POLYURETHANE FOAM COMPOSITION COMPRISING AN AROMATIC POLYESTER POLYOL COMPOSITION, AND PRODUCTS MANUFACTURED THEREOF

Abstract

A polyurethane foam composition comprising: (a) an isocyanate compound; (b) one or more isocyanate-reactive compounds, at least one of the isocyanate-reactive compounds comprising an aromatic polyester polyol compound comprising an imide portion, wherein the aromatic polyester polyol is the reaction product of: (i) a cyclic anhydride compound; (ii) a phthalic acid-based compound; (iii) a primary amine compound; (iv) an aliphatic diol compound; (v) optionally, a high-functionality, low-molecular-weight polyether polyol compound; (vi) optionally, a hydrophobic compound; and wherein the weight ratio of Component (i) to Component (ii) is from 1:24 to 24:1; and wherein the aromatic polyester polyol is liquid at 25°C and comprises a hydroxyl number ranging from approximately 30 to approximately 600; and (c) a blowing or expanding agent.

Description

POLYURETHANE FOAM COMPOSITION COMPRISING AN AROMATIC POLYESTER POLYOL COMPOSITION, AND PRODUCTS MANUFACTURED THEREOF FIELD OF INVENTION This description refers in general to a polyurethane foam composition comprising an aromatic polyester polyol compound, and products manufactured therefrom. BACKGROUND OF THE INVENTION Polyurethane (PU) and polyisocyanurate (PIR) based foam products are widely used in the building construction industry due to their superior insulating and sealing properties compared to other building insulation solutions used in the industry. Local building codes often dictate that materials used in building construction, such as PU and / or PIR-based foam products, must meet certain flammability criteria before they can be used in building construction. Consequently, formulators of these foam products often include fire-retardant additives in the foam compositions to ensure the final foam product complies with the relevant building codes. Although the use of a flame retardant additive in a foam composition is beneficial in most cases, there are inherent disadvantages to using such additives in foam compositions. For example, the use of a flame retardant additive can increase the overall cost of the composition, impacting the economic benefit of using a PU and / or PIR foam product in building construction. Furthermore, adding flame retardant additives to a foam composition can cause storage and handling problems (e.g., uneven distribution or changes in reactivity), which may discourage a builder from using PU and / or PIR foam products in building construction. BRIEF DESCRIPTION OF THE FIGURE A full understanding of disclosure can be obtained from the following description of certain disclosure modalities when read together with the accompanying figure in which: Figure 1 is a photograph comparing three polyurethane foam products that were subjected to a fire test. DETAILED DESCRIPTION OF THE INVENTION As used in this document, unless otherwise specified, all numbers such as those expressing values, ranges, quantities, or percentages may be read as if preceded by the word approximately, even if the term does not appear explicitly. Plural encompasses singular and vice versa. As used herein, "plurality" means two or more, while the term "number" means one or a whole number greater than one. As used herein, "includes" and similar terms mean that they include without limitation. anj Lnn / zznz / E / Yi When referring to any numerical range of values, it is understood that such ranges include every number and / or portion between the minimum and maximum of the established range. For example, a range of “1 to 10” is intended to include all sub-ranges between (and including) the mentioned minimum value of 1 and the mentioned maximum value of 10; that is, those with a minimum value equal to or greater than 1 and a maximum value equal to or less than 10. As used herein, molecular weight means weight average molecular weight (Mw) determined by gel permeation chromatography. Unless otherwise stated herein, reference to any compound shall also include any isomers (e.g., stereoisomers) of such compounds. As used in this document, the “isocyanate index” or NCO index is the ratio of isocyanate groups to isocyanate-reactive hydrogen atoms present in a given composition, expressed as a percentage: [NCO] x 100 _____________________ (%) [active hydrogen] It should be noted that the NCO index expresses the percentage of isocyanate used in a composition relative to the amount of isocyanate theoretically required to react with the amount of isocyanate-reactive hydrogen in the composition during the polymerization step. Any isocyanate groups consumed in a preliminary step to produce a modified polyisocyanate compound (e.g., a prepolymer), or any active hydrogen consumed in a preliminary step (e.g., that reacted with isocyanate to produce modified polyols or polyamines), are not considered in the NCO index calculation. Only free isocyanate groups and free isocyanate-reactive hydrogens (including those from water, if used) present in the actual polymerization step are considered in the NCO index calculation. For the purpose of calculating the NCO index, the expression “isocyanate-reactive hydrogen atoms” refers to the total number of active hydrogen atoms in the hydroxyl and amine functional groups present in the composition. In other words, during the polymerization step, a hydroxyl group is considered to comprise one reactive hydrogen; a primary amine group is considered to comprise one reactive hydrogen; and a water molecule is considered to comprise two active hydrogens. As used herein, liquid means having a viscosity of less than 200 Pa.s as measured in accordance with ASTM D445-1 1a at 20°C. As used herein, "trimerization catalyst" means a catalyst that catalyzes (promotes) the formation of isocyanurate groups from isocyanates. Polyurethane / polyisocyanurate foam composition PU and PiR foam products are used in a variety of applications, including building construction, transportation, piping, shipbuilding, sporting goods, furniture, and packaging. The widespread use of these foam products across numerous industries can be attributed to their ability to be formulated with a broad range of properties. For example, in building construction applications, low-density PU and PiR foams (e.g., 0.5–4 pcf) are used as insulation in sandwich or building panels (e.g., panels used in roofs, walls, ceilings, and floors or floors) or as spray-in-place foam due to their: (i) solid insulation / sealing performance; (ii) ability to meet or exceed building codes related to flammability and heat resistance / retardance; and (iii) ability to improve the structural integrity of a structure even if the structure is subjected to intense heat. Similarly, low-density PU and PIR foams (e.g., 1.5–4 pcf) are also used as insulation in transportation, pipeline, and shipbuilding applications. For example, these foam products are widely used in refrigerated vehicles, district heating systems (e.g., pipes used to transport steam or hot water), and industrial pipelines or storage tanks used in the transportation and storage of petroleum and other hydrocarbons. Unlike low-density PU and PIR foams, high-density PU and PIR foams are often used in non-insulating applications, such as vehicle interior trim and roof linings, office furniture, molded chair frames, simulated wood furniture, and rigid moldings. As previously stated, some PU and PIR foam compositions contain flame retardants to enhance the overall flame-retardant properties of the final foam product. However, there are inherent disadvantages to using a flame-retardant additive in a foam composition. The polyurethane foam composition described herein, however, allows a formulator to reduce or possibly eliminate the need for a flame-retardant additive in a polyurethane composition while maintaining the flammability properties exhibited by polyurethane compositions that use flame retardants. The polyurethane foam composition described herein comprises: (A) an isocyanate compound; (B) one or more isocyanate-reactive compounds, at least one of the isocyanate-reactive compounds comprises an aromatic polyester polyol comprising an imide portion, wherein the aromatic polyester polyol is the reaction product of: (i) a cyclic anhydride compound comprising Structure (1), Structure (2), or combinations thereof; (ii) an italic acid-based compound; a primary amine compound comprising Structure (3) (defined below); (iii) a primary amine compound; and (iv) an aliphatic diol; wherein the weight ratio of Component (i) to Component (ii) is from 1:24 to 24:1; and wherein the aromatic polyester polyol is liquid at 25°C and comprises a hydroxyl number ranging from 30 to 600; (C) a blowing or expanding agent; and (D) optionally, other additives. Isocyanate compound The polyurethane foam composition described herein comprises one or more isocyanate compounds. In some embodiments, the isocyanate compound is a polyisocyanate compound. Suitable polyisocyanate compounds that may be used include aliphatic, aliphatic, and / or aromatic polyisocyanates. Isocyanate compounds typically have the structure R-(NCO)x, where x is at least 2, and R comprises an aromatic, aliphatic, or combined aromatic / aliphatic group. Non-limiting examples of suitable polyisocyanates include diphenium-2-diisocyanate (MDI) type isocyanates (e.g., 2,4'-, 2,2'-, 4,4'-MDI or mixtures thereof), mixtures of MDI and oligomers thereof (e.g., polymeric MDI or "crude" MDI), and reaction products of polyisocyanates with components containing hydrogen atoms reactive with isoclanate (e.g., polymeric polyisocyanates or prepolymers).Therefore, suitable isocyanate compounds that may be used include SUPRASEC® DNR isocyanate, SUPRASEC® 2185 isocyanate, RUBINATE® M isocyanate, and RUBINATE® 1840 isocyanate, or combinations thereof. SUPRASEC® and RUBINATE® isocyanates are available from Huntsman Corporation. Other examples of suitable isocyanate compounds also include tolylene diisocyanate (TDI) (e.g., 2,4 TDI, 2,6 TDI, or combinations thereof), hexamethiene diisocyanate (HMDI or HDI), isophorone diisocyanate (IPDI), butylene diisocyanate, trimethylhexamethylene