JP2015199934A - Lubricant compound and lubricant composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel compound that can be used as a lubricant exhibiting excellent lubrication performance in a wide temperature range from low temperature to high temperature.SOLUTION: A lubricant compound is represented by the general formula (1) or (3) in the figure.

Description

  The present invention relates to a novel compound excellent in lubricity, a lubricant composition containing the same, and the like.

  Lubricants are liquids that are more viscous and have a stronger coating than water, and have a function to reduce friction between objects, and are used to reduce friction between machine elements of machinery and equipment. Is done.

  Such a lubricant is required to have various characteristics according to the use environment of the machine and the like used. For example, long-term viscosity stability, oxidation resistance, corrosion resistance, and viscosity stability against temperature changes are required.

  Furthermore, various technological innovations in recent years have led to advances in miniaturization, weight reduction, and high-speed rotation of machine elements in various mechanical devices, increased use in a wide temperature range, and improved characteristics required for lubricants. Yes. For example, in addition to the above characteristics, a low coefficient of friction, wear resistance, durability, low temperature fluidity, high temperature stability, etc. are required.

  Various lubricants have been proposed as lubricants that can meet such various requirements. For example, Patent Documents 1 and 2 disclose diester type lubricating oil compounds having ester structures at both molecular ends. .

  It has also been proposed to use a liquid crystal compound as a lubricant (Patent Documents 3 to 5). The liquid crystal compound is generally a compound having a rigid core portion (mesogen group) and a flexible chain portion. In addition, since a single liquid crystal compound has a narrow temperature range showing a liquid crystal phase and cannot sufficiently cope with the temperature range used as a lubricant, it is widely used not only as a single substance but also as a mixture (mixed liquid crystal). It has been broken.

Republished patent WO2011-125842 JP2013-82900A JP-A-6-128582 JP 2005-139398 A JP 2008-214603 A

  An object of the present invention is to provide a novel compound that can be used as a lubricant exhibiting excellent lubricating performance in a wide temperature range from low temperature to high temperature.

  As a result of intensive studies to solve the above problems, the present inventors have found that a compound having a predetermined ester structure and a chain ether structure, and a compound having a predetermined chain ether structure and a rigid core structure are excellent in lubricity. The present inventors have found that it can be suitably used as a lubricant and have completed the present invention.

That is, the gist of the present invention is as follows.
<1> Lubricating compound represented by the following general formula (1):

(In the formula, R ¹ and R ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; An alkenyl group having 2 to 20 carbon atoms which may be substituted with a group or a cyano group; or may have a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group An alkynyl group having 2 to 20 carbon atoms,
R ³ and R ⁴ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group or a cyano group, which may be substituted and optionally branched, an alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group Or an alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may have a branch; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group Or an alkynyl group having 2 to 20 carbon atoms,
R ² and R ⁵ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, or may have a branch; or a fluorine atom, a hydroxyl group or An alkenylene group having 2 to 20 carbon atoms which may be substituted with a cyano group or may have a branch;
m is an integer of 1-6,
When m is 2 or more, a plurality of R ^{2 s} , R ^{3 s} , R ^{4 s} , and R ^{5 s} may be the same as or different from each other. ).

<2> In the general formula (1), R ¹ and R ⁶ may each independently be substituted with a fluorine atom, a hydroxyl group, or a cyano group, and may have a branch. An alkyl group, wherein R ³ and R ⁴ are each independently a hydrogen atom; or a C 1-20 alkyl which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may be branched. R ² and R ⁵ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch, <1 > Lubricating compound as described in>.

  <3> The lubricating compound according to <1> or <2>, wherein m is an integer of 1 to 3 in the general formula (1).

<4> In the general formula (1), R ² and R ⁵ in the parenthesized unit with a subscript m are the same group (in the case where m is 2 or more, The lubricating compound according to any one of <1> to <3>, wherein R ² and R ⁵ in the unit and another unit may be the same or different.

  <5> The lubricating compound according to any one of <1> to <4>, wherein the lubricating compound is a compound represented by the following general formula (2):

(In the formula, R ^{1 ′} has the same meaning as R ¹ in the general formula (1), and R ^{2 ′} and R ^{2 ″} each independently has the same meaning as R ² in the general formula (1). , R ^{3 'and} R ^3''are each independently have the same meaning as ^{R 3} in formula (1), R ^4''has the same meaning as ^{R 4} in the general formula (1), R ^{5 ′} and R ^{5 ″} are each independently synonymous with R ⁵ in the general formula (1), R ^{6 ′} is synonymous with R ⁶ in the general formula (1), and n is 1 to Is an integer of 3, p is an integer of 0 to 3, and a unit enclosed in parentheses with a subscript n and a unit enclosed in parentheses with a p subscript exist in a block Or it may exist randomly.)

  <6> Lubricating compound represented by the following general formula (3):

[Where:
The group A may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; may be substituted with a fluorine atom, a hydroxyl group or a cyano group An optionally branched alkenyl group having 2 to 20 carbon atoms; an alkynyl group having 2 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; Alternatively, it is a monovalent organic residue represented by the following general formula (4):

(In the formula, R ¹¹ is optionally substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; substituted with a fluorine atom, a hydroxyl group or a cyano group. An alkenyl group having 2 to 20 carbon atoms which may be branched or optionally branched; alternatively, it may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branched carbon number 2 -20 alkynyl groups,
R ¹² and R ¹⁵ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group or a cyano group, which may be substituted and optionally branched, an alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group Or an alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may have a branch; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group Or an alkynyl group having 2 to 20 carbon atoms,
R ¹³ represents a single bond; a C 1-20 alkylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or a fluorine atom, a hydroxyl group or a cyano group; An alkenylene group having 2 to 20 carbon atoms which may be substituted or branched;
R ¹⁴ and R ¹⁶ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may be branched; or a fluorine atom, a hydroxyl group or It is a C2-C20 alkenylene group which may be substituted with a cyano group and may have a branch. )
The group W is a divalent group selected from the group consisting of a divalent tetralin group which may be substituted, a divalent polycyclic aromatic group which may be substituted, and a group represented by the following general formula (I). The mesogenic group of

(Wherein, ring D, ring E and ring F are each independently a benzene ring, cyclohexane ring, cyclohexene ring, pyridine ring, pyrimidine ring, dioxane ring, tetralin ring or polycyclic aromatic ring,
Y is independently hydrogen atom, deuterium atom, alkyl group having 1 to 8 carbon atoms, alkoxy group, alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkoxyalkyl group, alkanoyloxy group, alkoxycarbonyl. A group, a halogen atom, or a cyano group,
s1 to s3 are each independently an integer up to 1, or the number of sites to which a substituent of ring D, ring E or ring F can be bonded;
when s1 to s3 are 2 or more, a plurality of Y bonded to the same ring may be the same or different;
Z ₁ and _{Z 2} are each independently a single _{bond, -CO-O -, - O} -CO -, - CH 2 O -, - OCH 2 -, - CH 2 CH 2 -, - CH = CHCH 2 O-, _{-CH = CH -, - CF 2} O -, - OCF 2 -, - S -, - SO -, - SO 2 - or a -C≡C-,
r is 0, 1 or 2;
When r is 2, two Z ₁ may be the same or different, and the two rings D may be the same or different, and are bonded to the two rings D, respectively. Y may be the same or different. )
The group B is a monovalent organic residue represented by the following general formula (5):

(Wherein R ²¹ and R ²³ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; , An alkenylene group having 2 to 20 carbon atoms which may be substituted with a hydroxyl group or a cyano group and may have a branch;
R ²⁴ represents a single bond; a C 1-20 alkylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or a fluorine atom, a hydroxyl group or a cyano group; An alkenylene group having 2 to 20 carbon atoms which may be substituted or branched;
R ²² and R ²⁵ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group or a cyano group, which may be substituted and optionally branched, an alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group Or an alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may have a branch; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group Or an alkynyl group having 2 to 20 carbon atoms,
R ²⁶ may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; may be substituted with a fluorine atom, a hydroxyl group or a cyano group An optionally branched alkenyl group having 2 to 20 carbon atoms; or an optionally substituted alkynyl group having 2 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group It is a group. ]].

  <7> In the general formula (3), the group A may be substituted with a fluorine atom, a hydroxyl group, or a cyano group, and may be branched, or an alkyl group having 1 to 20 carbon atoms, or The lubricating compound according to <6>, which is an organic residue represented by the general formula (4).

In <8> Formula (4), R ¹¹ is a fluorine atom, an alkyl group of a hydroxyl group or a cyano group carbon atoms which may have a well-branched optionally substituted with 1 to 20, R ¹² And R ¹⁵ are each independently a hydrogen atom; or a C 1-20 alkyl group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may be branched, and R ¹³ , <6> or <7, wherein R ¹⁴ and R ¹⁶ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch. > Lubricating compound as described in>.

<9> In the general formula (5), R ²¹ , R ^23, and R ²⁴ may each independently be substituted with a fluorine atom, a hydroxyl group, or a cyano group, and may have a branch. To 20 alkylene groups, and each of R ²² and R ²⁵ independently represents a hydrogen atom; or may be substituted with a fluorine atom, a hydroxyl group, or a cyano group, and may have a branched carbon number 1 to <6> to <8, which is an alkyl group of 20 and R ²⁶ is an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branch. > The lubricating compound according to any one of the above.

