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WO 2015/026689 Al 26 February 2015 (26.02.2015) P O P C T

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WO 2015/026689 Al 26 February 2015 (26.02.2015) P O P C T (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 WO 2015/026689 Al 26 February 2015 (26.02.2015) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every CIOG 33/04 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US2014/05141 1 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 18 August 2014 (18.08.2014) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (25) Filing Language: English OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (26) Publication Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (30) Priority Data: ZW. 61/867,328 19 August 2013 (19.08.2013) US (84) Designated States (unless otherwise indicated, for every (71) Applicant: GEORGIA-PACIFIC CHEMICALS LLC kind of regional protection available): ARIPO (BW, GH, [US/US]; 133 Peachtree Street NE, Atlanta, Georgia 30303 GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (US). UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (72) Inventors: HURD, Phillip W.; 188 1 Lancaster Drive, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, Conyers, Georgia 30013 (US). HINES, John B.; 1092 MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Colquitt Avenue, Atlanta, Georgia 30307 (US). JOHN¬ TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, SON, Roger Scott; 146 1 Sandford Trail, Lilburn, Georgia KM, ML, MR, NE, SN, TD, TG). 30047 (US). MPOFU, David T.; 1305 Charleston Place, Dunwoody, Georgia 30338 (US). RIFE, Nathan P.; 4607 Published: Morning Cloud Lane, Sugar Land, Texas 77479 (US). — with international search report (Art. 21(3)) COTHRAN, Anne M.; 3748 Windy Hill Drive, S.E., Con yers, Georgia 30013 (US). (74) Agents: SABNIS, Ram W. et al; Georgia-Pacific LLC, 133 Peachtree Street NE, Atlanta, Georgia 30303 (US). (54) Title: METHODS FOR PRODUCING EMULSIFIERS FOR OIL-BASED DRILLING FLUIDS O o J R NH[(CH 2) N(CH2) NH R (I) R o O 00 (Π) OH © (57) Abstract: Methods for making emulsifiers, emulsified drilling fluids, and methods for using the same are provided. In one or o more embodiments, the method for making an emulsifier can include mixing a tall oil and a triamide. The triamide can have the chemical formula (I) where: x, y, and z are integers independently selected from 1 to 10, R 1 is a -C20 alkyl, a -C20 alkenyl, a Cs- 4 C 20 dialkenyl, or a C -C2o alkynyl, R 2 is H or (II) independently selected for each [(CH 2)xN R (CH 2)y] unit, where R is a -C al- o 2 3 kylene or a C 1 alkylene alcohol, and where at least one R is (II), and R is a Cs-C2oalkyl, a Cs-C20 alkenyl, a Cs-C2odialkenyl, or a C -C2 alkynyl. METHODS FOR PRODUCING EMULSIFIERS FOR OIL-BASED DRILLING FLUIDS CROSS-REFERENCE TO RELATED APPLICATION [0001] This application claims benefits of U.S. Provisional Patent Application No. 61/867,328, filed August 19, 2013, which is incorporated by reference herein in its entirety. BACKGROUND Field [0002] Embodiments described generally relate to methods for making emulsifiers that can include one or more tall oils and one or more triamides, emulsified drilling fluids, and methods for using same. Description of the Related Art [0003] The oil and gas industry has used drilling fluids or "drilling muds" for a number of years to tap subterranean deposits of natural resources. As the total reserves of oil diminish, it has become necessary to drill in areas that were previously inaccessible due to technological or economic difficulties. This has led to the widespread use of oil-based drilling fluids or invert emulsion drilling fluids, which offer greater thermal and chemical stability than water-based fluids, allowing for drilling at extended depths and in other demanding services, such as those involving exposure to high electrolyte concentrations and soluble gases. For example, invert emulsion drilling fluids have been used successfully in drilling hot (e.g., greater than 150°C) formations as well as those containing hydrogen sulfide. Also, to maximize recovery from each platform in offshore drilling, invert emulsion drilling fluids are favored due to their effectiveness for drilling deviated wells (e.g., angled wells). In particular, the high lubricity of invert emulsion drilling fluids is