diisocyanate, di(isocyanocyclohexyl)methane (e.g., 4,4'-diisocyanaiodicchlorohexylmethane), meth-1,8-octane isocyanate diisocyanate, tetramethylxylene diisocyanate (TMXDI), 1,5-naphthalene diisocyanate (NDI), p-phenylenediisocyanate (PPDI), 1,4-cyclohexane diisocyanate (GDI), tolidine diisocyanate (TODI), or combinations thereof. They can also be used as component (1) modified polyisocyanates containing isocyanurate, carbodiimide or uretonimine groups. Blocked polyisocyanates may also be used as Component (1) provided that the reaction product has a release temperature below the temperature at which Component (1) will react with Component (2). Suitable blocked polyisocyanates may include the reaction product of: (a) a phenol or an oxime compound and a polyisocyanate, or (b) a polyisocyanate with an acidic compound, such as benzyl chloride, hydrochloric acid, thionium chloride, or combinations thereof. In certain embodiments, the polyisocyanate may be blocked prior to introduction into the reactive ingredients / components used in the composition described herein. Mixtures of isocyanates, for example, a mixture of TDi isomers (e.g., mixtures of 2,4- and 2,6-TDI isomers), or mixtures of higher diisocyanates and polyisocyanates produced by phosgenation of aniiin / formaldehyde condensates may also be used as Component (1). In some embodiments, the isocyanate compound is liquid at room temperature. A mixture of isocyanate compounds can be produced according to any technique known in the field of the invention. The isomer content of the diphenylmethane diisocyanate can be brought within the required ranges, if necessary, by techniques well known in the field of the invention. For example, one technique for changing the isomer content is to add monomeric MDI (e.g., 2,4-MD!) to an MDI mixture containing a higher than desired amount of polymeric MDI (e.g., MDI comprising 30% to 80% w / w of 4,4'-MDI, the remainder of which comprises MDI oligomers and MDI homologs). In some embodiments, the isocyanate compound comprises from 30% to 65% (e.g., from 33% to 62% or from 35% to 60%) by weight of the total polyurethane foam composition. anj Lnn / zznz / B / Yi Reactive compound with Isocyanate The polyurethane foam composition described herein comprises one or more isocyanate-reactive compounds. As stated above, at least one of the isocyanate-reactive compounds used in the polyurethane foam composition comprises an aromatic polyester polyol compound comprising an imide portion (Aromatic Polyol Compound Containing an Imidite Portion). Any of the known organic compounds containing at least two isocyanate-reactive portions per molecule may be used as the other isocyanate-reactive compound in the polyurethane foam composition (Other Polyol Compound). In some embodiments, the isocyanate-reactive compound comprises 20% to 50% (e.g., dei 23% to 47% or dei 25% to 45%) by weight of the polyurethane foam composition. Aromatic polyol compound containing an imide portion The aromatic polyol compound containing an imide portion used herein is the reaction product of a composition comprising: (i) a cyclic anhydride compound; (ii) an italic acid-based compound; (iii) a primary amine compound; (iv) a diol; (v) optionally, a low molecular weight, high-functionality polyether polyol compound; and (vi) optionally, a hydrophobic compound; wherein the weight ratio of Component (i) to Component (ii) is from 1:24 to 24:1 (collectively, the imide portion polyol composition). A detailed description of the various reactive components used to form the aromatic polyol compound containing an imide portion can be found below. In some embodiments, the aromatic polyol compound containing an imide portion is formed by mixing components (i)–(vi) and allowing one or more of the reactive ingredients to react. In some embodiments, the aromatic polyol compound containing an imide portion is synthesized using a single-vessel process (i.e., one-pot synthesis) rather than a multi-vessel process. For example, in certain embodiments, components (i)–(iv) are placed in the same reaction vessel along with the optional reactive components (e.g., components (v) and (vi)) and subjected to esterification / transesterification reaction conditions. Such reaction conditions, in certain modalities, occur at a temperature ranging from 0°C to 300°C, (e.g., from 70°C to 250°C), for a period of time ranging from 1 hour to 24 hours (e.g., from 3 hours to 10 hours).In certain embodiments, the aromatic polyol compound containing a portion of amide may be preformed before being added to a reaction vessel with the optional reactive components described above. The aromatic polyol compound containing a portion of amide and the optional reactive components are then subjected to esterification / transesterification reaction conditions. In certain formulations, an esterification / transesterification catalyst can be used to increase the reaction rate of the reacting components. Examples of suitable catalysts include tin catalysts (e.g., Fastcat™ catalysts (based on tin oxide) available from Arkema, Inc.), titanium catalysts (e.g., titanium catalysts include Tyzor® TBT (titanium tetra-n-butoxide) catalysts; Tyzor® TE catalyst (a triethanolamine titanate chelate) available from Dori Ketal Specialty Catalysts), alkali catalysts (e.g., NaOH, KOH, sodium and potassium ioxides), acid catalysts (e.g., sulfuric acid, phosphoric acid, hydrochloric acid, and sultanatic acid), enzymes, or combinations thereof. In some embodiments, the catalyst can be used in an amount ranging from 0.001 to 0.2 percent by weight based on the total weight of the imide portion polyol composition. One advantage of using a one-pot synthesis process to form the aromatic polyol compound containing an imide portion is that such a process can be easily adopted in an industrial manufacturing environment. For example, using a one-pot synthesis process not only reduces the overall capital expenditure and equipment required to manufacture the aromatic polyol compound containing the imide portion, but also reduces the total amount of space required to manufacture the aromatic polyol compound containing the imide portion. It should be noted that, in some embodiments, the imide portion polyol composition is solvent-free. As used herein, “solvent-free” means that no solvents (e.g., acetone, tetrahydrofuran) are present in the composition; however, in some cases, trace or incidental amounts of solvent (e.g., <5%, <3%, <1% by weight of the total imide portion polyol composition) may be present in the composition. It is observed that, in some embodiments, minor amounts of Component (iv) may be present after the formation of the aromatic polyol compound containing the imide portion. Consequently, the composition may comprise up to 30 percent by weight (e.g., 0% to 20% or 1% to 15%) of Component (iv) (i.e., unreacted free aliphatic diol), based on the total weight of the imide portion polyol composition. Component (i): Cyclic anhydride compound Suitable cyclic anhydride compounds that can be used as Component (i) of the imide portion polyol composition include one or more cyclic anhydride compounds comprising Structure (1), Structure (2), or combinations thereof: Structure (1): anj Lnn / zznz / E / Yi Structure (2): where X is a portion of cyclic anhydride, OH or COOH, which is attached directly to the structure or through R, which is an aromatic ring, an aliphatic ring, an aliphatic chain radical each containing from 1 to 12 carbon atoms with or without alkyl branching, and with or without heteroatoms comprising O, N, S, etc. and n is an integer from 0 to 1. Examples of suitable cyclic anhydrides that can be used as a component (i) include trimellitic anhydride, hemimellitic anhydride, pyromellitic dianhydride, melolianic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3-hydroxyphthalic anhydride, 4-hydroxyphthalic anhydride, bis(3,4-dicarboxyphenyl)ether dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, cyclobutantetracarboxylic dianhydride, carbalic or carolylic anhydride, 3-hydroxynaphthalic anhydride, naphthalenetetracarboxylic anhydride, α-(2-carboxyethyl)glutaric anhydride. In some embodiments, component (i) comprises from 1% to 68%, (e.g., from 3% to 20%), by weight based on the total weight of the polyol composition of the amide portion. Component (ii): Italic acid-based compound Examples of suitable italic acid-based compounds that may be used as a Component (i) of the polyamide portion composition include one or more italic acid-based compounds derived from: (a) substantially pure sources of italic acid, such as italic anhydride, italic acid, isophthalic acid, terephthalic acid, 2,6-naphthalene dicarboxylic acid; methyl esters of italic, isophthalic, terephthalic, 2,6-naphthalene dicarboxylic acid; dimethyl terephthalate, polyethylene terephthalate, or combinations thereof; or (b) more complex ingredients, such as side stream, waste and / or manufacturing residues from the manufacture of italic acid, terephthalic acid, dimethyl terephthalate, polyethylene terephthalate, polybutylene terephthalate, polytrimethylene terephthalate, polyethylene naphthalate, or combinations thereof. In some embodiments, component (ii) comprises from 1% to 70% (e.g., from 1% to 50%, from 2% to 40%) by weight based on the total weight of the polyol composition of the amide portion. Furthermore, in certain embodiments, the weight ratio of component (i) to component (ii) varies from 1:14 to 24:1 (e.g., 1:19 to 9:1 or 1:20 to 4:1). Component (iii): Primary amine compound Suitable primary amine compounds that can be used as Component (ii) of the amide portion polyol composition include a primary amine compound comprising Structure (3): Structure (3): NHε-RX where X is -NH2, -OH or -COOH, and R is an aromatic ring, an aliphatic ring, an aliphatic chain radical each containing 1 to 12 carbon atoms with or without alkyl branching, and with or without heteroatoms comprising O, N, S, or combinations thereof. Examples of suitable amine compounds that may be used as Component (iii) include diamines such as ethylenediamine; 1,3-propanediamine; tetramethylenediamine; hexamethylenediamine; isophoronediamine; diaminodiphenylmethane; diaminodiphenyl