Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
  • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
  • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C67/00—Preparation of carboxylic acid esters
  • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C67/00—Preparation of carboxylic acid esters
  • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
  • C07C69/604—Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1981—Condensation polymers of aldehydes or ketones
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  • 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
  • C10M129/72—Esters of polycarboxylic acids
• • 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
  • 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
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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
  • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
  • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
  • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/0005—Other compounding ingredients characterised by their effect
  • C11D3/0073—Anticorrosion compositions
• • C—CHEMISTRY; METALLURGY
  • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
  • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
  • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
  • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
  • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
  • C23F11/12—Oxygen-containing compounds
  • C23F11/128—Esters of carboxylic acids
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1625—Hydrocarbons macromolecular compounds
  • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
  • C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
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  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/1802—Organic compounds containing oxygen natural products, e.g. waxes, extracts, fatty oils
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1983—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyesters
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
  • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0415—Light distillates, e.g. LPG, naphtha
  • C10L2200/0423—Gasoline
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  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
  • C10L2200/0446—Diesel
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  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0461—Fractions defined by their origin
  • C10L2200/0469—Renewables or materials of biological origin
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  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0461—Fractions defined by their origin
  • C10L2200/0469—Renewables or materials of biological origin
  • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
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  • C10L2200/00—Components of fuel compositions
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  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/40—Fatty vegetable or animal oils
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
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  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/64—Environmental friendly compositions
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Definitions

• This invention relates newly developed multifunctional environmentally friendly macromolecular corrosion inhibitors utilize mainly the renewable and biobased raw material source. Most of the current corrosion inhibitors used in the industrial applications are not necessarily environmentally friendly and are based on petroleum based chemicals involving organic and inorganic species.
• This invention is directed to multifunctional macromolecular corrosion inhibitors and to fluid compositions containing minor amounts thereof.
• Multifunctional properties of this inhibitor include but not limited to rust inhibition, copper corrosion inhibition, and water and oil separating (demulsifier) capabilities.
• Fluids include but not limited to lubricants, biolubricants, bio-oils, bio-based oils, synthetic lubricants, fuels, bio-fuel, greases, bio-greases, aviation fuels, kerosene, gasoline, diesel, biodiesel, adhesives, and paints etc.
• Corrosion in general terms is the degradation of a material caused by an aggressive environment such as water, air (oxygen), chemicals (acids, bases), organic liquids, oil, and gas, etc.
• Materials subject to corrosion include metals and their alloys, plastics, paints and coatings, concrete, or composites. Corrosion is a major concern in the durability of these materials, impacting safety, causing environmental damage, and incurring enormous repair and replacement costs. This is a major national concern. According to one United States federal government study in 2002, the total estimated cost of corrosion is a staggering $276 billion (approximately 3.1% of GDP) (Report FHWA-RD-01-156).
• Corrosion inhibitors are typically added or treated (0.001% to 5%) to the corroding materials (metals, lubricants, fuels, plastics, oils and gas, adhesives, greases, paints and coating materials, cement, water reservoir, etc.) to protect against the corrosion from the surrounding environments like fluid, water, oxygen, moisture, weather, temperature, or their combinations, etc.
• corroding materials metal, lubricants, fuels, plastics, oils and gas, adhesives, greases, paints and coating materials, cement, water reservoir, etc.
• Corrosion inhibitors are added to fluids based on petroleum, synthetic and/or bio-oils, bio-based oils like lubricants, greases, adhesives, and fuels; and paints and coating 55 materials.
• the present invention is a new material composition technology, Macromolecular Corrosion Inhibitors (McIn), described herein. McIn is envisioned as a disruptive technology that adds value to the supply chains of multiple market sectors.
• This invention is essentially directed to macromolecular corrosion inhibitors that are
• the present invention pertains to a compound represented by structural formula I and IA:
• an element means one element or more than one element.
• polymer is art-recognized and refers to a macromolecule comprising a repeating monomeric unit.
• the number of repeat units may vary as low as 2 and as high as million. In the present invention this number may vary from 2 to about 10,000, or less than 1,000, or less than about 100, or even less than about 10.
• the term “monomer” is art-recognized and refers to a compound that is able to combine in long chains with other like or unlike molecules to produce.
• “Small molecule” is an art-recognized term. In certain embodiments, this term refers to a molecule which has a molecular weight of less than about 2000 amu, or less than about 1000 amu, and even less than about 200 amu.
• aliphatic is an art-recognized term and includes linear, branched, and cyclic alkanes, alkenes, or alkynes.
• aliphatic groups in the present invention are linear or branched and have from 1 to about 30 carbon atoms.
• alkyl is art-recognized and includes saturated aliphatic groups, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl substituted cycloalkyl groups, and cycloalkyl substituted alkyl groups.
• a straight chain or branched chain alkyl has about 30 or fewer carbon atoms in its backbone (e.g., C 1 -C 30 for straight chain, C 3 -C 30 for branched chain), and alternatively, about 20 or fewer.
• cycloalkyls have from about 3 to about 10 carbon atoms in their ring structure, and alternatively about 5, 6 or 7 carbons in the ring structure.
• alkyl is also defined to include halosubstituted alkyls.
• aralkyl is art-recognized, and includes alkyl groups substituted with an aryl group (e.g., an aromatic or heteroaromatic group).
• alkenyl and alkynyl are art-recognized, and include unsaturated aliphatic groups analogous in length and possible substitution to the alkyls described above, but that contain at least one double or triple bond respectively.
• lower alkyl refers to an alkyl group, as defined above, but having from one to ten carbons, alternatively from one to about six carbon atoms in its backbone structure. Likewise, “lower alkenyl” and “lower alkynyl” have similar chain lengths.
• heteroatom means nitrogen, oxygen, or sulfur and includes any oxidized form of nitrogen and sulfur and the quaternized form of any basic nitrogen.
• nitrogen includes substitutable nitrogen of a heteroaryl or non-aromatic heterocyclic group.
• the nitrogen in a saturated or partially unsaturated ring having 0-3 heteroatoms selected from oxygen, sulfur or nitrogen, the nitrogen may be N (as in 3,4-dihydro-2H-pyrrolyl), NH (as in pyrrolidinyl) or NR′′ (as in N-substituted pyrrolidinyl), wherein R′′ is a suitable substituent for the nitrogen atom in the ring of a non-aromatic nitrogen-containing heterocyclic group.
• aryl is art-recognized, and includes 5-, 6- and 7-membered single-ring aromatic groups that may include from zero to four heteroatoms, for example, benzene, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, pyridazine and pyrimidine, and the like.
• aryl groups having heteroatoms in the ring structure may also be referred to as “aryl heterocycles” “heteroaryls,” or “heteroaromatics.”
• the aromatic ring may be substituted at one or more ring positions with such substituents as described above, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, sulfonamido, ketone, aldehyde, ester, heterocyclyl, aromatic or heteroaromatic moieties, —CF 3 , —CN, or the like.
• aryl also includes polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjoining rings (the rings are “fused rings”) wherein at least one of the rings is aromatic, e.g., the other cyclic rings may be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or heterocyclyls.
• ortho, meta and para are art-recognized and apply to 1, 2-, 1, 3- and 1, 4-disubstituted benzenes, respectively.
• the names 1, 2-dimethylbenzene and ortho-dimethylbenzene are synonymous.
• heterocyclyl and “heterocyclic group” are art-recognized, and include 3- to about 10-membered ring structures, such as 3- to about 7-membered rings, whose ring structures include one to four heteroatoms. Heterocycles may also be polycycles.
• Heterocyclyl groups include, for example, thiophene, thianthrene, furan, pyran, isobenzofuran, chromene, xanthene, phenoxathiin, pyrrole, imidazole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indolizine, isoindole, indole, indazole, purine, quinolizine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, carboline, phenanthridine, acridine, pyrimidine, phenanthroline, phenazine, phenarsazine, phenothiazine, furazan, phenoxazine, pyrrolidine, o
• the heterocyclic ring may be substituted at one or more positions with such substituents as described above, as for example, halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, —CF 3 , —CN, or the like.
• substituents as described above, as for example, halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxy
• polycyclyl and “polycyclic group” are art-recognized, and include structures with two or more rings (e.g., cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or heterocyclyls) in which two or more carbons are common to two adjoining rings, e.g., the rings are “fused rings”. Rings that are joined through non-adjacent atoms, e.g., three or more atoms are common to both rings, are termed “bridged” rings.
• rings e.g., cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or heterocyclyls
• Each of the rings of the polycycle may be substituted with such substituents as described above, as for example, halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, —CF 3 , —CN, or the like.
• substituents as described above, as for example, halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, si
• Carbocycle is art recognized and includes an aromatic or non-aromatic ring in which each atom of the ring is carbon.
• nitro means —NO 2
• halogen designates —F, —Cl, —Br or —I
• sulfhydryl means —SH
• hydroxyl means —OH
• sulfonyl means —SO 2 ⁇ .
• amine and “amino” are art-recognized and include both unsubstituted and substituted amines, e.g., a moiety that may be represented by the general formulas:
• R50, R51 and R52 each independently represent a hydrogen, an alkyl, an alkenyl, —(CH 2 ) m —R61, or R50 and R51, taken together with the N atom to which they are attached complete a heterocycle having from 4 to 8 atoms in the ring structure;
• R61 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle or a polycycle; and
• m is zero or an integer in the range of 1 to 8.
• only one of R50 or R51 may be a carbonyl, e.g., R50, R51 and the nitrogen together do not form an imide.
• R50 and R51 each independently represent a hydrogen, an alkyl, an alkenyl, or —(CH 2 ) m —R61.
• alkylamine includes an amine group, as defined above, having a substituted or unsubstituted alkyl attached thereto, i.e., at least one of R50 and R51 is an alkyl group.
• acylamino is art-recognized and includes a moiety that may be represented by the general formula:
• R50 is as defined above
• R54 represents a hydrogen, an alkyl, an alkenyl or —(CH 2 ) m —R61, where m and R61 are as defined above.
