Compositions of inorganic saccharide fatty acid ester particles, article of manufacture and method of treatment of a cellulosic substrate

Abstract

Combinations of saccharide fatty acid ester inorganic particles. The present invention relates to methods of treating cellulosic materials with compositions that allow for greater retention of inorganic particles in cellulosic substrates. The methods, as described, provide for the combination of saccharide fatty acid esters (SFEAs) with such inorganic particles and the application of such combinations in cellulosic materials to eliminate or reduce the use of retention aids or binders for filling in the papermaking process. Compositions comprising such combinations of SFEAs and inorganic particles are also described.

Description

1 / 69 COMPOSITIONS OF INORGANIC SACCHARIDE FATTY ACID ESTER PARTICLES, ARTICLE OF MANUFACTURE AND METHOD OF TREATMENT OF A CELLULOSIC SUBSTRATE BACKGROUND OF THE INVENTION CROSS-REFERENCE TO RELATED REQUESTS

[0001] This application claims priority over U.S. Patent Application No. 16 / 456,433, filed June 28, 2019, in the U.S. Patent and Trademark Office, which is incorporated herein by reference in its entirety. FIELD OF THE INVENTION

[0002] The present invention relates generally to the treatment of cellulose-based materials and more specifically to the treatment of such materials with saccharide fatty acid esters (SFAEs) in combination with inorganic particles, including compositions containing such combinations. BACKGROUND INFORMATION

[0003] Inorganic particles such as kaolin, talc, calcium carbonate, and TiO2 are commonly used in papermaking processes as fillers. Calcium carbonate, for example, is used in paper mills as a filler material in the alkaline papermaking process. Currently, calcium carbonate dominates other filter materials for papermaking (e.g., kaolin). The main reason for the preference for calcium carbonate is the demand for brighter and bulkier papers. There are significant benefits to using calcium carbonate in the alkaline papermaking process (e.g., calcium carbonate is cheaper and, if it has high gloss, creates a porous surface on the paper sheet, improves permeability, decreases binder demand, increases machine speed and productivity, improves water drainage, improves machine operation, Petition 870260047896, dated 05 / 20 / 2026, page 6 / 172 2 / 69 being economical in paper manufacturing processes, it may reduce fiber consumption and may achieve greater retention compared to other paper fillers).

[0004] Generally, calcium carbonate occurs in three natural forms, such as limestone, chalk, and marble. Naturally, it is formed through the reactions of calcium salt and carbon dioxide. There are two types of calcium carbonate used in paper mills: ground calcium carbonate (GCC) and medium precipitated calcium carbonate (PCC).

[0005] Ground calcium carbonate is manufactured by grinding limestone or marble and is used due to its high brightness and purity. Generally, the particle shape of ground calcium carbonate is rhombohedral. This filler material is used in wood-free, alkaline papermaking processes. The brightness of GCC is approximately 86 to 95%.

[0006] The rough shape of the particles and the small amounts of quartz often found in GCC create a problem; it is more abrasive and shortens the life of the paper machine, forming pressing threads and felts.

[0007] Precipitated calcium carbonate is the form of CaCO3 that is produced by chemical reactions, and the process is known as carbonation. PCC improves upon the disadvantage of GCC, providing better gloss and opacity properties to the paper. The structure of PCC is different from the structure of GCC. The crystal structure of PCC can be controlled and includes needle, rhombohedral (cubic), scalenohedral (triangular), and prismatic shapes. The gloss of PCC is about 90 to 97%. However, paper sheets containing PCC may have poorer formation than paper sheets containing GCC.

[0008] In modern high-speed double-paper machines, the turbulence required to obtain good formation often Petition 870260047896, dated 05 / 20 / 2026, page 7 / 172 3 / 69 cause low charge retention. Furthermore, for both types of calcium carbonates, they do not adhere to cellulose on their own and require a retention aid or binder to attach to the pulp. Typically, such retention aids or binders include papermaker alum, synthetic polymers, polyacrylamides, microparticle systems, latex, starch, and polyvinyl alcohol (PvOH), whose retention aids or binders can increase costs or make products less green (e.g., synthetic polymers) where desired.

[0009] It would be desirable to bind calcium carbonates to make use of unnecessary retention aids or binders or to reduce the amount of retention aid or binder needed to attach inorganic particles to cellulosic surfaces. SUMMARY OF THE INVENTION

[0010] The present invention relates to methods of treating cellulosic materials with a composition that allows, inter alia, greater retention of organic particles (i.e., fillers). The methods as described provide combinations of saccharide fatty acid esters (SFAEs) with such fillers and application of such combinations to cellulose to eliminate or reduce the use of retention aids or fiber binders in the papermaking process. Compositions comprising combinations of SFAEs and inorganic particles are also described.

[0011] In embodiments, a composition comprising a saccharide fatty acid ester (SFAE) and inorganic particles is described, wherein the SFAE is present in a concentration sufficient to cause the inorganic particles to be retained in the cellulose-based material and wherein the substrate containing the composition exhibits greater water resistance and / or greater grease resistance compared to the substrate containing the composition comprising Petition 870260047896, dated 05 / 20 / 2026, page 8 / 172 4 / 69 inorganic particles or one or more SFAEs alone.

[0012] In one aspect, SFAE includes all saturated fatty acids, all saturated fatty acids, or a mixture of saturated and saturated fatty acids and optionally also includes one or more binders selected from PvOH or starch.

[0013] In another aspect, the SFAE is a mixture of two of the most Different SFAEs, where two or more SFAEs contain all saturated fatty acids.

[0014] In one aspect, the inorganic particles include clay, ground calcium carbonate, precipitated calcium carbonate, talc, titanium dioxide and combinations thereof, wherein said inorganic particles comprise at least 1% of the composition on a dry basis (db).

[0015] In another aspect, the SFAE contains at least one saccharide and at least one aliphatic group comprising 8 to 30 carbons. In one aspect, the inorganic particle is calcium carbonate, where the substrate exhibits water resistance; in a related aspect, the inorganic particle is clay, where the substrate exhibits fat resistance.

[0016] In one aspect, the cellulose-based substrate includes paper, cardboard, paper pulp, a cardboard food storage box, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant cover film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a compostable bag, release paper, cutlery, a hot or cold beverage container, a cup, paper towels, a plate, Petition 870260047896, dated 05 / 20 / 2026, page 9 / 172 5 / 69 a carbonated liquid storage bottle, insulating material, a non-carbonated liquid storage bottle, food packaging film, a waste container, a food handling instrument, a cup lid, a screw-on cup lid made of moldable paper, paper straws, a fabric fiber, a water transport and storage instrument, medical use card, release paper, an instrument for transporting and storing alcoholic or non-alcoholic beverages, wrapper, a good electronic external screen, an internal or external piece of furniture, a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic fiber material and combinations thereof.

[0017] In embodiments, a manufactured article is described including a coating containing one or more saccharide acid esters (SFAEs), inorganic particles, a cellulose-based substrate, and optionally, one or more binders, wherein the inorganic particles are present in the coating at a concentration of at least 1% on a dry basis (db).In a related aspect, cellulose-based substrate includes paper, cardboard, paper pulp, a cardboard food storage box, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant cover film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a compostable bag, release paper, cutlery, a beverage container. Petition 870260047896, dated 05 / 20 / 2026, page 10 / 172 6 / 69 hot or cold, cup, paper towels, plate, a carbonated liquid storage bottle, insulating material, a non-carbonated liquid storage bottle, food packaging film, a waste container, a food handling instrument, a cup lid, a screw-on moldable paper cup lid, paper straws, a fabric fiber, a water transport and storage instrument, medical use card, release paper, an instrument for transporting and storing alcoholic or non-alcoholic beverages, wrapper, a good electronic external screen, an internal or external piece of furniture, a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic fiber material and combinations thereof.

[0018] In embodiments, a method of treating a cellulosic substrate is described including adding at least one saccharide fatty acid ester (SFAE) to a composition comprising inorganic particles to form a mixture, b) applying said mixture to at least one surface of said cellulosic substrate; and c) curing for a time sufficient to allow the mixture to adhere to at least one surface, wherein the cured surface exhibits greater hydrophobicity and / or lipophobicity compared to a surface treated with at least one SFAE or the composition comprising the inorganic particles alone.

[0019] In one aspect, the treated cellulosic surface is hydrophobic. In another aspect, the treated cellulosic surface is lipophobic.

[0020] In one aspect, SFAE includes all saturated fatty acids or a mixture of saturated and unsaturated fatty acids; in another aspect, SFAE is a mixture of two or more SFAEs. Petition 870260047896, dated 05 / 20 / 2026, page 11 / 172 7 / 69 different.

[0021] In one aspect, the inorganic particles include clay, ground calcium carbonate, precipitated calcium carbonate, talc, titanium dioxide and combinations thereof, wherein said inorganic particles comprise at least 1% of the composition on a dry basis (db). In a related aspect, the composition also comprises polyvinyl alcohol or starch.

[0022] In one aspect, the inorganic particles include calcium carbonate, wherein calcium carbonate comprises more than or equal to about 30% of the mixture on a dry basis (db).

[0023] In another aspect, the cellulosic substrate includes paper, cardboard, paper pulp, a cardboard food storage box, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant cover film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a composting bag, release paper, cutlery, a hot or cold beverage container, a cup, paper towels, a plate, a carbonated liquid storage bottle, insulating material, a non-carbonated liquid storage bottle, food packaging film, a garbage container, a food handling instrument, a cup lid, a screw-on moldable paper cup lid,paper straws, a type of fabric fiber, a device for transporting and storing water, a medical device, a release paper, a device for transporting and storing alcoholic or non-alcoholic beverages, a wrapper, a good external electronic screen, an internal or external piece of furniture. Petition 870260047896, dated 05 / 20 / 2026, page 12 / 172 8 / 69 a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic material or combinations thereof. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] FIG. 1 shows a scanning electron micrograph (SEM) of untreated Whatman medium porosity filter paper (58x magnification).

[0025] FIG. 2 shows a SEM of untreated Whatman medium porosity filter paper (1070x magnification);

[0026] FIG. 3 shows a side-by-side comparison of SEMs of paper made from recycled pulp before (left) and after (right) coating of cellulose with myerofibrillated cellulose (MFC): (27x magnification).

[0027] FIG. 4 shows a side-by-side comparison of SEMs of paper made from recycled pulp before (left) and after (right) coating with MFC (98x magnification).

[0028] FIG. 5 shows the water penetration in paper treated with various coating formulations: polyvinyl alcohol (PvOH), diamonds; SEFOSE® + PvOH at 1:1 (v / v), squares; Ethylex (starch), triangles, SEFOSE® + PvOH at 3:1 (v), crosses. DETAILED DESCRIPTION OF THE INVENTION

[0029] Before the present composition, methods and methodologies are described, it should be understood that this invention is not limited to the particular compositions, methods and experimental conditions described, as such compositions, methods and maximum conditions vary. It should also be understood that the terminology used herein is for purposes of describing particular embodiments, and is not intended to be limiting, since the scope of the present invention will be limited only to the appended claims. Petition 870260047896, dated 05 / 20 / 2026, p. 13 / 172 9 / 69

[0030] As used in this specification and the appended claims, the singular forms a, an (a), a, an (a) and the, a include plural references, unless the context clearly indicates otherwise. Thus, for example, references to a saccharide fatty acid include one or more saccharide fatty acid esters and / or compositions of the type described herein, which will become apparent to those skilled in the art after reading this invention, and so forth.

[0031] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one skilled in the art to which this invention pertains. As used in this specification and the appended claims, the singular forms a, an (a), a, an (a) and the, a include plural references, unless the context clearly indicates otherwise. Thus, for example, references to a saccharide fatty acid include one or more saccharide fatty acid esters and / or compositions of the type described herein, which will become apparent to those skilled in the art after reading this invention, and so forth.

[0032] As used herein, “about,” “approximately,” “substantially,” and “significantly” will be understood by a person skilled in the art and will vary to some extent depending on the context in which they are used. If there are uses of the term that are not clear to those skilled in the art, given the context in which it is used, “about” and “approximately” will mean more or less <10% of the particular term, and “substantially” and “significantly” will mean more or less >10% of the particular term. “Comprising” and “consisting essentially of” have their usual meanings in the art.

[0033] All pigments must be retained uniformly in Petition 870260047896, dated 05 / 20 / 2026, page 14 / 172 10 / 69 sheet to be effective. Paper can be made cheaper by using fillers that are less expensive than fibers. However, the proportion of filler in the sheet is limited by the resulting reduction in strength, volume, and sizing quality. Although the trend is definitely towards higher filler contents, once the pigment concentration is above 10 or 20% in any barrier coating, the barrier properties are significantly reduced.

[0034] Although not a polymer per se, SFAEs assist in retaining inorganic fillers or particles, such as PCC. While not limited by theory, SFAEs can cross-link or provide network communication surfaces in fines and fibers. The combination performs well and allows for a higher level of bonding without compromising product quality, including delivering a high level of performance.

[0035] In addition, organic particles, such as uncooked starch, wood particles, oat hulls and the like, offer shell and caliber that are much needed in some products and can be added, while inorganic particles increase density. Furthermore, for hydrophobic polymers that can create undesirable particles and / or sticky masses or deposits, including wood resin, hot melt waxes, bioplastics and the like, the use of combinations of inorganic SFAE particles can overcome such undesirable agglomerations.

[0036] Furthermore, the addition of a composition comprising a mixture of inorganic particles and SFAEs would offer improved fine-tuning of the various properties of a sheet. For example, such sheets may contain wood fiber and include a bioplastic fiber along with combinations of SFAEs to waterproof such. Petition 870260047896, dated 05 / 20 / 2026, page 15 / 172 11 / 69 sheet. The proposed combinations would allow the use of more common and cheaper materials, such as mechanical or recycled pulp, to have a higher percentage of the sheet mass. In such a case, the addition of, for example, a calcium carbonate-SFAE mixture would offer the improvement of allowing control of the sheet density.

