Polyester polyol containing imide moiety and method for producing same

Abstract

A method for producing an aromatic polyester polyol compound containing an imide moiety, comprising reacting (i) a cyclic anhydride compound; (ii) a phthalic acid-based compound; (iii) a primary amine compound; and (iv) an aliphatic diol compound.

Description

[Technical Field]

[0001] background Field FIELD OF THE DISCLOSURE The present disclosure relates generally to polyester polyols containing imide moieties and methods for making the same. [Background technology]

[0002] Background information Polyurethane ("PU") and polyisocyanurate ("PIR") based foam products are widely used in the construction industry due to their superior sealing and insulating properties compared to other building insulation solutions used in the industry.

[0003] Local building codes often stipulate that materials used in building construction, such as PU and / or PIR-based foam products, must pass certain flammability standards before the product can be used in building construction. Accordingly, formulators of these foam products often include flame retardant additives in the foam composition to ensure that the final foam product passes the relevant building code.

[0004] While the use of flame retardant additives in foam compositions is beneficial in most cases, there are inherent drawbacks associated with the use of such additives in foam compositions. For example, the use of flame retardant additives can increase the overall cost of the composition, thereby affecting the economic benefits of using PU and / or PIR foam products in building construction. Furthermore, the inclusion of flame retardant additives in foam compositions can cause storage and handling problems (e.g., uneven distribution or reactivity changes) that can deter builders from using PU and / or PIR foam products in building construction.

[0005] 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 excellent flammability resistance. For example, PU and / or PIR foam insulation is used in various pipelines for the transportation of oil, natural gas, and other petroleum products. In these applications, the PU and / or PIR foam must be able to operate at temperatures greater than 121°C. Such applications include the extraction of oil from deep wells, the transportation of bitumen, and the transportation of steam for injection into heavy oil wells. These applications often require the PU and / or PIR foam to operate continuously at operating temperatures greater than 148.8°C for extended periods (e.g., decades).

[0006] 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 to transport steam or hot water in various district heating systems in the European Union must meet the EN253 standard. EN235 requires that pipe assemblies have a lifespan of at least 30 years at a continuous operating temperature of 120°C.

[0007] The use of aromatic polyester polyols with improved thermal stability for the production of polyurethane and polyisocyanurate foam products has the potential to provide products with improved heat resistance as well as improved flame retardancy. Summary of the Invention

[0008] Detailed Description As used herein, unless clearly specified otherwise, all numbers, such as those expressing values, ranges, amounts, or percentages, can be read as if preceded by the term "about" even if said term does not explicitly appear. The plural encompasses the singular and vice versa.

[0009] As used herein, "plurality" means two or more, while the term "number" means one or an integer greater than one.

[0010] As used herein, the words "including" and similar terms mean "including without limitation."

[0011] When any numerical range is referred to, it is understood that such range includes every number and / or portion between the minimum and maximum of the stated range. For example, a range of "1 to 10" is intended to include all sub-ranges between (and including) the recited minimum of 1 and the recited maximum of 10, i.e., having a minimum of 1 or more and a maximum of 10 or less.

[0012] As used herein, "molecular weight" refers to the weight average molecular weight (M) determined by gel permeation chromatography. W ) means

[0013] Unless otherwise stated herein, a reference to any compound also includes any isomers (eg, stereoisomers) of such compound.

[0014] As used herein, "liquid" means 25℃ This means that the viscosity is less than 200 Pa.s as measured in accordance with ASTM D445-1 1a.

[0015] Imide moiety-containing aromatic polyol compound The aromatic polyester polyol compounds containing imide moieties ("imide moiety-containing aromatic polyol compounds") used in this disclosure are the reaction products of an aromatic polyester polyol composition comprising: (i) a cyclic anhydride compound; (ii) a phthalic 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 in the preparation of the imide moiety-containing aromatic polyol compounds can be found below.

