USRE30698E - Hydraulic fluids comprising orthosilicate esters - Google Patents
Hydraulic fluids comprising orthosilicate esters Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- group
- monomethyl ether
- glycol monomethyl
- glycol monoalkyl
- monoalkyl ether
- 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 - Lifetime
Links
- 239000012530 fluid Substances 0.000 title claims abstract description 41
- 150000004762 orthosilicates Chemical class 0.000 title abstract description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 86
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 39
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 29
- -1 orthosilicate ester Chemical class 0.000 claims description 28
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical group COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 25
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical group COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 150000001346 alkyl aryl ethers Chemical group 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical group COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims 4
- 101100177155 Arabidopsis thaliana HAC1 gene Proteins 0.000 claims 1
- 101100434170 Oryza sativa subsp. japonica ACR2.1 gene Proteins 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 67
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 34
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- 229920001971 elastomer Polymers 0.000 description 21
- 239000005060 rubber Substances 0.000 description 21
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 17
- 239000000376 reactant Substances 0.000 description 17
- 239000007983 Tris buffer Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000003301 hydrolyzing effect Effects 0.000 description 11
- 238000005809 transesterification reaction Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000004359 castor oil Substances 0.000 description 9
- 235000019438 castor oil Nutrition 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 9
- 239000005049 silicon tetrachloride Substances 0.000 description 9
- 229920000459 Nitrile rubber Polymers 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 229920003052 natural elastomer Polymers 0.000 description 7
- 229920001194 natural rubber Polymers 0.000 description 7
- 229920001084 poly(chloroprene) Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000013049 sediment Substances 0.000 description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 239000011115 styrene butadiene Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052605 nesosilicate Inorganic materials 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- WYSSJDOPILWQDC-UHFFFAOYSA-N 2,4-ditert-butyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C WYSSJDOPILWQDC-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- JJMTXWDVOIYTSO-UHFFFAOYSA-N 2-hydroxy-4-nonoxy-2-(2-nonoxy-2-oxoethyl)-4-oxobutanoic acid Chemical compound CCCCCCCCCOC(=O)CC(O)(C(O)=O)CC(=O)OCCCCCCCCC JJMTXWDVOIYTSO-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- DGKBIBWNRROPKS-UHFFFAOYSA-N 4-(2-ethylhexoxy)-2-[2-(2-ethylhexoxy)-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid Chemical compound CCCCC(CC)COC(=O)CC(O)(C(O)=O)CC(=O)OCC(CC)CCCC DGKBIBWNRROPKS-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241000985973 Castilla ulei Species 0.000 description 1
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- KYMJNVNKFMZBFB-UHFFFAOYSA-N N-pentylpentan-1-amine phosphoric acid Chemical compound OP(O)(O)=O.CCCCCNCCCCC KYMJNVNKFMZBFB-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 229910003910 SiCl4 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GTLQZNKUEFUUIS-UHFFFAOYSA-N carbonic acid;cyclohexanamine Chemical compound OC(O)=O.NC1CCCCC1 GTLQZNKUEFUUIS-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- WLIGPBOVYTVHKD-UHFFFAOYSA-N dihydroxy-bis[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[Si](O)(O)OC(C)(C)C WLIGPBOVYTVHKD-UHFFFAOYSA-N 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000011549 displacement method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
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- RLSFMGRWULDCBG-UHFFFAOYSA-N n-nonylnonan-1-amine;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCNCCCCCCCCC RLSFMGRWULDCBG-UHFFFAOYSA-N 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- VAKMIIPDYZXBEV-DPMBMXLASA-M potassium;(z,12r)-12-hydroxyoctadec-9-enoate Chemical compound [K+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O VAKMIIPDYZXBEV-DPMBMXLASA-M 0.000 description 1
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- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
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- 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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- C10M2201/081—Inorganic acids or salts thereof containing halogen
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- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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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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Abstract
As novel compounds, orthosilicate esters having the general formula: ##STR1## wherein R1 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 R2, R3 and R4 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 R1 is a propylene glycol monoalkyl ether residue each of R2, R3 and R4 are also propylene glycol monoalkyl ether residues; the total number of carbon atoms in R1, R2, R3, and R4 being at least 15 and at least one of R1, R2, R3, and R4 being a glycol monoalkyl ether residue. Also disclosed are hydraulic fluids containing the novel compounds.
Description
This is a continuation of application Ser. No. 431,889, filed Jan. 9, 1974 and now abandoned.
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.
Recently, there has emerged a growing tendency in vehicle design to use a single hydraulic system to operate equipment, such as power-steering, shock absorbers and brakes, which hitherto were provided with separate hydraulic systems. This has created serious problems in the formulation of suitable fluids. The mineral oil based fluids hitherto used in power-steering systems and shock absorbers are satisfactory with respect to the nitrile and chloroprene rubber used for the seals and gaskets in such systems but are highly detrimental to the natural and synthetic rubbers used in the construction of hydraulic brake and clutch systems. This results in excessive swelling of the latter seals which can lead to a serious malfunction of the brake or clutch system. Conversely, 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. In the case of vehicle operation 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.
