JPH07507830A - 機能流体 - Google Patents
機能流体Info
- Publication number
- JPH07507830A JPH07507830A JP6501547A JP50154794A JPH07507830A JP H07507830 A JPH07507830 A JP H07507830A JP 6501547 A JP6501547 A JP 6501547A JP 50154794 A JP50154794 A JP 50154794A JP H07507830 A JPH07507830 A JP H07507830A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- composition
- phosphate
- alkyl
- butyl
- 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.)
- Granted
Links
- 239000012530 fluid Substances 0.000 title claims description 168
- 239000000203 mixture Substances 0.000 claims description 198
- 229910019142 PO4 Inorganic materials 0.000 claims description 117
- 235000021317 phosphate Nutrition 0.000 claims description 117
- 239000010452 phosphate Substances 0.000 claims description 96
- -1 phosphate ester Chemical class 0.000 claims description 87
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 59
- 239000002585 base Substances 0.000 claims description 57
- 238000005260 corrosion Methods 0.000 claims description 39
- 230000007797 corrosion Effects 0.000 claims description 39
- 239000003112 inhibitor Substances 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
- 230000003628 erosive effect Effects 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 25
- 239000003963 antioxidant agent Substances 0.000 claims description 24
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 22
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 21
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 20
- 230000003078 antioxidant effect Effects 0.000 claims description 19
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 239000002516 radical scavenger Substances 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 230000036961 partial effect Effects 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 235000013824 polyphenols Nutrition 0.000 claims description 11
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000011065 in-situ storage Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 125000005266 diarylamine group Chemical group 0.000 claims description 7
- 150000002118 epoxides Chemical class 0.000 claims description 7
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 7
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 238000006056 electrooxidation reaction Methods 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 claims description 4
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical group CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- TZOHKIXYILEQDW-UHFFFAOYSA-N bis(2-methylpropyl) phenyl phosphate Chemical group CC(C)COP(=O)(OCC(C)C)OC1=CC=CC=C1 TZOHKIXYILEQDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical class C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 49
