EP2285835A1 - Copolymère greffé, procédé de fabrication et utilisation - Google Patents

Copolymère greffé, procédé de fabrication et utilisation

Info

Publication number
EP2285835A1
EP2285835A1 EP08750360A EP08750360A EP2285835A1 EP 2285835 A1 EP2285835 A1 EP 2285835A1 EP 08750360 A EP08750360 A EP 08750360A EP 08750360 A EP08750360 A EP 08750360A EP 2285835 A1 EP2285835 A1 EP 2285835A1
Authority
EP
European Patent Office
Prior art keywords
acid
component
polymer according
silane
silica
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Withdrawn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
EP08750360A
Other languages
German (de)
English (en)
Inventor
Roland Reichenbach-Klinke
Johann Plank
Peter Lange
Gregor Keilhofer
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP2285835A1 publication Critical patent/EP2285835A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F30/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F30/08—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B40/00—Processes, in general, for influencing or modifying the properties of mortars, concrete or artificial stone compositions, e.g. their setting or hardening ability
    • C04B40/0028—Aspects relating to the mixing step of the mortar preparation
    • C04B40/0039—Premixtures of ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
    • 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
    • C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
    • C09K8/46—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement
    • C09K8/467—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement containing additives for specific purposes
    • C09K8/487—Fluid loss control additives; Additives for reducing or preventing circulation loss
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
    • C04B2103/46—Water-loss or fluid-loss reducers, hygroscopic or hydrophilic agents, water retention agents

