WO2008072740A1 - Additive for oil and lubricating oil containing the same - Google Patents

Abstract

An additive for oils which contains an ester represented by the formula (I). The additive is used in oils such as a lube base oil to impart friction-reducing properties and wear-reducing properties to the oils. R1 and R2 each is hydrocarbyl, etc.; a and b each is an integer of 0-5; X and Y each is sulfur or a single bond; and W and Z each is hydrogen, -NR3R4, etc.; provided that not both of W and Z are hydrogen and that when one of W and Z is hydrogen, then not both of X and Y are a single bond and R3 and R4 each is hydrogen, hydrocarbyl, etc.

Description

 Specification

 Oil additive and lubricating oil containing the same

 Technical field

 [0001] The present invention relates to an additive for oils added to oils such as lubricating oil and fuel oil, and a lubricating oil containing the same.

 This application claims to priority based on Japanese Patent Application No. 2006—337118 filed on December 14, 2006 and Japanese Patent Application No. 2007—123388 filed on May 8, 2007. I use it here.

 Background art

 [0002] In recent years, global energy demand has increased dramatically due to the rapid growth of industries in China, India and Southeast Asian countries and the increasing penetration of automobiles and electrical appliances. As a result, global environmental impacts are beginning to be a concern, and global warming, acid rain, destruction of the ozone layer, and the improvement of environmental problems caused by emissions such as those represented by the Kyoto Protocol Various regulations on energy saving have been made.

 [0003] As part of this, lubricating oils, especially automobile engine oils, are also strongly required to have fuel savings, long drains, etc., and at the same time, the upper limit concentration of metal, phosphorus and sulfur contained in the lubricating oil is limited. (See Non-Patent Documents 1 and 2). Therefore, there is a demand for lubricating oils that do not contain these components, particularly metals and phosphorus.

 [0004] Lubricating oil is generally obtained by adding an additive to a lubricating base oil. In order to improve the fuel efficiency of lubricating oils, it is said that it is effective to select a lubricating base oil with low viscosity and excellent heat resistance. As such materials, polar base oils such as esters are used. Is known (see Patent Document 1).

 [0005] Various other characteristics are also required for lubricating oils, and one of them is wear resistance.

 (Friction reduction and wear reduction). Therefore, for example, as described in Patent Documents 2 to 5, additives for imparting wear resistance characteristics to lubricating oils have been studied! Patent Document 1: JP-A-2005-48192

Patent Document 2: Japanese Patent Publication No. 6-4867 Patent Document 3: Japanese Patent No. 2563295

 Patent Document 4: Japanese Unexamined Patent Application Publication No. 2004-262964

 Patent Document 5: Japanese Patent Publication No. 1 501319

 Non-Patent Document 1: “Lubrication Economy”, 2005, July, p7

 Non-Patent Document 2: "Monthly Trypology", 2005, December, p36

 Disclosure of the invention

 Problems to be solved by the invention

[0006] However, these conventional additives for imparting wear resistance properties both contain a metal content and a phosphorus content, do not contain a metal content and a phosphorus content, and are polar base oils. Additives that can impart wear resistance properties to lubricating base oils such as these have not yet been found and are currently available.

 [0007] An object of the present invention is to provide an oil additive containing an ester that does not contain a metal component and a phosphorus component, and that contains an ester capable of imparting wear resistance to an oil such as a lubricating base oil. Another object is to provide a lubricating oil containing additives.

 Means for solving the problem

As a result of intensive studies, the present inventors have found that the above problems can be solved by using an ester into which a nitrogen atom has been introduced as an additive for oils, and have completed the present invention. That is, the present invention provides the following (1) to (; 16).

 (1) The following formula (I)

[0009] [Chemical 1]

[In the formula (I), R ¹ and R ² are the same or different and each represents a hydrocarbyl which may contain one or more selected from the group consisting of an oxygen atom and a sulfur atom, and a and b are the same or Differently, it represents an integer of 0 to 5, X and Y are the same or different and each represents a sulfur atom or a single bond, W and Z are the same or different, a hydrogen atom, formula (II)

[0011] [Chemical 2] R ^ (if)

[In the formula (II), R ³ and R ⁴ are the same or different and represent a hydrogen atom, an optionally substituted hydrocarbyl, an optionally substituted hydrocarbylcarbonyl, or a substituent. Have! /, May! /, Hydrocarbyloxycarbonyl, have substituents! /, May! /, Represent hydrolylsulfonyl, or R ³ and R ⁴ are adjacent It may have a substituent together with the nitrogen atom! /, Form a nitrogen-containing heterocyclic group},

 Formula (III)

 [0013] [Chemical 3]

[0014] {In Formula (III), R ⁵ and R ⁶ are the same or different and represent a hydrogen atom, a hydrocarbyl optionally having substituent (s), a hydrocarbylcarbonyl optionally having substituent (s), Or R ⁵ and R ⁶ together with the adjacent carbon atom have a substituent! /, ^May ! / Form a cyclic hydrocarbyl},

 Or formula (IV)

 [0015] [Chemical 4]

[In the formula (IV), n represents an integer of 1 to 10; R ⁷ and R ⁸ are the same or different and represent a hydrogen atom, an optionally substituted hydrocarbyl, and a substituent. A force representing an optionally substituted hydrocarbylcarbonyl, or an optionally substituted cycloalkane, or a substituent, wherein R ⁷ and R ⁸ together with two adjacent carbon atoms each Form an aromatic ring that may have a group (provided that W and Z are not a hydrogen atom at the same time, and if either W or Z is a hydrogen atom, X and Y are not a single bond at the same time)] The additive for oils containing ester represented by these.

 [0017] (2) The additive for oils according to (1), wherein X represents a sulfur atom.

(3) The additive for oils according to (1), wherein X and Y are the same and represent a sulfur atom. (4) The additive for oils according to (1) to (3), wherein a and b are the same;!

(5) 1 ^ and R ² are the same or different and represent alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, or aryl having 4 to 20 carbon atoms. (1) to (4)! /, An additive for oils according to any one of the above.

(6) 1 ^ and R ² are the same or different and each represents alkyl having 1 to 20 carbons or alkenyl having 2 to 20 carbons. Additives.

[0018] (7) W and / or Z represents the formula (II), R ³ and R ⁴ forces are the same or different, a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, May have a substituent

V, alkenyl having 2 to 20 carbon atoms, having a substituent, may be! /, Cycloalkyl having 3 to 20 carbon atoms, aryl having 4 to 20 carbon atoms which may have a substituent, It may have a substituent, aralkyl having 5 to 20 carbon atoms, having a substituent! /, May! /, An alkanol having 2 to 21 carbon atoms, having a substituent Alkenol of 3 to 21 carbon atoms, which may have a substituent! /, Aroyl of 5 to 21 carbon atoms, which has a substituent! /, May! /, 2 to carbon atoms 21 alkoxycarbonyl, optionally substituted alkylsulfonyl having 1 to 20 carbon atoms, having a substituent, may be! /, Arylsulfonylsulfonyl having 4 to 20 carbon atoms, substituent /, Which may represent a cycloalkylcarbonyl having 4 to 21 carbon atoms, or R ³ and R ⁴ together with the adjacent nitrogen atom, which has a substituent. Mogugu Forces to form a nitrogen-containing heterocyclic group ing to 10-membered ring;; parts. 5 to W and / or Z represents the formula (IV), R ⁷ and R ⁸ 1S same or different, a hydrogen atom, a substituted An alkyl having 1 to 20 carbon atoms which may have a group, an alkenyl having 2 to 20 carbon atoms which may have a substituent, and an aryl having 4 to 20 carbon atoms which may have a substituent. Or R ⁷ and R ⁸ together with two adjacent carbon atoms, each having a substituent, may be! /, A cycloalkane having 3 to 20 carbon atoms, or The additive for oils according to any one of (1) to (6), which has a substituent and may form an aromatic ring having 4 to 20 carbon atoms.

(8) W and / or Z represents the formula (II), R ³ and R ⁴ forces are the same or different, a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, May have a substituent

V, alkenyl having 2 to 20 carbon atoms, having a substituent! /, May! /, Alkano having 2 to 21 carbon atoms May have a substituent, may have a C 5-21 aryl, or may have a substituent.

V, alkylsulfonyl having 1 to 20 carbon atoms, or having a substituent! /, May! /, (1) to (6)! /, Representing arylarylsulfonyl having 4 to 20 carbon atoms Oil additive for crabs.

 (9) The additive for oils according to (1) to (6), wherein W or Z represents the formula (II)!

[0020] (10) W and Z force The oil additive according to any one of (1) to (6), which is the same or different and represents the formula (II).

(11) W and / or Z represents the formula (II), and R ³ and R ⁴ forces are the same or different and are a hydrogen atom or a hydrocarbylcarbonyl optionally having a substituent (1) to ( The additive for oils as described in any one of 6).

(12) W and / or Z represents the formula (IV), R ⁷ and R ⁸ are the same or different, and a hydrogen atom or an optionally substituted alkyl having 1 to 20 carbon atoms, a substituent A force representing alkenyl having 2 to 20 carbon atoms, or R ⁷ and R ⁸ together with two adjacent carbon atoms each having an alkyl substituent having 1 to 20 carbon atoms. A benzene ring or a naphthalene ring optionally having an alkyl substituent of 1 to 20 carbon atoms, and n = l, (1) to (6), (8), (9) The additive for oils according to any one of (11).

(13) W and / or Z represents the formula (III), and R ⁵ and R ⁶ are the same or different and are a hydrogen atom or a C 1-20 alkyl which may have a substituent. , May have a substituent, alkenyl having 2 to 20 carbon atoms, may have a substituent! /, ^May ! /, Aryl having 4 to 20 carbon atoms, or R ⁵ and R ⁶ may have a substituent attached to the adjacent carbon atom.

