DE3939475A1 - Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils - Google Patents

Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils

Info

Publication number
DE3939475A1
DE3939475A1 DE3939475A DE3939475A DE3939475A1 DE 3939475 A1 DE3939475 A1 DE 3939475A1 DE 3939475 A DE3939475 A DE 3939475A DE 3939475 A DE3939475 A DE 3939475A DE 3939475 A1 DE3939475 A1 DE 3939475A1
Authority
DE
Germany
Prior art keywords
amines
aromatic
alkali
salts
substituted
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.)
Ceased
Application number
DE3939475A
Other languages
German (de)
Inventor
Gerhard Prof Dr Eisenbrand
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.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE3818495A external-priority patent/DE3818495A1/en
Application filed by Individual filed Critical Individual
Priority to DE3939475A priority Critical patent/DE3939475A1/en
Publication of DE3939475A1 publication Critical patent/DE3939475A1/en
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/20—Materials not provided for elsewhere as substitutes for glycerol in its non-chemical uses, e.g. as a base in toiletry creams or ointments
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic 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
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
    • C10M133/14—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/067—Polyaryl amine alkanes
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
    • 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
    • C10M2215/26—Amines
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Birds (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Amines (I), which prevent formation of nitrosamines on reacting with NOx, or contain accepting groups for nitrosing agents, in which on further reaction produce no or very small amts. of carcinogenic nitrosamines, are used in body care preparations, cutting fluids and hydraulic oils as described in the patent application DE3818495. The novelty is that the amines can be trishydroxymethyl-aminomethane, aromatic (di)amines, aromatic aminophenols and aromatic methylsubd. amines opt. substd. with carboxylic acids or sulphonic acids, or their (alkali)ne earth and ammonium salts. They can also be aid amides of aliphatic or aromatic carboxylic and sulphonic acid substd. (di)amines, amino phenols, methyl substd. aryl amines or their (alkali)ne earth and ammonium amido sulphamate salts. ADVANTAGE - (I) neutralise the acidic components in the materials mentioned, thus inhibiting formation of nitrosamine.

Description

Es ist bekannt, daß durch die häufige Verwendung von stickstoffhaltigen Zusätzen in Körperpflegemitteln, Kühlschmiermitteln, Hydraulikflüssigkeiten durch NOx-Einwirkung krebserregende Nitrosamine entstehen. Deren Gehalt sollte zwar auf Mengen unterhalb der Nachweisgrenze von derzeit <10 ppb gedrückt werden, jedoch ist dies zur Zeit meist noch nicht möglich. Bei Verwendung von Diethanolamin oder des tertiären Amins Triethanolamin, das häufig eingesetzt wird, sind Kontaminationen von 10 bis 50 ppb in Körperpflegemitteln und weit höhere Gehalte in Kühlschmierstoffen und Hydraulikflüssigkeiten nicht ungewöhnlich.It is known that arise by the frequent use of nitrogenous additives in personal care products, coolants, hydraulic fluids by NO x exposure to carcinogenic nitrosamines. Although their content should be pressed below the detection limit of currently <10 ppb, this is currently not possible at all. When diethanolamine or the tertiary amine triethanolamine is widely used, contaminations of 10 to 50 ppb in personal care products and much higher levels in coolants and hydraulic fluids are not uncommon.

Der Zusatz der stickstoffhaltigen Verbindungen, insbesondere von Aminen zu den erwähnten Präparaten ist aber notwendig, da sie vor allem in kosmetischen Mitteln aber auch in Kühlschmierflüssigkeiten und Hydraulikflüssigkeiten zur Neutralisation saurer Komponenten, wie Fettsäuren, langkettiger Sulfonsäuren, Phosphorsäurederivaten und in Form entsprechender Alkanolamide als Emulgator erforderlich sind.The addition of the nitrogen-containing compounds, in particular of amines to the mentioned preparations is necessary, however especially in cosmetics but also in cosmetics Cooling fluids and hydraulic fluids for Neutralization of acidic components, such as fatty acids, long-chain sulfonic acids, phosphoric acid derivatives and in Form of appropriate alkanolamides required as an emulsifier are.

