CN102731771B - Hyperbranched polyaryletherketone, preparation method and application thereof - Google Patents
Hyperbranched polyaryletherketone, preparation method and application thereof Download PDFInfo
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- CN102731771B CN102731771B CN201210202255.7A CN201210202255A CN102731771B CN 102731771 B CN102731771 B CN 102731771B CN 201210202255 A CN201210202255 A CN 201210202255A CN 102731771 B CN102731771 B CN 102731771B
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- polyarylether ketone
- hyperbranched
- hyperbranched polyarylether
- liquid crystal
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4018—(I) or (II) containing halogens other than as leaving group (X)
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The present invention discloses hyperbranched polyaryletherketone, a preparation method and an application thereof. The hyperbranched polyaryletherketone comprises a compound represented by the following general formula, wherein a number average molecular weight of the compound is 27500-45000, a molecular weight distribution of the compound is 1.45-1.84, and R is-OH or a material represented by the following structure. The hyperbranched polyaryletherketone of the present invention can be used for preparation of a liquid crystal oriented film. The structure of the hyperbranched polyaryletherketone of the present invention is more similar to the structure of liquid crystal molecule so as to well provide acting force between the liquid crystal molecule and the liquid crystal oriented film.
Description
Technical field
The present invention relates to a kind of hyperbranched polyarylether ketone and preparation method thereof and application, relate in particular to hyperbranched polyarylether ketone of hydroxy-end capped hyperbranched polyarylether ketone and itrile group end-blocking and preparation method thereof and application.
Background technology
Liquid-crystal display requires liquid crystal molecule must be orientated according to certain orientation when display graphics under electric field action.What can make ordered liquid crystal molecule arrangement is the alignment films that is coated in liquid crystal cell internal surface, and the material that forms this film is exactly liquid crystal orientation film.In industrial production, be all macromolecule polymer material as the material of liquid crystal orientation film now, and the overwhelming majority is linear polymer material, after molecular weight is excessive, can there is deliquescent problem in linear polymeric polymkeric substance, simultaneously for grappling liquid crystal molecule need to be on linear molecular backbone chain introducing functional group as much as possible, thereby cause synthetic difficulty and cost higher.Used presoma polyamic acid material in order to improve the solubility problem of polyimide aligning film material, but the preservation of polyamic acid and use are all subject to the impact of time and environment very large, have restricted to a great extent the scope of its practical application.
Summary of the invention
The object of this invention is to provide a kind of solubility property good, good film-forming property, the hyperbranched polyarylether ketone strengthening with the reactive force of liquid crystal molecule between.
A kind of hyperbranched polyarylether ketone provided by the present invention, the following general formula compound that comprises number-average molecular weight 27500～45000, molecular weight distribution 1.45～1.84:
Wherein, R be-OH or
Another object of the present invention is to provide a kind of method of preparing hyperbranched polyarylether ketone.
The method of preparing hyperbranched polyarylether ketone provided by the present invention, comprises the steps:
Make 2,4 ', the fluoro-benzophenone of 6-tri-and Resorcinol generation polycondensation generate hydroxy-end capped hyperbranched polyarylether ketone; Described 2,4 ', the mol ratio 1:(2.1-2.25 of the fluoro-benzophenone of 6-tri-and described Resorcinol).
The method of hyperbranched polyarylether ketone of the present invention, also comprises that described hydroxy-end capped hyperbranched polyarylether ketone reacts the hyperbranched polyarylether ketone that generates itrile group end-blocking with described 4-nitro phthalic nitrile.
Wherein, described 2,4 ', the fluoro-benzophenone of 6-tri-and described Resorcinol, at 140-150 DEG C of salify 2-2.5 hour, are warmed up to 170-220 DEG C of reaction 6-8 hour.
Wherein, described 2,4 ', under the condition that the fluoro-benzophenone of 6-tri-and described Resorcinol exist at Anhydrous potassium carbonate and N-Methyl pyrrolidone, react.
Wherein, described hydroxy-end capped hyperbranched polyarylether ketone reacts under the condition of Anhydrous potassium carbonate and DMF existence with described 4-nitro phthalic nitrile.
The invention still further relates to above-mentioned hyperbranched polyarylether ketone in the application of preparing in liquid crystal orientation film.
Another object of the present invention is to provide the substrate of a kind of TFT-LCD.
The substrate of TFT-LCD provided by the present invention, comprises liquid crystal orientation film, and this liquid crystal orientation film comprises above-mentioned hyperbranched polyarylether ketone.
