CA2112775A1 - Polyphenylene ether lubricant containing hydrocargyl bis(dihydrocarbylphosphate) compound - Google Patents
Polyphenylene ether lubricant containing hydrocargyl bis(dihydrocarbylphosphate) compoundInfo
- Publication number
- CA2112775A1 CA2112775A1 CA002112775A CA2112775A CA2112775A1 CA 2112775 A1 CA2112775 A1 CA 2112775A1 CA 002112775 A CA002112775 A CA 002112775A CA 2112775 A CA2112775 A CA 2112775A CA 2112775 A1 CA2112775 A1 CA 2112775A1
- Authority
- CA
- Canada
- Prior art keywords
- lubricant
- compound
- polyphenylene ether
- bis
- dihydrocarbylphosphate
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
- C10M2209/1013—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/102—Polyesters
- C10M2209/1023—Polyesters used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Abstract
POLYPHENYLENE ETHER LUBRICANT CONTAINING
HYDROCARBYL BIS(DIHYDROCARBYLPHOSPHATE) COMPOUND
ABSTRACT OF THE DISCLOSURE
Polyphenylene ether-based lubricant compositions can be improved in regard to anti-wear properties by inclusion of a hydrocarbyl bis(dihydrocarbylphosphate) compound, for example, at up to about 10% by weight. The preferred compounds contain a hydrocarbyl group derived from a monoaromatic diol such as resorcinol or hydroquinone and are diphenylphosphate species.
HYDROCARBYL BIS(DIHYDROCARBYLPHOSPHATE) COMPOUND
ABSTRACT OF THE DISCLOSURE
Polyphenylene ether-based lubricant compositions can be improved in regard to anti-wear properties by inclusion of a hydrocarbyl bis(dihydrocarbylphosphate) compound, for example, at up to about 10% by weight. The preferred compounds contain a hydrocarbyl group derived from a monoaromatic diol such as resorcinol or hydroquinone and are diphenylphosphate species.
Description
2 ~ 7 7 ~
1 ACA 5737 :~
POLYPHENYLENE ETHER LUBRICANT CONTAINING
HYDROCARBYL BIS(DIHYDROCARBYLPHOSPHATE) COMPOUND
BACKGROUND OF THE INVENTION
Polyphenylene ether luhricants represent very stable organic structures which meet the needs of jet engines, high temperature hydraulic systems, nuclear power plants, and as the fluid component o~ high temperature greases~ Although :
this class of lubricant is thermally and oxidati~ely stable, :
they can cause significant wear of high-alloy steels that are typically used in supersonic and hyper~onic aircraft jet engines. :~
Polyphenylene ether lubricants have been proposed which contain various additives for a variety of purposes. A
representative, non-limiting listing of additives which have been proposed is as followso - chelates of a heavy metal of Groups I~IV and VI-VIII
of the Periodic Table of the ~lements for wear and oxidation - ~
resistance and non-sludging behavior (U.S. Patent No. : :
1 ACA 5737 :~
POLYPHENYLENE ETHER LUBRICANT CONTAINING
HYDROCARBYL BIS(DIHYDROCARBYLPHOSPHATE) COMPOUND
BACKGROUND OF THE INVENTION
Polyphenylene ether luhricants represent very stable organic structures which meet the needs of jet engines, high temperature hydraulic systems, nuclear power plants, and as the fluid component o~ high temperature greases~ Although :
this class of lubricant is thermally and oxidati~ely stable, :
they can cause significant wear of high-alloy steels that are typically used in supersonic and hyper~onic aircraft jet engines. :~
Polyphenylene ether lubricants have been proposed which contain various additives for a variety of purposes. A
representative, non-limiting listing of additives which have been proposed is as followso - chelates of a heavy metal of Groups I~IV and VI-VIII
of the Periodic Table of the ~lements for wear and oxidation - ~
resistance and non-sludging behavior (U.S. Patent No. : :
3,360,467); -- organolead compounds for increased resistance to :~ :
oxidation, improved viscosity stability, and increased color stability (U.SO Patent No. 3,423,4693;
- perfluorinated aliphatic dibasic acids for enhanced lubrication under high load at high temperatures (U.S. Patent No. 3,704,277);
- phenoxyphenylphosphinic acid for enhanced lubrication under high load at high temperature (U.S. Patent No.