[0016] In some embodiments, the imide moiety-containing aromatic polyol compound is prepared by combining components (i)-(vi) and reacting one or more reactive components. In some embodiments, the imide moiety-containing aromatic polyol compound is synthesized using a single pot (i.e., one-pot synthesis) rather than a multi-pot synthesis.

[0017] One advantage of using a single-pot synthesis method for producing imide moiety-containing aromatic polyol compounds is that such a method can be readily incorporated into an industrial manufacturing setting. For example, the use of a single-pot synthesis method not only reduces the overall capital expenditures and equipment required to produce imide moiety-containing aromatic polyol compounds, but it also reduces the overall amount of space required to produce imide moiety-containing aromatic polyols.

[0018] Properties of imide moiety-containing polyol compounds In some embodiments, the imide moiety-containing polyol compounds of the present disclosure have an average hydroxyl functionality ranging from 1.3 to 4 (eg, 1.5 to 3.5 or 1.8 to 3).

[0019] In some embodiments, the imide moiety-containing polyol compound has an average hydroxyl number ranging from 30 to 600 mg KOH per gram (e.g., 50 to 500 mg KOH per gram or 100 to 450 mg KOH per gram), while taking into account any free glycol that may be present.

[0020] In some embodiments, the imide moiety-containing polyol compound has an acid number ranging from 0.5 to 5 mg KOH per gram (eg, 0.5 to 2 mg KOH per gram).

[0021] In some embodiments, the imide moiety-containing polyol compound has a viscosity ranging from 200 to 150,000 centipoise (cps) (e.g., 1,000 to 100,000 cps or 1,500 to 50,000) at 25°C as measured using a Brookfield viscometer.

[0022] Surprisingly, in some embodiments, it has been found that the thermal stability of imide moiety-containing polyol compounds is at least 5% higher than that of conventional aromatic polyester polyol compounds when measured at 500°C under anaerobic conditions and at 400°C under aerobic conditions (wherein thermal stability is measured as TGA using the method described in the Examples below under "Polyol Thermal Stability Test"). As used herein, a "conventional aromatic polyester polyol compound" is an aromatic polyester polyol compound having the same hydroxyl number as the imide moiety-containing polyol compound and produced using the same reactive components (except for components (i) and (iii)) under the same reaction conditions as the imide moiety-containing polyol compound. For clarity, the conventional aromatic polyester compound lacks components (i) and (iii).

[0023] 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 containing structure (1), structure (2), or a combination thereof. Structure (1): [ka] Structure (2): [ka] In the formula, X is a cyclic anhydride moiety, OH, or COOH, which is attached to the structure directly or via R, and R is an aromatic ring, an aliphatic ring, or an aliphatic chain group, each containing 1 to 12 carbon atoms, with or without alkyl branching, and with or without heteroatoms, including O, N, S, etc., and n is an integer from 0 to 1.

[0024] Examples of suitable cyclic anhydrides that can be used as component (i) include trimellitic anhydride, hemimellitic anhydride, pyromellitic dianhydride, mellophanic 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, cyclobutanetetracarboxylic dianhydride, carballylic anhydride, 3-hydroxynaphthalic anhydride, naphthalenetetracarboxylic anhydride, and α-(2-carboxyethyl)glutaric anhydride.

[0025] In some embodiments, component (i) comprises 1% to 68% by weight (eg, 3% to 20% by weight) of the wholly aromatic polyester polyol composition.

[0026] Component (ii): Phthalic acid-based compounds Examples of suitable phthalic acid-based compounds that may be used as component (ii) of the aromatic polyester polyol composition include: (a) phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, acid; Phthalic acid, isophthalic acid, terephthalic acid Acida substantially pure source of phthalic acid such as methyl ester; dimethyl terephthalate, polyethylene terephthalate, or a combination thereof; or (b) phthalic acid, terephthalic acid, dimethyl terephthalate, polyethylene terephthalate, polybutylene terephthalate, polytrimethylene terephthalate Also These include one or more phthalate-based compounds derived from more complex components such as side streams, waste and / or scrap residues from the manufacture of these combinations.

