KR910006260A - 헤테로환상 티올 설펜이미드 화합물 - Google Patents
헤테로환상 티올 설펜이미드 화합물 Download PDFInfo
- Publication number
- KR910006260A KR910006260A KR1019900013899A KR900013899A KR910006260A KR 910006260 A KR910006260 A KR 910006260A KR 1019900013899 A KR1019900013899 A KR 1019900013899A KR 900013899 A KR900013899 A KR 900013899A KR 910006260 A KR910006260 A KR 910006260A
- Authority
- KR
- South Korea
- Prior art keywords
- composition
- rubber
- compound
- sulfenimide
- vulcanized
- Prior art date
Links
- -1 Heterocyclic Thiol Chemical class 0.000 title claims 12
- 150000001875 compounds Chemical class 0.000 title claims 7
- 239000000203 mixture Substances 0.000 claims 21
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 229920001971 elastomer Polymers 0.000 claims 8
- 239000005060 rubber Substances 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- 229920003051 synthetic elastomer Polymers 0.000 claims 3
- 239000005061 synthetic rubber Substances 0.000 claims 3
- 244000043261 Hevea brasiliensis Species 0.000 claims 2
- 229920003052 natural elastomer Polymers 0.000 claims 2
- 229920001194 natural rubber Polymers 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006378 chloropyridyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000005412 pyrazyl group Chemical group 0.000 claims 1
- 125000005495 pyridazyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
본 도면은 가황처리의 매개변수를 보여주는 대표적인 레오그래프(reograph)이다.
Claims (20)
- 일반식(I)의 구조식을 지닌 헤테로환상 티올 설펜이미드를 포함하는 물질.상기식에서 A1과 A2는 각각 하나이상의 질소원자가 포함된 적어도 하나의 헤테로환상 고리와, (1) 하나이상의 하이드로카빌 치환체, 또는 (2) 하나이상의 전자를 끄는 라디칼, 또는 (3) 하나이상의 전자를 내주는 라디칼을 포함하며, 상기 (1)의 하나이상의 하이드로카빌 치환체는 각각 치환제는 각각 1-12개의 탄소원자수를 포함하고, 상기 A1이나 A2기중 적어도 한 기는 베조티아졸일 기가 아니다. 또한, A1은 선택적으로 티아질이나 카보모일이 될 수 있다. 한편 R은 (a) 수소원자 또는 (b) 1-16개의 탄소원자로 된 하이드로카빌 라디칼 또는 (c) (b)의 탄화수소 라디칼로 하나이상의 탄소원자가 산소원자, 질소원자 또는 치환된 질소원자로서 이때 치환된 기는 알킬이고, 상기 질소원자는 총 1-7개의 탄소원자와 결합해 헤테로환상 고리를 형성하며, 또는 (d) 할로겐, 아미노, 시아노, 알콕시, 하이드록시 또는 알콕시카보닐 기를 지닌 (b)의 하이드로카빌 라디칼이다.
- 제1항에 있어서, A1과 A2각각은 적어도 하나, 둘 또는 세개의 질소원자를 가짐을 특징으로 하는 물질.
- 제1항에 있어서, A1과 A2는 각각 하나의 질소원자를 포함하는데, 여기서 A1과 A2는 각각 하나의 질소원자를 포함하고 하나이상의 하이드로카빌 치환체를 가지는 적어도 하나의 헤테로환상 고리이며 이때 상기 하이드로카빌 치환제는 각각 1-6개의 탄소원자를 가지며, 또한 상기 질소원자는 2번자리에 위치함을 특징으로 하는 물질.
- 제3항에 있어서, R은 1-8개의 탄소원자로 된 알킬임을 특징으로 하는 물질.
- 제4항에 있어서, A1과 A2는 각각 트리아지닐, 피라질, 피리다질, 피리미딜, 메틸피리미딜, 디메틸피리미딜, 피리딜, 피코릴, 퀴놀릴, 레피딜, 디메틸피리딜, 페닐피리딜, 메톡시피리딜, 클로로피리딜이며 A1은 또한 티아질이나 디티오카바모일임을 특징으로 하는 물질.
