WO2025151394A1 - Fatty acid ring-opened and esterified epoxidized vegetable oils - Google Patents

Abstract

A method for dedusting a fibrous insulation product using a fatty acid ring-opened and fatty acid esterified epoxidized vegetable oil, having an iodine value less than 50 cg I₂ per gram and an oxidation exotherm by pressure differential scanning calorimeter of less than 1000 joules/gram at an oven temperature of 130ºC and an oxygen inlet pressure of 500 PSIG. The fibrous insulation product typically is made with a binder composition that is applied to mineral fibers in addition to the fatty acid ring-opened and fatty acid esterified epoxidized vegetable oil prior to the binder composition being cured. The starting epoxidized vegetable oils comprise epoxidized soybean oil and epoxidized corn oil.

Description

FATTY ACID RING-OPENED AND ESTERIFIED EPOXIDIZED VEGETABLE OILS

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of United States Provisional Application No. 63/620,351, filed January 12, 2024, which is hereby incorporated by reference in its entirety.

TECHNICAL FIELD AND INDUSTRIAL APPLICABILITY OF THE INVENTION

[0002] The present invention relates to fatty acid ring-opened and fatty acid esterified epoxidized soybean oil ("FAREESO",). fatty acid ring-opened and fatty acid esterified epoxidized com oil ('‘FAREECO”) and methods for making such FAREESO and FAREECO materials. The FAREESO and FAREECO materials are useful for end-use applications, such as for use in dedusting mineral fiber insulation (such as fiberglass insulation and stone wool insulation).

BACKGROUND OF THE INVENTION

[0003] Conventional fibers are useful in a variety of applications including reinforcements, textiles, and acoustical and thermal insulation materials. Although mineral fibers (e.g., glass fibers and fibers made from stone) are typically used in insulation products, depending on the particular application, organic fibers such as polypropylene, polyester, and multicomponent fibers may be used in combination with mineral fibers in forming the insulation product.

[0004] Fibrous insulation is typically manufactured by fiberizing a molten composition of polymer, glass, or other mineral (e.g., stone) and spinning fine fibers from a fiberizing apparatus, such as a rotating spinner. To form an insulation product, fibers produced by the rotating spinner are drawn downwardly from the spinner towards a conveyor by a blower. As the fibers move downward, a binder composition is sprayed onto the fibers and the fibers are collected into a high loft, continuous blanket on the conveyor. The binder composition, once cured, gives the insulation product resiliency for recovery after packaging and provides stiffness and handleability so that the insulation product can be handled and applied as needed in the insulation cavities of buildings. The cured binder composition also provides protection to the fibers from inter-filament abrasion and promotes compatibility betw een the individual fibers.

[0005] During the formation of fiberglass insulation (or stone wool insulation), dust can be liberated by the process. A dedust fluid is often applied to the glass fibers during the process to reduce this dust. Mineral-oil based fluids and vegetable-oil based fluids are often utilized as dedust fluids.

[0006] Mineral-oil based fluids tend to smoke or ignite in the high temperatures utilized to cure the binder composition.

[0007] Vegetable-oil based dedust fluids have a lower potential to smoke or ignite than mineral-oil based fluids. However, conventional vegetable-oil based fluids used as dedust fluids do have a limited amount of unsaturation, which can oxidize when exposed to high temperatures in the presence of an oxidizing agent.

[0008] The blanket containing the binder-coated fibers is passed through a curing oven and the binder is cured to set the blanket to a desired thickness. After the binder has cured, the fiber insulation may be cut into lengths to form individual insulation products, and the insulation products may be packaged for shipping to customer locations. One typical insulation product produced is an insulation batt or blanket, which is suitable for use as wall insulation in residential dwellings or as insulation in the attic and floor insulation cavities in buildings.

SUMMARY OF THE INVENTION

[0009] The inventors have surprisingly discovered that fully epoxidized com oil (ECO) or soybean oil (ESO) which have been reacted with fatty acids to ring open the oxirane rings (a fattyacid ring-opened epoxidized com oil or a fatty acid ring-opened epoxidized soybean oil) may be further esterified with additional fatty acid to make a fatty acid ring-opened and fatty acid esterified epoxidized com oil (“FAREECO ’) or a fatty acid ring-opened and fatty acid esterified epoxidized soybean oil ( ‘FAREESO”), either of which can be advantageously utilized for several end-use application, including, but not limited to, as a dedust fluid for mineral fiber insulation production facilities. Examples of the use of dedust fluids with mineral fiber insulation production are described in US Patent Number 10,030,177 B2 to Lochel, Jr. et al issued July 24, 2018, which is incorporated by reference with regard to their description of the use of dedust fluids in the manufacture of mineral fiber insulation production.

