DE2400914C2 - Orthosilicic acid esters, process for their preparation and their use - Google Patents
Orthosilicic acid esters, process for their preparation and their useInfo
- Publication number
- DE2400914C2 DE2400914C2 DE2400914A DE2400914A DE2400914C2 DE 2400914 C2 DE2400914 C2 DE 2400914C2 DE 2400914 A DE2400914 A DE 2400914A DE 2400914 A DE2400914 A DE 2400914A DE 2400914 C2 DE2400914 C2 DE 2400914C2
- Authority
- DE
- Germany
- Prior art keywords
- tert
- glycol monomethyl
- monomethyl ether
- acid ester
- orthosilicic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title description 5
- 238000000034 method Methods 0.000 title description 2
- 230000008569 process Effects 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- -1 alkyl radical Chemical group 0.000 description 65
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
- 239000012530 fluid Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 31
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
- 229920001971 elastomer Polymers 0.000 description 19
- 239000005060 rubber Substances 0.000 description 19
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 239000000654 additive Substances 0.000 description 15
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 14
- 229910052710 silicon Inorganic materials 0.000 description 13
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 10
- 229920000459 Nitrile rubber Polymers 0.000 description 10
- 229910003902 SiCl 4 Inorganic materials 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
- 239000002199 base oil Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 229920001084 poly(chloroprene) Polymers 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000004359 castor oil Substances 0.000 description 8
- 235000019438 castor oil Nutrition 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 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 8
- 239000007788 liquid Substances 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 244000043261 Hevea brasiliensis Species 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229920003052 natural elastomer Polymers 0.000 description 7
- 229920001194 natural rubber Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 229940113120 dipropylene glycol Drugs 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 235000012239 silicon dioxide Nutrition 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- GJWHXWMUGWZNTO-UHFFFAOYSA-N 2,2-dimethylpropane Chemical compound [CH2]C(C)(C)C GJWHXWMUGWZNTO-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 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
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-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
- 239000012442 inert solvent Substances 0.000 description 2
- 230000007257 malfunction Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 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
- 239000011115 styrene butadiene Substances 0.000 description 2
- 230000002522 swelling effect Effects 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 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
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-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
- 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 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
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
- RGPBUVUVZKQNHD-MDZDMXLPSA-N 2-[2-[3,5-bis(2-hydroxyethoxy)oxolan-2-yl]-2-(2-hydroxyethoxy)ethoxy]ethyl (e)-octadec-9-enoate Chemical group CCCCCCCC\C=C\CCCCCCCC(=O)OCCOCC(OCCO)C1OC(OCCO)CC1OCCO RGPBUVUVZKQNHD-MDZDMXLPSA-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001233242 Lontra Species 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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 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
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom 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
- 239000004327 boric acid Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- GTLQZNKUEFUUIS-UHFFFAOYSA-N carbonic acid;cyclohexanamine Chemical compound OC(O)=O.NC1CCCCC1 GTLQZNKUEFUUIS-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-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
- 238000011549 displacement method Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation 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
- KQCITBQWXRFAOB-UHFFFAOYSA-N lithium;toluene Chemical compound [Li].CC1=CC=CC=C1 KQCITBQWXRFAOB-UHFFFAOYSA-N 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- RLSFMGRWULDCBG-UHFFFAOYSA-N n-nonylnonan-1-amine;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCNCCCCCCCCC RLSFMGRWULDCBG-UHFFFAOYSA-N 0.000 description 1
- UYOZJBDIXIOJFQ-UHFFFAOYSA-N n-pentylpentan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCNCCCCC UYOZJBDIXIOJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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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- 238000001556 precipitation Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
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- 230000000630 rising effect Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000013049 sediment Substances 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
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 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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Description
-^CH- CH-- ^ CH- CH-
(H)(H)
bedeuten, in der R ein Alkylrest mit 1 bis 2 Kohlen-Stoffatomen, η eine ganze Zahl von 2 bis 4 und R5 und R6 je ein WasserstofTatom oder ein Methylrest ist. mjt der Maßgabe, daß mindestens einer der Reste R5 und R6 ein WasserstofTatom ist, mit der Maßgabe, daß die Reste R1, R2, R3 und R* zusammen mindestens 15 bis 60 KohlenstofTatome enthalten. mean in which R is an alkyl radical with 1 to 2 carbon atoms, η is an integer from 2 to 4 and R 5 and R 6 are each a hydrogen atom or a methyl radical. with the proviso that at least one of the radicals R 5 and R 6 is a hydrogen atom, with the proviso that the radicals R 1 , R 2 , R 3 and R * together contain at least 15 to 60 carbon atoms.
2. Orthokieselsäureester der allgemeinen Formel I, worin2. Orthosilicic acid esters of the general formula I, in which
a) R1 ein tert.-Butylrest und —OR2. —OR3 und —OR4 jeweils ein Triäthylenglykolmonome-(hylätherrest, ottera) R 1 is a tert-butyl radical and —OR 2 . —OR 3 and —OR 4 are each a triethylene glycol monome- (hylätherrest, otter
b) R1 ein Neopentylrest und —OR2. —OR3 und —OR* jeweils ein Tripropylenglykolmonomethylätherrest. oderb) R 1 is a neopentyl radical and —OR 2 . —OR 3 and —OR * each represent a tripropylene glycol monomethyl ether radical. or
c) R1 und R2 jeweilsein tert.-Butylrest und—OR3 und —OR4 jeweils ein Dipropylenglykolmonomethylätherrest. oderc) R 1 and R 2 are each a tert-butyl radical and —OR 3 and —OR 4 are each a dipropylene glycol monomethyl ether radical. or
d) R1 und R2 jeweils ein tert.-Butylrest, —OR3 ein Dipropylenglykolmonomcthylätherrest und —OR4 ein Triäthylenglykolmonomethylätherrcst. oderd) R 1 and R 2 each represent a tert-butyl radical, —OR 3 a dipropylene glycol monomethyl ether radical and —OR 4 a triethylene glycol monomethyl ether radical. or
e) R1 ein tert.-Butylrest und —OR2. —OR3 und —OR4 jeweils ein Dipropylenglykolmonomethylälherrest. odere) R 1 is a tert-butyl radical and —OR 2 . —OR 3 and —OR 4 each represent a dipropylene glycol monomethyl ether radical. or
f) R' und R2jeweilscinlert.-Butylrestund—OR3 und —OR4 jeweils ein Triäthylenglykolmonomcthylätherrest, oderf) R 'and R 2 are each a tert-butyl radical and —OR 3 and —OR 4 are each a triethylene glycol monomethyl ether radical, or
g) R1 und R2 jeweilsein tert.-Butylrest und—OR' und—OR4 jeweils ein Tripropylenglykolmonomclhylätherrest, oderg) R 1 and R 2 are each a tert-butyl radical and —OR 'and —OR 4 are each a tripropylene glycol monomethyl ether radical, or
h) R1 ein tert.-Butylrest und —OR3, —OR3 und —OR4 jeweils ein Tripropylenslykolmonomethyläthcrrest ist.h) R 1 is a tert-butyl radical and —OR 3 , —OR 3 and —OR 4 are each a tripropylene glycol monomethyl ether radical.
3. Verfahren zur Herstellung von Orthokieselsäureester η nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, daß man in an sich bekannter Weise ein Siliciumletrahalogenid oder einen orthokieselsäureester mit einer oder mehreren der der Formel I entsprechenden Hydroxyverbindungen umsetzt. 3. Process for the preparation of orthosilicic acid ester η according to one of claims 1 and 2, characterized in that one known per se Way a silicon tetrahalide or an orthosilicic acid ester with one or more of the Formula I reacts corresponding hydroxy compounds.
4. Verwendung von Orthokieselsäureestern gemäß einem der Ansprüche I und 2 als Komponente für Hydraulikflüssigkeiten, die außerdem noch mindestensein übliches Hydraulikflüssigkeitsadditiv und/ oder -grundmaterial enthalten.4. Use of orthosilicic acid esters according to one of claims I and 2 as a component for Hydraulic fluids that also contain at least one common hydraulic fluid additive and / or base material.
Die Erfindung betrifft die in den Ansprachen gekennzeichneten Gegenstände.The invention relates to the objects characterized in the speeches.
Hydraulikflüssigkeiten werden allgemein in hydraulischen Systemen verwendet, die zahlreiche verschiedene Funktionen erfüllen. Die Kombination von Eigenschaften, die eine Hydraulikflüssigkeit besitzen muß, ist von Fall zu Fall verschieden. Zu den schärfsten Anforderungen ; gehören diejenigen, die an Brems- und Kupplungsflüssigkeiten in Kraftfahrzeugen gestellt werden. Die Fahrzeughersteller und andere maßgebliche Stellen haben für derartige Flüssigkeiten sehr strenge Spezifikationen festgesetzt, in denen sehr hohe Qualitätsnormen bezüglich zahlreicher Eigenschaften gefordert werden.Hydraulic fluids are widely used in hydraulic systems, which are many different Perform functions. The combination of properties which a hydraulic fluid must have differs from case to case. Among the toughest requirements ; include those that are used in brake and clutch fluids in motor vehicles. The vehicle manufacturers and other relevant bodies have very strict specifications for such liquids in which very high quality standards with regard to numerous properties are required will.