ether; methylene-4-cyclohexyldiamine; acetoguanamine; phenylenediamines; xylylenediamines; 1,2-cyclohexanediamine; 1,4-cyclohexanediamine, and mixtures thereof. Suitable amines may also include amino alcohols such as monoethanolamine; monopropanolamine; aminobenzyl alcohol; aminophenyl alcohol; hydroxyethylaniline; and mixtures thereof. Suitable amines may also include aminocarboxylic acids such as glycine; alanine, valine, aminopropionic acids, aminocaproic acid or aminobenzoic acids and mixtures thereof. In some forms, component (i¡¡) comprises from 0.3% to 25%, (e.g., from 1% to 15%), by weight based on the total weight of the polyol composition of the imide portion. Component (iv): Aliphatic diol compound Suitable aliphatic diol compounds that can be used as Component (iv) include an aliphatic diol compound comprising Structure (4): Structure (4): OH - R OH where R is a divalent radical selected from the group comprising: (x) alkylene radicals comprising 2 to 12 carbon atoms, with or without alkyl branching; or (y) radicals of Structure (5): Structure (5): - [(R'O)n - R'] - where R' is an alkylene radical containing 2 - 4 carbon atoms and n is an integer from 1 to 10. Examples of suitable aliphatic diol compounds that may be used as Component (iv) include ethylene glycol; diethylene glycol; propylene glycol; dipropylene glycol; trimethylene glycol; triethylene glycol; tetraethylene glycol; butylene glycols; 1,4-butanediol; neopentyl glycol; 2-methyl-2,4-pentanediol; 1,6-hexanediol; 1,2-cyclohexanediol; poly(oxyalkylene)polyols each containing two to four alkylene radicals derived from the condensation of ethylene oxide, propylene oxide, or combinations thereof. In some forms, component (iv) comprises from 5% to 70%, (e.g., from 5% to 40%, from 10% to 30%), by weight based on the total weight of the polyol composition of the portion of imide. Component (v): High-functionality, low molecular weight polyether polyols The reactive mixture used to form the aromatic polyol compound containing a portion of amide may also comprise high functionality (i.e., five or more active hydrogen atoms per molecule), low molecular weight (i.e., up to 1,000 Daltons) polyether polyol compounds. Examples of suitable low molecular weight, high functionality polyether polyols include glycerin, alkoxylated glycerin, 1,1,1-trimethyliodipropane, 1,1,1-trimethyliodiethane, pentaerythritol, dipentaerythritol, sucrose, alkoxylated sucrose, methyl glucoside, alkoxylated methyl glucoside, glucose, alkoxylated glucose, fructose, alkoxylated fructose, sorbitol, alkoxylated sorbitol, lactose, alkoxylated lactose, or combinations thereof. In some forms, component (v) comprises from 0% to 30%, (e.g. from 0% to 20%, from 0% to 10%), by weight based on the total weight of the polyol composition of the portion of the meal. anj Lnn / zznz / B / Yi Component (vi): Hydrophobic compound The reactive mixture used to form the aromatic polyol compound containing an amide portion may also comprise a hydrophobic compound. As used herein, hydrophobic compound means a compound or mixture of compounds comprising one or more substantially nonpolar organic portions. The hydrophobic compound is generally insoluble in water and normally contains at least one functional group capable of esterification or transesterification (e.g., a monocarboxylic acid group, a monocarboxylic acid ester group, a hydroxyl group, or combinations thereof). As used herein, "monocarboxylic acid group" and "monocarboxylic acid ester group" mean that the carboxylic acid portions present in the hydrophobic compound are monoacids. In some forms, the hydrophobic compounds used as Component (vi) are materials not derived from italic acid. Suitable hydrophobic compounds that can be used as Component (vi) include carboxylic acids (e.g., fatty acid compounds such as caproic, caprylic, 2-ethylhexanoic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, and ricinoleic acids), lower alkanoyl esters of carboxylic acids (e.g., fatty acid methyl ester compounds such as methyl caproate, methyl caprylate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl oleate, methyl stearate, methyl linoleate, and methyl linolenate), fatty acid alkanolamides (e.g., resin oil fatty acid diethanolamide, lauric acid diethanolamide, and monoethanolamide of fatty acid oieic), triglycerides (e.g., fats and oils such as castor oil, coconut oil (including cochineal oil), corn oil, cottonseed oil, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, soybean oil, sunflower oil, resin oil, tallow and natural or functionalized oil derivatives, such as epoxidized, natural oil), alkyl alcohols (e.g., alcohols containing 4 to 18 carbon atoms per molecule such as decyl alcohol, oleyl alcohol, cetyl alcohol, isodecyl alcohol, tridecyl alcohol, lauryl alcohol and mixed Ciz-Cu alcohol), or combinations thereof. In some embodiments, component (vi) comprises from 0% to 30%, (e.g., from 0% to 20%, from 0% to 10%), by weight based on the total weight of the imide portion polyol composition. Emulsifiers The aromatic polyol compound composition containing an imide portion may also contain a nonionic emulsifier (i.e., compounds containing one or more hydrophobic and one or more hydrophilic portions and lacking portions that dissociate in aqueous solution or disperse as cations and anions). While almost any nonionic emulsifying compound may be employed, in some embodiments, the nonionic emulsifier may be a polyoxyalkylene emulsifier containing an average of approximately 4 to approximately 200 individual oxyalkylene groups per molecule, typically selecting the oxyalkylene groups from the group consisting of oxyethylene and oxypropylene. Typically, the nonionic emulsifier may comprise, for example, Lnn / zznz / B / Yi, from approximately 0% to approximately 20% by weight of the composition (e.g., from 0% to approximately 10%). Characteristics of the polyol compound containing an imide portion In some embodiments, the polyol compound containing a portion of the imide of this disclosure has an average hydroxyl functionality ranging from 1.3 to 4 (e.g., 1.5 to 3.5 or 1.8 to 3). In some embodiments, the polyol compound containing a portion of amide has an average hydroxyl index value ranging from 30 to 600 mg KOH / g, (e.g., from 50 to 500 mg KOH / g or from 100 to 450 mg KOH / g), taking into account any free glycols that may be present. In some forms, the polyol compound containing a portion of imide has an acid value ranging from 0.5 to 5 mg KOH / g (e.g., from 0.5 to 2 mg KOH / g). In some embodiments, the polyol compound containing an imide portion has a viscosity ranging from 200 to 150,000 centipoises (cps), (e.g., 1,000 to 100,000 cps or 1,500 to 50,000), at 25°C measured using a Brookfield viscometer. Surprisingly, it was found that in some embodiments, the thermal stability of the polyol compound containing an imide portion, measured at 500°C under anaerobic conditions and at 400°C under aerobic conditions, is at least 5% greater than the thermal stability of conventional aromatic polyester polyol compounds (where thermal stability is measured as TGA using the method described in the Thermal Stability Test of Polyols of the examples cited below). As used herein, "conventional aromatic polyester polyol compounds" are aromatic polyester polyol compounds having the same hydroxyl number as the polyol compound containing an imide portion, and prepared using the same reactive ingredients (except components (i) and (iii)) and under the same reactive conditions as the polyol compound containing an imide portion.In other words, Conventional Aromatic Polyester Compounds lack Components (i) and (iii). Although the aromatic polyol compound containing a portion of imide is a reactive ingredient in a described polyurethane foam composition, it can also be used as a polyol compound in any composition that uses a polyol. However, in certain embodiments of this description, the aromatic polyol compound containing a portion of imide is not used in coating applications. In other words, the aromatic polyol compound containing a portion of imide is not used in a coating composition such as a paint composition. Another polyol compound As previously stated, the polyurethane foam composition described herein may also comprise other polyol compounds in addition to the aromatic polyol compound containing an imide portion described in the preceding sections. Polyol compounds or mixtures thereof that are liquid at 25°C, have a molecular weight ranging from 60 to 10,000 (e.g., 300 to 10,000 or less than 5,000), a nominal hydroxyl functionality of at least 2, and a hydroxyl equivalent weight of 30 to 2,000 (e.g., 30 to 1,500 or 30 to 800), may be used as the Other Polyol Compound. anj Lnn / zznz / B / Yi Examples of suitable polyols that can be used as the Other Polyol Compound include polyether polyols, such as those prepared by adding alkylene oxides to initiators, containing 2 to 8 active hydrogen atoms per molecule. In some embodiments, the initiators include glycols, glycerol, trimethylolpropane, triethanolamine, pentaerythritol, sorbitol, sucrose, ethylenediamine, ethanolamine, diethanolamine, aniline, toluenediamines (e.g., 2,4- and 2,6-toluenediamines), polymethylene polyenylene polyamines, N-alkylphenylenediamines, o-chloroaniline, p-aminoaniline, diaminonaphthalene, or combinations thereof. Suitable alkylene oxides that can be used to form polyether polyols include ethylene oxide, propylene oxide, and butylene oxide, or combinations thereof. Other suitable polyol compounds that can be used as the other polyol compound include Mannich polyols having a nominal hydroxyl functionality of at least 2 and having at least one secondary or tertiary amine nitrogen atom per molecule. In some embodiments, Mannich polyols are the condensates of an aromatic compound, an aldehyde, and an alkanolamine. For example, a Mannich condensate can be produced by the condensation of one or both of phenol and an alkylphenol with formaldehyde and one or more of monoethanolamine, diethanolamine, and diisopronolamine. In some embodiments, Mannich condensates comprise the reaction products of phenol or