Among the many varied types of fluids which have been proposed as base stocks for hydraulic fluids are certain orthosilicate esters. These have been proposed, and in some cases used, for certain categories of hydraulic fluid wherein hydrolytic stability is of comparatively low importance. However, such esters have been consistently rejected by manufacturers for fluids to be used for automotive purposes because of the totally inadequate hydrolytic stability for such purposes. We have now found certain novel orthosilicate esters having superior hydrolytic stability which, by virtue of their good balance of required properties such as boiling point, hydrolytic stability and rubber swell properties, are suitable for use in the formulation of hydraulic fluids for automotive equipment including central system fluids. These orthosilicate esters are characterized by the presence of at least one glycol monoether residue and at least one branched chain organic group (which in some cases may be the glycol monoether residue).
Accordingly, the present invention provides an orthosilicate ester having the general formula: ##STR2## wherein R1 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 R2, R3 and R4 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 R1 is a propylene glycol monoalkyl ether residue each of R2, R3 and R4 are also propylene glycol monoalkyl ether residues; the total number of carbon atoms in R1, R2, R3 and R4 being at least 15 and at least one of R1, R2, R3 and R4 being a glycol monoalkyl ether residue.
The term "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.
The 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 R5 and R6 is a hydrogen atom or methyl group, provided that R5 and R6 are not both methyl groups; R is an alkyl group containing from 1 to 8 carbon atoms; and n is an integer. Thus, the residues of such glycol monoalkyl ethers can be represented as: ##STR4##
It is preferred that 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. In general the larger the molecule of the orthosilicate ester the higher the boiling point and the carbon atom content of the orthosilicate ester molecule is a convenient indication of its size. Accordingly, a minimum carbon atom content of 15 is required to provide a compound of sufficiently high boiling point and such content will depend, inter alia, on the integer n. It is preferred therefore that n is at least 2 and it may be as high as 20, more preferably not more than 6. In general 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. As hereinbefore indicated, 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 R1, R2, R3 and/or R4, and the total carbon atom content will normally be in the range of 15 to 120, more preferably 15 to 60.
As hereinbefore indicated R1 may, alternatively, be a tertiary alkyl group and in this case R1 preferably contains 4 to 10, more preferably 4 to 8, carbon atoms. As also hereinbefore indicated any of R2, R3 or R4 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. However, at least one of the groups R1, R2, R3 and R4 must be a glycol monoalkyl ether residue of the type hereinbefore defined and preferably at least 2 of the groups R1, R2, R3 and R4 are glycol monoether residues.
Accordingly, in the two most preferred embodiments of the present invention there are provided orthosilicate esters having the general formula: ##STR5## In the case of formula (A):- i. Each of R7, R8, R9 and R10 is the same or different; and
ii. Each of R7, R8, R9 and R10 is a propylene glycol monoalkyl ether residue of the formula: ##STR6## in which:- a. in each adjacent R5 and R6 one is a hydrogen atom and the other is a methyl group;
b. 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; and
c. each R is the same or different and is a methyl or ethyl group.
In the case of orthosilicate esters of foregoing formula (B):-
i. R11 is a tertiary alkyl group containing 4 to 8 carbon atoms, particularly a tertiary butyl group;
ii. R12 is a glycol monoalkyl ether residue of the formula ##STR7## iii. R13 is the same as or different from R12 and is a glycol monoalkyl ether residue of the formula ##STR8## iv. R14 is a tertiary alkyl group containing 4 to 8 carbon atoms, particularly, a tertiary butyl group, and R14 is the same as or different from R11 or R14 is a glycol monoalkyl ether residue of the formula ##STR9## and is the same as either R12 or R13 or is different from both R12 and R13 ; and
v. In glycol monoalkyl ether residues of the formula ##STR10## a. each R5 and R6 is the same or different and both are hydrogen atoms or in each adjacent R5 and R6 one is a hydrogen atom and the other is a methyl group;
b. each n is the same or different and the total value of all integers n is from 4 to 8 when R14 is a branched chain alkyl group or from 6 to 12 when R14 is a glycol monoalkyl ether residue, it being especially preferred that each n is from 2 to 4; and
c. 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. In this case the orthosilicate esters will constitute all, or substantially all, of the hydraulic fluid, e.g. 70% or 99% by weight. When used in this manner the orthosilicate esters may, if desired, be blended with small quantities of other known base stocks.
