Two-part bio-based, water-reducible epoxy coating

Abstract

A two-part epoxy formulation that is both water-reducible and bio-based, exhibiting surprising durability comparable to or exceeding conventional petroleum-based epoxies and high UV resistance. The coating composition contains: (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives. The first part contains components (A) and (B), while the second part contains components (C) and (D).

Description

[0001] Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0002] TITLE OF THE INVENTION

[0003] Two-Part Bio-Based, Water- Reducible Epoxy Coating

[0004] CROSS-REFERENCE TO RELATED APPLICATIONS

[0005] The present application claims priority to U.S. Provisional Appl. No. 63 / 756,371, filed February 10, 2025, the entire contents of which are incorporated herein by reference.

[0006] FIELD OF THE INVENTION

[0007] This invention relates to a novel formulation that is both water-reducible and biobased, exhibiting surprising durability comparable to or exceeding conventional petroleumbased epoxies and high UV resistance. The coating composition contains: (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives. The first part contains components (A) and (B), while the second part contains components (C) and (D).

[0008] DISCUSSION OF THE BACKGROUND

[0009] Epoxy resins are widely used in various industries due to their excellent adhesion, chemical resistance, and mechanical properties. However, traditional epoxy primers and coatings often rely on petroleum-based resins and solvents, contributing to environmental pollution and health hazards. Furthermore, achieving both water reducibility and UV resistance in high-solids epoxy coatings has been a challenge. Water-reducible epoxies often sacrifice performance properties, while UV-resistant epoxies typically require specialized and expensive additives. Further, traditional epoxies often involve volatile organic compounds (VOCs) and toxic components.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0010] There is a growing need for sustainable and environmentally friendly alternatives that reduce reliance on fossil fuels and minimize harmful emissions. Bio-based epoxies derived from renewable resources have emerged as promising candidates to replace petroleum-based counterparts. However, achieving comparable performance characteristics, particularly in terms of durability and water resistance, has been a challenge.

[0011] In view of the foregoing, there remains a critical need in the art to develop safe coating compositions that utilize bio-based epoxies but that also have high performance characteristics.

[0012] SUMMARY OF THE INVENTION

[0013] It is an object of the present invention to provide a coating composition comprising: (A) a solids-based epoxy resin;

[0014] (B) an epoxidized plant-based oil;

[0015] (C) a polyester polyol; and

[0016] (D) a plant-based polyol; and

[0017] (E) optionally, one or more additives,

[0018] wherein the coating composition has a total solids content ranging from 70% to 95%.

[0019] In embodiment, the coating composition contains 30 wt% to 60 wt% of component (A), 1 wt% to 10 wt% of component (B), 2 wt% to 15 wt% of component (C), and 25 wt% to 50 wt% of component (D), wherein the percentages are based on the total of components (A) - (D).

[0020] It is an object of the present invention to provide a kit comprising, the coating composition comprising (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives together with instructions for use thereof.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0021] It is an object of the present invention to provide a method of making a coating composition, comprising

[0022] stirring, shaking, or agitating (A) a solids-based epoxy resin, (B) an epoxidized plantbased oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives for a time and under conditions sufficient to blend the components to substantial homogeneity thus forming the coating composition, wherein the coating composition has a total solids content ranging from 70% to 95% based on components (A) - (D).

[0023] It is an object of the present invention to provide a method of coating a surface of a material by:

[0024] (1) applying a layer of a coating composition comprising (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives to a surface of a material,, wherein the coating composition has a total solids content ranging from 70% to 95% based on components (A) – (D), and

[0025] (2) allowing the coating composition to cure.

[0026] It is an object of the present invention to provide a coated material wherein a surface of a material has a coating of a cured product of a coating composition comprising (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives.

[0027] The above objects highlight certain aspects of the invention. Additional objects, aspects and embodiments of the invention are found in the following detailed description of the invention.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0028] DETAILED DESCRIPTION OF THE INVENTION

[0029] Unless specifically defined, all technical and scientific terms used herein have the same meaning as commonly understood by a skilled artisan in chemistry (e.g., polyurethane chemistry), coatings, and adhesives.

[0030] All methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, with suitable methods and materials being described herein. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. Further, the materials, methods, and examples are illustrative only and are not intended to be limiting, unless otherwise specified.

[0031] The preferred embodiments of the present invention will now be described with reference to the drawings. Identical elements in the various figures are identified with the same reference numerals.

[0032] Reference will now be made in detail to each embodiment of the present invention. Such embodiments are provided by way of explanation of the present invention, which is not intended to be limited thereto. In fact, those of ordinary skill in the art may appreciate upon reading the present specification and viewing the present drawings that various modifications and variations can be made thereto.

[0033] For clarity, the terms “coating” and “coating composition” are used interchangeably herein unless otherwise indicated.

[0034] The present invention provides a coating composition containing:

[0035] (A) a solids-based epoxy resin;

[0036] (B) an epoxidized plant-based oil;

[0037] (C) a polyester polyol; andAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0038] (D) a plant-based polyol; and

[0039] (E) optionally, one or more additives,

[0040] wherein the coating composition has a total solids content ranging from 70% to 95%.

[0041] In embodiment, the coating composition contains 30 wt% to 60 wt% of component (A), 1 wt% to 10 wt% of component (B), 2 wt% to 15 wt% of component (C), and 25 wt% to 50 wt% of component (D), wherein the percentages are based on the total of components (A) - (D).

[0042] The coating composition exhibits excellent adhesion to various substrates, including metals, wood, and composites. It also provides outstanding corrosion protection and chemical resistance. Surprisingly, the high bio-based content and water reducibility do not compromise the performance properties of the coating composition. Moreover, the coating composition demonstrates unexpected resistance to UV degradation, maintaining its color and gloss even after prolonged exposure to sunlight.

[0043] In the coating composition described herein, where a wt% is recited it is based on the total weight of the coating composition unless otherwise specified.

[0044] (A) Solids-Based Epoxy Resin

[0045] The coating composition of the present invention contains one or more solids-based epoxy resins. Not to be bound to any theory, but in an embodiment, the solids-based epoxy resin serves as the primary binder, providing adhesion and film formation. The epoxidized plant-based oil also enhances the bio-based content of the coating and contributes to its UV resistance.

[0046] In an embodiment, the epoxy resin has a molecular weight of 200 g / mol to 5,000 g / mol, 400 g / mol to 4,000 g / mol, 500 g / mol to 3,500 g / mol, 600 g / mol to 3,000 g / mol, 700 to 2,500 g / mol.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0047] It is well understood by the skilled artisan that a solids-based epoxy resin is a term that relates to the epoxy resin (of varying types) with some hardener, without any water or solvents added. Where it is desired to create thicker coatings, a solids-based epoxy resin may be advantageously utilized.

[0048] Solids-based epoxy resins may be reacted (cross-linked) either with themselves through catalytic homopolymerization, or with a wide range of co-reactants including polyfunctional amines, acids (and acid anhydrides), phenols, alcohols and thiols (sometimes called mercaptans).

[0049] In an embodiment the solid epoxy resins are made via fusion with bisphenol A, for example a bisphenol-A diglycidyl ether, or biosphenol F, for example a bisphenol-F diglycidyl ether. Other examples include novalec epoxy resins (e.g., derived from phenol or cresol), aliphatic or cycloaliphatic epoxy resins, halogenated epoxy resins, and aromatic epoxy resins, and glycidylamine epoxy resins.

[0050] The epoxy compound can be a di-, tri- or tetraglycidyl ether or a di-, or tri- or tetraglycidyl ester. Examples of suitable epoxy compounds include diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, diglycidyl ester of phthalic acid, 1,4-cyclohexanedmethanol diglycidyl ether, 1,3-cyclohexanedmethanol diglycidyl ether, diglycidyl ester of hexahydrophthalic acid, epoxy novolac resins, or mixtures thereof.

[0051] In an embodiment, the coating composition contains a total of at least 30 wt%, at least 32.5 wt%, at least 35 wt%, at least 37.5 wt%, at least 40 wt%, at least 42.5 wt%, at least 45 wt%, at least 47.5 wt%, or at least 50 wt% of the epoxy resin. The coating composition contains a total of at most 60 wt%, at most 57.5 wt%, at most 55 wt%, at most 52.5 wt%, at most 50 wt%, at most 47.5 wt%, or at most 45 wt% of the epoxy resin. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e.,Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0052] “at most”) limit from those selected above. Exemplary ranges include 30 wt% to 60 wt%, 35 wt% to 60 wt%, 40 wt% to 60 wt%, 45 wt% to 60 wt%, 50 wt% to 60 wt%, 30 wt% to 55 wt%, 35 wt% to 55 wt%, 40 wt% to 55 wt%, 45 wt% to 55 wt%, 30 wt% to 50 wt%, 35 wt% to 50 wt%, 40 wt% to 50 wt%, 30 wt% to 45 wt%, and 35 wt% to 45 wt%.

[0053]

[0054] Plant-Based Oil

[0055] The coating composition of the present invention contains one or more epoxidized plant-based oil. Not to be bound to any theory, but in an embodiment, the epoxidized plantbased oil serves as a binder, providing adhesion and film formation. The epoxidized plantbased oil also enhances the bio-based content of the coating and contributes to its UV resistance.

[0056] In an embodiment, the epoxidized plant-based oil may include, may be derived from a synthetic and / or natural oil.

[0057] In an embodiment, the epoxidized plant-based oil can be any suitable epoxidized oil obtained from a sustainable source. The sustainable source can be a plant oil, vegetable oil, tree oil, or a nut oil.

[0058] In an embodiment, the oil is epoxidized using a suitable epoxidation agent, such as a peracid (e.g., peracetic acid) or m-chloroperoxybenzoic acid, to introduce epoxy groups into the triglyceride structure. The epoxidized oil can also be obtained by a simple reaction of a suitable oil with acid and hydrogen peroxide can yield epoxidized oil. A perester may also be used to form an epoxidized oil.

[0059] Epoxidation can be of a subject oil or an oil that has been synthetically or enzymatically modified to incorporate one or more non-conjugated carbon-carbon double bonds.

[0060] Non-limiting examples of oils that can be directly epoxidized include oils that have one or more non-conjugated carbon-carbon double bonds (i.e., an unsaturated fatty acid), two orAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0061] more non-conjugated carbon-carbon double bonds, three or more non-conjugated carboncarbon double bonds, four or more non-conjugated carbon-carbon double bonds, five or more non-conjugated carbon-carbon double bonds, six or more non-conjugated carbon-carbon double bonds, seven or more non-conjugated carbon-carbon double bonds, eight or more nonconjugated carbon-carbon double bonds, nine or more non-conjugated carbon-carbon double bonds, or ten or more non-conjugated carbon-carbon double bonds. As an upper limit to any of the foregoing ranges, twenty or less non-conjugated carbon-carbon double bonds, fifteen or less non-conjugated carbon-carbon double bonds, twelve or less non-conjugated carbon-carbon double bonds, ten or less non-conjugated carbon-carbon double bonds, nine or less nonconjugated carbon-carbon double bonds, eight or less non-conjugated carbon-carbon double bonds, seven or less non-conjugated carbon-carbon double bonds, six or less non-conjugated carbon-carbon double bonds, five or less non-conjugated carbon-carbon double bonds, four or less non-conjugated carbon-carbon double bonds, three or less non-conjugated carbon-carbon double bonds, or two or less non-conjugated carbon-carbon double bonds are envisioned. As such, envisioned are ranges of the foregoing where a lower limit and an upper limit are selected as illustrated by the following exemplary ranges one to ten non-conjugated carbon-carbon double bonds, one to eight non-conjugated carbon-carbon double bonds, one to six nonconjugated carbon-carbon double bonds, one to four non-conjugated carbon-carbon double bonds, one to three non-conjugated carbon-carbon double bonds, two to ten non-conjugated carbon-carbon double bonds, two to eight non-conjugated carbon-carbon double bonds, two to six non-conjugated carbon-carbon double bonds, two to four non-conjugated carbon-carbon double bonds, two to three non-conjugated carbon-carbon double bonds, three to ten nonconjugated carbon-carbon double bonds, three to eight non-conjugated carbon-carbon double bonds, three to six non-conjugated carbon-carbon double bonds, three to four non-conjugated carbon-carbon double bonds, four to ten non-conjugated carbon-carbon double bonds, four toAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0062] eight non-conjugated carbon-carbon double bonds, and four to six non-conjugated carboncarbon double bonds.

[0063] In an embodiment of the present invention, prior to epoxidation, a subject oil can be subjected to a dehydrogenation (i.e., desaturation) reaction to introduce one or more nonconjugated carbon-carbon double bonds into one more carboxylic chain of a constituent saturated fatty acid. Exemplary reactions of forming an unsaturated fatty acid are direct desaturation utilizing oxygen and NADPH, selective desaturation using a fatty acid desaturase, or anaerobic arrangement. In an embodiment of the present invention, desaturation conditions are controlled to engineer an oil having the foregoing number(s) of non-conjugated carboncarbon double bonds.

[0064] Epoxidation can be of a subject oil or an oil that has been synthetically or enzymatically modified to incorporate one or more non-conjugated carbon-carbon double bonds.