nonylphenol with formaldehyde and diethanolamine. The Mannich condensates of the present description can be prepared by any known process. In some embodiments, Mannich condensates serve as initiators for alkoxylation. Any alkylene oxide can be used (e.g.,e.g., the alkylene oxides mentioned above), to alkoxylate one or more Mannich condensates. When polymerization is complete, the Mannich polyol comprises primary hydroxyl groups and / or secondary hydroxyl groups attached to aliphatic carbon atoms. In certain embodiments, the polyols used are polyether polyols comprising propylene oxide (PO), ethylene oxide (EO), or a combination of PO and EO groups or portions in the polymer backbone of the polyols. These PO and EO units may be randomly arranged or in block sections along the polymer backbone. In some embodiments, the EO content of the polyol ranges from 0 to 100 wt% based on the total weight of the polyol (e.g., from 50 wt% to 100 wt%). In some embodiments, the PO content of the polyol ranges from 0 to 100 wt% based on the total weight of the polyol (e.g., from 100 wt% to 50 wt%). Therefore, in some forms, the EO content of a polyol can range from 99% to 33% by weight of the polyol, while the PO content ranges from 1% to 67% by weight of the polyol.Furthermore, in some embodiments, the EO and / or PO units may be located at the end of the polyol polymer backbone or within the interior sections of the main polyol polymer backbone. Suitable polyether polyols include poly(oxyethyleneoxypropylene)diols and triols obtained by the sequential addition of propylene and ethylene oxides to difunctional or trifunctional initiators known in the art. In certain embodiments, Another Polyol Compound comprises the diols or triols described above or, alternatively, mixtures thereof. anj Lnn / zznz / E / Yi Polyether polyols also include reaction products obtained by the polymerization of ethylene oxide with another cyclic oxide (e.g., propylene oxide) in the presence of polyfunctional initiators such as water and low-molecular-weight polyols. Suitable low-molecular-weight polyols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, cyclohexane dimethanol, resorcinol, bisphenol A, glycerol, trimethylolopropane, 1,2,6-hexantriol, pentaerythritol, or combinations thereof. Polyester polyols that can be used as the other polyol compound include polyesters that have a linear polymer structure and a number-average molecular weight (Mn) ranging from approximately 500 to approximately 10,000 (e.g., preferably from approximately 700 to approximately 5,000 or 700 to approximately 4,000), and an acid number generally less than 1.3 (e.g., less than 0.8). The molecular weight is determined by assaying the terminal functional groups and is related to the number-average molecular weight. Polyester polymers can be produced using techniques known in the art, such as: (1) an esterification reaction of one or more glycols with one or more dicarboxylic acids or anhydrides; or (2) a transesterification reaction (i.e., the reaction of one or more glycols with esters of dicarboxylic acids).Molar ratios generally greater than one mole of glycol to acid are preferred to obtain linear polymer chains with terminal hydroxyl groups. Suitable polyester polyols also include various lactones, typically manufactured from caprolactone and a bifunctional initiator such as diethylene glycol. The dicarboxylic acids of the desired polyester may be aliphatic, cycloaliphatic, aromatic, or combinations thereof. Suitable dicarboxylic acids that can be used alone or in mixtures generally have a total of 4 to 15 carbon atoms and include succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, dodecanedioic, isophthalic, terephthalic, cyclohexanedicarboxylic acids, or combinations thereof. Anhydrides of dicarboxylic acids can also be used (e.g., italic anhydride, tetrahydrophthalic anhydride, or combinations thereof). In some formulations, adipic acid is the preferred acid.The glycols used to form suitable polyester polyols can include aliphatic and aromatic glycols having a total of 2 to 12 carbon atoms. Examples of such glycols include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2-dimethyl-1,3-propanediol, 1,4-cyclohexanedimethanol, decamethylene glycol, dodecamine glycol, or combinations thereof. Additional examples of suitable polyols include hydroxyl-terminated polythioethers, polyamides, polyesteramides, polycarbonates, polyacetals, polyolefins, polysiloxanes, and simple glycols such as ethylene glycol, butanediols, diethylene glycol, triethylene glycol, propylene glycols, dipropylene glycol, tripropylene glycol, and mixtures thereof. Additional examples of suitable polyols include those derived from natural sources, such as vegetable oil, fish oil, lard, and tallow. Vegetable-based polyols can be manufactured from any vegetable oil or oil mixtures containing sites of unsaturation, including, but not limited to, soybean oil, castor oil, palm oil, canola oil, linseed oil, rapeseed oil, sunflower oil, safflower oil, olive oil, peanut oil, sesame seed oil, cottonseed oil, walnut oil, and chinawood oil. The hydrogen-active material may contain other isocyanate-reactive materials, such as polyamines and polythiols. Suitable polyamines include polyethers terminated with primary and secondary amines, aromatic diamines such as diethyltoluene diamine and the like, aromatic polyamines, or combinations thereof. Composed of blowing or expanding agents As previously stated, the polyurethane foam composition described herein also comprises a blowing agent. Any physical blowing agent known in the art of PU and PIR foams may be used in the composition described herein. For example, suitable blowing agent compounds include hydrocarbons, hydrochlorofluorocarbons, hydrofluorocarbons, hydrohaloolefins, or combinations thereof. Examples of hydrocarbon blowing agents that can be used include lower aliphatic or cyclic hydrocarbons, linear or branched (e.g., alkanes, alkenes, and cycloalkanes, preferably those compounds having 4 to 8 carbon atoms). Specific examples of suitable blowing agent compounds include n-butane, isobutane, 2,3-dimethylbutane, cyclobutane, n-pentane, isopentane, technical-grade pentane mixtures, cyclopentane, methylcyclopentane, neopentane, n-hexane, isohexane, π-heptane, isoheptane, cyclohexane, methylcyclohexane, 1-pentene, 2-methylbutene, 3-methylbutene, 1-hexene, or combinations thereof. Examples of suitable hydrochlorofluorocarbons include 1-chloro-1,2-difluoroethane, 1-chloro-2,2-difluoroethane, 1-chloro-1,1-difluoroethane, 1,1-dichloro-1-fluoroethane, monochlorodifluoromethane, or combinations thereof. Examples of suitable hydrofluorocarbons include 1,1,1,2-tetrafluoroethane (HFC 134a), 1,1,2,2-tetrafluoroethane, trifluoromethane, heptafluoropropane, 1,1,1-trifluoroethane, 1,1,2-trifluoroethane, 1,1,1,2,2-pentafluoropropane, 1,1,1,3-tetrafluoropropane, 1,1,1,3,3-pentafluoropropane (HFC 245fa), 1,1,3,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoro-n-butane (HFC 365mfc), 1,1,1,4,4,4-hexafluoro-n-butane, 1,1,1,2,3,3,3-heptafluoropropane (HFC 227ea), or combinations thereof. Examples of suitable hydrohaloolefins are trans-1-chloro-3,3,3-fluoropropene (HFO 1233zd), trans-1,3,3,3-tetrafluoropropene (HFO 1234ze), cis- and trans-1,1,1,4,4,4-hexafluoro-2-butene (HFO 1336mzz), or combinations thereof. Other suitable physical expanding agents are butane, tert-(2-methyl-2-propanol), methyl methoxymethane, and methyl formate. Chemical blowing or expansion agents, such as water, monocarboxylic acid, and polycarboxylic acid (e.g., formic acid), can also be used as the sole blowing agent in the polyurethane foam composition described herein. Alternatively, these chemical blowing agents can also be used in combination with the physical blowing agents described above as a joint blowing agent. anj Lnn / zznz / E / Yi In some embodiments, the blowing agent compounds are used in a sufficient quantity to give the final foam product the desired density of less than 320.36 Kg / m3 (20 Lb / ft³) (e.g., <160.18 Kg / m3 (10 Lb / ft³) or < 64.07 Kg / m3 (4 Lb / ft³)). Auxiliary compounds and additives The polyurethane foam composition described herein may also comprise one or more auxiliary compounds or additives that can be added to impart certain physical properties to the final foam product formed from the polyurethane foam composition. Examples of suitable auxiliary compounds and additives include catalysts, surfactants, fire retardants or flame retardants, smoke suppressants, crosslinking agents (e.g., triethanolamines and / or glycerol), viscosity reducers (e.g., propylene carbonate and / or dibasic esters), infrared pacifiers (e.g., carbon black, titanium dioxide, and metal flakes), cell size reducing compounds (e.g., inserts, insoluble fluorinated compounds, and perfluorinated compounds), pigments (e.g., azo / diazo dyes and phthalocyanines), fillers (e.g., calcium carbonate), and reinforcing agents (e.g.,, glass fibers and / or ground foam residues), release agents (e.g. zinc stearate), antioxidants (e.g. butylated hydroxytoluene), dyes, antistatic agents, biocidal agents or combinations thereof. Catalytic compounds that can accelerate / promote: (P) the reaction between isocyanate compounds and isocyanate-reactive compounds; or (I) the formation of isocyanurates (e.g., the reaction between isocyanate compounds) may be used in the polyurethane foam composition of this disclosure. Suitable catalysts include urethane catalysts (e.g., tertiary amine catalysts), blowing catalysts, trimerization catalysts, or combinations thereof.Examples of such catalysts include dimethylcyclohexylamine, triethylamine, pentamethylenediethylenetriamine, tris(dimethylaminopropyl)hexahydrotriazine, dimethylbenzylamine, bis-(2-dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylaminoethoxy) ethanol; organometallic compounds such as potassium octoate, potassium acetate, dibutylene dilaurate, dibutylene diacetate, bismuth neodecanoate, 1,1',1'-(1,2-ethanediyldinitrile)tetrakis[2-propanol] neodecanoate complexes, 2,2',2,2'-(1,2-ethanediyldinitrile)tetrakisphenylethanol neodecanoate complexes, quaternary ammonium salts such as 2-hydroxypropyltrimethylammonium