WO1991012305A1 - Elimination des substances huileuses - Google Patents
Elimination des substances huileuses Download PDFInfo
- Publication number
- WO1991012305A1 WO1991012305A1 PCT/DK1991/000042 DK9100042W WO9112305A1 WO 1991012305 A1 WO1991012305 A1 WO 1991012305A1 DK 9100042 W DK9100042 W DK 9100042W WO 9112305 A1 WO9112305 A1 WO 9112305A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethyl
- methyl
- ester
- oil
- compound
- Prior art date
Links
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/24—Cleaning or pickling metallic material with solutions or molten salts with neutral solutions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
Definitions
- the present invention relates to a method of removing oil or grease from solid surfaces including solid particles and the surface of plants or animals by applying a glycolipid surfac ⁇ tant on said surfaces.
- oil removal agents Another important application of oil removal agents is for the disposal of oil polluting the environment as a result of spillage from, for instance, an oil tanker or an oil bore.
- Surface-active agents owe their ability to reduce surface tension to their molecular structure which comprises a hydrophilic and a hydrophobic region. These regions enable the surface-active agent to interact with hydrophilic and hydrophobic substances simultaneously, thus for instance effecting the dispersion of hydrophobic substances in water.
- This mode of operation permits surface-active agents to detach oil adhering to solid surfaces or particles, after which the oil may readily be removed, e.g. by rinsing with water.
- a drawback of many commercial surfactants is that they are not readily biodegradable, and their applica ⁇ tion results in toxic effects on fish, daphniae, algae, etc. Consequently, there has been some reluctance to use such sur- factants for removing oil pollution in order not to introduce potential pollutants into the environment.
- An object of the present invention is therefore to provide a method of removing oil adhering to solid surfaces, whether applied deliberately or as a result of accidental spillage, by means of a glycolipid surfactant which exhibits improved properties relative to previously proposed oil removing sur ⁇ factants and which at the same time is easily biodegradable and has a low toxicity.
- the present invention relates to a method of removing oil or grease from solid surfaces including solid particles and the surface of plants and animals, wherein a compound of the general formula I
- R-CO is an acyl group with 4-24 carbon atoms, optio ⁇ nally an unsaturated or branched chain acyl group, O-X-O- is a monosaccharide moiety, and R 1 is hydrogen or an alkyl group with 1-6 carbon atoms, is applied on a solid surface or on solid particles smeared or soiled with oil or grease for a period of time which is sufficient to provide release of the oil or grease from the solid surface or the solid particles.
- the monosaccharide X in formula (I) above may be a pentose or a hexose, in particular in cyclic (furanose or pyranose) form.
- the monosaccharide may thus be selected from the group consisting of glucose, fructose, ribose, galactose, arabi- nose, xylose and mannose, preferably glucose and galactose.
- the monosaccharide is preferably a hexose in which case the ester bond linking the acyl group R-CO to the monosaccharide may advantageously be attached to the hexose in the 6-0-posi- tion.
- R-CO is an acyl group with 6-22 carbon atoms, in particular 8-18 carbon atoms.
- R-CO may be selected from the group consisting of hexanoyl, hepta- noyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, eicosanoyl, doco- sanoyl, 9-octadecenoyl, 9,12-octadecadienoyl, and 9,12,15- octadecatrienoyl.
- R-CO are co- conut oil fatty acyl and tallow fatty acyl which are mixtures of acyl groups derived from coconut oil and tallow, respect- ively, which typically have a chain length of from about C g to about C_ 0 .
- R' is hydrogen in which case the monosaccharide moiety O-X-O- may suitably be a glucose moiety.
- R 1 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl or hexyl, in particular methyl or ethyl, most preferred ethyl.
- some preferred compounds (I) for use in the met- hod of the invention may be selected from the group con ⁇ sisting of methyl 6-O-octanoylglucoside, methyl 6-O-nonanoyl- glucoside, methyl 6-O-decanolyglucoside, methyl 6-0- undecan- oylglucoside, methyl 6-0-dodecanoylglucoside, methyl 6-0- tetradecanoylglucoside, methyl 6-0-hexadecanoylglucoside, methyl 6-0-octadecanoylglucoside, methyl 6-0-octadecenoyl- glucoside, methyl glucoside 6-0-coconut oil fatty acid ester and methyl glucoside 6-0-tallow fatty acid ester.
