EP0429995A2 - Procédé d'hydrogénation d'huiles - Google Patents
Procédé d'hydrogénation d'huiles Download PDFInfo
- Publication number
- EP0429995A2 EP0429995A2 EP90121982A EP90121982A EP0429995A2 EP 0429995 A2 EP0429995 A2 EP 0429995A2 EP 90121982 A EP90121982 A EP 90121982A EP 90121982 A EP90121982 A EP 90121982A EP 0429995 A2 EP0429995 A2 EP 0429995A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- oils
- fats
- process according
- hydrogenated
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- 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
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
Definitions
- the invention relates to the field of food technology and refers to a process for hydrogenating vegetable and animal oils or fats into products with unique melt profile by means of catalytic hydrogen transfer from an appropriate donor as well as to the products of said hydrogenation.
- Textural characteristics of products which contain hydrogenated oils result from solid content index (SCI) of hydrogenated oils.
- SCI solid content index
- the basic hydrogenation process means the conversion of liquid oils into semi-solid substances and partially hydrogenated oils.
- Plastic fats are useful for preparing vegetable fats, margarine and special purpose fats.
- Hydrogenation represents the double bond addition in fat in the presence of a metallic catalyst.
- the purpose of the hydrogenation is the saturation of double bonds of fatty acids in fats.
- the hydrogenation reaction is not simple since it is accompanied by the simultaneous double bond isomerization, which may be a positional or a geometrical one.
- the position of the fatty acid in glycerol (1, 2 and 3) as well as the degree of unsaturation determine the physical properties of the molecule, especially the melting point of the fat, and thence influences on SCI.
- the stepwise conversion of the most unsaturated fatty acid form proceeded to the saturated state, i.e. linolenic to linoleic, then to oleic, and finally to stearic.
- a very narrow melting range or a controlled level of trans acids cannot be achieved by a common hydrogenation.
- European Patent Application 0 246 366 A1 discloses a simplified one-step process with partly deactivated Ni catalyst at a temperature range from 160 to 250 °C and gauge pressure of hydrogen from 0 to 7.105 Pa.
- the hydrogenation is carried on at a temperature fro 20 to 90 °C, usually at room temperature and at atmospheric pressure. However, better results are achieved at higher temperatures.
- the batch process is carried out in an organic solvent or in an aqueous emulsion.
- the continuous process is carried out in an organic solvent.
- Oils containing unsaturated fatty acids with at least 12 carbon atoms are hydrogenated.
- products having specific compositions which are the basis for producing margarine, creams, ice-creams etc., with improved edibility and appropriate melting properties as well as oxidation stability.
- the oil acceptor (A) containing double bonds, the hydrogen donor (DHx) and the catalyst are in contact.
- the hydrogen donor may be any organic compound having sufficiently low oxidation potential for carrying out the hydrogen transfer at relatively mild conditions.
- the hydrogenation rate depends upon the nature of oil, the nature of hydrogen donor, the activity and the concentration of the catalyst as well as upon the velocity of the adsorption and desorption step of the unsaturated oil and the hydrogen donor on the catalyst.
- the compositions and properties of hydrogenated products can vary with regard to the position of the double bonds to be hydrogenated and are due to the influence of the isomerization reactions, which accompany each hydrogenation step. They also largely depends on hydrogenation conditions.
- Vegetable oils or mixture of vegetable oils, which are suitable for hydrogenation are e.g. soya oil, sunflower oil, safflower oil, maize oil, olive oil, bamboo oil, peanut oil, palm oil, rape oil, grape oil, coconut oil, pumpkin oil and castor oil.
- cod-liver-oil or a mixture of cod-liver oil with vegetable oils may be used.
- regenerable catalysts such as 1 - 20% palladium on active carbon (Pd/C), Pd/C/FeCl3, Pd/C/Fe(III) hydroxide or oxide, 0.04 - 10% Pd/Al2O3, 5% Pt/C. 5% Pt/Al2O3, 5% rhodium on active carbon, Raney nickel, ruthenium black and platinum black.