Seit kurzem tendiert man im Fahrzeugbau dazu, zur Bedienung bzw. Betätigung *on Aggregata. wie Servolenkung. Stoßdämpfer und Bremsen, die bisher jeweils mit eigenen Hydrauliksystemen ausgerüstet wurden, ein einziges Hydrauliksystem zu verwenden. Dies hat zu schwerwiegenden Probiemen bei der Rezeptur geeigneter Hydraulikflüssigkeiten geführt. Die Hydraulikflüssigkeiten auf Mineralölbasis, die bislang in Servolenkungssystemen und Stoßdämpfern verwendet wurden, weisen zwar in Bezug auf die Nitril- und Chloroprenkautschuke, die für die Dichtungen und Manschetten in derartigen System verwendet werden, befriedigende Eigenschaften auf. schädigen aber die für den Bau von hydraulischen Brems- und Kupplungssystemen verwendeten synthetischen Kautschuke und Naturkautschuke erheblich. Dies führt zu einer zu starken Quellung dieses Dichtungsmaterials, was zu schwerwiegenden Funktionsstörungen des Brems- oder Kupplungssystems führen kann. Umgekehrt haben die in der Regel auf Basis von Glykolen. Glykoläthern und/oder Glykolätherestern aufgebauten Hydraulikflüssigkeiten, die bislang in Brems- und Kupplungssystemen eingesetzt wurden und in derartigen Systemen befriedigend gearbeitet haben, eine schädigende Wirkung auf die Nitril- und Chloroprenkautschukmanschetten. die in Servolenkungssystemen und Stoßdämpfern verwendet werden, was ebenfalls zu Funktionsstörungen führen kann. Beim Betrieb von Fahrzeugen ist die Betriebssicherheit bzw. -zuverlässigkeit, die bei allen mechanischen Vorrichtungen in hohem Maße erwünscht ist, eine Eigenschaft, der aus. Gründen der Sicherheit die Bedeutung einer absolut wesentlichen Forderung zukommt.Recently there has been a tendency in vehicle construction to operate or actuate * aggregates. like power steering. Shock absorbers and brakes, which were previously each equipped with their own hydraulic systems to use a single hydraulic system. This has serious problems in making the formulation more suitable Hydraulic fluids out. The mineral oil-based hydraulic fluids heretofore used in power steering systems and shock absorbers show with regard to the nitrile and chloroprene rubbers used for the seals and sleeves in such System used to have satisfactory properties. but damage the construction of hydraulic Brake and clutch systems made significant use of synthetic rubbers and natural rubbers. This leads to excessive swelling of this sealing material, which leads to serious malfunctions of the brake or clutch system. Conversely, they are usually based on glycols. Hydraulic fluids composed of glycol ethers and / or glycol ether esters, which were previously used in and coupling systems have been used and have worked satisfactorily in such systems, a damaging effect on the nitrile and chloroprene rubber sleeves. those in power steering systems and shock absorbers are used, which can also lead to malfunctions. When operating vehicles is the operational safety and reliability, which is very important for all mechanical devices Dimensions is desirable, a property that is made up. The importance of security is absolutely essential Claim is due.
Es bestand daher ein Bedürfnis für eine Hydraulikflüssigkeit, die in einem Zentralsyst; .ti. das die Bedienung bzw. den Betrieb einer Reihe verschiedener Aggregate rteuert, in befriedigender Weise verwendet werden kann.There was therefore a need for a hydraulic fluid in a central system; .ti. which controls the operation or the operation of a number of different units r , can be used in a satisfactory manner.
Unter der. zahlreichen verschiedenen Arten von Flüssigkeiten, die als Basismaterialien bzw. -öle für Hydraulikflüssigkeiten vorgeschlagen wurden, finden sich auch bestimmte Orthokieselsäureester. Diese Verbindungen wurden für bestimmte Arten von Hydraulikflüssigkeiten vorgeschlagen und in einigen Fällen auch verwendet, bei denen der Hydrolysebeständigkeit eine vergleichsweise geringe Bedeutung zukommt. Von den Fahrzeugherstellern wurden diese Hydraulikflüssigkeiten jedoch wegen ihrer für diese Zwecke völlig unzureichenden Hydrolysebeständigkeit durchweg abgelehnt.Under the. numerous different types of fluids used as base materials or oils for hydraulic fluids have been proposed, certain orthosilicic acid esters are also found. These connections have been proposed and used in some cases for certain types of hydraulic fluids, where the hydrolysis resistance is of comparatively little importance. From the vehicle manufacturers However, these hydraulic fluids were completely inadequate for these purposes because of their Resistance to hydrolysis rejected across the board.
Der Erfindung lag nun die Aufgabe zugrunde, neue Orthokieselsäureester zu schaffen, die als Basismaterial bzw. -öl für Hydraulikflüssigkeiten verwendet werden können und nicht mit den vorstehenden Nachteilen der für diesen Zweck bekannten Verbindungen behaftet sind, d.h. die insbesondere nicht zu einer zu starken Quellung der in Hydrauliksystemen der verschiedenstenThe invention was now based on the object of creating new orthosilicic acid esters that can be used as the base material or oil can be used for hydraulic fluids and not with the above disadvantages of for this purpose known compounds are afflicted, i.e. in particular not too strong Swelling of the most varied in hydraulic systems
3 43 4
Art üblicherweise eingesetzten Kautschuktypen fuhren damit der Orthokieselsäureester einen ausreichend hound die zudem eine gute Hydrolysebeständigkeit auf- hen Siedepunkt aufweist.The types of rubber that are commonly used give the orthosilicic acid ester a sufficient hound which also has good hydrolysis resistance at the boiling point.
weisen. ' Die erfindungsgemäßen Orthokieseisäureester eignenpoint. The orthocisic acid esters according to the invention are suitable
Es wurde, nun gefunden, daß sich diese Aufgabe sich als Hydraulikflüssigkeitsbestandteile und könnenIt has now been found that hydraulic fluid components and can do this
durch bestimmte neue Orthokieselsäureester lösen läßt, 5 für diesen Zweck als Basismaterial bzw. als Basisölecan be dissolved by certain new orthosilicic acid esters, 5 for this purpose as a base material or as base oils
die eine überlegene Hydrolysebständigkeit aufweisen und verwendet werden. In diesem Fall machen die erfin-which have superior resistance to hydrolysis and are used. In this case, the invented
sich aufgrund der guten Ausgewogenheit ihrer Eigen- dungsgemäßen Qrthokteselsäureester die gesamte, oderdue to the good balance of their proper Qrthocteselsäureester the entire, or
schäften, wie Siedepunkt, Hydrölysebeständigkeit und im wesentlichen die gesamte Hydraulikflüssigkeit, z.ilshafts, such as boiling point, resistance to hydrolysis and essentially all of the hydraulic fluid, e.g.
Kautschukquellung, für die Verwendung bei der Herstel- 70 oder 99 Gewichtsprozent der Hydraulikflüssigkeit,Rubber swelling, for use in manufacturing 70 or 99 percent by weight of hydraulic fluid,
lung von Hydraulikflüssigkeiten für Fahrzeugäggregate io aus. Wenn die erfindungsgemäßen Orthokieselsäure-management of hydraulic fluids for vehicle aggregates io. If the orthosilicic acid according to the invention
und insbesondere auch von Hydraulikflüssigkeiten für ester für diesen Zweck verwendet werden, können sieand in particular hydraulic fluids for esters can also be used for this purpose
zentrale Hydrauliksysteme eignen. gewünschtenfalls mit kleinen Mengen anderer bekanntercentral hydraulic systems are suitable. if desired with small amounts of other known ones
Die erfindungsgemäßen Orthokieselsäureester sind Basismaterialien oder Basisölen gemischt werden,The orthosilicic acid esters according to the invention are base materials or base oils are mixed,
solche der allgemeinen Formel I Die ;rfindungsgemäßen Orthokieselsäureester sindthose of the general formula I are the orthosilicic acid esters according to the invention
3 15 jedoch besonders zur Mischung mit beträchtlichen Men- 3 15 but especially for mixing with considerable people
OR gen von anderen bekannten Basismaterialien geeignet, OR gene suitable from other known base materials,
R ,n L OR4 n um deren Eigenschaften zu modifizieren oder eine Flßs- R , n L OR 4 n to modify their properties or to create a flow
K U j>i υ κ WJ gokelt herzustellen die ein Gemisch der EigenschaftenK U j> i υ κ WJ gokelt produce a mixture of properties
j WJ gokelt herzustellen, die ein Gemisch der Eigenschaftenj WJ gokelt produce a mixture of properties
Q£ 2 , p fi diQ £ 2, p fi di
20 können die erfindungsgemäßen OrthokieselsäureesterThe orthosilicic acid esters according to the invention can be used
(I)(I)
der einzelnen Komponenten aufweist. In diesem Fall Iof the individual components. In this case I
worin R1 eine, ein tertiäres Kohlenstoffatom enthal- in einem weiten Bereich von Mengenverhältnissen an-wherein R 1 contains a tertiary carbon atom in a wide range of proportions
tende Alkylgruppe mit 4 bis 8 Kohlenstoffatomen oder wesend seim, z. B. in Mengen von 1 bis 70 und ins-tend alkyl group having 4 to 8 carbon atoms or wesend seim, z. B. in quantities from 1 to 70 and ins-
die Neopentylgruppe ist, der Rest R2 eine tert.-Butyl- besondere 10 bis 60 Gewichtsprozent. Auf diese Weiseis the neopentyl group, the radical R 2 is a tert-butyl group, especially 10 to 60 percent by weight. In this way
gruppe bedeutet oder die Reste R2, R3 und R-* gleich kann man beispielsweise Hydraulikflüssigkeiten fürgroup means or the radicals R 2 , R 3 and R - * can be used, for example, hydraulic fluids for
oder verschieden sind und, unabhängig voneinander, 25 Zentralhydrauliksysteme formulieren, welche die gutenor are different and, independently of one another, formulate 25 central hydraulic systems which are the good ones
einen Rest der allgemeinen Formel Il Kautschukquelleigenschaften dererfindungsgemäßen Or-a radical of the general formula II rubber swelling properties of the or-
thokieselsäureester in Bezug aufNitrilkautschuke und derthosilicic acid esters in relation to nitrile rubbers and the
I 1 bekannten synthetischen Basismaterialien bzw. BasisöleI 1 known synthetic base materials or base oils
r pu ppj Öl·R (ΙΠ *"r Brcms" un<^ Kupplungssysteme in Bezug auf die inr pu ppj oil · R (ΙΠ * " r Brcms " un < ^ coupling systems in relation to the in
30 den Brems- und Kupplungssystemen von Kraftfahrbedeuten, in der R ein Alkylrest mit 1 bis 2 Kohlenstoff- zeugen üblicherweise verwendeten synthetischen Kauatomen,
η eine ganze Zahl von 1 bis 4 fcnd Rs und R6 tschuke und Naturkautschuke, aufweisen,
je ein Wasserstoffatom oder ein Nietüylrest ist, mit der Zu den Basismaterialien bzw. Basisölen, mit denen
Maßgabe, daß mindestens einer der Rests. R5 und R6 die erfindungsgemäßen Orthokieselsäureester gemischt
ein Wasserstoffatom ist, mit der Maßgabe, daß die 35 werden können, gehören die zu diesem Zweck bekannten
Reste R1, R2, R3 und R4 zusammen mindestens 15 bis und vielfach verwendeten Glykole. Polyoxyalkyiengly-60
Kohlenstoffatome enthalten. kole und deren Mono- und Dialkylester, die im Handel
Bevorzugte Orthokieselsäureester der allgemeinen erhältlich sind. Weitere Basismaterialien Hiw. Basisöle
Formel I sind solche, worin sind die aus der GB-PS 1341901 bekannten Borsäure-30 the brake and clutch systems of motor vehicles, in which R is an alkyl radical with 1 to 2 carbon atoms, synthetic chewing atoms commonly used, η an integer from 1 to 4 and R s and R 6 have chuke and natural rubbers,
each is a hydrogen atom or a Nietüylrest, with the To the base materials or base oils, with the proviso that at least one of the radicals. R 5 and R 6, the orthosilicic acid esters according to the invention are mixed a hydrogen atom, with the proviso that they can be 35, the radicals R 1 , R 2 , R 3 and R 4 known for this purpose belong together at least 15 up to and often used glycols. Polyoxyalkyiengly contain 60 carbon atoms. kole and their mono- and dialkyl esters, which are commercially available Preferred orthosilicic acid esters of the general. Further basic materials Hiw. Base oils formula I are those in which the boric acid known from GB-PS 1341901
a) R1 ein tert.-Butylrest und —OR2, —OR3 und 40 ester. Weitere Beispiele bekannter Basisöle, die mit den —OR4 jeweils ein Triäthylenglykolmonomethyl- erfindungsgemäßen Orthokieselsäureestern gemischt werätherrest, oder den können, sind die in der GB-PS 1341 901 erwähntena) R 1 is a tert-butyl radical and —OR 2 , —OR 3 and 40 esters. Further examples of known base oils which are or can be mixed with the —OR 4, in each case a triethylene glycol monomethyl orthosilicic acid ester according to the invention, are those mentioned in GB-PS 1341 901
b) R1 ein Neopentylrest und —OR2, —OR3 und und in den GB-PSen 1083324 und 1249803 ausführ-—OR4 jeweils ein Tripropylenglykolmonomethyl- licher beschriebenen Dicarbonsäureester und Glykolätherrest, oder 45 diester.b) R 1 is a neopentyl radical and —OR 2 , —OR 3 and and in GB-PSs 1083324 and 1249803 executes — OR 4 each a tripropylene glycol monomethyl dicarboxylic acid ester and glycol ether radical described, or 45 diesters.
