CN1308292C - Succinic acid semi-amides as anti-corrosives agents - Google Patents

Succinic acid semi-amides as anti-corrosives agents Download PDF

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CN1308292C
CN1308292C CNB038221683A CN03822168A CN1308292C CN 1308292 C CN1308292 C CN 1308292C CN B038221683 A CNB038221683 A CN B038221683A CN 03822168 A CN03822168 A CN 03822168A CN 1308292 C CN1308292 C CN 1308292C
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alkyl
oil
group
carboxyl
butyl
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CN1681772A (en
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H·卡门青德
P·汉吉
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BASF Schweiz AG
Ciba SC Holding AG
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Ciba Spezialitaetenchemie Holding AG
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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
    • C10M133/16—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • 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
    • C10M133/24—Nitriles
    • 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
    • C10M133/38—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/16—Nitriles
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Abstract

The invention relates to improved compositions based on lubricants and comprising succinic acid semi-amides and to the use of those lubricant compositions in improving the use properties of lubricants, such as hydraulic or metal-working fluids, greases, gear oils or engine oils.

Description

Succsinic acid half amide as resist
The composition and these compositions that the present invention relates to contain the succsinic acid half amide are improving the purposes that lubricant uses properties, and described lubricant for example is hydraulic pressure or metal working fluids lubricating grease, gear oil or machine oil.
Need to satisfy required task, high loading capacity for example resistance to wears and corrodes, and the additive of antioxygenation joins in the lubricant.The character of this external lubricant should not degenerate having in the presence of the pollutent, frequent with oil and the commercial interpolation enriched material that obtains easily or " packing material " mixing in mineral oil manufacturing enterprise, in mixing process, may there be water, the pollution of calcium washing composition and other lubricant residue, the anticorrosive effect that its result adds component has reduced, for example owing to form hydrolysate and insoluble calcium residue precipitation, this is to be disadvantageous especially because the latter stops up filtering system.
The present invention relates to produce lubricant compositions, described composition provides improved anticorrosive protection, and can compatible preferably combination with calcium ion.
U.S. a kind of lubricant compositions that resistance to wears with corrosion protection that provides is provided patent specification 4 462 918, wherein contains the component (aspartate) of N-aryl-N-alkylamino succinate type.
U.S. a kind of lubricant compositions that resistance to wears with corrosion protection that provides is provided patent specification 5 275 749, wherein contains the component of N-acyl group-N-alkoxyalkyl amino-succinate type.
Be surprised to find the succsinic acid half amide that obtains by succinyl oxide and beta amino acids derivatives reaction at present and can improve corrosion protection character in the lubricant compositions, can reduce forming precipitated product and residue simultaneously.
The present invention relates to a kind of composition, comprising:
A) compound of at least a following formula
R wherein 1Be to be selected from following substituting group: C 1-C 22Alkyl, the C that is replaced by hydroxyl 2-C 22Alkyl, middle insertion-C (=O)-,-O-C (=O)-or-NRa-C (=O)-C 2-C 22Alkyl, middle insertion-O-,-S-,-NR a-,-C (=O)-O-or-C (=O)-NR a-C 3-C 22Alkyl, wherein R aBe hydrogen or C 1-C22 alkyl, phenyl, benzyl, 1-or 2-phenylethyl, 2-phenoxy group ethyl, furfuryl, 1-naphthyl, 1-naphthyl methyl, cyclohexyl, cyclohexyl methyl and isobornyl;
R 2And R 3Be hydrogen, or R 2And R 3One of be hydrogen another be methyl; With
X is carboxyl or carboxylate salt, Y +It is the salifiable positively charged ion of shape that is suitable for lubricant composition; Perhaps
X is selected from following can deriving and is the group of carboxyl: cyano group, and by C 1-C 22The carboxyl of alkyl esterification is by hydroxyl-C 2-C 22The carboxyl of alkyl esterification, by middle insertion-C (=O)-,-C (=O)-O-or-C (=O)-NR a-C 2-C 22The carboxyl of alkyl esterification is particularly by centre insertion-O-,-S-,-NR a-,-O-C (=O)-or-NR a-(C=O)-C 3-C 22The carboxyl of alkyl esterification, wherein R aBe hydrogen or C 1-C 22Alkyl, by phenyl, benzyl, 1-or 2-phenylethyl, 2-phenoxy group ethyl, furfuryl, the 1-naphthyl, the 1-naphthyl methyl, cyclohexyl, cyclohexyl methyl, the formamyl of the carboxyl of isobornyl esterification and part following formula (A):
Figure C0382216800051
R wherein bAnd R CEach is hydrogen independently, C 1-C 22Alkyl or 2-hydroxyethyl, perhaps R bAnd R CBe C together 2-C 8Alkylidene group, C 2-C 8Alkenylene, C 2-C 8Alkadienylene or middle insertion-O-or-NR a-C 2-C 8Alkylidene group, C 2-C 8Alkenylene or C 2-C 8Alkadienylene, wherein R aDefinition as above; With
Y +It is the salifiable positively charged ion of hydrogen ion or the shape that is suitable for lubricant compositions; With
B) base oil of lubricant viscosity.
Compound (I) has fabulous inhibition of corrosion, and can and calcium ion (they particularly are present in the lubricant as the stain remover component) with good consistency combination.
An embodiment preferred that relates to described composition comprises:
A) at least a compound (I), wherein
R 1Be to be selected from following substituting group: C 1-C 22Alkyl, the C that is replaced by hydroxyl 2-C 22Alkyl, middle insertion-C (=O)-,-O-C (=O)-or-NR a-C (=O)-C 2-C 22Alkyl, middle insertion-O-,-S-,-NR a-,-C (=O)-O-or-C (=O)-NR a-C 3-C 22Alkyl, wherein R aBe hydrogen or C 1-C 22Alkyl, phenyl, benzyl, 1-or 2-phenylethyl, 2-phenoxy group ethyl, furfuryl, 1-naphthyl, 1-naphthyl methyl, cyclohexyl, cyclohexyl methyl and isobornyl;
R 2And R 3Be hydrogen, or R 2And R 3One of be hydrogen another be methyl; With
X is selected from following can deriving and is the group of carboxyl: cyano group, and by C 1-C 22The carboxyl of alkyl esterification is by hydroxyl-C 2-C 22The carboxyl of alkyl esterification, by middle insertion-C (=O)-,-C (=O)-O-or-C (=O)-NR a-C 2-C 22The carboxyl of alkyl esterification is particularly by centre insertion-O-,-S-,-NR a-,-O-C (=O)-or-NR a-(C=O)-C 3-C 22The carboxyl of alkyl esterification, wherein R aBe hydrogen or C 1-C 22Alkyl, by phenyl, benzyl, 1-or 2-phenylethyl, 2-phenoxy group ethyl, furfuryl, 1-naphthyl, 1-naphthyl methyl, cyclohexyl, cyclohexyl methyl, the formamyl of the carboxyl of isobornyl esterification and segment bounds (A), wherein R bAnd R CEach is hydrogen independently, C 1-C 22Alkyl or 2-hydroxyethyl, perhaps R bAnd R CBe C together 2-C 8Alkylidene group, C 2-C 8Alkenylene, C 2-C 8Alkadienylene or middle insertion-O-or-NR a-C 2-C 8Alkylidene group, C 2-C 8Alkenylene or C 2-C 8Alkadienylene, wherein R aDefinition as above; With
Y +It is the salifiable positively charged ion of hydrogen ion or the shape that is suitable for lubricant compositions; With
B) base oil of lubricant viscosity.
