SK143596A3 - Method of production for bis (silyalkyl) disulfides - Google Patents

Method of production for bis (silyalkyl) disulfides Download PDF

Info

Publication number: SK143596A3
Authority: SK; Slovakia
Prior art keywords: formula; mixture; iii; general formula; bis
Prior art date: 1995-11-07

Application number

SK1435-96A

Other languages

English (en)

Slovak (sk)

Inventor

Thomas Goebel

Joerg Muenzenberg

Original Assignee

Degussa

Priority date (The priority date 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 date listed.)

1995-11-07

Filing date

1996-11-06

Publication date

1997-05-07

1996-11-06 Application filed by Degussa filed Critical Degussa

1997-05-07 Publication of SK143596A3 publication Critical patent/SK143596A3/sk

Links

238000000034 method Methods 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title claims description 8
150000002019 disulfides Chemical class 0.000 title description 6
239000000203 mixture Substances 0.000 claims abstract description 29
239000002904 solvent Substances 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 12
229920001021 polysulfide Polymers 0.000 claims abstract description 12
239000007787 solid Substances 0.000 claims abstract description 9
125000005353 silylalkyl group Chemical group 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
230000000269 nucleophilic effect Effects 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000005425 toluyl group Chemical group 0.000 claims abstract description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 11
-1 alkylidene radical Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 3
239000012434 nucleophilic reagent Substances 0.000 claims description 3
150000003961 organosilicon compounds Chemical class 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 6
239000003513 alkali Substances 0.000 abstract description 2
150000001768 cations Chemical class 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 abstract 1
125000001118 alkylidene group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
238000001914 filtration Methods 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
235000019441 ethanol Nutrition 0.000 description 15
VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 9
239000003208 petroleum Substances 0.000 description 8
238000006477 desulfuration reaction Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
239000005077 polysulfide Substances 0.000 description 5
150000008117 polysulfides Polymers 0.000 description 5
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
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 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
RJWJCQLFAYQGBG-UHFFFAOYSA-L disodium;sulfite;hydrate Chemical compound [OH-].[Na+].[Na+].OS([O-])=O RJWJCQLFAYQGBG-UHFFFAOYSA-L 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012038 nucleophile Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 2
KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 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 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
229910000057 polysulfane Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
XWSQTXBRVIEOGT-UHFFFAOYSA-N triethoxy-[3-(tetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSS XWSQTXBRVIEOGT-UHFFFAOYSA-N 0.000 description 1
238000004073 vulcanization Methods 0.000 description 1
239000008096 xylene Substances 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0898—Compounds with a Si-S linkage

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1435-96A 1995-11-07 1996-11-06 Method of production for bis (silyalkyl) disulfides SK143596A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19541404A DE19541404A1 (de)	1995-11-07	1995-11-07	Verfahren zur selektiven Synthese von Silylalkyldisulfiden

Publications (1)

Publication Number	Publication Date
SK143596A3 true SK143596A3 (en)	1997-05-07

Family

ID=7776798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1435-96A SK143596A3 (en)	1995-11-07	1996-11-06	Method of production for bis (silyalkyl) disulfides

Country Status (18)

Country	Link
US (1)	US5663395A (ja)
EP (1)	EP0773224B1 (ja)
JP (1)	JPH09169774A (ja)
KR (1)	KR970027094A (ja)
CN (1)	CN1070862C (ja)
AU (1)	AU713295B2 (ja)
BR (1)	BR9605476A (ja)
CA (1)	CA2189601A1 (ja)
CZ (1)	CZ318096A3 (ja)
DE (2)	DE19541404A1 (ja)
ES (1)	ES2168424T3 (ja)
HR (1)	HRP960516B1 (ja)
HU (1)	HU217297B (ja)
PL (1)	PL183494B1 (ja)
PT (1)	PT773224E (ja)
SI (1)	SI0773224T1 (ja)
SK (1)	SK143596A3 (ja)
TW (1)	TW382018B (ja)

