GB2172284A - Nitrogen-containing additives for non-aqueous functional fluids - Google Patents
Nitrogen-containing additives for non-aqueous functional fluids Download PDFInfo
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- GB2172284A GB2172284A GB08605820A GB8605820A GB2172284A GB 2172284 A GB2172284 A GB 2172284A GB 08605820 A GB08605820 A GB 08605820A GB 8605820 A GB8605820 A GB 8605820A GB 2172284 A GB2172284 A GB 2172284A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
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- 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
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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- 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
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- 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
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
Description
1 GB2172284A 1
SPECIFICATION
Nitrogen-containing additives for non-aqueous functional fluids The present invention relates to non-aqueous functional fluids which contain nitrogen-containing 5 compounds, to novel nitrogen-containing compounds and to a process for the preparation of said nitrogen-containing compounds.
In US Patent Specification 2 856 363 there are described compounds of the formula RCH(OH)
CH(R')N(Y)R"OH, in which R 'S C2-C,,alkyl, R' is hydrogen or C2-C12alkyl, W is a C2-C,hydrocar bon chain and Y is hydrogen or R"-OH. Specifically disclosed compounds are those of formulae 10 C,,H2,-CH(OH)-CH2-NH-CH,-CH2-OH and C,,,H2,-CH(OH)-CH2-N(CH2-CH2-0H),. The compounds are described as corrosion inhibitors in lubricating oils.
Further, in GB Patent Specification 1 152947 there are described W(2hydroxy-3-alkoxypropy
1)ethanolamines and N-(2-hydroxy-3-alkoxypropyi)diethanolamines and quaternary ammonium salts thereof as antistatic agents for polymers. In GB Patent Specification 979 667 there are described 15 adducts of mono- or dialkanolamines with glycidyl alkyl esters as starting materials in the preparation of polyurethanes.
Furthermore, in GB Patent Specification 980003 there are described 1-Nalky]- and 1-Nhydroxyalky]-3-alkylcarboxy-2-propanols and the quaternary ammonium salts thereof for use in cosmetic preparations.
The present invention relates to compositions which contain a non-aqueous functional fluid and at least one compound of formula 1 R' 25 R-X-CH2-CH-CH2-N (1) OH R2 wherein X 'S -0-1 -S-, -So-, -S02-1 -C(O)-0- or -N(R 3)-, in which R' is hydrogen or Cl-CUalkyl, R' is unsubstituted Cl-C,alkyl or C,-C,alkyi substituted by one to three hydroxyl groups, R 2 is hydrogen, unsubstituted C,-C,alkyl or C,-C,alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R2 is hydroxy substituted, and wherein R 'S C2-CM-alkyl, a residue -CH2-CH(OH)-CH,- NR'R2, in which R' and R 2 have their previous significance, or R is C,-C,,#keny], C2-C,aWynyl or C, _ClAycloalkyl, with the 35 proviso that, when X is -C- or -C(O)-0-, R is branchedC4-C2,,aikyi, especially a tertiary alkyl group.
R as C2-CMalkyl may be straight chain or branched alkyl, e.g. ethyl, npropyl, isopropyl, n butyl, isobutyl, sec-butyl, tertbutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl, with C,-C,.alkyl 40 being preferred, C11-CMalkyl being particularly preferred and C,-C 2alkyl being most preferred. R is preferably branched, especially tertiary, alkyl.
R as C2-C,,alkenyl may be straight chain or branched alkenyl, e.g. vinyl, n-propenyl, isoprope nyl, n-butenyl, isobutenyl, n-pentenyl, n-hexenyi, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl, n dodecenyl, n-tetradecenyl, n-hexadecenyl or n-octadecenyl, with C2- CAlkenyl being preferred. 45 C2-C,Alkynyl groups are ethynyl or propargyl groups.
Cl-C12Cycloalkyl groups are exemplified by cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl and cyclododecyl groups.
Unsubstituted C,_C,2alkyl groups R3 may be straight chain or branched, e. g. methyl, ethyl, n propyl, n-butyl, n-hexyi, n-octyi, n-decyl, n-dodecyi, isopropyl, t-butyl or t-octyl.
Hydroxy-substituted C2-C,alkyl groups R' and R2 are e.g. -CH2-CH2-0H, CH2-CH2-CH2-0H, -CH2-CH(OH)-CH,, -CH(CH20H)2C21-1, or -C(CH20H),, with -CH2-CH,-OH being preferred.
Examples of compounds of formula 1 are listed in the following Table 1.
