EP0127132B1 - Verwendung von Alkenylbernsteinsäurehalbamiden als Korrosionsschutzmittel - Google Patents

Verwendung von Alkenylbernsteinsäurehalbamiden als Korrosionsschutzmittel Download PDF

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Publication number
EP0127132B1
EP0127132B1 EP84105906A EP84105906A EP0127132B1 EP 0127132 B1 EP0127132 B1 EP 0127132B1 EP 84105906 A EP84105906 A EP 84105906A EP 84105906 A EP84105906 A EP 84105906A EP 0127132 B1 EP0127132 B1 EP 0127132B1
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EP
European Patent Office
Prior art keywords
solution
mol
acid
alkenylsuccinic
ammonium salt
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.)
Expired
Application number
EP84105906A
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German (de)
English (en)
French (fr)
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EP0127132A1 (de
Inventor
Werner Dr. Ritschel
Horst Lorke
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Hoechst AG
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Hoechst AG
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Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0127132A1 publication Critical patent/EP0127132A1/de
Application granted granted Critical
Publication of EP0127132B1 publication Critical patent/EP0127132B1/de
Expired legal-status Critical Current

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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
    • 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
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal

Definitions

  • alkyl succinic acids From DE-PS 917 027 it is already known to add hydrocarbon oils as a rust inhibitor to alkyl succinic acids.
  • alkyl succinic acids In water-containing media, however, alkyl succinic acids have the disadvantage of forming insoluble alkaline earth metal salts with the hardness formers of the water and thus precipitating them out, so that they are unsuitable for use as water-soluble corrosion protection agents.
  • DE-AS 1 149 843 also discloses amine salts of amidic acids which are obtained as lubricants by reacting succinic or maleic anhydride with primary alkylamines which contain 4 to 30 carbon atoms in the alkyl chain and then neutralizing with such amines - or fuel additives with rust protection.
  • these compounds are oil-soluble and in most cases not water-soluble; as far as they are water-soluble, they develop much too strong foam or else they lose a large part of their anticorrosive effect with little foam effect.
  • the invention relates to the use of alkenylsuccinic acid halamides of the formulas wherein RC 6 -C, 2- alkenyl and K are a proton or an ammonium ion of the formula NHR 1 R 2 R 3 and R "R 2 and R 3 are identical or different and are hydrogen, Ci-C 12 alkyl, 2-hydroxyethyl or 2-hydroxypropyl.
  • the alkenylsuccinic acid halamides are obtained by reacting 1 mole of an alkenylsuccinic acid anhydride with at least 2 moles of ammonia, the alkenylsuccinic acid halide being obtained in the form of the ammonium salt.
  • the reaction can be carried out in an inert organic solvent such as petroleum ether or toluene with gaseous ammonia, the ammonium salt crystallizing out; the reaction can, however, just as well be carried out with aqueous ammonia, the ammonium salt being obtained in the form of an aqueous solution.
  • the free acid can be prepared from the ammonium salt by reaction with mineral acids.
  • alkanolamine salts particularly the mono-, di- or other alkanolamine salts such as butylethanolamine or isopropanolamine salts, are particularly preferred for use as corrosion inhibitors. These salts are obtained by reacting the ammonium salts initially obtained with an aqueous solution of the alkanolamine at elevated temperatures, ammonia escaping as a gas.
  • the removal of the released ammonia is not necessary, however, as complete a removal of ammonia residues as possible can be indicated due to the unpleasant smell.
  • the ammonia released can be completely removed by heating the aqueous solution of the alkanolammonium salt to 100 ° C. and passing a vigorous stream of nitrogen through the solution.
  • the removal of the ammonia can be supported by additionally distilling off a certain amount of water, and at the same time a certain concentration of the active substance can be set.
  • the alkenylsuccinic acid halamides described above are clearly water-soluble or easily emulsifiable products, which are generally in the form of viscous liquids. These products can be used with particular advantage as anti-corrosion agents in aqueous cooling lubricants, especially drilling, cutting and rolling fluids.
  • aqueous cooling lubricants To prepare these aqueous cooling lubricants, the reaction products are stirred into the required amount of water. It is preferred to use the aqueous solutions directly as they are obtained in the manufacture of these products.
  • the application concentration in the aqueous drilling, cutting and rolling liquids is generally about 0.1 to 10% by weight, preferably 2 to 5% by weight. If necessary, other active ingredients known for this application can also be added.
  • the aqueous anti-corrosion agents are low-foaming, clear aqueous solutions to emulsion-like liquids.
  • octenyl succinic anhydride prepared from octene-1 and maleic anhydride
  • the mixture is stirred for a further 2 hours without cooling and about 170 g of a pale yellow solution are obtained, which contains about 75% of the ammonium salt of octenylsuccinic acid hemamide.
  • tripropenylsuccinic acid prepared by hydrolysis of tripropenylsuccinic anhydride
  • 50 g (0.33 mol) of triethanolamine and 20 g of H 2 0 at 80 ° C. until a clear solution is formed.
  • 95 g of a light yellow solution with an active substance content of about 80% are obtained.
  • tripropenylsuccinic acid 25 g (0.1 mol) tripropenylsuccinic acid are stirred with 15 g (0.25 mol) ethanolamine and 10 g H 2 0 at 80 ° C until a clear solution is formed. 50 g of a clear, 80% solution are obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Lubricants (AREA)
EP84105906A 1983-05-27 1984-05-24 Verwendung von Alkenylbernsteinsäurehalbamiden als Korrosionsschutzmittel Expired EP0127132B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19833319183 DE3319183A1 (de) 1983-05-27 1983-05-27 Verwendung von alkenylbernsteinsaeurehalbamiden als korrosionsschutzmittel
DE3319183 1983-05-27

