Stepan Company

Stepan Corporation

Patrick Shane Wolfe

Randal J Bernhardt

Aaron Brown

Andrew D Malec

Dennis S Murphy

Ronald Anthony Masters

Dave R Allen

Patti Skelton

Marcos Alonso

Brian Sook

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

Ronald A Masters

John C Hutchison

Gregory Wallace

Gary Luebke

Xue Min Dong

Franz Josef Luxem

Jeremy Aaron Weitgenant

Lena Titievsky

Wilma Gorman

David R Allen

Teresa Cuasay Manuel

Mary Beddaoui

Scott Dillavou

Chris Spaulding

Irma Ryklin

Marshall J Nepras

Krista L Turpin

Anatoliy A Dameshek

Teresa Germain

Nicholas Pendleton

Franz Luxem

Ramakrishna Ravikiran

Timothy A Boebel

James A Faunce

Sebastian Flieger

Leonard Frank Zaporowski

Kathryn E Merwin

Mona Marie Knock

Sarah E Kovach

Renata A Butikas

Thomas Edward Waldman

Anatoliy A Damashek

Xue Dong

Krista Turpin

Teresa C Manuel

Clear, stable concentrated liquid compositions are disclosed that comprise from 30% to 90% by weight of an esterquat active, and from 10% to 50% by weight of a particular solvent system. The esterquat active is the quaternized reaction product of a fatty acyl source having an Iodine Value of 40 to 130 reacted with an alkanolamine at a fatty acyl to alkanolamine molar ratio of 1.0:1 to 2.2:1. The concentrated liquid compositions have a VOC content of less than 5%, a Biorenewable Carbon Index (BCI) of at least 20 and a viscosity of less than 5000 cP at 25° C. The concentrated liquid compositions can be easily diluted in water to form stable aqueous dispersions.

Concentrated liquid esterquat compositions

Dilutable concentrates useful for hard surface cleaners with improved film/streak performance on high-energy surfaces are disclosed. The concentrates comprise a nonionic alkoxylated surfactant and a polyetheramine. A relatively minor proportion of a polyetheramine can resolve film/streak issues that characterize hard surface cleaners formulated with nonionic surfactants. The efficacy of polyetheramines for improving film/streak performance of hard surface cleaners formulated with nonionic alkoxylated surfactants far exceeds the benefits available from known improvements, such as the use of hydrotropes. Other inventive dilutable concentrates and hard surface cleaners comprise an amine-functional hydrophobe and an auxiliary surfactant. Still other dilutable concentrates or hard surface cleaners comprise a nonionic alkoxylated surfactant and lactic acid. An improved method for measuring film/streak properties of hard surface cleaners is also disclosed.

Reduced-residue hard surface cleaner and method for determining film/streak

Esterquat compositions are disclosed that comprise, based on the weight of the composition, 0% to about 70% by weight of a solvent, and about 30% to 100% by weight of a mixture comprising about 50% to about 80% by weight, based on the weight of the mixture, of esterquats and about 20% to about 50% by weight, based on the weight of the mixture, of mono- and diglycerides. The esterquat compositions can be prepared by the direct esterification of a natural oil with an alkanolamine, followed by quaternization in the presence of the solvent. The esterquat compositions can be formulated into hair care compositions that provide improved wet and dry combing properties.

Esterquat compositions

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

Detergent compositions comprising one or more surfactants and a polyetheramine composition are disclosed. The polyetheramine composition comprises a compound having a polyglycerol core and an aminoalkyl group or an oxidized aminoalkyl group that is bonded directly or indirectly to each available oxygen of the polyglycerol core. Optionally, oxyalkylene groups link available oxygens of the polyglycerol core to the aminoalkyl or oxidized aminoalkyl groups. Methods for laundering textile articles and other cleaning methods using the detergent compositions are also disclosed. The polyetheramines can use diglycerol, a convenient plant-based starter. Laundry detergents comprising the polyetheramines provide enhanced cold-water cleaning performance for greasy or oily stains compared with similar detergents formulated without the polyetheramines.

Polyetheramine compositions for laundry detergents

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.

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

Growing community of inventors

Palatine, IL, United States of America

Patrick Shane Wolfe