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EP0608018A1 - Amino alkyl phosphonate as antiwear additive for lubricant containing hydrophylic basestock - Google Patents

Amino alkyl phosphonate as antiwear additive for lubricant containing hydrophylic basestock 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
Authority
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.)
Withdrawn
Application number
EP94200064A
Other languages
German (de)
French (fr)
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Akzo Nobel NV filed Critical Akzo Nobel NV
Publication of EP0608018A1 publication Critical patent/EP0608018A1/en
Withdrawn legal-status Critical Current

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    • 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
    • C10M173/00Lubricating compositions containing more than 10% water
    • C10M173/02Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34Polyoxyalkylenes
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    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04Phosphate esters
    • C10M137/10Thio derivatives
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    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
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    • C10M145/00Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10Macromolecular 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
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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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    • C10M2201/02Water
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/082Macromolecular 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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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/104Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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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
    • C10M2209/105Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C10M2209/1065Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only used as base material
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    • C10M2209/00Organic 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
    • C10M2209/107Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C10M2209/1075Polyethers, 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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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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    • C10M2209/109Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2223/04Phosphate esters
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10N2050/01Emulsions, 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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Abstract

Lubricants containing hydrophilic basestocks (e.g., water-based lubricants or organic-based lubricants with polyalkylene glycol basestocks containing free hydroxy groups) can be formulated with an amino alkyl phosphonate antiwear additive.

Description

    BACKGROUND OF THE INVENTION
  • A variety of 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:
    • (1) U.S. Patent No. 3,553,131 discloses use of a mixture of an organic phosphonate and an organic amine;
    • (2) U.S. Patent No. 4,077,892 mentions the reaction of a partially esterified multifunctional alcohol with a phosphorus trihalide or a dihydrocarbyl phosphonate;
    • (3) U.S. Patent No. 4,228,020 shows the combination of graphite and a di-lower alkyl hydrocarbyl phosphonate;
    • (4) U.S. Patent No. 4,231,781 teaches use of halophenoxy-alkoxy phosphonates as lubricants or lubricant additives;
    • (5) U.S. Patent No. 4,664,828 relates to the use of certain hydrogen phosphonates as additives in certain water-based fluids;
    • (6) U.S. Patent No. 5,059,335 teaches the use of hydroxyalkane phosphonic acids and derivatives as antiwear and extreme pressure additives in lubricants;
    • (7) French Patent No. 1,566,028 shows the use of certain phosphorus compounds as sludge control agents in functional fluids; and
    • (8) British Patent No. 748,137 shows the use of an ester or metal salt of a hydroxy phosphonic acid in lubricating oils.

    British Patent No. 899,101 shows that amino-phosphonates of the formula
    Figure imgb0001

    where R1 and R2 can, for example, be alkyl and R3 and R4 can also be alkyl, are useful as load-carrying additives in certain diester basestocks of the formula
    Figure imgb0002

    where n is from 4 to 14 and R is C4-C18 alkyl. These lubricants are hydrophobic in nature rather than hydrophilic. Most recently, U.S. Patent No. 5,124,055 shows lubricating oil compositions comprising an oil of suitable lubricating viscosity and a co-sulfurized blend of soybean oil and an ester, amide, ester-amide, or fatty amine derivative containing at least one substituent group. One class of suitable amines can be prepared by reacting a dialkyl phosphate with formaldehyde and a dialkanol amine to yield the following type of product:
    Figure imgb0003
    SUMMARY OF THE INVENTION
  • 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.
  • DETAILED DESCRIPTION OF THE INVENTION
  • The lubricant compositions to which the present invention relates are those which contain hydrophilic basestocks. The term "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).
  • 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. Generally speaking, it is contemplated that 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%.
  • The preferred type of amino alkyl phosphonate for use herein is an 0,0-dialkyl N,N-bis(hydroxyalkyl) amino methyl phosphonate of the formula
    Figure imgb0004
    where each R can be the same or different and are alkyl groups, preferably C1 to C4 alkyl groups, and each R1 can be the same or different and are alkylene groups, preferably C1 to C4 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.
  • In addition to the aforementioned types of basestock and phosphonate, the lubricant compositions intended by the present invention can contain other functional additives known to persons of ordinary skill in the art.
  • The present invention is further illustrated by the Examples which follow.
  • EXAMPLES 1-8
  • These Examples illustrate four ball wear test data for a number of compositions containing hydroxyl-containing and acetate ester-containing polyglycol lubricants. The four ball test was conducted at 600 rpm for one hour at 54°C using a 40 kg load. The various ingredients described in the data given below are:
    • Polyol A: a multifunctional polyether polyglycol containing terminal hydroxyls having CAS No. 025791-96-2. It was a viscous liquid having a specific gravity of 1.033.
  • 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.
  • In the wear test data which follows, a lower wear scar reading is more desirable:
    Figure imgb0005
  • 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.
  • EXAMPLES 9-12
  • These Examples illustrate the use of the present invention in a water-based conveyor chain lubricant. 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.
  • A series of blends were then formulated as described below under similar conditions and the following wear data was obtained. In the tests the following new ingredients, as compared to those used in Examples 1-8 were used:
    • DAPRAL®712 brand: a commercially available thickener which is an ester of a branched carboxylic acid copolymer having a comb-like structure with an average molecular weight of 7,000 from Akzo Chemicals Inc.
  • VICTAWET® 12 brand: a nonionic phosphate ester surfactant from Akzo Chemicals Inc.
  • The results are as follows:
    Figure imgb0006
  • The foregoing Examples should not be construed in a limitating sense since they are merely intended to illustrate certain embodiments of the invention. The scope of protection sought is set forth in the claims which follow.

Claims (5)

1. A lubricant composition comprising a hydrophilic basestock selected from the group consisting of water-based basestocks containing hydrophilic associative thickeners and organic molecule-containing basestocks, and an effective amount, as an antiwear additive, of an amino alkyl phosphonate.
2. A lubricant as claimed in Claim 1 wherein the amount of phosphonate is from 0.1 % to 10%, by weight of the composition.
3. A lubricant as claimed in any one of Claims 1-2 wherein the amino alkyl phosphonate is an 0,0-dialkyl N,N-bis(hydroxyalkyl) amino methyl phosphonate.
4. A lubricant as claimed in Claim 3 wherein the alkyl moieties are C1 to C4 alkyl.
5. A lubricant as claimed in Claim 4 wherein the alkyl moieties are ethyl.
EP94200064A 1993-01-22 1994-01-13 Amino alkyl phosphonate as antiwear additive for lubricant containing hydrophylic basestock Withdrawn EP0608018A1 (en)

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EP2570471A1 (en) * 2011-09-15 2013-03-20 Afton Chemical Corporation Preparation and use of aminoalkylphosphonic acid dialkyl ester compounds in a lubricant for antiwear and/or friction reduction

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2570471A1 (en) * 2011-09-15 2013-03-20 Afton Chemical Corporation Preparation and use of aminoalkylphosphonic acid dialkyl ester compounds in a lubricant for antiwear and/or friction reduction
CN102994192A (en) * 2011-09-15 2013-03-27 雅富顿公司 Preparation and use of aminoalkylphosphonic acid dilakyl ester compounds in a lubricant for antiwear, friction reduction, and/or micropitting prevention
CN102994192B (en) * 2011-09-15 2016-09-07 雅富顿公司 Preparing and for wear-resistant, reduction friction and/or the purposes of the lubricant of anti-microdot erosion of aminoalkylphosphonic dialkyl compound
CN106244293A (en) * 2011-09-15 2016-12-21 雅富顿公司 Lubricant compositions
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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