TW467888B - Process for the production of bisphenol A - Google Patents
Process for the production of bisphenol A Download PDFInfo
- Publication number
- TW467888B TW467888B TW088116866A TW88116866A TW467888B TW 467888 B TW467888 B TW 467888B TW 088116866 A TW088116866 A TW 088116866A TW 88116866 A TW88116866 A TW 88116866A TW 467888 B TW467888 B TW 467888B
- Authority
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- Prior art keywords
- melt
- cation
- phenol
- bisphenol
- strong acid
- Prior art date
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000007787 solid Substances 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000000155 melt Substances 0.000 claims abstract description 18
- 150000001768 cations Chemical class 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 4
- 150000001339 alkali metal compounds Chemical class 0.000 claims abstract description 3
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims abstract description 3
- 229940023913 cation exchange resins Drugs 0.000 claims abstract description 3
- 239000000919 ceramic Substances 0.000 claims abstract description 3
- 229910001410 inorganic ion Inorganic materials 0.000 claims abstract description 3
- 238000011049 filling Methods 0.000 claims description 6
- -1 ammonium ions Chemical class 0.000 claims description 3
- 230000002079 cooperative effect Effects 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims 2
- 239000002689 soil Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 description 11
- 239000000356 contaminant Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 239000003344 environmental pollutant Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 231100000719 pollutant Toxicity 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical compound CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
4 67888 A7 ___B7__ 五、發明說明纟) 技術範圍: 本發明係關於高純度雙酚A之製法。 --·請先閲讀背面之注意事項再填寫本頁) '背景技藝 —種製備雙酚A ( 2,2 -雙.(4 y —羥苯基)丙烷 )的習知方法包括將丙酮及過量的酚在強酸觸媒(例如磺 酸型陽離子交換樹脂)的存在下施以反應。產物通.常被施 以冷卻以形成雙酚A與酚之加合物的結晶(在下文中簡稱 爲 '' 晶形加合物〃)。收集晶形加合物並施以酚去除處理 即製得高純度雙酚A。酚去除處理通常藉以下方式實施, 即使用諸如蒸餾塔將加合物之熔漿施以加熱以使酚蒸發及 分離。 經濟部智慧財產局員工消費合作社印製 頃發現在酚去除處理期間,雙酚A會被熱分解並生成 不純物例如鼢及異丙烯酚。雙酚A之分解作用不但在酚去 除裝置中進行同時亦在酚去除裝置之下游管線中進行(分 離出的雙酚A經由彼卸出並用於回收)。此外亦發現,僅 藉酚去除步驟之條件的控制實難以避免酚去除步驟中之雙 酚A的分解作用。 本發明鑑於以上的問題而提出。 發明揭示 本發明提供雙酚A之製法,包含提供雙酚A與酚之晶 形加合物的熔漿(其含有強酸污染物),將該熔漿施以加 熱以自熔漿蒸發及去除酚,其特徵爲,在該加熱之前’該 本紙張尺度適用t國國家標準(CNS)A4規格(210 X 297公釐) ΓΤΙ 467888 A7 B7 五、發明說明ο ) 熔號與陽離子給予固體(cation donating solid)被施以接觸 並藉彼中和強酸污染物。 頃發現酚去除處理期間之雙酚A的熱分解作用係歸因 •於晶形加合物中之強酸污染物(例如硫酸或磺酸)的存在 。咸信強酸污染物係衍生自用於丙酮與酚之反應的強酸觸 媒》 晶形加合物之熔漿中強酸污染物的量通常爲 0 . 00.3毫當量/升或以下,其典型量爲〇 . oooi. —0 00 1毫當量/升。