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<ep-patent-document id="EP93116704B1" file="EP93116704NWB1.xml" lang="en" country="EP" doc-number="0593068" kind="B1" date-publ="19980422" status="n" dtd-version="ep-patent-document-v1-1">
<SDOBI lang="en"><B000><eptags><B001EP>......DE....FRGB..................................</B001EP><B005EP>J</B005EP><B007EP>DIM360   - Ver 2.7 (17 Nov 1997)
 2100000/1 2100000/2</B007EP></eptags></B000><B100><B110>0593068</B110><B120><B121>EUROPEAN PATENT SPECIFICATION</B121></B120><B130>B1</B130><B140><date>19980422</date></B140><B190>EP</B190></B100><B200><B210>93116704.3</B210><B220><date>19931015</date></B220><B240><B241><date>19940628</date></B241><B242><date>19960222</date></B242></B240><B250>en</B250><B251EP>en</B251EP><B260>en</B260></B200><B300><B310>301576/92</B310><B320><date>19921015</date></B320><B330><ctry>JP</ctry></B330></B300><B400><B405><date>19980422</date><bnum>199817</bnum></B405><B430><date>19940420</date><bnum>199416</bnum></B430><B450><date>19980422</date><bnum>199817</bnum></B450><B451EP><date>19970820</date></B451EP></B400><B500><B510><B516>6</B516><B511> 6C 10M 141/10   A</B511><B512> 6C 10M 169/04   B</B512><B513> 6C 10N  40/06   -</B513><B513> 6C 10N  40/08   -</B513><B514> 6C 10M 141/10   J</B514><B514> 6C 10M 133:08   J</B514><B514> 6C 10M 137:02   J</B514><B514> 6C 10M 137:04   J</B514><B517EP>// C10N40/06, C10N40/08 ,(C10M141/10, 133:08, 137:02, 137:04)</B517EP></B510><B540><B541>de</B541><B542>Stossdämpferflüssigkeit</B542><B541>en</B541><B542>Shock absorber fluid</B542><B541>fr</B541><B542>Fluide d'amortisseur</B542></B540><B560><B561><text>EP-A- 0 348 236</text></B561><B561><text>EP-A- 0 351 964</text></B561><B561><text>EP-A- 0 453 114</text></B561><B561><text>US-A- 3 799 878</text></B561><B561><text>US-A- 4 634 543</text></B561><B562><text>DATABASE WPI Week 9344, Derwent Publications Ltd., London, GB; AN 93-348678 &amp; JP-A-5 255 683 (TONEN CORP) 5 October 1993</text></B562></B560></B500><B700><B720><B721><snm>Miyagawa, Toru,
c/o Nippon Oil Co., Ltd.</snm><adr><str>Central Technical Res. Lab.,
8, Chidori-cho</str><city>Naka-ku,
Yokohama-shi,
Kanagawa</city><ctry>JP</ctry></adr></B721><B721><snm>Hirata, Shigeaki,
c/o Nippon Oil Co., Ltd.</snm><adr><str>Central Technical Res. Lab.,
8, Chidori-cho</str><city>Naka-ku,
Yokohama-shi,
Kanagawa</city><ctry>JP</ctry></adr></B721><B721><snm>Okada, Mitsuo,
c/o Nippon Oil Co., Ltd.</snm><adr><str>Central Technical Res. Lab.,
8, Chidori-cho</str><city>Naka-ku,
Yokohama-shi,
Kanagawa</city><ctry>JP</ctry></adr></B721></B720><B730><B731><snm>NIPPON OIL COMPANY, LIMITED</snm><iid>00464185</iid><adr><str>3-12, 1-chome, Nishi-Shimbashi
Minato-ku</str><city>Tokyo</city><ctry>JP</ctry></adr></B731></B730><B740><B741><snm>WILHELMS, KILIAN &amp; PARTNER
Patentanwälte</snm><iid>00100601</iid><adr><str>Eduard-Schmid-Strasse 2</str><city>81541 München</city><ctry>DE</ctry></adr></B741></B740></B700><B800><B840><ctry>DE</ctry><ctry>FR</ctry><ctry>GB</ctry></B840><B880><date>19940420</date><bnum>199416</bnum></B880></B800></SDOBI><!-- EPO <DP n="1"> -->
<description id="desc" lang="en">
<heading id="h0001"><b><u>BACKGROUND OF THE INVENTION</u></b></heading>
<heading id="h0002">1. Field of the Invention</heading>
<p id="p0001" num="0001">This invention relates to hydraulic working oil compositions for use in buffers and more particularly to such oil compositions suitable for car suspension devices such as shock absorbers.</p>
<heading id="h0003">2. Prior Art</heading>
<p id="p0002" num="0002">As conventional hydraulic working oils which have hitherto been used in car buffer devices such as shock absorbers, active suspensions, stay dampers and engine dampers, there have been known those which incorporate a phosphoric acid ester and/or a phosphorus acid ester to provide them with friction-reducing properties and wear-preventing properties. In addition, there have also widely used such hydraulic working oils in which a fatty acid, aliphatic alcohol, fatty acid ester, aliphatic amine and other oily agents are used to further improve the working oils in friction-reducing properties.</p>
<p id="p0003" num="0003">Hydraulic working oils are those which are required to be capable of reducing friction at friction surfaces simultaneously with preventing wear of the friction surfaces. Recently, there have been<!-- EPO <DP n="2"> --> increasingly used bush members impregnated with a Teflon resin in attempts to reduce friction at friction surfaces from the standpoint of material or substance used. Further, particularly gas-sealed type and damping force-variable type buffers have increasingly been used and, therefore, load applied to the friction surfaces of buffers has been increased and conditions under which the buffers are used have be come severe.</p>
<p id="p0004" num="0004">With a change in such conditions or circumstances under which hydraulic working oils are used, conventional oils incorporating only a phosphoric acid ester and/or a phosphorous acid ester, or those in which a fatty acid, aliphatic alcohol, a fatty acid ester and other oily agents are used, have raised problems in that they allow friction surfaces to be come considerably worn since their friction-reducing effects are low and poor. In addition, it has been found that the conventional working oils in which is used a phophoric acid ester and/or a phosphorous acid ester as well as an aliphatic amine which is an oily agent, will exhibit somewhat excellent wear-preventing and friction-reducing effects on the friction surfaces of a suspension device at the initial time when the working oils are used therein but the conventional working oils will raise problems that they cannot keep such effects durably and will greatly increase in<!-- EPO <DP n="3"> --> frictional coefficient during their use whereupon spherical particles produced by the wear of the friction surfaces are attached to the friction surfaces which are the surfaces of a Teflon resin-impregnated bush member.</p>
