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Patent 1090774 Summary

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(12) Patent: (11) CA 1090774
(21) Application Number: 1090774
(54) English Title: LOW WATER-SENSITIVE HYDRAULIC FLUIDS CONTAINING BORATE ESTERS AND FORMALS
(54) French Title: FLUIDES HYDRAULIQUES SENSIBLES A L'EAU, CONTENANT DES BORATES ET DES FORMALS
Status: Term Expired - Post Grant
Bibliographic Data
(51) International Patent Classification (IPC):
  • C10M 16/04 (2006.01)
  • C10M 10/52 (2006.01)
  • C10M 10/78 (2006.01)
  • C10M 12/16 (2006.01)
(72) Inventors :
  • SAWYER, ARTHUR W. (United States of America)
  • CSEJKA, DAVID A. (United States of America)
(73) Owners :
  • OLIN CORPORATION
(71) Applicants :
  • OLIN CORPORATION (United States of America)
(74) Agent: OSLER, HOSKIN & HARCOURT LLP
(74) Associate agent:
(45) Issued: 1980-12-02
(22) Filed Date: 1971-05-17
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
133,407 (United States of America) 1971-04-12

Abstracts

English Abstract


ABSTRACT OF THE DISCLOSURE
This invention relates to a low water-sensitive
hydraulic fluid composition which contains from about 20 to
about 96% by weight of at least one borate ester as the base
fluid and additionally, from about 2 to about 40% of a bis
(glycol ether) formal. Such low water-sensitive hydraulic
fluids are high boiling compositions which also have desirable
properties at low temperatures, particularly viscosity, and
thus are useful under a wide variety of climatic and
operational conditions.


Claims

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


WHAT IS CLAIMED IS:
1. A hydraulic fluid composition comprising (A) from
about 20 to about 96 percent by weight, based on the total
weight of the hydraulic fluid composition, of at least one base
fluid selected from the group consisting of (a) a borate ester
of the formula:
[R1(O-Ra)y-O]3-B ,
wherein R1 is alkyl of from 1 to 4 carbon atoms, Ra is
alkylene of from 2 to 4 carbon atoms and y is an integer of
from 2 to 4; (b) a borate ester of the formula:
[R1-(OCH2CHR2)m-(OCH2CHR3)nO]3-B ,
wherein R1 is alkyl of from 1 to 4 carbon atoms, R2 and R3
are independently selected from the group consisting of
hydrogen and methyl, m and n are positive integers whose
sum is from 2 to 20, and with the proviso that one of R2
and R3 is methyl and one of R2 and R3 is hydrogen; (c) a borate
ester of the formula:
(R1[Rg]O)3-B ,
wherein R1 is alkyl of from 1 to 4 carbon atoms, Rg is a
heteric oxyalkylene chain of the formula:
[- (OCH2CH2)r , (OCH2CHCH3)S -] ,
wherein the sum of r and s is not more than 20 and wherein
the weight percent of the oxyethylene units is not less than
20 based on the total weight of all the oxyalkylene units;
and (d) a borate ester of the formula:
<IMG>
wherein T1, T2 and T3 are each an independently selected
alkyl group having from 1 to 4 carbon atoms; R4, R5, R6, R7,
R8 and R9 are independently selected from the group consisting
of hydrogen and methyl, n and m are positive integers
-39-

independently selected in each chain and whose sum in each
chain is from 2 to 20, and with the proviso that in no more
than two of the chains is the sum of n and m the same;(B)
from about 2 to about 40 percent by weight, based on the
total weight of the hydraulic fluid composition, of at least
one bis(glycol ether) formal having the formula:
[RbO(RaO)X]2CH2 ,
wherein Rb is alkyl of 1 to 6 carbon atoms, Ra is alkylene
of 2 to 4 carbon atoms and x is an integer of 1 to 5 and
(C) from 0 to about 78 percent by weight, based on the total
weight of the fluid composition, of at least one diluent
selected from the group consisting of: (aa) glycol ethers
having the formula:
R[O-R']yOR' ,
wherein R is alkyl of from 1 to 4 carbon atoms, R1 is selected
from the group consisting of hydrogen and alkyl of from 1
to 4 carbon atoms, R" is alkylene of from 2 to 4 carbon atoms
and y is an integer of from 2 to 4; (bb) glycols and poly-
glycols having a molecular weight of from about 60 to about
450 and (cc) aliphatic saturated monohydric alcohols having
from 6 to 13 carbon atoms.
2. The hydraulic fluid composition of claim 1
wherein said formal has an alkyl Rb group of 1 to 4 carbon
atoms, an alkylene Ra group of 2 to 3 carbon atoms and x is
1 to 3.
3. The hydraulic fluid composition of claim 2
wherein from about 2 to about 15 percent by weight, based on
the total weight of the hydraulic fluid, of said formal is
present.
4. The hydraulic fluid composition of claim 3
wherein said formal is selected from the group consisting of:
-40-

[CH3O(C2H4O)]2CH2, [CH3O(C2H4O)3]2CH2, [C2H5O(C2H4O)2]2CH2,
[C4H9O(C2H4O)]2CH2, and [C4H9O(C2H4O)3]2CH2.
5. The hydraulic fluid composition of claim 2
wherein said base fluid is a borate ester of type (a).
6. The hydraulic fluid composition of claim 5
wherein said base fluid comprises from about 20 to about 54.4
percent by weight, based on the total weight of the hydraulic
fluid composition.
7. The hydraulic fluid composition of claim 5
wherein said base fluid comprises from about 54.5 to about
92 percent by weight, based on the total weight of the
hydraulic fluid composition.
8. The hydraulic fluid composition of claim 7
wherein said borate ester of type (a) has an alkyl R1 group
of 1 to 2 carbon atoms and an Ra alkylene group of 2 to
carbon atoms.
9. The hydraulic fluid composition of claim 7
wherein said base fluid is a borate ester selected from the
group consisting of: [CH3(OCH2CH2)3O]3-B, [C2H5(OCH2CH2)2O]3-B,
[C2H5(OCH2CH2)3O]3-B, [C2H5(OCH2CH2)4O]3-B,
[C3H7(OCH2CH2)3O]3-B, [C4H9(OCH2CH2)2O]3-B and
[C4H9(OCH2CH2)3O]3-B.
10. The hydraulic fluid composition of claim 9
wherein prom about 2 to about 15 percent by weight, based on
the total weight of the hydraulic fluid composition, of
said formal is used.
11. The hydraulic fluid composition of claim 10
wherein said formal is selected from the group consisting of:
[CH3O(C2H4O)]2CH2, [CH3O(C2H4O)2]2CH2, [CH3O(C2H4O)3]2CH2,
[C2H5O(C2H4O)2]2CH2, [C4H9O(C2H4O)]2CH2 and [C4H9O(C2H4O)3]2CH2.
-41-

12. The hydraulic fluid composition of claim 11
wherein said diluent comprises from about 2 to about 70
percent by weight, based on the total weight of the hydraulic
fluid composition.
13. The hydraulic fluid composition of claim 12
wherein said diluent is selected from the group consisting of
diethylene glycol monomethyl ether, diethylene glycol mono-
ethyl ether, diethylene glycol monobutyl ether, triethylene
glycol monomethyl ether, triethylene glycol monoethyl ether,
triethylene glycol monobutyl ether, tetraethylene glycol
monomethyl ether and tetraethylene glycol monobutyl ether.
14. The hydraulic fluid composition of claim 13
wherein from about 0.2 to about 6.0 percent by weight of an
inhibitor for pH and corrosion control is used.
15. The hydraulic fluid composition of claim 14
wherein said inhibitor is selected from the group consisting
of glycerin, butynediol, diethanolamine, methyl diethanolamine,
mixed isopropanolamines, diisopropanolamine and triisopro-
panolamine.
16. The hydraulic fluid composition of claim 15
wherein from about 0.001 to about 1.0 percent by weight,
based on the total weight of the hydraulic fluid composition,
of an antioxidant is used.
17. The hydraulic fluid composition of claim 16
wherein said antioxidant is selected from the group consisting
of sodium nitrite and dioctyl diphenylamine.
18. The hydraulic fluid composition of claim 5
wherein said diluent is a glycol ether of type (aa).
19. The hydraulic fluid composition of claim 18
wherein said diluent comprises from about 2 to about 70
percent by weight, based on the total weight of the hydraulic
fluid composition.
-42-

