EP0120665A2 - Soluble oil cutting fluid - Google Patents

Soluble oil cutting fluid Download PDF

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Publication number
EP0120665A2
EP0120665A2 EP84301863A EP84301863A EP0120665A2 EP 0120665 A2 EP0120665 A2 EP 0120665A2 EP 84301863 A EP84301863 A EP 84301863A EP 84301863 A EP84301863 A EP 84301863A EP 0120665 A2 EP0120665 A2 EP 0120665A2
Authority
EP
European Patent Office
Prior art keywords
oil
soluble
water
weight
cutting fluid
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.)
Granted
Application number
EP84301863A
Other languages
German (de)
French (fr)
Other versions
EP0120665B1 (en
EP0120665A3 (en
Inventor
Anthony Paul Rawlinson
James White
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.)
BP PLC
Original Assignee
BP PLC
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Publication date
Application filed by BP PLC filed Critical BP PLC
Priority to AT84301863T priority Critical patent/ATE27174T1/en
Publication of EP0120665A2 publication Critical patent/EP0120665A2/en
Publication of EP0120665A3 publication Critical patent/EP0120665A3/en
Application granted granted Critical
Publication of EP0120665B1 publication Critical patent/EP0120665B1/en
Expired 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
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
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    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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Definitions

  • This invention relates to a soluble-oil and to an oil-in-water emulsion containing the soluble-oil, which emulsion is suitable for use as a cutting fluid.
  • Soluble-oil emulsions are well known as cutting fluids.
  • the term "soluble-oil” although used throughout the industry is, in fact, a misnomer because the constituents are not soluble in water.
  • the soluble-oils are basically mineral oils blended with emulsifiers and other additives which, when added to water and stirred, form an oil-in-water emulsion.
  • the emulsion allows the good cooling properties of water to be utilised in the metal working process whilst the oil and additives provide lubrication and corrosion inhibiting properties.
  • the one or more emulsifiers included in the soluble-oil may not readily form a stable blend with the mineral oil and so a coupling agent is commonly required to bind the emulsifier to the oil.
  • Conventional coupling agents include, for example, volatile alcohols such as sec. butanol, butyl oxitol or cyclohexanol.
  • the volatility of these coupling agents means that over a period of time coupling agent is lost from the soluble-oil by vaporisation. This loss of coupling agent reduces the stability of the soluble-oil and is often associated with an objectionable smell.
  • the coupling agents have relatively low flash points which means that great care must be taken when they are blended or otherwise handled.
  • the present invention relates to a soluble-oil which is relatively stable without the need for a conventional coupling agent.
  • Soluble-oil emulsions may become contaminated by bacteria, yeasts and moulds. The growth of these micro-organisms may cause problems such as emulsion breakdown, the production of slimes and fungal mats and the evolution of foul odours.
  • Biocides are often therefore included in soluble-oil formulations to control microbial growth: It has surprisingly been found that at least some of the soluble-oils according to the present invention are bio-static even though conventional biocides are not included in the formulation.
  • the soluble-oil according to the present invention comprises the following amounts of the components;
  • the alkali metal or alkaline-earth metal of the alkyl benzene sulphonate is preferably potassium or calcium or more preferably sodium.
  • the alkyl group is preferably derived from polypropylene.
  • the alkali or alkaline-earth metal alkyl benzene sulphonate may be produced by known methods from synthetic sulphonic acids.
  • the molecular weight of the compound is from 400 to 520. A high molecular weight improves the corrosion inhibiting properties of the soluble oil whereas a low molecular weight improves emulsion stability and so the choice of molecular weight involves a compromise. Mixtures of alkyl benzene sulphonates may be used.
  • the fatty acid diethanolamides are preferably formed by the reaction of diethanolamine with naturally occurring fatty acids having from 12 to 20 carbon atoms.
  • the fatty acids may be saturated or unsaturated but are preferably unsaturated.
  • the mixed alkanolamine borate comprises the reaction products of more than one alkanolamine with boric acid.
  • the alkanolamines may be selected from monoethanolamine, diethanolamine, triethanolamine, N,N dimethyl ethanolamine.
  • a preferred combination of alkanolamines is mono- and di-ethanolamine.
  • the polyisobutenesuccinimide is preferably overbased with excess amine and preferably has a molecular weight of from 1000 to 3000.
  • the soluble-oil formulation also preferably contains a small amount of distilled water e.g. from 0 to 2% by weight of the total weight of the soluble-oil.
