JPS6366297A - 2-propanol derivative as corrosion inhibitor - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention This invention relates to compounds useful as corrosion inhibitors for ferrous metals. More particularly, the present invention relates to derivatives of propan-2-ol which have been found to exhibit excellent action as corrosion inhibitors for ferrous metals in contact with functional fluids.

[Prior art, problems to be solved by the invention, and means for solving the problems]

U.S. Pat. No. 4,134,846 and No. 4
147641, a) glycidyl of the formula: in which R represents an aliphatic hydrocarbon radical containing at least 8 carbon atoms and m is 1°2 or 3; A multipurpose hydrocarbon fuel and lubricating oil additive mixture is disclosed comprising a reaction product of an ether and a primary or secondary monoamine or polyamine, and b) each of a polyalkylene phenol or polycarboxylic acid ester.

Furthermore, Mamedov et al.
kad.

Nauk, Az, SIR34(7), 1980. p
In p. 51-s, a compound represented by the following formula is described as a biocide in lubricating oil.

The present invention provides a functional liquid that contacts ferrous metal and the following formula (I):
(8) [In the formula, R, R and R each independently represent a hydrogen atom, a straight or branched alkyl residue having 1 to 15 carbon atoms, a cycloalkyl residue having 5 to 12 carbon atoms, or a carbon atom. represents an aryl residue having 6 to 15 carbon atoms or an aralkyl residue having 7 to 12 carbon atoms, and R and R are each independently a hydrogen atom, a 2-hydroxyethyl group, or a 2-hydroxyethyl group.
Represents a hydroxypropyl group, provided that a) R and Rid do not represent hydrogen atoms at the same time, and b)
When R and R each represent a -Ct(2-CF(2-OH) group, R1 and R2 do not simultaneously represent a hydrogen atom, R does not represent a pentyl residue, and C) polyalkylenephenol or poly and an effective amount as a corrosion inhibitor of at least one propan-2-ol derivative and a salt thereof.

One or more of R2H and
to 15 straight-chain or branched alkyl residues, they are methyl, ethyl, n-propyl, isopropyl, n-, iso- or tert-butyl, '-
1iso- or 1di3-bentyl group, n-hexyl group, n
-heptyl group, n-octyl group, tertiary-octyl group, n
- or iso-nonyl group, rho or iso-decyl group, n-
or iso-undecyl group, n- or iso-dodecyl group,
n- or in-tridecyl group, n- or iso-tetradecyl group, n-pentadecyl group or C15 [(sl - or 6) or a mixture containing a large proportion of alkyl residues derived from C, H, residues derived from hydrogenated cashew oil.

a cycloalkyl residue having 5 to 12 carbon atoms,
R2 and R3 mainly represent cyclopentyl, cyclohexyl and cyclodecyl residues.

Aryl residue having 6 to 15 carbon atoms] "L".

几2 and 几3 mainly represent phenyl or naphyl residues, especially phenyl residues.

If one or more of R1, R2 and R3 represents a C7-C12 aralkyl radical, they represent a benzyl group, an α-methylbenzyl group or an α-methylbenzyl group.
, α-dimethylbenzyl group.

Inorganic acids such as hydrochloric acid, sulfuric acid, sulfonic acid, phosphonic acid or boric acid or suitable organic acids such as formic acid, acetic acid, propionic acid, gluconic acid, lauric acid, succinic acid, sebacic acid, maleic acid, citric acid, tartaric acid, Salts are formed from the amine functionality of compounds of formula I using oxalic acid, benzoic acid, phthalic acid or trimellidic acid.

The salt may be oil-soluble or water-soluble and is commonly
1. Total or partial salts of di- or tribasic acids. The salts may also be formed from partial esters of di- or tribasic acids such as methyl maleate or methyl succinate.

Most of the compounds of formula I are new, however, some compounds have been disclosed in which one or two of R1, R2 and R3 represent an alkyl group. Therefore, U.S. Pat. No. 3,033,640 describes a method useful for improving the dyeability of certain materials of the following formula: where A' is an aromatic group which may be alkylated, e.g. lower alkyl. represents a phenyl group or a di(lower alkyl)phenyl group, n is 1 or 2, and 几′ represents a hydrogen atom or a hydroxyalkyl group,
and R" specifically represents a hydrogen atom. However, in the examples disclosed herein, R' and R" are both hydroxyalkyl groups.

