CA1103652A - Oxysilane functional fluids - Google Patents
Oxysilane functional fluidsInfo
- Publication number
- CA1103652A CA1103652A CA306,086A CA306086A CA1103652A CA 1103652 A CA1103652 A CA 1103652A CA 306086 A CA306086 A CA 306086A CA 1103652 A CA1103652 A CA 1103652A
- Authority
- CA
- Canada
- Prior art keywords
- group
- formula
- carbon atoms
- alkyl
- fluid according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000012530 fluid Substances 0.000 title claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
- 239000003921 oil Substances 0.000 claims abstract description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 6
- 239000010726 refrigerant oil Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- -1 2-octyl Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000002480 mineral oil Substances 0.000 claims description 4
- 150000004756 silanes Chemical class 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical group CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000013529 heat transfer fluid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 1
- 241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
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- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/04—Esters of silicic acids
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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
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Abstract
CANADA
ABSTRACT OF THE DISCLOSURE
"FUNCTIONAL FLUIDS "
A functional fluid having particular application as hydraulic fluid, refrigerant oil, electrical oil or heat transfer fluid comprises a major amount of a hydrocarbon oil and a minor amount of an oxysilane compound having the general formula:- wherein:-Rl is alkyl, alkenyl, aryl, alkaryl, aralkyl oralicyclic; R2 and R3 are each independently a group as defined for Rl or a group of the formula - (oR5) - oR6;
R4 is a group cf the formula - (OR )n - OR or a group of the formula:-
ABSTRACT OF THE DISCLOSURE
"FUNCTIONAL FLUIDS "
A functional fluid having particular application as hydraulic fluid, refrigerant oil, electrical oil or heat transfer fluid comprises a major amount of a hydrocarbon oil and a minor amount of an oxysilane compound having the general formula:- wherein:-Rl is alkyl, alkenyl, aryl, alkaryl, aralkyl oralicyclic; R2 and R3 are each independently a group as defined for Rl or a group of the formula - (oR5) - oR6;
R4 is a group cf the formula - (OR )n - OR or a group of the formula:-
Description
11t3~5Z
This invention relates to functional fluids and in particular to functional fluids based on hydrocarbon oils.
The performance of functional fluids based on hydro-carbon oils is often found in practice to be impaired by the presence of water, this problem being particularly acute when such fluids are used as hydraulic fluids e.g.
in aviation or automob-les, or as electrical or refrigerant oils. In hydraulic fluids for example, water may be present as the result of condensation or inadequate drving of the 10 hydraulic system prior to filling or subsequently, by entry through worn seals and it has been found that the effective vapour lock temperature (VLT) of the fluid can be reduced to the boiling point of water even by the presence of Jery minor amounts of water, e.g. of the order of 0. 5-Q . This 15 constitutes a serious deficiency with particularly dangerous consequences in those systems which are brake systems or central hydraulic systems including brake systems.
F~rthermore, in electrical oils the presence of free water increases conductivity and thus promotes electrical discharge 20 and in refrigerant oils water may ~eparate out as ice crvstals.
We have now found that certain silicon compounds are useful as water scavengers in functional fluids based on hydrocarbon oils and may thus alleviate the problems outlined above as previously encountered in the use of 25 such fluids~
According to the present invention there is provided a functional fluid comprising a major amount of a hydrocarbon oil and a minor amount of an oxysilane compound having the general formula:-Rl~ R3 wherein:-(i) Rl is alkyl, preferably containing from 1 to 20,more preferably 1 to 4, carbon atoms; alkenyl, preferably containing from 2 to 20 carbon atoms; aryl, preferably phenyl; alkaryl or aralkyl, preferably containing from 7 to 20 carbon atoms; or alicyclic, preferably containing from 6 to 20 carbon atoms;
(ii) R and R are each independently a group as defined for R or a group of the formula ~ ( oR5 )n ~ oR6 ;
(iii~ R is a group of the formuIa - (OR5)n - OR
or a group of the formula Rl - R7 - Si - R2 wherein R , R and R are independently as defined above;
(iv) R is alkylene, prefera~ly containing from 1 to 15, more preferably 1 to 4, carbon atoms, especially ethylene, propylene o~ butylene; and each R may be the same as or diferent from any other group R ;
- (v) R is alkyl, preferably containing from 1 to 20, more preferably 4 to 18, especially 6 to 15, carbon atoms;
alkenyl, preferably containing from 2 to 20 carbon atoms;
aryl, preferably phenyl; alkaryl or aralkyl, preferably containing from 7 to 20 carbon atoms; or alicyclic, preferably containing from 6 to 20 carbon atoms; and each R may be the same as or different from any other group R6;
(vi) n is zero or an integer, preferably zero or an integer of from 1 to 30, more preferably 1 to 10, particularly 1 to 4; and each n may be the same as or different from any other n; and (vii) R i~ a d rect linkage or a group of the 15 formula - ( oR5 ~tn - wherein R5 and n are independently as defined above, provided that when R is a direct linkage at least one group R or R is a grou~ of the formula -- (oR5 )-- oR6 .
