EP0511253A1 - Produits de nettoyage desemulsifiants et application. - Google Patents

Produits de nettoyage desemulsifiants et application.

Info

Publication number
EP0511253A1
EP0511253A1 EP91902214A EP91902214A EP0511253A1 EP 0511253 A1 EP0511253 A1 EP 0511253A1 EP 91902214 A EP91902214 A EP 91902214A EP 91902214 A EP91902214 A EP 91902214A EP 0511253 A1 EP0511253 A1 EP 0511253A1
Authority
EP
European Patent Office
Prior art keywords
weight
acid
contain
cleaning
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP91902214A
Other languages
German (de)
English (en)
Other versions
EP0511253B1 (fr
Inventor
Juergen Geke
Friedbert Zetzsche
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.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0511253A1 publication Critical patent/EP0511253A1/fr
Application granted granted Critical
Publication of EP0511253B1 publication Critical patent/EP0511253B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • 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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • 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
    • C11D1/02—Anionic compounds
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • 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
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the present invention relates to de-emulsifying, powdered or liquid cleaning agents with which painted and unpainted surfaces of vehicles, engines, floors in workshops or other work surfaces can be cleaned and degreased, the contaminants removed thereby being demulsified.
  • the invention further relates to the use of these cleaning agents.
  • US Pat. No. 3,663,445 describes liquid, storage-stable concentrates and cleaning and degreasing preparations, in particular for metallic surfaces, which are obtained from said concentrates by dilution with water and which consist of 6 to 45% by weight of a nonionic surfactant, for example a fatty alcohol ethoxylate, 4 to 33% by weight of an ethanolamine salt of a fatty acid, 2 to 90% by weight of an ethanol ins and 0 to 50% by weight of water.
  • a nonionic surfactant for example a fatty alcohol ethoxylate, 4 to 33% by weight of an ethanolamine salt of a fatty acid, 2 to 90% by weight of an ethanol ins and 0 to 50% by weight of water.
  • Austrian patent specification 308,936 relates to liquid storage-stable concentrates and to cleaning and degreasing agents which can be prepared by dilution with water and which contain at least 5% by weight of a nonionic surfactant, for example a fatty alcohol ethoxylate, at least 3% by weight of a saturated or unsaturated fatty acid with 8 up to 22 carbon atoms in the molecule, at least 4.5 wt .-% of one or more alkanolamines and conventional additives such as complexing agents, and water.
  • British Patent 1,321,513 relates to a cleaning process for metallic surfaces with two cleaning baths to be used in succession, the pre-cleaning bath and the degreasing bath.
  • the pre-cleaning bath consists of at least 5% by weight of a nonionic surfactant containing 3 to 5 moles of ethylene oxide, at least 3% by weight of a fatty acid and / or an alkyl polyethylene oxide carboxylic acid, at least 1.5% by weight of an alkanol and / or Oxazine and the rest water.
  • the degreasing bath consists of an inorganic or organic alkaline substance, for example potassium hydroxide, potassium carbonate, potassium orthophosphate, potassium pyrophosphate, potassium borate, alkanolamine, preferably mono-, di- or triethanolamine, morpholine, and a complexing agent, a low-foaming surfactant, for example a condensation product of Fatty acids with 3 to 5 moles of ethylene oxide, as well as other additives and the rest water.
  • an inorganic or organic alkaline substance for example potassium hydroxide, potassium carbonate, potassium orthophosphate, potassium pyrophosphate, potassium borate, alkanolamine, preferably mono-, di- or triethanolamine, morpholine, and a complexing agent, a low-foaming surfactant, for example a condensation product of Fatty acids with 3 to 5 moles of ethylene oxide, as well as other additives and the rest water.
  • Austrian patent specification 299,421 relates to an aqueous liquid composition for mechanical dishwashing, which contains 2 to 6% by weight of a nonionic surfactant, 15 to 25% by weight of an organic sequestering agent, 7 to 15% by weight of a hydrotropic substance, 3 to Contains 15% by weight of an ethanolamine and 0.1 to 0.6% of a corrosion inhibitor.
  • DE-OS 25 05 252 relates to a process for the industrial cleaning and degreasing of objects, in particular metals, by treating the objects with a solvent-free, aqueous solution which contains an organic sequestering agent and a hydrotropic substance, which is characterized in that that an aqueous solution is used which contains 0.1 to 20% by weight of an organic, hydrotropic electrolyte in the form of benzenesulfonates, lower alkylbenzenesulfonates, di- (lower alkyl) benzenesulfonates or mixtures thereof and from 0.1 to 25% by weight .-% of an organic Contains sequestering agent in the form of aminopolycarboxylic acids or aminopolyphosphonic acids or their salts or mixtures thereof, the weight ratio of the electrolyte to the sequestering agent being from 2: 1 to 1: 3 and the pH of the solution being from 9 to 13.
