WO2012028542A1 - Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors - Google Patents
Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors Download PDFInfo
- Publication number
- WO2012028542A1 WO2012028542A1 PCT/EP2011/064691 EP2011064691W WO2012028542A1 WO 2012028542 A1 WO2012028542 A1 WO 2012028542A1 EP 2011064691 W EP2011064691 W EP 2011064691W WO 2012028542 A1 WO2012028542 A1 WO 2012028542A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- use according
- group
- acid
- corrosion
- reaction
- Prior art date
Links
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
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
- C10G75/02—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of corrosion inhibitors
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
-
- 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
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
-
- 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
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/141—Amines; Quaternary ammonium compounds
- C23F11/143—Salts of amines
-
- 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
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/145—Amides; N-substituted amides
-
- 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
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/173—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4075—Limiting deterioration of equipment
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
- C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/041—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving a condensation reaction
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/64—Environmental friendly compositions
Definitions
- the present invention relates to the use of a polyesteramine or a polyester polyquaternary ammonium compound as a corrosion inhibitor for metal surfaces, and to a method for protecting a metal surface from corrosion by contacting the metal surface with said corrosion inhibitor.
- Corrosion is often a serious issue in oil- and gas field processes, e.g. in transportation of crude oil, and in oil or gas wells. This could be due to dissolved gases such as carbon dioxide or hydrogen sulfide causing so-called sweet and sour corrosion, respectively, on ferrous metal surfaces.
- Another serious source of corrosion is the often high electrolyte concentrations in the water which is co-produced with the oil and gas.
- severe risks of corrosion are obvious when inorganic or organic acids are used in so-called acid stimulation or fracturing operations encountered in order to increase the productivity of oil and gas wells.
- corrosion inhibitors e.g. in drilling fluids.
- Corrosion problems are also often an issue in downstream processes, such as refineries, when e.g. salts or acid components from crude oils being processed are causing corrosion of ferrous metal.
- Different types of nitrogen-containing compounds such as e. g . fatty am i nes , alkoxylated fatty amines, amidoamines, and quarternary ammonium compounds, are well-known bases for corrosion inhibitor formulations used in various kinds of systems.
- US 5 352 377 and US 5 456 731 disclose reaction products of hydrocarbyl-substituted carboxylic anhydrides, more specifically hydrocarbyl- substituted succinic anhydrides, and aminoalkanols, e.g. ethoxylated fatty alkyl monoamines or ethoxylated fatty alkyl propylenediamines, that can provide effective antiwear, antirust, and corrosion-inhibiting properties in lubricant and fuel applications.
- hydrocarbyl-substituted carboxylic anhydrides more specifically hydrocarbyl- substituted succinic anhydrides
- aminoalkanols e.g. ethoxylated fatty alkyl monoamines or ethoxylated fatty alkyl propylenediamines
- US 5 178 786 relates to corrosion-inhibiting compositions and their use in functional fluids, especially aqueous hydraulic fluids.
- These compositions comprise at least four components A, B, C, and D, where component D is an ester-salt formed by the reaction of an alkyl or alkenyl succinic anhydride with an alkanolamine.
- the preferred alkanolamines are, e.g., dimethylethanolamine, diethylethanolamine, and methylethylethanolamine, and thus the preferred products D are not polymers.
- US 5 034 444 discloses a Theological additive for non-aqueous coating compositions that may be the reaction product of an alkoxylated aliphatic nitrogen-containing compound and an organic polycarboxylic anhydride or acid.
- EP 0 035 263 A2 discloses polyester compounds produced by reaction between a dicarboxylic acid and an alkoxylated tertiary amine and their use as textile softeners.
- US 5 284 495 discloses oligomers/polymers, which can be prepared by polymerising an anhydride, e.g. phthalic anhydride, and long-chain amine containing diols, e.g. ethoxylated octadecylamine.
- US 5 710 110 discloses a drilling fluid composition containing an oil well fluid anti-settling additive, which is a reaction product wherein the reactants are one or more alkoxylated aliphatic amino compounds and an organic polycarboxylic anhydride or acid.
- polyester polyamine or polyester polyquaternary ammonium compounds obtainable by the condensation of a fatty acid, a dicarboxylic acid or a derivative thereof, and an alkanolamine, where the condensation product optionally has been quaternised by a suitable alkylating agent.
- the present invention relates to the use of the aforementioned products as corrosion inhibitors for metal surfaces.
- the present invention relates to a method for protecting a metal surface from corrosion by contacting the metal surface with an effective amount of a corrosion inhibitor as mentioned above.
