EP0192132A2 - Agent anticorrosif aqueux contenant un sel d'ammonium d'acide 2-benzthiazolylthiocarboxylique - Google Patents
Agent anticorrosif aqueux contenant un sel d'ammonium d'acide 2-benzthiazolylthiocarboxylique Download PDFInfo
- Publication number
- EP0192132A2 EP0192132A2 EP86101564A EP86101564A EP0192132A2 EP 0192132 A2 EP0192132 A2 EP 0192132A2 EP 86101564 A EP86101564 A EP 86101564A EP 86101564 A EP86101564 A EP 86101564A EP 0192132 A2 EP0192132 A2 EP 0192132A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- aqueous
- zolylthiocarboxylic
- benzothia
- agent containing
- 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- Withdrawn
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
- C23F11/165—Heterocyclic compounds containing sulfur as hetero atom
-
- 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
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- 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
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
-
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
-
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
-
- 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
- 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
- cooling lubricants in the form of aqueous mineral oil emulsions are often used.
- Purely aqueous cooling lubricants that do not contain oils are increasingly being used for this purpose.
- These are essentially combinations of salts of organic acids with water-soluble polyadducts, which are obtained by adding ethylene oxide, propylene oxide and / or butylene oxide to compounds having active hydrogen atoms.
- aqueous mineral oil emulsions When using the aqueous mineral oil emulsions as cooling liquids, it is disadvantageous that these emulsions break easily, which is particularly due to thermal influences, to a change in pH or to a change in the electrolyte charge. Consequently, changing these parameters will adversely affect the quality of the emulsions, so that after a certain time the emulsion is no longer usable.
- Another disadvantage of mineral oil emulsions is that their milky appearance makes it difficult to observe the machining process.
- DE-AS 11 49 843 describes additives for fuels and lubricating oils that contain salts of primary, aliphatic amines of some amido acids as rust preventives. From DE-AS 29 22 562 amine salts of dicarboxylic acids are known as rust inhibitors in aqueous systems, the lubricants containing 0.3% to 50% of these rust inhibitors. The use of 2-mercaptobenztriazole as a corrosion protection agent for copper is also known. In addition, the use of benzothiazolylmercapto-dicarboxylic acids as corrosion inhibitors is already known (EP 0 129 506).
- the object of the present invention is to find new compounds which have an anti-corrosion effect, which have no harmful effects on the operating personnel or on the environment and which can be used not only with ferrous metals but also with copper and aluminum.
- the invention thus relates to aqueous anticorrosive agents which contain an ammonium salt of 2-benzothiazolylthiocarboxylic acid of the formula contain, where n is a number from 1 to 6 and M is an organic ammonium ion.
- 2-benzothiazolylthiocarboxylic acids are prepared by reacting 2-mercaptobenzothiazole with M -halocarboxylic acids.
- M -halocarboxylic acids instead of the free mercaptobenzthiazole and the free halocarboxylic acid, it is also possible to use their alkali metal salts.
- the molar ratio of the two starting compounds is approximately 1: 1.
- the reaction is generally carried out at a temperature of 30 to 80 ° C. and for a period of 1 to 4 hours. After the reaction has ended, the mixture is acidified and the free acid obtained is separated off, purified and dried. To prepare the ammonium salts mentioned above, this free acid is then dissolved in an aqueous solution of the desired amine in accordance with the meaning of the symbol M. This solution can then be used directly, but is preferably further diluted with water.
- Suitable organic ammonium ions under the meaning of M are all ammonium ions which are derived from organic amines, in particular those organic ammonium ions which, together with the anion of benzothiazolylthiocarboxylic acid, form salts which are soluble or emulsifiable in water. Particularly noteworthy are the ammonium ions, which are derived from mono-, di- and tri-methylamine, mono-, di- and tri ethylamine, monoisopropylamine, mono- and di-butylamine, 3-methoxypropylamine, trimethylpentamine, mono-, di- and tri-ethanolamine, mono-, di- and tri-isopropanolamine. For economic reasons and because of the better action, salts with the mono-, di- and tri-ethanolamine are preferred.
- aqueous solutions of the salts of 2-benzothiazolylthiocarboxylic acids obtained are clear and also do not change when left to stand for 24 hours. No foam forms and the solutions have excellent corrosion protection for ferrous metals, copper and aluminum.