formate, or combinations thereof. In some embodiments, the catalyst compounds can be used in an amount of up to 5% (e.g., from 0.5% to 3%) by weight of the polyurethane foam composition. Foam formulators typically use surfactants in their foam compositions to control the cellular structure of the final foam product. Consequently, various surfactants (e.g., silicone-based and / or silicone-free surfactants) can be used in the polyurethane foam composition described herein. Examples of suitable surfactants include: (i) silicone surfactants, including: (a) L-5345, L-5440, L-6100, L-6642, L-6900, L-6942, L-6884, L-6972; Evonik Industries DC-193, DC5357, YES3102, YES3103 (each available from Momentíve Performance Materials Inc.); (b) Tegostab 8490, 8496, 8536, 84205, 84210, 84501, 84701, 84715 (each available from Evonik Industries AG), polyorganosiloxane polyether copolymers (for example, polyoxyalkylene polysiloxane block copolymers); (i) non-silicon surfactants, including nonionic, anionic, cationic, ampholytic, semipolar and dipolar or zwitterionic ion organic surfactants; (iii) nonionic surfactants including: phenol alkoxylates (e.g., ethoxylated phenol compounds), alkylphenol alkoxylates (e.g., ethoxylated nonylphenol compounds), LK-443 (available from Evonik Industries AG), Vorasurf 504 (available from Dow Chemical Co), (iv) or combinations thereof. In some forms, surfactants can be used in an amount of up to 5% (e.g., from 0.5% to 3%) by weight of the polyurethane foam composition. Although one of the primary objectives of this disclosure is to provide a polyurethane foam composition containing little or no flame retardant, these compounds may still be used in the polyurethane foam composition of this disclosure. Examples of suitable flame retardants that may be used include: (i) organophosphate compounds, such as organic phosphates, phosphites, phosphonates, polyphosphates, polyphosphites, polyphosphonates, ammonium polyphosphates, triethyl phosphate, tris(2-chloropropyl) phosphate, diethyl phosphonate, diethyl hydroxymethylphosphonate, diethyl hydroxymethylphosphonate, diethyl hydroxymethylphosphonate, N,N-bis(2-hydroxyethyljaminomethylphosphonate); (ii) halogenated flame retardants (e.g., tetrabromophthalate diol and chlorinated paraffin compounds); or (iii) combinations thereof. In some forms, fire retardants can be used in an amount of up to 15% (e.g., up to 10%) by weight of the polyurethane foam composition. Polyuretose foam product with polyisocyanurate A PU and / or PIR product is formed from the polyurethane foam composition of this disclosure. In certain embodiments, a PU and / or PIR foam can be formed from the polyurethane foam composition described herein by introducing the following components of the polyurethane foam composition together and allowing the reactive components to react: (1) an isocyanate compound; (2) one or more isocyanate-reactive compounds (including the polyol compound containing an amide portion); (3) a blowing or expanding agent; and (4) additional additives.In order to form a PU foam product, the molar ratio of the isocyanate compound to one or more isocyanate-reactive compounds is close to 1:1 (e.g., usually less than 2:1), whereas the molar ratio of the isocyanate compound to one or more isocyanate-reactive compounds is greater than 1:1 (e.g., 2:1) when forming a PIR foam product. The materials described above can be used as Components 1, 2, 3, or 4. The components can be introduced into each other in multiple streams (i.e., at least two streams). In some embodiments, one stream comprises the isocyanate compound, while the other stream comprises one or more isocyanate-reactive compounds. In certain embodiments, the stream comprising the isocyanate-reactive compounds may also comprise other materials (e.g., additives / auxiliary compounds) provided they are not reactive with the isocyanate-reactive compounds. Note that the stream comprising the isocyanate compound may also comprise other materials (e.g., additives / auxiliary compounds) provided the materials are not reactive with the isocyanate compound.In some embodiments, the blowing agent is introduced into a third stream that is separate and distinct from the streams comprising the isocyanate compound and the isocyanate-reactive compounds. While the additives / auxiliary compounds may be introduced into one or more of the streams, they may also be introduced into one or more additional streams (e.g., a catalyst stream), separate and distinct from the streams described above, if desired. The mixing of the streams can be carried out in a spraying apparatus (e.g., a spray gun), a mixing head (including those with or without a static mixer), or some other type of container that is configured to spray or otherwise deposit the components of the polyurethane foam composition described herein onto a substrate. In some embodiments, the isocyanate compound and one or more isocyanate-reactive compounds of the polyurethane foam composition are reacted with an NCO index of up to 1,000%. In some embodiments, the NCO index varies from 20% to 180% (e.g., from 40% to 160%). For urethane-modified polyisocyanurate foams, the NCO index is usually higher (e.g., from 180% to 1,000%, or from 200% to 500%, or from 50% to 500%). PU and / or PIR foam products can be either closed-cell or open-cell. As used herein, a foam is considered closed-cell if its closed-cell content is greater than 70% (e.g., 80% or >85%), as measured by ASTM D6226-15. It is considered open-cell when its closed-cell content is less than 50% (e.g., <40% or <30%), as measured by ASTM D6226-15. In some forms, PU and / or PIR foam products exhibit a thermal conductivity (K value) ranging from 0.10 to 0.17 Btu-in / hr.ft2oF, (e.g., 0.11 to 0.16 Btu-in / hr.ft2oF or 0.12 to 0.15 Btu-in / hr. ft2oF) as measured by ASTM C518-17 at an average plate temperature of 75°F (23.88°C). In certain embodiments, PU and / or PIR foam products have ASTM E1354-17 performance that is better than a comparator foam made of the same composition where the imide-containing aromatic polyester polyol is replaced by an imide-free aromatic polyester polyol where the weight ratio of component (i) to component (ii) is 0:100. In other embodiments, PU and / or PIR foam products have an ASTM E1354-17 performance that is equal to a comparator foam made of the same composition wherein the imide-containing aromatic polyester polyol is replaced by an imide-free aromatic polyester polyol wherein the weight ratio of component (i) to component (i!) is 0:100; and wherein the polyurethane foam uses less flame retardant than the comparator foam. anj Lnn / zznz / B / Yi Use of polyurethane foam composition The polyurethane foam composition described herein can be used in applications requiring high heat resistance (e.g., > 121.1°C), thermal distortion, flame retardancy, and / or char integrity. The PU and / or PIR slag product manufactured from the polyurethane foam composition described herein can be produced in a form well known to those skilled in the art of polyurethanes. Suitable forms include slabs, moldings, cavity fillers (e.g., pour-in-place foam), spray-in-place foam, foamed foam, or laminates (e.g., foam product combined with another material such as paper, metal, plastics, or wood panels). Construction and other industrial applications. In the United States of America, model building codes require that materials used in commercial / residential buildings and homes meet specific fire performance criteria depending on whether the material will be used in roofs, walls, ceilings, attics, or crawl spaces. These criteria are measured through fire tests that include ASTM E84, E108, E119, E662, E2074; FM 4450, 4880; NFPA 285, 286; and UL 1040, 1256. PUR and PIR foam produced from the polyurethane foam composition described herein can be used to meet one or more of the fire tests described above while significantly reducing or eliminating the use of fire retardants. While the polyurethane foam composition described herein can be applied to various substrates, in some embodiments, the substrate is a rigid or flexible facing sheet made of foil or other material (including another similar or different polyurethane layer) that is conveyed (continuously or intermittently) along a production line by means such as a conveyor belt. In certain embodiments, the facing sheet is used to manufacture construction panels for use in the building industry. In another embodiment, the polyurethane foam composition described herein is used in the continuous production of PU- or PIR-based metal panels. In this application, the polyurethane foam composition is applied through one or more mixing heads to a lower metal layer (which may be profiled) in a dual-belt laminator. In some embodiments, the laminator line speed is set to 75 ft / min or less. In the laminator, a metal panel is continuously manufactured as the rising foam composition reaches the upper surface layer. The formed metal panel is then cut to the desired length at the laminator's exit end. Suitable metals that can be used in this application include aluminum or steel, which can be coated with a polyester or epoxy layer to help reduce rust formation while promoting foam adhesion to the metal layer.In some models, the final foam metal panel comprises a foam thickness that varies from 2.54 cm to 20.32 cm (1 inch to 8 inches). In another embodiment, the polyurethane foam composition described herein is used in the continuous production of an insulating board and a laminated PU and / or PIR foam decking board, generically referred to as board. In this process, the foaming mixture is applied via one or more mixing heads to the lower liner layer in a double-belt laminator. In some embodiments, the laminator line speed is set to 1,524 m / s (300 ft / min) or less. In the laminator, a board is formed continuously as the rising foam mixture reaches the upper liner layer. Similar to the metal panels described above, the boards are cut to the desired length at the laminator's output end.Suitable materials for the facing include aluminum foil, cellulose fibers, reinforced cellulose fibers, craft paper, coated fiberglass mats, uncoated