EP0438709A1 - Huiles pour moteurs contenant des phénols alcoxylés - Google Patents

Huiles pour moteurs contenant des phénols alcoxylés Download PDF

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Publication number
EP0438709A1
EP0438709A1 EP90124070A EP90124070A EP0438709A1 EP 0438709 A1 EP0438709 A1 EP 0438709A1 EP 90124070 A EP90124070 A EP 90124070A EP 90124070 A EP90124070 A EP 90124070A EP 0438709 A1 EP0438709 A1 EP 0438709A1
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EP
European Patent Office
Prior art keywords
oxide
bisphenol
motor
butylene oxide
motor oil
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Application number
EP90124070A
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German (de)
English (en)
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EP0438709B1 (fr
Inventor
Helmut Dr. Mach
Helmut Schmidt
Knut Dr. Oppenlaender
Roland Dr. Schwen
Jürgen Dr. Mohr
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BASF SE
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BASF SE
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Priority to AT90124070T priority Critical patent/ATE88496T1/de
Publication of EP0438709A1 publication Critical patent/EP0438709A1/fr
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24Polyethers
    • C10M145/26Polyoxyalkylenes
    • C10M145/36Polyoxyalkylenes etherified
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02Petroleum fractions
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/36Esters of polycarboxylic acids
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/38Esters of polyhydroxy compounds
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    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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    • C10M169/00Lubricating 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
    • C10M169/04Mixtures of base-materials and additives
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    • C10M169/00Lubricating 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
    • C10M169/04Mixtures of base-materials and additives
    • C10M169/041Mixtures of base-materials and additives the additives being macromolecular compounds only
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102Aliphatic fractions
    • C10M2203/1025Aliphatic fractions used as base material
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/0206Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers used as base material
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/28Esters
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    • C10M2207/283Esters of polyhydroxy compounds
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines
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Definitions

  • the invention relates to engine oils containing phenol-started oil-soluble polyethers to improve the piston cleanliness of motor vehicle engines.
  • Modern lubricants are subject to increasing demands with regard to reducing wear, longer running times, reduced deposits, engine cleanliness and low-temperature properties. Since there are quantitative limits to the use of additives, the amount of ash formers (detergents) for gasoline engine oils must not exceed certain values, the proportion of wear protection (zinc dithiophosphates) is limited due to the three-way catalysts and dirt dispersers can attack the rubber sealing elements if the dose is too high. Attempts have been made to improve the performance of the motor oil by using new base oils. It was therefore the object of the invention to provide new engine oil components which bring about a significantly increased performance compared to the prior art.
  • R 2 O is derived from a mixture of butylene oxide and propylene oxide with a maximum of 80% by weight of propylene oxide and preferably from butylene oxide alone.
  • the phenol component is alkylated with 1 or 2 alkyl radicals having 6 to 24, preferably 9 to 12 carbon atoms or consists of a bisphenol.
  • the phenol alkoxylates mentioned are obtained in a manner known per se by alkoxylation of the phenols with butylene oxide or mixtures of butylene oxide and propylene oxide with alkali.
  • Butylene oxide alone in amounts of 5 to 25 mol / phenol group is particularly preferred.
  • Dodecylphenol, nonylphenol and bisphenol A are particularly suitable as alkylphenols.
  • Preparation example (general) Reaction of alkylphenol or bisphenol A with alkylene oxides
  • 0.1% by weight of KOH, finely pulverized, based on the entire batch are distributed in the alkylphenol with stirring and heated to 130 ° C. at 200 mbar. Remaining traces of water are removed.
  • the autoclave is then closed and alkylene oxide is metered in so that a pressure of 6 bar is not exceeded.
  • Different alkylene oxides can be metered in simultaneously or in succession, so that statistical polyethers or blocks are formed with more or less sharp transitions. After the alkylene oxides have run in, the pressure drops to 2 to 3 bar in the course of 3 to 10 h.
  • the mixture is cooled to 80 ° C. and relaxed via a membrane valve and evacuated to 20 to 30 mbar. After maintaining the reduced pressure for about 1 h, equivalent amounts of acidic ion exchanger are then added to remove potassium and the mixture is filtered.
  • Motor oils are liquids, based on selected base oils, to which additives are added to achieve special properties in the motor. These are e.g. Engine cleanliness, reduced deposits, high temperature resistance, reduced wear and longer running time (cf. Aral oil guide, 10th edition 1989.1, pp. 23-30, and 1989.2, pp. 4-9).
  • alkylphenoxylates to be used according to the invention are added to motor oils, especially those based on hydrocarbons, in amounts of up to 10%, in particular 1 to 8% by weight.
  • a representative engine oil blend contains, for example, the following essential components 80 to 95 wt .-% base oil components 0.5 to 2.5% by weight viscosity index improver (100%) 1.5 to 10% by weight of ashless dispersants 1.5 to 8 wt% detergent 20.5 to 6% by weight wear protection 1 to 8% by weight of the phenoxylates to be added according to the invention
  • the alkylphenoxylates to be used according to the invention have a significantly higher temperature stability (DTG) than conventional alkoxylates.
  • the temperature stability with very good lubricating performance of the alkylphenoxylates to be used according to the invention is particularly evident in the test in the engine of motor vehicles.
  • a motor oil of the higher performance class API SF / CD was chosen as the basis for the test, to which 5% alkylphenoxylate was added in each case.
  • the engine suitability was tested. It was surprisingly found that the motor oils with 5% of the alkylphenoxylates to be used according to the invention with performance ratings of up to 79 points (i.e. very good ratings) were significantly higher than the starting engine oil API SF / CD with 67 or 69 (table).
  • Alkoxylates eg started with tridekanol and 1-butene oxide as alkylene oxide did not improve the engine test results.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Fats And Perfumes (AREA)
EP90124070A 1990-01-16 1990-12-13 Huiles pour moteurs contenant des phénols alcoxylés Expired - Lifetime EP0438709B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT90124070T ATE88496T1 (de) 1990-01-16 1990-12-13 Motorenoel mit einem gehalt an phenolalkoxylaten.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4001043 1990-01-16
DE4001043A DE4001043A1 (de) 1990-01-16 1990-01-16 Motorenoel mit einem gehalt an phenolalkoxylaten

