EP0726335B1 - Lactobionamide containing corrosion inhibiting composition - Google Patents
Lactobionamide containing corrosion inhibiting composition Download PDFInfo
- 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
- Authority
- 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
Links
- 238000005260 corrosion Methods 0.000 title abstract description 43
- 230000007797 corrosion Effects 0.000 title abstract description 30
- 239000000203 mixture Substances 0.000 title description 16
- 230000002401 inhibitory effect Effects 0.000 title description 6
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229940099563 lactobionic acid Drugs 0.000 claims abstract description 40
- 150000001412 amines Chemical class 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 150000001408 amides Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000003760 tallow Substances 0.000 claims description 7
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 6
- 244000060011 Cocos nucifera Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005555 metalworking Methods 0.000 description 6
- 229940113162 oleylamide Drugs 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- -1 lactobionic acid lactone Chemical class 0.000 description 4
- 239000011814 protection agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910001060 Gray iron Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000005068 cooling lubricant Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
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)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (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)
Abstract
Description
Die Erfindung betrifft die Verwendung von Lactobionsäure-N-alkylamiden als Korrosionsschutzmittel.The invention relates to the use of Lactobionic acid N-alkyl amides as anti-corrosion agents.
Bei vielen Vorgängen der Metallbearbeitung wie z.B. Schneiden, Schleifen oder Bohren werden Korrosionsschutzmittel eingesetzt, um die bearbeiteten Metallgegenstände vor Rostbildung zu schützen. Viele der bisher üblichen Korrosionsschutzmittel enthalten schwefelhaltige Verbindungen wie z.B. Petrolsulfonate oder Alkylarylsulfonsäuren oder stickstoffhaltige Verbindungen wie z.B. sekundäre Amine oder Alkanolamine. Schwefelhaltige Korrosionsschutzmittel haben dabei den Nachteil, daß deren Wirkstoffe leicht von schwefelreduzierenden Mikroorganismen modifiziert bzw. abgebaut werden. Bei aminhaltigen Korrosionsschutzmitteln, welche insbesondere sekundäre Amine enthalten, besteht die Möglichkeit, daß aus ihren gesundheitsgefährdende Nitrosamine freigesetzt werden, welche sich zuvor durch unkontrollierte chemische Reaktionen gebildet haben. Es besteht somit immer noch der Bedarf nach neuen Korrosionsschutzmitteln, welche diese Nachteile des Standes der Technik nicht aufweisen. Hierbei sind insbesondere neue aminfreie Korrosionsschutzmittel wünschenswert, die als korrosionsinhibierendes Agens einen auch unter Umweltschutzgesichtspunkten günstigen Wirkstoff auf Basis nachwachsender Rohstoffe enthalten. In many metalworking processes such as Cutting, grinding or drilling become anti-corrosion agents used to protect the machined metal objects from rusting to protect. Many of the usual anti-corrosion agents contain sulfur-containing compounds such as Petroleum sulfonates or alkylarylsulfonic acids or nitrogenous ones Connections such as secondary amines or alkanolamines. Sulphurous Corrosion protection agents have the disadvantage that their active ingredients easily from sulfur-reducing microorganisms modified or dismantled. In the case of amine-containing corrosion protection agents, which contain in particular secondary amines, there is a possibility that from their health endangering Nitrosamines are released, which have previously passed through have formed uncontrolled chemical reactions. It exists hence the need for new anti-corrosion agents, which do not have these disadvantages of the prior art. In particular, there are new amine-free corrosion protection agents desirable, the one as a corrosion inhibiting agent active ingredient based on environmental protection contain renewable raw materials.
Aus EP 0 569 869 sind Lactobionsäureamidgemische bekannt, die durch Umsetzung von Lactobionsäure oder Lactobionsäurederivaten mit einem Fettamingemisch in einem niederen Alkylalkohol hergestellt werden. Auf Grund ihrer grenzflächenaktiven Eigenschaften und ihrem günstigen Schaumverhalten finden sie in Wasch-, Spül- und Reinigungsmittelzubereitungen, in Weichspülmitteln sowie kosmetischen Formulierungen Verwendung.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.