[0037] In embodiments, the present invention shows that by treating cellulosic materials with a combination of inorganic particles and saccharide fatty acid esters, the resulting material, inter alia, can be made strongly hydrophobic and / or lipophobic; furthermore, these saccharide fatty acid esters, for example, once removed by bacterial enzymes, are easily digested as such. The derivatized surface exhibits high heat resistance, being able to withstand temperatures up to 250 °C and can be more impermeable to gases than the underlying substrate. The material is therefore an ideal solution to the problem of derivatizing the hydrophilic surface of cellulose in any embodiment in which cellulose materials may be employed.

[0038] The advantages of the products and methods described here include that the coating composition is made from renewable agricultural resources – saccharides and vegetable oils; it is biodegradable; it has a low toxicity profile and is suitable for food contact; it can be adjusted to reduce the coefficient of friction of the paper / cardboard surface (i.e., it does not couple very slippery paper for in-line processing or end use), even at high levels of water resistance; it can be used with or without special emulsifying equipment or emulsifying agents, and is compatible with traditional paper recycling programs; i.e., it does not have an adverse impact on recycling operations, like polyethylene, polylactic acid or the Petition 870260047896, dated 05 / 20 / 2026, page 16 / 172 12 / 69 wax-coated papers do. Furthermore, the extended use of inorganics, such as PCC, takes advantage of the filler's inherent properties (e.g., less abrasive).

[0039] As used herein, bio-based means a material intentionally made from substances derived from living (or once living) organisms. In a related aspect, material containing at least about 50% of such substances is considered bio-based.

[0040] As used here, to connect, including grammatical variations thereof, means to adhere to or cause to be adhered to essentially as a single mass.

[0041] As used herein, cellulosic means natural, synthetic or semi-synthetic materials that can be molded or extruded into objects (e.g., bags, sheets) or films or filaments, which can be used to make such objects or films or filaments, which are structurally and functionally similar to cellulose, for example, coatings and adhesives (e.g., carboxymethylcellulose). In another example, cellulose, a complex carbohydrate (CeHieOsjn) which is composed of glucose units, which forms the main constituent of the cell wall in most plants, is cellulosic.

[0042] As used herein, coating weight is the weight of a material (wet or dry) applied to a substrate. It is expressed in pounds per specified ream or grams per square meter.

[0043] As used here, compostable means that these solid products are biodegradable in the soil.

[0044] As used herein, dry basis is the measure of the mass of all constituents, excluding water (e.g., solids),

[0045] As used herein, edge absorption means the sorption of water into a paper structure at the outer boundary of said structure. Petition 870260047896, dated 05 / 20 / 2026, p. 17 / 172 13 / 69 structure by one or more mechanisms, including, but not limited to, capillary penetration into the pores between the fibers, diffusion through the fibers and bonds, and surface diffusion in the fibers. In a related aspect, the saccharide fatty acid ester-containing coating, as described herein, prevents edge absorption in treated products. In another aspect, there is a similar problem with grease / oil entering the creases that may be present in paper or paper products. This grease crease effect can be defined as the sorption of grease into a paper structure that is created by folding, pressing, or crushing said paper structure.

[0046] As used here, effect, including grammatical variations thereof, means to impart a particular property to a specific material.

[0047] As used herein, hydrophobic means a substance that does not attract water. For example, waxes, rosins, resins, fatty acid esters of saccharides, dikethenes, shellac, vinyl acetates. PLA, PEI, oils, fats, lipids, other water-repellent chemicals or combinations thereof are hydrophobic.

[0048] As used herein, hydrophobicity means the property of being water-repellent, tending to repel rather than absorb water.

[0049] As used herein, lipid resistance or lipophobicity means the property of being lipid-repellent, tending to repel and not absorb lipids, fat, grease and the like. In a related aspect, fat resistance can be measured by a 3M KIT test from a TAPPI T559 test kit.

[0050] As used herein, cellulose-containing material or cellulose-based material means a composition consisting essentially of cellulose. For example, such material may include, but is not limited to, paper, cardboard, paper pulp, a box Petition 870260047896, dated 05 / 20 / 2026, page 18 / 172 14 / 69 cardboard food storage container, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant cover film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a composting bag, release paper, cutlery, a hot or cold beverage container, a cup, paper towels, a plate, a carbonated liquid storage bottle, insulating material, a non-carbonated liquid storage bottle, food packaging film, a trash can, a food handling instrument, a cup lid, a screw-on moldable paper cup lid, paper straws, a fabric fiber, a water transport and storage instrument,Medical prescription card, release paper, a container for transporting and storing alcoholic or non-alcoholic beverages, wrapper, a good electronic external screen, an internal or external piece of furniture, a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic material and combinations thereof.

[0051] As used herein, removable paper means a sheet of paper used to prevent a sticky surface from prematurely adhering to an adhesive or mastic. In one aspect, coatings, as described herein, can be used to replace or reduce the use of silicon or other coatings to produce a material with low surface energy. The determination of surface energy can be easily achieved by measuring the angle of Petition 870260047896, dated 05 / 20 / 2026, page 19 / 172 15 / 69 contact (e.g., Optical Tensiometer and / or High Pressure Chamber, Dyne Testing, Staffordshire, UK) or by using Surface Energy Test Pens or Inks (see, for example, Dyne Testing, Staffordshire, UK),

[0052] As used herein, releasable with reference to SFAE means that the SFAE coating, once applied, can be removed from the cellulose-based material (e.g., removable by manipulation of physical properties). As used herein, non-releasable with reference to SFAE means that the SFAE coating, once applied, is substantially and irreversibly bonded to the cellulose-based material (e.g., removable by chemical means).

[0053] As used herein, fibers in solution or pulp means a lignocellulosic fibrous material prepared by chemical or mechanical separation of cellulose fibers from wood, fiber crops, or waste paper. In a related aspect, where cellulose fibers are treated by the methods described herein, the cellulose fibers themselves contain linked saccharide fatty acid esters as isolated entities, and where the linked cellulose fibers have separate and distinct properties from the free fibers (e.g., cellulose pulp or fiber or material linked to cellulose saccharide fatty acid ester or microfibrillated nanocellulose would not form hydrogen bonds between the fibers as readily as unlinked fibers).

[0054] As used herein, repulpable means to make a paper or cardboard product suitable for being crushed into a soft, shapeless pulp for reuse in the production of paper or cardboard.

[0055] As used herein, tunable, including grammatical variations thereof, means to adjust or adapt a process to achieve a particular result. Petition 870260047896, dated 05 / 20 / 2026, page 20 / 172 16 / 69

[0056] As used herein, water contact angle means the angle measured through a liquid where a liquid / vapor interface meets a solid surface. It quantifies the wettability of the solid surface by the liquid. The contact angle is a reflection of how strongly liquid and solid molecules interact with each other, relative to how strongly each interacts with its own kind. On many highly hydrophilic surfaces, water droplets will exhibit contact angles of 0° to 30°. Generally, if the water contact angle is greater than 90°, the solid surface will be considered hydrophobic. The water contact angle can be easily obtained using an optical tensiometer (see, for example, Dyne Testing, Staffordshire, UK).

[0057] As used herein, water vapor permeability means breathability or the ability of a textile to transfer moisture. There are at least two different measurement methods. One, the MVTR (moisture vapor transmission rate) test, according to ISO 15496, describes the water vapor permeability (WVP) of a fabric and therefore the degree of transport of perspiration to the outside air. The measurements determine how many grams of moisture (water vapor) pass through a square meter of fabric in 24 hours (the higher the level, the greater the breathability).

[0058] In one aspect, the TAPPI T 530 Hercules size test (i.e., size test for paper by ink resistance) can be used to determine water resistance; ink resistance by the Hercules method is best classified as a direct measurement test for the degree of penetration. Others classify it as a penetration rate test. There is no ideal test for measuring sizing. The selection of the test depends on the end use and the factory's control needs. This method is especially suitable for batch use as a sizing test. Petition 870260047896, dated 05 / 20 / 2026, page 21 / 172 17 / 69 mill control to accurately detect changes in sizing level. It offers the sensitivity of the paint flotation test while providing reproducible results, shorter test times, and automatic endpoint determination.

[0059] Sizing, measured by the resistance to penetration or absorption of aqueous liquids into the paper, is an important characteristic of many papers. Typical examples are bag paper, container paper, butcher's packaging, writing paper, and some grades of printing paper.

[0060] This method can be used to monitor the production of paper or board for specific end uses, provided an acceptable correlation has been established between the test values ​​and the end-use performance of the paper. Due to the nature of the test and the penetrant, it will not necessarily correlate sufficiently to be applicable to all end-use requirements. This method measures downsizing by penetration rate. Other methods measure sizing by surface contact, surface penetration, or absorption. Sizing tests are selected based on their ability to simulate the means of water contact or absorption in end-use. This method can also be used to optimize the costs of using sizing chemicals.

[0061] As used herein, oxygen permeability means the degree to which a polymer allows the passage of a gas or fluid. The oxygen permeability (Δk) of a material is a function of diffusivity (D) (i.e., the rate at which oxygen molecules pass through the material) and solubility (k) (or the amount of oxygen molecules absorbed, by volume, in the material). Oxygen permeability (Δk) values ​​generally fall within the range of 10 to 150 x 10¹¹ (cm² ml O₂) / (s ml mm Hg). It has been demonstrated Petition 870260047896, dated 05 / 20 / 2026, page 22 / 172 18 / 69 a semilogarithmic relationship exists between the water content of the hydrogel and oxygen permeability (Unit; Barrer unit). The International Organization for Standardization (ISO) specified permeability using the SI unit heciopascdl (hPa) for pressure. Therefore, Dk = 1011(cm2ml O2) / (s ml hPa). The Barrer unit can be converted to hPa by multiplying it by the constant 0.75.

[0062] As used herein, biodegradable, including grammatical variations thereof, means capable of being broken down specifically into harmless products by the action of living beings (e.g., by microorganisms).

[0063] As used herein, recyclable, including grammatical variations thereof, means a material that is treatable or can be processed (with used items and / or waste) in such a way as to make said material suitable for reuse.

[0064] As used herein, filler means finely divided white mineral (or pigments) added to papermaking materials to improve the optical and physical properties of the sheet. The particles serve to fill the spaces and gaps between the fibers, thus producing a sheet with greater brightness, opacity, softness, gloss, and printability, but generally with less tackiness and tear resistance. Common papermaking fillers include clay (kaolin, bentonite), calcium carbonate (both GCC and PCC), talc (magnesium silicate), and titanium dioxide.

[0065] As used herein, a Gurley second or Gurley number is a unit describing the number of seconds required for 100 cubic centimeters (deciliter) of air to pass through 1.0 square inch of a material supplied at a differential pressure of 4.88 inches of water (0.16 psi) (ISO 5636-5; 2003) (Porosity). Additionally, for stiffness, a Gurley number is a Petition 870260047896, dated 05 / 20 / 2026, page 23 / 172 19 / 69 unit for a piece of fabric held vertically measuring the force required to deflect said material by a given amount (1 milligram of force). Such values ​​can be measured on a device from Gurley Precision Instruments (Troy, New York).

[0066] The hydrophilic-lipophilic balance (HLB) of a surfactant is a measure of the degree to which it is hydrophilic or lipophilic, determined by calculating values ​​for different regions of the molecule.

[0067] Griffin's method for nonionic surfactants, as described in 1954, works as follows: HLB = 20 * Mh / M

[0068] Where Mh is the molecular mass of the hydrophilic portion of the molecule, and M is the molecular mass of the entire molecule, giving a result on a scale of 0 to 20. An HLB value of 0 corresponds to a completely lipophilic / hydrophobic molecule and a value of 20 corresponds to a completely hydrophobic / lipophobic molecule.

[0069] The HLB value can be used to predict the surfactant properties of a molecule: <10: Lipid-soluble (water-insoluble) > 10: Water-soluble (lipid-insoluble) 1.5 to 3: antifoaming agent; 6: W / O (water-in-oil) emulsifier; 9: wetting and spreading agent; 15: detergent; 16: O / W (oil-in-water) emulsifier; 18: solubilizer or hydrotrope.

[0070] In some embodiments, the HLB values ​​for saccharide fatty acid esters (or composition comprising said ester), as described herein, may be in the lower range, in Petition 870260047896, dated 05 / 20 / 2026, p. 24 / 172 20 / 69 In other embodiments, the HLB values ​​for the saccharide fatty acid esters (or composition comprising said ester), as described herein, may be in the intermediate to upper range. In embodiments, a mixture of SFAEs with different HLB values ​​may be used.

[0071] As used herein, SEPOSE® means a sucrose fatty acid ester made from soybean (soybean) oil that is commercially available from Procter & Gamble Chemicals (Cincinnati, OH) under the trade name SEFOSE 161811 (see sucrose polysoyate below), containing one or more unsaturated fatty acids. As used herein, OLEAN® indicates a sucrose fatty acid ester that is available from Procter & Gamble Chemicals having the formula Cn+i2H2n+220i3, wherein all fatty acids are saturated. In addition, SFAEs may be purchased from Mitsubishi Chemicals Foods Corporation (Tokyo, JP), which supplies a variety of such SFAEs.

[0072] As used herein, soyate means a mixture of fatty acid salts of soybean oil.

[0073] As used herein, oilseed fatty acids means plant fatty acids, including but not limited to, soybeans, peanuts, rapeseed, barley, canola, sesame seeds, cottonseed, palm kernels, grape seeds, olives, safflower, sunflowers, copra, maize, coconuts, flaxseed, hazelnuts, wheat, rice, potatoes, cassava, legumes, camelina seeds, mustard seeds and combinations thereof.

[0074] As used herein, moisture resistance means the measure of how well the web of fibers that holds the paper together can resist a tearing force when the paper is wet. Moisture resistance can be measured using a Finch Moisture Resistance Device from Thwing-Albert Instrument Company (West Berlin, NJ). Where moisture resistance is typically performed by Petition 870260047896, dated 05 / 20 / 2026, page 25 / 172 21 / 69 moisture-resistant additives, such as kymene, cationic glyoxylated resins, polyamidoamine-epichlorohydrin resins, polyamine-epichlorohydrin resins, including epoxy resins. In embodiments, the cellulose-based material coated with SFAE, as described herein, affects moisture resistance in the absence of such additives.