The water scavenginq action of the oxysilane compounds 20 defined above has been found to be improved in the pres2nce of an amine and functional fluids in accordance with the invention which additionally comprise as an optional constituent a small amount, e.g. from 0.5 to 20%, more particularly from 1 to 10%, by weight of an amine are 25 accordingly preferred. Many amines have been found to be s~
suitable, including primary, secondary and tertiary amines, especially those containing a total of at least 5 carbon atoms. Amines which have been found to be particularly B useful include Primene 81 R and Primene JMT which are 5 commercially available primary amines with two methyl groups on the alpha carbon atom.
Other amines which may be useful are Mannich bases formed by condensation of an amine and formaldehyde with a phenol previously alkylated with di- or polyisobutylene;
10 polyisobutenylsuccinimides derived from di- or polyamines;
or amides derived from di- or polyalkylene polyamines and polyisobutenyl substituted monocarboxylic acids.
The amount of oxysilane compound employed in the functional fluids of the invention may vary over a wide 15 range, e.g. from 0.1% to 50% by weight based on the total weight of the fluid.
More particularly, the amount will depend on several factors such as:-(a) the nature of the fluid base-stock;
(b3 the normal use of the functional fluid;
(c) the physical properties required of the finished functional fluid; and (d) the amount of ~7ater likely to be encountered by the fluid in its final use.
~ I f~t~tlf/~' In hydraulic fluids for instance the oxysilane compound would normally be employed in an amount of from 1 to 35%, preferably from 10 to 20~, by weight. On the other hand, in refrigerant oils, electrical oils and heat transfer fluids the preferred amounts of oxysilane compound would generally be somewhat lower e.g. from 0.1 to 5.0% by weight.
The oxysilane compounds employed in the fluids of the present invention may be readily prepared from 10 chlorosilanes by reaction with appropriate hydroxy compounds us~ng well known techniques. A detailed description of such preparative methods is to be found in J. Amer. Chem.
Soc. 80, 1733 (Wright et al) and 68, 70 (Peppard et al).
The hydrocarbon oil used as base-stock in the 15 functional fluids of the invention is preferably a mineral oil, whether derived from crude oil or synthesised from hydrocarbons. Specific examples of such oils are hydrorefined mineral oils and alkylated benzenes.
The functional fuilds of the invention may optionally 20 comprise, e.g. in an amount from 0.1 to 30%, preferably 0.5 to 20%, by weight based on the total weight of the fluid, one or more silane derivatives having the general formula:~
R
R8 _ Si - R10 II
l Rll i~a)3652 wherein:
(a) R8 is a group of the formula R - (OR )m~ OR
(b) each of R9 and R10 is independently alkyl, preferably containing from 1 to 18 carbon atoms, more preferably methyl; alkenyl, preferably containing from
This invention relates to functional fluids and in particular to functional fluids based on hydrocarbon oils.
The performance of functional fluids based on hydro-carbon oils is often found in practice to be impaired by the presence of water, this problem being particularly acute when such fluids are used as hydraulic fluids e.g.
in aviation or automob-les, or as electrical or refrigerant oils. In hydraulic fluids for example, water may be present as the result of condensation or inadequate drving of the 10 hydraulic system prior to filling or subsequently, by entry through worn seals and it has been found that the effective vapour lock temperature (VLT) of the fluid can be reduced to the boiling point of water even by the presence of Jery minor amounts of water, e.g. of the order of 0. 5-Q . This 15 constitutes a serious deficiency with particularly dangerous consequences in those systems which are brake systems or central hydraulic systems including brake systems.
F~rthermore, in electrical oils the presence of free water increases conductivity and thus promotes electrical discharge 20 and in refrigerant oils water may ~eparate out as ice crvstals.
