by chemical bond
Together, the molecule-type hybrid composite material of formation has higher heat stability, good dissolubility and machinability, and
Novel reactive functionality etc..
The preparation method of POSS/ polymer nanocomposites mainly includes two class of physical blending and chemical copolymerization.Wherein,
Physical blending process process is simple, easy to operate but common POSS are difficult to be uniformly dispersed in the polymer.Chemical copolymerization method is to pass through
Reactive functional groups on POSS carry out nano composite material obtained from copolyreaction with organic monomer.It is prepared by chemical copolymerization method
Composite in POSS be not susceptible to reunite, be conducive to the raising of material property, but operating procedure be complicated, not easy-regulating.This
In patent of invention, POSS declines through the modified surface energy in EMOF surfaces, can be evenly dispersed in polymeric matrix, therefore
Simple solution blended process can be selected to prepare the long conjugation fluorene kind derivative 2- acetenyl -7- with high-fluorescence quantum yield
(4- (4- methoxyl-styrenes) styryl) -9,9- dioctyl fluorenes (EMOF)/PMMA (EMOF-POSS/PMMA) composite wood
Material.
To sum up, in prior art, luminescent material can produce aggregation quenching effect in coherent condition, and heat stability is poor,
POSS can improve the stability of luminescent material, but POSS is difficult uniformly to mix in luminescent material.
The content of the invention
The problem that the present invention is solved is that the fluorescence property of polymethyl methacrylate (PMMA) is poor, and heat stability is not
It is good；To solve the problem, the present invention provides a kind of preparation of fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate
Method.
The preparation method of fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate that the present invention is provided, its feature
It is, including preparing fluorescence polyhedral oligomeric silsesquioxane；Fluorescence polyhedral oligomeric silsesquioxane modified polymethyl acid first
Ester.
The preparation method of fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate that the present invention is provided, selects
EMOF fluorescent agents are modified to polyhedral oligomeric silsesquioxane by silicon hydrogenation, prepare fluorescence polyhedral oligomeric silsesquioxane
Alkane.
Further, silicon hydrogenation Schlenk technologies used in nitrogen atmosphere are carried out in biexhaust pipe；Including：To be many
Face oligomeric silsesquioxane is with EMOF fluorescent agents with mol ratio as 1：The ratio and mass content of (7～8) is 0.3～0.5%
It is in catalyst Pt input Schlenk pipes, with biexhaust pipe extraction nitrogen, injection solvent Isosorbide-5-Nitrae-dioxane and anti-at 75～83 DEG C
20～30h, stopping is answered to heat and be cooled to room temperature.
Further, described EMOF fluorescent agents are long conjugation fluorene kind derivative 2- acetenyl -7- (4- (4- methoxybenzene second
Thiazolinyl) styryl) -9,9- dioctyl fluorenes (EMOF), its structure is：
Described polyhedral oligomeric silsesquioxane has one of following structure：
Further, fluorescence polyhedral oligomeric silsesquioxane modified poly (methyl methacrylate) includes that just mass fraction is
0.5～4.0% fluorescence polyhedral oligomeric silsesquioxane, polymethyl methacrylate difference wiring solution-forming, after solution blending, rotation
Steam solvent and be dried.
Further, the solvent of the solution is THF solution, and mixing time is more than one hour.
Beneficial effects of the present invention：
In the novel fluorescence POSS/PMMA composites that the present invention is provided, EMOF-POSS not only has good thermally-stabilised
Property (modified PMMA starting degradation temperature temperature is 290～295 DEG C), and the addition of POSS effectively reduces fluorescence chromophore
Aggregation, improves the fluorescence quantum yield and luminescent properties of composite.In addition, the Schlenk methods that the present invention is adopted are
The mode of operation commonly used in POSS synthesis, industrial implementation are convenient；And the Combined Mining of EMOF-POSS and PMMA uses more simple molten
Liquid is blended, and cost of implementation is low；THF used by solution blending by revolving can realize recycling, therefore effect on environment compared with
It is little.
Specific embodiment
Hereinafter, with reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate
The present invention rather than restriction the scope of the present invention.In addition, it is to be understood that after the content for having read instruction of the present invention, this area
Technical staff can be made various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims
Limited range.
The preparation method of the fluorescence POSS modified PMMA resins that the present invention is provided, while giving PMMA fluorescence properties, carries
The Nano filling dispersibility of high material and heat stability.Preparation method bag of the present invention with regard to fluorescence POSS modified PMMA resins
Include：Prepare two steps of preparation of fluorescence POSS and fluorescence POSS modified PMMA composites.
