EP0726335B1 - Compositions inhibitrices de la corrosion contenant un amide de l'acide lactobionique - Google Patents

Compositions inhibitrices de la corrosion contenant un amide de l'acide lactobionique Download PDF

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Publication number
EP0726335B1
EP0726335B1 EP96101716A EP96101716A EP0726335B1 EP 0726335 B1 EP0726335 B1 EP 0726335B1 EP 96101716 A EP96101716 A EP 96101716A EP 96101716 A EP96101716 A EP 96101716A EP 0726335 B1 EP0726335 B1 EP 0726335B1
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EP
European Patent Office
Prior art keywords
lactobionic acid
alkylamides
corrosion
weight
amide
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 - Lifetime
Application number
EP96101716A
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German (de)
English (en)
Other versions
EP0726335A1 (fr
Inventor
Klaus-Günther Gerling
Helge Rau
Kornelia Wendler
Petra Schwarz
Karlheinz Uhlig
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Solvay GmbH
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Solvay Deutschland GmbH
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Filing date
Publication date
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Publication of EP0726335A1 publication Critical patent/EP0726335A1/fr
Application granted granted Critical
Publication of EP0726335B1 publication Critical patent/EP0726335B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or 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
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • 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
    • C10M2215/086—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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • 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
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C10M2215/122—Phtalamic acid
    • 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
    • C10M2215/28—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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • the invention relates to the use of Lactobionic acid N-alkyl amides as anti-corrosion agents.
  • Lactobionic acid amide mixtures are known from EP 0 569 869, by the reaction of lactobionic acid or lactobionic acid derivatives with a fatty amine mixture in a lower Alkyl alcohol can be produced. Because of its surfactant Properties and their favorable foaming behavior can be found in detergent, dishwashing and cleaning agent preparations, in fabric softeners and cosmetic formulations Use.
  • the present invention is based on the object to provide new anti-corrosion agents.
  • lactobionic acid N-alkylamides have a corrosion-inhibiting effect.
  • the object of the invention is thus the use of lactobionic acid-N-alkylamides as anti-corrosion agents.
  • P refers lactobionic acid N-alkylamides, their saturated via the amide function or partially unsaturated alkyl radicals one chain length from Have 8 to 18 carbon atoms used.
  • Lactobionic acid-N-alkylamides used which by the Conversion of lactobionic acid or reactive lactobionic acid derivatives, preferably lactobionic acid lactone, with a primary Fat amine mixture were obtained.
  • Fatty amines can e.g. can be obtained technically from fatty acids by first are converted into their nitriles, which are then converted into amines be reduced.
  • Fatty amine mixtures are preferably used, which are obtained from naturally occurring fatty acid mixtures will. The proportion of unsaturated fatty amines fluctuates in these fatty amine mixtures between approx. 5 and 85% by weight.
  • Lactobionic acid-N-alkylamides from the group lactobionic acid-N-oleylamide, lactobionic acid-N-coconut amide and lactobionic acid-N-tallow amide are particularly preferably used as corrosion inhibitors.
  • These particularly preferred lactobionic acid N-alkylamides can easily be prepared by reacting lactobionic acid or lactobionic acid derivative with the corresponding fatty amine mixtures.
  • So oleylamine is a fatty amine mixture that is derived from a fatty acid mixture derived from sunflower oil and / or soybean oil.
  • a corresponding fatty amine mixture derived from coconut fat is referred to as coconut fatty amine and a corresponding fatty amine mixture derived from tallow is described as tallow amine.
  • coconut fatty amine A corresponding fatty amine mixture derived from coconut fat
  • tallow amine a corresponding fatty amine mixture derived from tallow is described as tallow amine.
  • unsaturated fatty amines In addition to saturated fatty amines, a certain proportion of unsaturated fatty amines is always present in these natural fatty amine mixtures.
  • Oleylamine obtained from sunflower oil contains, for example, about 14% by weight of saturated fatty amines with 12 to 18 carbon atoms and about 85% by weight of unsaturated fatty amines with 14 to 18 carbon atoms.
  • Oleylamine (also called soy amine) obtained from soybean oil contains, for example, approximately 16% by weight of saturated C 16 fatty amines, approximately 15% by weight of saturated C 18 fatty amines and a proportion of approximately 63% by weight unsaturated fatty amines with 14 to 18 carbon atoms.
  • coconut fatty amine contains, for example, approx. 50% by weight of saturated C 12 fatty amines, approx. 18% by weight of saturated C 14 fatty amines, approx. 7% by weight of unsaturated C 18 fatty amines.
  • Tallow amine contains, for example, approximately 29% by weight of saturated C 16 fatty amines, approximately 23% by weight of saturated C 18 fatty amines and a proportion of approximately 42% by weight of unsaturated fatty amines with 14 to 18 carbon atoms.
  • lactobionic acid N-alkylamides in the form of a aqueous solution used.
  • the aqueous solutions of lactobionic acid N-alkylamides can be used alone or in a mixture with others Compounds are used as anti-corrosion agents.
  • the content of lactobionic acid N-alkyl amides, based on the aqueous solution, can be the usual for anti-corrosion agents Concentration range, expediently in the concentration range from 0.1 to 20% by weight, e.g. in the concentration range of 1 to 10% by weight.
  • the pH of aqueous corrosion inhibitors should be below pH 9.0.
  • the anti-corrosion agents according to the invention can be completely clear solutions or, especially in the presence other compounds, finely divided emulsions that can be transparent, opal or even milky cloudy.
  • the inventive Anti-corrosion agents all for anti-corrosion agents usual connections, e.g. Petroleum sulfonates, mineral oils or contain other additives.
  • lactobionic acid N-alkylamides used according to the invention show emulsifying and corrosion-inhibiting effect in mineral oil-containing, aqueous metalworking agents.
  • Another item The invention is therefore the use of lactobionic acid N-alkylamides in metal processing equipment, in particular water-containing metalworking agents. Under Metalworking tools are all used for metalworking usual liquids, especially cooling lubricants, Drilling, cutting and grinding oils, rust removal, paint stripping and Passivation agent understood.
  • Lactobionic acid-N-alkylamides it is possible to use metalworking emulsions to produce which contain a high level of water, without rusting. Besides a good one
  • the corrosion protection agents according to the invention are characterized by corrosion protection due to excellent skin tolerance and high biodegradability.
  • Lactobionic acid-N-alkylamides were made using the shavings / filter paper method determined according to DIN 51360, part 2.
  • lactobionic acid N-oleylamide As described by way of example for lactobionic acid N-oleylamide, the other lactobionic acid amides were also prepared.
  • the anti-corrosion properties were determined in accordance with the DIN standard 51360, part 2.
  • Gray cast iron chips (material DIN 1691-GG30 of approx. 5 mm x mm size) were washed with petroleum ether, through a wire sieve sieved and dried at about 105 ° C in a drying cabinet. After drying was avoided by hand touch.
  • a round filter made of filter paper (diameter 40 mm) was placed in a Petri dish and evenly sprinkled with 2 g ( ⁇ 0.1 g) of the dried chips. The chips were then uniformly wetted with 2 ml of the solution to be examined using a full pipette. The lid of the Petri dish was put on and the Petri dish was left to stand for 2 hours at room temperature. Then the chips were removed from the round filter, the round filter rinsed under running water, swirled in acetone for about 5 seconds and dried at room temperature. Immediately after cleaning and drying the round filter, the degree of corrosion of the corrosion marks on the round filter was determined by visual inspection. The degree of corrosion determined is given in the table below.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (6)

  1. Utilisation de N-alkylamides de l'acide lactobionique comme composition ou produit de protection contre la corrosion et/ou comme additif dans des compositions ou produits pour le travail de transformation de métaux.
  2. Utilisation de N-alkylamides de l'acide lactobionique selon la revendication 1, selon laquelle on utilise des N-alkylamides de l'acide lactobionique comportant des restes alkyles saturés ou partiellement insaturés, reliés par l'intermédiaire de la fonction amide et ayant une longueur de chaíne de 8 à 18 atomes de carbone.
  3. Utilisation de N-alkylamides de l'acide lactobionique selon l'une des revendications 1 et 2, selon laquelle on utilise des N-alkylamides de l'acide lactobionique qui ont été obtenus par réaction de l'acide lactobionique ou de dérivés de l'acide lactobionique avec des amines grasses.
  4. Utilisation de N-alkylamides de l'acide lactobionique selon l'une des revendications 1 à 3, selon laquelle on utilise des N-alkylamides de l'acide lactobionique choisis parmi l'ensemble formé par le N-oléylamide de l'acide lactobionique, le N-cocosamide de l'acide lactobionique, le N-amide de suif de l'acide lactobionique.
  5. Utilisation de N-alkylamides de l'acide lactobionique selon l'une des revendications 1 à 4, selon laquelle on utilise des N-alkylamides de l'acide lactobionique en une quantité de 0,1 à 20% en poids.
  6. Utilisation de N-alkylamides de l'acide lactobionique selon l'une des revendications 1 à 4, selon laquelle on utilise les N-alkylamides de l'acide lactobionique en une quantité de 0,1 à 10% en poids.
EP96101716A 1995-02-13 1996-02-07 Compositions inhibitrices de la corrosion contenant un amide de l'acide lactobionique Expired - Lifetime EP0726335B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19504639A DE19504639A1 (de) 1995-02-13 1995-02-13 Lactobionsäureamide enthaltende Korrosionsschutzmittel
DE19504639 1995-02-13

Publications (2)

Publication Number Publication Date
EP0726335A1 EP0726335A1 (fr) 1996-08-14
EP0726335B1 true EP0726335B1 (fr) 1998-05-06

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP96101716A Expired - Lifetime EP0726335B1 (fr) 1995-02-13 1996-02-07 Compositions inhibitrices de la corrosion contenant un amide de l'acide lactobionique

Country Status (4)

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US (2) US5779939A (fr)
EP (1) EP0726335B1 (fr)
AT (1) ATE165875T1 (fr)
DE (2) DE19504639A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19631959A1 (de) * 1996-08-08 1998-02-12 Solvay Deutschland Lactobionsäureamide enthaltende Korrosionsschutzmittel und Korrosions-Inhibitoren
JP4023079B2 (ja) * 2000-08-31 2007-12-19 株式会社日立製作所 面状照明装置及びこれを備えた表示装置
US8177407B2 (en) 2000-08-31 2012-05-15 Hitachi Displays, Ltd. Plane-like lighting units and display equipment provided therewith
US8136236B2 (en) * 2009-09-15 2012-03-20 John Mezzalingua Associates, Inc. Method for manufacturing a coaxial cable

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2752334A (en) * 1952-03-01 1956-06-26 Nat Dairy Res Lab Inc Nu-substituted lactobionamides
DE1155771B (de) * 1961-07-25 1963-10-17 Akad Wissenschaften Ddr Verfahren zur Herstellung von nichtionogenen Polyoxycarbonsaeure-N-alkylamiden
US3483127A (en) * 1966-06-20 1969-12-09 Lignosol Chem Ltd Nitrogen-containing aldonic acid composition and process of production
US4789553A (en) * 1985-09-23 1988-12-06 American National Can Company Method of thermally processing low-acid foodstuffs in hermetically sealed containers and the containers having the foodstuffs therein
JPH01212781A (ja) * 1988-02-18 1989-08-25 Kurita Water Ind Ltd ボイラ水系用腐食防止剤
US5389279A (en) * 1991-12-31 1995-02-14 Lever Brothers Company, Division Of Conopco, Inc. Compositions comprising nonionic glycolipid surfactants
DE4215478A1 (de) * 1992-05-11 1993-11-18 Solvay Deutschland Lactobionsäureamidzusammensetzungen und deren Verwenndung
US5521293A (en) * 1992-11-25 1996-05-28 Lever Brothers Company, Division Of Conopco, Inc. Heteroatom containing alkyl aldonamide compounds as superior foaming, more soluble nonionic surfactants and a process for their manufacture
US5597514A (en) * 1995-01-24 1997-01-28 Cortec Corporation Corrosion inhibitor for reducing corrosion in metallic concrete reinforcements

Also Published As

Publication number Publication date
US5756003A (en) 1998-05-26
DE19504639A1 (de) 1996-08-14
US5779939A (en) 1998-07-14
DE59600176D1 (de) 1998-06-10
ATE165875T1 (de) 1998-05-15
EP0726335A1 (fr) 1996-08-14

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