EP0272575B1 - Esters de polyols neutres ayant une viscosité élevée - Google Patents

Esters de polyols neutres ayant une viscosité élevée Download PDF

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Publication number
EP0272575B1
EP0272575B1 EP87118481A EP87118481A EP0272575B1 EP 0272575 B1 EP0272575 B1 EP 0272575B1 EP 87118481 A EP87118481 A EP 87118481A EP 87118481 A EP87118481 A EP 87118481A EP 0272575 B1 EP0272575 B1 EP 0272575B1
Authority
EP
European Patent Office
Prior art keywords
acids
class
acid
fatty acids
dipentaerythritol
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
Application number
EP87118481A
Other languages
German (de)
English (en)
Other versions
EP0272575A3 (en
EP0272575A2 (fr
EP0272575B2 (fr
Inventor
Karl-Heinz Dr. Schmid
Uwe Dr. Ploog
Alfred Dr. Meffert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0272575A2 publication Critical patent/EP0272575A2/fr
Publication of EP0272575A3 publication Critical patent/EP0272575A3/de
Publication of EP0272575B1 publication Critical patent/EP0272575B1/fr
Application granted granted Critical
Publication of EP0272575B2 publication Critical patent/EP0272575B2/fr
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Expired - Lifetime legal-status Critical Current

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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

  • esters so-called ester oils
  • ester oils have found increasing use as high-quality lubricating oils in recent years.
  • diesters of dibasic carboxylic acids with monohydric alcohols for example dioctyl sebacate
  • esters of polyols with monobasic acids such as trimethylolpropane tripelargonate
  • polyols e.g. uses trimethylolpropane, neopentyl glycol and / or pentaerythritol.
  • the good suitability of the synthetic esters as lubricants results from the fact that they have a more favorable viscosity-temperature behavior than conventional lubricating oils based on mineral oil and that the setting points are significantly lower when comparable viscosities are set.
  • US Pat. No. 4,234,497 describes polyol esters based on one or more polyhydric alcohols with 2 to 8 hydroxyl groups, isopalmitic acid and one or more monocarboxylic acids with 5 to 11 carbon atoms, which serve as the basis for synthetic lubricants. Dipentaerythritol is also mentioned as a polyhydric alcohol; Both straight-chain and branched can be used as monocarboxylic acids. These polyol esters are characterized, among other things, by good viscosity properties and by low pour points.
  • the present invention is based on the object of providing new synthetic polyol esters which are particularly suitable for use in the field of temperature-resistant lubricating oils such as gear and hydraulic oils and lubricating oil dispersions or lubricating greases and which are also optimally adapted to the aforementioned selection criteria can be.
  • the technical solution to this problem according to the invention is based on the selection of a specific polyol component as a hydroxyl group function for the production of the polyol esters and combines this selection on the side of the hydroxyl group component with a specific selection of mono- and polyfunctional carboxylic acids on the acid side for the production of the new ones synthetic polyol esters.
  • the invention relates to the use of the new synthetic polyol esters for the production of temperature-resistant transmission and hydraulic oils as well as lubricating oil dispersions and / or lubricating greases.
  • the new synthetic polyol esters of the invention can be branched as fatty acid components Contain fatty acids from class A or mixtures of branched fatty acids of class A with linear fatty acids from class B. Details of the preferred mixing ratios are given below.
  • synthetic polyol esters of the type mentioned with the lowest possible acid numbers are preferred, neutral esters or those with a limited excess of free hydroxyl groups being particularly affected.
  • 6.0 to 7.2 equivalents (corresponding to 1 to 1.2 mol) of dipentaerythritol are used in the preparation of the esters per 6 equivalents of the acids or acid mixtures used.
  • Preferred polyol esters of this type show hydroxyl numbers in the range from 0 to 25.
  • Esters preferred according to the invention furthermore have viscosity values at 40 ° C. in the range from 50 to 1000 mm 2 / s and have pour points in the range from approximately 0 to -30 ° C.
  • the nice polyol esters according to the invention are suitable carrier oils for temperature-resistant lubricating oil dispersions and lubricating greases and are moreover due to their good tribological properties - e.g. excellent pressure absorption capacity - also suitable as additional components or used alone for hydraulic and gear oils.
  • Usual additives such as oxidation and corrosion inhibitors, dispersants, high pressure additives, anti-foaming agents, metal deactivators and other additives can be added in the usual effective amounts.
  • Dipentaerythritol and the selected fatty acid mixture are in the presence of 0.5% tin grinding at 240 ° C esterified for 6 to 8 hours while distilling off the water formed in the reaction. Towards the end of the reaction, esterification continues at the same temperature but under reduced pressure. After cooling to 120 ° C., 1 percent by weight of activated bleaching earth is added, the mixture is heated again to 200 ° C. and excess monocarboxylic acid is distilled off in vacuo. After cooling, the reaction mixture is filtered.
  • the temperature / weight analysis gives the mass loss of the substance in percent, which occurs when heated with a continuous temperature rise of 20 ° C per minute.

