WO1991009096A2 - Solvant peu volatil pour substances actives contenant des elements de la serie aromatique - Google Patents

Solvant peu volatil pour substances actives contenant des elements de la serie aromatique Download PDF

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Publication number
WO1991009096A2
WO1991009096A2 PCT/EP1990/002083 EP9002083W WO9109096A2 WO 1991009096 A2 WO1991009096 A2 WO 1991009096A2 EP 9002083 W EP9002083 W EP 9002083W WO 9109096 A2 WO9109096 A2 WO 9109096A2
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WIPO (PCT)
Prior art keywords
benzoic acid
oils
diesters
carbon atoms
diols
Prior art date
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PCT/EP1990/002083
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German (de)
English (en)
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WO1991009096A3 (fr
Inventor
Karl Schmid
Josef Steber
Reinhold Wüst
Peter Gode
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to CA002098109A priority Critical patent/CA2098109A1/fr
Priority to JP91502392A priority patent/JPH05502262A/ja
Publication of WO1991009096A2 publication Critical patent/WO1991009096A2/fr
Publication of WO1991009096A3 publication Critical patent/WO1991009096A3/fr

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    • 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
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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Definitions

  • Non-volatile solvent for active ingredients containing aromatics
  • the invention relates to an improvement in the field of the use of oils, for example as hydraulic fluids for hydrostatic power transmission.
  • ester oils that can be used in practice, for example rapeseed oils and / or soybean oils that have been freed from mucilage, show decisive weaknesses compared to mineral oils:
  • ester oils based on unsaturated fatty acid systems tend to thicken rapidly even at only moderately elevated operating temperatures of, for example, 50 to 80 ° C.
  • the reason for this is the willingness of the olefinic double bonds of the ester-forming acids of the oil type affected here to react under the influence of atmospheric oxygen, which ultimately leads to Increase viscosity. It is generally known that such undesirable increases in viscosity can be retained to a certain extent, especially in hydraulic oils, by adding antioxidants. Nevertheless, it is difficult to set a satisfactory level of performance here, in particular for working over longer periods. Often there is a need to replenish antioxidants, corrosion inhibitors and the like after a certain period of use in order to ensure a sufficiently long operating period for ester oils of the type concerned here.
  • auxiliaries required here from the classes of antioxidants, corrosion inhibitors and the like are frequently, if not usually, compounds which contain at least a proportion of aromatic constituents.
  • phenolic structures and / or hydroquinone derivatives are predominant in the class of auxiliaries or active substances concerned here against undesirable attack by atmospheric oxygen.
  • D 8826 "Environmentally friendly base oil for the formulation of hydraulic oils”
  • the applicant describes a corresponding base oil based on natural substances for the formulation of hydraulic oils with improved viscosity and / or low-temperature stability in use, which contains the following components:
  • rapeseed oil and / or soybean oil as the main oil component
  • Antioxidants based on aromatic molecular constituents are used throughout as component (b).
  • component (b) For practical work with such environmentally friendly base oils, it proves desirable to additionally provide active ingredient concentrates which contain the stabilizing additives - preferably in high concentrations - in solution. The service life of the hydraulic oil can be extended effectively by replenishing these additives.
  • Active substance concentrates of the type described require a solvent which is flowable at ambient temperature and has a low volatility and is highly compatible with the aromatic basic structure of the active substances used in order to ensure the required high concentrations of the dissolved active substances.
  • a likewise aromatic basic structure of the solvent fulfills this requirement.
  • dibutyl phthalate which is widely used today, would be a suitable representative as a solvent for the preparation of the active ingredient concentrates required here.
  • DBP dibutyl phthalate
  • the invention is based on the object for the operation of environmentally friendly oil phases, such as those used as ester oils it is known from the applicant's older patent application mentioned to provide auxiliaries of the type also described at the beginning with at least a proportion of aromatic molecular structure, which in turn are characterized by high environmental compatibility.
  • the invention seeks to make it possible to make antioxidants and / or corrosion inhibitors of the type described available as dissolved concentrates in a solvent which itself can be assigned to water hazard class 0, while at the same time producing highly concentrated, more flowable at ambient temperature Solutions made possible and can be mixed into the ester-based hydraulic oils without any special effort and without hesitation.
  • the technical solution to the problem according to the invention lies in the use of selected benzoic acid diesters as a non-volatile solvent of high environmental compatibility.
  • the invention accordingly relates to the use of selected, straight-chain and / or branched aliphatic diols which flow at ambient temperature and have branched aliphatic diols with at least 4 C atoms as a non-volatile, environmentally friendly solvent for active substances such as oxidation and / or corrosion inhibitors with at least partially aromatic molecular structure in them Use in fats and / or oils with increased environmental compatibility, in particular in hydraulic oils based on ester oil.
  • the invention relates to an additive containing active ingredients such as antioxidants and / or corrosion inhibitors with an at least partially aromatic basic structure based on a low-volatile solvent which is free-flowing at room temperature and which is characterized in that the benzoic acid diester which is free-flowing at ambient temperature is straight-chain and / or branched aliphatic diols with at least 4 carbon atoms.
  • Preferred non-volatile solvents for the purposes of the invention are diol diesters of benzoic acid which have pour points below 0 ° C. and preferably below -10 ° C. and at the same time have flash points not below 150 ° C. and preferably above 200 ° C.
  • Benzoic acid diesters of this property profile are derived in particular from diols which have 4 to 9 C atoms and in particular 5 to 7 C atoms in a linear arrangement between the hydroxyl groups of the diol and. Have diol components in the ester.
  • This linear intermediate member of the diols can be unsubstituted or can be branched once or several times, in which case substitution with lower alkyl radicals with preferably up to a maximum of 3 carbon atoms is suitable.
  • Particularly suitable are diesters of benzoic acid of those diols which have a maximum of 10 carbon atoms in the diol radical.
  • Di-benzoic acid esters of the type described here show, in the sum of their properties, the requirement profile described at the outset. Because of their aromatic molecular component, esters of this type can absorb large amounts of the aromatic active ingredients to be dissolved in the additive. As a rule, active substance contents in the range from 5 to about 50% by weight, preferably in the range up to about 40% by weight. % can be set in the selected solvent type.
  • the benzoic acid esters themselves are environmentally compatible and, in particular, correspond to water hazard class 0. Their entry and homogeneous mixing into hydraulic oils, for example based on the ester oils described, succeed without any problems.
  • Preferred active ingredients for use via the additives according to the invention are antioxidants selected from the group consisting of methoxyphenol, ethoxyphenol, butylhydroxyanisole, butylhydroxytoluene, methoxyhydroquinone, ethoxyhydroquinone, tert-butylhydroquinone and / or tocopherol.
  • other conventional active ingredients can be added to the additive concentrates. Examples of these are high-pressure additives, wear protection additives and / or pour point depressants.
  • the benzoic acid diesters are used in admixture with polyalphaolefins as the solvent phase.
  • the term "the" polyalphaolefins encompasses oligomers of alpha olefins of a medium chain length. Oligomers which meet the theological requirements imposed on the benzoic acid diol diesters are particularly suitable here. I n particular suitable are Oligo ⁇ mers of alpha olefins having 6 to 12 carbon atoms in the monomeric Mo ⁇ lekül, with particular importance for the oligomers of C 1. Alpha-olefin have. The oligomers can in turn be formed, for example, from 2 to 6 units of the alpha olefin.
  • the benzoic acid diesters can be used with the polyalphaolefins in a wide mixing ratio, so that quantitative ratios of the two components to one another in the range from about 95: 5 to 5:95 and preferably those in the range from about 70: 30 to 30: 70 in Can come into consideration. Examples

