CA2309914C - Biodegradable oleic estolide ester base stocks and lubricants - Google Patents

Biodegradable oleic estolide ester base stocks and lubricants Download PDF

Info

Publication number: CA2309914C
Authority: CA; Canada
Prior art keywords: estolide; estolide compound; oleic; lubricants; formula
Prior art date: 1997-11-14
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.): Expired - Lifetime

Application number

CA002309914A

Other languages

English (en)

French (fr)

Other versions

CA2309914A1 (en

Inventor

Terry A. Isbell

Thomas P. Abbott

Svajus Asadauskas

Joseph E. Lohr, Jr.

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.)

Lambent Technologies Inc

US Department of Agriculture USDA

Original Assignee

Lambent Technologies Inc

US Department of Agriculture USDA

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.)

1997-11-14

Filing date

1998-11-16

Publication date

2007-03-06

1998-11-13 Priority claimed from US09/191,907 external-priority patent/US6018063A/en

1998-11-16 Application filed by Lambent Technologies Inc, US Department of Agriculture USDA filed Critical Lambent Technologies Inc

1999-05-27 Publication of CA2309914A1 publication Critical patent/CA2309914A1/en

2007-03-06 Application granted granted Critical

2007-03-06 Publication of CA2309914C publication Critical patent/CA2309914C/en

2018-11-16 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000314 lubricant Substances 0.000 title claims abstract description 33
-1 oleic estolide ester Chemical class 0.000 title claims description 44
150000002149 estolides Chemical class 0.000 claims abstract description 34
235000015112 vegetable and seed oil Nutrition 0.000 claims description 11
239000008158 vegetable oil Substances 0.000 claims description 11
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
229920013639 polyalphaolefin Polymers 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
150000008028 secondary esters Chemical class 0.000 claims description 6
125000005313 fatty acid group Chemical group 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 5
229920005862 polyol Polymers 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
238000005260 corrosion Methods 0.000 claims description 3
230000007797 corrosion Effects 0.000 claims description 3
239000012634 fragment Substances 0.000 claims description 3
239000002518 antifoaming agent Substances 0.000 claims description 2
239000003963 antioxidant agent Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000003086 colorant Substances 0.000 claims description 2
239000003599 detergent Substances 0.000 claims description 2
150000005690 diesters Chemical class 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
239000003879 lubricant additive Substances 0.000 claims description 2
239000002480 mineral oil Substances 0.000 claims description 2
239000003607 modifier Substances 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
230000001012 protector Effects 0.000 claims description 2
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 2
101150113676 chr1 gene Proteins 0.000 claims 2
230000003078 antioxidant effect Effects 0.000 claims 1
230000000994 depressogenic effect Effects 0.000 claims 1
235000010446 mineral oil Nutrition 0.000 claims 1
150000002148 esters Chemical class 0.000 abstract description 18
235000021313 oleic acid Nutrition 0.000 abstract description 8
239000000654 additive Substances 0.000 abstract description 7
230000001050 lubricating effect Effects 0.000 abstract description 3
150000002889 oleic acids Chemical class 0.000 abstract description 2
238000000034 method Methods 0.000 description 13
PGKKGBQMNNEIHV-PFONDFGASA-N 9-[(9Z)-octadecenoyloxy]octadecanoic acid Chemical class CCCCCCCCCC(CCCCCCCC(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC PGKKGBQMNNEIHV-PFONDFGASA-N 0.000 description 10
235000014113 dietary fatty acids Nutrition 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
229930195729 fatty acid Natural products 0.000 description 10
239000002253 acid Substances 0.000 description 8
150000004665 fatty acids Chemical class 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
230000001590 oxidative effect Effects 0.000 description 7
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
239000005642 Oleic acid Substances 0.000 description 6
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
239000012530 fluid Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 3
239000004808 2-ethylhexylester Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003860 storage Methods 0.000 description 3
ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000000539 dimer Substances 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
235000021122 unsaturated fatty acids Nutrition 0.000 description 2
150000004670 unsaturated fatty acids Chemical class 0.000 description 2
229940114072 12-hydroxystearic acid Drugs 0.000 description 1
KDUGNDDZXPJVCS-UHFFFAOYSA-N 6-oxo-6-tridecoxyhexanoic acid Chemical compound CCCCCCCCCCCCCOC(=O)CCCCC(O)=O KDUGNDDZXPJVCS-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
102000004882 Lipase Human genes 0.000 description 1
108090001060 Lipase Proteins 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000019519 canola oil Nutrition 0.000 description 1
239000000828 canola oil Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
238000005553 drilling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
235000020778 linoleic acid Nutrition 0.000 description 1
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019602 lubricity Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000010705 motor oil Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000011020 pilot scale process Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000011085 pressure filtration Methods 0.000 description 1
238000003908 quality control method Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
229960003656 ricinoleic acid Drugs 0.000 description 1
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
230000011664 signaling Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
- C10M101/04—Fatty oil fractions
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002309914A 1997-11-14 1998-11-16 Biodegradable oleic estolide ester base stocks and lubricants Expired - Lifetime CA2309914C (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US6572697P	1997-11-14	1997-11-14
US60/065,726		1997-11-14
US09/191,907		1998-11-13
US09/191,907 US6018063A (en)	1998-11-13	1998-11-13	Biodegradable oleic estolide ester base stocks and lubricants
PCT/US1998/024469 WO1999025794A1 (en)	1997-11-14	1998-11-16	Biodegradable oleic estolide ester base stocks and lubricants

Publications (2)

Publication Number	Publication Date
CA2309914A1 CA2309914A1 (en)	1999-05-27
CA2309914C true CA2309914C (en)	2007-03-06