<p id="p0005" num="0005">EP-A-351 964 and EP-A-348 236 each discloses a lubricating oil composition, comprising a lubricating oil and additives including a hydroxyl amine compound and an organic phosphite ester. These power transmission fluids can control the friction characteristics but not necessarily lower it.</p>
<p id="p0006" num="0006">US-A-4 634 543 discloses a fluid composition for use in a shock absorber, comprising as an essential component a phosphoric acid ester and a boron containing detergent in a lubricating base oil.</p>
<p id="p0007" num="0007">There have been eagerly desired the developments of novel hydraulic working oils for a buffer which meet new requirements such as excellent applicability to Teflon resin-impregnated bush members and excellent durability (little degradation during the use) of friction-reducing and wear-preventing effects, in addition to the conventional requirements, since said new requirements have come to be made much of.</p>
<heading id="h0004"><b><u>SUMMARY OF THE INVENTION</u></b></heading>
<p id="p0008" num="0008">The primary object of this invention is to provide shock absorber fluids which are excellent in applicability to Teflon resin-impregnated bush members as well as durability (little degradation with the time of use) of friction-reducing and wear-preventing effects.</p>
<p id="p0009" num="0009">The present inventors made intensive studies to achieve the object of this invention and, as the result of their studies, found that the combined use of (A) a phosphoric acid ester and/or a phosphorous acid ester and (B) an alkylene oxide of an aliphatic amine in a lubricating oil as a base oil will exert their<!-- EPO <DP n="4"> --><!-- EPO <DP n="5"> --> synergistic effect thereby to obtain a new hydraulic working oil exhibiting excellent performances when used, thus completing this invention.</p>
<p id="p0010" num="0010">The primary object of this invention is achieved by providing a shock absorber fluid prepared by adding to a lubricating oil as a base oil the following ingredients as essential components
<ul id="ul0001" list-style="none" compact="compact">
<li>(A) a phosphoric acid ester and/or a phosphorous acid ester and</li>
<li>(B) an alkylene oxide adduct of an aliphatic amine.</li>
</ul></p>
<p id="p0011" num="0011">This invention will be explained below in more detail.</p>
<p id="p0012" num="0012">The lubricating oils used as a base oil in this invention are not particularly limited, and both mineral oils and synthetic oils which are usually used as a base oil for lubricating oils may be used as the base oil in this invention.</p>
<p id="p0013" num="0013">The mineral oil-type lubricating oils which may be used as a base oil, include paraffinic and naphthenic oils obtained by refining, for example, lubricating oil fractions obtained by the atmospheric and reduced-pressure distillation of a crude oil, by means of a suitable combination of solvent deasphalting, solvent extraction, hydrocracking, solvent dewaxing, catalytic dewaxing, hydrorefining, sulfuric acid washing and clay treatment.<!-- EPO <DP n="6"> --></p>
<p id="p0014" num="0014">The synthetic oil-type lubricating oils which may be used as a base oil, include poly α-olefins (polybutene, 1-octene oligomers, 1-decene oligomers, etc.), alkylbenzenes, alkylnaphthalenes, diesters (ditridecyl glutarate, di-2-ethylhexyl adipate, diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl sebacate, etc.), polyol esters (trimethylolpropane caprylate, trimethylolpropane peralgonate, pentaerithritol 2-ethyl hexanoate, pentaerithritol peralgonate, etc.), polyoxyalkylene glycol, polyphenyl ethers, silicone oil and perfluoroalkyl ethers.</p>
<p id="p0015" num="0015">The lubricating oils used as a base oil are hereinafter sometimes referred to as "base lubricating oils" for simplicity.</p>
<p id="p0016" num="0016">The base lubricating oils may be used singly or jointly, but the mineral oil-type base lubricating oils are preferably used from the standpoint of their adaptability to, or compatibility with, gum sealants in this invention.</p>
<p id="p0017" num="0017">The base lubricating oils used in this invention are optional in viscosity, but those having a viscosity of 8 - 60 cSt, preferably 10 - 40 cSt, at 40°C are usually used from necessity for their applicability to damping force required in general buffers.</p>
<p id="p0018" num="0018">The component (A) which is an essential additive to be added to a base lubricating oil according to this<!-- EPO <DP n="7"> --> invention is a phosphoric acid ester and/or a phosphorous acid ester.</p>
<p id="p0019" num="0019">The phosphoric acid ester defined here is a compound represented by the following formula (1)
<chemistry id="chem0001" num="0001"><img id="ib0001" file="imgb0001.tif" wi="89" he="43" img-content="chem" img-format="tif"/></chemistry> and the phosphorous acid ester defined here is a compound represented by the following formula (2)
<chemistry id="chem0002" num="0002"><img id="ib0002" file="imgb0002.tif" wi="93" he="30" img-content="chem" img-format="tif"/></chemistry><!-- EPO <DP n="8"> --></p>
<p id="p0020" num="0020">In the formula (1) R<sup>1</sup> and R<sup>2</sup> are each a straight-chain or branched-chain alkyl or alkenyl group having 8 - 20 carbon atoms, and R<sup>3</sup> is hydrogen; in the formula (2) R<sup>4</sup> and R<sup>5</sup> are each a straight-chain ore branched-chain alkyl or alkenyl group having 8 - 20 carbon atoms, and R<sup>6</sup> is hydrogen.</p>