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 30
- 239000000654 additive Substances 0.000 description 14
- 229910052742 iron Inorganic materials 0.000 description 14
- 230000003301 hydrolyzing effect Effects 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 11
- 230000001590 oxidative effect Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 239000006210 lotion Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 239000002518 antifoaming agent Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 4
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 3
- 150000003862 amino acid derivatives Chemical class 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- OKLNGCVEHOKJIY-UHFFFAOYSA-N 3-butyl-4-methylphenol Chemical compound CCCCC1=CC(O)=CC=C1C OKLNGCVEHOKJIY-UHFFFAOYSA-N 0.000 description 2
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000270666 Testudines Species 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006105 batch ingredient Substances 0.000 description 2
- DIBUFQMCUZYQKN-UHFFFAOYSA-N butyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCC)OC1=CC=CC=C1 DIBUFQMCUZYQKN-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000501 nonneurotoxic Toxicity 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- PEIOZQQSLJIQOR-UHFFFAOYSA-N 1-butyl-2-phenylbenzene phosphoric acid Chemical compound P(=O)(O)(O)O.C(CCC)C1=C(C=CC=C1)C1=CC=CC=C1 PEIOZQQSLJIQOR-UHFFFAOYSA-N 0.000 description 1
- BBRHQNMMUUMVDE-UHFFFAOYSA-N 1-n,2-n-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1NC(C)CNC1=CC=CC=C1 BBRHQNMMUUMVDE-UHFFFAOYSA-N 0.000 description 1
- FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical compound C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 1
- WTFYGNVWNFVUIK-UHFFFAOYSA-N 2-(butylamino)phenol Chemical compound CCCCNC1=CC=CC=C1O WTFYGNVWNFVUIK-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- QKDQHBXHIDQBQR-UHFFFAOYSA-N 2-chloroheptanoic acid Chemical compound CCCCCC(Cl)C(O)=O QKDQHBXHIDQBQR-UHFFFAOYSA-N 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- JYDRKKMKDMWVQQ-UHFFFAOYSA-N 4-(6-methylheptylamino)phenol Chemical compound CC(C)CCCCCNC1=CC=C(O)C=C1 JYDRKKMKDMWVQQ-UHFFFAOYSA-N 0.000 description 1
- ACTPUQAHTZXJSC-UHFFFAOYSA-N 4-amino-3-phenylphenol Chemical group NC1=CC=C(O)C=C1C1=CC=CC=C1 ACTPUQAHTZXJSC-UHFFFAOYSA-N 0.000 description 1
- GPPRMDWJKBFBMZ-UHFFFAOYSA-N 4-morpholin-4-ylphenol Chemical compound C1=CC(O)=CC=C1N1CCOCC1 GPPRMDWJKBFBMZ-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- SDFLTYHTFPTIGX-UHFFFAOYSA-N 9-methylcarbazole Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C2=C1 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- ZIKXHZSORLSPCO-UHFFFAOYSA-N 9h-carbazol-3-ol Chemical compound C1=CC=C2C3=CC(O)=CC=C3NC2=C1 ZIKXHZSORLSPCO-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000252233 Cyprinus carpio Species 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 102000018251 Hypoxanthine Phosphoribosyltransferase Human genes 0.000 description 1
