EP0096281B1 - Procédé pour la préparation de liquides avec un haute indice de viscosité qui sont difficilement inflammables et leur application - Google Patents

Procédé pour la préparation de liquides avec un haute indice de viscosité qui sont difficilement inflammables et leur application Download PDF

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Publication number
EP0096281B1
EP0096281B1 EP83105092A EP83105092A EP0096281B1 EP 0096281 B1 EP0096281 B1 EP 0096281B1 EP 83105092 A EP83105092 A EP 83105092A EP 83105092 A EP83105092 A EP 83105092A EP 0096281 B1 EP0096281 B1 EP 0096281B1
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EP
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Prior art keywords
molecular weight
phenylene
weight
viscosity index
liquids
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.)
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EP83105092A
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German (de)
English (en)
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EP0096281A2 (fr
EP0096281A3 (en
Inventor
Karl-Heinz Dr. Hentschel
Bernhard Dr. Müssig
Rolf Dr. Dhein
Siegfried Kussi
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Bayer AG
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Bayer AG
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Publication of EP0096281A3 publication Critical patent/EP0096281A3/de
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    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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    • 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
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
    • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
    • C10M105/54—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen, halogen and oxygen
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/22—Polyesters
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    • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
    • C10M151/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
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    • C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
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    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
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    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
    • C10M2211/0245—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic used as base material
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    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/0406—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen used as base material
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    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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    • C10M2211/0425—Alcohols; Ethers; Aldehydes; Ketones used as base material
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    • C10M2211/044—Acids; Salts or esters thereof
    • C10M2211/0445—Acids; Salts or esters thereof used as base material
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    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
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    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
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    • C10M2223/003—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions used as base material
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    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin
    • C10M2223/103—Phosphatides, e.g. lecithin, cephalin used as base material
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    • 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 a method for producing flame-retardant liquids with a high viscosity index and their use as hydraulic fluids and / or as heat transfer fluids.
  • Phosphate esters or polychlorinated aromatics which can be used for HSD hydraulic oils, do not pose any corrosion problems because they are water-free and do not cause high wear at highly stressed friction points.
  • the widespread use of these two product classes is mainly hampered by their extraordinarily poor viscosity-temperature behavior.
  • the viscosities of the triaryl phosphates and low chlorinated aromatics which are not particularly thermally stable, are too low for the above-mentioned uses.
  • Known viscosity index improvers such as e.g. B. Polymethacrylates and polyolefin copolymers are known as thickening substances that also raise the viscosity index of this liquid sufficiently, but they lose considerable effectiveness at high shear rates at lubrication points.
  • the object of the invention is therefore that special polymers are added to the synthetic base oil, which have a favorable influence on their viscosity properties, without appreciably affecting the flame resistance and shear stability and are well compatible with the base oil.
  • the weight-average molecular weight, M W is determined here using the laser small-angle light scattering method.
  • the synthetic base oil is mixed with the higher molecular weight polyester.
  • This can be prepared by a polycondensation reaction from an aromatic or (cyclo) aliphatic dicarboxylic acid or a suitable aromatic or (cyclo) aliphatic dicarboxylic acid derivative and a polytetramethylene glycol according to known processes (WK Witsiepe, Advan. Chem. Ser; 1973, 129, 39-60).
  • High molecular weight polyesters are used to produce the liquids according to the invention. These are derivatives based on aromatic dicarboxylic acids, e.g. B. phthalic acid, isophthalic acid, terephthalic acid, naphthalic acid, naphthalenedicarboxylic acid 1,4, naphthalenedicarboxylic acid 1,5, diphenyl dicarboxylic acid 3,4, diphenyl dicarboxylic acid 2,2 ', diphenyl dicarboxylic acid 4,4, benzophenone dicarboxylic acid -3,4, benzophenone dicarboxylic acid 2,2 ', benzophenone dicarboxylic acid 2,2', benzophenone dicarboxylic acid 4,4 ', diphenyl ether dicarboxylic acid 3,4, diphenyl ether dicarboxylic acid 2,2', diphenyl ether -dicarboxylic acid-4,4 ', diphenyl sulfide-dicarboxylic
  • Phthalic acid, isophthalic acid and terephthalic acid are preferred. Terephthalic acid is particularly preferred.
  • the liquids according to the invention can furthermore contain customary further additives, for example antioxidants (for example 2,6 di-tert-butyl-p-cresol, 2,2 'methylene-bis- (4-methyl) -6-tert.- butylphenol etc.), stabilizers (e.g. carbodiimides), antiwear additives (e.g. zinc alkyldithiophosphates), foam-suppressing additives, corrosion inhibitors.
  • antioxidants for example 2,6 di-tert-butyl-p-cresol, 2,2 'methylene-bis- (4-methyl) -6-tert.- butylphenol etc.
  • stabilizers e.g. carbodiimides
  • antiwear additives e.g. zinc alkyldithiophosphates
  • foam-suppressing additives e.g. zinc alkyldithiophosphates
  • corrosion inhibitors for example 2,6 di-tert-butyl-p-cresol, 2,2 'm
  • Diols for example commercially available polytetramethylene glycols such as “Polymeg®” (Quaker Oats) or Teracol ”(Du Pont), are used as alcohol components to produce the polyester products according to the invention.
  • Polymeg® Quaker Oats
  • Teracol Teracol
  • polytetramethylene glycols with an average molecular weight of 360-10,000 (calculated from the hydroxyl number), preferably from 650-5,000 and particularly preferably from 860-3,600, are chosen.
  • the choice of catalyst depends on the dicarboxylic acid derivative used.
  • the molar ratio of dicarboxylic acid derivatives to alcohol component is generally 1: 1.
  • Suitable synthetic base oils are: aromatic phosphates such as tricresyl phosphate, dicresyl monophenyl phosphate. Monocresyl diphenyl phosphate and other phosphate esters of monophenols. Chlorinated aromatic compounds such as trichlorobiphenyl, tetrachlorobiphenyl, pentachlorobiphenyl, trichlorodiphenyl ether and tetrachlorodiphenyl ether can also be used. Pentachlorodiphenyl ether etc. can be used as base oils.
  • the flame-retardant liquids according to the invention consisting of a base oil and A higher molecular weight polyester can be used as a lubricant, lubricant additives in general. They can also be used as hydraulic fluids.
  • Table 1 clearly shows the superior thickening effect and the viscosity index-increasing effect.
  • Table 2 shows the results of shear tests based on DIN 51 382. The good shear strength of the liquids according to the invention can be seen from this. (See table 2 page 6 f.)