Particularly preferred embodiment relates to a kind of composition, comprising:
A) at least a compound (I), wherein
R 1Be selected from the substituting group of following group: C 1-C 22Alkyl, middle insertion-C (=O) or-O-C (=O) C 2-C 22Alkyl, middle insertion-O-,-S-or-O-C (=O)-C of O- 3-C 22Alkyl, phenyl and benzyl;
R 2And R 3Be hydrogen;
X is selected from following can deriving and is the group of carboxyl: cyano group, and by C 1-C 22The carboxyl of alkyl esterification is by hydroxyl-C 2-C 22The carboxyl of alkyl esterification, by middle insertion-C (=O)-or-C (=O)-C of O- 2-C 22The carboxyl of alkyl esterification, by middle insertion-O-,-S-or-O-C (=O) C 3-C 22The carboxyl of alkyl esterification is defined as the formamyl of the segment bounds (A) of heterocycle carbonyl; With
Y +Be hydrogen ion, ammonium ion, (C 1-C 4Alkyl) 1-4Ammonium or (2-hydroxyethyl) 1-4Ammonium; With
B) base oil of lubricant viscosity.
More particularly preferred embodiment relates to a kind of composition, comprising:
A) at least a compound (I), wherein
R 1Be selected from the substituting group of following group: C 1-C 22Alkyl, the C of middle insertion-O- 3-C 22Alkyl, phenyl and benzyl;
R 2And R 3Be hydrogen;
X is selected from following can deriving to be the group of carboxyl: cyano group, and by C 1-C 22The carboxyl of alkyl esterification is by the C of middle insertion-O- 3-C 22The carboxyl of alkyl esterification and be defined as piperidinyl carbonyl, the formamyl of the segment bounds of piperazine carbonyl and morpholinyl carbonyl (A); And Y +Be hydrogen ion, ammonium ion, (C 1-C 4Alkyl) 1-4Ammonium or (2-hydroxyethyl) 1-4Ammonium; With
B) base oil of lubricant viscosity.
Equally more particularly preferred embodiment relates to a kind of composition, comprising:
A) at least a compound (I), wherein
R 1Be selected from the substituting group of following group: C 1-C 18Alkyl, the C of middle insertion-O- 3-C 18Alkyl, phenyl and benzyl;
R 2And R 3Be hydrogen;
X is that carboxyl and Y are ammonium ions, (C 1-C 4Alkyl) 1-4Ammonium or (2-hydroxyethyl) 1-4Ammonium; Or
X is selected from following can deriving to be the group of carboxyl: cyano group, and by C 1-C 18The carboxyl of alkyl esterification is by the C of middle insertion-O- 3-C 18The carboxyl of alkyl esterification and morpholinyl formamyl; With
Y +Be hydrogen ion, ammonium ion, (C 1-C 4Alkyl) 1-4Ammonium or (2-hydroxyethyl) 1-4Ammonium; With
B) base oil of lubricant viscosity.
Compound (I) prepares according to known method own, for example with primary amine R 1-NH 2Join in the acrylic acid derivative
(X=carboxyl, carboxylate salt or deutero-carboxyl)
(amine being joined α, in the beta-unsaturated carbonyl compound) forms beta-aminoacid-derivatives:
Figure C0382216800081
Carry out acylation reaction with succsinic acid active functional derivative such as succinyl oxide or mono succinate acyl chlorides then.
DE-A-2 054 649 has described the addition reaction of primary amine to acrylate, and with the succinyl oxide reaction, wherein said compound particularly uses as textile auxiliary agent subsequently.
Term that uses in the specification sheets of the present invention and General Definition are preferably stipulated as follows:
Component is compound (I) a)
R 1And R aBe defined as C 1-C 22Alkyl comprises saturated, non-side chain or possible branched hydrocarbyl, particularly C 1-C 9Alkyl, methyl for example, ethyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, neo-pentyl, isopentyl, n-hexyl, 2-ethyl-butyl, 1-methyl amyl, 1,3-dimethylbutyl, n-heptyl, 3-heptyl, 1-methyl hexyl, different heptyl, n-octyl, the 2-ethylhexyl, 1,1,3, the 3-tetramethyl butyl, the 1-methylheptyl, n-nonyl or 1,1,3-trimethylammonium hexyl, and C 10-C 22Alkyl, particularly straight chain C 10-C 22Alkyl, for example positive decyl, dodecyl, n-tetradecane base, n-hexadecyl or Octadecane base or side chain C 10-C 22Alkyl for example 1,1,3-trimethylammonium hexyl, 1-methyl undecyl, 2-normal-butyl-n-octyl, isotridecyl, 2-n-hexyl-positive decyl or 2-n-octyl-dodecyl, or its higher homologue more.
R 1Be defined as the C that is replaced by hydroxyl 2-C 22Alkyl comprises saturated, the hydrocarbyl group of non-side chain, preferred 2-9 carbon atom, for example 2-hydroxyethyl or 2-or 3-hydroxypropyl.
R 1Insertion-C in the middle of being defined as (=O)-,-O-C (=O)-or-NR a-C (=O)-C 2-C 22Alkyl comprises the alkyl of non-side chain or side chain, preferably has 2-9 carbon atom, acetonyl for example, acetoxyl group carbonyl methyl, 2-acetoxyl group carbonyl ethyl, 2-tertbutyloxycarbonyl ethyl or N, N-diethylamino formyl radical.
R 1Insertion-O-in the middle of being defined as ,-S-,-NR a,-C (=O)-O-or-C (=O)-NR a-C 3-C 22Alkyl comprises non-side chain or branched hydrocarbyl, preferably has 3-18 carbon atom, for example the 2-methoxy ethyl; 2-or 3-methoxy-propyl, 2-, 3-or 4-methoxyl group butyl; the 2-ethoxyethyl group, 2-or 3-ethoxycarbonyl propyl, 2-; 3-or 4-oxyethyl group butyl, 2-positive propoxy ethyl, 2-or 3-positive propoxy propyl group; 2-, 3-or 4-positive propoxy butyl, 2-isopropoxy ethyl; 2-or 3-isopropoxide propyl, 2-, 3-or 4-isopropoxy butyl; 2-n-butoxy ethyl; 2-or 3-n-butoxy propyl group, 2-, 3-or 4-n-butoxy butyl; 2-tert.-butoxy ethyl; 2-or 3-tert.-butoxy propyl group, 2-, 3-or 4-tert.-butoxy butyl; 2-methyl sulphur ethyl; 2-or 3-methyl thiopropyl, 2-ethyl sulphur ethyl, 2-dimethyl aminoethyl; 2-or 3-dimethylaminopropyl; 2-diethylamino ethyl, 2-or 3-diethylamino propyl group, 2-ethanoyl oxygen base ethyl or 2-(N-ethanoyl oxygen base-N-methyl)-ethyl.
In compound (I), R 2And R 3Be hydrogen, or R 2And R 3One of be that hydrogen and another are methyl, preferred R 2And R 3Be hydrogen.
X in compound (I) be carboxyl or carboxylate salt [C (=O)-O -] time, Y +Be the salifiable positively charged ion of shape that is fit in the composition, for example ammonium, tetramethyl-ammonium, tetraethyl ammonium or 2-hydroxyethyl trimethyl ammonium.Only exist one for example with together the metastable form that do not dissociate of ammonium ion [C (=O)-OH] or salt form [C (=O)-O -] carboxyl, for example ammonium, tetramethyl-ammonium, tetraethyl ammonium or 2-hydroxyethyl-trimethyl ammonium.
In preferred embodiments, X is deutero-carboxyl or the formamyl unsubstituted or that replace that is defined as follows.Y +It is the salifiable positively charged ion of hydrogen ion or the shape that is suitable for lubricant compositions.