Hyperbranched polymer (hyper-branched) can simply be described as having the polymkeric substance of highly branched structure, and it is both different from branched polymer, also different with dendrimer.Unique like this structure, makes it have the molecular motion that is different from line polymer just, shows the property that many line polymers do not have.Hyperbranched poly hyperbranched polyarylether ketone of the present invention, due to carbonylate six-membered ring structure in dissaving structure, produces interactional group and introducing is more with liquid crystal molecule, and the reactive force between liquid crystal molecule and liquid crystal orientation film can be better provided.Hyperbranched poly solubility property of the present invention is good, good film-forming property.
Meanwhile, hydroxy-end capped hyperbranched polyarylether ketone further functionalization is introduced the structures similar to liquid crystal molecule such as itrile group, strengthens the reactive force to liquid crystal molecule.
Brief description of the drawings
Fig. 1 represents the Infrared Characterization collection of illustrative plates of the hyperbranched poly hyperbranched polyarylether ketone of the hydroxy-end capped hyperbranched polyarylether ketone of embodiment 1 and the itrile group end-blocking of embodiment 3.
Fig. 2 represents the Infrared Characterization collection of illustrative plates of the hydroxy-end capped hyperbranched polyarylether ketone of embodiment 2.
Fig. 3 represents that the nuclear-magnetism of the hyperbranched poly hyperbranched polyarylether ketone of the hydroxy-end capped hyperbranched polyarylether ketone of embodiment 1 and the itrile group end-blocking of embodiment 3 characterizes collection of illustrative plates.
Fig. 4 represents that the nuclear-magnetism of the hydroxy-end capped hyperbranched polyarylether ketone of embodiment 2 characterizes collection of illustrative plates.
Embodiment
Synthesizing of the hydroxy-end capped hyperbranched polyarylether ketone of embodiment 1.:
By 2.3619g BB
2' type monomer 2,4 ', the fluoro-benzophenone of 6-tri-(0.01mol), 2.3123g Resorcinol (0.021mol), 3.312g Anhydrous potassium carbonate (0.024mol), 25ml N-Methyl pyrrolidone (NMP), 10ml toluene is put into the 100ml there-necked flask that whipping appts is housed, logical nitrogen, stirring.Salify temperature is controlled at 140 DEG C of 2-2.5 hour; progressively be warmed up to 170 DEG C of reaction 6-8 hour; after cooling, reaction mixture is poured in acid deionized water; extremely neutral with hot wash under nitrogen protection; dry, then under nitrogen protection, use washing with alcohol 3 times, heat filtering; dry, obtaining terminal group is hydroxy-end capped hyperbranched polyarylether ketone (OH-HPEEK).
The number-average molecular weight 27500 ~ 45000 of hydroxy-end capped hyperbranched polyarylether ketone, molecular weight distribution 1.45 ~ 1.84, as shown in Figure 1, as shown in Figure 3, its structural formula is nuclear-magnetism characterization result its Infrared Characterization result:
Synthesizing of the hydroxy-end capped hyperbranched polyarylether ketone of embodiment 2.:
By 2.3619g BB
2' type monomer 2,4 ', the fluoro-benzophenone of 6-tri-(0.01mol), 2.4775g Resorcinol (0.0225mol), 3.312g Anhydrous potassium carbonate (0.024mol), 25ml N-Methyl pyrrolidone (NMP), 10ml toluene is put into the 100ml there-necked flask that whipping appts is housed, logical nitrogen, stirring.Salify temperature is controlled at 150 DEG C of 2-2.5 hour; progressively be warmed up to 220 DEG C of reaction 6-8 hour; after cooling, reaction mixture is poured in acid deionized water; extremely neutral with hot wash under nitrogen protection; dry, then under nitrogen protection, use washing with alcohol 3 times, heat filtering; dry, obtaining terminal group is hydroxy-end capped super hyperbranched polyarylether ketone (OH-HPEEK).
The number-average molecular weight 27500 ~ 45000 of hydroxy-end capped hyperbranched polyarylether ketone, molecular weight distribution 1.45 ~ 1.84, as shown in Figure 2, as shown in Figure 4, its structural formula is as follows for nuclear-magnetism characterization result for its Infrared Characterization result:
The hyperbranched polyarylether ketone of embodiment 3. itrile group end-blockings
By the hydroxy-end capped hyperbranched polyarylether ketone of 1.0g embodiment 1,0.69g 4-nitro phthalic nitrile (0.004mol), 1.10g Anhydrous potassium carbonate (0.008mol), 20ml N, dinethylformamide (DMF) is put into the 100ml there-necked flask that whipping appts is housed, logical nitrogen, stirring at room temperature is more than 24 hours.Reaction mixture is poured in deionized water, first washed with water to neutrality, dry, then under nitrogen protection, use washing with alcohol 3 times, and be dried, obtain the hyperbranched polyarylether ketone (CN-HPEEK) of itrile group end-blocking.