  • the distilled water improves the stability of the blend.
  • a defoaming agent such as a Friedel Krafts wax may also be included in the soluble oil.
  • a suitable wax is SASOL wax SH 105 supplied by Weber.
  • the amount of defoaming agent is preferably in the range 0-0.05% by weight of the total weight of the soluble-oil.
  • the soluble-oils according to the present invention may also contain other conventional additives for soluble-oils such as for example corrosion inhibiting additives.
  • a suitable commercially available corrosion inhibitor comprises a solution of benzene sulphonamido hexyl carboxylic acid in water and N,N-dimethyl amino propyl amine. This commercially available corrosion inhibitor is particularly effective when supplemented with triethanolamine. Alternatively, a mixture of triethanolamine and other carboxylic acids such as, for example, caprylic acid or capric acid may be used to inhibit corrosion. Typically, the corrosion inhibitor is used up to an amount of 2% by weight of the total weight of the soluble-oil. If the corrosion inhibitor comprises a mixture of triethanolamine and a carboxylic acid then the two compounds may be present in equal weights up to a combined weight of 2% of the total weight of the soluble-oil.
  • a biocidal soluble-oil If a biocidal soluble-oil is required, a conventional biocide may be included in the formulation.
  • the optional components of the soluble-oil are included in the composition in place of some of the mineral oil.
  • base oils designated 100 to 500 solvent neutral have been found to be particularly suitable, i.e. paraffinic oils typically having kinematic viscosities at 40°C in the range 12 to 100 cSt.
  • the soluble-oil according to the present invention is relatively stable and when mixed with water readily forms an emulsion which may be used in a number of metal working operations e.g. cutting, drilling and grinding.
  • the emulsion has a water to soluble-oil ratio of from 10:1 to 40:1 although higher and lower dilutions may be useful in certain applications.
  • the sodium alkyl benzene sulphonate had an average molecular weight of 440 and was used as a 60% by weight solution in a paraffinic mineral oil.
  • the fatty acid diethanolamine was oleic acid diethanolamide and was approximately 25% overbased with excess diethanolamine.
  • the mixed alkanolamine borate was a mixture of boric acid, monoethanolamine and diethanolamine in the approximate weight ratio 30:33:35.
  • the polyisobutene succinimide was formed by the reaction between a polyisobutene having a molecular weight of approximately 1000,succinic acid anhydride and diethanolamine and was overbased with a small excess of N,N dimethyl ethanolamine.
  • Samples of the two formulations were mixed with mains tap water at ratios of water to oil of from 10:1 to 25:1.
  • the oil readily emulsified in the water at each dilution and each emulsion was subjected to the Institute of Petroleum standard test method IP 125 Aqueous Cutting Fluid Corrosion of Cast Iron. There was no visible staining or pitting at the lower dilutions and the corrosion at the highest dilutions was hardly perceptible.
  • a test rig was used to evaluate the microbial degradation of the soluble-oil emulsions in a simulated workshop operation.
  • the rig comprised a reservoir for the cutting fluid and an air lift pump to transfer the fluid from the reservoir to a funnel containing metal cuttings, the funnel being mounted over the reservoir so that the fluid drained back into the reservoir.
  • Duplicate samples of Formulation A diluted with mains tap water in the ratio of water to oil of 20:1 were tested in the test rig.
  • An inoculum prepared from a mixed culture of fungi and bacteria originating from a spoiled cutting oil emulsion was added to the test samples so that an initial total viable count of approximately 10 6 micro-organisms per millilitre of emulsion was obtained.
  • the emulsion had not evolved H 2 S or encouraged yeast, mould or fungal growth.
  • the total viable bacteria count remained at approximately 10 6 organisms per millilitre of emulsion throughout the test.
  • the strength of the emulsion was relatively constant throughout the test and the pH which was initially 9.5 fell to around 8.5 after 12 days and then remained at this value for the remainder of the test period.
  • Formulation D is similar to Formulation C except that it contains a corrosion inhibiting mixture comprising triethanolamine and Hostacor H.
  • Hostacor H is a commercially available corrosion inhibitor comprising a solution of benzene sulphonamido hexyl carboxylic acid in water and N,N-dimethyl amino propyl amine.
  • Each of the formulations were mixed with mains tap water at ratios of water to soluble-oil of from 10:1 to 40:1.
  • the soluble-oils readily emulsified in the water at each dilution.
  • Each of the emulsions was subjected to the Institute of petroleum standard test method IP125, Aqueous Cutting Fluid Corrosion of Cast Iron.
  • Formulation C showed no pitting or staining up to dilutions of 20:1
  • Formulation D showed no pitting or staining up to dilutions of 40:1.

