WO1999052623A1 - Dispersionen enthaltend homo- oder copolymere von hydroxycarbonsäuren als rheologisches additiv - Google Patents
Dispersionen enthaltend homo- oder copolymere von hydroxycarbonsäuren als rheologisches additiv Download PDFInfo
- Publication number
- WO1999052623A1 WO1999052623A1 PCT/EP1999/002323 EP9902323W WO9952623A1 WO 1999052623 A1 WO1999052623 A1 WO 1999052623A1 EP 9902323 W EP9902323 W EP 9902323W WO 9952623 A1 WO9952623 A1 WO 9952623A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dispersion according
- copolymers
- dispersion
- acid
- ricinoleic acid
- Prior art date
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- 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
- C09K8/04—Aqueous well-drilling compositions
- C09K8/14—Clay-containing compositions
- C09K8/18—Clay-containing compositions characterised by the organic compounds
- C09K8/22—Synthetic organic compounds
- C09K8/24—Polymers
Definitions
- the present application relates to dispersions which contain certain homo- or copolymers as rheological additives, the use of such polymers as rheological additives and a process for reducing the viscosity of aqueous dispersions containing solids.
- liquids for example paints and pharmaceutical, cosmetic or food preparations
- Such liquids generally show thixotropic behavior under shear stress, i.e. that the viscosity of these systems, also referred to as non-Newtonian liquids, decreases under the influence of increasing shear stress or shear rate. In practice, this behavior can lead to problems if the liquids are to be transported or pumped and are exposed to different mechanical loads.
- drilling muds are liquid flushing systems for drilling rock holes while applying the detached cuttings.
- the drilling fluids have a certain density (usually greater than 1.5 g / cm) in order to prevent the formation from possibly collapsing.
- solids are added to the rinse for weighting. Barium sulfate is usually used.
- So-called thickeners are also used, which increase the viscosity of the mud in order to facilitate the removal of the cuttings. At the same time, the viscosity of the rinse must not become so high that the flow and pumpability are impaired.
- EP 549 958 B1 discloses hydrogenated castor oil as a suitable rheological additive for dispersions containing solids, in particular for paints.
- GB 1 514 586 describes reaction products of oligomers of hydroxycarboxylic acids with copolymers based on acrylate, which are suitable as dispersion auxiliaries for liquid media containing solids.
- Suitable additives especially for drilling fluids, especially for water-based systems are phosphates or lignites, as described, for example, by G. Gray and H.C.H. Darley, Composition and Properties of Oil Well Drilling Fluids, Gulf Publishing Company, Houston 1988, from page 564.
- additives when such additives are used in the area of drilling fluids, increased demands are made.
- the additives must be liquid over a wide temperature range, in particular those additives are sought which are still usable even at low temperatures of well below 0 ° C.
- the additives should withstand high pressures or shear loads and meet the requirements for biodegradability, which are increasingly placed on such systems.
- the use of these additives must not affect the stability of the drilling fluid system.
- the present invention therefore relates to dispersions which contain an oil and a water phase, at least one dispersed solid and, if appropriate, further auxiliaries, and as a rheological additive, homopolymers or copolymers which can be obtained by condensing ricinoleic acid with or in itself Presence of hydroxycarboxylic acids of formula (I) or their ring-closed derivatives,
- X is a linear or branched saturated alkylene radical having 1 to 23 carbon atoms.
- the solids-containing dispersions according to the invention can be used in the most varied areas of technology. In the context of the present application, however, those dispersions are preferably described which are used as drilling fluids. As is well known, these are limited thickened, flowable systems which can in principle be assigned to one of the three following classes: purely aqueous drilling fluid, oil-based drilling fluid systems, which are generally used as so-called invert emulsion muds, and the water-based O / W - Emulsions which contain a heterogeneous finely dispersed oil phase in the closed aqueous phase.
- Closed oil-based drilling fluids are generally constructed as a three-phase system: oil, water and fine-particle solids.
- the aqueous phase is heterogeneously finely dispersed in the closed oil phase.
