EP0029529A1 - Produits de réaction d'acides sulfone ou carboxamido carboxyliques avec des alcanolamines et leur utilisation comme inhibiteurs de corrosion pauvres en mousse - Google Patents

Produits de réaction d'acides sulfone ou carboxamido carboxyliques avec des alcanolamines et leur utilisation comme inhibiteurs de corrosion pauvres en mousse Download PDF

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Publication number
EP0029529A1
EP0029529A1 EP80106805A EP80106805A EP0029529A1 EP 0029529 A1 EP0029529 A1 EP 0029529A1 EP 80106805 A EP80106805 A EP 80106805A EP 80106805 A EP80106805 A EP 80106805A EP 0029529 A1 EP0029529 A1 EP 0029529A1
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European Patent Office
Prior art keywords
radical
carbon atoms
alkyl
hydrogen
formula
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EP80106805A
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German (de)
English (en)
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EP0029529B1 (fr
Inventor
Rudi Dr. Widder
Elmar Getto
Albert Dr. Hettche
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BASF SE
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BASF SE
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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
    • C23F11/16—Sulfur-containing compounds
    • C23F11/164—Sulfur-containing compounds containing a -SO2-N group
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/939—Corrosion inhibitor

Definitions

  • the invention relates to reaction products of sulfonic or carbonamido carboxylic acids with alkanolamines. It also relates to the use of these reaction products as water-soluble, low-foaming corrosion inhibitors for the weakly acidic to alkaline range. Finally, it relates to the use of these substances together with reaction products from orthoboric acid with alkanolamines for the technical field mentioned.
  • inhibitors have been proposed for this, especially organic compounds, such as acyl sarcosides, amines, alkanolamines or amides of longer-chain fatty acids (see also “Soaps, Oils, Fats, Waxes” 103, No. 6, pages 167 to 168 (1977)).
  • the subject of DE-PS 900 041 includes Salts of sulfonamidocarboxylic acids or carbonamidocarboxylic acids which are obtained by reacting aliphatic carboxylic acid chlorides or sulfonic acid chlorides with aliphatic aminocarboxylic acids or aromatic aminocarboxylic acids, such as anthranilic acid. They are recommended as anti-corrosion agents.
  • DE-PS 12 98 672 specifically describes reaction products of arylsulfonyl halides with aliphatic aminocarboxylic acids.
  • X denotes -CO- or (mostly) -S0 2 -, R 'is hydrogen or alkyl and Y is hydrogen, a metal or optionally substituted one Ammonium ion.
  • the substances described have good corrosion-inhibiting properties and are also partially low-foaming; However, they are still not fully satisfactory, especially with regard to corrosion protection in saline water.
  • the aim of the invention was to find substances which corrosion protection and low foaming ensure optimal in processes in which iron, iron alloys, aluminum or aluminum alloys as well as copper, zinc or their alloys with water, and especially hard and salzhalti- g em water come into contact .
  • R 1 and R 2 are hydrogen, fluorine, chlorine, bromine, an alkyl or alkoxy radical having 1 to 4 carbon atoms, the sum of the carbon atoms of the radicals R 1 and R 2 not exceeding the number seven, preferably 3,
  • A is a benzene, naphthalene or anthracene radical or a biphenyl system such as the diphenyl, diphenylmethane, diphenyloxide, diphenylsulfide, diphenylsulfoxide or diphenylsulfone radical
  • R 3 is hydrogen, an alkyl radical with not more than 4 carbon atoms, the ⁇ -cyanoethyl radical or a hydroxyalkyl radical having 2 to 4 carbon atoms and R 4 being hydrogen, fluorine, chlorine, bromine, an alkyl or alkoxy radical having 1 to 4 carbon atoms, the hydroxyl radical or the carboxy
  • the acids of the formula I can be obtained by known methods - for example, reference is made to the literature cited in Beilstein. From a technical point of view, however, it is mainly the reaction of aromatic acid halides, preferably the chlorides, with aromatic amino carboxylic acids.
  • the starting products are acid chlorides of the formula III in which R1, R 2 , A and X are defined according to formula I and Hal represents a chlorine, bromine or iodine atom.
  • Aromatics from which the carboxylic acid and (preferably) sulfochlorides are derived are e.g. Benzene, fluorine, chlorine, bromobenzene, toluene, xylene, naphthalene, methyl, dimethylnaphthalenes, anthracene, biphenyl, diphenylmethane, diphenyl oxide, diphenyl sulfoxide or diphenyl sulfone.
  • Preferred acid chlorides are benzenesulfochloride, o- and p-toluenesulfochloride, p-xylenesulfochloride and, of the carboxylic acid chlorides, especially benzoyl chloride, naphthoyl chloride or p-toluenesulfonic acid chloride.