The number-average molecular weight 27500 ~ 45000 of the hyperbranched polyarylether ketone of itrile group end-blocking, molecular weight distribution 1.45～1.84, as shown in Figure 1, as shown in Figure 3, its structural formula is as follows for nuclear-magnetism characterization result for its Infrared Characterization result:
Performance analysis:
(1) solvability test
In the conventional solvent of following 10ml, add 1g polymkeric substance at normal temperatures, observe its dissolution degree.
Can dissolve at normal temperatures expression completely ++.
The above results illustrates that hyperbranched polyarylether ketone solubility property of the present invention is good.
(2) film forming
Prepare the hyperbranched polyarylether ketone 1g of the itrile group end-blocking of embodiment 3 gained, be dissolved in the NMP(AR of 10ml, Tianjin Tian Tai fine chemicals company limited) in, stir until it dissolves completely, obtain hyperbranched polyarylether ketone dispersion liquid, by spin-coating method (MTI Spin coating, model VTC-100, spin coating parameter: 1000r/ minute) prepolymer dispersion liquid is coated on cleaning glass substrate (10cm × 10cm), in vacuum drying oven, heat up by the stage, concrete heat treatment process is as follows: under condition of nitrogen gas, 275 DEG C of 4h, 325 DEG C of 1h of 300 DEG C of 1h, 350 DEG C of 1h, 375 DEG C of 4h.Remove solvent film forming, its thickness is 44 μ m.Observe the even thickness of film by atomic force microscope.
(3) tilt angle test
Make liquid crystal analog device: on the glass substrate of the liquid crystal orientation film being formed by the hyperbranched polyarylether ketone of embodiment 3 itrile group end-blockings, respectively determine 3cm × 3cm two, with rubbing machine (M-2000 type rubbing machine, Xuanhua, Hebei trier factory) alignment films is carried out to cocurrent and parallel friction, afterwards so that the relative mode of alignment films, by sealed plastic box (S-WB21 type, Sekisui Fine Chemical Co., Ltd.) along three limits of glass substrate by two bonding one-tenth boxes of sheet glass, sealed plastic box is first used to UV(UV-light) solidified for 60 seconds, then thermofixation more than 1 hour at 120 DEG C, ensure that sealed plastic box cements two glass substrates completely, finally inject liquid crystal (MAT-09-1284 type, Merck liquid crystal company) 0.03mg, and again seal and repeat the step of above-mentioned curing sealed plastic box by a small amount of sealed plastic box, make a complete liquid crystal analog device that can be used for test.
Adopt PAT20 type tilt angle tester (Changchun Lian Cheng Instrument Ltd.) (measuring error is ± 0.1 °), respectively gained liquid crystal analog device is carried out to tilt angle test, its tilt angle is respectively 0.9 °, 1.1 °, 1.5 °, 1.2 °, is greatly improved compared with the tilt angle of 2 ~ 5 ° of traditional STN type alignment film of polyimide.
In sum, hyperbranched polyarylether ketone solubility property of the present invention is good, and good film-forming property strengthens with the reactive force of liquid crystal molecule, is suitable for making liquid crystal orientation film.
The invention still further relates to above-mentioned hyperbranched polyarylether ketone in the application of preparing in liquid crystal orientation film.
The present invention also provides the substrate of TFT-LCD, comprises liquid crystal orientation film, and this liquid crystal orientation film comprises above-mentioned hyperbranched polyarylether ketone.The substrate of described TFT-LCD can be the array substrate of liquid-crystal display, or color membrane substrates.
More than explanation is just illustrative for the purpose of the present invention; and nonrestrictive, those of ordinary skill in the art understand, in the case of not departing from the spirit and scope that claims limit; can make many amendments, variation or equivalence, but all will fall within the scope of protection of the present invention.
Claims (4)
1. hyperbranched polyarylether ketone is in the application of preparing in liquid crystal orientation film, and described hyperbranched polyarylether ketone is the following general formula compound of number-average molecular weight 27500～45000, molecular weight distribution 1.45～1.84:
Wherein, R be-OH or
The preparation method of described hyperbranched polyarylether ketone, comprises the steps:
Make 2,4 ', the fluoro-benzophenone of 6-tri-and Resorcinol generation polycondensation generate hydroxy-end capped hyperbranched polyarylether ketone;
Described hydroxy-end capped hyperbranched polyarylether ketone reacts the hyperbranched polyarylether ketone that generates itrile group end-blocking with 4-nitro phthalic nitrile;
Described 2,4 ', the mol ratio 1:(2.1-2.25 of the fluoro-benzophenone of 6-tri-and described Resorcinol).