The oil additive according to any one of (1) to (6), which forms V, cycloalkyl having 3 to 20 carbon atoms.

(14) W and / or Z represents the formula (III), and R ⁵ and R ⁶ are the same or different and are a hydrogen atom or an optionally substituted carbon atom having 1 to 10 alkyls, substituted 2 to 10 carbon atoms that may have a group; 10 to alkenyl, or 4 to 4 carbon atoms that may have a substituent; Oil additive for crabs.

[0022] (15) A lubricating oil comprising the additive for oils according to any one of (1) to (; 14) and a lubricating base oil. (16) Lubricating oil base oil is from mineral oil, vegetable oil, poly α-olefin, fatty acid ester, polyalkylene glycol, phosphate ester, silicone, silicate ester, polyphenyl ether, alkylbenzene, synthetic naphthene, gas-to-liquid. The lubricating oil according to (15), which is at least one selected from the group consisting of:

 The invention's effect

 [0023] According to the present invention, an additive for oils containing an ester which does not contain a metal component and a phosphorus component and which can impart wear resistance properties to oils such as lubricating base oils, and the oil It is possible to provide a lubricating oil containing a general additive.

 BEST MODE FOR CARRYING OUT THE INVENTION

In the present specification, an ester represented by the formula (I) may be referred to as an ester (I). The same applies to esters represented by other formulas.

[0025] The additive for oils of the present invention is added to oils such as lubricating base oils and fuel oils, and imparts wear resistance properties to these oils. Containing an ester represented by

[0026] In the present invention, the oils include, for example, engine oil, automatic transmission oil, continuously variable transmission oil, gear oil, power steering oil, shock absorber oil, turbine oil, hydraulic oil, refrigerating machine oil, rolling Oil, bearing oil, metal processing lubricant, sliding surface oil, grease, bio-lubricant, etc.

 [0027] Hydrocarbyl in the definition of ester (I) is a monovalent group formed by removing one hydrogen atom from a hydrocarbon, which may have a substituent, may be saturated or not. It may be saturated, or may have a linear, branched, cyclic or cyclic structure. Hydrocarbyl having 1-30 carbon atoms is preferred, and having 1-20 carbon atoms is more preferred. More preferably, examples include alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, aryl and the like.

 [0028] Examples of the saturated hydrocarbyl include alkyl, cycloalkyl and the like.

 Examples of the unsaturated hydrocarbyl include anolekenyl, anolequinyl, aryl, cycloalkenyl, aralkyl and the like.

As the linear hydrocarbyl, for example, linear alkyl, linear alkenyl, A linear alkynyl is mentioned, A C1-C20 thing is more preferable. Examples of the branched hydrocarbyl include branched alkyl, branched alkenyl, and branched alkynyl.

 Examples of the cyclic hydrocarbyl include cycloalkyl, cycloalkenyl, aryl and the like.

 Examples of the hydrocarbyl having a ring structure include hydrogen atoms of alkyl or alkenyl, those substituted by a cyclic hydrocarbyl, and those having 4 to 20 carbon atoms are preferable. Specific examples thereof include phenylbenzyl, biphenylmethyl, naphthylmethyl, 2-phenylvinyl-1-yl and the like.

 [0029] The hydrocarbyl may contain one or more of an oxygen atom and a sulfur atom. Examples of the hydrocarbyl containing an oxygen atom include those containing an ether bond. Examples of the hydrocarbyl containing a sulfur atom include those containing a disulfide bond, a sulfide bond, a polysulfide bond, and the like.

 [0030] The hydrocarbyl part of the hydrocarbyl carbonyl has the same meaning as the hydrocarbyl.

 As hydrocarbylcarbonyl, those having 2 to 21 carbon atoms are preferable, for example, alkenol, alkenol, aroyl and the like.

 [0031] The hydrocarbyl part of hydrocarbyloxycarbonyl has the same meaning as the hydrocarbyl.

 Hydrocarbyloxycarbonyl having 2 to 21 carbon atoms is preferred, for example, alkoxycarbonyl, cycloalkyloxycarbonyl, alkenyloxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl and the like. It is done.

 [0032] The hydrocarbyl moiety of hydrocarbylsulfonyl has the same meaning as the hydrocarbyl.

 As hydrocarbylsulfonyl, those having 1 to 20 carbon atoms are preferable, for example, alkynolsulfonyl, alkenylsulfonyl, and allylsulfonyl.

[0033] Examples of the alkyl include linear or branched alkyl having 1 to 20 carbon atoms. The linear alkyl having 1 to 20 carbon atoms is preferably, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, noel, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl. Octadecyl Doro force S is mentioned. More preferably, methyl, octadecyl, etc. are mentioned. Preferred examples of the branched alkyl having 3 to 20 carbon atoms include isobutyl, sec butyl, tert butynole and neopentyl.

 [0034] Examples of alkenyl include force S such as linear or branched alkenyl having 2 to 20 carbon atoms. As the straight chain alkenyl having 2 to 20 carbon atoms, preferably, for example, vinyl, vinylol, 3-butene 1-yl, 2-butene 1-yl, 1-butene 1-yl, 4-pentene 1-yl, 3-pentene 1-yl, 2-pentene 1-yl, 1-pentene 1-yl, octadecenyl, oleyl, octadecadienyl. More preferred are octadecenyl, oleyl and the like, and even more preferred is force S such as oleyl. Preferred examples of the branched alkenyl having 3 to 20 carbon atoms include isopropenyl and 2-methyl-1-propene-1-yl.

 [0035] Examples of alkynyl include linear or branched alkynyl having 2 to 20 carbon atoms. As the straight chain alkynyl having 2 to 20 carbon atoms, for example, Examples include tetradecininole, hexadecynyl, and octadecynyl. Preferred examples of the branched alkynyl having 4 to 20 carbon atoms include 3-methyl-1-butyne 1yl.

Yes

 [0036] Preferable examples of cycloalkanes having 3 to 20 carbon atoms include cyclohexanone, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclootatan, cyclononane, cyclodecane, cyclohexane. Pentadecane, cycloicosane, etc.

[0037] Preferable examples of cycloalkyl having 3 to 20 carbon atoms include cyclopropynole, cyclof, chinole, cyclopentinole, cyclohexinole, cyclopentinole, cyclooctyl, cyclononyl. , Cyclodecyl, cyclopentadecyl, cycloicosyl and the like.

[0038] Preferred examples of cycloalkenyl having 3 to 20 carbon atoms include cyclopropeninole, cyclopteninole, cyclopenteninole, cyclohexeninole, and cyclopente. Ninole, cyclootateninole, cyclononeninole, cyclodeceninole, cyclopentadecenole, cyclicosenyl and the like can be mentioned.

[0039] The alkyl part of the alkanoyl has the same meaning as the above alkyl.

 As alkanoyl, those having 2 to 21 carbon atoms are preferred. Examples include tridecanol, tetradecanol, hexadecanol, octadecanol, and oleo oil. More preferably, acetyl

And oleo oil.

[0040] The alkenyl part of the alkenol is as defined above.

 As the alkenol, those having 3 to 21 carbon atoms are preferable, for example, attaylroyl, methacroroyl, octadecenoyl, octadecadenoyl and the like.

[0041] Specific examples of aryl having 4 to 20 carbon atoms are phenyl, biphenyl, triphenyl, naphthyl, biranyl and the like.

[0042] The alkyl part of the aralkyl has the same meaning as the alkyl, and the aryl part has the same meaning as the aryl.

 As the aralkyl, those having 5 to 20 carbon atoms are preferred, and examples thereof include benzyl, phenethanol, 3-phenylpropyl, naphthylmethyl, biphenylmethyl and the like.

[0043] The reel part of the alloy is synonymous with the reel.

 As the aroyl, those having 5 to 21 carbon atoms are preferred, for example, benzoyl, naphthoyl, toluoyl, xyloyl and the like.

[0044] The cycloalkyl portion of the cycloalkyl carbonyl has the same meaning as the above cycloalkyl. The cycloalkylcarbonyl is preferably one having 4 to 21 carbon atoms. For example, cyclopropinorecanoleponinore, cyclobutinorecano Examples include reponinore, cyclopentinorecanoleponinole, cyclohexylcarbonyl and the like.

[0045] The alkyl moiety of alkoxycarbonyl has the same meaning as the above alkyl.

As the alkoxycarbonyl, those having 2 to 21 carbon atoms are preferable, for example, methoxycanoleboninore, ethoxycanoleponinore, propinoreoxycanoleponinore, tert-butoxycanoleponi Nore (BOC).

[0046] The cycloalkyl part of the cycloalkyloxycarbonyl is the same as the above cycloalkyl.

 Preferred examples of the cycloalkyloxycarbonyl include those having 4 to 21 carbon atoms, such as cyclopropinoreoxycanoleponinole, cyclopentinoreoxycanoleponinole, cyclohexyloxycarbonyl and the like.

[0047] The alkenyl part of alkenyloxycarbonyl has the same meaning as the above alkenyl.

 As alkenyloxycarbonyl, those having 3 to 21 carbon atoms are preferable, for example, alkoxycarbonyl and the like.

[0048] The aryl portion of the aryl boron is synonymous with the aryl.

 Examples of aryloxycarbonyl include those having 5 to 21 carbon atoms, preferably phenyloxycarbonyl, naphthyloxycarbonyl, biphenyloxycarbonyl and the like.

 [0049] The aralkyl portion of the aralkyloxycarbonyl is synonymous with the aralkyl.

 As the aralkyloxycarbonyl, those having 8 to 21 carbon atoms are preferable, for example, benzyloxycarbonyl, naphthylmethyloxycarbonyl and the like.

