Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
CA 02447044 2003-11-06 IyU. ~LSy C. Z3
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- ~Ua~zr,~~z~.TG os~ COMPOSITION CaflPR~SING .~N ?~.t7Dxf~V'~
y COMBINATION_OF~ ,A. C.1~.R~0~fT~TC ACID AND AN A.~LSN~~ AS ANTI- .
' ' ~ RUST AGENT ' ' ' '
' ' ' ~ ~ha present invention relates' to.~ a lubricating ~ oil~
.' ' : composition which ~has excellent -anti.-rust properties in
, sewers operating environments in ~~which wate~r ox ~seawatex
~ , is admixed, and~ which .also exhibits ~excel7.ent propert~.es
~5 ~ ~ in terms a.f both the' lubricating properties and anti
~ ' , ' corrosion praperti.es~ in ~rarious types. of ~mach~.n.ery.
~Ant.i-rust agents are added ~to lubri.cating oils to
' ~ . ' , prot~ect~~th~e znechanica~J. ,parts from rusting when water or,~
. . . . ' ~ ' seawater ~i.s admixed.~~. In general; ~ 'anti-rust agents are
~ _ ~y .~.~ .10 ~. .' ~, 'strongly, adsorbed on the ~.metal'~ surz,ace to
'form a rust- ~'
' . ' .. .proof .filan 'on. the ~zneta~.. ~surface,~, thus pre~renting direct
.. ~ ~, ~ ~ ~ . contact ~ between ~the .metal.. and water,~ :f~om~ occurring
and
. ~ . ' ~ thefeby inhibiting the formation of rust_ . ~ . ' ' . '
. ' . . ; . ~ ~ On, the other. hand. .the .'wear surfaces ~of equipment ~
1.5 ~ ~ ~ ~ are being subj ected to~ ever'~more severe~ ~ conditions ' as 'a
~ ~ ~ - ' ~ ' ,result of~. .increased running ~ speeds, increased loads and
~ increases: .iri. efficiency 'which haue .ar~.senv ixx recent ' ~ ~'
. times, and .scorching .of the wear ~surfa~ces is likely to:
~ , . . 'occur as 'a result~ of the breakdown .of the~ lubricating oil
' 20 : film. ~ . . ~ . . ' ~
. ~ : , GonsequentXy, extx~ane.pressure. additives, which ,
. ~ . . . ,' react with ~ the ~ metal. surface arid maintain ' the,
lubricating
properties at .the wear surface, are added in suitable
' ' amounts ~a ~the lubricating ails which axe used under~such
25~ severe conditions in. order to prevent sticl~~,ng. of the
wear. surfaces. ~.
EP-A-0.744456 describes a lubricant wh~,ck~ comprises
at ~l.east one oil ~ of lubricating viscosity and at least
~ ~ ~(a) .at least 'one oil-soluble metal-free sulphur- '
.~ ' . EmpfangsZeit ~1'O,Juli 10 443~ME~DEpSHIE~T~ . .~ ~. . . ' ..
_ ._. _..... . . . . ,. .. . . . .. . . .. . .. . _..~ .~_.___.__._..
._.__.~,__.___.. .. . .. .. . .. . . . .. ... . . .. .. _..... . ..___._.. .
.____.__...,.__~.__ ,
CA 02447044 2003-11-06
IU, JUL, 1UU3 y:y4 . JtItLL 11V1 1C ' -IVU, py f. y
w ,. a ~
~~~ Na a~~~~b'o~~~ ,. .:. ' ' ' ~ ~ - ~ ~ E~o~o~~aaa
.3:.,~,t ~ "a _,..~ .b:r...3rtif.M,... . . ..,:'?.f.:;..".".n..~....
,.....,..,:.l.:..,.,: ,
s
- 1a - . . . . . ..
.~ containing anti-wear and/or.extreme pressure agent having ,
.a copper corrosion tact activity of not more than 65: (b)' . '
at. least one oil soluble metal-free phosphorus-'and
- ~ r:'itrogen-containing ~anti.weax andlor e~txezne pressure .
. agent; (c?.~at least one. oil-soluble organic carboxylic
'acid; and (d) at least one oil-soluble organic amine.
. US-A-5152908 discloses a gear lubricant comprising a
major amount oW an'.oil'of lubricating viscosity and.a
.minor amount of an additive package~which.is comprised of
. (a) a treated zinc.dithiophosphate, (b} an overbased
:carboxylate which is preferably borated, (c)-an '.,
' ' alkylamine~ arid' ~ (d.) a sulphurised olefin. ~ .
'. ~.. WO--A-0/11122 .discloses a lubricating oil' - w
. . ~ composition comprising (Iy T00 parts by wei:ght'or a base
. 15 ~ ~.~ . 'oxl far a lubricating oil; (II) as. an' anti-wear agent,' ,
. (i) ~ (a) zrom 0..05 to~ 10, parts, by weight of ~a ~ - .
phosphoxoth~.onate as described therein,' and (b) .=rom 0.01 .
