EP0249162A1 - Verwendung von acylierten 3-Amino-1,2,4-triazolen als Korrosionsinhibitoren für Buntmetalle - Google Patents

Verwendung von acylierten 3-Amino-1,2,4-triazolen als Korrosionsinhibitoren für Buntmetalle Download PDF

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Publication number
EP0249162A1
EP0249162A1 EP87108160A EP87108160A EP0249162A1 EP 0249162 A1 EP0249162 A1 EP 0249162A1 EP 87108160 A EP87108160 A EP 87108160A EP 87108160 A EP87108160 A EP 87108160A EP 0249162 A1 EP0249162 A1 EP 0249162A1
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EP
European Patent Office
Prior art keywords
amino
triazoles
oils
triazole
corrosion
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.)
Withdrawn
Application number
EP87108160A
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German (de)
English (en)
French (fr)
Inventor
Karl-Heinz Dr. Schmid
Josef Dr. Penninger
Hinrich Dr. Möller
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
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Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0249162A1 publication Critical patent/EP0249162A1/de
Withdrawn legal-status Critical Current

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    • 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
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
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    • 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
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    • C10N2040/247—Stainless steel
    • 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 3-acylamino-1,2,4-triazoles and of 1-acyl-3-amino-1,2,4-triazoles and their mixtures as corrosion inhibitors for non-ferrous metals in aqueous systems, oils and oil-containing emulsions.
  • Non-ferrous metals for example copper or zinc, or alloys containing them, such as brass or bronze, are preferred as materials in technology due to their relatively high corrosion resistance.
  • industrial processes in which the surfaces of such metals come into contact with oil or oil-containing aqueous emulsions, possibly under extreme conditions of pressure and temperature, the problem of corrosion of the metal surfaces occurs.
  • Such processes are, for example, large-scale industrial cooling processes, metal surface cleaning and processing processes of the metal surfaces, such as drilling, cutting, rolling, etc.
  • oils or oil-containing emulsions are used without the influence of Water on the metal surface can be completely excluded.
  • the successive corrosion of the metal parts coming into contact with the oils or oil-containing liquids leads to a significant reduction in the life of such systems or to problems in the subsequent treatment of the metal surface.
  • non-ferrous metals are preferably used in the construction of water-carrying systems such as steam generating systems, heating systems, cooling water circuits or other technical systems. These materials are particularly important as condenser tube materials in steam power plants. Despite the relatively good resistance to corrosion, however, it is unavoidable that in the normal state analytically detectable amounts of the high-quality materials, in particular copper, are released into the water flowing through. Traces of copper, in particular, are deposited on downstream cooling water pipes made of steel or other less noble metals or metal alloys and lead to sometimes devastating pitting corrosion.
  • DE-OS 29 34 461 and EP-A 0 025 863 disclose the use of 3-amino-5-alkyl-1.2.4-triazoles for corrosion inhibition of non-ferrous metals in aqueous service water systems. Although these compounds have better application properties than the aforementioned corrosion inhibitors and are also relatively easily accessible.
  • German patent application P 35 19 522.2 describes the use of 1,2,4-triazole derivatives in which the alkyl group is terminally hydroxylated in the 5-position of the heterocyclic ring. Disadvantages of hitherto known triazole derivatives, such as their poor water solubility at acidic pH values, were thereby eliminated. However, the corrosion-inhibiting effect of such compounds fell well short of the requirements.
  • acyl-substituted 3-amino-1,2.4-triazoles have a high corrosion protection effect for non-ferrous metals both in aqueous systems and in oil and oil-containing emulsions and also have other excellent application properties.
  • the invention relates to the use of 3-acylamino-1,2,4-triazoles of the general formula (I) and of 1-acyl-3-amino-1,2,4-triazoles of the general formula (II) in which R is a straight-chain or branched alkyl radical with 1 to 11 carbon atoms or a phenyl radical, and mixtures thereof as corrosion inhibitors for non-ferrous metals in aqueous systems, oils and oil-containing emulsions.
  • Suitable 3-amino-1,2,4-triazole derivatives of the general formulas (I) and (II) are thus, for example, those compounds - or mixtures thereof - which have residues from the group acetyl, propionyl, n-butyryl, n-pentanoyl, n-hexanoyl, n-heptanoyl on the free amino group or on the N atom in the 1-position, N-octanoyl, n-nonanoyl, n-decanoyl, n-undecanoyl, n-dodecanoyl or benzoyl or corresponding branched radicals such as sec-butyryl, 2-ethylhexanoyl or the like.