- the hydrogen donor must correspond to the catalyst, therefore formic acid and hypophosphorous acid as well as the salts thereof, such as triethylammonium formate, tri-n-butylammonium formate, sodium formate, potassium formate and ammonium formate as well as sodium hypophosphite are used.
- solvents such as ethanol propan-2-ol, formic acid, acetic acid, acetone and ethyl acetate may be selected. Some solvents can also act as the hydrogen donor.
- the reaction may be directed into products, which may be totally or only partly hydrogenated oils.
- the reaction is especially suitable for obtaining partly hydrogenated oils. From soya oil, rape oil or some other vegetable oil, only within a few hours of hydrogenation, an oil containing less than 1 % linolenic acid is obtained.
- cod-liver oils having high contents of poly-unsaturated ⁇ 3 acids (especially C18:3 ⁇ 3, C20:5 ⁇ 3 and C22:6 ⁇ 3), there are obtained fats with lower iodine values and adequate melting properties.
- the continuous process is also very simple since neither mixing nor catalyst removal are necessary.
- the catalyst may also be regenerated in a column and can be used for almost an unlimited period of time.
- one disadvantage of the present process can be present, the solvent and the donor must be removed from the final product before its application.
- weight amounts of oil, catalyst and hydrogen donor, dissolved in an organic solvent or water were agitated mechanically at about 900 rpm in a 150 ml flask which was immersed in a water bath at chosen temperature.
- Iodine value was calculated from fatty acid composition.
- a mixture of sunflower oil (2 ml) having an iodine value of 139.2, acetone (25 ml) and formic acid (2 ml) was eluted through a column filled with celite and with 100 mg of Pd/C.
- the flow rate was 0.5 ml/min. After the removal of the solvent a hydrogenated product having an iodine value of 122.4 and with a fatty acid composition as given in the Table 2 was obtained.
- Example 4 (batch hydrogenation in an aqueous emulsion)
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
YU2204/89 | 1989-11-20 | ||
YU220489A YU46273B (sh) | 1989-11-20 | 1989-11-20 | Postopek za hidrogeniranje olj |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0429995A2 true EP0429995A2 (fr) | 1991-06-05 |
EP0429995A3 EP0429995A3 (en) | 1991-12-11 |
EP0429995B1 EP0429995B1 (fr) | 1996-02-28 |
Family
ID=25557224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90121982A Expired - Lifetime EP0429995B1 (fr) | 1989-11-20 | 1990-11-16 | Procédé d'hydrogénation d'huiles |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0429995B1 (fr) |
DE (1) | DE69025553T2 (fr) |
SI (1) | SI8912204A8 (fr) |
YU (1) | YU46273B (fr) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7498453B2 (en) | 2003-07-31 | 2009-03-03 | Cargill Incorporated | Low trans-fatty acid fats and fat compositions and methods of making same |
US7585990B2 (en) | 2003-07-31 | 2009-09-08 | Cargill, Incorporated | Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils |
US8021443B2 (en) | 2001-09-25 | 2011-09-20 | Elevance Renewable Sciences, Inc. | Triacylglycerol based wax composition |
US8202329B2 (en) * | 2000-03-06 | 2012-06-19 | Elevance Renewable Sciences, Inc. | Triacylglycerol-based alternative to paraffin wax |
US8344052B2 (en) | 2006-07-12 | 2013-01-01 | Elevance Renewable Sciences, Inc. | Hot melt adhesive compositions comprising metathesized unsaturated polyol ester wax |
US8481747B2 (en) | 2006-07-13 | 2013-07-09 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
US8487148B2 (en) | 2010-12-13 | 2013-07-16 | Exxonmobil Research And Engineering Company | Hydrothermal treatment of biomass with heterogeneous catalyst |