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JP3388531B2 (ja) *	1996-11-29	2003-03-24	信越化学工業株式会社	ポリスルフィドシランの脱硫方法
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DE19734295C1 (de) *	1997-08-08	1999-02-25	Degussa	Verfahren zur Herstellung von Organosiliciumdisulfanen hoher Reinheit
JP3465558B2 (ja) *	1997-09-26	2003-11-10	信越化学工業株式会社	ポリスルフィドシランの製造方法
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CA2414076A1 (en)	2000-06-08	2001-12-13	La Jolla Pharmaceutical Company	Multivalent platform molecules comprising high molecular weight polyethylene oxide
US6359046B1 (en)	2000-09-08	2002-03-19	Crompton Corporation	Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions
CN1271131C (zh) *	2001-03-12	2006-08-23	米其林技术公司	轮胎胎面用橡胶组合物
FR2823210B1 (fr) *	2001-04-10	2005-04-01	Rhodia Chimie Sa	Organoxysilanes polysulfures utilisables notamment en tant qu'agent de couplage, compositions d'elastomere(s) les contenant et articles en elastomere(s) prepares a partir de telles compositions
DE10122269A1 (de)	2001-05-08	2002-11-21	Degussa	Silanmodifizierter biopolymerer, biooligomerer, oxidischer oder silikatischer Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung
CN1547601B (zh) *	2001-06-28	2012-09-05	米其林技术公司	采用具有低比表面积的二氧化硅增强的轮胎胎面
CN1325549C (zh) *	2001-06-28	2007-07-11	米其林技术公司	采用具有非常低比表面积的二氧化硅增强的轮胎胎面
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US6433206B1 (en)	2001-11-05	2002-08-13	Crompton Corporation	Process for preparing silylorganomercaptans
WO2003046066A1 (fr)	2001-11-26	2003-06-05	Societe De Technologie Michelin	Composition de caoutchouc pour bande de roulement de pneu et son procede d'obtention
JP2003261580A (ja)	2002-03-08	2003-09-19	Shin Etsu Chem Co Ltd	スルフィド鎖含有有機珪素化合物の製造方法
DE10218350A1 (de)	2002-04-25	2003-11-20	Degussa	Silanmodifizierter oxidischer oder silikatischer Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung
KR20050057207A (ko) *	2002-09-04	2005-06-16	소시에떼 드 테크놀로지 미쉐린	타이어 트레드용 고무 조성물
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US7968635B2 (en)	2006-12-28	2011-06-28	Continental Ag	Tire compositions and components containing free-flowing filler compositions
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1995
- 1995-11-07 DE DE19541404A patent/DE19541404A1/de not_active Withdrawn
1996
- 1996-09-23 DE DE59608364T patent/DE59608364D1/de not_active Expired - Fee Related
- 1996-09-23 SI SI9630415T patent/SI0773224T1/xx unknown
- 1996-09-23 EP EP96115226A patent/EP0773224B1/de not_active Expired - Lifetime
- 1996-09-23 PT PT96115226T patent/PT773224E/pt unknown
- 1996-09-23 ES ES96115226T patent/ES2168424T3/es not_active Expired - Lifetime
- 1996-10-30 CZ CZ963180A patent/CZ318096A3/cs unknown
- 1996-10-30 TW TW085113256A patent/TW382018B/zh not_active IP Right Cessation
- 1996-10-30 PL PL96316746A patent/PL183494B1/pl unknown
- 1996-11-04 CN CN96120660A patent/CN1070862C/zh not_active Expired - Fee Related
- 1996-11-05 JP JP8292755A patent/JPH09169774A/ja not_active Abandoned
- 1996-11-05 US US08/743,842 patent/US5663395A/en not_active Expired - Fee Related
- 1996-11-05 CA CA002189601A patent/CA2189601A1/en not_active Abandoned
- 1996-11-05 HR HR960516A patent/HRP960516B1/xx not_active IP Right Cessation
- 1996-11-06 KR KR1019960052353A patent/KR970027094A/ko not_active Application Discontinuation
- 1996-11-06 AU AU70624/96A patent/AU713295B2/en not_active Ceased
- 1996-11-06 HU HU9603081A patent/HU217297B/hu not_active IP Right Cessation
- 1996-11-06 SK SK1435-96A patent/SK143596A3/sk unknown
- 1996-11-07 BR BR9605476A patent/BR9605476A/pt active Search and Examination

Also Published As

Publication number	Publication date
BR9605476A (pt)	1998-08-11
CA2189601A1 (en)	1997-05-08
JPH09169774A (ja)	1997-06-30
KR970027094A (ko)	1997-06-24
CN1070862C (zh)	2001-09-12
AU713295B2 (en)	1999-11-25
ES2168424T3 (es)	2002-06-16
PL316746A1 (en)	1997-05-12
SI0773224T1 (en)	2002-06-30
AU7062496A (en)	1997-05-15
HU217297B (hu)	1999-12-28
EP0773224A3 (de)	1998-03-18
EP0773224B1 (de)	2001-12-05
PT773224E (pt)	2002-05-31
CZ318096A3 (en)	1997-05-14
TW382018B (en)	2000-02-11
HU9603081D0 (en)	1996-12-30
HUP9603081A2 (en)	1997-10-28
DE59608364D1 (de)	2002-01-17
PL183494B1 (pl)	2002-06-28
CN1156149A (zh)	1997-08-06
HRP960516A2 (en)	1998-02-28
US5663395A (en)	1997-09-02
HRP960516B1 (en)	2002-04-30
EP0773224A2 (de)	1997-05-14
DE19541404A1 (de)	1997-05-15
HUP9603081A3 (en)	1998-09-28

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