However, 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. In this case 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. In this way one may for example, formulate central systems fluids combining in large measure the good rubber swell properties in respect of nitrile rubber of the orthosilicate esters and the good rubber swell properties, in respect of natural rubber and synthetic rubbers commonly used in automotive brake and clutch systems, of known synthetic base-stocks for brake and clutch systems.
Among 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.
It is highly desirable that 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.
In use the 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,
First Castor Oil
Castor Oil to Specification DTD72
Blown Castor Oil, i.e. castor oil blown with air or oxygen while being heated.
Special Pale Blown Castor Oil, i.e. a similarly blown castor oil.
"Hydricin 4", i.e. a commercially available ethylene oxide/propylene oxide treated castor oil.
Other 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
Diamylamine orthophosphate
Dinonylamine orthophosphate
Diamylamine sulphate
Dinonyl citrate
Di(2ethyl hexyl) citrate
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
Glutaric acid
Azelaic acid
Sebacic acid
Succinic acid
Di ethyl sebacate
Di 2-ethyl hexyl sebacate
Di iso octyl azelate
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
di n-butylamine
di n-amylamine
cyclohexylamine
morpholine
triethanolamine
and soluble salts thereof, e.g. cyclohexylamine carbonate.
Phosphites are also good corrosion inhibitors, e.g.
Tri phenyl phosphite
Di isopropyl phosphite
and certain inorganic salts may be incorporated, e.g. sodium nitrate.
Other additives which may be included are antioxidants such as diarylamines, e.g. diphenylamine, p,p'-dioctyl-diphenylamine, phenyl-α-naphthylamine or phenyl-β-naphthylamine. Other suitable antioxidants are those commonly known as hindered phenols which are exemplified by
2,4-dimethyl 6-t-butyl phenol
2,6-di-t-butyl-4-methyl phenol
2,6-di-t-butyl phenol
1,1-bis (3,5-di-t-butyl-4-hydroxyphenyl)-methane
3,3',5,5',tetra-t-butyl-4-4'-dihydroxy-diphenyl
3-methyl-4, 6-di-t-butyl phenol
4-methyl-2-t-butyl phenol
Yet further additives which may be used are 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.
Other 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. Moreover, long chain (e.g. C10-18) 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.
Conventional 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 Cl4 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. For example, to prepare an orthosilicate ester containing four identical glycol monoether residues 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 Cl4 or a larger excess in the case of a transesterification reaction.
To prepare 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 Cl4 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. Thus 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. Examples of 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.
In the case of 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. In this case it is preferred to introduce the alkyl group before the glycol monoether residues, for example by reaction of Si Cl4 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. When preparing orthosilicate esters containing alkyl groups by transesterification a suitable tetra (alkyl) silicate, e.g. tetra (t-butyl) silicate, containing the desired alkyl group(s), can be reacted with a glycol monoether in 1:1, 1:2 or 1:3 molar ratio to introduce 1,2 or 3 glycol monoether residues respectively. Alternatively, and preferably 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.
When preparation of the orthosilicate esters is by transesterification, 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. For example, 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.
In a preferred preparation of the novel orthosilicate esters by the transesterification route a catalyst is used, 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.
When preparation is by the transesterified route the 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 invention will now be illustrated with reference to the following examples:
______________________________________ Preparation of Tris(triethylene glycol mono- ethyl ether)t-butyl silicate Amount No. of Reactants Mol. Wt. Taken Moles ______________________________________ Silicon tetrachloride 170 170 g 1.0 Tertiary butanol 74 74 g 1.0 Triethylene glycol mono- methyl ether 164 492 g 3.0 Diethyl ether 600 ml Pyridine 85 g ______________________________________
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 addition of the tertiary butanol was completed over a period of 11/2 hours during which the temperature was allowed to rise as a result of the exothermic reaction, to a maximum of 35° C. at the end of the addition. The reaction mixture was then stirred for a further 1/2 hour at room temperature and then filtered.
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.). During the addition 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%).
______________________________________ Preparation of Tris(triethylene glycol mono- ethyl ether)t-butyl silicate Amount No. of Reactants Mol. Wt. Taken Moles ______________________________________ Silicon tetrachloride 170 170 g 1.0 Tertiary butanol 74 74 g 1.0 Triethylene glycol monomethyl ether 164 542 g 3.3 Pyridine 79g 347 g 4.4 Toluene 1800 ml ______________________________________
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 tertiary butanol, dissolved in 50 ml toluene, was then added to the flask over a period of 1/2 hour during which the temperature was maintained in the range 20° C. to 25° C. The contents of the flask were then heated to 80° C. for 11/2 hours.
