CN115322078A - 一种全氟正丙基乙烯基醚的制备方法 - Google Patents
一种全氟正丙基乙烯基醚的制备方法 Download PDFInfo
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- CN115322078A CN115322078A CN202210999019.6A CN202210999019A CN115322078A CN 115322078 A CN115322078 A CN 115322078A CN 202210999019 A CN202210999019 A CN 202210999019A CN 115322078 A CN115322078 A CN 115322078A
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- DAVCAHWKKDIRLY-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC=C DAVCAHWKKDIRLY-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims abstract description 118
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 37
- 239000000047 product Substances 0.000 claims abstract description 36
- 238000005406 washing Methods 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000012043 crude product Substances 0.000 claims abstract description 24
- 238000007259 addition reaction Methods 0.000 claims abstract description 23
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 22
- 239000011259 mixed solution Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 238000001914 filtration Methods 0.000 claims abstract description 19
- 238000001179 sorption measurement Methods 0.000 claims abstract description 18
- 238000000895 extractive distillation Methods 0.000 claims abstract description 17
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 14
- 239000003513 alkali Substances 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 151
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- 239000003463 adsorbent Substances 0.000 claims description 22
- 239000007789 gas Substances 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 21
- 150000004673 fluoride salts Chemical class 0.000 claims description 20
- 239000002798 polar solvent Substances 0.000 claims description 20
- 239000000539 dimer Substances 0.000 claims description 13
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 12
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 12
- HQSMEHLVLOGBCK-UHFFFAOYSA-N 1-ethenylsulfinylethene Chemical compound C=CS(=O)C=C HQSMEHLVLOGBCK-UHFFFAOYSA-N 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 10
- 238000005507 spraying Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000011698 potassium fluoride Substances 0.000 claims description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims description 6
- 239000011775 sodium fluoride Chemical group 0.000 claims description 6
- 235000013024 sodium fluoride Nutrition 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002071 nanotube Substances 0.000 claims description 3
- RXJQEVUMWUEEPT-UHFFFAOYSA-N methanetetrathiol Chemical compound SC(S)(S)S RXJQEVUMWUEEPT-UHFFFAOYSA-N 0.000 claims description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000003647 oxidation Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 230000001590 oxidative effect Effects 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000002041 carbon nanotube Substances 0.000 description 9
- 229910021393 carbon nanotube Inorganic materials 0.000 description 9
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- APRDMRHFBGQNEE-UHFFFAOYSA-N FC(C(OC1(C=CC=CC1)F)(F)F)(C(F)(F)F)F Chemical compound FC(C(OC1(C=CC=CC1)F)(F)F)(C(F)(F)F)F APRDMRHFBGQNEE-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UPVJEODAZWTJKZ-UPHRSURJSA-N (z)-1,2-dichloro-1,2-difluoroethene Chemical group F\C(Cl)=C(/F)Cl UPVJEODAZWTJKZ-UPHRSURJSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- LMFJKKGDLAICPF-UHFFFAOYSA-N phenanthrene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC3=CC=CC=C3C2=C1 LMFJKKGDLAICPF-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- -1 polytetrafluoroethylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/36—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN202210999019.6A CN115322078A (zh) | 2022-08-19 | 2022-08-19 | 一种全氟正丙基乙烯基醚的制备方法 |
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CN202210999019.6A CN115322078A (zh) | 2022-08-19 | 2022-08-19 | 一种全氟正丙基乙烯基醚的制备方法 |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000297060A (ja) * | 1999-04-13 | 2000-10-24 | Asahi Glass Co Ltd | ペンタフルオロプロピオニルフルオリドの製造方法 |
CN1884323A (zh) * | 2006-05-19 | 2006-12-27 | 浙江大学 | 含四甲基胍阳离子的交联型阴离子聚合物及制备方法和用途 |
CN101817728A (zh) * | 2009-10-21 | 2010-09-01 | 山东东岳神舟新材料有限公司 | 一种生产六氟环氧丙烷联产全氟乙烯基醚的方法 |
US20140330046A1 (en) * | 2011-11-16 | 2014-11-06 | Zhonghao Chenguang Research Institute Of Chemical Industry Company Limited | Method for Preparing Fluorine-Containing Vinyl Ether |
CN105017467A (zh) * | 2015-07-31 | 2015-11-04 | 苏州新区特氟龙塑料制品厂 | 一种pfa可溶性聚四氟乙烯的制备方法 |
CN111072461A (zh) * | 2019-12-19 | 2020-04-28 | 浙江巨圣氟化学有限公司 | 一种ppve的合成方法 |
CN113398899A (zh) * | 2020-09-27 | 2021-09-17 | 俞春亚 | 一种吸附剂及其制备方法 |
-
2022
- 2022-08-19 CN CN202210999019.6A patent/CN115322078A/zh active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000297060A (ja) * | 1999-04-13 | 2000-10-24 | Asahi Glass Co Ltd | ペンタフルオロプロピオニルフルオリドの製造方法 |
CN1884323A (zh) * | 2006-05-19 | 2006-12-27 | 浙江大学 | 含四甲基胍阳离子的交联型阴离子聚合物及制备方法和用途 |
CN101817728A (zh) * | 2009-10-21 | 2010-09-01 | 山东东岳神舟新材料有限公司 | 一种生产六氟环氧丙烷联产全氟乙烯基醚的方法 |
US20140330046A1 (en) * | 2011-11-16 | 2014-11-06 | Zhonghao Chenguang Research Institute Of Chemical Industry Company Limited | Method for Preparing Fluorine-Containing Vinyl Ether |
CN105017467A (zh) * | 2015-07-31 | 2015-11-04 | 苏州新区特氟龙塑料制品厂 | 一种pfa可溶性聚四氟乙烯的制备方法 |
CN111072461A (zh) * | 2019-12-19 | 2020-04-28 | 浙江巨圣氟化学有限公司 | 一种ppve的合成方法 |
CN113398899A (zh) * | 2020-09-27 | 2021-09-17 | 俞春亚 | 一种吸附剂及其制备方法 |
Non-Patent Citations (2)
Title |
---|
朱林华等著: "《功能高分子材料的基础理论及应用研究》", 北京:中国原子能出版社, pages: 285 * |
陈焱锋: ""全氟正丙基乙烯基醚(PPVE)的合成方法及性质研究"", 有机氟工业, no. 4, pages 20 - 23 * |
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