We have now found that certain silicon compounds are useful as water scavengers in functional fluids based on hydrocarbon oils and may thus alleviate the problems outlined above as previously encountered in the use of 25 such fluids~
According to the present invention there is provided a functional fluid comprising a major amount of a hydrocarbon oil and a minor amount of an oxysilane compound having the general formula:-Rl~ R3 wherein:-(i) Rl is alkyl, preferably containing from 1 to 20,more preferably 1 to 4, carbon atoms; alkenyl, preferably containing from 2 to 20 carbon atoms; aryl, preferably phenyl; alkaryl or aralkyl, preferably containing from 7 to 20 carbon atoms; or alicyclic, preferably containing from 6 to 20 carbon atoms;
(ii) R and R are each independently a group as defined for R or a group of the formula ~ ( oR5 )n ~ oR6 ;
(iii~ R is a group of the formuIa - (OR5)n - OR
or a group of the formula Rl - R7 - Si - R2 wherein R , R and R are independently as defined above;
(iv) R is alkylene, prefera~ly containing from 1 to 15, more preferably 1 to 4, carbon atoms, especially ethylene, propylene o~ butylene; and each R may be the same as or diferent from any other group R ;
- (v) R is alkyl, preferably containing from 1 to 20, more preferably 4 to 18, especially 6 to 15, carbon atoms;
alkenyl, preferably containing from 2 to 20 carbon atoms;
aryl, preferably phenyl; alkaryl or aralkyl, preferably containing from 7 to 20 carbon atoms; or alicyclic, preferably containing from 6 to 20 carbon atoms; and each R may be the same as or different from any other group R6;
(vi) n is zero or an integer, preferably zero or an integer of from 1 to 30, more preferably 1 to 10, particularly 1 to 4; and each n may be the same as or different from any other n; and (vii) R i~ a d rect linkage or a group of the 15 formula - ( oR5 ~tn - wherein R5 and n are independently as defined above, provided that when R is a direct linkage at least one group R or R is a grou~ of the formula -- (oR5 )-- oR6 .
The water scavenginq action of the oxysilane compounds 20 defined above has been found to be improved in the pres2nce of an amine and functional fluids in accordance with the invention which additionally comprise as an optional constituent a small amount, e.g. from 0.5 to 20%, more particularly from 1 to 10%, by weight of an amine are 25 accordingly preferred. Many amines have been found to be s~
suitable, including primary, secondary and tertiary amines, especially those containing a total of at least 5 carbon atoms. Amines which have been found to be particularly B useful include Primene 81 R and Primene JMT which are 5 commercially available primary amines with two methyl groups on the alpha carbon atom.
Other amines which may be useful are Mannich bases formed by condensation of an amine and formaldehyde with a phenol previously alkylated with di- or polyisobutylene;
10 polyisobutenylsuccinimides derived from di- or polyamines;
or amides derived from di- or polyalkylene polyamines and polyisobutenyl substituted monocarboxylic acids.
The amount of oxysilane compound employed in the functional fluids of the invention may vary over a wide 15 range, e.g. from 0.1% to 50% by weight based on the total weight of the fluid.
More particularly, the amount will depend on several factors such as:-(a) the nature of the fluid base-stock;
(b3 the normal use of the functional fluid;
(c) the physical properties required of the finished functional fluid; and (d) the amount of ~7ater likely to be encountered by the fluid in its final use.
~ I f~t~tlf/~' In hydraulic fluids for instance the oxysilane compound would normally be employed in an amount of from 1 to 35%, preferably from 10 to 20~, by weight. On the other hand, in refrigerant oils, electrical oils and heat transfer fluids the preferred amounts of oxysilane compound would generally be somewhat lower e.g. from 0.1 to 5.0% by weight.
The oxysilane compounds employed in the fluids of the present invention may be readily prepared from 10 chlorosilanes by reaction with appropriate hydroxy compounds us~ng well known techniques. A detailed description of such preparative methods is to be found in J. Amer. Chem.
Soc. 80, 1733 (Wright et al) and 68, 70 (Peppard et al).
The hydrocarbon oil used as base-stock in the 15 functional fluids of the invention is preferably a mineral oil, whether derived from crude oil or synthesised from hydrocarbons. Specific examples of such oils are hydrorefined mineral oils and alkylated benzenes.
