EP0289968A1 - Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras - Google Patents

Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras Download PDF

Info

Publication number: EP0289968A1
Authority: EP; European Patent Office
Prior art keywords: fatty; acid; fatty acid; glycerol; weight
Prior art date: 1987-05-08
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

Application number

EP88106971A

Other languages

German (de)

English (en)

Other versions

EP0289968B1 (fr

Inventor

Horst Dr. Eierdanz

Hans Dr. Pfeiffer

Michael Dr. Vogt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

Priority date (The priority date 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 date listed.)

1987-05-08

Filing date

1988-04-30

Publication date

1988-11-09

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6327129&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0289968(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-04-30 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1988-04-30 Priority to AT88106971T priority Critical patent/ATE62016T1/de

1988-11-09 Publication of EP0289968A1 publication Critical patent/EP0289968A1/fr

1991-03-27 Application granted granted Critical

1991-03-27 Publication of EP0289968B1 publication Critical patent/EP0289968B1/fr

2008-04-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 29
239000000194 fatty acid Substances 0.000 title claims abstract description 29
229930195729 fatty acid Natural products 0.000 title claims abstract description 29
-1 fatty acid monoglycerides Chemical class 0.000 title claims abstract description 14
239000010685 fatty oil Substances 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title claims description 7
235000003222 Helianthus annuus Nutrition 0.000 title claims description 5
244000020551 Helianthus annuus Species 0.000 title claims description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 50
150000004665 fatty acids Chemical class 0.000 claims abstract description 14
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 13
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 12
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 12
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 12
239000005642 Oleic acid Substances 0.000 claims abstract description 12
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 12
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 12
235000019197 fats Nutrition 0.000 claims abstract description 8
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims abstract description 6
235000020778 linoleic acid Nutrition 0.000 claims abstract description 6
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims abstract description 6
238000005809 transesterification reaction Methods 0.000 claims abstract description 4
230000007717 exclusion Effects 0.000 claims abstract description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
235000021355 Stearic acid Nutrition 0.000 claims description 5
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 5
239000008117 stearic acid Substances 0.000 claims description 5
235000021314 Palmitic acid Nutrition 0.000 claims description 4
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
238000003776 cleavage reaction Methods 0.000 claims description 3
DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 2
URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 2
230000003647 oxidation Effects 0.000 abstract description 8
238000007254 oxidation reaction Methods 0.000 abstract description 8
230000001804 emulsifying effect Effects 0.000 abstract description 2
235000011187 glycerol Nutrition 0.000 description 14
235000021313 oleic acid Nutrition 0.000 description 9
239000000839 emulsion Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000003925 fat Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
239000003760 tallow Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
235000019486 Sunflower oil Nutrition 0.000 description 2
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
230000001953 sensory effect Effects 0.000 description 2
239000002600 sunflower oil Substances 0.000 description 2
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 1
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000208818 Helianthus Species 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
235000020661 alpha-linolenic acid Nutrition 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
244000309466 calf Species 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000006735 deficit Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
229940108623 eicosenoic acid Drugs 0.000 description 1
BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000005313 fatty acid group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine 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
235000013310 margarine Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013384 milk substitute Nutrition 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
150000002889 oleic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
- 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
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol

Definitions

Glycerol mono- and distearate (GMS) and GMO glycerol mono- and dioleate
GMS is produced by glycerolysis of glycerol tristearate or of hardened fats, which contain at least 55% stearic acid, in continuous or discontinuous processes, since the starting material is easily accessible by hardening fats and oils.
GMO is usually produced by the esterification of oleic acid with glycerin, since the glycerol trioleate required for glycerolysis can only be produced technically in several stages.
the oleic acid used for the esterification with glycerol is obtained by enrichment (solvent or cross-linking process) of the oleic acid contained in tallow fatty acid.
enrichment solvent or cross-linking process
Fatty acid monoglycerides are mainly used in food technology as emulsifiers. They should therefore have the greatest possible resistance to oxidation, which is reduced by contents of polyunsaturated fatty acids, in particular linoleic acid.
fatty oils with the composition described at the outset from certain sunflowers (Helianthus annuus) species such as, for. B. are known from US Pat. No. 4,627,192, without using the preparation processes customary in the prior art for the production of fatty acid monoglycerides by transesterification known per se in the presence of glycerol or fat cleavage and reaction of the split fatty acid obtained with glycerol.
fatty acid monoglycerides based on these fatty oils have improved application properties.
the oxidative resistance is significantly greater than that of conventional fatty acid monoglycerides. This is surprising since the content of polyunsaturated fatty acids in the fatty acid monoglycerides obtained according to the invention is comparable to that in those obtained from tallow fatty acid. Furthermore, the fatty acid monoglycerides obtained according to the invention have improved emulsifier properties compared to those from the prior art.
the fatty oils used as starting materials are natural substances, the proportions of their main components are subject to certain fluctuations.
the fatty oils or the fatty acid monoglycerides obtained therefrom according to the invention typically have the following fluctuation ranges with regard to the fatty acids: Oleic acid: 78 to 92% by weight Linoleic acid: 2 to 10% by weight Palmitic acid: 2 to 5% by weight Stearic acid: 2 to 7% by weight
the glycerol monooleates produced according to the invention using the above-mentioned fatty oils have monoester contents of 40 to 60%, which can be obtained in the usual way, e.g. B. by Molecular distillation, increase to a monoester content of 90% and above.
the GMO produced using fatty oils of the abovementioned composition according to the invention was tested in the Rancimat against a GMO produced from fractional oleic acid according to the classic method with regard to its oxidation stability.
the Rancimat (from Metrohm) is an analytical device widely used in the food industry for testing the oxidation stability of unsaturated oils.
a constant air flow is conducted through a defined amount of sample at an elevated temperature (100 to 120 ° C); the volatile compounds formed during the oxidation are determined in a condensation vessel on the basis of their electrical conductivity.
the time until volatile, electrically conductive oxidation products are formed is called the induction time.
smell and taste were rated on a 10-point scale. 10 points mean a tasteless and odorless, 1 point a completely unusable product.
oils should have a score of at least 6. The color was measured in the Lovibond colorimeter with a 5 1 / 4 ⁇ cell.
the following comparative example demonstrates the excellent suitability of the monoglycerides obtained using fatty oils according to the above composition for the preparation of the emulsion: 0.5 part by weight of emulsifier from tallow fatty acid and according to the invention were dissolved at 40 ° C. in 35 parts by weight of soybean oil. 64.5 parts by weight of water were then added while stirring in a slow stream. Finally, the pre-emulsion was finely homogenized twice in a high-pressure homogenizer at 120 bar.
the glycerol monooleate according to the invention has superior emulsifier properties over that according to the prior art.
the sunflower oil had the following composition of the fatty acid components: Myristic acid 0.1% by weight Palmitic acid 3.1% by weight Stearic acid 2.0% by weight Oleic acid 86.2% by weight Linoleic acid 7.8% by weight Linolenic acid 0.2% by weight Arachic acid 0.2% by weight Eicosenoic acid 0.2% by weight Erucic acid 0.2% by weight
An oleic acid monoglyceride was obtained with the following characteristics: Acid number 1.3 Saponification number 163 Iodine number 74 OH number 239 Glycerol content: 0.6% by weight Monoglyceride content: 60% by weight.

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Edible Oils And Fats (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

EP88106971A 1987-05-08 1988-04-30 Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras Expired - Lifetime EP0289968B1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
AT88106971T ATE62016T1 (de)	1987-05-08	1988-04-30	Verwendung eines fetten oeles ex helianthus annuus zur herstellung von fettsaeure-monoglyceriden.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3715424A DE3715424C2 (de)	1987-05-08	1987-05-08	Verwendung eines fetten Öles aus Helianthus annuus zur Herstellung von Fettsäure-Monoglyceriden
DE3715424		1987-05-08

Publications (2)

Publication Number	Publication Date
EP0289968A1 true EP0289968A1 (fr)	1988-11-09
EP0289968B1 EP0289968B1 (fr)	1991-03-27

Family

ID=6327129

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP88106971A Expired - Lifetime EP0289968B1 (fr)	1987-05-08	1988-04-30	Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras

Country Status (6)

