EP0415626A1 - Lubrification et lubrifiants - Google Patents
Lubrification et lubrifiants Download PDFInfo
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- EP0415626A1 EP0415626A1 EP90309132A EP90309132A EP0415626A1 EP 0415626 A1 EP0415626 A1 EP 0415626A1 EP 90309132 A EP90309132 A EP 90309132A EP 90309132 A EP90309132 A EP 90309132A EP 0415626 A1 EP0415626 A1 EP 0415626A1
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- European Patent Office
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- 239000000314 lubricant Substances 0.000 title claims abstract description 11
- 238000005461 lubrication Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 18
- 239000012530 fluid Substances 0.000 claims description 17
- 230000001050 lubricating effect Effects 0.000 claims description 17
- 238000005260 corrosion Methods 0.000 claims description 12
- 230000007797 corrosion Effects 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 235000006708 antioxidants Nutrition 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005069 Extreme pressure additive Substances 0.000 claims description 6
- 239000007866 anti-wear additive Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000000047 product Substances 0.000 description 46
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 11
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 238000005115 demineralization Methods 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 231100000241 scar Toxicity 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000120020 Tela Species 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 2
- -1 alkenyl succinic acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- RRAJJSFZQXZPRJ-UHFFFAOYSA-N C=CC.C(C)O.C(C)O.C(C)O Chemical compound C=CC.C(C)O.C(C)O.C(C)O RRAJJSFZQXZPRJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 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
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- LMODBLQHQHXPEI-UHFFFAOYSA-N dibutylcarbamothioylsulfanylmethyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SCSC(=S)N(CCCC)CCCC LMODBLQHQHXPEI-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000010722 industrial gear oil Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/58—Amines, e.g. polyalkylene polyamines, quaternary amines
- C10M105/60—Amines, e.g. polyalkylene polyamines, quaternary amines having amino groups bound to an acyclic or cycloaliphatic carbon atom
- C10M105/62—Amines, e.g. polyalkylene polyamines, quaternary amines having amino groups bound to an acyclic or cycloaliphatic carbon atom containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/68—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/70—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/40—Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
- C10M107/44—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N2040/36—Release agents or mold release agents
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/40—Generators or electric motors in oil or gas winning field
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N2040/42—Flashing oils or marking oils
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/44—Super vacuum or supercritical use
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/46—Textile oils
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/50—Medical uses
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- THIS INVENTION relates to lubrication and lubricants
- the present invention comprises the use of compounds of formula X[AR] n wherein X is the residue of an active hydrogen-containing organic amine, amide or ammonia following active hydrogen removal; A is a random or block polyoxylalkylene residue, comprising 6 to 170 alkylene oxide residues having 2 to 4 carbon atoms; R is hydrogen or an alkyl or aryl group; and n is an integer having a value of at least 1 wherein each AR segment may be the same or different as lubricants. In a specific form of the invention they are used as mould release agents.
- the said compounds preferably have an average molecular weight of up to 40,000, for example from 300 to 10,000, more preferably from 600 to 8000, most preferably from 750 to 7000.
- Suitable compounds have a viscosity of from 10 to 1500 centistokes at 40°C, more preferably from to 1000 centistokes at 40°C, most preferably from 100 to 460 centistokes at 40°C.
- X may be a residue of a mono or polyhydric amine having primary and/or secondary amine groups or an amide.
- an alkyl, cycloalkyl or aromatic amine or amide having 1 to 200 carbon atoms, for example 1 to 50 carbon atoms preferably 1 to 30 carbon atoms and more preferably 1 to 15 carbon atoms and preferably 1 to 100, for example 1 to 35 and more preferably 1 to 20 amine or amide groups, more preferably 1 to 10 amine or amide groups, most preferably 1 to 6 amine or amide groups.