[0010] The FAREESO should have (i) an iodine value of less than 50 eg bper gram (for example, less than 40 eg b/gram, less than 35 eg IVgram) and typically from 20 to 40 eg IVgram, 20 to 35 eg b/gram, or from 25 to 35 eg IVgram, (ii) a viscosity of from 250 to 1000 cSt at 40°C, (iii) an AV of less than 5 mg KOH/g (for example, less than 3.5 mg KOH/g, less than 3.0 mg KOH/g, less than 2.0 mg KOH/g, or less than 1.5 mg KOH/g), (iv) a Cleveland Open Cup Flash point of at least 280°C, (v) an EOC content of less than less than 1.5 wt%, preferably less than 1.0 wt% (for example, less than 0.8 wt%, less than 0.5 wt%, or less than 0.2 wt%, or less than 0.1 wt%), and (vi) a hydroxyl value of from 1 mg to 100 mg KOH/g (for example from 3 mg to 60 mg KOH/g, from 3 mg to 40 mg KOH/g, or from 5 mg to 20 mg KOH/g, and (vii) a pour point of less than 23°C. The FAREESO also is some instances has an oxidation exotherm by pressure differential scanning calorimeter of less than 1000 joules/gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG (for example, less than 800 joules/gram, less than 700 joules/gram, and in some instances less than 500 joules/gram, or less than 200 joules/gram. Oxidation exotherm is measured according to the methods of ASTM D 6186-98 and with the parameters set forth herein using a Discovery DSC 25 P pressure differential scanning calorimeter available from TA Instruments.

[0011] A FAREESO meeting the above criteria will have a flash point high, which will be advantageous for several end-use applications, including as a dedust fluid where the temperature is high enough to not ignite at the high temperatures utilized for curing the binder system when manufacturing fibrous insulation products, it has a sufficient viscosity for those high temperatures, and the fatty acid ring-opened epoxidized soybean oil’s low unsaturation (as shown by the low iodine value) will minimize any tendency for it to oxidize during high temperature processes, such as the process of making the fibrous insulation product.

[0012] When used as a dedust fluid, the FAREESO effectively reduces the dust generated during the process of making the fibrous insulation product, and also reduces any potential oxidation that could occur with the dedust composition compared to conventional dedust fluids. [0013] In some aspects, the FAREESO has a pour point of less than 23°C. ty pically less than 20°C, and preferably 10°C or less (for example from about 0°C to 10°C). Having this low a pour point, will assist the FAREESO in trapping dust that may be generated by the fibrous insulation product during storage, shipping and handling.

[0014] The foregoing and other objects, features, and advantages of the invention will appear more fully hereinafter from a consideration of the detailed description that follows. It is to be expressly understood, however, that the drawings are for illustrative purposes and are not to be construed as defining the limits of the invention.

DETAILED DESCRIPTION OF THE INVENTION

[0015] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, the preferred methods and materials are described herein. All references cited herein, including published or corresponding U.S. or foreign patent applications, issued U.S. or foreign patents, and any other references, are each incorporated by reference in their entireties, including all data, tables, figures, and text presented in the cited references, unless indicated otherwise.

[0016] '‘Flash Point” or “Flash Point Temperature” is a measure of the minimum temperature at which a material wi 11 initially flash with a brief flame. It is measured according to the method of ASTM D-92 using a Cleveland Open Cup and is reported in degrees Celsius (°C).

[0017] “Pour Point” or “Pour Point Temperature” is a measure of the lowest temperature at which a fluid will flow. It is measured according to the method of ASTM D-97 and is reported in degrees Celsius (°C).

[0018] “Iodine V alue” (IV) is defined as the number of grams of iodine that will react with

100 grams of material being measured. Iodine value is a measure of the unsaturation (carboncarbon double bonds and carbon-carbon triple bonds) present in a material. Iodine Value is reported in units of grams iodine (b) per 100 grams (or alternatively centigrams iodine (I2) per gram) material and is determined using the procedure of AOCS Cd Id-92.

[0019] “Acid Value” (AV) is a measure of the residual hydronium groups present in a compound and is reported in units of mg KOH/gram material. The acid number is measured according to the method of AOCS Cd 3d-63.

[0020] “Epoxide Oxygen Content (“EOC”) content is a measure of the epoxide content of a vegetable oil, such as epoxidized soybean oil. EOC content is measured according to the method of ASTM D1652-11^E1 and is reported as weight percent of oxirane oxygen in the material.

[0021] “Hydroxyl value” is a measure of the hydroxyl functional groups present on a material. Hydroxyl value is measured according to the method of AOCS Method Cd 13-60 and is reported as milligrams KOH/gram material.

The FAREESO:

[0022] The FAREESO has a high flash point that will help minimize the chances of flash fires and/or explosions in high temperature environments and will also degrade slower than petroleum based mineral oils having lower flash points. Typically, FAREESO has a flash point of at least 280°C, preferably at least 290°C, and more preferably at least 295°C. and in some instances at least 300°C. The FAREESO typically has a viscosity at 40°C of from 250 to 1000 cSt, preferably from 300-700 cSt, more preferably from 300 to 600 cSt, and in some instances from 350 to 550 cSt at 40°C. The high flash point and relatively high viscosity of the FAREESO provide a composition that can withstand the high temperatures. This makes the FAREESO particular useful as a dedust fluid for the manufacture of mineral fiber insulation where high temperatures are utilized to cure the mineral fiber binders. Typically, the FAREESO has a pour point of less than 23°C, less than 20°C, 10°C or less (for example from about 0°C to about 10°C). This low pour point will allow the FAREESO to remain liquid during shipping and handling, with little or no special heating needed to maintain it as a liquid.

[0023] The FAREESO ty pically has a moisture content of less than 1.0 wt%, preferably less than 0.5 wt%, and more preferably less than 0. 1 wt%.

[0024] The FAREESO typically has an acid value (AV) of less than 5 mg KOH/g, preferably less than 4.0 mg KOH/g (for example less than 3.5 mg KOH/g), and in some instances more preferably less than 3.0 mg KOH/g, even more preferably less than 2.5 mg KOH/g, and in some instances where a high flash point is particularly desirable, less than 1.5 mg KOH/g. A low AV will ensure the FAREESO has a sufficiently high flash point as described herein.