_- to.l.0~part by weigh'' of an amine salt of a phosphorus
' ~ ~ . compound which: ,phosphorus compound is as described
2~0 , -therein, and/or (ii)~~ frorn 0.05 to 10 parts by weight o~ a ' ' .
.. ' dithiophosphate as described therein; (III) as a rust
. : , _ ~~preventyng , agent, from 0 . 01. to 1. 0 part by weight of a.
. polyalkylene polyamide obtained by reacting'(a) a
polyalkylene polyamine as'described therein, and (b) a~
.25 carboxylic acid having from 4.to 30 carbon atoms. ,
~p-A-0434464 describes a lubricant composition which
,comprises (a)~ a metal.-tree anti--wear or load carrying
,~ additive containing~sulphur and/or.phospharus, and (b) a
corrosion inhibitor in the form of an~am~.no succinate ~ '.
30 ~ ester of formula R100C (CR3R4 ) CR5 (NR6R~ ) COOR2 ~.ri which R1
and.R2 ars each alkyl of 1 to 30 carbon atoms, R3, R4 and
R5 are each hydrogen or alkyl o~ 1 to'4 carbon atoms, and
R6 and R7 are each'hydrogen, alkyl o.f ~. to 30 carbon
atoms, or an acyl group derived from a.saturated or
EmpfangsZeit lO.Juli 10:44q w ° a ~ . ' .. , . '
:AMENDE,D SHEET'
..._:_.. __.__~._...~_ .r._-~ . ...... . ._ .. .. .. . . .. .. . . .i~ .. .
._....-. _ __.v.__~w: ~~_~ ~._._ _____.._ ... . .. . . .. . . . . . . . . ...
. . ......:____
JUL 1UU~ y :4~ JIItLL 11V I 1 r CA 02447044 2003-11-06 IVU, ~ icy C I U
~ ~ ~1' ~~ yt ' . . . ' . . , . . . ~ . . ~ ~ ' . . - . 1v 7 El i.~~ ~Pp
i~1;0 07x~003~ ~ ,.~, ,.. _ ~ . . - . ~ EP02050,~C, ".
,.s~ r:r~SY.."..n.,..~..u. '~.».1;.....~~._,:I . ' ~ ~ ' . . i ~ fi.,:.m;:T ,
~ h..:~e. . J......'.~.."~
' ~ . .. ~. ,, . . .._.- , _ , . . ._, ~.b,_~ . - '~~ w :: ~:~ -. . .:.'...:
.~ unsaturated carboxylic acid o~ up to 30 carbon atoms,~~at ~ .
least one o~.R6 and R~ being an acyl~group.
However, it is known that the compounding of an . ~
. anti-rust agent. impedes the reaction betweew the~metal
_ surface-.and an. extreme pressure additive at the. wear .
s~.rface and that the e~=ect of the .extreme' pressure '
additive. is~.to -a large extent lost as a result. .' .
CA 02447044 2003-11-06
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_ 2 _
It is therefore desirable to provide ashless
lubricating oil compositions which contain no metal and.
which, from the viewpoints of the lubrication performance
and the anti-rust performance of the lubricating oil,
maintain excellent extreme pressure performance even
under severe lubrication conditions and at the same time
have excellent anti-rust properties.
It has now been surprisingly discovered that the
amount of anti-rust agent added can be greatly reduced by
combining specific alkylamines with the anti-rust agents,
with the result that the reduction in the extreme
pressure performance caused by the anti-rust agent can be
suppressed to a minimum level.
The present invention provides a lubricating oil
composition comprising a minor amount of an additive
combination comprising
(i) a carboxylic acid-based or carboxylic acid ester-
based anti-rust agent;
(ii) at least one type of amine selected from among the
group comprising (A) the alkyl amines which can be
represented by general formula (1),
(R1)nNH3_n (1)
wherein R1 represents a saturated or unsaturated alkyl
group which has from 12 to 30 carbon atoms, and n is an
integer of value 1 or 2and (B) the
N-alkylpolyalkylenediamines which can be represented by
general f ormula ( 2 ) ,
R2NH ( CH2 ) mNH2 ( 2 )
wherein R2 represents a saturated or unsaturated alkyl
group which has from 12 to 30 carbon atoms, and m is an
integer of value from 2 to 5; and a major amount of a
lubricating oil base oil.
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By "major amount" in the present invention is meant
at least 50 wt. o, with respect to the total weight of
the lubricating oil composition.
Said composition generally comprises from 0.001 to
0.5 part by weight of the carboxylic acid-based or
carboxylic acid ester-based anti-rust agent; and from
0.001 to 0.2 part by weight of the at least one type of
amine, per 100 parts by weight of lubricating oil base
oil.
Preferably, said composition comprises from 0.001 to
0.05 part by weight of the carboxylic acid-based or
carboxylic acid ester-based anti-rust agent, per 100
parts by weight of lubricating oil base oil. More
preferably, said composition comprises from 0.005 to 0.05
part by weight of said anti-rust agent, per 100 parts by
weight of lubricating oil base oil.