fiberglass mats, crushed glass, or combinations thereof. In some configurations, the final foam-laminated board has a foam thickness ranging from 0.635 cm to 12.7 cm (0.25 in to 5 in). It is observed that, in the examples described above, the top coating layer can be applied over the deposited composition before or after the polyurethane foam composition has partially or fully cured. In an alternative embodiment, the polyurethane foam composition described herein can be poured into an open mold (including distribution via open-mold placement equipment) or simply deposited into or toward a desired location (i.e., a pour-in-place application), such as between the inner and outer walls of a structure. Generally, such applications can be achieved using known one-action prepolymer or semi-prepolymer techniques in combination with conventional blending methods. Upon reaction, the polyurethane foam composition will take the shape of the mold or adhere to the substrate onto which it is deposited. The polyurethane foam composition is then allowed to cure fully or partially in place. In certain applications, the polyurethane composition can be injected into a closed mold, thus forming a molded polyurethane foam product. In these applications, the polyurethane composition can be injected with or without vacuum assistance. If a mold is used (regardless of whether it is an open or closed mold), then the mold can be heated to facilitate handling and the workability of the polyurethane composition (e.g., to facilitate the flow of the polyurethane foam composition into the mold). Applications in pipes To achieve the desired heat / thermal resistance and flammability resistance requirements, the polyurethane foam composition described herein can be used in piping applications (e.g., pipes used in the transport of oils, bitumen, natural gas, petroleum, hot water, or steam (both pressurized and unpressurized)). For example, the polyurethane foam composition described herein can be used in the production of pre-insulated pipes in the European Union for use in district heating systems. The European Union requires that such pipes meet or exceed DIN EN-253, which stipulates that the pipe assembly must have a service life of at least thirty (30) years at a continuous operating temperature of 120°C. anj Lnn / zznz / B / Yi In piping applications, the polyurethane foam composition described herein can be discontinuously injected into the hollow space between a pipe (e.g., a metal pipe made of steel) and an outer lining (e.g., a plastic lining made of polyethylene), thus forming an insulated pipe. Alternatively, the polyurethane foam composition can be applied continuously to a pipe, around which the lining layer is subsequently placed before or after the polyurethane foam composition has fully cured, thus forming an insulated pipe. Sprayed foam The polyurethane foam composition described herein can be applied to a substrate using a dosing system or some other spraying means. The dosing system, which may be a fixed-ratio system, comprises a resin composition supply vessel, an isocyanate component supply vessel, a spray machine, and a spray gun comprising a mixing chamber. The composition comprising the isocyanate-reactive compounds (e.g., the aromatic polyol compound containing the imide portion), the blowing agent, and other auxiliary additives (collectively, the Resin Composition) is pumped in a first stream from the resin composition supply vessel to the spray machine.The isocyanate compound is pumped in a separate stream, distinct from the resin composition, from the isocyanate component supply vessel to the spray machine. The isocyanate component and the resin composition are heated and pressurized in the spray machine and supplied to the spray gun via two separate heated hoses to form the polyurethane foam composition. The polyurethane composition is then supplied to the spray gun, which is used to: (i) mix the isocyanate compound and the resin composition, and (ii) spray the polyurethane composition onto the substrate. Suitable substrates that can be sprayed with the polyurethane foam composition include sheathing materials (e.g., oriented strand board (OSB), plywood, gypsum board, foam board, fiberboard, and cellulose sheathing); wood, concrete, polyvinyl chloride, metal, or combinations thereof. In certain embodiments, the PU and / or PIR foam product can be formed in situ on regular or irregular surfaces (e.g., walls, ceilings, floors, or other commercial and residential substrates) of a structure. In some embodiments, a spray-in-place foam made with the polyurethane foam composition described herein can achieve a Class I rating in ASTM E84 without using a fire retardant such as tris(1-chloro-2-propyl) phosphate (TCPP). Modifications Although specific embodiments of this description have been detailed, those skilled in the art will appreciate that various modifications and alternatives to these details could be developed by considering the general principles of the description. Accordingly, the provisions described are intended to be illustrative only and not limiting to the scope of the description, which should include the full extent of the appended claims and all their equivalents. Therefore, any of the features, properties, and / or elements listed above may be combined in any combination and still remain within the scope of this disclosure. Examples Raw materials and components: The examples refer to the following reaction components, raw materials, and terms: PTA: Purified Ie-rephthalic Acid (available from Grupo Petrotemex, SA de CV). DEG: Diethylene glycol (available from Equistar Chemicals, LP). TEG: Triethylene glycol available from (Dow Chemical Company). PEG 200: Polyethylene glycol 200 (available from Huntsman International LLC). Glycerin (available from Terra Biochem LLC). TYZOR® TE: Titanium isopropoxide (triethanolamine) solution 80% by weight in isopropanol (available from Dorf Ketal Specialty Catalysts LLC). TMA: Trimellitic anhydride (1,2,4-benzene carboxylic anhydride from Sigma Aidrich Corporation). Glycine (available from Sigma Aidrich Corporation). MDA: 4,4'-Diaminodiphenylmethane (available from Sigma Aidrich Corporation). TEROL® 250: Chicken! of aromatic polyester that has an OH index of 250 mg KOH / g (available from Huntsman International LLC). JEFFOL® R-470X: A reactive aromatic amine polyol that has an OH index of 470 mg KOH / g (available from Huntsman International LLC). JEFFCAT® H-1: A gas-blown balanced polyurethane amine catalyst (available from Huntsman International LLC). Pel-Cat 9540-A: A solution of potassium 2-ethylhexanoate in diethylene glycol (available from Ele Corporation). DC193: A silicone surfactant (available from Evonik Industries AG as DABCO® DC 193 Surfactant). BICAT 8210: Bismuth 2-Ethylhexanoate (available from The Shepherd Chemical Company). TCPP: Tris(2-chloro!opyl) phosphate (available from Lanxess Corporation as LEVAGARD® PP). SOLSTICE® LBA: 1-Chloro-3,3,3-trifluoropropene (available from Honeywell International Inc.). RUBINATE® M: Polymeric MDI having an NCO value of 30.5% (available from Huntsman International LLC). Analysis and testing: The examples refer to the following terms: Acid value: A measure of residual acid in polyester polyol determined by standard titration techniques, e.g. ASTM D4662. OH value or index: Hydroxyl value which is a measure of the number of OH groups determined by standard titration techniques, e.g. ASTM D4274. Viscosity: Viscosity measured using a Brookfield Viscometer, such as a Brookfield DV-tl Viscometer. TGA Analysis: A thermogravimetric analysis (TGA) was performed using a TGA 05000 from TA Instruments-Water LLC. It is a thermal analysis method in which the mass of a sample is measured over time as the temperature changes. Cream time: the time elapsed between the moment the isocyanate component of a composition is mixed with the isocyanate-reactive component of the composition and the formation of the fine foam or cream in the composition Gel time: the time elapsed between the moment the isocyanate component of a composition is mixed with the isocyanate-reactive component of the composition and the point at which the expanded foam begins to gel due to crosslinking. Experimentally, this gel time is determined when a 6-inch wooden tongue-clip (e.g., Puritan 705) is pushed under the surface of the rising foam and a string forms upon its removal. Tack-free time: The time elapsed between the moment the isocyanate component of a composition is mixed with the isocyanate-reactive component of the composition and the point at which the outer layer of the foam loses its tackiness or adhesive quality. Experimentally, such a loss of tackiness is when a 6” wooden tongue depressor (e.g., Puritan 705) is placed in contact with the surface of the reaction mixture and appears non-sticky when removed from the surface. FRD (Free Lift Density): the density of a foam sample taken from the center of a foam cup Tg (Glass transition temperature): the temperature at which an amorphous material transitions from a hard and relatively brittle glassy state to a viscous or rubbery state. Conical calorimeter test: The test was performed according to ASTM E1354-17 test method at a radiant heat intensity of 30 kW / m². The following parameters were recorded: PHRR: Maximum Heat Release Rate, the highest rate of heat generation by fire. THR: The total heat generated by the fire at a given time. TSR: The total amount of smoke generated by the fire at a given time. % ML: Percentage of mass loss at a given moment of the fire. Description of the synthesis of polio! Rouom: 286 g of PTA, 73 g of trimellitic anhydride (TMA), 38 g of MDA, 11 g of glycerin, 73 g of PEG 200, 194 g of TEG, and 197 g of DEG were added to a 500 mL cylindrical glass reactor. Under a nitrogen flow rate of 0.3–0.5 liters per minute (LPM), the reaction mixture was heated to 80°C and held at that temperature for 30 minutes. The mixture was then heated to 140°C and held at that temperature for 30 minutes before being heated to 246°C. The temperature was then maintained at 246°C, and the condensate was collected. When the head temperature fell below 70°C (approximately 2 hours later), 0.8 g of Tyzor TE was added. The reaction was then heated to 240°C until the acid number was below 2.0 mg KOH / g (~3 hours). The reaction was then cooled below 100°C and the Polioi-1 was collected.The OH value was measured, and then DEG was added to adjust the OH value to the calculated 250 mg KOH / g while mixing at 80°C for 30 minutes. The polyol was then cooled to room temperature, and the final OH index and viscosity were measured. anj Lnn / 77nz / E / Yii Poíioí-2: 273 g of PTA, 79 g of trimellitic anhydride (TMA), 31 g of glycine, 11 g of glycerin, 76 g of PEG 200, 202 g of TEG, and 205 g of DEG were added to a 500 mL cylindrical glass reactor. Under a nitrogen flow rate of 0.3–0.5 liters per minute (LPM), the reaction mixture was heated to 80°C and held at that temperature for 30 minutes. The mixture was then heated to 140°C and held at that temperature for 30 minutes before being heated to 246°C. The temperature was maintained at 246°C, and the condensate was collected. When the head temperature fell below 70°C (approximately 3 hours later), 0.8 g of Tyzor TE was added. The reaction was then heated to 24°C until the acid value fell below 2.0 mg KOH / g (5 hours). The reaction was then cooled below 100°C and the Polyol-2 was collected.The OH value was measured, and then DEG was added to adjust the OH value to the calculated 250 mg KOH / g while mixing at 80°C for 30 minutes. The polyol was then cooled to room temperature, and the final OH index and viscosity were measured. Summary of the properties of polio!: Table 1: Polyol acid value (mg KOH / g) OH value (mg KOH / g) Viscosity (cPs) TMA to PTA weight ratio Terol®250 1.2 250 5,560 0 Polyol-1 1.1 253 15,090 0.255 Polyol-2 1.3 250 8,060 0.9 Thermal stability test of polyol! The thermal stability of Polyol-1, Polyol-2 of the invention, and the comparative polyol TEROL® 250 was evaluated using TGA under nitrogen and air, respectively. TGA is a widely accepted analytical method that provides an indication of the relative thermal stability of the material in question. All polyols were heated from 25°C to 700°C at a temperature increase rate of 10°C / min. The percentage weight retention of the foam at a given temperature relative to the initial foam weight at 25°C is summarized in Tables 2 and 3 below. As expected, in all cases, the higher the temperature, the greater the degree of polyol decomposition and the lower the percentage retention. Polyol-1 and Polyol-2 of the invention showed greater weight retention at all temperatures compared to the comparative polyol TEROL® 250 under both anaerobic and aerobic conditions.A higher weight retention at a given temperature in TGA suggests better thermal stability for Polyol-1, (in which the ratio of TMA to PTA is. 0.29), and Polyol-2, (in which the ratio of TMA to PTA is 0.255), compared to TEROL® 250, (where the ratio of TMA to PTA was zero). Table 2: % by weight under nitrogen anj Lnn / zznz / E / Yi Temp(cC) Terol®250 Polyol-1 Polyol-2 350 66.96 72.38 71.33 400 46.82 62.93 60.16 450 4.41 20.66 14.76 500 2.73 16.71 11.39 550 2.45 15.93 10.41 600 2.18 14.67 9.08 Table 3: % by weight under air Temp(°C) Terol®25O Polyol-1 Polyol-2 350 33.53 64.98 60.34 400 18.21 48.64 41.87 450 5.61 21.89 14.08 500 3.09 16.36 9.10 550 0.10 4.78 0.67 600 0.03 0.03 0.14 Description of the manufacture of polyurethane cup foams The composition of two foam formulations, (i.e., Formulation-1 and Formulation-2), is listed in Table 4. Formulation 1 represents a polyurethane foam system containing a flame retardant (TCPP), while Formulation 2 does not contain any TCPP. The isocyanate-to-poul premix ratio is 1.10 for Formulation 1 and 1.15 for Formulation 2, so that both formulations have the same isocyanate index of 169. The foam used for the thermal stability and fire resistance properties tests was made by the following steps: (i) pouring the contents of Side A and Side B into a 907.18 g (32 oz) unwaxed paper cup (e.g., Solo H4325-2050), thereby combining the two components so that the total weight of Side A and Side B is between 110 grams and 120 grams; (ii) mix the combined components for ~4 to 5 seconds at 2500-3000 rpm using a mechanical mixer (e.g.(ii) allow the components of the composition to react, thus forming the polyurethane foam product, and record the reactivities (creaming time, gel or mellowing time, tack-free or non-sticky time, or touch-dry time); (iv) store the foam at room temperature and humidity for 24 hours; and (v) cut a 4 cm x 4 cm x 4 cm sample from about 6 cm below the top surface of the foam to measure the free lift density (FRD). The reactivities and FRD are summarized in Table 5. Table 4 Polyol Premix Formulations! Formulation-1 Formulation-2 Polyester Polyol 53.5 53.5 Jeffol R-470 13.4 13.4 DC 193 1.0 1.0 Pel-Cat 9540-A 0.6 0.6 JEFFCAT® H-1 0.3 0.3 BICAT 8210 0.1 0.1 Water 1.0 0.5 TCPP 15.6 Solt!ce®LBA 14.5 15.0 Total Polyol Premix 100.0 84.4 anj Lnn / zznz / E / Yi Isocyanate Rubyate M 110.0 97.1 Isocyanate / Premix Ratio 1.10 1.15 Isocyanate Index 169 169 Description of the thermal stability and fire properties tests of the foam: Glass Transition Temperature (Tg) Measurement: A piece of foam was taken from the center location above the rim height of the cup. It was tested in compression mode using a TA Instruments RSA-G2 solids analyzer. The compression mode direction was aligned with the foam's lifting direction. A temperature scan was performed at a frequency of 1 Hz with dynamic deformation within the linear viscoelastic region. After the temperature scan procedure was completed, the temperature at the peak of the tan delta was selected as the Tg (summarized in Table 5). Polyurethane foams exhibiting a higher glass transition temperature can maintain better physical properties, such as foam strength, at elevated temperatures. Cone calorimeter test: A 10 cm x 10 cm x 2.5 cm sample was cut approximately 3 cm below the top surface of a cup foam and tested for fire resistance in a cone calorimeter. Table 5 summarizes the PHRR, THR, TSR, and %ML data (all at 2 minutes). In the cone calorimeter test, a lower PHRR and lower THR indicate less fuel contribution from the material being tested to the fire and, therefore, better fire properties. A lower TSR indicates less smoke generation from the material being tested, again an indicator of better fire properties. A lower %ML suggests a greater amount of original material retained after exposure to radiant heat. A lower %ML for a foam is also an indicator of better fire properties. Figure 1 shows the residue remaining after the conical calorimeter fire test of foams made using Formulation 1. The residue from the foams made using the inventive Polyol-1 and Polyol-2 showed monolithic and intumescent charring compared to the foam made using the comparator TEROL® 250 polyol. Monolithic charring is advantageous because it indicates that the foam is likely to maintain its structural integrity when burned in a fire better than one that shows many cracks or fissures. Intumescent char can slow the heat transfer from the exposed to the unexposed side of an assembly better than ordinary char. anj Lnn / zznz / B / Yi Table 5: Formulation 1 Formulation 2 Polyol Terol® 250 Polyol-1 Polyol-2 Terol® 250 Polyol-1 Polyol-2 Cream Time(s) 9 9 8 6 6 6 Gel Time(s) 27 28 27 15 14 17 Tack-Free Time(s) 47 44 39 21 19 24 FRD (pcf) 2.25 2.18 2.16 2.22 2.15 2.13 Tq (°C) 133 147 135 153 173 155 PHRR (kW / m2) 87.7 73.1 76.5 122.5 101.6 112.5 THR (MJ / m2) 2.49 1.67 1.18 6.86 3.71 2.27 TSR (m2 / m2) 80.6 55.0 58.2 134.3 96.5 85.4 %ML ^%) 21.7 17.2 15.7 38.4 22.3 17.1 Thermal stability test of foam using TGA: The thermal stability of foams made with Polyol-1, the inventive Polyol-2, and the comparative TEROL® 250 was evaluated using TGA under nitrogen. TGA analysis under anaerobic conditions at elevated temperatures can simulate the degradation of polyurethane foam that will produce gaseous fuel for fire. The first test used the same ramp method as in the polyol stability test, with a temperature increase from 25°C to 700°C at a rate of 10°C / min. The second test rapidly increased the temperature from 25°C to 550°C at a rate of 100°C / min, followed by an isothermal hold at 550°C for 60 minutes. The results are summarized in Tables 6 and 7 below.The foams made with the polyols of the invention showed greater mass retention than the control foams at a given temperature in both tests, suggesting less and slower thermal degradation. Table 6: TGA Results Using Slow Ramp Method, % by Weight Under Nitrogen Formulation 1 Formulation 2 Temp(°C) Terol® 250 Polyol-1 Polyol-2 Terol® 250 Polyol-1 Polyol-2 100 99.67 99.59 99.44 99.82 99.68 99.46 150 96.83 97.07 96.35 98.26 98.6 97.91 200 90.15 89.69 88.38 94.78 94.92 94.08 250 85.67 84.79 83.62 91.31 90.88 90.14 300 75.36 73.92 71.95 79.58 78.42 77.09 350 55.82 56.82 55.57 59.62 61.72 60.34 400 47.67 48.75 48.57 50.05 53.23 52.39 450 41.86 41.94 41.88 43.15 46.4 45.67 500 37.06 36.91 36.49 37.99 41.56 40.46 550 32.89 33.12 32.68 34.1 38.06 36.28 600 29.71 29.91 29.45 30.57 33.88 32.65 650 28.53 28.67 28.24 29.17 32.4 31.26 an / ιηη / ζζηζ / Β / γΐι Table 7 TGA Results using the Isthermal Method, % by weight under Nitrogen Formulation 1 Formulation 2 Time (min) Temp CO Terol® 250 Polyol·· Polyol-2 Terol® 250 Polyol- 1 Polyol2 0 25 99.29 99.52 99.44 99.39 99.26 99.31 1 124 98.36 99.45 99.25 99.68 99.59 99.46 2 224 89.82 90.2 89.55 95.55 95.93 95.33 3 321 78.37 76.82 75.42 83.13 81.86 81.33 4 423 47.83 46.75 47.17 52.22 51.65 51.83 5 522 33.26 33.63 33.87 35.67 36.93 37.41 8 550 24.14 27.18 27.29 26.32 29.34 30.00 10 550 23.15 26.45 26.54 25.40 28.33 28.94 20 550 21.68 25.3 25.31 24.03 26.81 27.29 30 550 21.29 24.86 24.9 23.63 26.4 26.92 40 550 21.11 24.57 24.67 23.41 26.18 26.72 50 550 20.99 24.32 24.49 23.24 26.03 26.58 60 550 20.92 24.13 24.34 23.12 25.92 26.47 It should also be noted that the foam products manufactured from the compositions had an excellent internal appearance (e.g., uniform internal cell size and no internal voids) and had fine internal cells with no evidence of cell collapse. In other words, a good quality foam product was produced using the compositions described herein.

