CA1199906A - Water-based hydraulic fluids containing hydroxyalkylated isocyanurates - Google Patents
Water-based hydraulic fluids containing hydroxyalkylated isocyanuratesInfo
- Publication number
- CA1199906A CA1199906A CA000410516A CA410516A CA1199906A CA 1199906 A CA1199906 A CA 1199906A CA 000410516 A CA000410516 A CA 000410516A CA 410516 A CA410516 A CA 410516A CA 1199906 A CA1199906 A CA 1199906A
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- Prior art keywords
- hydraulic fluid
- weight
- water
- corrosion inhibitor
- phase corrosion
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- 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
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/082—Inorganic acids or salts thereof containing nitrogen
- C10M2201/083—Inorganic acids or salts thereof containing nitrogen nitrites
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/085—Phosphorus oxides, acids or salts
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/087—Boron oxides, acids or salts
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
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Abstract
WATER-BASED HYDRAULIC FLUIDS
CONTAINING HYDROXYALKYLATED ISOCYANURATES
Abstract of the Disclosure Disclosed are water-based, fire resistant hydraulic fluids which comprise:
(a) about 20% to about 60% by weight water;
(b) a sufficient amount of a hydroxyalkylated isocyanurate to form a hydraulic fluid with a viscosity from about 100 SUS to about 400 SUS at 100°F, said hydroxyalkylated isocyanurate having the formula:
wherein x, y and z are each from about 3 to about 15, and each R is individually selected from hydrogen and methyl;
(c) about 0.01% to about 5% by weight of a liquid phase corrosion inhibitor; and (d) about 0.01% to about 5% by weight of a vapor phase corrosion inhibitor.
These water-based isocyanurate fluids are comparable to known water-based glycol fluids in important operating properties such as lubricity and fire resistance, and have the additional advantage of offering a substantial reduction in the flammability of the residual material resulting from loss of water content.
CONTAINING HYDROXYALKYLATED ISOCYANURATES
Abstract of the Disclosure Disclosed are water-based, fire resistant hydraulic fluids which comprise:
(a) about 20% to about 60% by weight water;
(b) a sufficient amount of a hydroxyalkylated isocyanurate to form a hydraulic fluid with a viscosity from about 100 SUS to about 400 SUS at 100°F, said hydroxyalkylated isocyanurate having the formula:
wherein x, y and z are each from about 3 to about 15, and each R is individually selected from hydrogen and methyl;
(c) about 0.01% to about 5% by weight of a liquid phase corrosion inhibitor; and (d) about 0.01% to about 5% by weight of a vapor phase corrosion inhibitor.
These water-based isocyanurate fluids are comparable to known water-based glycol fluids in important operating properties such as lubricity and fire resistance, and have the additional advantage of offering a substantial reduction in the flammability of the residual material resulting from loss of water content.
Description
9~G
WA~ER-BASED HYDRAULIC FLUIDS
CONTAINING HYDROXYALKYLATED ISOCYANURATES
Background of the In~ention 1 Field of-the Invention Tha present invention relates ~o water-based~
fire resistant hydraulic fluids containing hydroxyalkylated isocyanurate base stocks.
WA~ER-BASED HYDRAULIC FLUIDS
CONTAINING HYDROXYALKYLATED ISOCYANURATES
Background of the In~ention 1 Field of-the Invention Tha present invention relates ~o water-based~
fire resistant hydraulic fluids containing hydroxyalkylated isocyanurate base stocks.
2. Description of the Prior Art , Water-based hydraulic fluids haviny fire-resistant propert'ies are well known.
See R. E. Hatton, Introduction to Hydraulic' Fluids, Chapter 13, "Water-Based Fluids", pages 273-2~7, Reinhold Publi~hing Corporation (1962).
Such water-based fluids have been used satisfactorily in hydraulic systems containing ~ane, gear or axial-piston pumps. I~he fire resis~ance o~ these water-based fluids has depended solely upon their water content, and they were generally considered to be satisfactorily ire resistant as long as the watex content was maintained. ~f the water is ~llowed to boil away or to evaporate by prolonged exposure to elevated temperatures, the residual material will burn when ignited.
Much of the work on the development of water-based fluids has centered around the use of glycol base stocks such as ethylene glycol. See J~ E. Brophy et al, "Aqueous Nonflammable Hydraulic Fluids", Industrial and Engineering Chemlstr~, Vol. 43, NoO 4, pag~s 884-g96 ~April 1954). These water-based glycol fluids require a water-soluble ~hickener to increase the visco~ity to an acceptable level, as well as requiring additives to impart corrosion-preventive properties and to enhance anti-wear and lubricity characteristics to the final product.
Therefore, thexe is a need in the art to find a water-based hydraulic fluid which will lea~e a xesidual that resists burning when subjected to ignition condition. Furthermore, there is a need for a water-base~ hydraulic fluid which requires fewer or a lesser amount of additives to ~implify manufacturing procedures. The present invention offers a solution to both of these needs.
Separately, hydroxyalkylated isocyanurates have been known as functional fluids~ See U.S, Patent No. 3,859,284, which issued to Formalni et al on January 7~ 1975~ Ho~ever, their desirable characteris-tics of ~1~ being fire resistant in water based fluids even after the water is removed and (2~ possessing good lubricating propert~es while in combination with water were not known prior to the pre~ent invention.
Brief Summary of the Invention Accordingly, the present invention is directed to, as novel compositions-of-matter, water-based hydraulic fluids which comprise ~a) about 20~ to about 60% by weight water;
(b) a sufficient amount of a hydroxyalkylated isocyanurate to form a hydraulic fluid with a visGOSity from about 100 Saybolt Universal Seconds (SUS~ to about 400 Saybolt Universal Seconds (S~S) at 100F, saia hydroxyalky-~
lated iSocyanurate hav7n~ the ~ormula (A):
H~-OH2C -HC) - T~ ~ - (CH--CHzO-~ H (A) O~/ ~ N ~ \\O
(CH--CH2O-~ H
wherein x, y and z are each from about 3 to about 15 and each R is individually selected fro~ hydrGgen and methyl;
(c) about 0.01% to about 5% ~y weight of a liquid phase corrosion inhibitor; and (d) about 0.~1% to about 5~ by weight of a vapor phase corrosion in~ibitor.
The present invention is also directed to the process of using the above noted water-based : isooyanurate 1uld~ in hydraulic operations~
~ ~ --D ~
The hydroxyalkyla~ed isocyanura~e base stock of the present invention may be prepared either (1) by the catalytic alkoxylation of cyanur.ic acid or (2) by the catalytic al~oxylation of tris(2-hydroxyethyl) isocyanurate (TH~IC). The former method is described in U~S~ Patent No. 3,26~,694, which issued to Walles et al on August 9, 1966~ The latter synthesis is described in U.S. Patent No. 3,741~966, which issued to 110 Weedon et al on June 26r 1973l and in U.S. Patent No.
See R. E. Hatton, Introduction to Hydraulic' Fluids, Chapter 13, "Water-Based Fluids", pages 273-2~7, Reinhold Publi~hing Corporation (1962).
Such water-based fluids have been used satisfactorily in hydraulic systems containing ~ane, gear or axial-piston pumps. I~he fire resis~ance o~ these water-based fluids has depended solely upon their water content, and they were generally considered to be satisfactorily ire resistant as long as the watex content was maintained. ~f the water is ~llowed to boil away or to evaporate by prolonged exposure to elevated temperatures, the residual material will burn when ignited.
Much of the work on the development of water-based fluids has centered around the use of glycol base stocks such as ethylene glycol. See J~ E. Brophy et al, "Aqueous Nonflammable Hydraulic Fluids", Industrial and Engineering Chemlstr~, Vol. 43, NoO 4, pag~s 884-g96 ~April 1954). These water-based glycol fluids require a water-soluble ~hickener to increase the visco~ity to an acceptable level, as well as requiring additives to impart corrosion-preventive properties and to enhance anti-wear and lubricity characteristics to the final product.
Therefore, thexe is a need in the art to find a water-based hydraulic fluid which will lea~e a xesidual that resists burning when subjected to ignition condition. Furthermore, there is a need for a water-base~ hydraulic fluid which requires fewer or a lesser amount of additives to ~implify manufacturing procedures. The present invention offers a solution to both of these needs.
Separately, hydroxyalkylated isocyanurates have been known as functional fluids~ See U.S, Patent No. 3,859,284, which issued to Formalni et al on January 7~ 1975~ Ho~ever, their desirable characteris-tics of ~1~ being fire resistant in water based fluids even after the water is removed and (2~ possessing good lubricating propert~es while in combination with water were not known prior to the pre~ent invention.