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. Addition of the glycol ether was then resumed and the remainder added at a temperature maintained in the range of 30° C. to 40° C., the addition being finally completed in a total of 21/2 hours with the remaining quantity of toluene (400 ml) being added after three-fourths of the glycol ether had been added. The reaction mixture was then stirred at 90° to 100° C. for 21/2 hours and then a further 7 hours at 80° C. Finally, the crude product was filtered, using a diatomaceous filter aid, stripped on a rotary evaporator and finally stripped to a temperature of 170° C. under a pressure of 0.4 to 0.5 mm. Hg to yield 236 g (40% by weight based on the silicon tetrachloride) of a deep yellow liquid containing 4.86% Si by weight (theory 4.75%) and 0.05% by weight residual chlorine (theory 0%).
______________________________________ Tris(tripropylene glycol monomethyl ether)neopentyl silicate Reactants ______________________________________ Silicon tetrachloride 174 g Tripropylene glycol monomethyl ether (commercially available material marketed under the trade name "DOWANOL TPM" 679 g Neopentyl alcohol 88 g Pyridine 340 g Toluene 2.5 liters ______________________________________
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 solvent was then stripped off on a rotary evaporator and the product finally stripped under high vacuum (200° C./0.1 mm Hg). to yield 484.4 g (66.3%) of the final product. Analysis:- 3.74% Si (theory 3.84%) residual chlorine 0.15%
______________________________________ Tris(tripropylene glycol monomethyl ether) silicate Reactants ______________________________________ SiCl.sub.4 170 g Tripropylene glycol monomethyl ether (as in Example 3.) 906 g Pyridine 348 g Toluene 2.5 liters + 50 ml + 250 ml ______________________________________
A mixture of the pyridine and tripropylene glycol monomethyl ether was added, over 1 hour, to the Si Cl4 dissolved in 2.5 liters toluene during which a water bath was used to keep the temperature below 50° C. During the addition the reaction mixture became more viscous and two 250 ml portions of toluene were added to facilitate stirring. The reaction mixture was then heated to 100° C. for 4 hours, cooled, filtered and the solvent stripped off (105° C./20 torr). The resulting product was then stripped under high vacuum (200° C./0.1 mm Hg) to yield 676.4 g (79.8%) of a pale yellow final product. Analysis:- 3.4% Si (theory 3.3%) residual chlorine 0.11%
______________________________________ Tris(triethylene glycol monomethyl ether)t-butyl silicate Reactants ______________________________________ SiCl.sub.4 170 G t-Butanol 74 g Triethylene glycol monomethyl ether 542 g Pyridine 347 g Toluene 2.5 liters + 250 ml ______________________________________
The SiCl4 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.). Further toluene (250 ml) was added to facilitate stirring and the reaction mixture was then heated to 100° C. for a total of 4 hours, cooled, filtered and toluene stripped off (100° C./20 torr.) The resulting product was then stripped under high vacuum (210° C./0.5 mm Hg) to yield 346 g (70.4%) of the final product. Analysis:- 4.92% Si (theory 5.68%) residual chlorine 0.04%
______________________________________ Bis(dipropylene glycol monomethyl ether)bis(t-butyl) silicate Reactants ______________________________________ SiCl.sub.4 170 g Dipropylene glycol monomethyl ether (commercially available material marked under the trade name "DOWANOL DPM") 326 g t-Butenol 148 g Pyridine 348 g Toluene 2.5 liters ______________________________________
The Si Cl4 and toluene were mixed and then a mixture of the t-butanol and 174 g pyridine added thereto over a period of 2 hours during which an exotherm was controlled so that the temperature of the reactants did not exceed 41° C. The reaction mixture was heated to 100° C. for 4 hours, allowed to cool and then a mixture of the dipropylene glycol monomethyl ether and the remainder of the pyridine added thereto. The resulting mixture was heated to 100° C. for 4 hours, cooled, filtered, toluene stripped off, refiltered and finally stripped under high vacuum (180° C./0.01 mm Hg.) to yield 248.2 g (53%) of the final product as a clear yellow liquid. Analysis:- 6.02% Si (theory 5.98%) residual chlorine 0.36%