<p id="p0021" num="0021">R<sup>1</sup>, R<sup>2</sup>, R<sup>4</sup> and R<sup>5</sup> each include an alkyl group such<!-- EPO <DP n="9"> --> as butyl groups (including all isomeric groups), pentyl groups (including all isomeric groups), hexyl groups (including all isomeric groups), heptyl groups (including all isomeric groups), octyl groups (including all isomeric groups), nonyl groups (including all isomeric groups), decyl groups (including all isomeric groups), undecyl groups (including all isomeric groups), dodecyl groups (including all isomeric groups), tridecyl groups (including all isomeric groups), tetradecyl groups (including all isomeric groups), pentadecyl groups (including all isomeric groups), hexadecyl groups (including all isomeric groups), heptadecyl groups (including all isomeric groups), octadecyl groups (including all isomeric groups), nonadecyl groups (including all isomeric groups), eicosyl groups (including all isomeric groups), heneicosyl groups (including all isomeric groups) and docosyl groups (including all isomeric groups); an alkenyl group such as butenyl groups (including all isomeric groups), pantenyl groups (including all isomeric groups),<!-- EPO <DP n="10"> --> hexenyl groups (including all isomeric groups), heptenyl groups (including all isomeric groups), octenyl groups (including all isomeric groups), nonenyl groups (including all isomeric groups), decenyl groups (including all isomeric groups), undecenyl groups (including all isomeric groups), dodecenyl groups (including all isomeric groups), tridecenyl groups (including all isomeric groups), tetradecenyl groups (including all isomeric groups), pentadecenyl groups (including all isomeric groups), hexadecenyl groups (including all isomeric groups), heptadecenyl groups (including all isomeric groups), octadecenyl groups (including all isomeric groups), nonadecenyl groups (including all isomeric groups), eicosenyl groups (including all isomeric groups), heneicosenyl groups (including all isomeric groups) and docosenyl groups (including all isomeric groups).<!-- EPO <DP n="11"> --></p>
<p id="p0022" num="0022">From the standpoint of excellency particularly in wear-preventing and friction-reducing effects, the phosphoric acid ester of the component (A) used in this invention is preferably a compound of the formula (1)<!-- EPO <DP n="12"> --> wherein R<sup>1</sup> and R<sup>2</sup> are each a member selected from a straight-chain alkyl or alkenyl group, and R<sup>3</sup> is hydrogen.</p>
<p id="p0023" num="0023">From the standpoint of excellency particularly in wear-preventing and friction-reducing effects in the same manner as in the phosphoric acid ester of the formula (1), the phosphorous acid ester of the component (A) used in this invention is preferably a compound of the formula (2) wherein R<sup>4</sup> and R<sup>5</sup> are each a straight-chain alkyl or alkenyl group, and R<sup>6</sup> is hydrogen.</p>
<p id="p0024" num="0024">The phosphoric acid ester which is among the components (A) used in this invention includes dioctyl acid phosphate (dicapryl acid phosphate), didecyl acid phosphate, didodecyl acid phosphate (dilauril acid<!-- EPO <DP n="13"> --> phosphate), ditetradecyl acid phosphate (dimyristyl acid phosphate), dihexadecyl acid phosphate (dipalmityl acid phosphate), dioctadecyl acid phosphate (distearyl acid phosphate) and di-9-octadecenyl acid phosphate (dioleyl phosphate). The phosphorous acid ester which is among the components (A), includes dioctyl hydrogen phosphite (dicapryl hydrogen phosphite), didecyl hydrogen phosphite, didodecyl hydrogen phosphite (dilauril hydrogen phosphite), ditetradecyl hydrogen phosphite (dimyristyl hydrogen phosphite), dihexadecyl hydrogen phosphite (dipalmityl hydrogen phosphite), dioctadecyl hydrogen phosphite (distearyl hydrogen phosphite), di-9-octadecenyl hydrogen phosphite (dioleyl hydrogen phosphite) and a mixture thereof.</p>
<p id="p0025" num="0025">In the shock absorber fluid of this invention, the amount of the phosphoric acid ester and/or phosphorous acid ester added may be arbitrary, but it is an amount of preferably 0.05 to 10% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.</p>
<p id="p0026" num="0026">Further, the component (B) which is another essential component used in this invention is an adduct of an aliphatic amine with an alkylene oxide. The alkylene oxide adduct of an aliphatic amine defined in this invention means a compound represeted by the following general formula (3)<!-- EPO <DP n="14"> -->
<chemistry id="chem0003" num="0003"><img id="ib0003" file="imgb0003.tif" wi="94" he="28" img-content="chem" img-format="tif"/></chemistry>    wherein R<sup>7</sup> represents a straight-chain or branched-chain alkyl or alkenyl group having 8 - 22 carbon atoms, R<sup>8</sup> and R<sup>9</sup> may be identical with, or different from, each other and are each a straight-chain or branched-chain alkylene group having 2 - 4 carbon atoms; and m and n may be identical with, or different from, each other and are each an integer of 0-10 with the proviso that m plus n equals 1-10, prefereably 1-5.</p>
<p id="p0027" num="0027">R<sup>7</sup> is exemplified by an alkyl group such as octyl groups (including all isomeric groups), nonyl groups (including all isomeric groups), decyl groups (including all isomeric groups), undecyl groups (including all isomeric groups), dodecyl groups (including all isomeric groups), tridecyl groups (including all isomeric groups), tetradecyl groups (including all isomeric groups), pentadecyl groups (including all isomeric groups), hexadecyl groups (including all isomeric groups), heptadecyl groups (including all isomeric groups), octadecyl groups (including all isomeric groups), nonadecyl groups (including all isomeric groups), eicosyl groups (including all isomeric groups), heneicosyl groups<!-- EPO <DP n="15"> --> (including all isomeric groups) and docosyl groups (including all isomeric groups); and an alkenyl group such as octenyl groups (including all isomeric groups), nonenyl groups (including all isomeric groups), decenyl groups (including all isomeric groups), undecenyl groups (including all isomeric groups), docenyl groups (including all isomeric groups), tridecenyl groups (including all isomeric groups), tetradecenyl groups (including all isomeric groups), pentadecenyl groups (including all isomeric groups), hexadecenyl groups (including all isomeric groups), peptadecenyl groups (including all isomeric groups), octadecenyl groups (including all isomeric groups), nonadecenyl groups (including all isomeric groups), eicosenyl groups (including all isomeric groups), heneicosenyl groups (including all isomeric groups) and docosenyl groups (including all isomeric groups). R<sup>8</sup> and R<sup>9</sup> include an ethylene group, trimethylene group, 1-methylethylene group, 2-methylethylene group, tetramethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 3-methyltrimethylene group, 1-ethylethylene group, 2-ethylethylene 1,2-dimethylethylene group, 1,1-dimethylethylene group, group and 2,2-dimethylethylene group.</p>
