USRE30698E - Hydraulic fluids comprising orthosilicate esters - Google Patents

Hydraulic fluids comprising orthosilicate esters Download PDF

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Publication number
USRE30698E
USRE30698E US05/950,047 US95004779A USRE30698E US RE30698 E USRE30698 E US RE30698E US 95004779 A US95004779 A US 95004779A US RE30698 E USRE30698 E US RE30698E
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Prior art keywords
group
monomethyl ether
glycol monomethyl
glycol monoalkyl
monoalkyl ether
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US05/950,047
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Inventor
John S. Elliott
Gerald J. J. Jayne
Herbert F. Askew
Colin J. Harrington
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Castrol Ltd
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Castrol Ltd
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    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/04—Esters of silicic acids
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F15—FLUID-PRESSURE ACTUATORS; HYDRAULICS OR PNEUMATICS IN GENERAL
    • F15B—SYSTEMS ACTING BY MEANS OF FLUIDS IN GENERAL; FLUID-PRESSURE ACTUATORS, e.g. SERVOMOTORS; DETAILS OF FLUID-PRESSURE SYSTEMS, NOT OTHERWISE PROVIDED FOR
    • F15B21/00—Common features of fluid actuator systems; Fluid-pressure actuator systems or details thereof, not covered by any other group of this subclass
    • F15B21/06—Use of special fluids, e.g. liquid metal; Special adaptations of fluid-pressure systems, or control of elements therefor, to the use of such fluids
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • This invention relates to novel compounds, suitable for use in hydraulic fluids, more particularly to certain new orthosilicate esters suitable for use in hydraulic fluids.
  • Hydraulic fluids are commonly used in hydraulic systems performing various different functions and the combination of properties required of the fluid varies from case to case.
  • One of the severest requirements is the case of automotive brake and clutch fluids. Vehicle manufacturers and other authorities lay down very stringent specifications for such fluids, requiring very high standards with respect to numerous properties.
  • the fluids hitherto used in brake and clutch systems which are normally based on glycols, glycol ethers and/or glycol ether esters, and which have operated satisfactorily in such systems, have a detrimental effect on the nitrile and chlroprene rubber gaskets used in power-steering systems and shock absorbers which can also lead to malfunctioning.
  • the characteristic of reliability in operation which is generally desirable in all mechanical devices, is increased in importance to an absolutely essential requirement by virtue of safety considerations. The need has therefore arisen for a fluid which can be used satisfactorily in a central system controlling the operation of a number of different items of equipment.
  • the present invention provides an orthosilicate ester having the general formula: ##STR2## wherein R 1 is a propylene glycol monoalkyl ether residue containing from 1 to 8 carbon atoms in the terminal alkyl group or is a tertiary alkyl group; each of R 2 , R 3 and R 4 is the same or different and is an ethylene or propylene glycol monoalkyl ether residue containing from 1 to 8 carbon atoms in the terminal alkyl group or is a tertiary alkyl group, provided that when R 1 is a propylene glycol monoalkyl ether residue each of R 2 , R 3 and R 4 are also propylene glycol monoalkyl ether residues; the total number of carbon atoms in R 1 , R 2 , R 3 and R 4 being at least 15 and at least one of R 1 , R 2 , R 3 and R 4 being a glycol monoalkyl ether residue.
  • tertiary alkyl group as employed herein is to be understood to mean an alkyl group containing a tertiary carbon atom, i.e. a carbon atom having no hydrogen atom substituted thereon.
  • glycol monoalkyl ether residues present in the orthosilicate esters of the present invention are derived from monoalkyl ethers of glycols which may be mono-, di- or poly-glycols and such monoalkyl esters can be represented by the formula: ##STR3## wherein each of the R 5 and R 6 is a hydrogen atom or methyl group, provided that R 5 and R 6 are not both methyl groups; R is an alkyl group containing from 1 to 8 carbon atoms; and n is an integer.
  • the residues of such glycol monoalkyl ethers can be represented as: ##STR4##
  • R contains from 1 to 4, most preferably 1 or 2, carbon atoms.
