CN110256643A - A method of preparing polyether-ether-ketone resin - Google Patents
A method of preparing polyether-ether-ketone resin Download PDFInfo
- Publication number
- CN110256643A CN110256643A CN201910563187.9A CN201910563187A CN110256643A CN 110256643 A CN110256643 A CN 110256643A CN 201910563187 A CN201910563187 A CN 201910563187A CN 110256643 A CN110256643 A CN 110256643A
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- Prior art keywords
- ether
- ketone resin
- solvent
- reaction
- preparing polyether
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- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000004696 Poly ether ether ketone Substances 0.000 title claims abstract description 27
- 229920002530 polyetherether ketone Polymers 0.000 title claims abstract description 27
- 239000011347 resin Substances 0.000 title claims abstract description 24
- 229920005989 resin Polymers 0.000 title claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 23
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 18
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940113088 dimethylacetamide Drugs 0.000 claims abstract description 7
- 239000011259 mixed solution Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 238000010792 warming Methods 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 230000001376 precipitating effect Effects 0.000 claims abstract description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 5
- 238000002242 deionisation method Methods 0.000 claims 1
- 238000010025 steaming Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- PZDAAZQDQJGXSW-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)benzene Chemical group C1=CC(F)=CC=C1C1=CC=C(F)C=C1 PZDAAZQDQJGXSW-UHFFFAOYSA-N 0.000 description 1
- -1 Isopropanol Dimethyl acetamide N-Methyl pyrrolidone Chemical compound 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
Abstract
The present invention provides a kind of method for preparing polyether-ether-ketone resin.The method of the present invention includes following steps: (1) polymerization reaction: by 4, 4'- difluoro benzophenone, hydroquinone and sodium carbonate are added in reactor, then solvent is added and water entrainer makes the solid-liquid volume ratio in reactor be 1:2-1:3, under nitrogen protection and stirring action, it is heated to 130-150 DEG C, water entrainer is removed after reaction 1h, it is heated slowly to 180-225 DEG C again, reaction 1 hour, then slowly it is warming up to 260-280 DEG C, reaction 2-3 hours, wherein the volume ratio of solvent and water entrainer is 2:1-3:1, the solvent uses mass ratio are as follows: the isopropanol of 10:10:1, dimethyl acetamide, the mixed solution of N-Methyl pyrrolidone；(2) the precipitating processing of reaction product；(3) wash: the product after vacuum flashing is dry after being washed with deionized.The present invention can effectively shorten the production cycle, reduce the production cost of polyether-ether-ketone resin, improve product purity.
Description
Technical field:
The present invention relates to a kind of methods for preparing polyether-ether-ketone resin, belong to technical field of organic chemistry.
Background technique:
Polyether-ether-ketone (PEEK) resin is aromatic series crystal type thermoplastic macromolecule material, with high mechanical strength, high temperature resistant,
Impact resistance, fire-retardant, acid and alkali-resistance, hydrolysis, wear-resisting, endurance, radiation resistance and good electrical property.Many special dimensions can be with
Substitute the traditional materials such as metal, ceramics.The high temperature resistants of the plastics, self-lubricating, wear-resistant and antifatigue etc. characteristics, make and work as
Modern most popular one of high performance engineering plastics, it is mainly used in aerospace, auto industry, electric and medical instrument
Equal fields.
The main method for preparing polyether-ether-ketone at present is to be using 4,4'- difluoro benzophenone, hydroquinone and sodium carbonate
Raw material is synthesized as solvent using diphenyl sulphone (DPS) and is made.Polycondensation reaction carries out at a temperature of 150 DEG C to 340 DEG C.Initial reaction temperature is wanted
It is low, in order to avoid loss hydroquinone, and reduce side reaction.Then slowly heating, polymer are dissolved in a solvent, are reacted at 320 DEG C
It is lower to carry out completely.Solvent diphenyl sulphone (DPS) first is removed by repeatedly extracting with water-miscible organic solvent after the completion of polymerization reaction, then uses water
By repeatedly extracting removal water-miscible organic solvent and by-product salt, production procedure is long, at high cost.
Summary of the invention:
The purpose of the present invention is providing a kind of method for preparing polyether-ether-ketone resin in view of the above problems, can effectively shorten
Production cycle reduces the production cost of polyether-ether-ketone resin, improves product purity.