Brief Summary of the Invention Accordingly, the present invention is directed to, as novel compositions-of-matter, water-based hydraulic fluids which comprise ~a) about 20~ to about 60% by weight water;
(b) a sufficient amount of a hydroxyalkylated isocyanurate to form a hydraulic fluid with a visGOSity from about 100 Saybolt Universal Seconds (SUS~ to about 400 Saybolt Universal Seconds (S~S) at 100F, saia hydroxyalky-~
lated iSocyanurate hav7n~ the ~ormula (A):
H~-OH2C -HC) - T~ ~ - (CH--CHzO-~ H (A) O~/ ~ N ~ \\O
(CH--CH2O-~ H
wherein x, y and z are each from about 3 to about 15 and each R is individually selected fro~ hydrGgen and methyl;
(c) about 0.01% to about 5% ~y weight of a liquid phase corrosion inhibitor; and (d) about 0.~1% to about 5~ by weight of a vapor phase corrosion in~ibitor.
The present invention is also directed to the process of using the above noted water-based : isooyanurate 1uld~ in hydraulic operations~
~ ~ --D ~
The hydroxyalkyla~ed isocyanura~e base stock of the present invention may be prepared either (1) by the catalytic alkoxylation of cyanur.ic acid or (2) by the catalytic al~oxylation of tris(2-hydroxyethyl) isocyanurate (TH~IC). The former method is described in U~S~ Patent No. 3,26~,694, which issued to Walles et al on August 9, 1966~ The latter synthesis is described in U.S. Patent No. 3,741~966, which issued to 110 Weedon et al on June 26r 1973l and in U.S. Patent No.
3,859~284, which issued to Formaini et al on January 7, 1975. Furthermore, a two-step method for making these hydroxyalkylated isocyanurates is described in UOS.
Patent No. 3,870~716, which issued to Belsky et al on March 11, 19751 wherein a first step of forming THEIC
from cyanuric acid is carried out in the presence of an alkaline catalyst followed by a second step of ~orming the hydroxyalkylated adduct in the presence of an acid catalyst.
~hen THEIC is used as the precursor for the - present hydroxyalkylated isocyanurates, it is preferred to employ boron trifluoxide etherate as an acidic catalyst and reaction temperatures of about 130C to about 140C and reaction pressures from atmospheric pressure to about 50 psigO Of coursP, the pre~ent invention is not to be limited to any specific method for making the hyd~oxyalkylated isocyanurates and any conventional method for making these compounds may be used.
The oxide precursors of these hydroxyalkylated isocyanurates are commercially avail--able chemicals which may be obtained ~rom many sources.
Mixtures o~ different oxides ~e~g~ ethylene oxide (E0) and propyl~ne oxide ~P0)] may also be employed as reactants, either added sequentially or mixed together.
It should be understood that the number of ~oles o~ ox~de reacted at each o~ the three reactive s~es o~ ~he ~socyanurate molecule will not always be t~e same. For example, if 12 moles of EO ~ere reacted to l mole of THEIC, ~t does not necessarily follow that
Patent No. 3,870~716, which issued to Belsky et al on March 11, 19751 wherein a first step of forming THEIC
from cyanuric acid is carried out in the presence of an alkaline catalyst followed by a second step of ~orming the hydroxyalkylated adduct in the presence of an acid catalyst.
~hen THEIC is used as the precursor for the - present hydroxyalkylated isocyanurates, it is preferred to employ boron trifluoxide etherate as an acidic catalyst and reaction temperatures of about 130C to about 140C and reaction pressures from atmospheric pressure to about 50 psigO Of coursP, the pre~ent invention is not to be limited to any specific method for making the hyd~oxyalkylated isocyanurates and any conventional method for making these compounds may be used.
The oxide precursors of these hydroxyalkylated isocyanurates are commercially avail--able chemicals which may be obtained ~rom many sources.
Mixtures o~ different oxides ~e~g~ ethylene oxide (E0) and propyl~ne oxide ~P0)] may also be employed as reactants, either added sequentially or mixed together.
It should be understood that the number of ~oles o~ ox~de reacted at each o~ the three reactive s~es o~ ~he ~socyanurate molecule will not always be t~e same. For example, if 12 moles of EO ~ere reacted to l mole of THEIC, ~t does not necessarily follow that
4 moles of EO were added at each site. Instead, it may be in some i~stances that only 3 moles, o~ none, ~11 react at one site and 5, or more, moles may xeact at another site. Furthermore, it should be understood t~at the tot~l num~er of alk~lene oxide moles on each resultiny adduct molecule Will ~e statistically dis-tribu~ed. Thus, the values f~r x, y and z in ~ormula (A) each represent the average amount of alkylene oxide units per reaction site and that the actual number may be less or greater than that amount.
These hydroxyalkylated (i.e~ hydroxyethylated and hydroxypropylated and mixtures thereofl isocyanurates are viscous fluids. Unlike ethylene and propylene glycols, they do not xequire additional th~ckeners to make w~ter-based hydraulic fluids of acceptable viscosities and lubricity. Generally, the viscosities of these hydroxyalkylated isocyanurates are from about 500 centistokes (cSt) to about 800 centi-stokes (cS~ at 100F, which when converted to SUS
vallles by the appropriate tables in ANSI/ASTM 2161-79, equals ~rom about 2300 S~S to about 3700 SUS~ For the most common use~ of water-hased hydraulic fluids, such as with vane-type pU~p5, the hydraulic 1uid may have viscosities ;n the ran~e ~rom about 100 SUS to about 400 SUS, preferably from about 150 SUS to about 300 SUS.
Accordingly, hydraulic ~luids having viscosities any-where in the 100 SUS to ~OQ SUS xanye (at 100~) may be pxep~red ~y var~n~ the ratio o~ i~oc~nurate base stock to ~ater. ~efe~ably, these Yi~cosIti2s are more easily ach;~eved when the ~mou~ of water i~ the fluid is from about ~2~ to ab~ut 50~ by we~ht and the preferxed amount o~ hydroxylakylated isocyanurate is from about ~ 6 -80% to a~out 25~ ~y wei~ht, dependin~ upon the specific thickeners and additiYes present. Furthermore, it is preferxed that x, ~ and z ~n Fo.rmula (A), above, be ~XQ~ ~bout 4 to about 10.
Another advanta~e of water-based isocyanurate ~lu;~ds o~ t~e present invention over the known water-based ylycol fluids is that these hydroxyalkylated isocyanurates per se ha~e better lubricating properties than the gl~cols. Therefore, lesser amounts o~ anti-wear and lubricit~ additi~es are need~d to achieve the Same lubricatin~ properties.
Besides water and the hydroxyalkylated isocy~nurate base stock, it i5 necessary to add corrosion inhibitors to the hydraulic fluids of the present invention. At least one liquid phase and at least one vapor phase corro~ion inhibitor are needed to prevent corrosion o~ metal hydraulic system parts.
These corrosion inhibitors are necessary because the water would otherwise corrode the metal in which the hydraulic fluid is contained.
Any conventional li~uid phase corrosion inhibitor may be employed~ Mercaptobenzothiazole or its alkali metal salts such as sodium mercaptobenzo-thiazole, tolutriazole~ secondary and tertiary amines and alkali metal borates, phosphates, nitrites, phos-p~ites and sil~cates, or other suitable liquid phase corrosion inhibitors may be employed. Preferably, the ~mount of liquid phase corrosion inhibitors is from about 0.1~ to about 1~ by weight of the total hydraulic ~luid formulation. More preferably~ the amount of liq~id phase corro~ion inhibitors is fxom about 0.2~
to about 0.5~ hy weight Q~ the total fluid formulation.
~ny con~entional yapor phase corrosion in~ibitor ma~ he used~ Vapor phase corrosion inhibitors such as morpholin~, o~ani ~ases such as cyclohexylamlne, dicyclohexylamine, pi:per~dine, and various thiazolines, pyrrolidines and hydrazines are required to protect parts 9~
not completely immersed in the fluid, especially in the flu~d reservoirs which would be ~ulnerable to corrosion above the liquid levei. Pre~erably, the amount of vapor phase corrosion inhibitors is from about 0,5% to about 2% of the total formulation. More pre~erably, this amount may be ~rom about 0.7~ ~o about 1~25~ b~ ~eight o~ the ~otal fluid formulation.