[0027] In some embodiments, component (ii) comprises 1% to 70% by weight (e.g., 1% to 50% by weight, 2% to 40% by weight) of the wholly aromatic polyester polyol composition. In further embodiments, the weight ratio of component (i) to component (ii) ranges from 1:24 to 24:1 (e.g., 1:19 to 9:1 or 1:20 to 4:1).

[0028] Component (iii): Primary amine compound Suitable primary amine compounds that can be used as component (iii) of the aromatic polyester polyol composition include primary amine compounds comprising the structure (3). Structure (3): NH2-RX wherein X is -NH, -OH, or -COOH, and R is an aromatic ring, an aliphatic ring, or an aliphatic chain group, each containing from 1 to 12 carbon atoms, with or without alkyl branching, and with or without heteroatoms, including O, N, S, or combinations thereof.

[0029] Examples of suitable amine compounds that can be used as component (iii) include diamines such as ethylenediamine, 1,3-propanediamine, tetramethylenediamine, hexamethylenediamine, isophoronediamine, diaminodiphenylmethane, diaminodiphenylether, methylene-4,4'-cyclohexyldiamine, acetoguanamine, phenylenediamine, xylenediamine, 1,2-cyclohexanediamine, 1,4-cyclohexanediamine, and mixtures thereof. Suitable amines may also include aminoalcohols such as monoethanolamine, monopropanolamine, aminobenzyl alcohol, aminophenyl alcohol, hydroxyethylaniline, and mixtures thereof. Suitable amines include glycine, alanine, valine, aminopropionic acid, aminocaproic acid, or aminobenzoic acid. Aminocarboxylic acids such as methyl methyl ketone and mixtures thereof may also be included.

[0030] In some embodiments, component (iii) comprises 0.3% to 25% by weight (eg, 1% to 15% by weight) of the wholly aromatic polyester polyol composition.

[0031] Component (iv): Aliphatic diol compound Suitable aliphatic diol compounds that can be used as component (iv) of the aromatic polyester polyol composition include aliphatic diol compounds comprising structure (4). Structure (4): OH-R-OH wherein R is: (x) an alkylene group containing from 2 to 12 carbon atoms, with or without alkyl branches; or (y) a divalent radical selected from the group including radicals of structure (5). Structure (5): -[(R'O) n -R']- wherein R' is an alkylene group containing 2-4 carbon atoms and n is an integer from 1 to 10.

[0032] 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; tetraethylene glycol; butylene glycol; 1,4 butanediol; neopentyl glycol; 2-methyl-2,4-pentanediol; 1,6-hexanediol; 1,2-cyclohexanediol; and poly(oxyalkylene) polyols each containing from 2 to 4 alkylene groups derived from the condensation of ethylene oxide, propylene oxide, or mixtures thereof.

[0033] In some embodiments, component (iv) comprises 5% to 70% by weight (eg, 5% to 40% by weight, 10% to 30% by weight) of the wholly aromatic polyester polyol composition.

[0034] Component (v): High functionality low molecular weight polyether polyol The reactive mixture used to prepare the imide moiety-containing aromatic polyol compound can also include 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.

[0035] In some embodiments, component (v) comprises 0% to about 30% by weight (eg, 0% to 20% by weight, 0% to 10% by weight) of the wholly aromatic polyester polyol composition.

[0036] Component (vi): Hydrophobic compound The reactive mixture used to prepare the imide moiety-containing aromatic polyol compound can also include a hydrophobic compound. As used herein, "hydrophobic compound" means a compound or mixture of compounds that contains one or more substantially non-polar organic moieties. Hydrophobic compounds are generally They are water-insoluble and typically contain at least one functional group (e.g., a monocarboxylic acid group, a monocarboxylic acid ester group, a hydroxyl group, or a combination thereof) that can be esterified or transesterified. As used herein, "monocarboxylic acid group" and "monocarboxylic acid ester group" mean that the carboxylic acid moieties present in the hydrophobic compound are monoacids.

