CN104497240A - Industrial synthesis method and application of high-fluidity polyether ether ketone resin - Google Patents
Industrial synthesis method and application of high-fluidity polyether ether ketone resin Download PDFInfo
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Abstract
The invention discloses an industrial synthesis method of high-fluidity polyether ether ketone resin. The industrial synthesis method comprises the following steps: in a reaction vessel, adding diphenyl sulfone, 4,4'-difluorobenzophenone and an alkali metal salt forming agent, starting stirring, heating until the monomer is completely dissolved, adding hydroquinone into the system, further uniformly stirring, heating, carrying out polymerization reaction, finally adding an end-capping reagent and further reacting to obtain a polymeric viscous liquid; cooling the polymeric viscous liquid with water, pulverizing into powder and filtering the powder, boiling the filtered powder with an organic solvent and deionized water, repeatedly washing and filtering to remove the solvent and by-product salt and drying to obtain polyether ether ketone resin, wherein the end-capping reagent is selected from one or more of 3,4'-difluorobenzophenone, 3-chloro-4-fluorobenzophenone, 3-fluoro-4-chlorobenzophenone and 3,4'-dichlorobenzophenone. The polyether ether ketone resin prepared by the industrial synthesis method has the advantages of low chroma, low melt viscosity, high fluidity and easiness in mold processing and can be used for preparation of heat-resistant and anti-corrosion coating and injection molded parts.
Description
Technical field
The invention belongs to technical field of polymer materials, be specifically related to a kind of Industrialized synthesis method and purposes of high workability polyether-ether-ketone resin.
Background technology
Polyether-ether-ketone is a kind of high performance engineering plastics, because it has thermotolerance, hot water resistance, wear resistance, resistance to fatigue, radioresistance, peel resistance, creep resistance, dimensional stability, shock-resistance, chemical proofing, the excellent over-all properties such as nontoxic, fire-retardant, thus for a long time electronics, electrical equipment, machinery, automobile, medical apparatus, aircraft industry, food-processing and not the field such as stickness paint obtain purposes widely.
Since the beginning of the sixties, water type coating came out, in succession develop multiple nothing (low) pollution, resource-saving, energy-saving coating new variety, wherein output is comparatively large, and what purposes was wider has following several: water type coating, high solid coating, powder coating and radiation curable coating.Powder coating is with the solid powdery synthetic resin coating of the composition such as solid resin and pigment, filler and auxiliary agent, has the features such as solvent-free pollution, the utilization ratio of coating when constructing is high, energy consumption is low.Along with the development of modern science technology, in the high-tech areas such as Aeronautics and Astronautics, electronics, machinery, more and more higher requirement is proposed to the thermotolerance of coating, due to the above characteristic of polyether-ether-ketone resin, its fine powder can be used as paint in material surface, formed there is good insulating, corrosion-resistant, heat-resisting, water-fast coated articles, can extensive use in chemical anticorrosion, household electrical appliance, electronics and mechanical field.
Because the solvent resistance of polyether-ether-ketone resin is excellent, therefore cannot make liquid coating as general protective system, pressed powder spraying can only be implemented.Even if but its more than fusing point 400 degree, the viscosity of fusing is also very large, poor fluidity.
The polyether-ether-ketone of general merchandise is because having higher crystallinity and higher melt viscosity, and its course of processing is only limitted to thermo forming, has the defects such as mold temperature is high, pressure is large, adds tooling cost.The polyether-ether-ketone of low melt viscosity, has lower flow temperature, therefore has good mobility under high temperature, is easy to forming process.In order to obtain the polyether-ether-ketone of low melt viscosity, Chinese patent CN 2014102190250 changes by changing molecular chain sequence the polyether-ether-ketone obtaining low melt viscosity by not changing the ratio of phenyl, ehter bond and ketone group, but this kind of method adds products material, add cost, process is uncontrollable; Also have US Patent No. 4920200 to utilize aromatic ring-shaped oligopolymer ring-opening polymerization to prepare polymkeric substance, this kind of method is equally applicable to the polyether-ether-ketone preparing low melt viscosity, but this kind of method introduces impurity, and involves great expense, also infeasible.
In sum, existing preparation high workability, all there is certain defect compared with the production method of the polyether-ether-ketone of low melting viscosity, the existence of these defects directly constrains purposes and the machine-shaping of polyether-ether-ketone coating.Therefore, need to find a kind of suitable method and produce low melting viscosity, polyether-ether-ketone that mobility is higher.