藉熔漿與陽離子給予固體之接 觸,此微量的強酸污染物經發現可以安定的方式有效地中 和且無關乎酸污染物之量的變異。使用液態鹼性物質,可 以安定的方式中和此微量的強酸。 就本發明之目的而言,任何陽離子給予固體均可使用 只要強酸污染物可藉彼中和或者轉化爲不再具有強酸之性 質的物質例如鹽類。 陽離子給予固體的實例包括陽離子交換樹脂(例如-COOM型其中Μ是陽離子),無機離子交換器(例如被 陽離子取代的矽酸鹽(例如沸石或矽沸石)),含有鹼金 屬氧化物(例如N a 2 0 )及/或鹼土金屬氧化物(例如 C a 0)的陶瓷(例如玻璃及瓷器),鹼金屬化合物及鹼 土金屬化合物。陽離子給予固體可爲任何所欲的形狀例如 粉末、顆粒(錠劑)、纖維狀、片狀、多孔片狀、薄膜, 板狀或圓柱狀。 至於陽離子,則可以使用鹼金屬離子,例如鈉離子、 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐) -5 - ί諝先聞讒背面之注$項再填窝本頁) I,— 訂.1. ^01. 經濟部智慧財產局員工消費合作社印製 4 6 7 8 8 8 A7 __B7 五、發明說明$ ) 鉀離子或鋰離子;鹼土金屬離子,例如鈣離子或鎂離子; 銨離子;及衍生自有機胺的有機銨離子。 ' 晶形加合物之熔漿和陽離子給予固體的接觸可以利用 •任何所欲的方法實施例如塡充塔法其中熔漿流經含有陽離 子給予固體的塡充塔,過濾塔法其中熔漿流經含有陽離子 給予固體層的過濾塔,分散法其中陽離子給予固體之粉末 分散於熔漿中,或者浸入法其中陽離子給予固體之模塑體 被浸入熔漿中。經由熔漿與陽離子給予固體之接觸,熔漿 中的強酸污染物可藉離子交換反應以固體表面上的陽離子 中和。 以下將參考附圖對本發明做較爲詳細的說明,其中圖 1係流程圖其以圖式例舉說明用以實施本發明之方法的裝 置。 參考圖1 ,雙酚Α與酚之晶形加合物的進料或者含有 晶形加合物之酚的進料經由管線1 1送至熔化裝置1中其 中進料在100 — 150 °C (最好在120-13 〇°C) 下加熱以使晶形加合物熔化或者液化並形成熔漿.(或液化 加合物)。 然後熔漿經由管線12及13與幫浦2流至接觸裝置 3其中熔漿與內含於其中的陽離子給予固體被施以接觸, 而使得熔漿中的強酸污染物爲陽離子給予固體所中和。然 後將由是施以處理的熔漿經管線1 4送至酚去除裝置4, 例如蒸餾塔或者薄膜型蒸發器,其中熔漿在160-220 °C (最好在180 — 200 °C)下加熱以使酚自熔 本紙張尺度適用中國囤家標準(CNS)A4規格(210 X 297公釐) -6 - (請先閲讀背面之#一意事項再填寫本頁) 訂 鍊g'_ 經濟部智慧財產局員工消費合作社印製 467 888 A7 B7 五、發明說明4 ) (請先閱讀背面之注意事項再填寫本頁) 漿蒸出及分離。蒸發出的酚自酚去除裝置抽至頂部並流經 管線1 5,而雙酚A則經管線1 6及幫浦5卸出並經管線 1 7送至下一步驟例如製粒裝置(未顯示)。 • 以下實例將對本發明做進一步的例舉說明。 實例1 使用如圖1所示的裝置,雙酚A係由晶形加合物製得 。操作條件槪述如下。 管線1 1 : 進料:酚中的晶形加合物(淤漿型態):雙酣A /酚 重量比爲60:40 管線1 2 :
熔漿溫度:1 2 0 °C 強酸濃度:0 · 00 1毫當量/升 經濟部智慧財產局員工消費合作社印製 接觸裝置3 : 陽離子給予固體:由含有N a 2〇及c a 0之玻璃纖維 製成的過濾器 管線1 4 :
熔漿溫度:1 5 0 °C 強酸濃度:未檢出 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐) Α7 4 6 7 8 8 8 _._Β7_ 五、發明說明(5 ) 管線1 6 : 雙酚A溫度:19 0°C 酚濃度:5 — 10 ppm重量比 比較例1 以等同於上述的方式重覆實例1但是此處未使用接觸 裝置3。因此,自熔化裝置1卸出的熔漿直接送至酚去除 裝置4。結果如下。 管線1 4 : 熔漿溫度:1 5 0 °C 強酸濃度:0.001毫當量/升 管線1 6 : 雙酚A溫度:190t 酣濃度:40 — 5 Op pm重量比 主要元件對照 (請先閲讀背面之注意事項再填#1'本頁) .素--------訂··!-------線; 經濟部智慧財產局員工消費合作社印製 1 熔化裝置 2 幫浦 3 ' 接觸裝置 4 酚去除裝置 5 幫浦 11 管線 12 管線 13 管線 14 管線 15 管線 16 管線 17 管線 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐)-8 -
Claims (1)
- A8 A8 467888 ------_ 六、申請專利範圍 附件一(A ): 公告本 ~ II 1 第88 1 1 6866號專利申請案之由雙 酚A與酚所形成的晶狀加合物的熔漿,加熱該熔漿以蒸發 及去除熔漿中的酚,其特徵爲在加熱之前,先令該熔漿與 陽離子給予固體接觸以中和其中所含的強酸,其中,該陽 離子給予固體包括陽離子交換樹脂、無機離子交換劑、陶 瓷、鹼金屬化合物及鹼土金屬化合物。 2 .如申請專利範圍第1項之方法,其中,該陽離子 係選自鹼金屬離子、驗土金屬離子、錢離子及有機銨離子· 〇 3 .如申請專利範圍第1項之方法,其中,該陽離子 給予固體爲玻璃纖維。 --i------‘裂-- (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 張 紙 本 準 標 家 國 國 中 用 Μ 釐 9 2
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP09255499A JP3903634B2 (ja) | 1999-03-31 | 1999-03-31 | ビスフェノールaの製造方法 |
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TW467888B true TW467888B (en) | 2001-12-11 |