[0037] In some embodiments, the hydrophobic compound used as component (vi) is a non-phthalate derived material.

[0038] Suitable hydrophobic compounds that can be used as component (vi) include carboxylic acids (e.g., fatty acid compounds such as caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and ricinoleic acid), lower alkanol 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 alkanols, Amides (e.g., tall oil fatty acid diethanolamide, lauric acid diethanolamide, and oleic acid monoethanolamide), triglycerides (e.g., fats and oils such as castor oil, coconut (including cochin) oil, corn oil, cottonseed oil, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, soybean oil, sunflower oil, tall oil, tallow, and derivatives of natural oils or functionalized natural oils such as epoxidized), alkyl alcohols (e.g., decyl alcohol, oleyl alcohol, cetyl alcohol, isodecyl alcohol, tridecyl alcohol, lauryl alcohol, and mixed C12 -C 14 alcohols containing from 4 to 18 carbon atoms per molecule), or combinations thereof.

[0039] In some embodiments, component (vi) comprises 0% to about 30% by weight (eg, 0% to 20% by weight, 0% to 10% by weight) of the wholly aromatic polyester polyol composition.

[0040] Method for producing an imide moiety-containing aromatic polyol compound To produce the imide moiety-containing aromatic polyol compound, each of components (i) through (iv) is placed in the same reaction vessel and subjected to esterification / transesterification reaction conditions. In some embodiments, any of the reactive components described above are also added to the reaction vessel. Reaction conditions typically include temperatures ranging from about 50° C. to about 300° C. (e.g., 70° C. to 250° C.) for times ranging from about 1 hour to about 24 hours (e.g., 3 hours to 10 hours).

[0041] In one embodiment, a pre-made aromatic polyester polyol made from components (i) through (iv), any 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 producing an imide moiety-containing aromatic polyol compound.

[0042] In some embodiments, an esterification / transesterification catalyst can be used to increase the rate of the reaction. 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 available from Arkema, Inc.); TM Catalysts (based on tin oxide), titanium catalysts (e.g. Tyzor TM TBT (titanium tetra-n-butoxide) catalyst; triethanolamine thianate chelate catalyst (e.g., Tyzor available from Dorf Ketal Specialty Catalysts); TMTE), alkaline catalysts (e.g., NaOH, KOH, sodium and potassium alkoxides) and acid catalysts (e.g., sulfuric acid, phosphoric acid, salt Typically, the catalyst is present at from about 0.001 to about 0.2 weight percent of the wholly aromatic polyester polyol composition.

[0043] After preparation, the imide moiety-containing aromatic polyol compound composition may contain a small amount of unreacted aliphatic diol. For example, in some embodiments, the composition may contain up to 30 wt. % free aliphatic diol, based on the total weight of the composition. However, the free aliphatic diol content of the composition generally ranges from 0 wt. % to 20 wt. % (e.g., 1 wt. % to 15 wt. %), based on the total weight of the composition.

[0044] It should be noted that in some embodiments, the aromatic polyester polyol composition is solvent-free. As used herein, "solvent-free" means that there is no solvent (e.g., acetone, tetrahydrofuran) present in the composition; however, in some cases, trace or incidental amounts of solvent (e.g., the amount of the solvent in the wholly aromatic polyester polyol composition) may be present. < 5% by weight, < 3% by weight, < 1% by weight may be present.