[0075] As used here, humid means covered or saturated with water or mother liquor.

[0076] In embodiments, a process as described herein includes mixing a saccharide fatty acid ester with inorganic particles (e.g., clay, talc, calcium carbonate) and applying said mixture to a cellulosic material that may allow said particles to adhere to said cellulosic material, wherein said process comprises contacting a cellulose-based material with the combination and exposing the contacting cellulose-based material at the rate to radiation by heat, a catalyst, or a combination thereof for a time sufficient to bind the combination to the cellulose-based material. In a related aspect, such radiation may include, but is not limited to, UV, IR, visible light, or a combination thereof. In another related aspect, the reaction may be carried out at room temperature (i.e., 25°C) to about 150°C, about 50°C to about 100°C, or about 60°C to about 80°C.

[0077] Furthermore, the binding reaction between the mixture and the cellulosic material can be carried out with or without substantially reduced retention aids (i.e., binders such as PvOH or starch). In one aspect, the mixture may contain a mixture of mono-, di-, tritetra-, penta-, hexa-, hepta- or octaesters. In another aspect, it may also contain proteins, polysaccharides and lipids, including, but not limited to, milk proteins (e.g., Petition 870260047896, dated 05 / 20 / 2026, p. 26 / 172 22 / 69 casein, whey protein and similar products), wheat gluten, gelatins, prolamins (e.g., with zeins), soy protein isolates, starches, modified starches, acetylated polysaccharides, alginates, carrageenans, chitosans, inulins, long-chain fatty acids, waxes and combinations thereof.

[0078] In embodiments, cellulosic material can be made lipophobic by the addition of polyvinyl alcohol (PvOH) and / or prolamins. In one aspect, prolamins include zein, gifedin, hordein, secaite, catirin, and avenin; in a related aspect, the prolamin is zein.

[0079] In embodiments, no catalyst and no organic carrier (e.g., volatile organic compounds) are required to carry out the bonding reaction, including that no material buildup is contemplated using the method as described. In a related aspect, the reaction time is substantially instantaneous (i.e., less than 1 second). Furthermore, the resulting material exhibits low blocking.

[0080] As described herein, all fatty acid esters of all saccharides, including mono-, di-, and trisaccharides, are adaptable for use in connection with this aspect of the present invention. In a related aspect, the saccharide fatty acid ester may be a mono-, di-, tri-, tetra-, penta-, hexa-, hepta-, or octaester and combinations thereof, including that the fatty acid moieties may be saturated, unsaturated, or a combination thereof.

[0081] Although not limited by theory, the interaction between the saccharide fatty acid ester and the cellulose-based material can be by ionic, hydrophobic, van der Wards, or covalent bonding, or a combination thereof. In a related aspect, the binding of the saccharide fatty acid ester to Petition 870260047896, dated 05 / 20 / 2026, p. 27 / 172 23 / 69 cellulose-based material can be substantially irreversible (e.g., using an SFAF comprising a combination of saturated and unsaturated fatty acids).

[0082] Furthermore, at a sufficient concentration, the linkage of the saccharide fatty acid ester alone is sufficient to render the cellulose-based material hydrophobic, i.e., hydrophobicity is achieved in the absence of the addition of waxes, rosins, resins, dikelenes, shellac, vinyl acetates, PLA, PEI, oils, other water-repellent chemicals or combinations thereof (i.e., secondary hydrophobics), including such other properties as, inter alia, strengthening, hardening and volume increase of the cellulose-based material are obtained by linkage of saccharide fatty acid ester alone.

[0083] One advantage of the invention, as described, is that multiple fatty acid chains are reactive with cellulose and with the two saccharide molecules in the structure, for example, the sucrose fatty acid esters, as described, give rise to a rigid cross-linking network, leading to improved strength in fibrous webs such as paper, cardboard, air- and moisture-laid nonwovens and textiles, thus overcoming the potential undesirable effects of some fillers (e.g., calcium carbonates help to decrease bonding and tear resistance). This is not normally found in other sizing or hydrophobic treatment chemistries. The saccharide fatty acid esters, as described herein, also generate / increase moisture resistance, a property absent when using many other water-resistant chemicals.

[0084] Another advantage is that saccharide fatty acid esters, as described, soften the fibers, increasing the space between them and thus increasing the volume without increasing Petition 870260047896, dated 05 / 20 / 2026, page 28 / 172 24 / 69 substantially the weight. Furthermore, the modified fibers and cellulose-based material, as described herein, can be repulped. Additionally, for example, water cannot be easily pushed past the low surface energy barrier into the sheet.

[0085] Saturated SFAEs are typically solid at nominal processing temperatures, while unsaturated SFAEs are typically liquid. This allows for the formation of uniform and stable dispersions of saturated SFAE in aqueous coatings without significant interactions or incompatibilities with other coating components, which are typically hydrophilic. Furthermore, this dispersion allows high concentrations of saturated SFAE to be prepared without adversely affecting coal rheology, uniform coating application, or coating performance characteristics. The coating surface will become hydrophobic as the saturated SFAE particles melt and spread under heating, drying, and coating layer consolidation. In embodiments, a method is described for producing bulky fibrous structures that retain strength even when exposed to water.Generally, fibrous pulps that are dried form dense structures that are easily broken when exposed to water. Formed fiber products made using the method as described can include paper plates, beverage holders (e.g., cups), lids, food trays, and packaging that would be lightweight, strong, and resistant to exposure to water and other liquids.

[0086] In embodiments, saccharide fatty acid esters can be mixed with polyvinyl alcohol (PvOH) to produce bonding agents for water-resistant coatings. As described herein, a synergistic relationship between saccharide fatty acid esters and PvOH has been demonstrated, including that with inorganic mixtures, the amount of PvOH can be reduced. Although it is Petition 870260047896, dated 05 / 20 / 2026, page 29 / 172 25 / 69 It is known in the art that PvOH, by itself, is a good film former and forms strong hydrogen bonds with cellulose; however, it is not very resistant to water, particularly hot water. In one aspect, the use of PvOH helps to emulsify the saccharide fatty acid esters in an aqueous coating. In another aspect, PvOH provides a rich source of OH groups for saccharide fatty acid esters for crosslinking along the fibers, which increases the paper's strength, for example, particularly moisture resistance and water resistance, beyond what is possible with PvOH alone. For saturated saccharide fatty acid esters with free hydroxyls in the saccharide, a crosslinking agent such as a dialdehyde (e.g., glyoxal, glutaraldehyde, and the like) can also be used.

[0087] In embodiments, the fatty acid esters of saccharide comprise or consist essentially of sucrose esters of fatty acids. Many methods are known and available for preparing or otherwise providing the fatty acid esters of saccharide of the present invention, and all such methods are considered available for use within the broad scope of the present invention. For example, in certain embodiments, it may be preferred that the fatty acid esters be synthesized by esterification of a saccharide with one or more fatty acid moieties obtained from oilseeds, including, but not limited to, soybean oil, sunflower oil, olive oil, canola oil, peanut oil, and mixtures thereof.

[0088] In embodiments, saccharide fatty acid esters comprise a saccharide moiety, including, but not limited to, a sucrose moiety, which has been replaced by an ester moiety at one or more of its hydroxyl hydrogens. In a related aspect, disaccharide esters have the structure of Formula I. Petition 870260047896, dated 05 / 20 / 2026, page 30 / 172 26 / 69 Formula 1 where A is hydrogen, or Structure 1 below; Structure 1 — R where R is a linear, branched or cyclic, saturated or unsaturated, aliphatic or aromatic portion of about eight to about 40 carbon atoms, and where at least one A is in at least one, at least two, at least three, at least four, at least five, at least six, at least seven and all eight A portions of the Formula are in accordance with Structure 1. In a related aspect, the saccharide fatty acid esters, as described herein, may be mono-, di-, tri-, tetra-, penta-, hexa-, hepta- or octaesters and combinations thereof, wherein the aliphatic groups may all be saturated or may contain saturated and / or unsaturated groups or combinations thereof.

[0089] Suitable R groups include any form of aliphatic moiety, including those containing one or more substituents; the moiety may occur on any carbon in the moiety. Also included are aliphatic moieties that include functional groups within the moiety, for example, an ether, ester, thio, amino, phospho, or similar. Also included are aliphatic oligomer and polymer moieties, for example, sorbitan, polysorbitan, and polyalcohol moieties. Examples of functional groups that may be attached to the aliphatic (or aromatic) moiety comprising the R group include, but are not limited to, halogen, alkoxy, hydroxyl, functional groups. Petition 870260047896, dated 05 / 20 / 2026, p. 31 / 172 27 / 69 amino, ether, and ester. In one aspect, these portions may have crosslinking functionalities. In another aspect, SFAE may be crosslinked onto a surface (e.g., activated clay / pigment particles). In yet another aspect, the double bonds present in SFAE may be used to facilitate reactions on other surfaces.

[0090] Suitable disaccharides include raffinose, maltodextrose, galactose, sucrose, glucose combinations, fructose combinations, maltose, lactose, mannose combinations, erythrose combinations, isomaltose, isomaltulose, trehalose, trealulose, cellobiose, laminaribiose, chitobiose and combinations thereof.

[0091] In embodiments, the substrate for the addition of fatty acids may include starches, hemicelluloses, lignins, or combinations thereof.

[0092] In embodiments, a composition comprises a starch fatty acid ester, wherein the starch may be derived from any suitable source, such as dentate maize starch, waxy maize starch, potato starch, wheat starch, rice starch, sago starch, tapioca starch, sorghum starch, sweet potato starch and mixtures thereof.

[0093] In more detail, starch can be unmodified starch or starch that has been modified by a chemical, physical, or enzymatic modification.

[0094] Chemical modification includes any treatment of a starch with a chemical that results in a modified starch (e.g., plastarch material). Chemical modification includes, but is not limited to, depolymerization of a starch, oxidation of a starch, reduction of a starch, etherification of a starch, esterification of a starch, nitrification of a starch, defatting of a starch, hydrophobization of a starch, and the like. Chemically modified starches may also be Petition 870260047896, dated 05 / 20 / 2026, page 32 / 172 28 / 69 prepared using a combination of any of the chemical treatments. Examples of chemically modified starches include the reaction of alkenyl succinic anhydride, particularly octenyl succinic anhydride, with starch to produce a hydrophobic esterified starch; the reaction of 2,3-epoxypropyltrimethylammonium chloride with starch to produce a cationic starch; the reaction of ethylene oxide with starch to produce hydroxyethyl starch; the reaction of hypochlorite with starch to produce an oxidized starch; the reaction of an acid with starch to produce an acid depolymerized starch; defatting a starch with a solvent, such as methanol, ethanol, propanol, methylene chloride, chloroform, carbon tetrachloride and the like, to produce a defatted starch.

[0095] Physically modified starches are any starches that are physically treated in any way to provide physically modified starches. Physical modification includes, but is not limited to, heat treatment of starch in the presence of water, heat treatment of starch in the absence of water, fracturing of starch granules by any mechanical means, pressure treatment of starch to fuse starch granules, and the like. Physically modified starches may also be prepared using a combination of any of the physical treatments.Examples of physically modified starches include heat treatment of starch in an aqueous environment to cause the starch granules to swell without granule rupture; heat treatment of anhydrous starch granules to cause polymer rearrangement; fragmentation of starch granules by mechanical disintegration; and pressure treatment of starch granules by means of an extruder to cause the starch granules to melt.

[0096] Enzymatically modified starches are any starches that are enzymatically treated in any way to Petition 870260047896, dated 05 / 20 / 2026, page 33 / 172 29 / 69 provide enzymatically modified starches. Enzymatic modification includes, but is not limited to, the reaction of an alpha amylase with starch, the reaction of a protease with starch, the reaction of a lipase with starch, the reaction of a phosphorylase with starch, the reaction of an oxidase with starch, and the like. Enzymatically modified starches can be prepared using a combination of any of the enzymatic treatments.Examples of enzymatic modification of starch include the reaction of the alpha-amylase enzyme with starch to produce a depolymerized starch; the reaction of the alpha-amylase debranching enzyme with starch to produce a debranched starch; the reaction of a protease enzyme with starch to produce a starch with reduced protein content; the reaction of a lipase enzyme with starch to produce a starch with reduced lipid content; the reaction of a phosphorylase enzyme with starch to produce an enzyme-modified phosphate starch; and the reaction of an oxidase enzyme with starch to produce an enzyme-oxidized starch.

[0097] Disaccharide fatty acid esters may be sucrose fatty acid esters according to Formula 1, wherein the R groups are aliphatic and are linear or branched, saturated or unsaturated, and have between about 8 and about 40 carbon atoms.

[0098] As used herein, the terms saccharide fatty acid esters and sucrose fatty acid ester include compositions having different degrees of purity as well as mixtures of compounds of any purity level. For example, the saccharide fatty acid ester compound may be a substantially pure material, that is, it may comprise a compound with a given number of A groups titrated by only one kind of Structure I portion (i.e., all R groups are Petition 870260047896, dated 05 / 20 / 2026, p. 34 / 172 30 / 69 equal and all sucrose moieties are substituted to the same degree). Also included is a composition comprising a mixture of two or more saccharide fatty acid ester compounds, which differ in their degrees of substitution, but in which all substituents have the same R-group structure. Also included are compositions that are a mixture of compounds with different degrees of substitution of the A-group, and in which the substituent moieties of the R-group are independently selected from two or more R-groups of Structure I. In a related aspect, the R-groups may be the same or different, including that said saccharide fatty acid esters in a composition may be the same or different (i.e., a mixture of different saccharide fatty acid esters).

[0099] For compositions of the present invention, the composition may comprise saccharide fatty acid ester compounds with a high degree of substitution. In embodiments, the saccharide fatty acid ester is a sucrose polysoyate.