c) R1 und R2 jeweils ein tert.-Butylrest und —OR3 Es ist im allgemeinen erwünscht, daß die unter Ver- und —OR4 jeweils ein Dipropylenglykolmono- wendung der erfindungsgemäßen Orthokieselsäureester methylätherrest, oder erhaltenen Hydraulikflüssigkeiten eine kinematische Vis-c) R 1 and R 2 each represent a tert-butyl radical and —OR 3. It is generally desirable that the dipropylene glycol mono-application of the orthosilicic acid ester according to the invention or the hydraulic fluids obtained under Ver and —OR 4 each have a kinematic vis-
d) R1 und R2 jeweils ein tert.-Butylrest, —OR3 ein kosilät von höchstens 50 und insbesondere nicht mehr Dipropylenglykolmonomethylätherrestund—OR4 50 als 20 cm2/s bei -40°C und einen Siedepunkt von minein Triäthylenglykolmonomelhylätherrcst, oder destens 230° und vorzugsweise mindestens 2600C be-d) R 1 and R 2 each have a tert-butyl radical, —OR 3 a cosile of at most 50 and in particular no more dipropylene glycol monomethyl ether radical and — OR 4 50 than 20 cm 2 / s at -40 ° C and a boiling point of min in triethylene glycol monomethyl ether, or at least 230 ° and preferably at least 260 0 C
e) R1 ein tert.-Butylrest und —OR2, —OR3 und sitzen.e) R 1 is a tert-butyl radical and —OR 2 , —OR 3 and sit.
—OR4 jeweils ein Dipropylenglykolmonomethyl- Den unter Verwendung der erfindungsgemäßen Ortho-—OR 4 each have a dipropylene glycol monomethyl den using the ortho according to the invention
ätherrest, oder · kieselsäureester erhaltenen Hydraulikflüssigkeiten wer-ether residue, or hydraulic fluids obtained from silicic acid esters
f) R1 und R2 jeweils ein tert.-Butylrest und —OR3 55 den in der Regel kleine Mengen verschiedener Additive und —OR4 jeweils ein Triälhylenglykolmono- der in Hydraulikflüssigkeiten üblicherweise verwendeten methylätherrest. oder Arten zugemischt.f) R 1 and R 2 are each a tert-butyl radical and —OR 3 55 are usually small amounts of various additives and —OR 4 are each a triethylene glycol mono of the methyl ether radical commonly used in hydraulic fluids. or species mixed in.
g) R1 und R2 jeweils ein lert.-Butylrest und —OR3 Typische verwendbare Additive sind die sciimierwirk- und —OR4 jeweils ein Tripropylenglykolmono- samen Additive aus der Gruppe Ricinusöl oder in vermethyläthcrrest. oder 60 schiedener Weise behandelter Ricinusölc. z.B.g) R 1 and R 2 each have a tert-butyl radical and —OR 3, typical additives that can be used are the sciimizing active and —OR 4, each a tripropylene glycol monosamic additive from the castor oil group or in a methyl ether radical. or 60 differently treated castor oilc. e.g.
H h) R1 ein tert.-Butylrest und —OR2, —OR3 und »Firsts« Ricinusöl.H h) R 1 is a tert-butyl radical and —OR 2 , —OR 3 and “Firsts” castor oil.
—OR4 jeweils ein Tripropylenglykolmonomethyl- Ricinusöl nach Spezifikation DTD 72.—OR 4 each a tripropylene glycol monomethyl castor oil according to specification DTD 72.
{£· ätherrest ist. geblasenes Ricinusöl. d.h. ein Ricinusöl. das unler{£ · ätherrest is. blown castor oil. i.e. a castor oil. the unler
fii. Der Siedepunkt der Orthokieselsäureester der Erfin- Erhitzen mit Luft oder Sauerstoff geblasen wurde.fii. The boiling point of the orthosilicic acid ester of the invention was heated with air or oxygen blown.
p dung ist im allgemeinen um so höher je größer das b"> spezial-hclles. geblasenes Ricinusöl. d.h. ein aufp is generally the higher the larger the b "> special hclles. blown castor oil. i.e. an on
"' Molekül ist, wobei die Zahl der C-Atome im Molekül ähnliche Weise geblasenes Ricinusöl"'Molecule is where the number of carbon atoms in the molecule is similar to blown castor oil
ψ. ein zweckmäßiger Parameter für dessen Größe ist. Dem- und ein im Handel erhältliches, mit Äthylenoxid und Il ψ. is a convenient parameter for its size. Dem and a commercially available one with ethylene oxide and II
;!■ entsprechend sind mindestens 15 C-Atome erforderlich. Propylenoxid behandeltes Ricinusöl. ||;! ■ at least 15 carbon atoms are required accordingly. Castor oil treated with propylene oxide. ||
Andere schmierwirksame Additive, die den unter Verwendung der erfindungsgemäßen Orthoki&selsäureesier erhaltenen Hydraulikflüssigkeiten einverleibt werden können, sind u.a. Borsäureester, tl.B. Trikresylborat. und Phosphorenthaltende Ester, insbesondere Phosphate. z.B. Trikresylphosphat.Other lubricating additives that can be incorporated into the hydraulic fluids obtained using the orthocoils according to the invention are, inter alia, boric acid esters, tl. B. tricresyl borate. and phosphorus-containing esters, especially phosphates. e.g. tricresyl phosphate.
Die unter Verwendung der erfindungsgemäßen Orthokieselsäuresster erhaltenen Hydraulikflüssigkeiten können auch kleinere Mengen an Polyoxyalkylenglykolen oder Polyoxyalkylenglykoläthern enthalten. Zweckmäßige Beispiele solcher Polyoxyalkylenglykole und ihrer Äther und Ester sind in der GB-PS 1055641 angegeben. Andeire geeignete scnmienvirksame Zusätze sind Orthophosphate oder Sulfate primärer oder sekundärer aliphatischer Amine mit insgesamt 4 bis 24 C-Atomen, die Allkylcitrate mit durchschnittlich 3j bis 13 C-Atomen in den Alkylresten, aliphatische Dicarbonsäuren und deren Ester. Spezielle Beispiele solcher Additive sind:Using the orthosilicic acid esters according to the invention The hydraulic fluids obtained can also contain smaller amounts of polyoxyalkylene glycols or contain polyoxyalkylene glycol ethers. Appropriate Examples of such polyoxyalkylene glycols and their Ethers and esters are given in GB-PS 1055641. Other suitable chemical additives are orthophosphates or sulfates of primary or secondary aliphatic Amines with a total of 4 to 24 carbon atoms, the alkyl citrates with an average of 3j to 13 carbon atoms in the alkyl radicals, aliphatic dicarboxylic acids and their esters. Specific examples of such additives are:
Diamylaminorthophosphat,
Dinonylaminorthophosphat,
Diamylaminsulfat.
Dinonylcitrat.
Di-( 2-äthyIhexyl)-citrat.Diamylamine orthophosphate,
Dinonylamine orthophosphate,
Diamylamine sulfate.
Dinonyl citrate.
Di- (2-ethyhexyl) citrate.
von einem Polyoxyäthylenglykol mit einem Molekulargewicht von 200 abgeleitetes Polyoxyäthylensebacat,
-azelat oder -adipat,
Polyoxyäthylen/Polyoxypropylen-GIutarat. abgeleitet
von einem Polyoxyglykolgemisch mit einem Durchschnittsmolekulargewicht von etwa 200.
Glutarsäure,
Azelainsäure,
Sebacinsäure,
Bernsteinsäure,
Diäthylsebacat,
Di-(2-älhylhexyl)-sebaeat und
Di-(isooctyl)-azelat.Polyoxyethylene sebacate, azelate or adipate derived from a polyoxyethylene glycol with a molecular weight of 200,
Polyoxyethylene / polyoxypropylene giarate. derived from a polyoxyglycol mixture with an average molecular weight of about 200.
