Sulfosuccinate compounds and methods of making and using them

Abstract

Sulfosuccinate and disulfosuccinate compounds are disclosed, specifically alkali glyceryl mono alkanoate sulfosuccinate and disulfosuccinate. Methods of making and using the same are also disclosed.

Description

[0001] PAT15806-WO-PCT

[0002] COMPOUNDS AND METHODS OF MAKING AND USING SAME

[0003] TECHNICAL FIELD

[0004] Sulfosuccinate and disulfosuccinate compounds are disclosed, specifically alkali glyceryl mono alkanoate sulfosuccinates and disulfosuccinates. Methods of making and using the same are also disclosed.

[0005] BACKGROUND

[0006] Sulfosuccinates were originally developed in 1939. See, e.g., Sulfosuccinates as Mild Surfactants, Journal of Oleo Science, Vol. 55, No. 9, pp. 429-439 (2006). Sulfosuccinates are formed by reacting maleic anhydride with fatty alcohol followed by sulfonation. Id.

[0007] Sulfosuccinates have been used as anionic surfactants in personal cleansing products, textiles, polymers, paints and coatings, leather, printing and agricultural industries. They are known for being mild, versatile, inexpensive, and biodegradable.

[0008] CN Pub. Pat. App. 108623459 to Changsha Rhon Pharma Tech Inc. discloses a preparation method of diacetyl monostearic acid glyceride using acetic anhydride and glyceryl monostearate.

[0009] US Pat No 2698856 to Carnes et al discloses complex polyesters and salts thereof.

[0010] US Pat No 2745749 to Feuge et al. discloses glyceridic mixtures exhibiting unique properties and processes for their production.

[0011] A need remains for new sulfosuccinates and disulfosuccinates and new uses of the same.

[0012] BRIEF SUMMARY

[0013] Sulfosuccinate and disulfosuccinate compounds are disclosed having a general formula:

[0014] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n

[0015] [HOCH2-](i-n)[-CH-CH2-O-C(=O)R], PAT15806-WO-PCT wherein each M is independently Li, Na, K, NH4, or combinations thereof; n=0 or 1 ; and R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20.

[0016] Methods of making the disclosed sulfosuccinate and disulfosuccinate compounds are also disclosed. Glyceryl C14-20 mono alkanoate having formula (a) is added to a reactor and heated to its melting temperature, wherein R is defined above. The temperature is maintained while maleic anhydride is added with stirring to form glyceryl monostearate maleate and glyceryl monostearate dimaleate. Alkali metal metabisulfite or alkali metal sulfite in an aqueous solution is added to the glyceryl monostearate maleate and glyceryl monostearate dimaleate to produce the disclosed sulfosuccinate and disulfosuccinate compounds.

[0017] Compositions comprising the disclosed sulfosuccinate and disulfosuccinate compounds are also disclosed.

[0018] TERMS AND DEFINITIONS

[0019] As used herein:

[0020] • the symbol and the terms “approximately” and “about” mean plus or minus 10% of the value stated;

[0021] • the term “a” or “an” means one or more;

[0022] • as used herein, M may refer to either the Molality of a solution (e.g., NaOH) or Li, Na, K, NH4, and will be evident in context;

[0023] • the abbreviation “MA refers to maleic anhydride;

[0024] • the abbreviation “GMS” refers to glyceryl monostearate;

[0025] • any and all ranges are inclusive of their endpoints, e.g., a range from 1 % w / w to 10 % w / w based on the total weight of the composition includes 1 % w / w and 10 % w / w and any concentration between 1 % w / w and 10 % w / w;

[0026] • when an ingredient does not contain close or equal to 100% w / w active material, two percentages may be provided: one for the weight of the raw material and one for the PAT15806-WO-PCT weight of the active in the raw material. For example, 9.65 kg of powdered glyceryl monostearate raw material contains approximately 95% w / w glyceryl monostearate with the balance including glycerol, water and other by-products, which equates to approximately 9.17 kg of glyceryl monostearate in the composition. This is represented as 9.65 kg (9.17 kg) of glyceryl monostearate;

[0027] • the term “comprising” is inclusive or open-ended and does not exclude any additional elements; the term “consisting of” excludes any additional elements; and the term “consisting essentially of” is in-between, only permitting additional elements that do not materially affect characteristics of the product or process;

[0028] • the phrase “substantially free” means a concentration of less than 0.3% w / w, preferably less than 0.2% w / w, more preferably less than 0.1 % w / w, and most preferably less than 0.05% w / w;

[0029] • the term “liquid” means a state of matter that conforms to the shape of the container in which it is held at room temperature (18-23°C) and which acquires a defined surface in the presence of gravity; the term “liquid” is readily distinguishable from the terms “solid” and “gas.” Liquids are not pastes, which behave as a solid until a sufficiently large load or stress is applied, even though a paste is also known as a Bingham plastic fluid;

[0030] • the term “soft water” means water having a conductivity equal to or below 20 pS / cm and / or below 60 ppm CaCCh, e.g., deionized water;

[0031] • the term “micelle” means spherical particles made up of amphiphilic molecules that self-assemble in an aqueous solution to form a colloidal suspension. Polar region (head) of these molecules is the hydrophilic region that faces the outside of the micelle and makes it water soluble. Nonpolar region (tail) of these molecules is the hydrophobic region and forms the core of the micelle;

[0032] • the abbreviation q.s. is for quantum satis and means a sufficient quantity to total 100% ingredients; and

[0033] BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWINGS

[0034] So that the manner in which the features of the disclosure can be understood, a detailed description may be had by reference to certain embodiments, some of which PAT15806-WO-PCT are illustrated in the accompanying drawings. It is to be noted, however, that the drawings illustrate only certain embodiments and are therefore not to be considered limiting of scope, for the scope of the disclosed subject matter encompasses other embodiments as well.

[0035] FIG 1 is a graph of the volume of 0.1 M NaOH in m L used to titrate maleic acid versus pH;

[0036] FIG 2 is a graph of the volume of NaOH used to calculate the moles COOH / Og sample versus pH in millivolts, with the end point of the reaction indicated by EP1 ;

[0037] FIG 3 is a graph of the esterification progress (value a) assessed for an esterification reaction mass versus time.

[0038] DETAILED DESCRIPTION

[0039] Consumers frequently associate disinfection with cleaning products having a white appearance, particularly hard surface cleaning products. Similarly, consumers associate opalescent laundry detergents and softeners with fabric care. Light scatters when it hits homogenously dispersed particles in a liquid phase, causing the opacifying effect and / or white color.

[0040] Polyacrylates are well known, inexpensive, and effective opacifiers. Polyacrylates are also a harmful source of microplastics.