Publications (2)

Publication Number Publication Date
EP0127132A1 EP0127132A1 (de) 1984-12-05
EP0127132B1 true EP0127132B1 (de) 1986-10-29

Family

ID=6199970

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84105906A Expired EP0127132B1 (de) 1983-05-27 1984-05-24 Verwendung von Alkenylbernsteinsäurehalbamiden als Korrosionsschutzmittel

Country Status (7)

Country Link
US (2) US4609531A (enrdf_load_stackoverflow)
EP (1) EP0127132B1 (enrdf_load_stackoverflow)
JP (1) JPS59229485A (enrdf_load_stackoverflow)
CA (1) CA1220933A (enrdf_load_stackoverflow)
CS (1) CS244138B2 (enrdf_load_stackoverflow)
DE (2) DE3319183A1 (enrdf_load_stackoverflow)
ES (1) ES532809A0 (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7495089B2 (en) 1995-10-23 2009-02-24 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3319183A1 (de) * 1983-05-27 1984-11-29 Hoechst Ag, 6230 Frankfurt Verwendung von alkenylbernsteinsaeurehalbamiden als korrosionsschutzmittel
GB8327911D0 (en) * 1983-10-19 1983-11-23 Ciba Geigy Ag Salts as corrosion inhibitors
DE3341013A1 (de) * 1983-11-12 1985-05-23 Henkel KGaA, 4000 Düsseldorf Bernsteinsaeure-mono-dialkylamide als wasserloesliche korrosionsschutzmittel
DE3501180A1 (de) * 1985-01-16 1986-07-17 Hoechst Ag, 6230 Frankfurt Salze von alkenylbernsteinsaeurehalbamiden, verfahren zu deren herstellung und deren verwendung als korrosionsinhibitoren
DE3534439A1 (de) * 1985-09-27 1987-04-02 Hoechst Ag Verwendung von alkenylbernsteinsaeurehalbamiden als korrosionsschutzmittel
DE3540246A1 (de) * 1985-11-13 1987-05-14 Henkel Kgaa Verwendung von alkoxyhydroxyfettsaeuren als korrosionsinhibitoren in oelen und oelhaltigen emulsionen
US4683081A (en) * 1986-06-27 1987-07-28 Ferro Corporation Aqueous corrosion inhibitor compositions of a half-amide and a dicarboxylic acid amine salt
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
DE3830068A1 (de) * 1988-09-03 1990-04-05 Hoechst Ag Amidoamin-salze von alkenylbernsteinsaeurederivaten, verfahren zu deren herstellung und deren verwendung als korrosionsinhibitoren
EP0394422B1 (en) * 1988-10-24 1994-01-12 Exxon Chemical Patents Inc. Amide containing friction modifier for use in power transmission fluids
EP0464473B1 (de) * 1990-06-23 1994-08-03 Hoechst Aktiengesellschaft Salze von Alkenylbernsteinsäurehalbamiden und deren Verwendung als Korrosionsschutzmittel und Emulgatoren für Metallbearbeitungsöle
US5176848A (en) * 1990-09-28 1993-01-05 Ppg Industries, Inc. Corrosion control composition
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
EP0501368B1 (de) * 1991-02-26 1995-11-29 Hoechst Aktiengesellschaft Verwendung von Alkenylbernsteinsäurehalbamiden
EP0584711B1 (de) * 1992-08-22 1998-02-04 Clariant GmbH Alkenylbernsteinsäurederivate als Metallbearbeitungshilfsmittel
US5401428A (en) * 1993-10-08 1995-03-28 Monsanto Company Water soluble metal working fluids
DE19833894A1 (de) * 1998-07-28 2000-02-03 Fuchs Dea Schmierstoffe Gmbh & Wassermischbares Kühlschmierstoff-Konzentrat