20. The hydraulic fluid composition of claim 19
wherein said diluent is selected from the group consisting of:
diethylene glycol monomethyl ether, diethylene glycol mono-
ethyl ether, diethylene glycol monobutyl ether, triethylene
glycol monomethyl ether, triethylene glycol monoethyl ether,
triethylene glycol monobutyl ether, tetraethylene glycol
monomethyl ether and tetraethylene glycol monobutyl ether,
21. The hydraulic fluid composition of claim 20
wherein said formal is selected from the group consisting of:
[CH3O(C2H4O)]2CH2. [CH3O(C2H4O)2]2CH2, [CH3O(C2H4O)3]2CH2,
[C2H5O(C2H4O)2]2CH2, [C4H9O(C2H4O)]2CH2, and
[C4H9O(C2H4O)3]2CH2.
22. The hydraulic fluid composition of claim 18
having incorporated therein from 0 to about 8.0 percent by
weight, based on the total weight of the hydraulic fluid
composition, of an inhibitor additive for pH and corrosion
control.
23. The hydraulic fluid composition of claim 22
wherein from about 0.2 to 6.0 percent by weight of said
inhibitor is used.
24. The hydraulic fluid composition of claim 23,
wherein said inhibitor is selected from the group consisting
of: glycerin, butynediol, diethanolamine, methyl diethanol-
amine, mixed isopropanolamines, diisopropanolamine and
triisopropanolamine.
25. The hydraulic fluid composition of claim 22
wherein from 0 to about 2 percent by weight, based on
the total weight of the hydraulic fluid composition, of an
antioxidant additive is incorporated therein.
26. The hydraulic fluid composition of claim 25
wherein from about 0.001 to about 1.0 percent by weight of
said antioxidant is used.
-43-

27. The hydraulic fluid composition of claim 26
wherein said antioxidant is selected from the group consisting
of sodium nitrite and dioctyl diphenylamine.
28. The hydraulic fluid composition of claim 27
wherein said inhibitor is selected from the group consisting
of glycerin, butynediol, diethanolamine, methyl diethanolamine,
mixed isopropanolamines, diisopropanolamines and triisopropanol-
amine.
29. The hydraulic fluid composition of claim 28
wherein said formal is selected from the group consisting of
[CH3O(2H4O)]2CH2, [CH3O(C2H4O)2]2CH2, [CH3O(C2H4O)3]2CH2,
[C2H5O(C2H4O)2]2CH2, [C4H9O(C2H4O)]2CH2 and
[C4H9O(C2H4O)3]2CH2.
30. A nonaqueous hydraulic fluid composition comprising
A. from 18 to 28% by volume of an orthoborate ester of a
glycol monoether selected from the group consisting of
triethylene glycol monomethyl ether, diethylene glycol
mono-(lower alkyl) ether, tetraethylene glycol monomethyl
ether or mixtures thereof;
B. from about 15 to 40% by volume of at least one bis
(glycol ether) formal having the formula CH3O(CH2CH2O)1-2
-CH2-(OCH2CH2)1-2OCH3;
C. from about 35 to 55% by volume of triethylene glycol
monomethyl ether;
D. from 0 to 31.5% by volume of at least one diluent
selected from the glycol ethers other than triethylene
glycol monomethyl ether having the formula R[O-R"]y OR',
wherein R is alkyl from 1 to 4 carbon atoms, R' is
selected from the group consisting of hydrogen and
44

alkyl of from 1 to 4 carbon atoms, R" is alkylene
of from 2 to 4 carbon atoms and y is an integer of
from 2 to 4;
E. from 0.5 to 4% by volume of compatible antioxidants
and corrosion inhibitors;
the total of components B and D not exceeding 40% by volume
and the total of components A to E being 80 to 100% by volume
of the hydraulic fluid composition.

Description

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


lU~ 7''1
This application relates to Canadian Patent No. 929,925
dated July 10, 1973.
This invention relates to new and improved, low
water-sensitive hydraulic pressure transmission fluids for use
in fluid pressure operating devices such as hydraulic brake
systems, hydraulic steering mechanisms, hydraulic transmissions,
hydraulic jacks, hydraulic lifts, etc. More particularly,
this invention relates to hydraulic fluids having a low
sensitivity to water which employ as the base fluid one or
more borate esters of glycol monoethers and additionally a
bis (glycol ether) formal. The term "base fluid" as used
throughout the specification and claims means the major active
ingredient (not necessarily present in the major or largest
proportion) of the hydraulic fluid, i.e. that ingredient
which is most active in maintaining the desired properties
of the hydraulic fluid especially in the face of aqueous
contamination.
A great number of hydraulic fluid compositions have
been suggested in the art. Commonly, the hydraulic pressure
transmission fluids, such as brake fluids are made up of
three principal units. The first is a base stock or lubricant
for the system which may include heavy bodied fluids such as
polyglycols, castor oil, mixtures of these materials, etc.
Diluents, which are employed for the purpose of controlling -;
the viscosity of the fluid as represented by glycol ethers,
glycols, alcohols, etc., form the second basic unit. Finally,
the third basic unit is represented by an additive or inhibitor
package comprising small quantities of materials which are
added to control or modify various chemical and physical
properties of the fluid, e.g. to reduce oxidation, to improve
~ $

lO~V~ 7~
C_5718 wetting and flow and to malntain the pH of the hydraulic system
above 7 ln order to minimize corrosion. By varying the
composition, particularly desired properties can generally be
attained. However, hydraulic fluids have been sub~ect to
increasingly stringent reguirements with regard to properties,
particularly boiling point and viscosity-temperature relation-
ship. This had made it extremely difficult to produce a
desirable fluid since very often a change in composition which
improves one or more of the properties will detrimentally
a~fect some other propertyO ~hus, it has been pos~ible to
-~ obtain hydraulic fluids having high boiling points by using
; higher molecular weight organic compounds, such as the
polyoxyalkylene glycol ethers, as the ma~or component,
however, the viscosity of these fluids is generally
unsatisfactory, particularly at low temperaturesO This
problem is magnified when water gets into the hydraulic fluid
since many of the properties are af~ected, some to a
substantial extent.
Hydraulic fluids, as exemplified by the commercial
motor vehicle brake fluids, are hygroscopic by nature and
therefore, absorb molsture from ambient atmospheres with
resulting degradation o~ their boiling point. mis ef~ect
that water has on the boiling polnt of hydraulic fluids has
been studied extensively and a great deal of public interest
has been generated concerning the safety qualities of hydraullc
fluids especially brake fluids as is pointed out, for example
by C. F. Pickett in an article entitled "Automotive Hydraulic
Brake Fluids" published as part of the 51st Mid-Year Meeting
Proceedings of the Chemical Specialties Manufacturing
Association, Inc.,N.Y. (1965). As indicated in the above-
noted artlcle, when small amounts of water, e.g. ~.5~ by welght
was added to various commercial brake fluids, some having