  • the benzoyl and n-octanoyl radicals are preferred.
  • the 3-acylamino-1,2,4-triazoles (I) or 1-acyl-3-amino-1,2,4-triazoles (II) used according to the invention are prepared by methods known per se. It is thus possible to prepare the 1,2,4-triazole which is amino-substituted in the 3-position of the heterocyclic ring by reacting formic acid with aminoguanidinium hydrogen carbonate. The manufacturing process is described in "Angewandte Chemie" 75, 1160 (1963).
  • a mixture of compounds (I) and (II) is formed in a ratio of approximately 1: 1. This mixture can - depending on the reaction temperature and the acylating reagent used - the compounds (I) and (II) in a ratio of 3: 2 to 2: 3. If, on the other hand, a reaction temperature in the region of room temperature is selected, compound (II), ie an 1-acyl-3-amino-1,2,4-triazole, is formed almost exclusively. On the other hand, by heating the mixture formed to temperatures in the range of approx.
  • compound (II) is rearranged into (I), so that compound (I), ie a 3-acylamino-1, 2, 4-triazole. It is thus possible to control the composition of the mixture or to obtain the individual compounds by the choice of the reaction temperature or by subsequent heating.
  • the compounds of the general formulas (I) and (II) and their mixtures can be used as corrosion inhibitors for non-ferrous metals, in particular for copper and brass, both in aqueous systems and in oil-containing emulsions and oily systems, in all fields of application known to the person skilled in the art , for example in drilling or cutting oils, rolling oils, wire drawing agents, deep-drawing agents, lubricating oils, greases, hydraulic oils, gear oils, cooling water, service water, metal cleaners, cleaners for household and industrial purposes etc.
  • the amount of the corrosion inhibitor according to the invention to be used in each case can vary within wide ranges.
  • the amount of corrosion inhibitor to be used for sufficient corrosion inhibition in cooling water systems is in the range from 0.1 to 5 g / m 3 , while that for copper wire drawing agents, for example 100 g / m 3 and possibly up to several 100 g / m 3 .
  • the 3-amino-1,2,4-triazole derivatives of the general formulas (I) and (II) used according to the invention have the advantage over previously known corrosion inhibitors for non-ferrous metals that they are accessible in chemically simple ways from inexpensive starting materials in high yields and without Use of complex plant parts can be manufactured.
  • Drilling and cutting oils which contain sulfur compounds, for example sulfurized sperm oil or sulfurized olefins, and which are known to those skilled in the art as so-called high-pressure additives.
  • test results can be found in Table 1 below, in which the evaluation of the copper sheets or the amount of copper ions in the solution after the test relates in each case to the 5% strength aqueous solution with the respective corrosion inhibitor.
  • Example 2 The corrosion protection test described in Example 2 was carried out using a substance known from the prior art - as a corrosion inhibitor according to DE-OS 29 34 461. 3-Amino-5- (heptyl- / nonyl-) 1.2.4-triazole was used as reference substance. The result is also shown in Table 1 above.
  • Example 2 The corrosion protection test described in Example 2 was also carried out in the absence of corrosion inhibitors gates for non-ferrous metals. Water was added to the concentrate in the same amount instead of the corrosion inhibitor (0.6 % ).
  • Example 2 The compounds (A) to (C) given in Example 2 were again used as the corrosion inhibitor.
  • the results are shown in Table 2 below, in which the assessment of the copper sheets or the amount of copper ions in the aqueous solution relates to the 5% aqueous solution.
  • Example 2 The corrosion test described in Example 2 was carried out with the concentrate formulation described in Example 3, the 3-amino-5- (heptyl- / nonyl-) 1.2.4-triazole known from the prior art for this purpose being used as the corrosion inhibitor has been. The result is shown in Table 2 above.
  • Example 2 The corrosion test described in Example 2 was carried out with the concentrate described in Example 3, the concentrate containing no corrosion inhibitor. Instead of a corrosion inhibitor (0.6%), additional water was added to the concentrate. The result is also shown in Table 2 above.
  • test water used as a corrosive medium was produced according to DIN 51360/2 and buffered with ammonia / ammonium chloride to a pH of 9.0.
  • the corrosion protection value S was calculated from the weight loss using the following equation: In this equation, a stands for the weight loss of the test sample and b for the weight loss of the blank sample.
  • 3-amino-1,2,4-triazole was used as the reference substance. The result is also shown in Table 3 above. It shows that the effect of the non-acylated 3-amino-1,2,4-triazole is considerably lower.