Japanese Patent Application No. 54-57776 (80,130359
) describes a compound of the following formula useful for forming sand molds.

DE 2559926 contains, for example, the following formula: [wherein R' represents a hydrogen atom and R'' represents a hydrogen atom or a 2- or 5-methyl group: R' represents a 2- or 5-methyl group;
- represents a methyl group, R" represents a 3-isopropyl group; R' represents a 3-methyl group, R" represents a 2-isopropyl group; or R' represents a 5-methyl group; R" represents a 2-isopropyl group" are described.

Conde et al., Congr, Nac,
Bfofarm.

Farmacocinet+(Actas) j7t
, No. 1, 1977, pages 455-456, describes pharmacokinetic studies on compounds of the formula: and Spanish Patent No. 41 by the same author.
No. 2965 discloses a compound represented by the following formula:

British Patent No. 1,439,719 discloses compounds of the following formula as starting materials for radiation-curable synthetic resins.

Accordingly, the present invention also provides the following formula (I): [In the formula, Bl, "B1", R3, R' and R5 have the same meanings as above, with the proviso that a) one of R", R2 and R3 or More than that.

represents an alkyl group having 1 to 15 carbon atoms, R4
or when R5 represents a hydrogen atom, b) R,' and R
When 5 each represents a -CH, CF((OH)CI(,) group, R1 and R2 represent a hydrogen atom, and 3 represents a hydrogen atom or a 4-CH2CH(CH3)2 group,
and c) when R' and R5 represent each k-C)I2CH20F (group, R1 represents a hydrogen atom, R2 represents a hydrogen atom or a methyl group, and R represents a hydrogen atom or an isopropyl group, d) [Excluding the case where R, 1, R2 and 几3 simultaneously represent a hydrogen atom] is provided.

Preferred compounds represented by formula (I) are those having 1.
R2 or R3 independently has 3 to 15 carbon atoms;
represents a branched alkyl residue, in particular a propyl, butyl, amyl, octyl, nonyl or dodecyl group.

More preferred compounds represented by formula (I) are
3 represents a hydrogen atom, R1 and 几2 are the same and represent a branched alkyl residue having 3 to 15 carbon atoms, and R
This is a compound in which 4 and R5 have the same meanings as above.

The most preferred compounds of formula (I) are those in which R
1 and R2 represent hydrogen atoms, and R3 has 3 to 154 carbon atoms at the meta- or para-position of the oxygen atom of the phenol ring. - represents a linear or branched alkyl residue having 9 carbon atoms, and R4 and R5 represent a 2-hydroxyethyl residue or a 2-hydroxypropyl residue.

In addition to the above, preferred compounds represented by the formula (I), where R, l, R2 and R3 are each i-C3)i,
A compound representing a group.

The compound represented by the formula (I) is a compound represented by the following formula (■):)t3 [wherein R'', R'' and 几3 represent the same meanings as above], or a metal salt thereof such as a sodium salt or The potassium salt is reacted with a compound represented by the following formula (IID: [wherein X represents a chlorine atom or a bromine atom], optionally in the presence of a catalyst such as an acid, a base, or a phase transfer catalyst to obtain the following formula (■ ): A compound represented by 3 is prepared, and then amine HNR [
wherein R and R have the same meanings as defined above] to form a compound represented by formula (I).