[0065] In an embodiment of the present invention, the oil that can be epoxidized (directly or after dehydrogenation) is almond oil, avocado oil, bay oil, basil oil, bergamot oil, oils derived from biomass, Brazil nut oil, broccoli oil, cade oil, canola oil, caraway seed oil, cashew oil, cashew nutshell liquid, castor oil, cinnamon leaf oil, citronella java oil, citrus seed oil, cod liver oil, com oil, cocoa butter, cottonseed oil, cumin oil, cypress oil, fish oil, flaxseed oil, geranium oil, grapefruit oil, hazelnut oil, lavender oil, lemongrass oil, linseed oil, macademia nut oil, mandarine oil, melissa oil, myrtle oil, neem oil, nutmeg oil, oat oil, olive oil, palm oil, palmarosa oil, peanut oil, pecan oil, peppermint oil, pine nut oil, pistachio oil, rapeseed oil, safflower oil, sage oil, sesame oil, soybean oil, spearmint oil, sunflower oil, high oleic sunflower oil, tea tree oil, thyme oil, triolein, vegetable oil, Vernonia oil, vetiver Haiti oil, walnut oil, wormwood oil, ylang ylang oil or any combination of two or more of the foregoing oils.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0066] The degree of epoxidation of the foregoing oil may be partial (at least 10%, at least 20%, at least 25%, at least 30%, at least 33%, at least 40%, at least 50%, at least 60%, at least 70%, at least 75%, at least 80%, at least 90%, or at least 95%) or complete (100%) of the nonconjugated carbon-carbon double bonds. The foregoing percentages are understood to be average degrees of epoxidation across all epoxidized oils present in the coating composition. For example, in an embodiment of the present invention two or more forms of the same or of different base epoxidized oils can be present in the coating composition and, when present, the average degree of epoxidation meets the foregoing ranges.

[0067] Thus, in an embodiment of the present invention, the coating composition comprises two or more epoxidized oils of the same (differ by degree of epoxidation) or different (differ by type and / or degree of epoxidation) base oil and, optionally, one or more oil of the same or different type that has not been epoxidized (i.e., 0% epoxidation). Where the epoxidized oil is mixed with an oil of the same or different type that has not been epoxidized, the ratio of the oils is such that the final average degree of epoxidation is at least 10%, at least 20%, at least 25%, at least 30%, at least 33%, at least 40%, at least 50%, at least 60%, at least 70%, at least 75%, at least 80%, at least 90%, or at least 95%. In an embodiment of the present invention, the total amount of non-epoxidized oil does not exceed 60% by weight, does not exceed 55%, does not exceed 50%, does not exceed 45%, does not exceed 40%, does not exceed 35%, does not exceed 30%, does not exceed 25%, does not exceed 20%, does not exceed 15%, or does not exceed 10% of the total amount of oil present in the coating composition.

[0068] The epoxidized plant-based oil of the present invention will have at least one, at least two, at least three, at least four, at least five, at least six, at least seven, at least eight, at least nine, at least ten epoxy groups. As an upper limit to any of the foregoing ranges, twenty or less, fifteen or less, twelve or less, ten or less, nine or less, eight or less, seven or less, six or less, five or less, four or less, three or less, or two or less epoxy groups are envisioned. As such,Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0069] envisioned are ranges of the foregoing where a lower limit and an upper limit are selected as illustrated by the following exemplary ranges one to ten, one to eight, one to six, one to four, one to three, two to ten, two to eight, two to six, two to four, two to three, three to ten, three to eight, three to six, three to four, four to ten, four to eight, and four to six epoxy groups. The epoxy groups may be internal or terminal epoxy groups.

[0070] In an embodiment of the present invention, the epoxidized plant-based oil has a viscosity of 100 to 1000 cps at 25°C, 200 to 800 cps at 25°C, 300 to 700 cps at 25°C, 400 to 650 cps at 25°C, and 450 to 550 cps at 25°C.

[0071] In an embodiment, the epoxidized plant-based oil is epoxidized soybean oil, epoxidized linseed oil, and epoxidized castor oil. An exemplary structure of the epoxidized soybean oil is as follows:

[0072]

[0073] In an embodiment, the coating composition contains a total of at least 1 wt%, at least 1.5 wt%, at least 2 wt%, at least 2.5 wt%, at least 3 wt%, at least 3.5 wt%, at least 4 wt%, at least 4.5 wt% or at least 5 wt% of the epoxidized plant-based oil. The coating composition contains a total of at most 10 wt%, at most 9.5 wt%, at most 9 wt%, at most 8.5 wt%, at most 8 wt%, at most 7.5 wt%, at most 7 wt%, at most 6.5 wt%, at most 6 wt%, at most 5.5 wt%, or at most 5 wt% of the epoxidized plant-based oil. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above. Exemplary ranges include 1 wt% to 10 wt%, 1.5 wt% to 10 wt%, 2 wt% to 10 wt%, 2.5 wt% to 10 wt%, 3 wt% to 10 wt%, 3.5 wt% to 10 wt%, 4 wt% to 10Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0074] wt%, 4.5 wt% to 10 wt%, 5 wt% to 10 wt%, 1 wt% to 9 wt%, 1.5 wt% to 9 wt%, 2 wt% to 9 wt%, 2.5 wt% to 9 wt%, 3 wt% to 9 wt%, 3.5 wt% to 9 wt%, 4 wt% to 9 wt%, 4.5 wt% to 9 wt%, 5 wt% to 9 wt%, 1 wt% to 8 wt%, 1.5 wt% to 8 wt%, 2 wt% to 8 wt%, 2.5 wt% to 8 wt%, 3 wt% to 8 wt%, 3.5 wt% to 8 wt%, 4 wt% to 8 wt%, 4.5 wt% to 8 wt%, 5 wt% to 8 wt%, 1 wt% to 7 wt%, 1.5 wt% to 7 wt%, 2 wt% to 7 wt%, 2.5 wt% to 7 wt%, 3 wt% to 7 wt%, 3.5 wt% to 7 wt%, 4 wt% to 7 wt%, 4.5 wt% to 7 wt%, 5 wt% to 7 wt%, 1 wt% to 6 wt%, 1.5 wt% to 6 wt%, 2 wt% to 6 wt%, 2.5 wt% to 6 wt%, 3 wt% to 6 wt%, 3.5 wt% to 6 wt%, 4 wt% to 6 wt%, 4.5 wt% to 6 wt%, and 5 wt% to 6 wt%.

[0075] (C) Polyester Polyol

[0076] The coating composition of the present invention contains one or more polyester polyols. Not to be bound to any theory, but in an embodiment, the polyester polyol serves as a flexibilizer and contributes to the water reducibility of the coating composition.

[0077] Polyester polyols are known for example from Ullmann's Enzyklopadie der technischen Chemie, 4th edition, volume 19, pages 62 to 65. It is preferred to use polyester polyols obtained by reacting dihydric alcohols with dibasic carboxylic acids. In place of the free polycarboxylic acids it is also possible to use the corresponding polycarboxylic anhydrides or corresponding polycarboxylic esters of lower alcohols or mixtures thereof to prepare the polyester polyols. The polycarboxylic acids may be aliphatic, cycloaliphatic, aromatic or heterocyclic and may optionally be substituted, by halogen atoms, for example, and / or unsaturated.

[0078] The following are illustrative examples of polyester polyols for use in the present invention:

[0079] A polyester polyol (1) which is a reaction product of a polyester obtained by a ringopening polymerization reaction of a cyclic ester compound such as propiolactone,Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0080] butyrolactone, ε-caprolactone, σ-valerolactone, and β-methyl-σ-valerolactone with a polyhydric alcohol such as the glycol, glycerin, trimethylolpropane, and pentaerythritol;

[0081] A polyester polyol (2) obtained by reacting a polyvalent carboxylic acid with a bifunctional polyol such as the glycol, dimer diol, and the bisphenol;

[0082] A polyester polyol (3) obtained by reacting a tri- or tetrafunctional aliphatic alcohol with a polyvalent carboxylic acid;

[0083] A polyester polyol (4) obtained by reacting a bifunctional polyol with the tri- or tetrafunctional aliphatic alcohol and a polyvalent carboxylic acid;

[0084] A polyester polyol (5) which is a polymer of a hydroxyl acid such as dimethylolpropionic acid and castor oil fatty acid;

[0085] Examples of the polyvalent carboxylic acid used in the synthesis of the polyester polyols include aromatic polybasic acids such as orthophthalic acid, terephthalic acid, isophthalic acid, phthalic acid anhydride, 1,4-naphthalene dicarboxylic acid, 2, 5 -naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, 2, 3 -naphthalene dicarboxylic acid anhydride, naphthalic acid, trimellitic acid, trimellitic acid anhydride, pyromellitic acid, pyromellitic acid anhydride, biphenyldicarboxylic acid, l,2-bis(phenoxy) ethane-p,p'-dicarboxylic acid, benzophenone tetracarboxylic acid, benzophenone tetracarboxylic acid anhydride, 5-sodium sulfoisophthalic acid, tetrachlorophthalic acid anhydride, and tetrabromo phthalic acid anhydride; methyl esterification products of an aromatic polycarboxylic acid, such as dimethyl terephthalate and dimethyl 2,6-naphthalenedicarboxylate aliphatic polybasic acids such as malonic acid, succinic acid, succinic acid anhydride, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, fumaric acid, maleic acid, maleic acid anhydride, and itaconic acid; alkyl esterification products of an aliphatic polybasic acid, such as dimethyl malonate, diethyl malonate, dimethyl succinate, dimethyl glutarate, dimethyl adipate, diethyl pimelate, diethylAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0086] sebacate, dimethyl fumarate, diethyl fumarate, dimethyl maleate, and diethyl maleate; alicyclic polybasic acids such as 1,1-cyclopentanedicarboxylic acid, 1,2-cyclopentanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, phthalic anhydride, tetrahydrophthalic acid anhydride, 4-methylhexahydrophthalic acid anhydride, hexahydrophthalic acid anhydride, cyclohexane-1,2,4-tricarboxylic acid-l,2-anhydride, himic acid anhydride, and het acid anhydride, and one or two or more kinds thereof can be used in combination.

[0087] In an embodiment, the polyester polyols is derived from adipic acid or phthalic anhydride.

[0088] In an embodiment, the coating composition contains a total of at least 2 wt%, at least 3 wt%, at least 4 wt%, at least 5 wt%, at least 6 wt%, at least 7 wt%, at least 8 wt%, at least 9 wt% or at least 10 wt% of the polyester polyol. The coating composition contains a total of at most 15 wt%, at most 14 wt%, at most 13 wt%, at most 12 wt%, at most 11 wt%, at most 10 wt%, at most 9 wt%, or at most 8 wt% of the polyester polyol. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above. Exemplary ranges include 2 wt% to 15 wt%, 3 wt% to 15 wt%, 4 wt% to 15 wt%, 5 wt% to 15 wt%, 6 wt% to 15 wt%, 7 wt% to 15 wt%, 8 wt% to 15 wt%, 2 wt% to 14 wt%, 3 wt% to 14 wt%, 4 wt% to 14 wt%, 5 wt% to 14 wt%, 6 wt% to 14 wt%, 7 wt% to 14 wt%, 8 wt% to 14 wt%, 2 wt% to 13 wt%, 3 wt% to 13 wt%, 4 wt% to 13 wt%, 5 wt% to 13 wt%, 6 wt% to 13 wt%, 7 wt% to 13 wt%, 8 wt% to 13 wt%, 2 wt% to 12 wt%, 3 wt% to 12 wt%, 4 wt% to 12 wt%, 5 wt% to 12 wt%, 6 wt% to 12 wt%, 7 wt% to 12 wt%, 8 wt% to 12 wt%, 2 wt% to 11 wt%, 3 wt% to 11 wt%, 4 wt% to 11 wt%, 5 wt% to 11 wt%, 6 wt% to 11 wt%, 7 wt% to 11 wt%, 8 wt% to 11 wt%, 2 wt% to 10 wt%, 3 wt%Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0089] to 10 wt%, 4 wt% to 10 wt%, 5 wt% to 10 wt%, 6 wt% to 10 wt%, 7 wt% to 10 wt%, and 8 wt% to 10 wt%.

[0090] (D) Plant-Based Polyol

[0091] The coating composition of the present invention contains one or more plant-based polyols. Not to be bound to any theory, but in an embodiment, the plant-based polyol serves to further increases the bio-based content and contributes to the water reducibility and UV resistance of the coating composition.

[0092] Plant-based polyols are derived from renewable resources such as vegetable oils, sugars, and other biomass sources.

[0093] The one or more plant-based polyols useful in the coating composition can include polyols containing ester groups that are derived from plant-based fats and oils. Accordingly, the one or more plant-based polyols can contain structural elements of fatty acids and fatty alcohols. Starting materials for the plant-based polyols of the coating composition can include fats and / or oils of plant-based origin with preferably unsaturated fatty acid residues.

[0094] The plant-based polyol for use in the coating composition of the present invention includes natural oil polyols, also known as NOPs or biopolyols, which are polyols derived from vegetable oils. The one or more plant-based polyols useful for the coating composition include, for example, castor oil, coconut oil, corn oil, cottonseed oil, lesquerella oil, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, sunflower oil, tall oil, maltitol, sucrose-based, isosorbide, sorbitol, glycerol, cellulose, and polyols derived from biomass, and mixtures thereof.

[0095] The plant-based polyol for use in the coating composition of the present invention can also be derived form a vegetable oil, such as soy bean oil, peanut oil, and canola oil, that contain carbon-carbon double bonds, but no hydroxyl groups and have been modified toAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0096] introduce hydroxyl groups onto the carbon chain of the fatty acids, for example, by oxidation of the C-C double bond.

[0097] Examples of commercially available plant-based polyols include plant-based polyether polyols, e.g. poly(trimethylene ether) glycols (PO3G) from SK Chemicals Co., Ltd. or WeylChem International GmbH and Agrol 2.0, 3.6, 4.3, 5.6 and 7.0 (plant-based polyols (soybean oil) commercially available from BioBased Technologies).

[0098] In an embodiment, the coating composition contains a total of at least 25 wt%, at least 27.5 wt%, at least 30 wt%, at least 32.5 wt%, at least 35 wt%, at least 37.5 wt%, or at least 40 wt% of the plant-based polyol. The coating composition contains a total of at most 50 wt%, at most 47.5 wt%, at most 45 wt%, at most 42.5 wt%, at most 40 wt%, at most 37.5 wt%, or at most 35 wt% of the plant-based polyol. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above. Exemplary ranges include 25 wt% to 50 wt%, 30 wt% to 50 wt%, 35 wt% to 50 wt%, 40 wt% to 50 wt%, 25 wt% to 45 wt%, 30 wt% to 45 wt%, 35 wt% to 45 wt%, 40 wt% to 45 wt%, 25 wt% to 40 wt%, 30 wt% to 40 wt%, 35 wt% to 40 wt%, 25 wt% to 35 wt%, and 30 wt% to 35 wt%.

