Abstract: 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.

Abstract: 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.

Abstract: Compositions comprising at least one dialkyl amino acid ester salt as a cationic active are disclosed. The compositions are useful for hair care, as well as in other applications, such as cleaning compositions, fabric softening compositions, and skin care compositions. The dialkyl amino acid ester salts are derived from the esterification reaction of an amino acid having at least two carboxylic acid groups with a fatty alcohol, wherein the amine group of the amino acid is protonated with an acid. The compositions may further include a glyceride component comprising monoglycerides, diglycerides, or a combination thereof.

Abstract: 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.

Abstract: Compositions comprising a synergistic mixture of at least one neutralized amino acid ester and a glyceride component as a composition active are disclosed. The mixture comprises from 35% to 85% by weight neutralized amino acid ester, and from 15% to 65% by weight of a glyceride component comprising selected monoglycerides, diglycerides, or a combination thereof. The compositions are useful for hair care, as well as in other applications, such as cleaning compositions, fabric softening compositions, and skin care compositions. When formulated into a hair care formulation, the compositions provide better wet combing than either the neutralized amino acid ester or the glycerides alone. Also disclosed are end use compositions comprising the mixture of neutralized amino acid ester and selected glycerides.

Abstract: Processes for making reactive surfactants are disclosed. In one such process, a fatty epoxide, a glycidyl ether, or a combination thereof is reacted with an olefin-functional nucleophile to produce an olefin-functional hydrophobe. The olefin-functional hydrophobe is reacted with ethylene oxide, propylene oxide, butylene oxides, or a combination thereof to produce an alkoxylate. Optionally, the alkoxylate is converted to the corresponding sulfate, phosphate, or maleate. Surfactant compositions comprising the reactive surfactants made by these processes are also described. The invention includes polymerizable mixtures comprising an acrylic monomer and the surfactant compositions as well as aqueous acrylic latex emulsions and coatings produced from the emulsions. The reactive surfactants deliver stable latex emulsions with reduced tendency for surfactant migration or excessive foaming. Coatings from the emulsions have improved wet adhesion, scrub resistance, and water resistance.

Abstract: Compositions comprising at least one esteramine active are disclosed in which the esteramine provides conditioning, softening, and/or cleaning properties. The compositions are useful for hair care, as well as in other applications, such as cleaning compositions, fabric softening compositions, and skin care compositions. Also disclosed are esteramine compositions that comprise a synergistic mixture of at least one esteramine and mono- and di-glycerides that provides better wet and dry combing than either the esteramine or mono- and di-glycerides alone. The synergistic mixture comprises about 50% to about 90% by weight esteramines and about 10% to about 50% by weight mono- and diglycerides.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C10-C17 monounsaturated 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 C10-C17 monounsaturated 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.

Abstract: 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.

Abstract: 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.

Abstract: 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 C10-C17 monounsaturated 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 C10-C17 monounsaturated 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 C10-C17 monounsaturated 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.

Abstract: Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated 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 C10-C17 monounsaturated 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.

Abstract: 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.

Abstract: Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C10-C17 monounsaturated 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 C10-C17 monounsaturated 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.

Abstract: 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.