• amino is art recognized as an amino-substituted carbonyl and includes a moiety that may be represented by the general formula:
• alkylthio is art recognized and includes an alkyl group, as defined above, having a sulfur radical attached thereto.
• the “alkylthio” moiety is represented by one of —S-alkyl, —S-alkenyl, —S-alkynyl, and —S—(CH 2 ) m —R61, wherein m and R61 are defined above.
• Representative alkylthio groups include methylthio, ethyl thio, and the like.
• carbonyl is art recognized and includes such moieties as may be represented by the general formulas:
• X50 is a bond or represents an oxygen or a sulfur
• R55 represents a hydrogen, an alkyl, an alkenyl, —(CH 2 ) m —R61 or a pharmaceutically acceptable salt
• R56 represents a hydrogen, an alkyl, an alkenyl or —(CH 2 ) m —R61, where m and R61 are defined above.
• X50 is oxygen and R55 or R56 is not hydrogen
• the formula represents an “ester”.
• X50 is oxygen, and R55 is as defined above, the moiety is referred to herein as a carboxyl group, and particularly when R55 is hydrogen, the formula represents a “carboxylic acid”.
• X50 is an oxygen, and R56 is hydrogen
• the formula represents a “formate”.
• the oxygen atom of the above formula is replaced by sulfur
• the formula represents a “thiocarbonyl” group.
• X50 is a sulfur and R55 or R56 is not hydrogen
• the formula represents a “thioester.”
• X50 is a sulfur and R55 is hydrogen
• the formula represents a “thiocarboxylic acid.”
• X50 is a sulfur and R56 is hydrogen
• the formula represents a “thioformate.”
• X50 is a bond, and R55 is not hydrogen
• the above formula represents a “ketone” group.
• X50 is a bond, and R55 is hydrogen
• the above formula represents an “aldehyde” group.
• alkoxyl or “alkoxy” are art recognized and include an alkyl group, as defined above, having an oxygen radical attached thereto. Representative alkoxyl groups include methoxy, ethoxy, propyloxy, tert-butoxy and the like.
• An “ether” is two hydrocarbons covalently linked by an oxygen. Accordingly, the substituent of an alkyl that renders that alkyl an ether is or resembles an alkoxyl, such as may be represented by one of —O-alkyl, —O-alkenyl, —O-alkynyl, —O—(CH 2 ) m —R61, where m and R61 are described above.
• R57 is an electron pair, hydrogen, alkyl, cycloalkyl, or aryl.
• R57 is as defined above.
• R58 is one of the following: hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl.
• R60 represents a lower alkyl or an aryl.
• non-aromatic carbocyclic ring as used alone or as part of a larger moiety refers to a non-aromatic carbon containing ring which can be saturated or unsaturated having three to fourteen atoms including monocyclic and polycyclic rings in which the carbocyclic ring can be fused to one or more non-aromatic carbocyclic or heterocyclic rings or one or more aromatic (carbocyclic or heterocyclic) rings.
• An optionally substituted aryl group as defined herein may contain one or more substitutable ring atoms, such as carbon or nitrogen ring atoms.
• suitable substituents on a substitutable ring carbon atom of an aryl group include halogen (e.g., —Br, Cl, I and F), —OH, C1-C4 alkyl, C1-C4 haloalkyl, —NO 2 , C1-C4 alkoxy, C1-C4 haloalkoxy, —CN, —NH 2 , C1-C4 alkylamino, C1-C4 dialkylamino, —C(O)NH 2 , —C(O)NH(C1-C4 alkyl), —C(O)(C1-C4 alkyl), —OC(O)(C1-C4 alkyl), —OC(O)(aryl), —OC(O)(substituted aryl), —OC(O
• substituents on a substitutable ring nitrogen atom of an aryl group include C1-C4 alkyl, NH 2 , C1-C4 alkylamino, C1-C4 dialkylamino, —C(O)NH 2 , —C(O)NH(C1-C4 alkyl), —C(O)(C1-C4 alkyl), —CO 2 R**, —C(O)C(O)R**, —C(O)CH 3 , —C(O)OH, —C(O)O—(C1-C4 alkyl), —SO 2 NH 2 —SO 2 NH(C1-C3 alkyl), —SO 2 N(C1-C3 alkyl) 2 , NHSO 2 H, NHSO 2 (C1-C4 alkyl), —C( ⁇ S)NH 2 , —C( ⁇ S)NH(C1-C4 alkyl), —C( ⁇ S)N(
• An optionally substituted alkyl group or non-aromatic carbocyclic or heterocyclic group as defined herein may contain one or more substituents.
• suitable substituents for an alkyl group include those listed above for a substitutable carbon of an aryl and the following: ⁇ O, ⁇ S, ⁇ NNHR**, ⁇ NN(R**) 2 , ⁇ NNHC(O)R**, ⁇ NNHCO 2 (alkyl), ⁇ NNHSO 2 (alkyl), ⁇ NR**, spiro cycloalkyl group or fused cycloalkyl group.
• R** in each occurrence independently is —H or C1-C6 alkyl.
• Preferred substituents on alkyl groups are as defined throughout the specification. In certain embodiments optionally substituted alkyl groups are unsubstituted.
• a “spiro cycloalkyl” group is a cycloalkyl group which shares one ring carbon atom with a carbon atom in an alkylene group or alkyl group, wherein the carbon atom being shared in the alkyl group is not a terminal carbon atom.
• Analogous substitutions may be made to alkenyl and alkynyl groups to produce, for example, aminoalkenyls, aminoalkynyls, amidoalkenyls, amidoalkynyls, iminoalkenyls, iminoalkynyls, thioalkenyls, thioalkynyls, carbonyl-substituted alkenyls or alkynyls.
• selenoalkyl is art recognized and includes an alkyl group having a substituted seleno group attached thereto.
• exemplary “selenoethers” which may be substituted on the alkyl are selected from one of —Se-alkyl, —Se-alkenyl, —Se-alkynyl, and —Se—(CH 2 ) m —R61, m, and R61 are defined above.
• triflyl, tosyl, mesyl, and nonaflyl are art-recognized and refer to trifluoromethanesulfonyl, p-toluenesulfonyl, methanesulfonyl, and nonafluorobutanesulfonyl groups, respectively.
• triflate, tosylate, mesylate, and nonaflate are art-recognized and refer to a trifluoromethanesulfonate ester, p-toluenesulfonate ester, methanesulfonate ester, and nonafluorobutanesulfonate ester functional groups and molecules that contain said groups, respectively.
• Me, Et, Ph, Tf, Nf, Ts, and Ms are art recognized and represent methyl, ethyl, phenyl, trifluoromethanesulfonyl, nonafluorobutanesulfonyl, p-toluenesulfonyl and methanesulfonyl, respectively.
• a more comprehensive list of the abbreviations utilized by organic chemists of ordinary skill in the art appears in the first issue of each volume of the Journal of Organic Chemistry ; this list is typically presented in a table entitled Standard List of Abbreviations.
• OSA is for octenyl succinic anhydride
• DDSA is for dodecenyl succinic anhydride
• ODSA is for octadecenyl succinic anhydride
• PIBSA is for polyisobutylene succinic anhydride preferably with low molecular weights (300-1500 molecular weight)
• OASA is for oleic acid succinic anhydride.
• an isomer is understood a molecule with the same molecular formula as another molecule, but with a different chemical structure. Isomers contain the same number of atoms of each element but have different arrangements of their atoms. Isomers do not necessarily share similar properties unless they also have the same functional groups. In structural isomers, sometimes referred to as constitutional isomers, the atoms, and functional groups are joined together in different ways.
• compositions of the present invention may exist in particular geometric or stereoisomeric forms.
• compositions of the present invention may also be optically active.
• the present invention contemplates all such compounds, including cis- and trans-isomers, R- and S-enantiomers, diastereomers, (D)-isomers, (L)-isomers, the racemic mixtures thereof, and other mixtures thereof, as falling within the scope of the invention.
• Additional asymmetric carbon atoms may be present in a substituent such as an alkyl group. All such isomers, as well as mixtures thereof, are intended to be included in this invention.
• a particular enantiomer of a compound of the present invention may be prepared by asymmetric synthesis, or by derivation with a chiral auxiliary, where the resulting diastereomeric mixture is separated and the auxiliary group cleaved to provide the pure desired enantiomers.
• the molecule contains a basic functional group, such as amino, or an acidic functional group, such as carboxyl, diastereomeric salts are formed with an appropriate optically active acid or base, followed by resolution of the diastereomers thus formed by fractional crystallization or chromatographic means well known in the art, and subsequent recovery of the pure enantiomers.
• substitution or “substituted with” includes the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g., which does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, or other reaction.
• substituted is also contemplated to include all permissible substituents of organic compounds.
• the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds.
• Illustrative substituents include, for example, those described herein above.
• the permissible substituents may be one or more and the same or different for appropriate organic compounds.
• the heteroatoms such as nitrogen may have hydrogen substituents and/or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatoms. This invention is not intended to be limited in any manner by the permissible substituents of organic compounds.
• hydrocarbon is art recognized and includes all permissible compounds having at least one hydrogen and one carbon atom.
• permissible hydrocarbons include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic organic compounds that may be substituted or unsubstituted.
• protecting group is art recognized and includes temporary substituents that protect a potentially reactive functional group from undesired chemical transformations.
• Examples of such protecting groups include esters of carboxylic acids, silyl ethers of alcohols, and acetals and ketals of aldehydes and ketones, respectively.
• the field of protecting group chemistry has been reviewed. Greene et al., Protective Groups in Organic Synthesis 2 nd ed., Wiley, New York, (1991).
• hydroxyl-protecting group is art recognized and includes those groups intended to protect a hydroxyl group against undesirable reactions during synthetic procedures and includes, for example, benzyl or other suitable esters or ethers groups known in the art.
• electron-withdrawing group is recognized in the art and denotes the tendency of a substituent to attract valence electrons from neighboring atoms, i.e., the substituent is electronegative with respect to neighboring atoms.