X is defined as by C 1-C 22The carboxyl of alkyl esterification is for example by as above R 1The C of definition 1-C 22The carboxyl of alkyl group esterification, for example by saturated, non-side chain maybe may be the alkyl of side chain, methyl for example, ethyl, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, n-pentyl, neo-pentyl, isopentyl, n-hexyl, 2-ethyl-butyl, 1-methyl amyl, 1,3-dimethyl-butyl, n-heptyl, 3-heptyl, 1-methyl hexyl, different heptyl, n-octyl, 2-ethylhexyl, 1,1,3,3-tetramethyl--butyl, 1-methylheptyl, n-nonyl or 1,1,3-trimethylammonium hexyl and by C 10-C 22Alkyl, particularly straight chain C 10-C 22Alkyl, for example positive decyl, dodecyl, n-tetradecane base, the carboxyl of n-hexadecyl or the esterification of Octadecane base.
X is defined as by hydroxyl-C 2-C 22The carboxyl of alkyl esterification, for example by as above-mentioned to R 1Hydroxyl-the C of definition 2-C 22The carboxyl of alkyl esterification, for example 2-hydroxyl-oxethyl-carbonyl or 2-or 3-hydroxyl propoxycarbonyl.
X be defined as by centre insertion-C (=O)-,-C (=O)-O-or-C (=O)-NR a-C 2-C 22The carboxyl of alkyl esterification, for example by as above-mentioned to R 1Insertion-C in the middle of the definition (=O)-,-C (=O)-O-or-C (=O)-NR a-C 2-C 22The carboxyl of alkyl esterification, for example acetone oxygen base carbonyl, acetoxyl group carbonyl methoxycarbonyl or 2-acetoxyl group carbonyl ethoxy carbonyl.
X is defined as by centre insertion-O-,-S-,-NR a-,-O-C (=O)-or-NR a-(C=O)-C 3-C 22The carboxyl of alkyl esterification is for example by centre insertion-O-,-S-,-NR 2-,-O-C (=O)-or-NR a-(C=O)-C 3-C 22Alkyl (definition as above-mentioned R 1) carboxyl of esterification, 2-methoxy ethoxy-carbonyl for example, 2-or 3-methoxy propoxy carbonyl, 2-, 3-or 4-methoxyl group butoxy carbonyl, 2-ethoxy ethoxy carbonyl, 2-or 3-oxyethyl group propoxycarbonyl, 2-, 3-or 4-oxyethyl group butoxy carbonyl, 2-methyl sulphur ethoxy carbonyl, 2-or 3-methyl sulphur propoxycarbonyl, 2-ethyl sulphur ethoxy carbonyl, 2-dimethylamino ethoxy carbonyl, 2-or 3-dimethylamino propoxy carbonyl, 2-diethylamino-ethoxy carbonyl, 2-or 3-diethylamino propoxycarbonyl, 2-acetoxyethoxy carbonyl or 2-(N-acetoxyl group-N-methyl)-ethoxy carbonyl.
The formamyl that X is defined as segment bounds A for example is a formamyl, dimethyl-or diethyl-formamyl, R in addition bAnd R CCan connect together becomes C 2-C 8Alkylidene group, for example 1, the inferior normal-butyl or 1 of 4-, inferior n-pentyl of 5-or C 2-C 8Alkenylene, for example 2-crotonylidene or C 2-C 8Alkadienylene for example 1, the inferior dibutene base of 3-, and and-N＜form heterocycle together, heterocycle can also contain other heteroatomss for example N or O.Formula A is equivalent to heterocycle carbonyl substituted base in this case, for example piperidinyl carbonyl, piperazine carbonyl or morpholine carbonyl.
In above-mentioned compound (I), be present in R 1Be preferably greater than 10 with the total number of carbon atoms among the X.
For Y +The definition of using " the salifiable positively charged ion of shape that is suitable for lubricant compositions " comprises the positively charged ion that forms the metal-salt that is suitable for lubricant compositions with acid group together, basic metal for example, alkaline-earth metal, zinc (Zn 2+) or copper (Cu 2+) salt, sodium for example, potassium, calcium, Zn 2+Or Cu 2+Ion.
In the preferred embodiment of the invention, for Y +The definition of using " the salifiable positively charged ion of shape that is suitable for lubricant compositions " also is understood that to form together with acid group the positively charged ion of suitable non-metal salt, ammonium for example, (C 1-C 22Alkyl) 1-4Ammonium or (2-hydroxyethyl) 1-4Ammonium, for example tetramethyl-ammonium, tetraethyl ammonium or 2-hydroxyethyl trimethyl ammonium.
Compound (I) is dissolved in the oil easily, and can be with the base oil of known mode own and lubricant viscosity, for example mix lubricant.
Components b) base oil
Definition " base oil of lubricant viscosity " comprises and for example can be used in hydraulic pressure, or the lubricant of metal working fluids, lubricating grease, gear oil or machine oil.
Examples of suitable lubricants is for example based on mineral oil or synthetic oil, or their mixture.
Those skilled in the art can be familiar with lubricant, and they are recorded in the relevant technical literature, for example Chemistry and Technology of Lubricants of LubricantsMortier, R.M. and Orszulik, S.T. (publisher); 1992 Blackie and Son Ltd.GB, VCH-Publishers N.Y., U.S., ISBN 0-216-92921-0 is referring to 208 ff and 269 ff; Kirk-Othmer Encyclopedia of Chemical Technology, the 4th edition 1969, J.Wiley ﹠amp; Sons, New York, Vol.13, P.533 ff (hydraulic fluid); Performance Testing of Hydraulic FluidsR.Tourret and E.P.Wright, Hy-den ﹠amp; Son Ltd.GB, Behalf of The Institute of Petroleum London, ISBN 085,501 3176; Ullmann ' s Encyclopaedia of Ind.Chem., the 5th revision, Verlag Chemie, DE-Weinheim, VCH-Publishers for U.S., Vol.A15, P.423ff (lubricant), vol.A 13, P.165ff (hydraulic fluid).
Lubricant is particularly for example based on the oil or the lubricating grease of mineral oil or vegetables oil, and animal oil, lubricating grease, butter and paraffin or its mixture.Vegetables oil and animal oil, lubricating grease, butter and paraffin for example are palmit seed oils, plam oil, sweet oil, rapeseed oil, rape oil, linseed oil, soybean oil, Oleum Gossypii semen, sunflower oil, Oleum Cocois, Semen Maydis oil, Viscotrol C, Walnut oil. and composition thereof; Fish oil and their chemically modified form, for example epoxidised and thio-oxidizing form, or the form that obtains by common process, for example the common process soybean oil of producing.
The example of synthetic lubricant comprises based on aliphatics or aromatic carboxylicesters, polymer esters, polyoxyethylene, phosphoric acid ester, poly-alpha olefins or polysiloxane, the diester of dihydric acid and unit alcohol, sebacic acid dioctyl ester for example, hexanodioic acid dinonyl ester, three esters of TriMethylolPropane(TMP) and unit acid or its mixture, trimethylolpropane tris pelargonate for example, trimethylolpropane tris octanoate or its mixture, four esters of tetramethylolmethane and unit acid or its mixture, tetramethylolmethane four octanoates for example, or the mixed ester of unit acid or diprotic acid and polyvalent alcohol, for example mixed ester of TriMethylolPropane(TMP) and sad or sebacic acid, or its mixture.Except mineral oil, specially suitable for example is poly-alpha olefins, the lubricant of ester group, phosphoric acid ester, glycol, poly-glycol and polyalkylene glycol, and the mixture of they and water.