Claims

1. A polyurethane foam composition characterized in that it comprises: an isocyanate compound; one or more isocyanate-reactive compounds, at least one of the isocyanate-reactive compounds comprising an aromatic polyester polyol compound comprising an amide portion, wherein the aromatic polyester polyol is the reaction product of: (i) a cyclic anhydride compound comprising Structure (1), Structure (2), or combinations thereof; Structure (1): XR anj Lnn / zznz / B / Yi Structure (2): wherein X is a cyclic anhydride portion, OH, or COOH, directly attached to the structure or via R, which is an aromatic ring, an aliphatic ring, an aliphatic chain radical each containing from 1 to 12 carbon atoms with or without alkyl branching, and with or without heteroatoms comprising O, N, S, etc.yn is an integer from 0 to 1; (ii) an italic acid-based compound, (iii) a primary amine compound, (iv) an aliphatic diol compound; (v) optionally, a high-functionality, low-molecular-weight polyether polyol compound; (vi) optionally, a hydrophobic compound; and wherein the weight ratio of Component (i) to Component (ii) is from 1:24 to 24:1; and wherein the aromatic polyester polyol is liquid at 25°C and comprises a hydroxyl number ranging from approximately 30 to approximately 600; and a blowing or expanding agent.

2. The polyurethane foam composition according to claim 1, further characterized in that the viscosity of the aromatic polyester polyol compound comprising a portion of [unclear] ranges from approximately 200 to approximately 150,000 centipoises at 25°C.

3. The polyurethane foam composition according to claim 1, further characterized in that the acid value of the aromatic polyester polyol compound comprising a portion of amide ranges from approximately 0.1 mg KOH / g to approximately 10 mg KOH / g.

4. The polyurethane foam composition according to claim 1, further characterized in that the aromatic polyester polyol compound comprising an imide portion does not comprise a solvent.

5. A polyurethane foam manufactured from the composition according to claim 1, further characterized in that the foam has better performance according to ASTM E1354-17 than a comparator foam manufactured from the same composition wherein the imide-containing aromatic polyester polyol is replaced by an imide-free aromatic polyester polyol, wherein the weight ratio of component (i) to component (ii) is 0:

100.

6. The polyurethane foam according to claim 1, further characterized in that the polyurethane foam is applied to a surface of a roof, wall, pipe or storage tank assembly.

7. The polyurethane foam manufactured from the composition according to claim 1, further characterized in that the polyurethane foam exhibits performance according to ASTM E1354-17 that is equal to that of a comparator foam made from the same composition, wherein the imide-containing aromatic polyester polyol is replaced by an imide-free aromatic polyester polyol, wherein the weight ratio of component (i) to component (ii) is 0:100; and wherein the polyurethane foam uses less flame retardant than the comparator foam.

8. The polyurethane foam according to claim 7, further characterized in that the polyurethane foam adheres to a roof, wall, pipe or storage tank assembly.

9. A method for forming a polyurethane foam product characterized in that it comprises: reacting, in the presence of a blowing or expanding agent, a reactive mixture comprising an isocyanate compound and one or more isocyanate-reactive compounds, at least one of the isocyanate-reactive compounds comprising an aromatic polyester polyol compound comprising an imide portion, wherein the aromatic polyester polyol is the reaction product of: (i) a cyclic anhydride compound comprising Structure (1), Structure (2) or combinations thereof;Structure (1): anj Lnn / zznz / B / Yi Structure (2): anj Lnn / zznz / E / Yi O er¡ where X is a cyclic anhydride portion, OH or COOH, which is directly attached to the structure or through R, which is an aromatic ring, an aliphatic ring, an aliphatic chain radical each containing from 1 to 12 carbon atoms with or without alkyl branching, and with or without heteroatoms comprising O, N, S, etc. and n is an integer from 0 to 1; (ii) an italic acid-based compound, (iii) a primary amine compound, (iv) an aliphatic diol compound; (v) optionally, a high-functionality, low-molecular-weight polyether polyol compound; (vi) optionally, a hydrophobic compound; and wherein the weight ratio of Component (i) to Component (i) is from 1:24 to 24:1; and wherein the aromatic polyester polyol is liquid at 25°C and comprises a hydroxyl number ranging from approximately 30 to approximately 600.

10. The method according to claim 9, further characterized in that the viscosity of the aromatic polyester polyol compound ranges from approximately 200 to approximately 150,000 centipoises at 25°C.

11. The method according to claim 9, further characterized in that the acid value of the aromatic polyester polyol compound ranges from approximately 0.1 mg KOH / g to approximately 10 mg KOH / g.

12. The method according to claim 9, further characterized in that the polyurethane foam composition does not comprise a solvent.

13. The method according to claim 9, further characterized in that the foam has a performance according to ASTM E1 354-17 that is better than that of a comparative foam made of the same composition wherein the aromatic polyester polyol containing amide is replaced by an amide-free aromatic polyester polyol, wherein the weight ratio of component (i) to component (ii) is 0:

100.

14. The method according to claim 9, further characterized in that the polyurethane foam exhibits performance according to ASTM E1354-17 that is equal to that of a comparator foam made of the same composition wherein the imide-containing aromatic polyester polyol is replaced by an imide-free aromatic polyester polyol wherein the weight ratio of component (ϊ) to component (i) is 0:100; and wherein the polyurethane foam uses less flame retardant than the comparator foam.

15. The polyurethane foam according to claim 9, characterized in that the polyurethane foam is applied to a surface of a roof, wall, pipe or storage tank assembly.