EP0608018A1 - Aminoalkyl phosphonate en tant qu'additif anti-usure pour lubrifiant ayant une composition de base hydrophile - Google Patents

Aminoalkyl phosphonate en tant qu'additif anti-usure pour lubrifiant ayant une composition de base hydrophile Download PDF

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Publication number
EP0608018A1
EP0608018A1 EP94200064A EP94200064A EP0608018A1 EP 0608018 A1 EP0608018 A1 EP 0608018A1 EP 94200064 A EP94200064 A EP 94200064A EP 94200064 A EP94200064 A EP 94200064A EP 0608018 A1 EP0608018 A1 EP 0608018A1
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EP
European Patent Office
Prior art keywords
phosphonate
lubricant
basestock
alkyl
amino alkyl
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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Application number
EP94200064A
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German (de)
English (en)
Inventor
Theodore Alan Marolewski
Eric William Burkhardt
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.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
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Publication date
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Publication of EP0608018A1 publication Critical patent/EP0608018A1/fr
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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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/082—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type monocarboxylic
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
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    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C10M2209/1065—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only used as base material
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    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C10M2209/1075—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106 used as base material
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    • C10M2223/042—Metal salts thereof
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • organophosphorus compounds either alone, reacted with, or in admixture with other compounds have been suggested as lubricant additives in the following prior art disclosures, for example:
  • the present invention relates to lubricants comprising a hydrophilic basestock which also comprise an amino alkyl phosphonate as an antiwear additive.
  • a preferred amino alkyl phosphonate is an 0,0-dialkyl N,N-bis(hydroxyalkyl) amino methyl phosphonate.
  • hydrophilic basestock as used herein is intended to cover non-petroleum and non-organic, hydrophilic basestocks and be inclusive of both water-based lubricants, which may contain hydrophilic associative thickeners (such as nonionic polyalkylene glycol), and those lubricants containing an organic molecule as the basestock component, such as polyalkylene glycols containing free hydroxy groups.
  • Such types of lubricants are well known to persons of ordinary skill in the art and are useful, for example, as hydraulic fluids and lubricants (e.g., polyalkylene glycol-based products) or as chain lubricants and metal working fluids (e.g., water-based lubricants).
  • hydraulic fluids and lubricants e.g., polyalkylene glycol-based products
  • chain lubricants and metal working fluids e.g., water-based lubricants
  • the present invention relates to the use of an effective amount of an amino alkyl phosphonate in such type of lubricants as an antiwear additive.
  • an effective amount of an amino alkyl phosphonate in such type of lubricants as an antiwear additive.
  • the amount of this type of phosphonate additive can range from about 0.1% to about 10%, by weight of the lubricant, preferably from about 0.2% to about 2%.
  • amino alkyl phosphonate for use herein is an 0,0-dialkyl N,N-bis(hydroxyalkyl) amino methyl phosphonate of the formula where each R can be the same or different and are alkyl groups, preferably C 1 to C 4 alkyl groups, and each R 1 can be the same or different and are alkylene groups, preferably C 1 to C 4 alkylene groups.
  • a more preferred material for use in the present invention is 0,0-diethyl N,N-bis(2-hydroxyethyl) amino methyl phosphonate which is available commercially under the trademark FYROL® 6 from Akzo Chemicals Inc.
  • the lubricant compositions intended by the present invention can contain other functional additives known to persons of ordinary skill in the art.
  • Polyol B a multifunctional polyether glycol in which the terminal hydroxyl groups of Polyol A have been converted to the corresponding acetate ester. It has CAS No. 76308-92-4.
  • FYROL® 6 brand a commercially available flame retardant, 0,0-diethyl N,N-bis(2-hydroxyethyl) amino methyl phosphonate, from Akzo Chemicals Inc.
  • DAPRAL® GE 202 brand a commercially available thickener, from Akzo Chemicals Inc., which is a partial ester of a branched carboxylic acid copolymer having a comb-like structure with an average molecular weight of 20,000.
  • the main chain consists of carbon atoms only, the alkyl branches are hydrophobic, and the ester and ether groups are hydrophilic.
  • SYN-O-AD® 8478 brand is a commercially available lubricant additive, tert-butylphenyl diphenyl phosphate ester from Akzo Chemicals Inc.
  • Test Nos. 3 and 4 A comparison of the results of Test Nos. 3 and 4, above illustrates the importance of using a hydrophilic lubricant basestock (Polyol A) as compared to one in which a hydroxyl group, for example, is replaced with a less hydrophilic group, such as acetate (Polyol B).
  • Test No. 6 illustrates the inferior results obtained using a conventional hydrocarbon additive, whereas Test No. 7 illustrates the lack of positive effect using a conventional thickener.
  • a composition was formulated comprising deionized water and 5% of a non-ionic polyalkylene glycol thickener having a molecular weight of 3000, which is commercially available under the trademark DAPRAL@ GT 282 from Akzo Chemicals Inc.
  • a four ball wear test was conducted at 75°C, 40 kg load, for one hour at 1800 rpm. The test, which was quite noisy, was only conducted for one-half hour and was terminated. The scar was 2.6 mm.
  • VICTAWET® 12 brand a nonionic phosphate ester surfactant from Akzo Chemicals Inc.