Compounds of the formula (0) are particularly suitable as starting materials for the synthesis of compounds of the formula (I), including the following compounds: 2-methylphenol, 3-methylphenol, 4-methylphenol, 2-ethylphenol. Phenol, 3-ethylphenol, 4-ethylphenol, 2-isopropylphenol, 3-isopropylphenol, 4-isopropylphenol, 2-secondary butylphenol, 3-secondary methylphenol, 4-secondary methylphenol, 2 -isobutylphenol, 3-isobutylphenol, 4-
Isobutylphenol, 2-tert-butylphenol, 3
-tert-butylphenol, 4-tert-butylphenol,
2-tertiary amylphenol, s-tertiary amylphenol, 4-tertiary amylphenol, 2-cyclohexylphenol, 3-cyclohexylphenol, 4-cyclohexylphenol, 2-tertiary octylphenol, 6-
Tertiary octylphenol, 4-tertiary octylphenol, 2-nonylphenol, 3-nonylphenol, 4-
Nonylphenol, 2-dodecylphenol, 3-dodecylphenol, 3-bentadecylphenol, C15 pentadecylphenol, including phenolic mixtures obtained from cashew oil, 4-dodecylphenol, 2-phenylphenol, 3- Phenylphenol, 4-phenylphenol, 2-cumylphenol, 3-S-ruphenol, 4-cumylphenol, 2
．． 4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 5.5-dimethylphenol, 2.4-diethylphenol, 2,5-diethylphenol, 2.6-diethylphenol, 3,5
-diethylphenol, 2,4-diisopropylphenol, 2,5-diisopropylphenol, 2゜6-diisopropylphenol, 3,5-diisopropylphenol, 2,4-di-nibutylphenol, 2,5-
Di-nibutylphenol, 2,6-di-nibutylphenol, 3゜5-di-nibutylphenol, 2,4
-di-tert-butylphenol, 2,5-di-tert-butylphenol, 2,6-di-tert-butylphenol, 5,
5-di-tert-butylphenol, 2゜4-di-tert-butylphenol, 2.5-di-tert-amylphenol, 2
, 6-di-tertiary amylphenol, 3,5-di-tertiary amylphenol, 2,4-dicyclohexylphenol, 2,5-dicyclohexylphenol, 2,6-dicyclohexylphenol, 3.5-dicyclohexylphenol, 2,4 -Dinonylphenol, 2,4.6-
Contains doliisoglobilphenol.

Many of the above substituted phenolic starting materials are not always readily available in isomerically pure form.

To synthesize the compounds of formula (I), mixtures of isomers are used, if appropriate. for example,
Commercially available p-nonylphenol is believed to consist of a mixture of several C9 branched alkyl residues and may additionally contain small and variable amounts of ortho- and meta-isomers.

In the compound represented by formula (I) in which R and R are the same and represent a 2-hydroxyethyl group or a 2-hydroxypropyl group, the epoxide represented by formula (IV) is converted to jetanolamine or diisopropyl It is conveniently prepared by dropwise addition to equimolar amounts of patoolamine, and the preferred reaction temperature is in the range 70-90°C. The product thus obtained is sufficiently pure69 and does not require any purification.

In the compound represented by formula (I) in which R4 represents a hydrogen atom and R5 represents a 2-hydroxyethyl group or a 2-hydroxypropyl group, the epoxide represented by formula (IV) is converted to ethanolamine or isopropyl. Conveniently prepared by dropwise addition of a tool amine in excess, preferably about 5 times molar, the preferred reaction temperature is 70-90 molar excess.
℃ range. The product thus obtained is preferably isolated by fractional distillation of the reaction mixture.

Compounds of formula (I) are useful in imparting desired properties to functional fluids, particularly corrosion protection.

This compound has [101-5 heavy tt4,
It is particularly effective as a corrosion inhibitor in functional fluids in amounts of 0.02-1% by weight. Preferably, the functional fluid is a non-aqueous functional fluid.

The non-aqueous functional fluid may be a lubricating oil such as a natural or synthetic lubricating oil; a refined petroleum product such as fuel oil, diesel oil, oil, kerosene, gasoline or aviation fuel; or a hydraulic fluid such as a phosphatase synthetic oil.

The lubricating oil may be mineral oil, synthetic oil or any mixture of these oils. Mineral oils, especially steam turbine oils, are particularly useful; examples thereof include paraffinic hydrocarbon oils, e.g.
Mineral oil with a viscosity of 46 J/S at 0°C;
solvent, which is a purified neutral mineral oil containing albicans, a viscosity of 32 J/s at 40°C; 1 solvent bright-stocks (5 solvent bright-stocks)
”, obtained from mineral oil refining process, 46 a/m at 40°C
Mention may be made of high-boiling residues having a viscosity of S.

Synthetic lubricating oils that may be present include synthetic hydrocarbons such as polybutenes, alkylbenzenes and polyalpha-olefins as well as single di-, tri- and tetra-esters, complex esters and
7 [In the formula, "alkylene" represents an alkylene residue having 2 to 14 carbon atoms, and R and R are the same or different and each represents an alkyl group having 6 to 18 carbon atoms] It may be a polyester obtained from an ester.