- additives are provided, in particular emulsifiers, weighting agents, fluid loss additives, alkali reserves, viscosity regulators and the like.
- PA Boyd et al. New Base Oil Used in Low-Toxicity Oil Muds
- Fluid loss additives fluid loss additives
- alkali reserves alkali reserves
- viscosity regulators viscosity regulators
- Drilling fluids based on water-based O / W emulsion systems occupy an intermediate position between the purely aqueous systems and the oil-based inverting fluids.
- Detailed factual information can be found here in the relevant specialist literature, reference is made, for example, to the specialist book George R. Gray and HCH Darley "Composition in Properties of Oil Well Drilling Fluids", 4th edition, 1980/81, Gulf Publishing Company, Houston and the extensive the literature cited therein and the "Applied Drilling Engineering” manual, Adam T. Borgoyne, Jr. et al., First Printing Society of Petroleum Engineers, Richardson, Texas (USA). Even today, the oil-based W / O inverter systems are undisputedly the safest tools, especially when drilling through water-sensitive clay layers.
- the homopolymers and copolymers described as rheological additives in the context of the present application are prepared by condensation of ricinoleic acid alone or in the presence of the hydroxycarboxylic acids of the formula (I) described at from 180 to 220 ° C. with elimination of water.
- the condensation is preferably carried out over a period of 2 to 6 hours.
- the details of such reactions are described, for example, by S.N. Modak and J.G. Kane in JAOCS, vol. 42, 1965, pages 428 to 432.
- the condensation is usually carried out without the addition of a catalyst. In certain cases, however, it may be advantageous to use suitable catalysts, e.g.
- Ricinoleic acid is used in a commercially available form. It is obtained by saponifying castor oil.
- Hydroxycarboxylic acids of the formula (I) are those compounds in which the radical X is an alkylene radical having 1 to 23, preferably 1 to 12 and in particular 1 to 6, carbon atoms. Examples of such acids are hydroxystearic acid, glycolic acid, lactic acid or hydroxybutyric acid or their ring-closed derivatives. Ring-closed derivatives are understood to mean compounds which are derived from the corresponding ones by intramolecular esterification Acids are formed. For example, ⁇ -butyrolcatone or ⁇ -caprolactone are suitable.
- the dispersions according to the invention preferably contain homopolymers of ricinoleic acid as rheological additives, preference being given to using homopolymers whose acid number, measured according to DGF method C-V 2, is less than 45 and in particular less than 40. If, on the other hand, copolymers of ricinoleic acid and hydroxycarboxylic acid are used as the rheological additive, those dispersions are preferred which contain copolymers of ricinoleic acid and 12-hydroxystearic acid.
- the polymers have a low pour point (measured according to DIN ISO 3016) of at most 0 ° C., preferably from -5 to -35 ° C.
- the dispersions according to the invention usually contain the additives in amounts of between 0.1 to 1.0% by weight, and preferably in amounts of 0.2 to 0.8% by weight, based on the total dispersion.
- the dispersions according to the invention are three-phase systems consisting of an oil, a water and a solid phase.
- Preferred dispersions are those whose volume ratio of water to oil phase is in the range from 90 to 10 parts of water to 10 to 90 parts of oil.
- Dispersions containing 70 to 90 parts by volume of oil and 30 to 10 parts by volume of water phase are particularly preferred.
- Preferred dispersions are those in the form of a W / O emulsion of the type described above.
- Such systems are referred to as invert systems in the field of drilling fluids.
- the solids content of the dispersions is in the range from 1 to 70% by weight, preferably in the range from 10 to 55% by weight, based on the dispersion.
- the density is preferably in the range from 1.5 g / cm to 2.5 g / cm.