<p id="p0028" num="0028">The alkylene oxide adduct of an aliphatic amine, which is represented by formula (3) and is the component (B) used in this invention, is preferably a<!-- EPO <DP n="16"> --> compound of the formula (3) in which R<sup>7</sup> is a straight-chain alkyl or alkenyl group having 12-18 carbon atoms, and R<sup>8</sup> and R<sup>9</sup> are each an ethylene group, in view of excellent wear-reducing effects.</p>
<p id="p0029" num="0029">The particularly preferable alkylene oxide adducts of an aliphatic amine, which are the component (B) used in this invention, include ethylene oxide adducts of an aliphatic amine and a mixture of the adducts, and more particularly they are alkylene oxide adducts of an aliphatic amine such as octyl amine (capryl amine), decyl amine, dodecyl amine (lauril amine), tetradecyl amine (mylystyl amine), hexadecyl amine (palmitil amine), octadecyl amine (stearyl amine) or 9-octadecenyl amine (oleyl amine).</p>
<p id="p0030" num="0030">In the shock absorber fluid of this invention, the amount added of the alkylene oxide adduct of an aliphatic amine, which is the component (B), may be arbitrary, but it is desirable to add the adduct in an amount of preferably 0.05 to 10% by weight, more preferably 0.1 to 5% by weight, based on the total weight of the composition.</p>
<p id="p0031" num="0031">As described above, although the shock absorber fluid of this invention having excellent performances can be obtained by only adding to the base lubricating oil the phosphoric ester and/or phosphorous ester which is the component (A), and the alkylene oxide adduct of an aliphatic amine,<!-- EPO <DP n="17"> --> which is the component (B), into the base lubricating oil. To further enhance the thus obtained hydraulic working oil composition in such performances, heretofore known additives for lubricating oils may be used singly or jointly.</p>
<p id="p0032" num="0032">These additives include friction-reducing agents other than the components of the oil composition of this invention, such as an aliphatic alcohol, aliphatic acid, aliphatic amine and aliphatic amide; antioxidants such as phenol-, amine-, sulphur-, zinc dithiophosphate- and phenothiazine-based compounds; extreme-pressure agents such as sulfurized fats and oils, sulfides and zinc dithiophosphate; rust preventives such as petroleum sulfonates and dinonylnaphthalene sulfonate; metal deactivators such as benzotriazole and thiadiazole; metallic detergents such as alkaline earth metal sulfonates, alkaline earth metal phenates, alkaline earth metal salicylates and alkaline earth metal phosphonates; ashless dispersants such as succinic imide, succinic esters and benzyl amine; antifoaming agents such as methylsilicone and fluorosilicone; viscosity index improvers such as polymethacrylate, polyisobutylene and polystyrene; and pour point depressants.</p>
<p id="p0033" num="0033">Although the amount of these additives added may be arbitrary, the contents of the antifoaming agent, the viscosity index improver, the metal inactivator and<!-- EPO <DP n="18"> --> each of the other additives in the oil composition are ordinarily 0.0005 - 1% by weight, 1 - 30% by weight, 0.005 - 1% by weight and 0.1 - 15% by weight in this order, based on the total amount of the oil composition, respectively.</p>
<p id="p0034" num="0034">The process for preparing the hydraulic working oil compositions of this invention is not particularly limited. This process, however, may usually comprise mixing a base lubricating oil and additives including the essential components (A) and (B) together, heating the resulting mixture to 30 - 100°C and then maintaining it at this temperature under agitation for 20 minutes to 5 hours, or may comprise separately heating all the additives (solid additives having beforehand been solved in a small amount of the base lubricating oil) to 30 - 100°C, mixing these additives in portions or in full into the base lubricating oil heated to 20 - 80°C and then maintaining the resulting mixture at 30 - 100°C under agitation for 20 minutes to 5 hours.</p>
<heading id="h0005"><b><u>DESCRIPTION OF PREFERRED EMBODIMENTS</u></b></heading>
<p id="p0035" num="0035">This invention will be better understood by the non-limitative Examples and Comparative Examples.</p>
<heading id="h0006"><u>Examples 1 - 3 and Comparative Examples 1 - 4</u></heading>
<p id="p0036" num="0036">In each of the Examples, the ingredients shown in Table 1 were mixed together and the resulting<!-- EPO <DP n="19"> --> mixture was heated to 50°C under stirring for two hours thereby to prepare a hydraulic working oil composition of this invention (Examples 1 - 3). The oil compositions of this invention so prepared were subjected to a duration test using an actual device to evaluate them for their friction-reducing effects and wear-preventing effects.</p>
<p id="p0037" num="0037">Comparative hydraulic working oil compositions were prepared by following the procedure of the above Examples except that the component (A) was used singly (Comp. Example 1), except that the component (B) was used singly (Comp. Example 2), except that an aliphatic amine was substituted for the component (B) (Comp. Example 3) or except that a fatty acid was substituted for the component (A) (Comp. Example 4).</p>
<p id="p0038" num="0038">The comparative oil compositions so prepared were subjected to the same duration test as above.</p>
<heading id="h0007"><u>Duration Test Using Actual Device</u></heading>
<p id="p0039" num="0039">Using two commercially available strut-type shock absorbers, duration tests were made under the following conditions until the end of two million frequency of oscillation application. 