Triesters used as lubricating oil base stocks are those obtained from trimethylolpropane and C6 to C18 monocarboxylic acids or mixtures thereof, while suitable tetraesters are pentaerythritol and C6 to C18 monocarboxylic acids or mixtures thereof. 18 monocarboxylic acids or mixtures thereof.

Complex esters suitable for use as components of the compositions of the invention are those obtained from monobasic acids, dibasic acids and polyhydric alcohols, such as those obtained from trimethylolpropane, caprylic acid and sebacic acid.

Suitable polyesters 1d are obtained from C4-C1-14 aliphatic dicarboxylic acids and at least one C3-C12 aliphatic dihydric alcohol, such as azelaic acid or sebacic acid, and 2.2. It is obtained from 4-trimethylhexane-1,6-diol.

The lubricating oil application medium also contains other additives that may be added to improve the basic performance of the lubricant, such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants. It may also contain detergents, detergents, extreme pressure additives and anti-wear additives.

2.6-di-tert-butyl-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2.6-di-tert-butyl-4-ethylphenol, 2.6-di-tert-butyl-4- n-Butylphenol, 2.6-di-tert-butyl-4-i-butylphenol, 2.6-di-cyclopentyl-4-methylphenol, 2-(β-methylcyclohexyl)-4°6-dimethylphenol2. 6-di-octadecyl-4-methylphenol, 2,4.6-)dicyclohexylphenol, 2.6-di-tert-butyl-4-methoxymethylphenol 2 Alkylated hydroquinone 2.6-di-tert-butyl-4 -methoxyphenol 21 s-di-tert-butyl-hydroquinone, 2.5-
Di-tert-butyl-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol 2,2'-thio-bis(6-tert-butyl-4-methylphenol), 2,2'-thio-bis( 4-octylphenol), 4.4'-thio-bis(6-tert-butyl-3-methylphenol), 4.4'-thio-bis(6-tert-butyl-2-methylphenol)6 2.2 '-Methylene-bis(6-tert-butyl-4-methylphenol), 2.2'-methylene-bis(6-tert-butyl-4-ethylphenol), 2.2'-methylene-bis(4- Methyl-6-(α-methylcyclohexyl)phenol), 2.2'-methylene-bis(4-methyl-6-cyclohexylphenol), 2.2'-methylene-bis(6-nonyl-4-methylphenol) ), 2.2'-methylene-bis(4,6-di-tert-butylphenol), 2.2'-ethylidene-bis(4,6-di-tert-butylphenol), 2.2'-ethylidene-bis(6 -tert-butyl-5-isobutylphenol), 2,2'-methylene-bis(6-(α-methylbenzyl-4-nonylphenol), 2,2'-methylene-bis(6-(α,α-dimethyl benzyl)-4-nonylphenol), 4,4'-methylene-bis(6-tert-butyl-2-methylphenol), 1,1'-bis(5-tert-butyl-4-hydroxy-2
-methylphenol)phthane, 2,6-di(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1.3-)lis(5-tert-butyl-4- hydroxy-2-methylphenyl)-5-n-dodecyl)mercaptobutane, ethylene glycol-bis(5,3-bis(3'-i37'thyl-4'-hydroxyphenyl)butyrate], di(3- Tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, di[(5'-tert-butyl-2'-hydroxy-5'-,)Z thyl-benzyl)
-6-tertiary 7'thyl-4-methyl-phenyl]terephthalate.

1,5.5-)su(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, di(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide , bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiol terephthalate, 1,3.5-)lis(3,5-di-tert-butyl-4-
hydroxybenzyl) isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 5,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid Dioctadecyl ester, 5,5-cy 1 g, triphthyl-4-hydroxybenzyl-phosphate monoethyl ester calcium salt.

4-hydroxy-laurylic acid anilide, 4-hydroxy-stearic acid anilide, 2,4-bis-octylmercapto-6-(3,5-di-tert-butyl-4-hydroxyanilino)-8-) riazine, N -(3,s-di-tert-butyl-4-hydroxyphenyl)carbamic acid octyl ester.

Polyhydric alcohols such as methanol, diethylene glycol, octadecanol, triethylene glycol, 1.
Esters with 6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl-isocyanurate, thiodiethylene glycol, dihydroxyethyl oxalic diamide.

is a polyhydric alcohol such as methanol, diethylene glycol, octadecanol, triethylene glycol, 1
, 6-Hexanediol, Bentae IJ) Esters with TJ toll, neopentyl glycol, tris-hydroxyethyl-isocyanurate, thiodiethylene glycol, di-hydroxyethyl oxalic diamide.

