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WO1995007967A1 - Procede d'enlevement d'huiles de silicone - Google Patents

Procede d'enlevement d'huiles de silicone Download PDF

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Publication number
WO1995007967A1
WO1995007967A1 PCT/DK1994/000343 DK9400343W WO9507967A1 WO 1995007967 A1 WO1995007967 A1 WO 1995007967A1 DK 9400343 W DK9400343 W DK 9400343W WO 9507967 A1 WO9507967 A1 WO 9507967A1
Authority
WO
WIPO (PCT)
Prior art keywords
cis
ethyl
isopropyl
silicone
butyl
Prior art date
Application number
PCT/DK1994/000343
Other languages
English (en)
Inventor
Otto Andresen
Original Assignee
Novo Nordisk A/S
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.)
Filing date
Publication date
Application filed by Novo Nordisk A/S filed Critical Novo Nordisk A/S
Priority to JP7508921A priority Critical patent/JPH09503006A/ja
Priority to EP94926814A priority patent/EP0719318A1/fr
Priority to AU76518/94A priority patent/AU687875B2/en
Publication of WO1995007967A1 publication Critical patent/WO1995007967A1/fr

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Classifications

    • 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 for removing silicone fluids or compositions containing silicone fluids from a surface. More specifically, the invention relates to a method fr removing silicone fluids from a surface by means of ap_ --ying to the surface a monosaccha- ride ester or a composition comprising a monosaccharide ester.
  • Silicone fluids are widely used today both industrially and domestically and an immense number of industrial pro ⁇ ducts comprises silicone fluids.
  • silicone fluids are extremely dif ⁇ ficult to remove. Further, they have a tendency to creep, i.e. to migrate and sprea ⁇ over adjacent surfaces. For instance, it is a common experience that applications of silicone fluid as e.g. a lubricant in one corner of a room soon leads to occurrence of silicone film all over the surfaces of said room, e.g. floor, walls, furniture.
  • EP 0 199 227 Bl discloses a process for removing sili- cones from fibres, yarns or sheetlike textile material wherein agueous solutions of surface-active eguilibration catalysts which are capable of reversibly breaking sil- oxane bonds, e.g. organic esters of sulfuric acid and phosphoric acid and organic ammonium compounds, are used at elevated temperatures and high or low extremes of pH.
  • surface-active eguilibration catalysts which are capable of reversibly breaking sil- oxane bonds, e.g. organic esters of sulfuric acid and phosphoric acid and organic ammonium compounds, are used at elevated temperatures and high or low extremes of pH.
  • the active substances applied in the process are environ ⁇ mentally undesirable.
  • GB Patent Specification 1.267.509 discloses a composition for removing silicone-containing materials from a glass surface, e.g. an automobile wind screen, which contains as the active substances eerie oxide and an organic det ⁇ ergent or surfactant.
  • the disclosed compositions are ex- pensive in use.
  • European Patent Application EP 0 437 216 A2 discloses a silicone-dissolving agent comprising one or more mono- esters of a long chained branched carboxylic acid with a long chained branched alcohol.
  • the use of such esters are undesirable from an environmental point of view since it is well known that long chained branched compounds are slowly biodegradable.
  • esters may be applied in an aqueous solution, pre ⁇ ferably in a concentration of 0.001 - 10%, more preferab- ly in a concentration of 0.005 - 8%, especially in a con ⁇ centration of 0.01 - 5%.
  • the removal or cleaning effect may be obtained with or without mechanical treatment de ⁇ pending on the surface and the type of silicone fluid or silicone-containing composition to be removed.
  • the method of the present invention there are several advantages of the method of the present invention such as simple and easy cleaning under mild conditions, often ambient temperature and a low consump- tion of the active compound, i.e. the monoester.
  • the active monoesters are non-irritating to skin and ey ⁇ es, and are non-toxic. Furthermore, they are very quickly biodegraded and exhibit low aquatoxicity.
  • a further advantage which is due to the efficiency, low price and non-toxic and non-irritant properties of the esters applied in the method of the invention is that a range of new applications for silicone fluids become pos ⁇ sible, i.e. applications which hitherto have been imposs ⁇ ible because of the resistance of the silicone fluid to removal.
  • new applications are as mold release agents, metal working fluids, or for vehicle wash.