  • R 3 and R 4 are preferably hydrogen atoms, and R 4 is also a carboxyl group, and anthranilic acid (o-aminobenzoic acid), p-aminobenzoic acid and aminobenzene dicarboxylic acids may be mentioned as representatives of the aminocarboxylic acids.
  • Preferred alkanolamines are especially triethanolamine, triisopropanol- or -n-propanolamine, methyl-diethanol- or -isopropanolamine, then simply ethoxylated or propoxylated ethylenediamine per active H atom.
  • the equivalent ratio of amidocarboxylic acid to alkanolamine should be 1: 1 to 1: 4, preferably 1: 1.4 to 1: 2.
  • the reaction which can be carried out by simply combining the reactants with stirring, optionally with cooling of the reaction vessel, produces salts (equivalent ratio 1: 1) and mixtures of the salts with free alkanolamine, which can be used directly as inhibitors.
  • reaction products of orthoboric acid and alkanolamine can be present in the inhibitors.
  • the starting point for their preparation is mono-, di- or trialkanolamines with 2 or 3 carbon atoms per alkanol group or mixtures thereof.
  • the dialkanolamines are preferably chosen from the individual alkanolamines. Mixtures of the type which arise from the alkoxylation of ammonia in the production of alkanolamines are technically particularly valuable. Such a mixture contains dialkanolamine as the main component in addition to smaller proportions of mono- and trialkanolamine.
  • Preferred individual compounds are diethanolamine and diisopropanolamine and mixtures which are formed by ethoxylation or propoxylation of ammonia and which mostly contain diethanolamine or diisopropanolamine.
  • alkanolamines are those which are simply substituted on the nitrogen atom by methyl, ethyl or n or isopropyl groups, e.g. Methyl, ethyl or isopropyl diethanol (diisopropanol) amine or mixtures thereof, which can be obtained by alkoxylation of the corresponding primary amines.
  • the corrosion inhibitors according to the invention can be used in all aqueous systems which come into contact with iron, its alloys (steels), aluminum, its alloys, zinc or copper and their alloys.
  • Examples include Hydraulic fluids, cooling lubricants, neutral to alkaline technical cleaners or mine water, which are particularly hard and salt-rich, and which are used directly in mining as mixing water e.g. are used for hydraulic processes and which have a particularly strong corrosive effect.
  • concentrations of the inhibitors according to the invention vary depending on the area of use and the type of aqueous medium and the metals to be protected. In general, based on the aqueous preparation, 0.01 to 5% by weight is used. Falling below this limit reduces the protective effect; exceeding this does not result in any additional advantages.
  • the concentration should preferably be 0.1 to 3% by weight.
  • the corrosion test was carried out as follows:
  • the corrosion test consists of the gray cast iron filter sample.
  • a petri dish with an inner diameter of approx. 10 cm is used with a suitable lid dish.
  • a black band round filter is placed in the Petri dish.
  • a suitable spoon is used to distribute 5 to 10 g of coarse gray cast iron GG-20 chips onto the filter in such a way that a uniform heap is formed in the middle, which is around 1.5 cm from the edge.
  • the chips have a length of approx. 5 to 8 mm and must be obtained from clean gray cast iron GG-20 material without the use of drilling oil or other cooling lubricants. All fine components must be screened off.
  • r 5 ml of the solution or emulsion to be checked for corrosivity are evenly poured onto the chips with a Meppipette.
  • the pH of the test liquid is registered because it is essential for the assessment. It can be set to a certain standard value, for example 8.5.
  • the lid shell is put on and left for 2 hours under normal laboratory conditions at 23 to 25 ° C and approx. 70% relative air humidity. Then the lid is removed and the filter is briefly inverted and placed on the surface of tap water, which frees it from the chips. Immediately afterwards the filter paper thus freed is sprayed with an indicator solution of the following composition and soaked:
  • the impact method was used based on DIN 53 902.
  • the simple test procedure was sufficient, in which the punch with the perforated plate 30 ml was evenly drawn in and out in 30 s and then carefully pulled out (IG impact method).
  • the foam volume is read on the graduated foam cylinder after 1, 5 and 10 min in ml. Information about temperature, concentration and water hardness are also important.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
EP80106805A 1979-11-24 1980-11-05 Produits de réaction d'acides sulfone ou carboxamido carboxyliques avec des alcanolamines et leur utilisation comme inhibiteurs de corrosion pauvres en mousse Expired EP0029529B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792947418 DE2947418A1 (de) 1979-11-24 1979-11-24 Umsetzprodukte aus sulfon- oder carbonamidocarbonsaeuren mit alkanolaminen und ihre verwendung als schaumarme korrosionsinhibitoren
DE2947418 1979-11-24

