CN102731771A - Hyperbranched polyaryletherketone, preparation method and application thereof - Google Patents
Hyperbranched polyaryletherketone, preparation method and application thereof Download PDFInfo
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- CN102731771A CN102731771A CN2012102022557A CN201210202255A CN102731771A CN 102731771 A CN102731771 A CN 102731771A CN 2012102022557 A CN2012102022557 A CN 2012102022557A CN 201210202255 A CN201210202255 A CN 201210202255A CN 102731771 A CN102731771 A CN 102731771A
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- aryl ether
- ether ketone
- hyperbranched poly
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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)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 poly aryl ether ketone and preparation method thereof and application, relate in particular to hydroxy-end capped hyperbranched poly aryl ether ketone and the end capped hyperbranched poly aryl ether ketone of itrile group and preparation method thereof and application.
Background technology
Liquid-crystal display requires liquid crystal molecule under electric field action, must be orientated according to certain orientation during display graphics.What can make the ordered liquid crystal molecule arrangement is the alignment films that is coated in the liquid crystal cell internal surface, and the material that forms this film is exactly a liquid crystal orientation film.The material as liquid crystal orientation film all is a macromolecule polymer material on the industrial production now; And the overwhelming majority is the linear polymer material; Can there be deliquescent problem in the linear polymeric polymkeric substance after molecular weight is excessive; Simultaneously for the grappling liquid crystal molecule need be on linear molecular backbone chain introducing functional group as much as possible, thereby cause synthetic difficulty and cost higher.For the solubility problem of improving the polyimide aligning film material has been used presoma polyamic acid material, but the preservation of polyamic acid and use all receive the influence of time and environment very big, have restricted the scope of its practical application to a great extent.
Summary of the invention
It is good to the purpose of this invention is to provide a kind of solubility property, and good film-forming property is with the reactive force enhanced hyperbranched poly aryl ether ketone of liquid crystal molecule between.
A kind of hyperbranched poly aryl ether ketone provided by the present invention comprises the formula compound of number-average molecular weight 27500～45000, MWD 1.45～1.84:
Wherein, R is-OH or
Another object of the present invention provides a kind of method for preparing the hyperbranched poly aryl ether ketone.
The method for preparing the hyperbranched poly aryl ether ketone provided by the present invention comprises the steps:
Make 2,4 ', 6-three fluoro-benzophenone and Resorcinol generation polycondensation generate hydroxy-end capped hyperbranched poly aryl ether ketone; Said 2,4 ', the mol ratio 1 of 6-three fluoro-benzophenone and said Resorcinol: (2.1-2.25).
The method of hyperbranched poly aryl ether ketone of the present invention comprises that also the reaction of said hydroxy-end capped hyperbranched poly aryl ether ketone and said 4-nitro phthalic nitrile generates the end capped hyperbranched poly aryl ether ketone of itrile group.
Wherein, said 2,4 ', 6-three fluoro-benzophenone and said Resorcinol were warmed up to 170-220 ℃ of reaction 6-8 hour at 140-150 ℃ of salify 2-2.5 hour.
Wherein, said 2,4 ', 6-three fluoro-benzophenone and said Resorcinol react under the condition that Anhydrous potassium carbonate and N-Methyl pyrrolidone exist.
Wherein, said hydroxy-end capped hyperbranched poly aryl ether ketone and said 4-nitro phthalic nitrile react under the condition that dinethylformamide exists at Anhydrous potassium carbonate and N.
The invention still further relates to the application of above-mentioned hyperbranched poly aryl ether ketone in the preparation liquid crystal orientation film.
Another purpose of the present invention provides 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 poly aryl ether ketone.
Hyperbranched polymer (hyper-branched) can simply be described as having the polymkeric substance of highly branched structure, and it was both different with branched polymer, and is also different with dendrimer.So just particular structure makes it have the molecular motion that is different from line polymer, shows the property that many line polymers do not have.Hyperbranched poly hyperbranched poly aryl ether ketone of the present invention, owing to carbonylate six-membered ring structure in dissaving structure, and introducing is more and liquid crystal molecule produces interactional group, and the reactive force between liquid crystal molecule and the liquid crystal orientation film can better be provided.Hyperbranched poly solubility property of the present invention is good, good film-forming property.
Simultaneously, hydroxy-end capped hyperbranched poly aryl ether ketone further functionalization is introduced the structures similar with liquid crystal molecule such as itrile group, strengthens the reactive force to liquid crystal molecule.
Description of drawings
Fig. 1 representes the IR Characterization collection of illustrative plates of the end capped hyperbranched poly hyperbranched poly of itrile group aryl ether ketone of hydroxy-end capped hyperbranched poly aryl ether ketone and the embodiment 3 of embodiment 1.