[0050] The alkyl moiety of the alkylsulfonyl has the same meaning as the above alkyl.

 Examples of alkylsulfonyl include those having 1 to 20 carbon atoms, preferably methanesulfonyl, ethanesulfonyl, and isopropylsulfonyl.

[0051] The alkenyl part of alkenylsulfonyl is as defined above.

 Examples of alkenylsulfonyl include those having 2 to 20 carbon atoms, preferably vinylsulfonyl and arylsulfonyl.

[0052] The aryl moiety of arylsulfonyl is as defined above.

 Examples of arylsulfonyl include those having 4 to 20 carbon atoms, preferably p-toluenesulfonyl and benzenesulfonyl.

[0053] Examples of the aromatic ring include aromatic hydrocarbons having 4 to 20 carbon atoms, preferably

, Benzene, naphthalene, anthracene, naphthacene, pyrene and the like.

[0054] As the nitrogen-containing heterocyclic group, in addition to one nitrogen atom, for example, a nitrogen atom, an oxygen atom, and A 5- or 6-membered monocyclic heterocyclic group which may contain an atom selected from a sulfur atom and a bicyclic or tricyclic condensed 3- to 8-membered ring and selected from a nitrogen atom, an oxygen atom and a sulfur atom Examples include condensed heterocyclic groups that may contain atoms, and more specifically, aziridinyl, azetiduyl, pyrrolidinyl, piperidino, piperidinyl, azepanyl, 1, 2, 5, 6-tetrahydropyridyl, imidazolidinyl, pyrazolidinyl, Perajul, Homopiperadul, Birazolinyl, Oxazolidinyl, Morpholino, Thiazolidinyl, Thiomorpholino, 2H-Oxazolyl, 2H-thiazolyl, Dihydroindolyl, Dihydroisoindolinole, Benzimidazolidinyl, Dihydrobenzoxazolyl, Dihydrobenzoxazolyl, Dihydrobenzoxazolyl Tetrahydroisoquinori , Tetrahydroquinoxalinyl, tetrahydroquinazolinyl, 2-pyrrolidinone 1-1-yl, 2-piberidinone 1-1-yl and the like.

 It may have a substituent, may! /, An alkanoyl substituent,

 It may have a substituent, may! /, An alkenol substituent,

 With substituents, may! /, Hydrocarbyl substituents,

 May have a substituent, may! /, A hydrocarbylcarbonyl substituent,

 An optionally substituted hydrocarbyloxycarbonyl substituent,

 May have a substituent, may! /, A hydrocarbylsulfonyl substituent,

 With substituents! /, May! /, Alkyl substituents,

 It may have a substituent, may! /, An alkenyl substituent,

 It may have a substituent, may! /, An aryl substituent,

 It may have a substituent, may! /, An aralkyl substituent,

 It may have a substituent, may! /, A substituent of alkoxycarbonyl,

 It may have a substituent, may! /, A substituent of alkylsulfonyl,

 With substituents! /, May! /, Arylsulfonyl substituents,

 It may have a substituent, may! /, Aroyl substituent,

 Having a substituent, may be, a substituent of cycloalkylcarbonyl,

 Examples of the substituent in are:

Each is the same or different and has 1 to 5 substitutions of hydroxyl, formyl, epoxy, force noreboxinore, menorecapto, amino, hydrazino, imino, azo, nitro, nitrinore, talented quix, Funoleo mouth and so on.

[0056] An aromatic ring substituent which may have a substituent,

 It may have a substituent, may! /, A substituent of cycloalkane,

 With substituents, may! /, Cycloalkyl substituents,

 It may have a substituent, may! /, A nitrogen-containing heterocyclic group,

 Examples of the substituent in are:

 Each may be the same or different and may be substituted or substituted 1-5 alkyl, alkenyl, alkynole, hydroxyl, formyl, epoxy, carboxyl, mercapto, amino, hydrazino, imino, azo, nitro, nitrile, oxime, fluoro, etc. . The alkynole, alkenyl, and alkynyl shown here are as defined above.

[0057] a benzene ring optionally having an alkyl substituent of 1 to 20 carbon atoms,

 Has an alkyl substituent of 1 to 20 carbon atoms! /, May! /, Naphthalene ring

 Examples of the alkyl having 1 to 20 carbon atoms include, for example, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, noel, and decyl, each having the same or different number. , Pentadecyl, icosyl, etc.

 [0058] Among such esters (I), as a more preferred example, a and b are simultaneously 1 or

Is an integer of 2, X and Y are simultaneously sulfur atoms, W and Z forces are simultaneously represented by formula (II) {in formula (II), R ³ and R ⁴ are the same or different, and are hydrogen atom, hydrocarbyl carbonyl And represents hydrocarbylsulfonyl}, and at the same time, the formula (III) {in the formula (III), R ⁵ and R ⁶ are the same or different, and optionally substituted hydrocarbyl, or R ⁵ and R ⁶ represents an optionally substituted cyclic hydrocarbyl formed together with an adjacent carbon atom}, or at the same time the formula (IV) {wherein n is 1 R ⁷ and R ⁸ are the same or different and are a hydrogen atom, an optionally substituted carbon having 1 to 20 alkyls, and an optionally substituted carbon number. An alkenyl having 2 to 20 carbon atoms, a force representing an aryl having 4 to 20 carbon atoms which may have a substituent, R ⁷ and R ⁸ together with two adjacent carbon atoms have a substituent! /, May! /, Force to form a cycloalkane of 3 to 20 carbon atoms, or A fragrance having 4 to 20 carbon atoms which may have a substituent An ester (I) represented by

[0059] More preferably, for example, the following esters (I 1 1) to esters (I 1 11) may be mentioned.

[0060] [Chemical 5]

[0061] [Chemical 6] (Le 2)

 [0062] [Chemical 7]

[0063] [Chemical 8]

(

[0064] [Chemical 9] (μ ₅₎

[0065] [Chemical 10]

[0066] [Chemical 11]

[0067] [Chemical 12]

[0068] [Chemical 13]

[0069] R represents a saturated or unsaturated hydrocarbyl having 1 to 10 carbon atoms, or an aryl having 4 to 10 carbon atoms.

[0070] [Chemical 14]

[0071] [Chemical 15] {lH}

[0072] MsOH represents methanesulfonic acid.

 The ester (I) described above can be used as an additive for oils or the like as it is, but it can also be used after being modified into a salt, for example.

 Examples of the salt include acid addition salts and amino acid addition salts.

[0073] Examples of acid addition salts include organic acid salts and inorganic acid salts. Examples of the organic acid salt include carboxylate and sulfonate, and preferably, formate, acetate, trifluoroacetate, propionate, methanesulfonate, p-toluenesulfonate, and triflurate. For example, chloromethane sulfonate, and more preferably methane sulfonate. Examples of inorganic acid salts include hydrochloride and hydrobromide

, Hydroiodide, nitrate, sulfate, carbonate, borate, etc. (however, phosphate is not included), preferably borate.

[0074] Examples of amino acid addition salts include lysine, glycine, phenylalanine, and aspartic acid.

And addition salts such as glutamic acid.

[0075] The salt of the ester (I) has been obtained! / When the ester (I) is obtained in the form of a salt, it can be purified as it is, or when it is obtained in the free form, the ester (I ) Is dissolved or suspended in a suitable solvent, and an acid or base is added to isolate and purify.

 The ester (I) and its salt may exist in the form of an adduct with water or various solvents, and these adducts can also be used as the additive for oils of the present invention.

[0076] Some esters (I) may have stereoisomers such as geometrical isomers, optical isomers, tautomers, etc. In the present invention, all possible isomerisms including these are possible. Bodies and mixtures thereof can also be used as additives for oils.

[0077] The ester (I) can be produced by reacting a dibasic acid corresponding to this ester with an alcohol in the presence of a basic compound at 0-100 ° C using a condensing agent.

In this case, it is preferable to use 2 to 10 equivalents of alcohol with respect to the corresponding dibasic acid. It is more preferable to use 2 to 5 equivalents. Further, it is preferable to use a basic compound in an amount of 0.;! To 20 equivalents, preferably 0.5 to 5 equivalents, and a condensing agent in an amount of 0 .;! To 20 equivalents, preferably 0.5 to 5 equivalents. .

[0078] The corresponding dibasic acid is not limited as long as it corresponds to the ester (I), that is, R ¹ and R ^{2 in} the formula (I) are hydrogen atoms.

 [0079] Specific examples of the dibasic acid having an amino group include S-carboxymethylcysteine, lanthionine, cystine, homocystine, penicillamine disulfide and the like. Examples of the substituent of the amino group which may have a substituent include hydrocarbyl, hydrocarbylcarbonyl, hydrocarbyloxycarbonyl, hydrocarbylsulfonyl and the like. Most of the dibasic acids can be produced according to the methods described in, for example, JP-A-62-48394 and JP-A-51-136619.

[0080] As the alcohol, those corresponding to the ester (I), that is, those consisting of R ¹ or R ² and hydroxyl (R ¹ — OH or R ² — OH) in the formula (I) are not limited. Absent. Many of these alcohols are commercially available, and can be produced according to the methods described in, for example, JP-A Nos. 2000-344695 and 2001-89403. .

 [0081] Examples of the basic compound include amine compounds such as pyridine lutidine, 4-dimethylaminopyridine, and triethylamine.

[0082] Examples of the condensing agent include 1-ethyl-3- (N, N, -dimethylaminopropyl) carbopositimide, and calpositimide compounds such as N, N'-dicyclohexylcarbopositimide.