Table 1
R' R-X-CH2-CH-CH2-N 1 OH R2 2 GB2172284A 2 R X RI p2 i-C9H19 -0- CH2CH20H R i-C9H19 -0- CH2CH20H CH2CH20H i-C9H19 -0- CH2CHOWCH20H CH2CH(MCH20H i-Cl2H25 -0- CH2CH2CH20H CH2CH20R i-Cl2H25 -0- CH2CH20H CH2CH(MCH3 t-C9H19 -S- CH2CH20H CH2CH20H t-C9H19 -S- CH2CH(M)CH20H CH2CH(MCH20H t-CizH25 -SCH2CH20H CH2CH20H t-Cl2H25 -S- CH2CH20H CH2CH(OWCH3 t-Cl6H33 -S- CH2CH20H CH2CH2OR t-C16H33 -S- C(CH20W3 H t-C9H19 -CO-0- CH2CH20H CH2CHAH t-Cl2HZ5 -CO-0- CH2CH20H CH2CH20H n-CisH37 -CO-0- CH2CH20H CH2CH20H n-C20H41 -CO-0CHZCH20H CH2CH20H C4H9CH(C2HOCH2 -SO- CH2CH20H CH2CH20H C4H9CH(C2ROCH2 -S02- CH2CH20H CH2CH20H n-CBH17 _N(CH3)- CH2CH20H CH2CH20H i-COH17 -N(CH3)- CH2CH20H H t-C9H19 -N(CH3)- CH2CH(OWCH20111 CH2CH(MCH20H Preferred compositions are those which contain a non-aqueous functional fluid and at least one compound of formula 1, wherein X is -0-, -S- or -C(O)-0-, as well as those which contain at 30 least one compound of formula 1, wherein R' and R 2 are hydroxy- substitutedC2-C,alkyi, espe C'a"Y C2-C,alkyl monosubstituted by hydroxy. R is preferably Q,-C,,,alkyl, in particular branched Q,-C,,alkyl, most preferably tertiaryC,-C 12alkyl.
A further embodiment comprises compositions which contain a non-aqueous functional fluid and at least one compound of formula 1, wherein X is -S-, R' is hydroxy- substitutedCI-C5alkyi, 35 especially C,-C,alkyl polysubstituted by hydroxy, and R2 is hydrogen and R 'S C2-CWalky], preferably, branchedC,- C2(,aikyi, most preferably tertiary C,-C,',alkyl.
Some of the compounds of formula 1 are known and some of the compounds of formula 1 are novel.
Accordingly, the invention further relates to compounds of formula 1 R' R-X-CH2-CH-CH2-N 1 OH R2 wherein X 'S -0-1 -S-, -So-, -S02-1 -C(O)-0- or -N(R3)-, in which R3 is hydrogen or C,-CUalkyl, R' is unsubstituted Cl-C4alkyl or C2-C,alkyl substituted by one to three hydroxyl groups, R2 is hydrogen, unsubstituted Cl-C4alkyl or C2-C,alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R2 is hydroxysubstituted, and wherein R is C4-C20alkyl, a residue -CH2-CH(OH)-CH2-NRIR 2, in which R' and R2 have their previous significance, or R is C2-C,,,aikenyi, C2-C,alkynyl or CS- CUCYCloalkyl, with the proviso that, when X is -0-, -S- or -N(R 3)-, R is branchedC8-C20alkyl and, when X is C(O)-0-, R is different fromC4-C2()aikyl.
Preferred compounds of formula 1 are those wherein X is -0-, -S-or -C(O)0-, and/or R, and R2 are C2-C,alkyl monosubstituted by hydroxy.
Especially preferred compounds of formula 1 are those wherein X is -Sand/or R is preferably tertiary C,-C,,,alkyl.
Further preferred compounds of formula 1 are those wherein X is -S-, R' is hydroxy-substi- 60 tuted C4-C,alkyi, especially C4-C,alkyl polysubstituted by hydroxy, and R 2 is hydrogen and R is C4-C2,,alkyi, preferably C8-CWalkyl, in particular branched C,-CMalkyl, most preferably tertiary C,-C,alkyl.
A further object of the present invention is a process for the preparation of compounds of formula 1 by reacting -a compound of formula 11 3 GB2172284A 3 R-XH (11) wherein X is -0-, -S-, -SO-, S021 -C(O)-0- or N(R3)-, in which R3 is hydrogen or Cl-CUal kyl, and wherein R is C,-C,,alkyl, a residue -CH2-CH(OH)-CH2-NR'R2, in which R' is unsubstituted C,-C,alkyl or C2-C,alkyl substituted by one to three hydroxyl groups, and R 2 is hydrogen, unsubstitutedCl-C4alkyl or C,-C,alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R 2 is hydroxy-substitued, or R 'S C2-C,aIkeny], C2-C3alkynyl or CS-CUCYCloalkyl, with the proviso that, when X is -0-, -S- or -N(R3)-, R is branched C,_CWalkyl and, when X is -C(O)-0-, R is different from C4- CWalkyl, or of a metal salt 10 thereof, e.g. the sodium or potassium salt, in the absence or presence of a catalyst, with a compound of formula Ill CICH2-C-CH2 0 (111) to produce a compound of formula IV R-X-CH2-CH -CH2 20 0 (]V) R2 which is then reacted with an amine of formula V R' H-N (V) wherein R' and R2 have their previous significance.