Fig. 2 representes the IR Characterization collection of illustrative plates of the hydroxy-end capped hyperbranched poly aryl ether ketone of embodiment 2.
Fig. 3 representes that the nuclear-magnetism of the end capped hyperbranched poly hyperbranched poly of itrile group aryl ether ketone of hydroxy-end capped hyperbranched poly aryl ether ketone and the embodiment 3 of embodiment 1 characterizes collection of illustrative plates.
Fig. 4 representes that the nuclear-magnetism of the hydroxy-end capped hyperbranched poly aryl ether ketone of embodiment 2 characterizes collection of illustrative plates.
Embodiment
Synthesizing of embodiment 1. hydroxy-end capped hyperbranched poly aryl ether ketones:
With 2.3619g BB
2' type monomer 2,4 ', 6-three fluoro-benzophenone (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.The salify temperature be controlled at 140 ℃ 2-2.5 hour, progressively be warmed up to 170 ℃ the reaction 6-8 hour, after the cooling reaction mixture is poured in the acid deionized water; Extremely neutral with hot wash under nitrogen protection; Drying, again under nitrogen protection with washing with alcohol 3 times, heat filtering; Drying, obtaining terminal group is hydroxy-end capped hyperbranched poly aryl ether ketone (OH-HPEEK).
The number-average molecular weight 27500 ~ 45000 of hydroxy-end capped hyperbranched poly aryl ether ketone, MWD 1.45 ~ 1.84, the result is as shown in Figure 1 for its IR Characterization, and the nuclear-magnetism characterization result is as shown in Figure 3, and its structural formula is:
Synthesizing of embodiment 2. hydroxy-end capped hyperbranched poly aryl ether ketones:
With 2.3619g BB
2' type monomer 2,4 ', 6-three fluoro-benzophenone (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.The salify temperature be controlled at 150 ℃ 2-2.5 hour, progressively be warmed up to 220 ℃ the reaction 6-8 hour, after the cooling reaction mixture is poured in the acid deionized water; Extremely neutral with hot wash under nitrogen protection; Drying, again under nitrogen protection with washing with alcohol 3 times, heat filtering; Drying, obtaining terminal group is hydroxy-end capped ultra hyperbranched poly aryl ether ketone (OH-HPEEK).
The number-average molecular weight 27500 ~ 45000 of hydroxy-end capped hyperbranched poly aryl ether ketone, MWD 1.45 ~ 1.84, the result is as shown in Figure 2 for its IR Characterization, and the nuclear-magnetism characterization result is as shown in Figure 4, and its structural formula is following:
The end capped hyperbranched poly aryl ether ketone of embodiment 3. itrile groups
Hydroxy-end capped hyperbranched poly aryl ether ketone with 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 is more than 24 hours.Reaction mixture is poured in the deionized water, and first water is washed till neutrality, drying, again under nitrogen protection with washing with alcohol 3 times, drying obtains the end capped hyperbranched poly aryl ether ketone of itrile group (CN-HPEEK).
The number-average molecular weight 27500 ~ 45000 of the end capped hyperbranched poly aryl ether ketone of itrile group, MWD 1.45～1.84, the result is as shown in Figure 1 for its IR Characterization, and the nuclear-magnetism characterization result is as shown in Figure 3, and its structural formula is following:
Performance analysis:
(1) solvability test
In the conventional solvent of following 10ml, add the 1g polymkeric substance at normal temperatures, observe its dissolution degree.
Can dissolve expression fully at normal temperatures ++.
The above results explains that hyperbranched poly aryl ether ketone solubility property of the present invention is good.
(2) film forming
Prepare the end capped hyperbranched poly aryl ether ketone of the itrile group 1g of embodiment 3 gained, it is dissolved among the NMP (AR, the safe fine chemicals in sky, Tianjin ltd) of 10ml; Stirring is dissolved until it fully; Obtain hyperbranched poly aryl ether ketone dispersion liquid, through spin-coating method (MTI Spin coating, model VTC-100; Spin coating parameter: 1000r/ minute) the prepolymer dispersion liquid is coated on the cleaning glass substrate (on the 10cm * 10cm); In vacuum drying oven, heat up through the stage, concrete heat treatment process is following: under condition of nitrogen gas, and 275 ℃ of 4h, 325 ℃ of 1h of 300 ℃ of 1h, 350 ℃ of 1h, 375 ℃ of 4h.Remove solvent and film forming, its thickness is 44 μ m.The thickness of observing film through AFM AFM is even.