- solutions of higher concentration with an active substance content of approximately 20 to 50% are first prepared. These commercial forms are then further diluted when used and the finished working solution contains about 0.3 to 5% by weight of active substance.
- aqueous solutions of the ammonium salts of 2-benzothiazolylthiocarboxylic acids are generally suitable as anti-corrosion agents for ferrous metals, copper and aluminum, in particular for cooling circuits, hydraulic liquids and preferably for aqueous cooling lubricants in metal processing.
- all of these functional fluids also contain the usual active substances necessary for the respective purpose.
- the respective composition of these functional fluids is sufficiently known to the person skilled in the art and does not require any further explanation here.
- the reaction is continued for a further 2 hours in the temperature range between 40 and 50 ° C.
- the water / methanol ratio is 1: 1.
- the solution is then acidified with hydrochloric acid or acetic acid until a pH between 1 and 3 is reached.
- reaction is continued for two hours at a temperature of 60-70 ° C, then acidified with hydrochloric acid until no more precipitations occur.
- 2-Benzthiazolylthiopropionic acid is obtained as a white powder which, after cleaning and drying, has a melting point of 145-147 ° C.
- the corrosion test on copper and aluminum was carried out as follows. In four test tubes with 100 cc. 1.5 g of mixtures A, B, C and D are added to water and copper foils or aluminum foils according to DIN 1791 - E-CU 57 F30 with the dimensions 2 x 12 x 75 mm are immersed in these solutions. The test tubes are closed and Leave at 20 ° C for 20 days. At the end of the experiment, the color taken up by the solution is observed:
Landscapes
- 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)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1956285 | 1985-02-19 | ||
IT19562/85A IT1185511B (it) | 1985-02-19 | 1985-02-19 | Agenti anticorrosivi acquosi contenenti un sale ammonico dell'acido 2-benzotiazoliltiocarbossilico |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0192132A2 true EP0192132A2 (fr) | 1986-08-27 |
EP0192132A3 EP0192132A3 (fr) | 1988-06-08 |
Family
ID=11159084
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86101564A Withdrawn EP0192132A3 (fr) | 1985-02-19 | 1986-02-06 | Agent anticorrosif aqueux contenant un sel d'ammonium d'acide 2-benzthiazolylthiocarboxylique |
Country Status (4)
Country | Link |
---|---|
US (1) | US4741847A (fr) |
EP (1) | EP0192132A3 (fr) |
JP (1) | JPS61190083A (fr) |
IT (1) | IT1185511B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2765595A1 (fr) * | 1997-07-01 | 1999-01-08 | Lorraine Laminage | Composition pour protection temporaire contre la corrosion de pieces metalliques, ses procedes de preparation et d'application et pieces metalliques obtenues a partir de cette composition |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4917809A (en) * | 1986-11-11 | 1990-04-17 | Ciba-Geigy Corporation | High-temperature lubricants |
US5194167A (en) * | 1991-05-08 | 1993-03-16 | Mobil Oil Corporation | Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives as antioxidant and antiwear additives |
CN104060276B (zh) * | 2014-06-26 | 2016-08-17 | 衢州市万能达清洗有限公司 | 一种金属表面硅烷涂层缓蚀剂 |
EP3440165A1 (fr) * | 2016-04-07 | 2019-02-13 | The Lubrizol Corporation | Dérivés mercaptoazole utilisés en tant qu'additifs de graissage |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1028924A (en) * | 1962-03-13 | 1966-05-11 | Castrol Ltd | Lubricating compositions containing heterocyclic thio-ethers of saturated carboxylic acids |
EP0126030A2 (fr) * | 1983-05-14 | 1984-11-21 | Ciba-Geigy Ag | Procédé de préparation d'acides bêta-(benzothiazolylthio)- et bêta-(benzimidazolylthio)-carboxyliques |
EP0129506A2 (fr) * | 1983-05-14 | 1984-12-27 | Ciba-Geigy Ag | Acides thio-(cyclo)-alcane polycarboxyliques substitués par des hétérocycles |