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TW088116866A TW467888B (en) | 1999-03-31 | 1999-09-30 | Process for the production of bisphenol A |
Country Status (10)
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US (1) | US6512148B1 (zh) |
EP (1) | EP1165476B1 (zh) |
JP (1) | JP3903634B2 (zh) |
KR (1) | KR100551922B1 (zh) |
CN (1) | CN1174951C (zh) |
AU (1) | AU5446699A (zh) |
DE (1) | DE69908824T2 (zh) |
SA (1) | SA99200786B1 (zh) |
TW (1) | TW467888B (zh) |
WO (1) | WO2000059853A1 (zh) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4140171B2 (ja) * | 2000-05-02 | 2008-08-27 | 三菱化学株式会社 | 高品位ビスフェノールa製造のためのビスフェノールaとフェノールとの結晶アダクトの製造方法 |
JP4658355B2 (ja) * | 2001-03-05 | 2011-03-23 | 出光興産株式会社 | ビスフェノールaの製造方法 |
US9290618B2 (en) | 2011-08-05 | 2016-03-22 | Sabic Global Technologies B.V. | Polycarbonate compositions having enhanced optical properties, methods of making and articles comprising the polycarbonate compositions |
US8962117B2 (en) | 2011-10-27 | 2015-02-24 | Sabic Global Technologies B.V. | Process for producing bisphenol A with reduced sulfur content, polycarbonate made from the bisphenol A, and containers formed from the polycarbonate |
WO2013061274A1 (en) * | 2011-10-27 | 2013-05-02 | Sabic Innovative Plastics Ip B.V. | Process for producing bisphenol a with reduced sulfur content, polycarbonate made from the bisphenol a, and containers formed from the polycarbonate |
US9490405B2 (en) | 2012-02-03 | 2016-11-08 | Sabic Innovative Plastics Ip B.V. | Light emitting diode device and method for production thereof containing conversion material chemistry |
WO2013130606A2 (en) * | 2012-02-29 | 2013-09-06 | Sabic Innovative Plastics Ip B.V. | Polycarbonate made from low sulfur bisphenol a and containing converions material chemistry, and articles made therefrom |
US9287471B2 (en) | 2012-02-29 | 2016-03-15 | Sabic Global Technologies B.V. | Polycarbonate compositions containing conversion material chemistry and having enhanced optical properties, methods of making and articles comprising the same |
US9346949B2 (en) | 2013-02-12 | 2016-05-24 | Sabic Global Technologies B.V. | High reflectance polycarbonate |
PL217484B1 (pl) | 2012-04-16 | 2014-07-31 | Inst Ciężkiej Syntezy Organicznej Blachownia | Sposób otrzymywania bisfenolu A |
PL219656B1 (pl) | 2012-08-23 | 2015-06-30 | Inst Ciężkiej Syntezy Organicznej Blachownia | Sposób transformacji produktów ubocznych w procesie syntezy bisfenolu A |
US9821523B2 (en) | 2012-10-25 | 2017-11-21 | Sabic Global Technologies B.V. | Light emitting diode devices, method of manufacture, uses thereof |
EP2778186B1 (en) * | 2013-03-15 | 2017-07-12 | SABIC Global Technologies B.V. | Production of a polycarbonate with limited metal residuals |
