Cross Reference to Related Application

This application claims benefit of and priority to US Provisional Application 62/598,255 filed December 13, 2017 and to US Provisional Application 62/607,492 filed on December 19, 2017. Each of these applications is hereby incorporated by reference, each in its entirety.

Field

This Application is in the field of cleaning compositions.

Introduction

Various chemicals commonly used in the cleaning of textiles (“dry-cleaning”) such as hydrocarbons, chlorocarbons and fluorocarbons, are environmentally toxic. The most widely used chlorocarbon chemical in non-aqueous“dry-cleaning” of textiles is tetrachloroethylene, also known as perchloroethylene, PERC or PCE. However, this chemical and its breakdown products of trichloroethylene, dichloroethylene and vinyl chloride are considered pollutants that can contaminate soil and groundwater. Other solvents used for dry cleaning include petroleum-based solvents such as“Stoddard solvent” which is a mixture of C _{5 -} C12 petroleum hydrocarbons containing 30 - 50% straight- and branched -chained alkanes, 30 - 40% cycloalkanes, and 10 - 20 % alkyl aromatic compounds; Dry cleaning Fluid-2000 or DF-2000™ Fluid (ExxonMobil Chemical Company) containing Cn to C13 hydrocarbons such as isoparaffins and cycloparaffins; ECOSOLV ^® Dry Cleaning Fluid (Chevron Phillips Chemical Company containing a mixture of C10 C13 isoparaffins; HYDROCLENE ^® Drycleaning Fluid

(Shell Chemical Company comprising a mixture of normal-, iso- and cyclo-paraffins; Shell Sol 140 HT (Shell Chemical Company) which is a mixture of predominantly C9 - C12 hydrocarbons. Yet other dry-cleaning solvents include carbon tetrachloride, 1,1,2- Trichlorotrifluoroethane, and l,l,l-Trichloroethane, as well as glycol ethers, liquid carbon dioxide, and n-Propyl Bromide.

“Green” alternatives to PERC include decamethylcyclopentasiloxane (D5), a silicone based solvent, and supercritical CO2. However, these alternatives are considered inferior to PERC in their cleaning effectiveness. Furoate esters are chemical compounds of structure

wherein R is an alkyl moiety of 1-4 carbons. The alkyl“R” moiety can be a linear, branched or cyclic alkyl moiety. Methods of production of furoate esters are known, and described in publications such as US Patents 8,710,250, 9,102,644 and 9,108,940, and US Patent Application Publication 2014/0194633.

What are needed are dry-cleaning chemical compositions that are non-toxic and biodegradable, yet have cleaning power that is comparable to that of PERC.

Petroleum is distributed via miles of pipelines. Water and heavy oil (asphaltenes) collect in low spots and in bends in the pipes and must be periodically cleaned to ensure reliable and dependable flow. Heavier-than-water solvents such as PCE have been used to remove water and heavy oil from points of collection. PCE has been replaced with hot diesel fuel due to the environmental concerns of PCE use. However, diesel fuel is lighter than water and is not effective at also removing water from low collection points in the piping. Those points in the piping where water collects are at risk for corrosion.

Environmentally benign formulations are required for use in pipeline cleaning.

Summary

The present inventors have developed cleaning compositions useful for the cleaning of garments and other textiles as well as the cleaning of metal surfaces and oil pipelines.

In various embodiments, a cleaning composition of the present teachings can be a mixture comprising, consisting essentially of, or consisting of a furoate alkyl ester and a surfactant.

In various embodiments, a cleaning composition of the present teachings can be a mixture comprising, consisting essentially of, or consisting of a first furoate alkyl ester, a second furoate alkyl ester, ethyl levulinate, and a surfactant.

In various embodiments, a cleaning composition of the present teachings can be a mixture comprising, consisting essentially of, or consisting of a first furoate alkyl ester, a second furoate alkyl ester, and a surfactant.

In various embodiments, a cleaning composition of the present teachings can be a mixture comprising, consisting essentially of, or consisting of a furoate methyl ester, a furoate ethyl ester, and a surfactant. In various embodiments, a cleaning composition of the present teachings can be a mixture comprising, consisting essentially of, or consisting of a first furoate alkyl ester, a second furoate alkyl ester, ethyl levulinate, and at least one surfactant.