US8501973B2 (en) | 2006-10-13 | 2013-08-06 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
US8614344B2 (en) | 2006-10-13 | 2013-12-24 | Elevance Renewable Sciences, Inc. | Metathesis methods involving hydrogenation and compositions relating to same |
US8624070B2 (en) | 2010-12-13 | 2014-01-07 | Exxonmobil Research And Engineering Company | Phosphorus recovery from hydrothermal treatment of biomass |
US8685118B2 (en) | 2005-01-10 | 2014-04-01 | Elevance Renewable Sciences, Inc. | Candle and candle wax containing metathesis and metathesis-like products |
US8704019B2 (en) | 2010-12-13 | 2014-04-22 | Exxonmobil Research And Engineering Company | Catalyst recovery in hydrothermal treatment of biomass |
US8704020B2 (en) | 2010-12-13 | 2014-04-22 | Exxonmobil Research And Engineering Company | Catalytic hydrothermal treatment of biomass |
US8815257B2 (en) | 2006-03-07 | 2014-08-26 | Elevance Renewable Sciences, Inc. | Compositions comprising metathesized unsaturated polyol esters |
US8888908B2 (en) | 2006-03-07 | 2014-11-18 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
US8895771B2 (en) | 2006-10-13 | 2014-11-25 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
US9051519B2 (en) | 2009-10-12 | 2015-06-09 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US9120742B2 (en) | 2006-10-13 | 2015-09-01 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis |
US9290719B2 (en) | 2012-01-10 | 2016-03-22 | Elevance Renewable Sciences, Inc. | Renewable fatty acid waxes and methods of making |
US9890348B2 (en) | 2012-06-20 | 2018-02-13 | Elevance Renewable Sciences, Inc. | Natural oil metathesis compositions and methods |
CN110564513A (zh) * | 2019-10-21 | 2019-12-13 | 黑龙江精益检测有限公司 | 一种在超声无需添加氢气条件下氢化大豆油脂的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5774042A (en) * | 1980-10-27 | 1982-05-10 | Asahi Denka Kogyo Kk | Preparation of hard butter |
EP0108571A2 (fr) * | 1982-11-04 | 1984-05-16 | Dai-Ichi Croda Chemicals Kabushiki Kaisha | Procédé de purification d'huiles grasses insaturées |
-
1989
- 1989-11-20 SI SI8912204A patent/SI8912204A8/sl unknown
- 1989-11-20 YU YU220489A patent/YU46273B/sh unknown
-
1990
- 1990-11-16 EP EP90121982A patent/EP0429995B1/fr not_active Expired - Lifetime
- 1990-11-16 DE DE1990625553 patent/DE69025553T2/de not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5774042A (en) * | 1980-10-27 | 1982-05-10 | Asahi Denka Kogyo Kk | Preparation of hard butter |
EP0108571A2 (fr) * | 1982-11-04 | 1984-05-16 | Dai-Ichi Croda Chemicals Kabushiki Kaisha | Procédé de purification d'huiles grasses insaturées |
Non-Patent Citations (8)
Title |
---|
CHEMICAL ABSTRACTS, vol. 69, 1968, page 385, abstract no. 3904h, Columbus, Ohio, US; H.A. BHAKARE et al.: "Hydrogenation of castor oil by hydrazine hydrate", & INDIAN J. TECHNOL., 6(1), 29-30 * |
CHEMICAL ABSTRACTS, vol. 83, 1973, page 144, abstract no. 181426a, Columbus, Ohio, US; L.A. BUVALKINA et al.: "Continuous conjugate hydrogenation of vegetable oils in a column apparatus", & PRIKL. TEOR. KHIM., VOLUME DATA 1971, 3, 148-53 * |
CHEMICAL ABSTRACTS, vol. 93, 1980, page 98, abstract no. 151996a, Columbus, Ohio, US; R.K. GOEL et al.: "Reduction of vegetable oils with hydrazine hydrate", & CHEM. ERA, 15(11), 15-16 * |
CHEMICAL ABSTRACTS, vol. 97, 1982, page 527, abstract no. 71163u, Columbus, Ohio, US; & JP-A-57 074 042 (ASAHI DENKA KOGYO K.K.) 10-05-1982 * |
JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 56, 1979, pages 36-44, Champaign, IL, US; J.I. GRAY et al.: "Hydrogenation catalysts - Their effect on selectivity" * |
JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 64, November 1987, pages 1529-1532, Champaign, IL, US; O. ARKAD et al.: "Catalytic transfer hydrogenation of soybean oil methyl ester using inorganic formic acid salts as donors" * |
