[go: up one dir, main page]

WO1992022677A1 - Utilisation de produits de sulfuration d'esters glyceridiques d'acides gras insatures pour l'inhibition d'un debut de developpement d'une corrosion sur des surfaces metalliques - Google Patents

Utilisation de produits de sulfuration d'esters glyceridiques d'acides gras insatures pour l'inhibition d'un debut de developpement d'une corrosion sur des surfaces metalliques Download PDF

Info

Publication number
WO1992022677A1
WO1992022677A1 PCT/EP1992/001209 EP9201209W WO9222677A1 WO 1992022677 A1 WO1992022677 A1 WO 1992022677A1 EP 9201209 W EP9201209 W EP 9201209W WO 9222677 A1 WO9222677 A1 WO 9222677A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
double bonds
unsaturated fatty
fatty acid
acid glyceride
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.)
Ceased
Application number
PCT/EP1992/001209
Other languages
German (de)
English (en)
Inventor
Jürgen Geke
Bernd Stedry
Frank Wangemann
Bernd Fabry
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1992022677A1 publication Critical patent/WO1992022677A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • 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
    • C23F11/16—Sulfur-containing compounds
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C10M135/06—Esters, e.g. fats
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • 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

Definitions

  • the invention relates to the use of sulfonation products of unsaturated fatty acid glyceride esters for inhibiting corrosion on metal surfaces, in particular steel surfaces, and agents containing these sulfonation products.
  • AI rust protection emulsions which contain mineral oil, carboxylic acids and nonionic surfactants of the fatty alcohol polyglycol ether type. However, the latter do not have any corrosion-inhibiting properties, but are the emulsifier component.
  • the object of the invention was to develop substances with corrosion-inhibiting properties which are distinguished by particularly advantageous ecological properties.
  • the invention relates to the use of sulfonation products of unsaturated fatty acid glyceride esters of the formula (I),
  • R 1 CO stands for an unsaturated acyl radical with 16 to 24 carbon atoms and 1 to 5 double bonds
  • R 2 CO and R ⁇ CO independently of one another for acyl radicals with 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, to inhibit corrosion Metal surfaces.
  • the substances to be used according to the invention not only have corrosion-inhibiting properties and good oil solubility, but are largely self-emulsifying in the aqueous phase, so that the use of additional emulsifiers is not absolutely necessary.
  • the invention includes the knowledge that the sulfonation products to be used according to the invention are completely biodegradable.
  • Sulfation products of unsaturated fatty acid glyceride esters are known products that are accessible by the relevant methods of preparative organic chemistry.
  • They are preferably prepared by reacting unsaturated triglycerides with gaseous sulfur trioxide.
  • 1 mol of the glyceride is brought into contact with 0.5 to 2 mol of gaseous sulfur trioxide at temperatures of 50 to 80 ° C.
  • the resulting acidic reaction product is then neutralized in the heat with an aqueous base, with simultaneous hydrolysis of the cyclic sulfonation products formed as by-products in the sulfonation.
  • the neutralization / hydrolysis is preferably carried out with an aqueous 25 to 55% by weight Performed sodium hydroxide solution; Accordingly, the sulfonation products are usually in the form of sodium salts.
  • the sulfonation of unsaturated triglycerides provides a complex mixture, the main components of which are tri- and partial glyceride sulfonates as well as sulfofatty acid soaps with an internal sulfonate group; it can also contain glycerol or glyceride sulfates as well as soaps, alpha-sulfo fatty acid soaps and free glycerin.
  • Unsaturated fatty acid glyceride esters of natural or synthetic origin come into consideration as starting material for the sulfonation products.
  • Fatty acid glyceride esters are primarily triglycerides; In particular in the case of starting materials which are derived from vegetable or animal raw materials, however, small amounts of at most 10% by weight of partial glycerides which do not have a disruptive effect can of course also be present.
  • the term unsaturated fatty acid glyceride esters is further understood only to mean those glycerides which have at least one unsaturated fatty acid in their fatty acid component.
  • R 1 CO represents an unsaturated acyl radical with 16 to 24 carbon atoms and 1 to 5 double bonds
  • R 2 CO and R 3 CO independently of one another represent acyl radicals with 6 to 24 carbon atoms and 0 or 1 to 5 double bonds.
  • R 1 CO can represent, for example, the rest of a palmitoleic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, gadoleic acid, erucic acid, arachidonic acid or clupanodonic acid.
  • the residues of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid or behenic acid are also suitable for R 2 CO and R 3 CO.
  • sulfonation products of unsaturated fatty acid glyceride esters are derived from natural triglycerides based on fats or oils, mixtures of various fatty acids, for example in the C number range from 12 to 18, can also be used as fatty acid components, as is customary in fat chemistry.