3,706l668).
. ~ . ,: :.
' '' :'.. '~ ~; ' '.'`' '''`', `'" ' ' : - - ~
~2~
SUMMARY OF THE INVENTION
The present invention relates to a polyphenylene ether lubricant comprising an effective amount of a hydrocarbyl bis(dihydrocarbylphosphate) compound a~ an anti~wear additive. These additives have been unexpectedly ~ound not to significantly affect the excellent thermal stability of the polyphenylene ether lubricant. Hydrocarbyl bis(dihydro-carbylphosphate) compounds have been used as additives in fuels for internal combustion engines (U.S. Patent No.
3,254,973), as extreme pressure and anti-wear additives in oleaginous or petroleum based lubricants (U.S. Patent No.
3,492,373; also see U.S. Patent No. 3,360,467 at Col. 1, line ::
58 to Col. 2, line 2, for the non-predictablD behavior of such additives when in a polyphenylene either fluid), and a~
a low flammability hydraulic oil, in general (U.S. Patent No.
oxidation, improved viscosity stability, and increased color stability (U.SO Patent No. 3,423,4693;
- perfluorinated aliphatic dibasic acids for enhanced lubrication under high load at high temperatures (U.S. Patent No. 3,704,277);
- phenoxyphenylphosphinic acid for enhanced lubrication under high load at high temperature (U.S. Patent No.
3,706l668).
. ~ . ,: :.
' '' :'.. '~ ~; ' '.'`' '''`', `'" ' ' : - - ~
~2~
SUMMARY OF THE INVENTION
The present invention relates to a polyphenylene ether lubricant comprising an effective amount of a hydrocarbyl bis(dihydrocarbylphosphate) compound a~ an anti~wear additive. These additives have been unexpectedly ~ound not to significantly affect the excellent thermal stability of the polyphenylene ether lubricant. Hydrocarbyl bis(dihydro-carbylphosphate) compounds have been used as additives in fuels for internal combustion engines (U.S. Patent No.
3,254,973), as extreme pressure and anti-wear additives in oleaginous or petroleum based lubricants (U.S. Patent No.
3,492,373; also see U.S. Patent No. 3,360,467 at Col. 1, line ::
58 to Col. 2, line 2, for the non-predictablD behavior of such additives when in a polyphenylene either fluid), and a~
a low flammability hydraulic oil, in general (U.S. Patent No.
4,212,832).
DESCRIPTION OF PREFERRED EMBODIMENTS :
The polyphenylene ether lubricant of the present .
invention comprises, as the base stock, a polyphenylene ether :~
of the formula Ar-O-[Ar-O]n-Ar where Ar stands for a phenyl ring, n is a whole number of generally from 2 to 5. This class of lubricant is well known to persons of ordinary skill in the art with the following patents, which are incorporated herein by reference, providing further disclosure: U.S. Patent Nos. 3,360,467;
3,423,469; 3,476,~15;`3,704,277; and 3,70~,668. Generally speaking, the polyphenylene ether base stock will comprise from about 90% to about 99.5%, by weight, of the entire ;~
lubricant composition.
~ 277~
The hydrocarbyl(bisdihydrocarbylphosphate) compounds which are used as an anti-wear additive with the previously described polyphenylene ether base stock are of the fsrmula RO O O OR ~: -\" "/
PO-A-OP
-~
RO OR
, where ~ is either unsubstituted or substituted hydrocarbyl such as alkyl or aryl and A is a bridging group containing alkylene, haloalkylene, arylene, two arylene groups joined by a bridging group (e.g., -C(CH3), -S02 or CO), or a bridging group containing biarylene. Such compounds are a known class of flame retardant in polymers and, as indicated above, have had some degree of use in certain fuel and lubricant ~ :~
compositions. Preferred R groups are phenyl with A also being phenylene, such a6 derived from a monoaromatic diol, such as either resorcinol of hydroquinoneO Generally, such :~:
diphosphate additive is present in relatively low amount such as about 0.1% to about 10%, by weight of the composition.
