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(12) STANDARD PATENT (11) Application No. AU 2014251001 B2 (19) AUSTRALIAN PATENT OFFICE

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(12) STANDARD PATENT (11) Application No. AU 2014251001 B2 (19) AUSTRALIAN PATENT OFFICE (12) STANDARD PATENT (11) Application No. AU 2014251001 B2 (19) AUSTRALIAN PATENT OFFICE (54) Title Choline-based crosslinker compositions for fracturing fluids (51) International Patent Classification(s) C08K 5/17 (2006.01) C08J 3/24 (2006.01) C08B 37/00 (2006.01) C08K 5/04 (2006.01) (21) Application No: 2014251001 (22) Date of Filing: 2014.04.09 (87) WIPO No: WO14/169044 (30) Priority Data (31) Number (32) Date (33) Country 61/810,498 2013.04.10 US (43) Publication Date: 2014.10.16 (44) Accepted Journal Date: 2018.02.15 (71) Applicant(s) Ecolab USA Inc. (72) Inventor(s) Song, Jingshe;Kurian, Pious;Street, Joseph Paul;Cason, Rhyn (74) Agent / Attorney Pizzeys Patent and Trade Mark Attorneys Pty Ltd, GPO Box 1374, BRISBANE, QLD, 4001, AU (56) Related Art US 2006116296 Al US 2007173414 Al US 2008287325 Al WARTELLE, L. H. et al., 'Chromate ion adsorption by agricultural by-products modified with dimethyloldihydroxyethylene urea and choline chloride', Water Research. 2005, vol. 39, pages 2869-2876. (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date W O 2014/169044 A1 16 October 2014 (16.10.2014) W IPO I PCT (51) International Patent Classification: DO, DZ, EC, EE, EG, ES, Fl, GB, GD, GE, GH, GM, GT, C08K5/17(2006.01) C08K 5/04 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, C08J3/24 (2006.01) C08B 37/00 (2006.01) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/US2014/033511 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 9 April 2014 (09.04.2014) ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated,for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (30) Priority Data: UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 61/810,498 10 April 2013 (10.04.2013) US TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, Fl, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, (71) Applicant: ECOLAB USA INC. [US/US]; 370 N. Wa- MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, basha Street, St. Paul, Minnesota 55102 (US). TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (72) Inventors: SONG, Jingshe; 1207 Windover Court, Sugar KM, ML, MR, NE, SN, TD, TG). Land, Texas 77479 (US). KURIAN, Pious; 5727 White Declarations under Rule 4.17: River Pass Lane, Sugar Land, Texas 77479 (US). - as to applicant'sentitlement to applyfor and be granted a STREET, Joseph Paul; 3 Queens Lane, Friendswood, patent (Rule 4.17(ii)) Texas 77546 (US). CASON, Rhyn; 15211 Park Row Boulevard, Apt. 2132, Houston, Texas 77084 (US). Published: (74) Agent: SORENSEN, Andrew D.; Ecolab USA Inc., 655 - with internationalsearch report (Art. 21(3)) Lone Oak Drive, Eagan, Minnesota 55121 (US). - before the expiration of the time limit for amending the (81) Designated States (unless otherwise indicated,for every claims and to be republished in the event of receipt of kind of nationalprotection available): AE, AG, AL, AM, amendments (Rule 48.2(h)) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (54) Title: CHOLINE-BASED CROSSLINKER COMPOSITIONS FOR FRACTURING FLUIDS (57) Abstract: Disclosed are compositions derived of mixtures of choline ion salts (typically choline chloride) in aqueous solution with suspended particulates of sparingly soluble borate minerals or with alkali or alkaline earth borate salts, boric acid and its ester derivatives and salts, or other aqueous soluble borate forms. These compositions are useful as cross-linkers for polysaccharides and other biopolymers and particularly as used in subterranean treatment fluids for completion and stimulation of oil and gas wells. Ad f4 vantages of the compositions are the combination into a single package of the properties of clay stabilizing actives (choline ion) and crosslinking actives (borates, etc.), in relatively high concentrations, and these compositions are easy to handle, being stable and pumpable at low temperatures, and with attractive environmental profiles. Also disclosed are the analogous choline solutions mixed 4 3 3 with metallic cross-linking ions know in the art such as Zr*, Ti *, Al +, & Fe . WO 2014/169044 PCT/US2014/033511 CHOLINE-BASED CROSSLINKER COMPOSITIONS FOR FRACTURING FLUIDS FIELD OF THE INVENTION [0001] The present invention relates to solutions and/or suspensions containing crosslinking agents in an aqueous brine of choline salts and is applied as a time released crosslinker for polymer solutions, methods of using these compositions, and methods of preparing the compositions. BACKGROUND OF THE INVENTION [0002] Fracturing, or hydraulic fracturing, involves the injection of specialized fluids into