N,N'-di(5,5-di-tert-butyl-4-hydroxyphenylglobionyl)hexamethylenediamine,
N,N'-di(3,5-di-tert-phthyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,
N'-di(3,5-di-tert-butyl-4-hydroxyphenylglobionyl)hydrazine.

Examples of amine antioxidants: N,N'-isopropyl-p-phenylenediamine, NIN'l-gnibutyl-p-phenylenediamine, N,N'-bis(1,4-dimethyl-pentyl)-p-
7 Enylenediamine, N,N'-bis(1-ethyl-3-methyl-pentyl)
-p-phenylenediamine, N,N'-bis(1-methyl-heptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine , N,N'-di(naphthyl-2)-p-phenylenediamine, N-isopropyl-N/-phenyl-p-phenylenediamine, N-(1,3-dimethyl-butyl)-N'-phenyl-
p-phenylenediamine, N-(1-methyl-heptyl)-N'-722p-
Phenylenediamine, N-7chlorohexyl-NZ-phenyl-p-phenylenediamine, 4-(p-toluene-sulfonamido)diphenylamine, N,N'-dimethyl-N,N'-di-tert-nibutyl-p-
Phenyl diamine, diphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, octylated N-phenyl-(also (I) naphthylamine), 4-n- Butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-monodecaylaminophenol, 4-octadecanoylaminophenol, di(4-methoxy-phenyl)amine, 2,6-di Tert-butyl-4-dimethylamino-methylphenol, 2,4'-diamino-diphenylmethane, 4,4'-diamino-diphenylmethane, N, N, N', N
'-Tetramethyl-4,4'-diamino-diphenylmethane, 1.2-1>(phenylamino)ethane, 1.2-di[
(2-Methyl-phenyl)aminocoethane, 1,3-di(phenylamino)propane, (0-tolyl)biguanide, di[4-(1', 3'-dimethyl-butyl)phenylamino.

Examples of metallic SSa forming agents include: For copper, for example, benzo) IJ azole, tetrahydrobenzotriazole, tolutriazole, 2-mercaptobenzothiazole, 2゜5-dimercaptothiadiazole, salicylidene-propylene of salicylaminoguanidine. Diamine salts and European Patent Application No. 160
1.2.4- as disclosed in No. 620
triazole and formaldehyde and amine HNR,
N,N-disubstituted aminomethyl of the following formula obtained by reacting R, , where R8 and R9 independently represent an alkyl group, an alkenyl group or a hydroxyethyl group. Mention may be made of triazoles and Mannich reaction products obtained from benzotriazole or toltriazole, formaldehyde and amines) (NR, 8R9).

Examples of further rust inhibitors include: a) Organic acids, their esters, metal salts and anhydrides such as N-oleo-sarcocne, sorbitan-mono-
oleate, lead naphthenate, tothycenyl-succinic acid, alkenyl-j-succinic acid partial esters, such as the product sold under the trade name Lubrizol 859 (Lubrizol Co.
rp, ).

United States of America] Alkenyl-succinic acid partial imide, e.g. Hitec 536 [trademark of Ethyl Corp., United States of America] and 4-nonyl-phenoxyacetic acid, b) Nitrogen-containing compounds, e.g. ．． Secondary or tertiary aliphatic or cycloaliphatic amines and amine salts of organic and inorganic acids, such as oil-soluble alkyl ammonium carboxylates, and (1) heterocyclic compounds such as substituted imidazolidines and oxazolidines, C) phosphorus-containing compounds For example, amine salts of phosphoric acid and phosphoric acid partial esters, d) sulfur-containing compounds such as barium dinonylnaphthalene sulfonate and petroleum sulfone cough calcium, e) γ-alkoxypropylamine as described in Japanese Patent Publication No. 1578+/1973. Derivatives, and the following formula: Y-NH3・f("CO2-[wherein, YF
i1%"X' CHI CH(OH) represents a CH2 group, in the above formula, R" and 几11 independently represent, for example, an alkyl group, and Xl represents 0XCO2, NH
, N (alkyl), N (alkenyl) or s6]
These salts include those prepared by mixing the amine Y-NH2 and the acid R10Co2H as described in British Patent Application No. 2148294. .