In various embodiments, a cleaning composition of the present teachings can be a mixture comprising, consisting essentially of, or consisting of methyl furoate

levulinate least one surfactant.

In various configurations, a cleaning composition can comprise, consist essentially of, or consist of at least 85%, at least 88%, at least 90%, at least 95% or at least 98% by weight of a furoate alkyl ester, such as methyl furoate or ethyl furoate, with the remainder comprising, consisting essentially of, or consisting of at least one surfactant.

In various configurations, a cleaning composition can comprise, consist essentially of, or consist of at least 85%, at least 90%, at least 95% or at least 98% by weight of a first furoate alkyl ester, about 1%, from 1% to 5%, or about 5% of a second furoate alkyl ester, about 0.0%, from 0.0% to 5%, or about 5% by weight of ethyl levulinate, with the remainder comprising, consisting essentially of, or consisting of at least one surfactant.

In various configurations, a cleaning composition can comprise about 88%, from 88% to 99%, or about 99% by weight of a first furoate alkyl ester, about 0.0%, from 0.0% to about 5%, or about 5% by weight of ethyl levulinate, about 1%, 1% to 5%, or about 5% by weight of a second furoate alkyl ester, and about 0.5%, 0.5% to 2%, or about 2% by weight of a surfactant.

In various configurations, a cleaning composition of the present teachings can comprise, consist essentially of, or consist of about 95%, from 95% to 99%, or about 99% by weight of a first furoate alkyl ester, about 0.0%, from 0.0% to about 5%, or about 5% by weight of ethyl levulinate, about 1%, 1% to 5%, or about 5% by weight of a second furoate alkyl ester, and about 1%, 1% to 2%, or about 2% by weight of a surfactant.

In various configurations, a cleaning composition of the present teachings can comprise, consist essentially of, or consist of 95% to 99% by weight of a first furoate alkyl ester, 0.1% to 5% by weight of ethyl levulinate, 1% to 5% by weight of a second furoate alkyl ester, and 1% to 2% by weight of a surfactant.

In some configurations, the first furoate alkyl ester can be methyl 5-methyl-2- furoate and the second furoate alkyl ester can be ethyl 5-methyl-2-furoate.

In some configurations, the first furoate alkyl ester can be ethyl 5-methyl-2- furoate and the second furoate alkyl ester can be methyl 5-methyl-2-furoate.

In various configurations, a cleaning composition of the present teachings can comprise, consist essentially of, or consist of 0.5% to 10% by weight of a non-ionic surfactant, with the remainder comprising, consisting essentially of, or consisting of at least one furoate alkyl ester.

In various configurations, a cleaning composition of the present teachings can comprise, consist essentially of, or consist of 0.5%, about 0.5%, 1%, about 1%, 2%, about 2%, 3%, about 3%, 4%, about 4%, 5%, about 5%, 6%, about 6%, 7%, about 7%, 8%, about 8%, 9%, about 9%, 10%, or about 10% by weight of a non-ionic surfactant, with the remainder comprising, consisting essentially of, or consisting of at least one furoate alkyl ester.

In various configurations, a cleaning composition of the present teachings can be a composition without water, or water in no more than trace quantities.

As used herein, a low HLB is an HLB below 3, a medium HLB is an HLB from 3 to 13, and a high HLB is an HLB above 13.

In some configurations, the surfactant can be a low HLB surfactant (HLB below 3, e.g., an HLB of 1.8)

In some configurations, the surfactant can be a medium HLB surfactant (HLB from 3 to 13, e.g., an HLB of about 10)

In some configurations, the surfactant can be a high HLB surfactant (HLB above 13, e.g., about 18).

In some configurations, the surfactant can be a non-ionic detergent.

In some configurations, the surfactant can be sorbitan trioleate (SPAN ^® 85; Croda Inc, Edison, NJ), polyoxyethylene sorbitan trioleate (TWEEN™ 85; Croda Inc., Edison, NJ), octylphenoxypolyethoxyethanol (TRITON ^® X-405; Dow Chemical Company, Midland, MI) or a combination thereof. In some configurations, the surfactant can be sorbitan trioleate (SPAN ^® 85; Croda Inc, Edison, NJ), polyoxyethylene sorbitan trioleate (TWEEN™ 85; Croda Inc., Edison, NJ), octylphenoxypolyethoxyethanol (TRITON ^® X-405; Dow Chemical Company, Midland, MI) or a combination thereof.