The present invention is to POSS to be modified fluorescence POSS by silicon hydrogenation from EMOF fluorescent agents, prepares silicon hydrogenation
Reaction Schlenk technologies used in nitrogen atmosphere are carried out in biexhaust pipe.By POSS and EMOF with mol ratio as 1：(7～8)
Ratio and gross mass 0.3～0.5% catalyst Pt input Schlenk pipes in, with biexhaust pipe extraction nitrogen, inject solvent 1,
4- dioxane simultaneously reacts 20～30h at 75～83 DEG C, and stopping is heated and is cooled to room temperature stopped reaction.Successively with normal hexane
Reactant liquor is carried out precipitating-dissolution process with THF, to remove catalyst and unnecessary monomer in reaction.Finally product is put
It is dried to constant weight, kept dry in vacuum drying oven.The molecular structural formula of EMOF is：
POSS in the embodiment of the present invention using hexahydro Quito face silsesquioxane, octahydro Quito face silsesquioxane, ten
Any one in hydrogen-based multiaspect silsesquioxane, ten dihydro Quito face silsesquioxanes, molecular structural formula is successively such as following formula institute
Show：
The preparation method of fluorescence POSS modified PMMA composites includes：It is 0.5～4.0% by EMOF mass fractions
EMOF-POSS and PMMA are made into THF solution respectively, and more than 1h is stirred after blending, and vacuum drying after revolving solvent obtains EMOF-
POSS/PMMA nano composite materials.The mass fraction of EMOF has influence on the thermally-stabilised and luminescent properties of fluorescence POSS.
Embodiment 1
By POSS and EMOF with mol ratio as 1：7 ratio and the catalyst Pt input Schlenk pipes of gross mass 0.3%
In, with biexhaust pipe extraction nitrogen 3 times, injection solvent Isosorbide-5-Nitrae-dioxane simultaneously reacts 20h at 75 DEG C, and stopping is heated and is cooled to
Room temperature stopped reaction.Reactant liquor is carried out precipitating with normal hexane and THF successively-dissolution process 3 times to be to remove the catalysis in reaction
Agent and unnecessary monomer.Product is placed in vacuum drying oven finally to be always dried to constant weight, kept dry.
EMOF-POSS that mass fraction is 0.5% and PMMA are made into into THF solution respectively, 1h after blending, is stirred, are rotated molten
Vacuum drying after agent obtains the EMOF-POSS/PMMA nano composite materials that POSS is uniformly dispersed, fluorescent emission intensity is high, is combined
Material starting degradation temperature is 290 DEG C.
Embodiment 2
By POSS and EMOF with mol ratio as 1：8 ratio and the catalyst Pt input Schlenk pipes of gross mass 0.5%
In, with biexhaust pipe extraction nitrogen 3 times, injection solvent Isosorbide-5-Nitrae-dioxane simultaneously reacts 30h at 83 DEG C, and stopping is heated and is cooled to
Room temperature stopped reaction.Reactant liquor is carried out precipitating with normal hexane and THF successively-dissolution process 3 times to be to remove the catalysis in reaction
Agent and unnecessary monomer.Product is placed in vacuum drying oven finally to be always dried to constant weight, kept dry.
EMOF-POSS that mass fraction is 4.0% and PMMA are made into into THF solution respectively, 1.5h after blending, is stirred, are rotated
Vacuum drying after solvent obtains the EMOF-POSS/PMMA nano composite materials that POSS is uniformly dispersed, fluorescent emission intensity is high, multiple
Condensation material starting degradation temperature is 295 DEG C.
Embodiment 3
By POSS and EMOF with mol ratio as 1:7.2 ratio and the catalyst Pt input Schlenk pipes of gross mass 0.4%
In, with biexhaust pipe extraction nitrogen 3 times, injection solvent Isosorbide-5-Nitrae-dioxane simultaneously reacts 24h at 81 DEG C, and stopping is heated and is cooled to
Room temperature stopped reaction.Reactant liquor is carried out precipitating with normal hexane and THF successively-dissolution process 3 times to be to remove the catalysis in reaction
Agent and unnecessary monomer.Product is placed in vacuum drying oven finally to be always dried to constant weight, kept dry.
EMOF-POSS that mass fraction is 2.0% and PMMA are made into into THF solution respectively, 2h after blending, is stirred, are rotated molten
Vacuum drying after agent obtains the EMOF-POSS/PMMA nano composite materials that POSS is uniformly dispersed, fluorescent emission intensity is high, is combined
Material starting degradation temperature is 292 DEG C.
Embodiment 4
By POSS and EMOF with mol ratio as 1:7.7 ratio and the catalyst Pt input Schlenk of gross mass 0.47%
Guan Zhong, with biexhaust pipe extraction nitrogen 3 times, injection solvent Isosorbide-5-Nitrae-dioxane simultaneously reacts 27h at 80 DEG C, and stopping is heated and cooled down
To room temperature stopped reaction.Reactant liquor is carried out precipitating with normal hexane and THF successively-dissolution process 3 times to be to remove urging in reaction
Agent and unnecessary monomer.Product is placed in vacuum drying oven finally to be always dried to constant weight, kept dry.
EMOF-POSS that mass fraction is 3.8% and PMMA are made into into THF solution respectively, 3h after blending, is stirred, are rotated molten
Vacuum drying after agent obtains the EMOF-POSS/PMMA nano composite materials that POSS is uniformly dispersed, fluorescent emission intensity is high, is combined
Material starting degradation temperature is 294 DEG C.
