EP0237959B1 - Wasserlösliche Mischungen von Fettsäure-Ammonium-Salzen und Polyolfettsäuren bzw. deren Alkali-oder Ammoniumsalzen, Verfahren zu ihrer Herstellung und ihre Verwendung als Korrosionsinhibitoren in wässrigen Systemen - Google Patents

Wasserlösliche Mischungen von Fettsäure-Ammonium-Salzen und Polyolfettsäuren bzw. deren Alkali-oder Ammoniumsalzen, Verfahren zu ihrer Herstellung und ihre Verwendung als Korrosionsinhibitoren in wässrigen Systemen Download PDF

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Publication number
EP0237959B1
EP0237959B1 EP87103577A EP87103577A EP0237959B1 EP 0237959 B1 EP0237959 B1 EP 0237959B1 EP 87103577 A EP87103577 A EP 87103577A EP 87103577 A EP87103577 A EP 87103577A EP 0237959 B1 EP0237959 B1 EP 0237959B1
Authority
EP
European Patent Office
Prior art keywords
general formula
fatty acids
water
salts
mixtures
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
EP87103577A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0237959A1 (de
Inventor
Karl Heinz Dr. Schmid
Alfred Dr. Meffert
Bert Dr. Gruber
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
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Henkel AG and Co KGaA
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Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT87103577T priority Critical patent/ATE57716T1/de
Publication of EP0237959A1 publication Critical patent/EP0237959A1/de
Application granted granted Critical
Publication of EP0237959B1 publication Critical patent/EP0237959B1/de
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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
    • 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