<tables id="tabl0001" num="0001">
<table frame="all">
<tgroup cols="2" colsep="1" rowsep="0">
<colspec colnum="1" colname="col1" colwidth="78.75mm"/>
<colspec colnum="2" colname="col2" colwidth="78.75mm"/>
<tbody valign="top">
<row>
<entry namest="col1" nameend="col1" align="left">Temperature of a test oil</entry>
<entry namest="col2" nameend="col2" align="left">80°C</entry></row>
<row>
<entry namest="col1" nameend="col1" align="left">Amount of a test oil used</entry>
<entry namest="col2" nameend="col2" align="left">330 ml/one shock absorber</entry></row>
<row>
<entry namest="col1" nameend="col1" align="left">Lateral load</entry>
<entry namest="col2" nameend="col2" align="left">200 kgf</entry></row>
<row>
<entry namest="col1" nameend="col1" align="left">Entire amplitude of oscillation applied</entry>
<entry namest="col2" nameend="col2" align="left">50 mm</entry></row>
<row rowsep="1">
<entry namest="col1" nameend="col1" align="left">Velocity of oscillation applied</entry>
<entry namest="col2" nameend="col2" align="left">0.5 m/s</entry></row></tbody></tgroup>
</table>
</tables><!-- EPO <DP n="20"> --></p>
<heading id="h0008">(1) Friction-reducing effects</heading>
<p id="p0040" num="0040">The shock absorbers were measured for their frictional coefficients at their surfaces at the time of oscillation application frequency of zero (at the initial stage of the duration test) and at the time of oscillation application frequency of two million (at the time of completion of the duration test), respectively. The frictional coefficients so measured are as shown in Table 1.</p>
<heading id="h0009">(2) Wear-preventing effects</heading>
<p id="p0041" num="0041">After the completion of the duration test, the shock absorbers were disassembled to visually evaluate the surface state of their friction surfaces (cylinders, pistons, rods and oil seals of the shock absorbers) with the results being as shown in Table 1. The degrees of the wear-preventing effects are represented in terms of six numerals 0 - 5 (numeral 5 being the best).</p>
<p id="p0042" num="0042">As is apparent from the results of the Examples, the hydraulic working oil compositions (Examples 1 - 3) are excellent in friction-reducing effects at the initial stage of the duration test and exhibit less degradation of their friction-reducing performances with the lapse of time. In addition, they exhibit less wear at the friction surfaces even at the time of end of the duration test whereby they are also excellent in wear-preventing effects.<!-- EPO <DP n="21"> --></p>
<p id="p0043" num="0043">The comparative hydraulic working oil compositions (Comp. Examples 1 - 4), on the other hand, are excellent in friction-reducing effects at the initial stage of the duration test but they exhibit much more degradation of their friction-reducing performances with the lapse of time. In addition, they are very also inferior in wear-preventing effects to those of this invention.</p>
<heading id="h0010"><u>Effects of this Invention</u></heading>
<p id="p0044" num="0044">As is apparent from the foregoing, the hydraulic working oil compositions of this invention are excellent not only in applicability to Teflon resin-impregnated bush members but also in durability (less degradation with the time) of friction-reducing effects and wear-preventing effects.<!-- EPO <DP n="22"> -->
<tables id="tabl0002" num="0002"><img id="ib0004" file="imgb0004.tif" wi="151" he="263" img-content="table" img-format="tif"/>
</tables></p>
</description><!-- EPO <DP n="23"> -->
<claims id="claims01" lang="en">
<claim id="c-en-01-0001" num="0001">
<claim-text>Shock absorber fluid comprising a lubricating oil as a base oil and (A) at least one ester selected from the group consisting of a phosphoric acid ester and a phosphorous acid ester and (B) an adduct of an aliphatic amine with an alkylene oxide as essential components, wherein the phosphoric acid ester, the phosphorous acid ester and the adduct of an aliphatic amine with an alkylene oxide are represented respectively by the following formulae (1), (2) and (3)
<chemistry id="chem0004" num="0004"><img id="ib0005" file="imgb0005.tif" wi="96" he="26" img-content="chem" img-format="tif"/></chemistry>
<chemistry id="chem0005" num="0005"><img id="ib0006" file="imgb0006.tif" wi="94" he="19" img-content="chem" img-format="tif"/></chemistry> and
<chemistry id="chem0006" num="0006"><img id="ib0007" file="imgb0007.tif" wi="95" he="17" img-content="chem" img-format="tif"/></chemistry><!-- EPO <DP n="24"> --> wherein in the formula (1) the R<sup>1</sup> and R<sup>2</sup> are each a straight-chain or branched-chain alkyl or alkenyl group having 8 - 20 carbon atoms, and R<sup>3</sup> is hydrogen; in the formula (2) the R<sup>4</sup> and R<sup>5</sup> are each a straight-chain or branched-chain alkyl or alkenyl group having 8 - 20 carbon atoms, and the R<sup>6</sup> is hydrogen; and in the formula (3) the R<sup>7</sup> is a straight-chain or branched-chain alkyl or alkenyl group having 8 - 22 carbon atoms, and the R<sup>8</sup> and R<sup>9</sup> may be identical with, or different from, each other and they are each a straight-chain or branched-chain alkylene group having 2 - 4 carbon atoms; m and n may be identical with, or different from, each other and they are each an integer of 0-10 with the proviso that m plus n equals 1-10.</claim-text></claim>
<claim id="c-en-01-0002" num="0002">
<claim-text>Shock absorber fluid according to claim 1, wherein said R<sup>1</sup>, R<sup>2</sup>, R<sup>4</sup> and R<sup>5</sup> are each a straight-chain alkyl or alkenyl group.</claim-text></claim>