  • the present invention relates to a method of substan ⁇ tially removing a silicone fluid or a silicone-containing composition from a surface which method comprises the steps of
  • X represents a mono- or disaccharide moiety carrying the group -OR 1 at the anomeric carbon atom and carrying the group R-COO- at a primary hydroxy group;
  • R 1 represents hydrogen, alkyl having 1 - 6 carbon atoms or one of the following groups
  • Y represents methylene or ethylene
  • R represents straight or branched alkyl, alkenyl, alkadi ⁇ enyl or alkatrienyl having 4 - 24 carbon atoms optionally substituted with hydroxy; or mixtures thereof;
  • the steps of the method of the invention are consecutive steps.
  • Silicones are polyorganosiloxanes having a structure si ⁇ milar to that of organically modified quartz and a back ⁇ bone of alternating silicon and oxygen atoms.
  • the back ⁇ bone can be modified in various ways through the incor ⁇ poration of carbon-based side groups such as methyl.
  • Di- methyl-based silicones may be fluid, resinous or elasto- meric in nature depending on the molecular weight and the configuration of the molecule. Silicone fluids are also known as silicone oils or uncured silicones.
  • silicone fluids can be modified by incorporating reactive groups such as amino into the molecules as a means of attaching other organic groups, e.g. polygly- cols, or they can be combined with various solid materi ⁇ als such as silica aerogels and xerogels and hydrophobic silicas of various types, or linear polymers and cyclo- polymers can be combined.
  • the resulting silicone copoly- mer fluids may have properties which are remarkable dif ⁇ ferent from the properties of the original fluids.
  • silicone fluids are polydimethyl siloxanes and copolymers thereof with polyalkyleneoxide; polydimet ⁇ hyl cyclosiloxanes, e.g. the tetramer and pentamer there ⁇ of, and mixtures thereof with e.g. polydimethyl siloxa- nes; polymethylphenylsiloxanes; trimethyl polysiloxanes; and stearoxy trimethyl silane wax.
  • Silicone fluids are transparent, tasteless and odourless liquids which are physiologically compatible, and their viscosity remains virtually constant over a wide range of temperatures.
  • the silicone fluids are highly stable in the temperature range of about -60°C to about 300°C, they are pourable at low temperatures and have excellent di ⁇ electric properties and low surface tension.
  • silicone fluids have very desirable pro ⁇ perties such as water repellency, lubricity, low volati ⁇ lity and good shear stability, i.e. they display a high degree of chemical inertness and resistance to weather- ing.
  • silicone fluids make them extremely useful substances which may form the basis of emulsions, greases, adhesives, sealants, coatings and chemical specialties.
  • silicone fluids are useful in a variety of applica- tions, e.g. as plastic additives, hydraulic fluids, vi ⁇ bration damping liquids, antifoamers, water repellent agents, impregnating agents, release agents, particle and fiber treatments, cosmetic additives, polishes, lubri- cants, surfactants and heat-transfer media.
  • si ⁇ cone fluid denotes a linear or branched polyorganosi- loxane compound, a polyorganocyclosiloxane compound or a copolymer thereof having a viscosity in the range of about 0.65 to 2,000,000 mm 2 /s, preferably in the range of about 0.65 to 150 mm 2 /s or the range of about 150 to 10,000 mm 2 /s or in the range of about 10,000 to 1,000,000 mm 2 /s, especially in the range of about 10 to 150 mm 2 /s or the range of about 150 to 10,000 mm 2 /s or the range of 10,000 to 700,000 mm 2 /s, in which the free valencies of the silicon atoms are fully or partly saturated with met ⁇ hyl groups. In case of partly saturation with methyl groups, the remaining free valencies are saturated with groups selected among amino, phenyl and vinyl groups.
  • silicone-containing composition as used herein relates to a composition comprising a silicone fluid.
  • surface as used herein relates to any surface which may be subjected to treatment with a silicone fluid or a silicone-containing composition.
  • surfac ⁇ es may be any hard surface such as metal, plastics, rub ⁇ ber, board, glass, wood, paper, concrete, rock, marble, gypsum and ceramic materials which optionally are coated, e.g with paint, enamel etc.; or any soft surface such as fibres of any kind (yarns, textiles, vegetable fibres, rock wool, hair etc.), skin (human or animal), and nails.
