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WO2006010375A1 - Formulation de degraissage de metal comprenant un agent desemulsionnant, utilisation de cet agent et procede de degraissage de metal - Google Patents

Formulation de degraissage de metal comprenant un agent desemulsionnant, utilisation de cet agent et procede de degraissage de metal Download PDF

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Publication number
WO2006010375A1
WO2006010375A1 PCT/EP2004/008433 EP2004008433W WO2006010375A1 WO 2006010375 A1 WO2006010375 A1 WO 2006010375A1 EP 2004008433 W EP2004008433 W EP 2004008433W WO 2006010375 A1 WO2006010375 A1 WO 2006010375A1
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WO
WIPO (PCT)
Prior art keywords
oil
formulation
metal
degreasing
agent
Prior art date
Application number
PCT/EP2004/008433
Other languages
English (en)
Inventor
Dalibor Satrapa
Original Assignee
Rhodia Chimie
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 Rhodia Chimie filed Critical Rhodia Chimie
Priority to PCT/EP2004/008433 priority Critical patent/WO2006010375A1/fr
Publication of WO2006010375A1 publication Critical patent/WO2006010375A1/fr

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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
    • 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
    • C23G1/14—Cleaning or pickling metallic material with solutions or molten salts with alkaline solutions

Definitions

  • Formulation for degreasing metal comprising a demulsifying agent, use of the agent, and process for degreasing metal
  • the invention relates to a formulation for degreasing metal, comprising degreasing agents and a demulsifying agent.
  • Metal working requires the use of lubricants such as oils.
  • the oil used during working operations needs to be removed by an appropriate treatment. It is referred to metal degreasing.
  • metal parts or plates often have, after working operation, an oil layer to be removed by a degreasing treatment.
  • aqueous compositions comprising a degreasing formulation can be used. Accordingly, oil-soiled metal is treated with an aqueous composition comprising a formulation having degreasing agents and a demulsifier, to obtain an emulsion of oil in water that will phase- separate. Then the phases are separated to recover and optionally re-use the oil and the aqueous composition.
  • ethoxylated amines as demulsifiers is known.
  • these compounds have a low biodegradability and their use at least in some areas might be banned in some countries. Therefore there is a need for a replacement solution, involving using replacement compounds preferably having a higher biodegradability, while delivering properties that are still interesting.
  • ethoxylated amides or “superamides”
  • surfactants or emulsifiers have been described in patents or patent applications including DE1916263, DT 2605502, DE 19650357. These documents describe very specific or modified ethoxylated amides, and/or their use in areas different from metal treatment, and/or as providing emulsification properties.
  • the invention addresses at least some of the above-mentioned problems. Accordingly, the invention provides a formulation for degreasing metal, comprising metal degreasing agents and a demulsifying agent, wherein the demusifying agent is a compound having one of the following formulae (I) or (II):
  • R-CO-N H-CH 2 -CH 2 -[EO] m -OH R-CO-N[CH 2 -CH 2 -[EO] n -OH][CH 2 -CH 2 -[EO] n -OH] (II) wherein: - R is a linear or branched, saturated or unsaturated C 7 -C 22 hydrocarbon group, optionally carrying at least one hydroxyl group, - EO represents a group having formula -0-CH 2 -CH 2 -,
  • n and n' are average numbers different from 0,
  • - n+n' is of from 1 to 50
  • - m is of from 1 to 50.
  • the invention also relates to the use of the above compounds as demulsifying agents, and advantageously as biodegradable demulsifying agents.
  • the invention also relates to a process for degreasing metal parts or plates with an aqueous compositions, comprising the following steps: a) treating oil-soiled metal plates with an aqueous composition comprising the formulation above, to obtain an oil-soiled composition comprising emulsified oil in water, b) subsequently or simultaneously allowing a phase separation of an oil phase comprising the oil, and of an aqueous phase, c) recovering separately the oil phase and the aqueous phase, d) optionally, re-using totally at least one of the recovered phase or ingredients therefrom.
  • the demulsifying agent is a compound having formula (I) or formula (II) above.
  • the demulsifying agent can also be a mixture compounds of formula (I) and formula (II).
  • n and n 1 are average numbers. These numbers result from an ethoxylation process (reaction with ethylene oxide). Thus, numbers m and n+n' might be considered as the number of moles of ethylene oxide per mole of reagent to be ethoxylated.
  • R is preferably a C 7 -C 22 linear or branched, saturated or unsaturated hydrocarbon group, preferably a Ci 0 -C 16 linear or branched linear or branched, saturated or unsaturated, hydrocarbon group, and more preferably a C 12 -C 14 linear or branched linear or branched, saturated or unsaturated, hydrocarbon group (for example a "coco" group).