<10> In the general formula (I), ring D, ring E and ring F each independently represent a benzene ring, cyclohexane ring, dioxane ring, tetralin ring or polycyclic aromatic ring, and Y each independently represents hydrogen. The lubricity according to any one of <6> to <9>, which represents an atom or a halogen atom, Z ₁ and Z ₂ each independently represents a single bond or —CO—O—, and r represents 0 or 1. Compound.

<11> In the general formula (4), R ¹⁴ and R ¹⁶ are the same group, and in the general formula (5), R ²¹ and R ²³ are the same group, <6> to <10> The lubricating compound according to any one of the above.

  <12> A lubricant composition comprising the lubricating compound according to any one of <1> to <11>.

  <13> A lubricant composition comprising the lubricating compound according to <6>, wherein the composition is a group selected from the options of the group A in the general formula (3) (first group And a plurality of compounds having a group selected from one group (second group) selected from the options of the group B as the group A and the group B in the general formula (3), In the general formula (3), the group A and the group B are the first group, the group A is the first group and the group B is the second group, and the group A is A lubricant composition, which is the compound that is the second group and the group B is the first group, and the compound that the group A and the group B are the second group.

  <14> A machine device having a plurality of machine elements that move relative to each other in contact with each other, and the lubricant composition according to <12> or <13> disposed on at least a part of a contact surface of the machine elements.

  ADVANTAGE OF THE INVENTION According to this invention, the novel compound which can be used as a lubricant which shows the outstanding lubricating performance in the wide temperature range from low temperature to high temperature is provided.

The time-dependent evaporation loss at 100 degreeC of the mixture of the compound B of this invention of Example 11 and Comparative Example 4 and DOS is shown.

  Hereinafter, the present invention will be described in detail. The lubricating compound of the present invention is a compound represented by the above general formula (1) or (3). First, in the following, the lubricating compound of the present invention represented by the general formula (1) (hereinafter, “ Also referred to as “Compound A of the present invention”) and the lubricating compound of the present invention represented by the general formula (3) (hereinafter also referred to as “Compound B of the present invention”. Also, Compound A of the present invention and the present invention. These compounds B are collectively referred to simply as “compounds of the present invention”).

[Compound A of the present invention]
Compound A of the present invention is represented by the following general formula (1). Hereinafter, each group in Formula (1) is demonstrated.

<About R ¹ and R ⁶ >
In the general formula (1), R ¹ and R ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch; An alkenyl group having 2 to 20 carbon atoms which may be substituted with an atom, a hydroxyl group or a cyano group; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group It is a C2-C20 alkynyl group which may have.

The compound A of the present invention is a chain compound having a repeating unit with a subscript m attached in parentheses as shown by the formula (1) and having an ester bond at one molecular end. , R ¹ and R ⁶ are chain groups constituting both ends of the compound A. By these, the molecular size (major axis) and polarity of the compound A can be adjusted.

  The alkyl group preferably has 4 to 14 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such alkyl groups are butyl, pentyl, 2-ethylhexyl, hexyl, heptyl, 2-methylheptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl. And a tetradecyl group.

  The alkenyl group preferably has 4 to 14 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such alkenyl groups include butenyl, pentenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, and tetradecenyl.

  The alkynyl group preferably has 4 to 14 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such alkynyl groups include butynyl, pentynyl, heptynyl, octynyl, noninyl, decynyl, undecynyl, dodecynyl, tridecynyl, and tetradecynyl groups.

  The alkyl group, alkenyl group and alkynyl group may be substituted with a cyano group, but the carbon atoms constituting the cyano group are not counted in the number of carbon atoms such as the alkyl group. The same applies hereinafter.

R ¹ and R ⁶ described above may be substituted with a fluorine atom, a hydroxyl group or a cyano group from the viewpoint of the volatility, lubricity and stability of the compound A of the present invention, and have a branch. Preferred is an alkyl group having 1 to 20 carbon atoms.

<About R ³ and R ⁴ >
In the general formula (1), R ³ and R ⁴ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group, or a cyano group, which may be substituted and may have 1 to 20 carbon atoms. An alkyl group; an alkenyl group having 2 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or substituted with a fluorine atom, a hydroxyl group or a cyano group; Or an alkynyl group having 2 to 20 carbon atoms which may be branched.

R ³ and R ⁴ are side chains in the parenthesized unit with m subscript, and by adjusting these structures, the compounds A of the present invention which are chain molecules, or the compound A And intermolecular distance and intermolecular force between various constituents in the lubricant composition of the present invention described later can be adjusted to desired values.

  The alkyl group preferably has 1 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such an alkyl group include a methyl group, an ethyl group, a 2-methylpropyl group, a propyl group, a butyl group, and a t-butyl group.

  The alkenyl group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such alkenyl groups include ethenyl, propenyl, and butenyl groups.

  The alkynyl group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such alkynyl groups include ethynyl group, propynyl group, and butynyl group.

R ³ and R ⁴ described above have a branch which may be substituted with a hydrogen atom, a fluorine atom, a hydroxyl group or a cyano group from the viewpoint of volatility and lubricity of the compound A of the present invention. An optionally substituted alkyl group having 1 to 20 carbon atoms is preferable, R ⁴ is a hydrogen atom, and R ³ is more preferably an alkyl group having 1 to 2 carbon atoms.

<For ^{R 2} and ^{R 5>}
In the general formula (1), R ² and R ⁵ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch; Or it is the C2-C20 alkenylene group which may be substituted by the fluorine atom, the hydroxyl group, or the cyano group, and may have a branch.

R ² and R ⁵ define the length of the unit to which the subscript m is attached, and thereby the molecular size (major axis) and polarity of the compound A of the present invention can be adjusted.

  The alkylene group preferably has 1 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such an alkylene group include a methylene group, an ethylene group, a propylene group, and a butylene group.

  The alkenylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound A of the present invention. Examples of such alkenylene groups include ethynylene groups, propynylene groups, and butynylene groups.

R ² and R ⁵ described above are carbons which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch from the viewpoint of the volatility and lubricity of the compound A of the present invention. The alkylene group of number 1-20 is preferable. Moreover, from the viewpoint of ease of synthesis of the compound A of the present invention, R ² and R ⁵ are preferably the same group. As will be described later, when m is 2 or more, there are a plurality of units enclosed in parentheses with a subscript m. In this case, R ² and R ⁵ in each unit are the same. The plurality of R ² and R ⁵ need not be the same, and may be the same or different.

<About m>
In the said General formula (1), m is an integer of 1-6. If m exceeds 6, it will be difficult to synthesize the compound A of the present invention, and it will be difficult to achieve a low viscosity and a low dynamic friction coefficient suitable for the lubricant application described below.

When m is 2 or more, there are a plurality of parenthesized units with a subscript m, and there are a plurality of R ² , R ³ , R ⁴ and R ⁵ , respectively. A plurality of R ^{2 s} , R ^{3 s} , R ^{4 s} , and R ^{5 s} may be the same as or different from each other.

  Thus, m indicating the number of repeating units in the compound A of the present invention is preferably an integer of 1 to 3 from the viewpoint of the volatility and lubricity of the compound A.

<Preferred embodiment of compound A>
The compound A of the present invention described above is preferably a compound represented by the following general formula (2).

In the formula, R ^{1 ′} has the same meaning as R ¹ in the general formula (1),
R ^{2 ′} and R ^{2 ″} are each independently synonymous with R ² in the general formula (1),
R ^{3 ′} and R ^{3 ″} are independently the same as R ³ in the general formula (1),
R ^{4 ″} is synonymous with R ⁴ in the general formula (1),
R ^{5 ′} and R ^{5 ″} are each independently synonymous with R ⁵ in the general formula (1),
R ^{6 ′} has the same meaning as R ⁶ in the general formula (1),
n is an integer of 1 to 3,
p is an integer from 0 to 3,
The unit enclosed in parentheses with an n subscript and the unit enclosed in parentheses with a p subscript may be present in blocks or randomly.

As described above, the compound A of the present invention in which one of the side chains in the repeating unit (R ³ or R ⁴ in the general formula (1)) is a hydrogen atom has a moderate temperature dependency of the lubrication characteristics and has a wide temperature range. Can be used.

[Compound B of the present invention]
Next, the compound B of the present invention will be described. Compound B of the present invention is represented by the following general formula (3). Hereinafter, each group in Formula (3) will be described.

<About Group A>
In the general formula (3), the group A may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branched alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group or cyano. An alkenyl group having 2 to 20 carbon atoms which may be substituted with a group and which may have a branch; a carbon number which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch 2 to 20 alkynyl groups; or a monovalent organic residue represented by the following general formula (4).

  As will be described later, most of the compound B of the present invention is a liquid crystal compound, but the group A constitutes a tail portion in such a compound B, and depending on the type of the compound B, the compounds B or the compound B and a book described later. The intermolecular distance and intermolecular force with the constituent components of the lubricant composition of the invention can be adjusted.

