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WO2024261017A1 - Composition lubrifiante biodégradable - Google Patents

Composition lubrifiante biodégradable Download PDF

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Publication number
WO2024261017A1
WO2024261017A1 PCT/EP2024/067024 EP2024067024W WO2024261017A1 WO 2024261017 A1 WO2024261017 A1 WO 2024261017A1 EP 2024067024 W EP2024067024 W EP 2024067024W WO 2024261017 A1 WO2024261017 A1 WO 2024261017A1
Authority
WO
WIPO (PCT)
Prior art keywords
lubricant composition
component
composition according
weight
biodegradable lubricant
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.)
Pending
Application number
PCT/EP2024/067024
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English (en)
Inventor
Angela SAGLIANO
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.)
Novamont SpA
Original Assignee
Novamont SpA
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 Novamont SpA filed Critical Novamont SpA
Publication of WO2024261017A1 publication Critical patent/WO2024261017A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids 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
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • 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
    • C10M2207/40—Fatty vegetable or animal 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended

Definitions

  • the present invention relates to a biodegradable lubricant composition
  • a biodegradable lubricant composition comprising at least one vegetable oil with a polyunsaturated fatty acid content from 30 to 70% by weight, at least one C5-C22 fatty acid ester with monoalcohols, and at least one surfactant belonging to the sorbitan class, which is particularly suitable for use as a penetrating lubricant.
  • Penetrating lubricants are products formulated from a range of base oils and chemical additives and are widely used to reduce friction and wear between metal surfaces in close contact. These lubricants are typically characterised by a high degree of penetration and impart wear and corrosion protection to the metal to which they are applied.
  • the main component of lubricants can be classified as mineral (of petroleum origin), or synthetic (for example polyalphaolefins, polyalkylene glycols, synthetic esters, silicones, etc.) or as biolubricants.
  • Mineral lubricants are a complex mixture of paraffinic (linear/branched), olefinic, naphthenic and aromatic hydrocarbons with 20 to 50 carbon atoms and are currently the most commonly used commercial lubricants.
  • mineral lubricants have poor renewability and biodegradability. If not handled properly, they can leak into the environment, for example through seepage, leakage or overflow, and cause severe environmental damage.
  • Synthetic lubricants have advantages over mineral lubricants in that they are more environmentally friendly, have a higher viscosity index, lower pour points and greater stability to oxidation. However, synthetic lubricants are more expensive and less effective than mineral lubricants.
  • Biolubricants typically produced from vegetable oils, are more expensive than mineral lubricants, but are nevertheless a promising alternative to mineral and synthetic lubricants. They possess good properties, such as a high viscosity index, good lubricity, superior anti-corrosive properties, high biodegradability and renewability, and low toxicity in water.
  • Document CN 102199480 describes a method of preparing a lubricant based on palm oil with a high saturated fatty acid content, chemically modified to increase its performance at low temperatures.
  • the document emphasises the need to use vegetable oils with a low unsaturated content, which cause poor stability to oxidation and a short service life for lubricants containing them.
  • Patent application WO 2003/106599 describes a penetrating lubricating oil based on vegetable oil blended with an organic solvent, an antioxidant, a wear inhibitor, an anti-corrosion agent and an emulsifier.
  • the document reiterates the need to reduce the polyunsaturated fatty acid content in vegetable oils, preferring oils with a high oleic acid content.
  • Document CN 102851006 describes a lubricating oil for drilling processes consisting of a base oil and a surfactant, where the base oil can be one of: biodiesel, a methyl ester of a fatty acid, a mixture of biodiesel and a mineral white oil, a mixture of a methyl ester of a fatty acid and a mineral white oil, a mixture of a mineral white oil and a vegetable oil.
  • the Applicant has now surprisingly found that the addition of at least one surfactant belonging to the class of sorbitans to a composition comprising at least one vegetable oil and at least one C5-C22 fatty acid ester with monoalcohols makes it possible to obtain a biodegradable lubricant that is stable to oxidation, has a high penetrating action and can provide excellent corrosion protection for different types of metal to which it is applied.