The functional fuilds of the invention may optionally 20 comprise, e.g. in an amount from 0.1 to 30%, preferably 0.5 to 20%, by weight based on the total weight of the fluid, one or more silane derivatives having the general formula:~
R
R8 _ Si - R10 II
l Rll i~a)3652 wherein:
(a) R8 is a group of the formula R - (OR )m~ OR
(b) each of R9 and R10 is independently alkyl, preferably containing from 1 to 18 carbon atoms, more preferably methyl; alkenyl, preferably containing from
2 to 18 carbon atoms; aryl, preferably phenyl; alkaryl, preferably alkyl substituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms; or aralkyl, preferably benzyl; a group of the formula - OR ; or a group of the formula Rl - (oR13)m - ORl -;
(c) R is a group of the formula R12 - (oR13) or a group of the formula:-R - Si - (oR13) oR17 and each R may be the same as or different from any other group Rll;
(d) R12 is alkyl, preferably containing from 1 to 18 carbon atoms; alkenyl, preferably containing from 2 to 18 carbon atoms; aryl, preferably phenyl; alkaryl, prefera~ly alkyl s~bstituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms; or aralkyl,preferably benzyl; and each R12 may be the same as or different from any other grsup R
- (e) R13 is an alkylene grcup, preferably containing 1~Lt)36S2 from 1 to 15, more preferably 1 to 4, carbon atoms, especially ethylene or propylene; and each Rl may be the same as or different from any other group R13;
(f) R14 is an alkylene group, preferably containing from 1 to 15, more pareferably 1 to 6, carbon atoms; and each R14 may be the same as or different from any other group R
(gj m is zero or an integer, preferably zero or an integer of from 1 to 4; and each m may be the same as or 10 different from any other m;
(h) each of R 5 and R 6 is independently alkyl, preferably containing from 1 to 18 carbon atoms, more preferably methyl; alkenyl, preferably cor.taining from 2 to 18 carbon atoms; aryl, preferably phenyl; alkaryl, 15 preferably alkyl substituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms; o : aralkyl, preferably benzyl; a group of the formula -oR17;
or a group of the formula R - (OR 3)m ~ ORl -; and (i) R 7 is a group of the formula R - (OR )m ~
20 and each R may be the same as or different from any other group R17 The above defined silane derivatives of Formula II
are more fully d~scribed in our U.K. Patent Application No. 48009/75 (e~uivalent to German Offenlegungsschrift 26 S2 71~) to which reference ~ay be ~ade for further )3~Z
details.
It will be understood that the functional fluids of - the present invention may contain small amounts e.~. 0.05 to 20%, par~icularly 0.1 to 2%, by weight of additives conventionally employed in such fluids.
In a further aspect of the present invention there is pro~ided a hydraulic system for transmitting power by hydraulic means which system contains as the hydraulic fluid, a functional fluid as hereinbefore described.
In yet another aspect of the present invention there is provided a method of operating a hydraulic system which comprises introducing into the hydraulic system as the hydraulic fluid a functional fluid as hereinbefore described and transmitting power by applying pressure to 15 the hydraulic fluid.
The invention will now be illustrated by the following Examples:-Examples 1 to 21 Functicnal fluids in accordance with the invention 20 were formulated and subjected to the followin~ tests:-(a) Kinematic viscosities at -40~C, in centistokes (cS!, were measured in the manner set forth in the current SAE J1703 specification;
(b) Rubber swell properties with res~ect to 25 nitrile (HN S7~ and urethane (HU723) rubbers were determined in the manner set forth in the BS 903 il~3~5Z
specification by measuring the increase in volume of 2.54 cm.
square, 2 mm. thick rubber specimens after immersion in the test fluid at 70~C for 3 days.
(c) Vapour lock temperatures were determined by the Gilpin Vapour Lock Test as specified in SAE Paper 710 253 entitled "Operating ~erformance of Motor Vehicle Braking Systems as affected by Fluid Water Content", the Gilpin vapour lock temperature (VLT) being taken to correspond with the appearance of 3 ml of vapour. This test was 10 performed upon fluids which had previously been subjected to a Humidity Test at a relative humidity (RH) of 80% and a temperature of about 23C substantially as described in the FMVSS 116 DOT 3/4 specification but extended to a 5 day period and without a reference fluid.
Details of the oxysilane compounds and propor,ions thereof in the fluids and of the results obtained in the above tests are given in Table l.
In each case the fluid also contained 2~ Primene JMT, a commercially available tertiary alkyl primary amine 20 containing approximately 18 carbon atoms.
The hydrocarbon oil constituting the balance of the fluid was in each case a naphthenic mineral oil having the following characteristics:
10 .
~)3~52 Viscosity:- 130 cS at -40F; 3.5 cS at 100F; and 1.31 cS at 210~F.
Pour Point:~ ~- 70F.
Boiling Point:- 248CC.
Flash Point (closed):- 208C.
Aniline Point:- 76~C.
