CA1232263A - Power transmission shift fluids containing two- component friction modifier additive - Google Patents

Power transmission shift fluids containing two- component friction modifier additive

Info

Publication number
CA1232263A
CA1232263A CA000441897A CA441897A CA1232263A CA 1232263 A CA1232263 A CA 1232263A CA 000441897 A CA000441897 A CA 000441897A CA 441897 A CA441897 A CA 441897A CA 1232263 A CA1232263 A CA 1232263A
Authority
CA
Canada
Prior art keywords
component
alkanol
bis
thio
succinic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000441897A
Other languages
French (fr)
Inventor
Harold E. Deen
Jack Ryer
William K.S. Cleveland
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Application granted granted Critical
Publication of CA1232263A publication Critical patent/CA1232263A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20Thiols; Sulfides; Polysulfides
    • C10M135/22Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M135/24Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/02Bearings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE

There are disclosed functional fluid compositions containing a two component friction modifier additive composed of a thio-bis-alkanol succinate ester and a phos-phate diester such as dioleyl phosphite. The compositions are especially useful as tractor fluids.

Description

~32.~

1 The present invention relates to functional fluid
2 compositions containing a two-component ester additive thereby
3 providing to functional fluid or power transmitting oleaginous
4 compositions, such as hydraulic fluids or automatic trays-s mission fluids (ATF),useful friction modification proprieties More particularly, the invention relates to the 7 use of moo- and divesters of Thebes alkanols and alkenyl 8 succinic acid or androids in combination with phosphate 9 esters which are especially effective as friction modifier lo additives for tractor hydraulic f lids.
11 US. Patent 4,344j853discloses that the esters I Of trio bis-alkanols and alkenyl succinic acid or android 13 do have useful friction properties. These are the same 14 materials which form one component of the two-component system of the present invention.
16 In accordance with the present invention, there 17 are provided mineral oil compositions useful as power trays-18 mission shift fluids containing a two-component additive in lo an amount effective to improve the friction characteristics of said composition, the first component being (i) a sue-21 Senate moo or dip ester, or mixture thereof, formed by 22 the reaction of (a) thio-bis-alkanols of the formula:

24 H ~OCH-(C~2)a So t (SCHICK H

26 wherein R and R' each independently may be hydrogen, methyl 27 or ethyl, x may be 1-4, a, b, c, and d each independently may 28 be 1-3; with (b) 1 to 2 moles, per mole of the Thebes-29 alkanol, of an aliphatic hydrocarbon-substituted succinic acid or android or mixtures thereof wherein the aliphatic 31 hydrocarbon group contains from 12 to 50 carbon atoms and the 32 second component being (ii) a phosphate divester of the 33 formula (R"0)2P(:O)H where R" is an alkyd or alkenyl group 34 of 6 to 20 carbon atoms.
us As used herein with respect to said first come 36 potent, the term "monster" or "hamster" refers to 37 product made from equimolar proportions of said Thebes-38 alkanol and a succinic acid or android, that is, one free ~%~

1 hydroxyl group remains; while the term "divester" refers to 2 those products wherein each hydroxyl group of the Thebes-3 alkanol is esterified with a hydrocarbyl substituted or 4 polyolefin-substituted succinlc acid or android. In either case, a succinic acid moiety remains, i.e., a -COY
6 group.
7 The relative amounts of the first and second 8 components are such that the ratio in parts by weight of the 9 succinate ester first component to phosphate divester second component it from about 2:1 to 1:2, preferably 1:1.
11 The hydrocarbyl-succinic acids or androids for 12 preparing the first component are per so known in the art and 13 the commonly used android may be represented by the 14 formula:
R"' SCHICK
I

17 wherein R''' is a C12-Cso aliphatic hydrocarbon group, such 18 as an alkyd, alkenyl, isoalkyl, isoalkenyl or cycloalkyl 19 hydrocarbyl group. Oligomers containing 12 to 50 carbon atoms are also suitable as the aliphatic hydrocarbyl group, 21 such as oligomers of C2-Cs monoolefins, such as isobutene.
22 The aliphatic hydrocarbyl group may be an us-23 substituted hydrocarbon group or it may contain substituents24 such as chlorine, bromide, sulfur, phosphorous, nitrogen or I oxygen which will not affect the utility of the final moo-26 or dip ester product. A preferred substituent is sulfur as 27 exemplified by 2-octadecylthio succinic android.
28 The thio-bis-alkanol useful in forming the sue-29 Senate ester first component includes those ester-forming dill compounds of the formula:

31 H t Shea ox t (SCHICK COO

I

1 wherein R and I each independently may be hydrogen, methyl 2 or ethyl, x may be 1-4, a, b, c and d each independently may 3 be 1-3. If b or d are greater than 1, then the formula is 4 meant to express ethoxylated derivatives of such alcohols.
Preferred embodiments are those thio-bis-alkanols 6 within the foregoing formula herein a, b, c and d are 7 each 1 or 2 and R is H or SHEA. Specific compounds include 8 2,2'-dithiodiethanol 2,2' thiodiethanol, do (2-hydroxypro-9 Pyle disulfide and 3,3'-thiodipropanol.
Formation of these moo and divesters pro-11 coeds by reacting the appropriate quantities of android 12 (or acid) and thio-bis-alkanol with or without an inert 13 organic solvent delineate and heating and stirring the mixture 14 at about 50 to 150C until esterification of the android 15 is complete. Equimolar quantities of each reactant will 16 provide mainly the moo- (or hem-) ester and reaction of 2 17 moles of hydrocarbon substituted succinic acid or android 18 per mole ox trio bis-alkanol will provide the divester 19 material. Also, products useful in the present invention 20 encompass mixtures of such moo- and dip esters.
21 Insofar as yields are concerned, the reaction of 22 an equimolar ratio of thio-bis-alkanol and hydrocarbon 23 succinic android will provide a product containing about 24 80% monster and about 20% divester. The divester is 25 produced in somewhat higher yields, about 90% of the product 26 being divester and about 10% monster when the mole ratio 27 of succinic android to thio-bis-alkanol is 2:1. The dip 28 ester compounds exhibit generally bette~~f~iction pro-29 parties.
In the case of a divester compound it is suitable 31 to use SUCCilliC androids hiving less than C12 hydrocarbon 32 substituent so long as the total number of carbon atoms of 33 the hydrocarbon substituents on the succinic moiety of the 34 ester compounds is at least C12 since oil volubility of the finished compound is the important property.
36 The second component of the friction modifier 37 additive of the present invention is a phosphate divester of -4- Jo 1 the formula (ROY POW where R may be an alkyd or alkenyl 2 group having about 6 to 20 carbon atoms and preferably about 3 it to 18 carbon atoms. Particularly preferred is Delilah 4 phosphate. These phosphate ester compounds are, per so,
5 well known in the art, and may be prepared by conventional
6 techniques. Examples of all other suitable phosphate dip
7 osiers are distearyl phosphate, di-2-ethylhexyl phosphate,
8 dicyclodecyl phosphate as well as phosphate divesters of
9 mixed fatty alcohols, such as Seattle, stroll and oilily alcohols, or tallow alcohols (C16-Clg fatty alcohols).
11 The particularly preferred embodiment of the pro-12 sent invention is a two component system composed of about 13 equal parts by weigh of 2,2'-thiodiethylbis (octadecenyl-14 succinic acid ester) as the first component and Delilah 15 phosphate as the second component.
16 The two-component system of the present invention 17 has been found to exhibit a synergistic effect upon friction 18 characteristics compared with either component used spear-19 lately at equivalent additive concentration levels. The additive system of this invention is especially useful in 21 functional fluids such as tractor hydraulic fluids which use 22 oil-immersed brakes and power takeoff clutches running in a 23 common oft supply with the transmission. Frictional char-24 acteristics of the fluid are important to meet the demands 25 of noiseless braking and power takeoff clutch capacity to 26 provide effective frictional coupling of two or more us-27 connected surfaces that are immersed or in contact with 28 the functional fluid.
29 The compositions of the present invention Wylie contain the two-component additive in amounts effective to 31 provide the desirable properties of friction modification 32 or retention to the power transmitting fluid. generally 33 there will be present 0.05 to 2 White of the two component 34 additive based on the total weight of the composition, 35 preferably there is employed about 0.1 to 1 5 wit% of the two-36 component additive in the hydrocarbon mineral oil fluid, 37 such as a tractor hydraulic fluid which is the preferred 38 Composition 39 Power transmission shift fluids are those functional I I

1 fluid compositions such as automatic transmission fluids, 2 power steering and brake fluids, hydraulic fluids and such 3 compositions contain a number of conventional additives 4 providing their normal attendant functions and are typical-5 lye blended into the mineral oil base in the following ranges:
6 Components Concentration Range (Vol. %) 7 V.I. Improver 1 - 15 8 Corrosion Inhibitor 0.01 - 1 9 oxidation Inhibitor Cool Dispersant 0.5 - 10 11 Pour point Depressant Oily - 1 12 Emulsifier 0.001 - Owl 13 Anti-Foaming Agents Oily - Owl 14 Anti-Wear Agents ~:.001 Seal Silent 0.1 - 5 16 Friction Modifies Oily l 17 Mineral Oil Base Balance 18 Typical base oils for hydraulic and other power trays-19 mission shift fluids include a wide variety of light 20 hydrocarbon mineral oils, such as, naphthenic base, paraffin 21 base and mixtures thereof, having a lubricating viscosity 22 range of about 34 to 45 SUP (Sublet Universal Seconds) at 23 38C.
24 The invention is further illustrated by the following 25 examples which are not to be considered as limitative of its 26 scope. Hydraulic fluids used in the following examples were 27 formulated in accordance with the components and concentra-28 lions noted above and are referred to as Base Fluid.