Definitions

  • the invention relates to water-soluble mixtures of fatty acid-ammonium salts and polyol fatty acids or their alkali metal or ammonium salts, a process for their preparation and the use of such mixtures for corrosion inhibition in aqueous systems.
  • the neutralization product of di-n-butylamine with a 1: 1 mixture of caprylic acid and capric acid has a better corrosion-inhibiting effect than the fatty acids neutralized with alkanolamines.
  • the disadvantage of this product is that it smells extremely unpleasant. Due to the large surfaces that are treated with such corrosion inhibitors, there is an unacceptable odor nuisance.
  • the object of the present invention was to provide a water-soluble corrosion protection agent which leads to good corrosion inhibition on metallic surfaces made of iron or iron-containing alloys.
  • the lowest possible foam tendency and water hardness sensitivity had to be ensured and, furthermore, it had to be ensured that no odor nuisance occurred due to the ingredients contained in such agents.
  • the invention also relates to the use of such water-soluble mixtures of fatty acid-ammonium salts and polyol fatty acids and / or their salts for corrosion inhibition in drilling oils, cutting oils, rolling oils, sleeping oils, solutions for metal cleaning, coolants and lubricants.
  • the water-soluble mixtures for corrosion inhibition according to the invention contain one or more ammonium salts of fatty acids of the above-mentioned general formula (I) as one component.
  • the alkyl radicals are therefore the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, and also n-pentyl or n-hexyl and their branched isomers.
  • Suitable hydroxyalkylene radicals are hydroxymethylene or hydroxyethylene radicals or their higher homologues with 3 to 6 carbon atoms in the alkylene radical.
  • Aminoalkylene radicals which can be mentioned are correspondingly aminoomethylene, aminoethylene or aminopropylene radicals or their higher homologs with 4 to 8 C atoms or corresponding aminoalkylene radicals which are substituted on the N atom by C 1-3 alkyl groups.
  • the radical R5 in the general formula (I) represents unbranched and / or branched alkyl radicals having 6 to 10 carbon atoms. Suitable radicals R5 are in particular i-heptyl, i / n-octyl, i-nonyl or n-decyl.
  • the ammonium salts (I) thus originate, for example, from caprylic acid, isononanoic acid or capric acid.
  • ammonium salts of two fatty acids are preferred as the ammonium salt component.
  • Mixtures of two ammonium salts in a weight ratio of 1: 1 have proven particularly useful.
  • Mixtures of ammonium salts (I), which result from the neutralization of a mixture of 50% capric acid and 50% capric acid with amines having 1 to 8 carbon atoms, such as, for example, with di-n-butylamine, have proven particularly advantageous.
  • the water-soluble mixtures according to the invention contain one or more of the ammonium salts of fatty acids with the general formula (I) in amounts of 10 to 90% by weight, based on the total weight of the mixtures according to the invention. Quantities in the range from 10 to 50% by weight are to be regarded as preferred.
  • R6 represents a straight-chain or branched alkyl or alkylene radical having 1 to 19 carbon atoms.
  • m stands for integers in the range from 0 to 18, preferably in the range from 8 to 14.
  • R 6 is n-octyl and m represents 7.
  • the alkoxy radical R 7 O- in the general formula (II) is formed in the course of the process according to the invention described below, in which di- or polyhydroxy compounds of the formula (IV) are added to an epoxide of an unsaturated carboxylic acid (III).
  • the products of the formula (11) also include mixtures of compounds in which two or more Fatty acid molecules are linked together by a di- or polyhydroxy compound of the formula (IV).
  • salts (II) in which M ⁇ represents H ⁇ , their water-soluble salts can also be used.
  • alkali metal salts for example sodium and / or potassium salts, in which M ⁇ is Na ⁇ or K ⁇ , are preferred.
  • salts (II) in which M ⁇ represents an ammonium cation [R i R 2 R 3 R4N] n + , where R 1 , R2, R3, and R4 and n have the meanings given above.
  • One or more polyol fatty acids or their salts of the general formula (II) can be contained in the water-soluble mixtures for corrosion inhibition according to the invention.
  • the total amounts of the compounds (II) mentioned are in the range from 10 to 90% by weight, based on the total weight of the mixtures, preferably in the range from 50 to 90% by weight.