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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)
EP94200064A 1993-01-22 1994-01-13 Aminoalkyl phosphonate en tant qu'additif anti-usure pour lubrifiant ayant une composition de base hydrophile Withdrawn EP0608018A1 (fr)

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US720493A 1993-01-22 1993-01-22
US7204 2001-11-08

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Cited By (1)

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EP2570471A1 (fr) * 2011-09-15 2013-03-20 Afton Chemical Corporation Préparation et utilisation de composés d'ester dialkylique de l'acide aminoalkylphosphonique dans un lubrifiant contre l'usure et/ou pour la réduction de la friction

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FR1222104A (fr) * 1958-04-14 1960-06-08 California Research Corp Composition détergente en barres
US3498969A (en) * 1967-10-11 1970-03-03 Swift & Co Phosphonate amine polyol compounds and a process for preparing same
US4260499A (en) * 1978-08-25 1981-04-07 Texaco Inc. Water-based lubricants
US4563299A (en) * 1983-11-02 1986-01-07 Mobil Oil Corporation Phosphorus-containing reaction products as antiwear and load carrying additives for lubricants
EP0335701A2 (fr) * 1988-03-31 1989-10-04 Ethyl Petroleum Additives, Inc. Composition d'huile lubrifiante
SU1659456A1 (ru) * 1989-05-12 1991-06-30 Уральский Научно-Исследовательский Институт Трубчатой Промышленности Смазка дл холодной обработки металлов давлением
WO1991018073A1 (fr) * 1990-05-17 1991-11-28 The Lubrizol Corporation Compositions a teneur en phosphore pour systemes de refrigeration

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US2635112A (en) * 1949-07-28 1953-04-14 Research Corp Process for producing aminomethylphosphonic acid compounds
FR1222104A (fr) * 1958-04-14 1960-06-08 California Research Corp Composition détergente en barres
US3498969A (en) * 1967-10-11 1970-03-03 Swift & Co Phosphonate amine polyol compounds and a process for preparing same
US4260499A (en) * 1978-08-25 1981-04-07 Texaco Inc. Water-based lubricants
US4563299A (en) * 1983-11-02 1986-01-07 Mobil Oil Corporation Phosphorus-containing reaction products as antiwear and load carrying additives for lubricants
EP0335701A2 (fr) * 1988-03-31 1989-10-04 Ethyl Petroleum Additives, Inc. Composition d'huile lubrifiante
SU1659456A1 (ru) * 1989-05-12 1991-06-30 Уральский Научно-Исследовательский Институт Трубчатой Промышленности Смазка дл холодной обработки металлов давлением
WO1991018073A1 (fr) * 1990-05-17 1991-11-28 The Lubrizol Corporation Compositions a teneur en phosphore pour systemes de refrigeration

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
EP2570471A1 (fr) * 2011-09-15 2013-03-20 Afton Chemical Corporation Préparation et utilisation de composés d'ester dialkylique de l'acide aminoalkylphosphonique dans un lubrifiant contre l'usure et/ou pour la réduction de la friction
CN102994192A (zh) * 2011-09-15 2013-03-27 雅富顿公司 氨基烷基膦酸二烷基酯化合物的制备及其用于抗磨、降低摩擦和/或防微点蚀的润滑剂的用途
CN102994192B (zh) * 2011-09-15 2016-09-07 雅富顿公司 氨基烷基膦酸二烷基酯化合物的制备及其用于抗磨、降低摩擦和/或防微点蚀的润滑剂的用途
CN106244293A (zh) * 2011-09-15 2016-12-21 雅富顿公司 润滑剂组合物
US10563146B2 (en) 2011-09-15 2020-02-18 Afton Chemical Corporation Preparation and use of aminoalkylphosphonic acid dilakyl ester compounds in a lubricant for antiwear, friction reduction, and/or micropitting prevention
US11149226B2 (en) 2011-09-15 2021-10-19 Afton Chemical Corporation Preparation and use of aminoalkylphosphonic acid dialkyl ester compounds in a lubricant for antiwear, friction reduction, and/or micropitting prevention

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