  • US Pat. No. 4,321,166 relates to liquid cleaners which contain 20 to 70% by weight of a surfactant, for example a fatty alcohol ethoxylate, 0.85 to 2% by weight of a corrosion inhibitor system which essentially consists of a mixture of an oligomeric olefinic fatty acid and an aromatic triazole exists, as well as 1 to 75 wt .-% water.
  • a surfactant for example a fatty alcohol ethoxylate
  • a corrosion inhibitor system which essentially consists of a mixture of an oligomeric olefinic fatty acid and an aromatic triazole exists, as well as 1 to 75 wt .-% water.
  • DE-OS 35 30 623 relates to demulsifying cleaning agents with a surface moisturizing effect, containing builders / complexing agents in an amount of 0.5 to 10% by weight, one or more alkanolamine (s) in an amount of 20 to 60% by weight. %, one or more nonionic surfactant (s) in an amount of 1 to 15% by weight and the balance water.
  • These cleaning agents and corresponding cleaning agent preparations are suitable for cleaning and degreasing painted and unpainted vehicle surfaces, engines, floors and walls of workshops, etc., even at room temperature, while removing the oily or greasy contaminants removed.
  • the demulsifying effect of these cleaning agents known from the prior art is unsatisfactory with regard to today's requirements. This means that the demulsification of the removed oil-containing impurities or the subsequent oil separation resulting therefrom is not sufficient to lower the residual oil values in the wastewater to the low values required today.
  • the demulsifying action of the cleaning agents should result in improved oil separation and thus lower residual oil values in the waste water.
  • the invention thus relates to demulsifying, powdered or liquid cleaning agents based on nonionic surfactants, carboxylic acids, anionic surfactants and optionally builder substances, characterized in that they contain a combination of the following constituents:
  • R- is a linear or branched alkyl radical having 6 to 9 carbon atoms and n is a number in the range from 3 to 10,
  • R and R 4 are each, independently of one another, linear or branched alkyl radicals having 10 to 18 carbon atoms, m is a number in the range from 1 to 6, R alkylbenzene radicals having 7 to 9 carbon atoms and Me are each an alkali metal atom,
  • the content of the cleaning agents in the above components a, b and c is a total of 1.5 to 15% by weight and the * weight ratio of a to b is in the range from 3: 1 to 1: 6 and the weight ratio of ( a + b): c is in the range from 3: 1 to 1: 3, d) 0 to 98.5% by weight of at least one organic or inorganic builder substance, selected from the group of the oligo- and polycarboxylic acids or their water-soluble salts and the alkali metal phosphates, silicates, borates, carbonates and hydroxides ,
  • the demulsifying cleaning agents according to the invention have an excellent cleaning potential. Due to the good demulsifying effectiveness of these cleaning agents, the removed oil-containing contaminants separate themselves when the aqueous application solution is diluted. Fats and oils washed off the substrate surfaces in this way can be easily and easily removed from aqueous media, for example using simple oil separators. In this way, wastewater suitable for receiving water always results.
  • the demulsifying cleaning agents contain 2.5 to 12.5% by weight of a combination of those defined above
  • R - stands for a linear or branched alkyl radical with 6 to 9 carbon atoms.
  • the following radicals are therefore suitable as substituent R *: n-hexyl, n-heptyl, n-octyl and n-nonyl and the branched chain isomers of the alkyl radicals mentioned.
  • the number of ethoxy radicals in the molecule - n - is in the range from 3 to 10.
  • corresponding addition products of ethylene oxide with fatty alcohols are used in particular as component (a).
  • Such fatty alcohol ethoxylates can be used either individually or in combination.
  • an adduct of 4 to 6 moles of ethylene oxide with n-octanol in particular the adduct of 4 moles of ethylene oxide with n-octanol, is used as component (a).
  • R 2 represents a linear or branched alkyl radical having 5 to 11 carbon atoms.
  • Monocarboxylic acids in the sense of this general formula are therefore the following linear fatty acids: hexanoic acid (caproic acid), heptanoic acid (onanthic acid), octanoic acid (capyrylic acid), nonanoic acid (pelargonic acid), decanoic acid (capric acid), undecanoic acid and dodecanoic acid (lauric acid).
  • the corresponding branched-chain monocarboxylic acids are also suitable as component (b).
  • These monocarboxylic acids of component (b) can also be used both alone and in combination.
  • Suitable water-soluble salts of such monocarboxylic acids are, in particular, the alkali metal salts, preferably their sodium salts.
  • branched-chain monocarboxylic acids having a total of 8 to 9 carbon atoms are used as component (b).
  • At least one anionic surfactant which is selected from the group of the alkyl sulfates of the general formula (III), the alkyl polyglycol ether sulfates of the general formula (IV) and the alkylarylsulfonates of the general formula (V), is used as component (c) in the demulsifying cleaning agents according to the invention.