[0025] The FAREESO typically has an iodine value of less than 50 eg h/gram, preferably less than 40 eg h/gram, and more preferably less than 35 eg h/gram. Typically, the iodine value ranges from 20 to 40 eg h/gram, preferably from 20 to 35 eg h/gram, and more preferably from 25 to 35 eg h/gram. This low iodine value will minimize any oxidation reactions that can take place when the FAREESO is exposed to high temperatures when being used, such as when being used as a dedust oil during the manufacture of the mineral fiber insulation product. This typically is exemplified by a low oxidation exotherm measured by pressure differential scanning calorimeter with an oven temperature of 130°C and oxygen inlet pressure of 500 PSIG (as described in the Examples) of less than 1000 joules/gram, less than 800 joules/gram, less than 700 joules/gram, and in some instances less than 500 joules/gram, and in some instances less than 200 joules/gram as measured pressure differential scanning calorimeter with an oven temperature of 130°C and oxygen inlet pressure of 500 PSIG.

[0026] The FAREESO typically has an EOC content of less than 1.5 wt%, preferably less than 1.0 wt%, less than 0.8 wt%, less than 0.5 wt%, most preferably an EOC content of less than 0.2 wt%, and in some instances less than 0.1 wt%. A too high EOC content before the esterification step will lead to undesirably high viscosity in the FAREESO, and also may raise the pour point of the FAREESO.

[0027] The FAREESO typically has a hydroxyl value from 1 mg to 100 mg KOH/g (for example from 3 mg to 60 mg KOH/g, from 3 mg to 40 mg KOH/g, or from 5 mg to 20 mg KOH/g). 0028] If utilized as a dedust composition in the manufacture of mineral fiber insulation, the FAREESO may be applied as a neat oil to the fibers or the dedust composition may be applied in the form of an oil in water emulsion comprising the FAREESO. The dedust composition typically is applied concurrently to the fibers with the binder composition, such as an aqueous curable binder system described above.

[0029] If the dedust composition is in the form of an oil in water emulsion, then preferably at least one emulsifying component is utilized to form the oil in water emulsion. The emulsion ty pically is ty pically formed by vigorously agitating the water and the oil in the presence of the at least one emulsifying component. Examples of apparatus that can be utilized to effectively use to form the oil in water emulsion include high shear mechanical devices/mixers, ultrasonic devices, and other equipment/devices known to those of skill in the art for use in forming oil in water emulsions. The weight ratio of the at least one emulsifying components to FAREESO is from 1 :200 to 15: 100, for example from 1:200 to 5: 100, from 1:200 to 3: 100 by weight.

[0030] If used as a dedust composition, then typically, excluding the weight of any water present in the dedust composition, the FAREESO is present in a cured insulation product, such as fiberglass insulation product at a weight percent of from about 0. 1 to about 5% by weight of mineral fiber, such as glass present (for example, from about 0.5 to about 4.0%, or from about 0.5% to about 3.0% by weight (and in some instances from 0.6% to 1.5% by weight) of the mineral fiber (glass) present). Excluding the weight of water, the weight ratio of the dedust composition to the solids of the binder composition (such as an aqueous curable binder system) typically is from about 1/100 to 34/100, for example from about 6/100 to 13/100, from about 4/100 to 10/100. [0031] In one aspect the at least one emulsifying component comprises a single emulsifier that is utilized to form the emulsion. In this aspect, the emulsifier typically is mixed into the FAREESO before water is introduced to form the emulsion. Examples of emulsifiers that can be utilized include, for example, ionic emulsifiers, non-ionic emulsifiers and mixtures thereof. To minimize competing reactions between the emulsifier and the components of the aqueous curable binder composition, non-ionic emulsifiers preferably are utilized. Examples of non-ionic emulsifiers include: alkoxylated alcohols (such as ethoxylated Cl 2-C18 alcohols) and alkoxylated fatty acids or alkoxylated plant-based oils (such as ethoxylated castor oil or ethoxylated castor fatty acid). Examples of ionic emulsifiers include amine-based emulsifiers (i.e., primary, secondary, tertiary, and quaternary amine-based emulsifiers) and amine modified fatty acids. Preferably ethoxylated alcohols and ethoxylated fatty acids are utilized. Most preferably, ethoxylated alcohols are utilized. 0032] In another aspect, the at least one emulsifying component comprises a first emulsifying component that is blended into the FAREESO, and a second emulsifying component that is blended into the water that is utilized to form the oil in water emulsion with the oil. Preferably, in this aspect the first emulsifying component and the second emulsifying component are mixed into the oil and water respectively before the oil and water are mixed together to form the oil in water emulsion. Examples of compounds that may be used for the first emulsifying component include the emulsifiers listed above. Examples of compounds that may be used for the second emulsifying component include: carboxymethylcellulose; maltodextrin; carbohydrates; polyols; natural viscosifiers, such as, xanthan gum, guar gum, schleroglucan; and mixtures thereof. Preferably, the second emulsifying component will increase the viscosity of the water and assist the formation of the oil in water emulsion and enhance the long-term stability of the oil in water emulsion. For example, preferably the second emulsifying component will provide an aqueous-based solution having a viscosity of from 15 to 35 centipoise at 25°C, for example from 17 to 33 centipoise at 25°C, preferably from 18 to 25 centipoise at 25°C for an aqueous solution containing less than 1 percent by weight of the second emulsifying component, preferably less than 0.5 percent by weight (for example less than 0.3 percent by weight) of the second emulsifying component. For stability, in some aspects, the oil in water emulsion will be stable for at least 4 hours, more preferably at least 14 hours and in some instances at least 24 hours (for example, at least 48 hours, 72, hours, 96, hours, or 120 hours. Where long term stability is particularly important, the oil in water emulsion will be stable for at least one week, and in some instances at least two weeks (for example, at least three weeks). Preferably the second emulsifying component comprises carboxymethylcellulose.