[0041] To replace the polyacrylate opacifier, the compound must form micelles in a solvent, such as water. Opacifying micelles typically have a diameter ranging from approximately 50 nm to approximately 200 nm, preferably from approximately 75 nm to approximately 150 nm, and more preferably from approximately 80 nm to approximately 120 nm. To form a micelle, the compound must have a long aliphatic tail linked to a polar head. The long aliphatic tail is designed to curl up at the center of the micelle while the polar head is oriented outward. The micelle scatters the light, providing a white color and an opacifying effect. The opacifier compound will preferably be biodegradable.

[0042] Applicant has developed novel sulfosuccinate and disulfosuccinate compounds that may be used for opacifying water-based formulations, among other functions. The PAT15806-WO-PCT novel sulfosuccinate and disulfosuccinate compounds were created using standard and affordable starting materials. The compounds have the general formula:

[0043] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n [HOCH2-](i-n)[-CH-CH2-O-C(=O)R], wherein each M is independently Li, Na, K, NH4, or combinations thereof; n=0 or 1 ; and R = C14-20 hydrocarbon group, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20 group. Each of R, R2, R3, and R4may independently be saturated or unsaturated, linear or branched. Saturation provides low polarity and colorlessness to the molecule. M is preferably Na, K, or combinations thereof. R is preferably a linear hydrocarbon group, which may be saturated or unsaturated. One of ordinary skill in the art will recognize that each chain is bound to the other at the end.

[0044] When n=0 and R= C14-20, the sulfosuccinate compounds have the formula: the structure:

[0045] When M = K and R = C17H35, the sulfosuccinate compound has the formula:

[0046] One of ordinary skill in the art will recognize that the potassium cations (K+) depicted in the formula above may be substituted by Na+, Li+, NF , or combinations thereof, preferably K, Na, or combinations thereof. The SO3 group provides hydrophilicity to the molecule. In contrast, the saturated C17 alkyl tail is hydrophobic. As a result, the hydrophobic alkyl groups on adjacent molecules cluster to form the center of the micelle, while the hydrophilic SO3 groups form the perimeter of the micelle and remain in contact with the surrounding aqueous medium. The diameter of the micelles range PAT15806-WO-PCT from approximately 50 nm to approximately 150 nm, preferably from approximately 75 nm to approximately 125 nm, and more preferably from approximately 90 nm to approximately 110 nm.

[0047] When n=1 and R= C14-20, the disulfosuccinate compounds have the formula: [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-] [-CH-CH2-O-C(=O)R], and the structure:

[0048] R is preferably a linear hydrocarbon group, which may be saturated or unsaturated.

[0049] When M = K and R = C17H35, the disulfosuccinate compound has the formula:

[0050] Once again, the potassium cations (K+) in this formula may be substituted by Na+, Li+, NH4+, or combinations thereof, preferably K, Na, or combinations thereof. The two SO3 groups provide hydrophilicity to the molecule. In contrast, the saturated C17 alkyl tail is hydrophobic. As a result, the hydrophobic alkyl groups on adjacent molecules gather together to form the center of the micelle, while the hydrophilic SO3 groups form the perimeter of the micelle and remain in contact with the surrounding aqueous medium. The diameter of the micelles range from approximately 50 nm to approximately 150 nm, PAT15806-WO-PCT preferably from approximately 75 nm to approximately 125 nm, and more preferably from approximately 90 nm to approximately 110 nm.

[0051] To synthesize the compounds in which R=C14-20, preferably R= C17H35, glyceryl C15-21 mono alkanoate having formula (a) is added to a reactor and heated to its melting temperature

[0052] One of ordinary skill in the art will easily recognize how to determine the melting point of the glyceryl mono alkanoate. When R=Ci7H35, the resulting reactant is glyceryl

[0053] Even though R=C17, one of ordinary skill in the art will recognize that this molecule is referred to as a glyceryl monostearate and its carbon chain referred to as C18:0. C18:0 is shorthand for a C18 chain length that includes the C doubly bonded to the 0 and 0 double bonds. In formula (a) above, R does not include the C doubly bonded to the 0. Therefore, the C17 carbon chain length for R is one carbon short of the C18:0 chain length for the named stearate.

[0054] Applicant believes that the isomer (a1 ) above makes up a predominant portion of the raw material. However, some of the following isomer (a2) may also be present in the raw material without detracting from the teachings herein. PAT15806-WO-PCT

[0055] This glyceryl monostearate raw material is commonly used to produce baked goods and is inexpensive and commercially available from numerous sources. The raw material is readily available as a powder at 95% wt purity, with glycerol, water and other by-products providing the balance. Alternatively, other suitable reactants (a) include glyceryl monopentadecanoate (C15:0) from R=C14, glyceryl monopalmitate (C16:0) from R=C15, glyceryl monooleate (C17: 1 ) from R=C16, glyceryl monolinoleate (C17:2) from R=C16, glyceryl monononadeconoate (C18:0) from R=C17, glyceryl monoarachidate (C19:0) from R=C18, glyceryl monoarachidonate C19:4) from R=C18.

[0056] The temperature is maintained while maleic anhydride is added with stirring. During initial research, Applicant has maintained a ratio of approximately 5 moles to approximately 5.5 moles of maleic anhydride to approximately 4 moles glyceryl mono alkanoate. As shown in the examples and recognized by one of ordinary skill in the art, similar results are expected when more or less than 4 moles of the glyceryl mono alkanoate and more or less than 5 moles of the maleic anhydride, provided the ratio of 4:5 moles glyceryl mono alkanoate:maleic anhydride is maintained (e.g., 43 moles maleic anhydride and 34 moles glyceryl monostearate).

[0057] Maleic anhydride (MA) is the limiting reactant. A hydroxy group on reactant (a) reacts with the maleic anhydride. The MA ring is opened, becoming maleic acid, and forms an ester with reactant (a). No byproducts, such as water, are generated by this reaction. Since testing was performed with multipliers of approximately 5 moles of MA and approximately 4 moles glyceryl monostearate, all MA should be consumed by the end of the reaction. Reactant (a) will still have available -OH groups when all of the MA has been consumed. A slight excess of MA may be used as compared to reactant (a) to try to produce more di ester reaction product (e.g., ~4 to ~8 moles MA and ~4 moles PAT15806-WO-PCT glyceryl monostearate). Alternatively, less MA may result in production of more ester reaction product (e.g., ~1 to ~3 moles MA and ~4 moles glyceryl monostearate).

[0058] The reaction of MA and glyceryl mono alkanoate is substantially free of any catalyst or added solvent, including water. The only potential solvent present would be the trace amounts contained in the raw materials.