The catalyst may be for example an acid, a base or a phase transfer catalyst.
The known compounds are prepared in analogous manner.
The compounds of formula i are very suitable for improving the properties, especially the 35 corrosion-inhibiting properties in non-aqueous functional fluids.
The compounds of formula 1 are employed as corrosion inhibitors in nonaqueous functional fluids in amounts of 0.001 to 5% by weight, especially 0.05 to 3% by weight, based on the non-aqueous functional fluid.
The non-queous functional fluid may be a lubricating oil e.g. a natural or synthetic lubricating 40 oil; a refined petroleum product such as a fuel oil, diesel oil, kerosene, gasoline or aviation fuel; or a hydraulic fluid, e.g. a phosphate-based synthetic oil.
The lubricating oil may be a mineral oil, a synthetic oil or any mixture of such oils. Mineral oils are preferred and examples of these include paraffin oils, e.g. a mineral oil having a viscosity of 46 MM2/ s at 4WC;---150 Solvent Neutral-, a solvent refined neutral mineral oil having a viscosity of 32 MM2/ s at 4WC; and -Solvent brightstocks-, a high-boiling residue from the process of refining mineral oil, and having a viscosity of 46 MM2 /s at 4WC.
Synthetic lubricating oils which may be present are for example synthetic hydrocarbons such as polybutenes, alkyl benzenes and poly-alpha olefins as well as simple di-, tri- and tetraesters, complex esters and polyesters. Diesters are derived e.g. from carboxylic acid esters of the formula R5-0(0)C-alkylene-C(O)O-R4 wherein "alkylene" is a C2-Cl4alkylene residue and R4 and R5 are the same or different and each 55 is a C,-C,,,alkyl group.
Triesters which may be used as lubricating oil base-stocks are those derived from trimethylol propane and C,-C,,monocarboxylic acids or mixtures thereof, whereas suitable tetraesters include e.g. those derived from pentaerythritol and a C,-C,,,monocarboxylic acid or mixtures thereof.
Complex esters suitable for use as components of the compositions of the present invention 60 are e.g. those derived from monobasic acids, dibasic acids and polyhydric alcohols, for instance the complex ester derived from trimethylolpropane, caprylic acid and sebacic acid.
Suitable polyesters are e.g. those derived from a C4-C,,dicarboxylic acid and at least one aliphatic dihydricCl-Cl2alcohol, e.g. those derived from azelaic acid or sebacic acid and 2,2,4- trimethylhexane-1,6-diol.
4 GB2172284A 4 The lubricating oils can also contain other additives which may be added to improve the basic properties of lubricants, e.g. anti-oxidants, metal passivators, rust inhibitors, viscosity-index improvers, pour-point depressants, dispersing agents, emulsifiers, extreme pressure additives and anti-wear additives. Examples of such additives are indicated below.
Examples of phenolic antioxidants 1. Alkylated monophenols 2,6-di-tertbutyi-4-methylphenol 2,6-di-tert-butylphenol 2-tert-butyl-4,6-dimethylphenot 2,6-di-tert-butyl-4-ethylphenol 2,6-ditert-butyl-4-ethylphenol 2,6-di-tert-butyl-4-n-butylphenol 2,6-di-tertbutyi-4-isobutylphenol 2,6-dicyclopentyi-4-methylphenol 2(a-methyicyclohexyl)-4,6-dimethylphenol 2,6-dioctadecy]-4-methylphenol 2,4,6-tricyclohexylphenol 2,6-di-tert- butyl-4-methoxymethylphenoI o-tert-butylphenol 2. Alkylated hydroquinones 2,6-di-tert-buty]-4-methoxyphenol 2,5-di-tert- butyihydroquinone 2,5-di-tert-amyihydroquinone 2,6-diphenyi-4-octadecyloxyphenoi 3. Hydroxylated thiodiphenyl ethers 2,2'-thiobis(6-tert-butyl-4methylphenol) 2,2'm-thiobis(4-octylphenol) 4,4'-thiobis(6-tert-butyl-3-methylphenol) 4, 4'-thiobis(6-tert-butyl-2-methylphenol) 4. Alkylidenebisphenols 2,2'-methylenebis (6-tert-butyi-4-methyl phenol) 2,2'-methylenebis(6-tertbutyi-4-ethylphenol) 2,2'-methylenebis[4-methyi-6-((i-m ethylcyclohexyl) phenol] 2,2'-methyienebis(4-methyi-6-cyclohexylphenol) 2,2'methylenebis(6-nony]-4-methylphenol) 2,2'-methylenebis(4,6-di-tert-butylphenol) 2,2'-ethylidenebis(4,6-di-tertbutyiphenol) 2,2'ethylidenebis(6-tert-butyl-4-isobutylphenol) 2,2'methylenebis[6-((i-methyibenzyi)-4-nonyJ phenol] 2,2'-methylenebis[6-((L, (ú-dimethyibenzyi)-4-nonylphenolj 4,4'-methylenebis(2,6-di-tert-butylphenol) 4,4'-methylenebis(6-tert-butyi2-methylphenol) 1, 1 -bis (5-tert-butyi-4-hydroxy-2-methylphenyi) butane 2,6-di(3-tert-butyi-5-methyi-2-hydroxybenzyi)-4-methylphenol 1, 1,3tris(5-tert-butyi-4-hydroxy-2-methylphenyl)-3-n-dodecyimercaptobutane ethylene glycol bis[3,3-bis(3'-tert-buty]-4'-hydroxyphenyi)butyratej di(3tert-butyi-4-hydroxy-5-methylphenyi)dicyclopentadiene di[2-(3'-tert-buty]2'-hydroxy-5'-methyibenzyi)-6-tert-butyi-4-methylphenyi] terephthalate.