  • substituents R 3 and R 4 each independently represent linear or branched alkyl radicals having 10 to 18 carbon atoms.
  • the following radicals are therefore suitable as substituents R 3 and R 4 : n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl and n-octadecyl and the branched chain isomers of the alkyl radicals mentioned.
  • the number of ethylene oxide units - m - in the alkylpolyglycol ether sulfates of the general formula (IV) is in the range from 1 to 6.
  • the radical R - in the alkylarylsulfonates of the general formula (V) is selected from alkylbenzene radicals having 7 to 9 carbon atoms the group of toluene, xylene, mesithylene and cumene.
  • Me each represents an alkali metal atom, preferably sodium.
  • the content of components (a), (b) and (c) defined above in the cleaning agents according to the invention is 1.5 to 15% by weight in total. It is also important in the context of the invention that the weight ratio of component (a) to component (b) is in the range from 3: 1 to 1: 6 and also the weight ratio of the sum of components (a) and (b) to component (c) in the range from 3: 1 to 1: 3.
  • component (c) is a Ci2-i4-fatty alcohol sulfate sodium salt and / or a Ci2-i4-fatty alcohol ether sulfate.
  • these may optionally contain at least one organic or inorganic builder.
  • organic or inorganic builder such as, for example, oligo- or polycarboxylic acids and their water-soluble salts, for example ethylene-diamine-tetraacetic acid, nitrilotriacetic acid, diethylenetriamine-pentaacetic acid or n- (2-hydroxyethyl) -ethylenediamine-triacetic acid, preferably in the form of their alkali metal salts, especially the sodium salts.
  • Further suitable builder substances within the meaning of the invention are alkali metal phosphates, polyphosphates, silicates, borates, carbonates and / or hydroxides, preferably likewise in the form of the corresponding sodium salts.
  • the sodium salts of ethylenediaminetetraacetic acid and / or nitrilotriacetic acid are preferably used as builder substances.
  • the cleaning agents according to the invention also contain powdery or liquid auxiliaries and / or adjusting agents which add up to 100% by weight of the components (a), (b), (c) and optionally (d) contained in the cleaning agents . They are used in particular for the packaging of either powdered or liquid formulations of the cleaning agents according to the invention. If liquid formulations are desired, water is used in particular as an adjusting agent. Suitable powdered adjusting agents which then lead to powdered formulations are alkali metal sulfates or carbonates, especially in the form of sodium salts, or urea. Furthermore, the cleaning agents according to the invention can also contain small amounts of oleic acid or its sodium salt and of diethanolamine and / or triethanolamine as auxiliaries.
  • the cleaning agents according to the invention are produced by mixing the abovementioned components in the respective amounts by methods known per se.
  • the cleaning agents are generally stored or shipped in the form of an aqueous or powdery concentrate containing the combination of the specified components, to which the stated amounts (in% by weight) also relate.
  • the demulsifying cleaning agents according to the invention depending on the type of application and degree of contamination of the surfaces to be cleaned - are used in any dilution with water.
  • the cleaning agents are used in water-diluted application solutions for cleaning and degreasing hard surfaces, the concentration of components (a), (b) and (c) in these application solutions being 0.01 in total up to 3% by weight, in particular 0.025 to 1% by weight.
  • EO ethylene oxide
  • a liquid detergent is made by mixing
  • a powder detergent is mixed by Misc: -n of 3.0 wt .-% of a condensation product of n-octanol with 4 mol E0
  • Ci2-Ci4-fatty alcohol sulfate sodium salt 1.0% by weight of Ci2-Ci4-fatty alcohol sulfate sodium salt
  • a comparative cleaner was made by mixing
  • Ratio 2 1, and 49.0 wt .-% water.
  • oil-containing waste water was produced in accordance with the technical delivery specification of the German Federal Railroad TL 918 81, sheet 6.
  • the concentration of the cleaning agents in the aqueous solutions was 1.2% by weight; the oil pollution - produced with squalane as mineral oil - 1000 ppm.
  • the residual oil values in the latter were determined in accordance with the technical delivery specification cited.
  • the following residual oil values in the wastewater resulted:
  • Example 1 12 ppm
  • Example 2 31 ppm Comparative example: 78 ppm
  • a painted, heavily soiled inside of a car bonnet was placed vertically. 2.5% by weight of cleaning agent solutions as test solutions were prepared from the cleaning agents according to Examples 1, 2 and the comparative example by dilution with water (16 ° d).
  • viscose sponges with the dimensions 90 ⁇ 50 ⁇ 40 mm were placed, saturated soaked, and placed individually upright for 3 minutes to allow the excess solution to run out.
  • the cleaning agent compositions had the following values: Detergent composition according to Example 1: 2.4 Detergent composition according to Example 2: 2.6 Detergent composition according to comparative example (standard): 1.0