C-571~ inltlal bolling points o~ 500~., the resulting ~luid
compositions exhibited boiling polnts below 300F. In
contrast, the hydraulic ~luid composltions o~ this invention
generally malntain boiling points o~ greater than 300F. and
more o~ten greater than 320F. and 350Fo when pre~erred
embodiments are used, after the addition o~ 7.5% water.
The importance o~ having a hydraulic fluid which has
a low æensitivity to water and thus can maintain the boiling
point at levels above those previously found in available
commercial ~luids is more readily understood when the follow-
lng ~acts are considered. First o~ all, it is known that
hydraulic brake ~luid temperatures can reach rather high
levels and o~ten approach and even exceed the 300F. level.
This is substantiated by the results o~ field studies in 1966
by the Society of Automotive Engineers (See SP-338, "Automotive
Brake Evaluation Under Customer Usage Condit~ons", pp. 1 and 2,
~1968))wherein it was shown that brake ~luid temperatures
approached 270~. under typical driving conditions o~ vehicles `
which were loaded only to their manu~acturer's recommended
limit. It could reasonably be assumed ~rom these results,
that when abnormal conditions are encountered temperatures
would exceed 270F. and approach and even pass 300F.
It ls also known that so-called conventional type
motor ~ehicles often accumulate small amounts o~ moisture
in their hydraulic fluids during usage. This is substantiated
by results disclosed in a meeting of the SAE Hydraulic Brake
Systems Actuating Committee in 1966 (See minutes o~ meeting
o~ October 26_27, 1966) and further by the report o~ Charles
B. Jordan, '~ffect of Water on Hydraulic Brake Fluid", U.S~
Army Coating and Chemical Laboratory, May, 1966. These
articles clearly show that amounts o~ water have been
accumulated in hydraulic brake ~luids under use conditions
--4--

~ 7~
C-5718 ln varying proportlons and have o~ten reached levels o~ up
to 3.5~ and even have been as high as 5~ by weight. The fact
that hydraulic ~luids do accumulate ~ome water durlng usage
i8 further supported by the SAE Standard J-1703, Motor Vehicle
~rake Fluld, which requires certain water tolerance tests to
be passed a~ter the addition of 3.5~ water and also, requires
a corro~ion test to be passed a~ter the addition o~ 5% water
to the brake fluid.
From the above discusslon, it can readlly be under~tood
that hydraulic fluids under certain conditions can approach
temperatureæ o~ the magnitude o~ 300F. and higher and ~urther-
more such ~luids can accumulate small amounts o~ moisture
durlng usage. Thus, hydraulic ~luids which have low dry
boillng polnts and are ~ensitive to water to a large degree
can encounter problems such as vapor lock which can result
in the ~ailure of a hydraulic brake system and consequently
cause an accident. This clearly illustrates the advantage of
the hydraulic fluids o~ this inventlon which possess a high
degree o~ water tolerance and are able to maintain their
boiling points at higher and sa~er levels.
The seriousness o~ the problem o~ water accumulation
and its e~ects on the hydraulic ~luid system is ~urther
signified by the fact that the U.S. Department of Transporta-
tion presently is considering acceptance o~ standards for
motor vehicle brake ~luids which would ~or the first time
include a minimum wet re~lux boiling point (equivalent to
approximately 3.5~ by weight o~ water addedj. The proposed
standards include one for a ~luid having a minimum dry reflux
bolling point o~ ~01F. and a minimum wet reflux boiling polnt
of 284F. and another for a ~luid having a minimum dry re~lux
boiling point of ~46F. and a minimum wet re~lux boiling point
o~ 320F. The term "dry reflux boillng point" as used herein

10~3U"~7~
C_5718 ls de~ined as the bolling point o~ the hydraulic ~luid as
delivered to the consumer or distributors (i.e. ~luid ready
for use). Wet reflux boiling point i5 the boiling point o~
the hydraulic fluid a~ter a discrete amount o~ water has been
added thereto.
The above considerations clearly point out the need
; for a hydraulic ~luid which has a low sensit~ vity to water
and thus is able to maintain certain properties and
characteristics when amounts o~ water commonly encountered
during use are present. In addition, a hydraulic ~luid
which will be used under various climatic and operational
conditions must maintain adequate viscosity (~luidity)
over the temperature range o~ anticipated operating conditions
; so as to assure proper ~unctionality o~ the system.
` There are various hydraulic ~luids known in the art
as shown for example in Introduction to Hydraulic ~luids by
Roger E. Hatton, Reinhold Publishing Corp<, (1962); U.S. ~ -
Patent 2,998,~89 issued to Chester M. White on August 29,
1961 and U.S. Patent 3,~77,288 issued to Arthur W. Sawyer
on April 9, 1968~ Generally, these fluids do not have the
low water sensitivity that is required to maintain their
orlginal properties after there is an accumulation o~
moisture and additionally such ~luids generally do not have
the ability to operate under a wide variation o~ conditions.
One o~ the basic ob~ects of this invention is to
provide hydraulic pressure transmission ~luids ~or use in
hydraulic systems which retain to a high degree their
original properties when water is added, l.e. they have a
low sensitivity to water.
Another ob~ect is to provide hydraulic pressure
transmission ~luids whlch are high boiling compositions and
..~
~ -6-

l~J(~ 7~
_5718 which malntain relatively high boiling points even when water
is added to the ~nitial fluid composltion.
Another ob~ect o~ this invention is to provide
hydraulic pressure transmission ~luids having a high degree
o~ lubricity while maintaining desired viscosities within a
predetermined range under wide var~ations of temperature
conditions, especially subrreezing temperaturesO
The hydraulic fluids of this invention generally
comprise from about 20 to about 96 percent by weight, based
on the total hydraulic fluid weight, of at least one borate
ester of a glycol monoether as the base ~luid and from about
2 to about 40 percent by weight o~ a ~ormal o~ the glycol
ethers. Generally the remainder o~ the ~luid is made up of
diluent and one or more additives.
The hydraulic fluids of this invention are especially
desirable because they have a low water-sensitiv~ty and also
have a desired viscosity-temperature relationship over a wide
range of temperature conditions. These properties make such
~luids particularly attractive because they can satis~actorily
per~orm at low winter temperatures where the viscosity
requirements are stringent and also can be used in warm
weather climates and under heavy duty conditions particularly
because of their high boiling points and low sensitivity to
water. Additionally, the hydraulic ~luids of thls invention
are o~ low cost, are essentially odorless and colorless,
possess a high degree of compatibility with other ~luids and
exhibit a very low rate of corrosivity.
Another ~eature o~ the hydraulic ~luids o~ this
invention is that they have a satis~actory rubber compatibilityO
m e significance o~ rubber compatibility and the ru~ber swell-
ing properties of the fluids cannot be overlooked since too

` 1111~ 7~
little swelling will result in lea]~age of the fluid past
the rubber cup sealing means and past the piston and
hydraulic cylinders with corresponding loss of power. On
the other hand, fluids which cause too much rubber swelling
are not desirable since they destroy the structural properties
of the rubber sealing cups and rubber cylinders which, in
turn, results in malfunction or inoperativeness of the unit.
The hydraulic fluids of this invention generally
comprise four principal units: 1) base fluid, 2) formal,
3) diluent and 4) additives.
Base Fluid
The base fluid employed in the novel hydraulic fluids
of this invention generally comprises at least one borate ~ -
ester of a glycol monoether. More particularly, the hydraulic
fluids of this invention will comprise from about 20 to about
96 percent by weight, based on the total hydraulic fluid
weight, of at least one borate ester of a glycol monoether.
Preferably, the amount of borate ester will vary from about
30 to about 92 percent and more preferably from about 54.5
to about 92 percent by weight based on the total hydraulic
fluid weight. When using hydraulic fluids which can safely
operate under somewhat lower temperature conditions, the
range of borate ester used may vary from about 20 to about
54.4 percent and preferably from about 30 to about 54.4 percent
by weight, based on the total weight of the hydraulic fluid.
Although a wide variety of borate esters can be
employed as the base fluid in the novel hydraulic fluids of
this invention, an especially useful class of borate esters
are the so-called tri-borate esters of glycol monoethers
having the general formula:
[Rl(~Ra)y~]3-B ' (I)
-8-