5. Benzyl compounds 1,3,5-tri(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene di(3, 5-di-tert-butyl-4-hydroxybenzyl) sulfide 3,5-di-tert-butyl-4hydroxybenzy[mercaptoacetic acid isooctyl ester bis(4-tert-butyl-3hydroxy-2,6-dimethylbenzyl) dithiolterephthalate 1,3,5-tris(3,5-di-tertbutyl-4-hydroxybenzyl) isocyanurate 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate 3,5-ditert-butyl-4-hydroxybenzy[phosphonic acid dioctadecyl ester 3,5-di-tertbutyl-4-hydroxybenzylphosphonic acid monoethyl ester calcium salt.
6. Acylaminophenots 65 4-hydroxylauric acid anilide GB2172284A 5 4-hydroxystearic adid anilide 2,4-bis-octyimercapto-6-(3,5-di-tert-butyl4-hydroxyanilino)-s-triazine N-(3,5-di-tert-butyl4-hydroxyphenyi)carbamic acid octyl ester.
7. Esters of,8-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol diethylene glycol octadecanol triethylene glycol 1,6-hexanediol pentaerythritol neopentyl glycol tris(hydroxyethyl) isocyanurate thiodiethylene glycol di(hydroxyethyl) oxalic acid diamide 8. Esters of fl-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic adid with mono- or polyhydric alcohols, e.g. with methanol octadecanol 1,6- hexanediol neopentyl glycol triodiethylene glycol diethylene glycol triethylene glycol pentaerythritol tri(hydroxyethyi) isocyanurate di(hydroxyethyi) oxalic acid diamide 9. Amides ofO-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid e.g. N,N'-di(3,5-di-tert-butyl-4- hydroxyphenylpropionyi)hexamethylenediamine N,N'-di(3,5-di-tert-butyi-4- hydroxyphenylpropionyi)trimethylenediamine N,N'-di(3,5-di-tert-butyi-4- hydroxyphenylpropionyi)hydrazine.
Examples of amine antioxidants: N,N'-diisopropyl-p-phenylenediamine N,N'-di-sec-butyi-p-phenylenediamine N,N'-bis(1,4-dimethylpentyi)-pphenylenediamine N,W-bis(l -ethyi-3-methylpentyi)-p-phenylenediamine N, Wbis(l -methyiheptyi)-p-phenylenediamine N,N'-diphenyl-p-phenylenediamine N,N'-di(naphthyi-2)-p-phenylenediamine N-isopropyi-N'-phenyi-pphenylenediamine N-(1,3-dimethyibutyi)-N'-phenyi-p-phenylenediamine W(1 methyiheptyi)-N'-phenyi-p-phenylenediamine N-cyclohexy]-N'-phenyl-pphenylenediamine 4-(p-toluenesuifonamido)diphenylamine N,N'-dimethyl-N,N'-di-sec-butyi-p- phenylenediamine diphenylamine 4-isopropoxydiphenylamine N-phenyl- 1 - naphthylamine N-pheny]-2-naphthylarnine octylated diphenylamine 4-n-butylaminophenol 4butyrylaminophenol 4-nonanoylaminophenol 4-dodecanoylaminophenol 4-octadecanoylaminophenol di(4- methoxyphenyl)amine 2,6A i-tert-butyl-4-dimethyla m inomethyl phenol 2,4'- diaminodiphenyimethane 4,4'-diaminodiphenyimethane N, N, N', N'-tetra methyl-4,4'-d ia minod iphenyl methane 1, 2-d i[(2-methyl phenyl) amino]etha ne 1,2di(phenylamino)propane (o-tolyl)biquanide di[4-1',3'-dimethylbutyi)phenyi)amine tert-octylated N-phenyl-lnaphthylarnino mixture of mono- and dialkylated tert-butyi-/tertoctyidiphenylamines.
Examples of metal passivators are:
for copper, e.g.:
6 GB2172284A 6 triazole', benzotriazole and their derivatives, 2-mercaptobenzothiazole, 2,5-dimercaptothiadiazole, salicylidenepropylenediamine, salts of salicylaminoguanidine.