- 108010091358 Hypoxanthine Phosphoribosyltransferase Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010034962 Photopsia Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
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Classifications
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- C10M129/04—Hydroxy compounds
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- C10M133/14—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
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Abstract
Description
Claims (45)
- 1.アルキル置換基が3〜8個の炭素原子を含み且つ第一級炭素原子を介してリ ン酸部分に結合したトリアルキルホスフェート約50〜約72重量%、アルキル 置換基が3〜8個の炭素原子を含み且つ第一級炭素原子を介してリン酸部分に結 合したジアルキルアリールホスフェート約18〜約35重量%、及びアルキルジ アリールホスフェート0〜約5重量%からなる耐火性リン酸エステルベーススト ックと; 前記ベースストックのリン酸エステルの加水分解により現場で形成されるリン酸 部分エステルを中和するために有効な量の酸掃去剤と; 油圧系における油圧サーボ弁の流量測定エッジの液流誘発電気化学的又はζ腐食 を防止するために有効な量のエロージョン防止剤と; 流体組成物が約210°Fで少なくとも約3.0センチストークス、約100° Fで少なくとも約9.0センチストークス、−65°Fで約4200センチスト ークス未満の粘度指数を示すために有効な量の粘度指数向上剤と;酸化剤の存在 下で流体組成物成分の酸化を防止するために有効な童の酸化防止剤とからなる、 航空機作動流体として使用するのに適した流体組成物。
- 2.アルキル置換基が実質的にC4又はC5であるトリアルキルホスフェート約 50〜約72重量%、アルキル置換基が実質的にC4又はC5であるジアルキル アリールホスフェート約18〜約35重黄%、及びアルキルジアリールホスフェ ート0〜約5重量%からなる耐火性リン酸エステルベースストックと; 前記ベースストックのリン酸エステルの加水分解により現場で形成されるリン酸 部分エステルを中和するために有効な量の酸掃去剤と; 油圧系における油圧サーボ弁の流量測定エッジの液流誘発電気化学的又はζ腐食 を防止するために有効な量のエロージョン防止剤と; 流体組成物が約210°Fで少なくとも約3.0センチストークス、約100° Fで少なくとも約9.0センチストークス、−65°Fで約4200センチスト ークス未満の粘度指数を示すために有効な量の粘度指数向上剤と;酸化剤の存在 下で流体組成物成分の酸化を防止するために有効な量の酸化防止剤とからなる、 航空機作動流体として使用のに適した流体組成物。
- 3.前記ジアルキルアリールホスフェートがジアルキルフェニルホスフェートで ある請求項2に記載の流体組成物。
- 4.流体組成物が約210°Fで約3〜約5センチストークス及び約100°F で約9〜15センチストークスの粘度指数を示すために有効な量で前記粘度指数 向上剤が存在する請求項2に記載の組成物。
- 5.前記組成物の約3〜約10重量%の割合の粘度指数向上剤を含有し、該粘度 指数向上剤が、実質的にブチル及びヘキシルメタクリレートからなる反復単位を 含むメタクリル酸エステルポリマーからなり、該ポリマーの少なくとも95重量 %が約50,000〜約1,500,000の分子量を有する請求項2に記載の 組成物。
- 6.組成物の約0.1〜約1.0重量%の割合の2,4,6−トリアルキルフェ ノールと、組成物の約0.3〜約1重量%の割合のジ(アルキルフェニル)アミ ンと、組成物の約0.3〜約1重量%の割合のピス(3,5−ジアルキル−4− ヒドロキシアリール)メタン、1,3,5−トリアルキル−2,4,6−トリス (3,5−ジ−第3ブチル−4−ヒドロキシアリール)ベンゼン及びその混合物 からなる群から選択されるヒンダードポリフェノール組成物とを含有する請求項 2に記載の組成物。
- 7.アリール置換基を含むエステルが前記ベースストックの約25重量%以上を 構成しない請求項2に記載の組成物。
- 8.前記アルキル置換基が実質的にイソブチル又はイソペンチルである請求項1 に記載の組成物。