Glutaric acid,
Azelaic acid,
Sebacic acid,
Succinic acid,
Diethyl sebacate,
Di- (2-ethylhexyl) sebaeate and
Di (isooctyl) azelate.
Ungesättigte aliphatische Säuren oder deren Salze, z.B. Ölsäure oder Kaliumricinoleat. können ebenfalls verwendet werden.Unsaturated aliphatic acids or their salts, e.g. oleic acid or potassium ricinoleate. can also be used.
Verwendbare Korrosionsinhibitoren können aus heterocyclischen. Stickstoff enthaltenden Verbindungen. z.B. Benzotriazol und Benzotriazolderivate, wie die in der GB-PS 1061904 beschriebenen, oder Mercaptobenzthiazoien, ausgewählt werden. Als Korrosionsinhibitoren eignen sich auch viele Amine oder Aminderivate. Z.B. können den Hydraulikflüssigkeiten als Korrosionsinhibitoren Usable corrosion inhibitors can be selected from heterocyclic. Compounds containing nitrogen. e.g., benzotriazole and benzotriazole derivatives such as those in US Pat GB-PS 1061904 described, or mercaptobenzthiazoien, to be selected. Many amines or amine derivatives are also suitable as corrosion inhibitors. E.g. hydraulic fluids can be used as corrosion inhibitors
Di-(n-butylamin),
Di-(n-amylamin),
Cyclohexylamin,
Morpholin,
Triäthanülamin,Di- (n-butylamine),
Di- (n-amylamine),
Cyclohexylamine,
Morpholine,
Triethanulamine,
und deren lösliche Salze, z.B. Cyclohexylamincarbonat. and their soluble salts, e.g., cyclohexylamine carbonate.
Phosphite, ζ. B. Triphenylphosphit und
Di-(isopropyl)-phosphit, die ebenfalls gute Korrosionsinhibitoren sind,Phosphites, ζ. B. triphenyl phosphite and
Di- (isopropyl) -phosphite, which are also good corrosion inhibitors,
und bestimmte anorganische Salze, z. B. Natriumnitrat, and certain inorganic salts, e.g. B. Sodium Nitrate,
zugesetzt werden.can be added.
Andere Additive, die den unter Verwendung der erfindungsgemäiier· Orthokieselsäureester erhaltenen Hydraulikflüssigkeiten zugesetzt werden können, sind Antioxidantien, wie Dia?ylamine, z.B. Diphenylamin. p.p'-Dioctyl-diphenylamin, Phenyl-a-naphthylamin oder Phenyl-ß-miphthykimin. Andere brauchbare AntioxidantienOther additives that make use of the inventive · Orthosilicic acid esters can be added to hydraulic fluids obtained are antioxidants, like dialylamines, e.g. diphenylamine. p.p'-dioctyl-diphenylamine, Phenyl-a-naphthylamine or phenyl-ß-miphthykimin. Other useful antioxidants
sind die allgemein als »gehinderte Phenole« bekannten Verbindungen, z. B.are the compounds commonly known as "hindered phenols"; B.
2,4-DimethyI-6-tert.-butyIphenol,
2,6-Di-tert.-butyI-4-methylphenoI,
2.6-Di-tert.-butylphenol.2,4-dimethyl-6-tert-butylphenol,
2,6-di-tert-butyI-4-methylphenol,
2,6-di-tert-butylphenol.
l,l-Bis(3,5-di-tert.-butyI-4-hydroxyphenyl)-methan,
S.S'.S.S'-Tetra-tert.-butyM^'-dihydroxy-di-phenyl.
3-MethyI-4,6-di-tert.-butylphenol und
4-Methyl-2-tert.-butylphenol.1,1-bis (3,5-di-tert-butyI-4-hydroxyphenyl) methane, S.S'.S.S'-tetra-tert.-butyM ^ '- dihydroxy-di-phenyl. 3-methyl-4,6-di-tert-butylphenol and
4-methyl-2-tert-butylphenol.
Wieder andere Additive, die verwendet werden können, sind Phenothiazin und dessen Derivate. z.B. diejenigen mit an das Stickstoffatom oder die Arylgruppen im Phenothiazinmolekül gebundenen Alkyl- oder Arylresten. Still other additives that can be used are phenothiazine and its derivatives. e.g. those with on the nitrogen atom or the aryl groups in the Phenothiazine molecule bonded alkyl or aryl radicals.
Als weitere Additive können außerdem u.a. Alkylenoxid/Ammoniak-Kondensationsprodukte. z.B. das in der GB-PS 1249803 beschriebene Propylenoxid/Amraoniak-Kondensationsprodukt. verwendet werden, und rA-ar als Korrosionsinhibitoren: Ais schmienvirksame Additive können ferner im Handel befindliche komplexe Ester und auch die in der GB-PS 1249803 beschriebenen Produkte verwendet werden. Außerdem lassen sich als Additive langkettige (z. B. C)10_lg,-primäre Aminkorrosionsinhibitoren und polymerisierte Chinolinharzantioxidantien. wie in der GB-PS 1249803 beschrieben),verwenden. Other additives that can be used include alkylene oxide / ammonia condensation products. for example the propylene oxide / ammonia condensation product described in GB-PS 1249803. can be used, and rA-ar as corrosion inhibitors: As lubricant additives, commercially available complex esters and also the products described in GB-PS 1249803 can be used. In addition, long-chain (e.g. C ) 10- lg primary amine corrosion inhibitors and polymerized quinoline resin antioxidants can be used as additives. as described in GB-PS 1249803).
Gebräuchliche Additive, wie dvi vorstehend beschriebenen, werden normalerweise in kleinen Mengen. z.B.Common additives such as dvi described above are usually used in small amounts. e.g.
3e 0.05 bis 10 und insbesondere 0.1 bis 2 Gewichtsprozent, verwendet.3e 0.05 to 10 and in particular 0.1 to 2 percent by weight, used.
Die Orthokieselsäureester der Erfindung lassen sich hersfeilen, indem man z.B. in an sich bekannter Weise ein Siliciumtetrahalogenid oder einen Orthokieselsäure-The orthosilicic acid esters of the invention can be refined by, for example, in a manner known per se a silicon tetrahalide or an orthosilicic acid
J5 ester mit einer oder mehreren der der Formel I entsprechenden Hydroxyverbindungen umsetzt.J5 ester with one or more of the formula I corresponding hydroxy compounds.
Zur Herstellung von Ort hosilikaten. die cfcvcn oder zwei Alkylrest(e) enthalten, kann man beispielsweise SiCl4 oder einen Orthokieselsäureester schrittweise mit demFor the production of in-situ hosilicates. which contain cfcvcn or two alkyl radical (s), for example, SiCl 4 or an orthosilicic acid ester can be added stepwise with the
4C gewünschten Glykolmonoälher im entsprechenden stöchiometrischen Verhältnis (z.B. 1:2) umsetzen und das Reaktionsprodukt dann mit Alkenol {■£ B. im Verhältnis 1:2) umsetzen. Vorzugsweise kann man auch einen Orthokieselsäureester, wie Kieselsäuretetraäthylester, mit einem entsprechenden Alkohol umestern. um die gewünschte Anzahl der erforderlichen Alkylreste einzuführen und die dabei erhaltene Verbindung mit einem Glykolmonoäther weiter umestern. um die restlichen Äthylreste gegen Glykolmonoätherreste auszutauschen.4C convert the desired glycol monohydric alcohol in the appropriate stoichiometric ratio (eg 1: 2) and then react the reaction product with alkenol ( e.g. in a ratio 1: 2). An orthosilicic acid ester, such as tetraethyl silicic acid, can preferably also be transesterified with a corresponding alcohol. to introduce the desired number of alkyl radicals required and further transesterify the compound obtained with a glycol monoether. to exchange the remaining ethyl residues for glycol monoether residues.
Bei der Herstellung der erfindungsgemäßen Orthokieselsäureester durch Umestern wird vorzugsweise ein Katalysator verwendet. z.B. Natriummetall, das die Reaktion über die Bildung des Alkoxids des Glykolmonoäthers crj :ichtert, oder ein bekannter Umestcrungskatalysator, wie p-Toluolsulfonsäuie oder ein Telraalkyl-, z.B. Tetraisopropyltitanat.In the preparation of the orthosilicic acid esters according to the invention by transesterification, a Catalyst used. E.g. sodium metal, which the reaction via the formation of the alkoxide of the glycol monoether crj: ichtert, or a known transesterification catalyst, such as p-Toluolsulfonsäuie or a Telraalkyl-, e.g. tetraisopropyl titanate.
Die Herstellung der erfindungsgemäßen Orthokieselsäureester aus ^iliciumtetrahalogeniden kann durch Umsetzen der entsprechenden Hydroxy verbindung mil dem Tetrahalogenid bei einer Temperatur vcn —40° bis l50aC. vorzugsweise von 40° bis 100°C. ohne Schwierigkeiten, gegebenenfalls in Gegenwart eines inerten Lösungsmittels, wie Alkyläthern. Toluol und Petroläther. durchgeführt werden. Außerdem kann ein Säure« akzeptor, z.B. ein tertiäres Amin. verwendet werden, um den bei der Umsetzung entstehenden Halogenwasserstoffabzufangen. Can iliciumtetrahalogeniden The preparation of the invention Orthokieselsäureester from ^ by reacting the corresponding hydroxy compound mil tetrahalide the VCN at a temperature -40 ° to l50 a C. preferably from 40 ° to 100 ° C. without difficulty, optionally in the presence of an inert solvent such as alkyl ethers. Toluene and petroleum ether. be performed. In addition, an acid acceptor, for example a tertiary amine. can be used to trap the hydrogen halide formed during the reaction.
Bei der Herstellung der erfindungsgemüßen Ortho-In the production of the inventive ortho
7 87 8
kieselsäureester durch Umcstcrn kann eine Reaktion*- Analyse: 4.92% Si (Theorie 5.68%); Restchlorgehalt:Silicic acid esters can cause a reaction when converted * - Analysis: 4.92% Si (theory 5.68%); Residual chlorine content:
temperatur von beispielsweise XO bis 250 und vor- 0.04%.temperature from, for example, XO to 250 and before 0.04%.