The hydraulic fluids of the present in~ention may be suitable for industrial hydraulic service throughout the temperature range from about -20C to about 65C at atmospheric pressure (hi~her temperatures may be used under pxessurized conditions) and re homogeneous at all temperatures between about -45C to about 80C. T~ey require no special packings or seals or filters 3 These fluids~ besides being fire resistant~
are non-explosive, will not attack ru~ber packings, are corrosion~inAibited, nontoxic, oxidation resistant, and have low pour points, good lubricity and stability in service. Furthermore, they are economical to make.
The hydraulic-type fluid systems in which the ~luids of the pre~ent invention may be used include any system wherein a me~hanical effort is converted to pxessure at a ~irst location, the pressure is transmitted from this first location to a second location via a hydraulic fluid, and the pressure is converted to a second mechanical effort at the second location. Thus, the hydraulic systems contemplated by the present invention include hydraulic brake systems, hydraulic steering mechanisms, hydraulic transmissions, hydraulic jacks and hydraulic li~ts, especially those that re~uir~
a high dagree o~ ~tre resistance. Included among these are the hydrauiic systems used in hea~y equipment and transportation Yeh;cles încluding highway and con~
struction equip~ent, xailways, and aquatic vehicles.
Various additiyes, besides the above-mentioned corrosion inhibitors, may be added to the flu~ds used ~n the systems of this invention to control or mod~f~ per~ormance properties. In~luded among the ~axiou~ types of additIves which can be added to the fluids are thlcken~rs, bu~e~s or pH control a~ents, antioxidants, v~scosit~ index improver~, pour point depressants, lubricat~n~ additi~es, defoamers, stabil~zers, rubber sweiling adjusters, demulsifiers, dyes and odor suppressants~ Generally, the total amoun~ of addltiYes which m~y be incorporated into the fluid composition will yar~ between 0% to about 30%, - preferably rro~ about 0.1~ ~o 20% and more preferably from about 0.2% to about 10% by wei~ht, based on the total wei~ht o~ the fluid formulation.
Thickeners such as polyoxyalkylene glycol-type thickeners such as the ~ater-initiated co-polymers of ethylene oxide and propylene oxide may optionally be added to the ~luids o~ the present invention to effect an increase in the viscosity index of the fluid.
Generally, the amount of thickeners added may be from a~out ~% ~o a~out 20%, preferably ~rom about 0% to about 15%, by weiyht of the total fluid formulation~
However, it should be understood that the addition of thickeners reduces b~th fire-resistance of the residual material and the lubricity of the ~luid.
~uffer~ or pH control agents may optîonally be employed in an amount sufficient to maintain alkaline conditions in the fluid compositions, e.g. at an apparent p~ value o~ about 7 to about 11.5 if desired. Acidity might:accelerate coxrosîon and render some corrosion inhibitor~ ineffecti~e.
Desirablé huf~er3 include potassium laurate and triethanolamine, ammoni~m pho~phate, borates and the like~ These ~u~fers may generally be added to the ~l-u~d3 in amounts from about 0% to about 5% by weight of flu;~d fo~muiationr preferably from about 0.1% to abou~ 1% by we~ht of the mixture.
An antioxidant may optionally be used, i desired. Typical antioxidants include 2~2-di(4-hydroxyphenyl) propane, phenothiazin~, amines such as phenylalphanaphthylamine and hindered phenols such as dibutyl cresol. Generally, the amount of antioxidant used will vary from 0~ ~o about 3% by weight, preerably from about 0.001~ to about 2% by weight, based on the total weight of the fluid formulation.
A defoamer such as a silicone type may be optionally used, if desiredO Genexally, the amount of defoamer used will vary from 0~ to abou~ 0.1% by weight o~ the fluid formulation; preferably, the zmount will b from about 0~01% to about 0.1~ by weight of the formulationO
~dditionally, o~her additives, if desired, .may be incorporated into the fluid composition.
For exampler rubber swelling adjusters su h a~ dodecyl benzene may be used.
The above-noted inhibitors and additives are ~0 - merely ex~mplary and are not intended as an exclusive listing of the many well-kn~wn materials which can be added to fluid compositions to obtain various desired properties~ Other illustrations of additives which may be used can be found in U.S~ Patent : 25 No. 3,377,288, and in Introduction t~ Hydraulic Fluids by Roger Eo Hatton, Reinhold Publishing Corporation t~96~).
The ollo~ing examples depict ~rious embodiments o the present invention; they are intended to bs 111ustrat~é and not limiting in nature.
All parts and percentages are by weight unless otherwi~e ~peciied.
Example 1 To a one-liter steel aut.oclave, 195.9 grams ~0~75 molesl o~ tr~s(2-hydroxyethyl) isocyanurate ~THEIC) and ~.0 ~rams o~ boron trifluoride etherate w~re added~ T~e latter compound ~as used as a catalyst ;~n an amount e~ual to about 1.0~ of the weight of the THEIC~ The autocla~e was sealed and the reaction mixtux~ ~as heated to about 140C to melt the THEIC.
The reaction pressure was maintained at about 50 psig.
Ethylene oxide tEO~ was then added to the autoclave o~er ~ peri~od of a~out 3 hQurs until 436 grams (9.9 moles) EO was char~ed. The reaction mixture was then post-reacted ~or 1 hour at 138-150C. After this post-react~on time, the reactox was cooled to room temperature, vented to remove any unreacted EO, and the contents were weighed (44~.3 grams? and OH number determined (234) which corresponds to a calculated molecular weight of 719~ The approximate structural formula of the product, as calculated from the uptake 3 3O3~(CH2CH2O)4.1H]3 whose formula weight is 6~Q.
A ~ater-based hy~raulic fluid haYing ~ 200 SUS viscos~ty at 100F, comprising 73.G~ by weight of the abo~e hydxoxyalk~lated isocyanurate and 27.0%
distilled water, was prepared and tested for various properties. See Table I for the results of these test~.
- x~-~
The ~droxyalk~lated isocyanurate product made ~n ~x~mple 1 was ~lended with water and a pol~alk~lene glycol thickenerl prepared by base-catalyzed, water initiated copolymerization of a mixture of 75% EO and 25% PO by wei~ht (36,000 cSt at 100F~ ~o fonm a hydraulic fluid haYing a viscosity of 200 SUS at 100F. This fluid comprised 39~0 of th~ isocyanurate product, S0.0% water and 11.0 ~hickener. The fluid was also tested for various prop~rties. See Table I for the results.
lPoly-G~ polyalkylene gl~col thickener concentrate manufactured by Olin Corporation of S~amford, Connecticut.
0~
Example 3 To ~ ~50 ml glass fl~sk equipped wi~h a thermome~er, addition funnel, and a cold finger condenser, 52.~ ~rams (0.2 moles) of T~EIC was added.
The fla~k was heated to melt the THEIC ~at about 131C~ at atmospheric pressure~ Then, 0.52 grams of boron trifluoricle etherate ~as added to the flask, ~ollo~ed by the dropwise addition of 116.3 grams ~2.64 moles) of EO at about 133C to abouk 140C over a period of 6~5 hours. Then, the reaction mixture ~as heated at about 125C for an additional 16 hours, cooled to room temperature and the contents weighed tl59.0 grams) and the OH number was determined (208), which corresponded to a calculated molecular formula of 809. The approximate structural formula of the product, as calculatad by the uptake of EO, was C3N3O3ItCH2CH2)5H]3 whose ormula weight is 790O
A water-~ased hydraulic fluid having about ~OO SUS viscosit~ at 10~F comprising 73.0~ by weight of tha above hyd~oxyalkylated isocyanurate and 27.0~ dist~lled water ~as prepared and tested for various pxoperties. See Table I for the results.
~xampl-e 4 To a 500 ml ~lass ~lask equipped with a the~mometer, ~dd~tion ~unnel and cold finger condenser ~as c~arged 31~3 ~rams tQ.12 moles~ of THEIC. The flask ~as h~ated ~o ~elt the TH~IC a~ atmospheric pressure. Boron trifl~oride etherate (0.1 gram) was t~en ~dded ~o t~le flas~ 156.8 Grams (3.56 moles~ of EO w~s added o~er ~ period o~ 16 hours while main-taining the temperature at ahout 1319C to about 137C at a~mospheric pressure. Boron trifluoride etherate catalyst ~as added durin~ the EO addition as required to sustain the reaction. The total amount of catalyst was 2.8% of the THEIC added (0.89 grams~.
After addi~ion of EO ~as o~er, the reaction mixture was heated at abou~ 125~C fox about 16 hours, cooled to room tempera~ure and the contents wei~hed (173.5 grams) and the OH number was determined (152~ which corresponded ko a ~olecular weight of 1107. The appro~imate structural formula of the product, as 20 . calculated ~y the uptake o~ EO, was C3N303~(CH2CH2Olg gH~3 whose formula weight is 1439.