  • the integer n is 1 in the case of a mono-glycol monoether, 2 in the case of a di-glycol monoether and 3 or more in the case of a poly-glycol monoether.
  • n is at least 2 and it may be as high as 20, more preferably not more than 6.
  • n is most preferably from 2 to 4. However, it is to be understood that, for example, it is also possible for n to be 1 in some glycol monoether residues and to be counter-balanced by n being much larger in other residues.
  • total carbon atom content is a convenient indicator of molecular size, i.e. the cumulative effect of the value of each integer n plus the size of any alkyl groups constituting R 1 , R 2 , R 3 and/or R 4 , and the total carbon atom content will normally be in the range of 15 to 120, more preferably 15 to 60.
  • R 1 may, alternatively, be a tertiary alkyl group and in this case R 1 preferably contains 4 to 10, more preferably 4 to 8, carbon atoms.
  • any of R 2 , R 3 or R 4 may be a tertiary alkyl group. In this case also any such alkyl groups preferably contain 4 to 10, more preferably 4 to 8 carbon atoms.
  • at least one of the groups R 1 , R 2 , R 3 and R 4 must be a glycol monoalkyl ether residue of the type hereinbefore defined and preferably at least 2 of the groups R 1 , R 2 , R 3 and R 4 are glycol monoether residues.
  • orthosilicate esters having the general formula: ##STR5##
  • formula (A) ##STR5##
  • R 7 , R 8 , R 9 and R 10 is the same or different;
  • R 7 , R 8 , R 9 and R 10 is a propylene glycol monoalkyl ether residue of the formula: ##STR6## in which:- a. in each adjacent R 5 and R 6 one is a hydrogen atom and the other is a methyl group;
  • each n is the same or different and the total value of all integers n is from 8 to 16, especially wherein each n is from 2 to 4;
  • each R is the same or different and is a methyl or ethyl group.
  • R 11 is a tertiary alkyl group containing 4 to 8 carbon atoms, particularly a tertiary butyl group;
  • R 12 is a glycol monoalkyl ether residue of the formula ##STR7##
  • iii. is the same as or different from R 12 and is a glycol monoalkyl ether residue of the formula ##STR8##
  • R 14 is a tertiary alkyl group containing 4 to 8 carbon atoms, particularly, a tertiary butyl group, and R 14 is the same as or different from R 11 or R 14 is a glycol monoalkyl ether residue of the formula ##STR9## and is the same as either R 12 or R 13 or is different from both R 12 and R 13 ; and
  • each R 5 and R 6 is the same or different and both are hydrogen atoms or in each adjacent R 5 and R 6 one is a hydrogen atom and the other is a methyl group;
  • each n is the same or different and the total value of all integers n is from 4 to 8 when R 14 is a branched chain alkyl group or from 6 to 12 when R 14 is a glycol monoalkyl ether residue, it being especially preferred that each n is from 2 to 4;
  • each R is the same or different and is a methyl or ethyl group.
  • the orthosilicate esters of the present invention are useful hydraulic fluid components and for this purpose they may be used as the base-stock.
  • the orthosilicate esters will constitute all, or substantially all, of the hydraulic fluid, e.g. 70% or 99% by weight.
  • the orthosilicate esters may, if desired, be blended with small quantities of other known base stocks.
  • the orthosilicate esters are particularly useful for blending with substantial quantities of other known base-stocks to modify the properties of the latter or to provide a fluid with a blend of the properties of the separate components.
  • the orthosilicate esters may be present in a wide range of proportions, e.g. from 1% to 70% by weight, but more preferably 10% to 60% by weight.
  • the base-stocks with which the orthosilicate esters of the present invention may be blended are the well-known and widely used glycols, polyoxyalkylene glycols and mono- and di- alkyl esters thereof. Such materials are commercially available, for example under the Registered Trade Mark “Ucon”. Other examples of these materials are those available under the trade names "Oxitol” and "Cellosolve”.
  • Other base-stocks are the borate esters of U.K. Pat. Specification No. 1341901.
