POLYESTER POLYOL COMPRISING AN IMIDE PORTION AND METHODS FOR MANUFACTURING THE SAME.

Abstract

A method for forming an aromatic polyester polyol compound comprising an imide portion, wherein the method comprises reacting: (i) a cyclic anhydride compound; (ii) a phthalic acid-based compound; (iii) a primary amine compound; and (iv) an aliphatic diol compound

Description

POLYESTER POLYOL COMPRISING AN IMIDE PORTION AND METHODS OF MANUFACTURING THE SAME FIELD OF INVENTION This description refers in general to a polyester polyol comprising a portion of amide, and methods of manufacturing the same. 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. Aromatic polyester polyols are also widely used in the manufacture of PU and / or PIR foams whenever the application requires high heat resistance and / or good flame resistance. For example, PU and / or PIR foam insulation is used in various pipelines for transporting oil, natural gas, and other petroleum products. In these applications, the PU and / or PIR foam must be able to operate at temperatures exceeding 121°C. Such applications include deep-well oil extraction, bitumen transport, and steam injection in heavy oil wells. These applications often require the PU and / or PIR foam to operate continuously at temperatures exceeding 148.8°C for extended periods (e.g., decades). In some cases, PU and / or PIR foam-insulated pipes are used to transport steam or hot water in district heating systems. In these applications, the PU and / or PIR foam must meet specific high-temperature performance requirements. For example, PU and / or PIR foam-insulated pipes used for steam or hot water transport in various district heating systems in the European Union must comply with EN253. EN235 requires that the pipe assembly have a service life of at least 30 years at a continuous operating temperature of 120°C. The use of an aromatic polyester polyol that has improved thermal stability to produce polyurethane and polyisocyanurate foam products has the potential to produce products with improved thermal resistance, as well as improved flame retardant properties. 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. When referring to any numerical range of values, it is understood that these ranges include every number and / or fraction 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, any sub-range 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 (PM) 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, liquid means having a viscosity of less than 200 Pa.s as measured in accordance with ASTM D445-1 at 20°C. Aromatic polyol compound containing an imide portion The aromatic polyester polyol compound comprising an imide portion (Aromatic Polyol Compound Containing an Imide Portion) used herein is the reaction product of an aromatic polyester polyol composition comprising: (i) a cyclic anhydride compound; (ii) an italic acid-based compound; (iii) a primary amine compound; (iv) an aliphatic diol; (v) optionally, a high-functionality, low-molecular-weight 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. 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 amide 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 amide portion is synthesized using a one-pot process (i.e., one-vessel synthesis) rather than a multi-pot process. One advantage of using a one-pot synthesis process to manufacture 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 an imide portion, but also reduces the total amount of space required to manufacture the aromatic polyol containing the imide portion. 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 an imide portion has an average hydroxyl numerical 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 an imide portion 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., from 1,000 to 100,000 cps or from 1,500 to 50,000), at 25°C as 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 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.For clarity purposes, Conventional Aromatic Polyester Compounds lack Components (i) and (iii). Component (i): Cyclic anhydride compound Suitable cyclic anhydride compounds that can be used as Component (i) of the aromatic polyester polyol composition include one or more cyclic anhydride compounds comprising Structure (1), Structure (2), or combinations thereof. ci / Lnn / zznz / E / Yi Structure (1): ci / 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 Component (i) include trimellitic anhydride, hemimelly anhydride, pyromellitic dianhydride, melophanic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 3-hydroxyphthalic anhydride, 4-hydroxyphthalic anhydride, bis(3,4-dicarboxyphenyl) ether dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, cyclobutanetracarboxylic dianhydride, carallylic or carbalytic 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 of the total aromatic polyester polyol composition. Component (ii): Italic acid-based compound Examples of suitable italic acid-based compounds that may be used as a component (i) of the aromatic polyester polyol 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 sidestream, waste and / or scrap or waste 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 (i) comprises from 1% to 70% (e.g., from 1% to 50%, from 2% to 40%) by weight of the total aromatic polyester polyol composition. Furthermore, in certain embodiments, the weight ratio of component (i) to component (i) varies from 1:24 to 24:1 (e.g., from 1:19 to 9:1 or from 1:20 to 4:1). Component (iii): Primary amine compound Suitable primary amine compounds that can be used as a Component (ii) of the aromatic polyester polyol composition include a primary amine compound comprising Structure (3). Structure (3): NH2-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 a Component (ii) include diamines such as ethylenediamine; 1,3-propanediamine; tetramethylenediamine; hexamethylenediamine; isophoronediamine; diaminodiphenylmethane; diaminodiphenyl ether; methylene-4,4'-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 embodiments, component (ii) comprises from 0.3% to 25%, (e.g., from 1% to 15%), by weight of the total aromatic polyester polyol composition. Component (iv): Aliphatic diol compound Suitable aliphatic diol compounds that can be used as Component (iv) of the aromatic polyester polyol composition 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-Ríen where R' is an alkylene radical containing 2 to 4 carbon atoms, and n is an integer from 1 to 10. Examples of suitable aliphatic diol compounds that can be used as Component (iv) include ethylene glycol; diethylene glycol; propylene glycol; dipropylene glycol; trimethylene glycol; triethylene glycol; ci 7 Lnn / zznz / E / Yi 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 embodiments, component (iv) comprises from 5% to 70%, (e.g., from 5% to 40%, from 10% to 30%) by weight of the total aromatic polyester polyol composition. Component (v): High-functionality, low molecular weight polyether polyols The reactive mixture used to form the aromatic polyol compound containing an amide portion may also comprise a high-functionality (i.e., three or more active hydrogen atoms per molecule), low-molecular-weight (i.e., up to 1,000 Daltons) polyether polyol. Examples of suitable high-functionality, low-molecular-weight polyether polyols include glycerin, alkoxylated glycerin, 1,1,1-trimethylolpropane, 1,1,1-trimethylolethane, 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 embodiments, Component (v) comprises from 0% to 30%, (e.g., from 0% to 20%, from 0% to 10%) by weight of the total aromatic polyester polyol composition. 