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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)

Abstract

On utilise des diesters d'acide benzoïque, fluides à la température ambiante, de diols à chaîne droite et/ou ramifiée ayant au moins 4 atomes de carbone comme solvants peu volatils, non polluants, de substances actives, telles que des inhibiteurs de la corrosion et/ou de l'oxydation, ayant au moins en partie une structure moléculaire aromatique, lorsque ces substances actives sont ajoutées à des graisses et/ou à des huiles à biocompatibilité élevée, notamment des huiles hydrauliques à base d'huiles-esters.
PCT/EP1990/002083 1989-12-09 1990-12-03 Solvant peu volatil pour substances actives contenant des elements de la serie aromatique WO1991009096A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002098109A CA2098109A1 (fr) 1989-12-09 1990-12-03 Solvant non volatil pour ingredients actifs aromatiques
JP91502392A JPH05502262A (ja) 1989-12-09 1990-12-03 芳香族成分を含む活性物質の為の低揮発性溶剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3940803.5 1989-12-09
DE3940803A DE3940803A1 (de) 1989-12-09 1989-12-09 Schwerfluechtige loesungsmittel fuer aromatenhaltige wirkstoffe

Publications (2)

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WO1991009096A2 true WO1991009096A2 (fr) 1991-06-27
WO1991009096A3 WO1991009096A3 (fr) 1991-07-25

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PCT/EP1990/002083 WO1991009096A2 (fr) 1989-12-09 1990-12-03 Solvant peu volatil pour substances actives contenant des elements de la serie aromatique

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EP (1) EP0505484A1 (fr)
JP (1) JPH05502262A (fr)
CA (1) CA2098109A1 (fr)
DE (1) DE3940803A1 (fr)
WO (1) WO1991009096A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114317083A (zh) * 2021-12-31 2022-04-12 上海恩坤工业技术有限公司 一种润滑组合物、制备方法及润滑方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10137130C1 (de) * 2001-07-30 2003-03-13 Excor Korrosionsforschung Gmbh Dampfphasen-Korrosionsinhibitoren, Verfahren zu deren Zubereitung und Verwendung
CN101668835B (zh) 2007-04-23 2014-03-05 出光兴产株式会社 液压工作油以及液压装置

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1001351A (en) * 1963-04-05 1965-08-18 Ethyl Corp Halogenated bisphenols and applications thereof
FR1557509A (fr) * 1967-03-29 1969-02-14
GB1182851A (en) * 1968-01-02 1970-03-04 Mobil Oil Corp Lubricating Compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1001351A (en) * 1963-04-05 1965-08-18 Ethyl Corp Halogenated bisphenols and applications thereof
FR1557509A (fr) * 1967-03-29 1969-02-14
GB1182851A (en) * 1968-01-02 1970-03-04 Mobil Oil Corp Lubricating Compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114317083A (zh) * 2021-12-31 2022-04-12 上海恩坤工业技术有限公司 一种润滑组合物、制备方法及润滑方法

Also Published As

Publication number Publication date
JPH05502262A (ja) 1993-04-22
EP0505484A1 (fr) 1992-09-30
WO1991009096A3 (fr) 1991-07-25
DE3940803A1 (de) 1991-06-13
CA2098109A1 (fr) 1991-06-10

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