- the present invention relates to the use of a product obtainable by the condensation of a fatty acid, or mixture of acids, having the formula R 1 COOH (I), wherein R 1 CO is an acyl group having 8 to 24, preferably 12 to 24, more preferably 14 to 24, and most preferably 16-24, carbon atoms, that may be saturated or unsaturated, linear or branched; and a dicarboxylic acid or a derivative thereof having the formula (I la) or (lib) I II (Ha) or
- each x independently is a number between 1 and 5, and ⁇ x on molar average is a number between 2 and 10
- AO is an alkyleneoxy group having 2-4, preferably 2, carbon atoms
- R 4 is a C1-C3 alkyl group or a group [AO] x wherein AO and x have the same meaning as above, or a partial or wholly quaternised derivative thereof; optionally said reaction between the fatty acid, the dicarboxylic acid, and the alkanolamine is followed by a further reaction step wherein part or all of the nitrogen atoms are quaternised by reaction with an alkylating agent R 5 X, wherein R 5 is a hydrocarbyl group, preferably a C1-C4 alkyl group or the benzyl group, and X " is an anion derived from the alkylating agent R 5 X; as a corrosion inhibitor for metal surfaces.
- R 1 , AO, x, R2, and R 4 have the same meaning as above;
- R 5 is a hydrocarbyl group, preferably a C1-C4 alkyl group or the benzyl group, and X " is an anion derived from the alkylating agent R 5 X;
- t is a number 0 or 1 , preferably 1
- p is typically a number within the range 1-15, and is on average at least 1 , preferably at least 2, and most preferably at least 3. The average value of p will depend on the molar ratios of the compounds (I), (lla) or (lib) and (III) in the reaction mixture, as well as on the reaction conditions.
- Suitable examples of fatty acids of formula (I) are 2-ethylhexanoic acid, n-octanoic acid, n-decanoic acid, n-dodecanoic acid, n-tetradecanoic acid, n-hexadecanoic acid, palmitoleic acid, n-octadecanoic acid, oleic acid, linoleic acid, linolenic acid, eicosanoic acid, docosanoic acid, tetracosanoic acid, coco fatty acid, rape seed fatty acid, soya fatty acid, tallow fatty acid, tall oil fatty acid, gadoleic acid and erucic acid.
- the dicarboxylic acid derivative of general formula (lla) or (lib) may be a dicarboxylic acid as such, a dicarboxylic acid chloride, a diester of a dicarboxylic acid, or a cyclic anhydride of a dicarboxylic acid.
- the most suitable derivatives are the dicarboxylic acids and their corresponding cyclic anhydrides.
- dicarboxylic acid derivatives include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, phthalic acid, tetrahydrophthalic acid, maleic acid, malic acid, tartaric acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides.
- Suitable alkanolamines are N-methyl diethanolamine and N-methyl diisopropanolamine, optionally alkoxylated with ethylene oxide, propylene oxide, butylene oxide or mixtures thereof. If more than one alkylene oxide is reacted with the alkanolamine, the different alkylene oxides may be added in blocks in any order, or may be added randomly.
- the alkoxylation may be performed by any suitable method known in the art by using e.g. an alkaline catalyst, such as KOH, or an acid catalyst.
- a suitable method for the preparation of the products which are the subject of the present invention comprises the steps of mixing a compound of formula (I) as defined above with a compound of formula (lla) or (l ib) as defined above and a compound of formula (III) as defined above, effecting an esterification condensation reaction between the compounds in the mixture, adding an alkylating agent to the condensation reaction product, and effecting a quaternisation reaction of the condensation product.
- esterification condensation reactions taking place between the compounds (I), (I la) or (l i b) , and (I I I) are well-known per se in the art.
- the reactions are preferably performed in the presence of an esterification catalyst, such as a Bronstedt or Lewis acid, for example methanesulfonic acid, p-toluenesulfonic acid, citric acid or BF 3 .
- an esterification catalyst such as a Bronstedt or Lewis acid, for example methanesulfonic acid, p-toluenesulfonic acid, citric acid or BF 3 .
- a dicarboxylic acid derivative of formula (lla) wherein D is O-R 4
- the reaction is a transesterification, which alternatively could be performed in the presence of an alkaline catalyst.
- the carboxylic acid (I) may be added as e.g. its methyl ester.
- other conventional techniques known by the person skilled in the art could be used
- the different esterification reactions could be performed in more than one step, e.g. by first condensing the dicarboxylic acid derivative (lla) or (lib) with the alkanolamine (III), and then adding the carboxylic acid (I) in a next step.
- the reactions can take place with or without solvents added. If solvents are present during the reaction, the solvents should be inert to esterification, e.g. toluene or xylene.
- the esterification condensation reaction between the components (I), (lla) or (lib), and (II I) is suitably effected by heating the mixture at a temperature suitably between 120 and 220°C for a period of from 2 to 20 hours, optionally at a reduced pressure of from 5 to 200 mbar.
- the product is a tertiary polyesteramine compound, and when t is 1 , the product is a polyester polyquaternary ammonium compound.
- Quaternisation is a reaction type that is well-known in the art.
- the alkylating agent R 5 X is suitably selected from the group consisting of methylchloride, methylbromide, dimethylsulfate, diethylsulfate, dimethylcarbonate, and benzylchloride, the most preferred alkylating agents being methylchloride, dimethylsulfate, dimethylcarbonate or benzyl chloride.