|0033] The ESO used to make the FAREESO typically is made using formic acid or acetic acid (or other suitable organic acids, such as fatty acids) are used together with hydrogen peroxide to epoxidize the soybean oil. The formic acid or acetic acid reacts with a peroxide to form a peracid (i.e., performic and/or peracetic acid). The peracid then reacts with unsaturated carbon-carbon bond in the soybean oil to form oxirane groups. The organic acid is liberated from the reaction of the peracid with the soybean oil and is typically recycled for reuse. In some aspects, formic acid ty pically is used instead of acetic acid to form the peracid, due to a strong mineral acid often being necessary to form a peracid when acetic acid is used. However, acetic acid typically is used to form a peracid when recycling the acetic acid is desired.

[0034] The FAREESO typically is made by ring opening and esterifying an ESO with a fatty acid source having the desired unsaturation. Preferably, the fatty acid source is comprised primarily of saturated fatty acids having C6 to C18 carbon chain lengths. A preferred fatty acid source to use contains a significant percentage of fully saturated C6 to C20 fatty acids (such as stearic acid (a Cl 8 saturated fatty acid)). Examples of preferred sources of fatty acids include fatty acid by product streams produced by the processing of plant-based oils, such as palm oil (that are saturated C6 to Cl 8 fatty acids). Examples of such fatty acid streams include deodorizer distillate streams from the processing of vegetable oil. Preferred streams include deodorizer distillate streams from the processing of palm oil, commonly referred to as palm fatty acid distillate.

[0035] While, it is preferably for the fatty acid streams to comprise a high percentage of saturated fatty acids, the fatty acid streams also preferably comprise a sufficient level of unsaturated fatty acids to provide for a final FAREESO that is liquid at room temperature. Too high levels of saturated fatty acids in the fatty acid source can lead to fatty acid ring-opened epoxidized soybean oil that solidifies at room temperature (i.e., 21-22°C). Typically, the fatty acid source has a sufficient unsaturation to provide a final FAREESO having a pour point of 20°C or less, preferably 10°C or less. Preferably, the IV of fatty acid source is from 10 eg h per gram to 95 eg h per gram, for example from 10 eg h/g to 75 eg h/g, preferably from 30 eg IVg to 70 eg 12/g, and more preferably from 40 eg h/g to 65 eg h/g. Because of their tendency to have higher percentages of short chain and medium chain fatty acids the IV of fatty acid sources derived from tropical oils can be lower and still be utilized to make a FAREESO that is liquid at the desired low temperatures than the IV of the fatty acid sources that are derived from non-tropical vegetable oils (such as fatty acid sources derived from canola oil, com oil, rape seed oil and soybean oil).

[0036] Too high levels of unsaturated fatty acids can cause the resulting FAREESO to not exhibit the iodine values described herein.

[0037] The percentage of unsaturated and unsaturated fatty acids in the fatty acid source can be obtained by blending sources of fatty acids together to obtain the desired fatty acid profile. For example, if the fatty⁷ acid stream contains too high levels of saturated fatty⁷ acids, another fatty⁷ acid stream that comprises a higher percentage of unsaturated fatty acids (such as a fatty acid stream obtained from soybean oil) can be blended with the fatty acid stream comprising a higher percentage of saturated fatty acids, to obtain a fatty⁷ acid source that comprises the desired amounts of unsaturated and saturated fatty⁷ acids. As another example, if a fatty⁷ acid stream comprises too low a percentage of saturated fatty acids, another source having a higher percentage of saturated fatty acids (such as stearic fatty acid) can be blended with it.

[0038] The FAREESO typically is made from epoxidized soybean oil (ESO) as described above as further described below. |0039] First, the ESO is ring opened with the fatty acid source by using from about 1 :2 to 2: 1 mole ratio of fatty acid to moles of epoxide present in the ESO. This first step typically is carried out in a reactor with from 10 to 1000 ppm (for example, from 100 to 1000 ppm) of a base or acid catalyst. Examples of catalysts that can be used include the following: KOH. NaOH, sulfuric acid, hydrochloric acid, phosphoric acid, CaOH2 and other base or acid catalysts known to one of ordinary skill in the art for ring opening. The contents in the reactor typically are agitated and a nitrogen blanket or sparge is applied as the reactor is heated. The mixture in the reactor is heated to 100-150°C to accelerate the ring opening reaction. During the reaction the epoxide oxygen content (EOC) is monitored until it reaches the desired value (typically less than about 1.0 wt%, preferably, less than 0.5 wt%, more preferably less than 0.2 wt%, and furthermore preferably less than 0.1 wt%. The mole ratio of fatty acid to moles of epoxide present are chosen to obtain a FAREESO having the viscosities described herein. If a highly saturated fatty acid source is utilized and not enough fatty acid is reacted with the epoxides present (as indicated by the EOC content), the final FAREESO produced will be at least partially solid at room temperature. The reaction temperature is maintained high enough to drive the epoxide ring opening reaction, but preferably is maintained below 150°C to minimize side reactions that may take place (such as polymerization reactions that can occur between epoxidized soybean oil molecules). The side reactions will use up the epoxide rings and reduce the percentage of fatty acids that can be grafted onto the ESO and increase the viscosity of the final product above the desired viscosity.