[0083] As another method for producing the ester (I), for example, a dibasic acid and an alcohol corresponding to this ester are mixed in the presence of an acid catalyst such as methanesulfonic acid or p-toluenesulfonic acid. The method of making it react at ° C is also mentioned. In addition, a method using hydrogen chloride, thionyl chloride, or the like as the catalyst can be used. Also in these cases, it is preferable to use 2 to 10 equivalents of alcohol with respect to the dibasic acid, more preferably 2 to 5 equivalents. [0084] In each of these production methods, when the corresponding dibasic acid reacts with an alcohol, if necessary, active groups such as amide-containing carboxyl, hydroxy, mercapto, etc. possessed by the dibasic acid or alcohol. Protecting groups may be introduced into, and the protecting groups may be removed as appropriate after the reaction.

 The introduction and removal of the protecting group from the active group can be carried out by a known method [for example, Protective Groups In Organic Synthesis, third edition, Green, Γ. W. Greene ) By John Wiley & Sons Inc. (1999).

 [0085] Examples of the protecting group include benzyloxycarbonyl, pmethoxybenzyloxy canoleponinole, tert butoxycanoleponinole, 9 fluorenolemethoxycanoleponinole, 3-dinitro 2-pyridinesulfenyl, 2 —Bendioxycarbonyl halide, tert-butyl, benzyl, benzyl halide, tosyl, 4-methoxy 2, 3, 6 trimethylbenzenesulfonyl, 2, 2, 5, 7, 8 pentamethylchroman 6 sulfonyl, 2, 4 Dinitrophenyl, Tritinole, Benzyloxymethylenole, 4 Methylbenzyl, 4-Methoxybenzinole, Acetamidomethylenole, Honoreminole, Acetinole, 4, 4, Dimethoxybenzhydrinore, 2, 4, 6-Trimethoxybenzyl Can be mentioned.

 [0086] The ester (I) described above can impart antiwear characteristics to oils such as lubricating base oils and fuel oils when used as an additive for oils. It can be used in place of friction modifiers (friction reducing agents, oil-based agents), wear reducing agents (extreme pressure agents, etc.). Further, depending on the case where the wear resistance can be imparted only by using the ester (I), these conventional products and the ester (I) may be used in combination.

 Further, two or more esters (I) having different structures in the present invention may be used as a mixture.

[0087] The lubricating oil of the present invention comprises a lubricating base oil and an oil additive containing the ester (I) described above. The content of the additive for oils in the lubricating oil is preferably 0.00;! To 300 mmol (millimono), more preferably 0.0;! To 200 mmol, and 0.; More preferably, lOOmmol. If it is within this range, the force S will give sufficient wear resistance. [0088] As the lubricating base oil, for example, various lubricating base oils represented by natural base oil and synthetic base oil can be used. These may be either polar base oils or nonpolar base oils.

 [0089] Examples of natural base oils include mineral oils, vegetable oils, and animal oils, and examples of mineral oils include, for example, paraffin-based crude oils, intermediate-based crude oils, and naphthenic-based crude oils. It is not limited. In addition, a solvent refined oil obtained by treating a lubricating oil raw material derived by atmospheric pressure or vacuum distillation with an aromatic extraction solvent such as phenol or furfural, and hydrogen under severe cracking reaction conditions in the presence of a hydrocracking catalyst. In the presence of hydrocracking oil obtained by contact with the catalyst, hydrotreating catalyst such as cobalt and molybdenum as silica-alumina support, the lubricating oil feedstock is treated with hydrogen under hydrotreating conditions. Hydrotreated oil obtained by contact; by a method using multiple stages of hydrotreating, by hydrotreating or solvent purification, followed by alkali distillation or sulfuric acid washing, or by hydrotreating after catalyst removal The resulting highly refined oil can be preferably used. Examples of vegetable oils include, but are not limited to, rapeseed oil, sunflower oil, soybean oil, olive oil, palm oil, and corn oil.

 [0090] Synthetic base oils include polybutene, polypropylene, poly-olefins such as α-olefin oligomers having 8 to 14 carbon atoms; fatty acid monoesters, aromatic monoesters, fatty acid diesters, aromatic diesters, and aliphatic polyesters. Esters such as basic acid esters, aromatic polybasic acid esters and polyol polyesters; polyalkylene glycols, phosphate esters, silicones, silicate esters, polyphenyl ethers, alkylbenzenes, synthetic naphthenes, gas-to-liquid (GTL), Forces that include fluorocarbons, ionic liquids, etc.

 Among these, preferable lubricant base oils include solvent refined oil, hydrocracked oil, highly refined oil, vegetable oil, poly-α-olefin, fatty acid ester (fatty acid monoester, fatty acid diester, Basic acid esters), polyalkylene glycols, phosphate esters, silicones, silicate esters, polyphenyl ethers, alkylbenzenes, synthetic naphthenes, gas-to-liquids (GTUs), one or more of which may be used I like it.

[0092] The lubricating oil of the present invention includes the additive for oils containing the lubricating base oil and ester (I). In addition, as optional components, detergent dispersant, antioxidant, wear reducing agent (antiwear agent, anti-seizure agent, extreme pressure agent, etc.), friction modifier (friction reducing agent, oily agent), antifungal agent, It may contain additives such as a phase inhibitor, a pour point depressant, a viscosity index improver, a thickener, an antiseptic, an antifoaming agent, a demulsifier, a dye, and a fragrance. The addition amount of these additives can be set as appropriate, but is preferably contained in the lubricating oil from 0.00;

 [0093] The cleaning dispersant is a dispersion action that stably disperses sludge in oil generated over time and suppresses the accumulation of these sludges; unstable intermediates such as water, organic acids, sludge precursors, etc. Solubilization of the varnish and sludge by solubilization; Lubricating base oil, organic acid produced by deterioration of additives, neutralization of sulfuric acid and corrosion of the base material and corrosion It is an additive mainly intended for acid neutralization and the like that suppresses causative wear. Cleaning dispersants can be broadly divided into metal-based detergents that contain metals and ashless dispersants that do not contain metals. Typical examples of the former are neutral / basic sulfonates and overbased ones. This is a colloidal dispersion of metal hydroxides and carbonates in sulfonate, overbased phenate, overbased salicylate, phosphonate, overbased strength lupoxylate and the like. Examples of the metal include calcium, magnesium, and sodium. Examples of the ashless dispersant include monosuccinimide and bissuccinimide. As the detergent dispersant, one of these may be used alone, or two or more may be used in combination.

 [0094] The antioxidant is an additive whose main purpose is to suppress degradation and decomposition caused by the reaction of the lubricating base oil or additive with oxygen in the air. The mechanism of action is to stop the chain transfer reaction, decompose peroxides, and inactivate metal compounds that can serve as oxidation catalysts. Those that act as chain terminators include phenolic and aromatic amine compounds. Examples of substances that act as peroxide decomposing agents include sulfur-based and sulfur-phosphorus-based compounds. Examples of the metal deactivator include compounds having the ability to form a complex with a metal such as benzotriazole. As the antioxidant, one of these may be used alone, or two or more may be used in combination.

[0095] A wear reducing agent is a frictional surface of friction generated by relative motion, and forms a film of an inorganic compound by chemically reacting with a metal or metal oxide forming the friction surface, thereby reducing wear and burning. It is an additive mainly intended to prevent sticking. Mainly intended to suppress wear Anti-seizure agents are mainly intended to prevent seizures, and anti-seize agents are primarily intended to prevent seizures, and those that are primarily intended to prevent seizures and suppress wear under severe conditions. Sometimes called pressure agents. Wear reducing agents are broadly classified into sulfur, phosphorus, chlorine, and organometallic, and sulfur compounds include olefin sulfide and sulfide. Typical examples include dibenzyl disulfide (DBDS). Can be mentioned. Phosphorous compounds include phosphites, phosphates, and amine phosphates, and typical examples include tricresyl phosphate (TCP). Chlorinated compounds include chlorinated paraffins. Typical examples of organometallic materials include zinc-dialkyldithiophosphate (ZnDTP), zincate (MoDTC), and molybdenum-dialkyldithiophosphate (MoDTP). As the wear reducing agent, one of these may be used alone, or two or more may be used in combination.

 [0096] When the additive for oils of the present invention containing ester (I) is used, these sulfur-based, phosphorus-based, chlorine-based, and organometallic wear-reducing agents may be used in combination. If the additive for oils of the present invention is used, excellent wear reduction properties can be imparted to oils such as lubricating base oils without using these known wear reducing agents in combination. Therefore, for example, it is possible to prevent an increase in the concentration of metal or phosphorus in oils by using a phosphorus-based or organometallic wear-reducing agent in combination.

[0097] The friction modifier mainly reduces or increases friction by physical adsorption or chemical adsorption on the metal or metal oxide forming the friction surface in the friction surface of friction generated by relative motion. The target additive. Those whose main purpose is to reduce friction may be referred to as oiliness agents or friction reducing agents. Friction modifiers can be broadly classified into ashless friction modifiers that do not contain metals, metal-based friction modifiers that contain metals, and solid lubricants. Ashless friction modifiers have a structure that has both a polar group that binds strongly to the metal surface in the molecule and a long-chain carbon chain. Typical examples include stearic acid, oleic acid, stearylamine, oleyl alcohol, And oleylamine, oleylamide, glycerin monooleate (GMO) and the like. Examples of metal friction modifiers include MoDTC and MoDTP. Examples of solid lubricants include graphite and molybdenum disulfide. Friction As the preparation, one of these may be used alone, or two or more may be used in combination.

[0098] When the oil additive of the present invention containing ester (I) is used, a friction modifier such as an ashless friction modifier, a metal friction modifier, or a solid lubricant is used in combination. However, if the additive for oils of the present invention is used, an excellent friction reducing property is imparted to oils such as lubricating base oils without using these known friction modifiers in combination. can do. Therefore, for example, it is possible to prevent an increase in the concentration of metals in oils by using a metal friction modifier in combination.