  • Further examples of known base-stocks which may be blended with the orthosilicate esters of the present invention are the dicarboxylic acid esters and glycol di-esters referred to in U.K. Pat. Specification No. 1341901 and more fully described in U.K. Pat. Specification Nos. 1083324 and 1249803 respectively.
  • the present invention in one of its aspects, includes hydraulic fluid containing at least 70% of an orthosilicate ester of the present invention, or a mixture of such esters, or a blend of one or more orthosilicate esters of the present invention with one or more known hydraulic fluid base-stocks.
  • the hydraulic fluids of the present invention have a kinematic viscosity at -40° C. of not more than 5,000 cSt., especially not more than 2,000 cSt., and a boiling point of at least 230° C., especially at least 260° C.
  • hydraulic fluids of the present invention will normally be blended with small quantities of various additives of the type commonly employed in hydraulic fluids.
  • Typical additives which may be used in the invention are lubricity additives selected from castor oil or castor oil treated in various ways, for example,
  • Blown Castor Oil i.e. castor oil blown with air or oxygen while being heated.
  • Hydricin 4" i.e. a commercially available ethylene oxide/propylene oxide treated castor oil.
  • lubricity additives which may be incorporated in hydraulic fluids in accordance with the present invention include borate esters, e.g., tricresyl borate and phosphorus-containing esters, especially phosphates, e.g. tricresyl phosphate.
  • the hydraulic fluids of the present invention may also include minor proportions of polyoxyalkylene glycols or ethers thereof, e.g. those sold by Union Carbide Corporation under the Registered Trade Mark “Ucon", particularly those of the LB and HB series. Suitable examples of these polyoxyalkylene glycols and their ethers and esters are given in British Pat. Specification No. 1,055,641.
  • Other suitable lubricity agents are orthophosphate or sulphate salts of primary or secondary aliphatic amines having a total of from 4 to 24 carbon atoms, dialkyl citrates having an average of from 31/2 to 13 carbon atoms in the alkyl groups, aliphatic dicarboxylic acids and esters thereof, specific examples being
  • Polyoxyethylene sebacate derived from a polyoxyethylene glycol of M.W. 200
  • Polyoxyethylene adipate derived from polyoxyethylene glycol of M.W. 200
  • Polyoxyethylene azelate derived from a polyoxyethylene glycol of M.W. 200
  • Polyoxyethylene/polyoxypropylene glutarate derived from mixed polyoxyglycols of average M.W. of about 200
  • Unsaturated aliphatic acids or their salts may also be used, e.g. oleic acid or potassium ricinoleate.
  • Corrosion inhibitors which may be used in the present invention may be selected from heterocyclic nitrogen containing compounds, e.g. benzotriazole and benzotriazole derivatives such as those described in British Patent Specification No. 1,061,904 or mercapto benzothiazole. Many amines or derivatives thereof are also suitable as corrosion inhibitors, for example
  • Phosphites are also good corrosion inhibitors, e.g.
  • inorganic salts may be incorporated, e.g. sodium nitrate.
  • antioxidants such as diarylamines, e.g. diphenylamine, p,p'-dioctyl-diphenylamine, phenyl- ⁇ -naphthylamine or phenyl- ⁇ -naphthylamine.
  • suitable antioxidants are those commonly known as hindered phenols which are exemplified by
  • phenothiazine and its derivatives for example those having alkyl, or aryl, groups attached to the nitrogen atom or to the aryl groups of the molecule.
  • additives which may be used include alkylene oxide/ammonia condensation products as corrosion inhibitor, for example the propylene oxide/ammonia condensation product described in U.K. Patent Specification No. 1,249,803.
  • Further lubricity additives which may be used are complex esters, such as that sold under the trade name "Reoplex 641" and also described in Specification No. 1,249,803.
  • long chain (e.g. C 10-18 ) primary amine corrosion inhibitors and polymerised quinoline resin antioxidants as described in Specification No. 1,249,803, may be used, examples of such amines and resins being the commercially available materials Armeen 12D and Agerite resin D respectively.