  • a silicone fluid or a silicone-con ⁇ taining composition may be removed completely or may be substatially removed, i.e. that the cleaned surface gives a clean impression by visual inspection and/or may be subjected to an assay showing a substantial removal of the silicone, e.g. preferably a removal of silicone of at least 70%, more preferably at least 85%, even more pre ⁇ ferably at least 95%, especially at least 98%, as com ⁇ pared to the amount of silicone fluid or silicone-con ⁇ taining composition present on the surface prior to applying the method of the invention.
  • a compound of formula I wherein X represents a monosaccharide moiety carrying the group -OR 1 at the anomeric carbon atom and carrying the group R-COO- at a primary hydroxy group;
  • R 1 represents alkyl with 2 - 6 carbon atoms or one of the following groups
  • Y represents methylene or ethylene; and R represents alkyl with 4 - 24 carbon atoms.
  • R 1 is hydrogen or a linear or branched alkyl group, preferably an unsubstituted alkyl group.
  • R 1 contains 1, 2, 3 or 4 carbon atoms. Examples of specific, preferred groups R 1 are methyl, et- hyl, propyl, isopropyl and butyl, most preferred ethyl and isopropyl.
  • X is a mono- or disaccharide moiety consisting of one he- xose or pentose unit.
  • Preferred mono- or disaccharides corresponding to the moiety X are glucose, fructose, ri- bose, annose, galactose, ahalose and sucrose, the most preferred monosaccharides being glucose, sucrose and ga ⁇ lactose.
  • R-COO- in formula I are saturated and unsaturated fatty acids, preferably containing 6 - 22 carbon atoms, more preferably containing 8 - 22 carbon atoms.
  • preferred fatty acids are hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, dode- canoic acid, tetradecanoic acid, hexadecanoic acid, oc- tadecanoic acid, eicosanoic acid, docosanoic acid, cis-9- octadecenoic acid, cis,cis-9,12-octadecadienoic acid, cis,cis,cis-9,12,15-octadecatrienoic acid and 12-hydroxy- 9-octadecenoic acid.
  • the selection of the optimal chain length of the fatty acid moiety depends on the surface to be cleaned as well as on the type of silicone fluid to be removed and may be determined by routine experimentation of a person skilled in the art.
  • a compound of formula I selected among the following compounds: ethyl 6-0-hexanoylglucoside, ethyl 6-0-heptanoylglucosi de, ethyl 6-0-octanoylglucoside, ethyl 6-O-nonanoylgluco side, ethyl 6-O-decanoylglucoside, ethyl 6-0-dodecanoyl glucoside, ethyl 6-O-tetradecanoylglucoside, ethyl 6-0- hexadecanoylglucoside, ethyl 6-O-octadecanoylglucoside, ethyl 6-O-eicosanoylglucoside, ethyl 6-O-docosanoylgluco side, ethyl 6-0-cis-9-octade
  • the monoesters used in the method according to the pres- ent invention can be prepared as described in US Patent 5,191,071 or by conventional methods of preparation.
  • US 5,191,071 discloses that the monoesters of the general formula I may be prepared by enzymatic syntheses of sugar esters in very high yields by using as substrates for the enzymatic esterification a carbohydrate carrying an alkyl group with 2 - 6 carbon atoms, phenyl or alkyl phenyl at the hydroxy group at the terminal anomeric carbon atom and a free fatty acid or an ester thereof as the ether substrate for the reaction.
  • the products of the reaction are sugar esters carrying an alkyl group at the hydroxy group at the anomeric carbon atom.
  • the enzymes which can be applied by the process are enzymes capable of forming ester linkages.
  • This group of enzymes comprises hydrolases, such as esterases, and lipases.
  • the enzymes applied by the process may be used in a soluble state or the enzymes may be immobilised, if desired.
  • the enzymes may be modified by chemical or genetic methods in order to optimise their reactivity in regard to a speci ⁇ fic reaction of interest. Examples of specific enzymes which may be used by the process are porcine pancreatic lipase and microbial lipases obtained, e.g.
  • lipases are obtainable from Humicola brevispora. brevis var. ther oidea and insolens which were deposited at DSM under the Nos. 4110, 4111 and 1800, respectively, on 4 May 1987, 4 May 1987 and 1 October 1981, respectively. Additional lipases are obtainable from the following strains, which are freely available to the public from Centralbureau voor Schimmelculturen
  • Candida antarctica CBS 5955, ATCC 34888, NRRL Y-8295, CBS 6678, ATCC 28323, CBS 6821 and NRRL Y-7954;
  • Candida tsukubaensis CBS 6389, ATCC 24555 and NRRL Y- 7792;
  • Candida auriculariae CBS 6379, ATCC 24121 and IFO 1580;
  • Candida humicola CBS 571, ATCC 14438, IFO 0760, CBS 2041, ATCC 9949, NRRL Y-1266, IFO 0753 and IFO 1527 and Candida foliorum: CBS 5234 and ATCC 18820.
  • the process may be carried out simply by mixing a glycoside of the general formula HO - X - OR 1 , where X and R 1 each is as defined above, with an acid or an ester thereof of the general formula R-COOR 2 , where R 2 repre ⁇ sents hydrogen or lower alkyl, in the presence of the enzyme and, optionally, the reaction may be carried out in a solvent in which the enzyme exhibits the desired activity.