Summary of the invention
The object of the invention is to the defect overcoming above-mentioned prior art, the Industrialized synthesis method of the polyether-ether-ketone resin of a kind of high workability, low melting viscosity is provided.
For achieving the above object, the technical solution used in the present invention is:
An Industrialized synthesis method for high workability polyether-ether-ketone resin, comprises the following steps:
(1) in the reactor of nitrogen protection, add sulfobenzide, 4, start to stir after 4 '-difluoro benzophenone and basic metal salt forming agent, be warming up to 130 ~ 140 DEG C, the solid content of system is 15 ~ 40%, after monomer all dissolves, in system, add Resorcinol again, heat up after continuing to stir and carry out polyreaction, finally add end-capping reagent, continue reaction 10 ~ 30 minutes, obtain polymerization mucus;
(2) polymerization mucus is ground into powder after water cooling, the powder priority organic solvent after filtration, deionized water is boiled, repetitive scrubbing, and excessively filter solvent and by-product salt, namely obtain polyether-ether-ketone resin after drying.
Further, polyreaction described in step (1) refers to and system is warming up to 180 ~ 220 DEG C, react 1 ~ 2 hour, then 240 ~ 260 DEG C are warmed up to, react 0.5 ~ 2 hour, be then warmed up to 270 ~ 280 DEG C, react 0.5 ~ 2 hour, be warming up to 310 ~ 320 DEG C again, be polymerized 1 ~ 4 hour.
Further, the molar weight of described Resorcinol comparatively 4,4 '-difluoro benzophenone excessive 0.1 ~ 2%, or 4, the molar weight excessive compared with Resorcinol 0.1 ~ 2% of 4 '-difluoro benzophenone.
Further, described basic metal salt forming agent is sodium carbonate and/or salt of wormwood.
Further, described end-capping reagent is selected from 3,4 '-difluoro benzophenone, 3-chloro-4-fluorine benzophenone, the fluoro-4-chlorobenzophenone of 3-and 3, one or more in 4 '-dichloro benzophenone.
Further, the molar weight of described end-capping reagent is 2 ~ 5% of Resorcinol molar weight.
Further, the molar weight of described end-capping reagent is 4% of Resorcinol molar weight.
Further, step (2) described organic solvent is selected from methyl alcohol, ethanol or acetone.
The end-capping reagent that the present invention adopts is the asymmetric aromatic ketone radical derivative of a class, and its structural formula is as follows:
Such end-capping reagent has different functions, both can react and end-blocking with terminal hydroxy group, simultaneously has again certain polymerizing power and prevents the function of system depolymerization.In certain temperature range, such feature functionality group derivative has different substitutabilities, as 3,4 '-difluoro benzophenone, 4 '-position fluorine activity is obviously greater than 3-position fluorin radical, therefore 4 '-position fluorine participates in reaction fast plays end-blocking function, 3-position fluorin radical also has certain reactive behavior simultaneously, can participate in polyreaction, thus when ensure that end-blocking, system DeR does not occur.
When the molar weight comparatively 4 of Resorcinol, 4 '-difluoro benzophenone excessive 0.1 ~ 2% time, produce the resin obtained and be mainly applicable to injection moulding; When the molar weight of 4,4 '-difluoro benzophenone excessive compared with Resorcinol 0.1 ~ 2% time, produce the resin obtained and be mainly applicable to coating.
The invention has the beneficial effects as follows:
(1) the present invention passes through the asymmetric aromatic ketone monomer of employing one class as end-capping reagent, it not only has good end-blocking effect, and can polyreaction be participated in, thus when ensure that end-blocking there is not depolymerization phenomenon in system, avoid adding again of LiCl, reduce the post-processing difficulty of production cost and system, preparation-obtained end capped polyether sulphone resin has high workability simultaneously;
(2) salt forming agent of the present invention adopts the Na that is produced from China's Mainland
2cO
3, excessive Na
2cO
3be present in the form of a powder in system, hydrolyzed alkaline is obviously than KOH, NaOH and K
2cO
3system is low, weak to the toxic side effect of system, and adopts domestic Na
2cO
3the polyether-ether-ketone product of explained hereafter and use import Na
2cO
3the product produced for salt forming agent is distinguished without color and luster, reduces production cost;
(3) the polyether-ether-ketone range of molecular weight distributions prepared by the present invention is narrow, and there is low colourity, low melting viscosity, high workability, be easy to forming process, melting index is 90-150g/10min (400 DEG C, 5Kg), after sieving, particle order number is obtained at 200 ~ 400 orders.Adopt Electrostatic Spray Technology to be sprayed at smooth solid skin, high temperature resistant, corrosion-resistant finishes can be obtained.Polyether-ether-ketone prepared by the present invention can be used for preparing heat-resistant anticorrosive erosion coating and moulding, heat-resistant anticorrosive erosion coating can be used for army's industry such as submarine etc. and is often in the parts of briny environment, some that can be used for preparing under non-resistance to compression, hot conditions of heat-resistant anticorrosive moulding connect mouldings, and oil pump sealing member, the packing ring under high temperature and pad etc.