[0045] The imide moiety-containing aromatic polyol compound composition can also contain a nonionic emulsifier (i.e., a compound containing one or more hydrophobic moieties and one or more hydrophilic moieties, without dissociating into cations and anions in aqueous solution or dispersion). While almost any nonionic emulsifier compound can be used, in some embodiments, the nonionic emulsifier can be a polyoxyalkylene emulsifier containing an average of from about 4 to about 200 oxyalkylene groups per molecule, the oxyalkylene groups typically being selected from the group consisting of oxyethylene and oxypropylene. Typically, the nonionic emulsifier can comprise, for example, from about 0% to about 20% by weight (e.g., 0% to about 10% by weight) of the composition.

[0046] Fixes While particular embodiments of the present disclosure have been described in detail, it will be recognized by those skilled in the art that various modifications and changes to these details may occur in light of the entire disclosure. Accordingly, the disclosed arrangements are intended to be exemplary only and not limiting on the scope of the disclosure, which scope is to be given the full scope of the appended claims and all equivalents thereof. Accordingly, any of the above-listed features, properties, and / or elements can be combined with each other in any combination and still be within the breadth of the present disclosure. DETAILED DESCRIPTION OF THE INVENTION

[0047] Example Ingredients: In the examples, reference is made to the following reaction components, materials and terminology:

[0048] PTA: Purified terephthalic acid (available from Grupo Petrotemex, SA de CV).

[0049] DEG: Diethylene glycol (available from Equistar Chemicals, LP).

[0050] TEG: Triethylene glycol (available from Dow Chemical Company).

[0051] PEG 200: Polyethylene glycol 200 (available from Huntsman International LLC).

[0052] Glycerin (available from Terra Biochem LLC).

[0053] TYZOR® TE: 80% by weight solution of titanium (triethanolaminato) isopropoxide in isopropanol (available from Dorf Ketal Specialty Catalysts LLC).

[0054] TMA: Trimellitic anhydride (1,2,4-benzenetricarboxylic anhydride from Sigma Aldrich Corporation).

[0055] Glycine (available from Sigma Aldrich Corporation).

[0056] MDA: 4,4'-diaminodiphenylmethane (available from Sigma Aldrich Corporation).

[0057] TEROL® 250: An aromatic polyester polyol having an OH number of 250 mg KOH per gram (available from Huntsman International LLC).

[0058] Analysis and testing: In the examples, reference is made to the following terms:

[0059] Acid Number: A measure of the residual acid in a polyester polyol as determined by standard titration methods, such as ASTM D4662.

[0060] OH Number: Hydroxyl number, a measure of the number of OH groups determined by standard titration methods, e.g., ASTM D4274.

[0061] Viscosity: Using a Brookfield viscometer such as a Brookfield DV-II viscometer At 25°C The viscosity to be measured.

[0062] TGA Analysis: Thermogravimetric analysis (TGA) was performed using a TGA Q5000 from TA instruments-Water LLC, which is a method of thermal analysis that measures the mass of a sample over time as the temperature is changed.

[0063] Cone calorimeter test: The test is performed according to test method ASTM E1354-17 at 30 kW / m 2 The following parameters were recorded:

[0064] PHRR: Peak Heat Release Rate, the highest rate of heat release from a fire.

[0065] THR: Total heat generated by combustion at a given point in time.

[0066] TSR: Total smoke produced by combustion at a given point in time.

[0067] ML%: The percentage of mass loss at a given point during combustion.

[0068] Description of Polyol Synthesis Polyol-1: 286g PTA, 73g trimellitic anhydride (TMA), 38g MDA, 11g glycerin, 73g PEG 200, 194g TEG and 197g DEG were mixed in 500ml A 100 mL cylindrical glass reactor was charged with 1 mL of ethanol. The reaction mixture was heated to 80°C under a nitrogen flow of 0.3-0.5 liters per minute (LPM) and held at that temperature for 30 minutes. The mixture was then heated to 140°C, held at that temperature for 30 minutes, and then heated to 246°C. The temperature was then held at 246°C, and condensed water was collected. Once the head temperature dropped below 70°C (after approximately 2 hours), 0.8 g of Tyzor TE was added. The reaction mixture was then heated at 240°C until the acid number was less than 2.0 mg KOH per gram (after approximately 3 hours). The reaction mixture was cooled to less than 100°C, and Polyol-1 was collected. The OH number was measured, and then DEG was added to adjust the OH number to a calculated 250 mg KOH per gram while blending for 30 minutes at 80°C. The polyol was then cooled to room temperature, and the final OH number and viscosity were measured.

