EP3967739B1 - Utilisation de diester d'isosorbide en tant qu'agent de contrôle de dépôt - Google Patents

Utilisation de diester d'isosorbide en tant qu'agent de contrôle de dépôt Download PDF

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Publication number
EP3967739B1
EP3967739B1 EP20305997.7A EP20305997A EP3967739B1 EP 3967739 B1 EP3967739 B1 EP 3967739B1 EP 20305997 A EP20305997 A EP 20305997A EP 3967739 B1 EP3967739 B1 EP 3967739B1
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EP
European Patent Office
Prior art keywords
isosorbide
carbon atoms
weight
diester
base oils
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Application number
EP20305997.7A
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German (de)
English (en)
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EP3967739A1 (fr
Inventor
Karima ZITOUNI
Micky-Lee FU-XIANG
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Oleon NV
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Oleon NV
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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
    • C10M105/38—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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/74—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
    • 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
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
    • 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
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property

Definitions

  • the present invention relates to the use of at least one diester as a deposit control agent.
  • a deposit control agent prevents or reduces agglomerates formation and their deposits.
  • the deposit control agent reduces the formation of sludge, varnish or lacquer and their deposits.
  • Sludge, varnish and lacquer are different formats of deposit composed of residues of oxidized base oil formed when a lubricant composition is exposed to high temperature conditions in the presence of oxygen, nitrogen oxides and oxidation-derived hydroperoxides, resulting in the oxidation of the base oil comprised in the lubricant composition.
  • Varnish and lacquer forms when resin (polymeric compounds from oxygenates) deposits on the hot surface and subsequently dehydrated to form a firm film.
  • lacquer occurs in lubricant composition in the case of diesel engine pistons while varnish is the normally fuel-derived. Sludge occurs at a cooler place ( ⁇ 200°C). It can be watery or hard depending on the dehydration extent ( Bouman, C.A. Properties of Lubricating Oils and Engine Deposits. London, U.K.: MacMillan and Co., 1950, pp. 69-92 .)
  • WO2017/0116897 discloses lubricating oil compositions optimized to avoid sludge comprising a dicarboxylic acid ester additive.
  • a lubricant composition typically comprises a base oil, usually the major constituent (the constituent whose content is the highest), and one or more additive(s).
  • An additive is used to enhance one or more intrinsic property(ies) of the base oil and / or provide it with one or more additional property(ies).
  • API American Petroleum Institute
  • main base oils used in lubricant compositions in various industries such as in engine oils, hydraulic fluids (oils), gear oils, metalworking fluids (oils) or compressor oil were of Group I for their attractive properties, especially for their viscosity and their ease in solubilizing additives due to the presence of aromatics.
  • Group V base oils are generally not used as base oils themselves, but as co-base oils to improve the solubility of additives.
  • adipates, trimethylolpropane esters and alkylated naphtalenes are used for this purpose with mineral oils from Group II and III and PAO, and besides their aid in solubilizing additives, they can also improve one or more property(ies) of the base oil, in particular they can contribute to reduce the formation of sludge, varnish or lacquer.
  • a solubilizer is not necessarily a deposit control agent.
  • a deposit control agent is an agent that has deposit control property i.e. it prevents or reduces the formation of sludge, varnish and/or lacquer.
  • Typical examples of deposit control agent is sulfonates, phenates, salicylates, polymeric compounds derived from polyisobutylene with polar moiety.
  • the present invention therefore relates to the use of one or a mixture of isosorbide diester(s) of formula I, wherein R 1 and R 2 , identical or different, each represents a linear, straight or branched, saturated or unsaturated, hydrocarbon chain comprising from 3 to 17 carbon atoms; as a deposit control agent, wherein the isosorbide diester has a pour point of at most 15°C.
  • the hydrocarbon chain R 1 and R 2 independently comprise from 5 to 17 carbon atoms.
  • the pour point refers to the lowest temperature at which a liquid remains pourable.
  • isosorbide diesters with a pour point of at most 15°C are liquid and they can be more easily used.
  • the pour point can be determined according to method described in ASTM D97.
  • the pour point of the isosorbide diesters is of at most 10°C.
  • isosorbide diesters of formula I present good deposit control property. In particular, they reduced the sludge formation.
  • R 1 and R 2 are identical.
  • each hydrocarbon chain R 1 and R 2 comprises from 3 to 9 carbon atoms.
  • hydrocarbon chain R 1 and R 2 are unsaturated and comprise 17 carbon atoms.
  • R 1 and R 2 are different.