______________________________________ Bis(t-butyl)(dipropylene glycol monomethyl ether) (triethylene glycol monomethyl ether) silicate Reactants ______________________________________ SiCl.sub.4 170 g t-Butanol 148 g Dipropylene glycol monomethyl ether ("DOWANOL DPM") 148 g Triethylene glycol monomethyl ether 197 g Toluene 2.5 liters Pyridine 332 g ______________________________________
A mixture of the t-butanol and pyridine (158 g) was added to the toluene and Si Cl4 previously mixed in a 5-liter flask (with water bath cooling to maintain temperature below 50° C.). The reactants were then heated to between 80° C. and 100° C. for 4 hours, allowed to cool and a mixture of the dipropylene glycol monomethyl ether and pyridine (79 g) was added thereto (very little exotherm). The reaction mixture was then heated to 80° C. for 4 hours, allowed to cool and a mixture of the triethylene glycol monomethyl ether and the remainder of the pyridine (95 g) was added thereto (with water bath cooling). Thereafter the reaction mixture was heated to 100°-104° C. for 6 hours, allowed to cool, filtered, toluene stripped off and stripped under high vacuum (180° C./0.05 mm Hg.). The resulting product was filtered to yield 413.1 g (86%) of a clear yellow liquid. Analysis:- 5.85% Si (theory 5.78%) residual chlorine 0.24%
______________________________________ Tris(dipropylene glycol monomethyl ether)t-butyl silicate Reactants ______________________________________ Si Cl.sub.4 170 g t-Butanol 74 g Dipropylene glycol monomethyl ether ("DOWANOL DPM") 488 g Pyridine 348 g Toluene 1 liter + 200 ml + 200 ml 200 ml + 400 ml + 1 liter ______________________________________
The t-butanol and pyridine 80 g were mixed and added to a previously prepared mixture of the Si Cl4 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. Following the addition the reaction mixture was transferred to a 5 liter flask using a further 1 liter of toluene and then heated to 80° C. for 12 hours. The resulting product was filtered, the solvent stripped off and the product stripped under high vacuum (200° C./0.1 mm Hg.). Finally the product was refiltered to yield 399 g (73.6 %) of clear yellow liquid. Analysis:- 5.48% Si (theory 5.17%) residual chlorine 0.15%
______________________________________ Bis(triethylene glycol monomethyl ether(bis (t-butyl)silicate Reactants ______________________________________ SiCl.sub.4 170 g t-Butanol 148 g Triethylene glycol monomethyl ether 361 g Pyridine 348 g Toluene 2.5 liters + 250 ml ______________________________________
A mixture of the t-butanol and pyridine (174 g) was added to a previously prepared mixture and the Si Cl4 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. The resulting crude product was cooled, filtered, toluene stripped off, then stripped under high vacuum to yield 323.1 g (64.6%) of the final product as a clear, pale yellow liquid. Analysis:- 5.7% Si (theory 5.6%) residual chlorine 0.05%.
______________________________________ Bis(tripropylene glycol monomethyl ether)bis(t- butyl)silicate Reactants ______________________________________ SiCl.sub.4 170 g t-Butanol 148 g Tripropylene glycol monomethyl ether ("DOWANOL TPM") 453 g Pyridine 348 g Toluene 2.5 liters ______________________________________
A mixture of t-butanol and pyridine (174 g) was added to a mixture of the Si Cl4 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. for 4 hours, cooled, filtered, solvent stripped off and the product finally stripped under high vacuum (180° C./0.1 mm. Hg.) to yield 367.2 g (63%) of the final product. Analysis: 4.96% Si (theory 4.8%) residual chlorine not measured
______________________________________ Tris(tripropylene glycol monomethyl ether) t-butyl silicate reactants ______________________________________ SiCl.sub.4 119 g t-Butanol 51.8 g Tripropylene glycol monomethyl ether ("DOWANOL TPM") 474 g Pyridine 237 g Toluene 250 ml + 300 ml + 600 ml + 200 ml ______________________________________
A mixture of the t-butanol and 80 g pyridine was added to a mixture of the Si Cl4 and toluene (250 ml) in a flask fitted with a water bath for cooling. The resulting exotherm raised the temperature to 30° C. A further 300 ml toluene was added to maintain fluidity and the reaction mixture was then refluxed for 2 hours. The reaction mixture was then cooled and a mixture of the tripropylene glycol monomethyl ether and the remaining pyridine was added over a period of 1 hour during which little exotherm was noticed. A further 600 ml toluene was also added. The reaction mixture was heated to 90° C. for 10 hours after transferring to a larger flask with the aid of a further 200 ml toluene. The crude product was worked up by filtering, stripping off the solvent on a rotary evaporator and finally stripping under high vacuum (180° C./0.1 mm Hg.) to yield 380 g (75.9%) of the final product as a light yellow liquid. Analysis:- 3.86% Si (theory 3.91%) residual chlorine 0.76%
______________________________________ Tetra(dipropylene glycol monomethyl ether) silicate Reactants ______________________________________ SiCl.sub.4 170 g Dipropylene glycol monomethyl ether ("DOWANOL DPM") 650 g Pyridine 348 g Toluene 2.5 liters ______________________________________
The dipropylene glycol monomethyl ether and pyridine were mixed together and added to the previously mixed Si Cl4 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%
Infra-red spectra of the products of all of the foregoing Examples 1 to 12 were consistent with the expected product having been obtained in each case.