A w~ter-~ased hydraulic fluid having a 200 SUS ~iscosi~ of 100~F comprising 75. a~ by ~eight of this i~ocyanurate product and 25.0% by weight of distilled ~ater was then prepared and tested. The results o~ those tests are in Table I.
_xamp;le 5 ~ hydr~y~lk~lated isocyanurat~ compound was pxepared ~ e continuous addition of 41.4 lbs. of EO
~o 15.4 l~s. of THEIC and 60 grams of BF3 etherate in a 10-gallon reactor~ The reactor was heated to 295F to melt the T~IC at which point agitation and EO addition ~ere be~un. Only half of the EO had been added ~hen the pressure re~ched its maximum of 65 psig.
A second 60 gram catalyst charge was added to the ~apor ~p~ce above t~e li~uid reaction mixture and the run continued until the EO was consumed. The resultin~
~luid had an 0~ number of 205. The molecular weight was calculated from the 0~ number to be 821. The average composition fxom calculated molecular weight lS was C3N3o3~cH2c~2o)5~2 ]3 A two quart batch of hydraulic fluid having a viscosity of approximately 20Q SUS was prepared by mixing 1579.8 grams of the isocyanurate base stock, 630.2 grams of distilled water, 11.0 grams of morpholine and 0.4 ~x~ms of SAG-10 silicone defoaming a~ent2 in a beaker. The pH was raised to 9,5 by the additiQn of 14~6 grams o~ 1-amino-2-propansl. See Tables I and TI for test results. The final compo-sition of the fluid was:
2Manufactured by Union Car~ide Co. o~
Ne~ ~ork, ~ew York.
~g~
- ~5 -1569.8g Hydroxyalkylated isocyanurate 70.52~
630.2g Distilled water 28.31%
ll.Og Morpholine 0.49%
14~6g 1-~mino-2-propanol 0,66%
0.4g Silicone defoaming agent 0.02%
~ 16 -The hydro~yalkylated isocyanurate product ~r t~is ex~mple ~as prepared by a reaction similar to that of Example 5 except that only 34.4 lbs. of EO
~as added and the 60 ~rams of catalyst was charged into the melted THEIC~ No further catalyst addition was necessary~ T~e resul~ing fluid had an OH number of 195 and as in ~xample 5, the molecular weight wa~
calculated to be 845 which corresponded to an average 3 3 3I cH2cH2o)5~4H]3.
Two quarts of hydraulic fluid having a viscosity of approximately 200 SUS were prepared. The same polyoxyalkylene glycol thickener (36,000 cs at . 100F) as used in Example 2 was used to increase the ~iscosit~ index. The viscosity of the thickener allows a lower isocyanurate 1uid to water ratio to be used. Corrosion lnhibitors, buffers and defoamer were also added. Two hundred grams of thickener were dissolved in 925~6 grams of water with stirring and heating ~ollowed by the addition of 7B8.4 gra~s of the base stock. An additi~e package was prepared on adding 4 grams of rnercapto~enzothiazole, 18 grams o~ morpholine and la ~rams of ~riethanolamine to 50 grams of 20% aqueous potassium laurate bu~fer solution~
This package was blended with the fluid along with four ~rams of potassium nitrite dis~olved in four grams of water. Finally, 6 drops (0.4 grams) of SA&-10 defoamer were added. The composition of the fluid was:
.
925.6g Distilled watex 46.27 788.4g Hydroxyalk~lated isoc~anurate 39.41 200~0g Polyalkylene glycol ~hickener 10.00 50.0g 20% Aqueou~ pot~ssiu~ l~urate 2.5 %
4.0g Mercaptobenzothiazole 0.20%
3L ~ ? ?
18.0g Morpholine 0.90%
lO.Og Triethanolamine 0~5 %
4.0g Potassium nitrite 0.~ %
0.4g SAG-10 silicone defoaming agent 0.02 This fluid was also tested. See Tables I and II.
Example 7 The hydro~yalkylated isocyanurate product fo~
this f~rmulation was prepared by a reaction similar to that described in Example 6. ~he resulting product had an OE number o~ 209. I~s molecular weight was calculated to be 805 which corresponds to an average composition of: C3N303~(CH~CH~O)5 1H]3~
~wo quarts of h~draulic ~luid ha~ing ~ ~iscos~ty of approximateIy 275 SUS at 100~F were prepared as in Example 6 and tested.tsee Tables ~ and II)e The 1u~d had the follo~ing composition:
1603?8y H~droxyalkylated isocyanurate 72.89%
499.4g Distilled ~ater . 22,69%
55.0g 20% Potassiu~ laurate solution 2.50%
8.8g 50% Sodium mercapto~e~zothiazole ~aqueous solut~Qn) 0.40 2q2g Tolutri~zole 0~10~
19~8~ Mo~phol~ne OD90%
11.0g T~ietha~olamine 0.50%
0.4g ~AG~10 ~ COn~ de~oam~g agen~ 0.20 E~
The hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7.
Ab~ut-four quarts o hy~raulic fluid;~avi~g 200 SUS vi5c05ity at 100F were prepared and tested (see Tables I and II)4. The fluid had he following composition:
2893~ag Hydroxyalkylated isocyanurate 68~89%
1121.4g Distilled wa~er 26.69%
105.0g 20% Potassium laurate (aqueous solution) 2~50%
16.8g 50% Sodium mercaptobenzothiazole laqueous solution) 0.40%
4.2g Tolutriazole 0.10%
37.8g Morpholine 0.90%
21.0g Triethanolamine 0.50~
O.~g SAG~10 silicone defoaming agent0,02%
0~ ~
Exam~le 9 The hydroxyalkylated lsocyarlurate product ~or this formulation was the same as in Example 7.
About four quarts of hydraulic fluid having 150 SUS viscosity at 100F were prepared and tested (see Ta~les I and II). The fluid had the following composition 2600O0g Hydroxyalkylated isocyanurate 64.9g%
1224.0g Distilled water 30O59%
lOO.Og 20% Potassium laurate (aqueous solution) 2.50 16.0g 50% Sodium mercaptobenzothiazole (aqueous solution) 0.40%
4.0g Tolutriazole 0.10%
36.0g Morpholine 0.90%
20.0g Triethanolamine 0.50~
0.8g SAG-10 ~ilicone de~oaming agent 0.02%
990~ !
_ 21 -~1~'1 The hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7. About four qu3rts-o~ hydrauli~ fiuid:having 100 SU~ vis~o~ity at 100F were prepared and tested (see ~ables I and II~v The fluid had the following composition:
2268.6g ~y~roxyalkylated isocyanurate 59.69%
1364.2g Distilled water 35.89%
95,0g 20% Potassium laurate (aqueous solutio~) 2.50%
15~2g 50% Sodium mercaptobenzothiazole (aqueous solution) 0.40%
3.8g Tolutriazole 0.10%
34.2g Morpholine 0990 l9.0g Triethanolamine 0~50%
0.6g SAG-10 silicone de~oaming agent Q.Q2%
- ~2 The utility of the fluids prepaxed in Examples 1-10 as ~ire-resistant hydraulic ~luids and speci~cally the~r advanta~e as replacements ~or the water ~l~col type~ was established by the determinat.ion of the follo~in~ properties of the isocyanurate based fluids and CGmpar~sOn with the properties of Hou~htosafe 620, a commercial water glycol hydraulic fluid manufactu~ed by EA F. Houghton. The results are ~ummartxed ;n Tables ~ and II.
A) Viscosity (measured by ANSI/ASTM
D-2270-77? - The viscosities at 100F indicate the ability to formulate a hydroxyalkylated isocyanurate base stock to meet the viscosity specifications of the most commonly used pumps, The kinematic viscosity in centistokes was measured and converted to SUS values b~ the appropr~ate tables Xound in ANSI/AS~M 2161-79.
B) Yiscosity Index (measured by ANSI/ASTM
D-2270-79) ~ The viscosity of the fluids will vary . during use due to chan~es in the ~luid temperature.
The hydraul~c system may not operate properly if the ~luid beco~es too thin or too thickq The viscosity ~ndex (VI~- predicts the extent of these changes with a higher value indicating less of a change. A VI of at least 100 would be considered suitable. Only the fluid of Example 3 failed to mePt these criteria. Also, the 1uids employin~ thickener are seen to have VI's superîor to those ~luids without it. The VI's were calculated by utilizin~ the ~alue ~or 100F viscosity and an est~nated value for 21~ ~iscosity obtained by extrapolation on the A~TM 5t~ndard Vi~cosity Temper~ture chart u~ z~n~ the vlscosit~ Yalues at 100~F and either 130~-~ or 150~F.