  • unsaturated fatty acids of the general formula (III) or of the di- or polyhydroxy compounds of the formula (IV) also includes unsaturated fatty acids with more than one double bond or di- or polyhydroxy compounds, such as those generally obtained from industrially available oils and fats, such as Soybean oil, linseed oil, rape oil etc. are available.
  • polyol fatty acid or its salts of the general formula (II) obtained in this way is then, if desired, combined with further polyol fatty acids of the general formula mentioned and with one or more ammonium salts of fatty acids with the general formula (I) in a weight ratio of 10: 1 to 1:10, preferably 3: 1, and optionally mixed with water.
  • the water-soluble mixtures according to the invention obtained in this way are outstandingly suitable as agents for inhibiting corrosion in drilling oils, cutting oils, rolling oils, grinding oils, solutions for metal cleaning, coolants and lubricants. It is surprising in the use of such mixtures that polyol fatty acids and their salts of the general formula (11) as such have no corrosion-inhibiting properties. However, in combination with the ammonium salts of fatty acids with the general formula (I), the compounds mentioned have a strong synergistic effect in that they significantly increase their ability to inhibit corrosion on metal surfaces.
  • the concentration of the ammonium salts of fatty acids which as such - as known from the prior art - have corrosion-inhibiting properties by up to 50%, without any deterioration in the corrosion protection.
  • the mixtures according to the invention are also extremely soluble in extremely hard water. This property is also significantly improved in mixtures which, in addition to one or more ammonium salts of fatty acids with the general formula (I), also contain one or more polyol fatty acids and / or their salts of the general formula (II).
  • 150 g of the substance produced according to Example 5 were mixed with 50 g of the neutralizate of 50% by weight of caprylic acid and 50% by weight of capric acid with di-n-butylamine.
  • the commercially available amine salt of a 1: 1 mixture of caprylic acid and capric acid with di-n-butylamine hereinafter referred to as "comparative substance" was used. Its concentration in the application solution was 1 or 2% by weight.
  • the results for corrosion inhibition in the products of Examples 3 and 4 according to the invention are significantly better than in the comparison substance, even in very hard water. Results of the corrosion inhibition that are comparable with the comparison substance are achieved with a reduced use amount of the mixtures according to the invention.
  • Test method 50 ml of a test solution containing 3% of the mixtures according to the invention were shaken ten times in a 100 ml measuring cylinder and the foam volume in ml and the foam disintegration time in min were measured. The results are shown in Table 2 below.
  • the neutralization product of a 1: 1 mixture of caprylic acid and capric acid with di-n-butylamine was again used as the reference substance.
  • Both the product according to Example 4 and that according to Example 3 shows a foam breakdown which is surprisingly rapid for amine soaps in comparison with the comparison substance.
  • the polyol fatty acid in the mixture according to the invention therefore has a synergistic effect on the foam decomposition in the products mentioned.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Detergent Compositions (AREA)
EP87103577A 1986-03-20 1987-03-12 Wasserlösliche Mischungen von Fettsäure-Ammonium-Salzen und Polyolfettsäuren bzw. deren Alkali-oder Ammoniumsalzen, Verfahren zu ihrer Herstellung und ihre Verwendung als Korrosionsinhibitoren in wässrigen Systemen Expired - Lifetime EP0237959B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87103577T ATE57716T1 (de) 1986-03-20 1987-03-12 Wasserloesliche mischungen von fettsaeure-ammonium- salzen und polyolfettsaeuren bzw. deren alkali- oder ammoniumsalzen, verfahren zu ihrer herstellung und ihre verwendung als korrosionsinhibitoren in waessrigen systemen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863609401 DE3609401A1 (de) 1986-03-20 1986-03-20 Wasserloesliche mischungen von fettsaeure-ammonium-salzen und polyolfettsaeuren bzw. deren alkali- oder ammoniumsalzen, verfahren zu ihrer herstellung und ihre verwendung als korrosionsinhibitoren in waessrigen systemen
DE3609401 1986-03-20