  • At least R 1 or R 2 is a saturated hydrocarbon chain comprising from 3 to 9 carbon atoms or an unsaturated hydrocarbon chain comprising 17 carbon atoms.
  • hydrocarbon chains R 1 and R 2 comprise independently from 7 to 15 carbon atoms, more preferably from 7 to 9 carbon atoms.
  • hydrocarbon chains R 1 and R 2 comprise 7 or 9 carbon atoms, preferably in a weight ratio hydrocarbon chains comprising 7 carbon atoms / hydrocarbon chains comprising 9 carbon atoms, comprised between 1 and 2, more preferably between 1.05 and 1.85.
  • the mixture of isosorbide diesters may comprise at least two isosorbide diesters of formula I.
  • the mixture may comprise at least two isosorbide diesters, at least one isosorbide diester of formula I comprising identical R 1 and R 2 but said R 1 and/or R 2 being able to be different from the first isorsorbide diester to the other one.
  • hydrocarbon chains R 1 and R 2 comprise independently from 7 to 15 carbon atoms.
  • isosorbide diester may be prepared from at least two different fatty acids, such as caprylic acid and capric acid.
  • caprylic acid and capric acid such as caprylic acid and capric acid.
  • isosorbide diesters of formula I present other properties, such as lubricant additives solubilizer.
  • isosorbide diesters of formula I are effective in the solubilization of additives usually used in the field of lubricants.
  • At least 30% by weight of hydrocarbon chains R 1 and R 2 comprise 7 carbon atoms and at least 30% by weight of hydrocarbon chains R 1 and R 2 comprise 9 carbon atoms, weight percent being based on the weight of all hydrocarbon chains R 1 and R 2 of isosorbide diester(s).
  • At least 50% by weight of hydrocarbon chains R 1 and R 2 comprise 7 carbon atoms, based on the weight of all hydrocarbon chains R1 and R2 of isosorbide diester(s).
  • the weight ratio hydrocarbon chains comprising 7 carbon atoms / hydrocarbon chains comprising 9 carbon atoms is comprised between 1 and 2.
  • the weight ration hydrocarbon chains comprising 7 carbon atoms / hydrocarbon chains comprising 9 carbon atoms is comprised between 1.05 and 1.85.
  • hydrocarbon chains R 1 and R 2 comprise 7 or 9 carbon atoms.
  • Such advantageous isosorbide diesters can solubilize even more easily different types of additives in different base oils.
  • the isosorbide diester is further used to solubilize an additive used in the field of lubricants.
  • the additive(s) is/are preferably chosen from the group constituted by:
  • isosorbide diesters of formula I present good thermal-oxidative stability and a good hydrolytic stability.
  • the isosorbide diesters of formula I are obtainable by a process comprising a step of esterification reactions of isosorbide with at least one linear carboxylic acid, straight or branched, saturated or unsaturated, comprising from 4 to 18 carbon atoms. More particularly, the linear carboxylic acid, straight or branched, saturated or unsaturated, comprising from 4 to 18 carbon atoms is a fatty acid.
  • Isosorbide and 1.9 weight equivalents of fatty acid(s) were introduced in a reaction vessel.
  • the esterification was carried out at elevated temperature (from 180 to 230°C) and stopped when acid value was less than 5 mg KOH/g.
  • Oxygen-induced degradation was used to evaluate the sludge formation in mineral oils with and without the use of isosorbide diester or other known products with deposit control property.
  • RPVOT is a test that utilizes an oxygen-pressured vessel to evaluate the oxidation stability of new and in-service turbine oils.
  • the mixtures were filtered through Milipore MF membrane filter (0.8 um) using 50 ml of hexane to ease the filtration and for rinsing purpose.
  • Table 2 Contents of additive packages 1-8 according to the invention GII + 10wt% of - ISD1 ISD2 ISD3 DITA AN TMP C8-C10 Sludge retained on filter (mg) 120.0 49.3 47.6 48.1 58.5 80.7 59.1 Reduction of sludge formation (%) - 59.0 60.3 59.9 51.2 32.8 50.7 *based on the weight of the additive package
  • isosorbide diesters were added into mixtures comprising Group III and IV base oils and one additive known to be not soluble in those base oils.
  • a base oil was added until the mixture correspond to 80 wt%, letting 20wt% left for the addition of isosorbide diester or Comparative Group V base oils.
  • Isosorbide diester or Comparative Group V base oils was thus added to the mixture, starting from 1 wt% and the resulting mixture was stirred via vortex mixer for 20 seconds before evaluating the solubility. If the solubility is insufficient, more isosorbide diester or Comparative Group V base oils was added. The evaluation of solubility of additives was determined with the help of a visual aid (line background). The additive was considered soluble when the line appeared as clear as in the case of only base oil (control) was used.
  • Isosorbide diesters solubilize EGD in mineral oil of Group III and MoDTC and CaDNNS in PAO 150.
  • ISD1 exhibits better performances, since lower quantities are needed to solubilize additives. Therefore, IDS1 helps solubilizing all those additives in different base oils with better performances than Comparative Group V base oils, as shown by results gathered in Table 4.
  • Table 4 Quantities of IDS1 or Comparative Group V base oils to solubilize additives Additive Base oil Isosorbide diester or Comparative Group V base oils (wt%*) ISD1 DITA AN TMP C8-C10 Gill 0.5wt%* SML not soluble +++ not soluble ++ - PAO4 0.5wt%* EGD not soluble - not soluble not soluble - *based on the weight of the resulting mixture