Abstract

A soluble-oil, suitable when diluted with water, for use as a cutting fluid comprises an alkali or alkaline-earth metal alkyl benzene sulphonate, a fatty acid diethanolamide, a mixed alkanolamine borate, a polyisobutenesuccinimide and a major proportion of mineral oil. The soluble-oil is relatively stable without the need for a conventional coupling agent and some soluble-oil emulsions are bio-static even though conventional biocides are not included.

Description

  • This invention relates to a soluble-oil and to an oil-in-water emulsion containing the soluble-oil, which emulsion is suitable for use as a cutting fluid.
  • Soluble-oil emulsions are well known as cutting fluids. The term "soluble-oil" although used throughout the industry is, in fact, a misnomer because the constituents are not soluble in water. The soluble-oils are basically mineral oils blended with emulsifiers and other additives which, when added to water and stirred, form an oil-in-water emulsion. The emulsion allows the good cooling properties of water to be utilised in the metal working process whilst the oil and additives provide lubrication and corrosion inhibiting properties.
  • The one or more emulsifiers included in the soluble-oil may not readily form a stable blend with the mineral oil and so a coupling agent is commonly required to bind the emulsifier to the oil. Conventional coupling agents include, for example, volatile alcohols such as sec. butanol, butyl oxitol or cyclohexanol. The volatility of these coupling agents means that over a period of time coupling agent is lost from the soluble-oil by vaporisation. This loss of coupling agent reduces the stability of the soluble-oil and is often associated with an objectionable smell. Further, the coupling agents have relatively low flash points which means that great care must be taken when they are blended or otherwise handled.
  • The present invention relates to a soluble-oil which is relatively stable without the need for a conventional coupling agent.
  • Thus according to the present invention a soluble-oil suitable, when diluted with water, for use as a cutting fluid comprises an alkali or alkaline-earth metal alkyl benzene sulphonate, a fatty acid diethanolamide, a mixed alkanolamine borate, a polyisobutenesuccinimide and a major proportion of mineral oil.
  • Soluble-oil emulsions may become contaminated by bacteria, yeasts and moulds. The growth of these micro-organisms may cause problems such as emulsion breakdown, the production of slimes and fungal mats and the evolution of foul odours. Biocides are often therefore included in soluble-oil formulations to control microbial growth: It has surprisingly been found that at least some of the soluble-oils according to the present invention are bio-static even though conventional biocides are not included in the formulation.
  • Suitably, the soluble-oil according to the present invention comprises the following amounts of the components;
    Figure imgb0001
  • The alkali metal or alkaline-earth metal of the alkyl benzene sulphonate is preferably potassium or calcium or more preferably sodium. The alkyl group is preferably derived from polypropylene. The alkali or alkaline-earth metal alkyl benzene sulphonate may be produced by known methods from synthetic sulphonic acids. Preferably the molecular weight of the compound is from 400 to 520. A high molecular weight improves the corrosion inhibiting properties of the soluble oil whereas a low molecular weight improves emulsion stability and so the choice of molecular weight involves a compromise. Mixtures of alkyl benzene sulphonates may be used.
  • The fatty acid diethanolamides are preferably formed by the reaction of diethanolamine with naturally occurring fatty acids having from 12 to 20 carbon atoms. The fatty acids may be saturated or unsaturated but are preferably unsaturated.