[0040] Second, the reaction product from the first step is further reacted with fatty acids through an esterification of at least some of the hydroxyl groups present on the ring opened ESO with fatty acids. Additionally, oxirane groups remaining from the first step will be ring opened by the fatty acids. The fatty acid source utilized typically is the same as used for the first step. Prior to the second step, the Acid value and hydroxyl value of the product from the first step are measured. Sufficient additional fatty' acids are added to the reactor so that the hydroxyl value of the reactive mixture is 0 to 70 units higher (preferably from 10-60 units higher or 15 to 35 units higher) than the acid value (AV of the reaction mixture). For example, if the first step results in a material having a hydroxyl value of 100 mg KOH/gram and an acid value of 10 mg KOH/gram, then enough fatty' acid should be added to increase the acid value of the material to be reacted to a range of from 30 to 100 mg KOH/g, and preferably increase the acid value of the reactants to a range of from 40 to 90 mg KOH/g. Depending on fatty acid molecular weight this could be 10- 45% additional fatty acid. Adding additional fatty' acids in this range will ensure sufficient fatty acid is esterified on the fatty acid ring opened material from the first reaction while minimizing unreacted fatty acid present at the end of the esterification step.

[0041] During the second step, from about 10-1000 ppm (for example from 100 to 1000 ppm) of a base or acid catalyst can be utilized to catalyze the esterification reaction. The catalyst used include those known to one of skill in the art for esterification reactions, such as: KOH, NaOH, sulfuric acid, hydrochloric acid, phosphoric acid, CaOH2 and other base or acid catalysts known to one of ordinary skill in the art for ring opening. During the second step reaction, the reactor’s contents are agitated and a nitrogen sparge or blanket are applied.

[0042] During the second step reaction the mixture typically is heated to 160-250°C, the acid value and hydroxyl values of the contents are monitored, and the reaction is continued until the acid value is less than 5 mg KOH/gram (preferably less than 4 mg KOH/gram, more preferably, less than 3 mg KOH/gram) and the hydroxyl value is from 0 to 50 mg KOH/gram. The FAREESO may be further stripped with steam or nitrogen at a temperature of from 200 to 250°C (for example 220 to 240°C) to further reduce the acid value if a higher flash point is desirable.

[0043] If the same fatty acid source is used for both the first step (ring opening) and second step (esterification), then all the fatty acid can be added during the first step (with a potential adjustment at the end of the first step if necessary to adjust the acid value). Preferably, not all the total required fatty acid source for both first and second step is added during the first step, with at least some of the required fatty acid source being added during or prior to the second step. This will allow the desired acid value to be readily met for the second step and reduce the probability of excess fatty acid being present at the end of the second step reaction. If all the total required fatty acid is added at the start of the first step, the change in the temperature will control when the esterification reaction commences.

[0044] Surprisingly, the resulting FAREESO may have a lower viscosity⁷ than the ring opened material from the first step, even though the FAREESO typically has a molecular weight higher than the material from the first step. While not intending to be bound by theory⁷, it is believed that this results from the hydroxy groups on the material from the first step being esterified with the additional fatty acid utilized in the second step.

EXAMPLES

[0045] The invention of this application has been described above both generically and with regard to specific embodiments. Although the invention has been set forth in what is believed to be the preferred embodiments, a w ide variety⁷ of alternatives known to those of skill in the art can be selected within the generic disclosure. The invention is not otherwise limited, except for the recitation of the claims set forth below.

[0046] The materials for use in the following examples are the following:

RBD-1 : RBD-1 Technical grade soybean oil available from Cargill, Incorporated.

- TS210 Soy Fatty Acid: is a soybean fatty acid available from Twin Rivers Technologies of Quincy, MA having an IV of from 120 to 135 eg k/gram.

Stearic Acid: 95% stearic acid available from Twin Rivers Technologies of Quincy, MA having an IV of less than 3 eg k/gram.

- Palm Fatty Acid Distillate 1 : Palm fatty acid deodorizer distillate comprising 75% free fatty acids and having an IV of 50 to 58 eg I2 per gram.

Example 1-1: Method of making epoxidized soybean oil one (ESO 1)

[0047] 376g of RBD-1, 30.5g of glacial acetic acid, and 3g of 98% sulfuric acid were added to a 1 liter, 4 neck, jacketed reactor with a mechanical stirrer. The reactor was heated to 66°C using a temperature-controlled waler bath. Once the reactor was at 66°C, 194g of 50% hydrogen peroxide were slowly added over 3 hours using an addition funnel. The bath temperature was altered throughout the reaction in order to maintain 66°C in the reactor. Once the hydrogen peroxide addition was complete, the reactor was sampled hourly for iodine value of the organic phase. Once the iodine value was < 3 eg k/g, the reactor was cooled to 40°C. At 40°C the agitation was stopped, and the aqueous and organic phases were allowed to separate. When the phases separated the bottom aqueous layer w as decant off. The top organic layer was then washed 2 times with 220 g of water and allowed to separate. The organic layer was then transferred to a 1 liter, 4 neck, round bottom flask. 0.9g of calcium hydroxide were added to the flask and the flask was heated to 110°C with a mechanical agitator and nitrogen sparge. Once the flask was at 1 10°C, 50 torr of vacuum w as applied and 25g of water were added, over 2 hours, through a sparge needle in order to steam strip the product. The product was then allowed to dry at 110°C and 50 torr vacuum for 30 minutes. After 30 minutes, vacuum was broken, and the product was cooled to 70°C before filtering through a celite coated Buchner funnel. The resulting epoxidized soybean oil had an acid value of 0.05 mg KOH/g, iodine value of 2.4 eg h/g, epoxy oxygen content of 6.95%, a viscosity of 182 cSt at 40°C, and a pour point of 5°C. Example 1-2: Method of making epoxidized soybean oil two (ESO 2)