[0099] (E) Additives

[0100] In an embodiment of the present invention, the two-part coating composition components (A) and (B) are mixed together and components (C) and (D) are mixed together. In an embodiment, the mixture of components (A) and (B) may further contain one or more additives (E). In an embodiment, the mixture of components (C) and (D) may further contain one or more additives (E). In an embodiment, the mixture of components (A) and (B) or the mixture of components (C) and (D) contain one or more additives (E). In an embodiment, theAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0101] mixture of components (A) and (B) and the mixture of components (C) and (D) contain one or more additives (E), wherein the additives (E) in each mixture may be the same or different.

[0102] In an embodiment, component (E) (i.e., one or more additives) are added to the mixture of components (A) and (B). In an embodiment, component (E) (i.e., one or more additives) are added to the mixture of components (C) and (D). In an embodiment, component (E) (i.e., one or more additives) are added to the mixture of components (A) and (B) and the mixture of components (C) and (D) contain one or more additives (E), wherein the additives (E) in each mixture may be the same or different.

[0103] Examples of such additives include:

[0104] • Solvent: To adjust viscosity and facilitate water-based dispersion.

[0105] • Fillers: To enhance mechanical properties and further increase the bio-content.

[0106] • Plasticizers: To improve flexibility and processability.

[0107] • Stabilizers: To enhance shelf life and prevent premature curing.

[0108] • Water-based epoxy resin: To enhance adhesion and film formation properties.

[0109] • Bio-based hardeners: Reacts with the resin to initiate the curing process, forming a cross-linked network that imparts strength and durability.

[0110] • Inorganic salts: Serve various functions including structural, functional, and aesthetic purposes.

[0111] • One or more other additives: To affect the properties of the composition based on the intended use.

[0112] (E-l) Solvent

[0113] In an embodiment, the coating composition comprises one or more solvents.

[0114] Inclusion of a solvent may facilitate adjustment of the viscosity and facilitate water-based dispersion.

[0115] The solvent includes, but is not limited to, alcohols such as ethanol or methanol, water, chloroform, dichloromethane, dimethyl sulfoxide, and dimethyl formamide.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0116] The coating composition may contain a total of at least 2.5 wt%, at least 5 wt%, at least 7.5 wt%, at least 10 wt%, at least 12.5 wt%, at least 15 wt%, at least 17.5 wt%, or at least 20 wt% of a solvent. The coating composition contains a total of at most 40 wt%, at most 35 wt%, at most 30 wt%, at most 25 wt%, at most 20 wt%, or at most 15 wt% of a solvent. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above.

[0117] In an embodiment, the solvent is water-based (i.e., is contained in water as a solvent). In an embodiment, the solvent is water. In an embodiment, the solvent has low VOC content or is free from (i.e., has zero) VOCs. In and embodiment, the solvent is free from VOCs. In an embodiment, the coating composition is free from organic solvents.

[0118] In an embodiment, the solvent is added to the coating composition prior to application. For example, the components of the coating composition may be mixed and then diluted prior to application. In another application, one or more of components (A) - (D), in part or in full or in any combination thereof, may be pre-mixed with solvent and then mixed with the remaining components prior to application.

[0119] (E-2) Fillers

[0120] In an embodiment, the coating composition contains one or more fillers. Inclusion of fillers may enhance mechanical properties and / or further increase the bio-based components content.

[0121] In an embodiment, the filler is selected from ground or precipitated calcium carbonate, optionally coated with fatty acid (e.g., stearates), baryte (heavy spar), talc, quartz flour, quartz sand, silicon carbide, iron mica, dolomite, wollastonite, kaolin, mica (potassium aluminum silicate), molecular sieves, aluminum oxide, zinc oxide, aluminum- doped zinc oxide, aluminum hydroxide, magnesium hydroxide, silica, cement, gypsum, fly ash, carbonAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0122] black, graphite, metal powders (e.g., as aluminum, copper, iron, zinc, silver or steel), PVC powder or hollow beads or a combination thereof.

[0123] In an embodiment, the filler is a bio-based filler. The use of a bio-based filler is particularly advantageous in some embodiments as it can be used to increase the total biobased components content in the coating composition. Bio-based fillers include lignin powder, pulverized nutshells, fruit stones, wood flour, cork powder, cellulose fibers or a combination thereof.

[0124] (E-3) Plasticizers

[0125] In an embodiment, the coating composition contains one or more plasticizers.

[0126] Inclusion of plasticizers may improve flexibility and processability. It is advantageous in some embodiments to utilize a bio-based plasticizer to further increase the bio-based components content.

[0127] Suitable plasticizers include carboxylic acid esters, such as phthalates, especially diisononyl phthalate (DINP), diisodecyl phthalate (DIDP) or di(2-propylheptyl)phthalate (DPHP), hydrogenated phthalates (e.g., hydrogenated diisononyl phthalate or diisononyl cyclohexane- 1,2-dicarboxylate (DINCH)), terephthalates (e.g., bis(2-ethylhexyl) terephthalate or diisononyl terephthalate), hydrogenated terephthalates (e.g., hydrogenated bis(2-ethylhexyl) terephthalate or diisononyl terephthalate), or bis(2-ethylhexyl) cyclohexane- 1,4-dicarboxylate, trimellitates, adipates (e.g., dioctyl adipate), azelates, sebacates, benzoates, glycol ethers, glycol esters, organic phosphoric or sulfonic acid esters, polybutenes, polyisobutenes or plasticizers.

[0128] In an embodiment, the plasticizer is a bio-based plasticizer. The bio-based plasticizer may be derived from natural fats or oils, examples include epoxidized oil (see above)Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0129] including epoxidized soybean oil or epoxidized linseed oil. The bio-based plasticizer may be a glycerol derivative.

[0130] (E-4) Stabilizers

[0131] In an embodiment, the coating composition contains one or more stabilizers.

[0132] Inclusion of a stabilizer may enhance shelf life and prevent premature curing.

[0133] In an embodiment, the stabilizer may be a light stabilizer such as UV absorbers and sterically hindered amines (HALS). UV absorbers include substituted benzotriazoles, S-phenyltriazines or oxalanilides. Sterically hindered amines, especially those having a 2, 2,6,6-tetramethylpiperidyl structure, is described by way of example in A. Valet, Lichtschutzmittel für Lacke [Light stabilizers for paints], Vincentz Verlag, Hanover, 1996.

[0134] The stabilizer may also include defoaming agents, anti-cratering and / or wetting agents, levelling agents, film-forming auxiliaries, reactive diluents, biocides, solvents or substances for rheology control.

[0135] Stabilizers, for example free-radical scavengers, and other polymerization inhibitors such as sterically hindered phenols stabilize components during storage and are intended to prevent discoloration during curing. Wetting and levelling agents improve surface wetting and / or the levelling of coatings. Examples are fluorosurfactants, silicone surfactants and specific poly acrylates. Rheology-control additives are important in order to control the properties of the two-component system on application and in the levelling phase on the substrate and are disclosed, for example, in WO 9422968, EP0276501, EP0249201 or WO 9712945, which are incorporated herein by reference. It is additionally possible to employ water scavengers, for example triethyl orthoformate, toluenesulfonyl isocyanate, monooxazolidines or molecular sieves, and hydrolysis stabilizers, for example carbodiimides.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0136] (E-5) Water-based epoxy resin

[0137] In an embodiment, the coating composition contains one or more water-based epoxy resin. The water-based epoxy resin may operate as an additional binder, enhancing adhesion and film formation properties.

[0138] In an embodiment, the water-based epoxy resin may include, but is not limited to, epoxidized animal oils, epoxidized natural rubber, or modified plant-based starches with epoxy functionality.

[0139] In an embodiment, the water-based epoxy resin is a modified plant-based starch with epoxy functionality. In an embodiment, the starch is, for example, acorn squash starch, arrowroot starch, barley starch, butternut squash starch, cassava starch, corn starch (maize starch), manioc starch, lentil starch, lima bean starch, oat starch, pea starch, potato starch, rice starch, sorghum starch, sweet potato starch, tapioca starch, wheat starch, white potato starch, or mixtures thereof. In an embodiment, the bio-based component is corn starch. In an embodiment, the bio-based component is a potato starch.

[0140] When present, the water-based epoxy resin makes up at most 2.5 wt%, at most 2.25 wt%, at most 2 wt%, at most 1.75 wt%, at most 1.5 wt%, at most 1.25 wt%, at most 1 wt%, at most 0.75 wt%, at most 0.5 wt%, or at most 0.25 wt% of the total coating composition.

[0141]

[0142] Bio-Based Hardener

[0143] In an embodiment, the coating composition contains one or more bio-based hardener. The hardener reacts with the resin to initiate the curing process, forming a cross-linked network that imparts strength and durability.

[0144] In an embodiment, the bio-based hardener component is derived from a modified nut oil. The specific type and amount of nut oil used in the hardener can be adjusted to tailor the curing time, mechanical properties, and final characteristics of the epoxy.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0145] Suitable nut oils may include, but are not limited to, almond oil, argan oil, avocado oil, Brazil nut oil, cashew oil, cashew nutshell liquid, groundnut oil, hazelnut oil, macademia nut oil, nutmeg oil, pecan oil, pine nut oil, pistachio oil, and walnut oil, which are modified to provide amine functionality for curing the epoxy resin. In an embodiment, the nut oil is cashew nutshell liquid (CNSL), almond oil, walnut oil, or pistachio oil.

[0146] In an embodiment of the present invention, the bio-based hardener is a polyamide including, but not limited to, a dimer acid and tall oil fatty acid.

[0147] In an embodiment of the present invention, the bio-based hardener is a furanyl based curing agents which may be derived from polysachharides and sugars. Examples of furanyl based curing agents include 5,5 ’-methylenedifurfurylamine (DFDA), 5,5’-ethylidenedifurfurylamine (CH3-DFDA), bis(furfurylamine)A, furfuryl amine, 2,5-bis(aminomethyl)furan, and difurfurylamine.

[0148] In an embodiment of the present invention, the bio-based hardener is a phenylalkamine (also referred to as phenalkamine) or phenylalkamide (also referred to as phenalkamide). Suitable phenylalkamines may include, but are not limited to, phenalkamine curing agents disclosed in U.S. Pat. No. 6,262,148, the entire contents of which is incorporated herein by reference, phenylethanolamine and phenylpropanol amine. Suitable phenylalkamides may include, but are not limited to, phenyl acetamide and phenyl propionamide.

[0149] Another example of phenalkamine curing agents suitable for use in the present invention are biobased phenalkamine produced using cardanol derived from cashew nut shell liquid and an amine in the Mannich reaction, (e.g., Cardolite products 2009SF, 2002, 3025, and 3070).Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0150]

[0151] Phenalkamines may be particularly advantageous in some embodiments and provide fast cure time, excellent low-temperature curing, excellent flexibility, excellent water, corrosion, and chemical resistance properties, and long pot lives.

[0152] In an embodiment, the coating composition contains a total of at most 2.5 wt%, at most 2.25 wt%, at most 2 wt%, at most 1.75 wt%, at most 1.5 wt%, at most 1.25 wt%, at most 1 wt%, at most 0.75 wt%, at most 0.5 wt%, or at most 0.25 wt% of the bio-based hardener.

[0153] (E-7) Inorganic Salts

[0154] In an embodiment, the coating composition contains one or more inorganic salts. The inorganic salts are versatile components in coatings, serving structural, functional, and aesthetic purposes. Their proper selection and formulation are crucial for achieving the desired performance and durability of the coating system.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0155] Some general examples of inorganic salts include: alkali metal salts (e.g., sodium chloride (NaCl), potassium chloride (KCl), lithium carbonate (Li2CO3), sodium bicarbonate (NaHCO3), sodium hydroxide (NaOH)); alkaline earth metal salts (e.g., calcium carbonate (CaCO3), magnesium sulfate (MgSO4), calcium chloride (CaCl2), barium sulfate (BaSO4), strontium nitrate (Sr(NO3)2)); halide salts (e.g., sodium fluoride (NaF), potassium bromide (KBr), calcium iodide (CaI2), ammonium chloride (NH4Cl)); transition metal salts (e.g., iron(III) chloride (FeCl3), copper(II) sulfate (CuSO4), zinc oxide (ZnO), nickel sulfate (NiSO4), manganese(II) sulfate (MnSO4)); sulfates (e.g., aluminum sulfate (Al2(SO4)3), sodium sulfate (Na2SO4), ammonium sulfate ((NH4)2SO4), magnesium sulfate (MgSO4)); phosphates (e.g., sodium phosphate (Na3PO4), calcium phosphate (Ca3(PO4)2), ammonium phosphate ((NH4)3PO4), potassium phosphate (K3PO4)); nitrates (e.g., sodium nitrate (NaNO3), potassium nitrate (KNO3), calcium nitrate (Ca(NO3)2), ammonium nitrate (NH4NO3)); carbonates (sodium carbonate (Na2CO3), calcium carbonate (CaCO3), potassium carbonate (K2CO3), magnesium carbonate (MgCO3)); borax (Na2B4O7·10H2O); alum (KAl(SO4)2·12H2O); chromium(III) oxide (Cr2O3); and titanium dioxide (TiO2).

[0156] Inorganic salts play several critical roles in coating compositions, depending on their type, concentration, and the specific application of the coating. Their functions include:

[0157] 1. Pigmentation and Color Development

[0158] Some inorganic salts act as pigments, imparting color, opacity, and aesthetic properties to coatings. Examples: Titanium dioxide (TiO2): A widely used white pigment for opacity and brightness. Chromium oxide (Cr2O3): Provides green coloration. Iron oxides: Used for red, yellow, and brown hues.