Country	Link
EP (1)	EP0289968B1 (fr)
JP (1)	JPS63287749A (fr)
AT (1)	ATE62016T1 (fr)
CA (1)	CA1313381C (fr)
DE (2)	DE3715424C2 (fr)
ES (1)	ES2021786B3 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994010003A1 (fr) *	1992-10-28	1994-05-11	Daimler-Benz Aktiengesellschaft	Agencement de transfert inductif d'energie sur des consommateurs mobiles
WO1996005740A1 (fr) *	1994-08-19	1996-02-29	Croda International Plc	Compositions a base d'acide nervonique
EP0826765A1 (fr) *	1996-08-27	1998-03-04	Institut Francais Du Petrole	Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant
US5844132A (en) *	1996-06-24	1998-12-01	Institute Francais Du Petrole	Method and system for real-time estimation of at least one parameter linked with the behavior of a downhole tool
WO2017085737A1 (fr) *	2015-11-19	2017-05-26	Fine Research & Development Centre Pvt Ltd	Monoglycéride naturel présentant une odeur et un arôme améliorés

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2789119A (en) *	1954-02-09	1957-04-16	Boake Roberts & Co Ltd	Production of fatty acid monoglycerides
DE1099520B (de) *	1957-01-04	1961-02-16	E F Drew & Co Inc	Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen
US2976251A (en) *	1957-04-19	1961-03-21	Eastman Kodak Co	Glycerol fatty acid partial ester gels
US4627192A (en) *	1984-11-16	1986-12-09	Sigco Research Inc.	Sunflower products and methods for their production

1987
- 1987-05-08 DE DE3715424A patent/DE3715424C2/de not_active Expired - Fee Related
1988
- 1988-04-30 AT AT88106971T patent/ATE62016T1/de not_active IP Right Cessation
- 1988-04-30 DE DE8888106971T patent/DE3862147D1/de not_active Revoked
- 1988-04-30 EP EP88106971A patent/EP0289968B1/fr not_active Expired - Lifetime
- 1988-04-30 ES ES88106971T patent/ES2021786B3/es not_active Expired - Lifetime
- 1988-05-09 CA CA000566299A patent/CA1313381C/fr not_active Expired - Fee Related
- 1988-05-09 JP JP63113412A patent/JPS63287749A/ja active Pending

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2789119A (en) *	1954-02-09	1957-04-16	Boake Roberts & Co Ltd	Production of fatty acid monoglycerides
DE1099520B (de) *	1957-01-04	1961-02-16	E F Drew & Co Inc	Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen
US2976251A (en) *	1957-04-19	1961-03-21	Eastman Kodak Co	Glycerol fatty acid partial ester gels
US4627192A (en) *	1984-11-16	1986-12-09	Sigco Research Inc.	Sunflower products and methods for their production
US4627192B1 (en) *	1984-11-16	1995-10-17	Sigco Res Inc	Sunflower products and methods for their production

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994010003A1 (fr) *	1992-10-28	1994-05-11	Daimler-Benz Aktiengesellschaft	Agencement de transfert inductif d'energie sur des consommateurs mobiles
WO1996005740A1 (fr) *	1994-08-19	1996-02-29	Croda International Plc	Compositions a base d'acide nervonique
US5994404A (en) *	1994-08-19	1999-11-30	Croda International Plc	Nervonic acid compositions
US5844132A (en) *	1996-06-24	1998-12-01	Institute Francais Du Petrole	Method and system for real-time estimation of at least one parameter linked with the behavior of a downhole tool
EP0826765A1 (fr) *	1996-08-27	1998-03-04	Institut Francais Du Petrole	Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant
FR2752850A1 (fr) *	1996-08-27	1998-03-06	Inst Francais Du Petrole	Compositions d'additifs ameliorant le pouvoir lubrifiant des carburants et carburants les contenant
WO2017085737A1 (fr) *	2015-11-19	2017-05-26	Fine Research & Development Centre Pvt Ltd	Monoglycéride naturel présentant une odeur et un arôme améliorés

Also Published As

Publication number	Publication date
DE3715424A1 (de)	1988-11-17
EP0289968B1 (fr)	1991-03-27
ATE62016T1 (de)	1991-04-15
JPS63287749A (ja)	1988-11-24
CA1313381C (fr)	1993-02-02
ES2021786B3 (es)	1991-11-16
DE3715424C2 (de)	1995-01-26
DE3862147D1 (de)	1991-05-02

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