- the quaternisation may suitably be performed on the condensation product between the fatty acid, alkanolamine, and diacid. Principally, following an alternative synthesis route, the quaternisation of the alkanolamine (III) may be performed as a first step, which would then be followed by an esterification reaction between (I), (I la) or (lib), and quaternised (III). Either a part of, or all of, the nitrogen atoms may be quaternised.
- a reaction product between the tertiary alkanolamine (III) and a dicarboxylic acid derivative (I la) or (lib) may be reacted with an alkylating agent, e.g. methylchloride or dimethylsulfate, to yield a product that is partly or totally quaternised, before reaction with the carboxylic acid (I).
- an alkylating agent e.g. methylchloride or dimethylsulfate
- Quaternisation reactions are normally performed in water or a solvent, such as isopropanol (IPA) or ethanol, or in mixtures thereof.
- solvents could be ethylene glycol monobutyl ether, di(ethylene glycol) monobutyl ether (BDG), and other ethylene and propylene glycols, such as monoethylene glycol (MEG) and diethylene glycol (DEG).
- the reaction temperature of the quaternising reaction is suitably in the range of from 20 to 100°C, preferably at least 40, more preferably at least 50, and most preferably at least 55°C, and preferably at most 90°C.
- the heating is preferably stopped when the amount of basic nitrogen is ⁇ 0.1 mmol/g, as measured by titration with 0.1 M perchloric acid in glacial acetic acid.
- Corrosion inhibiting products where all nitrogen atoms of the product are quaternary are preferred.
- the molar ratio between the fatty acid, or mixture of acids, having the formula R 1 COOH (I) and the alkanolamine (III) in the reaction mixture is suitably 1 : 1.2 to 1 : 10, more preferably 1 :1.5 to 1 :5, still more preferably 1 :2 to 1 :4, and most preferably 1 :2 to 1 :3, and the ratio between the fatty acid (I) and the dicarboxylic acid or derivative (I la) or (lib) is suitably 2: 1 to 1 :8, preferably 1 :1 to 1 :8, more preferably 1 :1.2 to 1 :6, still more preferably 1 :1.5 to 1 :5, even more preferably 1 :1.5 to 1 :4, yet more preferably 1 : 1.5 to 1 :3, and most preferably 1 : 1.5 to 1 :2.5.
- the products of the present invention have been shown by GPC/SEC analysis to consist for > 86% w/w of polymer molecules with two fatty acid units, two or more alkanolamine units, and one or more diacid/acid anhydride units.
- the products of the present invention should preferably consist for > 65% w/w, more preferably for > 75% w/w, and most preferably for > 85% w/w of molecules with two fatty acid units, two or more alkanolamine units, and one or more diacid/acid anhydride units.
- the corrosion inhibitors of the present invention may be used for protection of metal surfaces, preferably ferrous metals or alloys, such as iron and steel, of pipelines, pumps, tanks and other equipment preferably used in oil- and gas fields or refineries in all of the above-mentioned situations.
- the fluid content can vary over wide ranges, e.g. oil cuts may vary from 1 % in field situations to 100% in e.g. refineries, and the composition of the possibly co-transported water can vary a lot as well when it comes to e.g. dissolved solids and salts contents.
- oil cuts may vary from 1 % in field situations to 100% in e.g. refineries
- composition of the possibly co-transported water can vary a lot as well when it comes to e.g. dissolved solids and salts contents.
- the vast majority of seawater has a salinity of 3.1 - 3.8% by weight, being on the average about 3.5% in the world's oceans, but the water in the flow lines, when present, could even have a salt content of up to 7% by weight, e.g. up to 6%, such as up to 4%.
- the water may also be fresh or brackish water with lower salt contents, for example as low as 0.3%, even as low as 0.05% and down to ⁇ 0.01 %; brackish water may exhibit a large variation from time to time having a salt content of about 0.05% up to about 3%.
- the metal surfaces to be protected will be in contact with water of differing salt content, as exemplified above.
- the polymeric esteramine or polymeric quaternary ammonium ester corrosion inhibitors are added to a flowing liquid which may contain both oil and water, at any point in a flow line upstream of the point or line that is intended to be protected.
- the dosage of corrosion inhibitor needed to obtain sufficient protection varies with the application, but dosing is suitably in such an amount that the concentration at the point of protection is between 1 and 2,000 ppm (by weight), preferably between 1 and 500 ppm, and most preferably between 1 and 150 ppm.
- continuous dosage is the preferred use of the compounds of this invention, another possible mode is batch treatment, where the preferred dosage is between 1 and 5,000 ppm.
- polymeric esteramine or polymeric quaternary ammonium ester corrosion inhibitor bases of this invention may also be added to the corrosion-inhibiting compositions in order to e.g. improve handling under different climate conditions or to further improve the performance under different conditions.
- ingredients are organic or inorganic acids, such as acetic acid, citric acid, and hydrochloric acid, in which case the amines will be predominantly present as salts; a dispersing or cleaning surfactant, such as nonionic ethylene oxide adducts; water-miscible solvents, such as methanol, ethanol, isopropanol, butanol or glycols such as butyl diglycol, ethylene glycol monobutyl ether, monoethylene glycol; scale inhibitors; biocides, such as alkylbenzyldimethyl ammonium chloride, dialkyldimethyl ammonium chloride, alkylamidopropyldimethylamine oxides or quaternary ammonium salts, e.g.
- organic or inorganic acids such as acetic acid, citric acid, and hydrochloric acid, in which case the amines will be predominantly present as salts
- a dispersing or cleaning surfactant such as nonionic ethylene oxide a
- alkylbis(hydroxyethyl)methyl quaternary ammonium chloride alkylbis(hydroxyethyl)methyl quaternary ammonium chloride; and other corrosion inhibitors, such as other amines, amides, imidazolines or amphoterics.
- a synergist such as sodium thiosulfate or 2-mercaptoethanol could be added.
- the molecular weights and/or molecular weight ranges given in the examples in the experimental section were determined by the following method: For separation, a SEC (Size Exclusion Chromatography) column was used. This means that porous particles are used to separate molecules of different sizes, and the molecules with the largest space-filling volume (more strictly, hydrodynamic radius) have the shortest retention times. Thus, in essence, in a SEC system the largest molecules elute first and the smallest molecules elute last.
- SEC Size Exclusion Chromatography
- the samples were dissolved in tetrahydrofuran and injected on a GPC/SEC-system (Gel Permeation Chromatography/Size Exclusion Chromatography), and then the fractions collected were analysed by mass spectrometry.
- GPC/SEC-system Gel Permeation Chromatography/Size Exclusion Chromatography
- Tallow fatty acid (Tefacid; 230.1 g, 0.82 mole), methyl diethanolamine (195.3 g, 1.64 mole) from Fluka, and adipic acid (179.7 g, 1.23 mole) from Fluka were added to a round-bottomed flask fitted with a condenser, a thermometer, a heating mantle, a nitrogen inlet, and a mechanical stirrer.
- the reaction mixture was slowly heated to 174°C.
- 150°C the water produced during the reaction started to distil off.
- vacuum was applied gradually in order to more completely remove the water. I n 4h, the endpoint vacuum of 16 mbar was reached.
- the progress of the reaction was monitored by titration for acid value as well as by 1 H-NMR spectroscopy. After 7h at 174°C and 16 mbar the desired product was obtained. The acid value of the product was then 0.183 meq/g. 541 g of product were obtained.
- the product was shown consist for > 86 SEC area-% of molecules with two fatty acid units, two or more alkanolamine units, and one or more diacid/acid anhydride units. Further, the GPC/SEC analysis in combination with fraction analysis using mass spectroscopy reveals that almost all molecule components in the product (> 85% w/w) have a molecular weight > 700.
- a polyester polyquaternary amine was synthesised as follows: In the first step, oleic acid (479.3 g, 1.69 mole), methyl diethanolamine (498.5 g, 4.18 mole) from Fluka, and adipic acid (458.6 g, 3.14 mole) from Fluka were added to a round-bottomed flask fitted with a condenser, a thermometer, a heating mantle, a nitrogen inlet, and a mechanical stirrer. The reaction mixture was slowly heated to 174°C. Commencing at 156°C, the water produced during the reaction started to distil off. After 3h, vacuum was applied gradually in order to more completely remove the water. In 3h, the endpoint vacuum of 37 mbar was reached.
- a polyester polyquaternary amine was synthesised as follows: The first step is described in Example 1.
- Example 4 Corrosion Inhibition performance in brine with inhibitor dosed to a model oil phase
- Procedure Prepare solution and purge with C0 2 until oxygen is less than 10 ppb. Polish electrodes and place them in the electrochemical test cell under a N 2 blanket. Transfer the solution to the test cell under N 2 blanket. Control the temperature using a proportional controller. Switch gas supply to the required gas mixture. Monitor the corrosion rate for at least 4 hours. Inject neat inhibitor using a micropipette and monitor the corrosion rate until stable.
- the corrosion inhibitor is dosed into the kerosene phase and dosages given refer to active corrosion inhibitor (10, 25 and 50 ppm).
- a negative % protection value indicates higher corrosion than the baseline value with no inhibitor added.
- Example 5 Biodegradability It is nowadays a well-established fact that a reasonable biodegradability often is required by society and authorities for man-made organic compounds that are used in applications where they could end up reaching the environment. For certain geographical and/or application areas certain minimum levels of biodegradability are in addition stated by regulatory bodies.
- Compounds of the present invention were tested for biodegradability in seawater, following GLP standards, according to OECD Guideline for testing of chemicals, section 3; Degradation and accumulation, No. 306: biodegradability in seawater, Closed Bottle test. The biodegradation after 28 days for the products synthesised in Example 2 and Example 3 was > 60%. These examples demonstrate the generally good biodegradability of the compounds according to the invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Combustion & Propulsion (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2011298474A AU2011298474B2 (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
BR112013004075-0A BR112013004075B1 (en) | 2010-08-30 | 2011-08-26 | USE OF PRODUCT OBTAINABLE BY REACTING A FATTY ACID OR ACID MIXTURE WITH THE R1COOH FORMULA AND METHOD FOR PROTECTION OF A METAL SURFACE AGAINST CONTACTING THE METAL SURFACE WITH THE PRODUCT OF INHIBITION |
EA201390270A EA024280B1 (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
EP11748949.2A EP2611889B1 (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
CN201180041837.5A CN103080284B (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
US13/819,371 US8940227B2 (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
CA2807646A CA2807646C (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37811510P | 2010-08-30 | 2010-08-30 | |
US61/378,115 | 2010-08-30 | ||
EP10174517.2 | 2010-08-30 | ||
EP10174517 | 2010-08-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012028542A1 true WO2012028542A1 (en) | 2012-03-08 |
Family
ID=42735696
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2011/064691 WO2012028542A1 (en) | 2010-08-30 | 2011-08-26 | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors |
Country Status (8)
Country | Link |
---|---|
US (1) | US8940227B2 (en) |
EP (1) | EP2611889B1 (en) |
CN (1) | CN103080284B (en) |
AU (1) | AU2011298474B2 (en) |
BR (1) | BR112013004075B1 (en) |
CA (1) | CA2807646C (en) |
EA (1) | EA024280B1 (en) |
WO (1) | WO2012028542A1 (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013092440A1 (en) * | 2011-12-19 | 2013-06-27 | Akzo Nobel Chemicals International B.V. | Compositions comprising polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors and chelating agents |
WO2017141118A1 (en) * | 2016-02-16 | 2017-08-24 | Arkema France | Use of alkoxylated amines as collector agents for ore beneficiation |
US10011908B2 (en) | 2013-10-29 | 2018-07-03 | Instituto Mexicano Del Petroleo | Corrosion inhibition composition for pipelines, process of elaboration and synthesis |
US10100146B2 (en) | 2013-12-18 | 2018-10-16 | Akzo Nobel Chemicals International, B.V. | Polyester polyquaternary ammonium compound collectors for reverse froth flotation of silicates from nonsulfidic ores |
FR3119395A1 (en) | 2021-02-04 | 2022-08-05 | Arkema France | POLYESTERAMINES AND POLYESTERQUATS |
WO2022243367A1 (en) | 2021-05-18 | 2022-11-24 | Nouryon Chemicals International B.V. | Polyester polyquats in cleaning applications |
WO2023011800A1 (en) | 2021-08-05 | 2023-02-09 | Clariant International Ltd | Use of complex polyester amines and polyester quaternary ammonium compounds as corrosion inhibitors |
US20230076540A1 (en) * | 2021-08-05 | 2023-03-09 | Ecolab Usa Inc. | Polyamine-polyesters as corrosion inhibition |
US11802179B2 (en) | 2017-08-16 | 2023-10-31 | Arkema France | Polyesteramines and polyesterquats |
US11845892B2 (en) | 2021-08-05 | 2023-12-19 | Clariant International Ltd | Use of complex polyesteramines and polyester polyquaternary ammonium compounds as corrosion inhibitors |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3111919B1 (en) * | 2015-07-02 | 2018-03-21 | Evonik Degussa GmbH | Emulsions containing cationic emulsifiers based on mdipa esterquats |
AU2017205434A1 (en) | 2016-01-06 | 2018-07-05 | Championx Usa Inc. | Temperature-stable paraffin inhibitor compositions |
AU2017205435B2 (en) | 2016-01-06 | 2020-11-19 | Championx Usa Inc. | Temperature-stable paraffin inhibitor compositions |
MX2019010808A (en) | 2017-04-03 | 2019-10-17 | Halliburton Energy Services Inc | Water-soluble corrosion inhibitor for subterranean treatments. |
US10858575B2 (en) * | 2017-06-02 | 2020-12-08 | Championx Usa Inc. | Temperature-stable corrosion inhibitor compositions and methods of use |
WO2020023401A1 (en) * | 2018-07-26 | 2020-01-30 | Halliburton Energy Services, Inc. | Emulsifiers for direct emulsion drilling fluids |
CN109762537A (en) * | 2019-02-27 | 2019-05-17 | 郑州智锦电子科技有限公司 | A kind of preparation method of environment universality Multi-effect oilfield additive |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2638449A (en) * | 1949-12-30 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of fatty acids, dialkanolamines, and alkenyl succinic acid anhydrides |
EP0035263A2 (en) | 1980-03-01 | 1981-09-09 | Henkel Kommanditgesellschaft auf Aktien | Polyester compounds, a process for their preparation, and their use as textile softeners |
US4781730A (en) | 1987-06-05 | 1988-11-01 | The Lubrizol Corporation | Fuel additive comprising a hydrocarbon soluble alkali or alkaline earth metal compound and a demulsifier |
US5034444A (en) | 1988-08-26 | 1991-07-23 | Rheox, Inc. | Rheological additive for coating compositions |
US5178786A (en) | 1989-08-04 | 1993-01-12 | The Lubrizol Corporation | Corrosion-inhibiting compositions and functional fluids containing same |
EP0572881A1 (en) | 1992-05-30 | 1993-12-08 | Hoechst Aktiengesellschaft | Process for the separation of water in oil emulsions |
US5284495A (en) | 1992-09-17 | 1994-02-08 | Mobil Oil Corporation | Oligomeric/polymeric multifunctional additives to improve the low-temperature properties of distillate fuels |
US5352377A (en) | 1993-02-08 | 1994-10-04 | Mobil Oil Corporation | Carboxylic acid/ester products as multifunctional additives for lubricants |
US5456731A (en) | 1993-02-08 | 1995-10-10 | Mobil Oil Corporation | Carboxylic acid/ester products as multifunctional additives for fuels |
US5582792A (en) * | 1995-08-24 | 1996-12-10 | Petrolite Corporation | Corrosion inhibition by ethoxylated fatty amine salts of maleated unsaturated acids |
US5710110A (en) | 1995-05-15 | 1998-01-20 | Rheox, Inc. | Oil well drilling fluids, oil well drilling fluid anti-settling and method of providing anti-setting properties to oil well drilling fluids |
WO1999059958A1 (en) * | 1998-05-20 | 1999-11-25 | The Associated Octel Company Limited | Biodegradable corrosion inhibitors |
US6432895B1 (en) | 1997-10-06 | 2002-08-13 | Cognis Deutschland Gmbh | Detergent mixtures containing oligomeric esterquats |
EP1949963A1 (en) | 2007-01-26 | 2008-07-30 | Cognis IP Management GmbH | Process for the flotation of non-sulfidic minerals and ores |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2689828A (en) | 1952-06-04 | 1954-09-21 | Gulf Oil Corp | Mineral oil compositions |
US3014864A (en) | 1958-03-03 | 1961-12-26 | Petrolite Corp | Process of inhibiting corrosion |
US3123634A (en) | 1961-04-28 | 1964-03-03 | Chzchsocchzchzcoh | |
US3762873A (en) | 1971-02-16 | 1973-10-02 | Petrolite Corp | Corrosion inhibiting method using substituted succinimides |
JPS5815543B2 (en) | 1975-12-26 | 1983-03-26 | 栗田工業株式会社 | Kinzokufushiyokuboushizai |
US4238349A (en) | 1977-11-16 | 1980-12-09 | Malaco Ag | Method and a composition for inhibiting corrosion |
JPS57151700A (en) | 1981-03-13 | 1982-09-18 | Sanyo Chem Ind Ltd | Oil composition for skinpass rolling |
JPS58162697A (en) | 1982-03-23 | 1983-09-27 | Nippon Steel Corp | Water-soluble oil composition for temper rolling |
JPS58198593A (en) | 1982-05-13 | 1983-11-18 | Sanyo Chem Ind Ltd | Water-soluble temper-rolling oil composition |
DE3237109A1 (en) | 1982-10-07 | 1984-04-12 | Basf Ag, 6700 Ludwigshafen | USE OF AMINE SALTS OF MALEINAMID ACIDS AS INHIBITORS AGAINST THE CORROSION OF CO (DOWN ARROW) 2 (DOWN ARROW) AND H (DOWN ARROW) 2 (DOWN ARROW) S IN WATER-IN-OIL EMULSIONS |
DE3676315D1 (en) | 1985-02-04 | 1991-02-07 | Ge Chemicals Inc | METAL WORKING LIQUID COMPOSITION. |
DE3526600A1 (en) | 1985-07-25 | 1987-01-29 | Hoechst Ag | QUATERNAIRE OXALKYLATED POLYCONDENSATES, METHOD FOR THE PRODUCTION AND THEIR USE |
DE3638744A1 (en) | 1986-11-13 | 1988-05-26 | Hoechst Ag | BRANCHED, QUATERNAIRE POLYOXALKYLENE MIXED POLYESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
DE3723068A1 (en) | 1987-07-11 | 1989-01-19 | Hoechst Ag | METHOD FOR PRODUCING POLYCONDENSATION COMPOUNDS FROM OXALKYLATED FATTY AMINES, DIOLES AND ALIPHATIC DICARBONIC ACIDS |
DE3809065A1 (en) | 1988-03-18 | 1989-09-28 | Hoechst Ag | ESTERESTED GLYCIDYL ETHER ADDITION PRODUCTS AND THEIR USE |
US5250225A (en) | 1991-02-04 | 1993-10-05 | Basf Aktiengesellschaft | Ammonium salt of an alkenylsuccinic half-amide and the use thereof as corrosion inhibitor in oil and/or gas production technology |
DE4103262A1 (en) | 1991-02-04 | 1992-08-13 | Basf Ag | ALMONIUM SALTS OF ALKENYLSBERSTIC ACID HALBAMIDES AND THEIR USE AS CORROSION INHIBITORS IN OIL AND / OR GAS PRODUCTION |
US5599777A (en) | 1993-10-06 | 1997-02-04 | The Lubrizol Corporation | Methods of using acidizing fluids in wells, and compositions used therein |
US5599779A (en) | 1996-03-20 | 1997-02-04 | R. T. Vanderbilt Company, Inc. | Synergistic rust inhibitors and lubricating compositions |
US6224642B1 (en) | 1999-11-23 | 2001-05-01 | The Lubrizol Corporation | Additive composition |
US20040102332A1 (en) | 2002-11-25 | 2004-05-27 | Elementis Specialties, Inc. | Compositions for drilling fluids useful to provide flat temperature rheology to such fluids over a wide temperature range and drilling fluids containing such compositions |
DE10307727B3 (en) | 2003-02-24 | 2004-11-11 | Clariant Gmbh | Use of compounds as corrosion and gas hydrate inhibitors with improved water solubility and increased biodegradability and these compounds |
WO2004099350A1 (en) | 2003-04-30 | 2004-11-18 | The Lubrizol Corporation | Ethoxylated surfactants for water in oil emulsions |
US7566744B2 (en) | 2004-12-20 | 2009-07-28 | Nalco Company | Environmentally friendly demulsifiers for crude oil emulsions |
WO2011000895A1 (en) | 2009-07-03 | 2011-01-06 | Akzo Nobel Chemicals International B.V. | Polymeric corrosion inhibitors |
-
2011
- 2011-08-26 WO PCT/EP2011/064691 patent/WO2012028542A1/en active Application Filing
- 2011-08-26 BR BR112013004075-0A patent/BR112013004075B1/en active IP Right Grant
- 2011-08-26 AU AU2011298474A patent/AU2011298474B2/en active Active
- 2011-08-26 CA CA2807646A patent/CA2807646C/en active Active
- 2011-08-26 EP EP11748949.2A patent/EP2611889B1/en active Active
- 2011-08-26 US US13/819,371 patent/US8940227B2/en active Active
- 2011-08-26 CN CN201180041837.5A patent/CN103080284B/en not_active Expired - Fee Related
- 2011-08-26 EA EA201390270A patent/EA024280B1/en not_active IP Right Cessation
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2638449A (en) * | 1949-12-30 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of fatty acids, dialkanolamines, and alkenyl succinic acid anhydrides |
EP0035263A2 (en) | 1980-03-01 | 1981-09-09 | Henkel Kommanditgesellschaft auf Aktien | Polyester compounds, a process for their preparation, and their use as textile softeners |
US4781730A (en) | 1987-06-05 | 1988-11-01 | The Lubrizol Corporation | Fuel additive comprising a hydrocarbon soluble alkali or alkaline earth metal compound and a demulsifier |
US5034444A (en) | 1988-08-26 | 1991-07-23 | Rheox, Inc. | Rheological additive for coating compositions |
US5178786A (en) | 1989-08-04 | 1993-01-12 | The Lubrizol Corporation | Corrosion-inhibiting compositions and functional fluids containing same |
EP0572881A1 (en) | 1992-05-30 | 1993-12-08 | Hoechst Aktiengesellschaft | Process for the separation of water in oil emulsions |
US5284495A (en) | 1992-09-17 | 1994-02-08 | Mobil Oil Corporation | Oligomeric/polymeric multifunctional additives to improve the low-temperature properties of distillate fuels |
US5352377A (en) | 1993-02-08 | 1994-10-04 | Mobil Oil Corporation | Carboxylic acid/ester products as multifunctional additives for lubricants |
US5456731A (en) | 1993-02-08 | 1995-10-10 | Mobil Oil Corporation | Carboxylic acid/ester products as multifunctional additives for fuels |
US5710110A (en) | 1995-05-15 | 1998-01-20 | Rheox, Inc. | Oil well drilling fluids, oil well drilling fluid anti-settling and method of providing anti-setting properties to oil well drilling fluids |
US5582792A (en) * | 1995-08-24 | 1996-12-10 | Petrolite Corporation | Corrosion inhibition by ethoxylated fatty amine salts of maleated unsaturated acids |
US6432895B1 (en) | 1997-10-06 | 2002-08-13 | Cognis Deutschland Gmbh | Detergent mixtures containing oligomeric esterquats |
WO1999059958A1 (en) * | 1998-05-20 | 1999-11-25 | The Associated Octel Company Limited | Biodegradable corrosion inhibitors |
EP1949963A1 (en) | 2007-01-26 | 2008-07-30 | Cognis IP Management GmbH | Process for the flotation of non-sulfidic minerals and ores |
Non-Patent Citations (2)
Title |
---|
MANUELA PAVAN, ANDREW P. WORTH, TATIANA . NETZEVA: "EUR 22327 EN", 2006, INSTITUTE FOR HEALTH AND CONSUMER PROTECTION, article "Review of QSAR Models for Bioconcentration" |
NACE INTERNATIONAL, vol. 46, no. 5, May 2007 (2007-05-01), pages 46 - 51 |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013092440A1 (en) * | 2011-12-19 | 2013-06-27 | Akzo Nobel Chemicals International B.V. | Compositions comprising polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors and chelating agents |
US10011908B2 (en) | 2013-10-29 | 2018-07-03 | Instituto Mexicano Del Petroleo | Corrosion inhibition composition for pipelines, process of elaboration and synthesis |
US10676829B2 (en) | 2013-10-29 | 2020-06-09 | Instituto Mexicano Del Petroleo | Corrosion inhibition composition for pipelines, process of elaboration and synthesis |
US10100146B2 (en) | 2013-12-18 | 2018-10-16 | Akzo Nobel Chemicals International, B.V. | Polyester polyquaternary ammonium compound collectors for reverse froth flotation of silicates from nonsulfidic ores |
WO2017141118A1 (en) * | 2016-02-16 | 2017-08-24 | Arkema France | Use of alkoxylated amines as collector agents for ore beneficiation |
US10744517B2 (en) | 2016-02-16 | 2020-08-18 | Arkema France | Use of alkoxylated amines as collector agents for ore beneficiation |
US11802179B2 (en) | 2017-08-16 | 2023-10-31 | Arkema France | Polyesteramines and polyesterquats |
FR3119395A1 (en) | 2021-02-04 | 2022-08-05 | Arkema France | POLYESTERAMINES AND POLYESTERQUATS |
WO2022167756A1 (en) | 2021-02-04 | 2022-08-11 | Arkema France | Polyesteramines and polyester quats |
WO2022243367A1 (en) | 2021-05-18 | 2022-11-24 | Nouryon Chemicals International B.V. | Polyester polyquats in cleaning applications |
WO2023011800A1 (en) | 2021-08-05 | 2023-02-09 | Clariant International Ltd | Use of complex polyester amines and polyester quaternary ammonium compounds as corrosion inhibitors |
US20230076540A1 (en) * | 2021-08-05 | 2023-03-09 | Ecolab Usa Inc. | Polyamine-polyesters as corrosion inhibition |
US11845892B2 (en) | 2021-08-05 | 2023-12-19 | Clariant International Ltd | Use of complex polyesteramines and polyester polyquaternary ammonium compounds as corrosion inhibitors |
Also Published As
Publication number | Publication date |
---|---|
EA201390270A1 (en) | 2013-10-30 |
AU2011298474A1 (en) | 2013-02-28 |
AU2011298474B2 (en) | 2014-01-16 |
CA2807646A1 (en) | 2012-03-08 |
US20130156638A1 (en) | 2013-06-20 |
CN103080284A (en) | 2013-05-01 |
BR112013004075A2 (en) | 2017-10-31 |
BR112013004075B1 (en) | 2018-07-31 |
CA2807646C (en) | 2018-09-04 |
CN103080284B (en) | 2014-11-05 |
US8940227B2 (en) | 2015-01-27 |
EP2611889B1 (en) | 2014-11-26 |
EP2611889A1 (en) | 2013-07-10 |
EA024280B1 (en) | 2016-09-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2011298474B2 (en) | Use of polyester polyamine and polyester polyquaternary ammonium compounds as corrosion inhibitors | |
EP2449153B1 (en) | Polymeric corrosion inhibitors | |
EP2659028B1 (en) | Polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors | |
WO2006034101A1 (en) | Polymeric quaternary ammonium salts useful as corrosion inhibitors and biocides | |
US11802179B2 (en) | Polyesteramines and polyesterquats | |
CA2723948A1 (en) | New gemini surfactants, obtaining process and use as multifunctional corrosion inhibitors | |
WO2013092440A1 (en) | Compositions comprising polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors and chelating agents | |
US20150024977A1 (en) | Method for inhibiting the plugging of conduits by gas hydrates | |
US11845892B2 (en) | Use of complex polyesteramines and polyester polyquaternary ammonium compounds as corrosion inhibitors | |
EP4381023A1 (en) | Use of complex polyester amines and polyester quaternary ammonium compounds as corrosion inhibitors | |
CN116806171A (en) | Polyesteramine and Polyesterquat |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201180041837.5 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11748949 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011748949 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2807646 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13819371 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2011298474 Country of ref document: AU Date of ref document: 20110826 Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 201390270 Country of ref document: EA |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112013004075 Country of ref document: BR |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01E Ref document number: 112013004075 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112013004075 Country of ref document: BR Kind code of ref document: A2 Effective date: 20130221 |