15)~ J7~
C-5718 wherein Rl ls a lower alkyl radical containing from 1 to 4
carbon atoms prererably 1 to 2, Ra ls alkylene o~ from 2 to
4 carbon atoms, pre~erably 2 to 3, ~nd y 18 an lnteger ~rom
2 to 4 lncluslve. The Rl and Ra gr~ups may be elther stralght
or branched chaln structures. Borates o~ the a~ove-mentloned
type include, ~or example: r H3(0CH2CH2)2~ 3-B,
Hs(OCH2CH2)3 ~3-B, r 3H7(0CH2CH2)g ~3-B,
H3(OCH2CHCH3)2 ~3-B, ~ H3(OCH2CHCH3)3 ~3-B,
H3(0CH2CHCH3)g~3_B, ~ 2H5(0CH2CHCH3)2 ~3-B,
~2H5(OCH2CHCH3)3 ~3-B, ~ 2H5(0CH2CHCH3)4~3-B,
r3H7(0CH2CHCH3)2-g ~3-B, ~ gH9(0CH2CHCH3)2-4~ 3-B,
~H30(oCHCH9CH2)2-4~73-B, ~2H5(ocHcH3cH2)2-g~73-B~
~ H3(W HCH3CHCH3)2_g ~3-B, ~ 2H5(0CHCH3CHCH3)2-g~3-B,
H3(0CH2CHCH2CH3)2-g~3-B, ~ 2H5(0CH2CHCH2CH3)2-g~3-B,
CH2CH3 IH2CH3
~ r H3(0CH - CH2)2-g~3-B, ~ 2H5(0CH - CH2)2-4~3-B-
: While any o~ khe borate esters de~ined by formula
(I) may be u~ed, the ~ollowing borate esters are part~cularly
use~ul: ~ H3(0CH2CH2)3 ~3-B, ~ 2H5(0CH2CH2)2 ~3-BJ
~zH5(0CH2CH2)3 ~3_B, ~ 2H5(OCH2CH2j~ ~3-B,
r3H7(0CH2CH2)3 ~3-B, ~ gH9(0CH2CH2)2~ 3-B and
~ gHg(OCH2CH2)3 ~3-B.
, '
_g_
.,

ll)~3V'-~ 7~
C-5718 Borate~ o~ the above-mentloned type can be conveniently
prepared by reacting orthoboric acid and the glycol monoether
while in the presence Or a water-azeotrope ~orming solvent.
Water ~ormed ln the esteri~ication reaction is continuously
removed as the azeotrope. At rirst, the temperature Or the
reaction mixture is maintained between about 0C. and about
l90~C. and desirably at the distillation temperature o~ the
water-solvent azeotrope. Arter essentially complete removal
o~ the water formed durlng esteri~ication, the excess
solvent is conveniently removed from the reaction mixture by
distillatlon. The borate ester product, which is left in a
residue, may then be recovered by distilling under reduced
pressure or by extraction with a suitable solvent ~ollowed
by evaporatlon o~ the solvent. For example, the compound
H5(OCH2CH2)2~-B can be prepared by reacting two moles
o~ C2H5(0CH2CH2)20H, 0.67 mole o~ orthoboric acid and 700 ml.
Or ethylbenzene with heating and mixing to yield 198 grams o~
the ester, a water-white liquid boiling at 222~_223C. (5 mm.
Hg). It i~ noted that in the preparation o~ these esters,
a small proportion Or concomitant reaction products may be
formed and other minor impurities may al~o be present.
Generally, the predominant portion Or ~uch other reaction
products ~ormed will be a boroxine type compound
havlng the following general structure:
/0\
Rz - B B Rz
\ B
Rz
whereln Rzis derived from the particular glycol ether belng
used, e.g. CH3(OCH2CH2)20-, C2H5(OCH2CH2)20-, etc. The
amount of such concomltant reaction products rormed and other
lmpuritles present may be up to about 10~ by welght lr the
--10--
. -

~ V'7 7~
C-5718 reacted mixture is not dlstilled. Dlstillatlon will reduce
the amount o~ other reaction product~ and impurities to
about 1% or less, however, either the distllled or undistilled
- product can be used provided the reaction medium or solvent
18 stripped off. me term "borate ester" as used in the
speoi~ication and claims is intended to include relatively pure
borate ester as well as crude borate ester which contains
impurltles and other by-products ~ormed during preparation as
described above. The preparation o~ the tri-borate esters
per se is more completely described in U. S. Patent 3,080,412
issued to D. M. Young on March 5, 1963. It i8 0~ lnterest
to note that this patent (U.S. 3,080,412) dlscloses the use
of trl-borate esters, such as tris ~ -(2-ethoxyethoxy)ethy~
borate, as stabllizer and corroslon inhibltors ~or lubricants
and non-aqueous hydraulic ~luids. However, use o~ these esters
~or such purposes, i.e. as a stabilizer or corrosion inhlbitor,
would not impart satisfactory low water sensitivity to the ~ -
hydraulic ~luid since such usage would generally be in very
small or mlnor proportions (e.g. ~rom 0.5 to 2%) in accordance
with the generally accepted practice in the art (e.g. see
U.S. Patent ~403J104 issued to P. B. Sullivan on September
24J 1968). Additionally ~luids containing such amounts of
esters would not have desired temperature-viscosity relatlon-
ship over the wide range of operating conditions as provlded
~y the hydraulic fluids o~ thi~ invention.
A second highly use~ul class of borate esters includes
compounds of the general ~ormula:
~ l-(ocH2cHR2)m-(ocH2cHR3)n~3-B (II)
wherein R2 and R3 are independently selected from the group
con~isting of hydrogen and methylJ m and n are positive
integers whose sum is ~rom 2 to 20 and Rl is alkyl o~ ~rom 1
, -11--

J~J()'~ 7~}
C-5718 to 4 carbon atom~ and with provi~o that one o~ R2 and R3 is
methyl and one of R2 and R9 1~ hydrogen. Rl may be a
straight chain or branched alkyl. Borate esters of Type II
can be prepared in the general way as those esters previously
described (Type I) above, utllizing the so-called block type
glycol monoethers. The preparation of esters of Type II
18 described in detail in U.S. Patent 3,316,287 issued to
L. G. Nunn, Jr. et al on Aprll 25, 1967.
Type II borate esters use~ul in preparlng the novel
~luids o~ thl~ invention include, ~or example:
~H3(0CHzCH2)-(OCH2CHCH3) ~3-B
Hs(OCHzCHCH3)~(0CH2CH2) ~3-B
~3H7(0CH2CHCH3)2-(OCHzCH2) ~3-B
4Hg(OCH2CH2)5-(OCH2CHCH3) ~3-B
~H3(0CHzCH2)a-(OCH2CHCH3)5~3-B
~ 2H5(OCH2CHCH3) 12- ( OCHzCH2)8~3-B
r3~7(OCH2CHCH3) lo-(OCH2CH2)3-B
Another class o~ borate ester~ useful in the fluid
composltions o~ this invention include esters having heteric
oxyalkylene chalns, that is, oxyalkylene chalns in which
oxyethylene and oxypropylene units are distr~buted randomly
throughout the chain. These Type III esters have the
general ~ormula:
(Rlr ~ 0)3-B , (III)
Rg represents a heteric oxyalkylene chain havlng the ~ormula:
~ (OCHzCH2)r , (OCH2CHCH3)8 ~7
where the sum o~ r and 8 is not more than 20 and whereln
the welght percent of oxyethylene units in the said chain
is not less than 20 based on the total weight of all the
oxyalkylene Imits in the chain and Rl is alkyl o~ ~rom 1
to 4 carbon atoms and may be straight or branched chain.
The preparation of Type III esters can be aocompllshed ln
the same general manner as the preparatlon o~ Types I and II
_12-
. -