The suitability of orthosilicate esters of the present invention for use in hydraulic fluids was demonstrated by measuring the Reflux Boiling Point, Hydrolytic Stability and Rubber Swelling Effect of various esters. Reflux Boiling point was measured in the manner specified by the SAE J1703c specification. Rubber Swell was measured by placing a rubber square (approximately 1×1×(1/10 inches) in a 2-ounce bottle provided with a layer of glass beads at the bottom. The bottle was then filled with the test fluid and placed in an oven for 3 days at a constant temperature, whereafter the rubber square was removed, washed with ethanol and dried. The volume of the rubber square was accurately measured before and after the test by the well known displacement method and the percentage volume increase calculated. In this manner styrene-butadiene rubber squares were used at 120° C. and natural rubber squares, being more temperature-sensitive, at 70° C., these being the usual temperatures at which to carry out these tests. In addition nitrile and chloroprene rubber squares were also used and in these cases a temperature of 70° C. was used, there being no established practice in this respect since hitherto it has not been normal for nitrile and chloroprene rubber to come into contact with brake fluids and hence these rubbers have not been tested in this manner.
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 obervations, according to the scale:
______________________________________ 0 test mixture gelled 3 small sediment formed 1 heavy sediment formed 4 very slight sediment formed 2 sediment formed 5 clear ______________________________________
The 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.
The results of Boiling Point determination, Hydrolytic Stability tests and Rubber Swell tests on styrene butadiene rubber and natural rubber are shown in the following Table 1. The results of Rubber Swell tests on nitrile rubber and chloroprene rubber are shown in the following Tables 2 and 3 respectively.
From the results set out in the Tables it is seen that the tested orthosilicate esters have satisfactory Boiling Points and superior Hydrolytic Stability. In addition low Rubber Swell values for nitrile and chloroprene rubbers were obtained. Rubber Swell values for styrene-butadiene and natural rubbers were high but the low chloroprene and nitrile values were considered to be of much greater importance in order to obtain fluids compatible with all these rubbers. When the orthosilicate esters are blended with known automotive hydraulic fluid base stocks (which are very poor with respect to chloroprene and nitrile but good with respect to styrene-butadiene and natural rubber) the Rubber Swell values of the blended fluid in comparison with the values of the orthosilicate ester will be lower in the case of styrene-butadiene and natural rubbers but higher in the case of nitrile and chloroprene rubbers.
In the following Tables 1 to 3 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%).
TABLE 1 __________________________________________________________________________ 3-day Rubber Swell Tests (% Swell) Boiling Hydrolytic Styrene Point Stability butadiene Natural Orthosilicate Tested (°C.) Rating Rubber Rubber __________________________________________________________________________ Tris(triethylene glycol mono- methyl ether) t-butyl silicate 290 3 0.5 3.9 Tris(tripropylene glycol mono- methyl ether) neopentyl silicate * 3 34.2 23.7 Tetra(tripropylene glycol mono- methyl ether) silicate * 3 23.5 12.5 Bis(dipropylene glycol mono- methyl ether) bis (t-butyl) silicate * 4 51.7 55.5 Bis(t-butyl)(dipropylene glycol monomethyl other)(triethylene glycol monomethyl ether) silicate * 4 51.2 41.8 Tris(dipropylene glycol mono- methyl ether) t-butyl silicate 309 4 47.1 36.5 Bis(triethylene glycol monomethyl ether) bis (t-butyl) silicate 303 5 44.4 19.2 Bis(tripropylene glycol mono- methyl ether) bis (t-butyl) silicate 226 5 39.9 44.1 Tris(tripropylene glycol mono- methyl ether) t-butyl silicate 253 5 60.9 37.6 Silicate A 308 0 9.3 5.5 Silicate B 310 1 2.4 -0.7 Silicate C 282 1 14.2 8.0 __________________________________________________________________________ *Not measured
TABLE 2 ______________________________________ 3-day Rubber Swell Test on Orthosilicate Tested Nitrile Rubber (% Swell) ______________________________________ Tetra(tripropylene glycol mono- methyl ether) silicate -2.4 Bis(dipropylene glycol monomethyl ether) bis (t-butyl) silicate 0 Bis(t-butyl)(dipropylene glycol monomethyl ether)(triethylene glycol monomethyl ether) silicate 2.6 Tris(dipropylene glycol mono- methyl ether) t-butyl silicate -0.01 Bis(triethylene glycol monomethyl ether bis t-butyl) silicate 7.2 Bis(tripropylene glycol monomethyl ether) bis (t-butyl) silicate -0.34 Silicate A 20.8 Silicate C 6.5 ______________________________________