  • additives such as those hereinbefore described are normally employed in small amounts such as 0.05% to 10% for example, 0.1% to 2% by weight.
  • the orthosilicate esters of the present invention may be prepared by the techniques conventionally employed in the preparation of such esters, examples of which are the reaction of a silicon tetrahalide such as Si Cl 4 with four parts of hydroxy compound such as glycol monoether or alkanol or the transesterification of a tetra (hydrocarbyl) silicate with the appropriate quantities of a hydroxy compound.
  • silicon tetrachloride can be reacted with a glycol monoether in 1:4 molar ratio or a tetra (hydrocarbyl) silicate can be transesterified with a glycol monoether in 1:4 molar ratio but preferably this reaction or transesterification is carried out in the presence of an excess of glycol monoether, e.g. about 10% excess in the case of reaction with Si Cl 4 or a larger excess in the case of a transesterification reaction.
  • an excess of glycol monoether e.g. about 10% excess in the case of reaction with Si Cl 4 or a larger excess in the case of a transesterification reaction.
  • an orthosilicate ester containing 2 residues of one glycol monoether plus 2 residues of a different glycol monoether a sequential procedure can be followed, i.e. reaction with Si Cl 4 in 2:1 molar ratio or transesterification in 2:1 molar ratio followed by further reaction or transesterification with a different glycol monoether in 2:1 molar ratio.
  • the nature of the glycol monoether residues is determined by selection of the glycol monoether used and the number of each species of residue is determined by the molar ratio used.
  • suitable tetra (hydrocarbyl) silicates are tetramethyl silicate, tetraphenyl silicate and tetraethyl silicate, the last being especially preferred.
  • Other suitable tetra (hydrocarbyl) silicates are described in U.K. Patent Specification No. 1,075,236.
  • orthosilicate esters containing one or more alkyl groups in place of glycol monoether residues the same preparative techniques can be used except in that part of the glycol monoether is replaced by the appropriate alkanol.
  • it is preferred to introduce the alkyl group before the glycol monoether residues for example by reaction of Si Cl 4 with an alkanol such as t-butanol in the quantity required to provide the desired number of alkyl groups followed by reaction with glycol monoether.
  • a suitable tetra (alkyl) silicate e.g.
  • tetra (t-butyl) silicate containing the desired alkyl group(s)
  • a glycol monoether in 1:1, 1:2 or 1:3 molar ratio to introduce 1,2 or 3 glycol monoether residues respectively.
  • a tetra (hydrocarbyl) silicate such as tetraethyl silicate can transesterified with an appropriate alcohol to introduce the desired number of the required alkyl groups and the compound so formed transesterified with glycol monoether to replace the remaining ethyl groups with glycol monoether residues.
  • the tetra (hydrocarbyl) silicate starting material and the reaction conditions may be chosen so that liberated hydroxy compounds can be removed from the reaction mixture by distillation.
  • transesterification of tetraethyl silicate with glycol monoether yields ethanol as well as tetra (glycol monoether ) orthosilicate.
  • the comparatively low boiling ethanol can be stripped off so that the transesterification, which is an equilibrium reaction, can proceed to completion.
  • a catalyst for example, sodium metal which facilitates the reaction via formation of the alkoxide of the glycol monoether or known transesterification catalysts such as p-toluene sulphonic acid or a tetraalkyl, e.g. tetraisopropyl, titanate.
  • Preparation of the othosilicate esters of the present invention from a silicon tetrahalide may be readily carried out by reaction of the appropriate hydroxy compound with the tetrahalide at a temperature of from -40° C. to 150° C., preferably 40° C. to 100° C. If desired this reaction may be carried out in the presence of an inert solvent such as alkyl ethers, toluene, petroleum ether, etc. In addition an acid acceptor, such as a tertiary amine may be used to neutralise hydrogen halide formed in the reaction.
  • an inert solvent such as alkyl ethers, toluene, petroleum ether, etc.
  • an acid acceptor such as a tertiary amine may be used to neutralise hydrogen halide formed in the reaction.