Examples include polymethacrylate, vinylpyrrolidone/methacrylate copolymer, polybutene, olefin copolymer, and styrene/acrylate copolymer.

Examples of pour point depressants include, for example, polymethacrylates and alkylated naphthalene derivatives.

Mention may be made of polybutenylsuccinimide, polybutenylphosphonic acid derivatives and basic magnesium-, calcium-1 and barium sulfonates and -ferulates.

Sulfur- and/or phosphorus- and/or nitrogen-containing compounds include, for example, sulfurized vegetable oils, zinc dialkyldithioates, tritolyl phosphates, chlorinated paraffins and alkyl- and aryl disulfides.

In less preferred embodiments, the functional fluid may be partially aqueous, for example an aqueous cutting oil formulation, such as a water-dilutable cutting or grinding fluid, or an industrial cleaning fluid.

The aqueous cutting formulation treated according to the invention may be, for example, a metalworking formulation. 1. The term "metalworking" includes reaming, broaching, drawing, spinning, cutting, grinding, yt'-+)yy(boring), milling, application, sawing, This refers to uncut forming, rolling, or quenching. Examples of water-dilutable cutting or grinding fluids in which corrosion-inhibiting compounds may be used include:

a) aqueous sacrificial fluids, usually used as grinding fluids, consisting of one or more corrosion inhibitors and optionally one or more anti-wear additives; b) biocides, corrosion inhibitors; C) a polyglycol in a cutting operation or grinding pool, containing additives and anti-wear additives; C) an additional 10 to 25 oils with sufficient emulsifier to make the water-diluted product free-flowing; b
), d) emulsifying mineral oil concentrates containing e.g. emulsifiers, corrosion inhibitors, extreme pressure/anti-wear additives, biocides, defoamers, coupling agents, etc. (usually a white opaque emulsion when diluted with water); e) a translucent emulsion upon dilution; similar to (d) for cutting or grinding operations, containing a small amount of oil and a larger amount of emulsifier; product of.

For the partially aqueous systems mentioned above, where the functional fluid is an aqueous working fluid formulation, inhibitor component B) is used alone or in admixture with other additives, such as other known corrosion inhibitors or extreme pressure additives. It is possible.

Examples of other corrosion inhibitors that can be used in these aqueous systems in addition to the compounds of formula I used according to the invention include:

a) Organic acids, their esters or ammonium, amines, alkanolamines and metals and their salts, such as benzoic acid, p-tert-butylbenzoic acid, disodium sebacate, triethanolamine laurate, isononanoic acid, 1) -) Triethanolamine salt of luenesulfonamidocaproic acid, triethanolamine salt of benzenesulfonamidocaproic acid, European Patent No. 4192
b) Nitrogen-containing substances such as the following types: fatty acid alkanolamides; ; imidacillins such as 1-hydroxyethyl-2-oleyl-imidacillin; oxazolines; triazoles such as benzotriazole; or Mannich base derivatives thereof; triethanolamine; fatty amines, inorganic salts such as sodium nitrate; and European Patent Application No. 46159 C) Phosphorus-containing substances such as the following types: amine phosphates, phosphonic acids or inorganic salts such as dihydrogen phosphate)
d) temporary yellow-containing compounds sodium, calcium or barium dipetroleum sulfonates, such as the following types, or heterocyclic compounds such as sodium mercaptobenzothiazole.

Nitrogen-containing substances are preferred, especially triethanolamine.

When applied to partially aqueous functional fluids, the compounds of formula (I) can be combined with water-soluble derivatives such as organic acids such as C6 -C20 carboxylic acids such as lauric acid, or inorganic acids such as hydrochloric acid, nitric acid or boric acid. Preferred are the salt forms formed using

The functional fluid may be a substantially aqueous system such as a water-based cutting fluid, a water-based surface paint such as a dispersion paint, an emulsion paint or an electrocoated paint; or an entirely aqueous system such as a cooling water system, an air conditioning system, a water vapor generation system, a seawater evaporation system, It may be a pressure cooker system, or a closed circuit heating system or a refrigeration cooling system.

The compounds of formula (I) are particularly useful as additives to lubricating systems, especially turbine and engine oils, where they exhibit corrosion-inhibiting properties.

[Examples and effects of the invention]

The invention is illustrated in greater detail in the following examples. All parts and percentages are by weight.

Example 1 While stirring at 80°C, 276 parts of p-nonylphenylglycidyl ether was added to 105 parts of jetanolamine. After complete addition, the reaction temperature is maintained at 80° C. for an additional hour. The quantitatively obtained product 1-[:N,N-bis(2
-hydroxyethyl)amine]-3-(4-nonylphenoxy)propan-2-ol is a colorless, viscous oil and does not require any purification. t(nmr (CDC/!3
); δ7.2-6.5 (m, 4F(); 4.
6 (S, 3H): 4.1-! 1.2 (m, 7
H);! LO-2,1 (m, /IH): 2.0-
0.3 (m, 19H).

Example 2 Using the method described in Example 1, 206 parts p-tert-butylphenyl glycidyl ether t') was reacted with 105 parts ethanolamine to give 1-tert-butylphenyl glycidyl ether as a colorless, viscous oil.
(N,N-bis(2-hydroxyethyl)amine)-3
-(4-tert-butylphenoxy)propan-2-ol is obtained which, when cooled, becomes a white solid with a melting point of 45-7°C.

'Hnmr (CDCl3): δ7.4-1. ．． 6
(m, 4H); 4.9(s, 3H);
4.3-15 (m, 7H); &1-2
．． 2 (m.

6H); t5 (s, 9H).

Example 5 Using the method described in Example 1, 234 parts of 2,4-diisopropylphenyl glycidyl ether are reacted with 133 parts of diisopropanolamine to give 1-[N,N-bis as a colorless, viscous oil. (2-Hydroxypropyl)amine]-3-(2,4-diisopropylphenoxy)propan-2-ol is obtained. 'Hnmr (CDCl3
); 7.0-B5 (m, 3H): 4.8
(s, 3H): 4.2-2.0 (m.

13H); 1.5-B9(m, 18H).

Example 4 101 parts of 4-tertiary octylphenyl glycidyl ether were mixed with 12 parts of ethanolamine while stirring at 80-85°C.
Added to part 2. After complete addition, the reaction mixture was kept at 80-85°C for an additional hour.

Excess ethanolamine was removed by total distillation of the reaction mixture at a pressure of 3525 mbar.

The remaining oil was then distilled under high vacuum to form a colorless, viscous oil with a temperature of 230°C/a93 mm IJ bar (
When left to stand, a white solid with a melting point of 64-6°C and 1-(
100 parts of N-2-hydroxyethyl)-3-(4-tertiary octylphenoxy)propan-2-ol are obtained. 1
Hnmr (CDCl5); δ7.0 (d, 2H
): 6.6 (d, 2H): 4.5-14
(m.

8H); xo-2,4(m, 4H): 1.6
(s, 2H); t3(s, 6H) :B7(s
, 9H).

The following formula: [where Bl, B2, BS, B4 and R5
have the same meanings as above] are produced by the same method and are shown in Table 1.

Examples 30 to 39 Some products of formula (I) have a viscosity of 31.6 wJ/s at 40°C and a viscosity of 4.6 at 100°C.
/S1 Typical Sulfur Content (A8TM I as a Corrosion Inhibitor in 16-inch Turbine Grade Mineral Oil) Tested Using Method 66513. Passing this test indicates that there are no traces of rust on the test spindle. In the absence of additives, severe rust occurs on the test spindle. The results are shown in Table 2.

Table 2

Claims (14)

[Claims] (1) Functional liquid that comes into contact with ferrous metal and the following formula (I): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) [In the formula, R^1, R^2 and R^3 are independent of each other. a hydrogen atom, a straight-chain or branched alkyl residue having 1 to 15 carbon atoms, a cycloalkyl residue having 5 to 12 carbon atoms, an aryl residue having 6 to 15 carbon atoms or an alkyl residue having 7 to 12 carbon atoms; represents an alkyl residue, and R^4 and R^5 independently of each other represent a hydrogen atom, a 2-hydroxyethyl group or a 2-hydroxypropyl group, provided that a) R^4 and R^5 simultaneously represent does not represent a hydrogen atom, b) R^4 and R^5 are each -CH_2-CH_2-OH
When representing a group, R^1 and R^2 do not simultaneously represent a hydrogen atom, R^3 does not represent a pentyl residue, and c) no polyalkylene phenol or polycarboxylic acid ester co-additive is present. A composition comprising an effective amount as a corrosion inhibitor of at least one of a compound represented by the following formula, or a derivative thereof, or a salt thereof. (2) The composition according to claim 1, wherein the amount of the compound represented by formula (I) is in the range of 0.01-5% by weight based on the weight of the functional fluid. (3) The composition according to claim 1, wherein the functional fluid is a lubricating oil, a refined petroleum product, or a hydraulic fluid. (4) The composition according to claim 3, wherein the lubricating oil is mineral oil. (5) Claim 4 in which the mineral oil is steam turbine oil
Compositions as described in Section. (6) The lubricating oil further contains one or more antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, extreme pressure and anti-wear additives. 4. The composition according to claim 3, which comprises an agent. (7) The following formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1, R^2 and R^3 each independently represent a hydrogen atom, a carbon atom number of 1 or 15 straight-chain or branched alkyl residues, C5 -C12 cycloalkyl residues, C6 -C15 aryl residues or C7 -C12 aralkyl residues, and R ^4 and R^5 each independently represent a hydrogen atom, a 2-hydroxyethyl group or a 2-hydroxypropyl group, provided that a) one or more of R^1, R^2 and R^3; The above represents an alkyl group having 1 to 15 carbon atoms, and R
When ^4 or R^5 represents a hydrogen atom, b) R^4 and R^5 each represent -CH_2CH(OH)CH
_3 group, R^1 and R^2 represent hydrogen atoms,
And R^3 is a hydrogen atom or 4-CH_2CH(CH_
3) _2 group, and c) R^4 and R^5 each represent a -CH_2CH_2OH group, R^1 represents a hydrogen atom, R^2 represents a hydrogen atom or a methyl group, and R^ When 3 represents a hydrogen atom or an isopropyl group, d) Except when R^1, R^2 and R^3 simultaneously represent a hydrogen atom]. (8) The compound according to claim 7, wherein in formula (I), R^1, R^2 or R^3 independently represent a branched alkyl residue having 3 to 15 carbon atoms. (9) The compound according to claim 8, wherein in formula (I), R^1, R^2 and R^3 each represent an i-C_3H_7 group. (10) In formula (I), the branched alkyl residue R^1, R^2 or R^3 having 3 to 15 carbon atoms is a propyl group, a butyl group, an amyl group, an octyl group, a nonyl group or a dodecyl group; 9. A compound according to claim 8, which represents (11) In formula (I), R^3 represents a hydrogen atom, and R^1 and R^2 are the same and represent branched chain alkyl residues having 3 to 15 carbon atoms, Claim 7 Compounds described. (12) In formula (I), R^1 and R^2 represent hydrogen atoms, and R^3 is meta- to the oxygen atom of the phenol ring.
or a straight-chain or branched alkyl radical having 3 to 15 carbon atoms in the para-position, and R^4 and R^5 represent a 2-hydroxyethyl group or a 2-hydroxypropyl radical; A compound according to scope item 7. (13) The compound according to claim 12, wherein in formula (I), R^3 represents a linear or branched alkyl residue having 9 carbon atoms. (14) The following formula (I) as a corrosion inhibitor in functional fluid:
▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R^1, R^2 and R^3 are each independently a hydrogen atom, a linear or branched alkyl residue having 1 to 15 carbon atoms, represents a cycloalkyl residue having 5 to 12 carbon atoms, an aryl residue having 6 to 15 carbon atoms or an aralkyl residue having 7 to 12 carbon atoms, and R^4 and R^5 are mutually independent. represents a hydrogen atom, 2-hydroxyethyl group or 2-hydroxypropyl group, provided that a) one or more of R^1, R^2 and R^3 has 1 to 15 carbon atoms; represents an alkyl group, R
When ^4 or R^5 represents a hydrogen atom, b) R^4 and R^5 each represent -CH_2CH(OH)CH
_3 group, R^1 and R^2 represent hydrogen atoms,
And R^3 is a hydrogen atom or 4-CH_2CH(CH_
3) _2 group, and c) R^4 and R^5 each represent a -CH_2CH_2OH group, R^1 represents a hydrogen atom, R^2 represents a hydrogen atom or a methyl group, and R^ When 3 represents a hydrogen atom or an isopropyl group, d) Except when R^1, R^2 and R^3 simultaneously represent a hydrogen atom].