Embodiment 5
By POSS and EMOF with mol ratio as 1:7.2 ratio and the catalyst Pt input Schlenk of gross mass 0.48%
Guan Zhong, with biexhaust pipe extraction nitrogen 3 times, injection solvent Isosorbide-5-Nitrae-dioxane simultaneously reacts 29h at 76 DEG C, and stopping is heated and cooled down
To room temperature stopped reaction.Reactant liquor is carried out precipitating with normal hexane and THF successively-dissolution process 3 times to be to remove urging in reaction
Agent and unnecessary monomer.Product is placed in vacuum drying oven finally to be always dried to constant weight, kept dry.
EMOF-POSS that mass fraction is 3.6% and PMMA are made into into THF solution respectively, more than 1.5h after blending, is stirred,
Vacuum drying after revolving solvent obtains the nano combined materials of EMOF-POSS/PMMA that POSS is uniformly dispersed, fluorescent emission intensity is high
Material, composite starting degradation temperature is 295 DEG C.
To sum up, the preparation method of fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate that the present invention is provided is obtained
The fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate fluorescence property for arriving is good, and mixture be uniformly dispersed, it is thermally-stabilised
Property is good.
Claims (6)
1. a kind of preparation method of fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate, it is characterised in that including system
Standby fluorescence polyhedral oligomeric silsesquioxane；Fluorescence polyhedral oligomeric silsesquioxane modified poly (methyl methacrylate).
2. according to the preparation method of the fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate described in claim 1, its
It is characterised by, polyhedral oligomeric silsesquioxane is modified by silicon hydrogenation from EMOF fluorescent agents, prepares fluorescence many
Face oligomeric silsesquioxane.
3. according to the preparation method of the fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate described in claim 2, its
It is characterised by, silicon hydrogenation Schlenk technologies used in nitrogen atmosphere are carried out in biexhaust pipe；Including：By polyhedral oligomeric
Silsesquioxane is with EMOF fluorescent agents with mol ratio as 1：The ratio and mass content of (7～8) are 0.3～0.5% catalyst
In Pt input Schlenk pipes, with biexhaust pipe extraction nitrogen, inject solvent Isosorbide-5-Nitrae-dioxane and at 75～83 DEG C reaction 20～
30h, stopping are heated and are cooled to room temperature.
4. according to the preparation method of the fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate described in claim 2, its
It is characterised by, described EMOF fluorescent agents are long conjugation fluorene kind derivative 2- acetenyl -7- (4- (4- methoxyl-styrenes) benzene
Vinyl) -9,9- dioctyl fluorenes (EMOF), its structure is：
Described polyhedral oligomeric silsesquioxane has one of following structure：
5. according to the preparation method of the fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate described in claim 1, its
It is characterised by, by the fluorescence polyhedral oligomeric silsesquioxane modified poly (methyl methacrylate) bag that mass fraction is 0.5～4.0%
Include fluorescence polyhedral oligomeric silsesquioxane, polymethyl methacrylate difference wiring solution-forming, after solution blending, revolving solvent is simultaneously
It is dried.
6. according to the preparation method of the fluorescence polyhedral oligomeric silsesquioxane/polymethyl methacrylate described in claim 5, its
It is characterised by, the solvent of the solution is THF solution, and mixing time is more than one hour.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109786823A (en) * | 2019-01-22 | 2019-05-21 | 广东天劲新能源科技股份有限公司 | A kind of PMMA base method for preparing gel polymer electrolyte |
| CN111423596A (en) * | 2020-05-19 | 2020-07-17 | 常州大学 | Trackable auxiliary agent and preparation method thereof |
| CN111785845A (en) * | 2019-04-04 | 2020-10-16 | 上海和辉光电有限公司 | Thin film packaging material, manufacturing method thereof, thin film packaging structure and electronic device |
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| KR20140092470A (en) * | 2012-12-28 | 2014-07-24 | 코오롱플라스틱 주식회사 | Polycabonate resin composition and polycabonate resin molded articles comprising the same |
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2016
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101538463A (en) * | 2008-03-18 | 2009-09-23 | 王广武 | Light-storable self luminous transparent film |
| KR20140092470A (en) * | 2012-12-28 | 2014-07-24 | 코오롱플라스틱 주식회사 | Polycabonate resin composition and polycabonate resin molded articles comprising the same |
Non-Patent Citations (3)
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| 黄棋尤译: "《塑料制品设计工程手册》", 30 June 1990, 轻工业出版社 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109786823A (en) * | 2019-01-22 | 2019-05-21 | 广东天劲新能源科技股份有限公司 | A kind of PMMA base method for preparing gel polymer electrolyte |
| CN111785845A (en) * | 2019-04-04 | 2020-10-16 | 上海和辉光电有限公司 | Thin film packaging material, manufacturing method thereof, thin film packaging structure and electronic device |
| CN111423596A (en) * | 2020-05-19 | 2020-07-17 | 常州大学 | Trackable auxiliary agent and preparation method thereof |
| CN111423596B (en) * | 2020-05-19 | 2022-03-01 | 常州大学 | Trackable auxiliary agent and preparation method thereof |
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Application publication date: 20170426 |