GB738093A - Azomethine compounds and compositions comprising the same - Google Patents

Azomethine compounds and compositions comprising the same

Info

Publication number
GB738093A
GB738093A GB536/53A GB53653A GB738093A GB 738093 A GB738093 A GB 738093A GB 536/53 A GB536/53 A GB 536/53A GB 53653 A GB53653 A GB 53653A GB 738093 A GB738093 A GB 738093A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
chain
carbon atoms
azomethines
benzaldehyde
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
Application number
GB536/53A
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.)
Bayer AG
Original Assignee
Bayer AG
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
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB738093A publication Critical patent/GB738093A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/005—Amines or imines
    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0071—Preserving by using additives, e.g. anti-oxidants containing halogens, sulfur or phosphorus
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092—Mixtures
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more 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
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2050/10—Semi-solids; greasy

Abstract

The invention comprises the azomethines obtained by condensing equimolecular proportions of a cyclic hydrocarbon substituted by at least one carbonyl group and at least one hydroxyl group in ortho position to each other and an aliphatic primary monoamine the amino group of which is approximately in the middle of the carbon chain and which contains no hydroxyl group, and a process for the preparation thereof as above. By approximately in the middle of the carbon chain is meant nearer to the middle of a chain containing at least 3 carbon atoms than to the end thereof, if not at the middle of the chain. The aliphatic monoamine may contain from 9 to 18 carbon atoms in the chain. Ortho-hydroxy cyclic carbonyl compounds which may be used are o-hydroxy-, 2-hydroxy-3,5-dichloro-, 2-hydroxy-4-methyl-, 2 - hydroxy - 5 - (tert. - butyl) -, 2 - hydroxy - 3,5 - dimethyl -, 2 - hydroxy - 3,5 - diisobutyl - and 2,6 - dihydroxy - benzaldehyde, resorcinol - dialdehyde - 2,4, 2 - hydroxy - naphthaldehyde, 2 - hydroxy - acetophenone, o - hydroxy - propiophenone, 2 - hydroxy - 5 - (tert. - butyl) - acetophenone and 2,21 - dihydroxy - benzophenone. In the examples azomethines are formed by reacting o-hydroxybenzaldehyde with a primary aliphatic amine having a carbon chain of about 14 carbon atoms, and by reacting 2 - hydroxy - 3,5 - dichlorobenzaldehyde, 2 - hydroxy - naphthaldehyde, 2 - hydroxy - 5 - (tert. - butyl) - benzaldehyde and 2 - hydroxy - acetophenone with a primary aliphatic amine containing about 10 carbon atoms in the chain. The azomethines may be used as antioxidants.ALSO:Mineral oils and fats are stabilized by the addition of an azomethine obtained by condensing equimolecular proportions of a cyclic hydrocarbon substituted by at least one carbonyl group and at least one hydroxyl group in ortho position to each other and an aliphatic primary monoamine free from hydroxy groups, the amino group of which is at the middle of the carbon chain of said amine or is nearer to the middle of the carbon chain than to the end thereof, the said carbon chain containing at least 3 carbon atoms. A mixture of said azomethines may also be used. A mineral oil lubricant may also contain an ester of phosphoric or phosphinic acid such as an ester of a lower aliphatic alcohol with a phosphinic acid containing an aromatic hydrocarbon radical. A suitable quantity of additive is 0.2 to 0.5 per cent by weight based on the weight of oil or fat. In the examples, an azomethine obtained by reacting o-hydroxy-benzaldehyde and a primary aliphatic amine containing about 14 carbon atoms is added to a paraffin oil with the butyl ester of bis-(p-chlorophenyl)-phosphinic acid, and an azomethine obtained by reacting 2-hydroxy-3,5-dichloro-benzaldehyde and a primary aliphatic amine containing about 10 carbon atoms is added to a mineral oil.
GB536/53A 1952-01-08 1953-01-07 Azomethine compounds and compositions comprising the same Expired GB738093A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE313565X 1952-01-08

Publications (1)

Publication Number Publication Date
GB738093A true GB738093A (en) 1955-10-05

Family

ID=6141184

Family Applications (1)

Application Number Title Priority Date Filing Date
GB536/53A Expired GB738093A (en) 1952-01-08 1953-01-07 Azomethine compounds and compositions comprising the same

Country Status (4)

Country Link
CH (1) CH313565A (en)
FR (1) FR1069476A (en)
GB (1) GB738093A (en)
NL (1) NL91136C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948680A (en) * 1957-03-15 1960-08-09 Standard Oil Co Lubricant compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948680A (en) * 1957-03-15 1960-08-09 Standard Oil Co Lubricant compositions

Also Published As

Publication number Publication date
CH313565A (en) 1956-04-30
NL91136C (en)
FR1069476A (en) 1954-07-08

Similar Documents

Publication Publication Date Title
US2736706A (en) Lubricant containing a phosphorus acid ester-aldehyde condensation product
US3024277A (en) Amides of alkylenediamine polyalkylenecarboxylic acids
US2591651A (en) Stabilized organic compositions containing bis (hydroxy alkoxy phenyl) alkanes
US2401993A (en) Corrosion resistant composition
US2587546A (en) Rust inhibiting composition
GB646952A (en) Stabilised mineral oils
US2413718A (en) Lubricant
GB1445850A (en) Silicone fluid useful as a brake fluid
GB738093A (en) Azomethine compounds and compositions comprising the same
GB843169A (en) Improved lubricating oil compositions and fuels suitable for use in two-stroke internal combustion engines
GB807102A (en) Antioxidant compositions
US2964479A (en) Stabilizing mixture of 4, 4'-diaminodiphenyl ether and 2, 4'-diaminodiphenyl ether
US3124533A (en) Fluorine containing esters of poly-
GB1252790A (en)
GB731323A (en) Cyclohexyl benzidine compounds and mineral oil compositions containing the same
US2833719A (en) Lubricating oil additive compositions and lubricating oil compositions
US2719123A (en) Fluid compositions containing a cyclopolysiloxane
US2518577A (en) Stabilization of organic compounds
ES386327A1 (en) Organic compounds for use as fuel additives
GB955357A (en) Organophosphorus-substituted dimethyl disulphides, and lubricant and fuel compositions containing the same
US2718502A (en) Lubricant compositions
GB654968A (en) Improvements in liquid hydrocarbon stabilised against deterioration caused by oxidation or polym erisation
US2763616A (en) Alkylthiohydroquinones-formaldehyde-amine reaction products and petroleum fractions, containing the same
GB708006A (en) Fuels for internal combustion engines and compositions for the production of such fuels
US3173871A (en) Lubricating oils containing benzalcyclohexylamine and bis-phenols