  • a solvent in which the enzyme exhibits the desired activity.
  • no solvent is added. If an organic solvent is used, it should have no deleterious effect on the enzyme. Examples of such solvents are ketones, hydro ⁇ carbons and ethers.
  • Preferred solvents are pentan, hexan, heptan and 2-butanone.
  • the reaction medium is non-aqueous or contains only the approximate amount of water which is needed to ensure a good reactivity and life-time of the applied enzyme.
  • the reac ⁇ tion temperature is in the range of about 20 - 100°C, preferably about 30 - 80°C.
  • the reaction is performed at a low pressure, preferably below about 0.05 bar.
  • the monoesters used in the method according to the inven- tion may be used in dilute aqueous solutions alone, i.e. as the only active ingredient, and without builders or other ingredients. Under certain conditions it may be de ⁇ sirable to formulate the monoesters with other detergent ingredients known in the art, for instance to aid in par ⁇ ticle removal or to prevent particle redeposition on the surface to be cleaned.
  • the monoesters are applied in an aqueous solution, preferably in a concentration of between about 100 ppm and about 100,000 ppm, more preferably in a concentration of between about 500 ppm and about 80,000 ppm, especially in a concentration of between about 1000 ppm and about 50,000 ppm.
  • the present invention relates to a cleaning composition
  • a cleaning composition comprising a monoester of the for- ro-.ila I capable of substantially removing silicone fluids or silicone elastomers or silicone-containing composi ⁇ tions from a surface.
  • a cleaning composition may comprise an efficient amount of a monoester of the for ⁇ mula I and water and optionally one or more builders, surfactants and/or additives.
  • the pH of the cleaning com- position is preferably neutral or near-neutral such as below 8, whereby the conventional hazards of alkaline or highly alkaline cleaning composition may be avoided.
  • a cleaning composition comprising a compound of formula I may be in any convenient form, such as a powder or a li ⁇ quid.
  • Liquid and powder cleaning compositions may be formulated in analogy with "Frame formulations for liquid/powder heavy-duty detergents" (J. Falbe: Surfactants in Consumer Products. Theory, Technology and Application, Springer- Verlag 1987) by replacing all or part (e.g. 50%) of the non-ionic surfactant with a compound of formula I.
  • liquid cleaning compositions may in addition to the com ⁇ pound of formula I comprise anionic surfactants, non-io ⁇ nic surfactants, cationic surfactants, amphoteric surfac- tants, suds controlling agents, foaming boosters, enzy ⁇ mes, builders, formulation aids, chelating agents, anti- corrosion agents, optical brighteners, stabilizers, fab ⁇ ric softeners, fragrances, dyestuffs and water.
  • powder cleaning compositions may comprise an ⁇ ionic surfactants, non-ionic surfactants, cationic sur ⁇ factants, amphoteric surfactants, suds controlling agents, foaming boosters, chelating agents, ion exchan ⁇ gers, alkalis, cobuilders, bleaching agents, bleach ac- tivators, bleach stabilizers, fabric softeners, antirede- position agents, enzymes, optical brighteners, anticorro- sion agents, fragrances, dyestuffs and blueing agents, formulation aids, fillers and water.
  • the cleaning composition of the invention may be useful at any pH and any temperature usually applied in cleaning processes. Accordingly, the present method may preferably be applied at any tempera ⁇ ture between about 5°C and about 100°C, more preferably at a temperature below about 70°C. For a substantial removal of certain types of silicone fluids or silicone- containing compositions from certain surfaces, it may be advantageous to apply the method at a temperature above ambient temperature. The determination of the optimum or near optimum temperature is a matter of routine experi ⁇ mentation for the skilled person. Also, the present method may be applied at any pH. However, it may be con ⁇ venient to apply the method at neutral or near-neutral pH for safety and environmental reasons.
  • the present invention provides a method which is believed to solve problems of the nature stated above.
  • the method of the invention is useful in the petrochemical industry, the agrochemical industry, the food industry, the detergent industry, the tyre industry, in the treatment of sewage, in the cosme ⁇ tics industry, the pharmaceuticals industry, the textile industry, the leather industry, the plastics industry, the metal industry, in construction, and in the surface and coating industry.
