WO2002094889A2 - Emulsifiants de masses moleculaires faibles et elevees a base de polyisobutylene, et melanges de ces emulsifiants - Google Patents

Emulsifiants de masses moleculaires faibles et elevees a base de polyisobutylene, et melanges de ces emulsifiants Download PDF

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Publication number
WO2002094889A2
WO2002094889A2 PCT/EP2002/005516 EP0205516W WO02094889A2 WO 2002094889 A2 WO2002094889 A2 WO 2002094889A2 EP 0205516 W EP0205516 W EP 0205516W WO 02094889 A2 WO02094889 A2 WO 02094889A2
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weight
general formula
compound
group
compounds
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PCT/EP2002/005516
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German (de)
English (en)
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WO2002094889A3 (fr
Inventor
Stephan Hüffer
Peter Schwab
Gregor Schürmann
Hans Peter Rath
Helmut Mach
Eckard Schauss
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Basf Aktiengesellschaft
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Priority to EP02750949A priority Critical patent/EP1404726A2/fr
Priority to AU2002338977A priority patent/AU2002338977A1/en
Priority to CA002448033A priority patent/CA2448033A1/fr
Priority to JP2002592363A priority patent/JP2004531614A/ja
Priority to US10/478,476 priority patent/US20040154216A1/en
Publication of WO2002094889A2 publication Critical patent/WO2002094889A2/fr
Publication of WO2002094889A3 publication Critical patent/WO2002094889A3/fr

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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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1857—Aldehydes; Ketones
    • 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
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/12—Partial amides 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles
    • C10N2050/013—Water-in-oil

Definitions

  • Low and high molecular weight emulsifiers especially those based on polyisobutylene, and their mixtures
  • the present invention relates to low and high molecular weight compounds, in particular based on polyisobutylene, and mixtures thereof, which are suitable as emulsifiers for water-in-oil emulsions, processes for the preparation of such compounds and the emulsions themselves.
  • the invention also relates to the use of such compounds as additives for fuels and lubricants, and as a corrosion-inhibiting additive in water-containing liquids, and also fuels, lubricants, fuel and lubricant additive concentrates and water-containing liquids containing the compounds according to the invention.
  • US Pat. No. 4,225,447 describes water-in-oil emulsions which are used as lubricants and a succinic anhydride substituted with an alkylenyl group (such as a polyisobutylenyl group), preferably with a number average molecular weight M n of 300 to 3000 g / mol Contain (earth) alkali metal salt of a succinic acid substituted with an alkenyl group or a succinic acid amide substituted with an alkenyl group as an emulsifier, optionally in combination with the salt of a resin acid.
  • an alkylenyl group such as a polyisobutylenyl group
  • EP-A 0 156 572 describes the use of surface-active substances based on succinic acid derivatives substituted with polyisobutylenyl groups, preferably with a cell-average molecular weight M n of 400 to 5000, with an anionic group for the preparation of water-in-oil or oil -in water emulsions.
  • Suitable anionic groups are phosphate, phosphonate, sulfate, sulfonate and carboxymethyl groups.
  • the applicant's German application filed on January 25, 2000 with the file number 100 03 105.6 describes the use of alkoxylated polyisobutylenes as emulsifiers in water-in-fuel emulsions.
  • R is a polyisobutylene with a weight average molecular weight of 300 to 2300, preferably 500 to 2000.
  • A is an alkylene radical with 2 to 8 carbon atoms.
  • the number m is a number from 1 to 200, which is chosen so that the alkoxylated polyisobutylene contains 0.2 to 1.5 alkylene oxide units per C 4 unit, preferably 0.5 alkylene oxide units per C unit; n is either 0 or 1.
  • R 1 is derived, inter alia, from a poly-1-butylene, -2-butylene or -to-butylene or mixtures thereof, and R 2 can be a polyalkylenepolyarnine or a polyalkylenimine radical.
  • WO 00/15740 discloses water-in-fuel emulsions which contain, as emulsifiers, two succinic acid derivatives which are linked via a linker such as alkanolamine, polyamine or polyol and which are substituted by hydrocarbon radicals such as polyisobutylenyl groups, in one embodiment the one succinic acid derivative being a polyisobutylenyl group with 8 to 25 carbon atoms and the other succinic acid derivative contains a polyisobutylenyl group with 50 to 400 carbon atoms.
  • a linker such as alkanolamine, polyamine or polyol and which are substituted by hydrocarbon radicals such as polyisobutylenyl groups
  • drilling fluids which contain both graft or block copolymers of polycarboxylic acids and polyethylene glycol and also compounds which consist of a succinic anhydride substituted with a polyisobutylenyl group, preferably with a number average molecular weight M n of 400 to 5000, and polyols, Polyamines, hydroxycarboxylic acids or amino alcohols are produced.
  • No. 4,708,753 discloses water-in-fuel emulsions which contain, inter alia, mono- or disalts of succinic acid with amines or amine salts of succinic acid monoesters as emulsifiers. These salts are formed by reacting alkanolamines, polyamines, oligoalcohols or polyols with succinic anhydrides which are substituted with C 2 o-C5 ⁇ ö hydrocarbon radicals such as polyisobutylenyl groups. In The examples only describe the salts of succinic acids or their monoesters which carry a polyisobutylenyl group with a number average molecular weight of 950 or 1700.
  • Friction-reducing additives for fuels and lubricants as well as emulsifiers are already known from the prior art.
  • US Pat. No. 5,858,029 describes friction-reducing additives for fuels and lubricants, in particular compounds of the formula R 1 (-OR -) a NH (CO) -R 3 -OH being used as friction-reducing additives, wherein R 1 is for a C] - bis C ⁇ so- alkyl radical, R is a C to C 4 alkylene radical, a is an integer from 1 to 12 and R is Ci to C alkylene or substituted alkylene or cycloalkylene.
  • Succinimides substituted with polyisobutylenyl groups may also be present as dispersants and polyalkylene amines such as polyisobutylene amines may be present as surfactants.
  • the object of the present invention is to provide further compounds which can be used as emulsifiers in water-in-oil emulsions.
  • L a stands for a polyisobutylenyl group with a number average molecular weight M n of 300 to 1000
  • L b represents a polyisobutylenyl group with a number average molecular weight M n of 2,000 to 20,000
  • -A- stands for -O- -N (H) - or -N (R ') -
  • M + stands for H 1 " , an alkali metal ion, 0.5 alkaline earth metal ions or NH, where one or more H in NH + can be replaced by alkyl radicals,
  • R represents a linear or branched saturated hydrocarbon radical which bears at least one substituent selected from the group OH, NH 2 or NH 3 + and optionally one or more C (O) H groups and optionally one or more non-adjacent -O- and / or contains secondary amines and / or tertiary amines, and wherein in the NH 2 - or NH 3 + groups one or more H may be replaced by alkyl radicals, and R 1 represents a linear or branched saturated hydrocarbon radical, which optionally has one or carries several substituents selected from the group OH, NH 2 , NH 3 + or C (O) H and optionally contains one or more non-adjacent -O- and / or secondary amines and / or tertiary amines, and wherein in the NH 2 - or NH 3 + groups one or more H may be replaced by alkyl radicals, and
  • the proportion of A-R in the compound of the general formula (Ia) or (Ib) is at least 20% by weight.
  • the compounds according to the invention can be used both individually and in a mixture as emulsifiers in water-in-oil emulsions. More stable emulsions can be produced than when using conventional emulsifiers.
  • the compounds of the general formula (Ib) can be regarded as diblock emulsifiers linked via a linker, the lipophilic block L a or L b via a covalent CC bond and the hydrophilic block R or R 1 via an ester or amide bond is linked to the left succinic acid.
  • Preferred compounds of the general formula (Ia) are those in which
  • - L a stands for a polyisobutylenyl group with a number average molecular weight M n from 350 to 950, in particular from 350 to 650, and / or
  • L a stands for a polyisobutylenyl group which has a polydispersity ⁇ 3.0, preferably from 1.1 to 2.5, particularly preferably from 1.1 to 2.0, and / or
  • A-R in the compound of general formula (Ia) is at least 25% by weight, in particular 35 to 60% by weight, and / or
  • R is composed of [-CH 2 -CH 2 -X] -, [-CH (CH 3 ) -CH 2 -X] - and / or [-CH 2 -CH (CH 3 ) -X] units, with X - O or NH.
  • Preferred compounds of the general formula (Ib) are those in which
  • L stands for a polyisobutylenyl group with a number average molecular weight from 2000 to 12000, in particular from 2300 to 5000, and / or
  • L b stands for a polyisobutylenyl group which has a polydispersity 3,0 3.0, preferably from 1.1 to 2.5, particularly preferably from 1.1 to 2.0, and / or
  • Particularly preferred are compounds of the general formula (Ia) or (Ib) in which A -O- and R is a monovalent radical of an oligomer or polymer of ethylene and / or propylene oxide or a monovalent radical of a block copolymer of ethylene and propylene oxide ,
  • Particularly effective emulsifiers are compounds of the general formula (Ia) in which L a stands for a polyisobutylenyl group with a number average molecular weight M n of 350 to 950, in particular 350 to 650, this polyisobutylenyl group optionally having a polydispersity 3,0 3.0 from 1.1 to 2.5, particularly preferably from 1.1 to 2.0.
  • L a is a polyisobutylenyl group with a number average molecular weight M n of 300 to 1000 and L b is a polyisobutylenyl group with a number average molecular weight M n of 2000 to 20,000,
  • -A- stands for -O- -N (H) - or -N (R ! ) -
  • M * stands for Ff 1 " , an alkali metal ion, 0.5 alkaline earth metal ions or NELt 4" , it being possible for one or more H in NHt + to be replaced by alkyl radicals,
  • R represents a linear or branched saturated hydrocarbon radical which bears at least one substituent selected from the group OH, NH 2 or NH 3 + and optionally one or more C (O) H groups and optionally one or more non-adjacent -O- and / or contains secondary amines and or tertiary amines, and wherein one or more H in the NH 2 - or NH 3 + groups can be replaced by alkyl radicals, and
  • R 1 stands for a linear or branched saturated hydrocarbon radical which optionally carries one or more substituents selected from the group OH, NH 2 , NH 3 + or C (O) H and optionally one or more non-adjacent -O- and / or contains secondary amines and / or tertiary amines, and wherein one or more H in the NH 2 - or NH 3 + groups can be replaced by alkyl radicals, and
  • the proportion of A - R in the compound of the general formula (Ia) is at least 10% by weight and in the compound of the general formula (Ib) at least 20
  • Effective emulsifier mixtures are obtained not only when using compounds of the general formula (Ia) with hydrophilic parts of at least 20% by weight, but also when using compounds of the general formula (Ia) with hydrophilic parts of at least 10% by weight.
  • n is from 350 to 950, in particular from 350 to 650, and / or the proportion of AR in the connection of the general formula (Ia) is at least 15% by weight, preferably at least 20% by weight, particularly preferably at least 25% by weight, very particularly preferably 35 to 60% by weight.
  • L b is a polyisobutylenyl group with a number average molecular weight M n of 2000 to 12000, in particular from 2300 to 5000, and or the proportion of AR in the compound of the general formula (Ib) is at least 25% by weight, in particular 35 to 60% by weight.
  • the present invention also relates to processes for the preparation of the compounds of the general formula (Ia) or (Ib).
  • polyisobutylene with fumaric acid dichloride, fumaric acid, maleic acid dichloride, maleic anhydride or maleic acid preferably with maleic anhydride or maleic acid dichloride, particularly preferably with maleic anhydride
  • the reaction is carried out by the processes known to the person skilled in the art and, for example, analogously to the processes for the reaction of polyisobutylenes with maleic anhydride described in German Offenlegungsschriften DE-A 195 19 042, DE-A 43 19 671 and DE-A 43 19 672.
  • the number average molecular weight M n of the resulting succinic anhydride derivative, which is substituted by a polyisobutylenyl group can be characterized by the saponification number [mg KOH / g substance].
  • R is a linear or branched saturated hydrocarbon radical which has at least one substituent selected from the group OH, NH 2 or NH 3 + and optionally one or more C (O) H groups and optionally contains one or more non-adjacent -O- and / or secondary amines and / or tertiary amines, and wherein in the NH 2 - or NH + groups one or more H may be replaced by alkyl radicals, and
  • R 1 stands for a linear or branched saturated hydrocarbon radical which optionally carries one or more substituents selected from the group OH, NH 2 , NH 3 + or C (O) H and optionally one or more non-adjacent -O- and / or contains secondary amines and / or tertiary amines, and one or more H in the NH - or NH + groups can be replaced by alkyl radicals.
  • alkyl radicals that can replace the H atoms are - - alkyl radicals.
  • Suitable polar reactants ROH and RR ⁇ H are alkanolamines, polyamines, oligoalcohols, polyols, oligoalkylene glycols, polyalkylene glycols as well as carbohydrates and sugar.
  • Polar reactants can also be ethylene oxide and / or propylene oxide. The reaction with polyethylene glycol, polypropylene glycol, their (block) copolymers, ethylene oxide or propylene oxide is preferred.
  • reaction with alkanolamines such as di- / triethanolamine, tris (hydroxymethyl) aminomethane and their salts, oligoalcohols such as sorbitol and pentaerythritol or carbohydrates and sugars is also preferred.
  • alkanolamines such as di- / triethanolamine, tris (hydroxymethyl) aminomethane and their salts, oligoalcohols such as sorbitol and pentaerythritol or carbohydrates and sugars is also preferred.
  • the reaction with tris (hydroxymethyl) aminomethane, choline, sugars and polyethylene glycol is particularly preferred for the preparation of compounds of the general formula (Ia).
  • the amount of polar reactant is chosen so that the proportion of the hydrophilic radical AR in the compound of general formula (Ia) or (Ib) is at least 20 % By weight, preferably 25% by weight, particularly preferably 35 to 60% by weight.
  • Compounds of the general formula (Ia) in which the hydrophilic content is 10 to 20% by weight can also be prepared by the processes described.
  • the conversion ratio of the substituted succinic acid derivatives (Ha), (üb) or (IIc) to the alkanolamines, polyamines, oligoalcohols, polyols, oligoalkylene glycols or polyalkylene glycols is generally 1: (0.75 to 2), preferably 1: (0.8 to 1.2), particularly preferably 1: 1.
  • the amount of ethylene and / or propylene oxide is selected in accordance with the desired chain length of the hydrophilic radical AR.
  • succinic acid semiesters or half amides are obtained.
  • alkanolamines the hydroxyl and / or amino groups react, so that mixtures of succinic acid and succinic acid halamides are generally obtained.
  • maleic or fumaric acid dichloride is used as the starting material, the C (O) Cl group still present after the reaction steps mentioned is hydrolyzed to the CO 2 H group.
  • the free CO 2 H group present in the succinic acid semiesters and half amides can then be reacted with NH 3 , amines, alkali metal or alkaline earth metal salts to give the corresponding A 1, alkali metal or alkaline earth metal salts.
  • salts are compounds of the general formula (Ia) or (Ib) in which M * "is an alkali metal ion, 0.5 alkaline earth metal ion or NEU, where one or more H in NELi * can be replaced by alkyl radicals
  • Suitable amines for salt formation are primary, secondary and tertiary amines which carry linear C 1 -C 4 or branched C 3 -C 6 alkyl groups.These alkyl groups can also be substituted by one or more hydroxyl groups.
  • suitable alkyl amines are Diethylamine, diisopropylamine, trimethylamine, mono-, di- and triethanolamine and tris (hydroxymethyl) aminomethane.
  • polyisobutylenes with a number average molecular weight M n of 300 to 1000, preferably from 350 to 950, particularly preferably from 350 to 650, are used to prepare the compounds of the general formula (Ia).
  • polyisobutylenes with a number average molecular weight M n of 2,000 to 20,000, preferably from 2,000 to 12,000, particularly preferably from 2,300 to 5,000, are generally used.
  • polyisobutylenes with a number-average molecular weight M n in the ranges mentioned preference is given to those which have a high content of vinylidene groups.
  • Polyisobutylenes which have a number-average molecular weight M n in the abovementioned ranges, a high content of vinylidene groups and a uniform polymer skeleton structure are particularly preferably used.
  • polyisobutylenes with a number-average molecular weight M n in the ranges mentioned, a high content of vinylidene groups and a uniform structure, which have a polydispersity pers 3.0, preferably from 1.1 to 2.5, particularly preferably from 1.1 to 2.0.
  • Polydispersity means the quotient M w / M n from the weight-average molecular weight M w and the number-average molecular weight M n .
  • Polyisobutylenes with a number average molecular weight M n in the ranges mentioned, which are essentially composed of isobutylene units and have a high content of vinylidene groups, are available, for example, from BASF AG under the trade name Glissopal®, such as Glissopal® 1000 with an M n of 1000 , Glissopal® V 33 with an M n of 550 and Glissopal® 2300 with an M n of 2300.
  • Glissopal® such as Glissopal® 1000 with an M n of 1000
  • Glissopal® V 33 with an M n of 550 and Glissopal® 2300 with an M n of 2300.
  • suitable alkanolamines, polyamines, oligoalcohols, polyols and polyalkylene glycols which can be used for the preparation of the compounds according to the invention are described in WO 00/15740.
  • alkanolamines are monoethanolamine, diethanolamine, 2-amino-1-butanol, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1, 3-propanediol, 2-amino-2-ethyl- 1,3-propanediol, N- (2-hydroxypropyl) -N '- (2-aminoethyl) piperazine, tris (hydroxymethyl) amino-methane, 2-amino-1-butanol, ß- (2-hydroxyethoxy) ethylamine, glucamine , Glucosamine, 4-amino-3-hydroxy-3-methyl-1-butene, N- (3-aminopropyl) -4- (2-hydroxyethyl) piperidine, 2-amino-6-methyl-6-heptanol, 5- Amino-1-pentanol, N- (2-hydroxyethyl) -l, 3-diaminopropane
  • the salts of the alkanolamines mentioned can also be used.
  • one or more of the H atoms bound to N atoms can optionally be replaced by linear d-C ⁇ -alkyl or branched C 3 -C 6 -alkyl groups.
  • Choline may be mentioned as an example.
  • polyalkylene polyamines such as polymethylene polyamines, polyethylene polyamines, polypropylene polyamines, polybutylene polyamines and polypentylene polyamines; see also “Ethylene Amines” in Kirk Othmer's “Encyclopedia of Chemical Technology", 2nd Edition, Volume 7, pp. 22-37, Interscience Publishers, New York 1965.
  • oligoalcohols and polyols examples include 1,2-butanediol, 2,3-dimethyl-2,3-butanediol, 2,3-hexanediol, 1,2-cyclohexanediol, (mono-, di-) - pentaerythritol, 1.7 - and 2,4- heptanediol, 1,2,3-, 1,2,4-, 1,2,5- and 2,3, 4-hexanetriol, 1,2,3- and 1,2,4- Butanetriol, 2,2,6,6-tetrakis (hydroxymethyl) cyclohexanol, 1,10-decanediol, 2-hydroxymethyl-2-methyl-1,3-propanediol, 2-hydroxymethyl-2-ethyl-1,3-propanediol, Sorbitol, mannitol and inositol.
  • C 5 and C 6 sugars such as glucose and fructose are also
  • Examples of (oligo) alkylene glycols are (tri, tetra, penta-, hexa-) ethylene glycol, (tri-, tetra-, penta-, hexa-) propylene glycol and (tri-, tetra-, penta-, hexa-) butylene glycol.
  • Examples of polyalkylene glycols are polytetrahydrofuran, polyethylene glycol and polypropylene glycol.
  • Preferred polyalkylene glycols are polyethylene glycol and polypropylene glycol.
  • Polyethylene glycol and polypropylene glycol and their block copolymers are particularly preferred which have a number average molecular weight M n of 300 to 5000, preferably 300 to 2000, particularly preferably 500 to 1500.
  • Such polyethylene glycols are available, for example, under the trade name Pluriol® E from BASF AG, such as Pluriol® E 300 with an M n of 300, Pluriol® E 600 with an M "of 600, Pluriol® E 4000 with an M" of 4000 and Pluriol® E 5000 with an M n of 5000.
  • Polyethylene-polypropylene glycol block copolymers are available, for example, from BASF AG under the trade name Pluronic® PE, such as Pluronic® PE 3500 with an M n of 1900 and an ethylene oxide content of 50% by weight.
  • the compounds according to the invention and or the mixtures according to the invention are used in oil-in-water emulsions, stable vesicles can be produced. This can be done, for example, by the action of ultrasound.
  • the compounds of the invention and / or the mixtures of the invention can also be used in a variety of ways, e.g. B. as additives in fuels and lubricants, as a corrosion-inhibiting additive in water-containing liquids and as dispersants for inorganic and organic solid dispersions.
  • the compounds according to the invention and / or the mixtures according to the invention can also be used as surfactants for washing and cleaning formulations.
  • the high-molecular compounds of the general formula (Ib) which contain a monovalent residue of a polyethylene glycol as a hydrophilic block are particularly suitable for stabilizing inorganic and organic solid dispersions.
  • the compounds according to the invention and / or mixtures according to the invention are also suitable as emulsifiers for water-in-oil emulsions in which the oil phase is formed from a vegetable, animal or synthetic oil or fat.
  • emulsifiers for water-in-oil emulsions in which the oil phase is formed from a vegetable, animal or synthetic oil or fat.
  • oils or fats are triglycerides and glycol esters of lauric acid, myristic acid, stearic acid, palmitic acid, oleic acid, linoleic acid and linolenic acid.
  • the compounds and / or mixtures according to the invention are particularly advantageously used as emulsifiers for water-in-oil emulsions, in which the oil phase is formed by a fuel, light or heavy heating oil.
  • a fuel light or heavy heating oil.
  • All common types of fuel can be used, for example diesel fuel, petrol and kerosene. Diesel fuel is preferably used.
  • Water-in-oil emulsions according to the invention generally contain 95 up to 60% by weight of oil, 3 to 35% by weight of water and 0.2 to 10% by weight of at least one compound according to the invention and / or a mixture according to the invention.
  • Water-in-fuel emulsions according to the invention can also contain one or more C 4 alcohols and / or monoethylene glycol, in particular monoethylene glycol.
  • the amount of C 1 -C 4 alcohol and / or monoethylene glycol used is from 5 to 50% by weight, based on the amount of water.
  • the temperature range in which the emulsion is stable can be broadened.
  • the water-in-fuel emulsions according to the invention have high stability and good combustion efficiency. Good exhaust gas values can still be obtained, the emission of soot and NO x being significantly reduced, particularly in the case of diesel engines. A largely complete and residue-free combustion can be achieved without deposits on the assemblies of the combustion apparatus, for example injection nozzles, pistons, annular grooves, valves and cylinder head.
  • the water-in-fuel emulsions according to the present invention can have further components in addition to the components mentioned above. These are, for example, other emulsifiers such as sodium lauryl sulfate, quaternary ammonium salts such as
  • Sorbitan monooleate, C 13 oxo alcohol ethoxylates and alkylphenol ethoxylates, for example octyl and nonylphenol ethoxylates, are preferably used as further emulsifiers.
  • a combination of one or more of the above-mentioned further emulsifiers together with the compounds according to the invention and / or mixtures thereof is preferably used for the water-in-fuel emulsions according to the invention.
  • these further emulsifiers are used, this is done in amounts of 0.5 to 5% by weight, preferably 1 to 2.5% by weight, based on the overall composition.
  • the amount of this further emulsifier is chosen so that the total amount of emulsifier does not exceed the amount of 0.2 to 10% by weight given for the compounds according to the invention and their mixtures alone.
  • the compounds and / or mixtures according to the invention are mixed with the oil, the water and the further, optionally usable components and emulsified in a manner known per se.
  • the emulsification can be carried out in a rotor mixer, by means of a mixing nozzle or by an ultrasound probe. Particularly good results were achieved when a mixing nozzle of the type used as disclosed in German application, file number: 198 56 604 by the applicant on December 8, 1998 was used.
  • Water-in-oil emulsions for the cosmetics sector can be produced as well as water-in-fuel emulsions.
  • the compounds and / or mixtures according to the invention also have a lubricity-improving and corrosion-inhibiting effect. They also improve the wear protection behavior of liquids.
  • the compounds and / or mixtures according to the invention are therefore used as additives for lubricants, fuels and water-containing liquids such as coolant liquids or drilling and cutting liquids. This use is also the subject of the present invention.
  • the compounds and / or mixtures according to the invention can be added directly to the fuels and lubricants — together with other components.
  • the compounds according to the invention and or mixtures according to the invention can first be mixed with other components to give fuel or lubricant additive concentrates.
  • These fuel or lubricant additive concentrates according to the invention can be added to the fuels or lubricants undiluted or diluted with one or more solvents or carrier oils. The addition in dilute form is preferred.
  • the fuels, lubricants, fuel additive and lubricant additive concentrates, and also water-containing liquids which contain the compounds and / or mixtures according to the invention are likewise the subject of the present invention and are to be explained in more detail below.
  • Fuels according to the invention generally contain - in addition to conventional components - at least one compound according to the invention and / or a mixture according to the invention in an amount of 10 to 5000 ppm, preferably in an amount of 20 to 2000 ppm, based on the total amount.
  • Lubricants according to the invention generally contain between 90 and 99.9% by weight, preferably between 95 and 99.5% by weight, of a liquid, semi-solid or solid lubricant and between 0.1 and 10% by weight, preferably between 0 , 5 and 5 wt .-% of at least one compound according to the invention and / or a mixture according to the invention, based on the total amount.
  • Fuel additive and lubricant additive concentrates according to the invention contain - in addition to conventional components - at least one compound according to the invention and / or a mixture according to the invention in proportions of 0.1 to 80% by weight, in particular 0.5 to 60% by weight, based on the total weight of the concentrate.
  • Typical components for fuels or fuel additive concentrates are, for example, additives with detergent action, as described in the applicant's German application, file number 100 36 956.1, dated July 28, 2000 (page 14 ff.), In the applicant's German application, file number 100 03 105.6, dated 25.1.2000 and in the PCT application of the applicant with the file number PCT / EP / 01/00496.
  • the additives mentioned there and other fuel additives described there with polar Generations are part of the present application and are incorporated by reference.
  • the fuels and fuel additive concentrates according to the invention can also contain fuel additives as described, for example, in European patent applications EP-A 0 277 345, 0 356 725, 0 476 485, 0 484 736, 0 539 821, 0 543 225, 0 548 617, 0 561 214, 0 567 810, 0 568 873, German patent applications DE-A 39 42 860, 43 09 074, 43 09 271, 43 13 088, 44 12 489, 44 25 834, 195 25 938, 196 06 845, 196 06 846, 196 15 404, 196 06 844, 196 16 569, 196 18 270, 196 14 349, and WO-A 96/03479.
  • biocides such as glutardialdehyde or glyoxal.
  • the biocides are usually used in an amount of 0.01 to 3% by weight, based on the total weight of the concentrate.
  • further corrosion-inhibiting additives are those based on ammonium salts of organic carboxylic acids, which tend to form films, or on heterocyclic aromatics in the case of non-ferrous metal corrosion protection.
  • stabilizers are those based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or on phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid.
  • organometallic compounds examples include ferrocene or methylcyclopentadienylmanganese tricarbonyl.
  • cetane number improvers are organic C -C 10 nitrates such as 2-ethylhexyl nitrate, and inorganic cetane number improvers for the aqueous phase such as ammonium nitrate. 2-Ethylhexyl nitrate and ammonium nitrate are preferably used.
  • the cetane number improvers are usually used in an amount of 0.05 to 5% by weight, based on the total weight of the concentrate.
  • Solvents for the fuel and lubricant additive concentrates according to the invention are aliphatic and aromatic hydrocarbons such as solvent naphtha, isododecane, mihagol (a technical mixture of the fuels and lubricants themselves as well as carrier oils.
  • Carrier oils which also serve to dilute the fuel and lubricant additive concentrates, are, for example, mineral carrier oils (base oils), in particular those of the viscosity class "Solvent Neutral (SN) 100 to 500", as well as synthetic carrier oils based on polyolefins, (poly) esters, ( Alkylphenol-started) polyethers, (aliphatic) (alkylphenol-started) polyetheramines, and carrier oils based on alkoxylated long-chain alcohols or phenols.
  • base oils mineral carrier oils
  • base oils in particular those of the viscosity class "Solvent Neutral (SN) 100 to 500”
  • synthetic carrier oils based on polyolefins polyolefins
  • poly poly esters
  • Alkylphenol-started polyethers Alkylphenol-started polyethers
  • aliphatic alkylphenol-started polyetheramines
  • carrier oils based on alkoxylated long-chain alcohols or phenols.
  • Polyethylene oxides, polypropylene oxides, polybutene oxides and mixtures thereof are also suitable carrier oils. Further suitable carrier oils and carrier oil mixtures are described, for example, in the publications DE-A 38 38 918, DE-A 38 26 608, DE-A 41 42241, DE-A 43 09074, US 4,877,416 and EP-A 0452 328.
  • Water-containing liquids according to the invention contain the compounds and / or mixtures according to the invention, if appropriate in combination with other customary corrosion-inhibiting additives, generally in a proportion of about 1 to 10% by weight, based on the total amount.
  • composition of the compounds produced can be found in Table 1.
  • Glissopal® from BASF AG with a number average molecular weight M n of 380 to 8400 and a proportion of vinylidene end groups of> 70 was used as polyisobutylene
  • Pluriol® E from BASF AG with a number average molecular weight M n of 300 to 5000 was used as the polyethylene glycol.
  • Pluronic® PE 3500 from BASF AG with a number-average molecular weight M n of 1900 and an ethylene oxide content of 50% by weight was used as the polyethylene / polypropylene-glycol block copolymer.
  • Heptane Mihagol, a mixture of C 10 -C 12 paraffins from Wintershall, and Solvesso® 150, a mixture of aromatic hydrocarbons from ExxonMobil Chemical, were used as solvents.
  • Clariant commercially available under the name Ambossol®, was used as the ion exchanger.
  • the compounds obtained were characterized via the acid number, the OH number, the viscosity and / or the IR spectra.
  • the OH number was determined using solvent when using high-boiling solvents, i. H. that the OH number of the compounds in the respective solvent was measured and then extrapolated to the pure substance.
  • high-boiling solvents i. H. that the OH number of the compounds in the respective solvent was measured and then extrapolated to the pure substance.
  • low-boiling solvents such as heptane
  • the solvent was removed by distillation and the OH number was determined from the pure substance.
  • Table 1 Composition of the compounds of the general formula (Ia) or (Ib)
  • An 11 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 250 g PIBSA 550 and heated to 90 ° C. 67 g of diethanolamine are metered in via a dropping funnel within 5 minutes. The mixture is gradually heated to 130 ° C or 170 ° C. After 2 hours at 170 ° C, the brown reaction product is filtered at 100 ° C.
  • An 11 four-necked flask with stirrer, distillation bridge and thermocouple is filled with 310 g PIBSA 750 and 60 g D-sorbitol.
  • the mixture is gradually heated to 160 ° C or 220 ° C. Released water is removed using a stream of nitrogen; after 3 hours at 220 ° C, diluted with 200 g of Mihagol and filtered hot. A yellow, viscous product solution (65%) is obtained.
  • a 21 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 350 g Pluriol® E 300 and degassed at 90 ° C for 30 minutes in a vacuum.
  • a solution of 650 g of PIBSA 380 in 350 g of heptane is metered into a dropping funnel at 80 ° C. in the course of 5 minutes. The mixture is gradually heated to 110 ° C or 140 ° C. Heptane is distilled off under reduced pressure (350 mbar).
  • a 21 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 300 g Pluriol® E 300 and degassed at 90 ° C for 30 minutes in a vacuum.
  • a solution of 750 g of PIBSA 550 in 450 g of heptane is metered into a dropping funnel at 80 ° C. within 5 minutes. The mixture is gradually heated to 110 ° C or 140 ° C. Heptane is distilled off under reduced pressure (350 mbar). After 3 hours at 140 ° C, 105 g of diethanolamine are added in portions at 95 ° C. After a further 20 minutes at 95 ° C, the orange-brown product is filtered hot. OH number: 55; IR: intense band at 1736 cm "1 (ester).
  • a 21 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 400 g Pluriol® E 600 and degassed in a vacuum at 90 ° C for 30 minutes.
  • a solution of 790 g of PIBSA 1000 in 450 g of heptane is metered in at 80 ° C. in the course of 5 minutes.
  • the mixture is gradually heated to 110 ° C or 140 ° C.
  • Heptane is distilled off under reduced pressure (350 mbar). After 3 hours at 140 ° C., a yellow product with a viscosity of 1650 mm 2 / s (100 ° C.) is obtained.
  • An 11 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 150 g Pluriol® E 4000 and degassed in a vacuum at 90 ° C for 30 minutes.
  • a solution of 250 g PIBSA 5200 in 300 g Mihagol is dosed within 5 minutes at 80 ° C using a dropping funnel.
  • the mixture is gradually heated to 110 ° C or 140 ° C. After 3 hours at 140 ° C, a beige wax is obtained.
  • the product is isolated as a cream-colored wax (60% in Mihagol); IR: 1737 cm “1 .
  • the product is isolated as an orange-yellow, highly viscous liquid. Viscosity: 2100 mm / s; 100 ° C.
  • An 11 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 75 g of a 45% methanolic solution of choline from Fluka and 150 g of Mihagol. Methanol is then removed at 50 ° C and reduced pressure (50 mbar) (45 minutes). 200 g of PIBSA 550 are added to this suspension and the mixture is heated to 90 ° C. in the course of 15 minutes. After 60 minutes, the temperature is raised to 170 ° C. and the mixture is stirred for a further two hours. The brown reaction product is filtered at 100 ° C.
  • An 11 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 300 g PIBSA 2300, 200 g PIBSA 1000 and 200 g Mihagol and heated to 95 ° C. 17.2 g of ethylene glycol are metered in at 95.degree. The mixture is heated to 130 ° C. and stirred at this temperature for three hours. The brown reaction product is filtered at 100 ° C.
  • the emulsifier of comparative example 2 was produced according to the principle of WO 00/15740 according to example C-1, p. 34.
  • a 21 four-necked flask with stirrer, dropping funnel and thermocouple is filled with 100 g Pluriol® E 200 and degassed in a vacuum at 90 ° C for 30 minutes.
  • a solution of 590 g of PIBSA 1000 in 450 g of heptane is metered into a dropping funnel at 80 ° C. within 5 minutes.
  • the mixture is gradually heated to 110 ° C or 140 ° C.
  • Heptane is distilled off under reduced pressure (350 mbar). After 3 hours at 140 ° C., an amber-colored product with a viscosity of 1450 mm 2 / s (100 ° C.) is obtained.
  • the hydrophilic or water-soluble components were previously dissolved in the aqueous phase, lipophilic components in the diesel oil.
  • an Ultra-Turrax® (Jahnke and Kunkel laboratory device T25) 500 g of this mixture were homogenized with 100 ml water for 15 minutes at a speed of 24000 / min.
  • the emulsion was produced on an industrial scale and the motor tests were carried out analogously to DE-A 198 56 604 by the applicant (registered on December 8, 1998), with a mixing nozzle described there.
  • the pressure in the mixing apparatus was 50 to 200 bar (in front of the orifice), preferably 120 bar, with a conversion of (total) 12 kg / h.
  • Example 3 Studies on the stability of the water-in-fuel emulsions
  • the size of the water drops was physically determined by laser diffraction (X3, 2 values) using a Malvem Mastersizer 2000 from Malvem Instruments GmbH. The measurement method is described, for example, in Terence Allen, Particle Size Measurement, Volume 1, 5 ft Edition, Kluwer Academic Publishers, Dordrecht, Netherlands 1999. Depending on the actual size distribution, there are other methods besides laser light diffraction such as: B. the dynamic light scattering, single particle counter and ultrasonic extinction in question.
  • the size of the water drops is a measure of the quality of the emulsion.
  • the corresponding values for the drop size (the X3, 2 values) are summarized in Table 3.
  • Table 3 the emulsions using the compounds according to the invention and also the mixtures according to the invention sometimes have significantly smaller drop sizes than the comparison emulsions.
  • the fact that the drop size is really a measure of the stability of the emulsion at room temperature is shown by the stability values determined by storage tests.
  • the emulsions with larger droplet sizes also have poorer storage stability.
  • the stability of the emulsions was checked in a static storage test at 20 ° C (for 12 weeks) and additionally under changing temperatures (-20 ° C and 70 ° C, each for 1 week).
  • the emulsion was filled into a scaled 100 ml standing cylinder and its quality was assessed visually in accordance with the specified conditions.
  • the storage tests at -20 ° C were then assessed at room temperature.
  • the emulsion according to Example 2 is comparatively homogeneous even without the addition of anti-freeze (e.g. monoethylene glycol). Otherwise, phase separation, a so-called "breaking" of the emulsion, took place after or even when heated.
  • anti-freeze e.g. monoethylene glycol
  • Example 4 Use of the compounds of the general formula (I) according to the invention as rust protection and wear protection additives
  • a 20 x 40 mm sheet of iron is blasted with 40 ⁇ m glass beads and then - based on ASTM D-665 - immersed in the emulsions prepared in Example 2 and stored at 40 ⁇ 1 ° C for 24 hours. After 24 hours, the iron sheet is examined for rust formation.
  • ASTM D-665 - immersed in the emulsions prepared in Example 2 and stored at 40 ⁇ 1 ° C for 24 hours. After 24 hours, the iron sheet is examined for rust formation.
  • Example 5 Use of the compounds of the general formula (I) according to the invention in fuels and their wear protection behavior
  • the connections listed in the table were solved in an unadditized diesel fuel (Miro, Düsseldorf).
  • the concentration of additive in the diesel fuel was 75 ppm.
  • the wear protection behavior was assessed using the HFRR test (High Frequency Roller Rig Test), which was carried out in accordance with ISO 12156-1.
  • the length of the resulting grooves was measured and used as a measure of wear. The shorter the scoring, the better the wear protection of the additive added. Unaddivated diesel fuel was used for comparison.
  • Table 4 the compounds according to the invention protected against wear.

Abstract

L'invention concerne des émulsifiants à deux blocs de masses moléculaires faibles et élevées, notamment à base de polyisobutylène, de la formule générale (Ia) et (Ib), ainsi que les mélanges de ces émulsifiants. Selon l'invention, La est un groupe polyisobutylène de masse molaire moyenne M¿n? de 300 à 1000, et L?b¿ est un groupe polyisobutylène de masse molaire moyenne M¿n? de 2000 à 20000 ; -A- est -O-, -N(H)- ou N(R?1)- ; M+ est H+¿, un ion de métaux alcalins, 0,5 ions de métaux alcalins ou NH¿4?+, un ou plusieurs H pouvant être remplacés par des restes alkyle dans NH¿4?+ ; R est un reste hydrocarbure saturé, linéaire ou ramifié, portant au moins un substituant choisi dans le groupe OH, NH¿2? ou NH3?+¿, et éventuellement un ou plusieurs groupes C(O)H, et éventuellement un ou plusieurs O- non adjacents et/ou des amines secondaires et/ou des amines tertiaires, un ou plusieurs H pouvant être remplacés par des restes alkyle dans les groupes NH¿2?- ou NH3?+¿ ; et, R1 est un reste hydrocarbure saturé, linéaire ou ramifié, portant éventuellement un substituant choisi dans le groupe OH, NH¿2? ou NH3?+¿ ou C(O)H, et éventuellement un ou plusieurs -O- non adjacents et/ou des amines secondaires et/ou des amines tertiaires, un ou plusieurs H pouvant être remplacés par des restes alkyle dans les groupes NH¿2?- ou NH3?+¿, et la teneur en A-R du composé de formule générale (Ib) étant d'au moins 20 % en poids.
PCT/EP2002/005516 2001-05-22 2002-05-17 Emulsifiants de masses moleculaires faibles et elevees a base de polyisobutylene, et melanges de ces emulsifiants WO2002094889A2 (fr)

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AU2002338977A AU2002338977A1 (en) 2001-05-22 2002-05-17 Low-molecular and high-molecular emulsifiers, particularly based on polyisobutylene, and mixtures thereof
CA002448033A CA2448033A1 (fr) 2001-05-22 2002-05-17 Emulsifiants de masses moleculaires faibles et elevees a base de polyisobutylene, et melanges de ces emulsifiants
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DE10125158A DE10125158A1 (de) 2001-05-22 2001-05-22 Nieder-und hochmolekulare Emulgatoren, insbesondere auf Bassis von Polyisobutylen, sowie deren Mischungen
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Cited By (9)

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Publication number Priority date Publication date Assignee Title
WO2003085011A1 (fr) * 2002-04-05 2003-10-16 Basf Aktiengesellschaft Polyisobutene-amines
WO2004055137A1 (fr) * 2002-12-13 2004-07-01 The Lubrizol Corporation Carburants emulsionnes melanges a de l'eau produits par un procede a faible consommation d'energie et nouveau tensioactif
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WO2005018321A1 (fr) * 2003-08-18 2005-03-03 Basf Aktiengesellschaft Utilisation de certains copolymeres comme adjuvants et agents destines au domaine agrotechnique
WO2007014915A1 (fr) * 2005-08-04 2007-02-08 Basf Se Dispersions aqueuses et leur utilisation
DE112006003163T5 (de) 2005-11-29 2009-01-29 Akzo Nobel N.V. Grenzflächenaktives Polymer und seine Verwendung in einer Wasser-in-Öl-Emulsion
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WO2017016909A1 (fr) * 2015-07-24 2017-02-02 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants
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DE10147650A1 (de) * 2001-09-27 2003-04-10 Basf Ag Hydrophile Emulgatoren auf Basis von Polyisobutylen
US8511259B2 (en) * 2002-03-28 2013-08-20 Cam Technologie S.P.A. Method for reducing emission of pollutants from an internal combusion engine, and fuel emulsion comprising water and a liquid hydrocarbon
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MX2007014194A (es) * 2005-05-30 2008-02-07 Basf Ag Composicion de polimero que comprende poliolefinas y copolimeros de bloque anfifilicos y opcionalmente otros polimeros y/o rellenos y metodo para tenir composiciones de ese tipo o imprimir en los mismos.
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JP4131748B1 (ja) * 2008-01-16 2008-08-13 株式会社タイホーコーザイ 燃料添加剤
GB201003579D0 (en) * 2010-03-04 2010-04-21 Croda Int Plc Friction reducing additive
MX340883B (es) * 2010-05-12 2016-07-29 Basf Se Emulsiones de poliisobutenos, sustancia y proceso.
US20120010112A1 (en) 2010-07-06 2012-01-12 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
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RU2610439C2 (ru) * 2011-11-11 2017-02-10 Басф Се Самоэмульгируемые полиолефиновые композиции
US8759274B2 (en) 2011-11-11 2014-06-24 Basf Se Self-emulsifiable polyolefine compositions
WO2013068272A1 (fr) 2011-11-11 2013-05-16 Basf Se Compositions de polyoléfines auto-émulsifiables
CA2878830C (fr) * 2012-07-16 2019-02-19 Emulco Laboratories C.V.B.A. Procede pour la preparation d'emulsions stables de polyisobutene
SG11201500299UA (en) * 2012-07-16 2015-03-30 Emulco Lab C V B A Stable emulsions of polyisobutene and their use
WO2014150663A1 (fr) * 2013-03-15 2014-09-25 Cytec Industries Inc. Inhibiteurs de corrosion et leurs procédés d'utilisation
KR101904585B1 (ko) 2015-02-17 2018-10-08 주식회사 엘지화학 변성 이소부틸렌-이소프렌 고무, 이의 제조방법 및 경화물
US10597576B2 (en) 2015-11-02 2020-03-24 The Lubrizol Corporation Lubricant for water based drilling fluid
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US10479953B2 (en) * 2018-01-12 2019-11-19 Afton Chemical Corporation Emulsifier for use in lubricating oil
JP7400806B2 (ja) * 2019-03-14 2023-12-19 日油株式会社 潤滑油用添加剤、潤滑油用添加剤組成物およびこれらを含有する潤滑油組成物
CN115895752A (zh) 2021-09-30 2023-04-04 中国石油化工股份有限公司 一种抗磨添加剂、其制备方法及在油品中的应用

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3522179A (en) * 1963-04-23 1970-07-28 Lubrizol Corp Lubricating composition containing esters of hydrocarbon-substituted succinic acid
FR2369240A1 (fr) * 1976-10-28 1978-05-26 Shell Int Research Esterification d'anhydrides hydrocarbyl-succiniques
US4368133A (en) * 1979-04-02 1983-01-11 The Lubrizol Corporation Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives
GB2231873A (en) * 1989-03-10 1990-11-28 Shell Int Research Lubricating compositions
EP0658572A1 (fr) * 1993-12-16 1995-06-21 Mol Magyar Olaj Es Gazipari Reszvenytarsasag Mélanges sans cendres d'additifs polymères dispersants et détergents, leur procédé de préparation
WO1998023843A1 (fr) * 1996-11-22 1998-06-04 Clariant Gmbh Additifs pour empecher la formation d'hydrates de gaz
US5824372A (en) * 1996-03-13 1998-10-20 E. I. Du Pont De Nemours And Company Maleic acid copolymers with fluorinated thioether end cap
DE19941166A1 (de) * 1998-08-31 2000-05-04 Yokohama Rubber Co Ltd Polymer, enthaltend Isobutylen als wiederkehrende Einheit, und Gummizusammensetzung, enthaltend dasselbe

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4225447A (en) * 1979-01-08 1980-09-30 Mobil Oil Corporation Emulsifiable lubricant compositions
US4708753A (en) * 1985-12-06 1987-11-24 The Lubrizol Corporation Water-in-oil emulsions
US5858029A (en) * 1997-01-13 1999-01-12 Mobil Oil Corporation Friction reducing additives for fuels and lubricants

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3522179A (en) * 1963-04-23 1970-07-28 Lubrizol Corp Lubricating composition containing esters of hydrocarbon-substituted succinic acid
FR2369240A1 (fr) * 1976-10-28 1978-05-26 Shell Int Research Esterification d'anhydrides hydrocarbyl-succiniques
US4368133A (en) * 1979-04-02 1983-01-11 The Lubrizol Corporation Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives
GB2231873A (en) * 1989-03-10 1990-11-28 Shell Int Research Lubricating compositions
EP0658572A1 (fr) * 1993-12-16 1995-06-21 Mol Magyar Olaj Es Gazipari Reszvenytarsasag Mélanges sans cendres d'additifs polymères dispersants et détergents, leur procédé de préparation
US5824372A (en) * 1996-03-13 1998-10-20 E. I. Du Pont De Nemours And Company Maleic acid copolymers with fluorinated thioether end cap
WO1998023843A1 (fr) * 1996-11-22 1998-06-04 Clariant Gmbh Additifs pour empecher la formation d'hydrates de gaz
DE19941166A1 (de) * 1998-08-31 2000-05-04 Yokohama Rubber Co Ltd Polymer, enthaltend Isobutylen als wiederkehrende Einheit, und Gummizusammensetzung, enthaltend dasselbe

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003085011A1 (fr) * 2002-04-05 2003-10-16 Basf Aktiengesellschaft Polyisobutene-amines
US7291681B2 (en) 2002-04-05 2007-11-06 Basf Aktiengesellschaft Polyisobutenamines
WO2004055137A1 (fr) * 2002-12-13 2004-07-01 The Lubrizol Corporation Carburants emulsionnes melanges a de l'eau produits par un procede a faible consommation d'energie et nouveau tensioactif
US7674863B2 (en) 2003-06-27 2010-03-09 Chevron Oronite Company Llc Esterified copolymers of polyalkenes/unsaturated acidic reagents useful as lubricant and fuel additives
EP1491561A1 (fr) * 2003-06-27 2004-12-29 Chevron Oronite Company LLC Copolymères estérifiés de polyalkylènes et de composés d'acides carboxyliques insaturés, utiles comme additifs pour lubrifiants et carburants
US7256242B2 (en) 2003-06-27 2007-08-14 Chevron Oronite Company, Llc Esterified copolymers of polyalkenes/unsaturated acidic reagents useful as lubricant and fuel additives
US7863390B2 (en) 2003-06-27 2011-01-04 Chevron Oronise Company LLC Esterified copolymers of polyalkenes/unsaturated acidic reagents useful as lubricant and fuel additives
WO2005018321A1 (fr) * 2003-08-18 2005-03-03 Basf Aktiengesellschaft Utilisation de certains copolymeres comme adjuvants et agents destines au domaine agrotechnique
WO2007014915A1 (fr) * 2005-08-04 2007-02-08 Basf Se Dispersions aqueuses et leur utilisation
DE112006003163T5 (de) 2005-11-29 2009-01-29 Akzo Nobel N.V. Grenzflächenaktives Polymer und seine Verwendung in einer Wasser-in-Öl-Emulsion
US8044232B2 (en) 2005-11-29 2011-10-25 Akzo Nobel N.V. Surface-active polymer and its use in a water-in-oil emulsion
US10351791B2 (en) 2013-07-26 2019-07-16 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
US10626341B2 (en) 2013-07-26 2020-04-21 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
US11066617B2 (en) 2013-07-26 2021-07-20 Innospec Limited Quaternary ammonium compounds as fuel or lubricant additives
GB2535253A (en) * 2014-07-28 2016-08-17 Innospec Ltd Compositions and methods
US10087384B2 (en) 2014-07-28 2018-10-02 Innospec Limited Quaternary ammonium compounds and their use as fuel or lubricant additives
GB2535253B (en) * 2014-07-28 2019-04-17 Innospec Ltd Compositions and methods
AU2015295049B2 (en) * 2014-07-28 2019-07-11 Innospec Limited Quaternary ammonium compounds and their use as fuel or lubricant additives
WO2017016909A1 (fr) * 2015-07-24 2017-02-02 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants

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CN1511167A (zh) 2004-07-07
US20040154216A1 (en) 2004-08-12
DE10125158A1 (de) 2002-12-05
CA2448033A1 (fr) 2002-11-28
AU2002338977A1 (en) 2002-12-03
JP2004531614A (ja) 2004-10-14
EP1404726A2 (fr) 2004-04-07

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