- the oil phase of the dispersions can in principle contain any compounds which are immiscible or difficult to mix with water and are liquid at room temperature. If the dispersions are used as drilling fluid or other similar borehole treatment agents, the oil phases are limited to the substances known to the person skilled in the art for this technical field. Mineral oil fractions were originally used as the oil phase in drilling fluids. However, this is associated with a not inconsiderable impact on the environment, for example if the drilling mud is drilled directly or through the drilling Get rock into the environment. Mineral oils are difficult and practically not biodegradable and therefore can be regarded as long-term pollution. In the past decade in particular, a large number of proposals have been made to replace the mineral oil fractions with more environmentally compatible and more easily degradable oil phases.
- Preferred dispersions are those in which the oil phase is formed partially or completely from carboxylic acid esters of saturated and unsaturated, linear or branched alcohols having 1 to 22 C atoms and saturated and unsaturated, linear or branched carboxylic acids having 1 to 22 C atoms.
- oil phases which contain more than 50% by volume of the abovementioned esters are preferred.
- esters, as well as invert drilling fluids containing these esters are described in detail in the documents EP 374 671 B1, 374 672 B1, EP 386 638 B1 and 386 636 B1 of the applicant. The disclosure of these documents also becomes part of the present application.
- esters of saturated monocarboxylic acids with 12 to 16 C atoms and monofunctional alcohols with 2 to 12 C atoms are particularly preferred.
- esters of polyfunctional alcohols with monocarboxylic acids and in particular glycerol esters of natural and / or synthetic origin can be used effectively as an oil phase or as a component of the oil phase Come into play.
- triglycerides of plant and / or animal origin - for example of the type of rape oil or fish oil - can be used, which can be interesting both from ecological considerations and from considerations of the cost / benefit ratio.
- Solids which are not or only partially soluble in water or the oil phase are also suitable as solids.
- Solids selected from the group barium sulfate (barite) and / or calcium carbonate, which serve as weighting agents, are preferably used in drilling fluids.
- organophilic clay minerals such as bentonites or montmorillonites, are used as viscosity formers or "thickeners”.
- Another important component of drilling fluids are basic compounds for regulating the pH value, since the collapse of acidic gases, such as CO or H 2 S, from the formation can lead to considerable corrosion problems. It is therefore preferred to set the pH of the water phase of the rinse in the weakly alkaline range, preferably at pH values of 8.5 to 9.0. Usually, Ca (OH) 2 or CaO (Lime or Quick-Lime) is added to the rinse as an alkali reserve. In invert drilling fluids based on ester oils in particular, however, it is observed that excessive amounts of lime lead to undesired hydrolysis of the esters.
- the fatty acids formed as reaction products of the hydrolysis then react preferably with Ca ions to form the corresponding soaps, which can lead to an uncontrolled thickening of the rinsing systems. It is therefore preferred to limit the amount of free lime present as an alkali reserve in the drilling fluid to a maximum of about 2 lb / bbl drilling fluid.
- the dispersions can also contain further auxiliaries or additives known to the person skilled in the art. These preferably include emulsifiers, fluid loss additives, corrosion inhibitors or wetting agents. When selecting the emulsifiers, preference is given to those compounds or mixtures thereof which are described in the applicant's German application DE 196 43 840.3. Water-soluble salts, preferably calcium chloride or potassium chloride, may also be present, the salts preferably being used in amounts such that the aqueous phase is saturated.
- the dispersions according to the invention are distinguished by a low viscosity, which is largely retained even under shear stress.
- the dispersions of the invention preferably have a plastic viscosity (PV) in the range of 10 to 60 mPa ⁇ s, and a flow limit (yield point YP) in the range of 5 to 50 lb / 100 ft 2, in each case measured at 50 ° C on. These values refer to freshly prepared systems that are not thermally stressed.
- PV plastic viscosity
- Yield point YP yield point
- yield point YP yield point
- These theological parameters are measured using customary methods, which are described, for example, in the "Manual of Drilling Fluids Technology" from Baroi ⁇ V NL Industries, Inc., 1979. Due to the low pour point of the polymers contained in the additives, the rheological additives retain their effect even at low temperatures and can be used, for example, for drilling in arctic or antarctic areas.