The polyphenylene ether lubricants of the present invention can contain other additives, particularly those recognized for use in fluids of that type. Inclusive of such -~
additives are pour point depressants, viscosity index -~
improvers, dyes, rust inhibitors, other anti-wear additives, and the like. - ~ x The present invention is further illustrated by the Examples which follow.
-~` 2~27 ~
This Example sets forth the wear data at various temperatures and loads (Four-Ball Wear scar at 600 rpm for two hours, two runs) for a control polyphenylene ether fluid and similar flu~ds containing certain bisphosphate additives:
Bisphosphate in ~ Temperature, Load, Steel --~
Sample (%~ 75CL40 kgLA** 204C/10 kq~B** 260C/10 kq/B**
None* (0%) 1.13; 1.20 1.44; 0.99 N.D.
NGBDP (1%) 0.71; 0.73 N.D. N.D.
BABDP (1%) 0.92; 0.91 N.D. N.D.
RBDP (1%) 0.87, 0.86N.D. N.D.
NGBDP (3~) 0.69; 0.68 N.D. N.D.
BABDP (3%) 0.70; 0.69 N.D. N.D.
RBDP ~3%) 0.80; 0.720.65; 0.670.43; 0.54 ~ :
NGBDP (5%) 0.70; 0.71 N.D. N.D.
BABDP (5%) 0.70; 0.70 N.D. N.D.
RBDP (5%) 0.78; 0.770.73; 0.79 N.D. ; `~
. ................. ....................................................... ... .. : . i N.D. = not determined.
* = The control fluid was a po].yphenylene ether fluid containing antioxidants ancl metal deactivators at a total concentration o~ leiss than 5~ by weight. It .
conformed to MIL-L-87100 speci~icationO
** = A = 521000 a high-carbon ~teel, aircraft grade, meeting QQ-S-624 specification.
B = M50: tool steel, meeting AMS 6490 specification. ~
NGEIDP = Neopentyl glycol bis (diphenyl phosphate) O ! : BABDP = Bisphenol A bis(diphenyl phosphate~.
R~DP = Resorcinol bis(diphenyl phosphate).
:
All three of the bisphosphate additives tested showed good -~
performance in the Four-Ball wear test. :~
~2~7~
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:
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.~
:',' '~::.
. :, ~., :' .~
2~12~7~
6 ACA 5737 : :
The above data illustrate the poorer performance for the neopentyl glycol bis(diphenyl phosphate additive ("NGBDP") as compared to either the bisphenol A or resorcinol derived ~:
bisphosphates ("BABDP" and '~RBDP", respectively).
The foregoing Examples should not be construed in a limiting sense since they merely serve to illustrate certain embodiments of the invention. The scope of protection sought is set forth in the claims which follow.
.-,: .., -' ~;
~ ~ ;
DESCRIPTION OF PREFERRED EMBODIMENTS :
The polyphenylene ether lubricant of the present .
invention comprises, as the base stock, a polyphenylene ether :~
of the formula Ar-O-[Ar-O]n-Ar where Ar stands for a phenyl ring, n is a whole number of generally from 2 to 5. This class of lubricant is well known to persons of ordinary skill in the art with the following patents, which are incorporated herein by reference, providing further disclosure: U.S. Patent Nos. 3,360,467;
3,423,469; 3,476,~15;`3,704,277; and 3,70~,668. Generally speaking, the polyphenylene ether base stock will comprise from about 90% to about 99.5%, by weight, of the entire ;~
lubricant composition.