[0159] 2. Anti-Corrosion Properties

[0160] Inorganic salts such as phosphates and chromates create protective layers to prevent metal surfaces from corroding. Examples: Zinc phosphate: A corrosion inhibitor in primersAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0161] for metal. Strontium chromate: Protects against corrosion in aerospace and automotive applications.

[0162] 3. Rheology Modifiers

[0163] Certain salts adjust the viscosity and flow behavior of coatings, improving application properties. Examples: Magnesium aluminum silicate: Used as a thickener or viscosity stabilizer. Sodium carbonate: Helps regulate pH and flow in waterborne coatings.

[0164] 4. Catalytic Functions

[0165] Some inorganic salts act as catalysts to accelerate curing or polymerization of the coating material. Examples: Zinc chloride: Promotes crosslinking in certain resin systems. Tin salts (e.g., dibutyltin dilaurate): Catalysts for polyurethane coatings.

[0166] 5. Conductivity Enhancement

[0167] Salts improve the electrical conductivity of certain coatings, especially in anti-static or electroconductive applications. Examples: Sodium chloride or potassium chloride: Added to enhance ionic conductivity in electrostatic coatings. Lithium salts: Used in electrochemical coatings.

[0168] 6. Flame Retardancy

[0169] Inorganic salts can improve the flame -retardant properties of coatings by forming protective char layers or releasing inert gases during combustion. Examples: Ammonium polyphosphate: A flame retardant additive. Borates: Reduce flammability in coatings.

[0170] 7. Surface Preparation and Adhesion Promotion

[0171] Inorganic salts may modify surface energy or create a chemically reactive surface, enhancing adhesion. Examples: Sodium silicate: Improves adhesion in primers. Zinc oxide: Promotes adhesion between layers of coatings.

[0172] 8. UV and Thermal StabilityAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0173] Certain salts protect coatings from UV degradation or thermal damage, extending the service life of the coating. Examples: Cerium oxide: UV stabilizer in high-performance coatings. Barium sulfate: Enhances thermal and UV resistance.

[0174] 9. Texturing and Mattifying Agents

[0175] Inorganic salts can modify the surface finish of coatings, providing matte or textured appearances. Examples: Silica: Used for matting effects. Calcium carbonate: Adds texture and reduces gloss.

[0176] 10. Fillers and Extenders

[0177] Inorganic salts act as fillers to improve the mechanical properties, reduce costs, and enhance specific characteristics of coatings. Examples: Talc: Improves scratch resistance and durability. Barite (BaSO4): Increases density and enhances gloss control.

[0178] 11. pH and Stability Regulation

[0179] Some salts stabilize the pH of waterborne coatings and prevent premature coagulation or settling. Examples: Sodium bicarbonate: Maintains pH balance. Ammonium salts:

[0180] Stabilize emulsions.

[0181] (E-8) Other Additives

[0182] The coating of the present invention may include a further optional additive component. Exemplary additive components include one or more of a pH modifier, a promoter, a defoamer, a deaerating agent, a wetting agent, a dispersant, a levelling agent, a dispersed paraffin wax, a thickener, a rheology modifier, an emulsifier, a dye, a pigment, an antimicrobial agent, a nanotube, a microcarrier, a curative agent, a catalyst, a surfactant, a plasticizer, a filler, a reinforcement, a chain extender, a corrosion inhibitor, an oil resin (e.g., soy oil resin), a bio-based starch, and / or a crosslinker.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0183] Where the additive is a nanotube or a microcarrier, the nanotube and / or microcarrier may contain additives including at least one of titanium dioxide, a pigment, and an antimicrobial agent.

[0184] Exemplary catalysts include catalysts include tertiary amines, Mannich bases formed from secondary amines, nitrogen-containing bases, alkali metal hydroxides, alkali phenolates, alkali metal alcoholates, hexahydrothiazines, and organometallic compounds. An exemplary catalyst is dibutyltin dilaurate, an organotin compound. The catalyst may be added, in amount from 0.001 wt % to 10 wt %, based on the total weight of the system. The catalyst may accelerate the curing time of isocyanate moieties (e.g., in the isocyanate component or in prepolymers) and active hydrogens (e.g., polyols and / or chain extenders) to offer mechanical properties.

[0185] In an embodiment, the crosslinker is a bio-based crosslinker. In an embodiment, the bio-based crosslinker is a propanediol.

[0186] An exemplary antimicrobial agent is a 2:1 blend of emulsified water-based silver solution and zinc-pyrithione.

[0187] Dyes and / or pigments (such as titanium dioxide and / or carbon black), may be included in the additive component to impart color properties to the coating composition to tune reflective properties and / or UV protective properties. Pigments may be in the form of solids or a dispersion in a resin carrier. Suitable pigments include titanium dioxides, iron oxides, chromium (III) oxides, organic pigments, carbon black or anticorrosion pigments, phosphates, orthophosphates or polyphosphates containing, for example, chromium, zinc, aluminum, calcium, strontium or a combination of these metals as counterions. In an embodiment, the pigment is titanium dioxide.

[0188] Reinforcements (e.g., flake or milled glass and / or fumed silica), may be used to impart certain properties.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0189] The coating composition may be a curable composition that includes curing agent / hardener component in addition to the coating composition or as part of the coating composition. The amount of the hardener component used may vary depending on whether the hardener component is used in addition to or as part of the coating composition. In exemplary embodiments, an amine-based hardener (e.g., one that is known in the art for use in curing epoxy systems) may be excluded because the sprayable polyurethane systems rely on urethane curing chemistry due to minimal residual epoxy content.

[0190] In an embodiment, the oil resin is an epoxidized oil. The epoxidized oil may be derived from a synthetic and / or natural oil. In an embodiment, the epoxidized oil can be any suitable epoxidized oil obtained from a sustainable source. The sustainable source can be a plant oil, vegetable oil, tree oil, nut oil (which is different from (A)), or animal oil. In an embodiment of the present invention, the oil that can be epoxidized (directly or after dehydrogenation) is almond oil, avocado oil, bay oil, basil oil, bergamot oil, oils derived from biomass, Brazil nut oil, broccoli oil, cade oil, canola oil, caraway seed oil, cashew oil, cashew nutshell liquid, cinnamon leaf oil, citronella java oil, citrus seed oil, cod liver oil, com oil, cocoa butter, cottonseed oil, cumin oil, cypress oil, fish oil, flaxseed oil, geranium oil, grapefruit oil, hazelnut oil, lavender oil, lemongrass oil, linseed oil, macademia nut oil, mandarine oil, melissa oil, myrtle oil, neem oil, nutmeg oil, oat oil, olive oil, palm oil, palmarosa oil, peanut oil, pecan oil, peppermint oil, pine nut oil, pistachio oil, rapeseed oil, safflower oil, sage oil, sesame oil, soybean oil, spearmint oil, sunflower oil, high oleic sunflower oil, tea tree oil, thyme oil, triolein, vegetable oil, Vernonia oil, vetiver Haiti oil, walnut oil, wormwood oil, ylang ylang oil or any combination of two or more of the foregoing oils. In an embodiment, the epoxidized oil is epoxidized soybean oil.

[0191] In an embodiment, the bio-based starch additive is, for example, acorn squash starch, arrowroot starch, barley starch, butternut squash starch, cassava starch, corn starch (maizeAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0192] starch), manioc starch, lentil starch, lima bean starch, oat starch, pea starch, potato starch, rice starch, sorghum starch, sweet potato starch, tapioca starch, wheat starch, white potato starch, or mixtures thereof. In an embodiment, the bio-based component is corn starch. In an embodiment, the bio-based component is a potato starch.

[0193] Other additives include, e.g., UV light stabilizers, antioxidants, air release agents, and adhesion promoters, which may be independently used depending on the desired characteristics of the coating composition.

[0194] The additives addition amount will vary depending upon the end use. In an embodiment, the total amount of all additives (based on the total of the coating composition) is no more than 25 wt% no more than 20 wt%, no more than 15 wt%, not more than 10 wt%, or no more than 5 wt%. As an example, where the additive is a defoamer, the total amount is 2 to 9 wt%, 3 to 8 wt%, or 4 to 7 wt%. Alternatively, where the coting composition contains a UV light stabilizer, the amount ranges from 1 to 4 wt% or 2 to 3 wt%. Where the coating composition contains a corrosion inhibitor, the amount ranges from 0.1 to 5 wt%, 0.5 to 4 wt%, 1 to 3 wt%, or 1.5 to 2.5 wt%. Where the coating composition contains an oil resin additive, the amount ranges from 0.1 to 5 wt%, 0.5 to 4 wt%, 1 to 3 wt%, or 1.5 to 2.5 wt%. Where the coating composition contains a bio-based starch additive, the amount ranges from 1 to 20 wt%, 2.5 to 17.5 wt%, 5 to 15 wt%, 7.5 to 12.5 wt%, or 10 to 12 wt%.

[0195] Other exemplary additives and amounts include:

[0196] A reactive surfactant, for example 3-n-pentadecylphenol, with an equivalent weight of from 250 to 300, at an amount of from 1 to 5 wt% or 2 to 4 wt%.

[0197] A diamine with an equivalent weight ranging from 130 to 160, and an amount of from 3 to 9 wt% or 5 to 7 wt%.

[0198] An antimicrobial agent, for example, silver solution and zinc pyrithione, at an amount of from 0.5 to 1.5 wt% or 0.75% to 1.25%.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0199] A comprehensive review of coatings additives is given in “Lehrbuch der Lacke und Beschichtungen [Textbook on paints and coatings], volume III, “Losemittel, Weichmacher, Additive, Zwischenprodukte” [Solvents, plasticizers, additives, intermediates], H. Kittel, Verlag W. A. Colomb in der Heenemann GmbH, Berlin-Oberschwandorf, 1976, pp. 237-398.

[0200] Properties and Attributes

[0201] In an embodiment, the coating composition has low VOC content or is free from (i.e., has zero) VOCs.

[0202] As low VOC content, it is envisioned that there is less than 2 wt%, less than 1.5 wt%, less than 1.0 wt%, less than 0.05 wt%, less than 0.01 wt% total VOCs.

[0203] In an embodiment, the coating composition has no detectable odor.

[0204] In an embodiment, the coating composition has a pH after mixing the components in a solvent ranging from 4.0 to 8.0, from 4.5 to 8.0, from 5.0 to 8.0, from 5.5 to 8.0, from 6.0 to 8.0, from 6.5 to 7.5, from 6.7 to 7.3, from 6.9 to 7.1.

[0205] In an embodiment, the coating composition has a dynamic viscosity at 25°C ranging from 800 to 4000 cps. As a lower viscosity limit, at least 800 cps, at least 850 cps, at least 900 cps, at least 950 cps, at least 1000 cps, at least 1100 cps, at least 1200 cps, at least 1300 cps, at least 1400 cps, at least 1500 cps, at least 1750 cps, and at least 2000 cps are mentioned. As an upper viscosity limit, at most 4000 cps, at most 37500 cps, at most 3500 cps, at most 3250 cps, at most 3000 cps, at most 2750 cps, at most 2500 cps, at most 2250 cps, and at most 2000 cps are mentioned. Ranges and sub-ranges based on a selection of a lower limit and an upper limit from the foregoing are mentioned. Exemplary viscosity ranges include formulations having a viscosity of 800 to 4000 cps, 1000 to 3500 cps, and 1200 to 3000 cps.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0206] The coating composition contains a total of at least 24 wt%, at least 25 wt%, at least 27.5 wt%, at least 30 wt%, at least 35 wt%, at least 40 wt%, at least 45 wt%, at least 50 wt%, at least 55 wt%, or at least 60 wt% of bio-based materials (e.g., the bio-based component as well as other plant-based and / or bio-renewable polymers). The coating composition contains a total of at most 99 wt%, at most 95 wt%, at most 90 wt%, at most 85 wt%, at most 80 wt%, at most 75 wt%, at most 70 wt%, at most 65 wt%, at most 60 wt%, at most 55 wt%, at most 50 wt%, at most 45 wt%, at most 40 wt%, or at most 35 wt% of bio-based materials (e.g., the bio-based component as well as other plant-based and / or bio-renewable polymers). In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above. Exemplary ranges include: 24 wt% to 99 wt%, 30 wt% to 99 wt%, 35 wt% to 99 wt%, 40 wt% to 99 wt%, 24 wt% to 95 wt%, 30 wt% to 95 wt%, 35 wt% to 95 wt%, 40 wt% to 95 wt%, 24 wt% to 85 wt%, 30 wt% to 85 wt%, 35 wt% to 85 wt%, 40 wt% to 85 wt%, 24 wt% to 75 wt%, 30 wt% to 75 wt%, 35 wt% to 75 wt%, 40 wt% to 75 wt%, 24 wt% to 65 wt%, 30 wt% to 65 wt%, 35 wt% to 65 wt%, 40 wt% to 65 wt%, 24 wt% to 50 wt%, 30 wt% to 50 wt%, 35 wt% to 50 wt%, and 40 wt% to 50 wt%.

[0207] In an embodiment, after mixing, the coating composition has a high solids content (prior to dilution with water, i.e., based on the combination of components (A) - (D)) of over 70%, over 75%, over 80%, over 85%, over 90% and up to 95%, up to 90%, up to 85%, up to 80%, up to 75%, inclusive of any sub-range bound by a lower limit and an upper limit for example from 70 to 95%, from 70 to 90%, from 70 to 85%, from 70 to 80%, from 70 to 75%, from 75 to 95%, from 75 to 90%, from 75 to 85%, from 75 to 80%, from 80 to 95%, from 80 to 90%, from 80 to 85%, from 85 to 95%, and from 85 to 90%. This very high solids content reduces transportation costs.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0208] The coating composition of the present invention can be formulated in various forms, such as liquids, pastes, films, depending on the desired application method. The coating is designed to be easily applied to the substrates, either manually or through automated dispensing equipment. Upon application, the coating cures at ambient temperatures, forming a strong and lasting bond to the surface upon which it is applied.