geologic formations to create fractures. These fractures, in combination with flow paths drilled by wellbores, allow hydrocarbons, such as oil or natural gas, to flow from the deep recesses of the geologic formations to the ground surface. The injected specialized fluids are called fracturing fluids, which carry proppant into the fractures. [0003] For many years, fracturing fluid technology has centered on a wide range of polymers. Polysaccharides such as guar, hydroxypropyl guar (HPG) and hydroxyethylcellulose (HEC) are the most commonly used polymers to provide the fluid viscosity. Since high viscosities are needed to carry the required amount of proppant, high concentrations of polymer are used and the polymers are frequently crosslinked to achieve the necessary viscosity. Cross-linked polymer gels, such as those based on guar crosslinked with borate or other polymers crosslinked with metal ions, are typically used to attain a sufficient fluid viscosity and thermal stability in high temperature reservoirs. [0004] The crosslinking agents for polysaccharide solutions used in well treating fluids are well known in the art. One common type of crosslinker is transition metal containing compounds including titanium (4), zirconium (4'), chromium (3), iron(3) and aluminum (3) formulated as a product so as to release transition metal ions when dissolved in an aqueous liquid. The most commonly used crosslinker is based on borate releasing compounds due to its reversibility of crosslinking. The borate source may include easily soluble borate oxides such as boric acid and/or sodium borate (borax). The borate source can also be lowly soluble borate minerals such as ulexite, colemanite, probertite, and mixtures thereof. Products of this type have a 1 WO 2014/169044 PCT/US2014/033511 technical advantage of delayed crosslinking action upon use, which is a desired property for many fracturing applications, and is a consequence of the low solubility. The borate source can also be a mixture of lowly soluble borate minerals and/or boric acid and/or ester derivatives of boric acid and/or borax and/or alkali borate salts and/or alkali earth borate salts. [0005] In order to add borate or metallic crosslinkers easily and accurately into the fracturing fluids, it is better for the crosslinker to be in a liquid form. In many cases, it is advantageous to have highly concentrated formulations with actives present in excess of their solubility limits, typically dispersed as a suspension of the particular active in an appropriate liquid suspension medium. One common medium is non aqueous liquids such as hydrocarbon solvents. See US 6,024,170, which is incorporated fully herein by reference. [0006] Numerous problems exist when utilizing non-aqueous suspensions. Many of the non-aqueous liquid suspensions are environmentally unacceptable due to the choice of the oil and have poorer suspension and stability characteristics, and may be more expensive and difficult to prepare. [0007] US 2003/0144154 A1, which is fully incorporated herein by reference, discloses a concentrate for the crosslinking of polymers in aqueous solutions, which comprises an alkali metal formate solution, a crosslinking agent, a suspension agent, and optionally a deflocculant. The preferred alkaline metal formate is potassium formate. The preferred suspension agent is a clay mineral selected from the group consisting of smectite clays, palygorskite clays and mixtures thereof. The key of this technology is the addition of formate salt, which decreases the freezing point of the product and increases the density of the suspension. Under this technology, however, clay minerals are also required. [0008] Solutions of low molecular weight quaternary ammonium compounds have also been used in hydraulic fracturing fluids for their clay stabilizing properties, in which the presence of this type of ion helps prevent the swelling of clay minerals present in the subterranean formation, which come into contact with water as a result of the fracturing operation. Clay swelling and associated fines migration leads to reservoir permeability damage. Tetramethyl ammonium chloride is the historically most used substance in this category, but the natural product choline in the form of its 2 WO 2014/169044 PCT/US2014/033511 chloride salt has in recent years become the product of choice because of its inherently non-toxic and bio-assimilation properties. [0009] A perhaps lesser appreciated property of choline chloride is the high water solubility (70-75 weight % are typical solution concentrations) and corresponding high solution density and low freezing point. This makes choline chloride solutions ideal media for suspension of dense materials such as sparingly soluble borate minerals and metal ions.
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