  The alkyl group preferably has 4 to 14 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkyl groups are butyl, pentyl, 2-ethylhexyl, hexyl, heptyl, 2-methylheptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl. And a tetradecyl group.

  The alkenyl group preferably has 4 to 14 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenyl groups include butenyl, pentenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, and tetradecenyl.

  The alkynyl group preferably has 4 to 14 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkynyl groups include butynyl, pentynyl, heptynyl, octynyl, noninyl, decynyl, undecynyl, dodecynyl, tridecynyl, and tetradecynyl groups.

  Next, each group in the general formula (4) will be described.

(For ^{R 11)}
In the general formula (4), R ¹¹ may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group or An alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may be branched; alternatively, it may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may be branched. It is a good C2-C20 alkynyl group.

  The alkyl group preferably has 1 to 12 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkyl groups are methyl, ethyl, propyl, butyl, pentyl, 2-ethylhexyl, hexyl, heptyl, 2-methylheptyl, octyl, nonyl, decyl. , Undecyl group and dodecyl group.

  The alkenyl group preferably has 2 to 12 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl.

  The alkynyl group preferably has 2 to 12 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkynyl groups include ethynyl, propynyl, butynyl, pentynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, and dodecynyl.

As R ¹¹ explained above, from the viewpoints of volatility, lubricity and stability of the compound B of the present invention, carbon which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch. A C1-C20 alkyl group is preferable.

(About R ¹² and R ¹⁵ )
In the above general formula (4), R ¹² and R ¹⁵ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group, or a cyano group, and may have a branch and may have 1 to 20 carbon atoms. An alkyl group; an alkenyl group having 2 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or substituted with a fluorine atom, a hydroxyl group or a cyano group; Or an alkynyl group having 2 to 20 carbon atoms which may be branched.

  The alkyl group preferably has 1 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such an alkyl group include a methyl group, an ethyl group, a 2-methylpropyl group, a propyl group, a butyl group, and a t-butyl group.

  The alkenyl group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenyl groups include ethenyl, propenyl, and butenyl groups.

  The alkynyl group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkynyl groups include ethynyl group, propynyl group, and butynyl group.

R ¹² and R ¹⁵ described above may be substituted with a hydrogen atom, a fluorine atom, a hydroxyl group or a cyano group from the viewpoints of volatility, lubricity and stability of the compound B of the present invention. The C1-C20 alkyl group which may have this is preferable.

(For ^{R 13)}
In the general formula (4), R ¹³ represents a single bond; a C 1-20 alkylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch; It is a C2-C20 alkenylene group which may be substituted with an atom, a hydroxyl group or a cyano group and may have a branch.

  The alkylene group preferably has 1 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such an alkylene group include a methylene group, an ethylene group, a propylene group, and a butylene group.

  The alkenylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenylene groups include ethynylene groups, propynylene groups, and butynylene groups.

As R ¹³ described above, from the viewpoints of volatility, lubricity and stability of the compound B of the present invention, carbon which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch may be used. The alkylene group of number 1-20 is preferable.

(About R ¹⁴ and R ¹⁶ )
In the general formula (4), R ¹⁴ and R ¹⁶ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch; Or it is the C2-C20 alkenylene group which may be substituted by the fluorine atom, the hydroxyl group, or the cyano group, and may have a branch.

  The alkylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such an alkylene group include an ethylene group, a propylene group, and a butylene group.

  The alkenylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenylene groups include ethynylene groups, propynylene groups, and butynylene groups.

R ¹⁴ and R ¹⁶ described above may be substituted with a fluorine atom, a hydroxyl group or a cyano group from the viewpoints of volatility, lubricity and stability of the compound B of the present invention, and have a branch. Preferred are alkylene groups having 1 to 20 carbon atoms. These groups are preferably the same group from the viewpoint of ease of production of the compound B of the present invention.

(About Group A)
In the general formula (3) showing the structure of the compound B of the present invention, the group A is a predetermined alkyl group, alkenyl group, alkynyl group or a monovalent organic residue of the general formula (4) as described above. is there.

  Among these, as the group A, from the viewpoint of volatility, lubricity and stability of the compound B of the present invention, the alkyl group and the organic residue represented by the general formula (4) are preferable.

<About Group W>
In the general formula (3), the group W is a divalent tetralin group which may be substituted, a divalent polycyclic aromatic group which may be substituted, and a group represented by the following general formula (I). A divalent mesogen group selected from the group consisting of

The group W has a rigid structure and is a liquid crystal forming element (core portion) in the compound B of the present invention.

  The polycyclic aromatic group is an aromatic group having two or more aromatic rings. These two or more aromatic rings may be bonded by a single bond such as biphenyl, or may be bonded in a condensed ring state such as naphthalene. Further, the ring-constituting atoms of the aromatic ring may be only carbon atoms or may contain heteroatoms.

  Examples of such polycyclic aromatic groups include the following.

  Examples of the substituent in the tetralin group and the polycyclic aromatic group include a deuterium atom, a fluorine atom, and an alkyl group having 1 to 3 carbon atoms.

  In the general formula (I), Ring D, Ring E and Ring F are each independently a benzene ring, cyclohexane ring, cyclohexene ring, pyridine ring, pyrimidine ring, dioxane ring, tetralin ring or polycyclic aromatic ring. The polycyclic aromatic ring is the same as the polycyclic aromatic group described above as a candidate for the group W.

  In the general formula (I), each Y is independently a hydrogen atom, a deuterium atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or carbon. C2-C8 alkenyloxy group, C2-C8 alkynyl group, C2-C8 alkynyloxy group, C2-C8 alkoxyalkyl group, C2-C8 alkanoyloxy group, carbon number 2-8 alkoxycarbonyl groups, a halogen atom, or a cyano group is represented. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

  In the above general formula (I), s1 to s3 are each independently an integer up to 1, or the number of sites to which the substituents of ring D, ring E or ring F can bind. For example, when the ring D is a benzene ring, s1 is an integer of 1 to 4, and when the ring D is a naphthalene ring, s1 is an integer of 1 to 6.

  Here, when s1 to s3 is 2 or more, a plurality of Ys are bonded to each of the rings D to F, but a plurality of Ys bonded to the same ring are the same or different. Also good. Of course, Y bonded to different rings may be the same or different.

In the general formula (I), Z ₁ and Z ₂ are each independently a single bond, —CO—O—, —O—CO—, —CH ₂ O—, —OCH ₂ —, —CH ₂ CH ₂ —, —CH═CHCH ₂ O—, —CH═CH—, —CF ₂ O—, —OCF ₂ —, —S—, —SO—, —SO ₂ — or —C≡C—, where r is 0, 1 or 2 is represented.

Here, when r is 2, two rings D and Z ₁ exist, but two Z ₁ may be the same or different, and two rings D exist. May be the same or different. Further, Ys bonded to the two rings D may be the same or different.

  Furthermore, Y is preferably a hydrogen atom, a deuterium atom, a halogen atom, a methyl group, or an ethyl group, more preferably a hydrogen atom, a deuterium atom, or a halogen atom from the viewpoint of achieving low viscosity in a wide temperature range. Particularly preferred are a hydrogen atom and a halogen atom.

As Z ₁ and Z ₂ , from the viewpoint of achieving low viscosity in a wide temperature range, a single bond, —CO—O—, —O—CO—, —CH ₂ CH ₂ —, —CH ₂ O— , —OCH ₂ — and —SO ₂ — are preferable, a single bond, —CO—O—, and —CH ₂ O— are more preferable, and a single bond and —CO—O— are particularly preferable.

  As the ring D, the ring E, and the ring F, a benzene ring, a cyclohexane ring, a dioxane ring, a tetralin ring, and a polycyclic aromatic ring are preferable from the viewpoint of achieving low viscosity in a wide temperature range. From the same viewpoint, r is preferably 0 or 1.

  Specific examples of the divalent mesogen group represented by the general formula (I) described above include the following divalent organic residues.

<About Group B>
Next, the group B in the general formula (3) will be described. In the general formula (3), the group B is a monovalent organic residue represented by the following general formula (5).

  The group B also constitutes a tail portion in the compound B of the present invention in the same manner as the group A, and depending on the type thereof, the intermolecular distance between the compounds B or components of the lubricant composition of the present invention described later. And the intermolecular force can be adjusted. Hereinafter, each group in the general formula (5) will be described.

(For ^{R 21} and ^{R 23)}
In the general formula (5), R ²¹ and R ²³ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branch; It is a C2-C20 alkenylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch.

R ²¹ and R ²³ together with R ²⁴ and R ²⁶ form a main chain in the group B, and thereby, the size (major axis) of the group B and the polarity of the compound B can be adjusted.

  The alkylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such an alkylene group include an ethylene group, a propylene group, and a butylene group.

  The alkenylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenylene groups include ethynylene groups, propynylene groups, and butynylene groups.

R ²¹ and R ²³ described above may be substituted with a fluorine atom, a hydroxyl group or a cyano group from the viewpoint of the volatility, lubricity and stability of the compound B of the present invention, and have a branch. Preferred are alkylene groups having 1 to 20 carbon atoms. Further, from the viewpoint of ease of synthesis of the compound B of the present invention, these groups are preferably the same group.