/ugsweise 120' bis 200"C angewandt und gewünschten- „ . . . . ^/ possibly 120 'to 200 "C applied and desired-".... ^
falls auch ein inertes Lösungsmitlei verwendet werden. ' "if an inert solvent is also used. '"
Weitere Einzelheiten der Herstellung von Glykolmono- 5 Bis(dipropylenglykolmonomethyläthcr)-bis(tert.-butyl)-ätherorlhokiesclsäureestern sind aus »Journal of Inor- kieselsäureesterFurther details of the preparation of glycol mono- 5 bis (dipropylene glycol monomethyl ether) bis (tert.-butyl) ether sulfate esters are from the »Journal of Inor- silicic acid esters
aanic Nuclear Chemistry«. I96X. Band 30. Seiten 721 bis 727 /u entnehmen.aanic Nuclear Chemistry ". I96X. Volume 30. Pages 721 to 727 / u.
Die nachstehenden Beispiele dienen zur Erläuterung der Erfindung.The following examples serve to illustrate the invention.
Tris<iripropylenglykolmonome.hyläther)-neoPentylkie-Tris (propylene glycol monomers, ethyl ether) -neo P entylkie-
sels.iurcester ); GemjSL.h von tert.-Butanol und 174 g Pyridin im Ver-sels.iurcester ); GemjSL . h of tert-butanol and 174 g of pyridine in the
Reaktionstcilnehmer: laufe von 2 Stunden versetzt, wobei die Wärmeentwicklung so geregelt wird, daß die Temperatur 41 3C nicht übersteigt. Dann wird das Reakiiuiisgcniiscli 4 Stunden lang auf KX)1C erhitzt, abkühlen gelassen 20 und dann mit einem Gemisch aus dem Dipropylenglykolmonomcthyläther und dem Rest des Pyridins versetzt. Das erhaltene Gemisch wird 4 Stunden lang auf In einem 5 Liter-Kolben werden das Toluol und SiIi- 100 C erhitzt, abgekühlt und filtriert, worauf man das ciumtetrachlorid gemischt und das Gemisch unter Toluol abstreift, das Reaktionsprodukt erneut filtriert Kühlen mit einer Mischung aus Neopentylalkohol 25 und schließlich im Hochvakuum (1803CzO1OI3 mbar) und 79 g Pyridin versetzt, wobei die Reaktionstempe- abstreift. Man erhält 248.2 g (53%) des Endprodukts ratur infolge der exothermen Reaktion auf maximal als klare gVibe Flüssigkeit.Reaction component: run for 2 hours, the heat development being regulated so that the temperature does not exceed 41 3 C. The reaction mixture is then heated to KX) 1 C for 4 hours, allowed to cool, and a mixture of dipropylene glycol monomethyl ether and the remainder of the pyridine is then added. The resulting mixture is heated for 4 hours in a 5 liter flask, the toluene and SiI-100 C, cooled and filtered, whereupon the cium tetrachloride is mixed and the mixture is stripped under toluene, the reaction product is filtered again, cooling with a mixture of neopentyl alcohol 25 and finally in a high vacuum (180 3 CzO 1 OI3 mbar) and 79 g of pyridine are added, the reaction temperature stripping off. 248.2 g (53%) of the end product temperature are obtained as a result of the exothermic reaction to a maximum of clear gVibe of liquid.
42"C ansteigt. Dann wird das Reaktionsgemisch 4 Stun- Analyse: 6,02% Si (Theorie 5,98%); Restchlorgehalt:42 "C. Then the reaction mixture becomes 4 hours analysis: 6.02% Si (theory 5.98%); residual chlorine content:
den lang auf 100 C erhitzt und über Nacht abkühlen 0,36%.the heated to 100 C for a long time and cool overnight 0.36%.
gelassen. Anschließend wird Tripropylenglykolmono- 30 Beispiel 4calmly. Then tripropylene glycol mono- 30 Example 4
methyläther und der Rest des Pyridins im Verlauf einermethyl ether and the rest of the pyridine in the course of a
halben Stunde zugegeben, wobei die exotherme Rcak- Bis(tert.-butyl)-(dipropylenglykolmonomethyläther)-(trition
durch Kühlen mit einem Wasserbad gesteuert wird. äthylenglykolmonomethyläther)-kieselsäureester
Man erhitzt das Reaktionsgemisch 5 Stunden und 20 Reaktionsteilnehmer-Minuten auf 112° bis 114 C. kühlt anschließend ab und J5 . . ]7f)
nitriert das ausgefallene Pyridinhydrochlorid ab. Hierauf blC 'a j^g jj
wird das Lösunasmittel in einem Rotationsverdampfer tert.-Butano .... . , 1O "
abgestreift und das Produkt schließlich im Hochvakuum D.propylenglykolmonomethylalher 48 g
(200 C/0.1333 mbar) abgestreift. Man erhält 484.4 g Tr.athylenglykolmonomethylather 197 g
(66.3%) des Endprodukts. 40 toluol 2 5 Literadded half an hour, the exothermic Rcak bis (tert-butyl) - (dipropylene glycol monomethyl ether) - (trition is controlled by cooling with a water bath. Ethylene glycol monomethyl ether) silicic acid ester
The reaction mixture is heated to 112 ° to 114 ° C. for 5 hours and 20 minutes of reactants, then cools and J5. . ] 7f)
nitrates the precipitated pyridine hydrochloride. Then blC ' a j ^ g jj
is the solvent in a rotary evaporator tert-butano ..... , 1O "
stripped and the product finally in a high vacuum D.propylenglykolmonomethylalher 48 g
(200 C / 0.1333 mbar) stripped. 484.4 g of potassium glycol monomethyl ether 197 g are obtained
(66.3%) of the final product. 40 toluene 2 5 liters
Analyse: 3,74% Si (Theorie 3.84%): Restchloridge- Pyndin S3- gAnalysis: 3.74% Si (theory 3.84%): residual chloride pyndin S3- g
halt: 0.15%. Eine in einem 5 Liter-Kolben vorgelegte Mischungstop: 0.15%. A mixture placed in a 5 liter flask
aus Toluol und SiCI4 wird mit einem Gemisch aus tert.-Beispiel 2 Butanol und 158 g Pyridin versetzt, wobei die Tempe-from toluene and SiCl 4 is mixed with a mixture of tert-Example 2 butanol and 158 g of pyridine, the temperature
... .,·..,, ι·· ι. ,- . „ . , , ■ 45 ratur durch Kühlen mit einem Wasserbad auf unterhalb...., · .. ,, ι ·· ι. , -. ". ,, ■ 45 temperature by cooling with a water bath to below
Tris(tnathylenglykolmonomethylather)-tert.-butyl-kie- ^ geha|ten wjrd Das Reaktionsgemisch wird dann Tris (ethylene glycol monomethyl ether) -tert-butyl- kie | th is held. The reaction mixture is then
selsdureester 4 Stunden ,ang auf 80» bjs ,0(rc ernitzt, abkühlenselsdureester 4 hours , ang to 80 » bjs , 0 (rc heated , cool
Reaktionsteilnehmer: gelassen und mit einem Gemisch aus Dipropylenglykol-Reactants: left and with a mixture of dipropylene glycol
monomethyläther und 79 g Pyridin versetzt. Dabei findet 50 eine sehr schwache exotherme Reaktion statt. Das Reaktionsgemisch wird dann 4 Stunden lang auf 80°C erhitzt, wiederum abkühlen gelassen und mit einem Gemisch aus Triäthylenglykolmonomethyläther und dem Rest des Pyridins (95 g) versetzt, wobei mit einem Wasserbad Ein Gemisch aus SiCI4 und 2.5 Liter Toluol wird mit 55 gekühlt wird.monomethyl ether and 79 g of pyridine were added. A very weak exothermic reaction takes place. The reaction mixture is heated to 80 ° C for 4 hours, allowed to cool again and with a mixture of triethylene glycol monomethyl ether and the remainder of pyridine (95 g) was added, thereby using a water bath a mixture of SiCl 4 and 2.5 liters of toluene cooled with 55 will.
einem Gemisch aus tert.-Butanol und 87 g Pyridin ver- Hierauf erhitzt man das Reaktionsgemisch 6 Stundena mixture of tert-butanol and 87 g of pyridine. The reaction mixture is then heated for 6 hours
setzt, wobei die Temperatur unter 50:C gehalten wird. auf 100° bis 104°C, läßt es dann abkühlen, filtriert, streift
Das Reaktionsgemisch wird dann 4 Stunden lang auf das Toluol ab und streift schließlich das Reaktionsgemisch
100=C erhitzt, abgekühlt und dann mit einem Gemisch im Hochvakuum (180°C/0,0667 mbar) ab. Das dabei
aus Triäthylenglykolmonomethyläther und dem Rest 60 erhaltene Produkt wird filtriert und man erhält 413,1 g
des Pyridins versetzt, wobei die Temperatur wiederum (86%) einer klaren, gelben Flüssigkeit,
unter 50=C gehalten wird. Um das Rühren zu erleichtern. Analyse: 5.85 % Si (Theorie 5,78 %); Restchlorgehalt:sets, keeping the temperature below 50 : C. to 100 ° to 104 ° C, then allowed to cool, filtered, stripped The reaction mixture is then stripped for 4 hours on the toluene and finally stripped the reaction mixture 100 = C, cooled and then with a mixture in a high vacuum (180 ° C / 0.0667 mbar). The product obtained from triethylene glycol monomethyl ether and the remainder 60 is filtered and 413.1 g of the pyridine are obtained, the temperature in turn (86%) of a clear, yellow liquid,
is kept below 50 = C. To make stirring easier. Analysis: 5.85% Si (theory 5.78%); Residual chlorine content:
gibt man weiteres Toluol (250 ml) zu und erhitzt das 0,24%.
Reaktionsgemisch dann insgesamt 4 Standen lang auf
100°C. Hierauf wird abgekühlt, filtriert und das Toluol 65more toluene (250 ml) is added and the 0.24% is heated.