In various embodiments, the present teachings include methods of removing a soil from a textile. In various configurations, a method can comprise a) contacting a soiled textile with a composition comprising at least one furoate alkyl ester of structure wherein R is an alkyl moiety of 1-8 carbon atoms, 1-7 carbon atoms, 1-6 carbon atoms, 1-5 carbon atom, or 1-4 carbon atoms, and at least one non ionic surfactant and b) heating the textile and the composition. In some compositions, the methods can further include c) agitating the heated textile. In various configurations, a method can comprise a) contacting a soiled textile with a composition comprising at least

one furoate alkyl ester of structure wherein R is an alkyl moiety of 1-4 carbon atoms, and at least one non-ionic surfactant, and b) agitating the textile.

In some configurations, the at least one furoate alkyl ester can be methyl 5- methyl-2-furoate (“methyl furoate”).

In some configurations, the at least one furoate alkyl ester can be ethyl 5-methyl- 2-furoate (“ethyl furoate”).

In some configurations, the at least one furoate alkyl ester can be isopropyl 5-

methyl-2-furoate

In some configurations, the at least one furoate alkyl ester can be a mixture of methyl 5-methyl-2-furoate and ethyl 5-methyl-2-furoate.

In some configurations, in a composition comprising a furoate and a surfactant, the surfactant can be any non-ionic surfactant with a Hydrophilic - Lipophilic Balance (HLB) in an appropriate range. In various configurations, the HLB of a surfactant that can be used in a cleaning solution of the present teachings can be low (HLB about 3), medium (HLB about 10) or high (HLB about 18). For example, sorbitan trioleate (SPAN ^® 85; Croda Inc, Edison, NJ) has a low HLB (1.8), Polyoxyethylene sorbitan trioleate (TWEEN™ 85; Croda Inc., Edison, NJ) has a medium HLB (11.0) and octylphenoxypolyethoxyethanol (TRITON ^® X-405; Dow Chemical Company, Midland, MI) has a high HLB (17.6, www.dow.com). In some configurations, a formulation can comprise a mixture of surfactants.

In some configurations of these methods, a composition can further comprise ethyl levulinate.

In some configurations of these methods, a textile being cleaned can be heated to a temperature of about 40°C-50°C while being treated with a composition of the present teachings.

In various embodiments, a method of the present teachings can comprise applying a formulation of the present teachings to a metal surface. A metal surface that can be cleaned can be, for example and without limitation, the surface of a metal which is fabricated or forged, such as, without limitation, sheeting, plating, billets, and objects manufactured from metal, such as, without limitation a firearm or an automobile.

In various configurations, a method can comprise a) contacting a soiled metal surface with a composition comprising at least one furoate alkyl ester of structure wherein R is an alkyl moiety of 1-8 carbon atoms, 1-7 carbon atoms, 1-6 carbon atoms, 1-5 carbon atom, or 1-4 carbon atoms, and at least one non ionic surfactant and b) applying friction to the metal surface. In various configurations, a method can comprise flushing a pipeline with a composition comprising at least one

furoate alkyl ester of structure wherein R is an alkyl moiety of

1-4 carbons, and at least one non-ionic surfactant.

In some configurations, the at least one furoate alkyl ester can be methyl 5- methyl-2-furoate (“methyl furoate”).

In some configurations, the at least one furoate alkyl ester can be ethyl 5-methyl-

2-furoate (“ethyl furoate”).

In some configurations, the at least one furoate alkyl ester can be isopropyl 5- methyl-2-furoate

In some configurations, the at least one furoate alkyl ester can be a mixture of methyl 5-methyl-2-furoate and ethyl 5-methyl-2-furoate.

In some configurations, in a composition comprising a furoate and a surfactant, the surfactant can be any non-ionic surfactant with a Hydrophilic - Lipophilic Balance (HLB) in an appropriate range. In various configurations, the HLB of a surfactant that can be used in a cleaning solution of the present teachings can be low (HLB about 3), medium (HLB about 10) or high (HLB about 18). For example, sorbitan trioleate (SPAN ^® 85; Croda Inc, Edison, NJ) has a low HLB (1.8), Polyoxyethylene sorbitan trioleate (TWEEN™ 85; Croda Inc., Edison, NJ) has a medium HLB (11.0) and octylphenoxypolyethoxyethanol (TRITON ^® X-405; Dow Chemical Company, Midland, MI) has a high HLB (17.6, www.dow.com). In some configurations, a formulation can comprise a mixture of surfactants.

In some configurations of these methods, a composition can further comprise ethyl levulinate.

In some configurations of these methods, a formulation of the present teachings can be heated to a temperature of about 40°C-50°C before being applied to a metal surface or flushed through a pipeline.

The present teachings include, without limitation, the following aspects. In some embodiments, a composition of the present teachings can comprise a first furoate alkyl ester; and at least one surfactant. In some configurations, the first furoate alkyl ester can be at least 95% by weight and the at least one surfactant is at least 1% by weight. In some configurations, a composition of the present teachings can further comprise ethyl levulinate; and a second furoate alkyl ester. In various configurations, the first furoate alkyl ester can be isopropyl 5-methyl-2-furoate. In various configurations, the at least one surfactant can be a non-ionic surfactant. In various configurations, the at least one non-ionic surfactant can be a low HLB surfactant. In various configurations, the at least one non-ionic surfactant can be sorbitan trioleate. In various configurations, the at least one non-ionic surfactant can be a medium HLB surfactant. In various configuragions, the at least one non-ionic surfactant can be oleic acid. In various configurations, the at least one non-ionic surfactant can be a high HLB surfactant. In various configurations, the at least one non-ionic surfactant can be octylphenoxypolyethoxyethanol. In various configurations, the at least one surfactant can be selected from the group consisting of sorbitan trioleate, polyoxyethylene sorbitan trioleate and

octylphenoxypolyethoxyethanol. In various configuragions, the at least one surfactant can be from 1% to 5% by weight of a non-ionic surfactant.

In various embodiments, a composition of the present teachings can comprise a first furoate ester, ethyl levulinate, a second furoate ester and a surfactant.

In various embodiments, a composition of the present teachings can comprise 95% to 99% by weight of a first furoate ester, 0.1% to 5% by weight of ethyl levulinate, 1% to 5% by weight of a second furoate ester, and 1% to 2% by weight of a surfactant.

In various configurations, the first furoate ester can be methyl 5-methyl-2-furoate and the second furoate ester can be ethyl 5-methyl-2-furoate.

In various configurations, the first furoate ester can be ethyl 5-methyl-2-furoate and the second furoate ester can be methyl 5-methyl-2-furoate.

In various configurations, the surfactant can be selected from the group consisting of sorbitan trioleate (SPAN ^® 85), polyoxyethylene sorbitan trioleate (TWEEN™ 85), octylphenoxypolyethoxyethanol (TRITON ^® X-405) and a combination thereof.

In various embodiments, a method of removing a soil from a soiled textile, can comprise contacting a soiled textile with the compositions of the present teachings as described supra. In some configurations, the method can further comprise heating the soiled textile and the composition. In various configurations, the method can further comprise agitating the soiled textile and the composition. In various configurations, the heating the soiled textile and the composition can consist of heating the soiled textile and the composition to about 40-50°C. . In various configurations, the heating the soiled textile and the composition can consist of heating the soiled textile and the composition to 40-50°C. . In various configurations, the heating the soiled textile and the composition can consist of heating the soiled textile and the composition to about 40°C. . In various configurations, the heating the soiled textile and the composition can consist of heating the soiled textile and the composition to about 50°C.

In various embodiments, the present teachings provide for a method of removing a soil from a soiled textile comprising: a) providing a composition as described supra ; b) contacting a soiled textile with the composition; c) heating the soiled textile and the composition; and d) agitating the soiled textile and the composition. In some

configurations, the at least one furoate alkyl ester can be methyl 5-methyl-2-furoate. In various configurations, the at least one furoate alkyl ester can be ethyl 5-methyl-2- furoate. In various configurations, the at least one furoate alkyl ester can be isopropyl 5- methyl-2-furoate. In various configurations, the at least one furoate alkyl ester can be a mixture of methyl 5-methyl-2-furoate and ethyl 5-methyl-2-furoate. In various configurations, the composition can further comprise a surfactant. In some

configurations, the surfactant can be selected from the group consisting of sorbitan trioleate (SPAN ^® 85), Polyoxyethylene sorbitan trioleate (TWEEN™ 85),

octylphenoxypolyethoxyethanol (TRITON ^® X-405) and a combination thereof.