Preferably,.said composition comprises from 0.001
to 0.05 part by weight of the at least one type of amine,
per 100 parts by weight of lubricating oil base oil.
In a further embodiment of the present invention,
the lubricating oil composition comprises, as an extreme
pressure additive, a (3-dithiophosp~iorylpropionic acid
which can be represented by general formula (3),
S=P(0-R3)2SCH2CH(R4)COOH (3)
wherein R3 represents a branched alkyl group which has
from 3 to 8 carbon atoms, and R4 is a hydrogen atom or a
group selected from among the linear chain or branched
alkyl groups which have from 1 to 4 carbon atoms.
Said extreme pressure additive of formula (3) is
preferably present in an amount in the range of from
0.001 to 0.5 part by weight, more preferably from 0.001
to 0.02 part by weight, per 100 parts by weight of
lubricating oil base oil.
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- 4 -
In a still further embodiment of the present
invention, the lubricating oil composition comprises, as
an extreme pressure additive, a triaryl phosphorothioate
which can be represented by general formula (4),
S=P ( O-Ph-R5 ) 3 ( 4 )
wherein Ph represents a phenyl group, and R5 is a
hydrogen atom or a linear chain or branched alkyl group
which has from 1 to 9 carbon atoms.
Said extreme pressure additive of formula (4) is
preferably present in an amount in the range of from 0.05
to 5 parts by weight, more preferably from 0.05 to 0.5
part by weight, per 100 parts by weight of lubricating
oil base oil.
In another embodiment of the present invention, the
lubricating oil composition comprises, as an extreme
pressure additive, an acidic phosphate ester which can be
represented by general formula (5),
O=P (0R6) 3_r (OH) r (5)
wherein R6 is a linear chain or branched alkyl group
which has from 3 to 13 carbon atoms, and r is an integer
of value 1 or 2.
Said extreme pressure additive of formula (5) is
preferably present in an amount in the range of from 0_01
to 0.5 part by weight, more preferably from 0.01 to 0.1
part by weight, per 100 parts by weight of lubricating
oil base oil. x
The lubricating oil composition of the present
invention may optionally comprise one or more of
compounds of formulae (3) to (5) as extreme pressure
additives.
The lubricating oil base oil from which the
lubricating oil composition of the present invention is
CA 02447044 2003-11-06
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- 5 -
constituted is not subject to any particular limitation,
provided that it comprises petroleum-based oil and/or
synthetic hydrocarbon-based oil.
Lubricating oil base oils having a kinematic
viscosity of from 2 to 680 mm2/s (40°C), preferably of
from 5 to 320 mm2/s (40°C), and most preferably of from 8
to 220 mm2/s (40°C); a total sulphur content (wt. %) of
from 0 to 1 wt. o, and preferably of from 0 to 0.3 wt. o;
a total nitrogen content (wt. ppm) of from 0 to.100 ppm,
and preferably of from 0 to 30 ppm; and an aniline point
of from 80 to 130°C, and preferably of from 100 to 125°C,
are preferred.
The petroleum-based lubricating oil base oils which
can be used in the present invention may be, far example,
individual solvent refined base oils, hydrogenation
refined base oils or highly hydrogenated and cracked base
oils, or mixtures of such oils. Highly hydrogenated
cracked base oils are lubricating oil base oils which
have a viscosity index of at least 130 (typically from
145 to 155) obtained with a slack wax which has been
cracked and solvent de-waxed as the raw material by
isomerizing the linear chain paraffins to branched
paraffins by hydrogenation cracking in the presence of a
catalyst (contact cracking), or lubricating base oils
which have a viscosity index of at least 130 (typically
from 145 to 155) obtained using heavy linear chain
paraffins which have been obtained by Fischer-Tropsch
polymerization using the carbon monoxide and hydrogen
obtained by a gasification process (partial oxidation) of
a natural gas (such as methane) and subjecting this to
catalytic cracking and isomerization in the same way as
above.
Furthermore, the synthetic hydrocarbon-based base
oils which may be used in the present invention include
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- 6 -
the olefin oligomers obtained by the homopolymerization
or copolymerization of monomers which have been selected
from among the linear chain and branched olefinic
hydrocarbons which have from 3 to 15 carbon atoms, and
preferably from 4 to 12 carbon atoms.
In the present invention, the petroleum based
lubricating oil base oils and synthetic hydrocarbon based
base oils can be used individually or in the form of
mixtures.
The carboxylic acid based or carboxylic acid ester-
based anti-rust agents which can be used iri the present
invention have a carboxylic acid or carboxylic acid ester
group in the anti-rust agent molecule and they are widely
used generally in lubricating oils.
