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US-12624272-B2 - Pourable wetting agents and methods associated therewith

US12624272B2US 12624272 B2US12624272 B2US 12624272B2US-12624272-B2

Abstract

Pourable wetting agent compositions include a first condensation reaction product having a structure represented by the formula R″—NH—CH 2 —(CH 2 NR″CH 2 ) a —CH 2 —C 3 H 4 N 2 —R′; wherein a is 0 or a positive integer; R′ is a C 6 -C 30 hydrocarbyl group; and R″ is-CO—R′ or —CO-A-COOH, provided that at least one occurrence of R″ is-CO-A-COOH; wherein A is a divalent hydrocarbyl group.

Inventors

  • QUSAI A. DARUGAR
  • Ashok Santra
  • Nicolas OSORIO

Assignees

  • SAUDI ARABIAN OIL COMPANY

Dates

Publication Date
20260512
Application Date
20240530

Claims (8)

  1. 1 . A composition comprising: a first condensation reaction product having a structure represented by wherein: a is 0 or a positive integer; R′ is a C 6 -C 30 hydrocarbyl group; and R″ is-CO—R′ or —CO-A-COOH, provided that at least one occurrence of R″ is —CO-A-COOH; wherein A is a divalent hydrocarbyl group; a second condensation reaction product having a structure represented by wherein: b is a positive integer; R′ is a C 6 -C 30 hydrocarbyl group; and R″ is-CO—R′ or —CO-A-COOH, provided that at least one occurrence of R″ is-CO-A-COOH; and wherein the first condensation product and the second condensation product have a ratio from about 100:0 to about 31:69.
  2. 2 . The composition of claim 1 , wherein b is 1, 2, or 3.
  3. 3 . The composition of claim 1 , wherein A is a C 1 -C 3 alkyl group, a C 2 -C 3 alkenyl group, or a C 2 -C 3 alkynyl group.
  4. 4 . The composition of claim 1 , wherein R′ is a C 6 -C 30 alkyl group.
  5. 5 . The composition of claim 1 , wherein a is 0, 1, or 2.
  6. 6 . A drilling fluid comprising: an invert emulsion comprising an oil and water; and the composition of claim 1 .
  7. 7 . The drilling fluid of claim 6 , further comprising: an additive comprising at least one material selected from the group consisting of a primary emulsifier, a viscosifier, a weighting material, a fluid-loss control additive, an alkaline compound, and any combination thereof.
  8. 8 . A drilling method comprising: operating a drill in a wellbore in the presence of the drilling fluid of claim 6 .

Description

FIELD OF THE DISCLOSURE The present disclosure relates generally to oil-based drilling fluids and, more particularly, to oil-based drilling fluids containing wetting agents. BACKGROUND OF THE DISCLOSURE Drilling fluids, also referred to as drilling muds, are integral to the success of drilling programs, fulfilling several crucial functions. Drilling fluids are designed to maintain optimal wellbore pressure, provide cooling and lubrication to the drill bit, and facilitate the removal of solids and drill cuttings from the wellbore. Initial mud systems, comprising water and clay, remain in use today. However, these fluids are characterized by a reduced penetration rate and have the potential to interact adversely with clay and shale sections of subterranean formations, leading to complications such as wellbore collapse and stuck pipe, for example. To counteract these issues, drilling fluids based on non-aqueous or oil-based formulations have been developed. Early oil-based drilling fluids were deployed for reactive formations and to enhance drilling performance; however, these drilling fluids fell short in terms of possessing fluid properties suitable for operations under higher temperatures and pressures and lacked an effective supporting fluid structure to promote removal of drill cuttings from the borehole. To rectify the foregoing challenges, invert emulsion drilling fluids containing chemical additives (e.g., emulsifiers/emulsifying agents) to facilitate mixing of otherwise immiscible components (e.g., oil and water) have been developed. Oil-based drilling fluids have recently enjoyed significant improvements through the incorporation of additional chemical additives to enhance the fluids' performance in extreme conditions, including elevated temperatures and pressures. Despite these advancements, the emulsifying agents used have seen minimal change. Traditionally, drilling fluids have incorporated a combination of a primary emulsifier and a secondary emulsifier (e.g., a wetting agent). Primary emulsifiers commonly comprise complex mixtures derived from animal fats or oleaginous byproducts, such as tall oil from the pulp industry, for example. These low-cost commodity chemicals are typically used as-procured, without further chemical modification. Wetting agents play a critical role in the formulation of modern drilling fluids, especially in oil-based drilling fluid systems comprising an oil-based emulsion. Unfortunately, some wetting agents are notoriously viscous and are often not pourable from a storage container at ambient temperatures, thereby complicating the preparation of oil-based drilling fluids. Therefore, there exists a need for less viscous wetting agents that are still capable of maintaining the enhanced performance of modern oil-based drilling fluids. SUMMARY OF THE DISCLOSURE Various details of the present disclosure are hereinafter summarized to provide a basic understanding. This summary is not an extensive overview of the disclosure and is neither intended to identify certain elements of the disclosure, nor to delineate the scope thereof. Rather, the primary purpose of this summary is to present some concepts of the disclosure in a simplified form prior to the more detailed description that is presented hereinafter. According to an embodiment consistent with the present disclosure, pourable wetting agent compositions include a first condensation reaction product having a structure represented by wherein: a is 0 or a positive integer; R′ is a C6-C30 hydrocarbyl group; and R″ is —CO—R′ or —CO-A-COOH, provided that at least one occurrence of R″ is —CO-A-COOH; wherein A is a divalent hydrocarbyl group. In another embodiment, methods associated with pourable wetting agents include providing a composition comprising a first amidated imidazoline having a structure represented by wherein a is 0 or a positive integer; R′ is a C6-C30 hydrocarbyl group; and X is H or —CO—R′, provided that at least one occurrence of X is H; combining the composition with a dicarboxylic acid having a formula of HOOC-A-COOH to form a reaction mixture; wherein A is a divalent hydrocarbyl group; and heating the reaction mixture at a first reaction temperature for a first time period to form a second amidated imidazoline having a structure represented by wherein: a is 0 or a positive integer; R′ is a C6-C30 hydrocarbyl group; and R″ is —CO—R′ or —CO-A-COOH, provided that at least one occurrence of R″ is —CO-A-COOH. Any combinations of the various embodiments and implementations disclosed herein can be used in a further embodiment, consistent with the disclosure. These and other aspects and features can be appreciated from the following description of certain embodiments presented herein in accordance with the disclosure and the accompanying drawings and claims. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1A is an illustrative FTIR spectrum of an amidated imidazoline. FIG. 1B is an illustrative FTIR spectrum of an experimenta