TW213920B - - Google Patents
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- Publication number
- TW213920B TW213920B TW081102967A TW81102967A TW213920B TW 213920 B TW213920 B TW 213920B TW 081102967 A TW081102967 A TW 081102967A TW 81102967 A TW81102967 A TW 81102967A TW 213920 B TW213920 B TW 213920B
- Authority
- TW
- Taiwan
- Prior art keywords
- ester
- bromophenyl
- tris
- phosphate
- item
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 10
- -1 tri (bromophenyl) phosphate ester Chemical class 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 6
- OZEDYCTUPMFWEP-UHFFFAOYSA-N tris(2,4-dibromophenyl) phosphate Chemical group BrC1=CC(Br)=CC=C1OP(=O)(OC=1C(=CC(Br)=CC=1)Br)OC1=CC=C(Br)C=C1Br OZEDYCTUPMFWEP-UHFFFAOYSA-N 0.000 claims description 6
- 230000002079 cooperative effect Effects 0.000 claims description 3
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims 4
- 125000004799 bromophenyl group Chemical group 0.000 claims 4
- 239000007790 solid phase Substances 0.000 claims 2
- IVJLIUKQYNWCEZ-UHFFFAOYSA-N tris(2-bromophenyl) phosphate Chemical compound BrC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)Br)OC1=CC=CC=C1Br IVJLIUKQYNWCEZ-UHFFFAOYSA-N 0.000 claims 2
- BXRXEOQDLYSFCZ-UHFFFAOYSA-N (2-bromophenyl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1Br BXRXEOQDLYSFCZ-UHFFFAOYSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 241000219112 Cucumis Species 0.000 claims 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 229910052698 phosphorus Inorganic materials 0.000 description 14
- 239000011574 phosphorus Substances 0.000 description 14
- FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 13
- 239000000052 vinegar Substances 0.000 description 12
- 235000021419 vinegar Nutrition 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ULKGULQGPBMIJU-UHFFFAOYSA-N benzene;hydron;bromide Chemical compound Br.C1=CC=CC=C1 ULKGULQGPBMIJU-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RSSDWSPWORHGIE-UHFFFAOYSA-N $l^{1}-phosphanylbenzene Chemical compound [P]C1=CC=CC=C1 RSSDWSPWORHGIE-UHFFFAOYSA-N 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- CFDRQRFAQCJPBZ-UHFFFAOYSA-N 1-chlorohexan-1-ol Chemical compound CCCCCC(O)Cl CFDRQRFAQCJPBZ-UHFFFAOYSA-N 0.000 description 1
- FNAKEOXYWBWIRT-UHFFFAOYSA-N 2,3-dibromophenol Chemical compound OC1=CC=CC(Br)=C1Br FNAKEOXYWBWIRT-UHFFFAOYSA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical group OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NIYRKULWNMDRHQ-UHFFFAOYSA-N C1=CC=CC=C1.[Br].[Br] Chemical compound C1=CC=CC=C1.[Br].[Br] NIYRKULWNMDRHQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 241001417539 Liza Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- ATPYWZKDGYKXIM-UHFFFAOYSA-N acetic acid phosphoric acid Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.OP(O)(O)=O ATPYWZKDGYKXIM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- JVZSFAIVZDBMLX-UHFFFAOYSA-N phenanthrene phenol Chemical compound C1=CC=CC=2C3=CC=CC=C3C=CC12.C1(=CC=CC=C1)O JVZSFAIVZDBMLX-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical group [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/706,133 US5138085A (en) | 1991-05-28 | 1991-05-28 | Process for purifying polybrominated triaryl phosphate esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW213920B true TW213920B (enExample) | 1993-10-01 |