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(c) R is a group of the formula R12 - (oR13) or a group of the formula:-R - Si - (oR13) oR17 and each R may be the same as or different from any other group Rll;
(d) R12 is alkyl, preferably containing from 1 to 18 carbon atoms; alkenyl, preferably containing from 2 to 18 carbon atoms; aryl, preferably phenyl; alkaryl, prefera~ly alkyl s~bstituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms; or aralkyl,preferably benzyl; and each R12 may be the same as or different from any other grsup R
- (e) R13 is an alkylene grcup, preferably containing 1~Lt)36S2 from 1 to 15, more preferably 1 to 4, carbon atoms, especially ethylene or propylene; and each Rl may be the same as or different from any other group R13;
(f) R14 is an alkylene group, preferably containing from 1 to 15, more pareferably 1 to 6, carbon atoms; and each R14 may be the same as or different from any other group R
(gj m is zero or an integer, preferably zero or an integer of from 1 to 4; and each m may be the same as or 10 different from any other m;
(h) each of R 5 and R 6 is independently alkyl, preferably containing from 1 to 18 carbon atoms, more preferably methyl; alkenyl, preferably cor.taining from 2 to 18 carbon atoms; aryl, preferably phenyl; alkaryl, 15 preferably alkyl substituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms; o : aralkyl, preferably benzyl; a group of the formula -oR17;
or a group of the formula R - (OR 3)m ~ ORl -; and (i) R 7 is a group of the formula R - (OR )m ~
20 and each R may be the same as or different from any other group R17 The above defined silane derivatives of Formula II
are more fully d~scribed in our U.K. Patent Application No. 48009/75 (e~uivalent to German Offenlegungsschrift 26 S2 71~) to which reference ~ay be ~ade for further )3~Z
details.
It will be understood that the functional fluids of - the present invention may contain small amounts e.~. 0.05 to 20%, par~icularly 0.1 to 2%, by weight of additives conventionally employed in such fluids.
In a further aspect of the present invention there is pro~ided a hydraulic system for transmitting power by hydraulic means which system contains as the hydraulic fluid, a functional fluid as hereinbefore described.
In yet another aspect of the present invention there is provided a method of operating a hydraulic system which comprises introducing into the hydraulic system as the hydraulic fluid a functional fluid as hereinbefore described and transmitting power by applying pressure to 15 the hydraulic fluid.
The invention will now be illustrated by the following Examples:-Examples 1 to 21 Functicnal fluids in accordance with the invention 20 were formulated and subjected to the followin~ tests:-(a) Kinematic viscosities at -40~C, in centistokes (cS!, were measured in the manner set forth in the current SAE J1703 specification;
(b) Rubber swell properties with res~ect to 25 nitrile (HN S7~ and urethane (HU723) rubbers were determined in the manner set forth in the BS 903 il~3~5Z
specification by measuring the increase in volume of 2.54 cm.
square, 2 mm. thick rubber specimens after immersion in the test fluid at 70~C for 3 days.
(c) Vapour lock temperatures were determined by the Gilpin Vapour Lock Test as specified in SAE Paper 710 253 entitled "Operating ~erformance of Motor Vehicle Braking Systems as affected by Fluid Water Content", the Gilpin vapour lock temperature (VLT) being taken to correspond with the appearance of 3 ml of vapour. This test was 10 performed upon fluids which had previously been subjected to a Humidity Test at a relative humidity (RH) of 80% and a temperature of about 23C substantially as described in the FMVSS 116 DOT 3/4 specification but extended to a 5 day period and without a reference fluid.
Details of the oxysilane compounds and propor,ions thereof in the fluids and of the results obtained in the above tests are given in Table l.
In each case the fluid also contained 2~ Primene JMT, a commercially available tertiary alkyl primary amine 20 containing approximately 18 carbon atoms.
The hydrocarbon oil constituting the balance of the fluid was in each case a naphthenic mineral oil having the following characteristics:
10 .
~)3~52 Viscosity:- 130 cS at -40F; 3.5 cS at 100F; and 1.31 cS at 210~F.
Pour Point:~ ~- 70F.
Boiling Point:- 248CC.
Flash Point (closed):- 208C.
Aniline Point:- 76~C.
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Claims (16)
1. A functional fluid comprising a major amountof a hydrocarbon oil and a minor amount of an oxysilane compound having the general formula:-I
wherein:-(i) R1 is alkyl, alkenyl, aryl, alkaryl, aralkyl or alicyclic;
(ii) R4 and R3 are each independently a group as defined for R1 or a group cf the formula -( OR5)n - OR6 ;
(iii)R is a group of the formula - (OR5)n - OR6 or a group of the formula:- wherein R1, R2 and R3 are independently as defined above;
(iv) R5 is alkylene; and each R5 may be the same as or different from any other group R5;
(v) R6 is alkyl, alkenyl, aryl, alkaryl, aralkyl or alicyclic; and each R6 may be the same as or different from any other group R6 ;
(vi) n is zero or an integer; and each n may be the 15.
same as or different from any other n; and (vii) R7 is a direct linkage or a group of the formula -( OR5 )n O - wherein R5 and n are independently as defined above, provided that when R7 is a direct linkage at least one group R2 or R3 is a group of the formula -( OR5)n- OR6.
