WO1994012445A1 - Materiaux de cimentation de substitution pour le conditionnement des puits de petrole profonds a forte temperature - Google Patents

Materiaux de cimentation de substitution pour le conditionnement des puits de petrole profonds a forte temperature Download PDF

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Publication number
WO1994012445A1
WO1994012445A1 PCT/NO1993/000173 NO9300173W WO9412445A1 WO 1994012445 A1 WO1994012445 A1 WO 1994012445A1 NO 9300173 W NO9300173 W NO 9300173W WO 9412445 A1 WO9412445 A1 WO 9412445A1
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WO
WIPO (PCT)
Prior art keywords
resin
cementing material
cementing
curing
weight
Prior art date
Application number
PCT/NO1993/000173
Other languages
English (en)
Inventor
Harald Justnes
Einar DAHL-JØRGENSEN
Original Assignee
Sinvent A/S
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 Sinvent A/S filed Critical Sinvent A/S
Publication of WO1994012445A1 publication Critical patent/WO1994012445A1/fr

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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
    • C08F263/00—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00
    • C08F263/06—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00 on to polymers of esters with polycarboxylic acids
    • C08F263/08—Polymerisation of diallyl phthalate prepolymers
    • 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
    • C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
    • C04B26/02—Macromolecular compounds
    • C04B26/10—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C04B26/18—Polyesters; Polycarbonates
    • 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
    • C09K8/44—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing organic binders only
    • 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
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00034—Physico-chemical characteristics of the mixtures
    • C04B2111/00086—Mixtures with prolonged pot-life
    • 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
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/00241—Physical properties of the materials not provided for elsewhere in C04B2111/00
    • C04B2111/0031—Heavy materials, e.g. concrete used as ballast material
    • 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
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/34—Non-shrinking or non-cracking materials