Publications (2)

Publication Number Publication Date
EP0438709A1 true EP0438709A1 (fr) 1991-07-31
EP0438709B1 EP0438709B1 (fr) 1993-04-21

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP90124070A Expired - Lifetime EP0438709B1 (fr) 1990-01-16 1990-12-13 Huiles pour moteurs contenant des phénols alcoxylés

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EP (1) EP0438709B1 (fr)
AT (1) ATE88496T1 (fr)
CA (1) CA2034144C (fr)
DE (2) DE4001043A1 (fr)
ES (1) ES2042180T3 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000023544A1 (fr) * 1998-10-16 2000-04-27 Castrol Limited Huile de moteur comprenant un polyalkyleneglycol et utilisee dans un moteur a injection directe
WO2000052117A1 (fr) * 1999-03-04 2000-09-08 Rohmax Additives Gmbh Composition d'huile de moteur a tendance reduite a la formation de depots
WO2008002598A3 (fr) * 2006-06-27 2008-05-15 Exxonmobil Res & Eng Co Huiles de base lubrifiantes comprenant un éther phénolique synthétique et huiles lubrifiantes comprenant de telles huiles de base lubrifiantes mélangées à des huiles de co-base et/ou à des additifs
JP2013500358A (ja) * 2009-07-23 2013-01-07 ダウ グローバル テクノロジーズ エルエルシー グループi〜ivの炭化水素油のための潤滑添加剤として有用なポリアルキレングリコール
WO2013164449A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
WO2013164457A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
WO2014189712A1 (fr) * 2013-05-23 2014-11-27 Dow Global Technologies Llc Polymères de polyoxybutylène solubles dans l'huile en tant que modificateurs de frottement pour des lubrifiants
US10752858B2 (en) 2012-11-16 2020-08-25 Total Marketing Services Lubricant composition

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2968011B1 (fr) * 2010-11-26 2014-02-21 Total Raffinage Marketing Composition lubrifiante pour moteur
WO2014189711A1 (fr) 2013-05-23 2014-11-27 Dow Global Technologies Llc Polyalkylène glycols utilisables comme additifs pour lubrifiants dans des huiles de base hydrocarbonées

Citations (6)

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US3328284A (en) * 1965-01-06 1967-06-27 Petrolite Corp Oxyalkylate-sulfonate hydrocarbon inhibitor
US3696048A (en) * 1970-04-06 1972-10-03 Universal Oil Prod Co Corrosion inhibiting composition and use thereof
US3789003A (en) * 1971-08-25 1974-01-29 Texaco Inc Solubilizing process
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EP0246612A2 (fr) * 1986-05-20 1987-11-25 Dai-Ichi Kogyo Seiyaku Co., Ltd. Composition d'huile lubrifiante
EP0376236A1 (fr) * 1988-12-29 1990-07-04 BASF Aktiengesellschaft Utilisation de produits de réaction du 1,2-butylène oxyde avec des amines comme lubrifiants et lubrifiants contenant ces produits