  • the method of the invention is useful for removing silicone-containing hair care products, skin care products, deodorants, decorative cosmetics, oral hygiene products, softening products, water repellant products, defoaming products, adhesion promoting products, sewing-thread lubricants, laquer ad- ditives, thermostable paints, functional coatings, anti- corrosion protection products, coil coating products, silicone alkyds, printing inks, plasticising additives, toners, fuser oils, release agents, pharmaceutical prod- ucts, welding additives, automobile polishes, furniture polishes; and/or for removing silicone fluids used in the preparation or manufacture of such products.
  • the method of the present inven- tion may also prove useful for the removal of silicone elastomers or silicone resins (semi-cured or cured sili ⁇ cones) or compositions comprising such substances.
  • An object glass for use in a microscope was greased with conventional silicone-containing laboratory cockstopper grease whereafter it was placed in a laboratory ultra ⁇ sonic cleaning bath filled with a 0.5% aqueous solution of ethyl-6-0-decanoylglucoside.
  • the ultrasound was turned on for 5 minutes during which period the layer of silicone concentrated into droplets which finally left the glass slide and rose to the sur ⁇ face of the bath.
  • silicone fluid supplied by Dow- Corning, brand name DC 200, having a viscosity of 100 mm 2 /s
  • the flask was rinsed in tap water and finally wiped dry with a clean cloth. As a result the flask surface became completely clean.
  • Silicone joint filler which had contaminated a wooden kitchen table and where the stains were several months old were easily removed by rubbing with a cloth soaked in a 10% solution of ethyl 6-O-coconut fatty acyl glucoside followed by wiping with a clean moist cloth.
  • a washing machine which is used for washing flasks for insulin was sometimes used for washing ampoules which are siliconized on the inside. This leaves silicone on the washing machine's inner surfaces which is transferred to the non-siliconized flasks in the following many wash cycles. As a consequence the labels on the flasks fall off. Normally, it takes 5 to 6 washing cycles before the silicone oil is removed.
  • the silicone fluid used for siliconizing ampoules was a Wacker Silicone Fluid Emulsion E2 (35% dispersion of a non-reactive medium-viscosity (2000 - 7500 mPa/s) dimet ⁇ hyl polysiloxane in water) , supplied by Wacker-Chemie GmbH, Kunststoff, Germany. It was applied on the ampoules at a solids content of 1%.
  • PDMS Dimethyl silane, obtained from Wacker Chemie, type Wacker AK350, 350 cP
  • Pre-cleaning agent Deconex (Borer Chemie) . - De ineralised water.
  • D C 12 . 14 alkylpolyglycoside (DP 1,4) sold under the trade name "Plantaren 600" (manufactured by Henkel KGaA, D ⁇ sseldorf, Germany) .
  • E C g . 10 alkylpolyglycoside (DP 1,6) sold under the trade name "APG 225 UP” (manufactured by Henkel KGaA, D ⁇ sseldorf, Germany) .
  • F C, 6 -alkylether ethoxylate (C 6 E0 2 ) [AEO] sold under the trade name "BRIJ52” (manufactured by ICI Chemicals and Polymers, Ltd, Middlesborough, Cleveland, U.S.A.).
  • G Conventional laboratory cleaning agent sold under the trade name "RBS 35” (sold by Bie & Berntsen, Denmark, Catalogue No. 27000; manufactured by Carl Roth GmbH + Co. , Düsseldorf, Germany).
  • Cleaning compositions each containing one of the com- pounds to be tested were prepared by heating the ethyl glycoside in question to 60°C, mixing the ester with boiling demineralised water and performing the final dilution with cold demineralised water.
  • Compounds D, E, F and G are comparison compounds. Each compound was tested in various concentrations, i.e. con ⁇ centration (w/w%) of active compound in the cleaning or detergent solution in order to determine the minimum con ⁇ centration giving optimum cleaning effect.
  • the cleaning effect is expressed in terms of the differ ⁇ ence in reflectance measurements of soiled and cleaned discs, since the amount of silicone present on the metal discs after applying the method of the invention was too low to be determined by weighing the discs.
  • the cleaning effect is expressed as "% recovery of light reflection".
  • the cleaning effect is expressed as "% weight removal of silicone".
  • compound B ethyl 6-O-dodecanoylglucoside
  • RBS 35 conventional cleaning com ⁇ position G
  • ethyl 6-0-dodecanoylglucoside has a better cleaning effect on acrylic plast than com ⁇ pound G (RBS 35) and is much more effective (at least 20 times) .