[0059] Applicant believes that the 5 mole MA: 4 mole glyceryl monostearate (GMS) stereochemistry produces 1 mole of a diester in the first step of the reaction. The diester produced from MA and GMS is glyceryl monostearate dimaleate having the formula:

[0060] Applicant believes that the 5 moles MA: 4 moles GMS stereochemistry produces 3 moles of an ester in the first step of the reaction. The ester produced from MA and GMS is glyceryl monostearate maleate having the formula:

[0061] One of ordinary skill in the art will recognize that the ester and diester structures will differ when using different starting reactants ( / .e., having shorter or longer, linear or branched, saturated or unsaturated hydrocarbon tails). One of ordinary skill in the art will further recognize that the - COOH acid end groups on these reaction products make these products more water soluble than the -COCH3 acetyl groups produced by the acetic anhydride reactions found in the prior art. PAT15806-WO-PCT

[0062] As shown in the examples that follow, this stoichiometry provides the basis for the calculation of the esterification process. Once the reaction progress exceeds 90%, preferably 95%, the next reaction step may proceed.

[0063] In the second step of the reaction, alkali metal metabisulfite or alkali sulfite in an aqueous solution is added to the ester / diester mixture to produce the sulfosuccinate / disulfosuccinate mixture. In the examples that follow, Applicant used multipliers of approximately 2.5 to approximately 2.75 moles of sodium metabisulfite in 20% wt water. One of ordinary skill in the art will recognize that any alkali metabisulfite may be used without departing from the teachings herein. Alternatively, approximately 5 moles to approximately 5.5 moles of alkali sulfite may be used. Similarly, more or less water may also be used. Once again, a slight excess of the metabisulfite or sulfite reactant may be used as compared to reactant (a) to try to convert 100% of the ester or diester to the final sulfosuccinate and disulfosuccinate reaction products. Alternatively, no excess metabisulfite or sulfite is necessary to minimize and preferably avoid formation of any by-products.

[0064] The resulting synthesis product contains approximately 20% wt to approximately 30% wt of 1 :1 to 1 :5 molar ratio of glyceryl monostearate disulfosuccinate: glyceryl monostearate sulfosuccinate in water, having the following structures: glyceryl monostearate disulfosuccinate: PAT15806-WO-PCT glyceryl monostearate sulfosuccinate:

[0065] Preferably, the resulting synthesis product contains a 1 :2 to 1 :4 molar ratio of glyceryl monostearate disulfosuccinate: glyceryl monostearate sulfosuccinate, and more preferably a 1 :3 molar ratio.

[0066] The resulting synthesis product may also include unreacted glyceryl monostearate maleate: unreacted glyceryl monostearate bi maleate: PAT15806-WO-PCT

[0067] Once again, one of ordinary skill in the art will recognize that the structures of these reaction products will differ when using different starting reactants (e.g., having shorter or longer hydrocarbon tails).

[0068] Less than 5% mol of unreacted reactant (a) is expected in the aqueous blend when excess maleic anhydride is used, preferably less than 3% mol, and more preferably less than 1 % mol. Similarly, approximately 0.1 % mol to approximately 5% mol of unreacted ester and approximately 0.1 % mol to approximately 5% mol of unreacted diester are expected in the aqueous blend due to the excess metabisulfite or sulfite reactant, preferably approximately 0.1 % mol to approximately 3% mol of each, and more preferably approximately 0.1 % mol to approximately 1 % mol of each.

[0069] The resulting aqueous blend may also include approximately 0.1 % mol to approximately 5% mol alkali fumarate based on the ring-opening hydrolyzation reaction of maleic anhydride and water.

[0070] Another potential by-product is glyceryl monostearate maleate sulfosuccinate:

[0071] In sum, the resulting product comprises approximately 20% wt to approximately 30% wt of a 1 :5 molar ratio of disulfosuccinate to sulfosuccinate in water, plus less than 5% mol of each of unreacted glyceryl C15-21 mono alkanoate, diester, ester, and alkali fumarate. In other words, the resulting product comprises: approximately 4% mol to approximately 6% mol disulfosuccinate, approximately 12% mol to approximately 18% mol sulfosuccinate, approximately 0.1 % mol to approximately 6% mol, preferably approximately 0.1 % mol to approximately 4% mol, and more preferably approximately 0.1 % mol to approximately 1 % mol glyceryl C15-21 mono alkanoate, PAT15806-WO-PCT approximately 0.1 % mol to approximately 6% mol, preferably approximately 0.1 % mol to approximately 4% mol, and more preferably approximately 0.1 % mol to approximately 1 % mol diester, approximately 0.1 % mol to approximately 6% mol, preferably approximately 0.1 % mol to approximately 4% mol, and more preferably approximately 0.1 % mol to approximately 1 % mol ester, approximately 0.1 % mol to approximately 6% mol, preferably approximately 0.1 % mol to approximately 4% mol, and more preferably approximately 0.1 % mol to approximately 1 % mol alkali fumarate, and approximately 70% wt to approximately 80% wt water, preferably soft water.

[0072] Alternatively, the resulting product comprises less than 5% wt of each of unreacted glyceryl C15-21 mono alkanoate, diester, ester, and alkali fumarate. In other words, the resulting product comprises: approximately 5% wt to approximately 10% wt disulfosuccinate, approximately 15% wt to approximately 20% wt sulfosuccinate, approximately 0.1 % wt to approximately 6% wt, preferably approximately 0.1 % wt to approximately 4% wt, and more preferably approximately 0.1 % wt to approximately 1 % wt glyceryl C15-21 mono alkanoate, approximately 0.1 % wt to approximately 6% wt, preferably approximately 0.1 % wt to approximately 4% wt, and more preferably approximately 0.1 % wt to approximately 1 % wt diester, approximately 0.1 % wt to approximately 6% wt, preferably approximately 0.1 % wt to approximately 4% wt, and more preferably approximately 0.1 % wt to approximately 1 % wt ester, approximately 0.1 % wt to approximately 6% wt, preferably approximately 0.1 % wt to approximately 4% wt, and more preferably approximately 0.1 % wt to approximately 1 % wt alkali fumarate, and approximately 70% wt to approximately 80% wt water, preferably soft water.