WO2014141107A2 (en) | 2013-03-15 | 2014-09-18 | Sabic Innovative Plastics Ip B.V. | Process for purification of diphenyl carbonate for the manufacturing of high quality polycarbonate |
US9553244B2 (en) | 2013-05-16 | 2017-01-24 | Sabic Global Technologies B.V. | Branched polycarbonate compositions having conversion material chemistry and articles thereof |
KR102229148B1 (ko) | 2013-05-29 | 2021-03-23 | 사빅 글로벌 테크놀러지스 비.브이. | 색 안정한 열가소성 광투과 물품을 갖는 조명 장치 |
US9006378B2 (en) | 2013-05-29 | 2015-04-14 | Sabic Global Technologies B.V. | Color stable thermoplastic composition |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4876395A (en) * | 1988-07-11 | 1989-10-24 | General Electric Company | Process for color stabilization of bisphenol-A |
US5008470A (en) * | 1989-11-30 | 1991-04-16 | Shell Oil Company | Process for preparing a bisphenol |
US5091591A (en) * | 1990-11-13 | 1992-02-25 | General Electric Company | Process and composition |
EP0643032B1 (en) * | 1991-07-16 | 1997-02-05 | Chiyoda Corporation | Condensation process for recovery of bisphenol A and phenol |
JP3903644B2 (ja) * | 1999-05-20 | 2007-04-11 | 三菱化学株式会社 | ビスフェノールaの製造方法 |
-
1999
- 1999-03-31 JP JP09255499A patent/JP3903634B2/ja not_active Expired - Lifetime
- 1999-08-31 EP EP99940594A patent/EP1165476B1/en not_active Expired - Lifetime
- 1999-08-31 US US09/937,401 patent/US6512148B1/en not_active Expired - Lifetime
- 1999-08-31 WO PCT/JP1999/004724 patent/WO2000059853A1/en active IP Right Grant
- 1999-08-31 KR KR1020017012308A patent/KR100551922B1/ko not_active IP Right Cessation
- 1999-08-31 CN CNB998165204A patent/CN1174951C/zh not_active Expired - Lifetime
- 1999-08-31 DE DE69908824T patent/DE69908824T2/de not_active Expired - Lifetime
- 1999-08-31 AU AU54466/99A patent/AU5446699A/en not_active Abandoned
- 1999-09-30 TW TW088116866A patent/TW467888B/zh not_active IP Right Cessation
- 1999-11-30 SA SA99200786A patent/SA99200786B1/ar unknown
Also Published As
Publication number | Publication date |
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DE69908824D1 (de) | 2003-07-17 |
AU5446699A (en) | 2000-10-23 |
CN1174951C (zh) | 2004-11-10 |
EP1165476B1 (en) | 2003-06-11 |
CN1339019A (zh) | 2002-03-06 |
EP1165476A1 (en) | 2002-01-02 |
WO2000059853A1 (en) | 2000-10-12 |
JP2000290209A (ja) | 2000-10-17 |
US6512148B1 (en) | 2003-01-28 |
DE69908824T2 (de) | 2004-05-06 |
KR20010105398A (ko) | 2001-11-28 |
SA99200786B1 (ar) | 2006-08-06 |
KR100551922B1 (ko) | 2006-02-16 |
JP3903634B2 (ja) | 2007-04-11 |
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