The organic or inorganic thickening material can join in above-mentioned lubricant or its mixture (basic lubricating grease), metal working fluids and hydraulic fluid also can enough above-mentioned same material preparations for lubricant, and described fluid often is the emulsion of described material in water or other liquid.
Composition advantageously contains 0.005-10.0% weight, preferred 0.01-5.0% weight, the particularly compound of 0.01-0.9% weight (1).
The present composition for example is used for hydraulic pressure or metal working fluids, lubricating grease, gear oil or Otto, diesel engine, double stroke, the engine oil of Wankel or orbital type.
Above-mentioned lubricant can also comprise that other is used for further improving the additive of its essential property, described additive comprises oxidation inhibitor, metal deactivators, rust-preventive agent, viscosity index improver, pour point depressant, dispersion agent, stain remover, spy-pressure additive, antiwear additive and frictional force depressant.Above-mentioned in all cases additive is added into conventional quantity, and about 0.01-10.0% weight below is the example of additive.
The oxidation inhibitor of phenol type
1. alkylating unit phenol: 2,6 ,-di-tert-butyl-4-methy phenol, 2-butyl-4, the 6-xylenol, 2,6-di-t-butyl-4-ethylphenol, 2,6 ,-di-t-butyl-4-normal-butyl phenol, 2,6 ,-di-t-butyl-4-isobutyl-phenol, 2,6 ,-two cyclopentyl-4-methylphenol, 2-(Alpha-Methyl cyclohexyl)-4,6-xylenol, 2,6 ,-two-octadecyl-4-methylphenol, 2,4,6-thricyclohexyl phenol, 2,6 ,-di-t-butyl-4-methoxymethyl phenol, the nonylphenol of straight chain nonylphenol or side chain branching, for example 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(phenol of 1 '-methyl undecane-1 '-yl), 2,4-dimethyl-6-(phenol of 1 '-methyl heptadecane-1 '-yl), 2,4-dimethyl-6-(phenol of 1 '-methyl tridecane-1 '-yl), and composition thereof.
2. alkylthio methylphenol: 2,4-dioctyl thiomethyl-6-tert.-butyl phenol, 2,4-dioctyl thiomethyl-6-methylphenol, 2,4-dioctyl thiomethyl-6-ethylphenol, 2,4-two-dodecyl thiomethyl-4-nonylphenol.
3. hydroxyl benzoquinones and alkylating hydroxyl benzoquinones: 2,6-di-t-butyl-4-methoxyphenol, 2,5-di-t-butyl hydroxyl benzoquinones, 2,5-two tert-pentyl hydroxyl benzoquinones, 2,6-phenylbenzene-4-octadecyl oxy phenol, 2,6-di-t-butyl hydroxyl benzoquinones, 2,5-di-t-butyl-4-hydroxyanisol, 3,5-di-t-butyl-4-hydroxyanisol, 3,5-di-tert-butyl-hydroxy phenyl stearate, two (3, the 5-di-tert-butyl-hydroxy phenyl) adipic acid ester.
4. tocopherol: α, beta, gamma or methyltocol and composition thereof (vitamin-E).
5. hydroxylated sulfur phenenyl ether: 2,2 '-sulphur two (the 6-tertiary butyl-4-methylphenol), 2,2 '-sulphur two (4-octyl phenol), 4,4 '-sulphur two (the 6-tertiary butyl-3-methylphenol), 4,4 '-sulphur two (the 6-tertiary butyl-2-methylphenol), 4,4 '-sulphur two (3,6-di-sec-amyl phenol), 4,4 '-two (2,6-dimethyl-4-hydroxy phenyl) disulphide.
6. alkylidene diphenyl phenol: 2,2 '-methylene-bis (the 6-tertiary butyl-4-methylphenol), 2,2 '-methylene-bis (the 6-tertiary butyl-4-ethylphenol), 2,2 '-methylene-bis (4-methyl-6-(Alpha-Methyl cyclohexyl) phenol], 2,2 '-methylene-bis(4-methyl-6-cyclohexyl phenol), 2,2 '-methylene-bis (6-nonyl-4-methylphenol), 2,2 '-methylene-bis (4, the 6-DI-tert-butylphenol compounds), 2,2 '-ethylenebis (4, the 6-DI-tert-butylphenol compounds), 2,2 '-ethylenebis (the 6-tertiary butyl-4-isobutyl-phenol), 2,2 '-methylene-bis [6-(α-Jia Jibianji)-4-nonylphenol], 2,2 '-methylene-bis [6-(α, α-Er Jiajibianji)-4-nonylphenol], 4,4 '-methylene-bis (2,6 di t butyl phenol), 4,4 '-methylene-bis (the 6-tertiary butyl-2-methylphenol), 1, two (5-tertiary butyl-4-hydroxy-2-aminomethyl phenyl) butane of 1-, 2, two (the 3-tertiary butyl-5-methyl-2-hydroxybenzyl)-4-methylphenols of 6-, 1,1,3-three (5-tertiary butyl-4-hydroxy-2-aminomethyl phenyl) butane, 1, two (5-tertiary butyl-4-hydroxy-2-the aminomethyl phenyl)-3-dodecyl sulfydryl butane of 1-, ethylene glycol bis [3, two (3 '-tertiary butyl-4 '-hydroxy phenyl) butyric esters of 3-], two (3-tertiary butyl-4-hydroxy-5-aminomethyl phenyl) Dicyclopentadiene (DCPD), two [2-(3 '-tertiary butyl-2 '-hydroxyl-5 '-the methyl-benzyl)-6-tertiary butyl-4-aminomethyl phenyl] terephthalate, 1,1-two (3,5-dimethyl-2-hydroxy phenyl) butane, 2, two (3, the 5-di-tert-butyl-hydroxy phenyl) propane of 2-, 2, two (5-tertiary butyl-4-hydroxy-2-the aminomethyl phenyl)-4-dodecyl sulfydryl butane of 2-, 1,1,5,5-four (5-tertiary butyl-4-hydroxy-2-aminomethyl phenyl) pentane.
7.O-, N-and S-benzyl compounds: 3,5,3 ', 5 '-four-tertiary butyl-4,4 '-the dihydroxyl dibenzyl ether, octadecyl-4-hydroxyl-3,5-dimethyl benzyl mercaptoacetate, tridecyl-4-hydroxyl-3,5-di-t-butyl benzyl mercaptoacetate, three (3,5-two-tertiary butyl-4-hydroxy benzyl) amine, two (the 4-tertiary butyl-3-hydroxyl-2,6-dimethyl benzyl) two sulphur terephthalate, two (3,5-two-tertiary butyl-4-hydroxy benzyl) sulfide, iso-octyl-3,5-two-tertiary butyl-4-hydroxy benzyl mercaptoacetate.
8. the malonic ester of hydroxybenzylization: two-octadecyl 2, two (3, the 5-two-tertiary butyl-2-hydroxybenzyl) malonic esters of 2-, two-octadecyl 2-(3-tertiary butyl-4-hydroxy-5-methyl-benzyl) malonic ester, two-dodecyl mercaptoethyl 2, two (3, the 5-two-tertiary butyl-4-hydroxy benzyl) malonic esters of 2-, two-[4-(1,1,3, the 3-tetramethyl butyl) phenyl] 2, two (3, the 5-two-tertiary butyl-4-hydroxy benzyl) malonic esters of 2-.
9. hydroxybenzyl aromatic compound: 1,3,5-three (3,5-two-tertiary butyl-4-hydroxy benzyl)-2,4,6-Three methyl Benzene, 1, two (3,5-two-tertiary butyl-4-hydroxy benzyl)-2,3,5 of 4-, the 6-tetramethyl-benzene, 2,4,6-three (3,5-two-tertiary butyl-4-hydroxy benzyl) phenol.