[0048] 892g of RBD-1 and 55.4g of 88% formic acid were added to a 2 liter, 4 neck, jacketed reactor with a mechanical stirrer. The reactor was heated to 66°C using a temperature- controlled water bath. Once the reactor at 66°C, 450g of 50% hydrogen peroxide were slowly added over 2 hours using an addition funnel. The bath temperature was altered throughout the reaction in order to maintain 66°C in the reactor. Once the hydrogen peroxide addition was complete, the reactor was sampled hourly for iodine value of the organic phase until the iodine value was < 3 eg h/g. Once the iodine value was < 3 eg b/g, the reactor was cooled to 40°C. At 40°C the agitation was stopped, and the aqueous and organic phases were allowed to separate. When the phases separated the bottom aqueous layer was decant off. The top organic layer was then washed 3 times with 220 g of water and allowed to separate. The organic layer was then transferred to a 2-liter, 4 neck, round bottom flask and heated to 110°C with mechanical agitation and a nitrogen sparge. Once the flask was at 110°C, 50 torr of vacuum was applied and 50g of water were added, over 2 hours, through a sparge needle in order to steam strip the product. The product was then allowed to dry at 110°C and 50 torr vacuum for 30 minutes. After 30 minutes, vacuum was broken, and the product was cooled to 70°C before filtering through a celite coated Buchner funnel. The resulting epoxidized soybean oil had an acid value of 0.5 mg KOH/g, iodine value of 2.9 eg g, epoxy oxygen content of 6.87%. a viscosity of 178 cSt at 40°C, and a pour point of 4°C.

[0049] ESO 1 and ESO 2 were tested for Acid Value, Iodine Value, Viscosity, Oxirane content, Pour Point, and Open Cup Flash Point as described above.

[0050] The oxidation exotherms of fiberglass coated with 0.5 wt% ESO 1 and ESO 2 are measured as follows:

[0051] About 10 to 20 milligrams of ESO 1 and ESO 2 are loaded on a testing pan, is inserted into a testing cylinder. The testing cylinder is closed and inserted into a pressure differential scanning calorimeter having model number DSC25P available from TA Instruments in order to measure the oxidation exotherms exhibited by ESO 1 and ESO 2. The calorimeter heats the ESO samples from 40°C to 130°C in about a minute. Once the temperature reaches about 130°C, the sample cell/cylinder is pressurized with 500 PSIG oxygen. The sample is held at this temperature and pressure for about 5 hours. The calorimeter measures and outputs to a digital computer the total energy released (i.e., the exothermic reaction) during the evaluation of the samples, which occurs as a result of oxidation of the sample. The data output is analyzed using TA Instruments Trios software to calculate the enthalpy oxidation energy released by the sample in Joules/gram of sample tested.

[0052] The results of the analysis are set forth below in Table 1.

Table 1.

[0053] As can be seen from Table 1, ESO 1 and ESO 2 have vety high open cup flash point, and exhibit low oxidation exotherms. Also, as can be seen from Table 1, both ESO 1 and ESO 2 have pour points between 0°C and 10°C, so they both will remain liquid at room temperature.

Comparative Example 1: Method of making fatty acid ring opened epoxidized soybean oil with soy fatty acid distillate (epoxidized soybean oil two (CS-1))

[0054] Step 1 : 500g of ESO 1 and 1000g of TS210 soy fatty acid were added to a 2 -liter reactor in a distillation setup. 500ppm of KOH was added. A nitrogen sparge was applied to the reactor. While mixing, the reactor and contents were heated to 150°C for 6.5 hours.

[0055] Step 2: The AV was targeted to be <5 mg KOH/gram. The OH was targeted to be 30 mg KOH/gram. A nitrogen sparge was applied to the reactor. While mixing, the reactor and contents were heated to 230°C for 23 hours. The final AV was measured at 4.8 mg KOH/gram and the final OH was measured at 20.5 mg KOH/gram. The final viscosity is 659 cSt at 40°C. The final COC flash point is 290°C. The Final IV of the material is from 80 eg IVg to 90 eg I g. Comparative Example 2 (CS-2): ESO1 ring opened with Stearic Acid

[0056] Step 1: 175g of Epoxidized soybean Oil, 175g of stearic acid, and 0.38g of potassium hydroxide were added to a 500ml 4-neck round bottom with distillation condenser, nitrogen sparge, and mechanical agitation. The flask was heated 150°C and held for 8 hours until the EOC went < 0.1%.