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Claims (3)

1. Procédé de production de liquides difficilement inflammables à haut indice de viscosité, caractérisé en ce qu'on mélange ensemble 96 à 99,9 % en poids d'une huile de base très résistante à la flamme, qui contient des structures aromatiques et 0,1 à 4 % en poids d'un polyester de poids moléculaire élevé de formule I
Figure imgb0029
dans laquelle
Y est un reste 1,2-phénylène, 1,3-phénylène, 1,4-phénylène ou un reste de formule
Figure imgb0030
Figure imgb0031
Figure imgb0032
Figure imgb0033
n est un nombre entier de 5 à 140 et
x est un nombre choisi de manière que la moyenne en poids du poids moléculaire ait une valeur de 20 000 à 300 000.
2. Liquides difficilement inflammables à haut indice de viscosité, caractérisés en ce que le liquide contient 96 à 99,9 % en poids d'une huile de base de grande résistance à la flamme qui comporte des structures aromatiques et 0,1 à 4 % en poids d'un polyester de poids moléculaire élevé de formule 1
Figure imgb0034
dans laquelle
Y est un reste 1,2-phénylène, 1,3-phénylène, 1,4-phénylène ou un reste de formule
Figure imgb0035
Figure imgb0036
Figure imgb0037
Figure imgb0038
n est un nombre entier de 5 à 140 et
x est un nombre choisi de manière que la moyenne en poids du poids moléculaire ait une valeur de 20 000 à 300 000.
3. Utilisation de liquides difficilement inflammables suivant la revendication 2 comme lubrifiants.
EP83105092A 1982-06-04 1983-05-24 Procédé pour la préparation de liquides avec un haute indice de viscosité qui sont difficilement inflammables et leur application Expired EP0096281B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823221137 DE3221137A1 (de) 1982-06-04 1982-06-04 Verfahren zur herstellung von schwerentflammbaren fluessigkeiten mit hohem viskositaetsindex und deren verwendung
DE3221137 1982-06-04

Publications (3)

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EP0096281A2 EP0096281A2 (fr) 1983-12-21
EP0096281A3 EP0096281A3 (en) 1985-05-15
EP0096281B1 true EP0096281B1 (fr) 1987-07-29

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Publication number Priority date Publication date Assignee Title
DE3767855D1 (de) * 1986-12-19 1991-03-07 Ciba Geigy Gmbh Epoxidharze enthaltend polyester auf polyalkylenglykolbasis.
US5066409A (en) * 1990-09-12 1991-11-19 The Dow Chemical Company Novel aryl ether sulfones
US5128067A (en) * 1991-12-19 1992-07-07 Fmc Corporation Fire resistant low temperature grease
CA2136427C (fr) * 1993-03-25 2003-07-15 Asahi Denka Kogyo K. K. Lubrifiant pour utilisation dans les refrigerateurs et frigorigene contenant ce lubrifiant
DE4435548A1 (de) * 1994-10-05 1996-04-11 Rhein Chemie Rheinau Gmbh Stabilisierte Schmierstoff-Grundsubstanz
US5494595A (en) 1994-12-30 1996-02-27 Huntsman Corporation Oil soluble polyethers
US5783528A (en) * 1997-01-07 1998-07-21 Diversey Lever, Inc. Synthetic lubricant based on enhanced performance of synthetic ester fluids
US11339346B2 (en) * 2016-12-14 2022-05-24 Evonik Operations Gmbh Use of polyesters as viscosity index improvers for aircraft hydraulic fluids
JP7471022B1 (ja) * 2023-04-28 2024-04-19 築野グループ株式会社 二塩基酸とポリオキシアルキレングリコールとのエステル

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BE567232A (fr) * 1957-04-30
US3867298A (en) * 1971-02-19 1975-02-18 Ethyl Corp Lubricant
US3935116A (en) * 1972-02-28 1976-01-27 Mcdonnell Douglas Corporation Functional fluid compositions
US3951837A (en) * 1973-09-24 1976-04-20 Mcdonnell Douglas Corporation Functional fluid compositions
US3956154A (en) * 1974-02-11 1976-05-11 Stauffer Chemical Company Hydraulic fluid system
JPS53105677A (en) * 1977-02-25 1978-09-13 Kao Corp Flame retardant working oil composite and manufacturing method thereof

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EP0096281A2 (fr) 1983-12-21
EP0096281A3 (en) 1985-05-15
US4490266A (en) 1984-12-25
DE3221137A1 (de) 1983-12-08
DE3372782D1 (en) 1987-09-03

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