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US2783206A (en) * 1954-03-10 1957-02-26 Tide Water Associated Oil Comp Mineral oil lubricating compositions
US3231587A (en) * 1960-06-07 1966-01-25 Lubrizol Corp Process for the preparation of substituted succinic acid compounds
US3269946A (en) * 1961-08-30 1966-08-30 Lubrizol Corp Stable water-in-oil emulsions
US3230173A (en) * 1962-05-03 1966-01-18 Geigy Chem Corp Method and compositions for inhibiting corrosion
US3256196A (en) * 1963-11-13 1966-06-14 Sinclair Research Inc Amide load carrying agent
US3544467A (en) * 1966-02-07 1970-12-01 Chevron Res Acid-amide pour point depressants
US3324033A (en) * 1966-03-29 1967-06-06 Ethyl Corp Ester-amides of alkenyl succinic anhydride and diethanolamine as ashless dispersants
US3654346A (en) * 1968-06-03 1972-04-04 Petrolite Corp Poly-ester-amide-acids
US3903005A (en) * 1973-11-05 1975-09-02 Texaco Inc Corrosion inhibited compositions
US3965027A (en) * 1974-03-11 1976-06-22 Calgon Corporation Scale inhibition and corrosion inhibition
GB1532836A (en) * 1976-09-09 1978-11-22 Mobil Oil Corp Lubricant compositions
FR2364266A1 (fr) * 1976-09-13 1978-04-07 Mobil Oil Compositions lubrifiantes perfectionnees contenant des sels d'esters partiels d'acides alkyl- ou alcenylsucciniques
IT1098305B (it) * 1978-06-02 1985-09-07 Snam Progetti Antiruggine per sistemi acquosi e composizione lubrificante antiruggine
US4289636A (en) * 1979-10-01 1981-09-15 Mobil Oil Corporation Aqueous lubricant compositions
DE2943963A1 (de) * 1979-10-31 1981-05-14 Basf Ag, 6700 Ludwigshafen Verwendung von alkanolaminsalzen von alkenylbernsteinsaeuren als korrosionsinhibitoren in waessrigen systemen
US4326987A (en) * 1980-02-25 1982-04-27 Petrolite Corporation Reaction products of alkyl and alkenyl succinic acids and ether diamines
US4379063A (en) * 1981-02-20 1983-04-05 Cincinnati Milacron Inc. Novel functional fluid
US4473491A (en) * 1981-06-22 1984-09-25 Basf Aktiengesellschaft Alkanolamine salts of cyclic amide acids and their use as metal corrosion inhibitors in aqueous systems
DE3319183A1 (de) * 1983-05-27 1984-11-29 Hoechst Ag, 6230 Frankfurt Verwendung von alkenylbernsteinsaeurehalbamiden als korrosionsschutzmittel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7495089B2 (en) 1995-10-23 2009-02-24 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions
US7867975B2 (en) 1995-10-23 2011-01-11 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions

Also Published As

Publication number Publication date
CS244138B2 (en) 1986-07-17
JPS59229485A (ja) 1984-12-22
ES8600425A1 (es) 1985-10-01
DE3461108D1 (en) 1986-12-04
US4729841A (en) 1988-03-08
EP0127132A1 (de) 1984-12-05
ES532809A0 (es) 1985-10-01
US4609531A (en) 1986-09-02
CS394284A2 (en) 1985-08-15
JPH0377879B2 (enrdf_load_stackoverflow) 1991-12-11
CA1220933A (en) 1987-04-28
DE3319183A1 (de) 1984-11-29

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