[0209] Kits

[0210] The present invention includes an embodiment where a kit is provided such that the coating composition described above is present together with instructions for preparing and / or using the coating composition.

[0211] In the kits of the present invention, one or more of (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, and (D) a plant-based polyol may be stored in its own individual container or stored in a container in combination with any one or more of the other component(s).

[0212] In an embodiment, components (A) and (B) are stored mixed together.

[0213] In an embodiment, components (C) and (D) are stored mixed together.

[0214] In an embodiment, each of components (A) - (D) are stored individually.

[0215] In the kits of the present invention, one or more additives (E) may be present.

[0216] In an embodiment, the mixture of components (A) and (B) may further contain one or more additives (E).

[0217] In an embodiment, the mixture of components (C) and (D) may further contain one or more additives (E).

[0218] In an embodiment, the mixture of components (A) and (B) or the mixture of components (C) and (D) contain one or more additives (E).Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0219] In an embodiment, the mixture of components (A) and (B) and the mixture of components (C) and (D) contain one or more additives (E), wherein the additives (E) in each mixture may be the same or different.

[0220] In an embodiment, one or more additives (E) are contained in their own separate container(s) for addition as applicable to the desired use. For example, dyes and / or pigments may be stored in a separate container in the kit.

[0221] In an embodiment, each additive is stored in its own separate container(s) for addition as applicable to the desired use.

[0222] Storage temperatures for the kit should be 45° to 90°F, 55° to 85°F, or 60° to 80°F. Freezing temperatures, direct sunlight, & moisture should be avoided. Further, the kit should not be exposed to direct heat and / or should be kept away from heat sources.

[0223] In an embodiment, the coating composition is contained in a delivery device. In an embodiment the delivery device may contain the coating composition and a curing agent in separate chambers of a delivery device, wherein each container is connected to a mixing chamber by way of a tube, a channel, or other delivery vehicle.

[0224] In an embodiment, the delivery device further comprises a tip, tube, channel or other outlet for application of the coating to the desired surface.

[0225] Method of Preparing a Coating Composition

[0226] In an embodiment, the coating composition is prepared by: stirring, shaking, or agitating (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives, for a time and under conditions sufficient to blend (A) a solids-based epoxy resin, (B) an epoxidized plantbased oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives to substantial homogeneity thus forming the coating composition, wherein theAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0227] coating composition has a total solids content ranging from 70% to 95% based on components (A) - (D).

[0228] In an embodiment, a solvent is present and the solvent has low or is free from volatile organic compounds.

[0229] In an embodiment, (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives may be added in any order.

[0230] In an embodiment, all components are added together and the mixture is then stirred, shaken, or agitated. In this embodiment, one or more components may be dissolved in sufficient solvent to permit formation of a substantially homogenous dissolution or suspension.

[0231] In an embodiment, (A) the solids-based epoxy resin is dissolved in sufficient solvent to permit formation of a substantially homogenous dissolution or suspension followed by addition, in any order, individually or together, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives. In an embodiment, components (B) - (D) are pre-mixed before addition to component (A).

[0232] In an embodiment, (B) an epoxidized plant-based oil is dissolved in sufficient solvent to permit formation of a substantially homogenous dissolution or suspension followed by addition, in any order, individually or together, (A) the solids-based epoxy resin, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives. In an embodiment, components (A), (C), and (D) are pre-mixed before addition to component (B).

[0233] In an embodiment, (C) a polyester polyol is dissolved in sufficient solvent to permit formation of a substantially homogenous dissolution or suspension followed by addition, in any order, individually or together, (A) the solids-based epoxy resin, (B) an epoxidized plant-Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0234] based oil, (D) a plant-based polyol, and, optionally (E) one or more additives. In an embodiment, components (A), (B), and (D) are pre-mixed before addition to component (C).

[0235] In an embodiment, (D) a plant-based polyol is dissolved in sufficient solvent to permit formation of a substantially homogenous dissolution or suspension followed by addition, in any order, individually or together, (A) the solids-based epoxy resin, (B) an epoxidized plantbased oil, (C) a polyester polyol, and, optionally (E) one or more additives. In an embodiment, components (A) - (C) are pre-mixed before addition to component (D).

[0236] In an embodiment, (A) the solids-based epoxy resin and (B) an epoxidized plantbased oil, and, optionally (E) one or more additives are pre-mixed to form a substantially homogenous dissolution or suspension followed by addition, in any order, individually or together, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives. In an embodiment, components (C) and (D) are pre-mixed before addition to components (A) and (B).

[0237] In an embodiment, (C) a polyester polyol and (D) a plant-based polyol, and, optionally (E) one or more additives are pre-mixed to form a substantially homogenous dissolution or suspension followed by addition, in any order, individually or together, (A) the solids-based epoxy resin and (B) an epoxidized plant-based oil, and, optionally (E) one or more additives. In an embodiment, components (A) and (B) are pre-mixed before addition to components (C) and (D).

[0238] In the method of the present invention, the component(s) and mixtures thereof are stirred, shaken, or agitated for a time and under conditions suitable to fully disperse the component(s).

[0239] The time and conditions for stirring, shaking, or agitating (i.e., mixing) is not particularly limited so long as it is sufficient to ensure that (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and,Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0240] optionally (E) one or more additives, respectively, are fully dispersed (e.g., in a solvent). The time and conditions would be understood to the skilled artisan. Exemplary, times are from 15 seconds to 5 minutes, from 30 seconds to 4 minutes, from 1 minute to 3 minutes. Stirring can be accomplished by using a jiffy blade mixer at a slow speed (e.g., 400 rpm, 450 rpm, 500 rpm, 550 rpm, 600 rpm). Alternatively, hand shaking or agitation may be used.

[0241] “Substantially homogeneity” or “substantially homogeneous” in this context means that the (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives, as applicable, are mixed well and in a manner that permits creation of an approximately uniform dispersion. In an embodiment, the total mixing time is from 30 seconds to 5 minutes, from 1 minute to 4 minutes, from 2 minutes to 3 minutes.

[0242] In the preparation method above, the coating composition may optionally be allowed stand for a time ranging from 30 seconds to 5 minutes, from 1 minute to 4 minutes, from 2 minutes to 3 minutes prior to being applied to a surface of a material.

[0243] In an embodiment, after mixing a solvent is added to the coating composition prior to application. For example, the components of the coating composition may be mixed and then diluted prior to application. In another embodiment, one or more of components (A) - (D), and optionally one or more additives (E), in part or in full or in any combination thereof, may be pre-mixed with solvent and then mixed with the remaining components prior to application.

[0244] After dilution, the coating composition may contain a total of at least 2.5 wt%, at least 5 wt%, at least 7.5 wt%, at least 10 wt%, at least 12.5 wt%, at least 15 wt%, at least 17.5 wt%, or at least 20 wt% of a solvent. The coating composition contains a total of at most 40 wt%, at most 35 wt%, at most 30 wt%, at most 25 wt%, at most 20 wt%, or at most 15 wt%Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0245] of a solvent. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above.

[0246] In an embodiment, following dilution the coating composition may optionally be allowed stand for a time ranging from 30 seconds to 5 minutes, from 1 minute to 4 minutes, from 2 minutes to 3 minutes prior to being applied to a surface of a material.

[0247] In an embodiment, the coating composition has low VOC content or is free from (i.e., has zero) VOCs. As low VOC content, it is envisioned that there is less than 2 wt%, less than 1.5 wt%, less than 1.0 wt%, less than 0.05 wt%, less than 0.01 wt% total VOCs.

[0248] In an embodiment, the coating composition has no detectable odor after mixing. In an embodiment, the coating composition has a pH after mixing ranging from 4.0 to 8.0, from 4.5 to 8.0, from 5.0 to 8.0, from 5.5 to 8.0, from 6.0 to 8.0, from 6.5 to 7.5, from 6.7 to 7.3, from 6.9 to 7.1.

[0249] In an embodiment, the coating composition has a dynamic viscosity at 25°C after mixing ranging from 800 to 4000 cps. As a lower viscosity limit, at least 800 cps, at least 850 cps, at least 900 cps, at least 950 cps, at least 1000 cps, at least 1100 cps, at least 1200 cps, at least 1300 cps, at least 1400 cps, at least 1500 cps, at least 1750 cps, and at least 2000 cps are mentioned. As an upper viscosity limit, at most 4000 cps, at most 37500 cps, at most 3500 cps, at most 3250 cps, at most 3000 cps, at most 2750 cps, at most 2500 cps, at most 2250 cps, and at most 2000 cps are mentioned. Ranges and sub-ranges based on a selection of a lower limit and an upper limit from the foregoing are mentioned. Exemplary viscosity ranges include formulations having a viscosity of 800 to 4000 cps, 1000 to 3500 cps, and 1200 to 3000 cps.

[0250] The coating composition contains a total of at least 24%, at least 25 wt%, at least 27.5 wt%, at least 30 wt%, at least 35 wt%, at least 40 wt%, at least 45 wt%, at least 50 wt%, at least 55 wt%, or at least 60 wt% of bio-based materials (e.g., a plant-based and / or bio-Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0251] renewable polymer). The coating composition contains a total of at most 95wt%, at most 90 wt%, at most 85 wt%, at most 80 wt%, at most 75 wt%, at most 70 wt%, at most 65 wt%, at most 60 wt%, at most 55 wt%, at most 50 wt%, at most 45 wt%, at most 40 wt%, or at most 35 wt% of bio-based materials (e.g., a plant-based and / or bio-renewable materials). In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above. Exemplary ranges include: 24 wt% to 95 wt%, 30 wt% to 95 wt%, 35 wt% to 95 wt%, 40 wt% to 95 wt%, 24 wt% to 85 wt%, 30 wt% to 85 wt%, 35 wt% to 85 wt%, 40 wt% to 85 wt%, 24 wt% to 75 wt%, 30 wt% to 75 wt%, 35 wt% to 75 wt%, 40 wt% to 75 wt%, 24 wt% to 65 wt%, 30 wt% to 65 wt%, 35 wt% to 65 wt%, 40 wt% to 65 wt%, 24 wt% to 50 wt%, 30 wt% to 50 wt%, 35 wt% to 50 wt%, and 40 wt% to 50 wt%.

[0252] In an embodiment, after mixing, the coating composition has a high solids content (prior to dilution with water, i.e., based on the combination of components (A) - (D)) of over 70%, over 75%, over 80%, over 85%, over 90% and up to 95%, up to 90%, up to 85%, up to 80%, up to 75%, inclusive of any sub-range bound by a lower limit and an upper limit for example from 70 to 95%, from 70 to 90%, from 70 to 85%, from 70 to 80%, from 70 to 75%, from 75 to 95%, from 75 to 90%, from 75 to 85%, from 75 to 80%, from 80 to 95%, from 80 to 90%, from 80 to 85%, from 85 to 95%, and from 85 to 90%. This very high solids content reduces transportation costs.

[0253] Method of Using the Coating Composition and Resulting Material Construct

[0254] In an embodiment is a method of coating a surface of a material by:

[0255] (1) applying a layer of a coating composition comprising (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives to a surface of a material, wherein the coatingAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0256] composition has a total solids content ranging from 70% to 95% based on components (A) – (D), and

[0257] (2) allowing the coating composition to cure.

[0258] In an embodiment, the coating composition may be diluted with a solvent prior to application. For example, the components of the coating composition may be mixed and then diluted prior to application. In another embodiment, one or more of components (A) - (D), and optionally one or more additives (E), in part or in full or in any combination thereof, may be pre-mixed with solvent and then mixed with the remaining components prior to application.

[0259] After dilution, the coating composition may contain a total of at least 2.5 wt%, at least 5 wt%, at least 7.5 wt%, at least 10 wt%, at least 12.5 wt%, at least 15 wt%, at least 17.5 wt%, or at least 20 wt% of a solvent. The coating composition contains a total of at most 40 wt%, at most 35 wt%, at most 30 wt%, at most 25 wt%, at most 20 wt%, or at most 15 wt% of a solvent. In an embodiment of the invention is any range or sub-range bound by a lower (i.e., “at least”) and an upper (i.e., “at most”) limit from those selected above.

[0260] In an embodiment, following dilution the coating composition may optionally be allowed stand for a time ranging from 30 seconds to 5 minutes, from 1 minute to 4 minutes, from 2 minutes to 3 minutes prior to being applied to a surface of a material.

[0261] In an embodiment, the coating composition has low VOC content or is free from (i.e., has zero) VOCs. As low VOC content, it is envisioned that there is less than 2 wt%, less than 1.5 wt%, less than 1.0 wt%, less than 0.05 wt%, less than 0.01 wt% total VOCs.

[0262] In an embodiment, the coating composition has no detectable odor after mixing. In an embodiment, the coating composition has a pH after mixing ranging from 4.0 to 8.0, from 4.5 to 8.0, from 5.0 to 8.0, from 5.5 to 8.0, from 6.0 to 8.0, from 6.5 to 7.5, from 6.7 to 7.3, from 6.9 to 7.1.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0263] In an embodiment, the coating composition has a dynamic viscosity at 25°C after mixing ranging from 800 to 4000 cps. As a lower viscosity limit, at least 800 cps, at least 850 cps, at least 900 cps, at least 950 cps, at least 1000 cps, at least 1100 cps, at least 1200 cps, at least 1300 cps, at least 1400 cps, at least 1500 cps, at least 1750 cps, and at least 2000 cps are mentioned. As an upper viscosity limit, at most 4000 cps, at most 37500 cps, at most 3500 cps, at most 3250 cps, at most 3000 cps, at most 2750 cps, at most 2500 cps, at most 2250 cps, and at most 2000 cps are mentioned. Ranges and sub-ranges based on a selection of a lower limit and an upper limit from the foregoing are mentioned. Exemplary viscosity ranges include formulations having a viscosity of 800 to 4000 cps, 1000 to 3500 cps, and 1200 to 3000 cps.