10. triaizine compounds: 2, the two octyl group sulfydryl-6-(3,5-two-tertiary butyl-4-hydroxy phenylamino)-1,3 of 4-, the 5-triazine, 2-octyl group sulfydryl-4, two (3,5-two-tertiary butyl-4-hydroxy phenylamino)-1 of 6-, 3, the 5-triazine, 2-octyl group-sulfydryl-4,6-two (3,5-two-tertiary butyl-4-hydroxy phenoxy group)-and 1,3,5-triazines, 2,4,6-three (3,5-di-t-butyl-4-hydroxyphenoxy)-1,2, the 3-triazine, 1,3,5-three (3,5-two-tertiary butyl-4-hydroxy benzyl) isocyanic ester, 1,3,5-three (the 4-tertiary butyl-3-hydroxyl-2, the 6-dimethyl benzyl) isocyanic ester, 2,4,6-three (3,5-two-tert-butyl-hydroxy phenyl ethyl)-and 1,3,5-triazines, 1,3,5-three (3,5-two-tert-butyl-hydroxy phenyl propionyloxy) six hydrogen-1,3,5-triazine, 1,3,5-three (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanic ester.
11. amido phenol: 4-hydroxyl lauroyl aniline, 4-hydroxyl stearyl-aniline, N-(3, the 5-di-tert-butyl-hydroxy phenyl) carboxylamine octyl group ester.
12. β-(3,5-two-tert-butyl-hydroxy phenyl) propionic acid and single-or the ester of many-hydroxyl alcohol formation, for example and methyl alcohol, ethanol, n-Octanol, isooctyl alcohol, Stearyl alcohol, 1, the 6-hexylene glycol, 1,9-nonanediol, ethylene glycol, 1,2-propylene glycol, dimethyltrimethylene glycol, thio-diethylene glycol, Diethylene Glycol, triethylene glycol, tetramethylolmethane, the different hydrogen acid ether of three (hydroxyethyls), N, N '-two (hydroxyethyl) oxalic acid diamide, 3-thia hendecanol, 3-thia pentadecylic alcohol, the trimethylammonium hexylene glycol, TriMethylolPropane(TMP), 4-hydroxymethyl-1-phospha-2,6,7-trioxa-l-phosphabicyclo [2.2.2] octane.
13. β-(5-tertiary butyl-4-hydroxy-3-aminomethyl phenyl) propionic ester (and single-or many-hydroxyl alcohol): and methyl alcohol, ethanol, n-Octanol, isooctyl alcohol, Stearyl alcohol, 1, the 6-hexylene glycol, 1, the 9-nonanediol, ethylene glycol, 1, the 2-propylene glycol, dimethyltrimethylene glycol, thio-diethylene glycol, Diethylene Glycol, triethylene glycol, tetramethylolmethane, the different hydrogen acid ether of three (hydroxyethyls), N, N '-two (hydroxyethyl) oxalic acid acid amides, 3-thia hendecanol, 3-thia pentadecylic alcohol, the trimethylammonium hexylene glycol, TriMethylolPropane(TMP), 4-hydroxymethyl-1-phospha-2,6,7-trioxa-l-phosphabicyclo [2.2.2] octane.
14. the ester that β-(3,5-dicyclohexyl-4-hydroxy phenyl) propionic acid and single-or many-hydroxyl alcohol forms is for example with the ester of above-mentioned 13 alcohol formation.
15.3 the ester that 5-two-tert-butyl-hydroxy phenyl acetate and single-or many-hydroxyl alcohol forms is for example with the ester of above-mentioned 13 alcohol formation.
16. β-(3; 5-two-tert-butyl-hydroxy phenyl) acid amides of propionic acid; N for example, N '-two (3,5-two-tert-butyl-hydroxy phenyl propionyl) hexa-methylene bisamide; N; N '-two (3,5-di-tert-butyl-hydroxy phenyl propionyl) trimethylene bisamide, N; N '-two (3,5-two-tertiary butyl-4-hydroxy-phenyl propionyl) hydrazine.
The oxidation inhibitor of amine type
N; N '-two-sec.-propyl-p-phenylene bisamide; N; N '-two-sec-butyl-p-phenylene bisamide; N; N '-two (1; 4-dimethyl amyl group)-p-phenylene bisamide; N; N '-two (1-ethyl-3-methyl amyl)-p-phenylene bisamide; N; N '-two (1-methylheptyl)-p-phenylene bisamide; N; N '-dicyclohexyl-p-phenylene bisamide; N; N '-phenylbenzene-p-phenylene bisamide; N, N '-two (2-naphthyl)-p-phenylene bisamide, N-sec.-propyl-N '-phenyl-p-phenylene bisamide; N-(1; the 3-dimethylbutyl)-and N '-phenyl-p-phenylene bisamide, N-(1-methylheptyl)-N '-phenyl-p-phenylene bisamide, N-cyclohexyl-N '-phenyl-p-phenylene bisamide; 4-(p-tolylsulfonyl amino)-diphenylamine; N, N '-dimethyl-N, N '-two-sec-butyl-p-phenylene bisamide; diphenylamine; N-allyl group diphenylamine, 4-isopropoxy diphenylamine, N-phenyl-1-naphthyl-amine; N-(uncle's 4-octyl phenyl)-1-ALPHA-NAPHTHYL AMINE; N-phenyl-2-ALPHA-NAPHTHYL AMINE, octyldiphenylamine, for example p; p '-two-uncle octyldiphenylamine; 4-normal-butyl amino-phenol, 4-butyryl radicals-amino-phenol, 4-nonanoyl amino-phenol; 4-lauroyl amino-phenol; 4-octadecanoyl amino-phenol, two (4-p-methoxy-phenyl) amine, 2; 6-two-tertiary butyl-4-dimethylaminomethyl phenol; 2,4 '-diaminodiphenyl-methane, 4; 4 '-diaminodiphenyl-methane; N, N, N '; N '-tetramethyl--4; 4 '-diaminodiphenyl-methane, 1,2-two [(2-aminomethyl phenyl) amino] ethane; 1; 2-two (phenyl amino) propane, (o-tolyl)-biguanides, two [4-(1 '; 3 '-dimethylbutyl) phenyl] amine; uncle's octyl group N-phenyl-1-naphthylamine, single-and two-alkyl-tert-butyl-/mixture of uncle's octyl group-diphenylamine, single-and the mixture of dialkyl group nonyl diphenylamine; the mixture of list and dialkyl group dodecyl diphenylamine; single and dialkyl group sec.-propyl-/mixture of isohexyl-pentanoic, single-with the mixture of the tertiary butyl pentanoic of dialkyl groupization, 2; 3-dihydro-3; 3-dimethyl-4H-1,4-benzothiazine, thiodiphenylamine; list and the dialkyl group tertiary butyl/uncle's octyl group thiodiphenylamine mixture; single-and dialkyl group uncle octyl group thiodiphenylamine mixture, N-allyl group thiodiphenylamine, N; N; N ', N ' ,-tetraphenyl-1; 4-diamino but-2-ene; N, N-two (2,2; 6; 6-tetramethyl--piperidin-4-yl-hexa-methylene bisamide, two (2,2; 6; 6-tetramethyl--piperidin-4-yl) sebate, 2,2; 6; 6-tetramethyl piperidine-4-ketone, 2,2; 6,6-tetramethyl piperidine-4-alcohol.