- Another embodiment relates to the use of homopolymers or copolymers which can be obtained by condensation of ricinoleic acid with itself or in the presence of hydroxycarboxylic acids of the formula (I) as described above, or their ring-closed derivatives, as a rheological additive for aqueous dispersions containing solids.
- the addition of the additives according to the invention leads to a significant reduction in the viscosity without, for example, the emulsion stability being reduced.
- Dispersion homo- or copolymers which can be obtained by condensation of ricinoleic acid with itself or in the presence of hydroxycarboxylic acids of the formula (I) as described above, or their ring-closed derivatives, in amounts of 0.1 to 1.0% by weight, based on the dispersion.
- a drilling fluid was produced based on the following ingredients:
- Emulsifier 212.3g
- OMC 586 ester mixture of essentially saturated fatty acids based on palm kernel, which is mainly due to C 12 / ⁇ 4 fatty acids and 2-ethylhexanol.
- the volume ratio of the rinses was 25 parts water phase to 75 parts oil phase.
- the density was 1.52 g / cm.
- a diluent in the use concentration of 2 lb / bbl was then added to the rinses.
- the rheological characteristics were then determined.
- the viscosity was measured in each case at 50 ° C. in a Fann 35 viscometer from Baroid Drilling Fluids Inc.
- the products A to D according to the invention were measured as rheological additives in comparison to a commercially available product based on polyhydroxystearic acid V2 (Pou ⁇ oint: + 1 ° C). A rinse without thinner was also examined (VI).
- Ricinoleic acid is heated to 220 ° C. in an autoclave under a nitrogen atmosphere. After the reaction has ended, the product is allowed to cool and is used without further work-up.
- the additives according to the invention have a comparable or better effect on the rheology of the rinse than the commercially available product.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Colloid Chemistry (AREA)
- Lubricants (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002327422A CA2327422A1 (en) | 1998-04-11 | 1999-04-06 | Dispersions containing homopolymers or copolymers of hydroxy carboxylic acids as a rheological additive |
EP99919198A EP1083986A1 (de) | 1998-04-11 | 1999-04-06 | Dispersionen enthaltend homo- oder copolymere von hydroxycarbonsäuren als rheologisches additiv |
AU37059/99A AU754148B2 (en) | 1998-04-11 | 1999-04-06 | Dispersions containing homopolymers or copolymers of hydroxy carboxylic acids as a rheological additive |
NO20005097A NO20005097L (no) | 1998-04-11 | 2000-10-10 | Dispersjoner som inneholder homopolymerer eller kopolymerer av hydroksykarboksylsyrer som et reologisk additiv |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19816308.8 | 1998-04-11 | ||
DE19816308A DE19816308A1 (de) | 1998-04-11 | 1998-04-11 | Rheologisches Additiv |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999052623A1 true WO1999052623A1 (de) | 1999-10-21 |
Family
ID=7864360
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/002323 WO1999052623A1 (de) | 1998-04-11 | 1999-04-06 | Dispersionen enthaltend homo- oder copolymere von hydroxycarbonsäuren als rheologisches additiv |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1083986A1 (de) |
AU (1) | AU754148B2 (de) |
CA (1) | CA2327422A1 (de) |
DE (1) | DE19816308A1 (de) |
NO (1) | NO20005097L (de) |
WO (1) | WO1999052623A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006118995A1 (en) * | 2005-04-29 | 2006-11-09 | Dow Global Technologies, Inc. | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