Above-mentioned purpose is realized by following technical scheme:
A method of polyether-ether-ketone resin being prepared, this method comprises the following steps:
(1) polymerization reaction: 4,4'- difluoro benzophenone, hydroquinone and sodium carbonate are added in reactor, solvent is then added
The solid-liquid volume ratio in reactor is made to be that 1:2-1:3 is heated to 130- under nitrogen protection and stirring action with water entrainer
150 DEG C, water entrainer is removed after reacting 1h, then be heated slowly to 180-225 DEG C, reacts 1 hour, be then slowly warming up to 260-
280 DEG C, the heating-up time is 0.5 hour, is reacted 2-3 hours, wherein the volume ratio of solvent and water entrainer is 2:1-3:1, described
Solvent uses mass ratio are as follows: the isopropanol of 10:10:1, dimethyl acetamide, N-Methyl pyrrolidone mixed solution；
(2) the precipitating processing of reaction product: 100-120 DEG C is cooled to after polymerization reaction, the product produced to polymerization reaction
Middle that solvent as described in step (1) is added, stirring to reaction system uniformly carries out vacuum flashing afterwards；
(3) wash: the product after vacuum flashing is dry after being washed with deionized.
The method for preparing polyether-ether-ketone resin, in polymerization reaction described in step (1), 4,4'- difluorodiphenyl first
The molar ratio of ketone, hydroquinone and sodium carbonate is 1:0.995:1.
The method for preparing polyether-ether-ketone resin, water entrainer described in step (1) use dimethylbenzene.
The method for preparing polyether-ether-ketone resin, the pressure of vacuum flashing described in step (2) be not more than in
0.05MPa, temperature are 245-255 DEG C.
The method for preparing polyether-ether-ketone resin, the solid-liquid matter in deionized water washing process described in step (3)
Amount is than being 1:3.
The invention has the advantages that: the present invention is using the isopropanol of 10:10:1, dimethyl acetamide, N-Methyl pyrrolidone
Solvent of the mixed solution as reaction system, the product after reaction is recycled by the way of vacuum flashing, using deionized water
Washing avoids the step of repeatedly extracting using water-soluble organic solution, can effectively shorten the production cycle, reduces polyether-ether-ketone tree
The production cost of rouge, and product purity is obviously improved.
Specific embodiment:
A method of polyether-ether-ketone resin being prepared, this method comprises the following steps:
(1) polymerization reaction: 4,4'- difluoro benzophenone, hydroquinone and sodium carbonate are added in reactor, solvent is then added
The solid-liquid volume ratio in reactor is made to be that 1:2-1:3 is heated to 130- under nitrogen protection and stirring action with water entrainer
150 DEG C, water entrainer is removed after reacting 1h, then be heated slowly to 180-225 DEG C, reacts 1 hour, be then slowly warming up to 260-
280 DEG C, the heating-up time is 0.5 hour, is reacted 2-3 hours, wherein the volume ratio of solvent and water entrainer is 2:1-3:1, described
Solvent uses mass ratio are as follows: the isopropanol of 10:10:1, dimethyl acetamide, N-Methyl pyrrolidone mixed solution；
(2) the precipitating processing of reaction product: 100-120 DEG C is cooled to after polymerization reaction, the product produced to polymerization reaction
Middle that solvent as described in step (1) is added, stirring to reaction system uniformly carries out vacuum flashing afterwards；
(3) wash: the product after vacuum flashing is dry after being washed with deionized.
The method for preparing polyether-ether-ketone resin is 4,4'- difluoro benzophenones, right in polymerization reaction described in step (1)
The molar ratio of benzenediol and sodium carbonate is 1:0.995:1.
The method for preparing polyether-ether-ketone resin, water entrainer described in step (1) use dimethylbenzene.
The method for preparing polyether-ether-ketone resin, the pressure of vacuum flashing described in step (2) be not more than in
0.05MPa, temperature are 245-255 DEG C.
The method for preparing polyether-ether-ketone resin, the solid-liquid matter in deionized water washing process described in step (3)
Amount is than being 1:3.
