CH498795A - Procédé pour la préparation de cétones insaturées - Google Patents
Procédé pour la préparation de cétones insaturéesInfo
- Publication number
- CH498795A CH498795A CH1630968A CH1630968A CH498795A CH 498795 A CH498795 A CH 498795A CH 1630968 A CH1630968 A CH 1630968A CH 1630968 A CH1630968 A CH 1630968A CH 498795 A CH498795 A CH 498795A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- unsaturated ketones
- ketones
- unsaturated
- Prior art date
Links
- 150000002576 ketones Chemical class 0.000 title 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Toxicology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
- Seasonings (AREA)
- Cosmetics (AREA)
- Grain Derivatives (AREA)
- Tea And Coffee (AREA)
- Manufacture Of Tobacco Products (AREA)
- Fodder In General (AREA)
- Non-Alcoholic Beverages (AREA)
- Detergent Compositions (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1566767A CH520479A (fr) | 1967-11-09 | 1967-11-09 | Utilisation de cétones non saturées comme agents aromatisants |
| CH84770A CH503684A (fr) | 1968-11-01 | 1968-11-01 | Procédé pour la préparation de cétones insaturées |
| CH84870A CH503685A (fr) | 1968-11-01 | 1968-11-01 | Procédé pour la préparation de cétones insaturées |
| CH1630968A CH498795A (fr) | 1967-11-09 | 1968-11-01 | Procédé pour la préparation de cétones insaturées |
| GB52779/68A GB1240309A (en) | 1967-11-09 | 1968-11-07 | Cycloaliphatic unsaturated ketones |
| GB3392/71A GB1240310A (en) | 1967-11-09 | 1968-11-07 | Cycloaliphatic unsaturated alcohols |
| DE1807568A DE1807568C3 (de) | 1967-11-09 | 1968-11-07 | Cycloaliphatische ungesättigte Ketone, Verfahren zu deren Herstellung und deren Verwendung als Riech- und Geschmacksstoffe |
| DE19681817884 DE1817884C3 (de) | 1967-11-09 | 1968-11-07 | Ungesättigte cycloaliphatische Alkohole und Ketone und Verfahren zu deren Herstellung |
| SE15192/68A SE359086B (fr) | 1967-11-09 | 1968-11-08 | |
| BE723610D BE723610A (fr) | 1967-11-09 | 1968-11-08 | |
| NL686815985A NL146801B (nl) | 1967-11-09 | 1968-11-08 | Werkwijze voor de bereiding van een keton met geur- en smaakeigenschappen, en van dit keton bevattende materialen, alsmede de daarmede vervaardigde voorwerpen. |
| IT23548/68A IT1034009B (it) | 1967-11-09 | 1968-11-09 | Chetoni cicloalifatici insaturi |
| FR1591031D FR1591031A (fr) | 1967-11-09 | 1968-11-12 | |
| ES377483A ES377483A1 (es) | 1968-11-01 | 1970-03-13 | Un metodo para la preparacion de cetonas. |
| ES377485A ES377485A1 (es) | 1968-11-01 | 1970-03-13 | Un metodo para la preparacion de cetonas. |
| DE19702022216 DE2022216C3 (de) | 1969-05-07 | 1970-05-06 | 17.04.70 Schweiz 5725-70 Cycloaliphatische ungesättigte Ketone, Verfahren zu deren Herstellung und deren Verwendung als Riech- und Geschmacksstoffe |
| JP45096898A JPS4829216B1 (fr) | 1967-11-09 | 1970-11-05 | |
| JP45096899A JPS4831105B1 (fr) | 1967-11-09 | 1970-11-05 | |
| JP45096897A JPS4829215B1 (fr) | 1967-11-09 | 1970-11-05 | |
| JP45096901A JPS4828428B1 (fr) | 1967-11-09 | 1970-11-05 | |
| JP45096900A JPS4829217B1 (fr) | 1967-11-09 | 1970-11-05 | |
| US503794A US3928456A (en) | 1967-11-09 | 1974-09-06 | Cycloaliphatic unsaturated ketones as odour- and taste-modifying agents |
| US05/503,738 US3975310A (en) | 1967-11-09 | 1974-09-06 | Cycloaliphatic unsaturated ketones as odor- and taste-modifying agents |
| US05/523,743 US3931326A (en) | 1967-11-09 | 1974-11-14 | Alkenoyl-cyclohexadienes |
| NL7500196.A NL158159C (nl) | 1967-11-09 | 1975-01-08 | Werkwijze voor de bereiding van een keton met geur- en smaakeigenschappen, en van dit keton bevattende materialen. |