Embodiment
Embodiment 1
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 90.00Kg sulfobenzide, 30.00Kg4, start to stir after 4 '-difluoro benzophenone and 16.00Kg sodium carbonate, be warming up to 135 DEG C, after monomer all dissolves, 14.00Kg Resorcinol is added again in system, 200 DEG C are warming up to after continuing to stir, react 1.5 hours, then 250 DEG C are warmed up to, react 1 hour, then 275 DEG C are warmed up to, react 1 hour, be warming up to 315 DEG C again, be polymerized 2 hours, add 1.10Kg3, 4 '-difluoro benzophenone, continue reaction 20 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added alcohol reflux and boils 1 hour, so 10 times repeatedly, 1 hour is boiled again with deionized water, so 10 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
Gained polyether-ether-ketone resin melting index MI=125.5g/10min (365.0 DEG C, 5Kg, 5 minutes);
MI=125.0g/10min (365.0 DEG C, 5Kg, 30 minutes).
Result shows, gained polyether-ether-ketone resin has high workability, low melting viscosity.
Embodiment 2
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 90.00Kg sulfobenzide, 30.00Kg4, start to stir after 4 '-difluoro benzophenone and 16.00Kg sodium carbonate, be warming up to 135 DEG C, after monomer all dissolves, 14.00Kg Resorcinol is added again in system, 200 DEG C are warming up to after continuing to stir, react 1.5 hours, then 250 DEG C are warmed up to, react 1 hour, then 275 DEG C are warmed up to, react 1 hour, be warming up to 315 DEG C again, be polymerized 2 hours, add 832g3, 4 '-difluoro benzophenone, continue reaction 20 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added alcohol reflux and boils 1 hour, so 10 times repeatedly, 1 hour is boiled again with deionized water, so 10 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
Gained polyether-ether-ketone resin melting index MI=85.5g/10min (365.0 DEG C, 5Kg, 5 minutes);
MI=125.0g/10min (365.0 DEG C, 5Kg, 30 minutes).
Result shows, gained polyether-ether-ketone resin has high workability, low melting viscosity.
Embodiment 3
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 90.00Kg sulfobenzide, 30.00Kg4, start to stir after 4 '-difluoro benzophenone and 16.00Kg sodium carbonate, be warming up to 135 DEG C, after monomer all dissolves, 14.00Kg Resorcinol is added again in system, 200 DEG C are warming up to after continuing to stir, react 1.5 hours, then 250 DEG C are warmed up to, react 1 hour, then 275 DEG C are warmed up to, react 1 hour, be warming up to 315 DEG C again, be polymerized 2 hours, add 1.387Kg3, 4 '-difluoro benzophenone, continue reaction 20 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added alcohol reflux and boils 1 hour, so 10 times repeatedly, 1 hour is boiled again with deionized water, so 10 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
Gained polyether-ether-ketone resin melting index MI=155.5g/10min (365.0 DEG C, 5Kg, 5 minutes);
MI=155.0g/10min (365.0 DEG C, 5Kg, 30 minutes).
Result shows, gained polyether-ether-ketone resin has high workability, low melting viscosity.