 [0099] The antifungal agent is an additive whose main purpose is to prevent the base material from being distorted mainly due to oxygen and moisture present in the air. Antifungal agents include alkyl succinic acid derivatives, metal soaps, esters, sulfonates, phosphites, amines and the like.

 [0100] The pour point depressant is an additive whose main purpose is to further improve the low temperature fluidity by further lowering the wax pour point of the lubricating oil and further lower the minimum usable temperature of the lubricating oil. Typical examples include polyalkyl metatalates, polyalkyl acrylates, polybutyl acetates, polyalkyl styrenes, polybutenes, condensates of chlorinated paraffins and naphthalene, condensates of chlorinated paraffins and phenols, and the like.

 [0101] A viscosity index improver is an additive whose main purpose is to reduce the viscosity change due to the temperature of the lubricating oil by increasing the viscosity index, and to further expand the usable temperature range of the lubricating base oil. . Typical examples include polyalkylmetatalylate, polyisobutylene, polyalkylstyrene, ethylene-propylene copolymer, styrene-hydrogenated copolymer, styrene-maleic anhydride ester copolymer, and the like. These can be used alone or in combination.

 [0102] Anti-foaming agents are the main causes of bubbling of lubricant base oil, oil shortage and increased compressibility resulting in machine malfunction due to wear and seizure, lubricant base oil overflow, oxidation deterioration It is an additive whose main purpose is prevention. Typical examples include dimethylsiloxane, fluorosilicone, polyacrylate, perfluoroalkyl ether and the like.

[0103] Antifungal agents, pour point depressants, viscosity index improvers, antifoaming agents are V, among those exemplified for deviation One type may be used alone, or two or more types may be used in combination.

[0104] The lubricating oil of the present invention includes, for example, engine oil, automatic transmission oil, continuously variable transmission oil, gear oil, power steering oil, shock absorber oil, turbine oil, hydraulic oil, refrigerating machine oil, rolling oil, bearing It can be used for various applications such as oil, lubricating oil for metal processing, sliding surface oil, grease, and biological lubricant.

 [0105] Engine oil refers to automobiles, motorcycles, trains, ships, submersibles and other 4-cycle gasoline engines, 2-cycle gasoline engines, diesel engine piston ring and cylinder sliding parts, connecting rods and crankshaft bearings, cams Lubricant used to lubricate valve lifter valve systems and other parts.

 [0106] Automatic transmission oil is lubricating oil used for power transmission, wear adjustment, and lubrication of various gears consisting of a fluid transmission, a gear unit, a wet clutch and a hydraulic mechanism that controls them. is there.

 [0107] The continuously variable transmission oil is a lubricating oil used for a continuously variable transmission. There are two types of continuously variable transmissions, the belt drive type and the traction drive type, which are used as speed changers for automobiles, machine tools, and industrial machines. A belt-driven continuously variable transmission consists of two pulleys on the engine side and drive wheel side and a belt hung between them. Lubricating oil is used for lubrication and hydraulic operation of the belt, clutch plate, and hydraulic system. . Traction drive type continuously variable transmissions transmit torque between rolling elements through an oil film. Lubricating oil is used to transmit torque, prevent seizure of the rolling elements, and wear.

 [0108] Gear oil is lubricating oil used for the purpose of lubricating gears and bearings, and is roughly classified into automobile gear oil and industrial gear oil. Automobile gear oil is used to lubricate helical gears and hypoid gears used in manual transmissions, automatic transmission axles, and final reduction gears (diffs). Industrial gear oil is used to lubricate helical gears, bevel gears, worm gears, etc. used in industrial machinery, including steel equipment, and gears in equipment.

 [0109] The power steering oil is a lubricating oil used in the power steering device for the purpose of reducing the force applied to the steering wheel.

[0110] Shock absorber oil is used for the purpose of providing maneuverability, stability and ride comfort. It is a lubricating oil used for shock absorbers in pension equipment. Turbine oil is lubricating oil used to lubricate turbine bearings and reduction gears, and is used in steam turbines, gas turbines, nuclear turbines, etc. for generators, ships and aircraft.

 [0111] Hydraulic oil is lubricating oil used to lubricate the sliding parts of hydraulic equipment and devices, such as construction machinery, machine tools, metal and plastic processing machines, vehicles, ships and aircraft. Used for hydraulic equipment and devices.

 [0112] Refrigerating machine oil is a lubricating oil that is used in the presence of coexistence with refrigerants in compressors of refrigerators, and is used in refrigerators for air conditioning, refrigerators, freezing and refrigeration for food processing and distribution, industrial use, etc. Used

[0113] The rolling oil is a lubricating oil used for the purpose of imparting lubricity to an excessive rubbing portion between the material and the roll when rolling a metal material such as steel or aluminum alloy.

 [0114] Bearing oil is a lubricating oil that is the main lubrication object of bearings. For special bearings of various machine tools, oil film bearings used for large sliding bearings of rolling mill roll necks. There is oil. Recently, it is a lubricating oil used as a fluid bearing oil (dynamic pressure bearing oil) for bearings of precision machines such as spindle motors built into hard disk drives such as personal computers.

 [0115] The metal working lubricant is a lubricant used for lubrication and cooling in metal machining, and includes cutting oil, rolling oil, press working oil, and drawing oil.

 [0116] Sliding surface oil is used to impart friction characteristics to the stable surface of the table of various machine tools such as lathes and grinding machines where the sliding speed is very slow and no oil film is formed. Lubricating oils include dedicated oils and hydraulic oils that serve both as stable surface lubrication and hydraulic fluids.

[0117] Grease is a semi-solid or solid dispersion of a thickening agent in lubricating oil. For automobiles, wheel bearings, constant velocity ball joints, universal joints, propeller shaft center supports, clutches Release bearings, water pump bearings, steering and accelerator linkage mechanisms, electrical equipment bearings, propeller shaft splines, instrument wire cables, wind regulators, body parts such as door mirrors, brake parts For industrial use, rolling force, plain bearings, gears and Used in equipment with joints such as chains and machine sliding surfaces.

 [0118] Biolubricants are lubricants used for artificial joints, artificial cartilage, and artificial tears-type eye drops, and materials that not only have lubricity and durability but also have no impact on the body are required. The

 [0119] As described above, the additive for oils containing ester (I) imparts wear resistance characteristics to the lubricating base oil even though it does not contain metal or phosphorus. You can. Therefore, it is very preferable in terms of the environment and the use of conventional additives containing heavy metal phosphorus such as zinc and molybdenum is restricted due to concerns about influence on the human body and contamination of lubricating oil. It is also very effective for various applications (work machines such as belt competitors used in food processing and pharmaceutical manufacturing, medical equipment, etc.).

 [0120] In addition, the additive for oils containing ester (I) can reduce friction by adding to the lubricating base oil whether it is a polar base oil or a non-polar base oil. Wear resistance that combines wear resistance and wear resistance can be imparted. Therefore, conventionally, it is necessary to select and add both compatible friction modifiers and wear reducers (antiwear agents, anti-seizure agents, extreme pressure agents, etc.) according to the type of lubricant base oil. However, by adopting this oil additive, such complications can be eliminated.

 [0121] It should be noted that the additive for oils of the present invention can be added to other oils such as fuel oils that use only the lubricating base oil.

[0122] Examples of the fuel oil include highly hydrorefined, for example, high performance turbine fuel oil. Fuel oil that is highly hydrorefined in this way tends to have a particularly insufficient lubrication performance, and fuel pumps using such fuel oil are subject to wear. Therefore, the addition of the additive for oils of the present invention is very effective. The content of the additive for oils is in fuel derived 100 mass _^0/0, 0. 00001～; 10 mass _^0/0 Ca preferably <further (or 0.0000;! ~ 5 mass _^0/0 good Furthermore, it is preferably 0.00000 ;! to 1% by mass, and within this range, sufficient wear resistance can be imparted.

 The fuel oil may contain various additives in addition to the oil additives of the present invention.

[0123] Furthermore, the additive for oils of the present invention can be used as a solid lubricant as well as an additive to oils such as lubricating base oils and fuel oils. For example, solid lubricants can cause friction and wear on materials such as plastics and fibers, or on recording media, paints such as ink and film. It is added, coated or impregnated for the purpose of reducing.

[0124] More specifically, sliding members such as plastic gears, bearings, and cams, thermal recording media, magnetic recording media, transfer media, lithographic printing plate precursors, image receiving sheets, and toners used in electrophotographic parts It can be used in various applications such as protective coating layers such as photoconductors and electrophotographic photoreceptors or cleaning members, optical fiber optical fiber drop cables, polarizers, protective coating layers such as endoscopes, and optical films.

 Example

 [0125] The measurement data in the examples were obtained by the following measurement equipment and measurement method.

 (1) Nuclear magnetic resonance spectrum H-NMR; using tetramethylsilane as standard)

: GSX-400 (400MHz) (Enomoto Electronics)

 (2) Measurement of dynamic friction coefficient (Evaluation of friction reduction): Iwata-type pendulum friction tester (manufactured by Shinko Engineering)

 (3) Measurement of wear scar diameter (Evaluation of wear reduction): Shell-type four-ball friction tester (manufactured by Takachiho Seiki)

 [Production Example 1] N, N′-di (tert-butoxycarbonyl) cystine (Compound A)

 400 mL of lmol / L sodium hydroxide aqueous solution was added to 48 lg of cystine (manufactured by Kyowa Hakko Kogyo Co., Ltd.), and the mixture was stirred until evenly dissolved. To this, 200 mL of 1,4 dioxane was added, and tert-butyl carbonate 96 · Og (manufactured by Ibai) was added dropwise with stirring in an ice bath. After completion of dropping, the mixture was returned to room temperature and stirred for 10 hours. After the reaction, 1,4 dioxane was distilled off from the reaction solution at 50 ° C under reduced pressure, and the target product was extracted with ethyl acetate (manufactured by Kyowa Hakko Chemical). Furthermore, the aqueous layer was adjusted to pH 2 with lmol / L hydrochloric acid, and the target product was extracted again with ethyl acetate. The organic layer was washed with distilled water. The organic layer obtained above was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure at 50 ° C. to obtain 55.5 g of Compound A (yield: 63.0%). The physical properties of this compound A were as follows.