  • the Applicant has found that the use of vegetable oils with a polyunsaturated fatty acid content of more than 8% by weight and less than 80% by weight, preferably from 8 to 70% by weight, even more preferably from 30 to 70% by weight, allows greater protection from corrosion to be obtained for the metals to which the composition is applied.
  • the object of the present invention is therefore a biodegradable lubricant composition
  • a biodegradable lubricant composition comprising: a) at least one vegetable oil with a polyunsaturated fatty acid content from 30 to 70% by weight, b) at least one C5-C22 fatty acid ester with monoalcohols, c) at least one sorbitan ester with one or more C8-C18 fatty acids, in which the weight ratio between component a) and component b) varies from 5:95 to 60:40.
  • the present invention will be described in more detail below.
  • the composition according to the invention comprises at least one vegetable oil (component a)).
  • Vegetable oil is understood to be either the unmodified pressed product or an oil that has undergone chemical or physico/chemical modifications such as purification treatments or enzyme enrichment.
  • These vegetable oils are chosen from: soybean oil, sunflower oil, palm oil, coconut oil, Brassicaceae oil, maize oil, peanut oil, cottonseed oil, olive oil, safflower oil, thistle oil, castor oil, jojoba oil, Lesquerella oil, Jatropha oil, Cuphea oil, Limnanthaceae oil and mixtures thereof. Sunflower, safflower, thistle oils and their mixtures are preferred. Safflower, thistle oils and their mixtures are particularly preferred.
  • Oils with an unsaturated fatty acid content of more than 50% by weight, preferably more than 60% by weight are preferred.
  • Vegetable oils with a polyunsaturated fatty acid content of more than 8% by weight and less than 80% by weight, preferably from 8 to 70% by weight, even more preferably from 30 to 70% by weight, are preferred.
  • polyunsaturated fatty acids are fatty acids with 2 or 3 unsaturation, preferably 2.
  • compositions according to the invention surprisingly allows greater protection from corrosion to be obtained for the metals to which the composition is applied.
  • composition according to the invention comprises at least one C5-C22 fatty acid ester with mono-alcohols (component b)).
  • Said C5-C22 fatty acid ester with mono-alcohols preferably comprises or consists of a mixture of fatty acid methyl esters.
  • Said mixture preferably comprises 50 to 80% by weight of methyl oleate.
  • This mixture preferably also comprises 20 to 40% by weight of polyunsaturated fatty acid methyl esters.
  • the weight ratio between component a) and component b) is advantageously 5:95 to 60:40, preferably 10:90 to 50:50.
  • composition according to the invention comprises, with respect to the sum of components a)-c), 1-10% by weight, preferably at least 3% by weight, at least 4% by weight, at least 5% by weight, even more preferably 5 to 8% by weight, of at least one sorbitan ester with one or more C8-C18 fatty acids, preferably C12-C18 (component c)).
  • sorbitan monoesters Even more preferred are sorbitan monoesters with oleic acid.
  • composition according to the invention may comprise one or more additives chosen from: anti-oxidising agents, anti-wear agents, extreme pressure agents, corrosion inhibitors and deactivators of metals other than the sorbitan ester with one or more C8-C18 fatty acids (component c)), hydrolysis inhibitors, pour point depressants, viscosifying agents, detergents, dispersants, defoamers, emulsifiers or de-emulsifiers.
  • additives chosen from: anti-oxidising agents, anti-wear agents, extreme pressure agents, corrosion inhibitors and deactivators of metals other than the sorbitan ester with one or more C8-C18 fatty acids (component c)), hydrolysis inhibitors, pour point depressants, viscosifying agents, detergents, dispersants, defoamers, emulsifiers or de-emulsifiers.
  • antioxidant agent any type of antioxidant agent, anti-wear agent, extreme pressure agent, corrosion inhibitor and metal deactivator other than sorbitan ester with one or more C8-C18 fatty acids (component c)), hydrolysis inhibitor, pour point depressant, viscosifying agent, detergent, dispersant, antifoaming agent, emulsifier, demulsifier, commercially available from a variety of suppliers and manufacturers, can be used in the composition according to the invention.
  • Said additives may be added, individually or as a mixture, each in quantities of 0.01% to 10% by weight, more preferably 0.02% to 8% by weight, by weight of the lubricant composition.
  • antioxidant agents are sterically encumbered phenols that can be variously substituted, for example 2,6-di-t-butylphenol, 2,6-di-t-butyl-p-cresol and butylhydroxyanisole; t-butyl hydroquinone and all variously substituted derivatives with one or more functional groups; aromatic amines such as variously substituted diphenylamines, for example octylated and butylated diphenylamine, phenyl naphthylamines such as variously substituted alphanaphthylamine (PANA) and phenyl beta-naphthylamine (PBNA) metal alkylaryl dithiophosphates, such as variously substituted zinc dithiophosphate; metal dialkyldithiocarbamates, such as zinc and molybdenum dithiocarbamates; ashless dialkyldithiocarbamates such as alkylenebis(dialkyldithioc