C) Pour Point ~measured by ANsI/Asrr~
D-97 66 ~1971~] - The pour points of the fluids are important ~f they are to be shipped, stored or utilized outdoors ~n cold we~ther. E~cept for the fluid oE
E-~ample 5 which included a thickener, all of the tested Xluids had po~r point ~lues which would render them suitable for use at temperatur s below 0F.
D) Four Ball ~ear Test ~measured by ANS~/ASTM D-2266-~7 ~1977)~ - Lubricity testing of th~
fluids is required since a hydraulic fluid must separate ~nd lu~ricate ~he surfaces o~ system co~ponents wh~ch are in close contact. Employing conditions of 1 hour, 130F, 1200 rpm and 40 kg load for the test, the values for most of the isocyanurate based fluids were equal to or better than that o~
Houghtosafe 620. The fluids with higher values than Houghtosafe 620 still exhibited adequate lubricity performance.
E) Power Steering Pump Test - A test such as the Four Ball ~ear Test i5 useful to screen preliminary formulations. Such a test cannot, however, accurately predict pump performance and thus the fluid must be run through a pump test under end-use conditions to determine whether it has sufficient lubricity. The fluids were tested in a Saginaw power steering pump ha~ing a ~luid capacity of 1000 cc.
The rotor, rin~ and vanes o~ the pump are weighed prior to operation. The pump is then assembled and operated for 4 hours ~t a ~luid exit temperature o~ 150F and a pump outlet pressure of 500 psig. An external coolin~ coil ;n a water ~ath ma~ntaIns temperature control and ~ xel~e~ valve ~aintains the system pressure. At the end o~ the 4~hour period~ the pump is disassembled, the parts wei~hed and the weight 1055 recorded. The pump is re~assembled and operated under the same conditions for anot~er 24 hours. The weight loss occurring after the completion of the two cycles is reported as a measure of wear and should b~ less than about 150 mg for acceptable fluids. Resul~s are given in Table I.
F) Wick Flammability Test ~measured by U,S.
Bureau of Mines 5chedule 30~ July 1, 1978) - The test simulates fluid soaked in absorbent, flammable material and exposed to open flamesO It is performed by soaking a pipa clean~r ~n the fluid and cycling it into and out of a laboratory burner flame at 25 cycles/min. until a self-sustaining flame is attained.
The flammability of the fluids was compared by testing them as is, and after varying amounts of evaporative water loss. Thus, three samples were prepared, one was left in an opan petri dish at room temperature~ one was placed in an oven at 150F for 2 hours and one was placed in an oven at 150F for 4 hours. The Bureau of Z0 Mines standard is th~t the number of cycles before - attaining a self-sustainin~ flame sh~uld be 18 or more for the 2-hour sample and 12 or more for the 4-hour sample. As is seen in Table II, the residues of the isocyanurate based fluids retain a significant measure o~ their i~nition resistance while the residue o~ the glycol-based fluid does not.
In summary, the isocyanurate water-based ~luids are comparable in physical properties and lubricity characteristics to typical water glycol fire-resistant hydraulic fluids, but offer a substantial reduction in the flammability of the residual material resul~ing from loss of water content.
9~
Fluids of t~e present invention such as ~hese ma~ be ~esirable for improviny safety in Naval Sh~p h~draulic systems, die casting machines, forging and extrusion presses~ injection moldtng machines, continuous casters, rolling mills, furnace controls, automat~c welders, hydraulic shears, continuous coal miners and mine shuttle cars, and many other uses where the threat of fires existsr a ~
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These hydroxyalkylated (i.e~ hydroxyethylated and hydroxypropylated and mixtures thereofl isocyanurates are viscous fluids. Unlike ethylene and propylene glycols, they do not xequire additional th~ckeners to make w~ter-based hydraulic fluids of acceptable viscosities and lubricity. Generally, the viscosities of these hydroxyalkylated isocyanurates are from about 500 centistokes (cSt) to about 800 centi-stokes (cS~ at 100F, which when converted to SUS
vallles by the appropriate tables in ANSI/ASTM 2161-79, equals ~rom about 2300 S~S to about 3700 SUS~ For the most common use~ of water-hased hydraulic fluids, such as with vane-type pU~p5, the hydraulic 1uid may have viscosities ;n the ran~e ~rom about 100 SUS to about 400 SUS, preferably from about 150 SUS to about 300 SUS.
Accordingly, hydraulic ~luids having viscosities any-where in the 100 SUS to ~OQ SUS xanye (at 100~) may be pxep~red ~y var~n~ the ratio o~ i~oc~nurate base stock to ~ater. ~efe~ably, these Yi~cosIti2s are more easily ach;~eved when the ~mou~ of water i~ the fluid is from about ~2~ to ab~ut 50~ by we~ht and the preferxed amount o~ hydroxylakylated isocyanurate is from about ~ 6 -80% to a~out 25~ ~y wei~ht, dependin~ upon the specific thickeners and additiYes present. Furthermore, it is preferxed that x, ~ and z ~n Fo.rmula (A), above, be ~XQ~ ~bout 4 to about 10.
Another advanta~e of water-based isocyanurate ~lu;~ds o~ t~e present invention over the known water-based ylycol fluids is that these hydroxyalkylated isocyanurates per se ha~e better lubricating properties than the gl~cols. Therefore, lesser amounts o~ anti-wear and lubricit~ additi~es are need~d to achieve the Same lubricatin~ properties.
Besides water and the hydroxyalkylated isocy~nurate base stock, it i5 necessary to add corrosion inhibitors to the hydraulic fluids of the present invention. At least one liquid phase and at least one vapor phase corro~ion inhibitor are needed to prevent corrosion o~ metal hydraulic system parts.
These corrosion inhibitors are necessary because the water would otherwise corrode the metal in which the hydraulic fluid is contained.
Any conventional li~uid phase corrosion inhibitor may be employed~ Mercaptobenzothiazole or its alkali metal salts such as sodium mercaptobenzo-thiazole, tolutriazole~ secondary and tertiary amines and alkali metal borates, phosphates, nitrites, phos-p~ites and sil~cates, or other suitable liquid phase corrosion inhibitors may be employed. Preferably, the ~mount of liquid phase corrosion inhibitors is from about 0.1~ to about 1~ by weight of the total hydraulic ~luid formulation. More preferably~ the amount of liq~id phase corro~ion inhibitors is fxom about 0.2~
to about 0.5~ hy weight Q~ the total fluid formulation.
~ny con~entional yapor phase corrosion in~ibitor ma~ he used~ Vapor phase corrosion inhibitors such as morpholin~, o~ani ~ases such as cyclohexylamlne, dicyclohexylamine, pi:per~dine, and various thiazolines, pyrrolidines and hydrazines are required to protect parts 9~
not completely immersed in the fluid, especially in the flu~d reservoirs which would be ~ulnerable to corrosion above the liquid levei. Pre~erably, the amount of vapor phase corrosion inhibitors is from about 0,5% to about 2% of the total formulation. More pre~erably, this amount may be ~rom about 0.7~ ~o about 1~25~ b~ ~eight o~ the ~otal fluid formulation.
The hydraulic fluids of the present in~ention may be suitable for industrial hydraulic service throughout the temperature range from about -20C to about 65C at atmospheric pressure (hi~her temperatures may be used under pxessurized conditions) and re homogeneous at all temperatures between about -45C to about 80C. T~ey require no special packings or seals or filters 3 These fluids~ besides being fire resistant~
are non-explosive, will not attack ru~ber packings, are corrosion~inAibited, nontoxic, oxidation resistant, and have low pour points, good lubricity and stability in service. Furthermore, they are economical to make.
The hydraulic-type fluid systems in which the ~luids of the pre~ent invention may be used include any system wherein a me~hanical effort is converted to pxessure at a ~irst location, the pressure is transmitted from this first location to a second location via a hydraulic fluid, and the pressure is converted to a second mechanical effort at the second location. Thus, the hydraulic systems contemplated by the present invention include hydraulic brake systems, hydraulic steering mechanisms, hydraulic transmissions, hydraulic jacks and hydraulic li~ts, especially those that re~uir~
a high dagree o~ ~tre resistance. Included among these are the hydrauiic systems used in hea~y equipment and transportation Yeh;cles încluding highway and con~
struction equip~ent, xailways, and aquatic vehicles.