[0073] The resulting product looks like milk, namely a milky-white colored thin liquid having a viscosity slightly higher than water, typically approximately 50 cps to approximately 100 cps as measured at 25°C using spindle LV2 at 20 RPM. PAT15806-WO-PCT

[0074] Additionally, the resulting product is odorless, making it useful to formulate fragranced products without negatively impacting the aroma. The diameter of the micelles in the reaction product range from approximately 50 nm to approximately 150 nm, preferably from approximately 75 nm to approximately 125 nm, and more preferably from approximately 90 nm to approximately 110 nm. Finally, Applicant believes that the resulting product may be biodegradable in an aerobic aqueous mineral medium. Specifically, Applicant believes that the resulting product will be broken down into less complex compounds by means of microbial action within 28 days, or even faster, in accordance with the Office of Economic Co-operation and Development (OECD) Guidelines 301 B and / or 301 F adopted by Council on 17thJuly 1992. More specifically, Applicant believes that the resulting product will produce 60% theoretical CO2 evolution (ThCO2) in a 10-day window within the 28-day test period, starting after 10% ThCO2 has been reached in accordance with method disclosed in 301 B. Additionally, Applicant believes that the resulting product will provide 60% theoretical oxygen demand (ThOD) in a 10-day window within the 28-day test period, starting after 10% ThOD has been reached in accordance with the method disclosed in 301 F.

[0075] The maleic anhydride, glyceryl C15-21 mono alkanoate, alkali hydroxide, and alkali metal metabisulfite or alkali metal sulfite reactants are the only reactants needed to perform the reaction. Water is the only solvent used throughout the entire reaction. The process does not require the addition of any non-aqueous solvents to either reaction. The process also does not require the use of any catalysts to start or drive either reaction process.

[0076] More details about the synthesis process are provided in the examples that follow.

[0077] Any known solid purification techniques may be used to isolate the individual compounds, including but not limited to, sublimation, crystallization, distillation, chromatography, or combinations thereof. Applicant has found, however, that the blend of synthesis products is suitable for use in consumer good products as a mixture, without the need for purification. PAT15806-WO-PCT

[0078] As shown in the examples that follow, these sulfosuccinate and disulfosuccinate mixtures exhibit stability. However, a stabilizer and / or preservative may be added to the mixture to provide extended shelf life.

[0079] As discussed above, Applicant has discovered compounds having the general formula:

[0080] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n

[0081] [HOCH2-](i-n)[-CH-CH2-O-C(=O)R], wherein each M is independently Li, Na, K, NH4, or combinations thereof; n=0 or 1 ; and R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20. R, R2, R3, or R4may each independently be saturated or unsaturated, linear or branched.

[0082] When n=0, R= CHR2NHR3, and R2and R3= C14-20, the sulfosuccinate compounds have the formula:

[0083] [MO3SCH(COOM)CH2COO-][HOCH2-][-CH-CH2-O-C(=O)CHR2NHR3],

[0084] When n=1 , R= CHR2NHR3, and R2and R3= C14-20, the disulfosuccinate compounds have the formula:

[0085] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-] [-CH-CH2-O-C(=O) CHR2NHR3],

[0086] When n=0, R= NHR4, and R4= C14-20, the sulfosuccinate compounds have the formula:

[0087] [MO3SCH(COOM)CH2COO-][HOCH2-][-CH-CH2-O-C(=O) NHR4].

[0088] When n=1 , R= NHR4, and R4= C14-20, the compound has the formula: [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]

[0089] [-CH-CH2-O-C(=O) NHR4],

[0090] The synthesis of the compounds in which R= CHR2NHR3or NHR4is similar to that described above for R=C14-20 group, substituting the relevant R group in reactant (a). The amino derivatives of the glyceryl C15-21 mono alkanoate having formula (a3) may be obtained by esterification of glycerol with amino acids: PAT15806-WO-PCT

[0091] Both glycerol and amino acids are readily available commercially.

[0092] Alternatively, fatty isocyanates may be reacted with glycerol to form monoglycerol fatty urethane reactants (a4):

[0093] Synthesis methods are known for the fatty isocyanate reactants. Any of the sulfosuccinate and disulfosuccinate mixture may be stored in any suitable containers, including glass, LDPE, HDPE, PET, etc.

[0094] The sulfosuccinate and disulfosuccinate mixture may be used in cosmetic, food, personal care, pharmaceutical, or home care products, such as antidandruff shampoos, laundry sanitizers, or multipurpose cleaners. The sulfosuccinate and / or disulfosuccinate, purified or in the reaction mixture, may be used in the following exemplary multipurpose cleaner (MPC).

[0095] The exemplary MPC may further comprise fragrance or dyes.

[0096] For example, these exemplary MPCs comprise, consist essentially of, or consist of: PAT15806-WO-PCT

[0097] The sulfosuccinate and disulfosuccinate compounds may be used in the following liquid laundry detergent, which comprises, consists essentially of, or consists of:: PAT15806-WO-PCT

[0098] The sulfosuccinate and disulfosuccinate compounds may be used in the following exemplary liquid laundry sanitizer, which comprises, consists essentially of, or consists of:: The sulfosuccinate and disulfosuccinate compounds may be used in the following exemplary liquid laundry sanitizer and softener, which comprises, consists essentially of, or consists of:: PAT15806-WO-PCT

[0099] The sulfosuccinate and disulfosuccinate compounds may be also used in another exemplary liquid laundry sanitizer, which comprises, consists essentially of, or consists of::

[0100] The sulfosuccinate and disulfosuccinate compounds may be used in another exemplary liquid laundry sanitizer and softener, which comprises, consists essentially of, or consists of::

[0101] Any of the formulations above may further comprise fragrance and / or dyes, provided the fragrance and / or dye does not negatively affect the stability of the formulations. PAT15806-WO-PCT

[0102] Examples

[0103] The following examples illustrate an exemplary reaction as well as preferred embodiments of the invention. It is to be understood that these examples are provided by way of illustration only and that further useful formulations falling within the scope of the present invention and the claims may be readily produced by one skilled in the art without deviating from the scope and spirit of the invention.

[0104] The sulfosuccinate and disulfosuccinates were prepared in the following examples using the ingredients identified in Table A:

[0105] Table A:

[0106] Example 1

[0107] Preparation of ester and diester:

[0108] 12.8 kg (12.16 kg or 34.0 moles) of glyceryl monostearate (95% wt active)(GMS) was added to a four-neck round bottom flask with electrically-powered anchor stirrer immersed in a glycerol thermostatic bath. The temperature of the vessel was adjusted to approximately 80-85°C to melt the glyceryl monostearate. One of ordinary skill in the art will recognize that the purity of GMS may vary with different suppliers. Higher purity raw material is preferred because more reaction by-products may be produced from lower purity GMS reactants.