- Other preferred compounds (I) for use in the method of the invention may be selected from the group consisting of ethyl 6-0-octanoylglucoside, ethyl 6-0-nonanoylglucoside, ethyl 6- 0-decanoylglucoside, ethyl 6-0-undecanoylglucoside, ethyl 6- O-dodecanoylglucoside, ethyl 6-0-tetradecanoylglucoside, et ⁇ hyl 6-O-hexadecanoylglucoside, ethyl 6-0-octadeca- noylglucoside, ethyl 6-0-octadecenoylglucoside, ethyl gluco- side 6-0-coconut oil fatty acid ester and ethyl glucoside 6- 0-tallow fatty acid ester.
- Further preferred compounds (I) for use in the method of the invention may be selected from the group consisting of 6-0- octanoyl glucopyranose ester, 6-0-nonanoyl glucopyranose ester, 6-0-decanoyl glucopyranose ester, 6-0-undecanoyl glu ⁇ copyranose ester, 6-0-dodecanoyl glucopyranose ester, 6-0- tetradecanoyl glucopyranose ester, 6-0-hexadecanoyl gluco ⁇ pyranose ester, 6-O-octadecanoyl glucopyranose ester, 6-0- octadecenoyl glucopyranose ester, 6-O-coconut oil fatty acid glucopyranose ester and 6-O-tallow fatty acid glucopyranose ester.
- the compound (I) may suitably be applied as an aqueous dispersion either alone or in combina ⁇ tion with other substances which may exert an effect on its detergency, stability or other desirable properties, e.g. one or more other surfactants, chelating agents (e.g. EDTA) , antimicrobial agents, preservatives, buffers, builders, cor ⁇ rosion inhibitors, etc.
- the com ⁇ pound (I) may be formulated as a more viscous composition such as a paste or lotion which may be preferred for some uses such as application on human skin.
- the compound (I) in itself exhibits an excellent detergency effect, i.e. a detergency effect of up to virtually 100% (calculated on the basis of oil removed) for some compounds (I) .
- a detergency effect of up to virtually 100% (calculated on the basis of oil removed) for some compounds (I) .
- the compound (I) may suitably be formulated as a concentrate, in which case it may be present in a concentration of up to 90%, in particular up to 75%, such as up to 50%, by weight of the dispersion.
- the con ⁇ centrate may be used as such to remove ingrained soiling,
- the concentrate may be di ⁇ luted, preferably with water, to a ready-to-use dispersion in which the compound (I) may suitably be present in a concen ⁇ tration of 0.01-10%, preferably 0.05-1.0%, and more preferab- ly about 0.5% by weight.
- the solid surface on which the compound (I) is applied may be a metal surface, e.g. the sur ⁇ face of a metal part which has been rolled, drawn, milled, turned or cast and coated with cutting oil, lubricant, drawing oil, grease or the like.
- the metal surface may fur ⁇ thermore be the inner surface of an oil tank soiled with petroleum residues or other metal surfaces soiled with min ⁇ eral oil during production, transport or other handling oper ⁇ ations.
- the solid surface may also be a stone or ceramic, including glass, surface, e.g. the surface of stones which are located adjacent to an oil bore and which are frequently polluted with petroleum overflow.
- Other examples are ceramic, e.g. glass, surfaces of domestic implements, tiles and the like, which have become soiled with grease in the course of their use.
- the compound (I) may be used to clean vegeta ⁇ tion and/or animals which have become soiled with oil resulting from oil spillage.
- the solid sur- face may be the surface (leaves, stems, etc.) of plants or the surface (fur, feathers, etc.) of animals, including birds.
- the compound (I) may be used to remove oil from soil or sand particles which have become polluted with oil from an oil spillage.
- the present invention is further illustrated in the following examples which are not in'any way intended to limit the scope of the invention as claimed.
- test tubes When the rinsing was finished the test tubes were shaken just before the rinsing liquid was transferred to another test tube. The metal particles were then washed with 1 ml of water which was added to the rinsing liquid.