  • Sulfation products of unsaturated fatty acid glyceride esters of the formula (I) in which R 1 CO stands for an aliphatic acyl radical with 16 to 18 carbon atoms and 1 or 2 double bonds have proven to be particularly effective in the corrosion inhibition of steel surfaces.
  • Sulfation products of unsaturated fatty acid glyceride esters of the formula (I) in which R 1 CO stands for an aliphatic acyl radical with 16 to 18 carbon atoms and 1 or 2 double bonds and R 2 CO and R 3 CO independently of one another also contain aliphatic acyl radicals are particularly preferred 12 to 18 carbon atoms and 0, 1 or 2 double bonds.
  • products are used which are more recent by sulfonating natural triglycerides, for example sunflower oil
  • Use ratio of triglyceride: SO 3 of 1: 0.5 to 1: 2.0, in particular 1: 1.1 to 1: 1.5, can be obtained.
  • the sulfonation products of unsaturated fatty acid glyceride esters are preferably used in the form of their alkali, alkaline earth, ammonium, amine and alkanolamine salts.
  • the invention further relates to metal treatment compositions comprising a) oil bodies, b) sulfonation products of unsaturated fatty acid glyceride esters of the formula (I),
  • R 1 CO for an unsaturated acyl radical with 16 to 24 carbon atoms and 1 to 5 double bonds
  • R 2 CO and R 3 CO independently of one another for acyl radicals with 6 to 24 carbon atoms and 0 or 1 to 5 double bonds
  • optionally further customary corrosion inhibitors and / or emulsifiers optionally further customary corrosion inhibitors and / or emulsifiers.
  • oil bodies are mineral oils, paraffin oils and / or ester oils, i.e. H. To understand esters of fatty acids with lower aliphatic alcohols or glycerin.
  • the proportion of the oil bodies in the compositions can be 50 to 99, preferably 60 to 90% by weight, based on the compositions.
  • Metal treatment agents with particularly advantageous performance properties are based on sulfonation products of unsaturated fatty acid glyceride esters of the formula (I) in which R 1 CO represents an aliphatic acyl radical having 16 to 18 carbon atoms and 1 or 2 double bonds.
  • those agents are preferred which contain, as component b), sulfonation products of unsaturated fatty acid glyceride esters of the formula (I) in which R 1 CO is an aliphatic acyl radical having 16 to 18 carbon atoms and 1 or 2 double bonds and R 2 CO and R 3 CO independently of one another are aliphatic acyl radicals having 12 to 18 carbon atoms and 0, 1 or 2 double bonds.
  • the agents can contain the sulfonation products of unsaturated fatty acid glyceride esters of the formula (I) in amounts of 1 to 50, preferably 10 to 25% by weight, based on the agents.
  • the agents according to the invention can be further conventional ones Corrosion inhibitors and / or emulsifiers in amounts of 1 to 25, preferably 3 to 10 wt .-% - based on the agent - contain.
  • Typical examples are fatty alcohol polyglycol ether, alkyl phenol polyglycol ether or fatty acids and their ammonium and amine salts.
  • Another object of the invention finally relates to sulfonation products obtainable by unsaturated fatty acid glyceride esters of the formula (I)
  • Carbon atoms and 1 to 5 double bonds and R 2 CO and R 3 CO independently of one another represent acyl radicals having 6 to 24 carbon atoms and 0 or 1 to 5 double bonds, reacted with sulfur trioxide and then neutralizing the acidic reaction products with C 8 -C 22 -alkylamines .
  • alkylamines which can be considered as neutralizing components are octylamine, decylamine, laurylamine, myristylamine, cetylamine, stearylamine, oleylamine, behenylamine and / or erucylamine.
  • the amine salts are distinguished by particularly rapid application to surfaces and advantageous corrosion-inhibiting properties. Industrial applicability
  • the sulfonation products of unsaturated fatty acid glyceride esters to be used according to the invention have corrosion-inhibiting and emulsifying properties and are suitable as corrosion inhibitors in metal treatment agents, for.
  • the metal treatment agents according to the invention can be used as anhydrous concentrates. However, it is also possible to dilute the concentrates on site with water to concentrations of 1 to 50, preferably 2 to 20 and in particular 2 to 5% by weight, based on the composition, or to bring such emulsions directly onto the market.
  • A1 Sulforüböl sodium salt, 45 wt .-% aqueous solution
  • A2 Sulforuböl calcium salt, 55 wt .-% aqueous solution
  • A3 Sulforüböl octylamine salt, 100 wt .-%
  • A4 Sulforüböl stearylamine salt, 100 wt .-%
  • the anionic surfactant content (WAS) as well as the unsulfonated contents (US) were determined according to the DGF standard methods, Stuttgart 1950-1984, H-III-10 and G-II-6b.
  • the condensation water climate test uses the condensation of the air humidity on sample surfaces, whose temperatures due to radiation on the walls of the test chamber are lower than those of the saturated test room air for assessing signs of corrosion.
  • the test was carried out in accordance with DIN 50 017-KTW under the following conditions:
  • Test cycle length 8 h at 40 ° C (door closed)
  • c (inhib) concentration of the inhibitor on average