[00100] A sucrose polysoyate (SEFOSE® 1618U)

[00101] Fatty acid saccharide esters can be made by esterification with substantially pure fatty acids by known esterification processes. They can also be prepared by transesterification using fatty acid and saccharide esters in the form of fatty acid glyceride derivatives, for example, from natural sources, for example, those found in oil extracted from oilseeds, for example, soybean oil. The reactions of Petition 870260047896, dated 05 / 20 / 2026, p. 35 / 172 31 / 69 Transesterifications that provide fatty acid esters of sucrose using fatty acid glycerides are described, for example, in U.S. Patents Nos. 3,963,699; 4,517,360; 4,518,772; 4,611,055; 5,767,257; 6,504,003; 6,121,440; and 6,995,232 and WO1992004361 A1, which are incorporated herein by reference in their entirety.

[00102] In addition to preparing hydrophobic sucrose esters by transesterification, similar hydrophobic properties can be obtained in fibrous cellulosic articles by the direct reaction of acid chlorides with polyols containing ring structures analogous to sucrose.

[00103] As mentioned above, sucrose fatty acid esters can be prepared by transesterification of sucrose from methyl ester feedstocks that have been prepared from glycerides derived from natural sources (see, for example, 6,995,232, incorporated herein by reference in its entirety). As a consequence of the source of the complete acids, the feedstock used to prepare the sucrose fatty acid ester contains a range of saturated and unsaturated fatty acid methyl esters having fatty acid moieties containing between 12 and 40 carbon atoms.This will be reflected in the sucrose fatty acid esters of the product made from such a source, wherein the sucrose moieties comprising the product will contain a mixture of ester moiety substituents, in which, with reference to Structure I above, the R groups will be a mixture having between 12 and 26 carbon atoms with a ratio reflecting the raw material used to prepare the sucrose ester. Furthermore, to illustrate this point, sucrose esters derived from soybean oil will be a mixture of species, having R group structures that reflect that soybean oil comprises 26% by weight of oleic acid triglycerides (HhC-CHL·^). Petition 870260047896, dated 05 / 20 / 2026, p. 36 / 172 32 / 69 -CH = CH-[CH2]7-C(O)OH), 49 wt% of linoleic acid triglycerides (H3C4CH2H-CH2H-CH2-CH = CH]2-[-CH2-]2-C(O)OH), 11 wt% of linolenic acid triglycerides (H3C4-CH2-CH = CH-]3-[CH2 -]?-C(O)OH), and 14 wt% of triglycerides of various saturated fatty acids, as described in the Seventh Edition of the Merck Index, which is incorporated herein by reference. All these fatty acid moieties are represented in the R groups of the substituents in the sucrose fatty acid ester product. Consequently, when referring to a sucrose fatty acid ester here as the product of a reaction employing a fatty acid feedstock derived from a natural source, for example, soybean and sucrose, the term is intended to include all the various constituents that are typically found as a consequence of the source from which the sucrose fatty acid ester is prepared.In a related aspect, sucrose fatty acid esters, as described, can exhibit low viscosity (e.g., between about 10 and 2,000 centipoise at room temperature or under standard atmospheric pressure). In another aspect, unsaturated fatty acids can have one, two, three, or more double bonds.

[00104] In embodiments of the present invention, the saccharide fatty acid ester, and in some respects the disaccharide ester, is formed from fatty acids with more than about 6 carbon atoms, from about 8 to 16 carbon atoms, from about 8 to about 18 carbon atoms, from about 14 to about 18 carbon atoms, from about 16 to about 18 carbon atoms, from about 16 to about 20 carbon atoms, and from about 20 to about 40 carbon atoms, on average.

[00105] In embodiments, the saccharide fatty acid ester may be present in different concentrations to achieve hydrophobicity / lipophoscicity depending on the form of the material with Petition 870260047896, dated 05 / 20 / 2026, p. 37 / 172 33 / 69 based on cellulose. In one aspect, when a saccharide fatty acid ester (SFAE) is attached as a coating onto the cellulose-based material, the SFAE is present in a coating weight of at least about 0.1 g / m2 to about 1.0 g / m2, about 1.0 g / m2 to about 2.0 g / m2, about 2 g / m2 to about 3 g / m2 on a surface of the cellulose-based material. In a related aspect, it may be present from about 3 g / m2 to about 4 g / m2, about 4 g / m2 to about 5 g / m2, about 5 g / m2 to about 10 g / m2, about 10 g / m2 to about 20 g / m2. In another aspect, when the cellulose-based material is a solution containing cellulose fiber, SFAB is present at a concentration of at least about 0.025% (w / w) of the total fiber present.In a related aspect, it may be present at about 0.05% (w / w) to about 0.1% (w / w), about 0.1% (w / w) to about 0.5% (w / w), about 0.5% (w / w) to about 1.0% (w / w), about 1.0% (w / w) to about 2.0% (w / w), about 2.0% (w / w) to about 3.0% (w / w), about 3.0% (w / w) to about 4.0% (w / w), about 4.0% (w / w) to about 5.0% (w / w), about 5.0% (w / w) to about 10% (weight / weight), approx. 10% (weight / weight) to approximately 50% (weight / weight) of the total fiber present. In another related aspect, the amount of SFAE may be equal to the amount of fiber present. In some embodiments, SFAE may coat the entire outer surface of a cellulose-based material (e.g., coating an entire piece of paper or article containing cellulose).

[00106] In other embodiments, a coating may comprise between about 0.9% to about 1.0%, about 1.0% to about 5.0%, about 5.0% to about 10%, about 10% to about 20%, about 20% to about 30%, about 40% to about 50% of Petition 870260047896, dated 05 / 20 / 2026, p. 38 / 172 34 / 69 fatty acid ester of saccharide by weight of the coating (weight / weight). In a related aspect, the coating may contain between about 25% and about 35% of fatty acid ester of saccharide by weight of the coating (weight / weight).

[00107] In embodiments, cellulose-based material includes, but is not limited to, paper, cardboard, paper sheets, paper pulp, cups, boxes, trays, lids, removable papers / liners, compostable bags, shopping bags, shipping bags, bacon trays, tea bags, insulating material, coffee or tea containers, water pipes and conduits, food-grade disposable cutlery, plates and bottles, TV and mobile device screens, clothing (e.g., cotton or cotton blends), bandages, pressure-sensitive labels, pressure-sensitive adhesive tape, feminine products, and medical devices for use on or within the body, such as contraceptives, drug delivery devices, containers for pharmaceutical materials (e.g., pills, tablets, suppositories, gels, etc.) and the like.Furthermore, the coating technology, as described, can be used in furniture and upholstery, outdoor camping equipment, and similar items.

[00108] In one aspect, the coatings as described herein are pH resistant in the range of about 3 to about 9. In a related aspect, the pH may be about 3 to about 4, about 4 to about 5, about 5 to about 7, about 7 to about 9.

[00109] In embodiments, an alkanoic acid derivative is mixed with a saccharide fatty acid ester to form an emulsion, where the emulsion is used to treat cellulose-based material.

[00110] In embodiments, the saccharide fatty acid ester may be an emulsifying agent and may comprise a mixture of a Petition 870260047896, dated 05 / 20 / 2026, p. 39 / 172 35 / 69 or more mono-, di-, tri-, tetra-, penta-, hexa-, hepta- or octaesters. In another aspect, the fatty acid portion of the saccharide fatty acid ester may contain saturated groups, unsaturated groups, or a combination thereof. In one aspect, the emulsion containing saccharide fatty acid ester may contain proteins, polysaccharides and / or lipids, including, but not limited to, milk proteins (e.g., casein, whey protein and the like), wheat gluten, gelatins, prolamins (e.g., corn zein), soy protein isolates, starches, acetylated polysaccharides, alginates, carrageenans, chitosans, inulins, long-chain fatty acids, waxes and combinations thereof.

[00111] In embodiments, the saccharide fatty acid ester, as described herein, may be used in coatings with other chemicals used in papermaking, including, but not limited to, agallite, esters, diesters, ethers, ketones, amides, nitriles, aromatics (e.g., xylenes, toluenes), acid halides, anhydrides, alkyl ketone dimer (AKD), alabaster, alganic acid, alum, albrine, glues, barium carbonate, barium sulfate, chlorine dioxide, dolomite, diethylenetriamine pentaacetate, EDTA, enzymes, sulfuric formamidine acid, guar gum, gypsum, lime, magnesium bisulfate, milk of lime, milk of magnesia, polyvinyl alcohol (PvOH), rosin, rosin soaps, satins, soaps / fatty acids, Sodium bisulfate, sodium carbonate, titanium, surfactants, starches, modified starches, hydrocarbon resins, polymers, waxes, polysaccharides, proteins, latex and combinations thereof.In embodiments, the mixture, as described, may contain one or more SFAEs and one or more of the following inorganic particles: clay (kaolin, bentonite), calcium carbonate (both GGC and PCC), talc (magnesium silicate), and titanium dioxide. In a related aspect, the inorganic particles may... Petition 870260047896, dated 05 / 20 / 2026, p. 40 / 172 36 / 69 being present in concentrations ranging from about 1% to about 2%, about 2% to about 5%, about 5% to about 10%, about 10% to about 20%, about 20% to about 30%, about 30% to about 40%, about 40% to about 50%, about 50% to about 60%, or about 60% to about 70% in a coating composition. In another related aspect, SFAEs may be present in an equal, greater, or lesser ratio compared to the amounts of inorganic particles in a coating. In one aspect, coatings containing one or more SFAEs comprise all saturated fatty acids.

[00112] In embodiments, the cellulose-containing material generated by the methods described herein exhibits greater hydrophobicity or resistance to water compared to the untreated water-containing material. In a related aspect, the treated cellulose-containing material exhibits greater lipophobicity or resistance to grease compared to the untreated cellulose-containing material. In another related aspect, the treated cellulose-containing material may be biodegradable, compostable, and / or recyclable. In one aspect, the treated cellulose-containing material is hydrophobic (water-resistant) and lipophobic (grease-resistant).

[00113] In embodiments, the treated cellulose-containing material may have improved mechanical properties compared to the same untreated material. For example, paper bags treated by the process as described herein show increased tear strength, Gurley number, tensile strength, and / or maximum load energy. In one aspect, tear strength is increased by a factor of between about 0.5 to 1.0 times, between about 1.0 to 1.1 times, between about 1.1 to 1.3 times, between about 1.3 to 1.5 times. In another aspect, the Gurley Number increased by a factor of between about 3 to 4 times, between about 4 to 5 times, between about 5 to 6 times. Petition 870260047896, dated 05 / 20 / 2026, p. 41 / 172 37 / 69 and approximately 6 to 7 times. In yet another aspect, the tensile stress increased by a factor of approximately 0.5 to 1.0 times, approximately 1.0 to 1.1 times, approximately 1.1 to 1.2 times, and approximately 1.2 to 1.3 times. And in another aspect, the maximum load energy increased by a factor of approximately 1.0 to 1.1 times, approximately 1.1 to 1.2 times, approximately 1.2 to 1.3 times, and approximately 1.3 to 1.4 times.

[00114] In embodiments, the cellulose-containing material is a base paper comprising microfibrillated cellulose (MFC) or cellulose nanofiber (CNF), as described, for example, in U.S. Publication No. 2015 / 0167243 (incorporated herein by reference in its entirety), wherein the MFC or CNF is added during the paper forming and manufacturing process and / or added as a coating or a secondary layer to a previous forming layer to decrease the porosity of said base paper.In a related aspect, the base paper is contacted with the saccharide fatty acid ester as described above. In another related aspect, the contacted base paper is also contacted with a polyvinyl alcohol (PvOH). In embodiments, the resulting contacted base paper is tunably water and lipid resistant. In a related aspect, the resulting base paper may exhibit a Gurley value of at least about 10 to 15 (i.e., Gurley Air Resistance (sec / 100 cc, 20 oz. cyl.)), or at least about 100, at least about 200 to about 350. In one aspect, the saccharide fatty acid ester coating may be a laminate for one or more layers or may provide one or more layers as a laminate or may reduce the amount of coating to one or more layers to achieve the same performance effect (e.g., water resistance, grease resistance and the like).In a related aspect, the laminate may comprise a thermal seal or biodegradable and / or compostable adhesive. Petition 870260047896, dated 05 / 20 / 2026, p. 42 / 172 38 / 69

[00115] In embodiments, saccharide fatty acid esters can be formulated as emulsions, where the emulsifying agent of choice and the amount employed are dictated by the nature of the composition and the agent's ability to facilitate the dispersion of the saccharide fatty acid ester. In one aspect, emulsifying agents may include, but are not limited to, water, buffers, polyvinyl alcohol (PvOH), carboxymethylcellulose (CMC), latex, milk proteins, wheat gluten, gelatins, prolamins, soy protein isolates, starches, acetylated polysaccharides, alginates, carrageenans, chitosans, inulins, long-chain fatty acids, waxes, agar, alginates, glycerol, gums, lecithins, poloxamers, mono-, diglycerols, monosodium phosphates, monostearate, propylene glycols, detergents, cetyl alcohol, and combinations thereof.In another aspect, the ratios of the saccharide ester emulsifying agent can be about 0.1:99.9, about 1:99, about 10:90, about 20:80, about 35:65, about 40:60, and about 50:50. It will be evident to one skilled in the art that the ratios may vary depending on the desired property(ies) of the final product.

[00116] In embodiments, saccharide fatty acid esters may be combined with one or more coating components for internal and surface sizing (alone or in combination), including, but not limited to, binders (e.g., starch, soy protein, polymer emulsions, PvOH, latex) and additives (e.g., glyoxal, glyoxalated resins, zirconium salts, calcium stearate, lecithin oleate, polyethylene emulsion, carboxymethylcellulose, acrylic polymers, alginates, polyacrylate gums, polyacrylates, microbiocides, oil-based defoamers, silicone, stilbenes, direct colorants and additive colorants). In a related aspect, such components may provide a or Petition 870260047896, dated 05 / 20 / 2026, page 43 / 172 39 / 69 more properties, including, but not limited to, building a fine porous structure, providing a light-dispersing surface, improving ink receptivity, improving gloss, binding pigment particles, binding coatings to paper, reinforcing the base sheet, filling pores in the pigment structure, reducing water sensitivity, resisting moisture in offset printing, preventing blade scratches, improving gloss in supercalendering, reducing dust, adjusting coating viscosity, providing water retention, dispersing pigments, maintaining coating dispersion, preventing coating / coating color deterioration, controlling foam formation, reducing trapped air and coating craters, increasing whiteness and gloss, and controlling color and shadow. It will be evident to anyone skilled in the art that the combinations can be varied depending on the desired property(ies) for the final product.