  • anti-wear and extreme-pressure agents are olefins; vegetable oils; sulfur esters; chlorinated paraffins; metal alkylaryl-dithiophosphates, such as variously substituted zinc dithiophosphate; metal dialkyldithiocarbamates, such as zinc, antimony and molybdenum dithiocarbamates; ashless dialkyldithiocarbamates such as alkylene bis(dialkyldithiocarbamates) and similar phosphorothionates, such as butyltriphenyl phosphoro thionate; esters derived from dithiophosphoric acid in salt or acid form, such as dibutyl [[bis[(2-ethylhexyl)oxy]phosphinothio]thio] succinate, phosphate esters such as tricresyl phosphate or other esters of phosphoric acid and aliphatic alcohols whether or not neutralised with amines; variously substituted phosphite esters
  • Examples of corrosion inhibitors and metal deactivators other than the sorbitan ester with one or more C8-C18 fatty acids (component c)) are alkylsuccinic acid derivatives; ethoxylated phenols; fatty amines; fatty acid and amine salts; ethoxylated fatty acids and fatty alcohols; natural or synthetic waxes; variously substituted phosphate ester salts; variously substituted alkyl and alkylaryl metal or ammonium sulfonates, such as calcium salts of benzene sulfonic acid or variously substituted alkylnaphthalene sulfonic acid; polymeric sulfonate salts; amides and various derivatives such as sarcosine polycarboxylates; imidazoline derivatives; esterified amino acids; imidazoline derivatives; triazole derivatives; 2,5-dimercapto-l,3,4-thiadiazole derivatives; 4 fatty acid derivative
  • Hydrolysis inhibitors include, for example, monomeric and polymeric carbodiimides, or even glycidyl esters that act as acid scavengers.
  • pour point depressants are alkylated polystyrene or polyalkyl methacrylate.
  • viscosifiers are poly(alkyl methacrylates), olefin copolymers, styrene butadiene copolymers, complex esters or esters of high- viscosity polyols.
  • metal deactivators examples include benzotriazoles, 2-mercaptobenzothiazoles, variously substituted thiadiazoles and tolyl triazole derivatives.
  • detergents are phenates, alkyl, alkylaryl and naphthene sulfonates of barium, calcium and sodium, phosphate esters such as neutral or suprabasic long-chain alkylarylsulfonic acids, calcium and magnesium metal salts of alkylphenols and neutral or suprabasic alkyl sulfides, metal salts of alkyl salicylates, phosphates, thiophosphates and thiophosphonates obtained by the reaction of phosphorus pentasulfide with polyisobutenes (PIBs), olefins, fatty alcohols and esters neutralised after hydrolysis with metal hydroxide.
  • PIBs polyisobutenes
  • dispersants are polyisobutenyl succinimide, polyisobutenyl succinate ester, Mannich dispersants, olefin copolymers, polymethacrylates.
  • defoamers examples include oxirane polymers, poly siloxanes, polydimethylsiloxanes and acrylate polymers.
  • demulsifiers are polyalkoxylated phenols, polyalkoxy polyols, and poly alkoxy lated poly amines.
  • composition according to the invention advantageously imparts wear protection to the materials to which it is applied, which, when tested according to ASTM D4172, undergo wear of less than 0.5 mm.
  • composition according to the invention is resistant to extreme pressures exceeding 160 kgf (measured according to ASTM D2783).
  • the composition according to the invention advantageously protects metals to which it is applied from corrosion in corrosive acidic water for a period of more than 6 days.
  • metals are, for example, brass, copper, cast iron, soft iron, steel or aluminium.
  • the soft iron specimen showed no signs of oxidation after at least 15 days in corrosive water.
  • composition according to the invention applied for 3 hours to metals such as tin-plated steel, steel, aluminium, cast iron, brass and copper, protects them from corrosion when immersed in corrosive water for 7 days at 25°C.
  • metals such as tin-plated steel, steel, aluminium, cast iron, brass and copper.
  • the high oleic sunflower oil (HOSO)_used in comparative Example 1 had a polyunsaturated fatty acid content of 6.25%.
  • the thistle oil used in Examples 2 and 3 had a polyunsaturated fatty acid content of 59%. Protection against corrosion
  • Table 2 demonstrate that the composition according to the invention, applied to soft iron specimens subsequently placed in corrosive acidic water, protects the metal from corrosion for a period of at least 15 days. These results are comparable to those obtainable with a non-biodegradable reference product for this application. Furthermore, when thistle oil with a polyunsaturated fatty acid content higher than 30% by weight is used in the composition (Examples 2 and 3), the performance is definitely better than when using a sunflower oil with a high content of oleic acid (HOSO, Comparative Example 1)(.