Definitions

  • the binder in the new, alternative material is based on a diallyl phthalate resin with the setting/curing time controlled by the addition of a temperature sensitive peroxide initiator and a suitable inhibitor.
  • mineral fillers acting as weighting materials (density controlling agents) and extenders (to minimize the resin content) may be included.
  • High temperatures may in general cause problems in controlling the curing time of traditional cement-water slurries, where the proportioning of retarders is a delicate balance between flash setting and over-retardation resulting in unacceptable waiting-on-cement (OC) times.
  • the curing of a diallyl phthalate resin is more easy to control.
  • the new resin may be pre ixed with all components on-shore and stored for a longer period prior to the cementing job. This is possible, since it is the temperature in the well bore that activates the resin.
  • Such an operation may be squeeze cementing used in oil wells for the following purposes: (1) repairing micro-annulus formed in the primary cement causing leaks between formation zones, (2) correcting defective primary cement jobs, (3) isolation of abandoned pay zones and (4) temporary isolation of one reservoir formation in a multiple production zone well while producing the other to depletion.
  • the first system (Zeldin, A. ⁇ . , Kukacka, L.E. and Carciello, ⁇ : "New, Novel Well-Cementing Polymer Concrete Composite", American Concrete Institute (ACI) , Special Publication 69: "Application of Polymer Concrete", 1981, part 69-5, pp. 73- 92) is based on a resin with initiator and inhibitor. However, unlike the present invention, the complete curing of this resin depends on the presence of water. Furthermore, the main component of the resin is organic siloxanes, which are far from the present system based on diallyl phthalates.
  • the second system (Eilers, L.H. : "Process for cementing geothermal wells", United States Patent 4,556,109, 1985-12- 03, 3 pp.) is based on a completely different resin curing according to a condensation mechanism, rather than a free radical polymerization such as for the resin in the present invention.
  • the main component of that resin is furfuryl alcohol/furfural with a zinc accelerated, acid catalyzed curing.
  • the resin of the new, alternative cementing material is characterized by consisting of diallyl phthalates and prepoly ers/oligomers thereof. All three isomers of diallyl phthalate are included in the invention; ortho- (or 1,2-), meta- (or 1,3- or iso-) and para- (or 1,4- or ter-) diallyl phthalate.
  • the amount of diallyl phthalates in the formulation is 20 - 99 % by weight.
  • the resin is characterized by being cured due to the thermal decomposition of a dissolved organic peroxide generating free radicals.
  • organic peroxides are di-tert-butyl-peroxide, tert-butyl-hydroperoxide and 2,5-bis(tert-butyl peroxy)-2,5-dimetylhexyne-3.
  • the dosage of initiator required for a proper curing is 0.1 - 5 % by weight of the resin.
  • the required open time (pot life) for pumping the resin in place is obtained by dissolving a suitable inhibitor stabilizing free radicals.
  • a suitable inhibitor stabilizing free radicals is para-benzoquinone (PBQ) .
  • PBQ para-benzoquinone
  • the amount of inhibitor required depends on the temperature and the type of initiator used, but should be within the range 0.02 - 2 % by weight of the resin.
  • the density of the resin may be controlled by adding a heavy weight filler (weighting material) .
  • Weighting material Finely divided hematite (Fe 2 0 3 ) is preferred, but other materials such as baryte (BaSO and il enite (FeTi0 3 ) may be applicable as well.
  • the consistency of the resin may be controlled by adding an extender. Finely divided calcite (CaC0 3 ) is preferred, but silica flour and condensed silica fume (Si0 2 ) may be used as well.
  • the inherent shrinkage of the resin during curing may be compensated by adding bentonite predried at a temperature just below the circulation temperature of the application range in the well bore.
  • Example 1 Open time for a DAP resin as a function of static background temperature
  • a resin was made from 100 g ortho-diallyl phthalate (DAP) , 30 g DAP prepolymer, 1 g tert-butyl-hydroperoxide and 0.45 g para-benzoquinone.
  • the homogeneous liquid was placed in a 25 ml volumetric flask, which was placed in a silicone oil bath with a static temperature of 150 ⁇ C (302°F).
  • the temperature vs time was measured for both the resin and the bath.
  • Figure 1 shows the temperature profile of the surrounding (oil-bath) and the DAP-resin cured at 150°C. Apparently, the exothermic curing reaction started at 152 in, while the curing peak came after 243 in with a heat exotherm of 12 ⁇ C.
  • Example 2 Open times for an iso-DAP resin as a function of static background temperature
  • a resin was made by mixing 100 g meta-diallyl phthalate (iso-DAP) with 1 % 2,5-bis(tert-butyl peroxy)-2,5-dimethyl- hexyne-3 and 0.80 % para-benzoquinone (PBQ) , by weight of the resin.
  • the homogeneous liquid was placed in a 25 ml volumetric flask, which was placed in a silicone oil bath with a static temperature of 150"C (302°F).
  • the temperature vs time was measured for both the resin and the bath, as revealed in Figure 3, showing the temperature profile of the surroundings (oil-bath) and the iso-DAP resin cured at 150°C.
  • the exothermic curing reaction started at 140 min, while the curing peak came after 155 min with a heat exotherm of 55"C.
  • An iso-DAP resin was made as described in Example 2.
  • the curing chamber was now a high temperature - high pressure (HTHP) viscometer after the viscometer parts had been removed.
  • the curing of iso-DAP resin was carried out at 1, 500 and 900 bars, respectively, and the end temperature was set at 150°C. All samples were taken from the same batch in order to exclude concentration variations.
  • the temperature vs time profiles for the iso-DAP resin at different pressures when the end temperature was set at 150°C are shown in Figure 5. Initially, the effect of the pressure was difficult to see correctly, since the temperature vs time profile varied for each experiment. In order to correct for this, the activation energy for the resin was calculated.
  • the resin was contained in a glass cylinder surrounded by oil, and the temperature vs time was recorded by a thermocouple in the oil and one in intimate contact with the glass wall of the cylinder.
  • the composition of the complete iso-DAP resin was:
  • the above recipe will give a calculated fresh density of 2.11 g/cm 3 .
  • the high content of initiator in this case (usually 1 %) gave a shorter open time than the usual 2 h at 150°C, since it is the initiator/inhibitor ratio that determines the open time.
  • the shrinkage of the samples was calculated by the difference in density in the fresh and in the cured state.
  • the density of the cured resin was calculated by weighing the whole sample (after removing the glass container) in air (m a ) and when immersed in water (m ;
  • the densities of the samples cured at 10 and 900 bars were 2.21 and 2.15 g/cm 3 , respectively.
  • sample cured at 900 bars had a well defined heat profile curve (maximum difference compared to bath about 40°C) , while the temperature in the sample at 10 bars only was slightly different ( ⁇ 4°C) from the ambient temperature of 150"C, which comply well with the results in Example 3.
  • the compressive strengths of the corresponding samples were determined to 52.6 and 59.2 MPa, respectively.