• ⁇ Hammett sigma
• Exemplary electron-withdrawing groups include nitro, acyl, formyl, sulfonyl, trifluoromethyl, cyano, chloride, and the like.
• Exemplary electron-donating groups include amino, methoxy, and the like.
• Contemplated equivalents of the or oligomers, subunits and other compositions described above include such materials which otherwise correspond thereto, and which have the same general properties thereof, wherein one or more simple variations of substituents are made which do not adversely affect the efficacy of such molecule to achieve its intended purpose of the present invention.
• the methods of the present invention may be methods illustrated in the general reaction schemes as, for example, described below, or by modifications thereof, using readily available starting materials, reagents and conventional synthesis procedures. In these reactions, it is also possible to make use of variants which are in themselves known but are not mentioned here.
• the present invention pertains to a compound represented by structural formula I:
• the present invention addresses that relate to a compound represented by structural formula II derived from Structural Formula I.
• Each R 1 is H, independently an optionally substituted C 1 -C 20 linear or branched alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, and an optionally substituted C 1 -C 20 linear or branched alkoxy group, an optionally substituted carbonyl group, an optionally substituted C 1 -C 20 linear or branched alkoxycarbonyl group, an optionally-CH(R′′′)(R′′′COOH) wherein each R′′′ independently is C 1 -C 10 linear or branched alkyl chain, —OH, —SH or —NH 2 or an optionally substituted carbocyclic or heterocyclic C 1 -C 12 non-aromatic ring.
• Each R 2 , R 3 , R 4 independently is H, methyl, or a C 1 -C 24 linear or branched or cyclic alkyl chain.
• Each R 2 , R 3 , R 4 is H, independently an optionally substituted C 1 -C 24 alkyl group, an optionally substituted C 1 -C 10 alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, and optionally substituted C 1 -C 20 alkoxy group, an optionally substituted C 1 -C 20 carbonyl group, an optionally substituted C 1 -C 20 alkoxycarbonyl group, an optionally-CH(R′′′)(R′′′COOH) wherein each R′′′ independently C 1 -C 10 linear or branched alkyl chain, —OH, —SH or —NH 2 or an optionally substituted carbocyclic or heterocyclic C 1 -C 12 non-aromatic ring.
• R is a C 1 -C 24 linear or branched alkyl chain, C 1 -C 24 alkenyl chain or
• R a is a C 1 -C 24 alkenyl linear or branched chain.
• each R 2 , R 3 is independently an optionally a methyl group or H; independently an optionally a C 1 -C 8 linear, branched, a cyclic alkyl group or H.
• R is a linear or branched C 1 -C 26 alkyl chain
• Each R 1 is H, independently an optionally substituted C 1 -C 20 linear or branched alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, and an optionally substituted C 1 -C 20 linear or branched alkoxy group, an optionally substituted carbonyl group, an optionally substituted C 1 -C 20 linear or branched alkoxycarbonyl group, an optionally-CH(R′′′)(R′′′COOH) wherein each R′′′ independently is C 1 -C 10 linear or branched alkyl chain, —OH, —SH or —NH 2 or an optionally substituted carbocyclic or heterocyclic C 1 -C 12 non-aromatic ring, and i is 0, 1, 2 or 3, n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25,
• R is a saturated fatty acid derived from natural resources like plants, vegetable oils or animal fats.
• R is a saturated fatty acid, caprylic acid (8:0), capric acid (10:0), lauric acid (12:0), myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0), behenic acid (22:0), lignoceric acid (24:0), or cerotic acid(26:0).
• R is a mixture of saturated alkyl chains of saturated fatty acids derived natural resources like plants, vegetable oils or animal fat.
• the present invention is a compound of structural formula (III) where R 1 independently for each occurrence is selected from the group consisting of
• the present invention is a compound of structural formula (III) where R is represented by
• the present invention is a compound of structural formula (III) where R is a C 1 -C 26 linear or branched alkyl chain or a mixture of C 8 -C 24 linear or branched alkyl chains, i is an integer from 0 to 3, and R 1 independently for each occurrence is selected from the group consisting of
• n is an integer from 0 to 100 or 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10
• R is a C 1 -C 26 linear or branched alkyl chain or an alkyl chain of saturated fatty acids derived from renewable resources like plant oils like Jatropha, vegetable oils like canola oil, palm oil, vegetable oils like canola, rapeseed oil, soy oil, palms oil, and alike, and animal fats like tallow oil.
• the saturated fatty acids are, caprylic acid (8:0), capric acid (10:0), lauric acid (12:0), myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0), behenic acid (22:0), lignoceric acid (24:0), or cerotic acid(26:0).
• Each R 1 is H, independently an optionally substituted C 1 -C 20 linear or branched alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, and an optionally substituted C 1 -C 20 linear or branched alkoxy group, an optionally substituted carbonyl group, an optionally substituted C 1 -C 20 linear or branched alkoxycarbonyl group, an optionally-CH(R′′′)(R′′′COOH) wherein each R′′′ independently is C 1 -C 10 linear or branched alkyl chain, —OH, —SH or —NH 2 or an optionally substituted carbocyclic or heterocyclic C 1 -C 12 non-aromatic ring.
• n is an integer from 0 to 100 or 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10.
• the present invention is a compound or a mixture of compounds represented by Structural formula III, IV or IVa wherein the compound is the composition of that are the reaction products of a substituted phenol and an aldehyde which are esterified further with a linear or branched alkyl alcohol containing a C 1 -C 50 linear or branched alkyl chain or a mixture of C 1 -C 50 linear or branched alkyl chains or preferably linear C 1 -C 26 linear or branched alkyl chain or a mixture of linear or branched C 1 -C 26 alkyl chains or more preferably C 12 -C 18 lineal alkyl chain or a mixture of C 12 -C 18 alkyl chains.
• R is a C 1 -C 26 linear or branched alkyl chain or a mixture of C 8 -C 24 alkyl chains, i is an integer from >1 but ⁇ 3, and each R 1 independently is selected from the group consisting of
• the present invention is a compound or a mixture of compounds represented by structural formulas VI:
• R is a C 1 -C 26 linear or branched alkyl chain or a saturated fatty acid or mixture of saturated fatty acids derived from renewable resources like plant oils like Jatropha, vegetable oils like canola oil, palm oil, vegetable oils like canola, rapeseed oil, soy oil, palms oil, and alike, and animal fats like tallow oil.
• the saturated fatty acids are, caprylic acid (8:0), capric acid (10:0), lauric acid (12:0), myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0), behenic acid (22:0), lignoceric acid (24:0), or cerotic acid(26:0).
• R is a C 1 -C 26 linear or branched alkyl chain or a saturated fatty acid or saturated fatty acids derived from renewable resources like plant oils like Jatropha, vegetable oils like canola oil, palm oil, vegetable oils like canola, rapeseed oil, soy oil, palms oil, and alike, and animal fats like tallow oil.
• the saturated fatty acids are, caprylic acid (8:0), capric acid (10:0), lauric acid (12:0), myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0), behenic acid (22:0), lignoceric acid (24:0), or cerotic acid(26:0), and the remaining variables are as described in the immediately preceding paragraph or for structural formula (I), (II) or (III).
• R is an alkenyl isomer represented by
• R d is H or a C 1 -C 18 linear or branched alkyl chain, —[CH 2 ] p —CH 3 with p being an integer from 0 to 30.
• p is from 3 to 25
• p is 7 to 17
• p is from to 17, in some instances p from 13-15
• p is from 15 to 17, in some instances p is 0, 7, 9, 11, 13, 15, or 17 or a mixture thereof.
• Each R 1 is H, independently an optionally substituted C 1 -C 20 linear or branched alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, and an optionally substituted C 1 -C 20 linear or branched alkoxy group, an optionally substituted carbonyl group, an optionally substituted C 1 -C 20 linear or branched alkoxycarbonyl group, an optionally-CH(R′′′)(R′′′COOH) wherein each R′′′ independently is C 1 -C 10 linear or branched alkyl chain, —OH, —SH or —NH 2 or an optionally substituted carbocyclic or heterocyclic C 1 -C 12 non-aromatic ring.
• the present invention is a compound of structural formula (VII) where R 1 is an isomerized structure represented by
• R d is H or C 1 -C 18 linear or branched alkyl chains, —[CH 2 ] p —CH 3 with p being an integer from 0 to 30.
• p is from 3 to 25
• p is 7 to 17
• p is from to 17, in some instances p from 13-15
• p is from 15 to 17, in some instances p is 0, 7, 9, 11, 13, 15, or 17 or a mixture thereof.
• Each R 1 is H, independently an optionally substituted C 1 -C 20 alkyl group, a tertiary carbon group, a methyl group, a methoxy group, an optionally substituted aryl group, and optionally substituted C 1 -C 20 alkoxy group, an optionally substituted carbonyl group, an optionally substituted C 1 -C 20 alkoxycarbonyl group, an optionally-CH(R′′′)(R′′′COOH) wherein each R′′′ independently is C 1 -C 10 linear or branched alkyl chain, —OH, —SH or —NH 2 or an optionally substituted carbocyclic or heterocyclic C 1 -C 12 non-aromatic ring;
• i 0 or 1 or 2 or 3;
• the present invention is a compound of structural formula VIII where R 1 is selected from the group consisting of
• proviso substituted phenol is not a phenol, 2,4-dimethylphenol or resorcinol if R is arising from DDSA (dodecenyl succinic anhydride), ODSA (octadecenyl succinic anhydride), OSA (octenyl succinic anhydride), or PIBSA (polyisobutylene succinic anhydride).
• DDSA dodecenyl succinic anhydride
• ODSA octadecenyl succinic anhydride
• OSA octenyl succinic anhydride
• PIBSA polyisobutylene succinic anhydride
• the present invention is a compound of structural formula (VIII) where R 1 is an isomerized structure represented by
• in yet another embodiment of the present invention is a compound or a mixture of compounds represented by structural formulas VIII where is R is an alkenyl portion of [monosaturated fatty acid succinic anhydride] isomers when their anhydride rings are opened by a saturated fatty alcohol selected from the chain lengths ranging from C 8 to C 26 .