Eine korrosionsinhibierende Wirkung derartiger Lactobionsäuregemische kann dieser Schrift nicht entnommen werden. A corrosion-inhibiting effect of such lactobionic acid mixtures cannot be found in this document.
Der vorliegenden Erfindung liegt die Aufgabe zugrunde, neue Korrosionsschutzmittel zur Verfügung zu stellen.The present invention is based on the object to provide new anti-corrosion agents.
Überraschenderweise wurde nun gefunden, daß Lactobionsäure-N-alkylamide, eine korrosionsinhibierende Wirkung besitzen. Surprisingly, it has now been found that lactobionic acid N-alkylamides, have a corrosion-inhibiting effect.
Gegenstand der Erfindung ist somit die Verwendung von Lactobionsäure-N-alkylamiden als Korrosionsschutzmittel. Bevorzugt werden Lactobionsäure-N-alkylamide, deren über die Amidfunktion gebundene gesättigte oder teilweise ungesättigte Alkylreste eine Kettenlänge von 8 bis 18 Kohlenstoffatomen aufweisen, verwendet.The object of the invention is thus the use of lactobionic acid-N-alkylamides as anti-corrosion agents. Prefers 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.
Insbesondere werden solche Lactobionsäure-N-alkylamide verwendet welche durch die Umsetzung von Lactobionsäure oder reaktiven Lactobionsäurederivaten, vorzugsweise Lactobionsäurelacton, mit einem primären Fettamingemisch erhalten wurden. Als "primäre Fettamine" werden im Rahmen der vorliegenden Erfindung primäre Amine bezeichnet, welche einen dem aliphatischen Rest einer Fettsäure entsprechenden aliphatischen Rest enthalten. Fettamine können z.B. technisch aus Fettsäuren erhalten werden, in dem diese zunächst in ihre Nitrile überführt werden, welche anschließend zu Aminen reduziert werden. Bevorzugt werden Fettamingemische eingesetzt, welche aus natürlich vorkommenden Fettsäuregemischen gewonnen werden. Der Anteil an ungesättigten Fettaminen schwankt dabei in diesen Fettamingemischen zwischen ca. 5 und 85 Gew.-%.In particular, such 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. Be considered "primary fatty amines" designated primary amines in the context of the present invention, which corresponds to the aliphatic residue of a fatty acid contain aliphatic residue. 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.
Besonders bevorzugt werden als Korrosionsschutzmittel Lactobionsäure-N-alkylamide aus der Gruppe Lactobionsäure-N-Oleylamid, Lactobionsäure-N-Kokosamid und Lactobionsäure-N-Talgamid verwendet. Diese besonders bevorzugten Lactobionsäure-N-alkylamide können leicht durch die Umsetzung von Lactobionsäure bzw. Lactobionsäurederivat mit den entsprechenden Fettamingemischen hergestellt werden. So wird mit Oleylamin ein Fettamingemisch bezeichnet, welches aus einem aus Sonnenblumenöl und/oder Sojaöl stammenden Fettsäuregemisch gewonnen wurde. Mit Kokosfettamin wird ein entsprechendes sich aus Kokosfett herleitendes Fettamingemisch, mit Talgamin ein entsprechendes sich aus Talg herleitendes Fettamingemisch bezeichnet. Neben gesättigten Fettaminen ist in diesen natürlichen Fettamingemischen immer ein gewisser Anteil ungesättigter Fettamine vorhanden. Aus Sonnenblumenöl gewonnenes Oleylamin enthält z.B. ca. 14 Gew.-% an gesättigten Fettaminen mit 12 bis 18 Kohlenstoffatomen und ca. 85 Gew.-% an ungesättigten Fettaminen mit 14 bis 18 Kohlenstoffatomen. Aus Sojaöl gewonnenes Oleylamin (auch Sojaamin genannt) enthält z.B. ca. 16 Gew.-% an gesättigten C16-Fettaminen, ca. 15 Gew.-% an gesättigten C18-Fettaminen sowie einen Anteil von ca. 63 Gew.-% an ungesättigten Fettaminen mit 14 bis 18 Kohlenstoffatomen. Kokosfettamin enthält z.B. ca. 50 Gew.-% an gesättigten C12-Fettaminen, ca. 18 Gew.-% an gesättigten C14-Fettaminen ca. einen Anteil von ca. 7 Gew.-% an ungesättigten C18-Fettaminen. Talgamin enthält z.B. ca. 29 Gew.-% an gesättigten C16-Fettaminen, ca. 23 Gew.-% an gesättigten C18-Fettaminen sowie einen Anteil von ca. 42 Gew.-% an ungesättigten Fettaminen mit 14 bis 18 Kohlenstoffatomen.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. 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.
Lactobionsäure(=4-(β-D-Galacto)-D-Glukonsäure) und Lactobionsäurelacton sowie deren Herstellung sind bereits bekannt. Lactobionsäure kann beispielsweise auf bekannte Weise durch Oxidation von Lactose erhalten werden.Lactobionic acid (= 4- (β-D-galacto) -D-gluconic acid) and lactobionic acid lactone and their manufacture are already known. Lactobionic acid can, for example, in a known manner Oxidation of lactose can be obtained.
Vorzugsweise werden als erfindungsgemäße Korrosionsschutzmittel die Lactobionsäure-N-alkylamide in Form einer wäßrigen Lösung verwendet. Die wäßrigen Lösungen der Lactobionsäure-N-alkylamide können dabei alleine oder auch im Gemisch mit weiteren Verbindungen als Korrosionsschutzmittel eingesetzt werden. Der Gehalt an Lactobionsäure-N-alkyl-amiden, bezogen auf die wäßrige Lösung, kann dabei im für Korrionsschutzmittel üblichen Konzentrationsbereich, zweckmäßigerweise im Konzentrationsbereich von 0,1 bis 20 Gew.-%, z.B. im Konzentrationsbereich von 1 bis 10 Gew.-%, liegen. Der pH-Wert der wäßrigen Korrosionsschutzmittel sollte unterhalb pH 9,0 liegen.Are preferred as anti-corrosion agents according to the invention the 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.
Die erfindungsgemäßen Korrosionsschutzmittel, die Lactobionsäure-N-alkylamide in einer wäßrigen Lösung enthalten, können vollständig klare Lösungen oder, insbesondere bei Gegenwart anderer Verbindungen, feinverteilte Emulsionen sein, die transparent, opal oder auch milchig trüb sein können. The anti-corrosion agents according to the invention, the lactobionic acid N-alkylamides contained in an aqueous solution, can be completely clear solutions or, especially in the presence other compounds, finely divided emulsions that can be transparent, opal or even milky cloudy.
Neben Lactobionsäure-N-alkylamiden können die erfindungsgemäßen Korrosionsschutzmittel alle für Korrosionsschutzmittel üblichen Verbindungen, z.B. Petrolsulfonate, Mineralöle oder andere Additive enthalten.In addition to lactobionic acid N-alkylamides, the inventive Anti-corrosion agents all for anti-corrosion agents usual connections, e.g. Petroleum sulfonates, mineral oils or contain other additives.
Die erfindungsgemäß verwendeten Lactobionsäure-N-alkylamide zeigen emulgierende und korrosionsinhibierende Wirkung in mineralölhaltigen, wäßrigen Metallbearbeitungsmitteln. Ein weiterer Gegenstand der Erfindung ist daher die Verwendung der Lactobionsäure-N-alkylamide in Metallbearbeitungsmitteln, insbesondere wasserhaltigen Metallbearbeitungsmitteln. Unter Metallbearbeitungsmitteln werden dabei alle zur Metallbearbeitung üblichen Flüssigkeiten, insbesondere Kühlschmiermittel, Bohr-, Schneid- und Schleiföle, Entrostungs-, Entlackungs- und Passivierungsmittel verstanden. Mit den erfindungsgemäß verwendeten Lactobionsäure-N-alkylamiden ist es möglich, Metallbearbeitungsemulsionen herzustellen, welche in hohem Maße Wasser enthalten, ohne daß es dabei zur Rostbildung kommt. Neben einem guten Korrosionsschutz zeichnen sich die erfindungsgemäßen Korrosionsschutzmittel durch eine ausgezeichnete Hautverträglichkeit und hohe biologische Abbaubarkeit aus.The 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. With the used according to the invention 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.