Family
ID=24836337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW081102967A TW213920B (enExample) | 1991-05-28 | 1992-04-16 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5138085A (enExample) |
| EP (1) | EP0516212A2 (enExample) |
| JP (1) | JPH0637506B2 (enExample) |
| KR (1) | KR920021566A (enExample) |
| CN (1) | CN1067247A (enExample) |
| BR (1) | BR9201987A (enExample) |
| CA (1) | CA2067988A1 (enExample) |
| IL (1) | IL101958A0 (enExample) |
| MX (1) | MX9202252A (enExample) |
| TW (1) | TW213920B (enExample) |
| ZA (1) | ZA922737B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3291991B2 (ja) * | 1994-09-22 | 2002-06-17 | 住友化学工業株式会社 | Ｏ，ｓ−ジメチル ｎ−アセチルホスホルアミドチオエートの精製法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1866852A (en) * | 1929-04-05 | 1932-07-12 | Rubber Service Lab Co | Manufacture of triaryl phosphates |
| US2561493A (en) * | 1945-09-13 | 1951-07-24 | Celanese Corp | Plasticized and stabilized cellulose acetate |
| US2894015A (en) * | 1956-03-30 | 1959-07-07 | Pennsalt Chemicals Corp | Fungicidal compositions and their use |
| US3356775A (en) * | 1963-07-31 | 1967-12-05 | Monsanto Co | Purification of triaryl phosphates |
| US3436441A (en) * | 1964-12-24 | 1969-04-01 | Monsanto Co | Meta-chlorinated or brominated phenyl phosphates |
| DE1493613B2 (de) * | 1965-12-18 | 1974-02-14 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von halogenierten Estern des Phospors |
| US3526681A (en) * | 1967-04-25 | 1970-09-01 | American Cyanamid Co | Tris(chloro sulfonylaryl) phosphates and a method for preparing same |
| JPS5047953A (enExample) * | 1973-08-27 | 1975-04-28 | ||
| US3945891A (en) * | 1974-06-20 | 1976-03-23 | Fmc Corporation | Distillation process for purification of triaryl phosphate esters |
| US4059655A (en) * | 1975-11-24 | 1977-11-22 | Ppg Industries, Inc. | Process for preparing halogenated diaryl hydrogen phosphates |
| US4897502A (en) * | 1987-02-09 | 1990-01-30 | Fmc Corporation | Process for making solid polyhalotriaryl phosphate esters |
-
1991
- 1991-05-28 US US07/706,133 patent/US5138085A/en not_active Expired - Fee Related
-
1992
- 1992-04-14 ZA ZA922737A patent/ZA922737B/xx unknown
- 1992-04-16 TW TW081102967A patent/TW213920B/zh active
- 1992-05-05 CA CA002067988A patent/CA2067988A1/en not_active Abandoned
- 1992-05-13 EP EP92201376A patent/EP0516212A2/en not_active Withdrawn
- 1992-05-14 MX MX9202252A patent/MX9202252A/es unknown
- 1992-05-18 CN CN92103933A patent/CN1067247A/zh active Pending
- 1992-05-21 JP JP4171428A patent/JPH0637506B2/ja not_active Expired - Lifetime
- 1992-05-21 IL IL101958A patent/IL101958A0/xx unknown
- 1992-05-26 BR BR929201987A patent/BR9201987A/pt not_active Application Discontinuation
- 1992-05-27 KR KR1019920009007A patent/KR920021566A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN1067247A (zh) | 1992-12-23 |
| JPH05230084A (ja) | 1993-09-07 |
| EP0516212A3 (enExample) | 1994-03-16 |
| MX9202252A (es) | 1992-11-01 |
| EP0516212A2 (en) | 1992-12-02 |
| CA2067988A1 (en) | 1992-11-29 |
| JPH0637506B2 (ja) | 1994-05-18 |
| US5138085A (en) | 1992-08-11 |
| KR920021566A (ko) | 1992-12-18 |
| BR9201987A (pt) | 1993-01-12 |
| IL101958A0 (en) | 1992-12-30 |
| ZA922737B (en) | 1992-12-30 |
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