EP0272575B2 - Esters de polyols neutres ayant une viscosité élevée - Google Patents
Esters de polyols neutres ayant une viscosité élevée Download PDFInfo
- Publication number
- EP0272575B2 EP0272575B2 EP87118481A EP87118481A EP0272575B2 EP 0272575 B2 EP0272575 B2 EP 0272575B2 EP 87118481 A EP87118481 A EP 87118481A EP 87118481 A EP87118481 A EP 87118481A EP 0272575 B2 EP0272575 B2 EP 0272575B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- acids
- class
- acid
- dipentaerythritol
- polyol esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000007935 neutral effect Effects 0.000 title claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 37
- 229920005862 polyol Polymers 0.000 claims abstract description 27
- 150000007513 acids Chemical class 0.000 claims abstract description 24
- -1 polyol esters Chemical class 0.000 claims abstract description 24
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 claims abstract description 22
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 22
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 10
- 239000010687 lubricating oil Substances 0.000 claims abstract description 10
- 230000032050 esterification Effects 0.000 claims abstract description 7
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 7
- 150000003628 tricarboxylic acids Chemical class 0.000 claims abstract description 6
- 229920000728 polyester Polymers 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract 2
- 238000009833 condensation Methods 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims description 4
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 150000005846 sugar alcohols Polymers 0.000 abstract description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 235000020778 linoleic acid Nutrition 0.000 abstract 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 14
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012208 gear oil Substances 0.000 description 3
- 239000010720 hydraulic oil Substances 0.000 description 3
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- KDMAJIXYCNOVJB-UHFFFAOYSA-N 2,2-bis(nonanoyloxymethyl)butyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC KDMAJIXYCNOVJB-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000000034 method Methods 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
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
-
- 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
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/40—Esters containing free hydroxy or carboxyl 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/283—Esters of polyhydroxy 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
-
- 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
- C10N2040/02—Bearings
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the invention relates to the use of the new synthetic polyol esters for the production of temperature-resistant gear and hydraulic oils as well as lubricating oil dispersions and / or lubricating greases.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Claims (6)
- Esters de polyols synthétiques ayant des propriétés d'huile de graissage à base de produit d'estérification essentiellement neutres de dipentaérythrite avec des acides monocarboxyliques ramifiés et des acides carboxyliques choisis, caractérisés en ce que la dipentaérythrite est estérifiée par :a) des acides gras ramifiés dans la zone de chaîne carbonée allant de C₈ à C₁₆ (acides de la classe A), et,b) des acides gras linéaires dans la zone de chaîne carbonée allant de C₈ à C₁₄ (acides de la classe B)et pour cela renferme inclus par condensation en supplément des quantités limitées d'acides di- et/ou tricarboxyliques dans la zone des chaînes carbonées allant de C₆ à C₅₄ (acides de la classe C).
- Esters de polyols synthétiques selon la revendication 1, caractérisé en ce que comme acides di- et/ou tricarboxyliques on met en oeuvre de l'acide adipique et/ou des acides gras di- ou trimères.
- Esters de polyols synthétiques selon les revendications 1 et 2, caractérisés en ce que les restes acides dans le polyester se présentent dans les rapports équivalents suivants, à chaque fois rapporté aux six équivalents hydroxyle de la dipentaérythrite pour des rapports au moins stoechiométriques des groupes hydroxyle/acide, 4 à 5,8 équivalents de mélanges d'acides des classes A et B avec 0,2 à 2 équivalents d'acides de la classe C, dans lesquels dans le polyester les rapports en équivalents se situent de 1 à 4 équivalents en radicaux acide de classe A pour 2 à 5 équivalents en radicaux acide de classe B.
- Esters de polyols synthétiques selon les revendications 1 à 3, caractérisés en ce qu'ils possèdent un indice d'HO allant jusqu'à 25 pour un excès de dipentaérythrite, allant jusqu'à 0,2 mol/mol de dipentaérithrite pleinement estérifiée.
- Esters de polyols synthétiques selon les revendications 1 à 4, caractérisés en ce qu'ils possèdent des valeurs de viscosité à 40°C dans la zone allant de 50 à 1000 mm²/s et des points de solidification dans la zone allant de 0° à -30°C.