Abstract

Matériau de cimentation à délai de durcissement contrôlable, destiné à être utilisé pour la cimentation primaire et secondaire des puits de pétrole profonds à forte température, dont la température statique propre se situe entre 120 et 200 °C. Ce matériau renferme: a) une résine constituée d'ortho-, méta- et/ou para-diallylphtalates et/ou de prépolymères et/ou d'oligomères de ces substances; b) un agent de durcissement revêtant la forme d'un peroxyde organique dissous générant des radicaux libres; et c) un inhibiteur stabilisant les radicaux libres de manière à obtenir le délai nécessaire pour pomper la résine en place et, facultativement, les éléments suivants: d) une ou plusieurs charges de remplissage de poids élevé permettant de moduler la densité du ciment; e) des matériaux d'expansion permettant de moduler la consistance; et f) des matériaux compensant le retrait inhérent.
PCT/NO1993/000173 1992-11-20 1993-11-19 Materiaux de cimentation de substitution pour le conditionnement des puits de petrole profonds a forte temperature WO1994012445A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NO924493A NO176878C (no) 1992-11-20 1992-11-20 Sementeringsmateriale med regulert herdetid, for anvendelse i dype, varme oljebrönner
NO924493 1992-11-20

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WO1994012445A1 true WO1994012445A1 (fr) 1994-06-09

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NO (1) NO176878C (fr)
WO (1) WO1994012445A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2294693A (en) * 1994-10-25 1996-05-08 Sofitech Nv Cementig compositions and application thereof to cementing oil wells and the like
US5873413A (en) * 1997-08-18 1999-02-23 Halliburton Energy Services, Inc. Methods of modifying subterranean strata properties
AU708005B2 (en) * 1995-10-27 1999-07-29 Wellcem As Means and method for the preparation of sealings in oil and gas wells
US6006836A (en) * 1997-08-18 1999-12-28 Halliburton Energy Services, Inc. Methods of sealing plugs in well bores
US6006835A (en) * 1998-02-17 1999-12-28 Halliburton Energy Services, Inc. Methods for sealing subterranean zones using foamed resin
US6012524A (en) * 1998-04-14 2000-01-11 Halliburton Energy Services, Inc. Remedial well bore sealing methods and compositions
US6059035A (en) * 1998-07-20 2000-05-09 Halliburton Energy Services, Inc. Subterranean zone sealing methods and compositions
US6082456A (en) * 1996-10-25 2000-07-04 Wecem As Means and method for the preparation of sealings in oil and gas wells
US6098711A (en) * 1998-08-18 2000-08-08 Halliburton Energy Services, Inc. Compositions and methods for sealing pipe in well bores
US6124246A (en) * 1997-11-17 2000-09-26 Halliburton Energy Services, Inc. High temperature epoxy resin compositions, additives and methods
US6234251B1 (en) 1999-02-22 2001-05-22 Halliburton Energy Services, Inc. Resilient well cement compositions and methods
US6244344B1 (en) 1999-02-09 2001-06-12 Halliburton Energy Services, Inc. Methods and compositions for cementing pipe strings in well bores
US6454006B1 (en) 2000-03-28 2002-09-24 Halliburton Energy Services, Inc. Methods and associated apparatus for drilling and completing a wellbore junction
US7343974B2 (en) 2004-06-03 2008-03-18 Shell Oil Company Method and apparatus for performing chemical treatments of exposed geological formations
US7696133B2 (en) 2005-06-02 2010-04-13 Shell Oil Company Geosynthetic composite for borehole strengthening
WO2015084180A1 (fr) * 2013-12-04 2015-06-11 Wellcem As Matière de scellement pour puits souterrains
US10023783B2 (en) 2012-06-23 2018-07-17 Pumprock, Llc Compositions and processes for downhole cementing operations

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1247352A (fr) * 1984-11-19 1988-12-28 Robert H. Friedman Ciment chimique a resistance a la chaleur elevee

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1247352A (fr) * 1984-11-19 1988-12-28 Robert H. Friedman Ciment chimique a resistance a la chaleur elevee