<claim id="c-en-01-0003" num="0003">
<claim-text>Shock absorber fluid according to claim 1, wherein the phosphoric acid ester is dioctyl acid phosphate (dicapryl acid phosphate), didecyl acid phosphate, didodecyl acid phosphate (dilauryl acid phosphate), ditetradecyl acid phosphate (dimyristyl acid phosphate), dihexadecyl acid phosphate (dipalmityl acid phosphate), dioctadecyl acid phosphate (distearyl acid phosphate) and di-9-octadecenyl acid phosphate (dioleyl acid phosphate) or a mixture thereof; the phosphorous acid ester is dioctyl hydrogen phosphite (dicapryl hydrogen phosphite), didecyl hydrogen phosphite, didodecyl hydrogen phosphite (dilauryl hydrogen phosphite), ditetradecyl hydrogen phosphite (dimyristyl hydrogen phosphite), dihexadecyl hydrogen phosphite (dipalmityl hydrogen phosphite), dioctadecyl hydrogen phosphite (distearyl hydrogen phosphite), di-9-octadecenyl hydrogen phosphite (dioleyl hydrogen phosphite) or a mixture thereof; and the alkylene oxide adduct of an aliphatic amine is an ethylene oxide adduct of octyl amine (capryl amine), decyl amine, dodecyl amine (lauryl amine), tetradecyl amine (mylystyl amine), hexadecyl amine (palmityl amine),<!-- EPO <DP n="25"> --> octadecyl amine (stearyl amine) or 9-octadecenyl amine (oleyl amine).</claim-text></claim>
<claim id="c-en-01-0004" num="0004">
<claim-text>Shock absorber fluid according to any one of claims 1 to 3, wherein said R<sup>7</sup> is a straight-chain alkyl or alkenyl group having 12 - 18 carbon atoms.</claim-text></claim>
<claim id="c-en-01-0005" num="0005">
<claim-text>Shock absorber fluid according to any one of claims 1 to 4, wherein said R<sup>8</sup> and R<sup>9</sup> are each an ethylene group.</claim-text></claim>
<claim id="c-en-01-0006" num="0006">
<claim-text>Shock absorber fluid according to claims 1 to 5, wherein the m plus n equals 1 - 5.</claim-text></claim>
<claim id="c-en-01-0007" num="0007">
<claim-text>Shock absorber fluid according to any one of claims 1 to 6, wherein the base oil is a paraffinic or naphthenic oil refined by subjecting lubricating oil fractions produced by the atmospheric and reduced-pressure distillation of a crude oil to refining steps selected from solvent deasphalting, solvent extraction, hydrocracking, solvent dewaxing, catalytic dewaxing, hydrorefining, sulfuric washing and clay treatment, or is a synthetic oil selected from the group consisting of polybutene, 1-octene oligomers, 1-decene oligomers, alkylbenzenes, alkylnaphthalenes, tridecyl glutarate, di-2-ethylhexyl adipate, diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl sebacate, trimethylolpropane caprilate, trimethylolpropane peralgonate, pentaerithritol 2-ethyl hexanoate, pentaerithritol peralgonate, polyoxyalkylene glycol, polyphenyl ethers, silicone oil and perfluoroalkyl ethers.</claim-text></claim>
<claim id="c-en-01-0008" num="0008">
<claim-text>Shock absorber fluid according to any one of claims 1 to 7, wherein the base oil has a viscosity of 8 - 60 cSt at 40°C.<!-- EPO <DP n="26"> --></claim-text></claim>
<claim id="c-en-01-0009" num="0009">
<claim-text>Shock absorber fluid according to any one of claims 1 to 8, wherein the phosphoric acid ester and/or phosphorous acid ester is added to the base oil in an amount of 0.05 - 10% by weight of the total amount of the oil composition, and the alkylene oxide adduct of an aliphatic amine is added to the base oil in an amount of 0.05 - 10% by weight of the total amount of the oil composition.</claim-text></claim>
<claim id="c-en-01-0010" num="0010">
<claim-text>Preparation of a shock absorber fluid described in at least one of the foregoing claims 1 to 9, by adding component (A) and component (B) to the basis oil.</claim-text></claim>
<claim id="c-en-01-0011" num="0011">
<claim-text>Use of the fluid, comprising the basis oil, component (A) and component (B), described in at least one of the claims 1 to 9, as shock absorber fluid.</claim-text></claim>
</claims><!-- EPO <DP n="27"> -->
<claims id="claims02" lang="de">
<claim id="c-de-01-0001" num="0001">
<claim-text>Stoßdämpferflüssigkeit, enthaltend ein Schmieröl als Basisöl und (A) wenigstens einen Phosphorsäureester und/oder einen Ester einer phosphorigen Säure und (B) ein Addukt eines aliphatischen Amins mit einem Alkylenoxid als wesentliche Komponenten, wobei der Phosphorsäureester, der Ester der phosphorigen Säure und das Addukt eines aliphatischen Amins mit einem Alkylenoxid jeweils den folgenden Formeln (1), (2) und (3) entsprechen
<chemistry id="chem0007" num="0007"><img id="ib0008" file="imgb0008.tif" wi="100" he="27" img-content="chem" img-format="tif"/></chemistry>
<chemistry id="chem0008" num="0008"><img id="ib0009" file="imgb0009.tif" wi="100" he="20" img-content="chem" img-format="tif"/></chemistry> and
<chemistry id="chem0009" num="0009"><img id="ib0010" file="imgb0010.tif" wi="100" he="17" img-content="chem" img-format="tif"/></chemistry> wobei in Formel (1) R<sup>1</sup> und R<sup>2</sup> jeweils eine geradkettige oder verzweigtkettige Alkyl- oder Alkenylgruppe mit 8 bis 20 Kohlenstoffatomen und R<sup>3</sup> Wasserstoff sind; in Formel (2) R<sup>4</sup> und R<sup>5</sup> jeweils eine geradkettige oder verzweigtkettige Alkyl- oder Alkenylgruppe mit 8 bis 20 Kohlenstoffatomen und R<sup>6</sup> Wasserstoff sind; und in Formel (3) R<sup>7</sup> eine geradkettige oder verzweigtkettige Alkyl- oder Alkenylgruppe mit 8 bis 22 Kohlenstoffatomen und R<sup>8</sup> und R<sup>9</sup> gleich oder verschieden voneinander<!-- EPO <DP n="28"> --> sein können und jeweils eine geradkettige oder verzweigtkettige Alkylengruppe mit 2 bis 4 Kohlenstoffatomen sind; m und n gleich oder verschieden voneinander sein können und jeweils eine ganze Zahl von 0 bis 10 sind, unter der Voraussetzung, daß m plus n 1-10 ist.</claim-text></claim>