Said anti-rust agents include, for example,
monocarboxylic acids which have from 8 to 30 carbon
atoms, alkyl or alkenyl succinates or partial esters
thereof, hydroxy-fatty acids which have from 12 to 30
carbon atoms and derivatives thereof, sarcosines which
have from 8 to 24 carbon atoms and derivatives thereof,
amino acids and derivatives thereof, naphthenic acid and
derivatives thereof, lanolin fatty acid, mercapto-fatty
acids and paraffin oxides.
Particularly pref erred anti-rust agents are
indicated below.
Examples of Monocarboxylic Acids (C8 - C30)
Caprylic acid, pelargonic acid, decanoic acid,
undecanoic acid, lauric acid, myristic acid, palmitic
acid, stearic acid, arachic acid, behenic acid, cerotic
acid, montanic acid, melissic acid, oleic acid, docosanic
acid, erucic acid, eicosenic acid, beef tallow fatty
acid, soy bean. fatty acid, coconut oil fatty acid,
linolic acid, linoleic acid, tall oil fatty acid, 12-
hydroxystearic acid, laurylsarcosinic acid,
myritsylsarcosinic acid, palmitylsarcosinic acid,
CA 02447044 2003-11-06
WO 02/092735 PCT/EP02/05066
_ 7 _
stearylsarcosinic acid, oleylsarcosinic acid, alkylated
(C8 - C20) phenoxyacetic acids, lanolin fatty acid and C8
- C24 mercapto-fatty acids.
Examples of Polybasic Carboxylic Acids
The alkenyl (C20 - C100) succinic acids indicated in
CAS No. 27859-58-l and ester derivatives thereof, dimer
acid, N-acyl-N-alkyloxyalkyl aspartic acid esters
(US-A-5,275,749) which have the structural formula
indicated below and the compounds of CAS No. 68906-34-3.
R9
I
R'R$N-C-COORi2
. I
R1°-C-COORls
I
R11
wherein R7 and R8 each independently represent hydrogen
or a group selected from among the C1 to C30 alkyl
groups, the C1 to C30 acyl groups and the alkyloxide
groups, and R9 to R13 each independently represent
hydrogen or a group selected from among the C1 to C30
alkyl groups.)
Examples of the aforementioned alkylamines
represented by general formula (1) include primary amines
such as laurylamine, coconut-amine, n-tridecylamine,
myristylamine, n-pentadecylamine, palmitylamine, n-
heptadecylamine, stearylamine, n-nonadecylamine,
n-eicosylamine, n-heneicosylamine, n-docosylamine, n-
tricosylamine, n-pentacosylamine, oleylamine, beef
tallow-amine, hydrogenated beef tal~.ow-amine and soy
bean-amine. Examples of the secondary amines include
dilaurylamine, di-coconut-amine, di-n-tridecylamine,
dimyristylamine, di-n-pentadecylamine, dipalmitylamine,
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_ g _
di-n-pentadecylamine, distearylamine, di-n-
nonadecylamine, di-n-eicosylamine, di-n-heneicosylamine,
di-n-docosylamine, di-n-tricosylamine, di-n-pentacosyl-
amine, dioleylamine, di-beef tallow-amine, di-
hydrogenated beef tallow-amine and di-soy bean-amine.
Examples of the aforementioned N-
alkylpolyalkyenediamines which can be represented by
general formula (2) include ethylenediamines such as
laurylethylenediamine, coconut ethylenediamine, n-
tridecylethylenediamine, myristylethylenediamine, n-
pentadecylethylenediamine, palmitylethylenediamine, n-
heptadecylethylenediamine, stearylethylenediamine, n-
nonadecylethylenediamine, n-eicosylethylenediamine, n-
heneicosylethylenediamine, n-docosylethylendiamine, n-
tricosylethylenediamine, n-pentacosylethylenediamine,
oleylethylenediamine, beef tallow-ethylenediamine,
hydrogenated beef tallow-ethylenediamine and soy bean-
ethylenediamine; propylenediamines such as
laurylpropylenediamine, coconut propylenediamine, n-
tridecylpropylenediamine, myristylpropylenediamine,
n-pentadecylpropylenediamine, palmitylpropylenediamine,
n-heptadecylpropylenediamine, stearylpropylenediamine, n-
nonadecylpropylenediamine, n-eicosylpropylenediamine, n-
heneicosylpropylenediamine, n-docosylpropylendiamine, n-
tricosylpropylenediamine, n-pentacosylpropylenediamine,
oleylpropylenediamine, beef tallow-propylenediamine,
hydrogenated beef tallow-propylenediamine and soy bean-
propylenediamine; butylenediamines such as
laurylbutylenediamine, coconut butylenediamine,
n-tridecylbutylenediamine, myristylbutylenediamine, n-
pentadecylbutylenediamine, stearylbutylenediamine,
n-eicosylbutylenediamine, n-heneicosylbutylenediamine, n-
docosylbutylendiamine, n-tricosylbutylenediamine,
n-pentacosylbutylenediamine, oleylbutylenediamine, beef
tallow-butylenediamine, hydrogenated beef tallow-
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butylenediamine and soy bean butylenediamine; and
pentylenediamines such as laurylpentylenediamine, coconut
pentylenediamine, myristylpentylenediamine,
palmitylpentylenediamine, stearylpentylenediamine, oleyl-
pentylenediamine, beef tallow-pentylenediamine,
hydrogenated beef tallow-pentylenediamine and soy bean
. pentylenediamine.