Definitions

  • the present invention is a graft copolymer, a process for its preparation and its use.
  • Copolymers even in grafted form, are well known and are used because of their specific monomer composition in a variety of applications.
  • copolymers are also frequently used as water retention agents, which are also referred to as fluid loss additives.
  • a special field of application in this context is the cementation of boreholes in the development of underground oil and gas deposits.
  • Fluid loss additives or water retention agents are compounds which reduce the release of water from a cement slurry. This is particularly important in the field of oil and natural gas exploration, as cement slurries, which essentially consist of cement and water, are pumped during the cementation of the boreholes through the annulus between the so-called casing and the borehole wall. In this case, quantities of water can be released from the cement slurry to the subsoil formation. This is particularly the case when the cement slurry flows past porous rock layers during well cementing. The alkalized water from the cement slurry can then swell clays in the formations and form calcium carbonate precipitates with carbon dioxide from the natural gas or petroleum. These effects reduce the permeability of the deposits and, as a consequence, the production rates are negatively affected.
  • the cement slurry does not solidify due to the release of water to the porous subsoil formations and thus becomes permeable to gases as well as to liquid hydrocarbons and water. As a result, this leads to the escape of fossil fuels through the filled with porous cement annulus. It is therefore for some time continuously striving to reduce such water loss of the cement slurry used to a tolerable minimum.
  • EP 0 116 671 A1 describes a cement slurry for deep wells which, with its content of copolymers, is intended to reduce water loss.
  • An important component of the copolymers used are acrylamides and in particular acrylamido-methyl-propane sulfonic acid (AMPS).
  • AMPS acrylamido-methyl-propane sulfonic acid
  • the cement slurries should contain between 0.1 and 3% by weight of the suitable copolymers.
  • Borehole cementing and a composition suitable for this purpose is the subject of EP 1 375 818 A1.
  • a polymer additive is used which in addition to AMPS additionally contains maleic acid, N-vinylcaprolactam and 4-hydroxybutyl vinyl ether.
  • the water-soluble copolymers according to US Pat. No. 6,395,853 B1 also contain, among other things, the building blocks acrylamide and AMPS.
  • the building blocks acrylamide and AMPS At the forefront of this right is a process for reducing the loss of water in a slurry used to extract oil. Particularly noteworthy in this context are the drilling Lochzementtechnik and completion and the previous process steps preceding borehole sludge.
  • the focus of US 4,700,780 is a method for reducing the loss of water in cementitious compositions which also include defined salt concentrations.
  • the water retention agent is in turn a polymer or polymer salt of AMPS, in which case the building blocks styrene and acrylic acid still have to be present.
  • US Pat. No. 6,855,201 B2 discloses a cement composition consisting of a hydraulic cement component, water and a polymeric fluid loss control additive.
  • the copolymer is based on AMPS, the calcium salt of maleic acid, N-vinylcaprolactam and 4-hydroxybutyl vinyl ether. This polymer is added to the cement composition in amounts between 0.1 and 2% by weight.
  • Copolymers with inorganic and / or organic silicon compounds are also known:
  • Patent EP043159 describes a carrier material for chromatography.
  • This carrier material consists of inorganic, silanized particles to which a copolymer is covalently bonded.
  • the inorganic particles are first reacted with a saturated alkoxysilane.
  • Silanes which are mentioned are aminosilanes, mercaptosilanes, silanes containing ester groups and, preferably, glycidoxysilanes.
  • various acrylamides can be polymerized onto these silanized particles.
  • a suitable acrylamide is u. a. AMPS mentioned.
  • Patent EP0505230 describes silica particles in a polymer matrix having film-forming properties.
  • the silica particles are first functionalized with a silane, although these are double bond-containing silanes. Subsequently, various monomers are grafted onto these silanized silica particles.
  • the monomers mentioned are alkyl (meth) acrylates, unsaturated monocarboxylic acids, aromatic vinyl compounds, dienes (butadiene, chloroprene), vinyl acetate, styrene.
  • polybasic, unsaturated carboxylic acids or unsaturated sulfonic acids (eg AMPS) in proportions of up to 15% by weight. The use of these film-forming polymers is limited to the paint industry.
  • a coating consisting of a radical-curing monomer or oligomer and a surface-treated inorganic particle is known from WO
  • the particle is coated with a fluorosilane and a crosslinkable silane, wherein as crosslinkable silanes and double bond-containing silanes are called.
  • AMPS is mentioned as a suitable monomer.
  • DE102005000918 describes a process for the preparation of an aqueous multicomponent dispersion.
  • This dispersion is prepared by radical polymerization of various monomers in the presence of inorganic particles and a dispersant.
  • the monomer mixture contains at least one epoxide group-containing compound.
  • additional monomers also unsaturated silanes and sulfonic acids are mentioned.
  • the object of the present invention is to provide a novel graft copolymer which is based on the proven monomer building blocks, but by varying the grafting partners leads to a property profile which shows significant improvements especially in the presence of divalent salts and at very high temperatures.
  • this graft copolymer shows a significantly better performance as a water retention agent, with its advantages coming into play particularly under demanding conditions. Due to its monomer building this graft copolymer can be produced very economically. Especially under saline conditions it has been found that the fluid-loss effect of the graft copolymers of the invention over the hitherto known copolymers has significant advantages.
  • silica constituent in component a it has proved advantageous in the context of the provisional invention for this silica constituent to be based on an aqueous colloidally disperse solution of amorphous silicon dioxide (SiO 2). Particularly suitable for the subsequent reaction with an unsaturated silane, so-called nano- and microsilica has been shown.
  • SiO 2 amorphous silicon dioxide
  • Nanosilica are aqueous, colloidal solutions containing only silica.
  • the mean particle size of this silica ranges between 5 and 500 nm, with ranges between 15 and 100 nm, and in particular between 30 and 70 nm, being preferred.
  • Microsilica consists of particles with a size of 0.5 to about 100 microns. These include, for example, pyrogenic silicic acids, precipitated silicas, furnace dusts and fly ash.