[0057] Step 2: The reaction was then heated to 215°C at 10°C per hour and acid value was tracked. When the acid value was below 10 mg KOH/g sample 300 torr of vacuum was applied until the acid value was < 3 mg KOH/g. After the acid value was < 3 mg KOH/g the sample was cooled and loaded out. The resulting product was solid at room temperature (i.e., 21-22°C) with an acid value of 2.65 mg KOH/g, hydroxyl value of 105 mg KOH/g.

Example 2: Method of making FAREES0-1

[0058] 304g of ESO-1, 296g of Palm Fatty Acid Distillate 1, and 0.55g of potassium hydroxide were added to a 1 liter 4- round bottom flask with a distillation condenser, nitrogen sparge, and mechanical agitation. The reactor was heated up to 150°C and held for 17 hours until the EOC was < 0.1%. The resulting product had a hydroxyl value of 87 mg KOH/g, an acid value of 2. 15 mg KOH/g and an iodine value of 31 eg h/g.

[0059] 168g of the product and 82g of Palm Fatty Acid Distillate 1 were added to a 500ml

4-neck round bottom flask with a distillation condenser, nitrogen sparge, and mechanical agitation. The reactor was heated to 230°C until the acid value was less than 4, then 50 torr vacuum and a steam sparge were applied for 2 hours. The resulting product was liquid at room temperature (i.e., 21-22°C) and had an acid value of 1.3 mg KOH/g, hydroxyl value of 8. 1 mg KOH/g, iodine value of 31 eg h/g, EOC of 0.08%, viscosity at 40°C of 659 cSt, and a Cleveland open cup flash point of 309°C. Additionally, it exhibits an oxidative exotherm by pressure differential scanning calorimeter of less than 1000 joules/gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

Example 3: Making Fiberglass Insulation

[0060] One set of R-19 to R-20 fiberglass insulation batts are manufactured in a conventional manner known to one of ordinary skill in the art. All the fiberglass batts are manufactured with a target LOI of 6.0 + 0.5.

[0061] The set of batts are manufactured utilizing an aqueous curable binder system. FAREESO-1 is utilized for the dedust composition. The amount of dedust composition utilized in the manufacture of this set of fiberglass batts varies from 0.375 to 0.75 percent by weight based on the weight of the cured fiberglass insulation. Additionally, about thirteen percent (13%) by weight of a gamma-aminopropyl-trihydroxy-silane coupling agent and five percent (5%) by weight of Sodium Hypophosphite accelerant based on the weight of the binder composition, silane, and accelerant are utilized during the manufacture of the fiberglass batts. The extent of curing (high, medium, and low cure) is varied during the manufacture of the fiberglass batts of this first set.

[0062] All bats are made without the occurrence of any fire, explosion or runaway oxidation event. All the bats have excellent physical properties and are consistent throughout. [0063] Soybean oil and com oil have similar IVs (120 to 135 eg h per gram and 110 to 130 eg I2 per gram, respectively) and similar fatty acid residue distribution (e.g., 16:0, 18:0, 18: 1s, 18:2s and 18:3s), and when made according to the procedures set forth above, FAREECO will have similar properties as the FAREESO.

Claims

CLAIMS What is claimed is:

1. A fatty acid ring-opened and esterified epoxidized soybean oil (FAREESO), comprising:

(i) a viscosity of from 250 to 1000 cSt at 40°C, (ii) an AV of less than 5 mg KOH/g, (iii) a Cleveland Open Cup Flash point of at least 280°C, (iv) an iodine value of less than 50 eg T2 per gram, (v) an EOC content of less than 1.5 wt%, and (vi) a hydroxyl value of from 1 mg to 100 mg KOH/g, and (vii) a pour point of less than 23°C.

2. The FAREESO of claim 1, wherein the FAREESO has (vii) an oxidation exotherm by pressure differential scanning calorimeter of less than 1000 joules/ gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

3. The FAREESO of any of claims 1 or 2, wherein the FAREESO has (i) a viscosity from 250 to 750 cSt at 40°C.

4. The FAREESO of any of claims 1-3, wherein the FAREESO has an AV of less 3.0 KOH/g.

5. The FAREESO of any of claims 1-4, wherein the FAREESO has an AV of less than 2.0 KOH/g (for example, less than 1.5 KOH/g).

6. The FAREESO of any of claims 1-5, wherein the FAREESO has a Cleveland Open Cup Flash point of at least 290°C.

7. The FAREESO of any of claims 1-6, wherein the FAREESO has a Cleveland Open Cup Flash point of at least 295°C, for example at least 300°C.

8. The FAREESO of any of claims 1-7, wherein the FAREESO has an iodine value of less than 40 eg I2 per gram (for example, from 20 to 35 eg I2 per gram).

9. The FAREESO of any of claims 1-8, wherein the FAREESO has an iodine value of less than 35 eg I2 per gram (for example, from 25 to 35 eg I2 per gram).

10. The FAREESO of any of claims 1-9, wherein the FAREESO has an EOC content of less than 1.0 wt%.

11. The FAREESO of any of claims 1-10. wherein the FAREESO has an EOC content of less than 0.5 wt% (for example less than 0.2 wt% or less than 0.1 wt%).

12. The FAREESO of any of claims 1-11, wherein the FAREESO has an oxidation exotherm by pressure differential scanning calorimeter of less than 800 joules/gram (for example, less than 700 joules/gram) at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

13. The FAREESO of any of claims 1-12, wherein the FAREESO has an oxidation exotherm by differential scanning calorimeter of less than 500 joules/gram, or less than 200 joules/gram.