  • R groups are usually actually a mixture of different groups having different numbers of carbon atoms, being linear or branched, and having different numbers of insaturations. These mixtures come from the reagents used to prepare them, which are actually distillation cuts and/or have a natural origin.
  • the number of carbon atoms in the R group refers to the number of carbon atoms of the two most represented species. More precisely, group R can derive from fatty acids or oils of animal or plant origin. Examples of C- I0 -C 22 saturated fatty acids that can be cited include lauric acid, capric acid, decanoic acid, stearic acid, isostearic acid, gadoleic acid, myristic acid and mixtures thereof.
  • Non limiting examples of C 10 -C 22 fatty acids carrying at least one ethylenically unsaturated bond that can be cited are linderic acid, myristoleic acid, palmitoleic acid, oleic acid, petroselenic acid, doeglic acid, erucic acid, linoleic acid, Iinolenic acid, isanic acid, stearodonic acid, arachidonic acid, chypanodonic acid, ricinoleic acid and mixtures thereof.
  • group R can derive from fatty acids selected from palmitoleic acid, oleic acid, petroselenic acid, erucic acid, linoleic acid, Iinolenic acid, ricinoleic acid and mixtures thereof. Oils from which group R can derive include oils of animal or plant origin.
  • Suitable animal oils that can be cited include sperm whale oil, dolphin oil, whale oil, seal oil, sardine oil, herring oil, dogfish oil, cod liver oil; calves' foot oil and beef, pork, horse or sheep fat (tallow).
  • oils of plant origin examples include rapeseed oil, sunflower seed oil, peanut oil, olive oil, walnut oil, com oil, soya oil, linseed oil, hemp oil, grapeseed oil, coprah oil, palm oil, cottonseed oil, babassu oil, jojoba oil, sesame seed oil, castor oil and coriander oil.
  • R preferably derives from rapeseed.
  • group R can derive from products resulting from alcoholysis reactions, more precisely methanolysis of the above oils.
  • n+n', or m is of from 5 to 30, preferably of from 10 to 25.
  • the demulsifying agent has formula (II), with R being a C 12 -C 14 hydrocarbon group, and n+n' being of from 5 to 30, preferably of from 10 to 25, more preferably of from 16 to 25, even more preferably of from 16 to 20.
  • the demulsifying agent can be prepared by a process comprising the following steps: a) reacting a fatty acid R-COOH or a fatty acid ester of formula R-COOR' wherein R' is an alkyl group, preferably a methyl group, with an alkanolamine formula NH 2 -CH 2 -CH 2 -OH (monoethanol amine, «MEA», route for compounds of formula (I)) or NH-(CH 2 -CH 2 -OH) 2 (diethanol amide, «DEA», route for compounds of formula (II)), optionally in the presence of a basic compound, b) ethoxylating by reacting the product obtained at the end of step a) with ethylene oxide.
  • Step a) is carried out in the presence of a fatty acid or fatty acid ester or a mixture of such compounds.
  • fatty acids described in the definition of group R, the esters thereof, can be used and the list will not be repeated here.
  • this first step can advantageously be carried out from the products resulting from alcoholysis reactions (more particularly methanolysis) of oils of animal or plant origin, in particular selected from those mentioned above.
  • Step a) can be carried out in the presence or absence of a basic catalyst.
  • a basic catalyst Preferably, such a compound is employed. More particularly, this latter is selected from alkali metal alcoholates such as sodium methylate, sodium ethylate, potassium methylate or potassium ethylate. It is also possible to use alkali metal hydroxides such as sodium or potassium hydroxide; or alkali metal carbonates such as sodium carbonate or potassium carbonate.
  • the quantity of this catalyst, if present, is normally in the range 0.01 % to 5% by weight with respect to the product of step a).
  • the reaction temperature is generally in the range 5O 0 C to 15O 0 C. It is advantageously higher than the boiling point of the alcohol produced during the reaction to eliminate that alcohol as it appears in the mixture.
  • step b) can carried out under basic conditions, for example by employing a basic catalyst of the type used in step a). It is also possible to envisage said reaction being carried out in the presence of a Lewis acid such as titanium trichloride or boron trifluoride.
  • a Lewis acid such as titanium trichloride or boron trifluoride.
  • the number of moles of ethylene oxide introduced is such that it allows having numbers m or n+n', as mentioned above.
  • the temperature at which the reaction is carried out is normally of between 8O 0 C and 18O 0 C.
  • reaction conditions for example nitrogen
  • a solvent is selected from compounds that are inert under the reaction conditions.
  • Suitable compounds that can be cited are aromatic or non aromatic hydrocarbon solvents such as hexane, toluene or xylene.