~ )'7 7~
C-5718 described above by reaoting orthobor~c acid ln the presence
o~ toluene with a heteric glycol monoether o~ the ~ormula:
R ~ ~ OH
where Rl and Rg have the same meaning as previously set ~orth.
Glycol monoethers o~ this class can be conveniently prepared
by methods well known in the art such as the process described
ln U.S. Patent 2,425,845 issued to W. J. Toussaint et al on
August 19, 1947.
A ~ourth type o~ borate ester suitable for use in
the ~luid compositions o~ this inventlon have the general
formula:
T2(0CH2CHR7)m-(OCH2CHR~)nO O(R4CHCH20)n (R5CHCH20)mT
( CV) O(R8cHcH2o)n-(R9cHcH2o)mT3
wherein Tl, T2 and T3 are each an independently ~elected
alkyl group having ~rom 1 to 4 carbon atoms, R4, R5, R~, R7,
R8 and R~ are lndependently selected ~rom the group cons~st-
lng o~ hydrogen and methyl, n and m are poslt~ve ~ntegers
~ndependently selected ln each chaln and whose sum ln each
chain is from 2 to 20J and with the proviso that ln no more
than two o~ the chains i8 the sum o~ n and m the same. It
is also noted that Tl, T2, and T3 may be a straight or branched
chaln alkyl group.
Borate e ters o~ this type can be prepared ~n the
same way as the proces~ described ~or Type I esters previously
mentioned.
Type IV borate esters su~table for use in the ~luids
of this ~nvention ~nclude, for example: -
,,,., :, . . .. . . . .

tU~()'7 7~
`~ C-5718 O(CH3CHCH20)-(CH2CH20)CH3
C2H5(OCH2CHCH3) 3 - ( OCH2CH2)2-O-B\
O(CH3CHCH20)-(CH2CH20)2CH3
.O(CH3CHCH20)-(CH2CH20) loC4H~,
.. .
CH3(OCH2CH2) 6 - ( OCH2CHCH9)5-O-B
O(CH2CH20)6-(CH2CHCH20)l0C4H9
O(CH3CHCH20)15C3H7
j C2H5(OCH2CH2)2-(OCH2CHCH3)0-B\
,;; O(CH2CH20)-(CH3CHCH20)CH3
It is ~urther noted that borate esters of Types II,
III and IV will include concomitant reactlon products and
other impurities o~ the type as described above ~or Type I
~ esters. Re~eren¢e to these types o~ borate esters in the
,:"'! speci~icatlon and claims is intended to include relatively
pure borate ester as well as crude borate ester whlch contalns
impurities and other by-products formed durlng preparation
~ as described above ~or Type I.
;~ Formal Comonent
The formal portion of the hydrauli¢ ~luid composition
l 20 o~ this invention will generally comprise ~rom about 2 to about
;
40 percent by weight, based on the total weight of the
hydraulic ~luld, of one or more bis(glycol ether) formals
having the ~ormula:
~ . . .
~bQ(Ra)x ~ 2CH2 (V) -~
wherein Rbis alkyl of 1 to 6 carbon atoms, preferably 1 to 4,
~ Ra is alkylene o~ 2 to 4 carbon atoms, pre~erably 2 to 3
-; and x is an integer of 1 to 5, preferably 1 to 3. The ~ and
Ra groups may be straight or branched chained and it is also
intended that the alkylene oxide group (RaO) in the above
formula (V) include mixtures o~ said alkylene oxides.
Illustrative of the above type formals (V) are the
v
Jj -14_
.
.".' '' .

1~90~717
C-5718 ~ollowing compounds:
~H3(CZH4,~2CH2
rH3O(C2H40)~72CH2
rH3O(C2H40),~72CH2
~2H50(C2H40)272CH2
~4H90(C2H40~2CH2
~4H90(C2H40)~72CH2
~H30(CH2CHCH30~72CH2
~H30(CH2CHCH30)~72CH2
r2H50(CH2CHCH30)272CH2
~H3(C2H4)(CH2CHCH3~72CH2
While any of the above ~ormals defined by ~ormula
(V) may be used, the ~ollowing bls(glycol ether) ~ormals
are partlcularly use~ul:
~H3(C2H4~72CH2
~H30(C2H40)~72CH2
~H30(C2H40)~72CH2
~2H50(C2H40);z72CH2
~4H90(C2H40.~72CH2
~4H90(C2H40)~72CH2 ::
The above ~ormals may be prep`ared by reactlng the
appropriate glycol with paraformaldehyde and removing the
water o~ condehsation which forms. Preparative technigues
are commonly known in the art, e.g. British patent 506,613
(June 1, 1939); Chemical Abstracts, 33, 9325 (1939) discloses
a proce~s ~or the preparation o~ condensation products o~
aldehydes with polyhydric alcohols or partial ethers thereo~.
Other known methods of preparation are disclosed in Canadian
patent 390,733 (August 13, 1940); Chemical Abstracts, ~4,
6948 (1940), and in J.Am.Chem.Soc., "Formaldehyde bis(~ -ethoxy-
ethyl) and bis(~ -ethoxyethoxyethyl) acetal by M. Sulzbacher,
I~, 2795_6, (1950).
.

0'~'7~
C-571~ While the hydraullc fluld composition of this
invention may contain from about 2 to about 40 percent by
weight, based on the total weight o~ the hydraulic fluid,
of the above rormals (V), preferred embodiments include
about 2 to about 15 and more preferably ~rom about 2 to about
10 percent by weight.
The use of these formals enable the hydraulic ~luids
of this invention to function over a wide range of climatlc
and operational conditions particularly because o~ desirable
temperature_viscosity relationships which such hydraulic fluids
possess.
Dlluents
The diluent portion of the hydraulic fluid composition
of this invention generally will comprise one or more compounds
selected ~rom the group consisting of a) glycol monoethers or
diethers b) glycols and polyglycols and c) aliphatic saturated
alcohols.
More particularly, the glycol monoethers or diethers
s have the formula:
R~ -R~ yORI (VI)
wherein R is alkyl of from 1 to 4 carbon atoms,preferably 1 to
2, R~ is hydrogen or alkyl of from 1 to ~ carbon atoms,pr~ably
1 to 2, R" is alkylene of 2 to 4 carbon atoms, preferably
2 to 3, and y is 2 to 40 The R, R' and R" groups may be
straight chained or branched and it is also intended that the
alkylene oxide groups (O-R") in the above formula (VI) include
mixtures of said alkylene oxides.
Illustrative of the diluents o~ this type (VI) are
the following compounds: diethylene glycol monomethyl ether,
diethylene glycol monoethyl ether, diethylene glycol mono-
isopropyl ether, diethylene glycol monoisobutyl ether,
-16-

1~ ~0'7~7~
-5718 triethylene glycol monomethyl ether, triethylene glycol
monoethyl ether, triethylene glycol mono-n-butyl ether, tetra-
ethylene glycol monomethyl ether, tetraethylene glycol mono-
ethyl ether, dipropylene glycol monomethyl ether, dipropylene
glycol monoethyl ether, tripropylene glycol monomethyl ether,
trlpropylene glycol monoethyl ether, trlpropylene glycol
mono-n-butyl ethèr, tetrapropylene glycol monomethyl ether,
tetrapropylene glycol monoethyl ether, dibutylene glycol
monomethyl ether, dibutylene glycol monoethyl ether, tri-
butylene glycol monomethyl ether, tributylene glycol monoethyl
ether, tributylene glycol mono-n-propyl ether, tetrabutylene
glycol monomethyl ether, tetrabutylene glycol monoethyl ether,
tetrabutylene glycol mono-n-butyl ether and the corresponding
diethers thereo~. It is ~urther noted that the above diluents
include the various isomer3 o~ the respective compounds and
mixtures thereo~.
While any o~ the above glycol ethers de~ined by
formula (VI) may be used, the ~ollowing glycol ethers are
partlcuIarly use~ul: dlethylene glycol monomethyl ether,
dlethylene glycol monoethyl ether~ diethylene glycol monobutyl
ether, triethylene glycol monomethyl ether, trlethylene glycol
monoethyl ether, triethylene glycol monobutyl ether, tetra-
i
ethylene glycol monomethyl ether and tetraethylene glycol -
monobutyl ether.
The glycol ether~ are the most pre~erred diluent ~ince
their use will result in a ~luid having a de~irably high
boiling point with good vi~c~osity and water solubility
properties. Most pre~erred df the glycol ethers are the
ethylene glycols.
The second group o~ use~ul diluents are the glycols
and polyglycol3, including alkylene, polyalkylene and poly-
oxyalkylene glycols, having a molecular weight o~ ~rom about
-17-