Family

ID=26745921

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002309914A Expired - Lifetime CA2309914C (en)	1997-11-14	1998-11-16	Biodegradable oleic estolide ester base stocks and lubricants

Country Status (7)

Country	Link
EP (1)	EP1051465B1 (es)
AT (1)	ATE337390T1 (es)
AU (1)	AU1461399A (es)
CA (1)	CA2309914C (es)
DE (1)	DE69835694T2 (es)
ES (1)	ES2272013T3 (es)
WO (1)	WO1999025794A1 (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6541061B2 (en) *	2000-04-07	2003-04-01	Monsanto Technology Llc	Low calorie fat compositions
EP2480642A1 (en) *	2009-09-24	2012-08-01	Dow Global Technologies LLC	Estolide compositions having excellent low temperature properties
WO2012031048A1 (en)	2010-08-31	2012-03-08	Lubrigreen Biosynthetics, Llc	Acetic acid-capped estolide base oils and methods of making the same
JP6100768B2 (ja)	2011-06-17	2017-03-22	バイオシンセティックテクノロジーズ，リミティドライアビリティカンパニー	高い酸化安定性を示すエストリド組成物
EP2702124A1 (en)	2011-06-17	2014-03-05	Biosynthetic Technologies, LLC	Compositions comprising estolide compounds and methods of making and using the same
EP2702122B1 (en)	2011-06-17	2021-09-01	Biosynthetic Technologies, LLC	Grease compositions comprising estolide base oils
WO2013009471A1 (en) *	2011-07-08	2013-01-17	Lubrigreen Biosynthetics, Llc	Compositions and products containing estolide compounds
CA2877091C (en)	2012-06-18	2020-06-09	Biosynthetic Technologies, Llc	Processes of preparing estolide compounds that include removing sulfonate residues
KR20160046660A (ko)	2014-10-21	2016-04-29	에스케이이노베이션 주식회사	결합제를 이용한 에스톨라이드의 제조 방법
DE102018002891A1 (de) *	2017-04-13	2018-10-18	Klüber Lubrication München Se & Co. Kg	Neue Esterverbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2049072A (en) *	1933-08-29	1936-07-28	Standard Oil Dev Co	Lubricants
US2652411A (en) *	1952-07-18	1953-09-15	Howard M Teeter	Alkyl acyloxy stearates
US4431673A (en) *	1980-05-02	1984-02-14	Revlon, Inc.	Cosmetic compositions
US4428850A (en) *	1982-01-28	1984-01-31	Texaco Inc.	Low foaming railway diesel engine lubricating oil compositions
US4567037A (en) *	1984-11-20	1986-01-28	Revlon, Inc.	Fatty acid diesters
US4639369A (en) *	1986-03-03	1987-01-27	Revlon, Inc.	Higher acyl lower alkyl hydroxystearates useful in cosmetics
US4867965A (en) *	1986-10-02	1989-09-19	Revlon, Inc.	Fatty acid diesters
US4806572A (en) *	1987-05-04	1989-02-21	Creative Products Resource Asociates, Ltd.	Hydrophilic foam pad for makeup removal
US5518728A (en) *	1994-08-08	1996-05-21	L'oreal S.A.	Cosmetic compositions for non-white pigmented skin

1998
- 1998-11-16 ES ES98958608T patent/ES2272013T3/es not_active Expired - Lifetime
- 1998-11-16 AT AT98958608T patent/ATE337390T1/de not_active IP Right Cessation
- 1998-11-16 AU AU14613/99A patent/AU1461399A/en not_active Abandoned
- 1998-11-16 EP EP98958608A patent/EP1051465B1/en not_active Expired - Lifetime
- 1998-11-16 CA CA002309914A patent/CA2309914C/en not_active Expired - Lifetime
- 1998-11-16 DE DE69835694T patent/DE69835694T2/de not_active Expired - Lifetime
- 1998-11-16 WO PCT/US1998/024469 patent/WO1999025794A1/en not_active Ceased

Also Published As

Publication number	Publication date
ATE337390T1 (de)	2006-09-15
EP1051465A1 (en)	2000-11-15
ES2272013T3 (es)	2007-04-16
CA2309914A1 (en)	1999-05-27
AU1461399A (en)	1999-06-07
WO1999025794A1 (en)	1999-05-27
EP1051465A4 (en)	2002-06-05
EP1051465B1 (en)	2006-08-23
DE69835694T2 (de)	2007-08-23
DE69835694D1 (de)	2006-10-05

Legal Events

Date	Code	Title	Description
2003-09-11	EEER	Examination request
2019-01-20	MKEX	Expiry	Effective date: 20181116

Publication	Publication Date	Title
US6018063A (en)	2000-01-25	Biodegradable oleic estolide ester base stocks and lubricants
US6316649B1 (en)	2001-11-13	Biodegradable oleic estolide ester having saturated fatty acid end group useful as lubricant base stock
US4234497A (en)	1980-11-18	Iso-palmitate polyol ester lubricants
KR930011931B1 (ko)	1993-12-22	윤활유
AU724983B2 (en)	2000-10-05	Two-cycle engine oil formed from a blend of a complex alcohol ester and other basestocks
PL184718B1 (pl)	2002-12-31	Ulegająca degradacji biologicznej syntetyczna estrowa baza wyjściowa
US4152278A (en)	1979-05-01	Wax esters of vegetable oil fatty acids useful as lubricants
US4263159A (en)	1981-04-21	Automatic transmission fluid comprising esters derived from a particular monocarboxylic acid composition
CA2309914C (en)	2007-03-06	Biodegradable oleic estolide ester base stocks and lubricants
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