  • halogenated solvents such as chloroform, or cyclic or non cyclic ether type solvents such as dibutylether or tetrahydrofuran.
  • steps b) is carried out under basic conditions. More particularly, the quantity of base required for the this step is added at the beginning of the first step. Normally, the amount of base is between O.5%o and 0.7% by weight with respect to the product obtained in step a).
  • the excess base remaining in the medium is preferably neutralized.
  • the reaction medium is brought into contact with an acid that can be selected from organic acids such as carboxylic acids, more particularly acetic acid, for example; or sulphonic acids such as dodecylbenzene sulphonic acid.
  • a mineral acid such as hydrochloric acid or sulphuric acid.
  • the quantity of acid used is such that the pH of a mixture comprising 5 g of product supplemented with 45 g of ethanol and 50 g of water is in the range 8 to 11.
  • the demulsifying agent has preferably a biodegradability of at least 60% according to a respirometric test as defined in OECD Guidelines for testing chemicals 301 B: CO 2 Evolution Test (17 July 1992). The test is often referred to as OECD 301 B".
  • the demulsifying agent has more preferably a biodegradability of at least 70%.
  • the formulation according to the invention comprises the demulsifying agent and metal degreasing agents.
  • the formulation can also comprise water.
  • the amount of water in the formulation can be of from 0 to 70%.
  • the formulation can be in a powder form as well as in a liquid form.
  • the formulation can be diluted in water by the user, to obtain an aqueous composition comprising the formulation, for example in metal working facilities.
  • the formulation comprises degreasing agents, further to the demulsifying compounds.
  • Degreasing agents that can be used in the formulation are known by the one skilled in the art.
  • the formulation can comprise surfactants, and/or alkaline bases, and/or solvents. These ingredients, and mixtures thereof are considered as degreasing agents.
  • the surfactants can be anionic, cationic, amphoteric, non ionic surfactants, or mixtures thereof. Non ionic surfactants are usually preferred.
  • Useful anionic surfactants include:
  • C1O-C16 > alk y' radical
  • R' a C-
  • alkyl sulphates of formula ROSO3M where R represents a C5-C24, preferably C10-C-I8, alkyl or hydroxyalkyl radical, M representing a hydrogen atom or a cation with the same definition as above, and their ethoxylated (EO) and/or propoxylated (PO) derivatives exhibiting an average of 0.5 to 30, preferably of 0.5 to 10, EO and/or PO units;
  • RCONHROSO3M a C2-C22, preferably C6-C20.
  • RI represents a C2-C3 alkyl radical
  • M representing a hydrogen atom or a cation with the same definition as above, and their ethoxylated (EO) and/or propoxylated (PO) derivatives exhibiting an average of 0.5 to 60 EO and/or PO units;
  • the cation being an alkali metal (sodium, potassium, lithium), a substituted or unsubstituted ammonium residue (methyl-, dimethyl-, trimethyl- or tetramethylammonium, dimethylpiperidinium, and the like) or a residue derived from an alkanolamine (monoethanolamine, diethanolamine, triethanolamine, and the like).
  • Useful non ionic surfactants include:
  • polyoxyalkylenated (polyoxyethylenated, polyoxypropylenated or polyoxybutylenated) alkylphenols the alkyl substituent of which is C6-C12, comprising from 5 to 25 oxyalkylene units; mention may be made, by way of example, of Triton X-45, Triton X-114, Triton X-100 or Triton X-102, sold by Rohm & Haas Co.;
  • - polyoxyalkylenated C8-C22 aliphatic alcohols comprising from 1 to 25 oxyalkylene (oxyethylene or oxypropylene) units; mention may be made, by way of example, of Tergitol 15-S-9 or Tergitol 24-L-6 NMW, sold by Union Carbide Corp., Neodol 45-9, Neodol 23-65, Neodol 45-7 or Neodol 45-4, sold by Shell Chemical Co., or Kyro EOB, sold by The Procter & Gamble Co.;
  • amine oxides such as (C10-C18 alkyl)dimethylamine oxides or (C ⁇ -C22 alkoxy)ethyldihydroxyethylamine oxides;
  • the alkaline base can comprises the following compounds, or mixtures thereof:
  • - pH control agent such as a hydroxide, carbonate, sesquicarbonate, or alkali metal or alkaline- earth metal bicarbonate, for example Potassium hydroxide, Sodium Hydroxide or mixtures thereof,
  • - polyphosphates such as a tripolyphosphate, pyrophosphate, orthophosphate or hexametaphosphate of an alkali metal, alkaline-earth metal, N(R 4 + ) type ammonium where R represents hydrogen, a C 1 -C 4 alkyl radical that may optionally contain an oxygen atom,
  • alkali metal silicate or metasilicates such as alkali metal metasilicates, anhydrous or otherwise, or mixtures thereof.
  • the concentration of alkaline base in the aqueous composition after dilution can be of from 1 to 100 g/l, more particularly of from 5 to 20 g/l.
  • the pH of the aqueous composition can be of from 6 to 14, and preferably of above 9.
  • the alkaline base, or further bases or acids, can be used to trigger the pH.
  • the amount of demulsifying agent compared to the sum of the amounts of the surfactants and demulsifying agent is preferably of from 20 to 80% by weight.