Examples of rust inhibitors are:
a) organic acids, their esters, metal salts and anhydrides, e.g.: Noleoyl sarcosine, sorbitan mono-oleate, lead naphthenate, dodecenylsuccinic anhydride, alkenylsuccinic acid half esters, 4nonylphenoxyacetic acid; b) nitrogen-containing compounds, e.g.:
(1) primary, secondary or tertiary aliphatic or cycloaliphatic amines and amine salts of organic 10 and inorganic acids, e.g. oil-soluble alkylammonium carboxylates; and (11) heterocyclic compounds, e.g.: substituted imidazolines and oxazolines.
c) phosphorus-containing compounds, e.g.:
amine salts of phosphoric acid partial esters d) sulfur-containing compounds, e.g.: barium dinonyl naphthalene sulfonates and calcium petroleum sulfonates.
Examples of viscosity-index improvers are:
polymethlacrylates, vinylpyrrolidone/methacrylate copolymers, polybutenes, olefin copolymers, styrene/acrylate copolymers.
Examples of pour-point depressants are:
polymethacrylates and alkylated naphthalene derivatives.
Examples of dispersing agents1surfactants are:
polybutenylsuccinic acid imides, polybutenylphosphonic acid derivatives, and basic Mg, Ca and Ba sulfonates and Mg, Ca and Ba phenolates.
Examples of anti-wear additives are: compounds containing sulfur and/or phosphorus and/or halogen, e.g.: sulfurised vegetable oils, zinc dialkyl dithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl disulfides and aryl disulfides.
The compounds of formula I are useful as additives in particular to lubricating systems, especially engine oils, in which they exhibit corrosion-inhibiting properties. Relative to known compounds having comparable properties, the compounds of formula I are advantageous in that they are phosphorus- and tin-free so that not even the after-combustion of the exhaust gases is impaired.
Example 1:
10.5 parts of diethanolamine are added dropwise on to 22.8 parts of tertnonylcarboxyglycidyl ether at WC and the resultant solution is stirred for 3 hours. The crude product is distilled to give 28.1 parts of N,Ndi(hydroxyethyi)-2-hydroxy-3-tert-nonylcarbonyloxypropylamine. Boiling point: 225'C/0.13 mb.
Example 2:
10.5 parts of diethanolamine are heated to WC and 27.1 parts of tertdodecyigiycidyl thioether are added dropwise. After completion of the addition, the mixture is stirred for 1 hour at 7WC. 3-tert-Dodecyithio-l[di(2-hydroxyethyi)amino]propan-2-ol is obtained as a yellow vis- cous liquid having refractive index n 20---1.4972 in a yield of 100% of theory.
D_ Example 3:
By following a procedure analogous to that of Example 2, 21 parts of diethanolamine are reacted with 45.4 parts of tert-nonylgiycidyl thioether to produce 3-tert- nonylthio-l-[di(2-hydroxy- ethyi)aminolpropan-2-ol as a yellow viscous liquid having refractive index n2bc-- 1.5008 in a yield 55 of 100% of theory.
Examples 4 to 2 1:
Further compounds of formula 1 7 GB2172284A 7 R-X-CH2-CHCH,-N 1 R' OH R2 are prepared by following a procedure analogous to those of Examples 1 and 2. These compounds are listed in Table 2.
OD Table 2
Ex. R X RI R2 b.p.(C)/mb 4 t-cgnlg -CO-0- (CH2)30H (CH2)3011 viscous Oil t-C9H19 -CO-0- CH3 CH2CH20H 20010.065 6 t-e9H19 -CO-0- CH2CHOHCH3 CH2CHOHCH3 20010.05 7 i-C8H17 -0- CH2CH20H CH2CH2OR 19012.34 8 i-COH17 -0(CH2)30H (CH2)30H viscous Oil 9 i-Cl3H17 -0- CHY CH2CH2ON 18010.065 i-CeHI7 -0- CH2CHOHCH3 CH2CHOIICH3 18010.05 11 CH2"CHCH2 -0- CH2CH20H CHzCH20H 21010.05 12 CO9CH(C2%)CH2 -N(CH2CH(C4Hg)C2Hs)- CH2CH20H CH2CH20H viscous Oil 13 C4H9CH(C2MCHz -N(CH2CH(C09)CzHs)- (CH2)30H (CH2)30H viscous oil 9H / CH2CHzOH 17010.35 14 C112CHCH211. -N(ClzHzs)- CH2CHzOH CH2CHAH \CH2CH20H is t-c.)Hlg -S- CH2CH20H H 16 t-C9H19 -S- CH3 CH2CH20H 17 t-Ci2H2s -S- CH2CHzM CH2CH20H 15510.16 18 t-C9Hig -S- CH2CH20H CH2CH20H 19 t-Cl6H33 -S- CH2CH20H C%CH20H viscous oil t-C9H19 -S- C(CH2OW3 H m.p. 61-63C 21 t-Cl2H2s -S- C(CH2OH)2C2Hs H viscous oil 22 t-C16H33 -SC(CH2OW3 H viscous oil 23 '-CeHg -S- C(CH2OH)3 H 24 C2Hs -S- C(CH20W3 H CD 1 1 9 GB2172284A 9 Examples 22 to 28:
Several products of Examples 1 to 21 are tested as rust inhibitors in a turbine grade mineral oil of viscosity 26 MM2/9 at 4WC, 4.8 MM2/g at 1OWC and a typical sulphur content of 0.6%, using the ASTM D665A (deionised water) and D665B (synthetic sea water) methods. The results are set out in Table 3 and are expressed as the concentration (ppm) of the product which will prevent any trace of rusting of the test spindle. In both A and B tests, the absence of additive causes severe rusting of the test spindle to occur.