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DIALOG INFORMATION SERVICES, File 350, World Patent Index 63-80, Dialog Accession No. 001434167, WPI Accession No. 75-83910W/51, OSAKA SODA KK: "Injection Moulding Compsn.-Based on Poly (Diallyl Isophthalate) and Poly (Diallyl Phthalate) Prepolymer Blends"; & JP,A,50 078 638, 26-06-75, 7551, (Basic). *

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2294693A (en) * 1994-10-25 1996-05-08 Sofitech Nv Cementig compositions and application thereof to cementing oil wells and the like
AU708005B2 (en) * 1995-10-27 1999-07-29 Wellcem As Means and method for the preparation of sealings in oil and gas wells
US6082456A (en) * 1996-10-25 2000-07-04 Wecem As Means and method for the preparation of sealings in oil and gas wells
US5875846A (en) * 1997-08-18 1999-03-02 Halliburton Energy Services, Inc. Methods of modifying subterranean strata properties
US5875844A (en) * 1997-08-18 1999-03-02 Halliburton Energy Services, Inc. Methods of sealing pipe strings in well bores
US5911282A (en) * 1997-08-18 1999-06-15 Halliburton Energy Services, Inc. Well drilling fluids containing epoxy sealants and methods
US5957204A (en) * 1997-08-18 1999-09-28 Halliburton Energy Services, Inc. Method of sealing conduits in lateral well bores
US5969006A (en) * 1997-08-18 1999-10-19 Halliburton Energy Services, Inc. Remedial well bore sealing methods
US6006836A (en) * 1997-08-18 1999-12-28 Halliburton Energy Services, Inc. Methods of sealing plugs in well bores
US5875845A (en) * 1997-08-18 1999-03-02 Halliburton Energy Services, Inc. Methods and compositions for sealing pipe strings in well bores
US5873413A (en) * 1997-08-18 1999-02-23 Halliburton Energy Services, Inc. Methods of modifying subterranean strata properties
US6124246A (en) * 1997-11-17 2000-09-26 Halliburton Energy Services, Inc. High temperature epoxy resin compositions, additives and methods
US6006835A (en) * 1998-02-17 1999-12-28 Halliburton Energy Services, Inc. Methods for sealing subterranean zones using foamed resin
US6069117A (en) * 1998-02-17 2000-05-30 Halliburton Energy Services, Inc. Foamed resin compositions for sealing subterranean zones
US6012524A (en) * 1998-04-14 2000-01-11 Halliburton Energy Services, Inc. Remedial well bore sealing methods and compositions
US6059035A (en) * 1998-07-20 2000-05-09 Halliburton Energy Services, Inc. Subterranean zone sealing methods and compositions
US6098711A (en) * 1998-08-18 2000-08-08 Halliburton Energy Services, Inc. Compositions and methods for sealing pipe in well bores
US6244344B1 (en) 1999-02-09 2001-06-12 Halliburton Energy Services, Inc. Methods and compositions for cementing pipe strings in well bores
US6234251B1 (en) 1999-02-22 2001-05-22 Halliburton Energy Services, Inc. Resilient well cement compositions and methods
US6454006B1 (en) 2000-03-28 2002-09-24 Halliburton Energy Services, Inc. Methods and associated apparatus for drilling and completing a wellbore junction
US6786283B2 (en) 2000-03-28 2004-09-07 Halliburton Energy Services, Inc. Methods and associated apparatus for drilling and completing a wellbore junction
US7343974B2 (en) 2004-06-03 2008-03-18 Shell Oil Company Method and apparatus for performing chemical treatments of exposed geological formations
US7741249B2 (en) 2004-06-03 2010-06-22 Shell Oil Company Geosynthetic composite for borehole strengthening
US7696133B2 (en) 2005-06-02 2010-04-13 Shell Oil Company Geosynthetic composite for borehole strengthening
US10023783B2 (en) 2012-06-23 2018-07-17 Pumprock, Llc Compositions and processes for downhole cementing operations
WO2015084180A1 (fr) * 2013-12-04 2015-06-11 Wellcem As Matière de scellement pour puits souterrains
US9688578B2 (en) 2013-12-04 2017-06-27 Wellcem As Sealant material for subterranean wells

Also Published As

Publication number Publication date
NO176878C (no) 1995-06-14
NO924493D0 (no) 1992-11-20
NO924493L (no) 1994-05-24
NO176878B (no) 1995-03-06

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