Cited By (26)

* Cited by examiner, † Cited by third party
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WO2000023544A1 (fr) * 1998-10-16 2000-04-27 Castrol Limited Huile de moteur comprenant un polyalkyleneglycol et utilisee dans un moteur a injection directe
WO2000052117A1 (fr) * 1999-03-04 2000-09-08 Rohmax Additives Gmbh Composition d'huile de moteur a tendance reduite a la formation de depots
US6458750B1 (en) 1999-03-04 2002-10-01 Rohmax Additives Gmbh Engine oil composition with reduced deposit-formation tendency
JP2002538266A (ja) * 1999-03-04 2002-11-12 ローマックス アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツング 低い沈積物形成傾向を有するエンジンオイル組成物
WO2008002598A3 (fr) * 2006-06-27 2008-05-15 Exxonmobil Res & Eng Co Huiles de base lubrifiantes comprenant un éther phénolique synthétique et huiles lubrifiantes comprenant de telles huiles de base lubrifiantes mélangées à des huiles de co-base et/ou à des additifs
JP2013500358A (ja) * 2009-07-23 2013-01-07 ダウ グローバル テクノロジーズ エルエルシー グループi〜ivの炭化水素油のための潤滑添加剤として有用なポリアルキレングリコール
EP2456845B2 (fr) 2009-07-23 2020-03-25 Dow Global Technologies LLC Polyalkylène glycols utiles comme additifs lubrifiants pour des huiles hydrocarbonées des groupes i-iv
EP2456845B1 (fr) * 2009-07-23 2017-03-29 Dow Global Technologies LLC Polyalkylène glycols utiles comme additifs lubrifiants pour des huiles hydrocarbonées des groupes i-iv
KR20150020534A (ko) * 2012-05-04 2015-02-26 토탈 마케팅 서비스 엔진 윤활유 조성물
RU2635569C2 (ru) * 2012-05-04 2017-11-14 Тотал Маркетинг Сервисез Смазочная композиция для двигателя
CN111607451A (zh) * 2012-05-04 2020-09-01 道达尔销售服务公司 发动机润滑剂组合物
KR20150015455A (ko) * 2012-05-04 2015-02-10 토탈 마케팅 서비스 엔진용 윤활 조성물
FR2990213A1 (fr) * 2012-05-04 2013-11-08 Total Raffinage Marketing Composition lubrifiante pour moteur
JP2015516006A (ja) * 2012-05-04 2015-06-04 トータル・マーケティング・サービシーズ エンジン用潤滑剤組成物
JP2015516007A (ja) * 2012-05-04 2015-06-04 トータル・マーケティング・サービシーズ エンジン用潤滑剤組成物
KR102125478B1 (ko) 2012-05-04 2020-07-08 토탈 마케팅 서비스 엔진용 윤활 조성물
WO2013164457A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
FR2990215A1 (fr) * 2012-05-04 2013-11-08 Total Raffinage Marketing Composition lubrifiante pour moteur
RU2638542C2 (ru) * 2012-05-04 2017-12-14 Тотал Маркетинг Сервисез Смазочная композиция для двигателя
US10604717B2 (en) 2012-05-04 2020-03-31 Total Marketing Services Lubricant composition for an engine
WO2013164449A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
US10752858B2 (en) 2012-11-16 2020-08-25 Total Marketing Services Lubricant composition
CN105209583B (zh) * 2013-05-23 2018-05-04 陶氏环球技术有限责任公司 作为润滑剂的摩擦改进剂的油溶性聚氧化丁烯聚合物
US9914895B2 (en) 2013-05-23 2018-03-13 Dow Global Technologies Llc Oil soluble polyoxybutylene polymers as friction modifiers for lubricants
CN105209583A (zh) * 2013-05-23 2015-12-30 陶氏环球技术有限责任公司 作为润滑剂的摩擦改进剂的油溶性聚氧化丁烯聚合物
WO2014189712A1 (fr) * 2013-05-23 2014-11-27 Dow Global Technologies Llc Polymères de polyoxybutylène solubles dans l'huile en tant que modificateurs de frottement pour des lubrifiants

Also Published As

Publication number Publication date
DE4001043A1 (de) 1991-07-18
CA2034144A1 (fr) 1991-07-17
ES2042180T3 (es) 1993-12-01
EP0438709B1 (fr) 1993-04-21
DE59001259D1 (de) 1993-05-27
CA2034144C (fr) 1999-06-08
ATE88496T1 (de) 1993-05-15

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