[0109] 4.28 kg (4.19 kg or 43 moles) of maleic anhydride (98% active) was mixed into the melted glyceryl monostearate. Because maleic anhydride sublimes when heated, a reflux condenser was assembled on one of the necks of the four-neck round bottomed flask. The temperature of the vessel was maintained at approximately 80°C to approximately 85°C during the exothermic reaction. After completion of the addition, mixing continued for approximately 8 hours. The resulting mixture is a yellowish clear liquid at approximately 80°C to approximately 85°C, with no lumps or seeds. A sample was tested PAT15806-WO-PCT to determine the status of the esterification process. Mixing at 95°C is continued hourly until the esterification progress value is greater than 90%.

[0110] Determining Esterification Progress

[0111] The progress of the reaction of reactant (a) with maleic anhydride may be monitored. When maleic anhydride is titrated with a hydroxide solution (e.g., NaOH, KOH, etc), the anhydride is hydrolysed so that the furane ring opens:

[0112] The hydroxide solution removes the Hs from the hydroxyl groups in two steps, resulting in two pKa values: 1.91 and 6.33: FIG 1 is a graph of the volume of 0.1 M NaOH in rnL used to titrate maleic acid versus pH. The two pKa endpoints are shown very clearly in this graph. One of ordinary skill in the art will recognize that 0.1 M NaOH is the same as 0.1 N NaOH because NaOH has only one reactive hydroxide ion per molecule.

[0113] The maleic anhydride reactant is consumed during the esterification process. Five (5) moles of maleic anhydride (MA) are reacted with four (4) moles of glyceryl monostearate (GMS) to form 1 mole of glyceryl monostearate dimaleate (di M-GMS) and 3 moles of glyceryl monostearate maleate (M-GMS) as shown in the following reaction:

[0114] In other words, each mole of maleic anhydride reacts with one hydroxyl group on the GMS reactant. Using 5 moles of maleic anhydride with 4 moles of GMS causes the second hydroxyl group on one GMS reactant to form the dimaleate. Therefore, Applicant PAT15806-WO-PCT believes that the proportion of maleate and dimaleate produced may be controlled by the quantity of maleic acid used. As can be seen, the reaction is an addition reaction, with no gas or water formation. As a result, the weight of the reaction products equals the sum of the weights of the reactants.

[0115] The progress reaction is provided in the following table: x = the reaction process between 0 < x < 1 moles COOH (f(X)) = 10- 10x + 5x = 10-5x so when x=0, 10 moles COOH - 0% esterification (not started) and when x=1 , 5 moles COOH - 100% esterification (complete)

[0116] Based on this, at the start of the reaction (x=0), maleic anhydride provides 10 moles of -COOH over the total mass of 5 moles of Maleic anhydride, or:

[0117] Mol COOHo [mol / 100 g] = 10 x 100 / [(5 x MW MA) + (4 x MW GMS)]

[0118] = 10* 100 / (5*98+4*358) = 500 / 961 [mol / 100 g] where

[0119] COOHCF initial concentration of -COOH in mol / 100g

[0120] MW MA = molecular weight of maleic anhydride = 98 g / mol

[0121] MW GMS = molecular weight of glyceryl monostearate = 358 g / mol

[0122] At the end of the reaction (x=1), 5 moles of -COOH are available provided by 1 mol of GMS di-maleate and 3 moles GMS mono-maleate, or:

[0123] Mol COOHi [mol / 100 g] = 5 x 100 / [(5 x MW MA) + (4 x MW GMS)]

[0124] = 5 * 100 / (5*98 + 4x358) = 250 / 961 [mol / 100 g] where COOHi= final concentration of -COOH in mol / 100g

[0125] The concentration of -COOH groups at any time in the reaction (expressed as moles / 100 g esterification mass) is: PAT15806-WO-PCT

[0126] Mol COOHx [mol / 100 g] = (10 - 5x) x 100 / 1922 = 1000 / 1922 - 500x / 1922 = 500 / 961 - 250X / 961 where COOHX= concentration of -COOH in mol / 100g sample at any time with 0<x<1

[0127] The moles of COOHXare determined by titration of a sample taken from the reaction mass at any time during the reaction. The titer calculation is:

[0128] Mol COOHX[mol / g] = [(EP [mL] / 1000) x N NaOH x f NaOH] / w x 100 where

[0129] EP=volume of NaOH in mL,

[0130] N NaOH = normality of NaOH (eq / L), f NaOH = factor of NaOH solution w = sample weight = g esterification mass

[0131] Converting the calculation to solve for x and adding the titer calculation:

[0132] Mol COOHX[mol / 100 g] = 500 / 961 - 250x / 961 x = (500 / 961 - moles COOHX) x 961 / 250 x = [500 / 961 - {((EP (mL) / 1000) x N NaOH x f NaOH) / w x 100} x 961 / 250

[0133] = 2-[(EP (mL) x N NaOH x f NaOH) / w x 961 / 2500]

[0134] Converting this value to a percentage provides the calculation for esterification progress a [%] = x * 100 = 200 - [(EP (mL) x N NaOH x f NaOH x 961 ) / (w x 25)]

[0135] This progress was monitored along with time, using 0.5 N NaOH with a factor of 1 .0208.

[0136] The results are provided in the following table:

[0137] FIG 2 is a graph of the volume of NaOH used to calculate the moles COOH / 100g sample versus pH in millivolts, with the end point of the reaction indicated by EP1 . The titration curve shown in FIG 2 is obtained when the -COOH free groups of the esterification mass are titrated with NaOH, to calculate afterwards the amount of moles of COOH / 100 g that will be needed to assess the esterification progress shown in FIG 3

[0138] The graph of esterification progress a [%] as a function of time is provided in FIG 3. FIG 3 reveals that the esterification process occurs quickly during the first hour of the reaction and afterward follows a linear increment (R2 value of -0.9955) to reach a PAT15806-WO-PCT reaction progress of around 96.5% after 8 hours. Testing has revealed that esterification values of greater than approximately 90%, preferably great than about 95%, are suitable to provide emulsions with sufficient stability.

[0139] The speed of the reaction may be increased by heating to approximately 80-85°C during the first two hours to minimize sublimation of maleic anhydride and then increasing the temperature to approximately 90-95°C for the remainder of the esterification reaction. Applicant believes that this procedure may permit the esterification process to reach 95% more quickly. However, further experimentation is needed to verify whether these changes produce any unexpected by-products.

[0140] Neutralization of ester and diester:

[0141] When the esterification value is greater than 95%, the temperature of the vessel was decreased to 70°C. 1 kg (0.5 kg) of a 50% solution of potassium hydroxide was added with mixing to the yellowish clear liquid. The temperature of the vessel must be maintained below 80°C. Small white clumps may form but should be re-dissolved. After addition and dissolving, the temperature of the vessel was adjusted to approximately 75°C to approximately 80°C. The resulting mixture is a turbid liquid, with no seeds or lumps.

