CN103642031B - A kind of high-flow polyphenylene ether sulfone ketone resin and industrialized producing technology thereof - Google Patents
A kind of high-flow polyphenylene ether sulfone ketone resin and industrialized producing technology thereof Download PDFInfo
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- CN103642031B CN103642031B CN201310609135.3A CN201310609135A CN103642031B CN 103642031 B CN103642031 B CN 103642031B CN 201310609135 A CN201310609135 A CN 201310609135A CN 103642031 B CN103642031 B CN 103642031B
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- CN
- China
- Prior art keywords
- benzophenone
- polyphenylene ether
- ether sulfone
- ketone resin
- producing technology
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- 239000011347 resin Substances 0.000 title claims abstract description 30
- 229920005989 resin Polymers 0.000 title claims abstract description 30
- 229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 21
- -1 sulfone ketone Chemical class 0.000 title claims abstract description 21
- 238000005516 engineering process Methods 0.000 title claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 33
- 239000007787 solid Substances 0.000 claims abstract description 25
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 20
- 239000000126 substance Substances 0.000 claims abstract description 18
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 239000012965 benzophenone Substances 0.000 claims description 23
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 claims description 19
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 11
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 9
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 8
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- 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 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 210000003097 mucus Anatomy 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 150000005323 carbonate salts Chemical class 0.000 claims description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- XFTXWDDQIXYAGY-UHFFFAOYSA-N (3-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC(Cl)=C1 XFTXWDDQIXYAGY-UHFFFAOYSA-N 0.000 claims description 2
- FIFXBQVRZOTUNN-UHFFFAOYSA-N (4-chlorophenyl)-(3-fluorophenyl)methanone Chemical compound FC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1 FIFXBQVRZOTUNN-UHFFFAOYSA-N 0.000 claims description 2
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical class C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000003021 water soluble solvent Substances 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 abstract description 15
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 12
- 229920000570 polyether Polymers 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 9
- 150000008365 aromatic ketones Chemical class 0.000 abstract description 7
- 238000007334 copolymerization reaction Methods 0.000 abstract description 5
- 229920006260 polyaryletherketone Polymers 0.000 abstract description 3
- 238000007493 shaping process Methods 0.000 abstract description 2
- 229920000491 Polyphenylsulfone Polymers 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 15
- 125000000468 ketone group Chemical group 0.000 description 13
- 238000000034 method Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000004695 Polyether sulfone Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229920006393 polyether sulfone Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- ZHUXSAKDWNNBCQ-UHFFFAOYSA-N (3-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC(F)=C1 ZHUXSAKDWNNBCQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229920000090 poly(aryl ether) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QRFMXBKGNQEADL-UHFFFAOYSA-N 1,1'-biphenyl;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 QRFMXBKGNQEADL-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 150000001492 aromatic hydrocarbon derivatives Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Abstract
Description
Claims (11)
Priority Applications (1)
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CN201310609135.3A CN103642031B (en) | 2013-11-27 | 2013-11-27 | A kind of high-flow polyphenylene ether sulfone ketone resin and industrialized producing technology thereof |
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CN201310609135.3A CN103642031B (en) | 2013-11-27 | 2013-11-27 | A kind of high-flow polyphenylene ether sulfone ketone resin and industrialized producing technology thereof |
Publications (2)
Publication Number | Publication Date |
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CN103642031A CN103642031A (en) | 2014-03-19 |
CN103642031B true CN103642031B (en) | 2015-09-09 |
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CN201310609135.3A Active CN103642031B (en) | 2013-11-27 | 2013-11-27 | A kind of high-flow polyphenylene ether sulfone ketone resin and industrialized producing technology thereof |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103613763B (en) * | 2013-11-27 | 2015-08-26 | 江门市优巨新材料有限公司 | A kind of high-flow polyphenylene ether sulfone ketone resin and Industrialized synthesis method thereof |
CN104497300A (en) * | 2014-12-17 | 2015-04-08 | 江门市优巨新材料有限公司 | High-liquidity poly(phenylene ether sulfone ketone) resin and preparation method thereof |
CN104497301A (en) * | 2014-12-17 | 2015-04-08 | 江门市优巨新材料有限公司 | High-fluidity polysulfone ketone resin and production process thereof |
JP2023553775A (en) * | 2020-08-24 | 2023-12-26 | ビーエーエスエフ ソシエタス・ヨーロピア | polyphenylene sulfone |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101544760A (en) * | 2009-04-28 | 2009-09-30 | 吉林大学 | Random copolymer containing biphenyl structural polyether sulfone and polyether ketone sulfone and preparation method thereof |
CN101701067A (en) * | 2009-11-18 | 2010-05-05 | 吉林大学 | Tetramethyl-diphenol type polyarylether ketone (polyarylether sulphone) containing bromine at phenmethyl position and preparation method thereof |
Family Cites Families (1)
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US7153569B2 (en) * | 2004-03-19 | 2006-12-26 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic-aromatic copolyester films |
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- 2013-11-27 CN CN201310609135.3A patent/CN103642031B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101544760A (en) * | 2009-04-28 | 2009-09-30 | 吉林大学 | Random copolymer containing biphenyl structural polyether sulfone and polyether ketone sulfone and preparation method thereof |
CN101701067A (en) * | 2009-11-18 | 2010-05-05 | 吉林大学 | Tetramethyl-diphenol type polyarylether ketone (polyarylether sulphone) containing bromine at phenmethyl position and preparation method thereof |
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CN103642031A (en) | 2014-03-19 |
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Denomination of invention: High-fluidity polyphenylenesulfoneketone resin and industrial production technology thereof Effective date of registration: 20160902 Granted publication date: 20150909 Pledgee: Bank of China Limited by Share Ltd Jiangmen branch Pledgor: JIANGMEN YOUJU NEW MATERIALS CO., LTD. Registration number: 2016990000767 |
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Address after: 529040 Guangdong province Jiangmen City Road No. 291 dragon Jianghai District 1 buildings, 3 buildings Patentee after: Guangdong Youju advanced new material Co., Ltd Address before: 529080, No. 25, hi tech Zone, Jiangmen, Guangdong (Factory No. two) Patentee before: JIANGMEN YOUJU NEW MATERIALS Co.,Ltd. |
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PM01 | Change of the registration of the contract for pledge of patent right | ||
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Change date: 20201125 Registration number: 2016990000767 Pledgor after: Guangdong Youju advanced new material Co., Ltd Pledgor before: JIANGMEN YOUJU NEW MATERIALS Co.,Ltd. |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220217 Granted publication date: 20150909 Pledgee: Bank of China Limited by Share Ltd. Jiangmen branch Pledgor: Guangdong Youju advanced new material Co.,Ltd. Registration number: 2016990000767 |