- 9.アルキル置換基が3〜8個の炭素原子を含み且つ第一級炭素原子を介してリ ン酸部分に結合したトリアルキルホスフェート約10〜約90重量%、アルキル 置換基が3〜8個の炭素原子を含み且つ第一級炭素原子を介してリン酸部分に結 合したジアルキルアリールホスフェート約0〜約70重量%、及びアルキルジア リールホスフェート約0〜約25重量%からなる耐火性リン酸エステルペースス トックと; 組成物の約3〜約10重量%の割合で存在し、実質的にブチル及びヘキシルメタ クリレートからなる反復単位を含むメタクリレートエステルポリマーからなり、 該ポリマーの少なくとも95重量%が約50,000〜約1,500,000の 分子量を有する粘度指数向上剤と;組成物の約0.02〜約0.08重量%の割 合で存在し、アルキル置換基がヘキシル、へブチル、オクチル、ノニル、デシル 又はその混合物であるペルフルオロアルキルスンホン酸のアルカリ金属塩からな るエロージョン防止剤と;組成物の約1.5〜約10重量%の割合で存在し、エ ポキシド化合物からなる酸掃去剤と; 組成物の約0.1〜約1.0重量%の割合の2,4,6−トリアルキルフェノー ルと; 組成物の約0.3〜約1重量%の割合のジ(アルキルフェニル)アミンと; 組成物の約0.3〜約1重量%の割合のピス(3,5−ジアルキル−4−ヒドロ キシアリール)メタン、1,3,5−トリメチル−2,4,6−トリス(3,5 −ジ−第3ブチル−4−ヒドロキシアリール)ベンゼン及びその混合物からなる 群から選択されるヒンダードポリフェノール組成物とからなる、航空機作動流体 として使用するのに適した流体組成物。
- 10.アルキル置換基が実質的にブチル又はペンチルであるトリアルキルホスフ ェート約10〜約90重量%、アルキル置換基が実質的にブチル又はペンチルで あるジアルキルアリールホスフェート約0〜約70重量%、及びアルキルジアリ ールホスフェート約0〜約25重量%からなる耐火性リン酸エステルベーススト ックと;組成物の約3〜約10重量%の割合で存在し、実質的にブチル及びヘキ シルメタクリレートからなる反復単位を含むメタクリレートエステルポリマーか らなり、該ポリマーの少なくとも95重量%が約50,000〜約1,500, 000の分子量を有する粘度指数向上剤と;組成物の約0.02〜約0.08重 量%の割合で存在し、アルキル置換基がヘキシル、へブチル、オクチル、ノニル 、デシル又はその混合物であるペルフルオロアルキルスンホン酸のアルカリ金属 塩からなるエロージョン防止剤と;組成物の約1.5〜約10重量%の割合で存 在し、3,4−エポキシシクロヘキサンカルボキシレートの誘導体、式: ▲数式、化学式、表等があります▼ (式中、R3は1〜10個の炭素原子、0〜6個の酸素原子及び0〜6個の窒素 原子を含む有機基であり、R4〜R9は水素及び炭素原子数1〜5個の脂肪族基 から独立して選択される)に対応するジエポキシド化合物、及び前記3,4−エ ポキシシクロヘキサンカルボキシレートと前記ジエポキシド化合物の混合物から なる群から選択される酸掃去剤と; 組成物の約0.1〜約1.0重量%の割合の2,4,6−トリアルキルフェノー ルと; 組成物の約0.3〜約1重量%の割合のジ(アルキルフェニル)アミンと; 組成物の約0.3〜約1重量%の割合のピス(3,5−ジアルキル−4−ヒドロ キシアリール)メタン、1,3,5−トリメチル−2,4,6−トリス(3,5 −ジ−第3ブチル−4−ヒドロキシアリール)ベンゼン及びその混合物からなる 群から選択されるヒンダードポリフェノール組成物とからなる、航空機作動流体 として使用するのに適した流体組成物。
- 11.銅腐食防止剤として約0.005%〜約0.09ppmの割合のベンゾト リアゾール又はベンゾトリアゾール誘導体を更に含有する請求項10に記載の組 成物。
- 12.約0.0035〜約0.10重量%のアルカリ金属アリレートを更に含有 する請求項10に記載の組成物。
- 13.前記ベースストックが、アルキル置換基が実質的にブチル又はペンチルで あるトリアルキルホスフェート約35〜約90重量%、アルキル置換基が実質的 にブチル又はペンチルであるジアルキルアリールホスフェート約0〜約35重量 %、及びトリアリールホスフェート約0〜約20%からなる請求項10に記載の 流体組成物。
- 14.前記ベースストックが、アルキル置換基が実質的にブチル又はペンチルで あるトリアルキルホスフェート約80〜約90重量%、及びトリ(アルキルアリ ール)ホスフェート約10〜約20重量%からなる請求項13に記載の流体組成 物。
- 15.前記トリ(アルキルアリール)ホスフェートがトリ(イソプロピルフェニ ル)ホスフェートからなる請求項14に記載の流体組成物。
- 16.前記ベースストックが、アルキル置換基が実質的にブチル又はペンチルで あるトリアルキルホスフェート約10〜約72重量%、アルキル置換基が実質的 にブチル又はペンチルであるジアルキルアリールホスフェート約18〜約70重 量%、及びアルキルジアリールホスフェート約0〜約25%からなる請求項10 に記載の流体組成物。
- 17.前記ベースストックが、アルキル置換基が実質的にブチル又はペンチルで あるトリアルキルホスフェート約10〜約25重量%、アルキル置換基が実質的 にブチル又はペンチルであるジアルキルアリールホスフェート約45〜約70重 量%、及びアルキル置換基が実質的にブチル又はペンチルであるアルキルジアリ ールホスフェート約5〜約25%からなる請求項16に記載の流体組成物。
- 18.前記ベースストックが、アルキル置換基が実質的にブチル又はペンチルで あるトリアルキルホスフェート約50〜約72重量%、アルキル置換基が実質的 にブチル又はペンチルであるジアルキルアリールホスフェート約18〜約35重 量%、及びアルキルジアリールホスフェート約0〜約10%からなる請求項16 に記載の流体組成物。
- 19.前記ベースストックが、約0〜約5%のアルキルジアリールホスフェート を含有する請求項10に記載の流体組成物。
- 20.前記アルキル置換基が実質的にイソブチル又はイソペンチルである請求項 10に記載の組成物。
- 21.アルキル置換基が実質的にイソブチル又はイソペンチルであるトリアルキ ルホスフェート約10〜約90重量%、アルキル置換基が実質的にイソブチル又 はイソペンチルであるジアルキルアリールホスフェート約0〜約70重量%、及 びアルキルジアリールホスフェート0〜約25重量%からなる耐火性リン酸エス テルベースストックと;前記ベースストックのリン酸エステルの加水分解により 現場で形成されるリン酸部分エステルを中和するために有効な量の酸掃去剤と; 油圧系における油圧サーボ弁の流量測定エッジの液流誘発電気化学的腐食を防止 するために有効な量のエロージョン防止剤と; 流体組成物が約210°Fで少なくとも約3.0センチストークス、約100° Fで少なくとも約9.0センチストークス、−65°Fで約4200センチスト ークス未満の粘度指数を示すために有効な量の粘度指数向上剤と;酸化剤の存在 下で流体組成物成分の酸化を防止するために有効な量の酸化防止剤とからなる、 航空機作動流体として使用するのに適した流体組成物。