[00117] In embodiments, methods employing said saccharide fatty acid esters can be used to increase the cost of primary / secondary coating applications (e.g., silicone-based layer, starch-based layer, clay-based layer, PLA layer, Bio-PBS, PEI layer, and the like) by providing a material layer exhibiting a required property (e.g., water resistance, low surface energy, and the like), thereby reducing the amount of primary / secondary layer needed to achieve that same property. In one aspect, the materials can be coated on top of an SFAE layer (e.g., sealable curing agents). In embodiments, the composition is fluorocarbon-free and silicone-free.

[00118] In modalities, the compositions increase the mechanical and thermal stability of the treated product, in one aspect, the treatment Petition 870260047896, dated 05 / 20 / 2026, p. 44 / 172 The 40 / 69 surface is thermostable at temperatures between approximately ~100°C and approximately 300°C. In another related aspect, the surface of the cellulose-based material exhibits a contact angle with water between approximately 60° and approximately 120°. Furthermore, the surface treatment is chemically stable at temperatures between approximately 200°C and approximately 300°C.

[00119] The substrate, which can be dried before application (e.g., at about 8 to 150 °C), can be treated by modifying the composition by immersion, for example, and allowing the surface to be exposed to the composition for less than 1 second. The substrate can be heated to dry the surface, after which the modified material is ready for use. In one aspect, according to the method as described herein, the substrate can be treated by any suitable coating / sizing process typically carried out in a paper mill (see, for example, Smook, G., Surface Treatments in Handbook for Pulp & Paper Technologists, (2016), 4th Ed., Chapter 18, pp 293-309, TAPPI Press, Peachtree Corners, GA USA, incorporated herein by reference in its entirety).

[00120] No special preparation of the material is required in the practice of this invention, although for some applications, the material may be dried before treatment. In embodiments, the methods as described can be used on any cellulose-based surface, including, but not limited to, a film, a rigid container, fibers, pulp, a fabric or the like. In one aspect, the saccharide fatty acid esters or coating agents can be applied by conventional sizing press (vertical, inclined, horizontal), drawer roll sizing press, measuring sizing press, calender sizing application, tube sizing, in-machine, off-machine, one-sided coater, double-sided applicator, short Petition 870260047896, dated 05 / 20 / 2026, page 45 / 172 41 / 69 duration, simultaneous double-sided applicator, blade or rod coater, gravure coater, gravure printing, flexographic printing, inkjet printing, laser printing, supercalendering and combinations thereof.

[00121] Depending on the source, cellulose can be paper, cardboard, pulp, softwood fiber, hardwood fiber or combinations thereof, nanocellulose, cellulose nanofibers, whiskers or microfibrils, microfibrillated, cotton or cotton blends, other non-wood fibers (such as sisal, jute or hemp, flax and straw), cellulose nanocrystals or nanofibrillated cellulose.

[00122] In embodiments, the amount of saccharide fatty acid ester coating applied is sufficient to completely cover at least one surface of a cellulose-containing material. For example, in embodiments, the saccharide fatty acid ester coating may be applied to the entire outer surface of a container, the entire inner surface of a container, or a combination thereof, or one or both sides of a base paper. In other embodiments, the entire upper surface of a film may be covered by the saccharide fatty acid ester coating, or the entire lower surface of a film may be covered by the saccharide fatty acid ester coating, or a combination thereof.In some embodiments, the lumen of a device / instrument may be covered by the coating, or the external surface of the device / instrument may be covered by the saccharide fatty acid ester coating, or a combination thereof. In this embodiment, the amount of saccharide fatty acid ester coating applied is sufficient to partially cover at least one surface of a cellulose-containing material. For example, only surfaces exposed to the ambient atmosphere are covered. Petition 870260047896, dated 05 / 20 / 2026, p. 46 / 172 42 / 69 saccharide fatty acid ester coating, or only those surfaces that are not exposed to the ambient atmosphere are covered by the saccharide fatty acid ester coating (e.g., masking). As will be evident to one skilled in the art, the amount of saccharide fatty acid ester coating applied may be dependent on the use of the material to be coated. In one aspect, one surface may be coated with a saccharide fatty acid ester and the opposite surface may be coated with an agent including, but not limited to, proteins, wheat gluten, gelatins, prolamins, soy protein isolates, starches, modified starches, acetylated polysaccharides, alginates, carrageenans, chitosans, inulins, long-chain fatty acids, waxes, and combinations thereof. In a related aspect, SFAE may be added to a supply and the resulting web material may be provided with an additional SFAE coating.

[00123] Any suitable coating process may be used to release any of the various saccharide fatty acid ester coatings and / or emulsions applied in the course of practicing this aspect of the method. In embodiments, saccharide fatty acid ester coating processes include dipping, spraying, painting, printing, and any combination of any of these processes, alone or with other coating processes adapted to practice the methods as described.

[00124] Increasing the concentration of saccharide fatty acid ester, for example, the composition, as described here, can react more extensively with the cellulose being treated, with the net result again exhibiting water-repellent / lipid-resistant characteristics. However, higher layer weights do not necessarily translate into greater water resistance. In one aspect, various catalysts can Petition 870260047896, dated 05 / 20 / 2026, page 47 / 172 43 / 69 allows for faster curing by precisely adjusting the amount of saccharide fatty acid ester to meet specific applications.

[00125] It will be evident to anyone skilled in the art that the selection of the cellulose to be treated, the saccharide fatty acid ester, the reaction temperature and the exposure time are process parameters that can be optimized by routine experimentation to suit any particular application for the final product.

[00126] Derivatized materials have altered physical properties that can be defined and measured using appropriate tests known in the art. For hydrophobicity, the analytical protocol may include, but is not limited to, measurement of the contact angle and moisture uptake. Other properties include stiffness, WVTR, porosity, tensile strength, lack of substrate degradation, rupture and tear properties. A specific standardized protocol is defined by the American Society for Testing and Materials (ASTM protocol D7334-08).

[00127] The permeability of a surface to various gases, such as water vapor and oxygen, can also be altered by the saccharide fatty acid ester coating process as the barrier function of the material is increased. The standard unit of measurement for permeability is the Barrer and protocols for measuring these parameters are also available in the public domain (ASTM std F2476-05 for water vapor and ASTM std F2622-8 for oxygen).

[00128] In embodiments, the materials treated according to the procedure described herein exhibit complete biodegradability as measured by degradation in the environment under attack by microorganisms.

[00129] Several methods are available for defining and testing the Petition 870260047896, dated 05 / 20 / 2026, p. 48 / 172 44 / 69 biodegradability, including the shaken bottle method (ASTM E1279 - 89 (2008)) and the Zahn-Wellens test (OECD TG 302 B).

[00130] Several methods are available for defining and testing compostability, including, but not limited to, ASTM D6400.

[00131] Suitable materials for treatment by the process of this invention include various forms of cellulose, such as cotton fibers, vegetable fibers such as flax, wood fibers, regenerated cellulose (rayon and cellophane), partially alkylated cellulose (cellulose ethers), partially esterified cellulose (acetate rayon), and other modified cellulose materials that have a substantial portion of their surfaces available for reaction / bonding. As stated above, the term cellulose includes all these materials and others of similar polysaccharide structure and with similar properties. Among these, the relatively new microfibrillated cellulose material (cellulose nanofiber) (see, for example, U.S. Patent 374,702 and U.S. Publications Nos. 2015 / 0167243 and 2009 / 0221812, incorporated herein by reference in their entirety) is particularly suitable for this application.In other embodiments, celluloses may include, but are not limited to, cellulose triacetate, cellulose propionate, cellulose acetate propionate, cellulose acetate butyrate, nitrocellulose (cellulose nitrate), cellulose sulfate, celluloid, methylcellulose, ethylcellulose, ethylmethylcellulose, hydroxyethylcellulose, hydroxypropyl cellulose, cellulose nanocrystals, hydroxyethylmethylcellulose, hydroxypropylmethylcellulose, ethyl hydroxyethylcellulose, carboxymethylcellulose, and combinations thereof.

[00132] The modification of cellulose, as described herein, in addition to increasing its hydrophobicity, can also increase its tensile strength, flexibility, and rigidity, thus broadening its range of uses. All biodegradable and partially biodegradable products made from or using the modified cellulose described in this application fall within the scope of Petition 870260047896, dated 05 / 20 / 2026, page 49 / 172 45 / 69 scope of the invention, including recyclable and compostable products.

[00133] Among the possible applications of coating technology, such items include, but are not limited to, all-purpose containers such as paper, cardboard, paper pulp, cups, lids, boxes, trays, removable papers / liners, compostable bags, shopping bags, water pipes and conduits, disposable food-grade cutlery, plates and bottles, TV and mobile device screens, clothing (e.g., cotton or cotton blends), bandages, pressure-sensitive labels, pressure-sensitive adhesive tape, feminine products, and medical devices to be used on or within the body, such as contraceptives, drug delivery devices, and the like. Furthermore, coating technology as described can be used in furniture and upholstery, outdoor camping equipment, and the like.

[00134] The following examples are intended to illustrate, but not to limit, the invention. EXAMPLES Example 1. Fatty acid saccharide ester formulations

[00135] SBPOSE® is a liquid at room temperature and all coatings / emulsions containing this material were applied at room temperature using a benchtop rebate device. The rod type and size were varied to create a range of coating weights. Formulation 1

[00136] 50 ml of SEFOSE® were added to a solution containing 195 ml of water and 5 grams of carboxymethylcellulose (FINNFIX® 10; CP Kelco, Atlanta, GA). This formulation was mixed using a Silverson homogenizer set to 5000 rpm for 1 minute. This emulsion was coated onto a 50-gram base sheet. Petition 870260047896, dated 05 / 20 / 2026, page 50 / 172 46 / 69 made of bleached hardwood pulp and an 80-gram sheet composed of unbleached softwood. Both papers were placed in an oven (105 °C) for 15 minutes to dry. After removal from the oven, the sheets were placed on the laboratory bench and 10 drops of water (room temperature) were applied via pipette to each sheet. The base sheets selected for this test would absorb one drop of water immediately, while the sheets coated with varying amounts of SEFOSE® showed increasing levels of water resistance as the weight of the coating increased (see Table 1). Table 1. Baseline Data Sheet Results with SEFOSB® Coating weight g / m2 50 gr. Hardwood base water resistance (minutes) Solid wood base resistance (minutes) 3.2 1 0.5 4.1 14 9 6.4 30 25 8.5 50 40 9.2 100+ 100+ [I0137] It was observed that water resistance was lower in the heavier leaf, and no water resistance was obtained unless the leaf was dry. Formulation 2

[00138] Addition of SEPOSE® to cup raw material: (note that this is a single-layer raw material without treatment with 110 grams of MFC sheet made from eucalyptus cellulose). 50 grams of SEPOSE® were added to 200 grams of 5% cooked ethyl starch (Ethylex 2025) and stirred using a benchtop Kady mill for 30 seconds. Paper samples were coated and Petition 870260047896, dated 05 / 20 / 2026, page 51 / 172 47 / 69 were placed in an oven at 105 °C for 15 minutes. In test 10-15, droplets were placed on the coated side of the container and the water retention time was measured and recorded in the table below. Water penetration into the untreated leaf control was instantaneous (see Table 2). Table 2. Hot water penetration into SEFOSE® treated cup stock. Amount applied Time required for heat (80°C) water to penetrate 2.3 0.05 hr 4.1 0.5 hr 6.2 1.2 hr 8.3 3.5 hr 9.6 ~ 16 hr Formulation 3

[00139] Pure SEFOSE® was heated to 45°C and placed in a spray bottle. A uniform spray was applied to the paper raw material listed in the previous example, as well as to a piece of fiber sheet and a quantity of cotton fabric. When the water droplets were placed on the samples, penetration into the substrate occurred within 30 seconds, however after drying in an oven for 15 minutes at 105°C, the water droplets evaporated before being absorbed by the substrate.

[00140] Ongoing research concerns whether SEFOSE® is compatible with compounds used for oil and grease resistant coatings. SEFOSE® is useful for water resistance as well as stiffness improvements; 240-gram cardboard was used to perform stiffness tests. Table 3 shows the results. These data were obtained with a single layer weight: 5 grams / square meter with an average of 5 samples being reported. The results are in Taber stiffness units recorded with our Petition 870260047896, dated 05 / 20 / 2026, page 52 / 172 48 / 69 Taber / -5 Rigidity Tester Model 150-E. Table 3. Stiffness Test Sample tested | Machine direction stiffness | Cross direction stiffness | Control cardboard - uncoated | 77.6 | 51.8 | Sefose® | 85.9 | 57.6 | Erucic acid | 57.9 | 47.4 | Palmitoyl chloride | 47.7 Example 2. Saccharide ester binding to the cellulosic substrate

[00141] In an effort to determine if SEFOSE® was reversibly bound to a cellulosic material, pure SEFOSE® was mixed with pure cellulose in a 50:50 ratio. The SEFOSEs were read for 15 min at 300°F and the mixture was extracted with methylene chloride (non-polar solvent) or distilled water. The samples were refluxed for 6 hours, and gravimetric analysis of the samples was performed. Table 4. Extraction of SEFOSE® from Cellulosic Material Sample Total Mass Sefose® Extracted % of Sefose® Retained CH2CI2 2.85 1.42 0.25 83% H2O 2.28 1.14 0.08 93% Example 3. Examination of cellulosic surfaces

[00142] Scanning electron microscope images of base papers with and without MFC illustrate how a less porous base has the potential to require far fewer waterproofing agents reacting to the surface. FIGS. 1-2 show untreated Whatman filter paper of medium porosity. FIGS. 1 and 2 show the area of Petition 870260047896, dated 05 / 20 / 2026, p. 53 / 172 49 / 69 relatively high surface area exposed for a derivatizing agent to react, however, also shows a highly porous sheet with plenty of space for water to escape. FIGS. 3 and 4 show a side-by-side comparison of paper made with recycled pulp before and after MFC coating. (These are two magnifications of the same samples, without MFC obviously on the left side of the image). The test shows that derivatizing a much less porous sheet shows more promise for long-term water / vapor barrier performance. The last two images are just close-ups taken of a pore average on a filter paper sheet, as well as a similar magnification of CNF-coated paper for contrast purposes.