In addition to the aforementioned components,
suitable amounts of supplementary additives of the
various types which are generally used can be added to
the lubricating oil composition of the present invention,
as required, in order to further improve the performance
thereof. Supplementary additives that may be added to
the lubricating oil composition of the present invention
include the known lubricating oil additives such as
antioxidants, metal deactivators, extreme pressure
additives, antifoaming agents, viscosity index increasing
agents, flow-point reducing agents, cleaning and
dispersing agents, anti-rust agents and anti-
emulsification agents.
Examples of amine-based antioxidants include
dialkyldiphenylamines such as p,p'-dioctyldiphenylamine
(manufactured by the Seiko Kagaku Co. under the trade
designation "Nonflex OD-3"), p,p'-di-cc-
methylbenzyldiphenylamine and N-p-butylphenyl-N-p'-
octylphenylamine; monoalkyldiphenylamines such as mono-t-
butyldiphenylamine, and monooctyldiphenylamine;
bis(dialkylphenyl)amines such as di(2,4-
diethylphenyl)amine and di(2-ethyl-4-nonylphenyl)amine;
alkylphenyl-1-naphthylamines such as octylphenyl-1-
naphthylamine and N-t-dodecylphenyl-1-naphthylamine;
arylnaphthylamines such as 1-naphthylamine, phenyl-1-
naphthylamine, phenyl-2-naphthylamine, N-hexylphenyl-2-
naphthylamine and N-octylphenyl-2-naphthylamine,
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- 10 -
phenylenediamines such as N,N'-diisopropyl-p-
phenylenediamine and N,N'-diphenyl-p-phenylenediamine,
and phenothiazines such as phenothiazine (manufactured by
the Hodogaya Kagaku Co.: Phenothiazine) and 3,7-
dioctylphenothiazine.
Examples of sulphur-based antioxidants include
dialkylsulphides such as didodecylsulphide and
dioctadecylsulphide; thiodipropionic acid esters such as
didodecyl thiodipropionate, dioctadecyl thiodipropionate,
dimyristyl thiodipropionate and dodecyloctadecyl
thiodipropionate, and 2-mercaptobenzimidazole.
Examples of phenol-based antioxidants include 2-t-
butylphenol, 2-t-butyl-4-methylphenol, 2-t-butyl-5-
methylphenol, 2,4-di-t-butylphenol, 2,4-dimethyl-6-t-
butylphenol, 2-t-butyl-4-methoxyphenol, 3-t-butyl-4-
methoxyphenol, 2,5-di-t-butylhydroquinone (manufactured
by the Kawaguchi Kagaku Co. under trade designation
"Antage DBH"), 2,6-di-t-butylphenol and 2,6-di-t-butyl-4-
alkylphenols such as 2,6-di-t-butyl-4-methylphenol and
2,6-di-t-butyl-4-ethylphenol; 2,6-di-t-butyl-4-
alkoxyphenols such as 2,6-di-t-butyl-4-methoxyphenol and
2,6-di-t-butyl-4-ethoxyphenol, 3,5-di-t-butyl-4-
hydroxybenzylmercaptooctyl acetate, alkyl-3-(3,5-di-t-
butyl-4-hydroxyphenyl)propionates such as n-octyl-3-(3,5-
di-t-butyl-4-hydroxyphenyl)propionate (manufactured by
the Yoshitomi Seiyaku Co. under the trade designation
"Yonox SS"), n-dodecyl-3-(3,5-di-t-butyl-4-
hydroxyphenyl)propionate and 2'-ethylhexyl-3-(3,5-di-t-
butyl-4-hydroxyphenyl)propionate; 2,6-di-t-butyl-a-
dimethylamino-p-cresol, 2,2'-methylenebis(4-alkyl-6-t-
butylphenol) compounds such as 2,2'-methylenebis(4-
methyl-6-t-butylphenol) (manufactured by the Kawaguchi
Kagaku Co. under the trade designation "Antage W-400")
and 2,2'-methylenebis(4-ethyl-6-t-butylphenol)
CA 02447044 2003-11-06
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- 11 -
(manufactured by the Kawaguchi Kagaku Co. under the trade
designation "Antage W-500"); bisphenols'such as 4,4'-
butylidenebis(3-methyl-6-t-butylphenol) (manufactured by
the Kawaguchi Kagaku Co. under the trade designation
"Antage W-300"), 4,4'-methylenebis(2,6-di-t-butylphenol)
(manufactured by Laporte Performance Chemicals under the
trade designation "Ionox 220AH"), 4,4'-bis(2,6-di-t- '
butylphenol), 2,2-(di-p-hydroxyphenyl)propane (Bisphenol
A), 2,2-bis(3,5-di-t-butyl-4-hydroxyphenyl)propane, 4,4'-
cyclohexylidenebis(2,6-di-t-butylphenol), hexamethylene
glycol bis[3,(3,5-di-t-butyl-4-hydroxyphenyl)propionate]
(manufactured by the Ciba Speciality Chemicals Co. under
the trade designation "Irganox L109"), triethylene glycol
bis[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionate]
(manufactured by the Yoshitomi Seiyaku Co. under the
trade designation "Tominox 917"), 2,2'-thio[diethyl-3-
(3,5-di-t-butyl-4-hydroxyphenyl)propionate] (manufactured
by the Ciba Speciality Chemicals Co. under the trade
designation "Trganox L115"), 3,9-bis{1,1-dimethyl-2-[3-
(3-t-butyl-4-hydroxy-5-methylphenyl)-
propionyloxy]ethy1~2,4,8,10-tetraoxaspiro[5,5]undecane
(manufactured by the Sumitomo Kagaku Co. under the trade .