- 22.前記トリアルキルホスフェートがトリイソブチルホスフェートであり、前 記ジアルキルアリールホスフェートがジイソブチルフェニルホスフェートである 請求項21に記載の組成物。
- 23.銅腐食防止剤として約0.005重量%〜約0.09重量%の割合のベン ゾトリアゾール又はベンゾトリアゾール誘導体を更に含有する請求項21に記載 の組成物。
- 24.式: ▲数式、化学式、表等があります▼ (式中、R1は水素、アルキル、アルケニル、ヒドロキシアルキル、ヒドキシア ルケニル、アルコキシアルキル及びアルコキシアルケニルからなる群から選択さ れ、R2はアルキル、アルケニル及び脂肪族カルボキシレートからなる群から選 択される)に対応する4,5−ジヒドロイミダゾール化合物を更に含有する請求 項21に記載の流体組成物。
- 25.前記4,5−ジヒドロイミダゾールが2−(8−へブタデセニル)−4, 5−ジヒドロ−1H−イミダゾール−1−エタノール及びC14−18脂肪酸と 4,5−ジヒドロ−1H−イミダゾールの縮合物からなる群から選択される請求 項24に記載の組成物。
- 26.前記4,5−ジヒドロイミダゾール化合物がC16−18脂肪酸と4,5 −ジヒドロ−1H−イミダゾールの縮合物である請求項25に記載の組成物。
- 27.前記酸化防止剤がヒンダードフェノールからなる請求項24に記載の組成 物。
- 28.前記ヒンダードフェノールがピス(3,5−ジアルキル−4−ヒドロキシ アリール)メタン、1,3,5−トリアルキル−2,4,6−トリス(3,5− ジ−第3ブチル−4−ヒドロキシアリール)ベンゼン及びその混合物からなる群 から選択されるヒンダードポリフェノール化合物からなる請求項27に記載の組 成物。
- 29.前記酸化防止剤が更にアミン化合物を含有する請求項27に記載の組成物 。
- 30.更にジアリールアミン酸化防止剤を含有する請求項29に記載の組成物。
- 31.前記ジアリールアミンがジ(p−オクチルフェニル)アミンからなる請求 項30に記載の組成物。
- 32.約0.7重量%までの2,6−ジ−第3ブチル−p−クレゾールを更に含 有する請求項30に記載の組成物。
- 33.アルキル置換基が実質的にブチル又はペンチルであるトリアルキルホスフ ェート約10〜約90重量%、アルキル置換基が実質的にブチル又はペンチルで あるジアルキルアリールホスフェート約0〜約70重量%、及びアルキルジアリ ールホスフェート0〜約25重量%からなる耐火性リン酸エステルベースストッ クと; 前記ベースストックのリン酸エステルの加水分解により現場で形成されるリン酸 部分エステルを中和するために有効な量の酸掃去剤と; 油圧系における油圧サーボ弁の流量測定エッジの液流誘発電気化学的又はζ腐食 を防止するために有効な量のエロージョン防止剤と; 流体組成物が約210°Fで少なくとも約3.0センチストークス、約100° Fで少なくとも約9.0センチストークス、−65°Fで約4200センチスト ークス未満の粘度指数を示すために有効な量の粘度指数向上剤と、酸化剤の存在 下で流体組成物成分の酸化を防止するために有効な量の酸化防止剤と; エポキシド減耗により測定した場合に300°Fで組成物の安定性を少なくとも 25%増加させるために有効な量で存在しており、式: ▲数式、化学式、表等があります▼ (式中、R1は水素、アルキル、アルケニル、ヒドロキシアルキル、ヒドキシア ルケニル、アルコキシアルキル及びアルコキシアルケニルからなる群から選択さ れ、R2はアルキル、アルケニル及び脂肪族カルボキシレートからなる群から選 択される)に対応する4,5−ジヒドロイミダゾール化合物とからなる、航空機 作動流体として使用するのに適した流体組成物。
- 34.R1が水素又は低級アルキルであり、R2が脂肪酸残基である請求項33 に記載の組成物。
- 35.R1がヒドロキシアルキルであり、R2がアルケニルである請求項33に 記載の組成物。
- 36.前記4,5−ジヒドロイミダゾールが2−(8−へブタデセニル)−4, 5−ジヒドロ−1H−イミダゾール−1−エタノール及びC14−18脂肪酸と 4,5−ジヒドロ−1H−イミダゾールの縮合産物からなる群から選択される請 求項33に記載の組成物。
- 37.前記4,5−ジヒドロイミダゾール化合物がC16−18脂肪酸と4,5 −ジヒドロ−1H−イミダゾールの縮合物である請求項36に記載の組成物。
- 38.前記トリアルキルホスフェート及び前記ジアルキルアリールホスフェート のアルキル置換基が実質的にイソブチル又はイソペンチルである請求項37に記 載の組成物。
- 39.前記酸化防止剤がヒンダードフェノールからなる請求項33に記載の組成 物。
- 40.前記ヒンダードフェノールがピス(3,5−ジアルキル−4−ヒドロキシ アリール)メタン、1,3,5−トリアルキル−2,4,6−トリス(3,5− ジ−第3ブチル−4−ヒドロキシアリール)ベンゼン及びその混合物からなる群 から選択されるヒンダードポリフェノール化合物からなる請求項39に記載の組 成物。
- 41.前記酸化防止剤が更にアミン化合物を含有する請求項39に記載の組成物 。
- 42.更にジアリールアミン酸化防止剤を含有する請求項41に記載の組成物。
- 43.前記ジアリールアミンがジ(p−オクチルフェニル)アミンからなる請求 項42に記載の組成物。
- 44.約1.0重量%までの2,6−ジ−第3ブチル−p−クレゾールを更に含 有する請求項42に記載の組成物。
- 45.前記トリアルキルホスフェート及び前記ジアルキルアリールホスフェート のアルキル置換基が実質的にイソブチル又はイソペンチルである請求項33に記 載の組成物。
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1993
- 1993-06-01 ES ES93914295T patent/ES2072239T1/es active Pending
- 1993-06-01 EP EP93914295A patent/EP0644922B2/en not_active Expired - Lifetime