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

Un procédé permettant d'enlever pratiquement entièrement une huile de silicone ou une composition contenant de la silicone d'une surface, et consistant successivement à a) appliquer à la surface une quantité efficace d'un composé monoester de la formule générale R-COO-X-OR1, dans laquelle X représente une fraction mono- ou disaccharide portant le groupe -OR1 au niveau de l'atome de carbone anomérique et le groupe R-COO- au niveau d'un groupe hydroxy principal; R1 représente hydrogène, alkyle contenant 1 à 6 atomes de carbone ou l'un des groupes (a), (b) et (c), dans lesquels Y représente méthylène ou éthylène; et R représente alkyle, alcényle, alcadiényle ou alcatriényle linéaire ou ramifié contenant 4 à 24 atomes de carbone à substitution éventuelle par hydroxy; b) à soumettre éventuellement la surface à un traitement mécanique; et c) à enlever l'huile de silicone et ou les composés monoesters de la surface.
PCT/DK1994/000343 1993-09-15 1994-09-15 Procede d'enlevement d'huiles de silicone WO1995007967A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP7508921A JPH09503006A (ja) 1993-09-15 1994-09-15 シリコーン流体の除去方法
EP94926814A EP0719318A1 (fr) 1993-09-15 1994-09-15 Procede d'enlevement d'huiles de silicone
AU76518/94A AU687875B2 (en) 1993-09-15 1994-09-15 A method for removing silicone fluids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK103593A DK103593D0 (fr) 1993-09-15 1993-09-15
DK1035/93 1993-09-15

