Abstract: Aqueous hard surface cleaners and concentrates are disclosed. In one aspect, the cleaners comprise water, a monounsaturated C8-C14 fatty N,N-dialkylamide, and at least one anionic, cationic, nonionic, or amphoteric surfactant. The cleaners have a pH within the range of 6.0 to 9.0. Dilutable hard surface cleaner concentrates comprising the monounsaturated N,N-dialkylamide and a surfactant are also disclosed. Also included are aqueous hard surface cleaners which comprise a monounsaturated N,N-dialkylamide, and which by measure of ASTM D4488-95 A5 soil, provide superior percent cleaning at a pH less than 10 than they do at pH 10 and higher. Surprisingly, when a monounsaturated C8-C14 fatty N,N-dialkylamide is included in the aqueous hard surface cleaner or concentrate, rapid and thorough cleaning performance can be achieved even at relatively neutral pH. Consequently, the hard surface cleaners are effective on greasy soils, including baked-on soils, despite their low alkalinity.

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 N,N-dialkyl amides, N,N-dialkyl esteramines, and N,N-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 N,N-dialkyl amides, unexpectedly enables even dilute aqueous compositions to rapidly decolorize black permanent marker from hard, non-porous surfaces.

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: 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: Alkoxylated fatty ester compositions are disclosed. In one aspect, the compositions comprise a reaction product of a metathesis-derived C10-C17 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 C10-C17 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 C10-C17 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: 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: 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 N 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.

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 monoun-saturated 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.

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 C10-C17 monounsaturated acid, 5 octadecene-1,18-dioic acid, or their ester derivatives. In another aspect, aqueous hard surface cleaners comprising at least one nonionic or amphoteric surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. The aqueous cleaners noted above rival or outperform commercial baselines in a Gardner straight-line washability test. Industrial degreasers comprising a C10 or C12 amide solvent and derived from a metathesis-derived C10-C17 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: Compositions comprising sulfo-estolides and alkyl ester sulfonates are described. Detergent formulations, such as laundry detergents, softeners, and other materials, containing any of these materials are disclosed, as well as personal care formulations, hard surface cleaner formulations, and automatic dishwasher detergent formulations. Laundry methods employing these formulations are also disclosed. These formulations are useful as laundry detergents and can be biodegradable, heavy duty liquids, 2× or 3× and up to 6× concentrates, low foaming, and/or effective in a high efficiency washing machine.

Abstract: Compositions comprising sulfo-estolides and alkyl ester sulfonates are described. Detergent formulations, such as laundry detergents, softeners, and other materials, containing any of these materials are disclosed, as well as personal care formulations, hard surface cleaner formulations, and automatic dishwasher detergent formulations. Laundry methods employing these formulations are also disclosed. These formulations are useful as laundry detergents and can be biodegradable, heavy duty liquids, 2× or 3× and up to 6× concentrates, low foaming, and/or effective in a high efficiency washing machine.

Abstract: A method for interpreting a plurality of m-dimensional attribute vectors (m2) assigned to a plurality of locations in an n-dimensional interpretation space (n1), which method comprises arranging at least a subset of the attribute vectors as points in an m-dimensional attribute space; defining k classes (k2) of attribute vectors by identifying for each class at least one classification point in attribute space; postulating a classification rule for points in attribute space; determining a class-membership attribute of a point in attribute space using the classification points and the classification rule to obtain a classified point; and assigning a display parameter to the classified point which is related to the class-membership attribute. In one embodiment the display parameter is a mixed display parameter derived from probabilistic membership values each representing a probability that the classified point belongs to a selected class.

Abstract: Sulfo-estolides and methods of making them are described. Useful methods include acid side bleaching, partial hydrogenation of the fatty acid, pretreatment of the fatty acid to provide color inhibition, acid side hydrolysis of the sulfo-estolides, or conversion of SHP to an essentially fully hydrolyzed product (HSHP) or a partially hydrolyzed product (PHSHP). Formulations and concentrated formulations of automatic dishwasher detergent or machine wash detergent compositions containing sulfo-estolides, among others, are also included.

Abstract: Light duty liquid detergent formulations that contain sulfo-estolide surfactants, sulfo-estolide derivatives and salts of sulfo-estolides are disclosed. The compositions of the presently described technology are useful for soil removal applications including, but not limited to, washing dishes by hand.

Abstract: Sulfo-estolides and methods of making them are described. Useful methods include acid side bleaching, partial hydrogenation of the fatty acid, pretreatment of the fatty acid to provide color inhibition, acid side hydrolysis of the sulfo-estolides, or conversion of SHP to an essentially fully hydrolyzed product (HSHP) or a partially hydrolyzed product (PHSHP). Formulations and concentrated formulations of automatic dishwasher detergent or machine wash detergent compositions containing sulfo-estolides, among others, are also included.

Abstract: Light duty liquid detergent formulations that contain sulfo-estolide surfactants, sulfo-estolide derivatives and salts of sulfo-estolides are disclosed. The compositions of the presently described technology are useful for soil removal applications including, but not limited to, washing dishes by hand.

Abstract: Compositions comprising sulfo-estolides and alkyl ester sulfonates are described. Detergent formulations, such as laundry detergents, softeners, and other materials, containing any of these materials are disclosed, as well as personal care formulations, hard surface cleaner formulations, and automatic dishwasher detergent formulations. Laundry methods employing these formulations are also disclosed. These formulations are useful as laundry detergents and can be biodegradable, heavy duty liquids, 2× or 3× and up to 6× concentrates, low foaming, and/or effective in a high efficiency washing machine. Methods for laundering fabrics with the compositions are also disclosed.

Abstract: A method for interpreting a plurality of m-dimensional attribute vectors (m2) assigned to a plurality of locations in an n-dimensional interpretation space (n1), which method comprises arranging at least a subset of the attribute vectors as points in an m-dimensional attribute space; defining k classes (k2) of attribute vectors by identifying for each class at least one classification point in attribute space; postulating a classification rule for points in attribute space; determining a class-membership attribute of a point in attribute space using the classification points and the classification rule to obtain a classified point; and assigning a display parameter to the classified point which is related to the class-membership attribute. In one embodiment the display parameter is a mixed display parameter derived from probabilistic membership values each representing a probability that the classified point belongs to a selected class.