- 1993-06-01 HU HU9403526A patent/HUT69300A/hu unknown
- 1993-06-01 CA CA002136739A patent/CA2136739C/en not_active Expired - Lifetime
- 1993-06-01 WO PCT/US1993/005201 patent/WO1993025641A1/en not_active Application Discontinuation
- 1993-06-01 JP JP50154794A patent/JP3420235B2/ja not_active Expired - Fee Related
- 1993-06-01 DE DE69318555T patent/DE69318555T3/de not_active Expired - Lifetime
- 1993-06-01 RU RU94046225/04A patent/RU2167921C2/ru active
- 1993-06-01 AU AU44006/93A patent/AU669184B2/en not_active Expired
- 1993-06-01 AT AT93914295T patent/ATE166102T1/de not_active IP Right Cessation
- 1993-06-01 KR KR1019940704510A patent/KR0161554B1/ko not_active IP Right Cessation
- 1993-06-01 CZ CZ943087A patent/CZ308794A3/cs unknown
- 1993-06-01 NZ NZ253574A patent/NZ253574A/en unknown
- 1993-06-01 BR BR9306530A patent/BR9306530A/pt not_active IP Right Cessation
- 1993-06-10 MX MX9303478A patent/MX9303478A/es unknown
- 1993-06-10 CN CN93108716A patent/CN1040018C/zh not_active Expired - Lifetime
- 1993-06-10 ZA ZA934121A patent/ZA934121B/xx unknown
- 1993-06-10 IL IL10598193A patent/IL105981A/en not_active IP Right Cessation
- 1993-07-28 US US08/099,267 patent/US5464551A/en not_active Ceased
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1994
- 1994-12-09 FI FI945809A patent/FI945809A/fi not_active Application Discontinuation
- 1994-12-09 NO NO944776A patent/NO944776L/no unknown
Cited By (1)
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JP2007197336A (ja) * | 2006-01-24 | 2007-08-09 | Adeka Corp | 新規インドール化合物及びこれを含有する潤滑油組成物 |
Also Published As
Publication number | Publication date |
---|---|
EP0644922B1 (en) | 1998-05-13 |
CA2136739A1 (en) | 1993-12-23 |
IL105981A (en) | 1996-06-18 |
AU669184B2 (en) | 1996-05-30 |
EP0644922B2 (en) | 2007-06-13 |
MX9303478A (es) | 1994-02-28 |
CZ308794A3 (en) | 1996-01-17 |
KR0161554B1 (ko) | 1999-01-15 |
NO944776D0 (no) | 1994-12-09 |
DE69318555T3 (de) | 2008-02-21 |
AU4400693A (en) | 1994-01-04 |
CN1040018C (zh) | 1998-09-30 |
RU94046225A (ru) | 1996-09-27 |
CA2136739C (en) | 1999-10-05 |
DE69318555T2 (de) | 1998-12-03 |
ATE166102T1 (de) | 1998-05-15 |
DE69318555D1 (de) | 1998-06-18 |
CN1084551A (zh) | 1994-03-30 |
RU2167921C2 (ru) | 2001-05-27 |
US5464551A (en) | 1995-11-07 |
HUT69300A (en) | 1995-09-28 |
NZ253574A (en) | 1996-01-26 |
NO944776L (no) | 1995-01-25 |
ES2072239T1 (es) | 1995-07-16 |
EP0644922A1 (en) | 1995-03-29 |
FI945809A0 (fi) | 1994-12-09 |
ZA934121B (en) | 1994-01-17 |
BR9306530A (pt) | 1998-09-15 |
JP3420235B2 (ja) | 2003-06-23 |
KR950701967A (ko) | 1995-05-17 |
FI945809A (fi) | 1995-02-02 |
IL105981A0 (en) | 1993-10-20 |
WO1993025641A1 (en) | 1993-12-23 |
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