| NL7502981.A NL158160C (nl) | 1967-11-09 | 1975-03-13 | Werkwijze ter bereiding van een keton met geur- en smaakeigenschappen, en van dit keton bevattende materialen. |
| US05/782,536 US4187863A (en) | 1967-11-09 | 1977-03-29 | Cycloaliphatic unsaturated ketones as odor and taste modifying agents in tobacco products |
| US05/900,522 US4226892A (en) | 1967-11-09 | 1978-04-27 | Flavoring with cycloaliphatic unsaturated ketones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1566767A CH520479A (fr) | 1967-11-09 | 1967-11-09 | Utilisation de cétones non saturées comme agents aromatisants |
| CH1630968A CH498795A (fr) | 1967-11-09 | 1968-11-01 | Procédé pour la préparation de cétones insaturées |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH498795A true CH498795A (fr) | 1970-11-15 |
Family
ID=25716810
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1566767A CH520479A (fr) | 1967-11-09 | 1967-11-09 | Utilisation de cétones non saturées comme agents aromatisants |
| CH1630968A CH498795A (fr) | 1967-11-09 | 1968-11-01 | Procédé pour la préparation de cétones insaturées |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1566767A CH520479A (fr) | 1967-11-09 | 1967-11-09 | Utilisation de cétones non saturées comme agents aromatisants |
Country Status (9)
| Country | Link |
|---|---|
| JP (5) | JPS4828428B1 (fr) |
| BE (1) | BE723610A (fr) |
| CH (2) | CH520479A (fr) |
| DE (1) | DE1807568C3 (fr) |
| FR (1) | FR1591031A (fr) |
| GB (2) | GB1240309A (fr) |
| IT (1) | IT1034009B (fr) |
| NL (1) | NL146801B (fr) |
| SE (1) | SE359086B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2120413C3 (de) * | 1971-04-26 | 1981-04-09 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Trans-2,4,4-trimethyl-1-crotonoylcyclohex-2-en-Verbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Riech- bzw. Aromastoffe |
| US4028278A (en) * | 1971-08-17 | 1977-06-07 | Firmenich S.A. | Cycloaliphatic unsaturated ketones as fragrance modifying agents |
| GB1390654A (en) * | 1972-10-26 | 1975-04-16 | Beheer Bv Pfw | Materials for flavours and perfumes and process therefor |
| US3928645A (en) * | 1973-08-07 | 1975-12-23 | Int Flavors & Fragrances Inc | Enhancing red-berry flavor with 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanone and 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanone |
| JPS519114U (fr) * | 1974-07-10 | 1976-01-23 | ||
| JPS5341210A (en) * | 1976-09-27 | 1978-04-14 | Hitachi Ltd | Cassette tape recorder |
| CH648015A5 (de) * | 1977-03-28 | 1985-02-28 | Givaudan & Cie Sa | Cyclohexenonderivate mit riech- und/oder geschmackstoffeigenschaften. |
| JPS53163411U (fr) * | 1977-05-30 | 1978-12-21 | ||
| US4206090A (en) * | 1978-10-06 | 1980-06-03 | International Flavors & Fragrances Inc. | 3-Methyl-1-phenyl-pentanol-5 or its isomer and butanoyl cyclohexane derivatives |
| US4292447A (en) * | 1978-12-15 | 1981-09-29 | International Flavors & Fragrances Inc. | Process for hydrogenation of 2,6,6-trimethyl cyclohexene derivatives, products produced thereby and organoleptic uses of said products |
| US4324704A (en) | 1978-12-15 | 1982-04-13 | International Flavors & Fragrances Inc. | Process for hydrogenation of damascenone, products produced thereby and organoleptic uses of said products |
| US4225444A (en) | 1979-07-13 | 1980-09-30 | International Flavors & Fragrances Inc. | Fragrance compositions containing 3-methyl-1-phenyl-pentanol-5 or specific optical isomers thereof and one or more butanoyl cyclohexane derivatives |
| JPS5690413U (fr) * | 1980-11-26 | 1981-07-18 | ||