<claim id="c-de-01-0002" num="0002">
<claim-text>Stoßdämpferflüssigkeit gemäß Anspruch 1, wobei R<sup>1</sup>, R<sup>2</sup>, R<sup>4</sup> und R<sup>5</sup> jeweils eine geradkettige Alkyl- oder Alkenylgruppe sind.</claim-text></claim>
<claim id="c-de-01-0003" num="0003">
<claim-text>Stoßdämpferflüssigkeit gemäß Anspruch 1, wobei der Phosphorsäureester Dioctylsäurephosphat (Dicaprylsäurephosphat), Didecylsäurephosphat, Didodecylsäurephosphat (Dilaurylsäurephosphat), Ditetradecylsäurephosphat (Dimyristylsäurephosphat), Dihexadecylsäurephosphat (Dipalmitylsäurephosphat), Dioctadecylsäurephosphat (Distearylsäurephosphat) oder Di-9-octadecenylsäurephosphat (Dioleylsäurephosphat) oder eine Mischung davon; der Ester der phosphorigen Säure Diocytlwasserstoffphosphit (Dicaprylwasserstoffphosphit), Didecylwasserstoffphosphit, Didodecylwasserstoffphosphit (Dilaurylwasserstoffphosphit), Ditetradecylwasserstoffphosphit (Dimyristylwasserstoffphosphit), Dihexadecylwasserstoffphosphit (Dipalmitylwasserstoffphosphit), Dioctadecylwasserstoffphosphit (Distearylwasserstoffphospit), Di-9-octadecenylwasserstoffphosphit (Dioleylwasserstoffphosphit) oder eine Mischung davon; und das Alkylenoxidaddukt eines aliphatischen Amins ein Ethylenoxidaddukt von Octylamin (Caprylamin), Decylamin, Dodecylamin (Laurylamin), Tetradecylamin (Mylystylamin), Hexadecylamin (Palmitylamin), Octadecylamin (Stearylamin) oder 9-Octadecenylamin (Oleylamin) sind.</claim-text></claim>
<claim id="c-de-01-0004" num="0004">
<claim-text>Stoßdämpferflüssigkeit nach wenigstens einem der Ansprüche 1 bis 3, wobei R<sup>7</sup> eine geradkettige Alkyl- oder<!-- EPO <DP n="29"> --> Alkenylgruppe mit 12 bis 18 Kohlenstoffatomen ist.</claim-text></claim>
<claim id="c-de-01-0005" num="0005">
<claim-text>Stoßdämpferflüssigkeit nach wenigstens einem der Ansprüche 1 bis 4, wobei R<sup>8</sup> und R<sup>9</sup> jeweils eine Ethylengruppe sind.</claim-text></claim>
<claim id="c-de-01-0006" num="0006">
<claim-text>Stoßdämpferflüssigkeit nach wenigstens einem der Ansprüche 1 bis 5, wobei m plus n 1-5 ist.</claim-text></claim>
<claim id="c-de-01-0007" num="0007">
<claim-text>Stoßdämpferflüssigkeit nach mindestens einem der Ansprüche 1 bis 6, wobei das Basisöl ein paraffinisches oder naphthenisches Öl ist, das raffiniert wurde, indem Schmierölfraktionen, hergestellt durch atmosphärische und druckverminderte Destillation eines Rohöls, einer oder mehreren der folgenden Raffinierungsstufen unterzogen wurden: Lösungsmittel-Deasphaltierung, Lösungsmittel-Extraktion, Hydrokracken, Lösungsmittel-Entparaffinieren, katalyisches Entparaffinieren, Hydroraffinieren, Sulfatwäsche und/oder Tonerdebehandlung, oder eines der synthetischen Öle Polybuten, 1-Octenoligomer, 1-Decenoligomer, Alkylbenzen, Alkylnaphthalen, Tridecylglutarat, Di-2-ethylhexyladipat, Diisodecyladipat, Ditridecyladipat, Di-2-ethylhexylsebacat, Trimethylolpropancaprylat, Trimethylolpropanperalgonat, Pentaerithrit-2-ethylhexanoat, Pentaerithritolperalgonat, Polyoxyalkylenglykol, Polyphenylether, Silikonöl und/oder Perfluoralkylether ist.</claim-text></claim>
<claim id="c-de-01-0008" num="0008">
<claim-text>Stoßdämpferflüssigkeit nach wenigstens einem der Ansprüche 1 bis 7, wobei das Basisöl eine Viskosität von 8 bis 60 cSt bei 40 °C aufweist.</claim-text></claim>
<claim id="c-de-01-0009" num="0009">
<claim-text>Stoßdämpferflüssigkeit nach wenigstens einem der Ansprüche 1 bis 8, wobei der Phosphorsäureester und/oder der Ester der phosphorigen Säure zu dem Basisöl in einer Menge<!-- EPO <DP n="30"> --> von 0,05 bis 10 Gew.-% der Gesamtmenge der Ölzusammensetzung und das Alkylenoxidaddukt eines aliphatischen Amins zu dem Basisöl in einer Menge von 0,05 bis 10 Gew.-% der Gesamtmenge der Ölzusammensetzung gegeben werden.</claim-text></claim>
<claim id="c-de-01-0010" num="0010">
<claim-text>Herstellung einer Stoßdämpferflüssigkeit gemäß wenigstens einem der vorhergehenden Ansprüche 1 bis 9 durch Zugabe der Komponente (A) und der Komponente (B) zu dem Basisöl.</claim-text></claim>
<claim id="c-de-01-0011" num="0011">
<claim-text>Verwendung des Fluids gemäß wenigstens einem der Ansprüche 1 bis 9, welches das Basisöl, Komponente (A) und Komponente (B) enthält, als Stoßdämpferflüssigkeit.</claim-text></claim>
</claims><!-- EPO <DP n="31"> -->
<claims id="claims03" lang="fr">
<claim id="c-fr-01-0001" num="0001">
<claim-text>Fluide absorbeur de choc comprenant une huile lubrifiante en tant qu'huile de base et (A) au moins un ester choisi dans le groupe formé par un ester d'acide phosphorique et un ester d'acide phosphoreux et (B) un produit d'addition d'une amine aliphatique avec un oxyde d'alkylène comme composants essentiels, dans lequel l'ester d'acide phosphorique, l'ester d'acide phosphoreux et le produit d'addition d'une amine aliphatique avec un oxyde d'alkylène sont représentés respectivement par les formules suivantes (1), (2) et (3)
<chemistry id="chem0010" num="0010"><img id="ib0011" file="imgb0011.tif" wi="97" he="25" img-content="chem" img-format="tif"/></chemistry>
<chemistry id="chem0011" num="0011"><img id="ib0012" file="imgb0012.tif" wi="88" he="19" img-content="chem" img-format="tif"/></chemistry> et