(About R ²⁴ )
In the general formula (5), R ²⁴ is a single bond; a C 1-20 alkylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; , An alkenylene group having 2 to 20 carbon atoms which may be substituted with a hydroxyl group or a cyano group and may have a branch.

  The alkylene group preferably has 1 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such an alkylene group include a methylene group, an ethylene group, a propylene group, and a butylene group.

  The alkenylene group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenylene groups include ethynylene groups, propynylene groups, and butynylene groups.

As R ²⁴ described above, from the viewpoint of volatility, lubricity and stability of the compound B of the present invention, carbon which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch may be used. The alkylene group of number 1-20 is preferable.

(About R ²² and R ²⁵ )
In the general formula (5), R ²² and R ²⁵ are each independently a hydrogen atom; a C 1-20 alkyl which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may be branched. A group; a C 2-20 alkenyl group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or may be substituted with a fluorine atom, a hydroxyl group or a cyano group It is an alkynyl group having 2 to 20 carbon atoms that may be branched.

R ²² and R ²⁵ constitute a side chain in the group B, and by adjusting these structures, the compounds B of the present invention, or the compound B and various components in the lubricant composition of the present invention described later are used. Intermolecular distance and intermolecular force can be adjusted.

  The alkyl group preferably has 1 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such an alkyl group include a methyl group, an ethyl group, a 2-methylpropyl group, a propyl group, a butyl group, and a t-butyl group.

  The alkenyl group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenyl groups include ethenyl, propenyl, and butenyl groups.

  The alkynyl group preferably has 2 to 4 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkynyl groups include ethynyl group, propynyl group, and butynyl group.

R ²² and R ²⁵ described above may be substituted with a hydrogen atom, a fluorine atom, a hydroxyl group or a cyano group from the viewpoints of volatility, lubricity and stability of the compound B of the present invention. The C1-C20 alkyl group which may have is preferable.

(About R ²⁶ )
In the general formula (5), R ²⁶ may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branched alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group or cyano. An alkenyl group having 2 to 20 carbon atoms which may be substituted with a group and which may have a branch; alternatively, it may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch An alkynyl group having 2 to 20 carbon atoms.

  The alkyl group preferably has 1 to 12 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkyl groups are methyl, ethyl, propyl, butyl, pentyl, 2-ethylhexyl, hexyl, heptyl, 2-methylheptyl, octyl, nonyl, decyl. , Undecyl group and dodecyl group.

  The alkenyl group preferably has 2 to 12 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl.

  The alkynyl group preferably has 2 to 12 carbon atoms from the viewpoint of volatility and lubricity of the compound B of the present invention. Examples of such alkynyl groups include ethynyl, propynyl, butynyl, pentynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, and dodecynyl.

As R ²⁶ described above, from the viewpoint of volatility, lubricity and stability of the compound B of the present invention, carbon which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch may be used. A C1-C20 alkyl group is preferable.

<About Group A and Group B>
As described above, in the general formula (3), the group A and the group B are each independently defined, but there are some common options.

  For this reason, depending on the kind of group A and group B, these may be the same group. In such a case, the compound B of the present invention is preferable from the viewpoint of production because the number of raw materials used in the production of the compound B of the present invention described later is small.

  On the other hand, when the group A and the group B are different groups, the number of production raw materials to be used increases compared to the case where they are the same, but it is advantageous in terms of the usable temperature range of the lubricant composition described later. There are cases.

[Compound A and Compound B]
The compound A of the present invention described above has a predetermined ester structure and a chain ether structure, while the compound B of the present invention has a predetermined chain ether structure and a rigid core structure (group W). doing.

  These compounds are common in that they have a predetermined chain ether structure, and the compounds A and B of the present invention having a combination of such a structure and a predetermined structure (ester structure or core structure) are excellent in lubricity. Excellent.

  Specifically, the compound A of the present invention has a viscosity of usually 500 mPa · s or less, preferably 1 to 400 mPa · s, more preferably 3 to 300 mPa · s, and further preferably 5 in a temperature range of −20 to 60 ° C. It is in the range of ~ 200 mPa · s.

  The compound B of the present invention has a viscosity of usually 50,000 mPa · s or less, preferably 100 to 30,000 mPa · s, more preferably 200 to 20,000 mPa · s, in the temperature range of −20 to 60 ° C. Preferably it exists in the range of 300-20,000 mPa * s.

  In the present specification, the viscosity is measured with a rotational viscometer.

  The dynamic friction coefficient of the compound of the present invention is usually 0.05 to 0.21, preferably 0.05 to 0.19 from the viewpoint of lubricity, and more preferably in the range of −10 ° C. to 40 ° C. It is 0.12-0.17.

  The dynamic friction coefficient can be measured with a commercially available dynamic friction coefficient measuring device. In this specification, the dynamic friction coefficient is measured using a surface property measuring machine “TYPE: 14FW” manufactured by Shinto Kagaku Co., Ltd.

  Since the dynamic friction coefficient of the lubricating compound of the present invention and the lubricating composition described below is affected by temperature, the dynamic friction coefficient is measured at a predetermined measurement temperature in the range of −10 ° C. to 40 ° C.

  Specifically, a stainless steel plate is fixed to the moving table of the surface property measuring machine, the sample is dropped, and under the following conditions, point pressure is applied with a fixed ball and wear due to reciprocating motion is repeated. The dynamic friction coefficient is measured up to 1800 times, and the average value (average dynamic friction coefficient) is calculated. This average value is defined as a dynamic friction coefficient in the present invention.

(Measurement condition)
Vertical load: 100g
Friction speed: 600mm / min
Number of round trips: 1800
Reciprocating stroke: 5mm
Weighted transducer capacity: 19.61N
Test piece temperature: -10 ° C to 40 ° C
Friction mating material: SUS304 stainless steel sphere diameter 10mm
Sample volume: 0.2 mL

  As described above, the compound of the present invention has a low viscosity in a wide temperature range from a low temperature to a high temperature and also has a low coefficient of dynamic friction, so that it has excellent lubricity and is suitably used as a base oil or additive of a lubricant composition. be able to.

  Furthermore, since the compound B of this invention has little evaporation loss as evident from the below-mentioned Example, it is especially preferable as a base oil of a lubricant composition.

[Method for producing compound of the present invention]
Then, the manufacturing method of compound A and B of this invention is demonstrated.

<Method for Producing Compound A>
First, the manufacturing method of the compound A of this invention is demonstrated. The method for producing Compound A is not particularly limited, and Compound A can be produced by combining known reactions.

  The compound A has one or more units in the above general formula (1) that are subscripted with the suffix m, and in its synthesis, for example, the compound constituting the unit is It can be easily synthesized by reacting repeatedly a predetermined number of times and reacting with a compound that becomes an ester moiety of the general formula (1).

  In the above synthesis, for example, a diol represented by the following formula (II) is prepared.

R ^{2 to} R ⁵ are the same as those in the general formula (1).

The compound is first reacted with, for example, an alkyl halide (R ¹ X: X is a halogen atom such as a chlorine atom, a bromine atom or an iodine atom) to alkylate one hydroxyl group. By reacting the obtained alkylation product with the compound represented by the formula (II), a unit having a predetermined repeating number m in the compound A of the present invention can be formed.

  In this case, in order to control the reaction, for example, one hydroxyl group of the alkylation product or the compound of the formula (II) is converted to a metal alkoxide with, for example, metallic sodium, and the other hydroxyl group is halogenated. Both may be reacted.

And after making into the unit of predetermined repetition number (m), the compound A of this invention is obtained by esterifying a free hydroxyl group (or what made this the predetermined active group). Incidentally, the reaction to form the R ¹ in the general formula (1) halogenated alkyl, or after a predetermined number of repetitions of the unit may be performed after further carried out the esterification reaction.

A conventionally known esterification reagent can be used for the esterification, and for example, a known acid chloride (R ⁶ COCl) can be used.

  Various conventionally known organic solvents can be used for the reaction described above, and for example, ethanol, dimethylformamide (DMF), N-methylpyrrolidone (NMP), diethyl ether, and dichloromethane can be used.

<Method for producing compound B>
Next, the manufacturing method of the compound B of this invention is demonstrated. The method for producing Compound B is also not particularly limited, and Compound B can be produced by combining known reactions.

  The synthesis of compound B can be easily performed by sequentially or simultaneously bonding the group W (core portion) described in the general formula (3) and the group A or group B on both sides thereof with an ether bond. it can.

  As the reaction for bonding the group W and the group A or the group W and the group B by the ether bond, an alcohol compound (A-OH or B-OH), a phenol compound (HO-W-OH), an alkali metal or an alkali metal is used. A method of reacting with a halogen compound (AX, BX or XWX (X is a halogen atom such as a chlorine atom, a bromine atom or an iodine atom)) using an alcoholate can be used.

  Examples of the alkali metal include potassium carbonate, potassium hydroxide, and sodium hydroxide. Examples of the alkali metal alcoholate include sodium ethylate, sodium methylate, tert-butoxy sodium, and tert-butoxy potassium.