'74
C_~718 60 to about 450 and pre~erably ~rom about 100 to about 300~
Illustratlve Or such type diluents are the following compounds:
ethylene glycol, propylene glycol, ~lexylene glycol, diethylene
glycol, dlpropylene glycol, triethylene glycol, tripropylene
glycol, polyethylene glycol and polypropylene glycolO
The use o~ the glycols and polyglycols as diluents
is not as desirable as the glycol ethers since their use
may result in some loss o* fluidit~ at ~ery low temperatures,
however, they may be used in condi~ion~ ~here the reguirements
- are not as demanding.
The third type o~ use~ul diluents are aliphatic,
saturated monohydric alcohols containir~ ~rom 6 to 1~ carbon
atoms, preferably ~rom 8 to 10. Illustrative o~ such diluents
are the following alcohols: hexanol, octanol, isooctanol,
decanol, isodecanol, dodecanol, and tridecanol
Since the use o~ the allphatlc alcohols in a high
boiling hydraulic fluid may result in some loss of water
solubility, they are not as desirable as the glycol ethers.
However, they may be used in conditions where the requirements
are not as stringent.
The diluent portion of the hydraulic fluids o~ this
-18-

lt~3~ ' 7'~
- invention generally will comprise from 0 to about 78 percent
by weight, preferably from about 2 to about 70 and more
preferably from about 6 to about 45 percent by weight, based
on the total weight of the hydraulic fluid composition.
While the above diluents, especially the glycol ethers,
are particularly preferred, other diluents may be used if
the desired properties and characteristics of the hydraulic
fluid can be attained. For example, certain diesters
derived from organic aliphatic acids and aliphatic
alcohols might be usefully employed. Examples of diesters
which might be used include dibutyl adipate, bis(methoxyethyl)
azelate, diisopropyl succinate, dipropylene glycol dipropionate
and triethylene glycol dibutyrate.
Additives
When desired, various additives may be added to the
hydraulic fluids of this invention to control or modify
various chemical and physical properties of the fluids. Among
the various types of additives which can be added to the
hydaulic fluids of this invention are included: inhibitors -
for pH and corrosion control, antioxidants, rust inhibitors,
- viscosity index improvers, pour point depressants, lubricating
additives, antifoamants, stabilizers, demulsifiers, dyes and
odor suppressants. Generally, the total amount of additives
which may be incorporated into the fluid composition will vary
depending on the particular composition and the desired
properties. More particularly, the total amount of additives
will comprise from 0 to about 10 percent and preferably from
about 0.1 to about 8.0 percent by weight based on the total
weight of the hydraulic fluid composition.
For example, inhibitors for pH and corrosion control,
such as alkaline inhibitors as exemplified by the alkali
metal borates, can be employed in an amount sufficient to
.
1 9--
. .

maintain alkaline conditions in the fluid compositions, e.g. a
pH value of from about 7.0 to about 11.5. These inhibitors
are generally added in an amount of from 0 to about 8.0 per-
cent by weight based on the total weight of the hydraulic
fluid composition and preferably from about 0.2 to about 6.0
percent by weight on the same basis. Useful inhibitors in-
clude alkali metal borates, such as sodium borate, potassium
tetraborate, etc.; sodium meta arsenite; alkali metal salts of
fatty acids, such as potassium oleate, the potassium soap of
rosin or tall oil; alkylene glycol condensates with alkali
metal borates, such as the ethylene glycol condensate of pot-
assium tetraborate; amines, for example, ethanolamine, methyl
diethanolamine, diethanolamine, isopropanolamines (mono, di
and tri), di(2-ethylhexyl) amine, di-N-butyl amine, monoamyl
amine, diamylamine, dioctylamine, salicylal monoethanolamine,
di-~-naphthyl-p-phenylene diamine, N,N'-disalicylidene-1,2-
propanediamine, N,N'-disalicylal ethylene diamine, dicyclohexyl-
amine, and amine salts such as mono or dibutyl ammonium borate;
phosphites, such as triphenyl phosphite, tri(tertamylphenyl)
phosphite, diisopropyl phosphite, etc.; mercaptobenzotriazole;
morpholine compounds including alkyl morpholines having from
1 to 4 carbon atoms in the alkyl group such as N-ethyl morpho-
line, N-isopropyl morpholine, N-butyl morpholine; N-phenyl mor-
pholine, N-(2-aminoethyl) morpholine, N-(2-hydroxyethyl) mor-
pholine, etc.; phosphates, including the alkali metal phos-
phates, dibutyl amine phosphates, the dialkyl acid o-phos-
phates and amine salts thereof; triazoles including benzotri-
azole, 1,2-naphthotriazole, 4-nitrobenzotriazole, tolutriazole,
aminobenzotriazoles such as 5-acylaminobenzotriazole, and alkyl
triazoles having 1 to 10 carbon atoms in the alkyl group as ex-
emplified by methyl triazole, ethyl triazole, n-propyl triazole,
tertiary butyl triazole, hexyl triazole, isodecyl triazole,
etc. Other useful corrosion inhibitors
-20-

include adenine, 4-methylimidazole, 3,5-dimethyl pyrazole,
6-nitroimidazole, imidazole, benzimidazole, quinine, indazole,
ammonium dinonylnaphthalene sulfonate, dioleyl thiodipropionate, -
ethylbenzoate, ethyl-p-aminobenzoate, cyclohexyl ammonium
nitrite, diisopropyl ammonium nitrite, butynediol, glycerin,
1,3,5-trimethyl-2,4,6-tris (3,5-di-tert. butyl-4-hydroxybenzoyl),
4,4'-methylene bis(2,6-di-tert. butylphenol), 4-hydroxymethyl-
2,6-di-tert. butylphenol, 4,4'-methylene bis(4-methyl-6-tert.
butylphenol), salicylal-o-aminophenol, 2,6-di-tert. butyl-2-
dimethylamino-p-cresol, 4,4'-thio bis(6-tert. butyl-o-cresol).
Mixtures of the above-mentioned inhibitors can be employed
if desired.
While any of the above-mentioned inhibitors may be
used for pH and corrosion control, the following inhibitors
are particularly useful: glycerin, butynediol, diethanolamine,
methyl diethanolamine, mixed isopropanolamines, diisopropanol-
amine and triisopropanolamine.
An antioxidant may be used as an additive in the
hydraulic fluid compositions of this invention if desired.
Generally the amount of antioxidant used will vary from 0 to
about 2 percent and preferably will be from about 0.001 to
about 1.0 percent by weight based on the total weight of the
fluid composition. Typical antioxidants include phenolic
compounds, such as 2,2-di-(4-hydroxyphenol) propane,
-21-