In various configurations, the composition can further comprise ethyl levulinate.

In various configurations, the heating the soiled textile and the composition can consist of heating the soiled textile and the composition to about 40-50°C.

In various embodiments, the present teachings provide a method comprising a) forming a composition comprising: 95% to 99% by weight of a first furoate ester; 0.1% to 5% by weight of ethyl levulinate; 1% to 5% by weight of a second furoate ester; and 0.5% to 2% by weight of a surfactant; b) heating the composition; and c) agitating the composition. In some configurations, the first furoate ester can be methyl 5-methyl-2- furoate. In various configurations, the second furoate ester can be ethyl 5-methyl-2- furoate.

In various configurations, the heating the composition can consist of heating the composition to about 40-50°C.

In various configurations, the surfactant is selected from the group consisting of sorbitan trioleate (SPAN ^® 85), Polyoxyethylene sorbitan trioleate (TWEEN™ 85), octylphenoxypolyethoxyethanol (TRITON ^® X-405) and a combination thereof.

In various embodiments, the present teachings provide for a composition comprising: at least one furoate alkyl ester; and at least one non-ionic surfactant. In some configurations, the at least one furoate alkyl ester can be selected from the group consisting of methyl 5-methyl-2-furoate, ethyl 5-methyl-2-furoate and a combination thereof.

In various configurations, the at least one non-ionic surfactant can be a low HLB surfactant.

In various configurations, the at least one non-ionic surfactant can be sorbitan trioleate (SPAN® 85).

In various configurations, the at least one non-ionic surfactant can be a medium HLB surfactant. In various configurations, the at least one non-ionic surfactant can be oleic acid (TWEEN™ 85).

In various configurations, the at least one non-ionic surfactant can be a high HLB surfactant.

In various configururations, the at least one non-ionic surfactant can be octylphenoxypolyethoxyethanol (TRITON ^® X-405).

In various configurations, the at least one furoate alkyl ester can be from 95% to 99% of the furoate alkyl ester.

In various configurations, the at least one non-ionic surfactant can be from 1% to 5% of a non-ionic surfactant.

In various configurations, the composition can comprise about 98% of the furoate alkyl ester and about 2% of the non-ionic surfactant.

In various embodiments, a composition of the present teachings can comprise: at least one furoate alkyl ester; and at least one non-ionic surfactant. In various

configurations, the at least one furoate alkyl ester can be selected from the group consisting of methyl 5-methyl-2-furoate, ethyl 5-methyl-2-furoate and a combination thereof. In various configuragions, the at least one furoate alkyl ester is from 95% to 99% by weight. In various configurations, the at least one non-ionic surfactant is from 1% to 5% by weight. In various configurations, the composition can comprise about 98% of the at least one furoate alkyl ester and about 2% of the non-ionic surfactant. In various configurations, the at least one non-ionic surfactant can be selected from the group consisting of sorbitan trioleate, polyoxyethylene sorbitan trioleate and

octylphenoxypolyethoxyethanol. In various configurationsm, the at least one non-ionic surfactant can be a low HLB surfactant. In various configurations, the low HLB surfactant can be sorbitan trioleate. In various configurations, the at least one non-ionic surfactant can be a medium HLB surfactant. In various configurations, the at least one medium HLB surfactant can be oleic acid. In various configurations, the at least one non ionic surfactant can be a high HLB surfactant. In various configurations, the at least one non-ionic surfactant is octylphenoxypolyethoxyethanol.

In various embodiments, the present teachings provide for a method of cleaning a metal surface comprising: a) providing a composition in accordance with the present teachings; b) contacting a soiled metal surface with the composition; c) applying friction to the soiled metal surface. In various configurations, the composition can be heated prior to contacting it to the metal surface. In various embodiments, a method of cleaning a metal surface can comprise contacting a soiled metal surface with a composition in accordance with a composition of the present teachings.

In various embodiments, the present teachings provide for a method of cleaning a metal pipe comprising: a) providing a composition in accordance with the present teachings; and b) flushing the composition through the soiled metal pipe. In various configurations, the soiled metal pipe can be an oil distribution pipe. In various configurations, the soil on the metal pipe can comprise deposits of paraffin, asphaltenes or a combination thereof.