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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)
  • Lubricants (AREA)

Abstract

La présente invention concerne une composition lubrifiante biodégradable comprenant au moins une huile végétale ayant une teneur en acides gras polyinsaturés de 30 à 70 % en poids, au moins un ester d'acides gras en C5-C22 avec des monoalcools, et au moins un tensioactif appartenant à la classe des sorbitanes, qui est particulièrement appropriée pour une utilisation en tant que lubrifiant pénétrant.
PCT/EP2024/067024 2023-06-20 2024-06-19 Composition lubrifiante biodégradable Pending WO2024261017A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102023000012645 2023-06-20
IT102023000012645A IT202300012645A1 (it) 2023-06-20 2023-06-20 Composizione lubrificante biodegradabile

Publications (1)

Publication Number Publication Date
WO2024261017A1 true WO2024261017A1 (fr) 2024-12-26

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Family Applications (1)

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PCT/EP2024/067024 Pending WO2024261017A1 (fr) 2023-06-20 2024-06-19 Composition lubrifiante biodégradable

Country Status (2)

Country Link
IT (1) IT202300012645A1 (fr)
WO (1) WO2024261017A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969233A (en) * 1971-10-12 1976-07-13 Lucas William J Biodegradable internal combustion engine lubricants and motor fuel compositions
US20030069146A1 (en) * 2001-07-13 2003-04-10 Renewable Lubricants, Inc. Biodegradable penetrating lubricant
CN102199480A (zh) 2010-03-24 2011-09-28 河南工业大学 棕榈液油制备润滑剂的方法
CN102851006A (zh) 2012-09-30 2013-01-02 中国石油集团西部钻探工程有限公司 钻井用生物油润滑剂及其制备方法
CN108315087A (zh) * 2017-12-25 2018-07-24 柳州智臻智能机械有限公司 一种机械润滑剂及其制备方法
EP3763805A1 (fr) * 2018-03-06 2021-01-13 Nippon Grease Co., Ltd. Composition de graisse
EP3916037A1 (fr) * 2019-01-21 2021-12-01 NOF Corporation Dérivé d'oxyde d'alkylène, agent antimousse, lubrifiant, matériau cosmétique de base et produits cosmétiques le contenant, composition d'agent de nettoyage capillaire et composition d'agent de nettoyage corporel

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969233A (en) * 1971-10-12 1976-07-13 Lucas William J Biodegradable internal combustion engine lubricants and motor fuel compositions
US20030069146A1 (en) * 2001-07-13 2003-04-10 Renewable Lubricants, Inc. Biodegradable penetrating lubricant
WO2003106599A1 (fr) 2002-06-12 2003-12-24 Renewable Lubricants, Inc. Lubrifiant de penetration biodegradable
CN102199480A (zh) 2010-03-24 2011-09-28 河南工业大学 棕榈液油制备润滑剂的方法
CN102851006A (zh) 2012-09-30 2013-01-02 中国石油集团西部钻探工程有限公司 钻井用生物油润滑剂及其制备方法
CN108315087A (zh) * 2017-12-25 2018-07-24 柳州智臻智能机械有限公司 一种机械润滑剂及其制备方法
EP3763805A1 (fr) * 2018-03-06 2021-01-13 Nippon Grease Co., Ltd. Composition de graisse
EP3916037A1 (fr) * 2019-01-21 2021-12-01 NOF Corporation Dérivé d'oxyde d'alkylène, agent antimousse, lubrifiant, matériau cosmétique de base et produits cosmétiques le contenant, composition d'agent de nettoyage capillaire et composition d'agent de nettoyage corporel

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