Publications (2)

Publication Number Publication Date
EP0237959A1 EP0237959A1 (de) 1987-09-23
EP0237959B1 true EP0237959B1 (de) 1990-10-24

Family

ID=6296852

Family Applications (1)

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EP87103577A Expired - Lifetime EP0237959B1 (de) 1986-03-20 1987-03-12 Wasserlösliche Mischungen von Fettsäure-Ammonium-Salzen und Polyolfettsäuren bzw. deren Alkali-oder Ammoniumsalzen, Verfahren zu ihrer Herstellung und ihre Verwendung als Korrosionsinhibitoren in wässrigen Systemen

Country Status (10)

Country Link
US (1) US4719084A (xx)
EP (1) EP0237959B1 (xx)
JP (1) JPS62235487A (xx)
AT (1) ATE57716T1 (xx)
AU (1) AU586915B2 (xx)
CA (1) CA1275167C (xx)
DE (2) DE3609401A1 (xx)
ES (1) ES2018183B3 (xx)
TR (1) TR22976A (xx)
ZA (1) ZA872073B (xx)

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DE3540246A1 (de) * 1985-11-13 1987-05-14 Henkel Kgaa Verwendung von alkoxyhydroxyfettsaeuren als korrosionsinhibitoren in oelen und oelhaltigen emulsionen
GB8727323D0 (en) * 1987-11-21 1987-12-23 Ciba Geigy Ag Corrosion inhibitor
US5149451A (en) * 1989-02-07 1992-09-22 Henkel Corporation Water soluble salt precoats for wire drawing
US5012662A (en) * 1989-02-07 1991-05-07 Henkel Corporation Water soluble salt precoats for wire drawing
US5081333A (en) * 1989-03-17 1992-01-14 Mitsubishi Denki Kabushiki Kaisha Electric discharge machining fluid with a fatty acid amide additive for rust inhibition
US5573725A (en) * 1989-05-12 1996-11-12 Texaco Inc. Corrosion inhibition system featuring the reaction product of a polythioether polyol and fatty acid
US5174914A (en) * 1991-01-16 1992-12-29 Ecolab Inc. Conveyor lubricant composition having superior compatibility with synthetic plastic containers
ATE180941T1 (de) * 1991-11-22 1999-06-15 Mycogen Corp Neue fettsäuresalze mit herbizider wirkung
DK0624170T3 (da) * 1992-01-31 1999-05-25 Henkel Kgaa Fremgangsmåde til fremstilling af plastmaterialer indeholdende amidgrupper
AU3633895A (en) * 1994-10-13 1996-05-06 Henkel Corporation Defoamer composition and method of using the same
US6008169A (en) * 1996-04-17 1999-12-28 Idemitsu Kosan Co., Ltd. Refrigerator oil composition comprising saturated hydroxy fatty acids and derivatives thereof
US5723418A (en) * 1996-05-31 1998-03-03 Ecolab Inc. Alkyl ether amine conveyor lubricants containing corrosion inhibitors
ATE203048T1 (de) * 1996-05-31 2001-07-15 Ecolab Inc Förderanlageschmiermittel auf basis von alkyletheramin
US6247478B1 (en) 1996-11-15 2001-06-19 Ecolab Inc. Cleaning method for polyethylene terephthalate containers
US6554005B1 (en) 1996-11-15 2003-04-29 Ecolab Inc. Cleaning method for polyethylene terephthalate containers
US5932526A (en) * 1997-06-20 1999-08-03 Ecolab, Inc. Alkaline ether amine conveyor lubricant
US20030176517A1 (en) * 1997-12-17 2003-09-18 Striewski Hans R. Shaped body made from wood particles and a PU bonding agent, use and production thereof
JP4279454B2 (ja) 1998-01-05 2009-06-17 イーコラブ インコーポレイティド 飲料品に適合可能な抗微生物性コンベアー滑剤
DE19846434A1 (de) * 1998-10-08 2000-04-13 Henkel Kgaa Motoreneinlaufmittel
TW508368B (en) * 2000-09-21 2002-11-01 Takahashi Kinzoku Kk Water soluble cutting oil containing electrolytic ions, and apparatus for making the same
DE10060815A1 (de) * 2000-12-07 2002-06-20 Henkel Kgaa Steinverbundplatten
DE10356767A1 (de) * 2003-12-05 2005-07-07 Henkel Kgaa Platten und Formkörper auf Basis von Polyurethanbindemittel
EP1954139A4 (en) 2005-11-22 2011-07-06 Segetis Inc GLYCERYL ETHER COMPOUNDS AND ITS USE
JP5394691B2 (ja) * 2008-08-22 2014-01-22 出光興産株式会社 水溶性金属加工油剤および金属加工用クーラント
US9328278B2 (en) 2013-06-12 2016-05-03 Ashland Licensing And Intellectual Property Llc Extended operation engine coolant composition
US9540558B2 (en) 2013-06-12 2017-01-10 Ashland Licensing And Intellectual Property, Llc Extended operation engine coolant composition
CN109704977A (zh) * 2019-01-28 2019-05-03 中国科学院兰州化学物理研究所 一种油溶性仲铵盐类离子液体及其制备和应用
CN113557222A (zh) * 2019-05-28 2021-10-26 花王株式会社 化合物及组合物
US11702584B2 (en) 2019-05-28 2023-07-18 Kao Corporation Co-surfactant, surfactant composition, and composition for oil recovery
CN113557323A (zh) * 2019-05-28 2021-10-26 花王株式会社 防锈剂、防锈剂组合物、被膜形成材料、被膜、及金属部件
JPWO2020241787A1 (xx) * 2019-05-28 2020-12-03
EP3978106B1 (en) * 2019-05-28 2024-01-31 Kao Corporation Surfactant and surfactant composition
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US4468338A (en) * 1983-06-13 1984-08-28 Purex Corporation Transparent soap composition

Also Published As

Publication number Publication date
EP0237959A1 (de) 1987-09-23
DE3609401A1 (de) 1987-09-24
ATE57716T1 (de) 1990-11-15
US4719084A (en) 1988-01-12
CA1275167C (en) 1990-10-16
AU586915B2 (en) 1989-07-27
DE3765664D1 (de) 1990-11-29
TR22976A (tr) 1988-12-29
AU7040387A (en) 1987-09-24
JPS62235487A (ja) 1987-10-15
ES2018183B3 (es) 1991-04-01
ZA872073B (en) 1987-10-28

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