  • reaction temperature employed may be, for example, 80° C. to 250° C., preferably 120° C. to 200° C. and likewise an inert solvent may be used if desired. Further details of the manner in which glycol monoether orthosilicates may be prepared are given in Journal of Inorganic Nuclear Chemistry, 1968, Volume 30, pages 721 to 727.
  • the silicon tetrachloride and diethyl ether were placed in a 2-liter, round-bottomed, three-necked flask fitted with a stirrer, thermometer, thermocouple, nitrogen inlet, dropping funnel, condenser and water column with traps.
  • the tertiary butanol and pyridine (the latter being used as an acid acceptor to prevent reaction of tertiary butanol with hydrogen chloride produced in the reaction) were placed in the dropping funnel and added slowly to the flask at an initial temperature of 20° C. Temperature was recorded by the thermocouple due to the thermometer being obscured by a white precipitate.
  • the apparatus was reassembled as before and the filtered reaction mixture placed in the flask.
  • the triethylene glycol was then added to the reaction mixture via the dropping funnel, slowly at first which gave no detectable exotherm so the rate of addition was increased to give an exotherm of 5° C. (max.).
  • nitrogen was blown in stringly to remove hydrogen chloride.
  • the crude product was then heated to 70° C. for a total of 91/2 hours to ensure completion of the reaction and finally stripped to 170° C. at a pressure of 0.05 mm. Hg to yield 140 g (23.7% by weight based on the silicon tetrachloride) of a clear, brown liquid containing 4.95% Si by weight (theory 4.75%) and 0.17% by weight residual chlorine (theory 0%).
  • the silicon tetrachloride and 250 ml toluene were placed in a two-liter, round-bottomed, three-necked flask, fitted with a dropping funnel, stirrer, condenser, nitrogen inlet and thermocouple.
  • the flask was placed on an ice bath and 87 g pyridine added to the flask over a period of 40 minutes during which the temperature of the flask contents was maintained at 15° C ⁇ 1° C. Thereafter the flask was removed from the ice bath and stirred for 15 minutes during which its temperature was allowed to rise to ambient (about 20° C.).
  • the contents of the flask were then poured into a larger (3-liter) flask similarly equipped to the original reaction vessel and a further 500 ml toluene added. Thereafter the remaining pyridine (260 g) was added over a period of 11/2 hours during which the temperature was maintained in the range 20° C. to 25° C. The triethylene glycol monomethyl ether was then added slowly to the reaction mixture. Over a period of three-fourths hour one-third of the glycol ether was added with the temperature maintained in the range 20° C. to 35° C. At this the flask contents became too thick for further reaction and addition was stopped while a further 600 ml toluene was added.
  • the toluene and silicon tetrachloride were mixed in a 5 liter flask and a mixture of the neopentyl alcohol and 79 g pyridine added with cooling, during which the reaction temperature reached a maximum of 42° C. due to the exothermic reaction taking place.
  • the reaction mixture was heated to 100° C. for 4 hours and then allowed to cool overnight. Thereafter the tripropylene glycol monomethyl ether and the remainder of the pyridine was added over a period of 1/2 hour during which the resulting exotherm was controlled by cooling (water-bath).
  • the reaction mixture was then heated to 112°-114° C. for 5 hours 20 minutes, cooled and the precipitated pyridine hydrochloride filtered off.
  • the SiCl 4 and toluene (2.5 liters were mixed and a mixture of the t-butanol and 87 g pyridine added thereto, during which the temperature was maintained below 50° C.
  • the reaction mixture was then heated to 100° C. for four hours, cooled and then a mixture of triethylene glycol monomethyl ether and the remainder of the pyridine added (during which the temperature was maintained below 50° C.).
  • the t-butanol and pyridine 80 g were mixed and added to a previously prepared mixture of the Si Cl 4 and toluene (1 liter). During the addition water bath cooling was used to control the resulting exotherm. Thereafter the reactants were heated to 80° C. for 3 hours. The remainder of the pyridine and the dipropylene glycol monomethyl ether were mixed and then added to the reaction mixture. During this addition the reaction mixture became viscous and difficult to stir and further portions of toluene (3 ⁇ 200 ml and then 1 ⁇ 400 ml) were added as necessary. The exotherm during the addition was controlled by water bath cooling.