  For these reactions, various conventionally known organic solvents can be used. For example, diethyl ether, tetrahydrofuran (THF), acetone, and toluene can be used.

  In addition, when the compound B is a compound in which the group A and the group B are the same group in the general formula (3), the compound which is the group A in the general formula (3) and the group B described above. Therefore, the synthesis of compound B is easy because only two types of synthesis raw materials are required.

(Mixture formation)
On the other hand, when the group A and the group B are different groups, the compound X′-W—X ′ (core raw material) to be the group W in the general formula (3) and the compound AX to be the group A ( The raw material 1) is reacted with the compound BX (raw material 2) to be the group B. Here, when these are reacted at the same time, which of the two reaction points of the core raw material reacts with the raw material 1 or 2 becomes a problem of probability, and the reaction point on the left side in the group W of the general formula (3) The raw material 1 or 2 reacts, and the raw material 1 or 2 reacts at the reaction point on the right side to produce a total of four types of compounds. In the general formula (3), when the group W is a group having a symmetrical structure, three types of compounds are generated. The production of the plurality of types of compounds is shown by a reaction formula, for example, as follows.

(X is independently a halogen atom or hydroxyl group, and X ′ is independently a halogen atom or hydroxyl group.)

  The target compound B of the present invention is obtained as a mixture of such a plurality of compounds, but the mixture exhibits a low viscosity suitable for lubricant applications in a wider temperature range than the case of compound B alone. Therefore, the mixture can be suitably used as the lubricant composition of the present invention as described later.

[Lubricant composition]
As described above, the compound of the present invention has a low viscosity and a low coefficient of dynamic friction over a wide temperature range, so that it has excellent lubricity and can be suitably used as a base oil or additive of a lubricant composition.

  In the compound B of the present invention, since the group W in the general formula (3) is various rigid groups, most of the compound B can form a liquid crystal phase. Specifically, the compound B of the present invention usually forms a liquid crystal phase in the range of −20 to 150 ° C. (thermotropic liquid crystal). The liquid crystal phase to be formed may be any of a smectic liquid crystal phase, a nematic liquid crystal phase, a cholesteric liquid crystal phase, and a discotic liquid crystal phase. The presence or absence of liquid crystallinity can be determined by observation using a polarizing microscope.

  In addition, the compound B of the present invention can be contained in a solvent such as an organic solvent (such as a base oil in a lubricant composition described later) to form a liquid crystal phase depending on the concentration (lyotropic liquid crystal). .

  In the case of forming such a liquid crystal phase, when compound B is used as a component of the lubricant composition described later, the compound B is regularly arranged at the site of the machine element where the lubricant composition is used. However, since it is considered that the lubricant composition is less likely to be scattered due to a mechanical impact caused by rotation of a mechanical element or the like, it is preferable. Furthermore, since the compound B has little evaporation loss, it is considered that the compound B functions suitably as a component of the lubricant composition even in a severe environment such as a high temperature.

  The lubricant composition of the present invention contains such compound B and / or compound A of the present invention. In the lubricant composition of the present invention, one compound may be used alone as the compound A of the present invention, or two or more compounds may be used in combination. The same applies to Compound B of the present invention.

  The viscosity of the lubricant composition of the present invention is usually in the range of 1 to 50,000 mPa · s, preferably 3 to 10,000 mPa · s in the temperature range of −20 to 60 ° C., as described below. It can be used in a wide range of applications from low-lubricating oils to high-viscosity lubricating oils.

  And the dynamic friction coefficient of the lubricant composition of this invention is 0.05-0.5 normally in the range of -10 degreeC-40 degreeC, Preferably it is 0.08-0.2 from a lubrication viewpoint.

<Lubricant composition in the form of a mixture of compound B>
In addition, as described above in the description of the method for producing compound B of the present invention, the core raw material and raw material 1 (form group A in general formula (3)) and 2 (form group B in general formula (3)). When they are reacted at the same time, four types (or three types) of compounds are generated due to the problem of probability, and the compound B of the present invention is obtained as a mixture. The mixtures thus obtained are A-O-W-O-A, A-O-W-O-B, B-O-W-O-A, and B-O-W-O-B. Is a mixture of compounds having the structure

  In other words, these compounds have one group (first group) selected from the options of the group A in the general formula (3) and one group (second group) selected from the options of the group B, Compound having any combination on the left and right sides of the group W (a compound in which the group A and the group B are the first group, a compound in which the group A is the first group and the group B is the second group, the group A Is a second group and a group B is the first group, and a compound in which the group A and the group B are the second group).

  Such a mixture can also be used as the lubricant composition of the present invention, and the lubricant composition achieves a low viscosity in a wider temperature range than when Compound B is used alone. Can do. In addition, since the mixture is inevitably formed when the compound B is synthesized, an operation of adding a predetermined other compound to the compound B is unnecessary, and only the compound B may be isolated from the mixture. This is unnecessary and advantageous in terms of manufacturing cost.

<Other ingredients>
Next, other components that may be included in the lubricant composition of the present invention within a range not impairing the effects of the present invention will be described in order. These are basically known substances as components of the lubricant composition, and their contents can be appropriately selected by those skilled in the art within a conventionally known range unless otherwise specified. In addition, any of these components may be used alone or in combination of two or more.

(Liquid crystal compound)
Although compound B of the present invention is a liquid crystal compound, the lubricant composition of the present invention may contain other liquid crystal compounds.

  Examples of such a liquid crystal compound include a liquid crystal compound exhibiting a smectic phase or a nematic phase, an alkyl sulfonic acid, a compound having a Nafion membrane structure, an alkyl carboxylic acid, and an alkyl sulfonic acid.

  The combined use of these components can broaden the temperature range in which the liquid crystal compound contained in the lubricant composition of the present invention forms a liquid crystal phase, and the advantages of the above liquid crystal phase formation can be enjoyed in a wide temperature range. There is sex.

(Base oil)
When the compound of the present invention is included in the lubricant composition as an additive, various conventionally known lubricant base oils can be used as the base oil.

  Although it does not specifically limit as said base oil, For example, mineral oil, highly refined mineral oil, synthetic hydrocarbon oil, paraffinic mineral oil, alkyl diphenyl ether oil, ester oil, silicone oil, naphthenic mineral oil, fluorine oil, etc. can be used. The content of such base oil in the lubricant composition of the present invention is usually 80 to 99% by weight.

(Other additives)
When the compound of the present invention is included in the lubricant composition as a base oil, various conventionally known additives can be added to the lubricant composition. In addition, you may mix | blend the compound A of this invention as a base oil, and mix | blend the compound B of this invention as an additive. The reverse is also possible.

  Other additives that can be added to the lubricant composition of the present invention include various additives used in lubricants such as bearing oils, gear oils and hydraulic oils, that is, extreme pressure agents, oriented adsorbents, and wear prevention agents. Agents, wear modifiers, oiliness agents, antioxidants, viscosity index improvers, pour point depressants, cleaning dispersants, metal deactivators, corrosion inhibitors, rust inhibitors, antifoaming agents, solid lubricants, etc. Can be mentioned.

  Examples of the extreme pressure agent include chlorine compounds, sulfur compounds, phosphoric acid compounds, hydroxycarboxylic acid derivatives, and organometallic extreme pressure agents. By adding the extreme pressure agent, the wear resistance of the lubricant composition of the present invention is improved.

  Examples of the alignment adsorbent include organic silanes, organic titanium, and organic aluminum typified by various coupling agents such as a silane coupling agent, a titanium coupling agent, and an aluminum coupling agent. By adding an alignment adsorbent, when the lubricant composition of the present invention contains a liquid crystal compound, the liquid crystal alignment is strengthened, and the thickness of the film formed from the lubricant composition of the present invention, which will be described later, and its Strength can be enhanced.

<Method for preparing lubricant composition>
The lubricant composition of the present invention can be prepared by mixing the compound of the present invention described above and other components by a conventionally known method. An example of the method for preparing the lubricant composition of the present invention is as follows.

  The constituents of the lubricant composition are mixed by a conventional method, and then, if necessary, roll milling, defoaming treatment, filtering treatment, etc. are performed to obtain the lubricant composition of the present invention. Alternatively, the lubricant composition can also be obtained by first mixing the oil component of the lubricant composition, then adding and mixing other components such as additives, and performing the above defoaming treatment as necessary. Can be prepared.

[Use of lubricant composition]
As described above, the lubricant composition of the present invention exhibits good low viscosity in a wide temperature range, particularly in a low temperature range, and also has a small coefficient of dynamic friction, and can be used as a lubricant in various mechanical devices.

  In general, a mechanical device has a plurality of mechanical elements that move relative to each other in contact with each other. By arranging the lubricant composition of the present invention on at least a part of the contact surface of the mechanical elements, Friction caused by contact can be reduced and relative motion can be smoothed.

  In the present invention, the contact refers not only to the case where a plurality of objects are in direct contact but also to the case where the object is indirectly in contact with some substance such as a film formed by the lubricant composition of the present invention. Including. That is, when the lubricant composition of the present invention is disposed on the contact surfaces of a plurality of machine elements, a film made of the composition is formed between the plurality of machine elements, and direct contact between the machine elements is eliminated. Thereby, wear and seizure due to friction between machine elements can be suitably prevented.

