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:
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:
Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C 10 -C 12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.
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:
Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C 10 -C 17 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 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 compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.
Abstract:
Personal cleansers and surfactant blends useful therein are disclosed. The cleansers comprise a primary anionic surfactant, a saturated C 8 -C- 14 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 8 -C 14 alkyl Ν,Ν-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 Ν,Ν-dialkylamides are also valuable for formulating oil-in- water emulsions with good stability.
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:
A method of degrading 1,4-dioxane in the wastewater produced during the manufacture of alkyl ether sulfates is disclosed. The method includes the steps of (a) mixing from 100 to 10,000 ppm, preferably 1,000 to 4,000 ppm of ozone with the wastewater; (b) introducing H2O2 into the wastewater in an amount of 0.01 to 10, preferably 0.1 to 0.5 molar equivalents of H2O2 to ozone, and (c) mixing the ozone, H2O2, and wastewater to generate hydroxyl radicals reactive with the 1,4-dioxane, without the addition of a metal catalyst. The hydroxyl radicals react with the 1,4-dioxane and degrade it into carbon dioxide, water and/or carbonate. The method is effective to reduce a concentration of 1,4-dioxane in the wastewater from a range of about 10 ppm to about 1000 ppm of dioxane down to less than 5 ppb of 1,4-dioxane after treatment. The method is also effective for removing hydrocarbon species that may be present in the wastewater.
Abstract:
Aqueous hard surface cleaner compositions useful for removing permanent ink are disclosed. The compositions comprise 75 to 99 wt.% of water; 0.1 to 5 wt.% of a monoterpene; 0.1 to 5 wt.% of a C10-C17 fatty acid derivative; and 0.1 to 5 wt.% of one or more surfactants. The fatty acid derivative is selected from Ν,Ν-dialkyl amides, N,N- dialkyl esteramines, and Ν,Ν-dialkyl amidoamines. Preferably, a base such as sodium carbonate or monoethanolamine is also included. The invention includes concentrates comprising the non-aqueous components recited above, as well as other applications for the cleaners and concentrates such as graffiti removers and permanent ink erasers. The combination of a monoterpene and certain fatty acid derivatives, especially fatty Ν,Ν-dialkyl amides, unexpectedly enables even dilute aqueous compositions to rapidly decolorize black permanent marker from hard, non-porous surfaces.