Table 3
2. 45 3.
4. 5. 6. 7. 50 8.
Example Test compound Minimum concentration for zero rust A test ppm B test ppm 22 Product of Ex. 1 ( 250 ( 250 23 Product of Ex. 4 ( 500 24 Product of Ex. 7 ( 125 ( 125 Product of Ex. 8 ( 500 26 Product of Ex. 2 ( 500 27 Product of Ex. 3 ( 125 ( 125 28 Product of Ex. 15 ( 250 ( 500
Claims (1)
1. A composition which contains a non-aqueous functional liquid and at least one compound of formula 1 R' R-X-CH,-CH-CH,-N 1 OH R' (1) wherein X is -0-1 -S-, -So-, -S02-1 -C(O)-0- or -N(R3)-, in which R3 is hydrogen or C,-C, alkyl, R' is unsubstituted C,-C,alkyl or C,-C,alkyl substituted by one to three hydroxyl groups, R2 is hydrogen, unsubstituted C,-C,alkyi or C2-C,alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R2 is hydroxysubstituted, and wherein R 'S C2-CMaiky], a residue -CH,- CH(OH)-CH2-NR1R2, in which R' and R2 have their previous significance, or R 'S C2-Cffialkenyl, C2-C,alkynyl Or C5-C12CYCloalkyl, with the proviso that, when X is -C- or -C(O)-0-, R is branched Cl-CWalkyl. A composition according to claim 1, wherein in formula 1 R is C4-CMalkyl. A composition according to claim 2, wherein in formula 1 R is C8-C2,,alkyl. A composition according to claim 3, wherein in formula 1 R is C,-CUalkyl. A composition according to claim 2, wherein in formula 1 R is branchedC4- C2(,aikyl. A composition according to claim 5, wherein in formula 1 R is tertiaryC4-C,)alkyl.
composition according to claim 1, wherein in formula 1 X is -0-, -S- or C(O)-0-.
composition according to claim 1, wherein in formula 1 R' and R2 areC2-C, alkyl monosubstituted by hydroxy.
9. A composition according to claim 1, wherein in formula 1 X is -S-, R' 'S Cl-C5alkyl polysubstituted by hydroxy, R2 is hydrogen and R 'S C2-CMalkyl.
10. A composition according to claim 9, wherein in formula 1 R is branched CS-C20alky].
11. A composition according to claim 10, wherein in formula 1 R is tertiary C,-C,"alky]. 55 12. A composition according to claim 1, wherein the non-aqueous functional fluid is a lubricating oil, a refined petroleum product or a hydraulic fluid.
13. A composition according to claim 12, wherein the lubricating oil is a mineral oil.
14. A composition according to claim 12, wherein the hydraulic fluid is a synthetic oil.
15. A composition according to claim 1, wherein the amount of compound of formula 1 is 60 0.001 to 5% by weight, based on the non-aqueous functional fluid.
16. A composition according to claim 12, wherein the functional fluid contains further addi tives selected from the group consisting of antioxidants, metal passivators, rust inhibitors, viscosity-index improvers, pour-point depressants, dispersing agents, emulsifiers, extreme pres sure additives or anti-wear additives.