- Suitable compounds for use in the present invention include those in which X is a residue of an alkylamine for example butylamine, an alkanolamine for example ethanolamine, diethanolamine, triethanolamine, or tripropanolamine, an alkylene diamine for example ethylenediamine, diethylenetriamine, triethylenetetramine, or piperazine.
- A preferably comprises 10 to 140 and more preferably 10 to 120 alkylene oxide residues having 2 to 4 carbon atoms.
- Preferred compounds are those in which A comprises 0 to 10, more preferably from 0 to 8 and most preferably from 0 to 4 ethylene oxide residues for every 10 propylene oxide residues.
- Each R is individually hydrogen or an alkyl or aryl group containing 1 to 30 carbon atoms, preferably 1 to 15 carbon atoms and more preferably 1 to 6 carbon atoms for example a methyl, ethyl, propyl, isopropyl, or butyl group.
- n preferably has a value of 1 to 100 for example 1 to 20, more preferably 1 to 12, most preferably 1 to 8.
- the compounds for use in the present invention may in general be prepared by reacting the corresponding amine,amide or ammonia with the desired alkylene oxide(s) successively or simultaneously, normally in the presence as catalyst of an acid or an alkali, for example sodium or potassium hydroxide.
- the reaction is suitably carried out at a temperature in the range 100 to 180°C, preferably 150 to 160°C for ethoxylation, 105 to 115°C for propoxylation or butoxylation, or 120 to 130°C for reaction with a mixture of alkylene oxides.
- the reaction is carried out at elevated pressure, preferably at 1.5 to 5 bars absolute.
- the invention also comprises a lubricating fluid composition
- a lubricating fluid composition comprising a compound of formula X[AR] n , an anti-oxidant, a corrosion inhibitor, an anti-wear additive and an extreme pressure additive.
- Suitable anti-oxidants include for example butylhydroxyanisole, phenothiazine, hydroquinone monomethyl ether, and/or butylhydroxytoluene.
- Corrosion inhibitors which may be used include half esters of alkenyl succinic acids, N-acyl sarcosine and benzotriazole.
- Suitable anti-wear and extreme pressure additives include tricresylphosphate and methylenebis(dibutyldithiocarbamate).
- compositions preferably contain 0.1 to 2% of anti-oxidant, 0.1 to 2% of corrosion inhibitor and 0.1 to 2% each of anti-wear and extreme pressure additives dissolved in the compound of formula X[AR] n which may suitably comprise the whole of the remainder of the composition.
- additional lubricating and/or viscosity modifying substances may also be present if desired.
- the compositions are typically anhydrous but may be used with up to 5% water.
- the present invention also provides a process of lubrication for mechanical components in which mechanical parts to be lubricated are contacted with a compound of formula X[AR] n .
- mechanical parts include gears especially worm gears, and parts of rolling mills, plastics callenders, paper making machines, compressors for example for use in refrigeration and air conditioning systems based on non chlorine containing hydro fluoro carbon refrigerants for example 1,1,1,2 tetrafluoroethane and vacuum pumps.
- the present invention further provides a process of lubrication for use in mould release applications in which a mould is coated with a compound of formula X[AR] n before moulding a polymer, especially a plastics or rubber material, and also a process for lubrication of textiles in which a textile yarn is contacted with a compound of formula X[AR] n .
- the mixture was heated to 110-120°, under a vacuum of 5-15 mm Hg for a period of 1 hour to dehydrate the mixture, and to mix the products fully in an autoclave.
- the autoclave was charged with nitrogen to a pressure of 2 bar absolute, by bubbling N2 through the mixture.
- Propylene oxide (PO) was added in two stages. 1. 5.5kg PO was introduced to the reactor at 120-125°C over a period of 1 hour. The pressure in the reactor increased from 3 bars to 3.4 bars absolute.