• the preferred monosaturated fatty acid-succinic anhydride is an oleic acid-succinic anhydride (OASA).
• OASA oleic acid-succinic anhydride
• R is an alkenyl portion of [monosaturated fatty acid-succinic anhydride] isomers when their anhydride rings are opened by a fatty alcohol selected from the chain lengths ranging from C 8 to C 26 .
• the preferred monosaturated fatty acid-succinic anhydride compound is oleic acid-succinic anhydride (OASA) and the fatty acid alcohol is stearyl alcohol (CH 3 (CH 2 ) 17 OH).
• OASA oleic acid-succinic anhydride
• the isomer structures of OASA after reacting with a fatty alcohol, R d —OH are:
• R d is H or C 1 -C 18 linear or branched alkyl chains, —[CH 2 ] p —CH 3 with p being an integer from 0 to 30.
• p is from 3 to 25
• p is 7 to 17
• p is from 11 to 17, in some instances p from 13-15
• p is from 15 to 17, in some instances p is 0, 7, 9, 11, 13, 15, or 17 or a mixture thereof.
• the present invention is a compound or a mixture of compounds represented by structural formulas IX:
• R is an alkenyl structural isomer represented by
• R d is H or C 1 -C 18 linear or branched alkyl chains, —[CH 2 ] p —CH 3 with p being an integer from 0 to 30.
• p is from 3 to 25
• p is 7 to 17
• p is from to 17, in some instances p from 13-15
• p is from 15 to 17, in some instances p is 0, 7, 9, 11, 13, 15, or 17 or a mixture thereof.
• the present invention is a compound or a mixture of compounds represented by structural formulas X:
• R is an alkenyl structural isomer represented by
• R d is H or C 1 -C 18 linear or branched alkyl chains, —[CH 2 ] p —CH 3 with p being an integer from 0 to 30.
• p is from 3 to 25
• p is 7 to 17
• p is from 11 to 17, in some instances p from 13-15
• p is from 15 to 17, in some instances p is 0, 7, 9, 11, 13, 15, or 17 or a mixture thereof.
• the present invention relates to a compound represented by structural formula XI (a mixture of structural isomers):
• R is a C 1 -C 18 linear or branched alkyl chain, or an alkenyl chain of PIBSA, OSA, DDSA, and ODSA, and the remaining variables are as described for structural formula (I), (II) or (III).
• the present invention is a compound or a mixture of compounds represented by Structural formula XI wherein the polymers that are the reaction products of a substituted phenol and an aldehyde which is further esterified with PIBSA, DDSA, ODSA, or OSA.
• the present invention is a compound of isomerized structural formula (XI) where R 1 is represented by
• the present invention is a compound represented by structural formulas XII with optionally their corresponding structural isomer or mixture of structural isomers:
• OSA′, DDSA′, ODSA′, PIBSA′ are alkenyl chain portion of OSA, octenyl succinic anhydride; DDSA, dodecenyl succinic anhydride; ODSA, octadecenyl succinic anhydride; PIBSA, polyisobutylene succinic anhydride (low molecular weight, 300-1500 molecular weight), respectively; each R 2 , R 3 is independently an optionally a methyl group or H; independently an optionally a C 1 -C 8 linear, branched, a cyclic alkyl group, the remaining variables are as described for structural formula (I), (II) or (III).
• the present invention is a compound of structural formula (XII) where R 1 is represented by
• the present invention is a compound represented by structural formula I where n is 1, j is 0,
• Each R 5 , R 6 independently is H, methyl, or a C 1 -C 24 linear or branched or cyclic alkyl chain, Each n, n′ independently is 1 to 15, preferably 4 to 10.
• (c) can include reacting the product of (b) with oleic acid.
• a polymer that is a reaction product of starting materials comprising a substituted phenol and an aldehyde that is further esterified with an alkyl acid through the use of oxalyl chloride or thionyl chloride.
• the alklyl acid used in the methods of the present invention is selected from the group consisting of an alkyl with at least about 4 carbon atoms, preferably C 5 to C 26 acid such as saturated straight chain fatty acid including caprylic acid (8:0), capric acid (10:0), lauric acid (12:0), myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0), behenic acid (22:0), lignoceric acid (24:0), or cerotic acid(26:0).
• caprylic acid (8:0), capric acid (10:0), lauric acid (12:0), myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0), behenic acid (22:0), lignoceric acid (24:0), or cerotic acid(26:0).
• the aldehyde used in the methods of the present invention is selected from the group consisting of formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde.
• the methods of the present invention are the product above referred as a substituted phenol-aldehyde polymer.
• Scheme I-A illustrate the particular embodiments of this method
• a substituted phenol is selected from Structural formula XIV
• aldehyde is selected from formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde; all of the remaining variables are as described above or Structural formula III, n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10, all of the remaining variables are as described above or Structural formula II.
• in the method involves adding concentrated sulfuric acid to the reaction mixture of a substituted phenol and an aldehyde in distilled water and keep at the ice-bath temperature.
• the ratio of a substituted phenol to a suitable solvent is 1:1-10, 1:1-5, 1:1-3, 1:2 or 1:1 by volume.
• in the method above involves refluxing the reaction mixture under inert atmosphere between 1-48 hours, between 3 and 9 hours, between 6 and 12 hours, or between 12 and 36 hours.
• in the above method involves cooling the reaction mixture to room temperature and separating the product and washing with water.
• an acid added to the reaction mixture of a substituted phenol and an aldehyde in above solvents is selected from hydrochloric acid, p-toluenesulfonic acid, or oxalic acid, solid based acids, phosphoric acid and acetic acid.
• in the above method involves reacting alkyl chloride to the above (substituted phenol-aldehyde) product in a suitable solvent first at ice bath temperature and then bring it to the room temperature while stirring the reaction mixtures for 1 to 48 hours, 3 to 12 hours, or 6 to 24 hours.
• in the above method involves adding triethyl amine to the reaction mixture.
• alkyl acid chloride with carbons in the alkyl chain ranging from C 1 to C 26 .
• Preferred alkyl acid chlorides are, C 8 , C 12 , C 14 , C 16 , or C 18 linear or branched carbon alkyl acid chlorides.
• the methods of the present invention when the solvent is used it can be recycled by separting the solvents from the reaction mixture using distillation.
• aldehyde is selected from formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde; all of the remaining variables are as described above or Structural formula III; n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10.
• R is a linear or branched alkyl C 1 -C 26 chain, an alkyl C 12 or an alkyl C 16 or an alkyl C 18 or a mixture of alkyl C 12 , C 14 , C 16 and C 18 chains;
• n is an integer from 1 to 1000 or 0 to 100, 0 to or 0 to 25, 0 to 15, or preferably 0 to 10, all of the remaining variables are as described above or Structural formula II.
• an aldehyde is selected from a group of formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, or 2-methyl butanal, benzaldehyde; preferably formaldehyde or acetaldehyde; wherein, R is a linear or branched alkyl C 1 -C 26 chain, an alkyl C 12 or an alkyl C 16 or an alkyl C 18 or a mixture of alkyl C 12 , C 14 , C 16 and C 18 chains; n is an integer from 1 to or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10.
• R is a linear or branched alkyl C 1 -C 26 chain, an alkyl C 12 or an alkyl C 16 or an alkyl Cis or a mixture of alkyl C 12 , C 14 , C 16 and C 18 chains;
• n is an integer from 1 to 1000 or 0 to 100, 0 to or 0 to 25, 0 to 15, or preferably 0 to 10, all of the remaining variables are as described above or Structural formula II.
• the present invention is a method of producing a compound in Scheme IV where in a substituted phenol is selected from Structural formula XIV.
• the present invention is a method of producing a compound in Scheme IV wherein a substituted phenol is selected from Structural formula XIV.
• the present invention is a method of producing a compound in Scheme V wherein a substituted phenol is a phenol, ortho-cresol or a mixture of ortho, meta, para-cresols, or o-methoxyphenol, and R is a linear alkyl C12 or a C16 or C18 or a mixture of alkyl C 12 , C 14 , C 16 and C 18 chains, and n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10.
• n is an integer from 0 to 100 or 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10
• a macromolecular corrosion inhibitor that is a polymer which is the reaction product of the starting materials comprising a substituted phenol and an aldehyde and is further reacted with an alkenyl succinic anhydride to form an isomerized half ester product having a free carboxylic acid group in the repeating unit.
• the substituted phenol is selected from the Structural formulas XIV and an aldehyde is selected from formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde.
• an aldehyde is selected from formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde.
• an alkenyl succinic anhydride is selected from the group consisting of DDSA, ODSA, OSA, PIBSA to form an isomerized half ester product having free carboxylic acid groups in the alkenyl chain of the repeating group, and n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10 and all of the remaining variable are as described above or Structural formula XI and remaining variables are as described for structural formula II.
• the present invention is a method of producing a compound with a mixture of isomers (A) and (B) in Scheme VI.
• the present invention is a method of producing a compound with mixture of isomerized (A) and (B) in Structural formulas XII
• OSA′, DDSA′, ODSA′, PIBSA′ are alkenyl chain portion of OSA, octenyl succinic anhydride; DDSA, dodecenyl succinic anhydride; ODSA, octadecenyl succinic anhydride; PIBSA, polyisobutylene succinic anhydride (low molecular weight, 300-1500 molecular weight), respectively; and n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10, and all of the remaining variables are as described above or Structural formula II.
• the present invention is a method of producing a compound with mixture of isomers (A) and (B) in Structural formulas XII wherein the mixture of a substituted phenol-aldehyde polymer reacted with an alkenyl succinic anhydride selected from the group consisting of DDSA, dodecenyl succinic anhydride; ODSA, octadecenyl succinic anhydride; PIBSA, polyisobutylene succinic anhydride (low molecular weight, 300-1500 molecular weight) reaction temperatures between 80° C. to 175° C. between 1 and 24 hours, between 3 to 12 hours, or between 6-24 hours.