[0264] Depending upon the surface to be treated, the application method, and the desired application thickness, among other factors, the coating composition of the present invention may be diluted by up to 50% (i.e., add an equal amount of solvent to the volume of the mixed coating composition), up to 40%, up to 30%, up to 25%, up to 20%, up to 15%, or up to 10% with a solvent. In this regard, there would be a corresponding decrease in the solids content of the coating composition to be applied. Thinning by dilution may be desirable for some applications to avoid lap marks and / or to allow for proper self-leveling characteristics. In an embodiment, the solvent has low VOC content or is free from (i.e., has zero) VOCs. The solvent for dissolution may be water.

[0265] The coating composition of the present invention may be applied directly to a surface of a material.

[0266] Application of the coating composition can be in one coating layer or multiple coating layers.

[0267] Overall, the total application and / or dry film thickness may be at least 0.001 inches (1 mil), at least 0.002 inches (2 mils), at least 0.003 inches (3 mils), at least 0.004 inches (4Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0268] mils), at least 0.005 inches (5 mils), at least 0.006 inches (6 mils), at least 0.007 inches (7 mils), at least 0.008 inches (8 mils), at least 0.009 inches (9 mils), at least 0.010 inches (10 mils), at least 0.011 inches (11 mils), at least 0.012 inches (12 mils), at least 0.013 inches (13 mils), at least 0.014 inches (14 mils), at least 0.015 inches (15 mils), at least 0.016 inches (16 mils), at least 0.017 inches (17 mils), at least 0.018 inches (18 mils), at least 0.019 inches (19 mils), at least 0.020 inches (20 mils), at least 0.021 inches (21 mils), at least 0.022 inches (22 mils), at least 0.023 inches (23 mils), at least 0.024 inches (24 mils), at least 0.025 inches (25 mils), at least 0.026 inches (26 mils), at least 0.027 inches (27 mils), at least 0.028 inches (28 mils), at least 0.029 inches (29 mils), at least 0.030 inches (30 mils), at least 0.031 inches (31 mils), at least 0.032 inches (32 mils), at least 0.033 inches (33 mils), at least 0.034 inches (34 mils), at least 0.035 inches (35 mils), at least 0.036 inches (36 mils), at least 0.037 inches (37 mils), at least 0.038 inches (38 mils), at least 0.039 inches (39 mils), at least 0.040 inches (40 mils), at least 0.050 inches (50 mils), at least 0.060 inches (60 mils), at least 0.070 inches (70 mils), at least 0.080 inches (80 mils), at least 0.090 inches (90 mils), or at least 0.100 inches (100 mils). Overall, the total thickness may be at most 0.500 inches (500 mils), at most 0.400 inches (400 mils), at most 0.300 inches (300 mils), at most 0.250 inches (250 mils), at most 0.200 inches (200 mils), at most 0.150 inches (150 mils), at most 0.100 inches (100 mils), at most 0.090 inches (90 mils), at most 0.080 inches (80 mils), at most 0.070 inches (70 mils), at most 0.060 inches (60 mils), at most 0.050 inches (50 mils), at most 0.049 inches (49 mils), at most 0.048 inches (48 mils), at most 0.047 inches (47 mils), at most 0.046 inches (46 mils), at most 0.045 inches (45 mils), at most 0.044 inches (44 mils), at most 0.043 inches (43 mils), at most 0.042 inches (42 mils), at most 0.041 inches (41 mils), at most 0.040 inches (40 mils), at most 0.039 inches (39 mils), at most 0.038 inches (38 mils), at most 0.037 inches (37 mils), at most 0.036 inches (36 mils), at most 0.035 inches (35 mils), at most 0.034 inches (34 mils), at most 0.033 inches (33 mils), at most 0.032 inches (32 mils), at most 0.031 inches (31 mils),Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0269] or at most 0.030 inches (30 mils). Ranges and sub-ranges based on a selection of a lower limit and an upper limit from the foregoing are included in the present invention. Exemplary thickness ranges include coating thicknesses of from 0.001 to 0.500 inches (1 – 500 mils), from 0.002 to 0.250 inches (2 – 250 mils), from 0.003 to 0.200 inches (3 – 200 mils), from 0.004 to 0.100 inches (4 to 100 mils), from 0.005 to 0.050 inches (5 to 50 mils) or from 0.010 to 0.040 inches (10 to 40 mils).

[0270] Where multiple layers (i.e., applications) are used, the application thickness per layer may be 1 to 50 mils, 2 to 45 mils, 3 to 40 mils, 4 to 35 mils, 5 to 30 mils, 5 to 25 mils, 5 to 20 mils, 5 to 15 mils, or 5 to 10 mils. Of course, thinner coating ranges are also envisioned by selecting any lower and upper limit from the foregoing including, for example, from 1 to 10 mils, 2 to 10 mils, 2 to 15 mils, 2 to 20 mils, 3 to 10 mils, 3 to 15 mils, 3 to 20 mils, 4 to 10 mils, 4 to 15 mils, or 4 to 20 mils. Where multiple layers are used, there are at least 2, at least 3, at least 4, or least 5 layers to at most 10 layers, at most 9 layers, at most 8 layers, at most 7 layers, at most 6 layers, or at most 5 layers. Illustrative exemplary ranges including 2 to 10 layers, 2 to 8 layers, 2 to 5 layer, 3 to 10 layers, 3 to 8 layer, and 3 to 5 layers.

[0271] The coating composition may be applied to the surface of a material by brushing, rolling, or spraying.

[0272] The coating composition of the present invention has a coverage rate of approximately 250 to 400 sq. ft. per gallon; however, the coverage rate is impacted by the material (e.g., substrate) to be treated, the surface pretreatment, and whether or not the coating composition was diluted before application. The following table includes approximate coverage rates for different substrates:

[0273] Substrate Sq Ft / Gallon Textured Surface - 250-300

[0274] All Masonry Surface - 300

[0275]

[0276] Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0277] Painted Surfaces - 400

[0278] Wood Surfaces - 300

[0279] Metal - 400

[0280] Tile - 350

[0281]

[0282] Following application to the surface of a material, the coating composition of the present invention has a dry-time ranging from 2 to 15 hours, from 3 to 14 hours, from 4 to 13 hours, from 5 to 12 hours, from 6 to 11 hours, or from 7 to 10 hours, but the drying time varies depending upon the temperature, ventilation, and catalyst system being used. For example, the drying time at ambient temperature may be 8 hours or less.

[0283] After preparing the coating composition, a process for curing the composition may be used to form a thermoset or cured composition. For example, the composition or formulation may be cured under conventional processing conditions to form a coating bond. Curing the coating composition may be carried out at curing reaction conditions including a predetermined temperature and for a predetermined period of time sufficient to cure the composition. The curing conditions may be dependent on the various components used in the curable composition such as the hardener used in the formulation. The curing reaction conditions include, e.g., carrying out the reaction under a temperature, generally in the range of from -5° C. to 60° C. (e.g., 0° C. to 50° C., 5° C. to 45° C., 10° C. to 35° C., 15° C. to 30° C., 20° C. to 27.5° C. etc.), including ambient temperature. For sprayable applications, the coating may be applied to substrates, e.g., using airless sprayers and air-assisted pneumatic sprayers and the like. The applied composition may be cured by heating the composition at the aforementioned curing temperatures.

[0284] Following drying of a first layer or when the coating is tack free, a second coating layer may be applied by spraying, rolling, or brushing (which may be repeated for additionalAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0285] layers). However, for proper adhesion, it is desired to apply the second (or subsequent) coat within 24 hours, within 18 hours, within 12 hours, or within 6 hours of application of the first (or prior) coat. If the first (or prior) coat has dried longer than 24-hours, the surface may be abraded or etched to promote adhesion of the second (or subsequent) coat.

[0286] Temperature and humidity directly affect pot life and dry time. Accordingly, in an embodiment the conditions should be between 40 – 95 °F, between 50 and 85 °F, between 60 and 80 °F, or between 65 and 75 °F and the humidity should not exceed 80%, not exceed 70%, not exceed 60%, or not exceed 50%.

[0287] In an embodiment, the surface to be coated has a moisture content of no more than 25%, no more than 20%, no more than 15%, no more than 10%, or no more than 5% as measured with an electronic moisture meter.

[0288] Prior to application of the coating composition to a surface(s), the surface(s) may pretreated and / or cleaned.

[0289] In an embodiment, the surface(s) to be adhered may be cleaned prior to application of the coating composition. For example, to facilitate proper adherence, the surface can be cleaned to remove dirt, debris, grime, minerals such as lime and calcium, oils, release agents, grease, mud, excess mortar, and mold and mildew, etc.

[0290] In an embodiment, the surface may be pretreated with a primer (e.g., smooth surfaces) or a sealer or filler to remove pinholes (e.g., porous surfaces). Another envisioned pretreatment includes pointing and / or caulking all cracks. Further, all voids, beeholes, masonry surface defects and openings such as conduits, pipes, drains, door frames, vents, air conditioner openings, electrical openings, control joints, or any dissimilar materials should be repaired using urethane or other approved patching.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0291] Another form of surface pretreatment envisioned in the present invention includes fluting, scoring, sandblasting, and / or etching as well as raking joints. Pretreating a surface in this manner can increase the absorption, but will also lower coverage rates.

[0292] In an embodiment, the coating composition is not applied where freezing temperatures have existed prior to application. In such a situation, adequate time should be allowed for the application surface to thaw. In an embodiment, air, surface, and material temperatures should be above 40°F (4.4°C) and at least 5°F above the dew point prior to application. Further, it is not desirable to apply the coating composition where temperatures are below 40°F or when temperatures are expected to drop below 40°F within 48 hours of application. For exterior surfaces, application should also be avoided if rain, snow, or lower temperatures are expected within 48 hours. Further, the coating composition would be adversely affective if relative humidity is greater than 90% and, therefore, it should be avoided.

[0293] In the case of spills or following application excess coating composition can be cleaned up with water.

[0294] Coated Products

[0295] The coating composition of the present invention may find utility in many different industries including oil and gas, steel fabrication, bridge and highway, power generation, marine, food processing, pharmaceutical, veterinary, hospitals, and restaurants.

[0296] An exemplary use includes roofs (including asphalt shingles, metal roofs, concrete roofs, and concrete tiles, etc.), floors (concrete, ceramic, wood, metal, galvanized steel, ungalvanized steel, tile, etc.) in several industries including food processing, veterinary, hospitals, restaurants and other facilities. Other uses include warehouses, food and beverage facilities, USDA inspected facilities, commercial vehicles, airports, stadiums, sound walls,Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0297] stadiums, direct-to-metal, direct-to-aluminum, direct-to-galvanized steel, direct-to-ungalvanized steel.

[0298] Thus, the coating composition is suitable for and has excellent adherence properties with a broad scope of materials including asphalt, ceramic, glass, concrete, wood, metal, galvanized steel, ungalvanized steel, tile, paper packaging (e.g., cardboard), composites, textile and plastic.

[0299] Within the scope of the present invention are materials having a coating made from the coating composition of the present invention. In an embodiment, the coating on the materials is at a total dry film thickness of at least 0.001 inches (1 mil), at least 0.002 inches (2 mils), at least 0.003 inches (3 mils), at least 0.004 inches (4 mils), at least 0.005 inches (5 mils), at least 0.006 inches (6 mils), at least 0.007 inches (7 mils), at least 0.008 inches (8 mils), at least 0.009 inches (9 mils), at least 0.010 inches (10 mils), at least 0.011 inches (11 mils), at least 0.012 inches (12 mils), at least 0.013 inches (13 mils), at least 0.014 inches (14 mils), at least 0.015 inches (15 mils), at least 0.016 inches (16 mils), at least 0.017 inches (17 mils), at least 0.018 inches (18 mils), at least 0.019 inches (19 mils), at least 0.020 inches (20 mils), at least 0.021 inches (21 mils), at least 0.022 inches (22 mils), at least 0.023 inches (23 mils), at least 0.024 inches (24 mils), at least 0.025 inches (25 mils), at least 0.026 inches (26 mils), at least 0.027 inches (27 mils), at least 0.028 inches (28 mils), at least 0.029 inches (29 mils), at least 0.030 inches (30 mils), at least 0.031 inches (31 mils), at least 0.032 inches (32 mils), at least 0.033 inches (33 mils), at least 0.034 inches (34 mils), at least 0.035 inches (35 mils), at least 0.036 inches (36 mils), at least 0.037 inches (37 mils), at least 0.038 inches (38 mils), at least 0.039 inches (39 mils), at least 0.040 inches (40 mils), at least 0.050 inches (50 mils), at least 0.060 inches (60 mils), at least 0.070 inches (70 mils), at least 0.080 inches (80 mils), at least 0.090 inches (90 mils), or at least 0.100 inches (100 mils). Overall, the total thickness may be at most 0.500 inches (500 mils), at most 0.400 inches (400 mils), at mostAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0300] 0.300 inches (300 mils), at most 0.250 inches (250 mils), at most 0.200 inches (200 mils), at most 0.150 inches (150 mils), at most 0.100 inches (100 mils), at most 0.090 inches (90 mils), at most 0.080 inches (80 mils), at most 0.070 inches (70 mils), at most 0.060 inches (60 mils), at most 0.050 inches (50 mils), at most 0.049 inches (49 mils), at most 0.048 inches (48 mils), at most 0.047 inches (47 mils), at most 0.046 inches (46 mils), at most 0.045 inches (45 mils), at most 0.044 inches (44 mils), at most 0.043 inches (43 mils), at most 0.042 inches (42 mils), at most 0.041 inches (41 mils), at most 0.040 inches (40 mils), at most 0.039 inches (39 mils), at most 0.038 inches (38 mils), at most 0.037 inches (37 mils), at most 0.036 inches (36 mils), at most 0.035 inches (35 mils), at most 0.034 inches (34 mils), at most 0.033 inches (33 mils), at most 0.032 inches (32 mils), at most 0.031 inches (31 mils), or at most 0.030 inches (30 mils). Ranges and sub-ranges based on a selection of a lower limit and an upper limit from the foregoing are included in the present invention. Exemplary thickness ranges include coating thicknesses of from 0.001 to 0.500 inches (1 – 500 mils), from 0.002 to 0.250 inches (2 – 250 mils), from 0.003 to 0.200 inches (3 – 200 mils), from 0.004 to 0.100 inches (4 to 100 mils), from 0.005 to 0.050 inches (5 to 50 mils) or from 0.010 to 0.040 inches (10 to 40 mils).