- the product was stripped for 1 hour at 110°C, with a vacuum of 5-15 mm Kg to remove unreacted propylene oxide. 2. 40kg of propylene oxide was added at 115°C to the first stage product over a period of 7.5 hours. The pressure increased from 2 bar to 8.6 bar absolute. After all the propylene oxide had been added, the reaction was allowed to progress for a further 3 hours at 115°C.
- the product was stripped for 1 hour at 115°C, under a vacuum of 5-15 mm Hg, to remove unreacted propylene oxide.
- the mixture was stirred at room temperature under at 5 mm-15 mm Hg vacuum for 1/2 hour before being heated to 120°C for 1 1/2 hours to remove water (second water removal).
- the reacter was then charged to a pressure of 2 bar absolute using N2 bubbled through mixture, followed by the addition of 37.5 kg of propylene oxide over a period of 6.5 hours at 115°C. The pressure increased from 2 bar to 6.4 bar absolute.
- the product was stripped for 1 hour at 110°C under a 5-15 mm Hg vacuum to remove unreacted propylene oxide.
- the final product was demineralised using 1.5 kg of "Ambosol” aluminium silicate and 0.3 kg of a filter aid sold under the trade name "Dicalite”.
- the mixture was heated to 110°C for 1 hour then filtered using a Gauthier filter, at 110°C.
- Piperazine was propoxylated to give a product with a final viscosity of 150 cst at 40°C, and molecular weight of 1368.
- Piperazine was propoxylated to give a product with a final viscosity of 460 cst at 40°C, and molecular weight of 3909.
- Piperazine was propoxylated using similar techniques to those used for PIP 01 150, PIP 01 220, and PIP 01 460 to give a product with a final viscosity of cst 154 at 40°C (ASTM 0445) and a molecular weight of 1950.
- This product was then methyl end capped by the following process: 75 kg of the propoxylated piperazine (at ambient temperature) was mixed with 7.79 kg of sodium methoxide and stirred for 1 ⁇ 2 hour. The mixture was then heated under vacuum for 4 hours (120°C, 5-15 mm Hg). Methyl chloride (8 kg) was then slowly introduced to the reactor (120°C-130°C) over a period of 1 hour. Excess methyl chloride was then removed by vacuum stripping (5-15 mm Hg, 1 ⁇ 2 hour, 120°C). 4.5 Kg of 75% aqueous H3PO4 was then added to adjust the pH to 6.8. The reactor was then cooled from 120°C to 60°C and washed twice with water. The first water wash used 11 kg of water and the second water wash used 8.8 kg of water.
- the final product was essentially insoluble in water and slightly less dense, hence for both washes the water could be simply decanted from the bottom of the reactor.
- the washed product was vacuum stripped to remove excess water (1 Hr, 5-15 mm Hg, 120°C) and filtered with a Gauthier filter using "Dicalite” filter aid. This gave a final product of viscosity 240 cst at 40°C and with approximately 95% methyl end capping (calculated from hydroxyl number analysis ASTM D1957).
- R*N - (CH2 CH2 OH)2 in which R* is a mixture of C13 and C15 alkyl chains in the approximate weight ratio of 70:30, 50% of these groups being linear, and the balance comprising mainly 2-methyl branched species (five kilogrammes) was mixed with 140 grammes of a 90% solution of potassium hydroxide in water (126 grammes KOH). The mixture was then heated to 110-120°C, under a vacuum of 5 mm Hg. The temperature and pressure was maintained for 11/2 hours to dehydrate the mixture. N2 was charged to the reaction to a pressure of 2 bars absolute. Following dehydration an alkoxylation stage was carried out as follows. 45 kilogrammes of propylene oxide was introduced into the reactor over an 11 hour period at 115°C, during which time the pressure in the reaction was increased from 2 bars to 8 bars absolute. The temperature was maintained for a further 2 1/2 hours to ensure completion of reaction.
- the product was stripped for 1 hour at 115°C, under a vacuum of 5mm Hg.
- a 700 gramme sample was taken and the viscosity of the product was measured according to ASTM D445. The viscosity was found to be 205 cSt at 40°C.