Various additiyes, besides the above-mentioned corrosion inhibitors, may be added to the flu~ds used ~n the systems of this invention to control or mod~f~ per~ormance properties. In~luded among the ~axiou~ types of additIves which can be added to the fluids are thlcken~rs, bu~e~s or pH control a~ents, antioxidants, v~scosit~ index improver~, pour point depressants, lubricat~n~ additi~es, defoamers, stabil~zers, rubber sweiling adjusters, demulsifiers, dyes and odor suppressants~ Generally, the total amoun~ of addltiYes which m~y be incorporated into the fluid composition will yar~ between 0% to about 30%, - preferably rro~ about 0.1~ ~o 20% and more preferably from about 0.2% to about 10% by wei~ht, based on the total wei~ht o~ the fluid formulation.
Thickeners such as polyoxyalkylene glycol-type thickeners such as the ~ater-initiated co-polymers of ethylene oxide and propylene oxide may optionally be added to the ~luids o~ the present invention to effect an increase in the viscosity index of the fluid.
Generally, the amount of thickeners added may be from a~out ~% ~o a~out 20%, preferably ~rom about 0% to about 15%, by weiyht of the total fluid formulation~
However, it should be understood that the addition of thickeners reduces b~th fire-resistance of the residual material and the lubricity of the ~luid.
~uffer~ or pH control agents may optîonally be employed in an amount sufficient to maintain alkaline conditions in the fluid compositions, e.g. at an apparent p~ value o~ about 7 to about 11.5 if desired. Acidity might:accelerate coxrosîon and render some corrosion inhibitor~ ineffecti~e.
Desirablé huf~er3 include potassium laurate and triethanolamine, ammoni~m pho~phate, borates and the like~ These ~u~fers may generally be added to the ~l-u~d3 in amounts from about 0% to about 5% by weight of flu;~d fo~muiationr preferably from about 0.1% to abou~ 1% by we~ht of the mixture.
An antioxidant may optionally be used, i desired. Typical antioxidants include 2~2-di(4-hydroxyphenyl) propane, phenothiazin~, amines such as phenylalphanaphthylamine and hindered phenols such as dibutyl cresol. Generally, the amount of antioxidant used will vary from 0~ ~o about 3% by weight, preerably from about 0.001~ to about 2% by weight, based on the total weight of the fluid formulation.
A defoamer such as a silicone type may be optionally used, if desiredO Genexally, the amount of defoamer used will vary from 0~ to abou~ 0.1% by weight o~ the fluid formulation; preferably, the zmount will b from about 0~01% to about 0.1~ by weight of the formulationO
~dditionally, o~her additives, if desired, .may be incorporated into the fluid composition.
For exampler rubber swelling adjusters su h a~ dodecyl benzene may be used.
The above-noted inhibitors and additives are ~0 - merely ex~mplary and are not intended as an exclusive listing of the many well-kn~wn materials which can be added to fluid compositions to obtain various desired properties~ Other illustrations of additives which may be used can be found in U.S~ Patent : 25 No. 3,377,288, and in Introduction t~ Hydraulic Fluids by Roger Eo Hatton, Reinhold Publishing Corporation t~96~).
The ollo~ing examples depict ~rious embodiments o the present invention; they are intended to bs 111ustrat~é and not limiting in nature.
All parts and percentages are by weight unless otherwi~e ~peciied.
Example 1 To a one-liter steel aut.oclave, 195.9 grams ~0~75 molesl o~ tr~s(2-hydroxyethyl) isocyanurate ~THEIC) and ~.0 ~rams o~ boron trifluoride etherate w~re added~ T~e latter compound ~as used as a catalyst ;~n an amount e~ual to about 1.0~ of the weight of the THEIC~ The autocla~e was sealed and the reaction mixtux~ ~as heated to about 140C to melt the THEIC.
The reaction pressure was maintained at about 50 psig.
Ethylene oxide tEO~ was then added to the autoclave o~er ~ peri~od of a~out 3 hQurs until 436 grams (9.9 moles) EO was char~ed. The reaction mixture was then post-reacted ~or 1 hour at 138-150C. After this post-react~on time, the reactox was cooled to room temperature, vented to remove any unreacted EO, and the contents were weighed (44~.3 grams? and OH number determined (234) which corresponds to a calculated molecular weight of 719~ The approximate structural formula of the product, as calculated from the uptake 3 3O3~(CH2CH2O)4.1H]3 whose formula weight is 6~Q.
A ~ater-based hy~raulic fluid haYing ~ 200 SUS viscos~ty at 100F, comprising 73.G~ by weight of the abo~e hydxoxyalk~lated isocyanurate and 27.0%
distilled water, was prepared and tested for various properties. See Table I for the results of these test~.
- x~-~
The ~droxyalk~lated isocyanurate product made ~n ~x~mple 1 was ~lended with water and a pol~alk~lene glycol thickenerl prepared by base-catalyzed, water initiated copolymerization of a mixture of 75% EO and 25% PO by wei~ht (36,000 cSt at 100F~ ~o fonm a hydraulic fluid haYing a viscosity of 200 SUS at 100F. This fluid comprised 39~0 of th~ isocyanurate product, S0.0% water and 11.0 ~hickener. The fluid was also tested for various prop~rties. See Table I for the results.
lPoly-G~ polyalkylene gl~col thickener concentrate manufactured by Olin Corporation of S~amford, Connecticut.
0~
Example 3 To ~ ~50 ml glass fl~sk equipped wi~h a thermome~er, addition funnel, and a cold finger condenser, 52.~ ~rams (0.2 moles) of T~EIC was added.
The fla~k was heated to melt the THEIC ~at about 131C~ at atmospheric pressure~ Then, 0.52 grams of boron trifluoricle etherate ~as added to the flask, ~ollo~ed by the dropwise addition of 116.3 grams ~2.64 moles) of EO at about 133C to abouk 140C over a period of 6~5 hours. Then, the reaction mixture ~as heated at about 125C for an additional 16 hours, cooled to room temperature and the contents weighed tl59.0 grams) and the OH number was determined (208), which corresponded to a calculated molecular formula of 809. The approximate structural formula of the product, as calculatad by the uptake of EO, was C3N3O3ItCH2CH2)5H]3 whose ormula weight is 790O
A water-~ased hydraulic fluid having about ~OO SUS viscosit~ at 10~F comprising 73.0~ by weight of tha above hyd~oxyalkylated isocyanurate and 27.0~ dist~lled water ~as prepared and tested for various pxoperties. See Table I for the results.
~xampl-e 4 To a 500 ml ~lass ~lask equipped with a the~mometer, ~dd~tion ~unnel and cold finger condenser ~as c~arged 31~3 ~rams tQ.12 moles~ of THEIC. The flask ~as h~ated ~o ~elt the TH~IC a~ atmospheric pressure. Boron trifl~oride etherate (0.1 gram) was t~en ~dded ~o t~le flas~ 156.8 Grams (3.56 moles~ of EO w~s added o~er ~ period o~ 16 hours while main-taining the temperature at ahout 1319C to about 137C at a~mospheric pressure. Boron trifluoride etherate catalyst ~as added durin~ the EO addition as required to sustain the reaction. The total amount of catalyst was 2.8% of the THEIC added (0.89 grams~.
After addi~ion of EO ~as o~er, the reaction mixture was heated at abou~ 125~C fox about 16 hours, cooled to room tempera~ure and the contents wei~hed (173.5 grams) and the OH number was determined (152~ which corresponded ko a ~olecular weight of 1107. The appro~imate structural formula of the product, as 20 . calculated ~y the uptake o~ EO, was C3N303~(CH2CH2Olg gH~3 whose formula weight is 1439.
A w~ter-~ased hydraulic fluid having a 200 SUS ~iscosi~ of 100~F comprising 75. a~ by ~eight of this i~ocyanurate product and 25.0% by weight of distilled ~ater was then prepared and tested. The results o~ those tests are in Table I.
_xamp;le 5 ~ hydr~y~lk~lated isocyanurat~ compound was pxepared ~ e continuous addition of 41.4 lbs. of EO
~o 15.4 l~s. of THEIC and 60 grams of BF3 etherate in a 10-gallon reactor~ The reactor was heated to 295F to melt the T~IC at which point agitation and EO addition ~ere be~un. Only half of the EO had been added ~hen the pressure re~ched its maximum of 65 psig.