- 제1항에 있어서, 상기 헤테로환상 티올 설펜이미드는 N,N-비스(2-피리티일)-t-부틸 설펜이미드, N,N-비스(2-피리딜티일)-이소프로필 설펜이미드, N,N-비스(2-피리딜티일)-이소프로필 설펜이미드, N,N-비스(2-퀴놀일 티일)-t-부틸 설펜이미드이거나 N,N-비스(2-레피딜티일)-t-부틸 설펜이미드임을 특징으로 하는 물질.
- 제1항 화합물을 가속시키는데 효과적인 양을 포함함을 특징으로 하는 가속화 가황가능한 고무 조성물.
- 제3항 화합물을 가속시키는데 효과적인 양을 포함함을 특징으로 하는 천연고무, 하나이상의 상이한 합성고무 또는 이들의 블렌드인 가속화 가황가능한 고무 조성물.
- 제5항 화합물을 가속시키는데 사용함에 있어, 0.1-10 중량부로 사용함을 특징으로 하는 천연고무, 하나이상의 상이한 합성고무 또는 이들의 블렌드인 가속화 가황가능한 고무 조성물.
- 제6항 화합물을 가속시키는데 사용함에 있어, 0.2-2.0 중량부로 사용함을 특징으로 하는 천연고무, 하나이상의 상이한 합성고무 또는 이들의 블렌드인 가속화 가황가능한 고무 조성물.
- 제7항 조성물의 가황 생성물을 포함함을 특징으로 하는 가황처리된 조성물.
- 제8항 조성물의 가황 생성물을 포함함을 특징으로 하는 가황처리된 조성물.
- 제9항 조성물의 가황 생성물을 포함함을 특징으로 하는 가황처리된 조성물.
- 제10항 조성물의 가황 생성물을 포함함을 특징으로 하는 가황처리된 조성물.
- 제11항 조성물을 성분으로 포함함을 특징으로 하는 고무편.
- 제12항 조성물을 성분으로 포함함을 특징으로 하는 고무편.
- 제13항 조성물을 성분으로 포함함을 특징으로 하는 고무편.
- 제14항 조성물을 성분으로 포함함을 특징으로 하는 고무편.
- 제11항 조성물을 성분으로 포함함을 특징으로 하는 타이어.
- 제14항 조성물을 성분으로 포함함을 특징으로 하는 타이어.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US402741 | 1982-07-28 | ||
| US07/402,741 US5079305A (en) | 1989-09-05 | 1989-09-05 | Rubber compositions comprising sulfenimide accelerators |
| US07/402,741 | 1989-09-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910006260A true KR910006260A (ko) | 1991-04-29 |
| KR930005984B1 KR930005984B1 (ko) | 1993-07-01 |
Family
ID=23593129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900013899A KR930005984B1 (ko) | 1989-09-05 | 1990-09-04 | 헤테로환상 티올 설펜이미드 화합물 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5079305A (ko) |
| EP (1) | EP0417057B1 (ko) |
| JP (1) | JP2914733B2 (ko) |
| KR (1) | KR930005984B1 (ko) |
| AT (1) | ATE119155T1 (ko) |
| AU (1) | AU626102B2 (ko) |
| BR (1) | BR9004385A (ko) |
| CA (1) | CA2024595C (ko) |
| CZ (1) | CZ283117B6 (ko) |
| DE (1) | DE69017321T2 (ko) |
| HU (1) | HU210193B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5260454A (en) * | 1989-09-05 | 1993-11-09 | Monsanto Company | Bis-pyrimidyl thiol sulfenimide compounds |
| AU670437B2 (en) * | 1992-06-05 | 1996-07-18 | Monsanto Company | 4-pyrimidine sulfenamides and their use in rubber |
| US6019549A (en) * | 1996-06-11 | 2000-02-01 | Corrosion Control International Llc | Vortex shedding strake wraps for submerged pilings and pipes |
| US6180795B1 (en) * | 1999-07-30 | 2001-01-30 | Uniroyal Chemical Company, Inc. | Process for making N-alkyl bis(thiazolyl)sulfenimides |
| US6646029B1 (en) * | 2000-03-21 | 2003-11-11 | Flexsys America L.P. | Pyrimidine derivatives as hardness stabilizers |
| JP4426172B2 (ja) | 2001-12-20 | 2010-03-03 | マブチモーター株式会社 | 小型モータに一体化したエンコーダ装置 |
| US6844692B1 (en) | 2003-08-22 | 2005-01-18 | Hella Electronics Corp. | Climate control system and motor actuator therefor |