  • a mixture of the t-butanol and pyridine (174 g) was added to a previously prepared mixture and the Si Cl 4 and toluene (2.5 liters), the temperature being maintained below 50° C. during the addition.
  • the reaction mixture was heated to 100° C. for 4 hours, cooled and a mixture of the triethylene glycol monomethyl ether and the remainder of the pyridine added thereto. A slight exotherm resulted and the temperature was maintained below 50° C.
  • the reaction mixture was then heated to 100° C. four 4 hours during which time a further 250 ml toluene was added to render stirring easier.
  • a mixture of t-butanol and pyridine (174 g) was added to a mixture of the Si Cl 4 and the toluene, with water bath cooling, over a period of 2 hours during which the temperature of the reactants rose to 38° C. (max.) due to a moderate exotherm.
  • the reactants were then heated to 100° C. for 4 hours, cooled and then a mixture of the tripropylene glycol monomethyl ether and the remaining pyridine was added thereto over a period of 2 hours (during which a small exotherm raised the temperature of the reaction mixture to a maximum of 30° C.).
  • the reaction mixture was then heated to 100° C.
  • the dipropylene glycol monomethyl ether and pyridine were mixed together and added to the previously mixed Si Cl 4 and toluene (with exotherm to a maximum temperature of 38° C.).
  • the reaction mixture was then heated to 100° C. for 31/2 hours, cooled on a water bath, filtered to remove pyridine hydrochloride and the solvent stripped off on a rotary evaporator at 100° C./20 torr.
  • the crude product was then stripped under high vacuum (180° C./0.1 torr) and filtered twice to yield 152 g (20.5%) of a clear golden liquid. Analysis:- 5.0% Si (theory 5.43%) residual chlorine 0.05%
  • Hydrolytic Stability was measured by placing 1 g of water, 1 g, of the orthosilicate ester under test and 9 g of a commercially supplied glycol-ether hydraulic fluid base stock in a boiling tube, together with anti-bumping granules, and heating the mixture over a bunsen burner until it boiled, whereafter the boiling tube and contents were allowed to cool.
  • the test mixture was observed during boiling and subsequent cooling for visual signs of hydrolytic instability such as gelling of the mixture or formation of a sediment and the orthosilicate ester was assigned a merit rating, based on the devisvations, according to the scale:
  • glycol-ether base stock used in these tests was a 550° F. boiling point mixed ethylene/propylene glycol ether fluid partially inhibited with additives believed to be sodium nitrite, Agerite Resin D and benzotriazole. This was selected after preliminary tests in which the orthosilicate ester was boiled (a) with water, and (b) with water and glycol ether base stock containing no additives. These preliminary tests were found to be not sufficiently severe to evaluate the hydrolytic stability of the orthosilicate esters under test. The presence of the additives was found to increase deposit formation.
  • silicates A to C were glycol monoether orthosilicates not in accordance with the present invention, but prepared in the same manner as in Examples 1 to 12.
  • Silicate A was tris(triethylene glycol monomethyl ether) i-butyl silicate which was analysed as containing 5.0% by weight Si (theory 4.7%).
  • Silicate B was tetra (triethylene glycol monomethyl ether) silicate containing 3.77% by weight Si (theory 4.1%).
  • Silicate C was bis (tripropylene glycol monomethyl ether) bis (triethylene glycol monomethyl ether) silicate containing 4.17% by weight Si (theory 3.78%).