• an alkenyl succinic anhydride selected from the group consisting of DDSA, dodecenyl succinic anhydride; ODSA, octadecenyl succinic anhydride; PIBSA, polyisobutylene succinic anhydride (
• the present invention is a method of producing a compound with mixture of isomers (A) and (B) in Structural formulas XII wherein a substituted phenols is selected from Structural formulas XIV and an aldehyde is selected from an aldehyde is selected from formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde.
• the present invention is a method of producing a compound with a mixture of isomers (A) and (B) in Structural formulas XII wherein an aldehyde is formaldehyde or acetaldehyde.
• the present invention is a method of producing a compound with a mixture of isomerized structures in Structural formulas XII.
• a macromolecular corrosion inhibitor that is a polymer which is the reaction product of the starting materials comprising a substituted phenol and an aldehyde are further reacted with an alkylene oxide (e.g. propylene oxide) to form a phenol-derived alcohol in the repeating unit and is further reacted with an alkyl acid.
• an alkylene oxide e.g. propylene oxide
• Fischer esterification of a phenol with an alkyl acid is not an efficient one.
• the reaction is efficient if the phenolic-OH is converted to an alkyl alcohol and is further reacted with a linear or branched C 1 -C 26 alkyl acid.
• an aldehyde is selected from formaldehyde, acetaldehyde, valeraldehyde, butyraldehyde, isovalrealdehyde, 2-methyl butanal, benzaldehyde, cyclohexanecarbaldehyde, 3-methylcyclohexanecrabaldehyde, glyceraldehyde, glucose aldehyde; all of the remaining variables are as described above or Structural formula III.
• R 1 is selected from the group consisting of
• R d is an isomerized alkenyl chain
• n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10,
• R g is an isomerized oleate succinic anhydride chain (Scheme VII-I)
• R d is an isomerized oleate half-acid ester chain.
• R g is an isomerized oleate succinic anhydride chain (Scheme VII-I)
• R d is an isomerized oleate half-acid ester
• n is an integer from 1 to 1000 or 0 to 100, 0 to 50 or 0 to 25, 0 to 15, or preferably 0 to 10.
• R g is an isomerized oleate succinic anhydride chain (Scheme VII-I)
• R d is an isomerized oleate half-acid ester chain
• n is an integer from 1 to 1000 or 0 to 100, 0 to or 0 to 25, 0 to 15, or preferably 0 to 10.
• In one embodiment of the present invention is directed to forming a polymer by reacting a substituted phenol with a formaldehyde followed by post esterification of the reaction with oleoyl chloride is further reacted with maleic anhydride at reaction temperatures between 170° C. and 210° C. between 1 and 24 hours, between 3 to 12 hours, or between 6-24 hours.
• the molar ratio of the reaction product (of a substituted phenol with formaldehyde followed by post esterification of the reaction with oleoyl chloride) and maleic anhydride is 1:0.8, 1:0.9, 1:1.0, or 1:2.
• a suitable solvent is selected from the group consisting of toluene, xylene, chlorobenzene, dimethyl formamide, dimethyl sulfoxide, 1, 2-dichlorobenzene, dimethylsuccinate, diisobutyl adipate and diisobutyl glutarate.
• the weight ratio of a solvent and the reaction product is 0.1 to 1.0:1.0
• in the above method involves distilling the solvent from the reaction mixture.
• reaction product a substituted phenols reacted with formaldehyde followed by post esterification of the reaction with oleoyl chloride further reacted with maleic anhydride
• an alkyl alcohol to form half acid ester selected from the group consisting of linear or branched C 1 -C 24 chain at reaction temperatures between 80° C. and 150° C. between 1 and 24 hours, between 3 to 12 hours, or between 6-24 hours.
• each R 5 , R d independently is a linear or branched C 1 -C 24 alkyl chain.
• the compounds are in the salt forms to improve the solubility in certain fluids; for example, water or fluid mixtures, for example, metal working fluids, water based or oil based paints.
• R d is an C 1 -C 24 alcohol.
• R d is an C 1 -C 24 alcohol.
• R is an isomerized alkenyl chain represented by
• R d independently is a linear or branched C 1 -C 24 alkyl chain, the method comprising:
• lubricants and “lubricant oils” can be used interchangeably.
• examples of lubricants suitable for use in the compositions and methods of the present invention include, but are not limited to: i) petroleum based oils (Group I, II and III), ii) synthetic oils (Group IV, V) and iii) biolubricant oils (vegetable oils such as canola, soybean, high oleic canola, high oleic soybean oil, corn oil, castor oil, jatropha, etc.).
• Group I oils, as defined herein are solvent refined base oils.
• Group II oils as defined herein are modern conventional base oils made by hydrocracking and early wax isomerization, or hydroisomerization technologies and have significantly lower levels of impurities than Group I oils.
• Group III oils as defined herein are unconventional base oils. Groups I-III differ in impurities, and viscosity index as is shown in Kramer et al. “The Evolution of Base Oil Technology” Turbine Lubrication in the 21 st Century ASTM STP #1407 W. R. Herguth and T. M. Wayne, Eds., American Society for Testing and Materials, West Conshohocken, Pa., 2001 the entire contents of which are incorporated herein by reference.
• Group IV oils as defined herein are “synthetic” lubricant oils, including, for example, poly-alpha olefins (PAOs).
• Biolubricants, as defined herein are lubricants which contain at least 51% biomaterial (see Scott Fields, Environmental Health Perspectives, volume 111, number 12, September 2003, the entire contents of which are incorporated herein by reference).
• Other examples of lubricant oils can be found in Melvyn F. Askew “Biolubricants-Market Data Sheet” IENICA, August 2004 (as part of the IENICA work stream of the IENICA-INFORRM project); Taylor et al. “Engine lubricant Trends Since 1990” paper accepted for publication in the Proceedings I. Mech. E.
• Biolubricants are often but not necessarily, based on vegetable oils. Vegetable derived, for example, from rapeseed, sunflower, palm, and coconut can be used as biolubricants. They can also be synthetic esters which may be partly derived from renewable resources. They can be made from a wider variety of natural sources including solid fats and low grade or waste materials such as tallows. Biolubricants in general offer rapid biodegradability and low environmental toxicity.
• Group I, II and III oils are petroleum base stock oil.
• the petroleum industry differentiates their oil based on viscosity index and groups them as Group I, II and III.
• the synthetic oils are Group IV and Group V.
• Synthetic oils include hydrocarbon oil.
• Hydrocarbon oils include oils such as polymerized and interpolymerized olefins (polybutylenes, polypropylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene-alpha olefin copolymers, for example).
• Poly alpha olefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oil.
• PAOs derived from C 8 , C 10 , C 12 , C 14 olefins or mixtures thereof may be utilized.
• PAO is a bio-based oil.
• synthetic oils are polyolesters for example diesters, polyolesters such as neopentyl glycols (NPGs), trimethylolpropanes (TMPs), penterythritols (PEs), and dipentaerythritols (DiPEs).
• synthetic oils include monoesters and trimellitates.
• synthetic oils include polyalkylene glycols (PAGs).
• synthetic esters described herein are obtained by reacting one or more polyhydric alcohols with alkyl acids.
• Polyhydric alcohols preferably include the hindered polyols (such as the neopentyl polyols, e.g., neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl-1,3-propanediol, trimethylol propane, pentaerythritol, and dipentaerythritol) and alkyl acids include least about 4 carbon atoms, preferably C 5 to C 26 acids such as saturated straight chain fatty acids including caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures of any of these materials.
• the hindered polyols such as the ne
• mixtures of synthetic (Groups IV and V) and bio-oils or petroleum based oils (Groups I, II, III) and biooils, or petroleum based oils and synthetic oils, or mixtures of bio-oils, synthetic oils and petroleum base oils may be used.
• 0.001% to 10% by weight of the corrosion inhibitors of the present invention is added to lubricant oils. In certain other embodiments of the present invention, 10% to 5% by weight of the corrosion inhibitors of the present invention are added to lubricant oils. In certain other embodiments of the present invention, 0.001% to 2% by weight of the corrosion inhibitors of the present invention is added to lubricant oils. In certain other embodiments of the present invention, 0.001% to 0.5% by weight of the corrosion inhibitors of the present invention is added to lubricant oils. This percentage varies depending upon their end application and type of the base oil.
• the corrosion inhibitors of the present invention are usually added to lubricant oils with stirring at between 0 and 100° C., between 20 and 80° C. or between 40-60° C.
• the corrosion inhibitors of the present invention are usually added to lubricant and fuel oils (based on petroleum, synthetic, and/or bio-based oils) (examples, gasoline, diesel, biodiesel (B10, B20, up to B100 where numbers after letter B corresponds to percentage of fatty acid methyl esters (FAME) content in diesel) used in automotives, and industrial applications such as but not limited to transmission fluid, engine oil, break oil, metal working fluids, greases, gear oils, hydraulic fluids, transformer oils, elevator oils wire and rope oils, drilling oils, turbine oils used for hydro-power turbines, aviation turbines, wind turbines, metal working fluids, etc.
• lubricant and fuel oils based on petroleum, synthetic, and/or bio-based oils
• fuel oils based on petroleum, synthetic, and/or bio-based oils
• examples gasoline, diesel, biodiesel (B10, B20, up to B100 where numbers after letter B corresponds to percentage of fatty acid methyl esters (FAME) content in diesel
• FAME fatty acid
• the mixture of corrosion inhibitors of the present invention is preferred due to improved solubility characteristics as compared to a single component corrosion inhibitor.
• corrosion inhibitors have significantly improved solubility characteristics in petroleum (Group I-V oils), bio-based oils and bio-oils. This is mainly attributed to the design of the molecules of the current invention containing alkyl chains to increase the solubility.
• corrosion inhibitors is preferred due to multifunctional characteristics to protect against rust corrosion, copper, aluminum and alloy corrosion and also water separability from oil (as a demulsifier).
• three independent additives each one proving desired rust inhibition, copper protection, and demulsifiers are used in the formulation.
• the present invention provides all three protections by a single compound. This significantly reduces the number of additives required in the lubricant formulation at least from three additives to one single additive providing rust inhibition, copper protection against corrosion and performs as a demulsifier to separate water from oil. It is economically attractive by reducing three additives to one for the lubricant formulation.
• corrosion inhibitors is preferred in aftermarket automotive lubricant products.
• corrosion inhibitors have excellent solubility in bio-oils, bio-based oils, synthetic oils, petroleum based oils.
• the corrosion inhibitors of the present invention are usually added to lubricant and fuel oils along with other additional lubricant additives including but not limited to antioxidants, anti-foaming, a viscosity modifier, pour point depressants, and other phenolic and aminic antioxidants.
• the present invention is a composition comprising present invention corrosion inhibitors, and at least one additive selected from the group consisting of i) a surface additive; ii) a performance enhancing additive, and iii) a lubricant protective additive.
• the present invention is a lubricant composition
• a lubricant composition comprising: a lubricant or a mixture of lubricants, a present invention corrosion inhibitor and at least one additive selected from the group consisting of i) a surface additive; ii) a performance enhancing additive, and iii) a lubricant protective additive.
• the present invention is a method of improving a lubricant or a mixture of lubricants comprising combining the lubricant or mixture of lubricants with present invention corrosion inhibitor, and at least one additive selected from the group consisting of i) a surface additive; ii) a performance enhancing additive; and iii) a lubricant protective additive.
• compositions and methods of the present invention generally provide increased shelf life, increased oxidative resistance, enhanced performance and/or improved quality to materials, such as, for example, lubricants and lubricant oils and fuels.
• materials such as, for example, lubricants and lubricant oils and fuels.
• Other examples include. biolubricants and biolubricant oils and biofuel such as biodiesel.
• biolubricants and biolubricant oils and biofuel such as biodiesel.
• the additives exhibit several key functions such as corrosion inhibition, detergency, viscosity modification, and antiwear performance, dispersant properties, cleaning and suspending ability.
• the disclosed compositions in general, provide superior performance of lubricants in high temperatures applications due to the presence of high performance additives which are thermally stable at high temperatures with enhanced oxidation resistance.
• the present invention of corrosion inhibitors is suitable for other corrodible materials including but not limited to fuels, biofuel, diesel, biodiesel, aviation fuels, kerosene, etc.
• the present invention of corrosion inhibitors is suitable for additive packages for lubricants and fuels. These packages are for aftermarket products to enhance the performance of lubricants and fuel. Other additive packages designed for formulating lubricants and fuel by adding to base stock oils; petroleum based (Group I-V oils), bio-based, bio-oils, and gasoline, diesel, and biodiesel.
• the present invention is an additive package composition comprising present invention corrosion inhibitors, and at least one additive selected from the group consisting of i) a surface additive; ii) a performance enhancing additive, and iii) a lubricant protective additive.
• the present invention is an additive package composition
• a lubricant or a mixture of lubricants comprising: a lubricant or a mixture of lubricants, a present invention corrosion inhibitor and at least one additive selected from the group consisting of i) a surface additive; ii) a performance enhancing additive, and iii) a lubricant protective additive.
• the present invention is a method of improving an additive package composition
• combining the composition with present invention corrosion inhibitor comprising combining the composition with present invention corrosion inhibitor; and at least one additive selected from the group consisting of i) a surface additive; ii) a performance enhancing additive, and iii) a lubricant protective additive.
• the present invention is a method of improving an additive package composition
• corrosion inhibitor comprising additives one or more of an antioxidant, a metal deactivator, rust inhibitor, copper corrosion inhibitor, viscosity index modifier, pour point depressant, dispersing agent, detergent, an extreme-pressure, a dye, seal swell agents, a demulsifiers, and an anti-foaming additive; each additive present in the range 0.005%-5% and a carrier oil.
• a suitable carrier from petroleum, biobased, bio-oil is the one that dissolves all additives and easy to pour into a lubricant or a fuel.
• the ratio between additives and carrier oil may range from 1:99 to 99:1 by weight %, 5:95 by weight %, 10:90 by weight %, 20:90 by weight %, 30:70 by weight %, 40:60 by weight %, 50:50 by weight %, 60:40 by weight %, 70:30 by weight %, 80:20 by weight %, 90:10 by weight %, 95:5 by weight %.
• the present invention of corrosion inhibitors may typically apply to coatings and paints including multi-package systems which are usually mixed prior to use, the pigments, catalysts and other additives can be added.
• the present invention applications include base coat and clear coat formulations especially in the automotive, aviation, and marine industry.
• Lubricants, lubricant oils, mixtures thereof and compositions comprising lubricants and lubricant oils can be improved by the methods of the present invention, by contacting the lubricant, lubricant oil, mixtures thereof or composition comprising the lubricant or lubricant oil or mixtures thereof with corrosion inhibitors, additives and mixtures thereof as described herein.
• lubricants and “lubricant oils” can be used interchangeably.
• examples of lubricants suitable for use in the compositions and methods of the present invention include, but are not limited to: i) petroleum based oils (Group I, II and III), ii) synthetic oils (Group IV and V)) and iii) biolubricant oils (vegetable oils such as canola, soybean, corn oil etc.), and bio-based oils like polyol esters, biobased esters like estolides, bio-poly alpha olefins, bio alkylene glycols, bio poly alkylene glycols.
• Group I oils, as defined herein are solvent refined base oils.
• Group II oils as defined herein are modern conventional base oils made by hydrocracking and early wax isomerization, or hydroisomerization technologies and have significantly lower levels of impurities than Group I oils.
• Group III oils as defined herein are unconventional base oils. Groups I-III differ in impurities, and viscosity index as is shown in Kramer et al. “The Evolution of Base Oil Technology” Turbine Lubrication in the 21 st Century ASTM STP #1407 W. R. Herguth and T. M. Wayne, Eds., American Society for Testing and Materials, West Conshohocken, Pa., 2001 the entire contents of which are incorporated herein by reference.
• Group IV oils as defined herein are “synthetic” lubricant oils, including, for example, poly-alpha olefins (PAOs).
• Biolubricants, as defined herein are lubricants which contain at least 51% biomaterial (see Scott Fields, Environmental Health Perspectives, volume 111, number 12, September 2003, the entire contents of which are incorporated herein by reference).
• Other examples of lubricant oils can be found in Melvyn F. Askew “Biolubricants-Market Data Sheet” IENICA, August 2004 (as part of the IENICA work stream of the IENICA-INFORRM project); Taylor et al. “Engine lubricant Trends Since 1990” paper accepted for publication in the Proceedings I. Mech. E.
• Biolubricants are often but not necessarily, based on vegetable oils. Vegetable derived, for example, from rapeseed, sunflower, palm, and coconut can be used as biolubricants. They can also be synthetic esters which may be partly derived from renewable resources. They can be made from a wider variety of natural sources including solid fats and low grade or waste materials such as tallows. Biolubricants in general offer rapid biodegradability and low environmental toxicity.
• first additives suitable for use in the compositions and methods of the present invention include but are not limited to, surface additives, performance enhancing additives and lubricant protective additives.
• surface additives can protect the surfaces that are lubricated from wear, corrosion, rust, and frictions.
• these surface additives suitable for use in the compositions and methods of the present invention include, but are not limited to: (a) rust inhibitors, (b) corrosion inhibitors, (c) extreme pressure agents, (d) tackiness agents, (e) antiwear agents, (f) detergents and dispersants, (g) compounded oil (like fat or vegetable oil to reduce the coefficient of friction without affecting the viscosity), (h) antimisting, (i) seal swelling agents and (j) biocides.
• performance enhancing additives improve the performance of lubricants.
• these performance enhancing additives suitable for use in the Compositions and methods of the present invention include, but are not limited to: (a) pour-point depressants, (b) viscosity index modifiers (c) emulsifiers, and (d) demulsifiers.
• Lubricant protective additives maintain the quality of oil from oxidation and other thermal degradation processes.
• lubricant protective additives suitable for use in the compositions and methods of the present invention include, but are not limited to: (a) oxidation inhibitors and (b) foam inhibitors.
• a second additive can be used in the compositions and methods of the present invention in combination with the first antioxidant and the first additive as described above.
• second additives suitable for use in the compositions and methods of the present invention include, include but are not limited to, for example, dispersants, detergents, corrosion inhibitors, rust inhibitors, metal deactivators, antiwear and extreme pressure agents, antifoam agents, friction modifiers, seal swell agents, demulsifiers, viscosity index improvers, pour point depressants, and the like. See, for example, U.S. Pat. No. 5,498,809 for a description of useful lubricating oil composition additives, the disclosure of which is incorporated herein by reference in its entirety.
• Dispersants examples include, but are not limited to polybutenylsuccinic acid-amides, -imides, or -esters, polybutenylphosphonic acid derivatives, Mannich Base ashless dispersants, and the like.
• detergents suitable for use in the compositions and methods of the present invention include, but are not limited to metallic phenolates, metallic sulfonates, metallic salicylates, metallic phosphonates, metallic thiophosphonates, metallic thiopyrophosphonates, and the like.
• Corrosion Inhibitors examples include, but are not limited to: phosphosulfurized hydrocarbons and their reaction products with an alkaline earth metal oxide or hydroxide, hydrocarbyl-thio-substituted derivatives of 1,3,4-thiadiazole, thiadiazole polysulphides and their derivatives and polymers thereof, thio and polythio sulphenamides of thiadiazoles such as those described in U.K. Patent Specification 1,560,830, and the like.
• Rust Inhibitors examples include, but are not limited to: nonionic surfactants such as polyoxyalkylene polyols and esters thereof, anionic surfactants such as salts of alkyl sulfonic acids, and other compounds such as alkoxylated fatty amines, amides, alcohols and the like, including alkoxylated fatty acid derivatives treated with C9 to C16 alkyl-substituted phenols (such as the mono- and di-heptyl, octyl, nonyl, decyl, undecyl, dodecyl and tridecyl phenols).
• nonionic surfactants such as polyoxyalkylene polyols and esters thereof
• anionic surfactants such as salts of alkyl sulfonic acids
• other compounds such as alkoxylated fatty amines, amides, alcohols and the like, including alkoxylated fatty acid derivatives treated with C9 to C16 alky
• Metal deactivators as used herein, are the additives which form an inactive film on metal surfaces by complexing with metallic ions and reducing, for example, the catalytic effect on metal gum formation and other oxidation.
• metal deactivators suitable for use in the compositions and methods of the present invention include, but are not limited to N, N-disubstituted aminomethyl-1, 2, 4-triazoles, N, N-disubstituted aminomethyl-benzotriazoles, mixtures thereof, and the like.
• Antiwear and Extreme Pressure additives react with metal surfaces to form a layer with lower shear strength then metal, thereby preventing metal to metal contact and reducing friction and wear.
• antiwear additives suitable for use in the compositions and methods of the present invention include, but are not limited to: sulfurized olefins, sulfurized esters, sulfurized animal and vegetable oils, phosphate esters, organophosphites, dialkyl alkylphosphonates, acid phosphates, zinc dialkyldithiophosphates, zinc diaryldithiophosphates, organic dithiophosphates, organic phosphorothiolates, organic thiophosphates, organic dithiocarbamates, dimercaptothiadiazole derivatives, mercaptobenzothiazole derivatives, amine phosphates, amine thiophosphates, amine dithiophosphates, organic borates, chlorinated paraffins, and the like.
• Antifoam Agents examples include, but are not limited to: polysiloxanes and the like.
• Friction Modifiers suitable for use in the compositions and methods of the present invention include, but are not limited to: fatty acid esters and amides, organic molybdenum compounds, molybdenum dialkylthiocarbamates, molybdenum dialkyl dithiophosphates, molybdenum dithiolates, copper oleate, copper salicylate, copper dialkyldithiophosphates, molybdenum disulfide, graphite, polytetrafluoroethylene, and the like.
• Seal swell agents react chemically with elastomers to cause slight swell thus improving low temperature performance especially in, for example, aircraft hydraulic oil.
• seal swell agents suitable for use in the compositions and methods of the present invention include, but are not limited to: dioctyl sebacate, dioctyl adipate, dialkyl phthalates, and the like.
• Demulsifiers as used herein promote separation of oil and water in lubricants exposed to water.
• demulsifiers suitable for use in the compositions and methods of the present invention include, but are not limited to: the esters described in U.S. Pat. Nos. 3,098,827 and 2,674,619 incorporated herein by reference.
• Viscosity Index Improvers examples include, but are not limited to olefin copolymers, dispersant olefin copolymers, polymethacrylates, vinylpyrrolidone/methacrylate-copolymers, polyvinylpyrrolidones, polybutanes, styrene/-acrylate-copolymers, polyethers, and the like.
• Pour point depressants as used herein reduce the size and cohesiveness of crystal structure resulting in low pour point and increased flow at low-temperatures.
• pour point depressants suitable for use in the compositions and methods of the present invention include, but are not limited to: polymethacrylates, alkylated naphthalene derivatives, and the like.
• a second antioxidant or a stabilizer can be used in the compositions and methods of the present invention in combination with the first antioxidant and the first additive and optionally the second additive as described above.
• second antioxidants suitable for use in the compositions and methods of the present invention include, include but are not limited to:
• compositions for use in the methods of the present invention include but are not limited to:
• a first corrosion inhibitor in the concentration range, from about 0.0001% to about 50%, from about 0.0005% to about 20%, from about 0.005% to about 10%, from about 0.05% to about 5% or from about 0.01% to about 1%) with a first additive selected from the group comprising an antioxidant, a surface additive, a performance enhancing additive and a lubricant performance additive, for example, in amounts of from about 0.0005% to about 50%, from about 0.0001% to about 20%, from about 0.005% to about 10%, from about 0.05% to about 5% or from about 0.01% to about 1% by weight, based on the weight of lubricant to be stabilized.
• a first corrosion inhibitor in the concentration range, from about 0.0001% to about 50%, from about 0.0005% to about 20%, from about 0.005% to about 10%, from about 0.05% to about 5% or from about 0.01% to about 1% by weight, based on the weight of lubricant to be stabilized.
• the first corrosion inhibitor and the first additive as described in a. and a second additive for example, in concentrations of from about 0.0001% to about 50% by weight, about 0.0005% to about 20% by weight, about 0.001% to about 10% by weight, from about 0.01% to about 5% by weight, from about 0.05% to about 1% by weight from about 0.1% to about 1% by weight based on the overall weight of the lubricant to be stabilized.
• the first corrosion inhibitor and the first additive as described in a. and optionally the second additive as described in b. and a second corrosion inhibitor for example, Irgacor® 190, Irgacor® NPA, Cuvan® 303, Cuvan® 484, Cuvan® 826, in the concentration range, from about 0.0001% to about 50%, from about 0.0005% to about 20%, from about 0.005% to about 10%, from about 0.05% to about 5% or from about 0.01% to about 1%) by weight, based on the weight of lubricant to be stabilized.
• the antioxidant compositions for use in the methods of the present invention include but is not limited to: the first antioxidant from the present invention and the second antioxidant from the section.
• the antioxidant composition where in the weight ratio of the second antioxidant to the first antioxidant of the present invention is from about 1:99 to 99:1, from about 10:90, 20:80, 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10.
• the second antioxidant second antioxidant for example, Irganox® L 57, Irganox® L64, Irganox® 1330, Irganox® 1076, Irganox® 5057 and Irganox L 135, Polnox®7030, Polnox® 7070, Polnox® 8020, Polnox®8060, Polnox®8080.
• Example 2 The same method in Example 1 is used with a linear alkyl chain of C 12 , C 16 and C 18 atoms and a branched alkyl chain with C 8 atoms.
• Example 2 The same method in Example 1 is used for the synthesis of phenol and substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o, m, p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol, and phloroglucinol.
• substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o, m, p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol,
• Example 3 The same method in Example 1 is used with a linear alkyl chain of C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for phenol and substituted phenols in Example 3.
• Oxalyl chloride (6 mL, 67.06 mmol) was added slowly to the mixture of o-cresol (5.74 g, 53.12 mmol) and stearic acid (15.11 g, 53.12 mmol) in dichloromethane (15 mL) with a catalytic amount (a couple of drops) of DMF in ice-bath under a nitrogen atmosphere.
• the reaction mixture was stirred for 30 min at this temperature under nitrogen atmosphere. Then, the reaction mixture was stirred at 60° C. for 6-10 h. The completion of the reaction was confirmed by TLC and FTIR. After cooling, the crude product was extracted with saturated NaHCO 3 and brine. The organic phase was dried over anhydrous Na 2 SO 4 . It was then concentrated under reduced pressure. Concentration in vacuo gave the target compound.
• Example 5 The same method in Example 5 is used with a linear alkyl chain of C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms.
• Example 5 is synthesized using thionyl chloride instead of oxalyl chloride.
• Example 2 The same method in Example is used with a linear alkyl chain of C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for phenol and substituted phenols such as 2-methoxyphenol, 2-t-butyl-4-methoxyphenol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol and phloroglucinol.
• substituted phenols such as 2-methoxyphenol, 2-t-butyl-4-methoxyphenol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert
• Example 7 The same method in Example 7 is used with a linear alkyl chain of C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for phenol and substituted phenols such as 2-methoxyphenol, 2-t-butyl-4-methoxyphenol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol and phloroglucinol.
• substituted phenols such as 2-methoxyphenol, 2-t-butyl-4-methoxyphenol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-ter
• Example 10 The same method in Example 10 was used for the synthesis of o-cresol, o,m,p-cresol mixtures, 2-t-butyl-4-methoxyphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, and 4-t-butylphenol. It is also used others such as m-cresol, p-cresol, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, resorcinol, catechol, and phloroglucinol. This reaction was done using other solvents such as toluene and 1,2-dichloroethane. This reaction was done using oxalic acid as a catalyst.
• Example 12 The same method in Example 12 was used with a linear alkyl chain of C 8 , C 12 , C 16 and a branched alkyl chain of C 8 atoms. It is also used with a linear alkyl chain of C 18 atoms.
• Example 13 The same method in Example 5 is used with a linear alkyl chain of C 8 , C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for Example 13.
• Example 13 The same method in Example 5 is used with a linear alkyl chain of C 8 , C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for Example 13.
• Example 12 The same method in Example 12 was used with a linear alkyl chain of C 8 for 4-t-butylphenol and 2-t-butyl-4-methoxyphenol used as starting material in Example 11.
• Example 5 The same method in Example 5 is used with a linear alkyl chain of C 8 , C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for the other compounds obtained in Example 11.
• Example 11 The same method in Example 5 is used with a linear alkyl group of C 8 , C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for Example 11.
• Example 7 The same method in Example 7 is used with a linear alkyl chain of C 8 , C 12 , C 16 and C 18 atoms and a branched alkyl chain of C 8 atoms for Example 11.
• Oxalyl chloride (3.7 mL, 42.56 mmol) was added slowly to the mixture of 2-methoxyphenol (4.49 g, 35.47 mmol) and oleic acid (10.02 g, 35.47 mmol) with a catalytic amount (a couple of drops) of DMF in ice-bath under a nitrogen atmosphere.
• the reaction mixture was stirred for 30 min at this temperature under nitrogen atmosphere. Then, the reaction mixture was stirred at 60° C. for 6-10 h. The completion of the reaction was confirmed by TLC and FTIR. After cooling, the crude product was extracted with saturated NaHCO 3 and brine. The organic phase was dried over anhydrous Na 2 SO 4 . It was then concentrated under reduced pressure. Concentration in vacuo gave the target compound yellow oil. This reaction was done using thionyl chloride.
• Example 19 The same method in Example 19 was used for phenol, o-cresol, resorcinol and catechol. It is also used others such as 2-t-butyl-4-methoxyphenol, m-cresol, p-cresol, o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol and 4-t-butylphenol, and phloroglucinol. Dichloromethane was used as a solvent of substituted phenols which are solid at reaction temperature 60° C.
• Example 19 was synthesized using thionyl chloride instead of oxalyl chloride.
• Example 20 is synthesized using thionyl chloride instead of oxalyl chloride.
• Oxalyl chloride (3.6 mL, 41.3 mmol) was added slowly to the mixture of the product in Example (5 g, 9.39 mmol) and oleic acid (9 g, 31.9 mmol) in dichloromethane (25 mL) with a catalytic amount (0.1 mL) of DMF in ice-bath under a nitrogen atmosphere. The reaction mixture was stirred for 30 min at this temperature under nitrogen atmosphere. Then, the reaction mixture was stirred at 60° C. for 6-10 h. The completion of the reaction was confirmed FTIR. After cooling, the crude product was extracted with saturated NaHCO 3 and brine. The organic phase was dried over anhydrous Na 2 SO 4 . It was then concentrated under reduced pressure.
• Example 23 The compound in Example 23 was synthesized using thionyl chloride instead of oxalyl chloride.
• Example 24 The same method in Example 24 was used to attach oleic acid to the compounds obtained in Example 12 such as using o-cresol, o,m,p-cresol mixtures, resorcinol, and catechol. It is also used others such as using m-cresol, p-cresol, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, 2-t-butyl-4-methoxyphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol and 4-t-butylphenol and phloroglucinol.
• o-cresol o,m,p-cresol mixtures
• catechol catechol
• others such as using m-cresol, p-cresol, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, 2-t-buty
• Example 25 is synthesized using thionyl chloride instead of oxalyl chloride.
• Example 27 The same method in Example 27 was used for the attachment of C 4 alkyl chain. It is also used for the attachment of C 2 and C 3 alkyl chains.
• Example 29 The same method in Example 29 is used for the attachment of a linear alkyl chain of C 8 , C 12 and C 16 atoms and a branched alkyl chain of C 8 atoms.
• Example 30 is synthesized using apparatus Dean-Stark instead of molecular sieves.
• Example 30 The same method in Example 31 is used to make Example 30.
• Example 33 The same method in Example 33 was used for the compounds obtained in Example 19.
• Example 33 The same method in Example 33 was used for the compounds obtained in Example 20 such as using phenol, o-cresol, resorcinol, and catechol. It is also used others such as 2-t-butyl-4-methoxyphenol, m-cresol, p-cresol, o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol and 4-t-butylphenol, and phloroglucinol.
• 2-t-butyl-4-methoxyphenol m-cresol, p-cresol, o,m,p-cresol mixtures
• 2-sec-butylphenol 2-tert-amylphenol
• 2-tert-butylphenol 2-isopropyl-5-methylphenol
• eugenol isoeugeno
• Example 33 The same method in Example 33 was used for the compounds obtained in Example 23.
• Example 33 The same method in Example 33 was used for the compounds obtained in Example 25 such as using o-cresol, o,m,p-cresol mixtures, resorcinol, and catechol. It is also used others such as using m-cresol, p-cresol, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, 2-t-butyl-4-methoxyphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol and 4-t-butylphenol and phloroglucinol.
• o-cresol o,m,p-cresol mixtures
• catechol catechol
• others such as using m-cresol, p-cresol, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, 2-t-butyl-4-methoxyphenol
• Example 33 The same method in Example 33 was used for the compound obtained in Example 28. It is also used for the attachment of C 2 and C 3 alkyl chains.
• Example 33 The same method in Example 33 was used for the compound obtained in Example 29.
• Example 33 The same method in Example 33 is used for the compounds obtained in Example 30.
• Example 41 The same method in Example 41 is used for the substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol and phloroglucinol.
• substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol
• Example 41 The same method in Example 41 is used for the compound obtained in Example 10.
• Example 41 The same method in Example 41 is used for the compounds obtained in Example 11.
• Example 45 The same method in Example 45 is used for the compound obtained in Example 33 with a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms, ethylene glycol, hexanediol, neopentyl glycol, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaeryrthritol and di-pentaeryrthritol.
• a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms ethylene glycol, hexanediol, neopentyl glycol, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,
• Example 45 The same method in Example 45 is used for the compound obtained in Example 34 with the reaction of C 1 -C 24 mono alkyl alcohols, ethylene glycol, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, hexanediol, neopentyl glycol, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaeryrthritol, and di-pentaeryrthritol.
• C 1 -C 24 mono alkyl alcohols ethylene glycol, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, hexanediol, neopentyl glycol, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaeryrthritol, and di-p
• Example 45 The same method in Example 45 was used for the compound obtained in Example 35 with a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, ethylene glycol, hexanediol, neopentyl glycol, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaeryrthritol and di-pentaeryrthritol.
• a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, ethylene glycol, hexanediol, ne
• Example 45 The same method in Example 45 was used for the compound obtained in Example 36 with a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms.
• Example 45 The same method in Example 45 was used for the compound obtained in Example 37 with a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms.
• Example 45 The same method in Example 45 was used for the compound obtained in Example 39 with a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, ethylene glycol, hexanediol, neopentyl glycol, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaeryrthritol and di-pentaeryrthritol.
• a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, ethylene glycol, hexanediol, ne
• Example 45 The same method in Example 45 is used for the compound obtained in Example 40 with a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms, 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, ethylene glycol, hexanediol, neopentyl glycol, diethanolamine, trimethylolpropane, glycerol, triethanolamine, pentaeryrthritol and di-pentaeryrthritol.
• a linear alkyl alcohol of C 8 , C 12 and C 16 atoms and a branched alkyl alcohol of C 8 atoms 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, ethylene glycol, hexanediol, ne
• Example 45 The same method in Example 45 is used the compound obtained in Example 10 to react with succinic anhydrides such as a DDSA, ODSA, OSA, and PIBSA.
• succinic anhydrides such as a DDSA, ODSA, OSA, and PIBSA.
• Example 45 The same method in Example 45 is used the compound obtained in Example 11 to react with succinic anhydrides such as DDSA, ODSA, OSA, and PIBSA.
• succinic anhydrides such as DDSA, ODSA, OSA, and PIBSA.
• Example 45 substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol and phloroglucinol to react with succinic anhydrides such as a linear alkyl and a branched alkyl of octenyl succinic anhydride, tetradecenylsuccinic anhydride, hexadecenylsuccinic anhydride and polyisobutylene succinic anhydride.
• succinic anhydrides such as a linear alkyl and a branched alkyl of octenyl succ
• Example 45 substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol, and phloroglucinol to react with the compound obtained in Example 33.
• substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol
• Example 45 substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol, and phloroglucinol to react with the compound obtained in Example 38.
• substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol
• Example 45 substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol, and phloroglucinol to react with the compound obtained in Example 39.
• substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol
• Example 45 substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol, 4-t-butylphenol, resorcinol, catechol, and phloroglucinol to react with the compound obtained in Example 40.
• substituted phenols such as 2-methoxyphenol, o-cresol, m-cresol, p-cresol and o,m,p-cresol mixtures, 2-sec-butylphenol, 2-tert-amylphenol, 2-tert-butylphenol, 2-isopropyl-5-methylphenol, eugenol, isoeugenol, 4-ethyl-2-methoxyphenol
• Example 45 The same method in Example 45 was used the compound obtained in Example 41 to react with an octadecenylsuccinic anhydride.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with other succinic anhydrides such as DDSA, ODSA, OSA, and PIBSA.
• succinic anhydrides such as DDSA, ODSA, OSA, and PIBSA.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 33.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 34.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 35.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 36.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 37.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 38.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 39.
• Example 45 The same method in Example 45 is used the compound obtained in Example 41 to react with the compounds obtained in Example 40.
• the performance of corrosion inhibitor can be evaluated using ASTM D130 and ASTM D665 test methods for fluids like lubricants and fuels.
• ASTM D130 test method is suited to test the performance corrosion inhibitors for copper metals whereas ASTM D665 is of steel materials.
• the Copper Strip Tarnish Test assesses the relative degree of corrosivity of petroleum products, including aviation fuels, automotive gasoline, natural gasoline, solvents, kerosene, diesel fuel, distillate fuel oil, lubricating oil and other products.
• a polished copper strip is immersed in 30 mL of the sample at elevated temperature. After the test period, the strip is examined for evidence of corrosion and a classification number from 1-4 is assigned based on a comparison with the ASTM Copper Strip Corrosion Standards.
• corrosion inhibitors of this invention were also tested using ASTM D665 protocol.
• 300 ml of fluid treated with corrosion inhibitor and 30 ml of standard synthetic sea water are mixed thoroughly at 60° C. and a standard polished, cylindrical steel rod are immersed in the fluid for 4 hours. The rod will be examined for a pass or fail the test. If there is no sign of rust on the surface of the steel rod, a rating of Pass is given to the product.
• the products of this invention show no rust corrosion for steel rods in canola oil if they are treated with 0.4-0.5 weight % of the oil.
• the ASTM D 1401 test method was used to study water separability of the present invention.
• this method is a known amount of water and oil treated with the demulsifier, 40 ml were poured in to a graduated jar of a specified diameter. The sample was kept at a constant temperature (40° C.). Both oil and water were stirred using a motorized stirrer at a specified specific rotation speed of 1500 rpm. The time taken for the two separate was measured in minutes, the faster the separation better is the demulsibility. The results are quoted as ml-ml-emulsion (time, min). For example, 40-40-0 (30) means it took 30 minutes to separate the two with no emulsion.
• the sample of the present invention treated at the same level for corrosion inhibitor. For example, canola was treated at 0.5% with the sample of the present invention whereas Group II oil was tested at 0.05%.

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