wherein:-(i) R1 is alkyl, alkenyl, aryl, alkaryl, aralkyl or alicyclic;
(ii) R4 and R3 are each independently a group as defined for R1 or a group cf the formula -( OR5)n - OR6 ;
(iii)R is a group of the formula - (OR5)n - OR6 or a group of the formula:- wherein R1, R2 and R3 are independently as defined above;
(iv) R5 is alkylene; and each R5 may be the same as or different from any other group R5;
(v) R6 is alkyl, alkenyl, aryl, alkaryl, aralkyl or alicyclic; and each R6 may be the same as or different from any other group R6 ;
(vi) n is zero or an integer; and each n may be the 15.
same as or different from any other n; and (vii) R7 is a direct linkage or a group of the formula -( OR5 )n O - wherein R5 and n are independently as defined above, provided that when R7 is a direct linkage at least one group R2 or R3 is a group of the formula -( OR5)n- OR6.
2. A fluid according to elaim 1 wherein Rl and R6 are alkyl containing from 1 to 20 carbon atoms, alkenyl eontaining from 2 to 20 carbon atoms, phenyl, alkaryl or aralkyl containing from 7 to 20 carbon atoms or alicyclic containing from 6 to 20 carbon atoms; R5 is alkylene containing from 1 to 15 carbon atoms; and n is zero or an integer of from 1 to 30.
3. A fluid according to claim 2 wherein R1 is alkyl containing from 1 to 4 carbon atoms.
4. A fluid according to claim 2 wherein R5 is alkylene containing from 1 to 4 carbon atoms.
S, A fluid aceording to any one of claims 2 to 4 wherein R6 is alkyl containing from 6 to 15 carbon atoms.
16.
16.
16.
16.
6. A fluid according to any one of claims 2 to 4 wherein n is zero or an integer of from 1 to 10.
7. A fluid according to claim 1 wherein the oxysilane is selected from:-(i) compounds of the formula (RO)3 - Si - CH3 wherein R is 2-octyl, tridecyl or CH3 - ;
(ii) compounds of the formula (R0) 2-Si- (CH3) 2 wherein R is n-octyl, tridecyl, phenyl or CH3 2 ;
(iii)the compound having the formula (iv) the compound having the formula (v) compounds of the formula (RO) - Si - (CH3) 3 wherein R is 2-ethylhexyl, tridecyl, phenyl or CH3 -;
17.
(vi) the compound having the formula (vii) the compound having the formula ;
(viii) the compound having the formula ; and (ix) compounds of the formula R1 Si(OR)3 wherein R1 is phenyl and R is 2-ethylhexyl, R1 is ethyl and R is 2-methylcyclohexyl, R1 is ethyl and R is benzyl, R1 is vinyl and R is butyl triglycol or R1 is 2,4,4-trimethylpentyl and R is C4H9OCH2CH2-.
(ii) compounds of the formula (R0) 2-Si- (CH3) 2 wherein R is n-octyl, tridecyl, phenyl or CH3 2 ;
(iii)the compound having the formula (iv) the compound having the formula (v) compounds of the formula (RO) - Si - (CH3) 3 wherein R is 2-ethylhexyl, tridecyl, phenyl or CH3 -;
17.
(vi) the compound having the formula (vii) the compound having the formula ;
(viii) the compound having the formula ; and (ix) compounds of the formula R1 Si(OR)3 wherein R1 is phenyl and R is 2-ethylhexyl, R1 is ethyl and R is 2-methylcyclohexyl, R1 is ethyl and R is benzyl, R1 is vinyl and R is butyl triglycol or R1 is 2,4,4-trimethylpentyl and R is C4H9OCH2CH2-.
8. A fluid according to claim 1 which additionally comprises from 0.5 to 20% by weight of an amine.
9. A fluid according to claim 8 wherein the amine is a primary, secondary or tertiary amine containing at least 5 carbon atoms.
10. A fluid according to claim 1 wherein the hydrocarbon oil is a mineral oil.
18.
18.
11. A fluid according to claim 1 which additionally comprises one or more silane derivatives having the general formula:- II
wherein:
(a) R8 is a group of the formula R12 - (OR13)m- OR14-;
(b) each of R9 and R10 is independently alkyl, alkenyl, aryl, alkaryl, aralkyl, a group of the formula -OR11 or a group of the formula R12 - (oR13)M - oR14 - ;
(c) R11 is a group of the formula R12 - (OR )m-or a group of the formula:- and each R may be the same as or different from anyother group Rll (d) R12 is alkyl, alkenyl, Aryl, alkaryl or aralkyl;
and each R12 may be the same as or different from any other group R12;
(e) R13 is an alkylene group; and each R13 may be The sæme as or different from any other group R13 ;
19.