~ 277~
The hydrocarbyl(bisdihydrocarbylphosphate) compounds which are used as an anti-wear additive with the previously described polyphenylene ether base stock are of the fsrmula RO O O OR ~: -\" "/
PO-A-OP
-~
RO OR
, where ~ is either unsubstituted or substituted hydrocarbyl such as alkyl or aryl and A is a bridging group containing alkylene, haloalkylene, arylene, two arylene groups joined by a bridging group (e.g., -C(CH3), -S02 or CO), or a bridging group containing biarylene. Such compounds are a known class of flame retardant in polymers and, as indicated above, have had some degree of use in certain fuel and lubricant ~ :~
compositions. Preferred R groups are phenyl with A also being phenylene, such a6 derived from a monoaromatic diol, such as either resorcinol of hydroquinoneO Generally, such :~:
diphosphate additive is present in relatively low amount such as about 0.1% to about 10%, by weight of the composition.
The polyphenylene ether lubricants of the present invention can contain other additives, particularly those recognized for use in fluids of that type. Inclusive of such -~
additives are pour point depressants, viscosity index -~
improvers, dyes, rust inhibitors, other anti-wear additives, and the like. - ~ x The present invention is further illustrated by the Examples which follow.
-~` 2~27 ~
This Example sets forth the wear data at various temperatures and loads (Four-Ball Wear scar at 600 rpm for two hours, two runs) for a control polyphenylene ether fluid and similar flu~ds containing certain bisphosphate additives:
Bisphosphate in ~ Temperature, Load, Steel --~
Sample (%~ 75CL40 kgLA** 204C/10 kq~B** 260C/10 kq/B**
None* (0%) 1.13; 1.20 1.44; 0.99 N.D.
NGBDP (1%) 0.71; 0.73 N.D. N.D.
BABDP (1%) 0.92; 0.91 N.D. N.D.
RBDP (1%) 0.87, 0.86N.D. N.D.
NGBDP (3~) 0.69; 0.68 N.D. N.D.
BABDP (3%) 0.70; 0.69 N.D. N.D.
RBDP ~3%) 0.80; 0.720.65; 0.670.43; 0.54 ~ :
NGBDP (5%) 0.70; 0.71 N.D. N.D.
BABDP (5%) 0.70; 0.70 N.D. N.D.
RBDP (5%) 0.78; 0.770.73; 0.79 N.D. ; `~
. ................. ....................................................... ... .. : . i N.D. = not determined.
* = The control fluid was a po].yphenylene ether fluid containing antioxidants ancl metal deactivators at a total concentration o~ leiss than 5~ by weight. It .
conformed to MIL-L-87100 speci~icationO
** = A = 521000 a high-carbon ~teel, aircraft grade, meeting QQ-S-624 specification.
B = M50: tool steel, meeting AMS 6490 specification. ~
NGEIDP = Neopentyl glycol bis (diphenyl phosphate) O ! : BABDP = Bisphenol A bis(diphenyl phosphate~.
R~DP = Resorcinol bis(diphenyl phosphate).
:
All three of the bisphosphate additives tested showed good -~
performance in the Four-Ball wear test. :~
~2~7~
~
N CD 1~1 1 ~ ~ o ~ .~, ~q I mO~o -- + ~
Q) I ~!) In ~ 7 ~ _ In + + + + ~ ~
! -' + ~ ++++m~
o I C~ .
O
o I
O ~ '~ X
~: I ~ ~ . ~ ooooo~
o I ~ ~ ~/ ~ . o o o r~ I ~ ~ + _ ~ O ~ . . O ~, . - ., .
.~. I ~ o~l ~ ~ o o + ,4 ~~
~ a~ ~4 O ~P o X Q~ o ,"
'1 'I ~ o U~ O ~ oooo~, .C
X ~ o o ~ ~ + O o .~ I ~ _I .u~ ~1 ~1 0 0 0 3 ~D O O -~P I ~1 + O . - - - - O ~q ~rl.~ .~' ' '-: ::
~ OOOOO~
t~~: I O\ol O In O~1 + + + + +,~
rl ~1) I Inl 11~ 0 0 U~ al~ ~ ~ ~ ~ ~1 ~ I O O :~.: : : ~:
~:1 ~ ~d I ~ o ~ o ~ 'I 'I h ,1 1 P~
o ~ + O O O C~ H :
~3 ~ ~On a + + + + ~
li3 ~ ,~ ~ o ~ ~ 1~
:
m I ,1 c~ ~loooo ~ a) ~ a :-~ o o . o I I ~1 0 ~ ~ I + ~ ~
o o ~o~ ~ ~ ~ ~ ~ ,~ h II~1 ~ O ~ O~1 0~
a) I + ooooomc) E~ X ''~'' I + ~ +
I
O O ~ O o ~ ~~ 0 -~
~r o . . . o o o L~ ~ ~ ~ ~ ::::: :.