[0142] Over a period of approximately thirty (30) minutes, another 3.4 kg (1.7 kg) of a 50% solution of potassium hydroxide was added with mixing to the vessel. After addition is complete, the mixture is stirred for another 30 minutes at 80°C. The mixture remains a turbid liquid mass, with no seeds or lumps. The pH of a 10% wt solution of the mixture should be between approximately 5.3 to approximately 5.5. If it is not, additional potassium hydroxide solution is added. In this example, an additional 1 kg (0.5 kg) of the 50% solution brought the pH to 5.3 for this test batch.

[0143] Preparation of sodium metabisulfite solution:

[0144] The sodium metabisulfite solution was prepared separately. 4.07 kg (21 .41 moles) of sodium metabisulfite and 3.8 kg (1.9 kg) of 50% wt solution of potassium hydroxide were dissolved in 13.40 kg of soft water in a beaker with stirring. The initial pH was 6.8. The pH of the sodium metabisulfite solution was adjusted to a pH ranging from PAT15806-WO-PCT approximately 7.0 to approximately 7.3 using the 50% wt solution of potassium hydroxide, specifically 7.1 for this test batch. The resulting yellowish transparent solution is substantially free of any precipitates. The solution is also substantially free of sodium thiosulfite and preferably contains 0% wt sodium thiosulfite. As discussed above, 5.4 kg (42 moles) sodium sulfite in water at a pH of 7-7.3 may be used in place of the 4.07 kg (21 moles) of sodium metabisulfite.

[0145] Sulfonation:

[0146] Over a period of approximately sixty (60) minutes at a temperature of 78-82°C, 21.27 kg (21.41 mol) of the sodium metabisulfite solution previously prepared is added dropwise using a dropping funnel to the mixing vessel. After completion of the addition, mixing is continued for approximately 2 hours at 78-82°C. The mixture becomes a yellowish, creamy liquid with no seeds or lumps.

[0147] The temperature was decreased to 70°C and 55 kg water added with mixing.

[0148] The temperature was decreased to 60°C and 1 .25 kg water added with mixing.

[0149] The Karl Fischer water content should be 25% ± 1 %.

[0150] The pH of a 10% solution should be 7 to 10, preferably between 8 to 9.

[0151] The resulting product is an aqueous mixture of 3:1 molar ratio of glyceryl monostearate succinate to glyceryl monostearate disuccinate. The resulting product looks like milk, namely a milky-white colored thin liquid having a viscosity slightly higher than water, typically approximately 50 cps to approximately 100 cps as measured at 25°C using spindle LV2 at 20 RPM.

[0152] The individual components of the mixture may be isolated using crystallization, distillation, differentional extraction, and / or chromatography.

[0153] Stability:

[0154] The resulting mixture has been stored for approximately 5 months in 100 rnL Nessler tubes at ambient temperature ( / .e., uncontrolled indoor room temperature and humidity). The suspension remains uniform in some of the tubes. Separation occurs in other tubes, but the suspension has easily reformed with shaking. As a result, Applicant believes the reaction product will remain stable for up to 2 years at room temperature and PAT15806-WO-PCT humidity, although shaking may be needed for resuspension. Preservatives and / or suspending agents may be added to the reaction product to improve stability during warehouse and / or transport conditions.

[0155] Based on the disclosures herein, below are non-limiting exemplary embodiments that may be pursued in non-provisional applications that claim the benefit of this application. These embodiments are presented for illustration purposes only and do not in any way limit the scope of the inventive concepts describe herein:

[0156] 1. A compound having a general formula:

[0157] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n

[0158] [HOCH2-](i-n)[-CH-CH2-O-C(=O)R], wherein each M is independently Li, Na, K, or NH4; n=0 or 1 ; and R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20.

[0159] 2. The compound of embodiment 1 , wherein n = 0 and R = C14-20.

[0160] 3. The compound of embodiments 1 or 2, wherein the compound has the formula:

[0161] 4. The compound of embodiment 1 , wherein n = 1 and R = C14-20.

[0162] 5. The compound of embodiments 1 or 4, wherein the compound has the formula: PAT15806-WO-PCT

[0163] 6. The compound of embodiment 1 , having the formula:

[0164] [MO3SCH(COOM)CH2COO-][HOCH2-][-CH-CH2-O-C(=O)CHR2NHR3], wherein R2and R3= C14-20.

[0165] 7. The compound of embodiment 1 , having the formula:

[0166] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]

[0167] [-CH-CH2-O-C(=O)CHR2NHR3], wherein R2and R3= C14-20.

[0168] 8. The compound of embodiment 1 , having the formula:

[0169] [MO3SCH(COOM)CH2COO-][HOCH2-][-CH-CH2-O-C(=O) NHR4], wherein R4= C14-20.

[0170] 9. The compound of embodiment 1 , having the formula:

[0171] [MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n[-CH-CH2-O-C(=O)NHR4], wherein R4= C14-20.

[0172] 10. The compound of any one of embodiments 1 to 9, wherein M = Na and / or K.

[0173] 11 . A method of making the compound of any one of embodiments 1 to 10, the method comprising:

[0174] (i) adding glyceryl C15-21 mono alkanoate having formula (a) to a reactor and heating to its melting temperature, wherein R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20,

[0175] (ii) maintaining the temperature while adding maleic anhydride with stirring to form an ester and diester,

[0176] (iii) adding alkali metal metabisulfite or alkali metal sulfite in an aqueous solution to the ester and diester to produce the compound of any one of embodiments 1 to 10. PAT15806-WO-PCT

[0177] 12. A method of making the compound of any one of embodiments 1 to 10, the method comprising:

[0178] (i) adding approximately 1 to approximately 6 moles of glyceryl C15-21 mono alkanoate having formula (a) to a reactor and heating to its melting temperature, wherein R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20,

[0179] (ii) maintaining the temperature while adding approximately 1 to approximately 6 moles maleic anhydride with stirring to form an ester and diester,

[0180] (iii) adding (a) approximately 2.5 moles to approximately 2.75 moles of alkali metal metabisulfite in an aqueous solution or (b) approximately 5 moles to approximately 5.5 moles of alkali metal sulfite in an aqueous solution to the ester and diester to produce the compound of any one of embodiments 1 to 10.