- the product was stripped for 1 hour at 115°C, under a vacuum of 5mm Hg.
- the product was then treated in a demineralisation stage with an aluminium silicate sold under the trade mark "Ambosol” (2 kg) and, 1.5 to kilogrammes of "Dicalite” filter aid.
- the mixture was maintained at 110°C for 1 hour and then filtered using a Gauthier filter.
- the autoclave was charged to a pressure of 2 bar absolute using N2, bubbled through the mixture.
- the product was then stripped for 1 hour at 100°C under a vacuum of 5-15 mm Hg to remove unreacted propylene oxide.
- the mixture was heated to 50°C for 1/2 hour then 110-120°C for 11/2 hours under a vacuum of 5-15 mm Hg to dehydrate.
- the reactor was charged to 2 bar absolute using N2 bubbled through the mixture.
- the viscosity of the product, code DELA 01-220 at 40°C was 213 cSt.
- the adduct is a condensation product formed by the reaction of ethylene diamine and four moles of propylene oxide and is available commercially from Arco. It is sold under the trade name 'Arcol 3400'.
- the adduct (17 Kilogrammes) was charged to a reactor and mixed with 190 grammes of a 90% solution of potassium hydroxide. The mixture was dehydrated by stirring for 1 ⁇ 2 hour at ambient temperature under a vacuum of 5 mm Hg, and raising the temperature to 120°C for a further period of 1 1 ⁇ 2 hours. N2 was charged to the reactor to a pressure of 2 bars absolute. Then 57 kilogrammes of a mixture of propylene oxide and ethylene oxide (1:1 weight ratio, pre-mixed) was introduced into the reactor over a period of 8 hours, at 115-120°C, during which time the pressure in the reactor increased from 2 bars to 6.1 bars absolute. The temperature was maintained for a further 1 hour to ensure completion of reaction.
- the product was then treated in a demineralisation stage with an aluminium silicate sold under the trade mark 'Ambosol' (2kg) and 0.4 kg at a filter aid sold under the trade mark of 'Dicalite'.
- the mixture was maintained at a temperature of 110°C for 1 hour and then filtered using a Gauthier filter.
- the product was given the code Ethylene diamine adduct 11-175.
- the ethylene diamine adduct Arcol 3400 was reacted with propylene oxide in a similar manner to that previously described. The previous preparation was repeated except that propylene oxide only was used instead of the 1:1 mixture of ethylene oxide and propylene oxide until a product with a final viscosity of 210 cst at 40°C, and molecular weight 2137 was produced. This was given the code Ethylene diamine adduct 01-210.
- Aziridine Polymer 01-1200 An aziridine Polymer (thought to contain 35 N-H units) available from BASF and sold under the trade mark 'Polymin G35' was propoxylated, using techniques previously described, to give a product with a final viscosity of 1268 cst at 40°C, and molecular weight of approximately 30,000.
- Kinematic viscosity of a lubricating fluid was determined according ASTM (American Society of Testing Materials) D445-79. By measuring the viscosity of the fluid at 40°C and at 100°C the Viscosity Index of the fluid was determined according to ASTM D2270-79.
- Heat stability of the lubricating fluid was determined by placing triplicate samples in a forced draught oven at 180°C for a period of up to 180 hours. The weight loss, determined as a percentage of the original weight is recorded as a function of time.
- the lubricating properties of the lubricating fluid were determined using the Shell 4-ball technique, according to ASTM 4172.
- the lubricating fluid was tested at 75°C and 220°C.
- a 40 kg load is applied and the test was run for 1 hour at 1450 rpm, and the diameter of the scar produced was determined.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Lubricants (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8919505 | 1989-08-29 | ||
| GB898919505A GB8919505D0 (en) | 1989-08-29 | 1989-08-29 | Lubrication and lubricants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0415626A1 true EP0415626A1 (fr) | 1991-03-06 |
Family
ID=10662207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90309132A Withdrawn EP0415626A1 (fr) | 1989-08-29 | 1990-08-21 | Lubrification et lubrifiants |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0415626A1 (fr) |
| JP (1) | JPH03119096A (fr) |
| GB (1) | GB8919505D0 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992015658A1 (fr) * | 1991-03-05 | 1992-09-17 | Imperial Chemical Industries Plc | Lubrifiants pour installations de transfert de chaleur |
| WO1993018118A1 (fr) * | 1992-03-12 | 1993-09-16 | Imperial Chemical Industries Plc | Textile lubricant compositions |
| WO2000023648A1 (fr) * | 1998-10-20 | 2000-04-27 | The Dow Chemical Company | Composition lubrifiante |
| EP4108744A4 (fr) * | 2020-02-19 | 2024-03-20 | Idemitsu Kosan Co.,Ltd. | Composition d'huile pour machine frigorifique, et composition mixte pour machine frigorifique |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009096600A1 (fr) * | 2008-01-31 | 2009-08-06 | Matsumura Oil Research Corp. | Agent lubrifiant |
| JP7045272B2 (ja) * | 2018-06-29 | 2022-03-31 | 日華化学株式会社 | 加硫ゴム用離型剤 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017072A2 (fr) * | 1979-04-02 | 1980-10-15 | The Dow Chemical Company | Lubrifiant résistant à l'eau pour compresseurs et moteurs marins |
| EP0109515A2 (fr) * | 1982-09-29 | 1984-05-30 | Union Carbide Corporation | Composition lubrifiante tolérante à l'eau |
| US4851144A (en) * | 1989-01-10 | 1989-07-25 | The Dow Chemical Company | Lubricants for refrigeration compressors |
| EP0379175A1 (fr) * | 1989-01-18 | 1990-07-25 | The Dow Chemical Company | Lubrifiants à base de polyglycol pour compresseurs frigorifiques et leur procédé de préparation |
-
1989
- 1989-08-29 GB GB898919505A patent/GB8919505D0/en active Pending
-
1990
- 1990-08-21 EP EP90309132A patent/EP0415626A1/fr not_active Withdrawn
- 1990-08-29 JP JP2227893A patent/JPH03119096A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017072A2 (fr) * | 1979-04-02 | 1980-10-15 | The Dow Chemical Company | Lubrifiant résistant à l'eau pour compresseurs et moteurs marins |
| EP0109515A2 (fr) * | 1982-09-29 | 1984-05-30 | Union Carbide Corporation | Composition lubrifiante tolérante à l'eau |
| US4851144A (en) * | 1989-01-10 | 1989-07-25 | The Dow Chemical Company | Lubricants for refrigeration compressors |
| EP0379175A1 (fr) * | 1989-01-18 | 1990-07-25 | The Dow Chemical Company | Lubrifiants à base de polyglycol pour compresseurs frigorifiques et leur procédé de préparation |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992015658A1 (fr) * | 1991-03-05 | 1992-09-17 | Imperial Chemical Industries Plc | Lubrifiants pour installations de transfert de chaleur |
| WO1993018118A1 (fr) * | 1992-03-12 | 1993-09-16 | Imperial Chemical Industries Plc | Textile lubricant compositions |
| WO2000023648A1 (fr) * | 1998-10-20 | 2000-04-27 | The Dow Chemical Company | Composition lubrifiante |
| US6444627B1 (en) | 1998-10-20 | 2002-09-03 | Dow Global Technologies Inc. | Lubricant composition |
| EP4108744A4 (fr) * | 2020-02-19 | 2024-03-20 | Idemitsu Kosan Co.,Ltd. | Composition d'huile pour machine frigorifique, et composition mixte pour machine frigorifique |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03119096A (ja) | 1991-05-21 |
| GB8919505D0 (en) | 1989-10-11 |
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