[00143] The data above demonstrate a critical point: that the addition of more material results in a corresponding increase in performance. Although not limited by theory, the reaction appears to be faster with unbleached papers, suggesting that the presence of lignin may accelerate the reaction.

[00144] The fact that a product like SEFOSE® is a liquid means it can easily emulsify, suggesting that it can be easily adapted to work in coating equipment commonly used in paper mills. Example 4. Phluphi

[00145] Liquid SEFOSE® was mixed and reacted with bleached wood fiber to generate a variety of ways to create a waterproof paper layer. When sucrose ester was mixed with the pulp before sheet formation, it was found that most of it is retained with the fiber. With sufficient heating and drying, a brittle, fluffy, yet highly hydrophobic paper layer was formed. In this example, 0.25 grams of SEFOSE® were mixed with 4.0 grams of bleached hardwood fiber in Petition 870260047896, dated 05 / 20 / 2026, page 54 / 172 50 / 69 liters of water. This mixture was stirred by hand and the water drained into a standard sheet mold. The resulting fiber mat was removed and dried for 15 minutes at 325°F. The finished fabric produced exhibited significant hydrophobicity as well as considerably reduced hydrogen bonding between the fibers themselves. (The angle of contact with water was observed to be greater than 100 degrees). An emulsifier can be added. SEFOSE® for fiber can be from approximately 1:100 to 2:1.

[00146] Subsequent tests show that talc is only a bystander and was left out of further testing. Example 5. Environmental Effects on the Properties of the SEFOSE® Coating

[00147] In an effort to better understand the reaction mechanism of sucrose esters with fiber, low viscosity coatings were applied to a bleached kraft sheet that had added moisture-resistant resin but no water resistance (no location). The coatings were all below 250 cps, as measured using a Brookfield viscometer at 100 rpm.

[00148] SEFOSE® was emulsified with Ethylex 2025 (starch) and applied to paper using an gravure roller. For comparison, SEFOSE® was also emulsified with PvOH Weslcote 9050. As shown in FIG. 5, the oxidation of double bonds in SEFOSE® is increased by the presence of heat and additional chemical environments that enhance oxidative chemistry (see also Table 5). Table 5. Environmental Effects of SEFOSE® (Minutes to Failure) Time PVOH -PVOH Ethylex 3:1 0 0.08 0.07 0.15 2 1 0.083 0.11 0.15 1.8 2 0.08 0.18 0.13 1.8 5 0.09 0.25 0.1 1.3 Petition 870260047896, dated 05 / 20 / 2026, page 55 / 172 51 / 69 10 0.08 0.4 0.1 0.9 30 0.08 1.1 0.08 0.8 60 0.08 3.8 0.08 0.8 120 0.08 8 0.08 0.7 500 0.07 17 0.07 0.4 Example 6. Effect of unsaturated fatty acid chains vs saturated SEFOSE® was reacted with bleached softwood pulp and dried to form a sheet. Subsequently, extractions were performed with CH2Cl2, toluene, and water to determine the extent of the reaction with the pulp. The extractions were carried out for at least 10 hours using Soxhlet extraction glassware. The results of the extractions are shown in Table 6. Water CH2CI2 Toluene Dry pulp mass 8.772g 9.237g 8.090g Sephose © added 0.85g 0.965g 0.798g Amount extracted 0.007g 0.015g 0.020g

[0149] The data indicate that essentially all of the SEFOSE® remains in the leaf. To also verify this, the same procedure was performed on the pulp alone, and the results show that approximately 0.01 g per 10 g of pulp was obtained. Although not linked by theory, this could easily be accounted for as residual pulping chemicals or, more likely, extractives that were not completely removed.

[00150] Pure cellulose fibers (e.g., α-cellulose from Sigma Aldrich, St. Louis, MO) were used and the experiment was repeated. While the SEFOSE® loading levels remained below approximately 20% of the fiber mass, more than 95% of the SEFOSE® mass was retained with the fibers and could not be extracted with polar or nonpolar solvents. Although not limited by Petition 870260047896, dated 05 / 20 / 2026, page 56 / 172 52 / 69 theory, optimizing cooking time and temperature also increases the sucrose esters that remain with the fibers.

[00151] As shown, the data demonstrate a general inability to extract SEFOSE® from the material after drying. On the other hand, when fatty acids containing all saturated fatty acid chains are used instead of SEFOSE® (e.g., OLEAN®, available from Procter & Gamble Chemicals (Cincinnati, OH)), almost 100% of the material can be extracted with hot water (at or above 70°C). CLEAN® is identical to SEFOSE® with the only change being linked saturated fatty acids (CLEAN®) instead of unsaturated fatty acids (SEFOSE®).

[00152] Another notable aspect is that multiple My acid chains are reactive with cellulose, and with the two saccharide molecules in the structure, SEFOSE® gives rise to a rigid cross-linking network leading to improved strength in fibrous webs, such as paper, cardboard, air and moisture-settling nonwovens and textiles. Example 7. SEFOSE® Additions to Achieve Water Resistance

[00153] 2- and 3-gram hand-rolled sheets were made using hardwood and softwood kraft pulp. When SEFOSE® was added to the 1% pulp at a level of 0.1% or more and the water was drained out forming the paper sheet, the SEFOSE® was retained with the fibers, where it imparted water resistance. From 0.1% to 0.4% SEFOSE®, water dripped onto the surface for a few seconds or less. After SEFOSE® loading increased to 0.4%, the water resistance time rapidly increased to minutes and then to hours for loading levels above 1.5%. Example 8. Production of bulky fibrous material

[00154] The addition of SEFOSE® to the pulp acts to soften the fibers, increase the space between them, thus increasing the volume. For example, Petition 870260047896, dated 05 / 20 / 2026, page 57 / 172 53 / 69 A 3% hardwood pulp paste containing 125 g (dry) of pulp was drained, dried, and occupied a volume of 18.2 cubic centimeters. 12.3 g of SEFOSE® were added to the same 3% hardwood pulp paste containing the equivalent of 125 g of dry fiber. After water drainage and drying, the resulting mat occupied 45.2 cubic centimeters.

[00155] 30g of a standard bleached short-fiber cellulose (produced by Old Town Fuel and Fiber, LLC, Old Town, ME) was sprayed with SEFOSE® that had been reduced to 60°C. These 4.3 cm3 were placed in a disintegrator at 10,000 rpm and essentially repulped. The mixture was poured into a sheet mold and dried at 105°C. The resulting hydrophobic pulp occupied a volume of 8.1 cm3. A 2-inch square of this material was cut and placed in a hydraulic press with 50 tons of pressure applied for 30 seconds. The volume of the square was significantly reduced, but still occupied 50% more volume than the same 2-inch square cut for the control without applied pressure.

[00156] It is significant that not only was an increase in volume and softness observed, but that a forcibly repulped mat after water was drained resulted in a fiber mat where all hydrophobicity was retained. This quality, in addition to the observations that water cannot be easily pushed beyond the low surface energy barrier into the sheet, is valuable. The linking of hydrophobic single-chain fatty acids does not exhibit this property.

[00157] Although not limited by theory, this represents further evidence that SEFOSE® is reacting with cellulose and that the OH groups on the surface of the cellulose fibers are no longer available to participate in subsequent hydrogen bonding. Other hydrophobic materials interfere with hydrogen bonding. Petition 870260047896, dated 05 / 20 / 2026, page 58 / 172 54 / 69 initially, however after repulsion, this effect is reversed and the OH groups in the cellulose are free to participate in hydrogen bonding after drying. Example 9. Paper bag test data

[00158] The following table (Table 7) illustrates the properties imparted by coating 5 to 7 g / m2 with a mixture of polyvinyl alcohol (PVOH) and SEFQSE® onto a raw material for unbleached kraft paper bags (control). Commercial bags are also included for reference. Table 7. Paper Bag Tests Paper Type Gauge Tensile Strength Bursting Strength Test Bag (control) 3.26 9.45 52.1 Test Bag with SEFOSE® 3.32 15.21 62.6 Sub Sandwich Bag 2.16 8.82 25.2 Home Depot Foil Bag 5.3 17.88 71.5 [I0159] As can be seen in the Table, tensile strength and rupture increase with the coating of the control base paper with SETOSE® and PvOH. Example 10. Wet and dry tensile strength

[00160] 3-gram paper sheets were made from bleached pulp. The following compares the wet and dry tensile strength at different levels of SEFOSE® addition. Note that with these paper sheets, the SEFGSE® was not emulsified into any coating; it was simply mixed into the pulp and drained without the addition of any other chemical (see Table 8). Petition 870260047896, dated 05 / 20 / 2026, page 59 / 172 55 / Q9 Table 8. Wet / dry tensile strength SEFOSE® Charge Wet Strength (lb / in2) Dry Strength (lb / in2) 0% 0.29 9.69 0.5% 1.01 10.54 1% 1.45 11.13 5% 7.22 15.02 [I0161] Note also that adding 5% for wet strength is not much below the control dry strength. Example 11. Use of esters containing fewer than 8 saturated fatty acids.

[00162] A series of experiments was carried out with sucrose esters produced with less than 8 fatty acids linked to the sucrose moiety. Samples of SP50, SP10, SP01 and F20W (from Sisterna, Netherlands) containing 50, 10, 1 and essentially 0% monoesters, respectively. Although these commercially available products are made by reacting sucrose with saturated fatty acids, thus rendering them less useful for further crosslinking or similar chemistries, they have been useful in examining emulsification and water-repellent properties.

[00163] For example, 10g of SPOI were mixed with 10g of glyoxal in a 10% cooked PvOH solution. The mixture was cooked at 200°F for 5 minutes and applied by extraction to a porous base paper made of bleached hardwood kraft. The result was a reticulated waxy coating on the paper surface that exhibited good hydrophobicity. When a minimum of 3 g / m² was applied, the resulting contact angle was greater than 100°. Since glyoxal is a well-known crystallizer used in compounds with OH groups, this method is a potential means of attaching reasonably unreactive sucrose esters to a surface by linking groups. Petition 870260047896, dated 05 / 20 / 2026, p. 60 / 172 56 / 69 of the remaining alcohol in the sucrose ring with an alcohol group provided in the substrate or other coating materials. Example 12. HST and moisture absorption data

[00164] To demonstrate that SEFOSE® alone provides the observed waterproofing properties, porous Twins River backing paper (Matawaska, ME) was treated with various amounts of SEFOSE (and PvOH or Ethylex 2025 to emulsify, applied by sinking) and tested by Hercules Size Test. The results are shown in Table 9. Table 9. HST data with SEFOSE® HST-Seconds uptake of SEFOSE® C'™ emulsifier g / m1 <1 • 27 Ogm' 2 7g nr l'\OH 16 8 Ognr 4 5g'nr Lih'le.x 2<>25 <•5 2 2« rr> 2 3g nV Cthylex 2o25 389.7 1 6g m' 1 6g m P\OH 533 3 Oi» m 4 0g nr P\OH I4XO 5 Og m* 5 Og in: Itlh* lex 2025 23(XO <0gm' S.OgW P\OII

[00165] As can be seen in Table 9, increasing the amount of SEFOSE® applied to the paper surface leads to increased water resistance (as shown by the increase in HST in seconds).

[00166] This can also be seen using coatings of a saturated sucrose ester product. For this particular example, the product, F20W (available from Sisterna, Netherlands) is described as having a very low % monoester with most molecules in the 4 to 8 substitution range. Note that the uptake of the F20W product is only 50% of the total coating, as it was emulsified with PvOH using equal parts of each to make a stable emulsion. Thus, where the uptake is labeled 0.5 g / m2, there is also the same uptake of PvOH providing a total uptake of 1.0 g / m2. The results are shown in Table 10. Petition 870260047896, dated 05 / 20 / 2026, page 61 / 172 57 / 69 Table 10. HST F20W Data. HST-seconds Sisterna F20W Uptake <1 0 2.0 0.5 g / m2 17.8 1.7 g / m2 175.5 2.2 g / m2 438.8 3.5 g / m2 2412 4.1 g / m2 [I0167] As can be seen in Table 10, again, increasing F20W increases the water resistance of the porous sheet. Thus, the sucrose fatty acid ester itself is making the paper water-resistant.

[00168] Since water resistance is not simply due to the presence of a fatty acid forming an ester bond with cellulose, softwood sheets (bleached softwood kraft) were loaded with SEFOSE® and oleic acid was added directly to the pulp, where the oleic acid forms an ester bond with the cellulose in the pulp. The mass at time zero represents the bone-dry mass of the paper sheets removed from the oven at 105°C. Samples were placed in a room with controlled humidity maintained at 50% RH. The change in mass is observed over time (in minutes). The results are shown in Tables 11 and 12. Table 11. SEFOSE® Moisture Capture Time 2% SEFOSE® 30% SEFOSE® Control 0 3.859 4.099 3.877 1 3.896 4.128 3.911 3 3.912 4.169 3.95 5 3,961 4,195 3,978 Petition 870260047896, dated 05 / 20 / 2026, page 62 / 172 58 / 69 Time 2% SEFOSE® 30% SEFOSE® Control 10 4.01 4.256 4.032 15 4.039 4.276 4.054 30 4.06 4.316 4.092 60 4.068 4.334 4.102 180 4.069 4.336 4.115 Table 12. Oleic acid moisture absorption. Time (hrs) 30% oleic acid 50% oleic acid control 0 4.018 4.014 4.356 0.5 4.067 4.052 4.48 2 4.117 4.077 4.609 3 4.128 4.08 4.631 5 4.136 4.081 4.647 21 4.142 4.083 4.661 [I0169] Note the difference here, where oleic acid is added directly to the pulp, forming an ester bond, which greatly retards moisture absorption at higher concentrations, SEFOSE® does not. As such, although not limited by theory, the structure of the material bound to SEFOSE® cannot be simply explained by the structure formed by simple fatty acid esters and cellulose. Example 13. Saturated SFAEs

[00170] The saturated class of esters consists of waxy solids at room temperature which, due to saturation, are less reactive with the sample matrix or with themselves. Using elevated temperatures (e.g., at least 40°C and for all tested above 65°C) this material melts and can be applied as a liquid which then cools and solidifies forming a hydrophobic coating. The materials can be emulsified in solid form and applied as an aqueous coating to impart hydrophobic characteristics. Petition 870260047896, dated 05 / 20 / 2026, page 63 / 172 59 / 69

[00171] The data shown here represent HST (Hercules size test) readings obtained from papers coated with varying amounts of saturated SFAEs.