| FR2951167B1 (fr) * | 2009-10-08 | 2011-10-28 | Michelin Soc Tech | 1,2,4-triazine utilisable comme accelerateur de vulcanisation et son procede d'obtention |
| JP6969336B2 (ja) * | 2017-12-06 | 2021-11-24 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151122A (en) * | 1964-09-29 | Preparation of n-alkyl- and n-cyclo | ||
| US2321306A (en) * | 1939-06-24 | 1943-06-08 | Us Rubber Co | Accelerator of vulcanization |
| US2321305A (en) * | 1939-06-24 | 1943-06-08 | Us Rubber Co | Accelerator of vulcanization |
| GB795174A (en) * | 1954-10-13 | 1958-05-21 | Upjohn Co | Heterocyclic sulphonamides |
| DE1070815B (de) * | 1954-11-16 | 1959-12-10 | United States Rubber Company, New York, N. Y. (V. St. A.) | Beschleunigung der Vulkanisation von Kautschuk |
| US2889331A (en) * | 1956-09-28 | 1959-06-02 | Us Rubber Co | Manufacture of n-alkyl- and n-cycloalkylbis (2-benzothiazolesulfen) amides |
| US2873277A (en) * | 1956-09-28 | 1959-02-10 | Us Rubber Co | Manufacture of n-alkyl-and n-cycloalkylbis (2-benzothiazolesulfen) amides |
| NL98032C (ko) * | 1957-04-02 | |||
| US2930824A (en) * | 1958-05-15 | 1960-03-29 | Us Rubber Co | Certain n, n'-disubstituted ethylenebisbenzothiazolesulfenamides |
| US3071592A (en) * | 1961-07-07 | 1963-01-01 | Us Rubber Co | N, n'-thiodimaleimide and n, n'-dithiodimaleimide |
| FR1368623A (fr) * | 1962-09-17 | 1964-07-31 | Monsanto Chemicals | Nouveaux accélérateurs de vulcanisation |
| US3362937A (en) * | 1965-09-28 | 1968-01-09 | Polymer Corp | Process for curing golf ball cover stock containing a thio amine accelerator by treatment with hydrogen halide |
| US3394126A (en) * | 1966-01-06 | 1968-07-23 | Monsanto Co | Nu, nu'-polythio polymethylenimines |
| DE1620236B2 (de) * | 1966-12-08 | 1976-12-16 | Rhein-Chemie Rheinau Gmbh, 6800 Mannheim | N,n'-dilactamidsulfide |
| US3549650A (en) * | 1966-12-22 | 1970-12-22 | Monsanto Co | Process for preparing n-branched-chain alkyl and cycloalkyl 2-benzothiazole sulfenamides |
| DE1301482B (de) * | 1967-11-23 | 1969-08-21 | Rhein Chemie Rheinau Gmbh | Verfahren zum Vulkanisieren von Kautschuk |
| DE1962604A1 (de) * | 1969-12-13 | 1971-06-24 | Bayer Ag | Vulkanisationsverzoegerer |
| US3875177A (en) * | 1970-01-30 | 1975-04-01 | Rhone Poulenc Sa | Process for the manufacture of bis(benzot hiazylsulphene) amides |
| US3737431A (en) * | 1970-02-24 | 1973-06-05 | Monsanto Co | Preparation of sulfenamides by catalytic oxidation |
| GB1355801A (en) * | 1970-08-12 | 1974-06-05 | Ici Ltd | Substituted sulphenyl halides |
| CA992965A (en) * | 1971-02-08 | 1976-07-13 | John W. Fieldhouse | Diazine, triazine, pyridine, quinoline sulfenamides and their manufacture |