A second 60 gram catalyst charge was added to the ~apor ~p~ce above t~e li~uid reaction mixture and the run continued until the EO was consumed. The resultin~
~luid had an 0~ number of 205. The molecular weight was calculated from the 0~ number to be 821. The average composition fxom calculated molecular weight lS was C3N3o3~cH2c~2o)5~2 ]3 A two quart batch of hydraulic fluid having a viscosity of approximately 20Q SUS was prepared by mixing 1579.8 grams of the isocyanurate base stock, 630.2 grams of distilled water, 11.0 grams of morpholine and 0.4 ~x~ms of SAG-10 silicone defoaming a~ent2 in a beaker. The pH was raised to 9,5 by the additiQn of 14~6 grams o~ 1-amino-2-propansl. See Tables I and TI for test results. The final compo-sition of the fluid was:
2Manufactured by Union Car~ide Co. o~
Ne~ ~ork, ~ew York.
~g~
- ~5 -1569.8g Hydroxyalkylated isocyanurate 70.52~
630.2g Distilled water 28.31%
ll.Og Morpholine 0.49%
14~6g 1-~mino-2-propanol 0,66%
0.4g Silicone defoaming agent 0.02%
~ 16 -The hydro~yalkylated isocyanurate product ~r t~is ex~mple ~as prepared by a reaction similar to that of Example 5 except that only 34.4 lbs. of EO
~as added and the 60 ~rams of catalyst was charged into the melted THEIC~ No further catalyst addition was necessary~ T~e resul~ing fluid had an OH number of 195 and as in ~xample 5, the molecular weight wa~
calculated to be 845 which corresponded to an average 3 3 3I cH2cH2o)5~4H]3.
Two quarts of hydraulic fluid having a viscosity of approximately 200 SUS were prepared. The same polyoxyalkylene glycol thickener (36,000 cs at . 100F) as used in Example 2 was used to increase the ~iscosit~ index. The viscosity of the thickener allows a lower isocyanurate 1uid to water ratio to be used. Corrosion lnhibitors, buffers and defoamer were also added. Two hundred grams of thickener were dissolved in 925~6 grams of water with stirring and heating ~ollowed by the addition of 7B8.4 gra~s of the base stock. An additi~e package was prepared on adding 4 grams of rnercapto~enzothiazole, 18 grams o~ morpholine and la ~rams of ~riethanolamine to 50 grams of 20% aqueous potassium laurate bu~fer solution~
This package was blended with the fluid along with four ~rams of potassium nitrite dis~olved in four grams of water. Finally, 6 drops (0.4 grams) of SA&-10 defoamer were added. The composition of the fluid was:
.
925.6g Distilled watex 46.27 788.4g Hydroxyalk~lated isoc~anurate 39.41 200~0g Polyalkylene glycol ~hickener 10.00 50.0g 20% Aqueou~ pot~ssiu~ l~urate 2.5 %
4.0g Mercaptobenzothiazole 0.20%
3L ~ ? ?
18.0g Morpholine 0.90%
lO.Og Triethanolamine 0~5 %
4.0g Potassium nitrite 0.~ %
0.4g SAG-10 silicone defoaming agent 0.02 This fluid was also tested. See Tables I and II.
Example 7 The hydro~yalkylated isocyanurate product fo~
this f~rmulation was prepared by a reaction similar to that described in Example 6. ~he resulting product had an OE number o~ 209. I~s molecular weight was calculated to be 805 which corresponds to an average composition of: C3N303~(CH~CH~O)5 1H]3~
~wo quarts of h~draulic ~luid ha~ing ~ ~iscos~ty of approximateIy 275 SUS at 100~F were prepared as in Example 6 and tested.tsee Tables ~ and II)e The 1u~d had the follo~ing composition:
1603?8y H~droxyalkylated isocyanurate 72.89%
499.4g Distilled ~ater . 22,69%
55.0g 20% Potassiu~ laurate solution 2.50%
8.8g 50% Sodium mercapto~e~zothiazole ~aqueous solut~Qn) 0.40 2q2g Tolutri~zole 0~10~
19~8~ Mo~phol~ne OD90%
11.0g T~ietha~olamine 0.50%
0.4g ~AG~10 ~ COn~ de~oam~g agen~ 0.20 E~
The hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7.
Ab~ut-four quarts o hy~raulic fluid;~avi~g 200 SUS vi5c05ity at 100F were prepared and tested (see Tables I and II)4. The fluid had he following composition:
2893~ag Hydroxyalkylated isocyanurate 68~89%
1121.4g Distilled wa~er 26.69%
105.0g 20% Potassium laurate (aqueous solution) 2~50%
16.8g 50% Sodium mercaptobenzothiazole laqueous solution) 0.40%
4.2g Tolutriazole 0.10%
37.8g Morpholine 0.90%
21.0g Triethanolamine 0.50~
O.~g SAG~10 silicone defoaming agent0,02%
0~ ~
Exam~le 9 The hydroxyalkylated lsocyarlurate product ~or this formulation was the same as in Example 7.
About four quarts of hydraulic fluid having 150 SUS viscosity at 100F were prepared and tested (see Ta~les I and II). The fluid had the following composition 2600O0g Hydroxyalkylated isocyanurate 64.9g%
1224.0g Distilled water 30O59%
lOO.Og 20% Potassium laurate (aqueous solution) 2.50 16.0g 50% Sodium mercaptobenzothiazole (aqueous solution) 0.40%
4.0g Tolutriazole 0.10%
36.0g Morpholine 0.90%
20.0g Triethanolamine 0.50~
0.8g SAG-10 ~ilicone de~oaming agent 0.02%
990~ !
_ 21 -~1~'1 The hydroxyalkylated isocyanurate product for this formulation was the same as in Example 7. About four qu3rts-o~ hydrauli~ fiuid:having 100 SU~ vis~o~ity at 100F were prepared and tested (see ~ables I and II~v The fluid had the following composition:
2268.6g ~y~roxyalkylated isocyanurate 59.69%
1364.2g Distilled water 35.89%
95,0g 20% Potassium laurate (aqueous solutio~) 2.50%
15~2g 50% Sodium mercaptobenzothiazole (aqueous solution) 0.40%
3.8g Tolutriazole 0.10%
34.2g Morpholine 0990 l9.0g Triethanolamine 0~50%
0.6g SAG-10 silicone de~oaming agent Q.Q2%
- ~2 The utility of the fluids prepaxed in Examples 1-10 as ~ire-resistant hydraulic ~luids and speci~cally the~r advanta~e as replacements ~or the water ~l~col type~ was established by the determinat.ion of the follo~in~ properties of the isocyanurate based fluids and CGmpar~sOn with the properties of Hou~htosafe 620, a commercial water glycol hydraulic fluid manufactu~ed by EA F. Houghton. The results are ~ummartxed ;n Tables ~ and II.
A) Viscosity (measured by ANSI/ASTM
D-2270-77? - The viscosities at 100F indicate the ability to formulate a hydroxyalkylated isocyanurate base stock to meet the viscosity specifications of the most commonly used pumps, The kinematic viscosity in centistokes was measured and converted to SUS values b~ the appropr~ate tables Xound in ANSI/AS~M 2161-79.
B) Yiscosity Index (measured by ANSI/ASTM
D-2270-79) ~ The viscosity of the fluids will vary . during use due to chan~es in the ~luid temperature.
The hydraul~c system may not operate properly if the ~luid beco~es too thin or too thickq The viscosity ~ndex (VI~- predicts the extent of these changes with a higher value indicating less of a change. A VI of at least 100 would be considered suitable. Only the fluid of Example 3 failed to mePt these criteria. Also, the 1uids employin~ thickener are seen to have VI's superîor to those ~luids without it. The VI's were calculated by utilizin~ the ~alue ~or 100F viscosity and an est~nated value for 21~ ~iscosity obtained by extrapolation on the A~TM 5t~ndard Vi~cosity Temper~ture chart u~ z~n~ the vlscosit~ Yalues at 100~F and either 130~-~ or 150~F.
C) Pour Point ~measured by ANsI/Asrr~
D-97 66 ~1971~] - The pour points of the fluids are important ~f they are to be shipped, stored or utilized outdoors ~n cold we~ther. E~cept for the fluid oE
E-~ample 5 which included a thickener, all of the tested Xluids had po~r point ~lues which would render them suitable for use at temperatur s below 0F.
D) Four Ball ~ear Test ~measured by ANS~/ASTM D-2266-~7 ~1977)~ - Lubricity testing of th~
fluids is required since a hydraulic fluid must separate ~nd lu~ricate ~he surfaces o~ system co~ponents wh~ch are in close contact. Employing conditions of 1 hour, 130F, 1200 rpm and 40 kg load for the test, the values for most of the isocyanurate based fluids were equal to or better than that o~
Houghtosafe 620. The fluids with higher values than Houghtosafe 620 still exhibited adequate lubricity performance.
E) Power Steering Pump Test - A test such as the Four Ball ~ear Test i5 useful to screen preliminary formulations. Such a test cannot, however, accurately predict pump performance and thus the fluid must be run through a pump test under end-use conditions to determine whether it has sufficient lubricity. The fluids were tested in a Saginaw power steering pump ha~ing a ~luid capacity of 1000 cc.
The rotor, rin~ and vanes o~ the pump are weighed prior to operation. The pump is then assembled and operated for 4 hours ~t a ~luid exit temperature o~ 150F and a pump outlet pressure of 500 psig. An external coolin~ coil ;n a water ~ath ma~ntaIns temperature control and ~ xel~e~ valve ~aintains the system pressure. At the end o~ the 4~hour period~ the pump is disassembled, the parts wei~hed and the weight 1055 recorded. The pump is re~assembled and operated under the same conditions for anot~er 24 hours. The weight loss occurring after the completion of the two cycles is reported as a measure of wear and should b~ less than about 150 mg for acceptable fluids. Resul~s are given in Table I.
F) Wick Flammability Test ~measured by U,S.
Bureau of Mines 5chedule 30~ July 1, 1978) - The test simulates fluid soaked in absorbent, flammable material and exposed to open flamesO It is performed by soaking a pipa clean~r ~n the fluid and cycling it into and out of a laboratory burner flame at 25 cycles/min. until a self-sustaining flame is attained.
The flammability of the fluids was compared by testing them as is, and after varying amounts of evaporative water loss. Thus, three samples were prepared, one was left in an opan petri dish at room temperature~ one was placed in an oven at 150F for 2 hours and one was placed in an oven at 150F for 4 hours. The Bureau of Z0 Mines standard is th~t the number of cycles before - attaining a self-sustainin~ flame sh~uld be 18 or more for the 2-hour sample and 12 or more for the 4-hour sample. As is seen in Table II, the residues of the isocyanurate based fluids retain a significant measure o~ their i~nition resistance while the residue o~ the glycol-based fluid does not.
In summary, the isocyanurate water-based ~luids are comparable in physical properties and lubricity characteristics to typical water glycol fire-resistant hydraulic fluids, but offer a substantial reduction in the flammability of the residual material resul~ing from loss of water content.
9~
Fluids of t~e present invention such as ~hese ma~ be ~esirable for improviny safety in Naval Sh~p h~draulic systems, die casting machines, forging and extrusion presses~ injection moldtng machines, continuous casters, rolling mills, furnace controls, automat~c welders, hydraulic shears, continuous coal miners and mine shuttle cars, and many other uses where the threat of fires existsr a ~
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Claims (20)
1. A water-based hydraulic fluid, which comprises (a) about 20% to about 60% by weight water;
(b) a sufficient amount of a hydroxyalkylated isocyanurate to form a hydraulic fluid with a viscosity from about 100 SUS to about 400 SUS at 100°F, said hydroxyalkylated iso-cyanurate having the formula:
wherein x, y and z are each from about 3 to about 15 and each R is individually selected from hydrogen and methyl;
(c) about 0.01% to about 5% by weight of a liquid phase corrosion inhibitor; and (d) about 0.01% to about 5% by weight of a vapor phase corrosion inhibitor.
(b) a sufficient amount of a hydroxyalkylated isocyanurate to form a hydraulic fluid with a viscosity from about 100 SUS to about 400 SUS at 100°F, said hydroxyalkylated iso-cyanurate having the formula:
wherein x, y and z are each from about 3 to about 15 and each R is individually selected from hydrogen and methyl;
(c) about 0.01% to about 5% by weight of a liquid phase corrosion inhibitor; and (d) about 0.01% to about 5% by weight of a vapor phase corrosion inhibitor.
2. The hydraulic fluid of claim 1 which contains from about 22% to about 50% by weight water.
3. The hydraulic fluid of claim 1 wherein each R is hydrogen.
4. The hydraulic fluid of claim 1 wherein each R is methyl.
5. The hydraulic fluid of claim 1 wherein x, y and z are each from 4 to about 10.
6. The hydraulic fluid of claim 1 wherein said hydroxyalkylated isocyanurate is present in the amount from about 25% to about 80% by weight.
7. The hydraulic fluid of claim 1 wherein said liquid phase corrosion inhibitor comprises sodium mercaptobenzothiazole.
8. The hydraulic fluid of claim 1 wherein said liquid phase corrosion inhibitor comprises tolutriazole.
9. The hydraulic fluid of claim 1 wherein said liquid phase corrosion inhibitor comprises the combina-tion of sodium mercaptobenzothiazole and tolutriazole.
10. The hydraulic fluid of claim 1 wherein said vapor phase corrosion inhibitor is morpholine.
11. The hydraulic fluid of claim 1 which additionally contains from 0% to about 15% by weight of a thickener.
12. The hydraulic fluid of claim l which additionally contains from about 0.1% to about 1% by weight of at least one buffer.
13. The hydraulic fluid of claim l which additionally contains from about 0.01% to about 0.1% by weight of a defoamer.
14. A water-based hydraulic fluid which has a viscosity from about 100 SUS to about 400 SUS
at 100°F, which comprises (a) about 22% to about 50% by weight water;
(b) about 25% to about 80% by weight of a hydroxyalkylated isocyanurate having the formula:
wherein x, y and z are each from about 3 to about 15 and each R is individually selected from hydrogen and methyl;
(c) about 0.01% to about 5% by weight of a liquid phase corrosion inhibitor;
(d) about 0.01% to about 5% by weight of a vapor phase corrosion inhibitor;
(e) about 0% to about 15% by weight of a thickener;
(f) about 0.1% to about 1% by weight of at least one buffer; and (g) about 0.01% to about 0.1% by weight of a silicone defoaming agent.
at 100°F, which comprises (a) about 22% to about 50% by weight water;
(b) about 25% to about 80% by weight of a hydroxyalkylated isocyanurate having the formula:
wherein x, y and z are each from about 3 to about 15 and each R is individually selected from hydrogen and methyl;
(c) about 0.01% to about 5% by weight of a liquid phase corrosion inhibitor;
(d) about 0.01% to about 5% by weight of a vapor phase corrosion inhibitor;
(e) about 0% to about 15% by weight of a thickener;
(f) about 0.1% to about 1% by weight of at least one buffer; and (g) about 0.01% to about 0.1% by weight of a silicone defoaming agent.
15. The hydraulic fluid of claim 14 wherein said vapor phase corrosion inhibitor is morpholine.
16. The hydraulic fluid of claim 15 wherein said liquid phase corrosion inhibitor comprises sodium mercaptobenzothiazole.
17. The hydraulic fluid of claim 15 wherein said liquid phase corrosion inhibitor comprises the combination of sodium mercaptobenzothiazole and tolutriazole.
18. The hydraulic fluid of claim 16 wherein said thickener is a co-polymer of ethylene oxide and propylene oxide.
19. The hydraulic fluid of claim 17 wherein said buffer is selected from the group consisting of potassium laurate, triethanolamine, and mixtures thereof.
20. In a method wherein a first mechanical effort is converted to pressure at a first location, the pressure is transmitted from said first location to a second location via a hydraulic fluid, and said pressure is converted to a second mechanical effort at said second location;
wherein the improvement comprises employing the fluid of claim 1 as said hydraulic fluid.
wherein the improvement comprises employing the fluid of claim 1 as said hydraulic fluid.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US30792481A | 1981-10-02 | 1981-10-02 | |
US307,924 | 1994-09-16 |
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CA1199906A true CA1199906A (en) | 1986-01-28 |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000410516A Expired CA1199906A (en) | 1981-10-02 | 1982-08-31 | Water-based hydraulic fluids containing hydroxyalkylated isocyanurates |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0076595B1 (en) |
CA (1) | CA1199906A (en) |
DE (1) | DE3274557D1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102010782A (en) * | 2010-12-14 | 2011-04-13 | 上海德润宝特种润滑剂有限公司 | Flame-resistant hydraulic fluid composition and preparation method thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE734848A (en) * | 1968-06-21 | 1969-12-01 | Allied Chem | |
US4260505A (en) * | 1978-10-25 | 1981-04-07 | Olin Corporation | Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids |
-
1982
- 1982-08-31 CA CA000410516A patent/CA1199906A/en not_active Expired
- 1982-09-22 EP EP82304993A patent/EP0076595B1/en not_active Expired
- 1982-09-22 DE DE8282304993T patent/DE3274557D1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE3274557D1 (en) | 1987-01-15 |
EP0076595A2 (en) | 1983-04-13 |
EP0076595B1 (en) | 1986-12-03 |
EP0076595A3 (en) | 1983-07-20 |
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