[0301] Therefore, within the scope of the present invention is a material having a coating as defined that has low or is free from volatile organic compounds and the thickness has at least 24 wt% of the bio-based component based on the total solids content of the coating.

[0302] In an embodiment, the coating composition is a primer coating. In an embodiment of the invention, wherein the coating composition is a primer coating, one or more coating layer having a composition different that the coating composition of the present invention is applied over said coating composition.

[0303] Benefits of the

[0304]

[0305] Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0306] In some embodiments, the coating composition of the present invention provides one or more of the following advantages over conventional epoxy-based coatings:

[0307] • Low Cost: The use of a 100% solids epoxy resin that is made water-reducible allows for a much lower cost formula than a traditional water-based epoxy, which are approximately 50% and average $6 / lb.

[0308] • Higher Durability: The high solids of this water-reducible epoxy system makes it more durable than traditional water-based epoxies.

[0309] • Bio-based and sustainable: The high bio-based content reduces reliance on petroleum-based materials.

[0310] • Water-reducible: Reduces VOC emissions and environmental impact.

[0311] • High UV resistance: Provides long-lasting color and gloss retention.

[0312] • Excellent adhesion: Bonds strongly to various substrates.

[0313] • Corrosion protection: Protects metal surfaces from corrosion.

[0314] • Chemical resistance: Withstands exposure to various chemicals.

[0315] Exemplary embodiments of the present invention include:

[0316] [1] A coating composition comprising:

[0317] (A) a solids-based epoxy resin;

[0318] (B) an epoxidized plant-based oil;

[0319] (C) a polyester polyol; and

[0320] (D) a plant-based polyol; and

[0321] (E) optionally, one or more additives,

[0322] wherein the coating composition has a total solids content ranging from 70% to 95%.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0323] [2] The coating composition of [1], wherein the composition contains 30 wt% to 60 wt% of component (A), wherein the percentage is based on the total of components (A) - (D).

[0324] [3] The coating composition of [1] or [2], wherein the composition contains 1 wt% to 10 wt% of component (B), wherein the percentage is based on the total of components (A) – (D).

[0325] [4] The coating composition of any one of [1] - [3], wherein the composition contains 2 wt% to 15 wt% of component (C), wherein the percentage is based on the total of components (A) - (D).

[0326] [5] The coating composition of any one of [1] - [4], wherein the composition contains 25 wt% to 50 wt% of component (D), wherein the percentage is based on the total of components (A) - (D).

[0327] [6] The coating composition of any one of [1] - [5], wherein the composition contains 30 wt% to 60 wt% of component (A), 1 wt% to 10 wt% of component (B), 2 wt% to 15 wt% of component (C), and 25 wt% to 50 wt% of component (D), wherein the percentages are based on the total of components (A) - (D).

[0328] [7] The coating composition of any one of [1] - [6], wherein (A) is selected from the group consisting of a bisphenol A diglycidyl ether, a bisphenol F diglycidyl ether, and a novolac epoxy resin.

[0329] [8] The coating composition of any one of [1] - [7], wherein (B) is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil, and epoxidized castor oil.

[0330] [9] The coating composition of any one of [1] - [8], wherein (C) is derived from adipic acid or phthalic anhydride.

[0331]

[0010] The coating composition of any one of [1] - [9], wherein (D) is selected from the group consisting of sorbitol, glycerol, and a polyol derived from biomass.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0332]

[0011] The coating composition of any one of [1] -

[0010] , further comprising a solvent.

[0333]

[0012] The coating composition of

[0011] , wherein the solvent has low volatile organic compounds content.

[0334]

[0013] The coating composition of

[0011] or

[0012] , wherein the solvent is free of volatile organic compounds.

[0335]

[0014] The coating composition of any one of

[0011] -

[0013] , wherein the solvent is water.

[0336]

[0015] The coating composition of any one of [1] -

[0014] , wherein the coating composition has low volatile organic compounds content.

[0337]

[0016] The coating composition of any one of [1] -

[0015] , wherein the coating composition is free of volatile organic compounds.

[0338]

[0017] The coating composition of any one of [1] –

[0018] , wherein the composition has a pH ranging from 4.0 to 8.0.

[0339]

[0018] The coating composition of any one of [1] –

[0017] , wherein the coating composition has a dynamic viscosity at 25°C ranging from 800 to 4000 cps.

[0340]

[0019] The coating composition of any one of [1] –

[0018] , wherein (E) is present and is selected from the group consisting of a solvent, a filler, a plasticizer, a stabilizer, a waterbased epoxy resin, a bio-based hardener, an inorganic salt, and an other additive or a mixture thereof.

[0341]

[0020] The coating composition of any one of [1] –

[0019] , wherein the other additive is one or more selected from the group consisting of a pH modifier, a promoter, a defoamer, a deaerating agent, a wetting agent, a dispersant, a levelling agent, a dispersed paraffin wax, a thickener, a rheology modifier, an emulsifier, a dye, a pigment, an antimicrobial agent, a nanotube, a microcarrier, a curative agent, a catalyst, a surfactant, a plasticizer, a filler, a reinforcement, a chain extender, a corrosion inhibitor, an oil resin, a bio-based starch, and a crosslinker.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0342]

[0021] The coating composition of any one of [1] -

[0020] , wherein the coating composition has 24 wt% to 95 wt% bio-based materials.

[0343]

[0022] A kit comprising, the coating composition of claim 1 together with instructions for use thereof, wherein the coating composition comprises components (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives, wherein the coating composition has a total solids content ranging from 70% to 95% based on components (A) - (D).

[0344]

[0023] The kit of

[0022] , wherein one or more of (A), (B), (C), (D), and (E) are separately packaged.

[0345]

[0024] The kit of

[0022] or

[0023] , further comprising a delivery device.

[0346]

[0025] A method of making a coating composition, comprising

[0347] stirring, shaking, or agitating (A) a solids-based epoxy resin, (B) an epoxidized plantbased oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives, for a time and under conditions sufficient to blend (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives to substantial homogeneity thus forming the coating composition, wherein the coating composition has a total solids content ranging from 70% to 95% based on components (A) - (D).

[0348]

[0026] The method of

[0025] , further comprising adding a solvent after the components are blended to substantial homogeneity.

[0349]

[0027] The method of

[0026] , wherein the solvent has low volatile organic compounds content.

[0350]

[0028] The method of

[0026] or

[0027] , wherein the solvent is free of volatile organic compounds.

[0351]

[0029] The method of any one of

[0026] -

[0028] , wherein the solvent is water.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0352]

[0030] The method of any one of

[0026] -

[0029] , wherein after the solvent is added the coating composition comprises up to 40 wt% of the solvent.

[0353]

[0031] The method of any one of

[0025] -

[0030] , wherein the coating composition has low volatile organic compounds content.

[0354]

[0032] The method of any one of

[0025] -

[0031] , wherein the coating composition is free of volatile organic compounds.

[0355]

[0033] The method of any one of

[0025] -

[0032] , wherein the composition has a pH ranging from 4.0 to 8.0.

[0356]

[0034] The method of any one of

[0025] -

[0033] , wherein the coating composition has a dynamic viscosity at 25°C ranging from 800 to 4000 cps.

[0357]

[0035] The method of any one of

[0025] -

[0034] , wherein the composition contains 30 wt% to 60 wt% of component (A), wherein the percentage is based on the total of components (A) - (D).

[0358]

[0036] The method of any one of

[0025] -

[0035] , wherein the composition contains 1 wt% to 10 wt% of component (B), wherein the percentage is based on the total of components (A) - (D).

[0359]

[0037] The method of any one of

[0025] -

[0036] , wherein the composition contains 2 wt% to 15 wt% of component (C), wherein the percentage is based on the total of components (A) - (D).

[0360]

[0038] The method of any one of

[0025] -

[0037] , wherein the composition contains 25 wt% to 50 wt% of component (D), wherein the percentage is based on the total of components (A) - (D).

[0361]

[0039] The method of any one of

[0025] -

[0038] , wherein the composition contains 30 wt% to 60 wt% of component (A), 1 wt% to 10 wt% of component (B), 2 wt% to 15 wt% ofAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0362] component (C), and 25 wt% to 50 wt% of component (D), wherein the percentages are based on the total of components (A) - (D).

[0363]

[0040] The method of any one of

[0025] -

[0039] , wherein (A) is selected from the group consisting of a bisphenol A diglycidyl ether, a bisphenol F diglycidyl ether, and a novolac epoxy resin.

[0364]

[0041] The method of any one of

[0025] -

[0040] , wherein (B) is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil, and epoxidized castor oil.

[0365]

[0042] The method of any one of

[0025] -

[0041] , wherein (C) is derived from adipic acid or phthalic anhydride.

[0366]

[0043] The method of any one of

[0025] -

[0042] , wherein (D) is selected from the group consisting of sorbitol, glycerol, and a polyol derived from biomass.

[0367]

[0044] The method of any one of

[0025] -

[0043] , wherein (E) is present and is selected from the group consisting of a solvent, a filler, a plasticizer, a stabilizer, a water-based epoxy resin, a bio-based hardener, an inorganic salt, and an other additive or a mixture thereof.

[0368]

[0045] The method of any one of

[0025] -

[0044] , wherein the other additive is one or more selected from the group consisting of a pH modifier, a promoter, a defoamer, a deaerating agent, a wetting agent, a dispersant, a levelling agent, a dispersed paraffin wax, a thickener, a rheology modifier, an emulsifier, a dye, a pigment, an antimicrobial agent, a nanotube, a microcarrier, a curative agent, a catalyst, a surfactant, a plasticizer, a filler, a reinforcement, a chain extender, a corrosion inhibitor, an oil resin, a bio-based starch, and a crosslinker.

[0369]

[0046] The method of any one of

[0025] -

[0045] , wherein the coating composition has 24 wt% to 95 wt% bio-based materials.

[0370]

[0047] A method of coating a surface of a material by:

[0371] (1) applying a layer of a coating composition comprising (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and,Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0372] optionally (E) one or more additives to a surface of a material, wherein the coating composition has a total solids content ranging from 70% to 95% based on components (A) – (D), and

[0373] (2) allowing the coating composition to cure.

[0374]

[0048] The method of

[0047] , wherein (1) and (2) are repeated to form layers of the coating composition.

[0375]

[0049] The method of

[0047] or

[0048] , wherein there are 2 to 5 layers.

[0376]

[0050] The method of any one of

[0047] -

[0049] , wherein the total thickness of the coating composition after said applying ranges from 1 to 500 mils.

[0377]

[0051] The method of any one of

[0047] -

[0050] , wherein the total thickness of the coating composition after said applying ranges from 5 to 50 mils.

[0378]

[0052] The method of any one of

[0047] -

[0051] , wherein said allowing the coating composition to cure is at ambient temperature.

[0379]

[0053] The method of any one of

[0047] -

[0052] , wherein the coating composition further comprises a solvent.

[0380]

[0054] The method of

[0053] , wherein the solvent has low volatile organic compounds content.

[0381]

[0055] The method of

[0053] or

[0054] , wherein the solvent is free of volatile organic compounds.

[0382]

[0056] The method of any one of

[0053] -

[0055] , wherein the solvent is water.

[0383]

[0057] The method of any one of

[0053] -

[0056] , wherein the coating composition comprises up to 40 wt% of the solvent.

[0384]

[0058] The method of any one of

[0047] -

[0057] , wherein the coating composition has a dynamic viscosity at 25°C ranging from 800 to 4000 cps.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0385]

[0059] The method of any one of

[0047] -

[0058] , wherein the composition contains 30 wt% to 60 wt% of component (A), wherein the percentage is based on the total of components (A) - (D).

[0386]

[0060] The method of any one of

[0047] -

[0059] , wherein the composition contains 1 wt% to 10 wt% of component (B), wherein the percentage is based on the total of components (A) - (D).

[0387]

[0061] The method of any one of

[0047] -

[0060] , wherein the composition contains 2 wt% to 15 wt% of component (C), wherein the percentage is based on the total of components (A) - (D).

[0388]

[0062] The method of any one of

[0047] -

[0061] , wherein the composition contains 25 wt% to 50 wt% of component (D), wherein the percentage is based on the total of components (A) - (D).

[0389]

[0063] The method of any one of

[0047] -

[0062] , wherein the composition contains 30 wt% to 60 wt% of component (A), 1 wt% to 10 wt% of component (B), 2 wt% to 15 wt% of component (C), and 25 wt% to 50 wt% of component (D), wherein the percentages are based on the total of components (A) - (D).

[0390]

[0064] The method of any one of

[0047] -

[0063] , wherein (A) is selected from the group consisting of a bisphenol A diglycidyl ether, a bisphenol F diglycidyl ether, and a novolac epoxy resin.

[0391]

[0065] The method of any one of

[0047] -

[0064] , wherein (B) is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil, and epoxidized castor oil.

[0392]

[0066] The method of any one of

[0047] -

[0065] , wherein (C) is derived from adipic acid or phthalic anhydride.

[0393]

[0067] The method of any one of

[0047] -

[0066] , wherein (D) is selected from the group consisting of sorbitol, glycerol, and a polyol derived from biomass.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0394]

[0068] The method of any one of

[0047] -

[0067] , wherein (E) is present and is selected from the group consisting of a solvent, a filler, a plasticizer, a stabilizer, a water-based epoxy resin, a bio-based hardener, an inorganic salt, and an other additive or a mixture thereof.