7~
C-5718 phenothiazlne, phenothiazlne carboxylic acid esters, N-alkyl
or N-arylphenothiazines, such as N-ethyl phenothiazlne,
N-phenyl phenothiazine, etc.; polymerlzed trimethyldihydro-
guinoline, amines, such as phenyl-alpha-naphthylamine, phenyl-
beta_naphthylamine, dioctyl diphenylamine, N~N-di-~ -
naphthyl-p-phenylene diamine, p-isopropoxy diphenylamine,
N,N-dibutyl-p_phenylene diamine, diphenyl-p-phenylene diamine,
N,N'-b1s(1,4_dimethylpentyl)_p-phenylene diamine, N,N'-diiso-
propyl-p-phenylene diamine, p-hydroxydiphenylamine, etc O;
~ 10 hindered phenols such as dibutyl cresol, 2,6_dimethyl-p-cresol,
;; butylated 2,2_di-(4-hydroxyphenyl) propane, n-butylated
aminophenol, butylated hydroxyanisole~, such as 2,6-dibutyl-
p-hydroxyaniqole; anthraquinone, dihydroxyanthraquinone,
hydroquinone, 2,5_di_tertiarybutylhydroguinone, 2_tertiary
butylhydroquinone, quinoline, p-hydroxydiphenylamine, phenyl
benzoate, 2,6-dimethyl p-cresol, p-hydroxyanisole, nordihydro-
quaiaretic acid, pyrocatechol, styrenated phenol, polyalkyl
polyphenols, sodium nitrite, etc, Mixtures o~ the above-
mentioned antioxidants can be emplo~ed, i~ desired. It should
be emphasized that wlth a variety o~ the ~luids of this
lnvention, which are suitable ~or a wide range o~ industrial
- application, a separate antioxidant is not required.
While any of the above_mentioned antioxidants may
be used, the ~ollowing antioxidants are particularly pre~erred:
sodium nitrite and dioctyl diphenylamine.
The above-noted inhibitors and additives are merely
exemplary and are not intended a~ an exclusive listing o~ the
many well-known materials which can be added to fluid
.,
; compositlons to obtain various desired properties. Numerou~
~-dditives u~e~ul in hydraulic ~luids are disclosed in
Introduction to EYdraulic Fluids by Roger E. Hatton, Reinhold
Publishing Corp., (1962).
_22_
, . . . .

r~ 7~
C-5718 Formulation o~ the novel hydraulic fluids of this
invention 18 accomplished by blending the components to a
homogeneous stage in a mixing vessel~ The pre~erable blend-
ing temperature is ~rom about 50-125F. It ls preferable
to warm the solution during preparation to ~acilitate dis-
solution. The blending o~ the compounds is conveniently
conducted at atmospheric pressure in the absence o~ moi~tureO
In general, any suitable method can be used in pre-
paring the liguid compositions o~ this invention. The
components can be added together or one at a time, in any
desired sequence. It is pre~erable, however, to add the
antioxidant and alkaline inhibitor as a solution in the
glycol ether component. All components are mixed until a
single phase composition is obtainedO
The ~ollowing examples which illustrate varlous
embodiments of this invention are to be considered not
limitative.
_2~_

~ 4
C-571~ EXAMPLE 1
A hydraulic rluid was prepared having the ~ollowing
composition: .
Percent by
Wel~ht
Borate Ester
r2Hs ( OC2H4) 3~3 -B . 51.80
~ 2H5(0C2X4)4~ 3-B 18.20
Triethylene glycol monoethyl ether 14.35 .
rH3O(c2H~o)~72cH2 10. 00
l~xed isopropanolamine
. (10~15~ mono, 40-50% di, 40-50% trl) 3.00
Glycerin 2.00
~utynedlol 0.50
.P Dioctyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.~ 0.10
Sod-lum nitrlte 0.05
.~ , .
- 100. 00
This ~luid compositlon was tested accord~ng to the
~: 20 : procedures set forth in Society o~ Automotive En6ineers
- Standard J1703. The data relating to these tests, which
illustrate the outstanding properties Or this fluid is
i shown in Table 1.
~ he re~lux boiling point (dry) o~ the above fluid
was measured and ~ound to be 532F. at atmospheric pressure.
To test the water insensitivity of the fluid composition, a
- sample of 100 parts by volume o~ the fluid plus 3.5 parts
. by volume o~ water was prepared and it was found to have a
re~lux boiling point (wet) at atmosp~eric pressure o~ 367CF. .
indicating the high degree o~ water insensitivity.
., .
''- , ' ' ;
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. ~ o ~ :~ ~ o ~ :~ o
., O ~ U~ ~ ~1
O b9 ~ ~ ~ h h Ll~\ trd
o ~ ; 1- . a~ ~ o ~
~: rl ~ OC ~ O ~rl ~ O h
~ ~O 00 I ~ a~ ~ .
E~¦ U~ ~ 3a ~I N C ~ 1 ~5 o
.
27-

0'~7~
C_5718 EXAMPLE 2
A hydraulic ~luid was prepared havlng the ~ollowing
compositlon:
Percent by
Welght
Borate Ester
H5(OC2H4)3 ~3-B 51~80
2Hs(CC2H4)4~ 3-B 18.20
Hs(OC2H4)2~3-B 14.35
~H30(C2H40)~72CH2 lOo 00
Mixed isopropanolamines
(10-15~ mono, ~0-50%.di, 40-50~ tri) 3.00
Glycerin - 2.00
Butynediol 0.50
~ioctyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.) 0.10
Sodium nitrite : 0-05
~0. 00
Properties:
Reflux boiling point (dry) 515F
Re~lux boiling point (wet) -:
(3.5 ml~ water ~ 100 ml. ~luid) 365F.
Viscosity at -40Fo 1852 csO
_28-
~; ... . . .

~ ~.C~ t 7
C_5718 EXAMPLE 3
A hydraulic ~luid was prepared having the ~ollowlng
compositlon:
Percent by
Weight
Borate Ester
Hs(OC2H4)3 ~3.B 51.80
~ 2H5(0C2Hg) ~ 3-B 18.20
Triethylene glycol monoethyl ether 19.35
~ H30(C2H40~ 2CH2 5~00
Mixed isopropanolamines
(10-15% mono, 40~50~ dl, 40~50% tri) 3~00
Glycerin 2.00
Butynediol o. 50
Dioctyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.) 0.10
Sodium nitrite o.o5
., 100. 00
Properties:
Reflux boiling point (dry) 481Fo
Reflux boiling point (wet)
; (3~5 ml. water + 100 ml. ~luid) 339F.
V1soos1ty at -40F. 1515 8-
.
_29-
, . ,

~ ()7 7~
C-5718 EXAMPLE 4
A hydraulic ~luid was prepared having the following
compo~ition:
Peraent by
. Weight
Borate Ester
H5(0C2H4)3 ~9-B 51.80
H5(0C2H4)~ ~3-B 18.20
Triethylene glycol monoethyl ether 4-35
~ H30(C2H40~ 2CH2 20.00
Mlxed i~opropanolamines
(10-15~ mono, 40-50~ di, 40-50% tri)3.00
` Glycerin 2.00
Butynediol -5 :
Dioctyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.) 0.10
Sodlum nltrite . 0-05
100. 00 ~:
Properties:
Re~lux boiling point (dry) 453F.
Re~lux boillng point (wet)
(3.5 ml. water + 100 ml. ~luid)333F-
Vl~co~ity at -40F. 720 c~
.
~: .
~. .
" .
, .
. ' . ~
,,~,.. . . .

~ 7
C-5713 E~MP.IE 5
A hydraulic ~luid was preparecl having the ~ollowing
composition:
Percent by
Weight
Borate Ester
H5(oc2H4)3o73-B 51.80
~ 2H5(oC2H4)4o73_B 18020
Triethylene glycol monoethyl ether 19.35
r H30(C2HgO) ~ 2CH2 5
Mixed isopropanolamines
(10-15~ mono, 40-50~0 di, 40-50~0 tri) 3.00
Glycerin 2.00
Butynediol 0050
Dio¢tyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.) 0.10
Sodium nitrite 0.05
100- 00
Properties: -
Reflux boiling point (dry) 505Fo
Re~lux boiling point (wet)
(3.5 ml. water ~ lOQ ml. fluid)345 F~
Viscosity at -40Fo 1865 CS.
-31-
,

`7
C-5718 EXAMPL$ 6
A hydraulic ~luid was prepared having the ~ollowlng
composition:
Percent by
~; Weight
Borate Ester
H5(0C2H4)3 ~3-B 51.80
~H5(OC2H4)4 ~3-B 18.20
Triethylene glycol monoethyl ether 4.35
~ H30(C2H40) ~2CH2 20~00
Mlxed isopropanolamines
(10-15% mono, 40-50% di, 40-50% tri)3.00
Glycerln ~ 2.00
Butynediol 0.50
Dioctyl diphenylamine (Van Lube 81 produced by
R. T. ~anderbilt Co.3 0~10
Sodium nitrite 0.05
rOO. OO ~ ~
Properties:
Reflux boiling point (dry) 523F.
Re~lux boiling point (wet) :
(3.5 ml. water + 100 ml. fluid) 354~. :
Vlcoo~lty at -40~. 1415 o~.
.
:
,
_32_
.