designation "Sumilizer GA80") and 4,4'-thiobis(3-methyl-
6-t-butylphenol) (manufactured by the Kawaguchi Kagaku
Co. under the trade designation "Antage RC"), 2,2'-
thiobis(4,6-di-t-butylresorcinol); polyphenols such as
tetrakis[methylene-3-(3,5-di-t-butyl-4-
hydroxyphenyl)propionato]methane (manufactured by the
Ciba Speciality Chemicals Co. under the trade designation
"Irganox L101"), 1,1,3-tris(2-methyl-4-hydroxy-5-t-
butylphenyl)butane (manufactured by the Yoshitomi Seiyaku
Co. under the trade designation "Yoshinox 930"), 1,3,5-
trimethyl-2,4,6-tris(3,5-di-t-butyl-4-
hydroxybenzyl)benzene (manufactured by Ciba Speciality
Chemicals under the trade designation "Trganox 1330"),
CA 02447044 2003-11-06
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bas[3,3'-bas(4'-hydroxy-3'-t-butylphenyl)butyric acid
glycol ester, 2-(3',5'-di-t-butyl-4-hydroxyphenyl)-
methyl-4-(2",4"-di-t-butyl-3"-hydroxyphenyl)methyl-6-t-
butylphenol and 2,6-bis(2'-hydroxy-3'-t-butyl-5'-
methylbenzyl)-4-methylphenol; and phenol/aldehyde
condensates such as the condensates of p-t-butylphenol
and formaldehyde and the condensates of p-t-butylphenol
and acetaldehyde.
Examples of phosphorus-based antioxidants include
triaryl phosphates such as triphenyl phosphate and
tricresyl phosphate, trialkyl phosphates such as
trioctadecyl phosphate and tridecyl phosphate, and
tridodecyl trithiophosphite.
These antioxidants can be used individually or in
the form of mixtures, conveniently in amounts within the
range of from 0.01 to 2.0 parts by weight, per 100 parts
by weight of base oil.
The metal deactivating agents which can be used in
the lubricating oil a composition of the present
invention include benzotriazole and the
4-alkylbenzotriazoles such as 4-methylbenzotriazole and
4-ethylbenzotriazole; 5-alkylbenzotriazoles such as 5-
methylbenzotriazole, 5-ethylbenzotriazole; 1-
alkylbenzotriazoles such as 1-dioctylaminomethyl-2,3-
benzotriazole; benzotriazole derivatives such as the 1-
alkyltolutriazoles, for example, 1-dioctylaminomethyl-
2,3-tolutriazole; benzimidazole and benzimidazole
derivatives such as 2-(alkyldithio)-benzimidazoles, for
example, such as 2-(octyldithio)-benzimidazole,
2-(decyldithio)benzimidazole and 2-(dodecyldithio)-
benzimidazole; 2-(alkyldithio)-toluimidazoles such as 2-
(octyldithio)-toluimidazole, 2-(decyldithio)-
toluimidazole and 2-(dodecyldithio)-toluimidazole;
indazole and indazole derivatives of toluimidazoles such
as 4-alkylindazole, 5-alkylindazole; benzothiazole, 2-
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mercaptobenzothiazole derivatives (manufactured by the
Chiyoda I~agaku Co. under the trade designation "Thiolite
B-3100") and 2-(alkyldithio)benzothiazoles such as 2-
(hexyldithio)benzothiazole and
2-(octyldithio)benzothiazole; 2-(alkyl-
dithio)toluthiazoles such as 2-(benzyldithio)toluthiazole
and 2-(octyldithio)toluthiazole, 2-(N,N-
dialkyldithiocarbamyl)benzothiazoles such as 2-(N,N-
diethyldithiocarbamyl)benzothiazole, 2-(N,N-
dibutyldithiocarbamyl)benzotriazole and 2-N,N-dihexyl-
dithiocarbamyl)benzotriazole; benzothiazole derivatives
of 2-(N,N-dialkyldithiocarbamyl)toluthiazoles such as 2-
(N,N-diethyldithiocarbamyl)toluthiazole, 2-(N,N-
dibutyldithiocarbamyl)toluthiazole, 2-(N,N-dihexyl-
dithiocarbamyl)toluthiazole; 2-(alkyldithio)benzoxazoles
such as 2-(octyldithio)benzoxazole, 2-(decyl,dithio)-
benzoxazole and 2-(dodecyldithio)benzoxazole;~benzoxazole
derivatives of 2-(alkyldithio)toluoxazoles such as 2-
(octyldithio)toluoxazole, 2-(decyldithio)toluoxazole,
2-(dodecyldithio)toluoxazole; 2,5-bis(alkyldithio)-1,3,4-
thiadiazoles such as 2,5-bis(heptyldithio)-1,3,4-
thiadiazole, 2,5-bis-(nonyldithio)-1,3,4-thiadiazole,
2,5-bis(dodecyldithio)-1,3,4-thiadiazole and 2,5-bis-