Other oxidation inhibitor
Xitix (vitamins C), aliphatics or aromatic phosphite, the ester of thio-2 acid or thiodiglycolic acid, or the salt of dithiocarbamic acid or phosphorodithioic acid, 2,2,12,12-tetramethyl--5,9-dihydroxyl-3,7,11-three thia tridecanes and 2,2,15,15-tetramethyl--5,12-dihydroxyl-3,7,10,14-four thia n-Hexadecanes.
Metal deactivators (for example to copper)
1. benzotriazole and derivative thereof: 2-sulfydryl benzotriazole, 2,5-dimercapto benzo triazole, 4-or 5-alkyl benzotriazole (for example azimido-toluene) and derivative thereof, 4,5,6,7-tetrahydroxy benzo triazole, 5,5 '-methylene radical-two benzotriazoles; Manny breath alkali, for example 1-[two (2-ethylhexyl) amino methyl of benzotriazole or azimido-toluene] azimido-toluene and 1-[two (2-ethylhexyl)-amino methyl] benzotriazole; The alkoxyalkyl benzotriazole, 1-(undecane oxygen ylmethyl) benzotriazole for example, 1-(1-butoxyethyl group) benzotriazole and 1-(1-cyclohexyl oxygen Ji Dingji) azimido-toluene.
2.1,2,4-triazole and derivative thereof: the 3-alkyl-(or aryl-) 1,2,4-triazole, 1,2, Manny breath alkali, for example 1-[two (2-ethylhexyl) amino methyl of 4-triazole]-1,2, the 4-triazole; Alkoxyalkyl-1,2,4-triazole, 1-(1-butoxyethyl group)-1,2 for example, 4-triazole; Ethanoyl 3-amino-1,2, the 4-triazole.
3. imdazole derivatives: 4,4 '-methylene-bis (2-undecyl-5-Methylimidazole); Two [(N-methyl)-imidazoles-2-yl] methyl alcohol-Octyl Ether.
4. sulfur heterocyclic ring compound: 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazoles, 2,5-dimercapto benzo thiadiazoles and derivative thereof; 3, two [two (2-ethylhexyl) amino methyls]-1,3 of 5-, 4-thia diazole-2-ketone.
5. aminocompound: salicylidene-propylidene bisamide, salicyl aminoguanidine and salt thereof.
Rust-preventive agent
1. organic acid; its ester; metal-salt; ammonium salt and acid anhydrides: alkyl-and alkenyl-succsinic acid and they and alcohol; the part ester of glycol or hydroxycarboxylic acid, alkyl-and alkenyl-succsinic acid, the 4-nonylphenoxyacetic acid; alkoxyl group-and alkoxyl group oxyethyl group-carboxylic acid; dodecyloxy acetate for example, dodecyloxy (oxyethyl group) acetate and ammonium salt thereof, and N-oleoyl-sarkosine; sorbitol monooleate; lead naphthenate, alkenyl succinic anhydrides, for example dodecenyl succinic anhydride; 2-(2-carboxy ethyl)-1-dodecyl-3-methylglycerin(e) and salt thereof, particularly sodium salt and triethanolamine salt.
2. nitrogenous compound:
2.1. the aliphatics of organic or inorganic acid or alicyclic tertiary amine and ammonium salt, for example oil-soluble alkyl-carboxylic acid ammonium, and 1-[N, two (2-hydroxyethyl) amino of N-]-3-(4-Nonylphenoxy) propan-2-ol.
2.2. heterogeneous ring compound, for example tetrahydroglyoxaline of Qu Daiing and  azoles quinoline are as 2-heptadecyl-1-(2-hydroxyethyl)-tetrahydroglyoxaline.
3. sulfocompound: dinonyl naphthalene sulfonate barium, calcium mahogany sulfonate, the aliphatic carboxylic acid that alkylthio replaces, aliphatics 2-carbothioic acid ester and salt thereof.
Anti-extreme pressure and wear preventive additive
Sulfur-bearing and halide-containing, chlorating paraffinic hydrocarbon for example, sulfurized alkene or vegetables oil (soybean oil/rape seed oil), alkyl or aryl-two-or-trisulphide, benzotriazole or derivatives thereof such as two (2-ethylhexyl) amino methyl azimido-toluene, dithiocarbamate such as methylene radical-two-dibutyl dithiocaarbamate ester, the derivative of 2-sulfydryl-benzothiazole such as 1-[N, two (2-ethylhexyl) amino methyls of N-]-2-sulfydryl-1H-1, the 3-benzothiazole, 2,5-dimercapto-1,3, the derivative of 4-thiazole is as 2, two (uncle's nonyl two sulphur)-1,3 of 5-, the 4-thiadiazoles.
The frictional coefficient depressant
Lard, oleic acid, butter, rape seed oil, sulfurized fat, amine.Other example is referring to EP-A-0 565487.
Other additive
1. viscosity index improver: polyacrylic ester, polymethacrylate, the multipolymer of vinyl pyrrolidone/methacrylic ester, polyvinylpyrrolidone, polybutene, alkenes multipolymer, phenylethylene ethylene/propenoic acid ester copolymer, polyethers.
2. pour point depressor: poly-(methyl) acrylate, ethylene, alkyl-polystyrene, manthanoate multipolymer, alkylating naphthalene derivatives.
3. dispersant/: polybutylene-based succsinic acid acyl ammonium or imide, polybutylene-based phosphoric acid derivatives, alkaline sulfoacid magnesium, calcium sulphonate, barium sulfonate and phenol compound.
Special additive
Be used for water/oily metal working fluids and hydraulic fluid
1. emulsifying agent: sulfonated petro-leum, amine such as polyoxy ethyl fatty amine, nonionogenic tenside;
2. buffer reagent: alkanolamine;
3. biocide: triazines, thiazolinone, trinitromethane, morpholine, pyridine sodium mercaptides;
4. process velocity improving agent: calcium sulphonate and barium sulfonate.
Use blending means well known in the art that mentioned component is joined in the composition, also can use compound (I) or its mixture and optional other additive preparation concentrated solution or so-called additive packing thing, when making with lubricator, enriched material alkene be released then.Consisting of when enriched material of composition do not need other added ingredients b in the enriched material when room temperature is liquid) or solvent.
The invention still further relates to enriched material, comprise a) at least a compound (I), wherein R 1, R 2, R 3, X and Y definition as above, and other optional additive, and b) base oil of lubricant viscosity.
The invention still further relates to and improve the method that lubricant uses character, comprise that the composition that will contain at least a compound (I) joins in the lubricant, R in the compound (I) 1, R 2, R 3, X and Y definition are as above.
Following examples are used to illustrate the present invention.
Embodiment
Temperature: ℃; H: hour (s); Min.: minute; M.p.: fusing point; In vacuum dry (100 ℃, about 0.05mbar).
Synthetic embodiment
Embodiment 1
N-(the positive butoxy carbonyl ethyl of 2-n-)-N-(n-octadecyl)-mono succinate acid amides
1.1 14.1g (0.110mol) n-butylacrylate is in 60 ℃ of about 10min.Be added drop-wise in 28.4g (0.100mol) the n-octadecylamine, limpid reaction mixture stirs 2h in 100 ℃; The thick product of refrigerative is dissolved in the 100ml hexane, filters and with 50ml water washing twice, organic phase concentrates by evaporation in rotatory evaporator, and residue is drying under vacuum, obtains the limpid colourless moderately viscous oily matter of 40.0g.