[0181] 13. A method of making the compound of any one of embodiments 1 to 10, the method comprising:

[0182] (i) adding approximately 1 to approximately 3 moles of glyceryl C15-21 mono alkanoate having formula (a) to a reactor and heating to its melting temperature, wherein R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20,

[0183] (ii) maintaining the temperature while adding approximately 1 to approximately 3 moles maleic anhydride with stirring to form an ester and diester,

[0184] (iii) adding (a) approximately 2.5 moles to approximately 2.75 moles of alkali metal metabisulfite in an aqueous solution or (b) approximately 5 moles to approximately 5.5 moles of alkali metal sulfite in an aqueous solution to the ester and PAT15806-WO-PCT diester to produce the compound of any one of embodiments 1 to 10, preferably the sulfosuccinate of any one of embodiments 2, 3, 6, 8, or 10.

[0185] 14. A method of making the compound of any one of embodiments 1 to 10, the method comprising:

[0186] (i) adding approximately 1 to approximately 3 moles of glyceryl C15-21 mono alkanoate having formula (a) to a reactor and heating to its melting temperature, wherein R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20,

[0187] (ii) maintaining the temperature while adding approximately 3 to approximately 6 moles maleic anhydride with stirring to form an ester and diester,

[0188] (iii) adding (a) approximately 2.5 moles to approximately 2.75 moles of alkali metal metabisulfite in an aqueous solution or (b) approximately 5 moles to approximately 5.5 moles of alkali metal sulfite in an aqueous solution to the ester and diester to produce the compound of any one of embodiments 1 to 10, preferably the disulfosuccinate of any one of embodiments 4, 5, 7, 9, or 10.

[0189] 15. A method of making the compound of any one of embodiments 1 to 10, the method comprising:

[0190] (i) adding approximately 4 moles of glyceryl C15-21 mono alkanoate having formula (a) to a reactor and heating to its melting temperature, PAT15806-WO-PCT

[0191] (ii) maintaining the temperature while adding approximately 5 to approximately 5.5 moles maleic anhydride with stirring to form an ester and diester,

[0192] (iii) adding (a) approximately 2.5 moles to approximately 2.75 moles of alkali metal metabisulfite in an aqueous solution or (b) approximately 5 moles to approximately 5.5 moles of alkali metal sulfite in an aqueous solution to the ester and diester to produce the compound of any one of embodiments 1 to 10.

[0193] 16. The method of any one of embodiments 11 to 15, wherein the alkali metal metabisulfite or alkali metal sulfite is added after calculating an esterification value of greater than 90%, the esterification value having the formula: a [%] = 200 - [(EP (mL) x N NaOH x f NaOH x 961 ) / w x 25] wherein a = the esterification value, with 0< a<100%,

[0194] EP = volume in mL of NaOH,

[0195] N NaOH = normality of NaOH solution (eq / L), f NaOH = the factor of the NaOH solution, and w = the weight in g of the esterification sample tested.

[0196] 17. The method of any one of embodiments 11 to 16, wherein the alkali metal metabisulfite or alkali metal sulfite is contained at approximately 10% wt to approximately 50% wt in the aqueous solution.

[0197] 18. The method of any one of embodiments 11 to 17, wherein the alkali metal metabisulfite or alkali metal sulfite is contained at approximately 15% wt to approximately 40% wt in the aqueous solution.

[0198] 19. The method of any one of embodiments 11 to 18, wherein the alkali metal metabisulfite or alkali metal sulfite is contained at approximately 15% wt to approximately 30% wt in the aqueous solution.

[0199] 20. The method of any one of embodiments 11 to 19, wherein the alkali metal metabisulfite or alkali metal sulfite is contained at approximately 15% wt to approximately 25% wt in the aqueous solution.

[0200] 21 . The method of any one of embodiments 11 to 20, wherein formula (a) is selected from monoglyceryl pentadecanoate, monoglyceryl palmitate, monoglyceryl heptadecanoate, monoglyceryl stearate, monoglyceryl oleate, monoglyceryl linoleate, PAT15806-WO-PCT monoglyceryl nonadecanoate, monoglyceryl arachidate, monoglyceryl arachidonate, or combinations thereof, preferably from monoglyceryl stearate, monoglyceryl oleate, monoglyceryl linoleate, or combinations thereof.

[0201] 22. The method of any one of embodiments 11 to 21 , wherein the method does not require a non-aqueous solvent.

[0202] 23. The method of any one of embodiments 11 to 21 , wherein the method does not utilize a non-aqueous solvent.

[0203] 24. The method of any one of embodiments 11 to 21 , wherein the method does not include a non-aqueous solvent.

[0204] 25. The method of any one of embodiments 11 to 21 , wherein the method is substantially free of a non-aqueous solvent.

[0205] 26. The method of any one of embodiments 11 to 25, wherein the method does not require a catalyst.

[0206] 27. The method of any one of embodiments 11 to 25, wherein the method does not utilize a catalyst.

[0207] 28. The method of any one of embodiments 11 to 25, wherein the method does not include a catalyst.

[0208] 29. The method of any one of embodiments 11 to 25, wherein the method is substantially free of a catalyst.

[0209] 30. The method of any one of embodiments 11 to 29, wherein the glyceryl C15-21 mono alkanoate, the maleic anhydride, alkali hydroxide, and the alkali metal metabisulfite or alkali metal sulfite are the only reactants.

[0210] 31. A composition comprising the compound of any one of embodiments 1 to 10.

[0211] 32. A composition comprising a product of the method of any one of embodiments 11 to 30.

[0212] 33. The composition of embodiment 31 or 32, wherein the composition comprises a 1 :1 to 1 :5 molar ratio, preferably 1 :2 to 1 :4, and more preferably 1 :3, of the compound of embodiment 2 to the compound of embodiment 4.

[0213] 34. The composition of any one of embodiments 31 to 33, wherein the compound is an opacifier contained in a consumer goods product at a concentration ranging from approximately 1 % wt to approximately 15% wt. PAT15806-WO-PCT

[0214] 35. The composition of any one of embodiments 31 to 34, further comprising a preservative, such as an organic acid, like citric acid or lactic acid, or isothiazolinone, such as MIT or BIT.

[0215] 36. The composition of any one of embodiments 31 to 35, further comprising a stabilizer, such as a nonionic surfactant.

[0216] 37. The composition of any one of embodiments 31 to 36, wherein the composition is an all purpose cleaner further comprising between approximately 0.1 % wt to approximately 0.5% wt of para-chloro-meta-xylenol or a quaternary ammonium biocide, between approximately 1 % wt to approximately 5% wt of a nonionic surfactant, pH adjuster, and water.

[0217] 38. The composition of embodiment 37, wherein the nonionic surfactant comprises a C10-C18 alcohol alkoxylate having 1 to 5 EO, preferably a C12 to C16 alcohol alkoxylate with 2-4 EO.

[0218] 39. The composition of embodiment 37 or 38, wherein the all purpose cleaner comprises approximately 3% wt to approximately 15% wt of the compound of any one of embodiments 1 to 10, preferably between approximately 5% wt to approximately 10% wt.