[00172] A bleached #45 hardwood kraft sheet obtained from Turner Falls paper was used for test coatings. The Gurley porosity, measured at approximately 300 seconds, representing a fairly lightweight S-370 base sheet obtained from Mitsubishi Foods (Japan), was emulsified with xanthan gum (up to 1% of the mass of the saturated SFAE formulation) prior to coating.

[00173] Weight of saturated SFAE formulation coating (pounds per ton) HST (average of 4 measurements per sample). Table 13 S370 coating weight (pounds per ton) HST (average of 4 measurements per sample) control only #0 4 seconds #45 140 seconds #32 385 seconds #100 839 seconds #150 1044 seconds #200 1209 seconds [I0174] The generated laboratory data also support that limited quantities of saturated SFAE can increase the water resistance of coatings that are designed for other purposes / applications. For example, saturated SFAE was mixed with Ethylex starch-based and polyvinyl alcohol-based coatings, and increased water resistance was observed in each case.

[00175] The examples below were coated on a bleached recycled base #50 with a Gurley porosity of 18 seconds.

[00176] 100 grams of Ethylex 2025 were cooked in 10% of Petition 870260047896, dated 05 / 20 / 2026, page 64 / 172 60 / 69 solids (1 liter volume) and 10 grams of S-370 were added hot and mixed using a Silverson homogenizer. The resulting coating was applied using a common benchtop rebate device and the papers were dried under heat lamps.

[00177] With a coating weight of 300 # / ton, starch alone had an average HST of 480 seconds. With the same coating weight of the starch and saturated SFAE mixture, the HST increased to 710 seconds.

[00178] Sufficient polyvinyl alcohol (Selvol 205S) was dissolved in hot water to achieve a 10% solution. This solution was coated onto the same #50 paper described above and had an average HST of 225 to 150 pounds / ton of coating weight. Using this same solution, S-370 was added to obtain a mixture containing 90% PVOH / 10% S-370 on a dry basis (i.e., 90 ml of water, 9 grams of PVOH, 1 gram of S-370): the average HST increased to 380 seconds.

[00179] Saturated SFAEs are compatible with prolamins (specifically, zein: see U.S. Patent No. 7,737,200, incorporated herein by reference in its entirety). Since one of the main barriers to the commercial production of the subject of said patent is that the formulation be water-soluble, the addition of saturated SFAEs helps in this regard. Example 14. Other saturated SFAEs

[00180] Press evaluations of coating sizing based on saturated SFAE were performed on a bleached light sheet (approximately 35#) that had no sizing and had relatively weak formation. All evaluations were performed using PvOH Exceval HR 3010 cooked to emulsify the saturated SFAE. Sufficient saturated SFAE was added. Petition 870260047896, dated 05 / 20 / 2026, page 65 / 172 61 / 69 to represent 20% of the total solids. The focus was to evaluate the S-370 samples in comparison with C-1800 (available from Mitsubishi Foods, Japan). Both esters performed better than the control; some of the key data are shown in Table 14. Table 14 Average HST value: 10% polyvinyl alcohol kit alone 38 seconds; 2 PVOH with S-370 85 seconds; 3 PVOH with C-1800 82 seconds; 5 [I0181] Note that saturated compounds appear to provide an increase in the kit, with S-370 and C-1800 producing a 100% increase in HST. Example 13. Wet Strength Additive

[00182] Laboratory tests have shown that the chemistry of sucrose esters can be adjusted to achieve a variety of properties, including use as a moisture-resistant additive. When sucrose esters are made by attaching saturated groups to each alcohol functionality in sucrose (or another polyol), the result is a hydrophobic waxy substance with low miscibility / solubility in water. These compounds can be added to cellulosic materials to impart water resistance both internally and as a coating; however, since they do not chemically react with each other or any part of the sample matrix, they are susceptible to removal by solvents, heat, and pressure.

[00183] Where waterproofing and higher levels of water resistance are desired, sucrose esters containing unsaturated functional groups can be made and added to the cellulose material with the aim of achieving oxidation and / or Petition 870260047896, dated 05 / 20 / 2026, page 66 / 172 62 / 69 crosslinking helps to fix the sucrose ester in the matrix and make it highly resistant to removal by physical means. By adjusting the number of unsaturated groups, as well as the size of the sucrose esters, a crosslinking medium is obtained to confer resistance, but with a molecule that is not ideal for conferring water resistance.

[00184] The data shown here are obtained by adding SEFOSE® to a bleached kraft sheet at various levels and obtaining wet tensile data. The percentages presented in the table represent the percentage of sucrose ester in the treated 70# bleached paper (see Table 15). Table 15 Load Voltage / Module 0% 4.98 0.93 / 89.04 1% 5.12 1.88 / 150.22 5% 8.70 0.99 / 345.93 10% 10.54 1.25 / 356.99 Dry / Untreated 22.67

[00185] The data illustrate a trend where adding unsaturated sucrose esters to paper increases wet strength as the filler level increases. Dry tensile strength shows the maximum sheet strength as a reference point. Example 16. Method for producing sucrose esters using chlorides of acid

[00186] In addition to making hydrophobic sucrose esters via transesterification, similar hydrophobic properties can be achieved in fibrous articles by the direct reaction of acid chlorides with polyols containing ring structures analogous to sucrose.

[00187] For example, 200 grains of palmitoyl chloride (CAS 11267-4) were mixed with 50 grams of sucrose and stirred at room temperature. After mixing, the mixture was heated to 100°F and Petition 870260047896, dated 05 / 20 / 2026, page 67 / 172 63 / 69 maintained at this temperature overnight (ambient pressure). The resulting material was washed with acetone and deionized water to remove any hydrophilic or unreacted materials. Analysis of the remaining material using C-13 NMR showed that a significant amount of hydrophobic sucrose ester was formed.

[00188] Although it has been shown (by BT3 et al.) that the addition of fatty acid chlorides to cellulosic materials can impart hydrophobic properties, the reaction itself is undesirable on-site, as the released byproduct, gaseous HCl, creates several problems, including corrosion of surrounding materials and is hazardous to workers and the environment. An additional problem created by the production of hydrochloric acid is that the more is formed, i.e., the more polyol sites are reacted, the weaker the fibrous composition becomes.Palmitoyl chloride was reacted in increasing quantities with cellulose and cotton materials, and as hydrophobicity increased, the strength of the article decreased.

[00189] The above reaction was repeated several times using 200 grams of R-CO-chloride reacted with 50 grams each of other similar polyols, including corn starch, birch xylan, carboxymethylcellulose, glucose, and extracted hemicelluloses. Example 17. Peeling test

[00190] The peel test uses a wheel between the two jaws of the tensile tester to measure the force required to peel the tape from a paper surface at a reproducible angle (ASTM D1876; for example, Modular Peel Tester Series 100, TestResources, Shakopee, MN).

[00191] For this work, bleached kraft paper with Gurley high frontal Turner (600 seconds)

[00192] Falls paper (Turmerer's Falls, MA) was used. This 50-pound sheet represents a fairly narrow sheet, but quite Petition 870260047896, dated 05 / 20 / 2026, page 68 / 172 64 / 69 absorbent.

[00193] When 50-pound paper was coated with 15% Ethylex starch as a control, the average strength (over 5 samples) required was 0.55 pounds / inch. When treated with the same coating, but with SEFOSE® replaced by 25% Ethylex starch (so 23% uptake is SEFOSE®, 75% is still Ethylex), the average strength decreased to 0.081 pounds / inch. With a 50% replacement of SEFOSE® by Ethylex, the required strength decreased to less than 0.03 pounds per inch.

[00194] The preparation of this paper is in accordance with the TAPPI 404 standard method for determining the tensile strength of papers.

[00195] Finally, the same paper was used with S-370 at a loading rate of 750 pounds per ton – which effectively fills all the gaps in the sheet creating a complete physical barrier. This actually passes a TAPPI 12 kit flat. This brief experiment shows that it is possible to achieve grease resistance using saturated SFAE varieties. Example 18. Saturated SFAE and Inorganic Particles (Fills)

[00196] Saturated sucrose fatty acid esters (SFAEs) range from hydrophilic to hydrophobic, depending on the number of fatty acid chains (and chain length) attached to the sucrose molecule. These are not considered highly reactive compounds.

[00197] A range of substituted SFAEs was investigated, with side chains having 16 or 18 carbons in length. The materials examined are waxy solids with melting points below 150°C. When coated onto paper, the highly substituted esters confer significant levels of water resistance depending on the coating weight and the porosity of the sheet. For this example, the Petition 870260047896, dated 05 / 20 / 2026, page 69 / 172 65 / 69 paper was used with S-370 at a loading rate of 750 pounds per ton – which effectively fills all the pores of the sheet creating a complete physical barrier. The paper thus treated had a TAPPI 12 kit. This brief experiment shows that it is possible to obtain grease resistance using varieties of saturated SFAE. Notes:

[00198] More hydrophobic esters tend to aggregate in aqueous emissions / dispersions and therefore uniform coatings on paper become a challenge. The low melting point of several of these molecules results in melt coating on the sheet. If hydrophobic SFAEs are mixed with polymers to help stabilize the dispersion, these polymers (i.e., latex, starch, polyvinyl alcohol) will tend to envelop these esters in a way that silences the desired hydrophobic properties.

[00199] When mixed with calcium carbonate (e.g., precipitated calcium carbonate) there is an unexpected attraction. SFAE does not fuse to the paper under the same drying conditions. Calcium carbonate appears to aid in the dispersion of SFAE and the adhesion is such that SFAE acts as a binder to attach the calcium carbonate particles to the surface of the coated papers. Although not limited by theory, this uniform dispersion is believed to result in greater water resistance for a given amount of ester.

[00200] Table 16 shows the water resistance measured by the Hercules Size Test (HST) increasing with the formulations containing 50% calcium carbonate. A 40-pound unsized, porous sheet was coated by hand-counterfeiting. Coating weights were 7-10 g / m2. Petition 870260047896, dated 05 / 20 / 2026, page 70 / 172 66 / 69 Table 16. Coating composition HST with 50% PCC (precipitated CaCO3) HST without PCC uncoated base sheet 5 4 SFAE alone 3300 1750 SFAE with equal parts polyvinyl alcohol 1900 900 SFAE with equal parts ethyl starch 1475 640

[0201] The advantages of the combinations as demonstrated include reduced coating costs through the use of carbonate, as well as more efficient use of SFAE molecules, since they are more uniformly distributed across the surface of the paper substrate. Example 17. Mixtures of saturated SFAE and inorganic particles (fillers and clays)

[00202] A. This example was designed to examine the interaction between mixtures of saturated sucrose fatty acid ester and calcium carbonate.

[00203] A paper coating was made having the following composition (on a dry basis): 10% PVOH; 20% sucrose ester (mixture of SE-15 / 1803, SFAEs in equal proportions; SE15 is available from Hangzhou Union Biotechnology Co., Ltd, Hangzhou, China and C-1803 is available from Itochu Chemicals America, Inc., While Plains, NY) and 70% precipitated calcium carbonate (available from OMYA Inc., Blue Ash, OH). This mixture was applied to a bleached 65# kraft paper sheet at a coating weight of 8 g / m2. The calcium carbonate pulp alone does not exhibit a water contact angle and no HST when Petition 870260047896, dated 05 / 20 / 2026, page 71 / 172 67 / 69 coated on paper. The results using the coating composition are shown in Table 17. Sample HST (seconds) base sheet 0 base sheet + CaCO3 0 base sheet + sucrose ester mixture 35 base sheet + CaCO3 + sucrose ester mixture. 118

[0204] This example serves to illustrate that the ester-carbonate interaction is significant enough that the carbonate helps to keep the ester uniformly distributed on the sheet surface where the maximum effect can be observed. Furthermore, the data demonstrate that a bio-based material has been identified that can be used with CaCO3, resulting in a coated sheet exhibiting a high contact angle when CaCO3 is present as the main component of the composition. While not limited by theory, this effect becomes more apparent when heavy coating weights of a highly pigmented composition can be applied.

[00205] B: This example was designed to examine the interaction between saturated sucrose fatty acid esters and pigments (e.g., clays).

[00206] Kaolin-based materials have very different properties from calcium carbonate. Table 18: shows the results using another mixture of SPAE, 80 OE (available from Tensac, Sh, Tucuman, Argentina) and SE-15 in equal parts, and 80 OE, SE-15 and Imerys CAPIM™ (kaolin-based material, available from Imerys Clay, Inc., Roswell, GA) in equal parts, to produce an OGR coating. The following formulations were prepared with 10% solids and coated with 5 g / m2. Petition 870260047896, dated 05 / 20 / 2026, page 72 / 172 68 / 69 Table 18. Composition of the CAPIM™ Kit: 0 SE-15 3 80 OE 3 80 OE / SE 15 4 80 OE / SE-15 / CAPIM™ 5 / 6

[0207] Since the pigment is present above 10 to 20%, using only CAPIM™ the paper does not exhibit any kit, and as established above, once the concentration is above 10 or 20% of pigment in any barrier coating, typically the barrier properties are significantly reduced (e.g., grease is able to find pores to penetrate). The observation that esters provide better grease resistance with less liquid ester in the formulation is significant. Other Uses

[00208] It was found that the base raw material of the cup was heavily treated with rosin to increase water resistance. However, the Gurley in this sheet was found to be 50 seconds, indicating a fairly porous sheet. This material is repulpable and steam penetrates rapidly to soften it. Pure SEFOSE® was applied to this sheet and dried in an oven at 100°C overnight. The resulting material provided a plastic-like feel and was completely waterproof. By mass, it was 50% (weight / weight) cellulose / 50% (weight / weight) SEFOSE®. The Gurley was too high to be measured. Submerging a sample in water for 7 days did not significantly soften the material; however, from oven data, it appears to biodegrade in approximately 150 days. Common tapes and glues would not adhere to this composite material.