GB2172284A 10 17. A compound of formula 1 R' R-X-CH,-CH-CH,-N OH R2 wherein X is -0-, -S-, -SO-, -SO27-, -C(O)-0- or -N(R3)-, in which R3 is hydrogen or Cl-CUalkyl, R' is unsubstituted Cl-lC,alkyl or C2-IC,alkyl substituted by one to three hydroxyl 10 groups, R2 is hydrogen, unsubstituted C,-IC,alkyl or C2-C,alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R2 is hydroxysubstituted, and wherein R 'S C4-C2oalkyl, a residue -CH2-CH(OH)-CH,-NRIR2, in which R' and R2 have their previous significance, or R is C,-Claalkenyl, C27C,alkyrtyl or C,-C, cycloalkyl, with the proviso that, when X is -0-, -S- or -N(R3)-, R is branched C,-Coalkyl and, when X is -C(O)-0-, R is different fromC4-C20alkyl. 18. A compound according to claim 17, wherein in formula 1 X is -0-, -S- or -C(O)-0-. 19. A compound according to claim 17, wherein in formula 1 R' and R2 are C2-IC,alkyl monosubstituted by hydroxy. 20 20. A compound according to claim 18, wherein in formula 1 X is -S-. 21. A icompound according to claim 17, wherein in formula 1 R is tertiary C,-Cealkyl. 22. A compound according to claim 17, wherein in formula -1 X is -S-, R' is C,-C,alkyl polysubstituted by hydroxy, R2 is hydrogen and R is C4-C,,alkyl. 23. A process for the preparation of a compound of formula 1, which process comprises reacting a compound of formula 11 R-Xl-1 (11) wherein X is -0-, -S-, -SO-, SO, -C(O)-0- or -N(R3)-, in which R3 is hydrogen or C11-CUal kyl, and wherein R is C4-C2.alky], a residue -CH2-CH(OH)-CH2-NR'R2, in which R, is unsubsti- 30 tuted C,-C,alkyl or C2-C,alkyl substituted by one to three hydroxyl groups, and R2 is hydrogen, unsubstituted C,-CAlkyi or C2-C,alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R2 is hydroxy-substituted, or R 'S C2-C,ealkenyl, C,-C,alkynyl or C5-CUCYCloalkyl, with the proviso that, when X is -0-, -S- or -N(R3)-, R is branchedC,-C2,,aikyl and, when X is -C(O)-0-, R is different fromC4C2oalkyl, or of a metalsalt 35 thereof, in the absence or presence of a catalyst, with a compound of formula Ill CICI-12-C-CH2 0 to produce a compound of formula IV R-X-CH2-CH -CH2 0 (IV) which is then reacted with an amine of formula V R' - 50 H-N (V) R2 wherein R' and R2 have their previous significance.
24. Method of improving the corrosion inhibiting properties of a nonaqueous functional fluid by adding a compound of formula 1 to said nonaqueous functional fluid.
Printed in the United Kingdom for Her Majesty's Stationery Office, Eld 8818935, 1986. 4235. Published at The Patent Office. 25 Southampton Buildings, London, WC2A 1 AV, from which copies may be obtained.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08605820A GB2172284B (en) | 1985-03-12 | 1986-03-10 | Nitrogen-containing additives for non-aqueous functional fluids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858506352A GB8506352D0 (en) | 1985-03-12 | 1985-03-12 | Corrosion inhibition |
| GB08605820A GB2172284B (en) | 1985-03-12 | 1986-03-10 | Nitrogen-containing additives for non-aqueous functional fluids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8605820D0 GB8605820D0 (en) | 1986-04-16 |
| GB2172284A true GB2172284A (en) | 1986-09-17 |
| GB2172284B GB2172284B (en) | 1988-07-27 |
Family
ID=26288968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08605820A Expired GB2172284B (en) | 1985-03-12 | 1986-03-10 | Nitrogen-containing additives for non-aqueous functional fluids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2172284B (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0206998A2 (en) * | 1985-06-21 | 1986-12-30 | Ciba-Geigy Ag | Lubricant compositions, glucamin derivatives and complex compounds containing them |
| EP0233140A1 (en) * | 1986-01-10 | 1987-08-19 | Ciba-Geigy Ag | Lubricant additives containing sulphur and nitrogen |
| EP0237489A1 (en) * | 1986-03-13 | 1987-09-16 | Ciba-Geigy Ag | Conversion products of bis-glycidylthioethers |
| EP0239536A2 (en) * | 1986-03-22 | 1987-09-30 | Ciba-Geigy Ag | Lubricant compositions |
| EP0255126A2 (en) * | 1986-07-30 | 1988-02-03 | Gödecke Aktiengesellschaft | 2-Acyloxypropylamine derivatives, method for their preparation and medicaments containing them |
| US4888138A (en) * | 1988-11-10 | 1989-12-19 | Ethyl Corporation | Substituted ammonium carbamates and method for preparing same |
| EP0353854A1 (en) * | 1988-06-24 | 1990-02-07 | Exxon Chemical Patents Inc. | Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith |
| EP0378883A1 (en) * | 1987-12-07 | 1990-07-25 | Mobil Oil Corporation | Low temperature fluidity improver |
| GB2227757A (en) * | 1989-02-03 | 1990-08-08 | Ciba Geigy | Protection of metal surfaces |