In various embodiments, the present teachings provide for a method of cleaning an oil distribution pipe, comprising passing a composition of the present teachings through the interior of an oil distribution pipe. In various configurations, the interior of the oil distribution pipe comprises asphaltene, paraffin, or a combination thereof.

Detailed Description

The inventors have developed compositions comprising alkyl furoates and methods of use thereof. The compositions can be used for cleaning fabric and textiles (“dry cleaning”) and metal surfaces. The compositions can also be used for removing organic deposits that can accumulate in a petroleum environment such as a crude oil pipeline.

In various embodiments, a cleaning formulation of the present teachings can comprise a first furoate ester, ethyl levulinate, a second furoate ester, and a surfactant.

In various embodiments, a cleaning formulation of the present teachings can comprise a furoate ester and a surfactant.

Furoate esters

Furoate esters of the present teachings are alkyl furoate esters with a general

structure wherein R is an alkyl moiety. In various configurations, R can be an alkyl moiety consisting of, consisting essentially of, or comprising 1-10 carbon atoms, 1-9 carbon atoms, 1-8 carbon atoms, 1-7 carbon atoms, 1-6 carbon atoms, 1-5 carbon atoms, 1-4 carbon atoms, 1-3 carbon atoms, or 1-2 carbon atoms. In some embodiments, R can be an alkyl moiety of 1-2 carbon atoms. Furoate esters suitable for a composition of the present teachings include, without limitation, methyl 5-methyl-2-furoate, ethyl 5-methyl-2-furoate, and isopropyl 5-methyl-2-furoate. Furoate esters are available in commercial formulations including those sold under the trade names Methyl 408™, Ethyl 408™, and Isopropyl 408™ (xF Technologies, Albuquerque, NM). Other furoate esters (for example methyl furoate in the case of Et 408™ and ethyl furoate in the case of Me 408™) frequently occur in the manufacturing process for the esters from various cellulosic and sugar sources. In particular, a commercial formulation of Me 408™ could contain 2.5% of ethyl furoate and 2.5% of ethyl levulinate. It has been found that these minor impurities do not negatively affect the function of the primary ester.

Certain furoate esters, such as the ethyl and methyl furoate esters, can be used in dry-cleaning formulations for the cleaning of textiles. Certain commercial furoate products such as Methyl408, Ethyl408 and isopropyl408 by xF Technologies

(Albuquerque, NM) are characterized by the manufacturer as having applicability as cleaning solvents (xftechnologies.com). These furoates have properties such as lower toxicity and biodegradability that can render them preferable to traditional dry-cleaning chemicals.

Surfactants

A surfactant that can comprise a composition of the present teachings can be characterized in part by the value of its Hydrophilic - Lipophilic Balance (HLB). A surfactant of a composition of the present teachings can be a non-ionic surfactant.

It is a known property of surfactant systems that they can be mixed to achieve a desired HLB. Therefore, skilled artisans will appreciate that surfactants with similar properties can be mixed to achieve a desired HLB and similar results can be obtained using different surfactants. A surfactant mixture having a desired HLB can be obtained by combining surfactants.

As used herein, a low HLB is an HLB below 3, a medium HLB is an HLB from 3 to 13, and a high HLB is an HLB above 13.

Non-limiting examples of surfactants and their HLB values are listed in Table 1.

Table 1

Suitable surfactants for use in formulations of the present teachings include low HLB surfactants such as sorbitan trioleate (SPAN ^® 85; Croda Inc, Edison, NJ; HLB 1.8), medium HLB surfactants such as polyoxyethylene sorbitan trioleate (TWEEN™ 85; Croda Inc., Edison, NJ; HLB 11.0), and high HLB surfactants such as

octylphenoxypolyethoxyethanol (TRITON ^® X-405; Dow Chemical Company, Midland, MI; HLB 17.6).

In various embodiments, formulations of the present teachings can be effective for the cleaning of textiles or garments in a process without the use of water, or“dry cleaning.” In various embodiments, formulations of the present teachings can be effective for cleaning metals. In various embodiments, formulations of the present teachings can be effective for flushing oil pipelines to remove various soils that deposit on the interiors of pipes carrying crude oil. Such soils can include, for example, asphaltene and paraffin.