  Methods for disposing the lubricant composition of the present invention on the contact surfaces of the plurality of machine elements are known to those skilled in the art. Such methods include, for example, applying the composition to the contact surface, and filling the composition into a certain area in close proximity to the machine element, including the contact surface of the machine element.

  The mechanical elements are elements (parts, etc.) constituting various mechanical devices, which are conventionally lubricated with a lubricant and those that may be lubricated with a lubricant in the future. including.

  The contact surfaces of the plurality of machine elements, more broadly speaking, the contact sites of the machine elements may be flat or curved, and at least a part of such surfaces may have irregularities or holes. May be present. Moreover, surface treatments such as various modifications may be performed on the parts of the machine elements constituting the contact parts of the machine elements. The material of the machine element is not particularly limited, and may be made of any material such as a metal material or an organic / inorganic material. Further, the type of the constituent material may be different between one of the machine elements and the other.

  Examples of the machine device having such various machine elements include transportation machines, processing machines, computer-related equipment, office-related equipment such as copiers, and household products, and the lubricant composition of the present invention. Can be suitably used for lubrication of bearings of these various mechanical devices, for example.

  Specific examples of the bearings include bearings used in electrical equipment for automobiles such as electric fan motors and wiper motors; rolling bearings used in automobile engine accessories such as water pumps and electromagnetic clutch devices, and drive systems; industrial machinery Rolling bearings used in rotating devices such as small to large general-purpose motors for machines; high-speed and high-precision rotating bearings such as spindles for machine tools, motors and rotating devices for household appliances such as air conditioner fan motors and washing machines Rolling bearings used; rolling bearings used in rotating parts of computer-related equipment such as HDD devices and DVD devices; rolling bearings used in rotating parts of office machines such as copying machines and automatic ticket gates; and trains and Axle bearings for freight cars.

  In addition, the lubricant composition of the present invention lubricates resin pulleys used in automobile CVJ devices and electronic / electric control power steering devices, and lubricates mechanical elements of various rolling devices such as linear guides and ball screws. Can be used for

  The lubricant composition of the present invention includes, for example, engine oil, gear oil, automotive hydraulic oil, marine / aircraft lubricating oil, machine oil, turbine oil, hydraulic hydraulic oil, spindle oil, compressor oil, Vacuum pump oil, refrigerating machine oil, lubricant for metal processing, hinge oil, sewing machine oil, sliding surface oil, and HDD platter lubricant (using horizontal magnetic recording system and thermal assist recording technology, etc.) It can also be used for lubricants for magnetic recording media, lubricants for micromachines, lubricants for artificial bones, and the like.

  EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention further in detail, this invention is not limited at all by these.

[Example 1 and Comparative Example 1]
<Synthesis Example 1>
The compound A1 of the present invention was synthesized according to the reaction scheme shown below.

(1) Synthesis of Compound (A1-ii) 400 ml of ethanol was put into a 1000 ml eggplant type flask, and 13.8 g (0.6 mol) of metallic sodium was dissolved. To this, 71.0 g (0.6 mol) of 3-methyl-1,5-pentanediol was added, and ethanol was removed under reduced pressure by an evaporator.

  200 ml of DMF was added to the residue, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere. Thereafter, 82.2 g (0.6 mol) of 1-bromohexane was added, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere.

  The reaction solution was poured into 600 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 600 ml of diethyl ether using a 2 L separatory funnel. An ether layer was obtained, and 600 ml of distilled water was added thereto and shaken and washed well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 31.8 g (0.158 mol) of a colorless and transparent liquid compound (A1-ii) as a target product.

(2) Synthesis of Compound (A1-iii) 27.4 g (0.14 mol) of Compound (A1-ii) and 1.0 g (0.013 mol) of pyridine were placed in a 100 ml three-necked flask. A solution obtained by dissolving 36.6 g (0.14 mol) of phosphorus tribromide in 20 ml of toluene was placed in the dropping funnel, and the reaction solution was added dropwise while cooling in an ice bath to keep the temperature at 5 ° C. or lower. The mixture was stirred at room temperature for 24 hours under a nitrogen atmosphere.

  The reaction solution was poured into 300 ml of ice water, and the target product was extracted with 300 ml of diethyl ether. An ether layer was obtained, and 300 ml of distilled water was added to it and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 31.1 g (0.12 mol) of a colorless transparent liquid compound (A1-iii) which was the target product.

(3) Synthesis of Compound (A1-v) 100 ml of ethanol was put into a 500 ml eggplant type flask, and 2.2 g (0.1 mol) of metallic sodium was dissolved. To this, 8.1 g (0.08 mol) of compound (A1-iv) was added, and ethanol was removed under reduced pressure by an evaporator.

  100 ml of DMF was added to the residue, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere. Thereafter, 31.0 g (0.12 mol) of the compound (A1-iii) was added, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere.

  The reaction solution was poured into 300 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 300 ml of diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 8.5 g (0.029 mol) of a colorless and transparent liquid compound (A1-v) as a target product.

(4) Synthesis of Compound (A1) A 500 ml three-necked flask was charged with 80 ml of diethyl ether, 8.3 g (0.029 mol) of the compound (A1-v), and 2.3 g (0.029 mol) of pyridine. 1-decanoic acid chloride 5.5g (0.029mol) was put into the dropping funnel, and it was dripped, cooling with an ice bath so that a reaction liquid might be kept at 5 degrees C or less. The mixture was stirred at 50 ° C. for 24 hours under a nitrogen atmosphere.

  The reaction solution was poured into 300 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 300 ml of diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 9.6 g (0.022 mol) of a colorless and transparent liquid compound (A1) which was the target product.

<Viscosity evaluation>
The viscosity at various temperatures of the compound A1 obtained as described above was evaluated. The measuring method of a viscosity is as follows. Using a rotational viscometer (TV-22LT viscometer manufactured by Toki Sangyo Co., Ltd.), the viscosity of Compound A1 was measured at each measurement temperature shown in Table 1 below. The evaluation results are shown in Table 1 below.

  The same viscosity measurement results of DOS (the following structural formula: dioctyl sebacate) are shown in Table 2 below.

  When the viscosity evaluation results of the compound A1 of the present invention and DOS are compared, the results are shown in Table 3 below.

  As can be seen from this comparative table, the compound of the present invention has a viscosity lower than that of DOS which has been widely used as a lubricating oil at various temperatures, particularly at a low temperature of −20 ° C., which is much lower than that of DOS. It can be used well even in such a low temperature environment.

<Dynamic friction coefficient measurement>
A surface property measuring machine TYPE: 14FW manufactured by Shinto Kagaku Co., Ltd. was used. A stainless steel plate is fixed to the moving table of this apparatus, samples (compounds A1 and DOS) are dropped, point pressure is applied with the fixed ball, and wear due to reciprocating motion is repeated. And the dynamic friction coefficient of compound A1 of this invention was measured, and these average values (average dynamic friction coefficient) were computed. The results are shown in Tables 4 and 5 below. It can be seen that Compound A1 of the present invention has a smaller dynamic friction coefficient than DOS.

(Measurement condition)
Vertical load: 100g
Friction speed: 600mm / min
Number of round trips: 1800
Reciprocating stroke: 5mm
Weighted transducer capacity: 19.61N
Test piece temperature: 40 ° C
Friction mating material: SUS304 stainless steel sphere diameter 10mm
Sample volume: 0.2 mL

[Examples 2 to 5]
[Synthesis Examples 2 to 5]
As shown below, the compounds A2 to A5 of the present invention in which R ¹ is an alkyl group having various carbon chain lengths in the general formula (1) were produced.

<Synthesis Example 2>
(Synthesis of Intermediate of Compound A3 of the Present Invention)

200 ml of ethanol was put into a 500 ml Erlenmeyer flask, and 4.7 g (0.20 mol) of Na was dissolved. To this was added 25.0 g (0.19 mol) of the compound of formula (i) dissolved in 100 ml of ethanol, and ethanol was removed under reduced pressure using an evaporator.

  200 ml of DMF was added to the residue and dissolved by heating under a nitrogen atmosphere. Then, it stirred at 70 degreeC under nitrogen atmosphere for 24 hours.

  After stirring, 45.2 g (0.20 mol) of the compound of formula (ii) was added dropwise and reacted at 70 ° C. for 24 hours.

  After the reaction, the reaction solution was poured into cold dilute hydrochloric acid (ice 30 g + distilled water 200 ml + hydrochloric acid 30 ml), and the target product was extracted with 300 ml diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed and diethyl ether was removed under reduced pressure. The residue was distilled under reduced pressure to obtain the target compound of formula (iii) (intermediate of compound A3).

(Synthesis of Compound A3 of the Present Invention)

  200 ml of diethyl ether, 20.0 g (0.074 mol) of the compound of the formula (iii) and 5.8 g (0.074 mol) of pyridine are added to a 500 ml three-necked flask, and the compound of the formula (iv) 14. 0 g (0.074 mol) was added dropwise. After dropping, the mixture was refluxed at 50 ° C. for 24 hours using an oil bath.

