Stepan Company

Andrew D Malec

Patrick Shane Wolfe

Randal J Bernhardt

Aaron Brown

Ronald Anthony Masters

Patti Skelton

Dave R Allen

Brian Sook

Dennis S Murphy

Marcos Alonso

Michael Wiester

Renee Luka

Gary R Luebke

Michael R Terry

Laura Lee Whitlock

Sangeeta Ganguly-Mink

Kelly Buchek

Brian Holland

Irene Shapiro

Lawrence A Munie

Gregory Wallace

Gary Luebke

Jeremy Aaron Weitgenant

Xue Min Dong

Franz Josef Luxem

Wilma Gorman

David R Allen

John C Hutchison

Teresa Cuasay Manuel

Krista L Turpin

Lena Titievsky

Chris Spaulding

Mary Beddaoui

Irma Ryklin

Marshall J Nepras

Nicholas Pendleton

Scott Dillavou

Franz Luxem

Anatoliy A Dameshek

Anatoliy A Damashek

Timothy M Figley

Xue Dong

Krista Turpin

Ronald A Masters

Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed. The derivatives and sulfate compositions are valuable for many end-use applications, including, for example, agricultural dispersants, water-soluble herbicides, anionic emulsifiers for agricultural use, hard surface cleaners, light-duty liquid detergents, personal cleansers, gas well foamers for oilfield applications, laundry detergents, enhanced oil recovery compositions, latex paints, and specialty foams.

Unsaturated fatty alcohol derivatives from natural oil metathesis

This invention relates to a storage stable, aqueous, herbicidal formulation containing an ultra-high concentration of glyphosate in the isopropylamine, potassium or mixed salt form in combination with a surfactant system, to a method of making the formulation, and to a method of treating unwanted vegetation employing the formulation. The surfactant system employed in the concentrate comprises dialkoxylated alkylamine, water miscible solubilizer and amine oxide. The surfactant system unexpectedly permits the formulation of storage stable, ultra-high loaded aqueous glyphosate salt concentrates possessing high or no cloud points.

Ultra-high loading glyphosate concentrate

Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.

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

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

Unsaturated fatty alcohol alkoxylates, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol alkoxylate is made by reducing a metathesis-derived monounsaturated alkyl ester, followed by alkoxylation of the resulting monounsaturated alcohol. Microscopy reveals that the monounsaturated alkoxylates have isotropic and lamellar phases over a wider range of actives levels compared with their saturated analogs. This attribute expands formulating latitude for many end-use applications. The unsaturated fatty alcohol alkoxylates are valuable in, for example, agricultural solvents, nonionic emulsifiers for agricultural compositions, hard surface cleaners, laundry detergents, specialty foams, additives or surfactants for paints or coatings, and surfactant compositions for enhanced oil recovery.

Unsaturated fatty alcohol alkoxylates 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

A film may be formed from film forming compositions which comprise at least one carboxamide based coalescing solvent. These coalescing solvents impart equivalent or improved wet-scrub resistance, block resistance, gloss, dirt pick-up resistance and leveling characteristics to the films on a substrate, without contributing to total VOC levels, when replacing conventional coalescing solvents. The present invention also includes a method for forming a film comprising applying a film forming composition comprising polyunsaturated reactive carboxamides to a substrate and curing the film under ambient conditions. The coalescing carboxamide solvents are suitable for paint, latex based caulk, adhesives and floor care applications.

Film forming coating compositions containing carboxamide coalescing solvents and methods of use

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

Growing community of inventors

Chicago, IL, United States of America

Andrew D Malec