EP0161222A2 (fr) * | 1984-05-11 | 1985-11-13 | Ciba-Geigy Ag | Amides, imides et nitriles d'acides mercaptocarboxyliques hétérocycliques en tant qu'inhibiteurs de corrosion |
US4568753A (en) * | 1983-11-18 | 1986-02-04 | Sanshin Kagaku Kogyo Co., Ltd. | Rust-preventive agent |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2425426A (en) * | 1947-08-12 | Po-yhalogeno aliphatic nitriles | ||
NL258098A (fr) * | ||||
US2154097A (en) * | 1936-11-27 | 1939-04-11 | Standard Oil Co | Lubricating oil |
US3080314A (en) * | 1959-11-13 | 1963-03-05 | Pure Oil Co | Odor-free naphthas |
US3215641A (en) * | 1962-11-13 | 1965-11-02 | Shell Oil Co | Phenol derivative |
US3166563A (en) * | 1963-10-31 | 1965-01-19 | Stauffer Chemical Co | 2-lower alkyl sulfonyl-benzisothiazoline |
US3536706A (en) * | 1964-02-11 | 1970-10-27 | Geigy Chem Corp | Phenothiazine compounds |
US3537999A (en) * | 1968-12-11 | 1970-11-03 | Chevron Res | Lubricants containing benzothiadiazole |
US3663559A (en) * | 1969-12-03 | 1972-05-16 | Union Carbide Corp | Preparation of oxo-furo-pyridines from furylvinyl isocyanates |
US4113637A (en) * | 1974-09-10 | 1978-09-12 | Institut Francais Du Petrole | Alkyl-guanidino-heterocyclic compounds, their manufacture and use as additives for fuels and lubricants |
US4177155A (en) * | 1975-01-23 | 1979-12-04 | Ciba-Geigy Corporation | Additives for water-based functional fluids |
US4367152A (en) * | 1981-07-02 | 1983-01-04 | Exxon Research And Engineering Co. | Selected heteroaromatic nitrogen compounds as antioxidant/metal deactivators/electrical insulators in lubricating oils and petroleum liquid fuels |
-
1985
- 1985-02-19 IT IT19562/85A patent/IT1185511B/it active
-
1986
- 1986-02-06 EP EP86101564A patent/EP0192132A3/fr not_active Withdrawn
- 1986-02-18 JP JP61032104A patent/JPS61190083A/ja active Pending
- 1986-02-18 US US06/830,370 patent/US4741847A/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1028924A (en) * | 1962-03-13 | 1966-05-11 | Castrol Ltd | Lubricating compositions containing heterocyclic thio-ethers of saturated carboxylic acids |
EP0126030A2 (fr) * | 1983-05-14 | 1984-11-21 | Ciba-Geigy Ag | Procédé de préparation d'acides bêta-(benzothiazolylthio)- et bêta-(benzimidazolylthio)-carboxyliques |
EP0129506A2 (fr) * | 1983-05-14 | 1984-12-27 | Ciba-Geigy Ag | Acides thio-(cyclo)-alcane polycarboxyliques substitués par des hétérocycles |
US4568753A (en) * | 1983-11-18 | 1986-02-04 | Sanshin Kagaku Kogyo Co., Ltd. | Rust-preventive agent |
EP0161222A2 (fr) * | 1984-05-11 | 1985-11-13 | Ciba-Geigy Ag | Amides, imides et nitriles d'acides mercaptocarboxyliques hétérocycliques en tant qu'inhibiteurs de corrosion |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2765595A1 (fr) * | 1997-07-01 | 1999-01-08 | Lorraine Laminage | Composition pour protection temporaire contre la corrosion de pieces metalliques, ses procedes de preparation et d'application et pieces metalliques obtenues a partir de cette composition |
WO1999001590A1 (fr) * | 1997-07-01 | 1999-01-14 | Sollac | Composition pour protection temporaire contre la corrosion de pieces metalliques, ses procedes de preparation et d'application et pieces metalliques obtenues a partir de cette composition |
US6309697B1 (en) | 1997-07-01 | 2001-10-30 | Sollac | Composition for temporarily protecting metal components from corrosion, its processes of preparation and of application, and metal components obtained from this composition |
Also Published As
Publication number | Publication date |
---|---|
IT8519562A0 (it) | 1985-02-19 |
US4741847A (en) | 1988-05-03 |
EP0192132A3 (fr) | 1988-06-08 |
JPS61190083A (ja) | 1986-08-23 |
IT1185511B (it) | 1987-11-12 |
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Inventor name: CARGNINO, FRANCESCO, DR. Inventor name: LORKE, HORST Inventor name: NATOLI, GIUSEPPE, DR. |