TABLE 3 ______________________________________ 3-day Rubber Swell Test on Orthosilicate Tested Chloroprene Rubber (% Swell) ______________________________________ Tris(triethylene glycol mono- methyl ether) t-butyl silicate 1.5 Tris(tripropylene glycol mono- methyl ether) neopentyl silicate 0.2 Silicate A 17.4 Silicate C 11.3 ______________________________________
Claims (8)
- monoalkyl ether residue..]. .[.2. A compound according to claim 1 wherein the at least one glycol monoalkyl ether residue has the formula: ##STR12## wherein each of R5 and R6 is selected from the group consisting of a hdyrogen atom and a methyl group, provided that R5 and R6 are not both methyl groups; R is an alkyl group containing from 1 to 2
- carbon atoms; and n is an integer..]. .[.3. A compound according to claim 2 wherein n is an integer of from 2 to 4..]. .[.4. A compound according to claim 1 wherein the total number of carbon atoms in R1, R2, R3 and R4 is from 15 to 60..]. .[.5. A compound according to claim 1 wherein at least one of the groups R1, R2, R3 and R4 is a tertiary alkyl group containing 4 to 8 carbon atoms..]. .[.6. An orthosilicate ester having the general formula: ##STR13## wherein,i. each of R7, R8, R9, and R10 is the same or different; andii. each of R7, R8, R9 and R10 is a propylene glycol monoalkyl ether residue of the formula: ##STR14## in which:a. in each adjacent R5 and R6 one is a hydrogen atom and the other is a methyl group;b. each n is the same or different and the total value of all integers n is from 8 to 16; andc. each R is the same or different and is selected from the group
- consisting of a methyl group and an ethyl group..]. .[.7. A compound according to claim 6 wherein R7, R8, R9 and R10 are the same and each is selected from the group consisting of a tripropylene glycol monomethyl ether residue and a dipropylene glycol monomethyl ether residue..]. .[.8. An orthosilicate ester having the general formula: ##STR15## wherein,i. R11 is a tertiary alkyl group containing 4 to 8 carbon atoms;ii. R12 is a glycol monoalkyl ether residue of the formula: ##STR16## iii. R13 is the same as or different from R12 and is a glycol monoalkyl ether residue of the formula: ##STR17## iv. R14 is selected from the group consisting of tertiary alkyl groups containing 4 to 8 carbon atoms, being the same as or different from R11, and glycol monoalkyl ether residues of the formula: ##STR18## being the same as either R12 or R13 or being different from both R12 and R13 ; andv. in glycol monoalkyl ether residues of the formula: ##STR19## a. each R5 and R6 is the same or different and both are hydrogen atoms or in each adjacent R5 and R6 one is a hydrogen atom and the other is a methyl group;b. each n is the same or different and the total value of all integers n is from 4 to 8 when R14 is a branched chain alkyl group or from 6 to 12 when R14 is a glycol monoalkyl ether residue; andc. each R is the same or different and is selected from the group
- consisting of a methyl group and an ethyl group..]. 9. .[.A compound according to claim 8.]. .Iadd.An orthosilicate ester having the general formula: .Iaddend. ##STR20## wherein R11 is a t-butyl group and R12, R13 and R14 are triethylene glycol monomethyl ether residues; R11 is a neopentyl group and R12, R13 and R14 are tripropylene glycol monomethyl ether residues; R11 and R14 are t-butyl groups and R12 and R13 are dipropylene glycol monomethyl ether residues; R11 and R14 are t-butyl groups, R12 is a dipropylene glycol monomethyl ether residue and R13 is a triethylene glycol monomethyl ether residue; R11 is a t-butyl group and R12, R13 and R14 are dipropylene glycol monomethyl ether residues; R11 and R14 are t-butyl groups and R12 and R13 are triethylene glycol monomethyl ether residues; R11 and R14 are t-butyl groups and R12 and R13 are tripropylene glycol monomethyl ether residues; or R11 is a t-butyl group and R12, R13 and
- R14 are tripropylene glycol monomethyl ether residues. 10. A process comprising reacting a silicon tetrahalide or transesterifying a tetra (hydrocarbyl) silicate with a hydroxy compound to form a compound as
- defined in claim .[.1.]. .Iadd.9.Iaddend.. 11. A hydraulic fluid containing at least one compound as defined in claim .[.1.].