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Lubricants (AREA)

Abstract

Des produits de sulfuration d'esters glycéridiques d'acides gras insaturés ayant la formule (I) dans laquelle R1CO désigne un reste acyle insaturé de 16 à 24 atomes de carbone et de 1 à 5 doubles liaisons, et R?2CO et R3¿CO désignent, indépendamment l'un de l'autre, des restes acyle de 6 à 24 atomes de carbone et avec 0 ou 1 à 5 doubles liaisons, conviennent pour l'inhibition d'un début de développement d'une corrosion sur des surfaces métalliques.
PCT/EP1992/001209 1991-06-08 1992-06-01 Utilisation de produits de sulfuration d'esters glyceridiques d'acides gras insatures pour l'inhibition d'un debut de developpement d'une corrosion sur des surfaces metalliques Ceased WO1992022677A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4118955.8 1991-06-08
DE4118955A DE4118955A1 (de) 1991-06-08 1991-06-08 Verwendung von sulfierungsprodukten ungesaettigter fettsaeureglyceridester zur inhibierung von korrosionserscheinungen auf metalloberflaechen

Publications (1)

Publication Number Publication Date
WO1992022677A1 true WO1992022677A1 (fr) 1992-12-23

Family

ID=6433544

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/001209 Ceased WO1992022677A1 (fr) 1991-06-08 1992-06-01 Utilisation de produits de sulfuration d'esters glyceridiques d'acides gras insatures pour l'inhibition d'un debut de developpement d'une corrosion sur des surfaces metalliques

Country Status (3)