Die bei weitem wichtigste Kontamination ist die mit N-Nitrosodiethanolamin (NDELA), einem potenten Carcinogen, das die Haut überaus gut durchdringt. Wenn es also nicht möglich ist, die derzeit verwendeten Amine durch solche zu ersetzen, die nicht zu krebserregenden Nitrosaminen führen, muß man versuchen, durch Zusätze von Substanzen, welche NOx abfangen und somit die Nitrosierung der verwendeten Amine verhindern oder jedenfalls stark behindern, die Bildung schädlicher Nitrosamine in Grenzen zu halten oder gar auszuschließen.By far the most important contamination is that of N-nitrosodiethanolamine (NDELA), a potent carcinogen that penetrates the skin extremely well. If it is therefore not possible to replace the amines currently used by those that do not lead to carcinogenic nitrosamines, one must try by additions of substances that trap NO x and thus prevent the nitrosation of amines used or at least hinder the strong To limit or exclude the formation of harmful nitrosamines.

Dies ist insbesondere durch die in den Ansprüchen genannten Substanzen möglich. This is in particular by the mentioned in the claims Substances possible.  

Brauchbar sind z. B. Sulfanilsäure, Anthranilsäure sowie aromatische Amine, Diamine, Aminophenole und methylsubstituierte Amine, die zusätzlich mit Carbonsäure- oder Sulfonsäuregruppen substituiert sind:Are useful z. As sulfanilic acid, anthranilic acid and aromatic amines, diamines, aminophenols and methyl-substituted amines which are additionally treated with carboxylic acid or sulfonic acid groups are substituted:

sowie deren Alkali-, Erdalkali- und Ammoniumsalze, wobei letztere auch Salze mit primären Aminen wie Monoethanolamin oder Trishydroxymethylaminomethan, also quaternäre Ammoniumsalze, sein können. and their alkali, alkaline earth and ammonium salts, wherein the latter also salts with primary amines such as monoethanolamine or trishydroxymethylaminomethane, that is quaternary Ammonium salts, can be.  

Zusätzliche Methylsubstitution:
bei Monoaminen m-, o- und p-Stellung,
bei Diaminen und Aminophenolen in einer oder mehrere der noch freibleibenden Positionen dergestalt, daß Azokupplung, z. B. in o- oder p-Stellung blockiert wird.Additional methyl substitution:
at monoamines m-, o- and p-position,
for diamines and aminophenols in one or more of the remaining free positions such that azo coupling, z. B. is blocked in o- or p-position.

Voraussetzung für den Einsatz aromatischer Aminstrukturen und somit auch Amidstrukturen ist die Anwesenheit von mindestens einem Carboxyl- oder Sulfonsäurerest zusätzlich am Ring. Eine weitere Carboxyl- oder Sulfonsäuregruppe kann dann als Amid vorliegen (-CONH₂ · SO₂-NH₂).Prerequisite for the use of aromatic amine structures and thus also amide structures is the presence of at least one carboxyl or sulfonic acid residue in addition on the ring. Another carboxyl or sulfonic acid group can then present as amide (-CONH₂ · SO₂-NH₂).

Die technischen Alkansulfonamide sind eine Mischung aus primären und sekundären Alkansulfonamiden mit Kohlenstoffketten von C₁₂ bis C₁₈. Im vorliegenden Fall sind jedoch auch Alkansulfonamide ab C₁, also ab Methansulfonamid brauchbar.The technical alkanesulfonamides are a mixture of with primary and secondary alkanesulfonamides Carbon chains of C₁₂ to C₁₈. In the present case However, alkanesulfonamides from C₁, so from Methanesulfonamide useful.

Die Wirksamkeit der Verbindungen ist an ausgewählten Beispielen anhand der Nitrosierung von Diethanolamin durch Natriumnitrit in Tabelle 1 und 2 erläutert.The effectiveness of the compounds is selected Examples based on the nitrosation of diethanolamine by Sodium nitrite in Table 1 and 2 explained.

Inhibitorinhibitor Hemmunginhibition Tris(hydroxymethyl)aminomethan|65%Tris (hydroxymethyl) aminomethane | 65% technisches Alkansulfonamidtechnical alkanesulfonamide 73%73% Methansulfonamidmethanesulfonamide 40%40%

Der Wert ist im wäßrigen System unter modifizierten NaP-Bedingungen gewonnen.The value is modified in the aqueous system NaP conditions won.

Modifizierte NaP-Bedingungen: 10 mmol Diethanolamin, 40 mmol NaNO₂, 400 mmol Hemmstoff, pH = 4, Temperatur = 37°C, Versuchsdauer 4 h. Modified NaP conditions: 10 mmol diethanolamine, 40 mmol NaNO₂, 400 mmol inhibitor, pH = 4, temperature = 37 ° C, Duration of the test 4 h.  

Primäre Amine reagieren mit Nitrosierungsmitteln zu Diazoniumionen, die unter Stickstoffabspaltung in wäßrigen Systemen zu Alkoholen bzw. Phenolen auch in Azokupplungsreaktionen abreagieren. Hierbei wird dem System Nitrosierungsmittel entzogen.Primary amines react with nitrosating agents Diazoniumionen, with elimination of nitrogen in aqueous Systems to alcohols or phenols also in Azo coupling reactions abreactieren. This is the system Removed nitrosating agent.

In Emulsionen, die technisch natürlich praxisnäher sind, wird die Nitrosierung von Diethanolamin noch stärker gehemmt, wie die folgende Tabelle zeigt.In emulsions that are technically more natural, the nitrosation of diethanolamine becomes even stronger inhibited, as the following table shows.

Hemmung der Nitrosierung von Diethanolamin durch primäres AminInhibition of nitrosation of diethanolamine by primary amine Bedingungen: Emulsion mit 1% Diethanolamin, 0,1 mol/kg Hemmstoff (=1%), pH 6,8, 5 ppm NOx, 4 Stunden, Glasplatten 7,5×15 cmConditions: emulsion with 1% diethanolamine, 0.1 mol / kg inhibitor (= 1%), pH 6.8, 5 ppm NO x , 4 hours, glass plates 7.5 × 15 cm Inhibitorinhibitor Hemmunginhibition Tris(hydroxymethyl)aminomethan|77%Tris (hydroxymethyl) aminomethane | 77%

Hemmung der Nitrosierung von Diethanolamin durch primäre AmideInhibition of nitrosation of diethanolamine by primary amides Bedingungen: Emulsion mit 1% Diethanolamin, 0,1 mol/kg Hemmstoff (=18%), pH 6,8, 5 ppm NOx, 4 Stunden, Glasplatten 7,5×15 cmConditions: emulsion with 1% diethanolamine, 0.1 mol / kg inhibitor (= 18%), pH 6.8, 5 ppm NO x , 4 hours, glass plates 7.5 × 15 cm Inhibitorinhibitor Hemmunginhibition Methansulfonamid|85%Methanesulfonamide | 85% technisches Alkansulfonamidtechnical alkanesulfonamide 70%70% AmmoniumamidosulfamatAmmoniumamidosulfamat 56%56%

Bei gleichzeitigem Einsatz von Monoethanolamin und Diethanolamin wird die NDELAT-Bildung ebenfalls stark reduziert.With simultaneous use of monoethanolamine and Diethanolamine also strengthens NDELAT formation reduced.