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  • 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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

On propose des produits de nettoyage désémulsifiants pulvérulents ou liquides à base de tensio-actifs non ioniques, d'acides carboxyliques, de tensio-actifs anioniques et le cas échéant d'adjuvants, caractérisés en ce qu'ils contiennent une combinaison des constituants suivants: (a) au moins un éthoxylate d'alkyle de formule (I): R1-O-(CH2CH2O)n-H, dans laquelle R1 désigne un résidu alkyle linéaire ou ramifié avec 6 à 9 atomes de C et n un nombre compris entre 3 et 10, (b) au moins un acide monocarboxylique ou ses sels solubles dans l'eau de formule générale (II): R2-COOH, dans laquelle R2 désigne un résidu alkyle linéaire ou ramifié avec 5 à 11 atomes de C, (c) au moins un tensio-actif anionique choisi dans le groupe (c1) des sulfates d'alkyle de formule générale (III): R3-O-SO3Me, (c2) des sulfates d'alkyle et de polyglycoléther de formule générale (IV): R4-O-(CH2CH2O)m-SO3Me, (c3) des alkylarylsulfonates de formule générale (V): R5-SO3-Me, dans laquelle R3 et R4 désignent chacun, indépendamment l'un de l'autre, des résidus alkyle linéaires ou ramifiés avec 10 à 18 atomes de C, m un nombre de 1 à 6, R5 des résidus alkylbenzol avec 7 à 9 atomes de C et Me dans chaque cas un atome de métal alcalin, la concentration des composants a, b et c précédénts dans les produits de nettoyage représentant au total 1,5 à 15 % en poids et le rapport en poids de a à b étant dans la plage de 3:1 à 1:6 et le rapport en poids de (a+b):c dans la plage de 3:1 à 1:3, (d) 0 a 98,5 % en poids au moins d'un adjuvant organique ou inorganique, choisi dans le groupe des acides oligo et polycarboxyliques ou de leurs sels solubles dans l'eau ainsi que des phosphates, silicates, borates, carbonates et hydroxydes de métaux alcalins, (e) jusqu'à 100 % en poids d'adjuvants ou d'agents de fixation pulvérulents ou liquides.
EP91902214A 1990-01-20 1991-01-12 Produits de nettoyage desemulsifiants et application Expired - Lifetime EP0511253B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4001595A DE4001595A1 (de) 1990-01-20 1990-01-20 Demulgierende, pulverfoermige oder fluessige reinigungsmittel und deren verwendung
DE4001595 1990-01-20
PCT/EP1991/000039 WO1991010718A1 (fr) 1990-01-20 1991-01-12 Produits de nettoyage desemulsifiants et application

Publications (2)

Publication Number Publication Date
EP0511253A1 true EP0511253A1 (fr) 1992-11-04
EP0511253B1 EP0511253B1 (fr) 1995-02-22

Family

ID=6398453

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91902214A Expired - Lifetime EP0511253B1 (fr) 1990-01-20 1991-01-12 Produits de nettoyage desemulsifiants et application

Country Status (9)

Country Link
US (1) US5286402A (fr)
EP (1) EP0511253B1 (fr)
JP (1) JPH05504155A (fr)
AT (1) ATE118809T1 (fr)
DE (2) DE4001595A1 (fr)
DK (1) DK0511253T3 (fr)
ES (1) ES2068568T3 (fr)
NO (1) NO180202C (fr)
WO (1) WO1991010718A1 (fr)

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US7647993B2 (en) 2004-05-06 2010-01-19 Smith International, Inc. Thermally stable diamond bonded materials and compacts
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Also Published As

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DK0511253T3 (da) 1995-07-10
US5286402A (en) 1994-02-15
NO922692L (no) 1992-07-08
NO180202B (no) 1996-11-25
JPH05504155A (ja) 1993-07-01
DE59104713D1 (de) 1995-03-30
DE4001595A1 (de) 1991-07-25
ATE118809T1 (de) 1995-03-15
NO180202C (no) 1997-03-05
ES2068568T3 (es) 1995-04-16
NO922692D0 (no) 1992-07-08
EP0511253B1 (fr) 1995-02-22
WO1991010718A1 (fr) 1991-07-25

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