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 alkandes 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., fatty acid diethanolamide from resin or tall oil, lauric acid diethanolamide, and fatty acid monoethanolamide). oleic), 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 oil, natural), 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 C12-C14 mixed 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 of the total aromatic polyester polyol composition. Method for preparing the aromatic polyol compound containing an imide portion To prepare the aromatic polyol compound containing a portion of imide, each of the components (i) to (iv) is placed in the same reaction vessel and subjected to esterification / transesterification reaction conditions. In certain embodiments, the optional reactive components described above are also added to the reaction vessel. The reaction conditions typically involve a temperature ranging from approximately 50°C to approximately 300°C (e.g., 70°C to 250°C) for a period of time ranging from approximately 1 hour to approximately 24 hours (e.g., 3 hours to 10 hours). In certain embodiments, a preformed aromatic polyester polyol formed from components (i) to (iv), the optional reactive components described above, and components (v) and (vi) are placed in the same reaction vessel, and subjected to the esterification / transesterification reaction conditions described above, thereby forming the Aromatic Polyol Compound Containing an Imide Portion. In some formulations, an esterification / transesterification catalyst can be used to increase the reaction rate. Examples of catalysts that can be used include, but are not limited to, tin catalysts, titanium catalysts, alkali catalysts, acid catalysts, or enzymes. Suitable catalysts include: tin catalysts (e.g., Fastcat™ catalysts (tin oxide-based) available from Arkema, Inc.), titanium catalysts (e.g., Tyzor® TBT (titanium tetra-n-butoxide) catalysts); triethanolamine thianate chelate catalysts (e.g., Tyzor® TE available from Dorf Ketal Specialty Catalysts); alkali catalysts (e.g., NaOH, KOH, sodium and potassium alkoxides); and acid catalysts (e.g., sulfuric acid, phosphoric acid, hydrochloric acid, and sulfonic acid). The catalyst is typically present at approximately 0.001% to approximately 0.2% by weight of the total aromatic polyester polyol composition. After formation, the aromatic polyol compound composition containing a portion of imide may comprise a minor amount of an unreacted aliphatic diol. For example, in certain embodiments, the composition may comprise up to 30 wt% of a free aliphatic diol, based on the total weight of the composition. However, the free aliphatic diol content of the composition typically ranges from 0 wt% to 20 wt% (e.g., 1 wt% to 15 wt%), based on the total weight of the composition. ci 7 Lnn / zznz / E / Yi It should be noted that, in some embodiments, the aromatic polyester 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 aromatic polyester polyol composition) may be present. 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 dispersion into 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, the oxyalkylene groups typically being selected from the group consisting of oxyethylene and oxypropylene. Typically, the nonionic emulsifier may comprise, for example, from approximately 0% to approximately 20% by weight of the composition (e.g., 0% to approximately 10%). 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 terephthalic acid, (available from Grupo Petrotemex, SAde 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 (triethanolamine) isopropoxide solution 80% pp. in isopropanol, (available from Dorf Ketal Specialty Catalysts LLC). TMA: Trimellitic anhydride (Sigma Aldrich Corporation's 1,2,4-benzenetricarboxylic anhydride). Glycine, (available from Sigma Aldrich Corporation). MDA: 4,4'-Diaminodiphenylmethane (available from Sigma Aldrich Corporation). ci / Lnn / zznz / B / Yi TEROL® 250: Aromatic polyester polyol having an OH index of 250 mg KOH / g, (available from Huntsman International LLC). Analysis and essay: The examples refer to the following terms: Acid number: A measure of residual acid in polyester polyol determined by standard titration techniques, e.g. ASTM D4662. OH index: Hydroxyl value that 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-II Viscometer. TGA Analysis: A thermogravimetric analysis (TGA) was performed using a TGA Q5000 from TA Instruments-Water LLC. This is a thermal analysis method in which the mass of a sample is measured over time as the temperature changes. Conical calorimeter test: The test was performed according to the test method specified in ASTM E1354-17 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 polyol synthesis Polyol-1: 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 value fell below 2.0 mg KOH / g (approximately 3 hours). The reaction was then cooled to below 100°C and the Polyol-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. Polyol-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 240°C until the acid number fell below 2.0 mg KOH / g (approximately 5 hours). The reaction was cooled to 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 polyol properties: Table 1: cl? Lnn / zznz / E / Yi Polyol acid number (mg KOH / g) OH number (mg KOH / g) Viscosity (cPs) Weight ratio of TMA to PTA Teroi®250 1.2 250 5,560 0 Poiioi-1 1.1 253 15,090 0.255 Pohol-2 1.3 250 8,060 0.9 Thermal stability test of polyol The thermal stability of the inventive Polyol-1, Polyol-2, and the comparator 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. 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. The Polyol-1 and Polyol-2 of the invention showed greater weight retention at all temperatures compared to the comparator TEROL® 250 polyol under both anaerobic and aerobic conditions.Greater weight retention at a given temperature in TGA suggests better thermal stability for Polyol-1 (in which the TMA to PTA ratio is 0.29), and Polyol-2 (in which the TMA to PTA ratio is 0.255) compared to TEROL® 250 (in which the TMA to PTA ratio was zero). Table 2: % by weight under air Temp(°C) 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®250 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 cl? Lnn / zznz / B / Yi