 [0127] 'H-NMR CCD OD, δ ppm); 1. 45 (s, 18H), 2. 98 (m, 2H), 3. 23 (m, 2H)

 Three

 , 4. 42 (m, 2H)

 [Production Example 2] N, N, -di (tert-butoxycarbonyl) homocystine (Compound B)

Homocystine 5.00 g (manufactured by Tokyo Chemical Industry) lmol / L sodium hydroxide aqueous solution lOOmL And stirred until evenly dissolved. To this, 20 mL of 1,4 dioxane was added, and 8.95 g of di tert butyl carbonate (manufactured by Ibai) was added dropwise with stirring in an ice bath. After completion of dropping, the mixture was returned to room temperature and stirred for 10 hours. After the reaction, 1,4 dioxane was distilled off under reduced pressure at 50 ° C., and the target product was extracted with ethyl acetate (manufactured by Kyowa Hakko Chemical). Furthermore, the aqueous layer was adjusted to pH 2 with lmol / L hydrochloric acid, and the target product was extracted again with ethyl acetate. The obtained organic layer was washed with distilled water. The organic layer obtained above was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure at 50 ° C. to obtain 5.53 g of Compound B (yield: 64.5%). The physical property values of this compound were as follows.

[0129] 'H-NMR CCD OD, δ ppm); 1. 44 (s, 18H), 1. 98— 2. 03 (m, 2H), 2. 15

 Three

 -2. 30 (m, 2H), 2. 65— 2. 85 (m, 4H), 4. 20— 4. 23 (m, 2H), 4. 89 (br, 4H)

 [0130] [Example 1] Cystindiol (Estenole (I 1))

 N, N, monodi (tert-butoxycarbonyl) cystine (compound A) 18.5 g, 4 dimethylaminoviridine 10.3 g (Wako Pure Chemical Industries), and oleyl alcohol 22.6 g (Wako Pure Chemical Industries, Ltd.) methylene chloride Dissolve in lOOmL (manufactured by Wako Pure Chemical Industries, Ltd.) and stir well. Then add 1 · 7g of 1-ethyl-3— (N, Ν'-dimethylaminopropyl) carpositimide (manufactured by Aiby) for 3 hours at room temperature, then Heated and stirred at 40 ° C for 3 hours. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off at 50 ° C under reduced pressure to obtain 38.2 g (yield: 96.5%) of N, N'-di (tert-butoxycarbonyl) cystinediol. Obtained.

 The resulting N, N′-di (tert-butoxycarbonyl) cystinediol was dissolved in 150 mL of methylene chloride and stirred until uniform. Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto until the disappearance of the raw material was confirmed by thin layer chromatography (Trifluoroacetic acid addition amount: 39. lg). After completion of the reaction, the reaction solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate solution, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C to obtain ester (1-1): 11.6 g (yield: 98.5%). The physical properties of this were as follows.

[0131] 'H-NMR CCDCI, δ ppm); 0. 88 (t, 6H), 1. 17-1. 41 (m, 44H), 1. 65 ( m, 4H), 1.74 (s, 4H), 1.92— 2.05 (m, 8H), 2.91 (m, 8H), 3.14 (m, 2H), 3.80 ( m, 2H), 4. 14 (t, 4H), 5. 28— 5. 40 (m, 4H)

 Elemental analysis results; C H N O S

 42 80 2 4 2

 Calculated value <C: 68. 06%, H: 10. 88%, N: 3. 78%, S: 8. 65%)

 (Measured value C: 67. 96%, H: 10. 99%, N: 3.75%, S: 8.62%)

[0132] The following evaluation was performed on the ester (I1) thus obtained.

 (1) Measurement of dynamic friction coefficient (Evaluation of friction reduction)

 Poly (α-olefin) (lubricant base oil Α) or di (3,5,5-trimethylhexyl) adipate (lubricant base oil B) with ester (1-1) as an additive for oils In addition, a trial oil of lubricating oil was prepared so as to be 10 mmol / kg.

 Next, the dynamic friction coefficient of this prototype oil at 40 ° C and 80 ° C was measured by a Kamata pendulum type friction tester (manufactured by Shinko Engineering Co., Ltd.). The dynamic friction coefficient was calculated from the initial amplitude of the pendulum, the amplitude when it was vibrated, and the number of vibrations. The results are shown in Table 1.

 (2) Measurement of wear scar diameter (Evaluation of wear reduction)

 Prototype oil is prepared in the same manner as (1) above, and tested according to the method specified in (ASTM D4172) (load; 40 kgf, number of revolutions: 1200 rpm, time: 60 minutes, temperature: 75 ° C). The subsequent wear scar diameter was measured. A shell-type four-ball friction tester (manufactured by Takachiho Seiki) was used as the tester. The wear scar diameter was the average value of all three fixed spheres in the vertical and horizontal directions. The results are shown in Table 1.

 [Example 2] Cystine di noctyl (ester (I 2))

N, N, monodi (tert-butoxycarbonyl) cystine (compound A) 18.5 g, 4 dimethylaminoviridine 10.3 g (manufactured by Wako Pure Chemical Industries, Ltd.), and n octyl alcohol 11.2 g (manufactured by Wako Pure Chemical Industries, Ltd.) are chlorinated After dissolving in methylene lOOmL (manufactured by Wako Pure Chemical Industries, Ltd.) and stirring well, add 1 · 9g of 1-ethinole — 3— (N, Ν'-dimethylaminopropyl) carpositimide (manufactured by Ibai), room temperature, then 40 ° Heat at C. Stir. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C to obtain 26.2 g of N, N'-di (tert-butoxycarbonyl) cystinedioctyl (yield: 93.6%). It was. The obtained N, N′-di (tertbutoxycarbonyl) cystinedioctyl 10 · Og was dissolved in methylene chloride and stirred until uniform. Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto until the disappearance of the raw material was confirmed by thin layer chromatography (addition amount of trifluoroacetic acid: 32.0 g). After completion of the reaction, the reaction solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (I 2): 6.4 g (yield: 91.4%). The physical properties of this were as follows.

 [0134] 'H-NMRCCDCl, δ ppm); 0.89 (t, 6H), 1.28 (m, 20H), 1.66 (m, 4H),

 Three

 1.76 (s, 4H), 2.91 (m, 2H), 3.14 (m, 2H), 3.80 (m, 2H), 4.14 (t, 4H) Elemental analysis results; C H N O S

 22 44 2 4 2

 (Calculated value C: 56.86%, H: 9.54%, N: 6.03%, S: 13.80%)

 (Measured value C: 56.84%, H: 9.56%, N: 6.02%, S: 13.81%)

 [0135] A trial oil was prepared in the same manner as in Example 1 except that the ester (I2) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 1.

 [Example 3] N, N'-diacetylcystinediol (ester (I 3))

 The cystine dioleyl 5.3 · g (ester (I-1)) obtained in Example 1 was dissolved in 10 OmL of methylene chloride (manufactured by Wako Pure Chemical Industries, Ltd.), stirred well, and then 4.6 g of acetic anhydride ( Mitsui Pure Chemicals) was added dropwise. After the reaction, the reaction mixture was washed with distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine until neutral. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (1-3): 4.lg (yield: 70.7%). The physical properties of this were as follows.

 [0137] 'H-NMRCCDCl, δ ppm); 0.89 (t, 6H), 1.27 (m, 44H), 1.65 (m, 4H),

 Three

 1.97-2.08 (m, 14H), 3.21 (m, 4H), 4.15 (m, 4H), 4.85 (m, 2H), 5.3 5 (m, 4H), 6.52 (d, 2H)

 Elemental analysis results; C H N O S

 46 84 2 6 2

 (Calculated value C: 66.94%, H: 10.26%, N: 3.39%, S: 7.77%)

 (Measured value C: 66.90%, H: 10.30%, N: 3.35%, S: 7.78%)

[0138] The same as Example 1 except that the ester (I3) thus obtained was used as an additive for oils. In this manner, a trial oil was prepared and evaluated in the same manner as in Example 1. However, only lubricating base oil A was used as the lubricating base oil. The results are shown in Table 1.

[Example 4] N, N 'dioleoyl cystinediol (ester (I 4))

 Dissolve 4.4 g of cystinediol (ester 1) and 1.8 g of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) obtained in Example 1 in 50 mL of methylene chloride (manufactured by Wako Pure Chemical Industries), and stir well under a nitrogen atmosphere. After that, 3.6 g of oleic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise and stirred at room temperature for 2 hours. The reaction solution was distilled water, 0.5 mol / L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine. And washed. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (I 4): 5. Og (yield: 65.9%). The physical property values were as follows.

 [0140] 'H-NMRCCDCl, δ ppm); 0.89 (t, 12H), 1.28 (m, 84H), 1.63 (m, 8H)

 Three

 , 1.92-2.08 (m, 16H), 2.25 (t, 4H), 3.21 (m, 4H), 4.15 (m, 4H), 4. 87 (m, 2H), 5.35 (m, 8H), 6.43 (d , 2H)

 Elemental analysis results; C H N O S

 78 144 2 6 2

 (Calculated value C: 73.76%, H: ll. 43%, N: 2.21%, S: 5.09%)

 (Measured value C: 73.66%, H: ll. 55%, N: 2. 15%, S: 5.02%)

 [0141] A trial oil was prepared in the same manner as in Example 1 except that the ester (I4) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. However, only lubricating base oil A was used as the lubricating base oil. The results are shown in Table 1.