(octadecyldithio)-1,3,4-thiadiazole; 2,5-bis(N,N-dialkyl-
dithiocarbamyl)-1,3,4-thiadiazoles such as 2,5-bis(N,N-
diethyldithiocarbamyl)-1,3,4-thiadiazole, 2,5-bis(N,N-
dibutyldithiocarbamyl)-1,3,4-thiadiazole and 2,5-bis(N,N-
dioctyldithiocarbamyl)1,3,4-thiadiazole; thiadiazole
derivatives of 2-N,N-dialkyldithiocarbamyl-5-mercapto-
1,3,4-thiadiazoles such as 2-N,N-dibutyldithiocarbamyl-5-
mercapto-1,3,4-thiadiazole and 2-N,N-dioctyl-
dithiocarbamyl-5-mercapto-1,3,4-thiadiazole, and triazole
derivatives of 1-alkyl-2,4-triazoles such as 1-
dioctylaminomethyl-2,4-triazole.
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These metal deactivating agents can be used
individually or in the form of mixtures, conveniently in
an amount within the range of from 0.01 to 0.5 parts by
weight, per 100 parts by weight of base oil.
The materials which can be used as anti-foaming
agents include, fox example, dimethylpolysiloxane,
organosilicates such as diethylsilicate, the
fluorosilicones, and non-silicone based anti-foaming
agents such as poly(alkylene acrylate). These can be
added and used individually or in the form of mixtures,
conveniently in an amount of from 0.0001 to 0.1 part by
weight, per 100 parts by weight of base oil.
The viscosity index increasing agents which can be
used include, for example, polymethacrylates and
ethylene/propylene copolymers, other non-dispersion type
viscosity index increasing agents such as olefin
copolymers like styrene/diene copolymers, and dispersible
type viscosity index increasing agents where a nitrogen
containing monomer has been copolymerized in such
. materials. These materials can be added and used
individually or in the form of mixtures, conveniently in
an amount within the range of from 0.05 to 20 parts by
weight per 100 parts by weight of base oil.
Examples of flow-point reducing agents include
polymethacrylate based polymers.. These materials can be
added and conveniently used in an amount within the range
from 0.01 to 5 parts by weight per 100 parts by weight of
base oil.
Examples of the cleaning and dispersing agents which
can be used include metal-based detergents such as the
neutral and basic alkaline earth metal sulphonates,
alkaline earth metal phenates and alkaline earth metal
salicylates alkenylsuccinimide and alkenylsuccinimide
esters and their borohydrides, and ashless dispersing
agents which have been modified with sulphur compounds.
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These agents can be added and used individually or in the
form of mixtures, conveniently in an amount within the
range of from 0.01 to 1 part by weight per 100 parts by
weight of base oil.
Examples of extreme pressure additives include
sulphur-based extreme pressure additives such as dialkyl
sulphides, dibenzyl sulphide, dialkyl polysulphides,
dibenzyl disulphide, alkyl mercaptans, dibenzothiophene
and 2,2'-dithiobis(benzothiazole); phosphorus-based
extreme pressure additives such as trialkyl phosphates,
triaryl phosphates, trialkyl phosphonates, trialkyl
phosphates, triaryl phosphates and dialkylhydrozine
phosphates, and phosphorus- and sulphur-based extreme
pressure additives such as zinc dialkyldithiophosphates,
dialkylthiophosphoric acid, trialkyl thiophosphate
esters, acidic thiophosphate esters and trialkyl
tri:thiophosphates. These extreme pressure additives can
be used individually or in the form of mixtures,
conveniently in an amount within the range from 0.1 to 2
parts by weight, per 100 parts by weight of the base oil.
The known anti-emulsifying agents which are
generally used as lubricating oil additives can also be
used. These agents may be conveniently added and used in
an amount within the range from 0.0005 to 0.5 part by
weight, per 100 parts by weight of the base oil.
