Language selection

Search

Patent 2112775 Summary

Third-party information liability

Some of the information on this Web page has been provided by external sources. The Government of Canada is not responsible for the accuracy, reliability or currency of the information supplied by external sources. Users wishing to rely upon this information should consult directly with the source of the information. Content provided by external sources is not subject to official languages, privacy and accessibility requirements.

Claims and Abstract availability

Any discrepancies in the text and image of the Claims and Abstract are due to differing posting times. Text of the Claims and Abstract are posted:

  • At the time the application is open to public inspection;
  • At the time of issue of the patent (grant).
(12) Patent Application: (11) CA 2112775
(54) English Title: POLYPHENYLENE ETHER LUBRICANT CONTAINING HYDROCARGYL BIS(DIHYDROCARBYLPHOSPHATE) COMPOUND
(54) French Title: LUBRIFIANT A BASE DE POLY(OXYDE DE PHENYLENE) RENFERMANT DU BIS(DIHYDROCARBYLPHOSPHATE) D'HYDROCARGYLE
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • C10M 13/04 (2006.01)
  • C10M 14/04 (2006.01)
  • C10M 16/04 (2006.01)
(72) Inventors :
  • GENTIT, WILLIAM F. (United States of America)
(73) Owners :
  • AKZO N.V.
(71) Applicants :
  • AKZO N.V.
(74) Agent: GOWLING WLG (CANADA) LLP
(74) Associate agent:
(45) Issued:
(22) Filed Date: 1994-01-04
(41) Open to Public Inspection: 1994-07-07
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
08/001,008 (United States of America) 1993-01-06

Abstracts

English 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.


Claims

Note: Claims are shown in the official language in which they were submitted.


I Claim:
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).

Description

Note: Descriptions are shown in the official language in which they were submitted.


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. : :
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~
2 ACA 5737
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~
3 ACA 5737 -
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 ~
4 ACA 5737
EXAMPLE 1
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 +
UlO ~ oo O ~ ~ ~ ~ ~ ~ X S~ O r~
.. O . . . ~ O ~9 o ~ U
o O ~ 0-~ ~ O ~ O o o o o ,~
I Z; ~'~ + ~h o O m C) ~
~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.
.-,: .., -
' ~;
~ ~ ;

Representative Drawing

Sorry, the representative drawing for patent document number 2112775 was not found.

Administrative Status

2024-08-01:As part of the Next Generation Patents (NGP) transition, the Canadian Patents Database (CPD) now contains a more detailed Event History, which replicates the Event Log of our new back-office solution.

Please note that "Inactive:" events refers to events no longer in use in our new back-office solution.

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Event History , Maintenance Fee  and Payment History  should be consulted.

Event History

Description Date
Inactive: IPC from MCD 2006-03-11
Time Limit for Reversal Expired 1999-01-04
Application Not Reinstated by Deadline 1999-01-04
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 1998-01-05
Application Published (Open to Public Inspection) 1994-07-07

Abandonment History

Abandonment Date Reason Reinstatement Date
1998-01-05
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
AKZO N.V.
Past Owners on Record
WILLIAM F. GENTIT
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

To view selected files, please enter reCAPTCHA code :



To view images, click a link in the Document Description column. To download the documents, select one or more checkboxes in the first column and then click the "Download Selected in PDF format (Zip Archive)" or the "Download Selected as Single PDF" button.

List of published and non-published patent-specific documents on the CPD .

If you have any difficulty accessing content, you can call the Client Service Centre at 1-866-997-1936 or send them an e-mail at CIPO Client Service Centre.


Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Claims 1994-07-06 2 147
Abstract 1994-07-06 1 59
Drawings 1994-07-06 1 18
Descriptions 1994-07-06 6 391
Courtesy - Abandonment Letter (Maintenance Fee) 1998-02-09 1 187
Fees 1996-12-10 1 33
Fees 1995-12-05 1 32