| US4536583A (en) * | 1983-08-01 | 1985-08-20 | International Flavors & Fragrances Inc. | Process for preparing mixtures containing 8,9-epithio-1-p-menthene |
| EP0181475B1 (fr) * | 1984-10-15 | 1988-06-08 | Firmenich Sa | Cétone aliphatique non saturée et son utilisation à titre d'ingrédient parfumant |
| EP0231556A1 (fr) * | 1986-01-23 | 1987-08-12 | Naarden International N.V. | Isopropyl-méthyl-buténoyl-cyclohexanes, -cyclohexènes et cyclohexadiènes, compositions parfumantes et articles et produits parfumés comprenant les composés comme ingrédient parfumé |
| CN1055078C (zh) * | 1997-07-08 | 2000-08-02 | 云南省化工研究院 | 一种合成二氢突厥酮的方法 |
| ES2779460T3 (es) * | 2015-08-18 | 2020-08-17 | Basf Se | Proceso de preparación del alfa-damascona |
| JP7650627B2 (ja) * | 2020-07-29 | 2025-03-25 | アサヒ飲料株式会社 | 果汁含有飲料 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011881B (de) * | 1954-07-16 | 1957-07-11 | Hoffmann La Roche | Verfahren zur Herstellung von 8-[2', 6', 6'-Trimethylcyclohexen-(2')-yliden]-2, 6-dimethyloctadien-(2, 6)-in-(4)-al-(1) und 8-[2', 6', 6'-Trimethylcyclohexen-(2')-yliden]-2, 6-dimethyloctatrien-(2, 4, 6)-al-(1) |
| DE1005956B (de) * | 1954-12-22 | 1957-04-11 | Hoffmann La Roche | Verfahren zur Herstellung von Vitamin A bzw. dessen Estern |
| DE1030827B (de) * | 1956-02-23 | 1958-05-29 | Hoffmann La Roche | Verfahren zur Herstellung von 4-[3-AEthyl-2, 6, 6-trimethyl-cyclohexen-(2)-yl]-buten-(3)-on-(2) |
| DE1112736B (de) * | 1959-01-16 | 1961-08-17 | Hoffmann La Roche | Verfahren zur Herstellung von alicyclischen Ketonen mit wertvollen Riechstoffeigenschaften |
| US3354218A (en) * | 1963-05-10 | 1967-11-21 | Hoffmann La Roche | Process for preparing 4-(2, 6, 6-trimethyl-4-methoxy-1-cyclohexen-1-yl)-3-buten-2-one |
| GB1073609A (en) * | 1965-03-17 | 1967-06-28 | Reynolds Tobacco Co R | Synthesis of dehydroionone |
-
1967
- 1967-11-09 CH CH1566767A patent/CH520479A/fr not_active IP Right Cessation
-
1968
- 1968-11-01 CH CH1630968A patent/CH498795A/fr not_active IP Right Cessation
- 1968-11-07 DE DE1807568A patent/DE1807568C3/de not_active Expired
- 1968-11-07 GB GB52779/68A patent/GB1240309A/en not_active Expired
- 1968-11-07 GB GB3392/71A patent/GB1240310A/en not_active Expired
- 1968-11-08 SE SE15192/68A patent/SE359086B/xx unknown
- 1968-11-08 NL NL686815985A patent/NL146801B/xx not_active IP Right Cessation
- 1968-11-08 BE BE723610D patent/BE723610A/xx unknown
- 1968-11-09 IT IT23548/68A patent/IT1034009B/it active
- 1968-11-12 FR FR1591031D patent/FR1591031A/fr not_active Expired
-
1970
- 1970-11-05 JP JP45096901A patent/JPS4828428B1/ja active Pending
- 1970-11-05 JP JP45096898A patent/JPS4829216B1/ja active Pending
- 1970-11-05 JP JP45096899A patent/JPS4831105B1/ja active Pending
- 1970-11-05 JP JP45096900A patent/JPS4829217B1/ja active Pending
- 1970-11-05 JP JP45096897A patent/JPS4829215B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1034009B (it) | 1979-09-10 |
| NL6815985A (fr) | 1969-05-13 |
| DE1807568C3 (de) | 1982-05-13 |
| JPS4829217B1 (fr) | 1973-09-08 |
| DE1817884B2 (de) | 1976-11-11 |
| DE1817884A1 (de) | 1973-03-29 |
| NL146801B (nl) | 1975-08-15 |
| SE359086B (fr) | 1973-08-20 |
| CH520479A (fr) | 1972-03-31 |
| GB1240310A (en) | 1971-07-21 |
| BE723610A (fr) | 1969-05-08 |
| JPS4829215B1 (fr) | 1973-09-08 |
| DE1807568B2 (de) | 1975-04-10 |
| FR1591031A (fr) | 1970-04-20 |
| JPS4828428B1 (fr) | 1973-09-01 |
| JPS4829216B1 (fr) | 1973-09-08 |
| JPS4831105B1 (fr) | 1973-09-26 |
| GB1240309A (en) | 1971-07-21 |
| DE1807568A1 (de) | 1969-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |