EP0566956A1 - Inhibiteur de corrosion - Google Patents

Inhibiteur de corrosion Download PDF

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Publication number
EP0566956A1
EP0566956A1 EP93105957A EP93105957A EP0566956A1 EP 0566956 A1 EP0566956 A1 EP 0566956A1 EP 93105957 A EP93105957 A EP 93105957A EP 93105957 A EP93105957 A EP 93105957A EP 0566956 A1 EP0566956 A1 EP 0566956A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
weight
alkenyl
ester
succinic acid
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
EP93105957A
Other languages
German (de)
English (en)
Other versions
EP0566956B1 (fr
Inventor
Gernot Dr. Kremer
Horst Lorke
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of EP0566956A1 publication Critical patent/EP0566956A1/fr
Application granted granted Critical
Publication of EP0566956B1 publication Critical patent/EP0566956B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16Ethers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/76Esters containing free hydroxy or carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23FNON-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
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting 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
    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23FNON-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
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting 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
    • C23F11/12Oxygen-containing compounds
    • C23F11/128Esters of carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046Hydroxy ethers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/288Partial esters containing free carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/02Groups 1 or 11
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/22Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01Emulsions, colloids, or micelles

Definitions

  • Corrosion protection agents are used in many areas of metalworking when it comes to protecting the metal parts used from rust.
  • the previously used corrosion protection agents contain constituents such as petroleum sulfonates, salts of alkylsulfonamidocarboxylic acids and amine salts of a partial ester of an alkyl or alkenyl succinic acid.
  • DE-A-26 40 854 discloses lubricant compositions with anti-rust properties based on amine salts of a partial ester of an alkyl or alkenyl succinic acid.
  • Corrosion protection agents based on alkylarylsulfonic acids, alkanolamine and partial esters of an alkyl or alkenyl succinic acid are known from EP-A-336 467.
  • sulfur-containing compounds such as alkylarylsulfonic acids, petroleum sulfonates, salts of alkylsulfonamidocarboxylic acids
  • sulfur-containing compounds can easily be broken down by microorganisms, such as sulfur-reducing bacteria.
  • Nitrogen-containing corrosion protection agents, especially secondary amines, can e.g. are chemically converted into health-endangering nitrosamines.
  • the object of the invention is to provide anti-corrosion agents which are free of amines and which, when used, preclude the formation of substances which are hazardous to health, such as nitrosamines.
  • salts in particular alkali metal and alkaline earth metal salts of alkyl or alkenylsuccinic acid semiesters, can be used as corrosion inhibitors, and a risk from nitrosamines can thus be excluded.
  • the invention relates to corrosion protection agents, characterized by a content of amine-free salt of a half ester of an alkyl or alkenyl succinic acid, the alkyl or alkenyl substituents of which contain 8 to 30 carbon atoms, preferably 9 to 15 carbon atoms.
  • the amine-free salts are obtained by esterification of alkyl- or alkenylsuccinic anhydride with alcohol, preferably in equimolar amounts, optionally with the addition of a catalyst, such as alcoholate solution, at temperatures up to the boiling point of the solution, preferably 20 ° C. to boiling point, particularly preferably 40-80 ° C.
  • a catalyst such as alcoholate solution
  • the reaction is preferably carried out with nitrogen gas.
  • the solution is advantageously stirred at a temperature up to the boiling point of the solution, preferably from 60 ° C. to the boiling point of the solution.
  • the half-esters obtained are mixed with dilute alkali to a pH above 7, preferably up to a pH in the range of 9.
  • the half ester is derived from an alkyl or alkenyl succinic acid in which the alkenyl or alkyl substituent contains 8 to 30 carbon atoms, preferably 9 to 15 carbon atoms.
  • succinic acids are octenyl, dodecenyl, hexadecenyl, isooctadecenyl or triacontenyl succinic acid.
  • the substituent group can also consist of a polyolefinic group, such as a tri, tetra or pentapropenyl group.
  • the alcohol used to form the half ester preferably has 1 to 15 carbon atoms and preferably contains an alkyl alcohol (alkanol) such as methanol, ethanol, propanol or butanol.
  • alkyl alcohol alkanol
  • the lye, which is reacted with the half ester of the substituted succinic acid is preferably an aqueous hydroxide solution, such as sodium hydroxide solution or potassium hydroxide solution.
  • aqueous solutions of polyvalent metal hydroxides, such as alkaline earth metal hydroxides, are also suitable.
  • the aqueous solution of the amine-free salts thus obtained can be used directly as an anti-corrosion agent without further purification of the alkyl or alkenylsuccinic acid.
  • These amine-free salts can be used in the case of aqueous corrosion protection agents, and are preferably used in a concentration of 0.5 to 65% by weight, particularly preferably 1 to 10% by weight, based on the aqueous solution.
  • the pH of the aqueous anticorrosive agent is above pH 7, preferably at a pH of approximately 9.
  • the amine-free salts can also be used in a mixture with other compounds as corrosion inhibitors.
  • Such an anti-corrosion agent consists of, for example 40-80% by weight of a salt of a half ester of an alkyl or alkenyl succinic acid, 30-1% by weight of an oxyethylate of the formula R1 - O - (CH2CH2O) n H, where R1 is C10-C22-alkyl, C10-C22-alkenyl or alkaryl and n is 1 to 10, preferably 1 to 5, 30 - 1 wt .-% fatty acid of the formula R2 - COOH wherein R2 is C10-C20 alkyl or C10-C30 alkenyl and 30-0% by weight of ether carboxylic acid of the formula R3 - O - (CH2CH2O) n - CH2 - COOH, wherein R3 is C10-C22-alkyl, C10-C22-alkenyl or al
  • Such anti-corrosion agents are characterized by complete “solubility" in combination with water. When mixed with water, they form finely divided emulsions that can be clear (transparent) opal or milky.
  • Mixtures of the above-mentioned amine-free salts of the half esters of alkyl or alkenylsuccinic acid with oxethylates, fatty acids and optionally ether carboxylic acids are preferably used with mineral oils, in an amount of up to 70% by weight of mineral oil, based on the total weight, and show good properties as corrosion inhibitors.
  • Suitable mineral oils are mineral oils which consist of paraffins, naphthenes and partly of aromatics and usually have viscosities of 25 to 30 mm2 / s, measured at 20 ° C.
  • aqueous solutions of the amine-free salts of the half esters of alkyl or alkenylsuccinic acid, with oxethylates, fatty acids and optionally ether carboxylic acids and mineral oil are preferably used as corrosion inhibitors, where they show good results especially with regard to good hard water stability.
  • test results listed below show that the amine-free salts according to the invention are effective as anti-corrosion agents.
  • Table 1 shows the corrosion-inhibiting effect of an aqueous alkaline solution of the amine-free salt.
  • Table 2 shows the corrosion-inhibiting effect of a mixture.
  • the corrosion-inhibiting effect was determined using the Herbert test (DIN 51360/1) and the filter paper test (DIN 51360/2).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Lubricants (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
EP93105957A 1992-04-22 1993-04-13 Inhibiteur de corrosion Expired - Lifetime EP0566956B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4213150 1992-04-22
DE4213150 1992-04-22

Publications (2)

Publication Number Publication Date
EP0566956A1 true EP0566956A1 (fr) 1993-10-27
EP0566956B1 EP0566956B1 (fr) 1996-07-31

Family

ID=6457193

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93105957A Expired - Lifetime EP0566956B1 (fr) 1992-04-22 1993-04-13 Inhibiteur de corrosion

Country Status (10)

Country Link
EP (1) EP0566956B1 (fr)
JP (1) JPH0617268A (fr)
AT (1) ATE140982T1 (fr)
BR (1) BR9301612A (fr)
CA (1) CA2094556A1 (fr)
CZ (1) CZ287586B6 (fr)
DE (1) DE59303348D1 (fr)
ES (1) ES2092715T3 (fr)
RU (1) RU2110613C1 (fr)
SK (1) SK36493A3 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0657410A1 (fr) * 1993-12-07 1995-06-14 Hoechst Aktiengesellschaft Procédé pour la préparation d'alkoxylates utilisant des esters comme catalyseurs
WO1996012054A1 (fr) * 1994-10-14 1996-04-25 Henkel Kommanditgesellschaft Auf Aktien Utilisation de sels de guanidine d'acides gras insatures comme principes actifs anticorrosifs
GB2325238A (en) * 1997-03-21 1998-11-18 Castrol Ltd Metalworking fluid containing an alkyl (alk(en)yl) succinate monoester
EP1354905A2 (fr) * 2002-04-18 2003-10-22 Clariant GmbH Procédé de fabrication d'acides ether-carboxyliques à bas point d'écoulement
US8802605B2 (en) 2009-08-07 2014-08-12 Basf Se Lubricant composition
US8802606B2 (en) 2010-08-06 2014-08-12 Basf Se Lubricant composition having improved antiwear properties

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2483099C2 (ru) * 2006-05-23 2013-05-27 Циба Холдинг Инк. Замедляющая коррозию композиция для цветных металлов
MD1025Z (ro) * 2015-09-30 2016-11-30 Институт Химии Академии Наук Молдовы Inhibitor de coroziune a oţelului în apă

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053426A (en) * 1975-03-17 1977-10-11 Mobil Oil Corporation Lubricant compositions
EP0216280A2 (fr) * 1985-09-27 1987-04-01 Hoechst Aktiengesellschaft Utilisation de mono-amides d'acides alcénylsucciniques comme inhibiteurs de corrosion

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053426A (en) * 1975-03-17 1977-10-11 Mobil Oil Corporation Lubricant compositions
EP0216280A2 (fr) * 1985-09-27 1987-04-01 Hoechst Aktiengesellschaft Utilisation de mono-amides d'acides alcénylsucciniques comme inhibiteurs de corrosion

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 10, no. 219 (C-363)(2275) 31. Juli 1986 & JP-A-61 056 287 ( CHIYODA KAGAKU KENKYUSHO K.K ) 20. März 1986 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0657410A1 (fr) * 1993-12-07 1995-06-14 Hoechst Aktiengesellschaft Procédé pour la préparation d'alkoxylates utilisant des esters comme catalyseurs
US5600020A (en) * 1993-12-07 1997-02-04 Hoechst Aktiengesellschaft Process for the preparation of alkoxylates using ester compounds as catalyst
WO1996012054A1 (fr) * 1994-10-14 1996-04-25 Henkel Kommanditgesellschaft Auf Aktien Utilisation de sels de guanidine d'acides gras insatures comme principes actifs anticorrosifs
US5749947A (en) * 1994-10-14 1998-05-12 Henkel Kommanditgesellschaft Auf Aktien Use of guanidinium salts of unsaturated fatty acids as corrosion inhibitors
GB2325238A (en) * 1997-03-21 1998-11-18 Castrol Ltd Metalworking fluid containing an alkyl (alk(en)yl) succinate monoester
EP1354905A2 (fr) * 2002-04-18 2003-10-22 Clariant GmbH Procédé de fabrication d'acides ether-carboxyliques à bas point d'écoulement
EP1354905B1 (fr) * 2002-04-18 2006-01-11 Clariant GmbH Utilisation des acides ether-carboxyliques à bas point d'écoulement
US8802605B2 (en) 2009-08-07 2014-08-12 Basf Se Lubricant composition
US9340745B2 (en) 2009-08-07 2016-05-17 Basf Se Lubricant composition
US8802606B2 (en) 2010-08-06 2014-08-12 Basf Se Lubricant composition having improved antiwear properties

Also Published As

Publication number Publication date
ATE140982T1 (de) 1996-08-15
RU2110613C1 (ru) 1998-05-10
ES2092715T3 (es) 1996-12-01
DE59303348D1 (de) 1996-09-05
SK36493A3 (en) 1993-11-10
JPH0617268A (ja) 1994-01-25
CZ69193A3 (en) 1994-01-19
BR9301612A (pt) 1993-10-26
EP0566956B1 (fr) 1996-07-31
CA2094556A1 (fr) 1993-10-23
CZ287586B6 (en) 2000-12-13

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