14. The FAREESO of any of claims 1-13, wherein the FAREESO is utilized as a dedust fluid for the manufacture of mineral fiber insulation.

15. A dedust composition for the manufacture of mineral fiber insulation or marts, the dedust composition comprising the FAREESO of any of claims 1-14.

16. The dedust composition of claim 15, wherein the dedust composition comprises an aqueous emulsion comprising the FAREESO.

17. The dedust composition of claim 16, wherein the aqueous emulsion further comprises at least one emulsifying component.

18. The dedust composition of any of claims 16 and 17. wherein the dedust composition comprises an aqueous fraction and an organic fraction.

19. The dedust composition of any of claims 16-18, wherein dedust composition comprises an oil in water emulsion and wherein a first emulsifier component is mixed into the FAREESO before the emulsion is formed.

20. The dedust composition of claim 19, wherein a second emulsifying component is mixed into an aqueous solution before the oil water emulsion is formed by mixing the aqueous solution and the FAREESO.

21. The dedust composition of claim 20. wherein the second emulsifying component is selected from the group consisting of carbohydrates, maltodextrin, carboxymethyl cellulose, polyols, alkoxylated fatty acid, alkoxylated plant-based oils, and mixtures thereof.

22. The dedust composition of claim 17. wherein the at least one emulsifying component is selected from the group consisting of non-ionic emulsifiers, ionic emulsifiers, and mixtures thereof.

23. A method for ring opening and es ten T ing epoxidized soybean oil with a fatty acid source, the method comprising the steps of: a) obtaining an epoxidized soybean oil; b) adding a fatty acid source to the epoxidized soybean oil; c) adding an acidic or base catalyst; d) heating the epoxidized soybean oil, fatty acid source and catalyst to ring open the epoxide of the epoxidized soybean oil at atemperature from 100°C to 150°C until the EOC content of the mixture is less than 1.5 wt% (for example, less than 1.0 wt%, less than 0.5 wt%, less than 0.2 wt%, or less than 0.12 wt%; and e) raising the temperature of the reaction mixture to between 160°C to 250°C to the material resulting from step d) to produce a fatty acid ring opened and fatty acid esterified material.

24. The method of claim 23, wherein the fatty acid ring opened and fatty acid esterified material has: (i) a viscosity of from 250 to 1000 cSt at 40°C, (ii) an AV of less than 5 mg KOH/g, (iii) a Cleveland Open Cup Flash point of at least 280°C, (iv) an iodine value of less than 50 eg I2 per gram, (v) an EOC content of less than 1.5 wt%, a hydroxyl value of from 1 mg to 100 mg KOH/g, and (vi) a pour point of less than 23°C.

25. The method of any of claims 23 and 24, wherein the fatty acid ring opened and fatty acid esterified material has (vii) an oxidation exotherm by pressure differential scanning calorimeter of less than 1000 joules/gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

26. The method of any of claim 23-25. wherein the fatty acid source added in step b) has a IV of from 10 eg h/gram to 95 eg h/gram, for example, from 10 eg b/gram to 75 b/gram. from 30 eg h/gram to 70 eg h/gram, or from 40 eg h/gram to 65 eg h/gram.

27. The method of any of claims 23-26, wherein the fatty acid source comprises palm fatty acid deodorizer distillate.

28. The method of any of claims 23-27, wherein the fatty acid source is added in step b) and prior to or during step e).

29. Use of a dedust composition of any of claims 15-22 for dedusting a fibrous insulation product (such as fiberglass insulation).

30. Use of a dedust composition comprising the FAREESO of any of claims 1-14 for dedusting a fibrous insulation product (such as fiberglass insulation), wherein the FAREESO has an iodine value less than 50 eg h per gram and an oxidation exotherm by pressure differential scanning calorimeter of less than 1000 joules/gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

31. The use of any of claims 29 and 30, wherein the FAREESO has an iodine value of less than 40 eg h/gram (for example, less than 35 eg h per gram).

32. The use of any of claims 29 and 30, wherein the FAREESO has an iodine value from 20 to 40 eg h per gram.

33. The use of any of any of claims 29 and 30, wherein the FAREESO has an iodine value from 25 to 35 eg h per gram.

34. The use of any of claims 29-33, wherein the FAREESO has an oxidation exotherm by pressure differential scanning calorimeter of less than 800 joules/gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

35. The use of any of claims 29-34, wherein the FAREESO has an oxidation exotherm by differential scanning calorimeter of less than 700 joules/gram, less than 500 joules/gram, or less than 200 joules/gram, at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.

36. Any of the above claims, wherein the FAREESO has a pour point of 20°C or less.

37. Any of the above claims, wherein the FAREESO has a pour point of 10°C or less (for example from about 0°C to 10°C).

38. A fatty acid ring-opened and esterified epoxidized com oil (FAREECO), comprising:

(i) a viscosity of from 250 to 1000 cSt at 40°C, (ii) an AV of less than 5 mg KOH/g, (iii) a Cleveland Open Cup Flash point of at least 280°C, (iv) an iodine value of less than 50 eg h per gram, (v) an EOC content of less than 1.5 wt%, a hydroxyl value of from 1 mg to 100 mg KOH/g, and (vi) a pour point of less than 23°C.

39. The FAREECO of claim 38, wherein the FAREECO has (vii) an oxidation exotherm by pressure differential scanning calorimeter of less than 1000 joules/gram at an oven temperature of 130°C and an oxygen inlet pressure of 500 PSIG.