NO312135B1 - Fremstilling av materialer rike på konjugerte isomerer av langkjedede flerumettede fettsyrerestere - Google Patents
Fremstilling av materialer rike på konjugerte isomerer av langkjedede flerumettede fettsyrerestere Download PDFInfo
- Publication number
- NO312135B1 NO312135B1 NO19984207A NO984207A NO312135B1 NO 312135 B1 NO312135 B1 NO 312135B1 NO 19984207 A NO19984207 A NO 19984207A NO 984207 A NO984207 A NO 984207A NO 312135 B1 NO312135 B1 NO 312135B1
- Authority
- NO
- Norway
- Prior art keywords
- oil
- polyunsaturated fatty
- chain polyunsaturated
- solvent
- fatty acids
- Prior art date
Links
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 16
- 239000000463 material Substances 0.000 title claims abstract description 12
- 125000005313 fatty acid group Chemical group 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000003921 oil Substances 0.000 claims description 20
- 235000019198 oils Nutrition 0.000 claims description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 11
- 235000021588 free fatty acids Nutrition 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 235000013772 propylene glycol Nutrition 0.000 claims description 8
- 239000000344 soap Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical group OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims 1
- 235000013305 food Nutrition 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 238000006317 isomerization reaction Methods 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 8
- 235000015655 Crocus sativus Nutrition 0.000 description 6
- 244000124209 Crocus sativus Species 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004248 saffron Substances 0.000 description 6
- 235000013974 saffron Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 235000020778 linoleic acid Nutrition 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 229940108924 conjugated linoleic acid Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- IBWPUTAKVGZXRB-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)butan-2-ylhydrazine Chemical compound NNC(C)CCC1=CC=C2OCOC2=C1 IBWPUTAKVGZXRB-UHFFFAOYSA-N 0.000 description 1
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical class CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 125000005481 linolenic acid group Chemical group 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6409—Fatty acids
- C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
- C12P7/6431—Linoleic acids [18:2[n-6]]
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97307110 | 1997-09-12 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO984207D0 NO984207D0 (no) | 1998-09-11 |
NO984207L NO984207L (no) | 1999-03-15 |
NO312135B1 true NO312135B1 (no) | 2002-03-25 |
Family
ID=8229510
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19984207A NO312135B1 (no) | 1997-09-12 | 1998-09-11 | Fremstilling av materialer rike på konjugerte isomerer av langkjedede flerumettede fettsyrerestere |
Country Status (10)
Country | Link |
---|---|
US (2) | US6160140A (fr) |
EP (1) | EP0902082B1 (fr) |
AT (1) | ATE245688T1 (fr) |
AU (1) | AU727994B2 (fr) |
CA (1) | CA2246085C (fr) |
DE (1) | DE69816545T2 (fr) |
DK (1) | DK0902082T3 (fr) |
ES (1) | ES2206828T3 (fr) |
NO (1) | NO312135B1 (fr) |
ZA (1) | ZA987962B (fr) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6288114B1 (en) † | 1997-06-23 | 2001-09-11 | Cornell Research Foundation, Inc. | Method of altering nutritional components of milk produced by a lactating animal |
US6015833A (en) | 1998-03-17 | 2000-01-18 | Conlinco., Inc. | Conjugated linoleic acid compositions |
KR100619651B1 (ko) | 1998-03-17 | 2006-09-05 | 콘린코 인크. | 공액 리놀레산 조성물 |
US7776353B1 (en) | 1998-03-17 | 2010-08-17 | Aker Biomarine Asa | Conjugated linoleic acid compositions |
US7078051B1 (en) | 1998-08-11 | 2006-07-18 | Natural Asa | Conjugated linoleic acid alkyl esters in feedstuffs and food |
US6214372B1 (en) | 1998-05-04 | 2001-04-10 | Con Lin Co., Inc. | Method of using isomer enriched conjugated linoleic acid compositions |
US7101914B2 (en) * | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
JP2000144170A (ja) * | 1998-09-01 | 2000-05-26 | Janifu Tekku:Kk | 抗肥満及び内臓蓄積脂肪低減化機能を有する物質、及びその用途 |
AU5144901A (en) | 2000-04-06 | 2001-10-23 | Conlinco Inc | Conjugated linoleic acid compositions |
US20030149288A1 (en) * | 2000-04-18 | 2003-08-07 | Natural Asa | Conjugated linoleic acid powder |
WO2001078531A2 (fr) | 2000-04-18 | 2001-10-25 | Natural As | Poudre d'acide linoleique conjugue |
DE10046402B4 (de) | 2000-09-18 | 2006-04-20 | Cognis Ip Management Gmbh | Verfahren zur Herstellung von Rohstoffen für die Gewinnung von konjugierter Linolsäure |
US6677470B2 (en) | 2001-11-20 | 2004-01-13 | Natural Asa | Functional acylglycerides |