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0220512A1 (de) * 1985-10-08 1987-05-06 Hoechst Aktiengesellschaft Verfahren zum Betreiben von Hydraulikanlagen mit Flüssigkeiten auf der Basis von Glykolen
US20070014753A1 (en) * 2005-07-14 2007-01-18 Jozef Verborgt Solvent-free, self-polishing polyurethane matrix for use in solvent-free antifoulings
US20160024420A1 (en) * 2013-03-12 2016-01-28 The Lubrizol Corporation Lubricating composition containing lewis acid reaction product

Families Citing this family (2)

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GB1577715A (en) * 1975-11-21 1980-10-29 Castrol Ltd Hydraulic fluids
US4234441A (en) * 1979-04-27 1980-11-18 Olin Corporation Silicone oil compositions containing silicate cluster compounds

Citations (4)

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Publication number Priority date Publication date Assignee Title
GB960240A (en) 1961-11-28 1964-06-10 Ici Ltd New silicon compounds
US3308149A (en) * 1963-06-13 1967-03-07 Gen Aniline & Film Corp Organic polyalkyleneoxy silicates
US3320297A (en) * 1963-01-30 1967-05-16 Chevron Res Process for preparing polysiloxane mixtures
US3806549A (en) * 1971-11-03 1974-04-23 Owens Corning Fiberglass Corp Method of preparing organooxy silanes

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Publication number Priority date Publication date Assignee Title
US3085105A (en) * 1959-04-10 1963-04-09 Shell Oil Co Orthosilicate thiaesters
DE1262484B (de) * 1964-07-10 1968-03-07 Ruhrchemie Ag Schmiermittel auf Basis von Alkandiol-diorthokieselsaeure-(polyoxyalkylenglykolaether)-estern
DE1262486B (de) * 1964-09-11 1968-03-07 Ruhrchemie Ag Synthetische Schmiermittelzusaetze auf Basis von Diorthokieselsaeureestern

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
GB960240A (en) 1961-11-28 1964-06-10 Ici Ltd New silicon compounds
US3320297A (en) * 1963-01-30 1967-05-16 Chevron Res Process for preparing polysiloxane mixtures
US3308149A (en) * 1963-06-13 1967-03-07 Gen Aniline & Film Corp Organic polyalkyleneoxy silicates
US3806549A (en) * 1971-11-03 1974-04-23 Owens Corning Fiberglass Corp Method of preparing organooxy silanes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Emblem et al., J. Inorg. Nucl. Chem., 30, 721-727 (1968). *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0220512A1 (de) * 1985-10-08 1987-05-06 Hoechst Aktiengesellschaft Verfahren zum Betreiben von Hydraulikanlagen mit Flüssigkeiten auf der Basis von Glykolen
US20070014753A1 (en) * 2005-07-14 2007-01-18 Jozef Verborgt Solvent-free, self-polishing polyurethane matrix for use in solvent-free antifoulings
US9193875B2 (en) 2005-07-14 2015-11-24 The United States Of America, As Represented By The Secretary Of The Navy Solvent-free, self-polishing polyurethane matrix for use in solvent-free antifoulings
US20160024420A1 (en) * 2013-03-12 2016-01-28 The Lubrizol Corporation Lubricating composition containing lewis acid reaction product
US9868919B2 (en) * 2013-03-12 2018-01-16 The Lubrizol Corporation Lubricating composition containing lewis acid reaction product

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BE809559A (fr) 1974-05-02
AU6436874A (en) 1975-07-10
DE2400914C2 (de) 1983-12-15
SE414635B (sv) 1980-08-11
JPS5930758B2 (ja) 1984-07-28
NL169318B (nl) 1982-02-01
FR2213288B1 (no) 1977-09-09
NL7400295A (no) 1974-07-12
JPS56147792A (en) 1981-11-16
IE38727L (en) 1974-07-10
NL169318C (nl) 1982-07-01
IT1003345B (it) 1976-06-10
FR2213288A1 (no) 1974-08-02
NO149890B (no) 1984-04-02
JPS56147791A (en) 1981-11-16
GB1464712A (en) 1977-02-16
JPS4995925A (no) 1974-09-11
BR7400118D0 (pt) 1974-08-22
DE2400914A1 (de) 1974-07-18
NO149890C (no) 1984-07-11
JPS5757479B2 (no) 1982-12-04
ATA14274A (de) 1976-05-15
CA1029385A (en) 1978-04-11
ZA74164B (en) 1975-08-27

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