| FR2126370B1 (ko) * | 1971-02-24 | 1973-06-29 | Columbia Research Corp | |
| DE2121522A1 (en) * | 1971-05-03 | 1972-11-16 | Knapsack AG, 5033 Hürth-Knapsack | Natural and synthetic rubber vulcanisation accelerators - - comprising products of bis-(dialkylthiophosphoryl)-tetrasulphide an |
| BE786030A (fr) * | 1971-07-07 | 1973-01-08 | Rhone Poulenc Sa | Nouveaux bis-sulfenamides inhibiteurs de |
| SU504810A1 (ru) * | 1971-11-11 | 1976-02-28 | Предприятие П/Я В-8749 | Резинова смесь |
| US3847880A (en) * | 1973-01-29 | 1974-11-12 | Monsanto Co | Method for vulcanizing rubber with bis-sulfenamide accelerators |
| SU478010A1 (ru) * | 1973-10-08 | 1975-07-25 | Кировский Политехнический Институт | Способ получени -замещенных ненасыщенных циклических бис(2-бензтиазолил)-сульфенамидов |
| US3997605A (en) * | 1975-05-19 | 1976-12-14 | The Goodyear Tire & Rubber Company | Preparation of formamide compounds |
| US4166864A (en) * | 1977-03-28 | 1979-09-04 | Union Carbide Corporation | Pesticidal unsymmetrical bis-arylcarbamate disulfide compounds |
-
1989
- 1989-09-05 US US07/402,741 patent/US5079305A/en not_active Expired - Fee Related
-
1990
- 1990-09-04 CA CA002024595A patent/CA2024595C/en not_active Expired - Fee Related
- 1990-09-04 DE DE69017321T patent/DE69017321T2/de not_active Expired - Fee Related
- 1990-09-04 KR KR1019900013899A patent/KR930005984B1/ko not_active IP Right Cessation
- 1990-09-04 HU HU905783A patent/HU210193B/hu not_active IP Right Cessation
- 1990-09-04 CZ CS904292A patent/CZ283117B6/cs unknown
- 1990-09-04 BR BR909004385A patent/BR9004385A/pt not_active IP Right Cessation
- 1990-09-04 EP EP90870136A patent/EP0417057B1/en not_active Expired - Lifetime
- 1990-09-04 AU AU62119/90A patent/AU626102B2/en not_active Ceased
- 1990-09-04 AT AT90870136T patent/ATE119155T1/de not_active IP Right Cessation
- 1990-09-04 JP JP2234319A patent/JP2914733B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HUT54651A (en) | 1991-03-28 |
| AU626102B2 (en) | 1992-07-23 |
| EP0417057B1 (en) | 1995-03-01 |
| HU210193B (en) | 1995-02-28 |
| BR9004385A (pt) | 1991-09-10 |
| CZ283117B6 (cs) | 1998-01-14 |
| KR930005984B1 (ko) | 1993-07-01 |
| US5079305A (en) | 1992-01-07 |
| DE69017321T2 (de) | 1995-08-31 |
| CZ429290A3 (en) | 1997-08-13 |
| JP2914733B2 (ja) | 1999-07-05 |
| DE69017321D1 (de) | 1995-04-06 |
| JPH03106864A (ja) | 1991-05-07 |
| EP0417057A3 (en) | 1991-07-17 |
| CA2024595C (en) | 1998-08-18 |
| EP0417057A2 (en) | 1991-03-13 |
| ATE119155T1 (de) | 1995-03-15 |
| AU6211990A (en) | 1991-03-14 |
| CA2024595A1 (en) | 1991-03-06 |
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