Claims (5)

1. Verwendung von Aminen, die strukturbedingt bei Reaktion mit NOx nicht zu Nitrosaminen führen oder von Aminen, die Fängergruppen für nitrosierende Agentien enthalten, bei deren Weiterreaktion keine oder nur sehr geringe Mengen krebserregender Nitrosamine entstehen als Aminbestandteile in Körperpflegemitteln, Kühlschmiermitteln und Hydraulikölen gemäß Patent . . . (Patentanmeldung P 38 18 495.8), dadurch gekennzeichnet, daß als Amine Trishydroxymethylaminomethan, aromatische Amine, aromatische Diamine, aromatische Aminophenole und aromatische methylsubstituierte Amine, die zusätzlich mit Carbonsäure oder Sulfonsäuregruppen substituiert sind, sowie deren Alkali-, Erdalkali- und Ammoniumsalze, wobei letztere auch Salze mit primären Aminen wie Monoethanolamin und Trishydroxymethylaminomethan sein können, oder von Säureamiden von aliphatischen oder aromatischen Carbon- oder sulfonsäuresubstituierten Aminen, Diaminen, Aminophenolen oder methylsubstituierten Arylamine sowie deren Alkali- oder Erdalkalisalzen oder Ammoniumamidosulfamat eingesetzt werden.1. Use of amines, which do not lead to nitrosamines in the reaction with NO x or of amines containing scavenger groups for nitrosating agents in their further reaction no or only very small amounts of carcinogenic nitrosamines arise as amine constituents in personal care products, cooling lubricants and hydraulic oils according to patent , , , (Patent Application P 38 18 495.8), characterized in that as amines Trishydroxymethylaminomethan, aromatic amines, aromatic diamines, aromatic aminophenols and aromatic methyl-substituted amines, which are additionally substituted with carboxylic acid or sulfonic acid groups, and their alkali, alkaline earth and ammonium salts, the latter may also be salts with primary amines such as monoethanolamine and Trishydroxymethylaminomethan, or be used by acid amides of aliphatic or aromatic carboxylic or sulfonic acid-substituted amines, diamines, aminophenols or methyl-substituted arylamines and their alkali metal or alkaline earth metal salts or Ammoniumamidosulfamat. 2. Verwendung von Säureamiden aromatischer Amine, Diamine, Aminophenole und methylsubstituierter Arylamine nach Anspruch 1.2. Use of acid amides of aromatic amines, diamines, Aminophenols and methyl-substituted arylamines Claim 1. 3. Verwendung von o- oder m-Aminobenzoesäure oder o-, m- oder p-Sulfanilsäuren oder deren Alkali-, Erdalkali- oder Ammoniumsalzen oder deren Säureamiden nach Anspruch 1 eingesetzt werden. 3. Use of o- or m-aminobenzoic acid or o-, m- or p-sulphanilic acids or their alkali, alkaline earth or Ammonium salts or their acid amides according to claim 1 be used.   4. Verwendung von Amidosulfonsäure, ihren Alkali- und Erdalkali- und Ammoniumsalzen sowie ihren Salzen mit primären aliphatischen verzweigten und unverzweigten Aminen (C₂-C₁₈), die durch eine oder mehrere Hydroxy- oder Aminogruppen zusätzlich substituiert sind, insbesondere mit Monoethanolamin, Ethylendiamin, 1-Aminopropandiol und 2,3-Trishydroxymethylaminomethan, nach Anspruch 1.4. Use of amidosulfonic acid, their alkali and Alkaline earth and ammonium salts and their salts with primary aliphatic branched and unbranched Amines (C₂-C₁₈), which are replaced by one or more Hydroxy or amino groups are additionally substituted, especially with monoethanolamine, ethylenediamine, 1-aminopropanediol and 2,3-trishydroxymethylaminomethane, according to claim 1. 5. Verwendung von Alkansulfonamiden (C₁-C₁₈), die geradkettig oder verzweigt sein können, wobei die Sulfonamidgruppe -SO₂-NH₂ endständig oder innerhalb der Kette stehen kann, nach Anspruch 1.5. Use of alkanesulfonamides (C₁-C₁₈), the may be straight or branched, wherein the Sulfonamide group -SO₂-NH₂ terminally or within the chain can stand, according to claim 1.
DE3939475A 1988-05-31 1989-11-29 Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils Ceased DE3939475A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE3939475A DE3939475A1 (en) 1988-05-31 1989-11-29 Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3818495A DE3818495A1 (en) 1988-05-31 1988-05-31 USE OF SPECIAL AMINES TO PREVENT NITROSAMINE FORMATION
DE3939475A DE3939475A1 (en) 1988-05-31 1989-11-29 Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils

Publications (1)

Publication Number Publication Date
DE3939475A1 true DE3939475A1 (en) 1991-06-06

Family

ID=25868631

Family Applications (1)

Application Number Title Priority Date Filing Date
DE3939475A Ceased DE3939475A1 (en) 1988-05-31 1989-11-29 Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils

Country Status (1)

Country Link
DE (1) DE3939475A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1003076C2 (en) * 1995-05-11 1998-08-12 Akzo Nobel Surface Chem Composition containing a secondary amine and use of primary amines as inhibitors for the formation of N-nitrosamines.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1003076C2 (en) * 1995-05-11 1998-08-12 Akzo Nobel Surface Chem Composition containing a secondary amine and use of primary amines as inhibitors for the formation of N-nitrosamines.

Similar Documents

Publication Publication Date Title
DE2922562C2 (en) Rust-preventing agent for aqueous systems and rust-inhibiting slip or lubricating composition
DE3319183A1 (en) USE OF ALKENYLSBERSTALIC ACID HALBAMIDES AS AN ANTI-CORROSIVE AGENT
DE2610879A1 (en) CORROSION INHIBITOR FOR MONO AND POLYURA FATS
EP0002780A1 (en) Use of corrosion inhibitors in aqueous systems
DE19930683A1 (en) Corrosion inhibitors with improved water solubility
DE2943963C2 (en)
DE3939475A1 (en) Use of specific amine(s), in preventing nitrosamine formation - in body care preparations, cutting fluids and hydraulic oils
EP0029529B1 (en) Reaction products of sulfone or carboxamido carboxylic acids with alkanol amines, and their use as corrosion inhibitors with low foam formation
CH629540A5 (en) WATER-MIXABLE ANTI-CORROSIVE AGENT.
DE2225015A1 (en) Color stabilized alkanolamines
EP0031284B1 (en) Composition and method for inhibiting the formation of nitrosamine in organic amines by addition of 1,4-naphthoquinone, 1,4-naphthohydroquinone or alkyl derivatives thereof
DE1164591B (en) Process for stabilizing hydrocarbons
US4724124A (en) Use of alkenylsuccinic acid half-amides as anti-corrosion agents
EP0060455B1 (en) Inhibitors against corrosion by carbon dioxide and hydrogen sulfide in water-in-oil emulsions
DE949741C (en) Process for the preparation of new derivatives of dibenzothiophene dioxide
WO1989011870A1 (en) Use of special amines to prevent nitrosamine formation
EP0231524B1 (en) Application of alkylbenzoylacrylic acids as corrosion inhibitors
DE3341013A1 (en) AMBER ACID MONO-DIALKYLAMIDES AS WATER-SOLUBLE CORROSION PROTECTORS
EP0341536B1 (en) Mixtures of alkenylsuccinic acids, arylsulfonylanthranilic acids and alkanol amines and their use as corrosion inhibitors in aqueous systems
EP1184486A2 (en) Use of N-Alkyl-beta-alanine-Derivatives for the manufacture of cleaning corrosion inhibitors
EP0106234A1 (en) Use of amine salts of maleamic acid as corrosion inhibitors of C02 and H2S in water in oil emulsions
EP0726335A1 (en) Lactobionamide containing corrosion inhibiting composition
DE3701719A1 (en) Corrosion protection agent, containing mixtures with amido acids
EP0037949B1 (en) Mixture of a mixture salt of zinc-alconolimine, and its use as an anti-corrosion additive
DE2746913A1 (en) Corrosion inhibited aq. di:ethanolamine acid gas scrubbing system - contg. e.g. low molecular wt. poly:alkylene poly:amine, copper and sulphur

Legal Events

Date Code Title Description
AF Is addition to no.

Ref country code: DE

Ref document number: 3818495

Format of ref document f/p: P

8131 Rejection