Stepan Company

Dave R Allen

Randal J Bernhardt

Patrick Shane Wolfe

Aaron Brown

Andrew D Malec

Ronald Anthony Masters

Patti Skelton

Dennis S Murphy

Marcos Alonso

Brian Sook

Michael Wiester

Laura Lee Whitlock

Michael R Terry

Kelly Buchek

Sangeeta Ganguly-Mink

Irene Shapiro

Renee Luka

Gary R Luebke

Brian Holland

Lawrence A Munie

Jeremy Aaron Weitgenant

Lena Titievsky

Teresa Cuasay Manuel

Gregory Wallace

Ronald A Masters

Marshall J Nepras

Gary Luebke

Elodie Shaw

Anatoliy A Dameshek

Krista L Turpin

Scott Dillavou

Anatoliy A Damashek

Eric M Weber

Andrea B E Brayton

Julien Guillan

Agricultural compositions that employ structured surfactant systems to suspend water-insoluble or sparingly soluble agricultural actives and/or adjuvants are disclosed. Also disclosed are agricultural compositions that combine structured surfactant systems with electrolytes to form structured electrolyte compositions. The structured surfactant systems, both with and without electrolyte, suspend one or more agricultural actives and/or crop oil and non-aqueous adjuvants to provide agricultural compositions that can combine combinations of actives in a single, stable composition.

Agricultural compositions containing structured surfactant systems

Agricultural compositions having reduced aquatic toxicity are disclosed. The compositions comprise an agricultural active, a monounsaturated C-Cfatty amine ethoxylate, and optionally water. The compositions may further comprise an auxiliary surfactant, a solvent, or both. In certain preferred aspects, the agricultural active is a glyphosate salt. Agricultural compositions comprising a monounsaturated C-Cfatty amine ethoxylate have good herbicidal efficacy. Unexpectedly, the monounsaturated C-Cfatty amine ethoxylates have reduced aquatic toxicity when compared with their saturated analogs.

Agricultural compositions with reduced aquatic toxicity

Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a primary or secondary amine. Derivatives made by reducing, quaternizing, sulfonating, alkoxylating, sulfating, and sulfitating the fatty amide are also included. The amine reactant can be diethylenetriamine or (2-aminoethyl)ethanolamine, which provide imidazoline amides or esters, respectively. In one aspect, the ester derivative of the C-Cmonounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.

Fatty amides and derivatives from natural oil metathesis

Fatty amine compositions made from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. In another aspect, fatty amidoamines made by reacting a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with an aminoalkyl-substituted tertiary amine are disclosed. The fatty amines or amidoamines are advantageously sulfonated, sulfitated, oxidized, or reduced. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.

Fatty amines, amidoamines, and their derivatives from natural oil metathesis

Personal cleansers and surfactant blends useful therein are disclosed. The cleansers comprise a primary anionic surfactant, a saturated C-C-alkyl N,N-dialkylamide, and water. The cleansers have good foaming properties and improved viscosity build profiles compared with cleansers that rely on alkanolamides or betaines as the secondary surfactant. The saturated C-Calkyl N,N-dialkylamides are water-white liquids that solubilize cleanser components well, including high levels of fragrances, and can be formulated easily without heating at any actives level up to 100%. Importantly, the surfactant blends build viscosity with less added salt compared with alkanolamide or betaine-based blends, even with more challenging anionic surfactants. Moisturizing cleansers disclosed herein have excellent flash foaming character, foam volume, and foam feel and provide a luxurious, lotion-like after-feel. The personal cleansers include, among others, shampoos, body washes, facial cleansers, shower gels, liquid soaps, hand soaps, baby liquid cleansers, pet shampoos, and bubble baths. The fatty N,N-dialkylamides are also valuable for formulating oil-in-water emulsions with good stability.

Personal cleansers and surfactant blend therefor

Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C-Cmonounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride N made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Quaternized fatty amines, amidoamines and their derivatives from natural oil

Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C-Cmonounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Esteramines and derivatives from natural oil metathesis

Sulfonate compositions are disclosed. The compositions include alkanesulfonates, alkenesulfonates, sultones, and hydroxy-substituted alkanesulfonates. The sulfonates comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a sulfonating or sulfitating agent. In one aspect, the sulfonate composition is a sulfo-estolide made by reacting a metathesis-derived C10-C17 monounsaturated acid or octadecene-1,18-dioic acid with a sulfonating agent, optionally in the presence of a saturated fatty acid. The sulfonates are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), paint additives, antimicrobial compositions, agricultural uses, and oil field applications.

Sulfonates from natural oil metathesis

Imidazoline amides and derivitives from natural oil metathesis

Alkoxylated fatty ester compositions are disclosed. In one aspect, the compositions comprise a reaction product of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with one or more alkylene oxides in the presence of an insertion catalyst to give an alkoxylated fatty ester. In another aspect, the metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or its ester derivative is reacted with a glycol ether or a glycol ether alkoxylate, to give an alkoxylated fatty ester. In yet another aspect, the metathesis-derived C-Cmonounsaturated acid or octadecene-1,18-dioic acid is reacted with one or more alkylene oxides to give a fatty acid alkoxylate, followed by etherification of the fatty acid alkoxylate.

Alkoxylated fatty esters and derivatives from natural oil metathesis

Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C-Cmonounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Quaternized fatty amines, amidoamines and their derivatives from natural oil metathesis

Laundry detergents useful for cold-water cleaning and boosted bargain detergents are disclosed. The detergents include a surfactant composition derived from a metathesis-derived C-Cmonounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. For fatty alkyl ester sulfonate-containing detergents, the composition is selected from Cbetaines, Cor Camidoamines, Cethanolamine amides, Camidoamine sulfonates, Cdiamidoamine dioxides, quaternized Cdiamidoamine betaines, sulfonated Clow-EO fatty ester alkoxylates, Camidoamine carboxylates, and amidoamine oxides and sulfobetaines derived from cross-metathesis of palm or soybean oil. The bargain detergents include a performance booster selected from Clow-EO fatty ester alkoxylate sulfonates, Camidoamine oxide esters, Camidoamine oxide carboxylates, and amidoamine sulfobetaines made from self metathesized palm or soybean oil.

Laundry detergents based on compositions derived from natural oil metathesis

Aqueous hard surface cleaner compositions derived from metathesized natural oil feedstocks are disclosed. In one aspect, the compositions comprise at least one anionic surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, 5 octadecene-1,18-dioic acid, or their ester derivatives. In another aspect, aqueous hard surface cleaners comprising at least one nonionic or amphoteric surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. The aqueous cleaners noted above rival or outperform commercial baselines in a Gardner straight-line washability test. Industrial degreasers comprising a C10 or C12 amide solvent and derived from a metathesis-derived C10-C17 monounsaturated acid are superior to commercial standards.

Hard surface cleaners based on compositions derived from natural oil  metathesis

Growing community of inventors

Chicago, IL, United States of America

Dave R Allen