<chemistry id="chem0012" num="0012"><img id="ib0013" file="imgb0013.tif" wi="100" he="26" img-content="chem" img-format="tif"/></chemistry> dans lesquelles dans la formule (1), les R<sup>1</sup> et R<sup>2</sup> sont chacun un groupe alcényle ou alkyle à chaîne droite ou ramifiée ayant 8 à 20 atomes de carbone, et R<sup>3</sup> est un atome d'hydrogène; dans la formule (2), les R<sup>4</sup> et R<sup>5</sup> sont chacun un groupe alkyle ou alcényle à chaîne droite ou ramifiée ayant 8 à 20 atomes de carbone, et R<sup>8</sup> est un atome d'hydrogène; et dans la formule (3), R<sup>7</sup> est un groupe alkyle ou alcényle à chaîne droite ou ramifié ayant 8 à 22 atomes de carbone, et les R<sup>8</sup> et R<sup>9</sup> peuvent être identiques ou différents l'un de l'autre et ils sont chacun un groupe alkylène à chaîne droite<!-- EPO <DP n="32"> --> ou ramifiée ayant 2 à 4 atomes de carbone; m et n peuvent être identiques ou différents l'un de l'autre et ils sont chacun un nombre entier de 0 à 10 à condition que m plus n vaillent de 1 à 10.</claim-text></claim>
<claim id="c-fr-01-0002" num="0002">
<claim-text>Fluide absorbeur de choc selon la revendication 1, dans lequel lesdits R<sup>1</sup>, R<sup>3</sup>, R<sup>4</sup> et R<sup>5</sup> sont chacun un groupe alcényle ou alkyle à chaîne droite.</claim-text></claim>
<claim id="c-fr-01-0003" num="0003">
<claim-text>Fluide absorbeur de choc selon la revendication 1, dans lequel l'ester d'acide phosphorique est le phosphate acide de dioctyle (phosphate acide de dicapryle), le phosphate acide de didécyle, le phosphate acide de didodécyle (phosphate acide de dilauryle), le phosphate acide de ditétradécyle (phosphate acide de dimyristyle), le phosphate acide de dihexadécyle (phosphate acide de dipalmityle), le phosphate acide de dioctadécyle (phosphate acide de di-stéaryle) et le phosphate acide de di-9-octadécényle (phosphate acide de dioléyle) ou un de leurs mélanges; l'ester d'acide phosphoreux est l'hydrogénophosphite de dioctyle (hydrogénophosphite de dicapryle), l'hydrogénophosphite de didécyle, l'hydrogénophosphite de didodécyle (hydrogénophosphite de dilauryle), l'hydrogénophosphite de ditétradécyle (hydrogénophosphite de dimyristyle), l'hydrogénophosphite de dihexadécyle (hydrogénophosphite de dipalmityle), l'hydrogénophosphite de dioctadécyle (hydrogénophosphite de distéaryle), l'hydrogénophosphite de di-9-octadécényle (hydrogénophosphite de dioléyle) ou un de leurs mélanges; et un produit d'addition d'oxyde d'éthylène avec l'octylamine (caprylamine), la décylamine, la dodécyl-amine (laurylamine), la tétradécylamine (myrystylamine), l'hexadécylamine (palmitylamine), l'octadécylamine (stéarylamine) ou la 9-octadécénylamine (oléylamine).</claim-text></claim>
<claim id="c-fr-01-0004" num="0004">
<claim-text>Fluide absorbeur de choc selon l'une quelconque des revendications 1 à 3, dans lequel ledit R<sup>7</sup> est un groupe alkyle ou alcényle à chaîne droite ayant 12 à 18 atomes de carbone.<!-- EPO <DP n="33"> --></claim-text></claim>
<claim id="c-fr-01-0005" num="0005">
<claim-text>Fluide absorbeur de choc selon l'une quelconque des revendications 1 à 4, dans lequel lesdits R<sup>8</sup> et R<sup>9</sup> sont chacun un groupe éthylène.</claim-text></claim>
<claim id="c-fr-01-0006" num="0006">
<claim-text>Fluide absorbeur de choc selon les revendications 1 à 5, dans lequel m plus n valent de 1 à 5.</claim-text></claim>
<claim id="c-fr-01-0007" num="0007">
<claim-text>Fluide absorbeur de choc selon l'une quelconque des revendications 1 à 6, dans lequel l'huile de base est une huile naphténique ou paraffinique raffinée en soumettant des fractions d'huile lubrifiante produites par la distillation sous pression atmosphérique et réduite d'un pétrole brut à des étapes de raffinage choisies parmi le désasphaltage au solvant, l'extraction au solvant, l'hydrocraquage, le décirage au solvant, le décirage catalytique, l'hydroraffinage, le lavage à l'acide sulfurique et le traitement par l'argile, ou bien c'est une huile synthétique choisie dans le groupe formé par le polybutène, les oligomères de 1-octène, les oligomères de 1-décène, les alkylbenzènes, les alkylnaphtalènes, le glutarate de tridécyle, l'adipate de di-2-éthylhexyle, l'adipate de diisodécyle, l'adipate de ditridécyle, le sébacate de di-2-éthylhexyle, le caprylate de triméthylolpropane, le péralgonate de triméthylolpropane, le 2-éthylhexanoate de pentaérithritol, le péralgonate de pentaérithritol, le polyoxyalkylèneglycol, les poly(éthers phényliques), l'huile de silicone et les éthers perfluoroalkyliques.</claim-text></claim>
<claim id="c-fr-01-0008" num="0008">
<claim-text>Fluide absorbeur de choc selon l'une quelconque des revendications 1 à 7, dans lequel l'huile de base a une viscosité de 8 à 60 cSt à 40°C.<!-- EPO <DP n="34"> --></claim-text></claim>
<claim id="c-fr-01-0009" num="0009">
<claim-text>Fluide absorbeur de choc selon l'une quelconque des revendications 1 à 8, dans lequel l'ester d'acide phosphorique et/ou l'ester d'acide phosphoreux sont ajoutés à l'huile de base à raison de 0,05 à 10% en poids de la quantité totale de la composition d'huile, et on ajoute le produit d'addition d'oxyde d'alkylène avec une amine aliphatique à l'huile de base à raison de 0,05 à 10% en poids de la quantité totale de la composition d'huile.</claim-text></claim>
<claim id="c-fr-01-0010" num="0010">
<claim-text>Préparation d'un fluide absorbeur de choc décrit dans au moins une des revendications précédentes 1 à 9, en ajoutant le composant (A) et le composant (B) à l'huile de base.</claim-text></claim>
<claim id="c-fr-01-0011" num="0011">
<claim-text>Utilisation du fluide, comprenant l'huile de base, le composant (A) et le composant (B), décrits dans au moins une des revendications 1 à 9, en tant que fluide absorbeur de choc.</claim-text></claim>
</claims>
</ep-patent-document>