- Utilisation des esters de polyols synthétiques selon les revendications 1 à 5 pour la fabrication de dispersions d'huile de graissage et/ou de graisses de lubrification que l'on peut soumettre à des contraintes thermiques.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3643935A DE3643935C2 (de) | 1986-12-22 | 1986-12-22 | Synthetische Polyolester |
| DE3643935 | 1986-12-22 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| EP0272575A2 EP0272575A2 (fr) | 1988-06-29 |
| EP0272575A3 EP0272575A3 (en) | 1989-08-09 |
| EP0272575B1 EP0272575B1 (fr) | 1992-09-16 |
| EP0272575B2 true EP0272575B2 (fr) | 1995-12-13 |
Family
ID=6316900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87118481A Expired - Lifetime EP0272575B2 (fr) | 1986-12-22 | 1987-12-14 | Esters de polyols neutres ayant une viscosité élevée |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5057247A (fr) |
| EP (1) | EP0272575B2 (fr) |
| JP (1) | JP2661927B2 (fr) |
| AT (1) | ATE80607T1 (fr) |
| BR (1) | BR8706979A (fr) |
| CA (1) | CA1317974C (fr) |
| DE (2) | DE3643935C2 (fr) |
| ES (1) | ES2052537T5 (fr) |
| MX (1) | MX169267B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7018558B2 (en) | 1999-06-09 | 2006-03-28 | Cognis Corporation | Method of improving performance of refrigerant systems |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR950005694B1 (ko) * | 1989-07-05 | 1995-05-29 | 가부시끼가이샤 교오세끼 세이힝기주쓰 겡뀨쇼 | 냉각윤활제 |
| DE3927155A1 (de) * | 1989-08-17 | 1991-02-21 | Henkel Kgaa | Umweltfreundliches grundoel fuer die formulierung von hydraulikoelen |
| JP2967574B2 (ja) * | 1990-11-16 | 1999-10-25 | 株式会社日立製作所 | 冷凍装置 |
| US20030104956A1 (en) * | 1994-04-28 | 2003-06-05 | Schaefer Thomas G. | Synthetic lubricant base stock formed from high content branched chain acid mixtures |
| EP0518567B1 (fr) * | 1991-06-07 | 2000-09-13 | Hatco Corporation | Base lubrifiante synthétique formée à partir de mélanges d'acides dont une grande partie à chaínes ramifiées |
| JP3001679B2 (ja) * | 1991-07-19 | 2000-01-24 | 出光興産株式会社 | 2サイクルエンジンまたはロータリーエンジン用潤滑油組成物 |
| DE4214653A1 (de) * | 1992-05-02 | 1993-11-04 | Henkel Kgaa | Motorengrundoele mit verbesserter dichtungsvertraeglichkeit |
| ATE184310T1 (de) * | 1992-06-03 | 1999-09-15 | Henkel Corp | Polyol/ester-gemisch als schmiermittel für wärmeträgerflüssigkeiten in kälteanlagen |
| DE69231364T2 (de) | 1992-06-03 | 2001-04-05 | Henkel Corp., Gulph Mills | Schmiermittel auf basis von polyolester für kälteübertragungsmittel |
| US6183662B1 (en) | 1992-06-03 | 2001-02-06 | Henkel Corporation | Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures |
| CA2137263C (fr) * | 1992-06-03 | 2003-10-14 | Nicholas E. Schnur | Lubrifiants a base de polyol pour compresseurs frigorifiques fonctionnant a haute temperature |
| US5976399A (en) | 1992-06-03 | 1999-11-02 | Henkel Corporation | Blended polyol ester lubricants for refrigerant heat transfer fluids |
| JP2613526B2 (ja) * | 1992-07-04 | 1997-05-28 | 花王株式会社 | 冷凍機作動流体用組成物 |
| EP0656931A4 (fr) * | 1992-08-28 | 1997-05-02 | Henkel Corp | Compositions biodegradables d'huile pour moteurs a deux temps et matieres a base d'esters. |
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| WO1995032266A1 (fr) * | 1994-05-23 | 1995-11-30 | Henkel Corporation | Procede pour augmenter la resistivite electrique de lubrifiants bases sur des esters et destines en particulier a une utilisation avec des refrigerants bases sur des hydrocarbures fluores |
| EP0796308B1 (fr) * | 1994-12-08 | 2001-10-04 | ExxonMobil Chemical Patents Inc. | Bases constituees d'esters synthetiques ramifies biodegradables et lubrifiants fabriques a partir d'elles |
| US5665686A (en) * | 1995-03-14 | 1997-09-09 | Exxon Chemical Patents Inc. | Polyol ester compositions with unconverted hydroxyl groups |
| TW349119B (en) * | 1996-04-09 | 1999-01-01 | Mitsubishi Gas Chemical Co | Polyol ester based-lubricant |