[00209] Experiments with saturated SFAE and zein were Petition 870260047896, dated 05 / 20 / 2026, page 73 / 172 69 / 69 experiments were conducted, as zein demonstrated the ability to impart grease resistance to paper. Stable aqueous dispersions of zein (up to 25% in water), to which saturated SFAE was added at 2-5%, were generated. Observations demonstrated that saturated SFAE blocks zein in the paper, imparting water resistance to the formulation (in addition to grease resistance).

[00210] The combination of SFAEs, inorganic particles, and bioplastics can be mixed to produce a moldable paper for the design of a biodegradable coffee cup lid. Using wood fiber and sufficient bioplastic fiber (e.g., polybutylene succinate (Bio-PBS) or polylactic acid (PLA)) along with SFAE, the resulting paper base would be water-resistant, where the concentration of SFAE is optimized to ensure the water resistance of the article where the use of cheaper and more common materials, such as regular pulp, represents a larger percentage of the lid's mass. In this way, a relatively small amount (e.g., less than 10%) of the article's mass would be of other materials, such as biopolymers, thus allowing the addition of other additives that can be used to provide flexibility, improve tear or stretch properties, and the like.

[00211] The addition of a calcium carbonate / SFAE mixture allows control of the lid density.

[00212] Although the invention has been described with reference to the examples above, it will be understood that modifications and variations are included within the spirit and scope of the invention. Consequently, the invention is limited only by the following claims. All references described herein are incorporated herein by reference in their entirety. Petition 870260047896, dated 05 / 20 / 2026, pp. 74 / 172

Claims

1 / 9 CLAIMS 1. Composition capable of forming a coating, characterized in that it comprises one or more saccharide fatty acid esters (SFAEs) and inorganic particles, wherein said SFAE is present in a concentration sufficient to cause the inorganic particles to adhere to a cellulose-based substrate, wherein one or more SFAEs are present - in a coating of 0.1 g / m2 to 20 g / m2, if SFAE is attached to a coating on a cellulose-based substrate; - in 0.9% to 30% (w / w) or 40% (w / w) to 50% (w / w) of the weight of the coating; or - at a concentration of 0.025% (w / w) or 0.05% (w / w) to 50% (w / w) or 100% (w / w) of the total cellulose of the cellulose-based substrate, preferably if the cellulose-based material is a solution containing cellulose fibers;and said inorganic particles comprise at least 1% of the composition on a dry basis (dB), and wherein said substrate containing said composition exhibits greater water resistance and / or grease resistance compared to a substrate containing said composition comprising inorganic particles or one or more SFAEs alone.

2. Composition according to claim 1, characterized in that the SFAE comprises all unsaturated fatty acids, all saturated fatty acids, or a mixture of saturated and unsaturated fatty acids and, optionally, also comprises one or more binders selected from PvOH or starch. Petition 870260047896, dated 05 / 20 / 2026, p. 75 / 172 2 / 9 3. Composition according to claim 1, characterized in that the SFAE is a mixture of two or more different SFAEs, and wherein said two or more different SFAEs comprise all saturated fatty acids.

4. Composition, according to claim 1, characterized in that said inorganic particles are selected from the group consisting of clay, ground calcium carbonate, precipitated calcium carbonate, talc, titanium dioxide and combinations thereof, and in which said inorganic particles comprise at least 1% of the composition on a dry basis (db), preferably the inorganic particle is a calcium carbonate and in which the substrate exhibits water resistance or the inorganic particle is clay, and in which said substrate exhibits grease resistance.

5. Composition according to claim 1, characterized in that said SFAE contains at least one saccharide and at least one aliphatic group comprising 8 to 30 carbons.

6. Composition, according to claim 1, characterized in that the cellulose-based substrate is selected from the group consisting of paper, cardboard, paper pulp, a food storage cardboard box, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant covering film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a composting bag, release paper, cutlery, a hot or cold beverage container, a cup, towels. Petition 870260047896, dated 05 / 20 / 2026, p.76 / 172 3 / 9 paper, plate, a carbonated liquid storage bottle, insulating material, a non-carbonated liquid storage bottle, food packaging film, a waste container, a food handling instrument, a cup lid, a screw-on moldable paper cup lid, paper straws, a fabric fiber, a water transport and storage instrument, medical use card, release paper, an instrument for transporting and storing alcoholic or non-alcoholic beverages, wrapper, a good electronic external screen, an internal or external piece of furniture, a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic fiber material and combinations thereof.

7. A manufactured article, characterized in that it comprises a coating containing one or more saccharide fatty acid esters (SFAEs), inorganic particles, a cellulose-based substrate, and one or more binders, wherein the inorganic particles are present in the coating at a concentration of at least 1% on a dry basis (dB), and one or more SFAEs are present - in a coating from 0.1 g / m2 to 20 g / m2, if the SFAE is bonded to a coating on a cellulose-based substrate; - in 0.9% to 30% (w / w) or 40% (w / w) to 50% (w / w) of the weight of the coating; or - at a concentration of 0.025% (w / w) or 0.05% (w / w) to 50% (w / w) or 100% (w / w) of the total cellulose of the cellulose-based substrate, preferably, if the cellulose-based material is a solution containing cellulose fibers, preferably, the cellulose-based substrate is selected from the group consisting of paper, cardboard, paper pulp,a cardboard food storage box, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant cover film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a composting bag, release paper, cutlery, a hot or cold beverage container, a cup, paper towels, a plate, a carbonated liquid storage bottle, insulating material, a non-carbonated liquid storage bottle, food packaging film, a waste container, a food handling instrument, a cup lid, a screw-on moldable paper cup lid, paper straws, a fabric fiber, a water transport and storage instrument,Medical prescription card, release paper, a device for transporting and storing alcoholic or non-alcoholic beverages, wrapper, a good electronic external screen, an internal or external piece of furniture, a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic fiber material and combinations thereof.

8. Article according to claim 7, characterized in that the coating is a coating formed from a composition as defined in claim 1.

9. Method for treating a cellulosic substrate, characterized in that it comprises: Petition 870260047896, dated 05 / 20 / 2026, page 78 / 172 5 / 9 a) adding at least one saccharide fatty acid ester (SFAE) to a composition capable of forming a coating, wherein the composition comprises inorganic particles to form a mixture, b) applying said mixture to at least one surface of said cellulosic substrate; (ec) cure for a sufficient time to allow the mixture to adhere to at least one surface, wherein the cured surface exhibits greater hydrophobicity and / or lipophobicity compared to a surface treated with at least one SFAE or the composition comprising the inorganic particles alone, wherein one or more SFAEs are present - in a coating of 0.1 g / m2 to 20 g / m2, if the SFAE is bonded to a coating on a cellulose-based substrate; - in 0.9% to 30% (w / w) or 40% (w / w) to 50% (w / w) of the coating weight;or - at a concentration of 0.025% (w / w) or 0.05% (w / w) to 50% (w / w) or 100% (w / w) of the total cellulose of the cellulose-based substrate, preferably if the cellulose-based material is a solution containing cellulose fibers; and said inorganic particles comprise at least 1% of the composition on a dry basis (dB), preferably the treated cellulose surface is hydrophobic or lipophobic.

10. Method, according to claim 8, characterized in that the SFAE comprises all saturated fatty acids or a mixture of saturated and unsaturated fatty acids, and / or. Petition 870260047896, dated 05 / 20 / 2026, page 79 / 172 6 / 9 wherein the SFAE is a mixture of two or more different SFAEs.

11. Method according to claim 9, characterized in that said inorganic particles are selected from the group consisting of clay, ground calcium carbonate, precipitated calcium carbonate, talc, titanium dioxide and combinations thereof, and in which said inorganic particles comprise at least 1% of the composition on a dry basis (db), preferably in which the composition also comprises polyvinyl alcohol or starch.

12. Method according to claim 9, characterized in that the inorganic particles comprise calcium carbonate, and wherein the calcium carbonate comprises more than or equal to 30% of the mixture on a dry basis (db).

13. Method according to claim 11, characterized in that the calcium carbonate is precipitated calcium carbonate.

14. Method according to claim 9, characterized in that the cellulose substrate is selected from the group consisting of paper, cardboard, paper pulp, a food storage cardboard box, a food storage bag, a carrying bag, a coffee or tea container, a tea bag, a bacon tray, diapers, weed barrier / blocker fabric or film, plant covering film, plant pots, packaging beads, bubble wrap, oil absorbent material, laminates, envelopes, gift cards, credit cards, gloves, raincoats, OGR paper, a shopping bag, a composting bag, release paper, cutlery, a hot or cold beverage container, a cup, paper towels, a plate, a carbonated liquid storage bottle, material Petition 870260047896, dated 05 / 20 / 2026, p.80 / 172 7 / 9 insulator, a non-carbonated liquid storage bottle, food packaging film, a waste container, a food handling instrument, a cup lid, a screw-on moldable paper cup lid, paper straws, a fabric fiber, a water transport and storage instrument, medical use card, release paper, an instrument for transporting and storing alcoholic or non-alcoholic beverages, wrapper, a good electronic external screen, an internal or external piece of furniture, a curtain, upholstery, film, box, sheet, tray; tube, water conduit, clothing for packaging pharmaceutical products, medical device, contraceptive, camping equipment, molded cellulosic fiber material and combinations thereof.

15. Composition according to claim 1, characterized in that one or more SFAEs are present - in a coating of 0.1 g / m2 to 1.0 g / m2, 1.0 g / m2 to 2.0 g / m2, 2 g / m2 to 3 g / m2, 3 g / m2 to 4 g / m2, 4 g / m2 to 5 g / m2, 5 g / m2 to 10 g / m2, 10 g / m2 to 20 g / m2, if the SFAE is bonded to a coating on a cellulose-based substrate; - in 0.9% to 1.0%, 1.0% to 5.0%, 5.0% to 10%, 10% to 20%, 20% to 30%, 25% to 35% or 40% to 50% by weight of the coating weight (w / w); or - at a concentration of 0.05% (w / w), 0.1% (w / w), 0.1% (w / w) to 0.5% (w / w), 0.5% (w / w) to 1.0% (w / w), 1.0% (w / w) to 2.0% (w / w), 2.0% (w / w) to 3.0% (w / w), 3.0% (w / w) to 4.0% (w / w), 4.0% (w / w) to 5.0% (w / w), 5.0% (w / w) to 10% (w / w), or 10% (w / w) to 50% (w / w) of the total cellulose of the cellulose-based substrate, preferably if the cellulose-based material is a solution containing fibers of Petition 870260047896, of 20 / 05 / 2026, p. 81 / 172 8 / 9 cellulose.

16. Article of manufacture, according to claim 7, characterized in that one or more SFAEs are present - in a coating of 0.1 g / m2 to 1.0 g / m2, 1.0 g / m2 to 2.0 g / m2, 2 g / m2 to 3 g / m2, 3 g / m2 to 4 g / m2, 4 g / m2 to 5 g / m2, 5 g / m2 to 10 g / m2, 10 g / m2 to 20 g / m2, if the SFAE is bonded to a coating on a cellulose-based substrate; - in 0.9% to 1.0%, 1.0% to 5.0%, 5.0% to 10%, 10% to 20%, 20% to 30%, 25% to 35% or 40% to 50% by weight of the coating weight (w / w); or - at a concentration of 0.05% (w / w), 0.1% (w / w), 0.1% (w / w) to 0.5% (w / w), 0.5% (w / w) to 1.0% (w / w), 1.0% (w / w) to 2.0% (w / w), 2.0% (w / w) to 3.0% (w / w), 3.0% (w / w) to 4.0% (w / w), 4.0% (w / w) to 5.0% (w / w), 5.0% (w / w) to 10% (w / w), or 10% (w / w) to 50% (w / w) of the total cellulose of the cellulose-based substrate, preferably if the cellulose-based material is a solution containing cellulose fibers.

17. Method according to claim 9, characterized in that one or more SFAEs are present - in a coating of 0.1 g / m2 to 1.0 g / m2, 1.0 g / m2 to 2.0 g / m2, 2 g / m2 to 3 g / m2, 3 g / m2 to 4 g / m2, 4 g / m2 to 5 g / m2, 5 g / m2 to 10 g / m2, 10 g / m2 to 20 g / m2, if the SFAE is bonded to a coating on a cellulose-based substrate; - in 0.9% to 1.0%, 1.0% to 5.0%, 5.0% to 10%, 10% to 20%, 20% to 30%, 25% to 35% or 40% to 50% by weight of the coating weight (w / w); or - at a concentration of 0.05% (w / w) 0.1% (w / w), 0.1% (w / w) to 0.5% (w / w), 0.5% (w / w) to 1.0% (w / w), 1.0% (w / w) to 2.0% (w / w), Petition 870260047896, dated 05 / 20 / 2026, p. 82 / 172 9 / 9 2.0% (w / w) to 3.0% (w / w), 3.0% (w / w) to 4.0% (w / w), 4.0% (w / w) to 5.0% (w / w), 5.0% (w / w) to 10% (w / w), or 10% (w / w) to 50% (w / w) of the total cellulose of the cellulose-based substrate, preferably if the cellulose-based material is a solution containing cellulose fibers. Petition 870260047896, dated 05 / 20 / 2026, p. 83 / 172

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