(3) tilt angle test
Make the liquid crystal analog device: on the glass substrate of the liquid crystal orientation film that forms by the end capped hyperbranched poly aryl ether ketone of embodiment 3 itrile groups; Respectively determine 3cm * 3cm two; (M-2000 type rubbing machine, Xuanhua, Hebei trier factory) carries out the cocurrent and parallel friction to alignment films with rubbing machine, afterwards so that relative mode, usefulness envelope frame glue (the S-WB21 type of alignment films; Sekisui Fine Chemical Co., Ltd.) along three limits of glass substrate with two bonding one-tenth boxes of sheet glass; Use UV (UV-light) to solidify for 60 seconds earlier to envelope frame glue, more than 1 hour, guarantee that envelope frame glue cements two glass substrates fully 120 ℃ of following thermofixations then; Inject liquid crystal (MAT-09-1284 type at last; Merck liquid crystal company) 0.03mg, and use a small amount of envelope frame glue to seal and repeat the step of above-mentioned curing envelope frame glue once more, process a complete liquid crystal analog device that can be used for testing.
Adopt PAT20 type tilt angle tester (Changchun joins sincere Instr Ltd.) (measuring error is for ± 0.1 °); Respectively gained liquid crystal analog device is carried out the tilt angle test; Its tilt angle is respectively 0.9 °, 1.1 °, 1.5 °, 1.2 °, compares with the tilt angle of 2 ~ 5 ° of traditional STN type alignment film of polyimide to be greatly improved.
In sum, hyperbranched poly aryl ether ketone solubility property of the present invention is good, good film-forming property, and the reactive force enhancing with liquid crystal molecule is suitable for making liquid crystal orientation film.
The invention still further relates to the application of above-mentioned hyperbranched poly aryl ether ketone in the preparation 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 poly aryl ether ketone.The substrate of said 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 skills understand, under the situation of spirit that does not break away from accompanying claims and limited and scope; Can make many modifications, variation or equivalence, but all will fall in protection scope of the present invention.
Claims (8)
1. hyperbranched poly aryl ether ketone comprises the formula compound of number-average molecular weight 27500～45000, MWD 1.45～1.84:
Wherein, R is-OH or
2. a method for preparing the hyperbranched poly aryl ether ketone comprises the steps:
Make 2,4 ', 6-three fluoro-benzophenone and Resorcinol generation polycondensation generate hydroxy-end capped hyperbranched poly aryl ether ketone;
Said 2,4 ', the mol ratio 1 of 6-three fluoro-benzophenone and said Resorcinol: (2.1-2.25).
3. method according to claim 2 is characterized in that, comprises that also the reaction of said hydroxy-end capped hyperbranched poly aryl ether ketone and said 4-nitro phthalic nitrile generates the end capped hyperbranched poly aryl ether ketone of itrile group.
4. according to claim 2 or 3 described methods, it is characterized in that, said 2,4 ', 6-three fluoro-benzophenone and said Resorcinol were warmed up to 170-220 ℃ of reaction 6-8 hour at 140-150 ℃ of salify 2-2.5 hour.
5. method according to claim 3 is characterized in that, said hydroxy-end capped hyperbranched poly aryl ether ketone and said 4-nitro phthalic nitrile react under the condition that dinethylformamide exists at Anhydrous potassium carbonate and N.
6. method according to claim 2 is characterized in that, said 2,4 ', 6-three fluoro-benzophenone and said Resorcinol react under the condition that Anhydrous potassium carbonate and N-Methyl pyrrolidone exist.
7. the application of the described hyperbranched poly aryl ether ketone of claim 1 in the preparation liquid crystal orientation film.
8. the substrate of a TFT-LCD comprises liquid crystal orientation film, and this liquid crystal orientation film comprises the described hyperbranched poly aryl ether ketone of claim 1.
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 true CN102731771A (en) | 2012-10-17 |
| CN102731771B CN102731771B (en) | 2014-06-04 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013185437A1 (en) * | 2012-06-15 | 2013-12-19 | 京东方科技集团股份有限公司 | Hyperbranched polyaryletherketone, preparation method for same, application thereof, and substrate of thin-film transistor liquid crystal display device |
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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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 |
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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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| 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 |
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| 《Macromolecular Research》 20110531 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" 第19卷, 第5期 * |
| 《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》 20100819 严巍 "可交联聚芳醚酮及其复合材料的制备与性能研究" , * |
| 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》, vol. 19, no. 5, 31 May 2011 (2011-05-31) * |
| 严巍: "《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》", 19 August 2010, article ""可交联聚芳醚酮及其复合材料的制备与性能研究"" * |
| 李秀杰: "《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》", 6 September 2011, article ""超支化聚醚醚酮的制备及其作为粘度调节剂的研究"" * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013185437A1 (en) * | 2012-06-15 | 2013-12-19 | 京东方科技集团股份有限公司 | Hyperbranched polyaryletherketone, preparation method for same, application thereof, and substrate of thin-film transistor liquid crystal display device |
| 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 |
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| CN102731771B (en) | 2014-06-04 |
| WO2013185437A1 (en) | 2013-12-19 |
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