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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 (7)

  1. Utilisation d'un ou d'un mélange de diester(s) d'isosorbide de formule I
    Figure imgb0004
     dans laquelle R1 et R2 sont identiques ou différents et représentent chacun une chaîne hydrocarbonée linéaire, non ramifiée ou ramifiée, saturée ou insaturée, comprenant 3 à 17 atomes de carbone ;
    en tant qu'un agent de contrôle de dépôt, dans laquelle le diester d'isosorbide présente un point d'écoulement de 15 °C au maximum.
  2. Utilisation d'un diester d'isosorbide de formule I selon la revendication 1, dans laquelle R1 et R2 sont identiques.
  3. Utilisation d'un diester d'isosorbide de formule I selon la revendication 1, dans laquelle R1 et R2 sont différents.
  4. Utilisation selon l'une quelconque des revendications 1 à 3, dans laquelle un mélange de diesters d'isosorbide de formule I est utilisé.
  5. Utilisation selon l'une quelconque des revendications 1, 3 ou 4, dans laquelle au moins 30 % en poids de chaînes hydrocarbonées R1 et R2 comprennent 7 atomes de carbone et au moins 30 % en poids de chaînes hydrocarbonées R1 et R2 comprennent 9 atomes de carbone, le pourcentage en poids se rapportant au poids de toutes les chaînes hydrocarbonées R1 et R2 de diester(s) d'isosorbide.
  6. Utilisation selon l'une quelconque des revendications 1 ou 3 à 5, dans laquelle le rapport de poids des chaînes hydrocarbonées comprenant 7 atomes de carbone / les chaînes hydrocarbonées comprenant 9 atomes de carbone est compris entre 1 et 2.
  7. Utilisation selon l'une quelconque des revendications 1 à 6, dans laquelle le diester d'isosorbide est utilisé en outre pour solubiliser un additif utilisé dans le domaine des lubrifiants.
EP20305997.7A 2020-09-09 2020-09-09 Utilisation de diester d'isosorbide en tant qu'agent de contrôle de dépôt Active EP3967739B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20305997.7A EP3967739B1 (fr) 2020-09-09 2020-09-09 Utilisation de diester d'isosorbide en tant qu'agent de contrôle de dépôt

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Application Number Priority Date Filing Date Title
EP20305997.7A EP3967739B1 (fr) 2020-09-09 2020-09-09 Utilisation de diester d'isosorbide en tant qu'agent de contrôle de dépôt

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EP3967739A1 EP3967739A1 (fr) 2022-03-16
EP3967739B1 true EP3967739B1 (fr) 2023-04-26

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US20100210487A1 (en) * 2009-02-16 2010-08-19 Chemtura Coproration Fatty sorbitan ester based friction modifiers
US10316265B2 (en) * 2015-12-28 2019-06-11 Exxonmobil Research And Engineering Company Low viscosity low volatility lubricating oil base stocks and methods of use thereof

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