32~3 2 To samples of a Base Fluid useful as a tractor 3 hydraulic fluid was added 1% by weight of friction modifier 4 additives A, B and C listed below to provide three separate fluids:
6 Additive A: Delilah Phosphate 7 Additive B: 2,21-thiodiethylbis (oc~adecenyl 8 succinic acid ester) g Additive C: A mixture of 50% by weight A
and 50~ by weight B
11 The friction characteristics of the three fluids 12 were evaluated using the SUE #2 friction machine which 13 evaluates torque transfer and reports the values which is 14 the change in torque in lb-ft-as a function of time. The 15 results were:
16 Fluid US
17 Additive A, 1 White 9 18 additive B, 1 wit% 12 19 Additive C, 1 White 6 Lower values fox US in this test, ire less than 21 about 10, indicate improvement in frictional properties;
22 the two-component system of the invention exhibits a saner-23 fistic effect when compared with the same components used 24 separately at the same 1 wit% concentration level in the same 25 Base Fluid.

Claims (7)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A power transmission shift fluid composition comprising a mineral oil base containing a two-component additive in an amount effective to improve the friction characteristics of the fluid composition, the first com-ponent being (i) a succinate ester formed by the reaction of:
(a) a thio bis-alkanol of the formula:

wherein R and R' each independently may be hydrogen, methyl or ethyl, x may be 1-4, and a, b, c, d, each may be independently 1-3, with (b) 1 to 2 moles, per mole of the thio-bis-alkanol, or an aliphatic hydrocarbon-substituted succinic acid or anhydride wherein the aliphatic hydrocar-bon group contains from 12 to 50 carbon atoms, and the second component being (ii) a phosphite diester of the formula (R"0)2 P(O)H where R" is an alkyl or alkenyl group of 6 to 20 carbon atoms.
2. The composition of claim 1 wherein there is present 0.05 to 2.0 weight percent of said two-component additive and the weight ratio of said first component to said second component is about 1:2 to 2:1.
3. A composition according to claim 1 wherein the first component is formed by the reaction of 1 mole of said hydrocarbon succinic acid or anhydride per mole of said thio-bis-alkanol.
4. A composition according to claim 1 wherein the first component is formed by the reaction of 2 moles of said hydrocarbon succinic acid or anhydride per mole of said thio-bis-alkanol.
5. A composition according to claim 1 wherein said R' of said second component has 12 to 18 carbon atoms.
6. A composition according to claim 2 wherein said composition is a tractor fluid composition.
7. A composition according to claim 6 wherein said first component is 2,2'-thiodiethylbis(octadecenyl-succinic acid ester) and said second component is dioleyl phosphite.
CA000441897A 1982-12-27 1983-11-24 Power transmission shift fluids containing two- component friction modifier additive Expired CA1232263A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45312182A 1982-12-27 1982-12-27
US453,121 1982-12-27

Publications (1)

Publication Number Publication Date
CA1232263A true CA1232263A (en) 1988-02-02

Family

ID=23799292

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000441897A Expired CA1232263A (en) 1982-12-27 1983-11-24 Power transmission shift fluids containing two- component friction modifier additive

Country Status (3)

Country Link
EP (1) EP0113199B1 (en)
CA (1) CA1232263A (en)
DE (1) DE3377504D1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0251591A (en) * 1988-06-24 1990-02-21 Exxon Chem Patents Inc Synergic combination of additives useful in power transmitting composition
US5284591A (en) * 1991-05-15 1994-02-08 The Lubrizol Corporation Functional fluid with borated epoxides, carboxylic solubilizers, zinc salts, calcium complexes and sulfurized compositions
US5635459A (en) * 1995-10-27 1997-06-03 The Lubrizol Corporation Borated overbased sulfonates for improved gear performance in functional fluids

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3583915A (en) * 1968-07-22 1971-06-08 Mobil Oil Corp Load carrying additives
US4344853A (en) * 1980-10-06 1982-08-17 Exxon Research & Engineering Co. Functional fluid containing metal salts of esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols as antioxidants

Also Published As

Publication number Publication date
DE3377504D1 (en) 1988-09-01
EP0113199A2 (en) 1984-07-11
EP0113199A3 (en) 1986-02-12
EP0113199B1 (en) 1988-07-27

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