Die korrosionsinhibierende Wirkung der erfindungsgemäß verwendeten Lactobionsäure-N-alkylamiden wurde mittels des Späne/Filterpapier-Verfahrens nach der DIN 51360, Teil 2, ermittelt.The corrosion-inhibiting effect of those used according to the invention Lactobionic acid-N-alkylamides were made using the shavings / filter paper method determined according to DIN 51360, part 2.
Die nachfolgenden Beispiele sollen die Erfindung weiter erläutern, ohne sie jedoch in ihrem Umfang zu begrenzen.The following examples are intended to further illustrate the invention explain, but without limiting their scope.
500 g Lactobionsäurelacton wurden in einem Mörser fein gerieben und dann portionsweise bei 50 bis 60°C in 1,6 l Methanol gelöst. In diese Lösung wurden 324,4 g geschmolzenes Oleylamin unter Rühren zugegeben. Diese gesamte, noch klare Lösung wurde 1 Stunde bei Raumtemperatur gerührt und anschließend für ca. 12 Stunden stehengelassen. Es fiel ein weißer Niederschlag aus, der abfiltriert, mit Methanol gewaschen und dann im Vakuumtrockenschrank bei 30°C getrocknet wurde. Die Ausbeute betrug 93 Gew.-% Lactobionsäure-N-Oleylamid, bezogen auf Lactobionsäurelacton.500 g of lactobionic acid lactone were finely ground in a mortar and then dissolved in portions in 1.6 l of methanol at 50 to 60 ° C. Into this solution were added 324.4 g of molten oleylamine added with stirring. This entire, still clear solution was made Stirred for 1 hour at room temperature and then for approx. Let stand for 12 hours. A white precipitate fell out which is filtered off, washed with methanol and then in a vacuum drying cabinet was dried at 30 ° C. The yield was 93% by weight of lactobionic acid-N-oleylamide, based on lactobionic acid lactone.
Wie beispielhaft für Lactobionsäure-N-Oleylamid beschrieben, erfolgte auch die Herstellung der übrigen Lactobionsäureamide.As described by way of example for lactobionic acid N-oleylamide, the other lactobionic acid amides were also prepared.
Die Korrosionsschutzeigenschaften wurden gemäß der DIN-Norm 51360, Teil 2, durchgeführt.The anti-corrosion properties were determined in accordance with the DIN standard 51360, part 2.
Graugußspäne (Werkstoff DIN 1691-GG30 von etwa 5 mm x mm-Größe) wurden mit Petrolether gewaschen, durch ein Drahtsieb gesiebt und bei ca. 105°C im Trockenschrank getrocknet. Nach der Trocknung wurde es vermieden, die Späne mit der Hand zu berühren.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.
In eine Petri-Schale wurde ein Rundfilter aus Filtrierpapier
(Durchmesser 40 mm) gelegt und mit 2 g (± 0,1 g) der getrockneten
Späne gleichmäßig bestreut. Anschließend wurden die Späne
mit 2 ml der zu untersuchenden Lösung mittels einer Vollpipette
gleichmäßig benetzt. Es wurde der Deckel der Petri-Schale aufgelegt
und die Petri-Schale für 2 Stunden bei Raumtemperatur
stehengelassen. Dann wurden die Späne vom Rundfilter entfernt,
das Rundfilter unter fließendem Wasser abgespült, in Aceton
etwa für 5 Sekunden geschwenkt und bei Raumtemperatur getrocknet.
Sofort anschließend an das Reinigen und Trocknen des Rundfilters
wurde der Korrosionsgrad der Korrosionsabzeichnungen
auf dem Rundfilter durch Sichtprüfung festgestellt. In der
nachfolgenden Tabelle wird der ermittelte Korrosionsgrad
angegeben. Zur
besseren Beurteilung wurde ein Versuch nur mit reinem Leitungswasser
ohne weiteren Zusatz durchgeführt. Es wurde jeweils die
Korrosionsschutzwirkung für eine mit Leitungswasser angesetzte
3%ige wäßrige Lösung von Oleylamid, Kokosamid und Talgamid
ermittelt. Zusätzlich wurde noch eine weitere Versuchsreihe
durchgeführt, bei der der pH-Wert mit Triethanolamin auf pH 9,0
eingestellt wurde.