I + ~ ~ u ~1 I rl o ~ co ~ I +
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o O ~ 0-~ ~ O ~ O o o o o ,~
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~n I + + o s~
o ~ ~ z ~
X _ E~ O q ~ h ~ O ~ ~ ~ ~ ~ - -ul C~ I . ~ ~n G~ O ,. .
~,q O ~ ~
0 ~- ~ ~0~ aO ~ ~ ~ ~ 11 11 11 o ~ 0 ~n _ o o ~ ~ ~ o 11 11 "
O ~ ~q ~I ~ ~I O O O ~ O O C~
1 13-rl 0 rd ~ r-rl ~ 1 o o o ~1u x a~ I d' m d' ~
P ¢ O E~ ~
~' "
U~ O U~ O ~ O
.~
:',' '~::.
. :, ~., :' .~
2~12~7~
6 ACA 5737 : :
The above data illustrate the poorer performance for the neopentyl glycol bis(diphenyl phosphate additive ("NGBDP") as compared to either the bisphenol A or resorcinol derived ~:
bisphosphates ("BABDP" and '~RBDP", respectively).
The foregoing Examples should not be construed in a limiting sense since they merely serve to illustrate certain embodiments of the invention. The scope of protection sought is set forth in the claims which follow.
.-,: .., -' ~;
~ ~ ;
Claims (10)
1. A polyphenylene ether lubricant which comprises a polyphenylene ether base stock and an effective anti-wear amount of a hydrocarbyl bis(dihydrocarbylphosphate) compound.
2. A lubricant as claimed in Claim 1 wherein the compound is a bis(diphenylphosphate).
3. A lubricant as claimed in Claim 1 wherein hydrocarbyl is derived from a monoaromatic diol.
4. A lubricant as claimed in Claim 2 wherein hydrocarbyl is derived from a monoaromatic diol.
5. A lubricant as claimed in Claim 1 wherein the amount of compound is from about 0.1% to about 10%, by weight of the lubricant.
6. A lubricant as claimed in Claim 2 wherein the amount of compound is from about 0.1% to about 10%, by weight of the lubricant.
7. A lubricant as claimed in Claim 3 wherein the amount of compound is from about 0.1% to about 10%, by weight of the lubricant.
8. A lubricant as claimed in Claim 4 wherein the amount of compound is from about 0.1% to about 10%, by weight of the lubricant.
9. A lubricant as claimed in Claim 1 comprising from about 0.1% to about 10%, by weight, of resorcinol bis(diphenylphosphate).