  • the silane compound which is converted into component a) by reaction with said silica should, according to the invention, be an ethylenically unsaturated alkoxysilane.
  • the number of carbon atoms in these alkoxysilanes should be between 5 and 15.
  • Particularly suitable representatives are representatives of the series 3-
  • silanes which initially have no double bond but can be converted into a double bond-containing silane by reaction with a suitable ethylenically unsaturated compound.
  • a suitable ethylenically unsaturated compound is, for example, the reaction product of aminopropyltrimethoxysilane and maleic anhydride.
  • Copolymers of acrylamido-methyl-propanesulfonic acid (AMPS) or vinylsulfonic acid with further ethylenically unsaturated monomers have in particular been shown to be suitable water-soluble sulfonic acid-containing polymer components b).
  • Such monomers are preferably selected from the series of vinyl ethers, allyl ethers, acrylic acid, methacrylic acid, 2-ethylacrylic acid, 2-propylacrylic acid, vinylacetic acid, crotonic and isocrotonic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid and their amides.
  • styrenes, vinylphosphonic acid or ethylenically unsaturated silanes are also suitable in general.
  • ethylenically unsaturated compounds such as ethylene glycol dimethacrylate, glycerol dimethacrylate or Trimethylolpropantrimethacrylat can be used.
  • unsaturated amide compounds such as.
  • Copolymers show not only in the choices of its underlying monomers, but also in the mass ratio of component a) and b) to each other. According to the present invention, this may preferably be 10 to 1: 1 to 10, and more preferably 5 to 1: to 1 to 5. It has also been found to be advantageous if the proportion of component a) in the graft copolymer of 10 bis 90 wt .-% and in particular from 40 to 70 wt .-% is. The proportion of component b) in the copolymer should be from 10 to 90% by weight and in particular from 30 to 60% by weight. Also particularly advantageous is a variant of the graft copolymer according to the invention, in which it represents a nanocomposite. Here, the component b) should be covalently bonded via the silane to the surface of the silica.
  • the claimed graft copolymer may be present as a solid, and in this case in particular as a powder, but also as a gel, colloid or suspension. Included is also a variant in which the copolymer has a water content of 50 to 70 wt .-%. Regardless of which of these forms or suitable mixtures thereof the copolymer is in, its average particle size should be between 5 and 2000 nm and in particular between 50 and 1000 nm.
  • the present invention also includes a process for its preparation, which presents itself overall as very simple:
  • process step a) the respective silica is reacted with the unsaturated silane and then the monomers of the sulfonic acid-containing component b) are grafted in step b) the thus reacted silane.
  • the molar ratio of silica and silane in process step a) should be 200: 1 to 20.
  • sodium peroxodisulfate As the initiator of the polymerization reaction in process stage b), sodium peroxodisulfate has proven particularly suitable. But other common initiators such as peroxides, redox initiators or diazo compounds are suitable.
  • the process conditions are essentially uncritical. However, it has been found to be advantageous when the process steps a) and / or b) are performed independently of one another at temperatures between 30 and 100 0C.
  • temperatures between 60 and 75 ° are recommended, with a temperature around 70 0 C is particularly suitable.
  • a temperature range between 40 and 60 0 C should be selected, in which case temperatures around 50 0 C are particularly suitable.
  • the present invention also claims the use of the graft copolymer as an additive in building chemical applications, and in particular in the development, exploitation and completion of underground oil and gas deposits, its use as a water retention agent is considered to be particularly advantageous.
  • the proposed graft copolymers provide compounds which additionally further improve the use of sulfonic acid-containing additives in the construction chemical sector.
  • the graft copolymers according to the present invention are outstandingly suitable as water retention agents or fluid loss additives.
  • reaction mixture was rinsed with N 2 for 1 h; then 2.28 g of Na 2 S 2 Os were added as a starter and heated to 50 0 C. After a reaction time of 1.5 h, the mixture was allowed to cool to room temperature (about 22 ° C.). A white gel having a solids content of 26.6% by weight was obtained.
  • the fluid loss was determined according to API standard 10A at 125 ° F in the following sludge: 800 g Class G cement (Dyckerhoff Black Label) 352 g dist. H2O
  • the fluid loss was determined according to API standard 10A at 190 0 F in the following sludge: 800 g Class G - Cement (Dyckerhoff Black Label)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Ceramic Engineering (AREA)
  • Structural Engineering (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Graft Or Block Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un copolymère greffé à base d'un composant a) composé de silice ayant réagi avec un silane insaturé, et d'un composant polymère b) contenant de l'acide sulfonique. La silice employée est de préférence de la nanosilice et le silane insaturé est de préférence un alkoxysilane à insaturation éthylénique. Le composant b) est représenté par un copolymère à base d'acide acrylamido-méthyl-propane-sulfonique et d'un autre monomère à insaturation éthylénique. Le polymère selon l'invention, représentant en général un nanocomposite, est particulièrement adapté en tant qu'additif dans des applications chimiques de construction, et lors de la mise en exploitation, l'exploitation et la complétion de gisements souterrains de pétrole et de gaz naturel, l'effet dudit polymère en tant qu'agent de rétention d'eau à des salinités élevées et des températures augmentées étant particulièrement avantageux.
EP08750360A 2008-05-21 2008-05-21 Copolymère greffé, procédé de fabrication et utilisation Withdrawn EP2285835A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2008/056240 WO2009141007A1 (fr) 2008-05-21 2008-05-21 Copolymère greffé, procédé de fabrication et utilisation

Publications (1)

Publication Number Publication Date
EP2285835A1 true EP2285835A1 (fr) 2011-02-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP08750360A Withdrawn EP2285835A1 (fr) 2008-05-21 2008-05-21 Copolymère greffé, procédé de fabrication et utilisation

Country Status (8)

Country Link
US (2) US20110118382A1 (fr)
EP (1) EP2285835A1 (fr)
CN (1) CN102037023A (fr)
BR (1) BRPI0822660A2 (fr)
CA (1) CA2723941A1 (fr)
MX (1) MX2010012630A (fr)
RU (1) RU2470041C2 (fr)
WO (1) WO2009141007A1 (fr)

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WO2009141007A1 (fr) 2009-11-26
CN102037023A (zh) 2011-04-27
CA2723941A1 (fr) 2009-11-26
US20110118382A1 (en) 2011-05-19
RU2470041C2 (ru) 2012-12-20
MX2010012630A (es) 2010-12-14
US20130203951A1 (en) 2013-08-08
BRPI0822660A2 (pt) 2015-06-30
RU2010152013A (ru) 2012-06-27

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