  • The mixed alkanolamine borate comprises the reaction products of more than one alkanolamine with boric acid. The alkanolamines may be selected from monoethanolamine, diethanolamine, triethanolamine, N,N dimethyl ethanolamine. A preferred combination of alkanolamines is mono- and di-ethanolamine.
  • The polyisobutenesuccinimide is preferably overbased with excess amine and preferably has a molecular weight of from 1000 to 3000.
  • The soluble-oil formulation also preferably contains a small amount of distilled water e.g. from 0 to 2% by weight of the total weight of the soluble-oil. The distilled water improves the stability of the blend.
  • A defoaming agent such as a Friedel Krafts wax may also be included in the soluble oil. A suitable wax is SASOL wax SH 105 supplied by Weber. The amount of defoaming agent is preferably in the range 0-0.05% by weight of the total weight of the soluble-oil.
  • The soluble-oils according to the present invention may also contain other conventional additives for soluble-oils such as for example corrosion inhibiting additives. A suitable commercially available corrosion inhibitor comprises a solution of benzene sulphonamido hexyl carboxylic acid in water and N,N-dimethyl amino propyl amine. This commercially available corrosion inhibitor is particularly effective when supplemented with triethanolamine. Alternatively, a mixture of triethanolamine and other carboxylic acids such as, for example, caprylic acid or capric acid may be used to inhibit corrosion. Typically, the corrosion inhibitor is used up to an amount of 2% by weight of the total weight of the soluble-oil. If the corrosion inhibitor comprises a mixture of triethanolamine and a carboxylic acid then the two compounds may be present in equal weights up to a combined weight of 2% of the total weight of the soluble-oil.
  • If a biocidal soluble-oil is required, a conventional biocide may be included in the formulation.
  • It is to be understood that the optional components of the soluble-oil are included in the composition in place of some of the mineral oil.
  • Although a wide range of mineral oils may be used in the soluble-oil formulations according to the present invention, base oils designated 100 to 500 solvent neutral have been found to be particularly suitable, i.e. paraffinic oils typically having kinematic viscosities at 40°C in the range 12 to 100 cSt.
  • The soluble-oil according to the present invention is relatively stable and when mixed with water readily forms an emulsion which may be used in a number of metal working operations e.g. cutting, drilling and grinding. Preferably, the emulsion has a water to soluble-oil ratio of from 10:1 to 40:1 although higher and lower dilutions may be useful in certain applications.
  • The invention is illustrated with reference to the following example.
  • Example 1
  • Two soluble-oil formulations were prepared by mixing the following components:-
    Figure imgb0002
  • The sodium alkyl benzene sulphonate had an average molecular weight of 440 and was used as a 60% by weight solution in a paraffinic mineral oil. The fatty acid diethanolamine was oleic acid diethanolamide and was approximately 25% overbased with excess diethanolamine. The mixed alkanolamine borate was a mixture of boric acid, monoethanolamine and diethanolamine in the approximate weight ratio 30:33:35. The polyisobutene succinimide was formed by the reaction between a polyisobutene having a molecular weight of approximately 1000,succinic acid anhydride and diethanolamine and was overbased with a small excess of N,N dimethyl ethanolamine.
  • The thermal stability of each formulation was tested after . 14 days at temperatures in the range -5°C to 50°C using a method based on the Institute of Petroleum test method IP 311, Thermal Stability of Emulsifiable Cutting Oil. Both formulations were very viscous at temperatures of 0°C and below but were stable on warming. Formulation B was also stable at temperatures up to 50°C. Formulation A became unstable at temperatures above 40°C. However, in the presence of 0.5% wt of water, Formulation A was also stable up to 50°C.