  • the amount of demulsifying agent after dilution in water can be for example of from 0.2 g/L (20% of 1 g/L) to 2,4 g/L (80% of 3 g/L). Dilution rates can typically of from 1 to 300 to 1 to 1000.
  • the formulation can also comprise: - hydrotropic electrolytes such as benzenesulphonates, mono- or di-alkyl (Ci-C 4 ) benzene sulphonates, toluene-, xylene- or cumene-sulphonates, alcohols or glycols, phosphate esters,
  • - hydrotropic electrolytes such as benzenesulphonates, mono- or di-alkyl (Ci-C 4 ) benzene sulphonates, toluene-, xylene- or cumene-sulphonates, alcohols or glycols, phosphate esters,
  • - sequestrating agent such as nitriloacetic acid, ethylenediamine tetraacetic acid, ethylenediamine tetramethylphosphonic acid, nitrilotrimethylene phosphonic acid or salts thereof,
  • - buffer agents such as alkanolamines, ethylenediamine, - metal corrosion inhibitors,
  • compositions can especially comprise:
  • anionic or nonionic detergent surface-active agent such as (C8-Ci6)alkylbenzenesulphonates, (C8-C2 ⁇ )a'kyl sulphates, ethoxylated alkylphenols, ethoxylated fatty alcohols, or block polymers of ethylene oxide and of propylene oxide,
  • hydrotropic electrolyte such as benzenesulphonates, mono- or di(Ci-C4)alkylbenzene sulphonates, or toluene-, xylene- or cumenesulphonates
  • hydrotropic agents such as alcohols and glycols
  • sequestering agent such as nitriloacetic acid, ethylenediaminetetraacetic acid, ethylenediaminetetramethylenephosphonic acid, nitrilotrimethylenephosphonic acid or their salts
  • - buffer agents such as alkanolamines, ethylene-diamine, and the like.
  • a formulation in a powder form can comprise:
  • alkylbenzene sulfonates such as sodium alkylbenzene sulfonates, for example sodium dodecylbenzene sulfonate.
  • the invention also relates to a process for degreasing metal wherein the demulsifying agent is used.
  • the process involves treating metal, such as metal parts or plates, with an aqueous composition comprising the formulation diluted in water, and optionally further ingredients.
  • the process for degreasing metal can be used in processes including the following: - Vehicles metal body parts cleaning,
  • the process can comprise the following steps: a) treating oil-soiled metal parts or plates with an aqueous composition comprising the formulation above, to obtain an oil-soiled composition comprising emulsified oil in water, b) subsequently or simultaneously allowing a phase separation of an oil phase comprising the oil, and of an aqueous phase, c) recovering separately the oil phase and the aqueous phase, d) optionally, re-using totally at least one of the recovered phase or ingredients therefrom.
  • step a) treating is performed by dipping the metal parts or plates in an aqueous bath comprising the formulation. Dipping can be performed for example at temperatures of from 45 to 7O 0 C. According other embodiments, step a) treating can be performed by spraying the metal parts or plates with the aqueous composition.
  • Demulsifier 1 compound having formula (II), wherein R is a C 12 -C 14 "coco" group, and n+n' is of about 18.
  • Demulsifier 2 GN 8361 , marketed by Zschimmer & Schwarz, a coco ethoxylated amine, having about 8 EO groups. This is a comparative demulsifier.
  • Formulation 1 2 g/l of demulsifier 1
  • Formulation 2C 2 g/l of demulsifier 2
  • Oily metal panels (panels covered with a 20 ⁇ m thick layer of the oil, oil being applied just before the test) are degreased by dipping 5 minutes in the above described formulations.
  • the compounds according to the invention do not decrease significantly the cleaning.
  • the oil separation from the emulsion is tested by storing 11 in a round neck balloon for 16 hours at 50 0 C. Then quantity of separated oil (demulsification) is visually evaluated in the neck (thickness of the oil layer).
  • the demulsification with formulation 1 and formulation 2C is quite similar.
  • Biodegradability Demulsifier 1 has a biodegradability of 78% as defined by OECD 301 B respirometric test, within 28 days and readily biodegradable.
  • Demulsifier 2 has a biodegradability of lower than 60% as defined by OECD 301 B respirometric test.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Cette invention concerne une formulation de dégraissage de métal comprenant des agents de dégraissage de métal et un agent désémulsionnant, lequel agent désémulsionnant est un composé représenté par une des formules suivantes: R-CO-NH-CH2-CH2-[EO]m-OH (I) ou R-CO-N[CH2-CH2-[EO]n-OH][CH2-CH2-[EO]n'-OH] (II) dans lesquelles R désigne un groupe hydrocarbure C7-C22 saturé ou insaturé, linéaire ou ramifié, comprenant éventuellement au moins un groupe hydroxyl, EO désigne un groupe représenté par la formule -O-CH2-CH2-; m, n et n', identiques ou différents, désignent des nombres moyens différents de 0; n+n' est compris entre 1 et 50; et m est compris entre 1 et 50.
PCT/EP2004/008433 2004-07-27 2004-07-27 Formulation de degraissage de metal comprenant un agent desemulsionnant, utilisation de cet agent et procede de degraissage de metal WO2006010375A1 (fr)