` ~U ~)''37
C-5718 EXAMPLE ~
` A hydraulic fluid was prepared having the ~ollowing
¢omposition:
Percent by
Wei~ht
Borate Ester
r 2Hs(oc2H4)3 ~3-B 51.80
~ 2H5(0C2H4) 4~3 -B 18020
Triethylene glycol monoethyl ether 19.35
~ 4H90(C2H40~ 2CHz 5
: Mixed isopropanolamines
(10-15% mono, 40-50~0 di, 40-50% tri)3.00
Glycerin 2.00
Butynediol 0050
Dioctyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.) 0.10
Sodium nitrite 0.05
100. 00
Propertle~: -
; 20 Reflux boiling point (dry) 502F
Re~lux boiling point (wet)
(3.5 ml. water ~ 100 ml. ~luid)~4~ F.
ViDoo~1ty at -40~F. 1771 oa.
'
'
-3~-
. ''
.: .

~ ) 7
C_5718 EXAMPLE 8
A hydraulic ~luid was prepared having the ~ollowing
composition:
Percent by
Wei~ht
Borate Ester
zH5(0C2H4)3 ~3-B 51 ~ 80
~ zH5(0C2H4) ~ 3-B 18 ~ 20
Triethylene glycol monoethyl ether 19. 35
r H30(CzH40)~ zCHz 5000
Mixed isopropanolamines
(10-15% mono, 40~50% di, 40~50% tri) 3~00
Glycerin 2~ 00
Butynediol -5 ~:
Dioctyl diphenylamine (Van Lube 81 produced by
R. T. Vanderbilt Co.)0.10
Sodlum nitrite 0.05
lOOo 00
Propertie~:
Re~lux boiling point (dry) 504Fo
Re~lux boiling point (wet)
(3.5 ml. water ~ 100 ml. ~luid) 343
Viscosity at _40F~ 2083 c~
.'
-34-

J 7
C-5718 EXAMPLE 9
A hydraulic ~luid was prepared having the ~ollowlng
compo~ition:
Peraent by
Wei~ht
~H3 (OC2H4)35~73-13 20. 00
Triethylene glycol monomethyl ether 58.00
~Z2H50(C2H40)~72CH2 15.00
Polyethylene glycol (M.W. 300) 5000
Dlethanolamine 2.00
100. 00
Properties:
Reflux boiling point (dry) 490F.
Re~lux bo~ling point (wet)
(3.5 ml. water ~ 100 ml. ~luid)308 F.
Viscosity at -~0Fo 522.3 cs.
EXAMPLE 10
A hydraulic ~luid was prepared having the ~ollowing
composition: -
Weight
~2H5 ( OC2H4 ) 2S~73-B 25.00
Tetraethylene glycol monoethyl ether 15.00
Triethylene glycol monoethyl ether 39.00
~4Hgo(C2H40)972CH2 20.00
Monoethanolamlne 1.00
100. 00
Properties:
Reflux boiling point (dry3 436F.
Reflux boiling point (wet)
(3.5 ml. water ~ 100 ml. ~luid)30~ F.
Visco~ity at -~0F. 607.1 c~.
-35-

~ `7
C-5718 EX~MPLE 11
A hydraulic fluid ~Jas prepared having the ~ollowing
composition: ~
Percent by
Weight _
~ H3(0C2H~) 9 (OCH2CHCH3)(OC2Hg )~3 -B 30.00
Triethylene glycol monomethyl ether 57.00
H30(CzH40) ~2CH2 10.00
Triisopropanolamine 3.00
100-
Propertie~:
Reflux boiling poin~ (dry) 504F.
Re~lux boiling point (wet)
(3.5 ml. water + 100 ml. flu~d) 308F
Viscosity at -40F. 516.3 cs.
EXAMPLE 12
A hydraulic ~luid was prepared having the ~ollowing
composition:
- Percent by
~20 - Wei~h~
4Hg0(50% C2H40 + 50% CH2CHCH30) ~3B 35.00
(Prepared using Union Carbide glycols -
*UCON 50-B55)
Triethylene glycol monoethyl ether 22.00
Polyethylene glycol (M.W. ~00) 10.00
H30(C2X40) ~2CH2 3
Diisopropanolamine 2.5
Dioc~yl diphenylamine tVan Lube 81 produced by
R. T. Vanderbilt Co.) 0.5
'' ' '100.00 ,
Properties:
- Reflux boiling point (dry~ 542F.
; Re~lux boiling point (~et)
(~.5 ml. water + 100 ml. fluid) ~15F.
Viscosity at -40F. 848.8 cs.
" .
* Trade Mark
, ~ .
_~6-

~ C~ 7
C-5718 EXAMPLE 13
A hydraulic ~luid was prepared having the ~ollowing
composition:
Percent by
Wel~ht
Borate Ester
~ H3(OC2H4)3 ~ 3-B 3 ~
Tetraethylene glycol monomethyl ether 22.0
Triethylene glycol monoethyl ether 4200
~ H30(C2H40)~ 2CH2 5
Monoethanolamine 1.0
100. 0
Properties:
Reflux boiling polnt (dry) 467F~
Re~lux boiling point (wet) 321F~
(3~5 ml. water + 100 ml. ~luid)
Viscoslty at -40F. . 660 c8
EXAMPLE 14
A hydraullc ~luid was prepared havlng the ~ollowlng
composltlon:
Percent by
Wei~ht
Borate Ester
H3(OC2H4)3 J3_B 20.0
~ 2Hs(OC2H4)2 ~3-B 15 ~ 0
Trlethylene glycol monomethyl ether 20.0
Trlethylene glycol monobutyl ether 17~0
Polyethylene glycol (M.W. 300) 15~0
H50(C2H40)2J 2CH2 10.0
Monolsopropanolamine 3~ 0
Propertles:
Reflux bolllng polnt (dry) 445Fo
Re~lux boiling point (wet) 321F~
(3~5 ml. water + 100 ml. ~luid)
Viscosity at -40F. 2437 cs
~37~

)f~ 7~
C-5718 EXAMPLE 15
A hydraulic ~luid was prepared having the ~ollowlng - :
composition:
Percent by
Wei~ht
Borate ester
H5(0CzH4)3 ~3-B 2906
~ ~ 2H5(0C2H4)4~3-B 1004
: Tetraethylene glycol monoethyl ether 10.0
Triethylene glycol monoethyl ether 41.0
: ~ gHgO(C2H40) ~ 2CH2 50
M~thyl diethanolamine 4.0
0000
Propertie~:
~' Reflux boiling point (dry) 487F.
Reflux boiling point (wet) 319Fo
.5 ml. water + lOQ ml. ~luld)
Viscosity at -40F. 901 c~ -
., .
,. . . .
,
. . . ..
- .
~8

Representative Drawing

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Administrative Status

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Event History

Description Date
Inactive: IPC deactivated 2013-01-19
Inactive: IPC assigned 2012-03-06
Inactive: IPC assigned 2012-03-06
Inactive: IPC assigned 2012-03-06
Inactive: IPC assigned 2012-03-06
Inactive: First IPC assigned 2012-03-06
Inactive: Expired (old Act Patent) latest possible expiry date 1997-12-02
Grant by Issuance 1980-12-02

Abandonment History

There is no abandonment history.

Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
OLIN CORPORATION
Past Owners on Record
ARTHUR W. SAWYER
DAVID A. CSEJKA
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Claims 1994-04-20 7 241
Abstract 1994-04-20 1 16
Drawings 1994-04-20 1 8
Descriptions 1994-04-20 37 1,185