Lehrbuch der Lebensmittelchemie, H.-D. Belitz, W. Grosch; Springer Verlag, 2.Auflage, 1985, p.145 * |
TETRAHEDRON LETTERS, vol. 22, no. 18, 1981, pages 1709-1710, GB; R. BAR et al.: "Catalytic reductions with formate ion under phase transfer conditions" * |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8202329B2 (en) * | 2000-03-06 | 2012-06-19 | Elevance Renewable Sciences, Inc. | Triacylglycerol-based alternative to paraffin wax |
US8529924B2 (en) | 2000-03-06 | 2013-09-10 | Elevance Renewable Sciences, Inc. | Triacyglycerol-based alternative to paraffin wax |
US8021443B2 (en) | 2001-09-25 | 2011-09-20 | Elevance Renewable Sciences, Inc. | Triacylglycerol based wax composition |
US7820841B2 (en) | 2003-07-31 | 2010-10-26 | Cargill, Incorporated | Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils |
US7498453B2 (en) | 2003-07-31 | 2009-03-03 | Cargill Incorporated | Low trans-fatty acid fats and fat compositions and methods of making same |
US7585990B2 (en) | 2003-07-31 | 2009-09-08 | Cargill, Incorporated | Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils |
US8911515B2 (en) | 2005-01-10 | 2014-12-16 | Elevance Renewable Sciences, Inc. | Candle and candle wax containing metathesis and metathesis-like products |
US8685118B2 (en) | 2005-01-10 | 2014-04-01 | Elevance Renewable Sciences, Inc. | Candle and candle wax containing metathesis and metathesis-like products |
US8815257B2 (en) | 2006-03-07 | 2014-08-26 | Elevance Renewable Sciences, Inc. | Compositions comprising metathesized unsaturated polyol esters |
US8888908B2 (en) | 2006-03-07 | 2014-11-18 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
US9668955B2 (en) | 2006-03-07 | 2017-06-06 | Elevance Renewable Sciences, Inc. | Compositions comprising metathesized unsaturated polyol esters |
US8344052B2 (en) | 2006-07-12 | 2013-01-01 | Elevance Renewable Sciences, Inc. | Hot melt adhesive compositions comprising metathesized unsaturated polyol ester wax |
US8481747B2 (en) | 2006-07-13 | 2013-07-09 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
US9139605B2 (en) | 2006-07-13 | 2015-09-22 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
US9255117B2 (en) | 2006-07-13 | 2016-02-09 | Materia, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
US8569560B2 (en) | 2006-10-13 | 2013-10-29 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
US10906861B2 (en) | 2006-10-13 | 2021-02-02 | Wilmar Trading Pte Ltd | Methods of making organic compounds by metathesis |
US8895771B2 (en) | 2006-10-13 | 2014-11-25 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
US8614344B2 (en) | 2006-10-13 | 2013-12-24 | Elevance Renewable Sciences, Inc. | Metathesis methods involving hydrogenation and compositions relating to same |
US9120742B2 (en) | 2006-10-13 | 2015-09-01 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis |
US8501973B2 (en) | 2006-10-13 | 2013-08-06 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
US9464258B2 (en) | 2009-10-12 | 2016-10-11 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US9051519B2 (en) | 2009-10-12 | 2015-06-09 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
US8487148B2 (en) | 2010-12-13 | 2013-07-16 | Exxonmobil Research And Engineering Company | Hydrothermal treatment of biomass with heterogeneous catalyst |
US8704020B2 (en) | 2010-12-13 | 2014-04-22 | Exxonmobil Research And Engineering Company | Catalytic hydrothermal treatment of biomass |
US8704019B2 (en) | 2010-12-13 | 2014-04-22 | Exxonmobil Research And Engineering Company | Catalyst recovery in hydrothermal treatment of biomass |
US8624070B2 (en) | 2010-12-13 | 2014-01-07 | Exxonmobil Research And Engineering Company | Phosphorus recovery from hydrothermal treatment of biomass |