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Application Number Priority Date Filing Date Title
PCT/EP2004/008433 WO2006010375A1 (fr) 2004-07-27 2004-07-27 Formulation de degraissage de metal comprenant un agent desemulsionnant, utilisation de cet agent et procede de degraissage de metal

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PCT/EP2004/008433 WO2006010375A1 (fr) 2004-07-27 2004-07-27 Formulation de degraissage de metal comprenant un agent desemulsionnant, utilisation de cet agent et procede de degraissage de metal

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106191889A (zh) * 2016-08-25 2016-12-07 合肥绿洁环保科技有限公司 一种免水洗的脱脂防锈剂
CN106191888A (zh) * 2016-08-25 2016-12-07 合肥绿洁环保科技有限公司 一种免水洗脱脂防锈剂的制备及其使用方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1916283A1 (de) * 1969-03-29 1970-10-15 Hoechst Ag Mischemulgatoren zur Herstellung von OEl-in-Wasser-Emulsionen
DE2605502A1 (de) * 1976-02-12 1977-08-18 Exquisit Kosmetik Gmbh Fluessiges feinwaschmittel
EP0084411A1 (fr) * 1982-01-07 1983-07-27 Albright & Wilson Limited Composition et méthode pour l'élimination d'une huile hydrocarbonique des surfaces dures
EP0116151A1 (fr) * 1982-12-22 1984-08-22 Henkel Kommanditgesellschaft auf Aktien Procédé pour la régénération ou le recyclage de solutions aqueuses de dégraissage et de nettoyage
WO1996009368A1 (fr) * 1994-09-23 1996-03-28 Church & Dwight Company, Inc. Agent de nettoyage aqueux pour surfaces metalliques

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1916283A1 (de) * 1969-03-29 1970-10-15 Hoechst Ag Mischemulgatoren zur Herstellung von OEl-in-Wasser-Emulsionen
DE2605502A1 (de) * 1976-02-12 1977-08-18 Exquisit Kosmetik Gmbh Fluessiges feinwaschmittel
EP0084411A1 (fr) * 1982-01-07 1983-07-27 Albright & Wilson Limited Composition et méthode pour l'élimination d'une huile hydrocarbonique des surfaces dures
EP0116151A1 (fr) * 1982-12-22 1984-08-22 Henkel Kommanditgesellschaft auf Aktien Procédé pour la régénération ou le recyclage de solutions aqueuses de dégraissage et de nettoyage
WO1996009368A1 (fr) * 1994-09-23 1996-03-28 Church & Dwight Company, Inc. Agent de nettoyage aqueux pour surfaces metalliques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106191889A (zh) * 2016-08-25 2016-12-07 合肥绿洁环保科技有限公司 一种免水洗的脱脂防锈剂
CN106191888A (zh) * 2016-08-25 2016-12-07 合肥绿洁环保科技有限公司 一种免水洗脱脂防锈剂的制备及其使用方法

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