(f) R14 is an alkylene group; and each R14 may be the same as or different from any other group R14;
(g) m is zero or an integer; and each m may be the same as or different from any other m;
(h) each of R15 and R16 is independently alkyl, alkenyl, aryl, alkaryl, aralkyl, a group of the formula -OR17 or a group of the formula R12 - (OR13)m - OR14 -;
and (i) R17 is a group of the formula R12 - (oR13)m -and each R17 may be the same as or different from any other group R17.
wherein:
(a) R8 is a group of the formula R12 - (OR13)m- OR14-;
(b) each of R9 and R10 is independently alkyl, alkenyl, aryl, alkaryl, aralkyl, a group of the formula -OR11 or a group of the formula R12 - (oR13)M - oR14 - ;
(c) R11 is a group of the formula R12 - (OR )m-or a group of the formula:- and each R may be the same as or different from anyother group Rll (d) R12 is alkyl, alkenyl, Aryl, alkaryl or aralkyl;
and each R12 may be the same as or different from any other group R12;
(e) R13 is an alkylene group; and each R13 may be The sæme as or different from any other group R13 ;
19.
(f) R14 is an alkylene group; and each R14 may be the same as or different from any other group R14;
(g) m is zero or an integer; and each m may be the same as or different from any other m;
(h) each of R15 and R16 is independently alkyl, alkenyl, aryl, alkaryl, aralkyl, a group of the formula -OR17 or a group of the formula R12 - (OR13)m - OR14 -;
and (i) R17 is a group of the formula R12 - (oR13)m -and each R17 may be the same as or different from any other group R17.
12. A fluid according to claim 11 wherein each of R9 and R10 is independently alkyl containing from 1 to 18 carbon atoms, alkenyl containing from 2 to 18 carbon atoms, pheNyl, alkyl substituted phenyl in which the alkyl suBstituent contains from 1 to 12 carbon atoms, benzyl, a group of the formula -OR11 or a group of the formula R12 - (OR13)m -OR14 -; R12 is alkyl containing from 1 to 18 carbon atoms, alkenyl containing from 2 to 18 carbon atoms, phenyl, alkyl substituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms or benzyl;
R13 is an alkylene group containing from 1 to 15 carbon atoms; R14is an alkylene group containing from 1 to 15 carBon atoms; m is zero or an integer of from 1 to 4; and 20.
each of R15 and R16 is independently alkyl containing from 1 to 18 carbon atoms, alkenyl containing from 2 to 18 carbon atoms, phenyl, alkyl substituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms, benzyl, a group of the formula -OR17 or a group of the formula R12 (OR13) - ORl4 -.
R13 is an alkylene group containing from 1 to 15 carbon atoms; R14is an alkylene group containing from 1 to 15 carBon atoms; m is zero or an integer of from 1 to 4; and 20.
each of R15 and R16 is independently alkyl containing from 1 to 18 carbon atoms, alkenyl containing from 2 to 18 carbon atoms, phenyl, alkyl substituted phenyl in which the alkyl substituent contains from 1 to 12 carbon atoms, benzyl, a group of the formula -OR17 or a group of the formula R12 (OR13) - ORl4 -.
13. A fluid according to claim 11 or claim 12 wherein the silane derivative of formula II is present in an amount of from 0.5 to 20% by weight, based on the total weight of the fluid.
14. A fluid according to claim 1 wherein oxysilane compound of formula I is present in an amount of from 1 to 35%
by weight based on the total weight of the fluid.
by weight based on the total weight of the fluid.
15. A fluid according to claim 1 wherein oxysilane compound of formula I is present in an amount of from 0.1 to 5.0% by weight.
16. A fluid according to claim 1 which additionally comprises one or more additives conventionally employed in hydraulic fluids, refrigerant oils, electrical oils or heat transfer fluids.
21.