Publications (2)

Publication Number Publication Date
EP0029529A1 true EP0029529A1 (fr) 1981-06-03
EP0029529B1 EP0029529B1 (fr) 1983-05-25

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EP80106805A Expired EP0029529B1 (fr) 1979-11-24 1980-11-05 Produits de réaction d'acides sulfone ou carboxamido carboxyliques avec des alcanolamines et leur utilisation comme inhibiteurs de corrosion pauvres en mousse

Country Status (3)

Country Link
US (1) US4344862A (fr)
EP (1) EP0029529B1 (fr)
DE (2) DE2947418A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0142627A1 (fr) * 1983-08-22 1985-05-29 Henkel Kommanditgesellschaft auf Aktien Inhibiteurs de corrosion
EP0341536A1 (fr) * 1988-05-10 1989-11-15 BASF Aktiengesellschaft Mélanges d'acides alkénylsucciniques, d'acides arylsulfonylanthraniliques et d'alcanolamines et leur utilisation comme inhibiteurs la corrosion dans les systèmes aqueux

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3119376A1 (de) 1981-05-15 1982-12-02 Basf Ag, 6700 Ludwigshafen Inhibitoren gegen die korrosion von h(pfeil abwaerts)2(pfeil abwaerts)s und co(pfeil abwaerts)2(pfeil abwaerts) in wasser-in-oel-emulsionen
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
US4584104A (en) * 1984-06-29 1986-04-22 Nalco Chemical Company Silica inhibition: prevention of silica deposition by boric acid/orthorborate ion
US4532047A (en) * 1984-06-29 1985-07-30 Nalco Chemical Company Silica inhibition: prevention of silica deposition by addition of low molecular weight organic compounds
DE3616721A1 (de) * 1986-05-17 1987-11-19 Basf Lacke & Farben Zink- und/oder bleisalze von carbonsaeuren und deren verwendung als korrosionsschutzmittel
US4683081A (en) * 1986-06-27 1987-07-28 Ferro Corporation Aqueous corrosion inhibitor compositions of a half-amide and a dicarboxylic acid amine salt
US5250725A (en) * 1986-11-20 1993-10-05 Elf Sanofi Aromatic acid intermediates
DE3719046A1 (de) * 1987-06-06 1988-12-15 Basf Ag Verwendung von salzen von sulfonamidcarbonsaeuren als korrosionsinhibitoren in waessrigen systemen
DE3732374A1 (de) * 1987-09-25 1989-04-06 Basf Lacke & Farben Zink-, blei- und/oder calciumsalze von carbonsaeuren und deren verwendung als korrosionsschutzmittel
RU2245941C1 (ru) * 2003-07-21 2005-02-10 Закрытое акционерное общество "Опытный завод Нефтехим" Ингибитор кислотной коррозии

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB765018A (en) * 1954-03-11 1957-01-02 Wander Ag Dr A Novel salts of n-benzoyl-ªÐ-amino-salicylic acid and their production
DE2840112A1 (de) * 1977-09-19 1979-03-29 Hoechst Ag Wassermischbare korrosionsschutzmittel

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE900041C (de) 1943-04-22 1953-12-17 Hoechst Ag Korrosionsschutzmittel
US2578725A (en) * 1949-10-20 1951-12-18 Josef M Michel Process of protecting metals against corrosion
BE542184A (fr) * 1954-10-21
DE1298672B (de) * 1967-07-15 1969-07-03 Hoechst Ag Korrosionsverhinderndes Metallbearbeitungsmittel
DE2511400C2 (de) * 1975-03-15 1982-09-23 Basf Ag, 6700 Ludwigshafen Amidosulfocarbonsäuren und deren Salze, Verfahren zu deren Herstellung und deren Verwendung als Korrosionsschutzmittel

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB765018A (en) * 1954-03-11 1957-01-02 Wander Ag Dr A Novel salts of n-benzoyl-ªÐ-amino-salicylic acid and their production
DE2840112A1 (de) * 1977-09-19 1979-03-29 Hoechst Ag Wassermischbare korrosionsschutzmittel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0142627A1 (fr) * 1983-08-22 1985-05-29 Henkel Kommanditgesellschaft auf Aktien Inhibiteurs de corrosion
EP0341536A1 (fr) * 1988-05-10 1989-11-15 BASF Aktiengesellschaft Mélanges d'acides alkénylsucciniques, d'acides arylsulfonylanthraniliques et d'alcanolamines et leur utilisation comme inhibiteurs la corrosion dans les systèmes aqueux

Also Published As

Publication number Publication date
DE2947418A1 (de) 1981-06-04
DE3063538D1 (en) 1983-07-07
EP0029529B1 (fr) 1983-05-25
US4344862A (en) 1982-08-17

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