  • Samples of the two formulations were mixed with mains tap water at ratios of water to oil of from 10:1 to 25:1. The oil readily emulsified in the water at each dilution and each emulsion was subjected to the Institute of Petroleum standard test method IP 125 Aqueous Cutting Fluid Corrosion of Cast Iron. There was no visible staining or pitting at the lower dilutions and the corrosion at the highest dilutions was hardly perceptible.
  • The propensity to foam of Formulation B was less than that of Formulation A as determined by the Institute of Petroleum standard test method IP 312, Frothing Characteristics of Emulsifiable Cutting Oil. This is presumably due to the inclusion in Formulation B of Sasol wax, a known defoaming agent.
  • A test rig was used to evaluate the microbial degradation of the soluble-oil emulsions in a simulated workshop operation. The rig comprised a reservoir for the cutting fluid and an air lift pump to transfer the fluid from the reservoir to a funnel containing metal cuttings, the funnel being mounted over the reservoir so that the fluid drained back into the reservoir. Duplicate samples of Formulation A diluted with mains tap water in the ratio of water to oil of 20:1 were tested in the test rig. An inoculum prepared from a mixed culture of fungi and bacteria originating from a spoiled cutting oil emulsion was added to the test samples so that an initial total viable count of approximately 106 micro-organisms per millilitre of emulsion was obtained. Air was passed through the rig to circulate and aerate the fluid during normal working hours from Monday to Friday each week. Each Monday morning, viable counts of aerobic bacteria, yeasts and moulds were prepared and the presence of sulphide producing bacteria, evolution of H2S, pH and emulsion stability were determined.
  • Up to the end of 14 weeks, the emulsion had not evolved H2S or encouraged yeast, mould or fungal growth. The total viable bacteria count remained at approximately 106 organisms per millilitre of emulsion throughout the test. The strength of the emulsion was relatively constant throughout the test and the pH which was initially 9.5 fell to around 8.5 after 12 days and then remained at this value for the remainder of the test period.
  • The results show that Formulation A, which contains no conventional biocide or coupling agent, forms a stable emulsion which has biostatic properties and does not evolve H2S.
  • Example 2
  • Two soluble-oil formulations were prepared by mixing the following components:-
  • Figure imgb0003
  • Formulation D is similar to Formulation C except that it contains a corrosion inhibiting mixture comprising triethanolamine and Hostacor H. Hostacor H is a commercially available corrosion inhibitor comprising a solution of benzene sulphonamido hexyl carboxylic acid in water and N,N-dimethyl amino propyl amine.
  • The thermal stability of each formualtion was tested after 14 days at temperatures in the range 0 to 60°C using a method based on the Institute of Petroleum test method IP311, Thermal Stability of Emulsifiable Cutting Oil. Both formulations were stable throughout the temperature range.
  • Each of the formulations were mixed with mains tap water at ratios of water to soluble-oil of from 10:1 to 40:1. The soluble-oils readily emulsified in the water at each dilution. Each of the emulsions was subjected to the Institute of petroleum standard test method IP125, Aqueous Cutting Fluid Corrosion of Cast Iron. Formulation C showed no pitting or staining up to dilutions of 20:1 and Formulation D showed no pitting or staining up to dilutions of 40:1.
  • The results show that both formulations, which contain no conventioned coupling agent, form relatively stable emulsions with water and that the inclusion of the triethanolamine and Hostacor H improve the corrosion inhibiting properties of the soluble-oil.