- the oil removed from the particles was extracted from the rinsing liquid with 5 ml of 1,1,1-trichloroethane and the re ⁇ sidual oil on the particles was also extracted with 5 ml of 1,1,1-trichloroethane.
- the organic and aqueous phases were separated by centrifugation at 4000 rpm for 10 min. (Labofuge GL) . If necessary the organic phase was washed subsequently with water. The aqueous phase was removed, and the concen ⁇ tration of the oil in the organic phase was measured spectro- photometrically at 510 nm as Sudan Red B has an absorbtion maximum at this wavelength. Detergency was calculated as the percentage of oil in the rinsing liquid relative to the sum of oil in the rinsing liquid and the residual oil.
- Heptanoic acid C 7 ethylglucoside Octanoic acid Cgethylglucoside Nonanoic acid Cgethylglucoside Decanoic acid C 10 ethylglucoside Dodecanoic acid C 12ethylglucoside Tetradecanoic acid C 14 ethylglucoside Hexadecanoic acid C 16 ethylglucoside Octadecanoic acid C lg ethylglucoside Octadecenoic acid c 1 8 : i ethylglucoside Coconut fatty acids C coco ethylglucoside Tallow fatty acids C tallow ethylglucoside
- Sucrose esters available from Mitsubishi-Kasei Food Corpora ⁇ tion, Japan
- L-1695 95% lauric acid, 80% monoester, 20% di-, tri-, polyesters
- L-595 (95% lauric acid, 30% monoester, 70% di-, tri-, polyesters)
- S-1670 (70% stearic acid, 75% monoester, 25% di-, tri-, polyesters)
- Alcohol ethoxylates (available from Berol Kemi AB, Sweden) :
- Alkyl polyglycosides (available from Horizon Chemical, USA) :
- APG ® 300 (C 8 _ 11 H 17 -23O(C 6 H 10 O 5 ) 1 _ 10 H)
- APG ® 500 (C 12 -15 H 25- 31 °( C 6 H 10 0 5> 1 -1 0 H >
- APG ® 550 (C 12 -15 H 2 5 - 31 °( C 6 H 10 °5. 1 - 10 H )
- Nonyl phenol ethoxylates available from Berol Kemi AB, Sweden:
- Berol 09 (Nonyl phenol (E0) 10 )
- Berol 263 (Nonyl phenol (E0) 14 )
- Berol 26 43 1 Berol 09 46 20 Berol 263 33 12
- sucrose esters with a high content of monoester had far lower- detergencies than the compounds (I) with corresponding fatty acid chains (C 12 ethylglucoside and C 16 ethylglucoside) .
- the C- j ⁇ ⁇ ethylglucoside reaches its optimal deterging power at a concentration of about 0.50% at both pH 5 and 10 whereas the Solvex cleaner reaches its optimal deterging power at about 10% of the composition.
- the degrees of hydrolysis were 0%, 25%, 50% and 3075% with a total concentration of non- and hydrolyzed compo ⁇ und (I) of 0.10%. This suboptimal concentration was chosen for similar reasons as indicated in Example 3. The results are shown in table 5.
- Clearly the deterging effect is reduced as the compound (I) molecule is hydrolyzed to its main con ⁇ stituents, ethylglucoside and free fatty acid.
- Caps for medicine vials may be produced by stamping of alu ⁇ minium plates.
- the aluminium is lubricated with oil to facilitate the stamping. After the stamping the oil has to be removed from the caps. If the oil is not removed properly the further mechanical processing is rendered difficult due to the slippery caps.
- the bar was then placed in 1,1,1-trichloroethane and rubbed carefully to remove any excess oil and dried. The residual amount of oil removed was also determined gravimetrically.
- the detergency of the 2% C 12 ethylglucoside was 97%.
- a zinc tube greased with fat and oil from cooking was washed with an aqueous dispersion of 1% C- ⁇ ethylglucoside and rinsed with water.
- the tube was evaluated to be perfectly clean by visual inspection.
- the deterging power was not effected significantly except for C 10 ethylglucoside with respect to removal of Iloform TDN 81. In this case, the deterging power was reduced by about one third at pH 5 and 10.