necessary because of the increased torque exerted on the drill string in deviated drilling. [0004] Invert emulsion drilling fluids are typically formed by blending a hydrocarbon oil with water or brine under high shear conditions and in the presence of a suitable emulsifier. The emulsifier is required not only to form a stable dispersion of water droplets in the oil phase, but also to maintain any solids such as weighting material additives (e.g., barites) or drill cuttings in an oil-wet state. With space at some well sites limited, such as on offshore platforms, and with increasing costs of transport of materials to a well site, there is industry wide interest particularly in drilling fluid compositions that can be formulated and maintained (e.g., stored) with minimal or fewer quantities of solvent and other additives, compared to prior art compositions. [0005] There is a need, therefore, for improved emulsifiers for use in invert emulsions that can be used, for example, in oil well drilling. SUMMARY [0006] Methods for making emulsifiers, emulsified drilling fluids, and methods for using the same are provided. In one or more embodiments, the method for making an emulsifier can include mixing a tall oil and a triamide. The triamide can have the general chemical formula, Formula (I): where: x, y, and z are integers independently selected from 1 to 10, R is a C 8-C20 alkyl, a C 8-C20 alkenyl, a C 8-C20 dialkenyl, or a C 8-C20 alkynyl, 0 0 R is H or independently selected for each 4 [(CH 2)xN R (CH 2) ] unit, where R is a C1-C3 alkylene or a C1-C3 alkylene alcohol, O 0 Η and where at least one R is a n j R 3 is a C 8-C20 alkyl, a C 8-C20 alkenyl, a C 8-C20 dialkenyl, or a C 8-C20 alkynyl. [0007] In some embodiments, the method for making an emulsifier can include mixing a triamide and a tall oil. The triamide can be prepared by reacting a diamidoamine with a saturated dicarboxylic acid, a saturated acid anhydride, or a mixture thereof. The method can also include spray drying the emulsifier to provide a spray dried emulsifier. [0008] The method for making a drilling fluid can include mixing an oil phase, an aqueous phase, and a spray dried emulsifier to produce a drilling fluid. The spray dried emulsifier can include a mixture of a tall oil and a triamide, where the triamide can have Formula (I). DETAILED DESCRIPTION [0009] Methods for making emulsifiers, emulsified drilling fluids, and methods for using the same are provided. In one or more embodiments, the emulsifier can be made by mixing, blending, or otherwise combining one or more tall oils and one or more triamides. The one or more triamides can be represented by the general chemical formula, Formula (I): R where: x, y, and z are integers independently selected from 1 to 10, R is a C8-C20 alkyl, a C8-C20 alkenyl, a C8-C20 dialkenyl, or a C8-C20 alkynyl, O 0 R2 is H o R H independently selected for each 4 [(CH 2)xNR (CH 2) ] unit, where R is a C1-C3 alkylene or a C1-C3 alkylene alcohol, O O 2 and where at least one R is R ΟΗ and R3 is a C8-C20 alkyl, a C8-C20 alkenyl, a C8-C20 dialkenyl, or a C8-C20 alkynyl. 4 [0010] The C1-C3 alkylene for R can include, but is not limited to, a methylene or methanediyl group (-CH 2-), an ethylene or ethanediyl group (-CH 2CH2-), and a propylene or propanediyl group (-CH2CH2CH2-), which provides a saturated alkane moiety in the triamide. 4 The C1-C3 alkylene alcohol for R can include, but is not limited to, a methylene or methanediyl alcohol group (-C(OH)H-), an ethylene or ethanediyl alcohol group (-CH 2C(OH)H-), and a propylene or propanediyl alcohol group (-CH 2C(OH)HCH 2- or -CH 2CH2C(OH)H-), which provides a saturated alkane alcohol moiety in the triamide. [0011] In some embodiments, the emulsifier can be used for oil-based drilling fluids. It has 4 been surprisingly and unexpectedly discovered that when R is a C1-C3 alkylene or a C1-C3 alkylene alcohol, e.g. , a saturated carbon chain, the oil-based drilling fluids can exhibit one or more of the following properties: flatter low end rheology, lower high end rheology, higher electrical stability, lower plastic viscosity, lower gel strengths, and lower fluid loss to the subterranean formation, as compared to the same emulsifier, but having an unsaturated R4, e.g., an R4 having at least one carbon-carbon double bond.
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