[0395]

[0069] The method of any one of

[0047] -

[0068] , wherein the other additive is one or more selected from the group consisting of a pH modifier, a promoter, a defoamer, a deaerating agent, a wetting agent, a dispersant, a levelling agent, a dispersed paraffin wax, a thickener, a rheology modifier, an emulsifier, a dye, a pigment, an antimicrobial agent, a nanotube, a microcarrier, a curative agent, a catalyst, a surfactant, a plasticizer, a filler, a reinforcement, a chain extender, a corrosion inhibitor, an oil resin, a bio-based starch, and a crosslinker.

[0396]

[0070] A coated material wherein a surface of a material has a coating of a cured product of a coating composition comprising (A) a solids-based epoxy resin, (B) an epoxidized plant-based oil, (C) a polyester polyol, (D) a plant-based polyol, and, optionally (E) one or more additives, wherein the coating composition has a total solids content ranging from 70% to 95% based on components (A) - (D).

[0397]

[0071] The coated material of

[0070] , wherein the coating has at least 24 wt% of bio-based components based on the total solids content of the coating.

[0398]

[0072] The coated material of

[0070] or

[0071] , wherein the material is selected from the group consisting of asphalt, ceramic, glass, concrete, wood, metal, galvanized steel, ungalvanized steel, tile, paper packaging, composites, textile and plastic.

[0399]

[0073] The coated material of any one of

[0070] -

[0072] , wherein the total thickness of the coating ranges from 1 to 500 mils.

[0400]

[0074] The coated material of any one of

[0070] -

[0073] , wherein the total thickness of the coating ranges from 5 to 50 mils.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0401]

[0075] The coated material of any one of

[0070] -

[0074] , wherein the composition contains 30 wt% to 60 wt% of component (A), wherein the percentage is based on the total of components (A) - (D).

[0402]

[0076] The coated material of any one of

[0070] -

[0075] , wherein the composition contains 1 wt% to 10 wt% of component (B), wherein the percentage is based on the total of components (A) - (D).

[0403]

[0077] The coated material of any one of

[0070] -

[0076] , wherein the composition contains 2 wt% to 15 wt% of component (C), wherein the percentage is based on the total of components (A) - (D).

[0404]

[0078] The coated material of any one of

[0070] -

[0077] , wherein the composition contains 25 wt% to 50 wt% of component (D), wherein the percentage is based on the total of components (A) - (D).

[0405]

[0079] The coated material of any one of

[0070] -

[0078] , wherein the composition contains 30 wt% to 60 wt% of component (A), 1 wt% to 10 wt% of component (B), 2 wt% to 15 wt% of component (C), and 25 wt% to 50 wt% of component (D), wherein the percentages are based on the total of components (A) - (D).

[0406]

[0080] The coated material of any one of

[0070] -

[0079] , wherein (A) is selected from the group consisting of a bisphenol A diglycidyl ether, a bisphenol F diglycidyl ether, and a novolac epoxy resin.

[0407]

[0081] The coated material of any one of

[0070] -

[0080] , wherein (B) is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil, and epoxidized castor oil.

[0408]

[0082] The coated material of any one of

[0070] -

[0081] , wherein (C) is derived from adipic acid or phthalic anhydride.

[0409]

[0083] The coated material of any one of

[0070] -

[0082] , wherein (D) is selected from the group consisting of sorbitol, glycerol, and a polyol derived from biomass.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0410]

[0084] The coated material of any one of

[0070] -

[0083] , wherein (E) is present and is selected from the group consisting of a solvent, a filler, a plasticizer, a stabilizer, a waterbased epoxy resin, a bio-based hardener, an inorganic salt, and an other additive or a mixture thereof.

[0411]

[0085] The coated material of any one of

[0070] -

[0084] , wherein the other additive is one or more selected from the group consisting of a pH modifier, a promoter, a defoamer, a deaerating agent, a wetting agent, a dispersant, a levelling agent, a dispersed paraffin wax, a thickener, a rheology modifier, an emulsifier, a dye, a pigment, an antimicrobial agent, a nanotube, a microcarrier, a curative agent, a catalyst, a surfactant, a plasticizer, a filler, a reinforcement, a chain extender, a corrosion inhibitor, an oil resin, a bio-based starch, and a crosslinker.

[0412] In the context of the present description, all publications, patent applications, patents and other references mentioned herein, if not otherwise indicated, are explicitly incorporated by reference herein in their entirety for all purposes as if fully set forth, and shall be considered part of the present disclosure in their entirety.

[0413] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. In case of conflict, the present specification, including definitions, will control.

[0414] The descriptions of the various embodiments of the present invention have been presented for purposes of illustration, but are not intended to be exhaustive or limited to the embodiments disclosed. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the described embodiments. The terminology used herein was chosen to best explain the principles of the embodiments, the practical application or technical improvement over technologies found inAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0415] the marketplace, or to enable others or ordinary skill in the art to understand the embodiments disclosed herein.

[0416] Except where expressly noted, trademarks are shown in upper case.

[0417] Unless stated otherwise, all percentages, parts, ratios, etc., are by weight.

[0418] When an amount, concentration, or other value or parameter is given as a range, or a list of upper and lower values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper and lower range limits, regardless of whether ranges are separately disclosed. Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range. It is not intended that the scope of the present disclosure be limited to the specific values recited when defining a range. Further, where a numerical limit or range is stated herein, the endpoints are included. Also, all values and subranges within a numerical limit or range are specifically included as if explicitly written out.

[0419] Further, unless otherwise explicitly stated to the contrary, when one or multiple ranges or lists of items are provided, this is to be understood as explicitly disclosing any single stated value or item in such range or list, and any combination thereof with any other individual value or item in the same or any other list.

[0420] When the term “about” is used, it is used to mean a certain effect or result can be obtained within a certain tolerance, and the skilled person knows how to obtain the tolerance. When the term "about" is used in describing a value or an end-point of a range, the disclosure should be understood to include the specific value or end-point referred to.

[0421] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is notAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0422] necessarily limited to only those elements but can include other elements not expressly listed or inherent to such process, method, article, or apparatus.

[0423] The transitional phrase "consisting of" excludes any element, step, or ingredient not specified in the claim, closing the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consists of" appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

[0424] The transitional phrase "consisting essentially of" limits the scope of a claim to the specified materials or steps and those that do not materially affect the basic and novel characteristic(s) of the claimed invention. A “consisting essentially of’ claim occupies a middle ground between closed claims that are written in a “consisting of’ format and fully open claims that are drafted in a “comprising” format. Optional additives as defined herein, at a level that is appropriate for such additives, and minor impurities are not excluded from a composition by the term “consisting essentially of’.

[0425] As used herein, an "embodiment" means that a particular feature, structure or characteristic is included in at least one or more manifestations, examples, or implementations of this invention. Furthermore, the particular features, structures or characteristics may be combined in any suitable manner, as would be apparent to a person skilled in the art. Combinations of features of different embodiments are all meant to be within the scope of the invention, without the need for explicitly describing every possible permutation by example. Thus, any of the claimed embodiments can be used in any combination.

[0426] Further, unless expressly stated to the contrary, “and / or” refers to an inclusive and not to an exclusive. Thus, “and / or” should be understood to mean “either or both” of theAttorney Docket No. BIOB-20 / 01WO 40787 / 68

[0427] elements so conjoined, e.g., elements that are conjunctively present in some cases and disjunctively present in other cases. For example, a condition A and / or B, is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0428] The use of "a" or "an" to describe the various elements and components herein is merely for convenience and to give a general sense of the disclosure. This description should be read to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise. Similarly, the adjective “another,” when used to introduce an element, is intended to mean one or more elements. The terms “including” and “having” are intended to be inclusive such that there may be additional elements other than the listed elements.

[0429] The above written description of the invention provides a manner and process of making and using it such that any person skilled in this art is enabled to make and use the same, this enablement being provided in particular for the subject matter of the appended claims, which make up a part of the original description.

[0430] As used herein, the phrases “selected from the group consisting of,” “chosen from,” and the like include mixtures of the specified materials.

[0431] The above written description of the invention provides a manner and process of making and using it such that any person skilled in this art is enabled to make and use the same, this enablement being provided in particular for the subject matter of the appended claims, which make up a part of the original description.

[0432] Although this invention has been described with a certain degree of particularity, it is to be understood that the present disclosure has been made only by way of illustration and that numerous changes in the details of construction and arrangement of parts may be resorted to without departing from the spirit and the scope of the invention.Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0433] The above description is presented to enable a person skilled in the art to make and use the invention, and is provided in the context of a particular application and its requirements. Various modifications to the preferred embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments and applications without departing from the spirit and scope of the invention. Thus, this invention is not intended to be limited to the embodiments shown, but is to be accorded the widest scope consistent with the principles and features disclosed herein. It is, therefore, to be understood that within the scope of the accompanying claims, the invention may be practiced otherwise than as specifically described herein.

[0434] Having generally described this invention, a further understanding can be obtained by reference to certain specific examples, which are provided herein for purposes of illustration only, and are not intended to be limiting unless otherwise specified.

[0435] EXAMPLES

[0436] Example 1 - A two-part epoxy primer was prepared by mixing the following components:

[0437] • Part A: 50% solids-based epoxy resin (bisphenol A diglycidyl ether) and 4% epoxidized soybean oil.

[0438] • Part B: 8% polyester polyol and 38% plant-based polyol (sorbitol).

[0439] The primer was diluted with 20% water before application. The resulting coating exhibited excellent adhesion to steel substrates and provided outstanding corrosion protection.

[0440] Example 2 – A two-part epoxy primer was prepared by mixing the following components:Attorney Docket No. BIOB-20 / 01WO 40787 / 68

[0441] • Part A: 40% solids-based epoxy resin (novolac epoxy resin) and 2% epoxidized linseed oil.

[0442] • Part B: 10% polyester polyol and 48% plant-based polyol (glycerol).

[0443] The primer was diluted with 40% water before application. The resulting coating demonstrated exceptional UV resistance, maintaining its color and gloss even after prolonged exposure to sunlight.

[0444] Numerous modifications and variations on the present invention are possible in light of the above teachings. It is, therefore, to be understood that within the scope of the accompanying claims, the invention may be practiced otherwise than as specifically described herein.

Claims

Attorney Docket No. BIOB-20 / 01WO 40787 / 68CLAIMSWhat we claim is1. A coating composition comprising:(A) a solids-based epoxy resin;(B) an epoxidized plant-based oil;(C) a polyester polyol; and(D) a plant-based polyol; and(E) optionally, one or more additives,wherein the coating composition has a total solids content ranging from 70% to 95%.

2. The coating composition of claim 1, wherein the composition contains 30 wt% to 60 wt% of the solids-based epoxy resin, wherein the percentage is based on the total of the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plantbased polyol.

3. The coating composition of claim 1, wherein the composition contains 1 wt% to 10 wt% of the epoxidized plant-based oil, wherein the percentage is based on the total of the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plantbased polyol.

4. The coating composition of claim 1, wherein the composition contains 2 wt% to 15 wt% of the polyester polyol, wherein the percentage is based on the total of the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plant-based polyol.Attorney Docket No. BIOB-20 / 01WO 40787 / 685. The coating composition of claim 1, wherein the composition contains 25 wt% to 50 wt% of the plant-based polyol, wherein the percentage is based on the total of the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plant-based polyol.

6. The coating composition of claim 1, wherein the solids-based epoxy resin is selected from the group consisting of a bisphenol A diglycidyl ether, a bisphenol F diglycidyl ether, and a novolac epoxy resin.

7. The coating composition of claim 1, wherein the epoxidized plant-based oil is selected from the group consisting of epoxidized soybean oil, epoxidized linseed oil, and epoxidized castor oil.

8. The coating composition of claim 1, wherein the polyester polyol is derived from adipic acid or phthalic anhydride.

9. The coating composition of claim 1, wherein the plant-based polyol is selected from the group consisting of sorbitol, glycerol, and a polyol derived from biomass.

10. The coating composition of claim 1, further comprising a solvent, wherein the solvent is water.

11. The coating composition of claim 10, wherein the coating composition comprises up to 40 wt% of the solvent.Attorney Docket No. BIOB-20 / 01WO 40787 / 6812. A method of making a coating composition, comprising:stirring, shaking, or agitating a solids-based epoxy resin, an epoxidized plant-based oil, a polyester polyol, and a plant-based polyol for a time and under conditions sufficient to blend the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plant-based polyol to substantial homogeneity, thereby forming the coating composition, wherein the coating composition has a total solids content ranging from 70% to 95%.

13. The method of claim 12, further comprising adding a solvent after the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plant-based polyol are blended to substantial homogeneity.

14. The method of claim 13, wherein the solvent is water.

15. The method of claim 14, wherein after the solvent is added the coating composition comprises up to 40 wt% of the solvent.

16. The method of claim 12, wherein the composition contains 30 wt% to 60 wt% of the solids-based epoxy resin, 1 wt% to 10 wt% of the epoxidized plant-based oil, 2 wt% to 15 wt% of the polyester polyol, and 25 wt% to 50 wt% of the plant-based polyol, wherein the percentages are based on the total of the solids-based epoxy resin, the epoxidized plant-based oil, the polyester polyol, and the plant-based polyol.

17. A method of coating a surface of a material, comprising:applying a layer of a coating composition to a surface of a material, wherein the coating composition comprises a solids-based epoxy resin, an epoxidized plant-based oil, aAttorney Docket No. BIOB-20 / 01WO 40787 / 68polyester polyol, and a plant-based polyol, and wherein the coating composition has a total solids content ranging from 70% to 95%; andallowing the coating composition to cure.

18. The method of claim 17, wherein the applying and the allowing are repeated to form multiple layers of the coating composition on the surface of the material.

19. The method of claim 18, wherein 2 to 5 layers of the coating composition are formed on the surface of the material.

20. The method of claim 17, wherein the allowing the coating composition to cure is performed at ambient temperature.

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