Examples of anti-emulsifying agents include
polyalkylene glycol-based non-ionic surfactants, for
example, polyoxyethylenealkyl ethers, polyoxyethylene
alkylphenyl ethers and polyoxyethylene alkylnaphthyl
ethers.
The lubricating oil composition of the present
ivnention is useful as a hydraulic oil composition, a
compressor oil composition, a turbine oil composition, a
bearing oil composition and/or a gear oil composition.
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The present invention will now be described with
reference to the following Examples which are not
intended to limit the scope of the present invention in
any way.
Illustrative Examples
Sample oils were prepared by compounding extreme
pressure additives and carboxylic acid based and
carboxylic acid ester-based anti-rust agents and amines
at various concentrations as shown in Table 1 in a
hydrogenation refined base oil of kinematic viscosity
31 mm2/s at 40°C with a viscosity index of 107, a sulphur
content of less than 5 ppm, a nitrogen content of less
than 1 ppm and an aniline point of 112°C as the base oil.
The effect of the invention was investigated in
terms of the anti-rust agent performance and the extreme
pressure performance.
The test methods used for assessing performance in
the Examples and Comparative Examples were as indicated
below.
Anti-rust Test
In order to evaluate the anti-rust performance of
the sample oils, an anti-rust test was carried out for 24
hours at 60°C in the presence of artificial seawater in
accordance with ASTM D665. It was investigated whether
or not rust had formed on the steel specimen after the
test.
FZG Gear Wheel Test
In order to evaluate the lubrication performance of
the sample oils in gear wheel equipment, the A test gear
wheels were used in accordance with ISO/WD14635-1 and the
gears were run for 15 minutes at each loading stage at an
initial oil temperature of 90°C and a motor speed of 1450
rpm. The loading stage at which scorching occurred on
CA 02447044 2003-11-06
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- 17 -
the tooth surfaces of the test gear wheel as the load was
being increased in stages was observed.
Examples 1 to 9 and Comparative Examples 1 to 9
The compositions and test results are shown in
Tables 1 to 3.
CA 02447044 2003-11-06
WO 02/092735 PCT/EP02/05066
18
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CA 02447044 2003-11-06
WO 02/092735 PCT/EP02/05066
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CA 02447044 2003-11-06
WO 02/092735 PCT/EP02/05066
- 21 -
NOTES:
1. manufactured by the Lubrizol Co under the trade
designation "Lubrizol 859".
2. manufactured by the Ciba Speciality Chemicals Co.
under the trade designation "Sarcosil O".
3. manufactured by the Ciba Speciality Chemicals Co_
under the trade designation "Irgacore NPA".
4. manufactured by the Colonial Chemical Co. under the
trade designation "Korakoa 93".~
5. CAS No. 68906-34-3, 27136-73-8.
6. manufactured by the King Industries Co. under the
trade designation "K-CORR 100".
Anti-rust agent disclosed in US-A-5,275,749.
Comparative Example 1 had only the extreme pressure
additive compounded therein. Whilst said example and
exhibited good extreme pressure performance in the gear
wheel test, rust formed in the anti-rust test as no anti-
rust agent and amine had been added thereto.
In contrast, in Comparative Examples 3 to 8 the
minimum amount of carboxylic acid-based or carboxylic
acid ester-based anti-rust agent had been added thereto
and thus no rust formed in the anti-rust test. However,
there was a marked fall in the durable load in the FZG
gear wheel test as a result of the addition of the anti-
rust agent.
Furthermore, only the amine had been added in
Comparative Examples 2 and 9, with no carboxylic acid-
based or carboxylic acid ester-based anti-rust agent also
being added. Adequate anti-rust effect was not obtained.
With Examples 1 to 9, which are according to the
present invention, the amount of carboxylic acid-based or
carboxylic acid ester-based anti-rust agent required was
greatly reduced as a result of the synergistic effect
between the amine and the carboxylic acid-based or
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WO 02/092735 PCT/EP02/05066
- 22 -
carboxylic acid ester-based anti-rust agent which are
essential components of the invention, and there was a
great improvement in respect of the fall in the extreme
pressure performance which was caused by the anti-rust
agent.
The lubricating oil compositions of the present
invention are virtually free, or completely free, of
metals which are harmful in respect of both the
environment and safety and they maintain a good anti-rust
performance whilst also having good extreme pressure
performance to match the increased speeds, higher
pressures, more compact nature and improvement in
durability requirements of modern industrial machinery.
Furthermore, the amount of anti-rust agent added can
be reduced by means of the present invention and
lubricating oil compositions which have excellent
performance can be provided more cheaply.
The lubricating oil compositions of the present
invention are useful as lubricating oil compositions
where both anti-rust performance and extreme pressure
performance are required and they can be used as
hydraulic working oils, gear wheel oils, compressor oils,
turbine oils and bearing oils.