Embodiment 4
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 400mmol sulfobenzide, 100.01mmol 4, start to stir after 4 '-difluoro benzophenone and 150mmol salt of wormwood, be warming up to 130 DEG C, after monomer all dissolves, 100mmol Resorcinol is added again in system, 180 DEG C are warming up to after continuing to stir, react 1 hour, then 240 DEG C are warmed up to, react 0.5 hour, then 270 DEG C are warmed up to, react 0.5 hour, be warming up to 310 DEG C again, be polymerized 1 hour, add 4mmol 3-chloro-4-fluorine benzophenone, continue reaction 10 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added methanol eddy and boils 0.5 hour, so 8 times repeatedly, 0.5 hour is boiled again with deionized water, so 8 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
Embodiment 5
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 400mmol sulfobenzide, 102mmol 4, start to stir after 4 '-difluoro benzophenone and 140mmol salt of wormwood, be warming up to 140 DEG C, after monomer all dissolves, 100mmol Resorcinol is added again in system, 220 DEG C are warming up to after continuing to stir, react 2 hours, then 260 DEG C are warmed up to, react 2 hours, then 280 DEG C are warmed up to, react 2 hours, be warming up to 320 DEG C again, be polymerized 4 hours, add the fluoro-4-chlorobenzophenone of 2mmol 3-, continue reaction 30 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added acetone reflux and boils 2 hours, so 8 times repeatedly, 2 hours are boiled again with deionized water, so 8 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
Embodiment 6
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 350mmol sulfobenzide, 100mmol 4, start to stir after 4 '-difluoro benzophenone and 130mmol sodium carbonate, be warming up to 135 DEG C, after monomer all dissolves, 100.01mmol Resorcinol is added again in system, 200 DEG C are warming up to after continuing to stir, react 1.5 hours, then 250 DEG C are warmed up to, react 1 hour, then 275 DEG C are warmed up to, react 1 hour, be warming up to 315 DEG C again, polyase 13 hour, add 5mmol 3, 4 '-dichloro benzophenone, continue reaction 20 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added alcohol reflux and boils 1 hour, so 10 times repeatedly, 2 hours are boiled again with deionized water, so 10 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
Embodiment 7
In 200 liters of stainless steel cauldrons of nitrogen protection that high-efficiency stirrer is housed, first add 450mmol sulfobenzide, 100mmol 4, 4 '-difluoro benzophenone and 70mmol salt of wormwood, start after 70mmol sodium carbonate to stir, be warming up to 135 DEG C, after monomer all dissolves, 102mmol Resorcinol is added again in system, 200 DEG C are warming up to after continuing to stir, react 1.5 hours, then 250 DEG C are warmed up to, react 1 hour, then 275 DEG C are warmed up to, react 1 hour, be warming up to 315 DEG C again, polyase 13 hour, add 2mmol 3, 4 '-dichloro benzophenone and 2mmol 3, 4 '-difluoro benzophenone, continue reaction 20 minutes, mucus must be polymerized, polymerization mucus is ground into powder after water cooling, powder after filtration is added alcohol reflux and boils 1 hour, so 10 times repeatedly, 1 hour is boiled again with deionized water, so 10 times repeatedly, in water, chloride ion content is till below 5ppm, crosses and filters solvent and by-product salt, by filter after polymkeric substance vacuum-drying to moisture weight content lower than 0.5%, obtain polyether-ether-ketone resin.
The above; be only the specific embodiment of the present invention, but protection scope of the present invention is not limited thereto, anyly belongs to those skilled in the art in the technical scope that the present invention discloses; the change that can expect easily or replacement, all should be encompassed within protection scope of the present invention.Therefore, protection scope of the present invention should be as the criterion with the protection domain of claim.
Claims (9)
1. an Industrialized synthesis method for high workability polyether-ether-ketone resin, is characterized in that, comprises the following steps:
(1) in the reactor of nitrogen protection, add sulfobenzide, 4, start to stir after 4 '-difluoro benzophenone and basic metal salt forming agent, be warming up to 130 ~ 140 DEG C, after monomer all dissolves, then add Resorcinol in system, heat up after continuing to stir and carry out polyreaction, finally add end-capping reagent, continue reaction 10 ~ 30 minutes, obtain polymerization mucus;
(2) polymerization mucus is ground into powder after water cooling, the powder priority organic solvent after filtration, deionized water is boiled, repetitive scrubbing, and excessively filter solvent and by-product salt, namely obtain polyether-ether-ketone resin after drying.
2. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, it is characterized in that, polyreaction described in step (1) refers to and system is warming up to 180 ~ 220 DEG C, react 1 ~ 2 hour, be then warmed up to 240 ~ 260 DEG C, react 0.5 ~ 2 hour, then 270 ~ 280 DEG C are warmed up to, react 0.5 ~ 2 hour, then be warming up to 310 ~ 320 DEG C, be polymerized 1 ~ 4 hour.
3. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, it is characterized in that, the molar weight of described Resorcinol comparatively 4,4 '-difluoro benzophenone excessive 0.1 ~ 2%, or 4, the molar weight excessive compared with Resorcinol 0.1 ~ 2% of 4 '-difluoro benzophenone.
4. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, is characterized in that, described basic metal salt forming agent is sodium carbonate and/or salt of wormwood.
5. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, it is characterized in that, described end-capping reagent is selected from 3,4 '-difluoro benzophenone, 3-chloro-4-fluorine benzophenone, the fluoro-4-chlorobenzophenone of 3-and 3, one or more in 4 '-dichloro benzophenone.
6. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, is characterized in that, the molar weight of described end-capping reagent is 2 ~ 5% of Resorcinol molar weight.
7. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, is characterized in that, the molar weight of described end-capping reagent is 4% of Resorcinol molar weight.
8. the Industrialized synthesis method of high workability polyether-ether-ketone resin according to claim 1, is characterized in that, step (2) described organic solvent is selected from methyl alcohol, ethanol or acetone.
9. the high workability polyether-ether-ketone resin any one of claim 1 ~ 8 for the preparation of protective system and heat-resistant anticorrosive articles injection-moulded.
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| CN105524239A (en) * | 2016-01-28 | 2016-04-27 | 淄博迈特瑞工程材料有限公司 | Method for modifying PEEK (polyether-ether-ketone) by titanium |
| CN106752806A (en) * | 2017-01-25 | 2017-05-31 | 山东凯盛新材料股份有限公司 | The preparation method of the PEKK electrostatic spraying powder coating with cross-linking properties |
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| CN110256643A (en) * | 2019-06-26 | 2019-09-20 | 南京清研高分子新材料有限公司 | A method of preparing polyether-ether-ketone resin |
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| CN105418910A (en) * | 2015-11-30 | 2016-03-23 | 广东优巨先进材料研究有限公司 | Method for synthesizing end-capped bisphenol A polyaryletherketone resin with semi-flexible structure |
| CN105524239A (en) * | 2016-01-28 | 2016-04-27 | 淄博迈特瑞工程材料有限公司 | Method for modifying PEEK (polyether-ether-ketone) by titanium |
| CN107663272A (en) * | 2016-11-18 | 2018-02-06 | 中国科学院海洋研究所 | A kind of Pyrogentisinic Acid base polyether-ether-ketone resin in the wear-resisting composite coating of marine corrosion environment and preparation method thereof |
| CN106752806A (en) * | 2017-01-25 | 2017-05-31 | 山东凯盛新材料股份有限公司 | The preparation method of the PEKK electrostatic spraying powder coating with cross-linking properties |
| CN107383293B (en) * | 2017-08-16 | 2019-07-02 | 宜宾天原集团股份有限公司 | A kind of preparation method of the polyether-ether-ketone suitable for 3D printing |
| CN107383293A (en) * | 2017-08-16 | 2017-11-24 | 宜宾天原集团股份有限公司 | A kind of preparation method of polyether-ether-ketone suitable for 3D printing |
| CN107618122A (en) * | 2017-10-31 | 2018-01-23 | 山东凯盛新材料股份有限公司 | The preparation method of PEKK fine powder |
| CN108239245A (en) * | 2017-12-05 | 2018-07-03 | 宜宾天原集团股份有限公司 | A kind of preparation method of dissolvable polyether-ether-ketone |
| CN107936205A (en) * | 2017-12-14 | 2018-04-20 | 陈逊 | A kind of manufacture method of polyether-ether-ketone resin |
| CN109438640A (en) * | 2018-10-25 | 2019-03-08 | 宜宾天原集团股份有限公司 | A kind of preparation method of high fluidity low viscosity polyether-ether-ketone |
| CN110256643A (en) * | 2019-06-26 | 2019-09-20 | 南京清研高分子新材料有限公司 | A method of preparing polyether-ether-ketone resin |
| CN114031770A (en) * | 2021-06-25 | 2022-02-11 | 赵学强 | Method for preparing polyether-ether-ketone by using ionic liquid as solvent |
| CN113912799A (en) * | 2021-09-16 | 2022-01-11 | 吉林省中研高分子材料股份有限公司 | Polyetheretherketone and preparation method thereof |
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