 [0142] [Example 5] Cystine distearyl (ester (I 5))

N, N, monodi (tert-butoxycarbonyl) cystine (compound A) 18.5 g, 4 dimethylaminoviridine 10.3 g (manufactured by Wako Pure Chemical Industries), and stearyl alcohol 22.8 g (manufactured by Wako Pure Chemical Industries) 1-Ethyl-3- (N, Ν'-dimethylaminopropyl) carpositimide (Ibai) 17 · 7g was added, and the temperature was 3 hours at room temperature, then 40 ° C. And stirred for 3 hours. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain 38.0 g (yield: 95.6%) of N, N′-di (tert-butoxycarbonyl) cystine distearyl. The obtained N, N′-di (tert-butoxycarbonyl) cystine distearyl 15 · Og was dissolved in 150 mL of methylene chloride and stirred until uniform. Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto until the disappearance of the raw material was confirmed by thin layer chromatography (amount of trifluoroacetic acid: 40.2 g). After completion of the reaction, the reaction solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (I 5): 11.4 g (yield: 96.3%). The physical properties of this were as follows.

 [0143] 'H-NMR CCDCl, δ ppm); 0. 88 (t, 6H), 1. 20— 1. 40 (m, 60H), 1. 66 (

 Three

 m, 4H), 1.72 (s, 4H), 2.90 (dd, 2H), 3.15 (dd, 2H), 3.80 (dd, 2H), 4.14 (t, 4H)

 Elemental analysis results; C H N O S

 42 84 2 4 2

 (Calculated value C: 67. 69%, H: l l. 36%, N: 3. 76%, S: 8. 61%)

 (Measured value C: 67. 49%, H: 11-34%, N: 3. 66%, S: 8. 52%)

 [0144] A trial oil was prepared in the same manner as in Example 1 except that the ester (I5) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 2.

 [Example 6] N, N 'dioleoylcystine dimethyl (ester (I 6))

 N, N 'Di (tert-butoxycarbonyl) cystine (compound A) 4 · 4 g and 4-dimethylaminoamino lysine 2.4 g (manufactured by Wako Pure Chemical Industries, Ltd.) in methanol 1. Og (manufactured by Wako Pure Chemical Industries, Ltd.) and methyl chloride 25 mL After dissolving in (Wako Pure Chemical Industries, Ltd.) and stirring well, add 1-ethyl 3- (N, N'-dimethylaminopropyl) carpositimide (Ibai) 4.2g and then at room temperature for 2 hours, then Heated at 40 ° C for 3 hours and stirred. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain 4.2 g of N, N′-di (tert-butoxycarbonyl) cystine dimethyl (yield: 89.6%).

The obtained N, N′-di (tert-butoxycarbonyl) cystine dimethyl (2.3 g) was dissolved in 30 mL of methyl chloride and stirred until uniform. Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto until thinning chromatography confirmed the disappearance of the raw material (amount of trifluoroacetic acid-added caroten: 5.7 g). After completion of the reaction, the reaction solution is distilled water, saturated aqueous sodium hydrogen carbonate solution, saturated food. Washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain cystine dimethyl: 0.6 g (yield: 25.8%).

 0.6 g of cystine dimethyl and 0.7 g of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 20 mL of methyl chloride (manufactured by Wako Pure Chemical Industries, Ltd.), stirred well in a nitrogen atmosphere, and then 1.4 g of oleic acid chloride. (Manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with distilled water, 0.5 mol / L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (I 6): 1.7 g (yield: 89.7%). The physical property values thereof were as follows.

[0146] 'H-NMR CCDCl, δ ppm); 0. 88 (t, 6H), 1. 28 (m, 40H), 1. 65 (m, 4H),

 Three

 1.92- 2.08 (m, 8H), 2.24 (m, 4H), 3.21 (m, 4H), 3. 77 (s, 6H), 4. 89 (m, 2H), 5 .35 (m, 4H), 6. 40 (d, 2H)

 Elemental analysis results; C H N O S

 44 80 2 6 2

 (Calculated value C: 66.29%, H: 10.11%, N: 3.51%, S: 8.04%)

 (Measured value C: 66.10%, H: 10.20%, N: 3.52%, S: 7.96%)

 [0147] A trial oil was prepared in the same manner as in Example 1 except that the ester (I6) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 2.

 [Example 7] Homocystine dioleyl (ester (I7))

 N, N 'Di (tert-butoxycarbonyl) homocystine 2.50g, 4-dimethylaminopyridine 1.33g (Wako Pure Chemical Industries), oleyl alcohol 2.93g (Wako Pure Chemical Industries) 1) -Ethyl-3- (N, N'-dimethylaminopropyl) carpositimide (Ibai) 2 · 30g was added and stirred at room temperature for 3 hours, then 40 Heated at ° C for 3 hours and stirred. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid and distilled water. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure at 50 ° C to obtain 4.91 g (yield: 89.8%) of N, N'-di (tert-butoxycarbonyl) homocystinediol. It was.

The obtained N, N′-di (tert-butoxycarbonyl) homocystinediol was dissolved in 30 mL of methylene chloride and stirred until uniform. Trifluoroacetic acid (manufactured by Wako Pure Chemical Industries) was added to this until the disappearance of the raw material was confirmed by thin layer chromatography (Trifluoro Acetic acid addition amount: 6.20 g). After completion of the reaction, the reaction solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (1-7): 0.67 g (yield: 85.4%). The physical properties of this were as follows.

 [0149] 'H-NMRCCDCl, δ ppm); 0.88 (t, 6H), 1.05— 1.40 (m, 44H), 1.51—

 Three

 1.70 (m, 8H), 1.81— 1.92 (m, 2H), 1.92— 2.05 (m, 8H), 2.05— 2.20 (m, 2H), 2.75-2.85 (m, 4H), 3.50— 3.55 (m, 2H ), 4.05— 4.10 (t, 4 H), 5.25-5.40 (m, 4H)

 Elemental analysis results; C H N O S

 44 84 2 4 2

 (Calculated value C: 68.70%, H: ll.01%, N: 3.64%, S: 8.34%)

 (Measured value C: 68.55%, H: 11.14%, N: 3.55%, S: 8.28%)

 [0150] A trial oil was prepared in the same manner as in Example 1 except that the ester (I7) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 2.

 [0151] [Example 8] Cystindiolyl methanesulfonate (ester (1-11))

 2.8 g of cystinediol (ester I 1) obtained in Example 1 was dissolved in 30 mL of methylene chloride (manufactured by Wako Pure Chemical Industries, Ltd.) and stirred sufficiently in a nitrogen atmosphere, and then 1.7 g of methanesulfonic acid (manufactured by Kanto Chemical Co., Ltd.). ) Was added dropwise and stirred at room temperature for 1 hour, and the reaction solution was washed with distilled water. After the solvent in the organic layer was distilled off at 50 ° C. under reduced pressure, ester (1-11): 1.lg (yield: 39.3%) was obtained. The physical property values thereof were as follows.

 [0152] 'H-NMRCCD OD, δ ppm); 0.90 (t, 6H), 1.15— 1.48 (m, 44H), 1.73 (

 Three

 tt, 4H), 1.94-2. 10 (m, 8H), 2.71 (s, 6H), 3.29— 3.42 (m, 4H), 4.29 (t, 4H), 4.37-4.52 (m, 2H), 5.30— 5.41 (m, 4H)

 Elemental analysis results; C H N O S

 44 88 2 10 4

 (Calculated value C: 56.62%, H: 9.50%, N: 3.00%, S: 13.74%)

 (Measured value C: 56.44%, H: 9.55%, N: 2.87%, S: 13.54%)

 [0153] A trial oil was prepared in the same manner as in Example 1 except that the ester (I11) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 3.

[Comparative Example 1] 3,3′-Dioleyl dithiodipropionate (Ester (8)) 3, 3'-dithiodipropionic acid 5. Og (Wako Pure Chemical), 4-dimethylaminopyridine 5.8 g (Wako Pure Chemical), and oleyl alcohol 12.8 g (Wako Pure Chemical) Is dissolved in 10 mL of methylene chloride (manufactured by Wako Pure Chemical Industries, Ltd.), and after sufficient stirring, 1-ethyl-3- (N, N'-dimethylamino) propylcarbodiimide (manufactured by Ibai) 10. Add Og at room temperature, Heat at 40 ° C • Stir. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid, distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (8): 15. lg (yield: 89.3%). The physical properties of this were as follows.

[0155] 'H-NMR CCDCl, δ ppm); 0. 88 (t, 6H), 1. 27 (m, 44H), 1. 63 (m, 4H),

 Three

 2.00 (m, 8H), 2.73 (t, 4H), 2.92 (t, 4H), 4.09 (t, 4H), 5.34 (m, 4H)

 [0156] A trial oil was prepared in the same manner as in Example 1 except that the ester (8) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 4.

 [0157] (Comparative Example 2) Synthesis of 3,3'-dioleylthiodipropionate (ester (9))

 3, 3'-thiodipropionic acid 5. Og (manufactured by Wako Pure Chemical Industries), 4-dimethylaminopyridine 6.9 g (manufactured by Wako Pure Chemical Industries), and oleyl alcohol 15. lg (manufactured by Wako Pure Chemical Industries) Dissolve in lOOmL (manufactured by Wako Pure Chemical Industries, Ltd.) and stir well. Then add 1-ethyl-3- (N, N'-dimethylamino) pirical positive imide (manufactured by Ibai) 11. Heated with 'stir. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid, distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (9): 17.3 g (yield: 90.8%). The physical property values were as follows.