Claims

1. A method for forming an aromatic polyester polyol compound characterized in that it comprises an amide portion, wherein the method comprises reacting: (i) a cyclic anhydride compound comprising Structure (1), Structure (2) or combinations thereof; ci 7 Lnn / zznz / E / Yi Structure (1): Structure (2) O wherein X is a cyclic anhydride portion, OH or COOH, directly bonded 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.(i) yn is an integer from 0 to 1; (ii) an italic acid-based compound; (iii) a primary amine compound comprising Structure (3); Structure (3): NH2-RX wherein X is -NH2, -OH, or -COOH, and R 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, or combinations thereof; (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.

2. The method according to claim 1, further characterized in that the viscosity of the aromatic polyester polyol compound ranges from approximately 200 to approximately 150,000 centipoises at 25°C.

3. The method according to claim 1, further characterized in that the acidity index of the aromatic polyester polyol compound ranges from approximately 0.1 mg KOH / g to approximately 10 mg KOH / g.

4. The method according to claim 1, further characterized in that the method comprises reacting the components (i), (ii), (iii) and (iv) in a synthesis process in a single container.

5. The method according to claim 1, further characterized in that the reaction does not occur in the presence of a solvent.

6. The method according to claim 1, further characterized in that the aromatic polyester polyol compound has better thermal stability than an aromatic polyester polyol compound not containing an imide portion having similar aromatic content, hydroxyl number, functionality, and acid number.

7. An aromatic polyester polyol compound characterized in that it comprises an amide portion, wherein the aromatic polyester polyol is the reaction product of a reactive mixture comprising: (i) a cyclic anhydride compound comprising Structure (1), Structure (2) or combinations thereof; Structure (1): or ci / Lnn / zznz / E / Yi Structure (2): wherein X is a cyclic anhydride portion, OH or COOH, directly bonded 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.yn is an integer from 0 to 1; (i) an italic acid-based compound; (iii) a primary amine compound comprising Structure (3); Structure (3): NH2-RX wherein X is -NH2, -OH, or -COOH, and R 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, or combinations thereof; (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 25SC and comprises a hydroxyl index ranging from approximately 30 to approximately 600.

8. The aromatic polyester polyol compound according to claim 7, further characterized in that the viscosity of the aromatic polyester polyol compound ranges from approximately 200 to approximately 150,000 centipoises at 25°C.

9. The aromatic polyester polyol compound according to claim 7, 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.

10. The aromatic polyester polyol compound according to claim 7, further characterized in that the method comprises reacting the components (i), (ii), (iii) and (iv) in a single-vessel synthesis process.

11. The aromatic polyester polyol compound according to claim 7, further characterized in that the reaction does not occur in the presence of a solvent.

12. The aromatic polyester polyol compound according to claim 1, further characterized in that the aromatic polyester polyol compound has better thermal stability than an aromatic polyester polyol compound not containing an imide portion having similar aromatic content, hydroxyl number, functionality, and acid number.