US6743931B2 (en) | 2002-09-24 | 2004-06-01 | Natural Asa | Conjugated linoleic acid compositions |
US6897327B2 (en) * | 2003-05-08 | 2005-05-24 | Stepan Company | Manufacture of conjugated linoleic salts and acids |
US7193096B2 (en) | 2003-07-01 | 2007-03-20 | Loders Croklaan Usa Llc | Process for producing a conjugated di- or poly-unsaturated fatty acid of 12 to 24 carbon atoms or salt or ester thereof |
CA2436650A1 (fr) | 2003-08-06 | 2005-02-06 | Naturia Inc. | Compositions d'acides linoleniques conjugues : synthese, purification et utilisations |
EP1696873B1 (fr) * | 2003-12-23 | 2017-06-21 | Stepan Company | Fabrication et purification d'esters d'acides linoleiques conjugues |
HU227137B1 (en) * | 2003-12-30 | 2010-08-30 | Bunge Noevenyolajipari Zartkoe | Process for producing conjugated linoleic acid |
EP1729851A2 (fr) * | 2004-03-10 | 2006-12-13 | Natural ASA | Compositions comportant des isomeres inverses d'acide linoleique conjugue |
CA2513340A1 (fr) * | 2004-08-25 | 2006-02-25 | F. Hoffmann-La Roche Ag | Substrat reutilisable pour la production de micropuces d'adn |
DE102004043824A1 (de) * | 2004-09-10 | 2006-03-16 | Cognis Ip Management Gmbh | Emulsionen mit ungesättigten Fettsäuren und deren Estern |
ES2395254T3 (es) * | 2005-02-04 | 2013-02-11 | Lipid Nutrition B.V. | Procedimiento para la preparación de ácidos grasos |
US8203012B2 (en) * | 2005-12-05 | 2012-06-19 | Stepan Company | Process for preparing conjugated linoleic acid and derivatives thereof from ricinoleic acid |
US8614074B2 (en) | 2006-04-13 | 2013-12-24 | Stepan Specialty Products, Llc | Process for producing isomer enriched conjugated linoleic acid compositions |
US8038853B2 (en) * | 2007-06-18 | 2011-10-18 | E.I. Du Pont De Nemours And Company | Photo-induced reduction-oxidation chemistry of carbon nanotubes |
PT2055199E (pt) | 2007-10-29 | 2013-10-10 | Stepan Specialty Products Llc | Composição de tempero |
CN102229527B (zh) * | 2009-12-14 | 2016-05-04 | 脂质营养品有限公司 | 工艺方法 |
ES2618069T3 (es) | 2010-03-09 | 2017-06-20 | Stepan Specialty Products, Llc | Método para tratar un aceite comestible y el aceite obtenido de esta manera |
CN106978260A (zh) | 2010-12-31 | 2017-07-25 | 斯泰潘专业产品有限责任公司 | 共轭亚油酸的制备方法 |
SG2014010045A (en) * | 2011-08-24 | 2014-08-28 | J Oil Mills Inc | Oxidized partially hydrogenated oil |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2242230A (en) * | 1941-05-20 | Process of producing conjugation in | ||
US2343644A (en) * | 1941-07-30 | 1944-03-07 | Distillation Products Inc | Procedure for the preparation of substances containing conjugated double bonds |
US5208356A (en) * | 1989-02-17 | 1993-05-04 | Wisconsin Alumni Research Foundation | Octadecadienoic phospholipic esters, antioxidant and mold inhibiting compositions |
US5760082C1 (en) * | 1994-08-29 | 2001-03-06 | Wisconsin Alumni Res Found | Dietetic foods containing conjugated linoleic acids |
US5814663A (en) * | 1994-08-29 | 1998-09-29 | Wisconsin Alumni Research Foundation | Method for maintaining an existing level of body fat |
DE69615513T2 (de) * | 1995-11-14 | 2002-05-08 | Unilever N.V., Rotterdam | Essbarer Brotaufstrich |
JP3017108B2 (ja) * | 1996-10-30 | 2000-03-06 | リノール油脂株式会社 | 共役リノール酸の製造方法 |
US6015833A (en) | 1998-03-17 | 2000-01-18 | Conlinco., Inc. | Conjugated linoleic acid compositions |
US6060514A (en) | 1998-05-04 | 2000-05-09 | Conlin Co., Inc. | Isomer enriched conjugated linoleic acid compositions |
-
1998
- 1998-08-28 CA CA002246085A patent/CA2246085C/fr not_active Expired - Fee Related
- 1998-08-31 AT AT98202886T patent/ATE245688T1/de active
- 1998-08-31 EP EP98202886A patent/EP0902082B1/fr not_active Expired - Lifetime
- 1998-08-31 ES ES98202886T patent/ES2206828T3/es not_active Expired - Lifetime
- 1998-08-31 DK DK98202886T patent/DK0902082T3/da active
- 1998-08-31 DE DE69816545T patent/DE69816545T2/de not_active Expired - Lifetime
- 1998-09-01 ZA ZA9807962A patent/ZA987962B/xx unknown
- 1998-09-11 NO NO19984207A patent/NO312135B1/no not_active IP Right Cessation
- 1998-09-11 AU AU84160/98A patent/AU727994B2/en not_active Ceased
- 1998-09-11 US US09/151,776 patent/US6160140A/en not_active Expired - Lifetime
-
2000
- 2000-07-14 US US09/617,510 patent/US6271404B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA2246085C (fr) | 2004-04-27 |
AU727994B2 (en) | 2001-01-04 |
EP0902082A1 (fr) | 1999-03-17 |
DE69816545D1 (de) | 2003-08-28 |
US6271404B1 (en) | 2001-08-07 |
DE69816545T2 (de) | 2004-06-09 |
ATE245688T1 (de) | 2003-08-15 |
ES2206828T3 (es) | 2004-05-16 |
US6160140A (en) | 2000-12-12 |
DK0902082T3 (da) | 2003-10-20 |
EP0902082B1 (fr) | 2003-07-23 |
CA2246085A1 (fr) | 1999-03-12 |
ZA987962B (en) | 2000-03-01 |
NO984207D0 (no) | 1998-09-11 |
AU8416098A (en) | 1999-03-25 |
NO984207L (no) | 1999-03-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK1K | Patent expired |