 [0158] 'H-NMR CCDCl, δ ppm); 0. 88 (t, 6H), 1. 27 (m, 44H), 1. 62 (m, 4H),

 Three

 2.02 (m, 8H), 2.60 (t, 4H), 2.80 (t, 4H), 4.09 (t, 4H), 5.34 (m, 4H)

 [0159] A trial oil was prepared in the same manner as in Example 1 except that the ester (9) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 4.

 [0160] (Comparative Example 3) Synthesis of dioleyl suberate (ester (10))

Suberic acid 5. Og (Wako Pure Chemical Industries), 4-dimethylaminopyridine 7.0 g (Wako Pure Chemical Industries), and alcohol alcohol 15.4 g (Wako Pure Chemical Industries) methylene chloride lOOmL (Wako Pure Chemical Industries, Ltd.) Medicinal product) 1-Ethyl-3- (N, N'-dimethylamino) propylcarbodiimide (manufactured by Aiby) (12 lg) was added, and the mixture was heated and stirred at room temperature and then at 40 ° C. The reaction solution was cooled to room temperature and washed with 0.5 mol / L hydrochloric acid, distilled water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure at 50 ° C. to obtain ester (10): 18. lg (yield: 93.2%). The physical properties of this were as follows.

 [0161] 'H-NMR CCDCl, δ ppm); 0. 88 (t, 6H), 1. 26-1. 34 (m, 48H), 1. 62 (

 Three

 m, 8H), 2.02 (m, 8H), 2.29 (t, 4H), 4.05 (t, 4H), 5.35 (m, 4H)

 [0162] A trial oil was prepared in the same manner as in Example 1 except that the ester (10) thus obtained was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 4.

[0163] (Comparative Example 4)

 A trial oil was prepared in the same manner as in Example 1 except that dibenzyldisulfide (DBDS) manufactured by Tokyo Chemical Industry was used as an additive for oils, and evaluated in the same manner as in Example 1. The results are shown in Table 5.

[0164] [Table 1]

[]

0661

¾a

[0169] As is apparent from Tables 1 to 3, according to each example, regardless of the type and polarity of the lubricant base oil to be used, a prototype with excellent wear resistance! We were able to provide oil. On the other hand, the trial oils of Comparative Examples 1 to 3 tend to have particularly insufficient wear reduction, and the trial oil of Comparative Example 4 has a poor wear resistance.

 Industrial applicability

[0170] According to the additive for oils containing the ester of the present invention, it does not contain metal and phosphorus, and imparts wear resistance (friction reduction and wear reduction) to the oils. be able to. Therefore, according to the present invention, it is possible to provide oils such as lubricating oil and fuel oil having good wear resistance.

Claims

Claim Formula (I)

[Chemical 1] (

[In the formula (I), R ¹ and R ² are the same or different and each represents a hydrocarbyl that may contain one or more selected from the group consisting of an oxygen atom and a sulfur atom, and a and b are the same or different, Represents an integer of 0 to 5, X and Y are the same or different and each represents a sulfur atom or a single bond, W and Z are the same or different and represent a hydrogen atom, formula (II)

[Chemical 2]

{In Formula (II), R ³ and R ⁴ are the same or different and each has a hydrogen atom, an optionally substituted hydrocarbyl, an optionally substituted hydrocarbylcarbonyl, or a substituent. ! /, May! /, Hydrocarbyloxycarbonyl, with substituents! /, May! /, Represents hydro sulfonylsulfonyl, or R ³ and R ^{4 and} the adjacent nitrogen atom Together, it may have a substituent, may! /, Form a nitrogen-containing heterocyclic group},

 Formula (III)

[Chemical 3]

{In formula (III), R ⁵ and R ⁶ are the same or different and represent a hydrogen atom, a hydrocarbyl optionally having substituent (s), a hydrocarbylcarbonyl optionally having substituent (s), or R ⁵ and R ⁶ together with the adjacent carbon atom have a substituent! /, ^May ! / Form a cyclic hydrocarbyl},

 Or formula (IV)

[Chemical 4]

{In Formula (IV), η represents an integer of 1 to; and R ⁷ and R ⁸ are the same or different and each has a hydrogen atom, a hydrocarbyl which may have a substituent, or a substituent. Optionally representing a hydrocarbyl carbonyl, or R ⁷ and R ⁸ together with two adjacent carbon atoms each having an optionally substituted cycloalkane, or having a substituent. Form an aromatic ring that is optional} (where W and Ζ are not simultaneously hydrogen atoms, and if either W or Ζ is a hydrogen atom, X and Υ are not simultaneously a single bond)] Additive for oils containing ester.

[2] The additive for oils according to claim 1, wherein X represents a sulfur atom.

 [3] The additive for oils according to claim 1, wherein X and Υ are the same and represent a sulfur atom.

 [4] The additive for oils according to any one of claims 1 to 3, wherein a and b are the same; and represents an integer of! To 2.

[5] R ¹ and R ² are the same or different and each represents alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, or aryl having 4 to 20 carbon atoms. Claims 1-4. Additive for oils according to any one of claims 1 to 4.

[6] R ¹ and R ² are the same or different and are alkyl having 1 to 20 carbon atoms or ² to ² carbon atoms.

The additive for oils according to any one of claims 1 to 4, which represents 0 alkenyl.

[7] W and / or Z represents the formula (II), R ³ and R ⁴ forces are the same or different, and a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, a substituent May have an alkenyl having 2 to 20 carbon atoms, may have a substituent, may be! /, A cycloalkyl having 3 to 20 carbon atoms, or an optionally substituted carbon number 4 ~ 20 aryl, may have a substituent V, aralkyl having 5 to 20 carbon atoms, has a substituent! /, May! /, Alkanoinole having 2 to 21 carbon atoms, substituent Alkenol having 3 to 21 carbon atoms, optionally having substituents, aroyl having 5 to 21 carbon atoms, having substituents! /, May! /, Carbon An alkoxycarbonyl group having 2 to 21 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms which may have a substituent, an sulfonyl group having a substituent group! /, An arylsulfonyl having 4 to 20 carbon atoms, Replace The have! /, Even if A force representing ⁴ to 21 carbon atoms cycloalkylcarbonyl, or R ³ and R ⁴ together with the adjacent nitrogen atom, the ring part which may have a substituent is 5 to 10; Whether to form a nitrogen-containing heterocyclic group consisting of member rings;

W and / or Z represents the formula (IV), and R ⁷ and R ⁸ are the same or different and have a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, and a substituted group. May represent an alkenyl having 2 to 20 carbon atoms, having a substituent! /, May! /, An aryl having 4 to 20 carbon atoms, or R ⁷ and R ⁸ are adjacent to each other 2 Combined with one carbon atom, has a substituent! /, May! /, A cycloalkane having 3 to 20 carbon atoms, or has a substituent! /, May have 4 carbon atoms The additive for oils according to any one of claims 1 to 6, which forms -20 aromatic rings.

[8] W and / or Z represents the formula (II), and R ³ and R ⁴ forces are the same or different, and are a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, a substituent. An alkenyl having 2 to 20 carbon atoms, an alkanol having 2 to 21 carbon atoms which may have a substituent, an aryl having 5 to 21 carbon atoms which may have a substituent, An optionally substituted carbon number;! To 20 alkylsulfonyl, or an optionally substituted carbonyl 4 to 20 arylsulfonyl; Oil additives as described.

[9] The additive for oils according to any one of claims 1 to 6, wherein W or Z represents the formula (II).

 [10] The additive for oils according to any one of claims 1 to 6, wherein W and Z are the same or different and represent the formula (II).

[11] W and / or Z represents the formula (II), and R ³ and R ⁴ forces are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbylcarbonyl. The additive for oils according to any one of the above.

[12] W and / or Z represents the formula (IV), R ⁷ and R ⁸ are the same or different, and a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, a substituent A force representing alkenyl having 2 to 20 carbon atoms, or R ⁷ and R ⁸ together with two adjacent carbon atoms each having an alkyl substituent having 1 to 20 carbon atoms. A benzene ring which may be substituted, or a naphthalene ring which may have an alkyl substituent having 1 to 20 carbon atoms, and n = l; The additive for oils according to any one of 11

[13] W and / or Z represents the formula (III), R ⁵ and R ⁶ are the same or different and are a hydrogen atom, an optionally substituted alkyl having 1 to 20 carbon atoms, a substituent. An alkenyl having 2 to 20 carbon atoms, an aryl having 4 to 20 carbon atoms which may have a substituent, or R ⁵ and R ⁶ together with adjacent carbon atoms. The additive for oils according to any one of claims 1 to 6, which forms a cycloalkyl having 3 to 20 carbon atoms which may have a substituent.

[14] W and / or Z represents the formula (III), R ⁵ and R ⁶ are the same or different and are a hydrogen atom or an optionally substituted alkyl having 1 to 10 carbon atoms, substituted The alkenyl having 2 to 10 carbon atoms which may have a group, or an aryl having 4 to 10 carbon atoms which may have a substituent, according to any one of claims 1 to 6. Oil additives.

 [15] A lubricating oil comprising the oil additive according to any one of claims 1 to 14 and a lubricating base oil.

 [16] Lubricating oil base oils are mineral oil, vegetable oil, poly α-olefin, fatty acid ester, polyalkylene glycolate, phosphate esterolate, silicone, catenate ester, polyphenyl ether, alkylbenzene, synthetic naphthene, gas tool 16. The lubricating oil according to claim 15, wherein the lubricating oil is one or more selected from the group consisting of liquids.