Die vorstehenden Ergebnisse belegen, daß die erfindungsgemäß verwendeten Lactobionsäure-N-alkylamide Korrosionsschutzeigenschaften entsprechend der DIN-Norm 51360, Teil 2, besitzen.The above results demonstrate that the invention Lactobionic acid-N-alkyl amides used corrosion protection properties accordingly the DIN standard 51360, part 2.
Claims (6)
- The use of lactobionic acid N-alkylamides as anticorrosion agents and/or as an additive in metal-processing agents.
- The use of lactobionic acid N-alkylamides according to Claim 1, wherein lactobionic acid N-alkylamides having saturated or partially unsaturated alkyl radicals, bonded via the amide function, having a chain length of 8 to 18 carbon atoms are used.
- The use of lactobionic acid N-alkylamides according to Claims 1 and 2, wherein lactobionic acid N-alkylamides obtained by reaction of lactobionic acid or lactobionic acid derivatives with fatty amines are used.
- The use of lactobionic acid N-alkylamides according to Claims 1 to 3, wherein lactobionic acid N-alkylamides selected from the group consisting of lactobionic acid N-oleyl amide, lactobionic acid N-coconut amide and lactobionic acid N-tallow amide are used.
- The use of lactobionic acid N-alkylamides according to Claims 1 to 4, wherein lactobionic acid N-alkylamides are used in a quantity of 0.1 to 20% by weight.
- The use of lactobionic acid N-alkylamides according to Claims 1 to 4, wherein lactobionic acid N-alkylamides are used in a quantity of 0.1 to 10% by weight.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19504639 | 1995-02-13 | ||
| DE19504639A DE19504639A1 (en) | 1995-02-13 | 1995-02-13 | Corrosion inhibitors containing lactobionic acid amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0726335A1 EP0726335A1 (en) | 1996-08-14 |
| EP0726335B1 true EP0726335B1 (en) | 1998-05-06 |
Family
ID=7753769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96101716A Expired - Lifetime EP0726335B1 (en) | 1995-02-13 | 1996-02-07 | Lactobionamide containing corrosion inhibiting composition |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US5779939A (en) |
| EP (1) | EP0726335B1 (en) |
| AT (1) | ATE165875T1 (en) |
| DE (2) | DE19504639A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19631959A1 (en) * | 1996-08-08 | 1998-02-12 | Solvay Deutschland | Corrosion inhibitors and corrosion inhibitors containing lactobionic acid amides |
| JP4023079B2 (en) * | 2000-08-31 | 2007-12-19 | 株式会社日立製作所 | Planar illumination device and display device including the same |
| 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)
| 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 (en) * | 1961-07-25 | 1963-10-17 | Akad Wissenschaften Ddr | Process for the preparation of nonionic polyoxycarboxylic acid-N-alkylamides |
| 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 (en) * | 1988-02-18 | 1989-08-25 | Kurita Water Ind Ltd | Corrosion inhibitor |
| US5389279A (en) * | 1991-12-31 | 1995-02-14 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising nonionic glycolipid surfactants |
| DE4215478A1 (en) * | 1992-05-11 | 1993-11-18 | Solvay Deutschland | Lactobionic acid amide compositions and their use |
| 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 |
-
1995
- 1995-02-13 DE DE19504639A patent/DE19504639A1/en not_active Withdrawn
-
1996
- 1996-02-07 EP EP96101716A patent/EP0726335B1/en not_active Expired - Lifetime
- 1996-02-07 AT AT96101716T patent/ATE165875T1/en active
- 1996-02-07 DE DE59600176T patent/DE59600176D1/en not_active Expired - Fee Related
- 1996-02-13 US US08/600,613 patent/US5779939A/en not_active Expired - Fee Related
-
1997
- 1997-02-04 US US08/794,383 patent/US5756003A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5756003A (en) | 1998-05-26 |
| US5779939A (en) | 1998-07-14 |
| EP0726335A1 (en) | 1996-08-14 |
| DE19504639A1 (en) | 1996-08-14 |
| ATE165875T1 (en) | 1998-05-15 |
| DE59600176D1 (en) | 1998-06-10 |
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