- the compounds according to the present invention are therefore fully active under alkaline conditions, common in washing and degreasing, as well as under neutral and acidic conditions.
- the dispersions of the compounds (I) proved to be stable and active for at least six months.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Detergent Compositions (AREA)
Abstract
L'invention se rapporte à l'élimination de substances huileuses ou graisseuses, lesquelles peuvent être retirées de surfaces solides contenant des particules solides et de la surface de plantes ou d'animaux, grâce à l'application sur ces surfaces d'un agent tensio-actif à base de glyco-lipide représenté par la formule générale: R-COO-X-O-R', où R-CO représente un groupe acyle ayant 4 à 24 atomes de carbone, éventuellement un groupe acyle à chaîne ramifiée ou insaturé, O-X-O- représente une fraction de monosaccharide, et R' représente l'hydrogène ou un groupe alkyle ayant 1 à 6 atomes de carbone.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK410/90 | 1990-02-16 | ||
| DK41090A DK41090D0 (da) | 1990-02-16 | 1990-02-16 | Fremgangsmaade til fjernelse af olie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1991012305A1 true WO1991012305A1 (fr) | 1991-08-22 |
Family
ID=8093205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DK1991/000042 WO1991012305A1 (fr) | 1990-02-16 | 1991-02-15 | Elimination des substances huileuses |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU7341091A (fr) |
| DK (1) | DK41090D0 (fr) |
| WO (1) | WO1991012305A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995007967A1 (fr) * | 1993-09-15 | 1995-03-23 | Novo Nordisk A/S | Procede d'enlevement d'huiles de silicone |
| FR2713655A1 (fr) * | 1993-12-15 | 1995-06-16 | Inst Francais Du Petrole | Procédé de décontamination d'un milieu poreux pollué par des hydrocarbures utilisant une composition contenant un composé tensio-actif et des glycolipides. |
| DE19600743A1 (de) * | 1996-01-11 | 1997-07-24 | Henkel Kgaa | Verwendung von Mischungen aus Glycolipiden und Tensiden |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395365A (en) * | 1980-09-08 | 1983-07-26 | Nissan Motor Co., Ltd. | Metal cleaning composition containing a fatty acid succrose ester and other detergent components |
| WO1988009369A1 (fr) * | 1987-05-18 | 1988-12-01 | Staley Continental, Inc. | Composition de detergents peu moussante |
| WO1989001480A1 (fr) * | 1987-08-21 | 1989-02-23 | Novo-Nordisk A/S | Nouveaux composes organiques et procede de preparation desdits composes |
-
1990
- 1990-02-16 DK DK41090A patent/DK41090D0/da not_active Application Discontinuation
-
1991
- 1991-02-15 AU AU73410/91A patent/AU7341091A/en not_active Abandoned
- 1991-02-15 WO PCT/DK1991/000042 patent/WO1991012305A1/fr unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395365A (en) * | 1980-09-08 | 1983-07-26 | Nissan Motor Co., Ltd. | Metal cleaning composition containing a fatty acid succrose ester and other detergent components |
| WO1988009369A1 (fr) * | 1987-05-18 | 1988-12-01 | Staley Continental, Inc. | Composition de detergents peu moussante |
| WO1989001480A1 (fr) * | 1987-08-21 | 1989-02-23 | Novo-Nordisk A/S | Nouveaux composes organiques et procede de preparation desdits composes |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995007967A1 (fr) * | 1993-09-15 | 1995-03-23 | Novo Nordisk A/S | Procede d'enlevement d'huiles de silicone |
| AU687875B2 (en) * | 1993-09-15 | 1998-03-05 | Novo Nordisk A/S | A method for removing silicone fluids |
| FR2713655A1 (fr) * | 1993-12-15 | 1995-06-16 | Inst Francais Du Petrole | Procédé de décontamination d'un milieu poreux pollué par des hydrocarbures utilisant une composition contenant un composé tensio-actif et des glycolipides. |
| DE19600743A1 (de) * | 1996-01-11 | 1997-07-24 | Henkel Kgaa | Verwendung von Mischungen aus Glycolipiden und Tensiden |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7341091A (en) | 1991-09-03 |
| DK41090D0 (da) | 1990-02-16 |
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