Specific embodiment:
According to following table 1 by raw material 4,4'- difluoro benzophenone, hydroquinone and sodium carbonate are added in reactor, then plus
Enter mass ratio are as follows: the isopropanol of 10:10:1, dimethyl acetamide, N-Methyl pyrrolidone mixed solution as solvent, be added
Dimethylbenzene is as water entrainer, so that the solid-liquid volume ratio in reactor is that 1:2-1:3 adds under nitrogen protection and stirring action
Heat is to 150 DEG C, reaction 1h refluxing xylene draining, removes water entrainer after theory count value to be achieved, then be heated slowly to 200
DEG C, it reacts 1 hour, is then slowly warming up to 270 DEG C, the heating-up time is 0.5 hour, reacts 2-3 hour, wherein solvent and with water
The volume ratio of agent is 2:1-3:1；It is cooled to 100 DEG C after polymerization reaction, step is added in the product produced to polymerization reaction
(1) solvent described in, stirring to reaction system uniformly carry out vacuum flashing afterwards；Product after vacuum flashing is washed with deionized water
It is dry after washing, the ash content of polyether-ether-ketone resin is measured, as shown in the table: dosage is with weight basis:
| Diphenyl sulphone (DPS) | Isopropanol | Dimethyl acetamide | N-Methyl pyrrolidone | Ash content | |
| Comparative example 1 | 21 | 1.2‰ | |||
| Comparative example 2 | 0 | 21 | 0 | 0 | 0.8‰ |
| Comparative example 3 | 0 | 0 | 21 | 0 | 0.9‰ |
| Comparative example 4 | 0 | 10.5 | 10.5 | 0 | 0.9‰ |
| Comparative example 5 | 0 | 7 | 7 | 7 | 0.8‰ |
| Comparative example 6 | 0 | 8 | 8 | 5 | 0.6‰ |
| Comparative example 7 | 0 | 9 | 9 | 3 | 0.6‰ |
| Embodiment | 0 | 10 | 10 | 1 | 0.2‰ |
It can be seen that under the conditions of equivalent responses by the above comparative example and embodiment, under identical major ingredient conditions of mixture ratios, use
Mass ratio are as follows: the isopropanol of 10:10:1, dimethyl acetamide, N-Methyl pyrrolidone mixed solution as solvent, it is significant to drop
The low ash content of product, i.e. product purity are greatly improved.
The above is only highly preferred embodiment of the present invention, the method for the present invention includes but be not limited to the above embodiments, the present invention
Unaccomplished matter, belong to the common knowledge of those skilled in the art.
Claims (5)
1. a kind of method for preparing polyether-ether-ketone resin, it is characterized in that: this method comprises the following steps:
(1) polymerization reaction: 4,4'- difluoro benzophenone, hydroquinone and sodium carbonate are added in reactor, solvent is then added
The solid-liquid volume ratio in reactor is made to be that 1:2-1:3 is heated to 130- under nitrogen protection and stirring action with water entrainer
150 DEG C, water entrainer is removed after reacting 1h, then be heated slowly to 180-225 DEG C, reacts 1 hour, be then slowly warming up to 260-
280 DEG C, the heating-up time is 0.5 hour, is reacted 2-3 hours, wherein the volume ratio of solvent and water entrainer is 2:1-3:1, described
Solvent uses mass ratio are as follows: the isopropanol of 10:10:1, dimethyl acetamide, N-Methyl pyrrolidone mixed solution；
(2) the precipitating processing of reaction product: 100-120 DEG C is cooled to after polymerization reaction, the product produced to polymerization reaction
Middle that solvent as described in step (1) is added, stirring to reaction system uniformly carries out vacuum flashing afterwards；
(3) wash: the product after vacuum flashing is dry after being washed with deionized.
2. the method according to claim 1 for preparing polyether-ether-ketone resin, it is characterized in that: polymerization described in step (1) is anti-
Ying Zhong, the molar ratio of 4,4'- difluoro benzophenones, hydroquinone and sodium carbonate are 1:0.995:1.
3. the method according to claim 1 for preparing polyether-ether-ketone resin, it is characterized in that: water entrainer described in step (1)
Using dimethylbenzene.
4. the method according to claim 1 for preparing polyether-ether-ketone resin is dodged it is characterized in that: depressurizing described in step (2)
The pressure of steaming is not more than in 0.05MPa, and temperature is 245-255 DEG C.
5. the method according to claim 1 for preparing polyether-ether-ketone resin, it is characterized in that: deionization described in step (3)
Solid-liquid mass ratio during water washing is 1:3.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910563187.9A CN110256643B (en) | 2019-06-26 | 2019-06-26 | Method for preparing polyether-ether-ketone resin |
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| CN201910563187.9A CN110256643B (en) | 2019-06-26 | 2019-06-26 | Method for preparing polyether-ether-ketone resin |
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| CN110256643A true CN110256643A (en) | 2019-09-20 |
| CN110256643B CN110256643B (en) | 2020-03-31 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113583232A (en) * | 2021-08-13 | 2021-11-02 | 吉林省中研高分子材料股份有限公司 | High-strength low-chroma polyether-ether-ketone and preparation method thereof |
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| CN113583232A (en) * | 2021-08-13 | 2021-11-02 | 吉林省中研高分子材料股份有限公司 | High-strength low-chroma polyether-ether-ketone and preparation method thereof |
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| CN110256643B (en) | 2020-03-31 |
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