10. A lubricant as claimed in Claim 1 comprising from about 0.1% to about 10%, by weight, of hydroquinone bis(diphenylphosphate).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US100893A | 1993-01-06 | 1993-01-06 | |
| US08/001,008 | 1993-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2112775A1 true CA2112775A1 (en) | 1994-07-07 |
Family
ID=21693943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002112775A Abandoned CA2112775A1 (en) | 1993-01-06 | 1994-01-04 | Polyphenylene ether lubricant containing hydrocargyl bis(dihydrocarbylphosphate) compound |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0612837A1 (en) |
| CA (1) | CA2112775A1 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2405148B (en) * | 2002-05-07 | 2006-08-23 | Akzo Nobel Nv | Neopentyl glycol bis(diaryl phosphate) esters |
| JP4011441B2 (en) | 2002-05-10 | 2007-11-21 | ダイハツ工業株式会社 | Instrument panel structure of vehicle |
| JP5395453B2 (en) * | 2009-02-16 | 2014-01-22 | Ｊｘ日鉱日石エネルギー株式会社 | Continuously variable transmission oil composition |
| WO2011118707A1 (en) * | 2010-03-26 | 2011-09-29 | 株式会社Adeka | Lubricant composition |
| JPWO2011118708A1 (en) * | 2010-03-26 | 2013-07-04 | 株式会社Adeka | Lubricating oil additive and lubricating oil composition containing the same |
| US8722597B2 (en) | 2010-06-15 | 2014-05-13 | Adeka Corporation | Lubricating oil composition for internal combustion engine |
| SG187186A1 (en) * | 2010-07-27 | 2013-02-28 | Exxonmobil Res & Eng Co | Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants |
| US8618031B2 (en) | 2010-07-27 | 2013-12-31 | Exxonmobil Research And Engineering Company | Method for improving the deposit formation resistance performance of turbine oils containing amine antioxidants |
| US8623795B2 (en) | 2010-07-27 | 2014-01-07 | Exxonmobil Research And Engineering Company | Method for maintaining antiwear performance of turbine oils containing polymerized amine antioxidants and for improving the deposit formation resistance performance of turbine oils containing monomeric and/or polymeric antioxidants |
| JP6041223B2 (en) * | 2013-01-22 | 2016-12-07 | シチズン時計株式会社 | Lubricating oil composition for watch and watch |
| JP6041224B2 (en) * | 2013-01-22 | 2016-12-07 | シチズン時計株式会社 | Lubricating oil composition for watch and watch |
| WO2015026566A1 (en) * | 2013-08-20 | 2015-02-26 | Icl-Ip America Inc. | Lubricant having improved antiwear properties |
| US11230683B2 (en) | 2020-05-20 | 2022-01-25 | Nyco | Use of oils comprising non-neurotoxic anti-wear additives |
| FR3110593B1 (en) | 2020-05-20 | 2022-12-16 | Nyco | Use of oils containing non-neurotoxic anti-wear additives |
| US20230242830A1 (en) * | 2020-05-20 | 2023-08-03 | Nyco | Use of oils comprising non-neurotoxic anti-wear additives |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2722518A (en) * | 1952-06-27 | 1955-11-01 | Shell Dev | Synthetic lubricants |
| US3374175A (en) * | 1957-12-09 | 1968-03-19 | Shell Oil Co | Phenyl ether compositions |
| US3071548A (en) * | 1959-12-14 | 1963-01-01 | Universal Oil Prod Co | Stabilization of organic substances |
| US3169925A (en) * | 1961-06-26 | 1965-02-16 | Shell Oil Co | High temperature lubricants and phosphorus containing polymers |
| US3492373A (en) * | 1961-09-05 | 1970-01-27 | Sinclair Research Inc | Diphosphorous aromatic compounds |
| US3706668A (en) * | 1971-05-28 | 1972-12-19 | Frank S Clark | Polyphenyl ether lubricating compositions |
| DE2739843A1 (en) * | 1977-09-03 | 1979-03-15 | Bayer Ag | PROCESS FOR PRODUCTION OF HIGHER MOLECULAR PHOSPHORIC ACID OR. PHOSPHONIC ACID AYLESTERS |
| US4203757A (en) * | 1978-08-31 | 1980-05-20 | Gaf Corporation | Halophenoxyalkoxy phosphorous-containing sulfides |
| AU655284B2 (en) * | 1991-06-14 | 1994-12-15 | Ethyl Corporation | Organic phosphates and their preparation |
| US5196130A (en) * | 1991-12-09 | 1993-03-23 | The United States Of America As Represented By The Secretary Of The Air Force | Lubricity additive for high-temperature gas turbine engine oils |
-
1993
- 1993-12-23 EP EP93203669A patent/EP0612837A1/en not_active Withdrawn
-
1994
- 1994-01-04 CA CA002112775A patent/CA2112775A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0612837A1 (en) | 1994-08-31 |
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