  After refluxing, extraction was performed using a 1 L separatory funnel. First, 300 ml of diethyl ether was added to the reaction solution, poured into cold dilute hydrochloric acid (ice 30 g + distilled water 200 ml + hydrochloric acid 30 ml), and extracted using a 1 L separatory funnel. An ether layer was obtained, 100 ml of distilled water was added thereto and washed well by shaking, and the ether layer was obtained by liquid separation in a 500 ml Erlenmeyer flask. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed and diethyl ether was removed under reduced pressure. The residue was distilled under reduced pressure to obtain the target compound of the formula (v) (compound A3 of the present invention).

<Synthesis Examples 3-5>
In Synthesis Example 2, the same reaction was performed by replacing R of the compound (RBr) of the formula (ii) with C ₈ H ₁₇ , C ₁₂ H ₂₅ and C ₁₄ H ₂₉ , respectively, and the compounds A2, A4 and A5 was obtained.

<Evaluation of Compounds A2 to A5 and DOS (Examples 2 to 5 and Comparative Example 2)>
With respect to the compound A3 of the present invention produced in Synthesis Example 2 and DOS, the viscosity at various temperatures was measured. The results are shown in Table 6 below.

  Further, the dynamic friction coefficient of the compounds A2 to A5 and DOS of the present invention was measured in the same manner as described above. The results are shown in Table 7 below.

From Table 7, it can be seen that the compounds A2 to A5 of the present invention all have a lower dynamic friction coefficient than DOS and are excellent as a lubricant, and the dynamic friction coefficient can be adjusted by adjusting R ¹ in the general formula (1).

[Examples 6 to 10 and Comparative Example 3]
<Synthesis Example 6>
Compound B1 of the present invention was synthesized according to the reaction scheme shown below.

(1) Synthesis of Compound (B1-ii) 300 ml of ethanol was placed in a 500 ml eggplant-shaped flask to dissolve 19.0 g (0.83 mol) of metallic sodium. To this, 71.0 g (0.60 mol) of compound (B1-i) was added, and ethanol was removed under reduced pressure by an evaporator.

  To the residue was added 300 ml of DMF, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere. Thereafter, 104 g (0.76 mol) of 1-bromobutane was added, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere.

  The reaction solution was poured into 300 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 300 ml of diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed by filtration, and diethyl ether was removed under reduced pressure by an evaporator. The residue was distilled under reduced pressure to obtain 27.4 g (0.157 mol) of the objective colorless and transparent liquid compound (B1-ii).

(2) Synthesis of Compound (B1-iii) 25.4 g (0.15 mol) of Compound (B1-ii) and 2.0 g (0.026 mol) of pyridine were placed in a 100 ml three-necked flask. A solution obtained by dissolving 44.3 g (0.16 mol) of phosphorus tribromide in 30 ml of toluene was added to the dropping funnel, and the reaction solution was added dropwise while cooling in an ice bath to keep the temperature at 5 ° C. or lower. The mixture was stirred at room temperature for 12 hours under a nitrogen atmosphere.

  The reaction solution was poured into 300 ml of ice water, and the target product was extracted with 300 ml of diethyl ether. An ether layer was obtained, and 300 ml of distilled water was added to it and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed by filtration, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 17.4 g (0.073 mol) of a colorless and transparent liquid compound (B1-iii) as a target product.

(3) Synthesis of Compound (B1) 5.0 g (0.027 mol) of 4,4′-biphenol and 130 ml of DMF were added to a 500 ml three-necked flask and dissolved by stirring. Next, 15.38 g (0.11 mol) of potassium carbonate was added and stirred overnight at room temperature. Thereto was added 16.56 g (0.069 mol) of the compound (B1-iii), and the mixture was stirred at room temperature for 48 hours.

  The reaction solution was poured into 300 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 300 ml of diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed by filtration, and diethyl ether was removed under reduced pressure by an evaporator. 100 ml of methanol was added to the residue, and 2.36 g (0.0047 mol) of milky white solid compound (B1) as the target product was obtained by decantation.

<Synthesis Examples 7 to 10>
In Synthesis Example 6 (Synthesis of Compound B1-ii), “1-bromobutane” is changed to “1-bromo-2-methylbutane”, “1-bromohexane”, “1-bromo-2-ethylhexane”, and “1- A similar reaction was carried out in place of “bromodecane” to obtain compounds B2, B3, B4 and B5 of the present invention, respectively.

  For the synthesized compounds B1 to B5 and DOS of the present invention, the dynamic friction coefficient was measured in the same manner as described above (Examples 6 to 10 and Comparative Example 3). The results are shown in Table 8 below.

<Synthesis Example 11> Production of Compound B in Compound Embodiment According to the reaction scheme shown below, Compound B (B1, B3, and B6) in the mixture embodiment of the present invention was synthesized.

  To a 100 ml three-necked flask, 8.9 g (0.048 mol) of 4,4′-biphenol, 20.0 g (0.145 mol) of potassium carbonate, and 70 ml of DMF were added and stirred at room temperature for 1 hour. Further, 12.7 g (0.048 mol) of the compound (A1-iii) and 11.38 g (0.048 mol) of the compound (B1-iii) were added and stirred at 80 ° C. for 24 hours.

  The reaction solution was poured into 300 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 300 ml of diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

  Anhydrous sodium sulfate was removed by filtration, and diethyl ether was removed under reduced pressure by an evaporator. 80 ml of hexane was added to the residue, heated to 60 ° C., and purified by silica gel column chromatography. Hexane was removed under reduced pressure using an evaporator to obtain 17.0 g of a mixture of the compounds (B1), (B3) and (B6) of the present invention.

[Example 11 and Comparative Example 4]
<Synthesis Example 12>
As shown below, the compound B of the present invention (B3, B7 and B8) was synthesized.

{Synthesis of Compound (A2-iii)}
Compound (A2-iii) was synthesized according to the reaction scheme shown below.

(1) Synthesis of Compound (A2-ii) 400 ml of ethanol was placed in a 1000 ml eggplant-shaped flask to dissolve 13.8 g (0.6 mol) of metallic sodium. To this, 71.0 g (0.6 mol) of 3-methyl-1,5-pentanediol was added, and ethanol was removed under reduced pressure by an evaporator.

  200 ml of DMF was added to the residue, and the mixture was stirred at 70 ° C. for 24 hours under a nitrogen atmosphere. Thereafter, 73.8 g (0.6 mol) of 1-bromopropane was added, and the mixture was stirred at 70 ° C. for 24 hours in a nitrogen atmosphere.

  The reaction mixture was poured into 600 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 600 ml of diethyl ether using a 2 L separatory funnel. An ether layer was obtained, and 600 ml of distilled water was added thereto and washed well by shaking. An ether layer was obtained by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight. Anhydrous sodium sulfate was removed, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 24.0 g (0.15 mol) of a compound of formula (A2-ii) which was a colorless and transparent liquid.

(2) Synthesis of Compound (A2-iii) In a 100 ml three-necked flask, 22.4 g (0.14 mol) of the compound of formula (A2-ii) and 1.0 g (0.013 mol) of pyridine were added. A solution prepared by dissolving 36.6 g (0.14 mol) of phosphorus tribromide in 20 ml of toluene was added dropwise to the reaction solution through a dropping funnel while cooling the reaction solution in an ice bath so as to keep the reaction solution at 5 ° C. or lower. After completion of dropping, the mixture was stirred at room temperature for 12 hours under a nitrogen atmosphere.

  The reaction solution was poured into 300 ml of ice water, and the target product was extracted with 300 ml of diethyl ether. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight. Anhydrous sodium sulfate was removed, and diethyl ether was removed under reduced pressure using an evaporator. The residue was distilled under reduced pressure to obtain 26.7 g (0.12 mol) of a compound of formula (A2-iii) which is a colorless and transparent liquid.

<Production of Compound B (B3, B7 and B8) of the Invention in Mixture Mode>
According to the reaction scheme shown below, the compound B of the present invention (B3, B7 and B8) was synthesized in the form of a mixture.

  To a 100 ml three-necked flask, 8.9 g (0.048 mol) of 4,4′-biphenol, 20.0 g (0.145 mol) of potassium carbonate, and 70 ml of DMF were added and stirred at room temperature for 1 hour. Further, 10.7 g (0.048 mol) of the compound of formula (A2-iii) and 12.7 g (0.048 mol) of the compound of formula (A1-iii) were added and stirred at 80 ° C. for 24 hours.

  The reaction solution was poured into 300 ml of 10% cold dilute hydrochloric acid, and the target product was extracted with 300 ml of diethyl ether using a 1 L separatory funnel. An ether layer was obtained, and 300 ml of distilled water was added to the ether layer and shaken well to obtain an ether layer by liquid separation. Anhydrous sodium sulfate was added thereto and dehydrated overnight.

Anhydrous sodium sulfate was removed by filtration, and diethyl ether was removed under reduced pressure by an evaporator. 80 ml of hexane was added to the residue, heated to 60 ° C., and purified by silica gel column chromatography. Hexane was removed under reduced pressure using an evaporator to obtain 16.5 g of a mixture of the compounds (B7), (B8) and (B3) of the present invention.