The reaction mixture then stands up for a total of 4 times
100 ° C. It is then cooled, filtered and the toluene 65
(100aC/26,66 mbar) abgestreift. Das erhaltene Produkt Beispiel D(100 a C / 26.66 mbar) stripped. The product obtained Example D
wird dann im Hochvakuum (210°C/0,667 mbar) abge- Tris(dipropylenglykolmonornethyläther)-tert.-butyl-kiestreift. Man erhält 346 g (70,4%) des Endprodukts. selsäureesterTris (dipropylene glycol monomethyl ether) tert-butyl kiestrip is then removed in a high vacuum (210 ° C./0.667 mbar). 346 g (70.4%) of the end product are obtained. selsic acid ester
Reaktionsteilnehmer:Reaction participants:
SiCI4 170 gSiCl 4 170 g
tert.-Butiinol 74 gtert-Butiinol 74 g
Dipropylcnglykolmonomethyliitlier 488 g Pyridin " ' 348 gDipropyleneglycol monomethylitlier 488 g Pyridine "'348 g
Toli'ol 1 Liter + 2IX) ml + 20« mlToli'ol 1 liter + 2IX) ml + 20 «ml
200 ml +4(K) i«l +1 Liter200 ml +4 (K) i «l +1 liter
Eine Vormischung ;ius SiCI4 und 1 Liier Toluol wird mit einem Gemisch aus tert.-Bulanol u.id 80 g Pyridin versetzt. Während der Zugabe wird die exotherme Reaktion durch Kühlen mit einem Wasserbad geregelt. Hierauf werden die Reaktionsteilnehmer 3 Stunden lang auf 80 C erhitzt und dann ein Gemisch aus dem Rest des Pyridins und dem Dipropylenglykolmonomethyläther zugesetzt. Während der Zugabe wird das Reaktionsgemisch viskos und schwer zu rühren, so daß weitere Teilmengen Toliic! {3*300 m! und dann 1x400 ml) nach Bedarf zugesetzt werden. Die Wärmeentwicklung während der Zugabe wird durch Kühlen mit einem Wasserbad geregelt. Nach beendeter Zugabe wird das Reaktionsgemisch in einen 5 Liter-Kolben überführt, wobei ein weiterer Liter Toluol zugesetzt wird, und dann 12 Stunden lang auf 80"C erhitzt. Das dabei erhaltene Produkt wird filtriert, dann das Lösungsmittel abgestreift und hierauf das Produkt im Hochvakuum (2000C/ 0.1333 mbar) abgestreift. Schließlich wird das Produkt filtriert und man erhält 399 g (73.6%) einer klaren gelben Flüssigkeit.A premix; ius SiCl 4 and 1 lithium toluene is mixed with a mixture of tert-bulanol and 80 g of pyridine. During the addition, the exothermic reaction is regulated by cooling with a water bath. The reactants are then heated to 80 ° C. for 3 hours and then a mixture of the remainder of the pyridine and the dipropylene glycol monomethyl ether is added. During the addition, the reaction mixture becomes viscous and difficult to stir, so that further aliquots of Toliic! {3 * 300 m! and then 1x400 ml) can be added as required. The heat development during the addition is regulated by cooling with a water bath. When the addition is complete, the reaction mixture is transferred to a 5 liter flask, a further liter of toluene being added, and the mixture is then heated to 80 ° C. for 12 hours. The product obtained is filtered, then the solvent is stripped off and the product is then removed under high vacuum stripped (mbar 200 0 C / 0.1333). Finally, the product is filtered and is obtained 399 g (73.6%) of a clear yellow liquid.
.nalyse: 5.48% Si (Theorie 5,17%); Restchlorgehalt: JO 0.15%.Analysis: 5.48% Si (theory 5.17%); Residual chlorine content: JO 0.15%.
Bis (triäthylenglykolmonomethyläther) - bis (tert.- butyl) kieselsäureester Bis (triethylene glycol monomethyl ether) - bis (tert-butyl) silicic acid ester
Reaktionsteilnehmer:Reaction participants:
Eine Vormischung aus SiCI4 und 2.5 Liter Toluol wird mit einem Gemisch aus tert.-Butanol und 174 g Pyridin versetzt, wobei die Temperatur während der Zugabe unter 500C gehalten wird. Dann erhitzt man das Reaktionsgemisch 4 Stunden lang auf 100°C. kühlt es ab und versetzt es mit einem Gemisch aus Triäthylenglykolmonomethyläther und dem Rest des Pyridins. Dabei findet eine schwach exotherme Reaktion statt, wobei die Temperatur unter 50 °C gehalten wird. Das Reaktionsgemisch wird dann 4 Stunden lang auf 10O0C erhitzt. Während dieser Zeit gibt man weitere 250 ml Toluol zu. um das Rühren zu erleichtern. Das erhaltene Rohprodukt wir-d abgekühlt und filtriert, worauf man Toluol abstreift und das Produkt dann im Hochvakuum abstreift, wobei man als Endprodukt eine klare, hellgelbe Flüssigkeit in einer Ausbeute von 323,1 g (64,6%) erhält.A premix of SiCl 4 and 2.5 liters of toluene is mixed with a mixture of tert-butanol and 174 g of pyridine, the temperature being kept below 50 ° C. during the addition. The reaction mixture is then heated to 100 ° C. for 4 hours. it cools down and a mixture of triethylene glycol monomethyl ether and the rest of the pyridine is added. A slightly exothermic reaction takes place, the temperature being kept below 50 ° C. The reaction mixture is then heated for 4 hours at 10O 0 C. During this time, a further 250 ml of toluene are added. to make stirring easier. The crude product obtained is cooled and filtered, whereupon toluene is stripped off and the product is then stripped off in a high vacuum, the end product being a clear, light yellow liquid in a yield of 323.1 g (64.6%).
Analyse: 5,7% Si (Theorie 5,6%); Restchloreehalt: 0.05%.Analysis: 5.7% Si (theory 5.6%); Residual chlorine content: 0.05%.
Bis(tripropylenglykolmonomethyläther)-bis(tert.-butyl)-kieselsäureester Bis (tripropylene glycol monomethyl ether) bis (tert-butyl) silicic acid ester
Ein Gemisch aus SiCI4 und Toluol wird unter Kühlen mit einem Wasserbad im Verlaufe von 2 Stunden mit einem Gemisch aus terl.-Bulanol und I 74 g Pyridin versetzt, wobei die Temperatur des Rcuktionsgornischcs infolge einer mäßig starken Wärmeentwicklung auf maximal 38"C steigt. Das Reaklionsgemisch wird dann 4 Stunden lang auf 100 C erhitzt, abgekühlt und dann im Verlaufe von 2 Stunden mit einem Gemisch aus dem Tripropylenglykolmonomethyläther und dem restlichen Pyridin versetzt, wobei eine geringe Wärmeentwicklung ■>.c«.tfindcl welche die Teiri^cruiisr des ReiiklicMS'Temi" sches auf höchstens 30"C ansteigen läßt. Dann wird das Reaktionsgemisch 4 Stunden auf 1OO'JC erhitzt, abgekühlt und filtriert, das Lösungsmittel abgestreift und das Produkt schließlich im Hochvakuum (180'C 0,1333 mbar) abgestreift. Man erhält 367.2 g (63 %) Endprodukt. A mixture of SiCl 4 and toluene is mixed with a mixture of terl-Bulanol and 74 g of pyridine over the course of 2 hours, while cooling with a water bath, the temperature of the reduction gas rising to a maximum of 38 ° C. as a result of the moderately strong development of heat. The reaction mixture is then heated to 100 ° C. for 4 hours, cooled and then a mixture of the tripropylene glycol monomethyl ether and the remaining pyridine is added over the course of 2 hours, with a slight evolution of heat which is the part of the reason 'can be "ULTRASONIC to a maximum of 30" C rise T emi. Then the reaction mixture 4 hours at 1OO' J C heated, cooled and filtered, the solvent stripped and finally stripped off the product in high vacuo (0.1333 mbar 180'C). 367.2 g (63%) of the end product are obtained.
Analyse: 4,96% Si (Theorie 4.8%); Restchlorgehalt: Nicht bestimmt.Analysis: 4.96% Si (theory 4.8%); Residual chlorine content: Not determined.
Tris(tripropylcnglykolmonomethylät her)-tert.-butyl-kieselsäureester Tris (tripropylene glycol monomethyl ether) tert-butyl silicic acid ester
Reaktionsteilnehmer:Reaction participants:
SiCI4 119 gSiCl 4 119 g
tert.-Butanol 51.8gtert-butanol 51.8g
Tripropylenglykolmonoinethyläthcr 474 g
Pyridin 237 gTripropylene glycol monoinethyl ether 474 g
Pyridine 237 g
Toluol 250 ml+ 300 ml+ 600 ml+ 200 mlToluene 250 ml + 300 ml + 600 ml + 200 ml
In einem zur Kühlung mit einem Wasserbad ausgerüsteten Kolben wird ein Gemisch aus SiCI4 und 250 ml Toluol mit einem Gemisch aus tert.-Butanol und 80 g Pyridin versetzt. Durch die exotherme Reaktion erhöht sich die Temperatur auf 300C. Um das Reaktionsgemisch fließfähig zu halten, werden weitere 300 ml Toluol zugefügt, worauf man 2 Stunden lang am Rückfluß erhitzt. Das Reaktionsgemisch wird dann abgekühlt und im Verlaufe einer Stunde mit dem Tripropylenglykoimonomethyläther und dem restlichen Pyridin versetzt, wobei eine geringe Wärmeentwicklung festzustellen ist. Außerdem fügt man noch weitere 600 ml Toluol zu. Das Reaktionsgemisch wird mit Hilfe weiterer 200 ml Toluol in einen größeren Kolben überführt und hierauf 10 Stunden lang auf 900C erhitzt. Dann wird das Rohprodukt durch Filtrieren, Abstreifen des Lösungsmittels in einem Rotationsverdampfer und schließlich Abstreifen im Hochvakuum (I80°C/0,I333 mbar) aufgearbeitet, wobei man als Nebenprodukt 380g (75.9 %) einer hellgelben Flüssigkeit erhält.In a flask equipped with a water bath for cooling, a mixture of SiCl 4 and 250 ml of toluene is mixed with a mixture of tert-butanol and 80 g of pyridine. The exothermic reaction increases the temperature to 30 ° C. To keep the reaction mixture flowing, a further 300 ml of toluene are added, whereupon the mixture is refluxed for 2 hours. The reaction mixture is then cooled and the tripropylene glycol monomethyl ether and the remaining pyridine are added over the course of one hour, a slight evolution of heat being observed. A further 600 ml of toluene are also added. The reaction mixture is transferred to a larger flask with the aid of a further 200 ml of toluene and then heated to 90 ° C. for 10 hours. The crude product is then worked up by filtering, stripping off the solvent in a rotary evaporator and finally stripping in a high vacuum (180 ° C./0.1333 mbar), 380 g (75.9%) of a pale yellow liquid being obtained as a by-product.