Publications (1)

Publication Number Publication Date
WO1995007967A1 true WO1995007967A1 (fr) 1995-03-23

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PCT/DK1994/000343 WO1995007967A1 (fr) 1993-09-15 1994-09-15 Procede d'enlevement d'huiles de silicone

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EP (1) EP0719318A1 (fr)
JP (1) JPH09503006A (fr)
CN (1) CN1130919A (fr)
AU (1) AU687875B2 (fr)
CA (1) CA2171291A1 (fr)
DK (1) DK103593D0 (fr)
NZ (1) NZ273283A (fr)
WO (1) WO1995007967A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8568523B1 (en) * 2005-12-05 2013-10-29 Roland E. Ransom Method of treating tire surfaces
WO2018065545A1 (fr) * 2016-10-05 2018-04-12 Pierre Fabre Dermo-Cosmetique UTILISATION 6-O-(C8-C20 ALKYL ESTER) DE 1-O-(C1-C6 ALKYL)-ß-D-GLUCOSIDE COMME AGENT PROTECTEUR DE LA PEAU
US11491461B2 (en) 2017-03-14 2022-11-08 Dow Silicones Corporation Method of depleting an organosilicon component in a mixture using a sorbent copolymer and apparatus for practicing the method

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104071751B (zh) * 2014-06-13 2016-02-10 王金明 一种吸附脱除盐酸中硅氧烷的方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1267509A (en) * 1968-04-05 1972-03-22 Imp Smelting Corp Ltd Glass cleaner
EP0199227A2 (fr) * 1985-04-26 1986-10-29 Hansa Textilchemie GmbH Procédé pour enlever des silicones se trouvant sur des fibres, des fils ou des étoffes
EP0437216A2 (fr) * 1990-01-10 1991-07-17 The Nisshin Oil Mills, Ltd. Agents pour la dissolution et la solubilisation de silicones
WO1991012305A1 (fr) * 1990-02-16 1991-08-22 Novo Nordisk A/S Elimination des substances huileuses
US5191071A (en) * 1987-08-21 1993-03-02 Novo Nordisk A/S Monoesters of glycosides and a process for enzymatic preparation thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1267509A (en) * 1968-04-05 1972-03-22 Imp Smelting Corp Ltd Glass cleaner
EP0199227A2 (fr) * 1985-04-26 1986-10-29 Hansa Textilchemie GmbH Procédé pour enlever des silicones se trouvant sur des fibres, des fils ou des étoffes
US5191071A (en) * 1987-08-21 1993-03-02 Novo Nordisk A/S Monoesters of glycosides and a process for enzymatic preparation thereof
EP0437216A2 (fr) * 1990-01-10 1991-07-17 The Nisshin Oil Mills, Ltd. Agents pour la dissolution et la solubilisation de silicones
WO1991012305A1 (fr) * 1990-02-16 1991-08-22 Novo Nordisk A/S Elimination des substances huileuses

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8568523B1 (en) * 2005-12-05 2013-10-29 Roland E. Ransom Method of treating tire surfaces
WO2018065545A1 (fr) * 2016-10-05 2018-04-12 Pierre Fabre Dermo-Cosmetique UTILISATION 6-O-(C8-C20 ALKYL ESTER) DE 1-O-(C1-C6 ALKYL)-ß-D-GLUCOSIDE COMME AGENT PROTECTEUR DE LA PEAU
US11491461B2 (en) 2017-03-14 2022-11-08 Dow Silicones Corporation Method of depleting an organosilicon component in a mixture using a sorbent copolymer and apparatus for practicing the method

Also Published As

Publication number Publication date
EP0719318A1 (fr) 1996-07-03
CA2171291A1 (fr) 1995-03-23
AU687875B2 (en) 1998-03-05
NZ273283A (en) 1997-04-24
JPH09503006A (ja) 1997-03-25
AU7651894A (en) 1995-04-03
CN1130919A (zh) 1996-09-11
DK103593D0 (fr) 1993-09-15

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