<Measurement of evaporation loss with time (Example 11 and Comparative Example 4)>
1.0000 g of the mixture of (B7), (B8), and (B3) obtained in Synthesis Example 12 above and DOS (sebacic acid dioctyl ester), which is a representative lubricating oil, are put in a stainless steel container. Three pieces were prepared. They were placed in a constant temperature bath (normal pressure) at 100 ° C., taken out for a predetermined time, weighed with an electronic balance, and the average value of the reduced weight (evaporation loss) was plotted on a graph. The results are shown in FIG.

  FIG. 1 shows that the mixture of (B7), (B8), and (B3) has almost no evaporation loss in an environment of 100 ° C. as compared with DOS.

Claims (14)

Lubricating compound represented by the following general formula (1):

(In the formula, R ¹ and R ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; An alkenyl group having 2 to 20 carbon atoms which may be substituted with a group or a cyano group; or may have a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group An alkynyl group having 2 to 20 carbon atoms,
R ³ and R ⁴ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group or a cyano group, which may be substituted and optionally branched, an alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group Or an alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may have a branch; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group Or an alkynyl group having 2 to 20 carbon atoms,
R ² and R ⁵ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, or may have a branch; or a fluorine atom, a hydroxyl group or An alkenylene group having 2 to 20 carbon atoms which may be substituted with a cyano group or may have a branch;
m is an integer of 1-6,
When m is 2 or more, a plurality of R ^{2 s} , R ^{3 s} , R ^{4 s} , and R ^{5 s} may be the same as or different from each other. ). In the general formula (1), R ¹ and R ⁶ are each independently an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch. Yes,
R ³ and R ⁴ are each independently a hydrogen atom; or a C 1-20 alkyl group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and which may have a branch;
R ² and R ⁵ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch;
The lubricating compound according to claim 1.   The lubricating compound according to claim 1 or 2, wherein in the general formula (1), m is an integer of 1 to 3. In the general formula (1), R ² and R ⁵ in the parenthesized unit with the subscript m are the same group (in the case where m is 2 or more, one unit, 4. The lubricating compound according to claim 1, wherein R ² and R ⁵ in different units may be the same or different. The lubricating compound according to any one of claims 1 to 4, wherein the lubricating compound is a compound represented by the following general formula (2):

(In the formula, R ^{1 ′} has the same meaning as R ¹ in the general formula (1);
R ^{2 ′} and R ^{2 ″} are each independently synonymous with R ² in the general formula (1),
R ^{3 ′} and R ^{3 ″} are independently the same as R ³ in the general formula (1),
R ^{4 ″} is synonymous with R ⁴ in the general formula (1),
R ^{5 ′} and R ^{5 ″} are independently the same as R ⁵ in the general formula (1),
R ^{6 ′} has the same meaning as R ⁶ in the general formula (1),
n is an integer of 1 to 3,
p is an integer from 0 to 3,
The unit enclosed in parentheses with n subscripts and the unit enclosed in parentheses with p subscripts may exist in blocks or randomly. ). Lubricating compound represented by the following general formula (3):

[Where:
The group A may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; may be substituted with a fluorine atom, a hydroxyl group or a cyano group An optionally branched alkenyl group having 2 to 20 carbon atoms; an alkynyl group having 2 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; Alternatively, it is a monovalent organic residue represented by the following general formula (4):

(In the formula, R ¹¹ is optionally substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; substituted with a fluorine atom, a hydroxyl group or a cyano group. An alkenyl group having 2 to 20 carbon atoms which may be branched or optionally branched; alternatively, it may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branched carbon number 2 -20 alkynyl groups,
R ¹² and R ¹⁵ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group or a cyano group, which may be substituted and optionally branched, an alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group Or an alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may have a branch; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group Or an alkynyl group having 2 to 20 carbon atoms,
R ¹³ represents a single bond; a C 1-20 alkylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or a fluorine atom, a hydroxyl group or a cyano group; An alkenylene group having 2 to 20 carbon atoms which may be substituted or branched;
R ¹⁴ and R ¹⁶ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may be branched; or a fluorine atom, a hydroxyl group or It is a C2-C20 alkenylene group which may be substituted with a cyano group and may have a branch. )
The group W is a divalent group selected from the group consisting of a divalent tetralin group which may be substituted, a divalent polycyclic aromatic group which may be substituted, and a group represented by the following general formula (I). The mesogenic group of

(Wherein, ring D, ring E and ring F are each independently a benzene ring, cyclohexane ring, cyclohexene ring, pyridine ring, pyrimidine ring, dioxane ring, tetralin ring or polycyclic aromatic ring,
Y is independently hydrogen atom, deuterium atom, alkyl group having 1 to 8 carbon atoms, alkoxy group, alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkoxyalkyl group, alkanoyloxy group, alkoxycarbonyl. A group, a halogen atom, or a cyano group,
s1 to s3 are each independently an integer up to 1, or the number of sites to which a substituent of ring D, ring E or ring F can be bonded;
when s1 to s3 are 2 or more, a plurality of Y bonded to the same ring may be the same or different;
Z ₁ and _{Z 2} are each independently a single _{bond, -CO-O -, - O} -CO -, - CH 2 O -, - OCH 2 -, - CH 2 CH 2 -, - CH = CHCH 2 O-, _{-CH = CH -, - CF 2} O -, - OCF 2 -, - S -, - SO -, - SO 2 - or a -C≡C-,
r is 0, 1 or 2;
When r is 2, two Z ₁ may be the same or different, and the two rings D may be the same or different, and are bonded to the two rings D, respectively. Y may be the same or different. )
The group B is a monovalent organic residue represented by the following general formula (5):

(Wherein R ²¹ and R ²³ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; , An alkenylene group having 2 to 20 carbon atoms which may be substituted with a hydroxyl group or a cyano group and may have a branch;
R ²⁴ represents a single bond; a C 1-20 alkylene group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group; or a fluorine atom, a hydroxyl group or a cyano group; An alkenylene group having 2 to 20 carbon atoms which may be substituted or branched;
R ²² and R ²⁵ are each independently a hydrogen atom; a fluorine atom, a hydroxyl group or a cyano group, which may be substituted and optionally branched, an alkyl group having 1 to 20 carbon atoms; a fluorine atom, a hydroxyl group Or an alkenyl group having 2 to 20 carbon atoms which may be substituted with a cyano group and which may have a branch; or a branch which may be substituted with a fluorine atom, a hydroxyl group or a cyano group Or an alkynyl group having 2 to 20 carbon atoms,
R ²⁶ may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branched alkyl group having 1 to 20 carbon atoms; may be substituted with a fluorine atom, a hydroxyl group or a cyano group An optionally branched alkenyl group having 2 to 20 carbon atoms; or an optionally substituted alkynyl group having 2 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group It is a group. ]].   In the general formula (3), the group A is an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, or may have a branch, or the general formula The lubricating compound according to claim 6, which is an organic residue represented by (4). In the general formula (4), R ¹¹ is an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and may have a branch;
R ¹² and R ¹⁵ are each independently a hydrogen atom; or a C 1-20 alkyl group which may be substituted with a fluorine atom, a hydroxyl group or a cyano group, and which may have a branch;
R ¹³ , R ¹⁴ and R ¹⁶ are each independently an alkylene group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and which may have a branch. Or the lubricating compound according to 7. In the general formula (5), R ²¹ , R ^23, and R ²⁴ are each independently substituted with a fluorine atom, a hydroxyl group, or a cyano group, and may have a branched chain having 1 to 20 carbon atoms. An alkylene group,
R ²² and R ²⁵ are each independently a hydrogen atom; or a fluorine atom, a hydroxyl group, or a cyano group, which may be substituted and may have a branched alkyl group having 1 to 20 carbon atoms,
The lubricity according to any one of claims 6 to 8, wherein R ²⁶ is an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a hydroxyl group or a cyano group and may have a branch. Compound. In the general formula (I), ring D, ring E and ring F each independently represent a benzene ring, cyclohexane ring, dioxane ring, tetralin ring or polycyclic aromatic ring, and Y each independently represents a hydrogen atom or halogen. represents an atom, _{Z 1} and _{Z 2} each independently represents a single bond or -CO-O- and, r is 0 or 1, lubricious compound according to any one of claims 6-9. In the general formula ^{(4), R 14} and ^{R 16} are the same group, in the general formula ^{(5), R 21} and ^{R 23} are identical groups, according to any of claims 6-10 Lubricating compound.   A lubricant composition comprising the lubricating compound according to claim 1. A lubricant composition comprising the lubricating compound according to claim 6, wherein the composition comprises
A group selected from one group (first group) selected from the options of the group A in the general formula (3) and one group (second group) selected from the options of the group B is represented by the general formula A plurality of compounds having as group A and group B in (3),
In the general formula (3), the plurality of compounds are a compound in which the group A and the group B are the first group, a group A is the first group, and the group B is the second group. A compound, a compound in which the group A is the second group and the group B is the first group, and a compound in which the group A and the group B are the second group,
Lubricant composition.   A mechanical device comprising a plurality of mechanical elements that move relative to each other in contact with each other, and the lubricant composition according to claim 12 or 13 disposed on at least a part of a contact surface of the mechanical elements.