Analyse: 3,86% Si (Theorie 3,91 %): Restchlorgehalt: 0.76%.Analysis: 3.86% Si (theory 3.91%): residual chlorine content: 0.76%.
Die Infrarotspektren der Produkte der vorstehenden Beispiele 1 bis 8 bestätigen in jedem Fall, daß das erwartete Produkt erhalten wurde.The infrared spectra of the products of Examples 1 to 8 above confirm in each case that the expected product was obtained.
Die Brauchbarkeit der erfindungsgemäßen Orthokieselsäureester zur Verwendung in Hydraulikflüssigkeiten wurde durch Messen des Rückflußsiedepunkts, der Hydrolysebeständigkeit und der Kautschukquellwirkung verschiedener Ester nachgewiesen.The usefulness of the orthosilicic acid esters according to the invention for use in hydraulic fluids was determined by measuring the reflux point, hydrolysis resistance and the rubber swelling effect of various esters.
Der RücklluBsieJcpunkl wurde in der in der Spezifikation SAE J 1703c angegebenen Weise bestimmt.The return message was included in the specification SAE J 1703c specified manner.
Die Kautschukquellung wurde jeweils wie folgt ermittelt: The rubber swelling was determined as follows:
In eine 56.8262 cm1-Flasche mit einer Glasperlenschieht am Boden wurde jeweils eine quadratische Kautschukplatte init Abmessungen von etwa 2.54 mal 2,54 mal 0,254 cm eingebracht. Dann wurde die Flasche mit der Testflüssigkeit gefüllt und 3 Tage lang bei konstanter Temperatur in einen Ofen gestellt, worauf die Kautschukplatte herausgenommen, mit Äthanol gewaschen und getrocknet wurde. Das Volumen der Kautschukplatte wurde vor und nach dem Test nach der bekannten Verdrängungsmethoiie jeweils genau gemessen und aus den Meßwerten dann die Volumenänderung in Prozent berechnet. Styrol-Butadien-Kautschukplatten wurden bei I2O"C, Naturkautschukplatten, die temperaüirempfin'Jüchcr sind, hpi 70°C geprüft, d.h. bei den für die Durchführung dieser Tests üblichen Temperaturen. A square rubber plate with dimensions of about 2.54 by 2.54 by 0.254 cm was placed in a 56.8262 cm 1 bottle with a glass bead layer on the bottom. Then, the bottle was filled with the test liquid and placed in an oven at a constant temperature for 3 days, after which the rubber sheet was taken out, washed with ethanol and dried. The volume of the rubber sheet was measured precisely before and after the test using the known displacement method, and the change in volume in percent was then calculated from the measured values. Styrene-butadiene rubber sheets were tested at I2O "C, natural rubber sheets, which are temperaüirempfin'Jüchcr, hpi 70 ° C, ie at the temperatures customary for carrying out these tests.
Außerdem wurden auch Nitril- und Chloroprenkautschukplatten verwendet, die jeweils bei einer Temperatur von 70 C geprüft wurden. Es sei darauf hingewiesen, daß. da Nitril- und Chloroprenkautschuk bislang üblicherweise nicht mit Bremsflüssigkeiten in Berührung kamen und diese Kautschuke daher nicht auf diese Weise geprüft wurden, es diesbezüglich keine anerkannte bzw. übliche Praxis gibt.In addition, nitrile and chloroprene rubber sheets were also made used, each of which was tested at a temperature of 70 C. It should be noted that. since nitrile and chloroprene rubber have not usually come into contact with brake fluids until now came and these rubbers were therefore not tested in this way, it was not recognized in this regard or common practice there.
Die Hydrolysebeständigkeit wurde bestimmt, indem 1 g Wasser, I g des zu prüfenden Orthokieselsäureesters und 9 g eines handelsüblichen Glykoläther-Hydraulikflüssigkcit-Basismaterials, sowie Siedesteine in ein Siederohr gegeben und über einem Bunsenbrenner zum Sieden erhitzt wurden. Dann ließ man das Siederohr samtThe resistance to hydrolysis was determined by adding 1 g of water to 1 g of the orthosilicic acid ester to be tested and 9 g of a commercially available glycol ether hydraulic fluid base material, as well as boiling stones placed in a boiler pipe and over a Bunsen burner to simmer were heated. Then you left the boiler pipe together
I abeiie iI abeiie i
Inhalt abkühlen, t'· is zu prüfende Gemisch wurde während des Siedens und anschließenden Abkühlens auf visuell erkennbare Anzeichen für Hydrolyseunbeständigkeit, wie Gelieren des Gemisches oder Bildung eines ■> Niederschlags bzw. Desiments. beobachtet. Nach dem Ergebnis der visuellen Begutachtung wurde dann der Orlhokieselsäureester bezüglich seiner Hydrolysebeständigkeit nach folgender Bewertungsskala bewertet:Cool contents, t'is mixture to be tested was during of boiling and subsequent cooling visually detectable signs of unstability to hydrolysis, such as gelling of the mixture or formation of a ■> Precipitation or desiments. observed. After this The result of the visual assessment was then the silicic acid ester with regard to its resistance to hydrolysis rated according to the following rating scale:
0 = Tesigemisch geliert 3 = Geringe0 = Tesa mixture gelled 3 = Low
SedimentbildungSedimentation
1 = Starke Sedimentbildung 4= Sehr schwache1 = Heavy sedimentation 4 = Very weak
SedimentbildungSedimentation
2 = Sedimcntbildung 5 = Klar2 = sediment formation 5 = clear
Als Glykoläther-Basisöl wurde bei diesen Untersuchungen eine mit Additiven (vermutlich Natriumnitrit. Agerite Resin D und Benzotriazol) partiell inhibierte Äthylen/Propylenglykoläthergemisch-Flüssigkeit mit einem Siedepunkt von 288"C verwendet. Dieses Basisöl wurde nach Vorversuchen ausgewählt, bei denen der Orthokieselsäureester mitThe glycol ether base oil used in these investigations one with additives (presumably sodium nitrite. Agerite Resin D and benzotriazole) partially inhibited Ethylene / propylene glycol ether mixture liquid with a boiling point of 288 "C used. This base oil was selected after preliminary tests in which the orthosilicic acid ester with
a) Wasser unda) water and
b) Wasser und Glykoläther-Basisöl ohne Additive
zum Sieden erhitzt wurde.b) Water and glycol ether base oil without additives
was heated to boiling.
Diese Vorversuche erwiesen sich als nicht scharf genug, um die Hydrolysebeständigkeil des geprüfter. Orthokieselsäureesters zu ermitteln. Es wurde gefunden, daß die Anwesenheit der Additive die Niederschlagsbildung steigerte.These preliminary tests did not prove to be sharp enough to make the hydrolysis-resistant wedge of the tested. To determine orthosilicic acid ester. It has been found that the presence of the additives stimulates the formation of precipitates increased.
Die Ergebnisse der Siedepunktbestimmung, Hydrolysebeständigkeitstests und Kautschukquelltests bei Styrol-Butadien-Kautschuk und Naturkautschuk sind in der Tabelle I, die Ergebnisse von Kautschukquelltests bei Nitrilkautschuk und Chloroprenkautschuk in den Tabellen Il bzw. III wiedergegeben.The results of boiling point determination, hydrolysis resistance tests and rubber swell tests on styrene-butadiene rubber and natural rubber are in of Table I, the results of rubber swell tests on nitrile rubber and chloroprene rubber in Tables II and III reproduced.
Siedepunkt (0C)Boiling point ( 0 C)
kautschukrubber
Butadien-Butadiene
Kautschukrubber
5,5
-0,7
8,037.6
5.5
-0.7
8.0
9.3
2,4
14,260.9
9.3
2.4
14.2
Tris(triäthylenglykolmonomethyläther)-tert.-butyl-kieselsäureester Tris(tripropylenglykolmonomethyläther)-neopentyl-kieselsäureester *Tris (triethylene glycol monomethyl ether) tert-butyl silicic acid ester Tris (tripropylene glycol monomethyl ether) neopentyl silicic acid ester *
Bis(dipropylenglykolmonomelhyläther)-bis(tert.-butyl)-kiesefsäureester *Bis (dipropylene glycol monomelhyl ether) bis (tert-butyl) siliceous acid ester *
Bis(tert.-butyl)-(dipropylenglykolmonomethyläther)-(triäthylenglykolmonomethyläther)-kieselsäureester *Bis (tert-butyl) - (dipropylene glycol monomethyl ether) - (triethylene glycol monomethyl ether) silicic acid ester *
Tris(dipropylenglykolmonomethyläther)-terL-butyl-kieselsäureester Bis(triäthylenglykolmonomethyläther)-bis(tert.-butyl)-kieselsäureester Bis(tripropylenglykolmonomethyläther)-bis(tert.-butyl)-kieselsäureester Tris(tripropylenglykolmonomethyläther)-tert--butyl-kieselsäureester Orthokieselsäureester A Tris (dipropylene glycol monomethyl ether) -terL-butyl-silicic acid ester Bis (triethylene glycol monomethyl ether) -bis (tert-butyl) -silicic acid ester Bis (tripropylene glycol monomethyl ether) -bis (tert-butyl) -silicate ester A.