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)

1. Esters de polyols synthétiques ayant des propriétés d'huile de graissage à base de produits d'estérification essentiellement neutres de dipentaérythrite avec des acides monocarboxyliques ramifiés et des acides carboxyliques sélectionnés, caractérisés en ce que la dipentaérythrite est estérifiée avec :
1 - des acides gras ramifiés dans la zone des chaînes carbonées allant de 8 à 16 atomes de carbone (acides de classe A),
ou
II - des mélanges d'acides gras linéaires dans la zone des chaînes carbonées allant de C8 à C14 -(acides de classe B) en mélange avec des acides gras ramifiés de la classe A.
et renferme en outre en supplément des quantités limitées d'acides carboxyliques plurifonctionnels des classes suivantes C, D et/ou E condensés dans la molécule d'ester de polyols :
des acides de classe C : acides di- et/ou tricarboxyliques dans la zone allant de C6 à C54,
des acides de classe D : acides gras difonctionnels qui ont été produits par fixation d'acide acrylique sur les doubles liaisons de l'acide oléique, linoléique et/ou linolénique.
des acides de classe E : acides polycarboxyliques aromatiques et/ou paraffiniques, cycliques, avec 2 à 6 fonctions acides.
2. Esters de polyols synthétiques selon la revendication 1, caractérisés en ce que les restes d'acide dans le polyester se présentent dans les rapports en équivalents suivants, rapportés respectivement aux 6 équivalents hydroxyle de la dipentaérythrite, pour des rapports au moins stoechiométriques des groupes hydroxyle/groupes acide :
4 à 5,8 équivalents d'acide de classe A ou de mélange d'acides des classes A et a avec 0,2 à 2 équivalents d'acides des classes C, D et/ou E, pour l'utilisation commune des restes des acides provenant des classes A et B dans l'ester de polyols, des rapports en équivalents de 1 à 4 équivalents en restes acides de la classe A se présentant pour 2 à 5 équivalents en restes acide de la classe B.
3. Esters de polyols synthétiques selon les revendications 1 et 2, caractérisé en ce que comme acides de la classe B, C et/ou E les composants suivants sont sélectionnés :
Classe B : acides gras linéaires de la zone de chaînes carbonées allant de C8 à C10,
Classe C : l'acide adipique, l'acide triméthyl adipique, l'acide azélaïque, et/ou l'acide sébacique ainsi que les acides gras di- ou trimériques provenant de la polymérisation d'acides gras une fois ou plusieurs fois insaturés dans la zone carbonée allant de C1 6 à C22.
Classe E : Acide téréphtalique, acide triméllitique, l'acide pyroméllitique, et/ou l'acide cyclohexane carboxylique ou leur anhydride.
4. Esters de polyols synthétiques selon les revendications 1 à 3, caractérisés en ce qu'ils possèdent un indice d'hydroxyle allant jusqu'à 25 pour un excès de dipentaérythrite allant jusqu'à 0,2 mol/mol de dipentaérithrite pleinement estérifiée.
5. 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.
6. Utilisation des esters de polyols synthétiques selon les revendications 1 à 5 en vue de l'obtention de dispersions d'huile de graissage et/ou de graisses de lubrification que l'on peut soumettre à des contraintes thermiques.
EP87118481A 1986-12-22 1987-12-14 Esters de polyols neutres ayant une viscosité élevée Expired - Lifetime EP0272575B2 (fr)

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 true EP0272575B1 (fr) 1992-09-16
EP0272575B2 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)

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US4589900A (en) * 1983-03-17 1986-05-20 United Technologies Corporation High-strength thermally stable magnesium aluminosilicate glass-ceramic matrix sic fiber composite
US4589990A (en) * 1985-06-21 1986-05-20 National Distillers And Chemical Corporation Mist lubricant compositions
US4645615A (en) * 1986-02-27 1987-02-24 Fmc Corporation Fire-resistant hydraulic fluid

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
DE3781782D1 (de) 1992-10-22
ES2052537T5 (es) 1996-03-01
US5057247A (en) 1991-10-15
EP0272575B2 (fr) 1995-12-13
JP2661927B2 (ja) 1997-10-08

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