[0219] 40. The composition of any one of embodiment 31 to 36, wherein the composition is a laundry composition further comprising between approximately 5% wt to approximately 15% wt of an anionic surfactant and between approximately 0.5% wt to approximately 5% wt of a nonionic surfactant.

[0220] 41 . The composition of any one of embodiments 31 to 36, wherein the composition is a laundry composition further comprising between approximately 1.5% wt to approximately 8% wt of a quaternary ammonium biocide, pH adjuster, and water.

[0221] 42. The composition of embodiment 40 or 41 , further comprising a softening ingredient.

[0222] 43. The composition of any one of embodiments 40 to 42, wherein the laundry composition comprises approximately 0.05% wt to approximately 2% wt of the compound of any one of embodiments 1 to 10, preferably between approximately 0.07% wt to approximately 1 .5% wt. PAT15806-WO-PCT

[0223] The foregoing description of various aspects of the invention has been presented for purposes of illustration and description. Embodiments and / or features therein may be freely combined with one another. It is not intended to be exhaustive or to limit the invention to the precise form disclosed, and obviously, many modifications and variations are possible. Such modifications and variations that may be apparent to a person skilled in the art are intended to be included within the scope of the invention as defined by the accompanying claims.

Claims

PAT15806-WO-PCTCLAIMSWe claim:

1. A compound having a general formula:[MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n[HOCH2-](i-n)[-CH-CH2-O-C(=O)R], wherein each M is independently Li, Na, K, or NH4; n=0 or 1 ; and R = C14-20, CHR2NHR3, or NHR4, with R2, R3, and R4= a C14-20.

2. The compound of claim 1 , wherein n = 0 and R = C14-20.

3. The compound of claim 1 or 2, wherein the compound has the formula:

4. The compound of claim 1 , wherein n = 1 and R = C14-20.

5. The compound of claim 1 or 4, wherein the compound has the formula:PAT15806-WO-PCT6. The compound of claim 1 , having the formula:[MO3SCH(COOM)CH2COO-][HOCH2-][-CH-CH2-O-C(=O)CHR2NHR3], wherein R2and R3= C14-20.

7. The compound of claim 1 , having the formula:[MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-] [-CH-CH2-O-C(=O)CHR2NHR3], wherein R2and R3= C14-20.

8. The compound of claim 1 , having the formula:[MO3SCH(COOM)CH2COO-][HOCH2-][-CH-CH2-O-C(=O)NHR4], wherein R4= C14-20.

9. The compound of claim 1 , having the formula:[MO3SCH(COOM)CH2COO-][MO3SCH(COOM)CH2COOCH2-]n[-CH-CH2-O-C(=O)NHR4], wherein R4= C14-20.

10. The compound of any one of claims 1 to 9, wherein M = Na and / or K.11 . A method of making the compound of any one of claims 1 to 10, the method comprising:(i) adding glyceryl C15-21 mono alkanoate having formula (a) to a reactor and heating to its melting temperature,PAT15806-WO-PCT(ii) maintaining the temperature while adding maleic anhydride with stirring to form an ester and diester,(iii) adding alkali metal metabisulfite or alkali metal sulfite in an aqueous solution to the ester and diester to produce the compound of any one of claims 1 to 10.

12. The method of claim 11 , wherein the alkali metal metabisulfite or alkali metal sulfite is added after calculating an esterification value of greater than 90%, the esterification value having the formula: a [%] = 200 - [(EP (mL) x N NaOH x f NaOH x 961 ) / (w x 25)] wherein a = the esterification value, with 0< a<100%,EP = volume in mL of NaOH,N NaOH = normality of NaOH solution (eq / L), f NaOH = the factor of the NaOH solution, and w = the weight in g of the esterification sample tested.

13. The method of claim 11 or 12, wherein formula (a) is selected from monoglyceryl pentadecanoate, monoglyceryl palmitate, monoglyceryl heptadecanoate, monoglyceryl stearate, monoglyceryl oleate, monoglyceryl linoleate, monoglyceryl nonadecanoate, monoglyceryl arachidate, monoglyceryl arachidonate, or combinations thereof, preferably from monoglyceryl stearate, monoglyceryl oleate, monoglyceryl linoleate, or combinations thereof.

14. The method of any one of claims 11 to 13, wherein the method does not include a non-aqueous solvent or catalyst.

15. The method of any one of claims 11 to 14, wherein the glyceryl C15-21 mono alkanoate, the maleic anhydride, alkali hydroxide, and the alkali metal metabisulfite or alkali metal sulfite are the only reactants.PAT15806-WO-PCT16. A composition comprising the compound of any one of claims 1 to 10 and / or the reaction product of any one of claims 11 to 15.

17. The composition of claim 16, wherein the composition comprises a 1 :1 to 1 :5 molar ratio, preferably 1 :2 to 1 :4, and more preferably 1 :3, of the compound of claim 2 to the compound of claim 4.

18. The composition of claim 16 or 17, wherein the compound is an opacifier contained in a consumer goods product at a concentration ranging from approximately 1 % wt to approximately 15% wt.

19. The composition of any one of claims 16 to 18, wherein the composition is an all purpose cleaner further comprising between approximately 0.1 % wt to approximately 0.5% wt of para-chloro-meta-xylenol or a quaternary ammonium biocide, between approximately 1 % wt to approximately 5% wt of a nonionic surfactant, pH adjuster, and water.

20. The composition of claim 19, wherein the nonionic surfactant comprises a C10-C18 alcohol alkoxylate having 1 to 5 EO, preferably a C12 to C16 alcohol alkoxylate with 2-4 EO.21 . The composition of claim 19 or 20, wherein the all purpose cleaner comprises approximately 3% wt to approximately 15% wt of the compound of any one of claims 1 to 10, preferably between approximately 5% wt to approximately 10% wt.

22. The composition of any one of claim 16 to 18, wherein the composition is a laundry composition further comprising between approximately 5% wt to approximately 15% wt of an anionic surfactant and between approximately 0.5% wt to approximately 5% wt of a nonionic surfactant.PAT15806-WO-PCT23. The composition of any one of claims 16 to 18, wherein the composition is a laundry composition further comprising between approximately 1 .5% wt to approximately 8% wt of a quaternary ammonium biocide, pH adjuster, and water.

24. The composition of claim 22 or 23, further comprising a softening ingredient.

25. The composition of any one of claims 22 to 24, wherein the laundry composition comprises approximately 0.05% wt to approximately 2% wt of the compound of any one of claims 1 to 10, preferably between approximately 0.07% wt to approximately 1 .5% wt.

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