JP2011512453A5 - - Google Patents
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- Publication number
- JP2011512453A5 JP2011512453A5 JP2010547276A JP2010547276A JP2011512453A5 JP 2011512453 A5 JP2011512453 A5 JP 2011512453A5 JP 2010547276 A JP2010547276 A JP 2010547276A JP 2010547276 A JP2010547276 A JP 2010547276A JP 2011512453 A5 JP2011512453 A5 JP 2011512453A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- poly
- phenylene ether
- mixture
- oxidative polymerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 84
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 claims description 57
- 238000006116 polymerization reaction Methods 0.000 claims description 53
- 230000001590 oxidative effect Effects 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 18
- 239000012074 organic phase Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 230000009920 chelation Effects 0.000 claims description 12
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002738 chelating agent Substances 0.000 claims description 9
- 229910001431 copper ion Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 6
- KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 4
- 239000012296 anti-solvent Substances 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 4
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- RYPRIXSYXLDSOA-UHFFFAOYSA-L chromium(2+);sulfate Chemical compound [Cr+2].[O-]S([O-])(=O)=O RYPRIXSYXLDSOA-UHFFFAOYSA-L 0.000 claims 1
- 229910000334 chromium(II) sulfate Inorganic materials 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims 1
- 239000000843 powder Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- WLLZFOKCJMRIQJ-UHFFFAOYSA-N 2,3-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound C1=C(O2)C(C)=C(C)C2=C1 WLLZFOKCJMRIQJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3033608P | 2008-02-21 | 2008-02-21 | |
| US61/030,336 | 2008-02-21 | ||
| US12/255,694 US8025158B2 (en) | 2008-02-21 | 2008-10-22 | High molecular weight poly(2,6-dimethyl-1,4-phenylene ether) and process therefor |
| US12/255,694 | 2008-10-22 | ||
| PCT/IB2009/050454 WO2009104107A1 (en) | 2008-02-21 | 2009-02-04 | High molecular weight poly(2,6-dimethyl-1,4-phenylene ether) and process therefor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011512453A JP2011512453A (ja) | 2011-04-21 |
| JP2011512453A5 true JP2011512453A5 (enExample) | 2012-12-27 |
| JP5178846B2 JP5178846B2 (ja) | 2013-04-10 |
Family
ID=40674236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010547276A Active JP5178846B2 (ja) | 2008-02-21 | 2009-02-04 | 高分子量ポリ（２，６−ジメチル−１，４−フェニレンエーテル）とその製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US8025158B2 (enExample) |
| EP (2) | EP2252646B1 (enExample) |
| JP (1) | JP5178846B2 (enExample) |
| CN (1) | CN102007162B (enExample) |
| AT (1) | ATE527302T1 (enExample) |
| SG (1) | SG188176A1 (enExample) |
| WO (1) | WO2009104107A1 (enExample) |
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| US8557937B1 (en) | 2012-05-09 | 2013-10-15 | Sabic Innovative Plastics Ip B.V. | Rubber composition, method for its formation, and automotive tire containing the composition |
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| US9090999B2 (en) | 2011-09-28 | 2015-07-28 | Sabic Global Technologies B.V. | Polyamide/polyphenylene ether fibers and fiber-forming method |
| US8975329B2 (en) | 2011-12-02 | 2015-03-10 | Sabic Global Technologies B.V. | Poly(phenylene ether) articles and compositions |
| US20130253105A1 (en) | 2012-02-17 | 2013-09-26 | Sabic Innovative Plastics Ip B.V. | Stain and Color Change Resistant Poly(Phenylene Ether) Composition |
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| CN107849239B (zh) * | 2015-06-09 | 2019-03-08 | 沙特基础工业全球技术有限公司 | 用于聚(苯醚)制造的方法和相关聚(苯醚) |
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| US11897990B2 (en) | 2019-04-30 | 2024-02-13 | Shpp Global Technologies B.V. | Curable poly(polyphenylene ether) oligomer compositions for coatings |
| CN112111057B (zh) * | 2019-06-20 | 2023-07-14 | 南通星辰合成材料有限公司 | 聚苯醚及其制备方法 |
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| EP3885393B1 (en) | 2020-03-26 | 2024-06-19 | SHPP Global Technologies B.V. | Modified poly(phenylene ether) copolymers, compositions, and methods thereof |
| EP4023704A1 (en) | 2020-12-29 | 2022-07-06 | SHPP Global Technologies B.V. | Electrically conductive microwave shielding compositions |
| US20240218123A1 (en) | 2021-04-27 | 2024-07-04 | Shpp Global Technologies B.V. | Bifunctional sizing agent for improved adhesion to substrates |
| EP4486815A1 (en) | 2022-03-01 | 2025-01-08 | SHPP Global Technologies B.V. | Copolymers derived from dicyclopentadiene |
| WO2024236469A1 (en) | 2023-05-15 | 2024-11-21 | Shpp Global Technologies B.V. | Medium molecular weight poly(phenylene ether) and method for the manufacture thereof |
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2008
- 2008-10-22 US US12/255,694 patent/US8025158B2/en active Active
-
2009
- 2009-02-04 WO PCT/IB2009/050454 patent/WO2009104107A1/en not_active Ceased
- 2009-02-04 EP EP09711981A patent/EP2252646B1/en active Active
- 2009-02-04 EP EP11152221.5A patent/EP2311898B1/en active Active
- 2009-02-04 CN CN2009801130620A patent/CN102007162B/zh active Active
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2011
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