1.2 3.1g (0.030mol) succinyl oxide joins in the above-mentioned intermediate that obtains of 11.9g (0.030mol), limpid reaction soln stirs 1h in 100 ℃, the thick product of refrigerative is dissolved in the 100ml hexane, filter and with twice of 40ml water washing, hexane solution concentrates by evaporation in rotatory evaporator, residue is dry under vacuum, obtains the limpid yellow oil of 13.7g (92% theoretical amount), obtains crystallization after leaving standstill.
M.p.:50-52 ℃; Ultimate analysis: 70.24%C (calculated value 69.98), 10.91%H (calculated value 11.14), 2.80%N (calculated value 2.81).
Embodiment 2
N (3-n-butoxy propyl group)-N-(2-n-dodecyl oxygen base carbonyl ethyl)-mono succinate acid amides
Figure C0382216800191
2.1 26.7g (0.10mol) vinylformic acid n-dodecyl ester is added drop-wise in 13.3g (0.100mol) the 3-n-butoxy propyl group amine in 20min, reaction mixture stirs 2h in 100 ℃; The thick product of vacuum-drying refrigerative obtains the limpid colourless low viscosity oily thing of 37.0g.
2.2 4.2g (0.040mol) succinyl oxide joins among the above-mentioned intermediate product 14.9g that obtains (0.040mol), and reaction soln is stirred 2h; The thick product of refrigerative is dissolved in the 100ml hexane, filters and with 30ml water washing three times, hexane solution concentrates by evaporation in rotatory evaporator, and residue is drying under vacuum, obtains the moderately viscous limpid yellow oil of 18.0g (95% theoretical value).n D 201.4670; Ultimate analysis: 66.85%C (calculated value 66.21), 10.54%H (calculated value 10.47), 2.72%N (calculated value 2.97).
Embodiment 3
N-(2-morpholinyl carbonyl ethyl)-N-(n-octadecyl)-mono succinate acid amides
Figure C0382216800192
3.1 5.8g (0.040mol) 4-acryloyl morpholine joins in 10.7g (0.040mol) the oil base amine (Armeen ) with about 10min in 60 ℃; reaction mixture stirs 1h in 100 ℃; the thick product of vacuum-drying refrigerative obtains the limpid faint yellow low viscous oily matter of 16.0g.3.24.1g (0.040mol) succinyl oxide joins in the above-mentioned intermediate product that obtains of 16g (0.040mol), reaction soln stirs 1h, the thick product of refrigerative 200ml hexane and 100ml salt solution (saturated NaCL) vibration in 100 ℃.Intermediate phase in the three-phase is further used for 30ml salt solution washing three times, is dissolved in then in the 100ml toluene, filters and concentrates with rotatory evaporator; The product that vacuum-drying obtains obtains the limpid yellow oil of 15.6g (77% theoretical amount), becomes muddiness after the cooling.
Ultimate analysis: 68.24%C (calculated value 68.47), 10.23%H (calculated value 10.30), 5.34%N (calculated value 5.51).
Embodiment 4
Following compound (I) prepares according to the method for embodiment 1-3:
Table 1
Ex. R 1 X Productive rate [% theoretical amount] Apparent Ultimate analysis [measured value (calculated value)]
4.1 Oil base -C (=O)-O-(n-butyl) 99 Limpid faint yellow medium-viscosity oily matter n D 201.4761 70.79％C(70.26) 10.58％H(10.78) 2.82％N(2.83)
4.2 Oil base -C (=O)-the O-methyl 93 Limpid thickness oily matter n D 201.4804 69.97％C(70.08) 10.40％H(10.44) 3.10％N(3.10)
4.3 Oil base -C(＝O)-O(CH 2) 2-O-ethyl 96 Limpid medium-viscosity yellow oil n D 201.4768 69.02％C(68.07) 10.50％H(10.44) 2.77％N(2.74)
4.4 Oil base -C (=O)-O-(isobutyl-) 77 Limpid medium-viscosity yellow oil n D 201.4748 70.04％C(70.26) 10.76％H(10.78) 2.80％N(2.83)
4.5 Oil base -C (=O)-the O-ethyl 69 Limpid medium-viscosity yellow oil n D 201.4769 68.85％C(69.34) 10.50％H(10.56) 2.97％N(2.99)
4.6 Isotridecyl -C (=O)-O-(n-butyl) 90 Limpid faint yellow thickness oily matter n D 201.4711 67.56％C(67.41) 10.59％H(10.61) 3.35％N(3.28)
4.7 Isotridecyl -C (=O)-O-(isobutyl-) 87 Limpid faint yellow thickness oily matter n D 201.4709 67.63％C(67.41) 10.66％H(10.61) 3.36％N(3.28)
4.8 The n-butyl -C (=O)-the O-oil base 95 Limpid yellow medium-viscosity oily matter n D 201.4752 70.80％C(70.26) 10.79％H(10.78) 2.56％N(2.83)
4.9 The n-dodecyl -C (=O)-the O-ethyl 82 Limpid faint yellow medium-viscosity oily matter n D 201.4706 65.78％C(65.42) 10.39％H(10.20) 3.72％N(3.63)
4.10 Oil base Nitrile 87 Limpid faint yellow thickness oily matter n D 201.4783 72.13％C(71.39) 10.73％H(10.54) 6.23％N(6.66)
4.11 The n-octyl group -C (=O)-the O-oil base 97 Limpid yellow thickness oily matter n D 201.4745 72.04％C(71.69) 11.05％H(11.30) 2.41％N(2.53)
4.12 Oil base -C(＝O)-O-(CH 2) 2OH 59 Limpid faint yellow thickness oily matter n D 201.4855 66.92％C(67.05) 9.99％H(10.21) 2.86％N(2.90)
4.13 Oil base -C(＝O)-NH 2 82 Limpid yellow thickness oily matter n D 201.4745 68.10％C(68.45) 10.44％H(10.57) 6.26％N(6.39)
Table 1 (continuing)
Ex. R 1 X Productive rate [% theoretical amount] Apparent Ultimate analysis [measured value (calculated value)]
4.14 Cocoa oleyl amine (C 12mix) -C (=O)-O-(n-butyl) 87 Limpid faint yellow thickness oily matter n D 201.4701 67.68％C(67.73) 10.50％H(10.18) 3.31％N(3.29)
4.15 N-butoxy-propyl group -C (=O)-the O-oil base 97 Limpid yellow medium-viscosity oily matter n D 201.4744 69.75％C(69.40) 10.66％H(10.74) 2.40％N(2.53)
4.16 C 8-C 10Alkyl-O (CH 2) 3 -C (=O)-O-(n-butyl) 95 Limpid yellow medium-viscosity oily matter n D 201.4680 63.72％C 10.00％H 3.19％N
4.17 Isodecyl-O (CH 2) 3 -C (=O)-O-(n-butyl) 96 Limpid yellow medium-viscosity oily matter n D 201.4699 64.75％C(64.98) 10.11％H(10.22) 3.14％N(3.16)
4.18 The 2-ethylhexyl -C (=O)-O-(dodecyl) 96 Limpid faint yellow medium-viscosity oily matter n D 201,4684 69.60％C(69.04) 10.69％H(10.94) 2.67％N(2.98)
4.19 Methoxyl group-propyl group -C (=O)-O-(dodecyl) 98 Waxy solid 64.99％C(64.31) 10.14％H(10.09) 2.91％N(3.26)
4.20 C 8-C 10alk- O(CH 2) 3 Nitrile 97 Limpid yellow medium-viscosity oily matter n D 201.4731 63.62％C(64.38) 9.61％H(9.67) 7.69％N(7.90)
4.21 Benzyl -C (=O)-O-(dodecyl) 97 Waxy solid 70.02％C(69.77) 8.99％H(9.23) 3.10％N(3.13)
4.22 Oil base -C (=O)-the O-cyclohexyl 98 Limpid yellow medium-viscosity oily matter n D 201,4864 71,35％C(71,36) 10,12％H(10.62) 2,72％N(2,68)