Claims (10)

1. A soluble-oil suitable, when diluted with water, for use as a cutting fluid comprises an alkali or alkaline-earth metal alkyl benzene sulphonate, a fatty acid diethanolamide, a mixed alkanolamine borate, a polysiobutenesuccinimide and a major proportion of mineral oil.
2. A soluble-oil as claimed in claim 1 comprising the following proportion of the components as percentages of the total weight of the soluble oil:-
Figure imgb0004
3. A soluble-oil as claimed in either claim 1 or claim 2 in which the alkali or alkaline-earth metal alkyl benzene sulphonate has a molecular weight of from 400 to 520, the alkali metal or alkaline-earth metal is selected from the group comprising sodium, potassium and calcium and the alkyl group is derived from polypropylene.
4. A soluble-oil as claimed in any of claims 1 to 3 in which the fatty acid diethanolamide is the reaction product of diethanolamine with a naturally occurring fatty acid having from 12 to 20 carbon atoms.
5. A soluble-oil as claimed in any of claims 1 to 4 in which the mixed alkanolamine borate is the reaction product of boric acid and at least two alkanolamines selected from the group comprising monoethanolamine, diethanolamine, triethanolamine and N,N dimethyl ethanolamine.
6. A soluble-oil as claimed in claim 5 in which the alkanolamines are mono- and di-ethanolamine.
7. A soluble-oil as claimed in any of claims 1 to 6 in which the polyisobutenesuccinimide is overbased with excess amine and has a molecular weight of from 1000 to 3000.
8. A soluble-oil as claimed in any of claims 1 to 7 which contains up to 2% of distilled water by weight of the total weight of the soluble-oil.
9. A soluble-oil as claimed in any of claims 1 to 8 which contains up to 0.05% of a defoaming agent by weight of the total weight of the soluble oil.
10. An emulsion, suitable for use as a cutting fluid comprising water and a soluble-oil as claimed in any of the preceding claims in a volumetric ratio of 10:1 to 40:1.
EP84301863A 1983-03-23 1984-03-20 Soluble oil cutting fluid Expired EP0120665B1 (en)

Priority Applications (1)

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AT84301863T ATE27174T1 (en) 1983-03-23 1984-03-20 CUTTING FLUID FOR SOLUBLE OIL.

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GB838307975A GB8307975D0 (en) 1983-03-23 1983-03-23 Soluble-oil cutting fluid
GB8307975 1983-03-23

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178177A2 (en) * 1984-10-11 1986-04-16 The British Petroleum Company p.l.c. Soluble-oil cutting fluid
WO1986003513A1 (en) * 1984-12-06 1986-06-19 The Lubrizol Corporation Corrosion-inhibiting compositions, and oil compositions containing said corrosion-inhibiting compositions
WO1993006198A1 (en) * 1991-09-16 1993-04-01 The Lubrizol Corporation Oil compositions
EP0609623A1 (en) * 1992-12-21 1994-08-10 Oronite Japan Limited Low phosphorous engine oil compositions and additive compositions
US5507962A (en) * 1993-05-18 1996-04-16 The United States Of America As Represented By The Secretary Of Commerce Method of fabricating articles
US5629272A (en) * 1991-08-09 1997-05-13 Oronite Japan Limited Low phosphorous engine oil compositions and additive compositions
EP2778216A1 (en) * 2011-05-27 2014-09-17 JX Nippon Oil & Energy Corporation Additive for lubricating oils and lubricating oil composition
US9029304B2 (en) 2008-09-30 2015-05-12 Chevron Oronite Company Llc Lubricating oil additive composition and method of making the same
CN109852461A (en) * 2019-03-18 2019-06-07 富莱德科技(浙江)有限公司 A kind of preparation method of Environmental Protection Cutting Fluid
US10414964B2 (en) 2015-06-30 2019-09-17 Exxonmobil Chemical Patents Inc. Lubricant compositions containing phosphates and/or phosphites and methods of making and using same
US10844264B2 (en) 2015-06-30 2020-11-24 Exxonmobil Chemical Patents Inc. Lubricant compositions comprising diol functional groups and methods of making and using same
EP4015603A1 (en) * 2020-12-21 2022-06-22 Kraton Polymers Research B.V. Metal-working fluid compositions and methods for making

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
CN113583157A (en) * 2021-07-26 2021-11-02 新乡市瑞丰新材料股份有限公司 Multifunctional high-boron-content boration dispersing agent and preparation method thereof

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US2999064A (en) * 1959-02-11 1961-09-05 Master Chemical Corp Stable aqueous cutting fluid
FR2130714A1 (en) * 1971-03-24 1972-11-03 Mobil Oil Corp
US4010107A (en) * 1976-02-02 1977-03-01 Chevron Research Company Corrosion-inhibiting functional fluid