| US5320768A (en) * | 1988-06-24 | 1994-06-14 | Exxon Chemical Patents Inc. | Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith |
| FR2702772A1 (en) * | 1993-03-17 | 1994-09-23 | Bp Chemicals Snc | Hydraulic fluid composition. |
| FR2731010A1 (en) * | 1995-02-24 | 1996-08-30 | Renault | Multifunctional additive for petrol or diesel motor fuels |
| FR2730994A1 (en) * | 1995-02-24 | 1996-08-30 | Renault | Additives derived from 3-alkoxy-1-alkyl:amino:propan-2-ol (dimer) |
| EP0765929A1 (en) * | 1995-03-31 | 1997-04-02 | Kao Corporation | Additive for lubricating oils for diesel engines and lubricating oil compositions containing the same |
| US5670464A (en) * | 1993-01-25 | 1997-09-23 | Kao Corporation | Additive for lubricating oils for diesel engines and lubricating oil compositions containing the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB979667A (en) * | 1962-05-23 | 1965-01-06 | Shell Int Research | Nitrogen and hydroxyl containing ester adducts and the production of polyurethanes |
| GB980003A (en) * | 1961-11-02 | 1965-01-13 | Oreal | New amine and quaternary ammonium compounds,their preparation and their use |
-
1986
- 1986-03-10 GB GB08605820A patent/GB2172284B/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB980003A (en) * | 1961-11-02 | 1965-01-13 | Oreal | New amine and quaternary ammonium compounds,their preparation and their use |
| GB979667A (en) * | 1962-05-23 | 1965-01-06 | Shell Int Research | Nitrogen and hydroxyl containing ester adducts and the production of polyurethanes |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS COMPOUND OF REGISTRY NUMBER 96507-75-4 * |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0206998A2 (en) * | 1985-06-21 | 1986-12-30 | Ciba-Geigy Ag | Lubricant compositions, glucamin derivatives and complex compounds containing them |
| EP0206998A3 (en) * | 1985-06-21 | 1989-08-09 | Ciba-Geigy Ag | Lubricant compositions, glucamin derivatives and complex compounds containing them |
| US5002698A (en) * | 1986-01-10 | 1991-03-26 | Ciba-Geigy Corporation | Sulfur- and nitrogen-containing lubricant additives |
| EP0233140A1 (en) * | 1986-01-10 | 1987-08-19 | Ciba-Geigy Ag | Lubricant additives containing sulphur and nitrogen |
| US4863621A (en) * | 1986-01-10 | 1989-09-05 | Ciba-Geigy Corporation | Sulfur-and nitrogen-containing lubricant additives |
| US4835310A (en) * | 1986-03-13 | 1989-05-30 | Ciba-Geigy Corporation | Reaction products of bisglycidyl thioethers |
| EP0237489A1 (en) * | 1986-03-13 | 1987-09-16 | Ciba-Geigy Ag | Conversion products of bis-glycidylthioethers |
| EP0239536A3 (en) * | 1986-03-22 | 1989-07-26 | Ciba-Geigy Ag | Lubricant compositions |
| EP0239536A2 (en) * | 1986-03-22 | 1987-09-30 | Ciba-Geigy Ag | Lubricant compositions |
| EP0255126A3 (en) * | 1986-07-30 | 1989-01-11 | Godecke Aktiengesellschaft | 2-acyloxypropylamine derivatives, method for their preparation and medicaments containing them |
| EP0255126A2 (en) * | 1986-07-30 | 1988-02-03 | Gödecke Aktiengesellschaft | 2-Acyloxypropylamine derivatives, method for their preparation and medicaments containing them |
| EP0378883A1 (en) * | 1987-12-07 | 1990-07-25 | Mobil Oil Corporation | Low temperature fluidity improver |
| EP0353854A1 (en) * | 1988-06-24 | 1990-02-07 | Exxon Chemical Patents Inc. | Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith |
| US5320768A (en) * | 1988-06-24 | 1994-06-14 | Exxon Chemical Patents Inc. | Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith |
| US4888138A (en) * | 1988-11-10 | 1989-12-19 | Ethyl Corporation | Substituted ammonium carbamates and method for preparing same |
| GB2227757B (en) * | 1989-02-03 | 1992-10-07 | Ciba Geigy Ag | Protection method |
| GB2227757A (en) * | 1989-02-03 | 1990-08-08 | Ciba Geigy | Protection of metal surfaces |
| US5670464A (en) * | 1993-01-25 | 1997-09-23 | Kao Corporation | Additive for lubricating oils for diesel engines and lubricating oil compositions containing the same |
| FR2702772A1 (en) * | 1993-03-17 | 1994-09-23 | Bp Chemicals Snc | Hydraulic fluid composition. |
| EP0617116A1 (en) * | 1993-03-17 | 1994-09-28 | BP Chemicals Limited | Hydraulic fluid composition |
| FR2731010A1 (en) * | 1995-02-24 | 1996-08-30 | Renault | Multifunctional additive for petrol or diesel motor fuels |
| FR2730994A1 (en) * | 1995-02-24 | 1996-08-30 | Renault | Additives derived from 3-alkoxy-1-alkyl:amino:propan-2-ol (dimer) |
| EP0765929A1 (en) * | 1995-03-31 | 1997-04-02 | Kao Corporation | Additive for lubricating oils for diesel engines and lubricating oil compositions containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8605820D0 (en) | 1986-04-16 |
| GB2172284B (en) | 1988-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930310 |