21.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB26670/77A GB1595701A (en) | 1977-06-24 | 1977-06-24 | Fluids suitable for use as hydraulic fluids electrical oils heat transfer fluids and refrigerant oils |
GB26670/77 | 1977-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1103652A true CA1103652A (en) | 1981-06-23 |
Family
ID=10247328
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA306,086A Expired CA1103652A (en) | 1977-06-24 | 1978-06-23 | Oxysilane functional fluids |
Country Status (10)
Country | Link |
---|---|
JP (1) | JPS6051517B2 (en) |
AU (1) | AU524142B2 (en) |
BE (1) | BE868422A (en) |
CA (1) | CA1103652A (en) |
DE (1) | DE2827741A1 (en) |
FR (1) | FR2395308A1 (en) |
GB (1) | GB1595701A (en) |
IT (1) | IT1097273B (en) |
SE (1) | SE425608B (en) |
ZA (1) | ZA783614B (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5770196A (en) * | 1980-10-22 | 1982-04-30 | Toray Silicone Co Ltd | Hydraulic oil |
US4332957A (en) * | 1980-12-22 | 1982-06-01 | National Distillers & Chemical Corp. | Phenoxyalkoxy silanes |
DE4213321A1 (en) * | 1992-04-23 | 1993-10-28 | Bayer Ag | Thermal stabilization of aromatic polycarbonates |
JP5057630B2 (en) * | 2003-02-18 | 2012-10-24 | 昭和シェル石油株式会社 | Industrial lubricating oil composition |
JP7153323B2 (en) * | 2018-10-19 | 2022-10-14 | 国立研究開発法人産業技術総合研究所 | synthetic lubricating oil |
CN111039973B (en) * | 2019-12-30 | 2023-04-07 | 江苏奥克化学有限公司 | Organic silicon modified enol compound and preparation method thereof |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2129281A (en) * | 1936-03-23 | 1938-09-06 | Continental Oil Co | Lubricating oils |
FR1343967A (en) * | 1961-12-29 | 1963-11-22 | Monsanto Chemicals | Improvements to functional fluids |
US3814691A (en) * | 1970-09-25 | 1974-06-04 | Olin Corp | Alkyl(polyalkoxy)silanes as components in hydraulic fluids |
CA975347A (en) * | 1970-09-25 | 1975-09-30 | David A. Csejka | Alkyl (polyalkoxy) silanes as components in hydraulic fluids |
SU390096A1 (en) * | 1971-08-30 | 1973-07-11 | METHOD OF OBTAINING SUBSTITUTED ETHERS OF ORTHO-SILICA ACID | |
US4075115A (en) * | 1972-09-18 | 1978-02-21 | General Electric Company | Silicone fluid useful as a brake fluid |
US3816313A (en) * | 1972-11-17 | 1974-06-11 | Exxon Research Engineering Co | Lubricant providing improved fatigue life |
US3994948A (en) * | 1973-09-25 | 1976-11-30 | Castrol Limited | Hydraulic fluids |
US4016088A (en) * | 1973-09-25 | 1977-04-05 | Castrol Limited | Hydraulic fluids |
GB1480738A (en) * | 1973-09-25 | 1977-07-20 | Castrol Ltd | Hydraulic fluids |
JPS5061124A (en) * | 1973-09-28 | 1975-05-26 | ||
GB1506844A (en) * | 1974-03-27 | 1978-04-12 | Castrol Ltd | Hydraulic fluid compositions |
GB1577715A (en) * | 1975-11-21 | 1980-10-29 | Castrol Ltd | Hydraulic fluids |
US4141851A (en) * | 1975-11-21 | 1979-02-27 | Castrol Limited | Silane derivatives |
-
1977
- 1977-06-24 GB GB26670/77A patent/GB1595701A/en not_active Expired
-
1978
- 1978-06-22 SE SE7807146A patent/SE425608B/en not_active IP Right Cessation
- 1978-06-23 JP JP53076927A patent/JPS6051517B2/en not_active Expired
- 1978-06-23 ZA ZA783614A patent/ZA783614B/en unknown
- 1978-06-23 CA CA306,086A patent/CA1103652A/en not_active Expired
- 1978-06-23 BE BE188821A patent/BE868422A/en not_active IP Right Cessation
- 1978-06-23 DE DE19782827741 patent/DE2827741A1/en not_active Ceased
- 1978-06-23 IT IT24927/78A patent/IT1097273B/en active
- 1978-06-23 AU AU37416/78A patent/AU524142B2/en not_active Expired
- 1978-06-23 FR FR7818833A patent/FR2395308A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
DE2827741A1 (en) | 1979-01-18 |
AU3741678A (en) | 1980-01-03 |
SE7807146L (en) | 1978-12-25 |
FR2395308B1 (en) | 1984-12-28 |
FR2395308A1 (en) | 1979-01-19 |
JPS5417386A (en) | 1979-02-08 |
GB1595701A (en) | 1981-08-19 |
ZA783614B (en) | 1980-03-26 |
IT1097273B (en) | 1985-08-31 |
SE425608B (en) | 1982-10-18 |
IT7824927A0 (en) | 1978-06-23 |
BE868422A (en) | 1978-10-16 |
AU524142B2 (en) | 1982-09-02 |
JPS6051517B2 (en) | 1985-11-14 |
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