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.
Abstract:
Light-duty liquid detergents derived from metathesized natural oil feedstocks are disclosed. The detergents comprise water, at least one anionic surfactant, and at least one secondary surfactant derived from a metathesis-derived C 10 -C 17 monounsaturated acid or its ester derivatives. In particular, the secondary surfactant is selected from C 10 amidoamines, quaternized C 10 or C 12 amidoamines, C 12 amidoamine oxides, C 12 sulfobetaines, C 12 amidoamine sulfobetaines, and C 12 alkanolamides. The detergents noted above rival or outperform commercial baselines in standard foam tests for liquid detergents, particularly those used for dishwashing.
Abstract:
Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of of a metathesis-derived C 10 -C 17 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 C 10 -C 17 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 C 10 - C 17 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 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.
Abstract:
Agricultural compositions having reduced aquatic toxicity are disclosed. The compositions comprise an agricultural active, a monounsaturated C 10 -C 12 fatty 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 10 -C 12 fatty amine ethoxylate have good herbicidal efficacy. Unexpectedly, the monounsaturated C 10 -C 12 fatty amine ethoxylates have reduced aquatic toxicity when compared with their saturated analogs.
Abstract:
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 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. For fatty alkyl ester sulfonate-containing detergents, the composition is selected from C 10 betaines, C 12 or C 16 amidoamines, C 1 2 ethanolamine amides, C 16 amidoamine sulfonates, C 18 diamidoamine dioxides, quaternized C 18 diamidoamine betaines, sulfonated C 18 low-EO fatty ester alkoxylates, C 18 amidoamine carboxylates, and amidoamine oxides and sulfobetaines derived from cross- metathesis of palm or soybean oil. The bargain detergents include a performance booster selected from C 12 low-EO fatty ester alkoxylate sulfonates, C 18 amidoamine oxide esters, C 18 amidoamine oxide carboxylates, and amidoamine sulfobetaines made from self metathesized palm or soybean oil.
Abstract:
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 C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. Particular classes of sulfonated materials (e.g., certain amide sulfonates, sulfonated fatty ester alkoxylates, amidoamine sulfonates, amidoamine betaine sulfonates, sulfo-estolides) are identified as having value as the anionic surfactant. In another aspect, aqueous hard surface cleaners comprising at least one nonionic or amphoteric surfactant derived from a metathesis- derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. Particular classes of these surfactants (e.g., certain amides, imidazoline quat sulfonates, fatty ester alkoxylates, and amine oxides, betaines, amidoamine sulfobetaines) are also identified. The aqueous cleaners noted above rival or outperform commercial baselines in a Gardner straight-line washability test. Industrial degreasers comprising a C 10 or C 12 amide solvent and derived from a metathesis-derived C 10 -C 17 monounsaturated acid are superior to commercial standards.
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:
Alkoxylated fatty ester compositions are disclosed. In one aspect, the compositions comprise a reaction product of a metathesis-derived C 10 -C 17 monounsaturated 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 10 -C 17 monounsaturated 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 10 -C 17 monounsaturated 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.
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 sulfated. 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 quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfated 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:
Aqueous glyphosate formulations comprising a surfactant derived from metathesized natural oil feedstocks are disclosed. The formulations comprise a glyphosate salt, water, and a surfactant derived from a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives. The surfactant is selected from C 10 or C 12 amine oxides, C 10 or C 12 quats, C 10 , C 12 , or C 16 amidoamines, C 10 or C 12 amidoamine oxides, C 10 imidazoline quats, C 10 or C 12 amidoamine quats, C 10 , C 12 , or C 16 betaines, C 16 amidoamine betaines, C 18 diamidoamines, C 18 diamidoamine oxides, C 18 diamidoamine diquats, C 18 diamidoamine oxide quats, C 18 diamidoamine oxide betaines, Cis diamidoamine monobetaines, C 18 diamidoamine monobetaine quats, C 18 ester amidoamine quats, and amidoamines and their oxidized or quaternized derivatives made from self- or cross-metathesized palm or soybean oil. The surfactants noted above impart substantial stability to highly concentrated glyphosate formulations at, above, and below room temperature and perform as well or better than commercial alternatives.