Examples

The present teachings including descriptions provided in the Examples that are not intended to limit the scope of any claim or aspect. Unless specifically presented in the past tense, an example can be a prophetic or an actual example. The following non- limiting examples are provided to further illustrate the present teachings. Those of skill in the art, in light of the present disclosure, will appreciate that many changes can be made in the specific embodiments that are disclosed and still obtain a like or similar result without departing from the spirit and scope of the present teachings. As used in the present description and any appended claims, the singular forms“a”,“an” and“the” are intended to include the plural forms as well, unless the context indicates otherwise.

In Examples 2 and 3, the degree of removal in the examples is based on measured weight loss after the application of the soil and drying of the remaining soil on the fabrics. It is not based on subjective observation.

Examples 1-3 use the following formulations:

Formulation 1, comprising a low HLB surfactant (Table 2).

Table 2

Methyl 408™ is xF Technologies’ brand of methyl furoate (met lyl 5-methyl-2-furoate)

As an“off-the-shelf’ product, without further purification, Methyl 408™ can include some ethyl furoate (1% to 5%), small amounts of ethyl levulinate (0.1% to 5%), and trace amounts of other substances in addition to methyl furoate.

Formulation 2, comprising a medium HLB surfactant (Table 3).

Table 3

As an“off-the-shelf’ product, without further purification, Methyl 408™ can include some ethyl furoate (1% to 5%), small amounts of ethyl levulinate (0.1% to 5%), and trace amounts of other substances in addition to methyl furoate.

Formulation 3, comprising a high HLB surfactant (Table 4).

Table 4

As an“off-the-shelf’ product, without further purification, Methyl 408™ can include some ethyl furoate (1% to 5%), small amounts of ethyl levulinate (0.1% to 5%), and trace amounts of other substances in addition to methyl furoate.

Example 1

This example illustrates the removal of soils from a woven cotton polyester blend. A woven cotton polyester fabric swatch was soiled with carbon and vegetable oil, salad dressing or red wine and cleaned with formulations as presented in Table 5.

Table 5

*Best cleaning results for the indicated soil on a woven cotton polyester blend of the compositions tested.

The carbon and vegetable oil provide a mixture of both an oily soil and a particulate soil. With the dry-cleaning compositions of the present teachings, attacking either oily soils or particulate soils loosens the soil from the cloth matrix. Formulations 1 and 3 appear to be superior Formulation 2 at cleaning the carbon and vegetable oil.

In contrast, red wine is a highly particulate colored soil after the water and alcohol in the wine evaporate. In traditional formulations, a high HLB surfactant, is considered to be superior to a low HLB surfactant at removing wine stains. We found that Formulation 3 comprising a high HLB surfactant (TRITON ^® X-405, HLB 17.6), removes more wine. Therefore, with respect to these sorts of stains, formulations of the present teachings are able to remove a wider variety of stains compared to traditional dry-cleaning

formulations.

Example 2

This example illustrates the removal of stains from non-woven cotton polyester by formulations of the present teachings.

Soils were added to the cloth as described in Example 1. The results are presented in Table 6.

Table 6

*Best cleaning results for the indicated soil on non-woven cotton polyester of the compositions tested.

The efficacy on non-woven fabrics is exceptional. These results illustrate the effectiveness of the formulations for cleaning highly colored particulate fruit soils such as wine. The results also show that the Me 408™ can carry various types of surfactants.

Example 3

This example illustrates the ability of formulations of the present teachings to remove stains from coarse cotton.

Soils were added to the cloth as described in Example 1. The results are presented in Table 7.

Table 7

*Best cleaning results for the indicated soil on coarse cotton of the compositions tested.

Pure cotton is a very difficult substrate to clean and the across-the-spectrum performance of formulations of the present teachings is excellent. The cleaning ability of formulations with a High HLB surfactant in the case of wine on cotton can be

significantly better compared to lower HLB surfactants.

Example 4

This example illustrates the use of a composition of the present teachings for cleaning a metal pipe of crude oil deposits.

A formulation of 99% methyl furoate (Methyl 408TM (xF Technologies,

Albuquerque, NM)) and 1% sorbitan monooleate is subjected to an asphaltene dispersant test (ADT) in accordance with the ASTM D7061-17 standard (Turbiscan®). The formulation performs at least as well as a formulation of diesel fuel considered to be best-in-class.

All publications cited are herein incorporated by reference, each in its entirety.