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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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Lubricants (AREA)
EP87108160A 1986-06-13 1987-06-05 Verwendung von acylierten 3-Amino-1,2,4-triazolen als Korrosionsinhibitoren für Buntmetalle Withdrawn EP0249162A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3620025 1986-06-13
DE19863620025 DE3620025A1 (de) 1986-06-13 1986-06-13 Verwendung von acylierten 3-amino-1,2,4-triazolen als korrosionsinhibitoren fuer buntmetalle

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EP0249162A1 true EP0249162A1 (de) 1987-12-16

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Country Status (5)

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US (1) US4874579A (pt)
EP (1) EP0249162A1 (pt)
JP (1) JPS6310699A (pt)
BR (1) BR8702978A (pt)
DE (1) DE3620025A1 (pt)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0367080A1 (en) * 1988-10-31 1990-05-09 Idemitsu Kosan Company Limited Water-glycol hydraulic fluid
US5302304A (en) * 1990-12-21 1994-04-12 Ethyl Corporation Silver protective lubricant composition
EP0716164A1 (en) * 1994-12-05 1996-06-12 Mitsui Mining & Smelting Co., Ltd. Organic rust-proof treated copper foil
WO1999061683A1 (en) * 1998-05-27 1999-12-02 Solutia Inc. Corrosion inhibiting compositions and aqueous metal working compositions
WO2000006675A1 (de) * 1998-07-28 2000-02-10 Fuchs Petrolub Ag Wassermischbares kühlschmierstoff-konzentrat

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US6585933B1 (en) 1999-05-03 2003-07-01 Betzdearborn, Inc. Method and composition for inhibiting corrosion in aqueous systems
EP1123971A1 (en) * 2000-02-08 2001-08-16 Mobil Oil Francaise Water-soluble copper, copper alloys and non-ferrous metals intermediate cold and hot rolling composition
JP4208856B2 (ja) * 2004-04-28 2009-01-14 キヤノン株式会社 液体吐出ヘッドの製造方法
US20060264341A1 (en) * 2005-05-20 2006-11-23 Culley Scott A Transmission composition
WO2007119400A1 (ja) * 2006-03-31 2007-10-25 Idemitsu Kosan Co., Ltd. 潤滑油添加剤、それを含有する潤滑油組成物、各種低摩擦摺動部材、転がり軸受およびすべり軸受
US20080139422A1 (en) * 2006-12-06 2008-06-12 Loper John T Lubricating Composition
US20080139427A1 (en) * 2006-12-11 2008-06-12 Hutchison David A Lubricating composition
US20080139428A1 (en) * 2006-12-11 2008-06-12 Hutchison David A Lubricating composition
US20080139425A1 (en) * 2006-12-11 2008-06-12 Hutchison David A Lubricating composition
US20080287328A1 (en) * 2007-05-16 2008-11-20 Loper John T Lubricating composition
JP6727649B2 (ja) * 2016-05-24 2020-07-22 理研香料ホールディングス株式会社 金属腐食抑制剤及びそれを用いた金属腐食抑制方法
CN107417850B (zh) * 2017-06-08 2020-01-14 北京东方雨虹防水技术股份有限公司 纯丙乳液及其制备方法和金属屋面用防水防锈涂料

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GB2094776A (en) * 1981-03-11 1982-09-22 Dearborn Chemicals Ltd Prevention of corrosion in aqueous systems

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DE3519522A1 (de) * 1985-05-31 1986-12-04 Henkel KGaA, 4000 Düsseldorf Verwendung von 3-amino-5((omega)-hydroxyalkyl)-1,2,4-triazolen als korrosionsinhibitoren fuer buntmetalle in waessrigen systemen

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US4283296A (en) * 1978-08-21 1981-08-11 Texaco Inc. Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same
GB2094776A (en) * 1981-03-11 1982-09-22 Dearborn Chemicals Ltd Prevention of corrosion in aqueous systems

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0367080A1 (en) * 1988-10-31 1990-05-09 Idemitsu Kosan Company Limited Water-glycol hydraulic fluid
US5302304A (en) * 1990-12-21 1994-04-12 Ethyl Corporation Silver protective lubricant composition
EP0716164A1 (en) * 1994-12-05 1996-06-12 Mitsui Mining & Smelting Co., Ltd. Organic rust-proof treated copper foil
US6071629A (en) * 1994-12-05 2000-06-06 Mitsui Mining & Smelting Co., Ltd. Organic rust-proof treated copper foil
WO1999061683A1 (en) * 1998-05-27 1999-12-02 Solutia Inc. Corrosion inhibiting compositions and aqueous metal working compositions
US6238621B1 (en) 1998-05-27 2001-05-29 Solutia Inc. Corrosion inhibiting compositions
WO2000006675A1 (de) * 1998-07-28 2000-02-10 Fuchs Petrolub Ag Wassermischbares kühlschmierstoff-konzentrat
US6511946B1 (en) 1998-07-28 2003-01-28 Fuchs Petrolub Ag Water-miscible cooling lubricant concentrate

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DE3620025A1 (de) 1987-12-17
JPS6310699A (ja) 1988-01-18
US4874579A (en) 1989-10-17
BR8702978A (pt) 1988-03-08

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