KR880001557A - 저휘발성/유기 가용성 포스핀 리간드를 사용한 하이드로 포밀화 방법 - Google Patents
저휘발성/유기 가용성 포스핀 리간드를 사용한 하이드로 포밀화 방법 Download PDFInfo
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- KR880001557A KR880001557A KR1019870007423A KR870007423A KR880001557A KR 880001557 A KR880001557 A KR 880001557A KR 1019870007423 A KR1019870007423 A KR 1019870007423A KR 870007423 A KR870007423 A KR 870007423A KR 880001557 A KR880001557 A KR 880001557A
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- South Korea
- Prior art keywords
- carbon atoms
- radical
- alkyl
- group
- hydrogen
- Prior art date
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- 238000000034 method Methods 0.000 title claims 24
- 239000003446 ligand Substances 0.000 title claims 7
- 238000007037 hydroformylation reaction Methods 0.000 title claims 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 title 1
- -1 cycloalkyl radicals Chemical class 0.000 claims 21
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 239000004711 α-olefin Substances 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims 2
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 claims 2
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-O trioctylazanium Chemical compound CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-O 0.000 claims 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 150000003003 phosphines Chemical group 0.000 claims 1
- 125000003367 polycyclic group Polymers 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (20)
- 올레핀계 불포화 유기 화합물을, 유기 가용화Ⅷ 족 전이금속-포스포러스 리간드 착화합물 촉매 및 유리 포스포러스 리간드를 함유하는 비수성 하이드로포밀화 반응매질 중에서, 일산화탄소 및 수소와 반응시켜 알데히드를 제조하는 비수성 하이드로 포밀화 방법에 있어서, 상기 착화합물 촉매의 포스포러스 리간드 및 상기 유리포스러스 리간드로서 하기 일반식의 저취발성, 유기 가용성 일설폰화 3급 포시핀 염을 사용함을 특징으로 하는 방법.상기식에서, 각 R그룹은 각기 알킬, 아릴, 알크아릴, 아르아릴, 및 사이클로알킬 라디칼로 이루어진 군중에서 선택되는 탄소수 1내지 30의 라디칼을 나타내고, M은 일반식의야민 양이온을 나탸내며, 여기에서 R1수소 또는 알킬, 아릴, 알크아릴, 아르알킬 및 사이클로알킬 라디칼로 이루어진 군중에서 선택 되는 탄소수 1내지 30의 라디칼을 나태내고, 각 R², R³ 및 R⁴그룹은 각기 알킬, 아릴, 알크아릴, 아르알킬 및 사이클로 헥실 라디칼로 이루어진 군중에서 선택되는 라디칼을 나타내며, 상기 R1, R²,R³ 및 R⁴그룹중의 2개 또는 3개는 함께 결합하여 상기 아민 양이온 질소원자와 함께 모노-, 비-, 또는 폴리-사이클릭 환을 형성할 수 있으며 ; 단, 사용된 일설폰화 3급 포스핀염에서 아민 양이온 M 의 상기R¹, R²,R³및 R⁴그룹중의 하나 이상은 탄소수 8내지 30의 알킬 또는 아르알킬 라디칼을 나타내어야 한다.
- 제1항에 있어서, 하이드로포밀화 반응조건이 약45°C 내지 약200°C의 반응온도와 약 1500psia 미만의, 수소, 일산화탄소 및 올레핀계 불포화 화합물의 총기압을 포함하며, 기체상 소소 대 일산화탄소의 Hz : co 몰비가 약 1 : 10 내지 100 : 1 의 범위이며 : 반응 매질이 상기 매질중 Ⅷ 족 전이금속의 몰당 약 4몰 이상의 총유티 포스러스 리간드를 함유하는 방법.
- 제2항에 있어서, 기체상 수소 대 일산화탄소의 H₂: co몰비가 약1 :1 내지 50 :1의 범위인 방법.
- 제2항에서 있어서, Ⅷ족 전이금속이 로듐이고, 올레핀계 불포화 화합물이 2내지 20개의 탄소원자를 함유하며, 반응온도가 약60°C 내지 약140°C이고, 수소, 일산화탄소 및 올레핀계 불포화 화합물의 총기압이 약 500psia 미만이며, 일산화탄소 분압이 약 1내지 120psia 이고, 수소 분압이 약 15내지 160psia 인 방법.
- 제4항에 있어서, 올레핀계 불포화 화합물이 탄소수 2내지 5의 알파 올레핀인 방법.
- 제5항에 있어서, 각 R 이 각기 탄소수 3내지 9의 측쇄 알킬 라디칼, 페닐 및 사이클로헥실 라디칼로 이루어진 그룹중에서 선택되는 라디칼인 방법.
- 제6항에 있어서 R¹이 수소 또는 탄소수 1내지 20의 알킬 라디칼이고, R2및, R3가 각기 탄소수 1내지 20의 알킬 라디칼이며, R⁴가 탄소수 8내지 20의 알킬 또는 아르알킬 라디칼인 방법
- 제7항에 있어서, 각 R이 각기 페닐 또는 사이클로헥실 라디칼이고, R¹이 수소이며, R² 및, R³가 각기 탄소수 1내지 8의 알킬 라디칼이고, R⁴가 탄소수 8내지 16의 알킬 라디칼인 방법.
- 제8항에 있어서, 알파 올레핀이 프로필렌 또는 부텐-1이고,M+가 트리옥틸암모늄, 디메틸도데실 암모늄, 디메틸옥틸암모늄 및 디메틸세틸암모늄으로 이루어진 그룹중에 선택되는 4급 암모늄 라디칼을 나타내는 방법.
- 제4항에 있어서, 올레핀계 분포화 화합물이 탄소수 6내지 20의 알파 올레핀인 방법.
- 제10항에 있어서, 알파 올레핀이 6내지 14개의 탄소원자를 함유하는 방법.
- 제11항에 있어서, 각 R이 각기 탄소수 3내지 9의 측쇄 알킬 라디칼, 페닐 및 사이클로헥실 라디칼로 이루어진 그룹중에서 선택되는 라디칼인 방법.
- 제12항에 있어서, R¹이 수소 또는 탄소수 1내지 20의 알킬 라디칼이고, R² 및, R³가 각기 탄소수 1내지 20의 알킬 라디칼이며, R⁴가 탄소수 8내지 20의 알킬또는 아르알킬 라디칼인 방법.
- 제13항에 있어서, 각 R이 각기 페닐 또는 사이클로 헥실 라디칼이고, R¹이 수소이며, R² 및 R³가 각기 탄소수 1내지 8의 알킬 라디칼이고, R⁴가 탄소수 8내지 16의 알킬 라디칼인 방법.
- 제14항에 있어서,M+이 트리옥틸암모늄, 디메틸도데실암모늄, 디메틸옥틸암모늄 및 디메틸세틸 암모늄으로 이루어진 그룹중에서 선택되는 4급 암모늄 라디칼을 나타내는 방법.
- 제15항에 있어서, 알파 올레핀이 옥텐-1 방법.
- 제11항에 있어서, 일설폰화 3급 포스핀염 리간드가 3-(디페닐포스핀)벤젠설폰산 트리옥틸암모늄인 방법.
- 제17항에 있어서, 알파 올레핀이 옥텐-1인 방법.
- 제17항에 있어서, 알파 올레핀이 도데센-1인 방법.
- 제11항에 있어서, 하이드로 포밀화 방법이 연속적 촉매-함유 액체 재순환 공정을 포함하는 방법.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/884,197 US4716250A (en) | 1986-07-10 | 1986-07-10 | Hydroformylation using low volatile/organic soluble phosphine ligands |
| US884197 | 1986-07-10 | ||
| US884,197 | 1986-07-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR880001557A true KR880001557A (ko) | 1988-04-25 |
| KR910008369B1 KR910008369B1 (ko) | 1991-10-12 |
Family
ID=25384155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870007423A KR910008369B1 (ko) | 1986-07-10 | 1987-07-10 | 저휘발성/유기 가용성 포스핀 리간드를 사용한 하이드로포밀화 방법 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4716250A (ko) |
| EP (1) | EP0254937B1 (ko) |
| JP (1) | JPS6388150A (ko) |
| KR (1) | KR910008369B1 (ko) |
| CN (1) | CN1020720C (ko) |
| AR (1) | AR243490A1 (ko) |
| AT (1) | ATE74120T1 (ko) |
| AU (1) | AU605773B2 (ko) |
| BE (1) | BE1001190A5 (ko) |
| BR (1) | BR8703510A (ko) |
| CA (1) | CA1307006C (ko) |
| CS (1) | CS271475B2 (ko) |
| DE (2) | DE3722928A1 (ko) |
| DK (1) | DK359987A (ko) |
| ES (1) | ES2007367A6 (ko) |
| FI (1) | FI89351C (ko) |
| FR (1) | FR2603579B1 (ko) |
| GB (1) | GB2193494B (ko) |
| HU (1) | HU202468B (ko) |
| IN (1) | IN169702B (ko) |
| IT (1) | IT1221979B (ko) |
| MX (1) | MX166891B (ko) |
| NL (1) | NL8701626A (ko) |
| NO (1) | NO165877C (ko) |
| PL (1) | PL151795B1 (ko) |
| SE (1) | SE8702822L (ko) |
| SU (1) | SU1715202A3 (ko) |
| YU (1) | YU46424B (ko) |
| ZA (1) | ZA875058B (ko) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| US5180854A (en) * | 1988-07-14 | 1993-01-19 | Union Carbide Chemicals & Plastics Technology Corporation | Process for catalyst aldehyde product separation |
| US5113022A (en) * | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| US5059710A (en) * | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
| US4935550A (en) * | 1988-08-12 | 1990-06-19 | Union Carbide Chemicals And Plastics Company Inc. | Catalytic metal recovery from non-polar organic solutions |
| US4861918A (en) * | 1988-08-12 | 1989-08-29 | Union Carbide Corporation | Reactivation of hydroformylation catalysts |
| US4929767A (en) * | 1988-08-12 | 1990-05-29 | Union Carbide Chemicals And Plastics Company Inc. | Treatment of rhodium catalysts |
| DE3942954A1 (de) * | 1989-12-23 | 1991-06-27 | Hoechst Ag | Verfahren zur herstellung von aldehyden |
| EP0545997B1 (en) * | 1990-08-31 | 1995-11-02 | The Governors Of The University Of Alberta | Carbonylation of methanol using a novel transition metal catalyst precursor |
| US5087763A (en) * | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| CN1036388C (zh) * | 1992-12-29 | 1997-11-12 | 中国石化兰州炼油化工总厂 | 烯烃氢甲酰化合成醛的方法 |
| DE19619528A1 (de) * | 1996-05-15 | 1997-11-20 | Hoechst Ag | Substituierte Diphosphine und ein Verfahren zu ihrer Herstellung |
| EP0823282B1 (de) * | 1996-05-15 | 2001-11-14 | Celanese Chemicals Europe GmbH | Verfahren zur Herstellung von Aldehyden |
| ID21537A (id) * | 1997-12-22 | 1999-06-24 | Celanese Gmbh | Proses pembuatan aldehid |
| DE19756945C2 (de) * | 1997-12-22 | 2000-08-03 | Celanese Chem Europe Gmbh | Nichtwäßrige ionogene Ligandflüssigkeiten, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatorbestandteil |
| JP3921853B2 (ja) * | 1998-12-10 | 2007-05-30 | 三菱化学株式会社 | アルデヒド類及びアルコール類の製造方法 |
| FR2813305B1 (fr) * | 2000-08-23 | 2004-02-13 | Inst Francais Du Petrole | Procede ameliore d'hydroformylation mettant en oeuvre un catalyseur a base de cobalt et/ou de rhodium dans un solvant ionique non aqueux |
| SG93931A1 (en) * | 2001-04-13 | 2003-01-21 | Kuraray Co | Phosphonium salts and processes for production of and uses for the same, and phosphines deriving the same and processes for production of the phosphines |
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- 1986-07-10 US US06/884,197 patent/US4716250A/en not_active Expired - Lifetime
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- 1987-07-03 CA CA000541210A patent/CA1307006C/en not_active Expired - Lifetime
- 1987-07-08 IT IT21213/87A patent/IT1221979B/it active
- 1987-07-09 MX MX007263A patent/MX166891B/es unknown
- 1987-07-09 SE SE8702822A patent/SE8702822L/xx not_active Application Discontinuation
- 1987-07-09 BR BR8703510A patent/BR8703510A/pt active Search and Examination
- 1987-07-09 FR FR878709755A patent/FR2603579B1/fr not_active Expired - Lifetime
- 1987-07-09 GB GB8716161A patent/GB2193494B/en not_active Expired - Lifetime
- 1987-07-10 YU YU129787A patent/YU46424B/sh unknown
- 1987-07-10 KR KR1019870007423A patent/KR910008369B1/ko not_active IP Right Cessation
- 1987-07-10 AT AT87110014T patent/ATE74120T1/de not_active IP Right Cessation
- 1987-07-10 FI FI873054A patent/FI89351C/fi not_active IP Right Cessation
- 1987-07-10 AR AR87308111A patent/AR243490A1/es active
- 1987-07-10 BE BE8700760A patent/BE1001190A5/fr not_active IP Right Cessation
- 1987-07-10 AU AU75531/87A patent/AU605773B2/en not_active Ceased
- 1987-07-10 SU SU874202974A patent/SU1715202A3/ru active
- 1987-07-10 DK DK359987A patent/DK359987A/da not_active Application Discontinuation
- 1987-07-10 IN IN490/MAS/87A patent/IN169702B/en unknown
- 1987-07-10 EP EP87110014A patent/EP0254937B1/en not_active Expired - Lifetime
- 1987-07-10 NL NL8701626A patent/NL8701626A/nl not_active Application Discontinuation
- 1987-07-10 CN CN87105466A patent/CN1020720C/zh not_active Expired - Fee Related
- 1987-07-10 ES ES8702037A patent/ES2007367A6/es not_active Expired
- 1987-07-10 DE DE19873722928 patent/DE3722928A1/de not_active Withdrawn
- 1987-07-10 PL PL1987266758A patent/PL151795B1/pl unknown
- 1987-07-10 CS CS875276A patent/CS271475B2/cs unknown
- 1987-07-10 JP JP62171368A patent/JPS6388150A/ja active Granted
- 1987-07-10 DE DE8787110014T patent/DE3777714D1/de not_active Expired - Lifetime
- 1987-07-10 NO NO872887A patent/NO165877C/no unknown
- 1987-07-10 HU HU873163A patent/HU202468B/hu not_active IP Right Cessation
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