Country Link
DE (1) DE4118955A1 (fr)
MX (1) MX9202689A (fr)
WO (1) WO1992022677A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863837A (en) * 1955-05-07 1958-12-09 Henkel & Cie Gmbh Corrosion inhibiting bath
EP0327938A1 (fr) * 1988-02-09 1989-08-16 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation de sulfonates d'esters alkyliques inférieurs d'acides gras non saturés
EP0363781A1 (fr) * 1988-10-10 1990-04-18 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation de sels d'alkylester de alpha-sulfoacides gras de couleur claire

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863837A (en) * 1955-05-07 1958-12-09 Henkel & Cie Gmbh Corrosion inhibiting bath
EP0327938A1 (fr) * 1988-02-09 1989-08-16 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation de sulfonates d'esters alkyliques inférieurs d'acides gras non saturés
EP0363781A1 (fr) * 1988-10-10 1990-04-18 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation de sels d'alkylester de alpha-sulfoacides gras de couleur claire

Also Published As

Publication number Publication date
DE4118955A1 (de) 1992-12-10
MX9202689A (es) 1992-12-01

Similar Documents

Publication Publication Date Title
EP0222311B1 (fr) Utilisation d'acides gras alcoyloxy hydroxy substitués comme inhibiteurs de corrosion dans des huiles et des émulsions contenant de l'huile
EP0237959B1 (fr) Mélanges de sels d'ammonium d'acides gras et de polyacides gras respectivement leurs sels alcalins ou d'ammonium solubles dans l'eau, un procédé pour leur préparation et leur utilisation comme inhibiteurs de corrosion dans des systèmes aqueux
DD251748A5 (de) Verfahren zur herstellung von estern der zitronensaeure
DE3710064A1 (de) Verfahren zur herstellung von quaternaeren esteraminen und ihre verwendung
EP0561825A1 (fr) Procede de production en continu de sulfates de glycerides partiels.
CH503100A (de) Verfahren zur Verhinderung der Korrosion durch flüssige Brennstoffe
DE3617550A1 (de) Verwendung von salzen von estern langkettiger fettalkohole mit (alpha)-sulfofettsaeuren
EP0656346A1 (fr) Procédé pour la préparation des solutions des betaines qui sont fluxables et très concentrés
DE3941365A1 (de) Verfahren zur herstellung von salzen sulfierter fettsaeureglycerinester
EP0497849A1 (fr) Procede pour la sulfonation d'esters glyceriques insatures d'acides gras.
EP0677509B1 (fr) Procédé pour la préparation de dispersions aqueuses de bétaines fortement concentrées et fluides
WO1992022677A1 (fr) Utilisation de produits de sulfuration d'esters glyceridiques d'acides gras insatures pour l'inhibition d'un debut de developpement d'une corrosion sur des surfaces metalliques
EP0728176B1 (fr) Procede de fabrication d'alkylesters inferieurs d'acides gras
EP0617732A1 (fr) Procede de fabrication de triglycerides hydrophilises.
EP0786019B1 (fr) Utilisation de sels de guanidine d'acides gras insatures comme principes actifs anticorrosifs
WO1995002714A1 (fr) Agents permettant de nettoyer et de passiver des surfaces metalliques
EP0670828B1 (fr) Graisses sulfitees a teneur reduite en sulfite d'hydrogene libre
DE4323908A1 (de) Verfahren zur Herstellung von O/W-Emulsionen zum Reinigen und Passivieren von Metalloberflächen
DE4240945A1 (de) Korrosionsschutzmittel
EP0975717B1 (fr) Procede de production d'esters d'acide gras sulfates
DE4240153A1 (de) Sulfierte Umesterungspolyole
DE4430084B4 (de) Verfahren zur Herstellung von Betainen
DE4112501A1 (de) Verwendung von sulfierungsprodukten ungesaettigter fettsaeureglycerinester als schaumregulierungsmittel
DE4110179A1 (de) Verfahren zur kontinuierlichen herstellung von waessrigen loesungen anionischer tenside
DE845510C (de) Verfahren zur Herstellung einer Loesung von Petroleumsulfonaten in einem Mineraloel

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU MC NL SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA