WO1995030643A1 - Composes amides et imides et leur utilisation en tant qu'huiles lubrifiantes - Google Patents

Composes amides et imides et leur utilisation en tant qu'huiles lubrifiantes

Info

Publication number
WO1995030643A1
WO1995030643A1 PCT/GB1995/001014 GB9501014W WO9530643A1 WO 1995030643 A1 WO1995030643 A1 WO 1995030643A1 GB 9501014 W GB9501014 W GB 9501014W WO 9530643 A1 WO9530643 A1 WO 9530643A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
groups
blocked
alkyl
oil
Prior art date
Application number
PCT/GB1995/001014
Other languages
English (en)
Inventor
Kevin Wall
Pauline William Zard
David James Barclay-Miller
David William Martin
Original Assignee
The Burwood Corporation Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB9408613A external-priority patent/GB9408613D0/en
Application filed by The Burwood Corporation Limited filed Critical The Burwood Corporation Limited
Priority to GB9622227A priority Critical patent/GB2303133B/en
Priority to AU23502/95A priority patent/AU2350295A/en
Publication of WO1995030643A1 publication Critical patent/WO1995030643A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/41—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/34—Organic liquids
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C10M105/68—Amides; Imides

Definitions

  • the present invention relates to a compound.
  • the present invention relates to a polyamide or polyimide.
  • the present invention relates to the application of a poiyamide or a polyimide compound for use as a synthetic lubricant oil in applications such as oil- based drilling muds and machine cutting fluids, especially where resistance to hydrolytic breakdown at high temperature is required.
  • esters or polyesters There are problems associated with the known oils.
  • the esters are subject to hydrolysis at high temperature. Breakdown of the esters results not only in a loss of the expensive oil, but the alcohols are water soluble and can cause upset in the osmotic pressure balance of the aqueous phase.
  • the present invention seeks to overcome some or all of those problems.
  • an end-blocked polyamide or an end-blocked polyimide in or as a lubricant oil, especially a lubricant oil for use in well-bore drilling fluids.
  • a well-bore drilling process comprising use of an end-blocked polyamide or an end-blocked polyimide in or as a well-bore drilling fluid.
  • a well-bore drilling fluid comprising an end-blocked polyamide or an end-blocked polyimide.
  • each of w, x, y and z independently has an average value of from 0 to 6; each of n, u and v independently has an average value of from 0 to 1; u+v+x.(l+n)+z.(l+n)>2; and R 1 , R 2 , R 3 , R 4 and R 5 independently are organic groups.
  • each of w, x, y, z, n, u, v, R 1 , R 2 , R 3 , R 4 and R 5 need not be the same.
  • each R 3 can be different.
  • the present invention also covers compositions comprising the compound of the present invention.
  • a key advantage of the compound of the present invention is that it is biodegradable and nontoxic, allowing its use in environmentally sensitive areas in such applications such as outboard engine and chain saw lubricants.
  • the polyamide and/or the polyimide is obtainable from reacting a first entity having two reactive functional groups, which may be the same or different, with two second entities, which may be the same or different, wherein the second entities have functional groups which may be the same or different and which are reactive with the reactive functional groups of the first entity to link the entities by amide or imide bonds and wherein the second entities provide the end-blocked groups of the resultant end-blocked polyamide or end-blocked polyimide.
  • each entity can possess other functional groups but those other functional groups do not result in unwanted cross-linking reactions and products therefrom.
  • the polyamide and/or the polyimide is a compound according to the fourth aspect of the present invention or a composition comprising the compound according to the fourth aspect of the present invention.
  • the compound has an average molecular weight below 5,000 and preferably less than 500.
  • R 1 and R 5 are independently selected from C 4 _ 24 alkyl, alkenyl, cycloalkyl, cycloalkenyl or aromatic groups.
  • R 1 and R 5 are independently selected from C 4 _ 24 alkyl, alkenyl, cycloalkyl or cycloalkenyl groups.
  • R 2 and R 4 are C ⁇ alkyl, alkenyl, cycloalkyl, cycloalkenyl or aromatic groups.
  • R 2 and R 4 are C ⁇ _ 12 alkyl, alkenyl, cycloalkyl, or cycloalkenyl groups.
  • R 3 is a C j _ 12 alkyl, alkenyl, cycloalkyl, cycloalkenyl or an aromatic group.
  • R 1 and R 5 may be the same or different and may contain side groups which are unreactive in the production of the compound or composition;
  • R 2 and R 4 may be the same or different and may contain side groups which are unreactive in the production of the compound or composition; and
  • R 3 may contain side groups which are unreactive in the production of the compound or composition.
  • the polyamide or polyimide can contain a small number of other linkages, such as ester linkages.
  • the polyamide or polyimide contains at most two other linkages, more preferably at most one other linkage.
  • the polyamide or polyimide only contains amide and/or imide linkages.
  • the compound of the present invention may be the product of the reaction of a total of two moles of aliphatic amine, selected from one or more of: t-butyl amine, cyclohexyl amine, 2-ethylhexyl amine or dodecenyl amine, with one mole of the reactive derivative of one or more aliphatic diacids selected from succinic acid, glutaric acid or adipic acid.
  • the compound of the present invention may be the reaction product of one mole of aliphatic diamine, selected from one or more of: 1,2-diaminocyclohexane, l,3-diamino-2,2-dimethyl-propane or triethylene tetramine, with two moles of the reactive derivative of one or more of aliphatic acids, selected from: octanoic acid, 2-ethylhexanoic acid, or oleic acid.
  • aliphatic diamine selected from one or more of: 1,2-diaminocyclohexane, l,3-diamino-2,2-dimethyl-propane or triethylene tetramine
  • two moles of the reactive derivative of one or more of aliphatic acids selected from: octanoic acid, 2-ethylhexanoic acid, or oleic acid.
  • the compound of the present invention may be blended with other additives or synthetic oils, or even other compounds according to the present invention. This blending enables one to tailor the properties of the resultant compound or composition such that, for example, the finished blended oil has desired physical and chemical characteristics.
  • Varying the molecular weight and structure of the various reactants allows the production of oils with specific properties. For example, increasing the content of branched alkyl or aromatic components in the compound or composition increases the flash point, increases the hydrolytic stability and lowers the viscosity, but reduces the biodegradability. A predominance of straight-chain alkyl or alkenyl compounds results in high biodegradability at the expense of reduced fluidity at low temperatures. Longer chain lengths exhibit poorer low temperature viscosity and biodegradability but have higher flash points and somewhat higher hydrolytic stability. Increasing the proportionate mass of nitrogen in the compound or composition increases the solubility or dispersability in water and increases the metal surface wetting properties of the oil.
  • Blending together compounds or compositions with different properties allows the formation of an oil with the desired characteristics.
  • the compound or composition may also be blended with other base-oil types (such as esters for example) to obtain benefits in cost or performance for particular applications.
  • the desired characteristics are high flash point (>60 °C), low viscosity (less than lOcP at 40°C and pumpable at -5 °C), high biodegradability (>80%), low water solubility, good hydrolytic stability.
  • the oil should have a high flash point, high biodegradability and show good metal-wetting properties. In this case properties like viscosity, water solubility and hydrolytic stability are of lesser importance.
  • flash point is important as a measure of the fire risk. In general, products with flash points greater than 60 °C are considered to be low flammability.
  • any breakdown of the compound or compos.. ion is characterised by an increase in the free acid in the fluid. This can be determined by titration with a standard alkali.
  • the compound of the present invention may be used for chain lubricants, particularly for chain saws. Also, the compound may be used as internal combustion engine lubricants. Also the compound may be used as a component of a metal-working coolant/lubricant fluids. In addition, the compound may be used as a component of a hydraulic fluid.
  • the present invention is a synthetic oil based on low molecular weight polyamides or polyimides which are terminated by monofunctional groups.
  • the polyamide or polyimide according to the present invention may be obtained by reacting one or more aliphatic, cycloaliphatic or aromatic amine compounds, each having one or two reactive terminal sites, with one or more aliphatic, cycloaliphatic or aromatic acid derivatives, each having one or two reactive carbonyl groups, to form terminally-blocked polyamides or polyimides.
  • one or more aliphatic, cycloaliphatic or aromatic amine compounds each having one or two reactive terminal sites
  • one or more aliphatic, cycloaliphatic or aromatic acid derivatives each having one or two reactive carbonyl groups
  • the aliphatic, cycloaliphatic or aromatic amine compounds, each having one or two reactive terminal sites, and/or the aliphatic, cycloaliphatic or aromatic acid derivatives, each having one or two reactive carbonyl groups may have other functional groups that do not hinder the formation of the preparation of the polyamides or polyimides of the present invention.
  • the compound or composition of the present invention using an aliphatic, cycloaliphatic or aromatic amine compounds, each having one or two reactive terminal sites, and wherein a third terminal site is present which is "temporarily blocked" in the sense that it is non-reactive in the reaction process of the one or more aliphatic, cycloaliphatic or aromatic amine compounds, each having one or two reactive terminal sites, with the one or more aliphatic, cycloaliphatic or aromatic acid derivatives, each having one or two reactive carbonyl groups, to form the end-blocked polyamides or polyimides.
  • the temporarily blocked site may then be un-blocked and allowed to react, if desired, with a further reactant.
  • amides, or diamides with hydrocarbyl halides or dihalides may be used to obtain the compound or compositions of the present this invention.
  • from 1 to 7 groups derived from diacids are linked by up to 6 diamine groups and two monoamines occupy the terminal positions.
  • between 1 and 7 diamine groups are linked by up to 6 diacid groups and the structure terminated by two monofunctional acids.
  • the diamines may in fact be polyamines with up to 6 polyalkylene repeating units. Viscosity requirements limit the preferred maximum molecular weight of the compound used in the invention to approximately 5,000 and more preferably less than 500.
  • a preferred compound has terminal alkyl or alkenyl groups preferably derived from, for example, one or more of t-butyl amine, cyclohexyl amine, 2-ethylhexyl amine or dodecenyl amine and the terminal groups are linked by an entity having two reactive functional groups which may be the same or different.
  • the entity can possess other functional groups but those other functional groups do not result in unwanted cross-linking reactions and products therefrom.
  • the entity can be or derived from one or more of glutaric acid, succinic acid or adipic acid, giving a N,N'-dialkyl diamide product - for example N,N'-di-t-butyl adipamide.
  • the terminal groups are carbonyl derived from, for example, one or more of octanoic acid, ethylhexanoic or octadecanoic acids and the linking group is a disubstituted compound such as methylene diamine, 1,2-ethylene diamine, tetraethylene pentamine, 1,2-cyclohexyl diamine or neopentyl diamine, giving an alkylene bis(amide) - for example: 1,2-ethylene bis(octanoamide).
  • a preferred compound of the present invention is therefore a polyamide with the following general structure:
  • R 1 and R 5 are independently C 4 _ 24 alkyl, alkenyl, cycloalkyl or cycloalkenyl or, less preferably, aromatic groups.
  • R 2 and R 4 are C ⁇ _ n alkyl, alkenyl, cycloalkyl or cycloalkenyl or, less preferably, aromatic groups.
  • R 2 and R 4 may be the same or different and may contain side groups which are unreactive in the production of the compound or composition.
  • Preferred groups are CH 2 CH 2 , CHCH 3 CH 2 and (CH ⁇ R 3 is a C ⁇ alkyl, alkenyl, cycloalkyl or cycloalkenyl or, less preferably, aromatic group and may contain side groups which are unreactive in the production of the compound or composition.
  • Preferred R 3 groups are (CH ⁇ , (CH ⁇ , (CH ⁇ and (CH ⁇ .
  • R 1 and R 5 are either t-butyl, cyclohexyl,
  • the compound of the present invention is particularly suitable for use as a biodegradable oil phase in the drilling of well bores.
  • adipic acid (usually in the form of the acid dihalide or dimethyl ester) is reacted with two moles of dodecenyl amine to form N,N' didodecenyl adipamide.
  • the resulting liquid compound is found to be insoluble in water, having a boiling point of 250 °C, a density of 0.97 g/ml and a viscosity of 20 cP at 40 °C. The flash point was found to exceed 110 °C.
  • a 10 ml sample of the polyamide oil was agitated in 1 litre of seawater over a period of 28 days.
  • the liquids were allowed to separate and the volume of the upper oil phase measured and found to be 1.2 ml, indicating that 88% of the original oil had biodegraded.
  • 80 ml of the oil was placed in a rolling oven sample bomb and 120 ml of 20% w / w calcium chloride added. The bomb was sealed and pressurised with 100 psi nitrogen and then rolled for 16 hours at 200 °C. After this period, the sample was cooled and 25 ml of the aqueous layer extracted and neutralised using 2 ml of 0.1N NaOH.
  • a 10 g sample of Viton rubber was covered with the polyamide oil and left for 28 days. After this period the rubber was wiped clean and dry using a paper tissue and on weighing showed no loss or gain.
  • neopentyl diamine is reacted with two moles of oleic acid (for example as thr acid halide or methyl ester) to form neopentyl N,N' bis(oleamide).
  • the water-insoluble liquid product has a boiling point of 225 °C, density of 0.97 g/ml and a viscosity of 15 cP at 40 °C.
  • the oil was found to have a flash point of 105 °C.
  • the biodegradability was found to be 80%.
  • 1.5 ml of 0.1N NaOH was required for neutralisation. Viton rubber showed no loss or gain in weight after 28 days in the oil.
  • One mole of pentaethylene hexamine is reacted with two moles of ethyl hexanoic acid, or its more reactive derivatives (usually the acid halide or methyl ester), to yield a product, which after purification, is found to have a water solubility of 0.05g/l, density of 0.96 g/ml, a boiling point of 180 °C and a viscosity of 5 cP at 40 °C.
  • the flash point of the product was 85 °C. No swelling of Viton was observed after 28 days immersion.
  • One mole of triethylene tetramine is reacted with two moles of adipic acid (usually in the form of the acid dihalide or dimethyl ester) and then two moles of cyclohexylamine to yield a liquid, which after purification, has a boiling point of 170 °C, density 0.97 g ml and a viscosity of 7 cP at 40 °C.
  • the flashpoint of the oil was 69 °C. No swelling of Viton was observed after 28 days immersion.
  • One mole of 1,6 hexamethylene diamine is reacted with two moles of a reactive 2- ethyl hexanoic acid derivative to yield, after purification, a liquid with a boiling point of 240 °C, a density of 0.92 g/ml and a viscosity of 3.5 cP at 40 °C.
  • the flashpoint of the oil was >110 °C and no swelling of Viton was observed after 28 days immersion.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne un composé représenté par la formule (I) dans laquelle: R1[CO]u[NHR2]w[NHCOR3[CO]n][NHR4]y]x[NHCOR3[CO]n]zNH[CO]yR5 chacun de w, x, y et z indépendamment possède une valeur moyenne entre 0 et 6; chacun de n, u et v indépendamment possède une valeur moyenne entre 0 et 1; u+v+x.(1+n)+z.(1+n)»2; et R?1, R2, R4 et R5¿ représentent indépendamment des groupes organiques. Ce composé peut s'utiliser efficacement en tant que phase huileuse biodégradable dans le forage de puits.
PCT/GB1995/001014 1994-05-04 1995-05-04 Composes amides et imides et leur utilisation en tant qu'huiles lubrifiantes WO1995030643A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB9622227A GB2303133B (en) 1994-05-04 1995-05-04 Amide and imide compounds and their use as lubricant oils
AU23502/95A AU2350295A (en) 1994-05-04 1995-05-04 Amide and imide compounds and their use as lubricant oils

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9408613A GB9408613D0 (en) 1994-05-04 1994-05-04 Polyamide oil
GB9408613.9 1994-05-04
GB9409601A GB9409601D0 (en) 1994-05-04 1994-05-13 Polyamide oil
GB9409601.3 1994-05-13

Publications (1)

Publication Number Publication Date
WO1995030643A1 true WO1995030643A1 (fr) 1995-11-16

Family

ID=26304803

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1995/001014 WO1995030643A1 (fr) 1994-05-04 1995-05-04 Composes amides et imides et leur utilisation en tant qu'huiles lubrifiantes

Country Status (2)

Country Link
AU (1) AU2350295A (fr)
WO (1) WO1995030643A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6022833A (en) * 1996-10-30 2000-02-08 Henkel Kommanditgesellschaft Auf Aktien Multicomponent mixtures for use in geological exploration
US6165946A (en) * 1996-10-30 2000-12-26 Henkel Kommanditgesellschaft Auf Aktien Process for the facilitated waste disposal of working substances based on water-in-oil invert emulsions
JP2020534407A (ja) * 2017-09-18 2020-11-26 シェブロン・オロナイト・カンパニー・エルエルシー ポリイミド分散剤およびその製造および使用方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0438849A1 (fr) * 1990-01-25 1991-07-31 Ethyl Petroleum Additives Limited Succinimides ou succinamides modifiés par un acide dicarboxylique utiles dans des compositions dispersantes
WO1992012960A2 (fr) * 1991-01-29 1992-08-06 Pinaroo Ltd. Derives d'acides dicarboxyliques possedant de six a douze atomes de carbone, et utilisation de ces derives et des acides dicarboxyliques seuls pour la preparation de compositions pharmaceutiques destinees a la nutrition enterale et parenterale
WO1993023491A1 (fr) * 1992-05-18 1993-11-25 Exxon Chemical Patents Inc. Fluide de travail

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0438849A1 (fr) * 1990-01-25 1991-07-31 Ethyl Petroleum Additives Limited Succinimides ou succinamides modifiés par un acide dicarboxylique utiles dans des compositions dispersantes
WO1992012960A2 (fr) * 1991-01-29 1992-08-06 Pinaroo Ltd. Derives d'acides dicarboxyliques possedant de six a douze atomes de carbone, et utilisation de ces derives et des acides dicarboxyliques seuls pour la preparation de compositions pharmaceutiques destinees a la nutrition enterale et parenterale
WO1993023491A1 (fr) * 1992-05-18 1993-11-25 Exxon Chemical Patents Inc. Fluide de travail

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6022833A (en) * 1996-10-30 2000-02-08 Henkel Kommanditgesellschaft Auf Aktien Multicomponent mixtures for use in geological exploration
US6165946A (en) * 1996-10-30 2000-12-26 Henkel Kommanditgesellschaft Auf Aktien Process for the facilitated waste disposal of working substances based on water-in-oil invert emulsions
JP2020534407A (ja) * 2017-09-18 2020-11-26 シェブロン・オロナイト・カンパニー・エルエルシー ポリイミド分散剤およびその製造および使用方法

Also Published As

Publication number Publication date
AU2350295A (en) 1995-11-29

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