EP1083986A1 - Dispersions contenant des homo- ou des copolymeres d'acides hydroxycarboxyliques s'utilisant comme additif rheologique - Google Patents

Dispersions contenant des homo- ou des copolymeres d'acides hydroxycarboxyliques s'utilisant comme additif rheologique

Info

Publication number
EP1083986A1
EP1083986A1 EP99919198A EP99919198A EP1083986A1 EP 1083986 A1 EP1083986 A1 EP 1083986A1 EP 99919198 A EP99919198 A EP 99919198A EP 99919198 A EP99919198 A EP 99919198A EP 1083986 A1 EP1083986 A1 EP 1083986A1
Authority
EP
European Patent Office
Prior art keywords
dispersion according
copolymers
dispersion
acid
ricinoleic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99919198A
Other languages
German (de)
English (en)
Inventor
Heinz Müller
Stefan Podubrin
Claus-Peter Herold
Andreas Heidbreder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1083986A1 publication Critical patent/EP1083986A1/fr
Withdrawn legal-status Critical Current

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

L'invention concerne des dispersions contenant une phase huileuse et une phase aqueuse, au moins un solide en dispersion, ainsi qu'éventuellement d'autres additifs. Ces dispersions se caractérisent en ce qu'elles contiennent comme additif rhéologique, des homo- ou des copolymères, obtenus par condensation d'acide ricinoléique seul ou en présence d'acides hydroxycarboxyliques de la formule (I) HO-X-CO-OH ou de leurs dérivés à cycle fermé, X désignant un reste alkylène saturé linéaire ou ramifié ayant entre 1 et 23 atomes de carbone.
EP99919198A 1998-04-11 1999-04-06 Dispersions contenant des homo- ou des copolymeres d'acides hydroxycarboxyliques s'utilisant comme additif rheologique Withdrawn EP1083986A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19816308A DE19816308A1 (de) 1998-04-11 1998-04-11 Rheologisches Additiv
DE19816308 1998-04-11
PCT/EP1999/002323 WO1999052623A1 (fr) 1998-04-11 1999-04-06 Dispersions contenant des homo- ou des copolymeres d'acides hydroxycarboxyliques s'utilisant comme additif rheologique

Publications (1)

Publication Number Publication Date
EP1083986A1 true EP1083986A1 (fr) 2001-03-21

Family

ID=7864360

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99919198A Withdrawn EP1083986A1 (fr) 1998-04-11 1999-04-06 Dispersions contenant des homo- ou des copolymeres d'acides hydroxycarboxyliques s'utilisant comme additif rheologique

Country Status (6)

Country Link
EP (1) EP1083986A1 (fr)
AU (1) AU754148B2 (fr)
CA (1) CA2327422A1 (fr)
DE (1) DE19816308A1 (fr)
NO (1) NO20005097L (fr)
WO (1) WO1999052623A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0613186A2 (pt) * 2005-04-29 2010-12-21 Dow Global Technologies Inc co-poliéster, espuma de poliuretano e processo para preparar uma espuma flexìvel de poliuretano
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
EP3596152A1 (fr) * 2017-03-16 2020-01-22 Pivert Nouveaux polymères ramifiés, leur procédé de préparation et leurs utilisations
WO2024098126A1 (fr) * 2022-11-11 2024-05-16 Dioveritá Mundi, Llc Additif, procédé d'obtention d'additif, utilisation d'additif, produit et composition polymérique, ou polymère

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3778287A (en) * 1970-12-22 1973-12-11 Ici Ltd Pigment dispersions
GB2129467B (en) * 1982-11-03 1986-07-02 Halliburton Co The use of certain materials as thinners in oil based drilling fluids
GB8607596D0 (en) * 1986-03-26 1986-04-30 Ici Plc Dispersible composition of ceramic
DE3903785A1 (de) * 1989-02-09 1990-08-16 Henkel Kgaa Oleophile basische aminverbindungen als additive in invert-bohrspuelschlaemmen
DE4012105A1 (de) * 1990-04-14 1991-10-17 Henkel Kgaa Verwendung von hydriertem rizinusoel als viskositaetsbildner in oelbasierten bohrspuelsystems

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9952623A1 *

Also Published As

Publication number Publication date
AU3705999A (en) 1999-11-01
WO1999052623A1 (fr) 1999-10-21
CA2327422A1 (fr) 1999-10-21
DE19816308A1 (de) 1999-10-14
NO20005097L (no) 2000-11-07
AU754148B2 (en) 2002-11-07
NO20005097D0 (no) 2000-10-10

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