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US2999064A (en) * 1959-02-11 1961-09-05 Master Chemical Corp Stable aqueous cutting fluid
FR2130714A1 (en) * 1971-03-24 1972-11-03 Mobil Oil Corp
US4010107A (en) * 1976-02-02 1977-03-01 Chevron Research Company Corrosion-inhibiting functional fluid

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178177A2 (en) * 1984-10-11 1986-04-16 The British Petroleum Company p.l.c. Soluble-oil cutting fluid
EP0178177A3 (en) * 1984-10-11 1986-12-30 The British Petroleum Company P.L.C. Soluble-oil cutting fluid
US4778614A (en) * 1984-10-11 1988-10-18 The British Petroleum Company P.L.C. Soluble-oil cutting fluid
WO1986003513A1 (en) * 1984-12-06 1986-06-19 The Lubrizol Corporation Corrosion-inhibiting compositions, and oil compositions containing said corrosion-inhibiting compositions
US4618539A (en) * 1984-12-06 1986-10-21 The Lubrizol Corporation Corrosion-inhibiting compositions, and oil compositions containing said corrosion-inhibiting compositions
JPS62500937A (en) * 1984-12-06 1987-04-16 ザ ル−ブリゾル コ−ポレイシヨン Anticorrosion composition and oil composition containing this anticorrosion composition
US5629272A (en) * 1991-08-09 1997-05-13 Oronite Japan Limited Low phosphorous engine oil compositions and additive compositions
AU661038B2 (en) * 1991-09-16 1995-07-13 Lubrizol Corporation, The Oil compositions
WO1993006198A1 (en) * 1991-09-16 1993-04-01 The Lubrizol Corporation Oil compositions
US5773393A (en) * 1991-09-16 1998-06-30 The Lubrizol Corporation Oil compositions useful in hydraulic fluids
EP0609623A1 (en) * 1992-12-21 1994-08-10 Oronite Japan Limited Low phosphorous engine oil compositions and additive compositions
US5507962A (en) * 1993-05-18 1996-04-16 The United States Of America As Represented By The Secretary Of Commerce Method of fabricating articles
US9029304B2 (en) 2008-09-30 2015-05-12 Chevron Oronite Company Llc Lubricating oil additive composition and method of making the same
JPWO2012165106A1 (en) * 2011-05-27 2015-02-23 Jx日鉱日石エネルギー株式会社 Lubricating oil additive and lubricating oil composition
EP2778216A4 (en) * 2011-05-27 2015-03-04 Jx Nippon Oil & Energy Corp Additive for lubricating oils and lubricating oil composition
EP2778216A1 (en) * 2011-05-27 2014-09-17 JX Nippon Oil & Energy Corporation Additive for lubricating oils and lubricating oil composition
US10414964B2 (en) 2015-06-30 2019-09-17 Exxonmobil Chemical Patents Inc. Lubricant compositions containing phosphates and/or phosphites and methods of making and using same
US10844264B2 (en) 2015-06-30 2020-11-24 Exxonmobil Chemical Patents Inc. Lubricant compositions comprising diol functional groups and methods of making and using same
CN109852461A (en) * 2019-03-18 2019-06-07 富莱德科技(浙江)有限公司 A kind of preparation method of Environmental Protection Cutting Fluid
CN109852461B (en) * 2019-03-18 2021-11-05 富莱德科技(浙江)有限公司 Preparation method of environment-friendly cutting fluid
EP4015603A1 (en) * 2020-12-21 2022-06-22 Kraton Polymers Research B.V. Metal-working fluid compositions and methods for making
US11525102B2 (en) 2020-12-21 2022-12-13 Kraton Polymers Llc Metal-working fluid compositions and methods for making

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ATE27174T1 (en) 1987-05-15
ZA842146B (en) 1985-11-27
DK163284D0 (en) 1984-03-22
AU558608B2 (en) 1987-02-05
GB8307975D0 (en) 1983-04-27
AU2586784A (en) 1984-09-27
DE3463673D1 (en) 1987-06-19
DK163284A (en) 1984-09-24
EP0120665B1 (en) 1987-05-13
EP0120665A3 (en) 1985-04-03
CA1223243A (en) 1987-06-23

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