US9290719B2 (en) | 2012-01-10 | 2016-03-22 | Elevance Renewable Sciences, Inc. | Renewable fatty acid waxes and methods of making |
US9890348B2 (en) | 2012-06-20 | 2018-02-13 | Elevance Renewable Sciences, Inc. | Natural oil metathesis compositions and methods |
CN110564513A (zh) * | 2019-10-21 | 2019-12-13 | 黑龙江精益检测有限公司 | 一种在超声无需添加氢气条件下氢化大豆油脂的方法 |
Also Published As
Publication number | Publication date |
---|---|
YU46273B (sh) | 1993-05-28 |
DE69025553D1 (de) | 1996-04-04 |
EP0429995A3 (en) | 1991-12-11 |
SI8912204A8 (en) | 1997-08-31 |
EP0429995B1 (fr) | 1996-02-28 |
YU220489A (en) | 1991-08-31 |
DE69025553T2 (de) | 1996-09-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0429995B1 (fr) | Procédé d'hydrogénation d'huiles | |
EP0135436B1 (fr) | Nouveau procédé de fabrication d'oléfine linéaire à partir d'acide gras ou d'ester d'acide gras saturé | |
JP4278910B2 (ja) | エステルの製造法 | |
KR100414260B1 (en) | Selective acetylene hydrogenation | |
US4278609A (en) | Process for the selective hydrogenation of triglyceride oils with a metallic catalyst in the presence of ammonia | |
HU222744B1 (hu) | Szubsztrátumok hidrogénezése és ilyen eljárással elżállított termékek | |
US4229361A (en) | Hydrogenation catalyst and hydrogenation process | |
US4161483A (en) | Hydrogenation process | |
Šmidovnik et al. | Catalytic transfer hydrogenation of soybean oil | |
EP3013930A1 (fr) | Procédé d'hydrogénation sélective d'huiles végétales | |
US4307026A (en) | Process for the selective hydrogenation of triglyceride oils with a metallic catalyst in the presence of a diamine | |
Hsu et al. | Heterogeneous catalytic hydrogenation of canola oil using palladium | |
CA1117972A (fr) | Hydrogenation selective | |
US4320228A (en) | Preparation of olefinically unsaturated carbonyl compounds and alcohol | |
EP0219911A1 (fr) | Composé polymère catalytique à base de borure de nickel | |
US4728465A (en) | Nickelboride-polymer catalyst used in hydrogenation of fatty compounds | |
US4551441A (en) | Nickel boride-polymer in-oil catalyst | |
JPH06506005A (ja) | モノ不飽和脂肪酸またはその誘導体の製法 | |
CA1162563A (fr) | Methode d'hydrogenation selective d'acides adipeux, et produits ainsi obtenus | |
Morris et al. | Hydrogenation of triple bonds to double bonds in conjugated methyl octadecadiynoate and methyl santalbate | |
CA1236474A (fr) | Fluoronaphtalene-chrome-tricarbonyles utiles comme catalyseurs d'hydrogenation pour des melanges renfermant des acides gras polyinsatures residuels | |
US2367287A (en) | Hydrogenation process | |
SU1694638A1 (ru) | Способ получени технического саломаса | |
FR2670779A1 (fr) | Procede de preparation de l'acide adipique par hydrocarboxylation d'acides penteniques. | |
DE894555C (de) | Verfahren zur Herstellung von wertvollen, sauerstoffhaltigen Verbindungen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): DE FR NL |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): DE FR NL |
|
17P | Request for examination filed |
Effective date: 19920611 |
|
17Q | First examination report despatched |
Effective date: 19931208 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): DE FR NL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Effective date: 19960228 |
|
REF | Corresponds to: |
Ref document number: 69025553 Country of ref document: DE Date of ref document: 19960404 |
|
EN | Fr: translation not filed | ||
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19971028 Year of fee payment: 8 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19971130 Year of fee payment: 8 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990601 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 19990601 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990901 |