- .Iadd.10.Iaddend.. 12. A hydraulic fluid according to claim 11 containing
- from 1 to 99% by weight of the compound. 13. A hydraulic fluid according to claim 11 containing at least one conventional hydraulic fluid additive and/or base stock.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB01409/73 | 1973-01-10 | ||
GB140973A GB1464712A (en) | 1973-01-10 | 1973-01-10 | Hydraulic fluids |
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US43188974A Continuation | 1973-01-10 | 1974-01-09 | |
US05/679,440 Reissue US4051053A (en) | 1973-01-10 | 1976-04-22 | Hydraulic fluids comprising orthosilicate esters |
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USRE30698E true USRE30698E (en) | 1981-08-04 |
Family
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US05/950,047 Expired - Lifetime USRE30698E (en) | 1973-01-10 | 1979-10-10 | Hydraulic fluids comprising orthosilicate esters |
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US (1) | USRE30698E (en) |
JP (3) | JPS5930758B2 (en) |
AT (1) | AT334495B (en) |
BE (1) | BE809559A (en) |
BR (1) | BR7400118D0 (en) |
CA (1) | CA1029385A (en) |
DE (1) | DE2400914C2 (en) |
DK (1) | DK150186C (en) |
FR (1) | FR2213288B1 (en) |
GB (1) | GB1464712A (en) |
IE (1) | IE38727B1 (en) |
IT (1) | IT1003345B (en) |
NL (1) | NL169318C (en) |
NO (1) | NO149890C (en) |
SE (1) | SE414635B (en) |
ZA (1) | ZA74164B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0220512A1 (en) * | 1985-10-08 | 1987-05-06 | Hoechst Aktiengesellschaft | Method of running a hydraulic system with a fluid made on the basis of glycols |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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)
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 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3085105A (en) * | 1959-04-10 | 1963-04-09 | Shell Oil Co | Orthosilicate thiaesters |
DE1262484B (en) * | 1964-07-10 | 1968-03-07 | Ruhrchemie Ag | Lubricant based on alkanediol diorthosilicic acid (polyoxyalkylene glycol ether) esters |
DE1262486B (en) * | 1964-09-11 | 1968-03-07 | Ruhrchemie Ag | Synthetic lubricant additives based on diorthosilicic acid esters |
-
1973
- 1973-01-10 GB GB140973A patent/GB1464712A/en not_active Expired
-
1974
- 1974-01-09 SE SE7400260A patent/SE414635B/en not_active IP Right Cessation
- 1974-01-09 BR BR118/74A patent/BR7400118D0/en unknown
- 1974-01-09 JP JP49005850A patent/JPS5930758B2/en not_active Expired
- 1974-01-09 BE BE139656A patent/BE809559A/en not_active IP Right Cessation
- 1974-01-09 DE DE2400914A patent/DE2400914C2/en not_active Expired
- 1974-01-09 AT AT14274*#A patent/AT334495B/en not_active IP Right Cessation
- 1974-01-09 ZA ZA00740164A patent/ZA74164B/en unknown
- 1974-01-09 FR FR7400657A patent/FR2213288B1/fr not_active Expired
- 1974-01-09 IE IE45/74A patent/IE38727B1/en unknown
- 1974-01-09 NL NLAANVRAGE7400295,A patent/NL169318C/en not_active IP Right Cessation
- 1974-01-09 CA CA189,780A patent/CA1029385A/en not_active Expired
- 1974-01-09 NO NO740057A patent/NO149890C/en unknown
- 1974-01-09 DK DK009974A patent/DK150186C/en not_active Application Discontinuation
- 1974-01-09 IT IT19230/74A patent/IT1003345B/en active
-
1979
- 1979-10-10 US US05/950,047 patent/USRE30698E/en not_active Expired - Lifetime
-
1981
- 1981-03-04 JP JP3108081A patent/JPS56147792A/en active Pending
- 1981-03-04 JP JP3107981A patent/JPS56147791A/en active Granted
Patent Citations (4)
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)
Title |
---|
Emblem et al., J. Inorg. Nucl. Chem., 30, 721-727 (1968). * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0220512A1 (en) * | 1985-10-08 | 1987-05-06 | Hoechst Aktiengesellschaft | Method of running a hydraulic system with a fluid made on the basis of glycols |
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 |
Also Published As
Publication number | Publication date |
---|---|
ZA74164B (en) | 1975-08-27 |
NO149890C (en) | 1984-07-11 |
IT1003345B (en) | 1976-06-10 |
IE38727L (en) | 1974-07-10 |
NL169318B (en) | 1982-02-01 |
DK150186C (en) | 1987-10-19 |
BE809559A (en) | 1974-05-02 |
NO149890B (en) | 1984-04-02 |
AU6436874A (en) | 1975-07-10 |
DE2400914A1 (en) | 1974-07-18 |
DK150186B (en) | 1986-12-29 |
GB1464712A (en) | 1977-02-16 |
BR7400118D0 (en) | 1974-08-22 |
SE414635B (en) | 1980-08-11 |
JPS5757479B2 (en) | 1982-12-04 |
JPS5930758B2 (en) | 1984-07-28 |
NL7400295A (en) | 1974-07-12 |
IE38727B1 (en) | 1978-05-24 |
NO740057L (en) | 1974-07-11 |
DE2400914C2 (en) | 1983-12-15 |
JPS56147791A (en) | 1981-11-16 |
JPS4995925A (en) | 1974-09-11 |
AT334495B (en) | 1976-01-25 |
FR2213288B1 (en) | 1977-09-09 |
ATA14274A (en) | 1976-05-15 |
CA1029385A (en) | 1978-04-11 |
FR2213288A1 (en) | 1974-08-02 |
NL169318C (en) | 1982-07-01 |
JPS56147792A (en) | 1981-11-16 |
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