2. application according to claim 1, is characterized in that, described 2,4 ', the fluoro-benzophenone of 6-tri-and described Resorcinol, at 140-150 DEG C of salify 2-2.5 hour, are warmed up to 170-220 DEG C of reaction 6-8 hour.
3. application according to claim 1, is characterized in that, described hydroxy-end capped hyperbranched polyarylether ketone reacts under the condition of Anhydrous potassium carbonate and DMF existence with described 4-nitro phthalic nitrile.
4. application according to claim 1, is characterized in that, described 2,4 ', under the condition that the fluoro-benzophenone of 6-tri-and described Resorcinol exist at Anhydrous potassium carbonate and N-Methyl pyrrolidone, react.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210202255.7A CN102731771B (en) | 2012-06-15 | 2012-06-15 | Hyperbranched polyaryletherketone, preparation method and application thereof |
| PCT/CN2012/085264 WO2013185437A1 (en) | 2012-06-15 | 2012-11-26 | Hyperbranched polyaryletherketone, preparation method for same, application thereof, and substrate of thin-film transistor liquid crystal display device |
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| CN201210202255.7A CN102731771B (en) | 2012-06-15 | 2012-06-15 | Hyperbranched polyaryletherketone, preparation method and application thereof |
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| CN102731771A CN102731771A (en) | 2012-10-17 |
| CN102731771B true CN102731771B (en) | 2014-06-04 |
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| CN102731771B (en) * | 2012-06-15 | 2014-06-04 | 京东方科技集团股份有限公司 | Hyperbranched polyaryletherketone, preparation method and application thereof |
| WO2020163777A1 (en) * | 2019-02-08 | 2020-08-13 | The University Of North Carolina At Chapel Hill | Aromatic hyper branched polyaryletherketone-based membranes for high temperature gas separation |
| CN109810230A (en) * | 2019-02-18 | 2019-05-28 | 山东星火科学技术研究院 | A kind of preparation method of hyperbranched sulfonated polyether-ether-ketone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101357985A (en) * | 2008-09-23 | 2009-02-04 | 吉林大学 | Hyperbranched poly(aryl ether ketone), preparation method and application thereof in viscosity modifier |
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| JP2006267736A (en) * | 2005-03-24 | 2006-10-05 | Fuji Xerox Co Ltd | Hyper branch polymer for non-linear optics and non-linear optical member containing the same |
| TWI354579B (en) * | 2006-12-29 | 2011-12-21 | Ind Tech Res Inst | An exchange membrane containing modified maleimide |
| CN102731771B (en) * | 2012-06-15 | 2014-06-04 | 京东方科技集团股份有限公司 | Hyperbranched polyaryletherketone, preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101357985A (en) * | 2008-09-23 | 2009-02-04 | 吉林大学 | Hyperbranched poly(aryl ether ketone), preparation method and application thereof in viscosity modifier |
Non-Patent Citations (5)
| Title |
|---|
| Xiujie Li, Shuling Zhang, Fugui Zhou，et al.."Preparation and Characterization of Hyperbranched Poly(ether ether ketone)s Suitable as Rheology Control Agents for Linear Poly(ether ether ketone)s".《Macromolecular Research》.2011,第19卷(第5期), |
| Xiujie Li, Shuling Zhang, Fugui Zhou,et al.."Preparation and Characterization of Hyperbranched Poly(ether ether ketone)s Suitable as Rheology Control Agents for Linear Poly(ether ether ketone)s".《Macromolecular Research》.2011,第19卷(第5期), * |
| 严巍."可交联聚芳醚酮及其复合材料的制备与性能研究".《吉林大学硕士学位论文 可交联聚芳醚酮及其复合材料的制备与性能研究》.2010, |
| 严巍.可交联聚芳醚酮及其复合材料的制备与性能研究.《吉林大学硕士学位论文 可交联聚芳醚酮及其复合材料的制备与性能研究》.2010, * |
| 李秀杰."超支化聚醚醚酮的制备及其作为粘度调节剂的研究".《吉林大学博士学位论文 超支化聚醚醚酮的制备及其作为粘度调节剂的研究》.2011, |
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| WO2013185437A1 (en) | 2013-12-19 |
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