| DE19616733C2 (de) * | 1996-04-26 | 2000-07-13 | Stockhausen Chem Fab Gmbh | Verfahren zur thermisch-mechanischen Oberflächenbehandlung von flächenförmigen Materialbahnen, insbesondere aus Papier und Karton unter Verwendung von Abhäsivmitteln |
| US5728658A (en) * | 1996-05-21 | 1998-03-17 | Exxon Chemical Patents Inc | Biodegradable synthetic ester base stocks formed from branched oxo acids |
| US5798322A (en) * | 1996-08-30 | 1998-08-25 | Gateway Additive Company | Friction-modifying additives for slideway lubricants |
| US5942475A (en) * | 1996-09-06 | 1999-08-24 | Exxon Chemical Patents Inc. | Engine oil lubricants formed from complex alcohol esters |
| US5922658A (en) * | 1996-09-06 | 1999-07-13 | Exxon Chemical Patents Inc. | Two-cycle engine oil formed from a blend of a complex alcohol ester and other basestocks |
| US5698502A (en) * | 1996-09-11 | 1997-12-16 | Exxon Chemical Patents Inc | Polyol ester compositions with unconverted hydroxyl groups for use as lubricant base stocks |
| EP0890634A1 (fr) * | 1997-07-09 | 1999-01-13 | Voith Turbo GmbH & Co. KG | Fluide de travail pour machine hydrodynamique |
| JP2003522204A (ja) * | 1997-10-01 | 2003-07-22 | ユニケマ ケミー ベスローテン フェンノートシャップ | 複合エステル、これらのエステルを含む配合およびそれらの使用 |
| US20060229409A1 (en) * | 2005-04-08 | 2006-10-12 | Ilmenev Pavel E | Method for preparing polyurethane dispersions |
| DE102006027602A1 (de) * | 2006-06-13 | 2007-12-20 | Cognis Ip Management Gmbh | Schmierstoffzusammensetzungen enthaltend Komplexester |
| US9481852B2 (en) * | 2008-01-24 | 2016-11-01 | The Lubrizol Corporation | High viscosity synthetic ester lubricant base stock blends |
| US10336958B2 (en) | 2016-08-30 | 2019-07-02 | Resinate Materials Group, Inc. | Sustainable base oils for lubricants |
| WO2018110142A1 (fr) | 2016-12-13 | 2018-06-21 | 花王株式会社 | Huile de base lubrifiante et composition lubrifiante comprenant ladite huile de base lubrifiante |
| JP2018095840A (ja) | 2016-12-13 | 2018-06-21 | 花王株式会社 | 潤滑油基油、および該潤滑油基油を含有する潤滑油組成物 |
| JP6928445B2 (ja) | 2016-12-21 | 2021-09-01 | 花王株式会社 | 潤滑油基油、該潤滑油基油を含有する潤滑油組成物およびその製造方法 |
| JP7216563B2 (ja) * | 2019-02-12 | 2023-02-01 | 花王株式会社 | グリース基油、および該グリース基油を含有するグリース組成物 |
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-
1986
- 1986-12-22 DE DE3643935A patent/DE3643935C2/de not_active Expired - Fee Related
-
1987
- 1987-12-14 EP EP87118481A patent/EP0272575B2/fr not_active Expired - Lifetime
- 1987-12-14 MX MX009736A patent/MX169267B/es unknown
- 1987-12-14 DE DE8787118481T patent/DE3781782D1/de not_active Expired - Lifetime
- 1987-12-14 ES ES87118481T patent/ES2052537T5/es not_active Expired - Lifetime
- 1987-12-14 AT AT87118481T patent/ATE80607T1/de not_active IP Right Cessation
- 1987-12-21 BR BR8706979A patent/BR8706979A/pt not_active IP Right Cessation
- 1987-12-21 US US07/136,037 patent/US5057247A/en not_active Expired - Fee Related
- 1987-12-22 JP JP62326635A patent/JP2661927B2/ja not_active Expired - Lifetime
- 1987-12-22 CA CA000555085A patent/CA1317974C/fr not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7018558B2 (en) | 1999-06-09 | 2006-03-28 | Cognis Corporation | Method of improving performance of refrigerant systems |
Also Published As
| Publication number | Publication date |
|---|---|
| MX169267B (es) | 1993-06-28 |
| EP0272575A3 (en) | 1989-08-09 |
| DE3643935C2 (de) | 1995-07-06 |
| ES2052537T3 (es) | 1994-07-16 |
| BR8706979A (pt) | 1988-07-26 |
| ATE80607T1 (de) | 1992-10-15 |
| JPS63170337A (ja) | 1988-07-14 |
| DE3643935A1 (de) | 1988-06-23 |
| EP0272575A2 (fr) | 1988-06-29 |
| CA1317974C (fr) | 1993-05-18 |
| EP0272575B1 (fr) | 1992-09-16 |
| DE3781782D1 (de) | 1992-10-22 |
| ES2052537T5 (es) | 1996-03-01 |
| US5057247A (en) | 1991-10-15 |
| JP2661927B2 (ja) | 1997-10-08 |
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