4.23 Oil base -C(＝O)-O-(CH 2) 2-O-phenyl 98 Limpid yellow medium-viscosity oily matter n D 201,5025 71,20％C(70,81) 9,57％H(9,54) 2,43％N(2,50)
4.24 Oil base -C(＝O)-O-(CH 2) 2-O-methyl 94 Limpid yellow medium-viscosity oily matter n D 201,4791 67,82％C(67.43) 10,26％H(10.51) 2,85％N(2,81)
4.25 Oil base -C(＝O)-O-(CH 2) 2-O- (CH 2) 2-O-ethyl 94 Limpid yellow medium-viscosity oily matter n D 201.4771 66.55％C(67.54) 10,55％H(10,34) 2,51％N(2,52)
4.26 Benzyl -C (=O)-the O-dodecyl 98 Faint yellow waxy solid
Table 1 (continuing)
4.27 The 2-ethylhexyl -C (=O)-the O-dodecyl 96 Limpid yellow medium-viscosity oily matter n D 201,4684 69,60％C(69,04) 10,69％H(10,94) 2.67％N(2,98)
4.28 The n-butyl -C (=O)-the O-i-decyl 91 Limpid yellow medium-viscosity oily matter n D 201,4708 65,24％C(65,42) 10,20％H(10,20) 3,43％N(3,63)
4.29 Methyl-O-(CH 2) 3 -C (=O)-the O-dodecyl 99 Faint yellow waxy solid 64,99％C(64,31) 10,14％H(10,09) 2,91％N(3,26)
4.30 Ethyl-O-(CH 2) 3 -C (=O)-the O-dodecyl 95 Limpid yellow medium-viscosity oily matter n D 201,4681 65.25％C(64.98) 10,28％H(10,22) 2,85％N(3,16)
4.31 Ethyl-O-(CH 2) 3 -C (=O)-the O-oil base 95 Limpid yellow medium-viscosity oily matter n D 201,4755 69,09％C(68,53) 10,76％H(10,54) 2,57％N(2.66)
4.32 I-propyl group-O-(CH 2) 3 -C (=O)-the O-oil base 96 Limpid yellow medium-viscosity oily matter n D 201,4741 68,19％C(68,98) 10,09％H(10,64) 2.55％N(2,59)
4.33 I-decyl-O-(CH 2) 3 -C (=O)-the O-n-butyl 96 Limpid yellow medium-viscosity oily matter n D 201,4699 64,75％C(64,98) 10,11％H(10,22) 3,14％N(3,16)
4.34 I-decyl-O-(CH 2) 3 -C (=O)-the O-i-butyl 95 Limpid yellow medium-viscosity oily matter n D 201,4696 64,87％C(64,98) 10,38％H(10,22) 3,25％N(3,16)
4.35 Octadecyl-O-(CH 2) 3 -C (=O)-the O-i-butyl 96 Limpid yellow medium-viscosity oily matter n D 201,4682 66,76％C(67,30) 10,72％H(10,69) 2,91％N(2.80)
4.36 Oil base -C(＝O)-N(CH 2) 5 94 Limpid yellow medium-viscosity oily matter n D 201,4985 70,76％C(71,10) 10,98％H(10,74) 5,24％N(5,53)
Use embodiment
Embodiment 5
Carry out corrosion protection test (containing the industry of activeconstituents, circulation, turbine and hydraulic efficiency oil) according to ASTM D 665 (=DIN 51585)
The oil of 300ml prescription and 30ml synthetic sea water stir 24h in 60 ℃ of mixing, are dipped in simultaneously in the steel drum of circular section, after contact for some time, steel drum are carried out various corrosion tests.
Each test repeats twice, basic recipe is the mineral oil according to specific SN VG46, use oxidation inhibitor and metal deactivators to carry out stabilization, the concentration of the activeconstituents under the test conditions is 0.1mmol/kg (being equivalent to 0.03-0.06% weight or 300-600ppm), and the result is referring to table 2.
0: not corrosion
1: mild corrosion (less than hot spot＜6 of diameter 1mm)
2: moderate corrosion (surface corrosion＜5%)
3: heavy corrosion (surface corrosion＞5%)
Embodiment 6
Filterableness test in the presence of calcium ion
0.3g the calcium (6.9%Ca) in distilled water and the 30ppm calcium stain remover joins in the 300g test recipe, mixture homogenize in the quaterfoil mixing tank, under top speed, rotate 5min., emulsion stores 96 hours in 70 ℃ (+/-2 ℃), in dark place room temperature storage 48 hours, promptly stop test then if observed precipitation.Homogenize was carried out in the fierce once more vibration of test mixture in 1 minute before filtering, by 0.8u Millipore  strainer (model AAWP 04700) use pressurized air in 1bar (+/-0.05bar) direct draught filters, measure and filter 50,100,200 and the required time of 300ml test mixture, calculate filtered index FI (mean value of twice mensuration), according to following formula (referring to AFNOR NFE 48-691):
FI＝(t 300ml-t 200ml)/2(t 100ml-t 50m1)
FI=1 is meant does not have residue in the strainer
The requirement by test is satisfied in FI＜2nd
Strainer is blocked to be observed after 60 minutes up to the filter oil volume.
Table 2
Embodiment According to ASTM D 665 extent of corrosions At Ca 2+Strainability Filtration index Fl under existing
Basic recipe 3/3 1.25
1 1/0
2 0/0 1.20
3 0/0 1.25
4.1 0/0 1.13
4.2 0/0 1.11
4.3 0/0 1.05
4.4 1/1 1.05
4.5 0/1 1.1
4.6 1/0
4.7 0/0
4.8 0/0 1.05
4.9 0/0
4.10 0/0 1.05
4.11 1/1
4,12 1/1
4.13 1/1 1.20
4.14 1/0
4.15 0/0

Claims (4)

1. composition comprises:
A) compound of at least a following formula (I):
Figure C038221680002C1
Wherein:
R 1Be selected from the substituting group of following group: C 1-C 22Alkyl, the C of middle insertion-O- 3-C 22Alkyl, oil base, phenyl and benzyl;
R 2And R 3Be hydrogen;
X is the deutero-carboxyl, is selected from following group: cyano group, formamyl is by C 1-C 22The carboxyl of alkyl esterification is by the C of middle insertion-O- 3-C 22The carboxyl of alkyl esterification and by the carboxyl of oil base or cyclohexyl esterification, perhaps X is morpholinyl carbonyl or piperidinyl carbonyl; With
Y +It is hydrogen ion; With
B) base oil of lubricant viscosity.
2. according to the composition of claim 1, comprising:
A) at least a compound (I), wherein
R 1Be the substituting group that is selected from following group: C 1-C 18Alkyl, the C of middle insertion-O- 3-C 18Alkyl, oil base, phenyl and benzyl;
R 2And R 3Be hydrogen;
X is the deutero-carboxyl, is selected from following group: cyano group, and by C 1-C 18The carboxyl of alkyl esterification is by the C of middle insertion-O- 3-C 18The carboxyl of alkyl esterification, perhaps X is a morpholinyl carbonyl; With
Y +It is hydrogen ion; With
B) base oil of lubricant viscosity.
3. according to the composition of claim 1, comprise
B) be used for hydraulic pressure or metal working fluids, lubricating grease, the base oil of the lubricant viscosity of gear oil or machine oil.
4. improve the method that lubricant uses character, comprise that the composition with at least a claim 1 joins in the lubricant.
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