Orthokieselsäureester B Orthosilicic acid ester B
Orthokieselsäureester COrthosilicic acid ester C
*\ Nicht bestimmt * \ Not determined
3 43 4th
4
4
5
54th
4th
5
5
5
0
1
15
0
1
1
Aus den in den Tabellen wieuergegebenen Versuchsergebnisffin
ist zu ersehen, daß die untersuchten Orthokieselsäureester befriedigende Siedepunkte und eine überlegene
Hydrolysebeständigkeil besitzen. Außerdem wurden niedrige Kautschukquellwerte bei Nitril- und ChIoroprenkautschuk
festgestellt. Die Kautschukquellwertc bei Styrol-Butadicn- und Naturkautschuk waren zwar
hoch, jedoch ist dem keine große Bedeutung zuzumessen,
da die niedrigen Kautschukquellwerte bei Chloropren- und Nitrilkautschuk weitaus wichtiger sind, wenn Hydraulikflüssigkeiten
hergestellt werden sollen, die mit allen genannten Kautschuken verträglich sind. Wenn die
Orthokieselsäureesterder Erfindung mit bekannten Fahrzeug-Hydrauiikflüssigkeits-BasisöIen.
die in bezug auf Chloropren- und Nitrilkautschuke sehr schlechte, gegenüber Styrol-Butadien- und Naturkautschuk dagegen
gute Eigenschaften aufweisen, gemischt werden, so weist das Gemisch im Vergleich mit den Werten des
reinen Orthokieselsäureesters bezüglich Styrol-Butadien-Kautschuken
und Naturkautschuken niedrigere, gegenüber Nitril- und Chloroprenkaulschukcn dagegen höhere
Kautschukquellwerte auf.
Dei den in den Tabellen 1 bis III erwähnten Kicselsäureestern
A bis C handelt es sich um nicht der Lehre der Erfindung entsprechende, jedoch auf die in den
Beispielen I bis 8 beschriebene Weise hergestellte GIykolmonoätherorthokieseisäureestcr.
die zum Vergleich geprüft wurden. Der Orthokieselsäurccstcr A war Tris-(triiithylenglykolmonomcthyläther)-isobutyl-kieselsäu
reester mit einem analytisch bestimmten Siliciumgchult von 5.0 Gewichtsprozent (Theorie 4.74%). [5er Orthokieselsäureester
/? war Tetra (triäthylenglykolmonomethyläther)-kieselsäureesler
mit einem Siliciumgehalt von 3.77 Gewichtsprozent (Theorie 4.1%). Der OthokiesclsäureesterC\varBis(tripropylcnglykolmonomcthyläther)-bis
(triäthylenglykolmonomel hy lather) -kieselsäureester
mit einem Siliciumgehalt von 4.17 Gewichtsprozent (Theorie 3,78 %).From the test results given in the tables it can be seen that the orthosilicic acid esters examined have satisfactory boiling points and a superior hydrolysis-resistant wedge. In addition, low rubber swell values were found for nitrile and chloroprene rubber. The rubber swell values for styrene-butadiene and natural rubber were high, but this is not of great importance, since the low rubber swell values for chloroprene and nitrile rubber are far more important if hydraulic fluids are to be produced that are compatible with all of the rubbers mentioned. When the orthosilicic acid esters of the invention are used with known vehicle hydraulic fluid base oils. which have very poor properties with respect to chloroprene and nitrile rubbers, but good properties with respect to styrene-butadiene and natural rubber, the mixture has lower values compared with the values of the pure orthosilicic acid ester with respect to styrene-butadiene rubbers and natural rubbers, compared with nitrile - and chloroprene sleeves, on the other hand, have higher rubber swelling values.
The silica esters A to C mentioned in Tables 1 to III are not in accordance with the teaching of the invention, but are prepared in the manner described in Examples I to 8, glycol monoether-orthocisic acid esters. which have been checked for comparison. The Orthokieselsäurccstcr A was tris (triithylene glycol monomethyl ether) isobutyl kieselsäu ester with an analytically determined silicon concentration of 5.0 percent by weight (theory 4.74%). [5er orthosilicic acid ester /? was tetra (triethylene glycol monomethyl ether) silicic acid ester with a silicon content of 3.77 percent by weight (theory 4.1%). The othosilicic acid ester C \ varBis (tripropylene glycol monomethyl ether) bis (triethylene glycol monomethyl ether) silicic acid ester with a silicon content of 4.17 percent by weight (theory 3.78%).
Geprüfter OrthokieselsäureesterTested orthosilicic acid ester
3-Tagc Kautschuk-Quelliest
Nitrilkautschuk ( X !,'Heilung)3-day rubber source yeast
Nitrile rubber ( X !, 'cure)
Bis(dipropylenglykolmonomethyläther)-bis(tert.-bytul-kieselsäureester 0 Bis(tert.-butyl)-(dipropylenglykolmonomethyläther)-Bis (dipropylene glycol monomethyl ether) bis (tert.-bytulosilicic acid ester 0 Bis (tert-butyl) - (dipropylene glycol monomethyl ether) -
(triäthylenglykolmonomethylL(her)-kieselsäureester 2,6(triethylene glycol monomethylL (her) silicic acid ester 2,6
Tris(dipropyleng!ykolmonomethyläther)-tert.-butyl-kieselsäureester - 0.01Tris (dipropylene glycol monomethyl ether) tert-butyl silicic acid ester - 0.01
Bis(triäthylenglykolmonomethy!äther)-bis(tert.-butyl)-kieselsäureester 7.2Bis (triethylene glycol monomethyl ether) bis (tert-butyl) silicic acid ester 7.2
BisCtripropylenglykolmonomethylätheO-bisdert.-butyO-kieselsäureestcr -0.34BisCtripropyleneglykolmonomethylätheO-bisdert.-butyO-Kieselsäureestcr -0.34
Orthokieselsäureester A 20.8Orthosilicic acid ester A 20.8
Orthokieselsäureester C 6.5Orthosilicic acid ester C 6.5
Geprüfter OrthokieselsäureesterTested orthosilicic acid ester
3-Tage Kautschuk-Quelltesl
Chloroprenkautschuk (% Quelluni!)3-day rubber quelltesl
Chloroprene rubber (% Quelluni!)
Tris(triäthylenglykolmonornethyläther)-tert.-butyl-kieselsäureester 1.5Tris (triethylene glycol monomethyl ether) tert-butyl silicic acid ester 1.5
TrisUripiOpylenglykolmonomethylätheO-neopentyl-kieselsäureester 0.2TrisUripiOpyleneglykolmonomethylätheO-neopentyl-Silicic acid ester 0.2
Orthokieselsäureester A 17.4Orthosilicic acid ester A 17.4
Orthokieselsäureester C 11.3Orthosilicic acid ester C 11.3
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB140973A GB1464712A (en) | 1973-01-10 | 1973-01-10 | Hydraulic fluids |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2400914A1 DE2400914A1 (en) | 1974-07-18 |
DE2400914C2 true DE2400914C2 (en) | 1983-12-15 |
Family
ID=9721530
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2400914A Expired DE2400914C2 (en) | 1973-01-10 | 1974-01-09 | Orthosilicic acid esters, process for their preparation and their use |
Country Status (16)
Country | Link |
---|---|
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) |
Families Citing this family (5)
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 |
DE3535839A1 (en) * | 1985-10-08 | 1987-04-09 | Hoechst Ag | METHOD FOR OPERATING HYDRAULIC SYSTEMS WITH LIQUIDS BASED ON GLYCOLES |
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 |
CA2904215A1 (en) * | 2013-03-12 | 2014-10-09 | The Lubrizol Corporation | Lubricating composition containing lewis acid reaction product |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3085105A (en) * | 1959-04-10 | 1963-04-09 | Shell Oil Co | Orthosilicate thiaesters |
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 |
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 |
US3806549A (en) * | 1971-11-03 | 1974-04-23 | Owens Corning Fiberglass Corp | Method of preparing organooxy silanes |
-
1973
- 1973-01-10 GB GB140973A patent/GB1464712A/en not_active Expired
-
1974
- 1974-01-09 DE DE2400914A patent/DE2400914C2/en not_active Expired
- 1974-01-09 DK DK009974A patent/DK150186C/en not_active Application Discontinuation
- 1974-01-09 SE SE7400260A patent/SE414635B/en not_active IP Right Cessation
- 1974-01-09 AT AT14274*#A patent/AT334495B/en not_active IP Right Cessation
- 1974-01-09 BR BR118/74A patent/BR7400118D0/en unknown
- 1974-01-09 IT IT19230/74A patent/IT1003345B/en active
- 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 IE IE45/74A patent/IE38727B1/en unknown
- 1974-01-09 FR FR7400657A patent/FR2213288B1/fr not_active Expired
- 1974-01-09 NO NO740057A patent/NO149890C/en unknown
- 1974-01-09 NL NLAANVRAGE7400295,A patent/NL169318C/en not_active IP Right Cessation
- 1974-01-09 ZA ZA00740164A patent/ZA74164B/en unknown
- 1974-01-09 CA CA189,780A patent/CA1029385A/en not_active Expired
-
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
Also Published As
Publication number | Publication date |
---|---|
DK150186B (en) | 1986-12-29 |
GB1464712A (en) | 1977-02-16 |
AU6436874A (en) | 1975-07-10 |
DK150186C (en) | 1987-10-19 |
NL169318B (en) | 1982-02-01 |
NO149890B (en) | 1984-04-02 |
DE2400914A1 (en) | 1974-07-18 |
ATA14274A (en) | 1976-05-15 |
CA1029385A (en) | 1978-04-11 |
AT334495B (en) | 1976-01-25 |
JPS5930758B2 (en) | 1984-07-28 |
SE414635B (en) | 1980-08-11 |
ZA74164B (en) | 1975-08-27 |
FR2213288B1 (en) | 1977-09-09 |
JPS4995925A (en) | 1974-09-11 |
IT1003345B (en) | 1976-06-10 |
FR2213288A1 (en) | 1974-08-02 |
JPS56147791A (en) | 1981-11-16 |
JPS56147792A (en) | 1981-11-16 |
BR7400118D0 (en) | 1974-08-22 |
NL7400295A (en) | 1974-07-12 |
NO740057L (en) | 1974-07-11 |
NO149890C (en) | 1984-07-11 |
IE38727L (en) | 1974-07-10 |
IE38727B1 (en) | 1978-05-24 |
NL169318C (en) | 1982-07-01 |
BE809559A (en) | 1974-05-02 |
JPS5757479B2 (en) | 1982-12-04 |
USRE30698E (en) | 1981-08-04 |
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