WO2018167201A1 (en) * | 2017-03-16 | 2018-09-20 | Pivert | New branched polymers, their preparation process, and uses thereof |
WO2024098126A1 (pt) * | 2022-11-11 | 2024-05-16 | Dioveritá Mundi, Llc | Aditivo, processo para obtenção de aditivo, uso de aditivo, produto e composição polimérica ou polímero |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10253236B2 (en) | 2013-10-31 | 2019-04-09 | Amril Ag | Environmental friendly well treatment fluids comprising an ester |
CN105801923B (zh) * | 2016-04-03 | 2017-10-13 | 北京化工大学 | 一种基于蓖麻油酸均聚的不迁移的橡胶用增塑剂的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2162484A1 (de) * | 1970-12-22 | 1972-06-29 | Imperial Chemical Industries Ltd., London | Pigmentdispersionen |
EP0108546A2 (de) * | 1982-11-03 | 1984-05-16 | Halliburton Company | Bohrflüssigkeiten auf Ölbasis |
EP0240160A2 (de) * | 1986-03-26 | 1987-10-07 | Imperial Chemical Industries Plc | Zusammensetzung aus feinen keramischen Partikeln und einem organischen Dispergiermittel |
EP0382070A1 (de) * | 1989-02-09 | 1990-08-16 | Henkel Kommanditgesellschaft auf Aktien | Oleophile basische Aminverbindungen als Additiv in Invert-Bohrspülschlämmen |
WO1991016391A1 (de) * | 1990-04-14 | 1991-10-31 | Henkel Kommanditgesellschaft Auf Aktien | Verwendung von hydriertem rizinusöl als viskositätsbildner in ölbasierten bohrspülsystemen |
-
1998
- 1998-04-11 DE DE19816308A patent/DE19816308A1/de not_active Withdrawn
-
1999
- 1999-04-06 CA CA002327422A patent/CA2327422A1/en not_active Abandoned
- 1999-04-06 WO PCT/EP1999/002323 patent/WO1999052623A1/de not_active Application Discontinuation
- 1999-04-06 EP EP99919198A patent/EP1083986A1/de not_active Withdrawn
- 1999-04-06 AU AU37059/99A patent/AU754148B2/en not_active Ceased
-
2000
- 2000-10-10 NO NO20005097A patent/NO20005097L/no not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2162484A1 (de) * | 1970-12-22 | 1972-06-29 | Imperial Chemical Industries Ltd., London | Pigmentdispersionen |
EP0108546A2 (de) * | 1982-11-03 | 1984-05-16 | Halliburton Company | Bohrflüssigkeiten auf Ölbasis |
EP0240160A2 (de) * | 1986-03-26 | 1987-10-07 | Imperial Chemical Industries Plc | Zusammensetzung aus feinen keramischen Partikeln und einem organischen Dispergiermittel |
EP0382070A1 (de) * | 1989-02-09 | 1990-08-16 | Henkel Kommanditgesellschaft auf Aktien | Oleophile basische Aminverbindungen als Additiv in Invert-Bohrspülschlämmen |
WO1991016391A1 (de) * | 1990-04-14 | 1991-10-31 | Henkel Kommanditgesellschaft Auf Aktien | Verwendung von hydriertem rizinusöl als viskositätsbildner in ölbasierten bohrspülsystemen |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006118995A1 (en) * | 2005-04-29 | 2006-11-09 | Dow Global Technologies, Inc. | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
KR101224302B1 (ko) | 2005-04-29 | 2013-01-21 | 다우 글로벌 테크놀로지스 엘엘씨 | 2차 알콜 기를 함유하는 폴리에스테르 폴리올 및 가요성폴리우레탄 발포체와 같은 폴리우레탄의 제조에 있어서의이들의 용도 |
WO2018167201A1 (en) * | 2017-03-16 | 2018-09-20 | Pivert | New branched polymers, their preparation process, and uses thereof |
WO2024098126A1 (pt) * | 2022-11-11 | 2024-05-16 | Dioveritá Mundi, Llc | Aditivo, processo para obtenção de aditivo, uso de aditivo, produto e composição polimérica ou polímero |
Also Published As
Publication number | Publication date |
---|---|
AU3705999A (en) | 1999-11-01 |
CA2327422A1 (en) | 1999-10-21 |
DE19816308A1 (de) | 1999-10-14 |
NO20005097L (no) | 2000-11-07 |
AU754148B2 (en) | 2002-11-07 |
EP1083986A1 (de) | 2001-03-21 |
NO20005097D0 (no) | 2000-10-10 |
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