[0069] 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 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, held at that temperature for 30 minutes, and then heated to 246°C. The temperature was maintained at 246°C, and condensed water was collected. Once the peak temperature had dropped below 70°C (after approximately 3 hours), 0.8 g of Tyzor TE was added. The reaction mixture was then heated at 240°C until the acid number was less than 2.0 mg KOH per gram (approximately 5 hours). The reaction mixture was cooled to below 100°C, and Polyol-2 was collected. The OH number was measured and then DEG was added to adjust the OH number to a calculated 250 mg KOH per gram while compounding for 30 minutes at 80° C. The polyol was then cooled to room temperature and the final OH number and viscosity were measured.

[0070] Summary of polyol properties: [Table 1]

[0071] Polyol Thermal Stability Test: The thermal stability of inventive Polyol-1, Polyol-2, and comparative TEROL® 250 was evaluated using TGA under nitrogen and air, respectively. TGA is a widely accepted analytical method that provides an indication of relative thermal stability for the materials under consideration. All polyols were heated from 25°C to 700°C using a temperature ramp rate of 10°C / min. The percent retention of foam weight at a given temperature relative to the initial weight of the foam at 25°C is summarized in Tables 2 and 3 below. As expected, in all cases, the higher the temperature, the greater the extent of polyol degradation and the lower the percent weight retention. Inventive Polyol-1 and Polyol-2 exhibited higher weight retention compared to comparative TEROL® 250 polyol at all temperatures under both anaerobic and aerobic conditions. The higher weight retention at a given temperature in TGA is due to the relative thermal stability of Polyol-1 (where the TMA to PTA ratio is 0.29) and Polyol-2 (where the TMA to PTA ratio is zero) when compared to TEROL® 250 (where the TMA to PTA ratio is zero). A ratio is 0.255), suggesting better thermal stability relative to the [Table 2]

[0072] [Table 3]

Claims

1. A method for producing an aromatic polyester polyol compound containing imide moieties, comprising reacting a reactive mixture comprising: (i) Structure (1), Structure (2), or a combination thereof Structure (1): 【Chemistry 1】 Structure (2): 【Chemistry 2】 wherein X is a cyclic anhydride moiety, OH or COOH, which is attached to the structure directly or through R, R is a direct bond or an aromatic ring, an aliphatic ring, or an aliphatic chain group, each containing from 1 to 12 carbon atoms, with or without alkyl branching, and with or without heteroatoms, including O, N, S, etc., and n is an integer from 0 to 1. wherein component (i) is present in the reactive mixture in an amount of from 3% to 20% by weight; (ii) a phthalic acid-based compound, wherein component (ii) is present in the reactive mixture in an amount of 2% to 40% by weight; (iii) Structure (3) Structure (3): NH 2 -R-X wherein X is —NH, —OH, or —COOH, and R is an aromatic ring, an aliphatic ring, or an aliphatic chain group, each containing from 1 to 12 carbon atoms, with or without alkyl branching, and with or without heteroatoms, including O, N, S, or combinations thereof. wherein component (iii) is present in said reactive mixture in an amount of 1% to 15% by weight; (iv) an aliphatic diol compound, wherein component (iv) is present in the reactive mixture in an amount of 40% to 70% by weight; (v) optionally, a high functionality low molecular weight polyether polyol compound having 3 or more active hydrogen atoms per molecule and a molecular weight of up to 1000 Daltons; (vi) optionally, a hydrophobic compound having one or more substantially non-polar organic moieties; wherein the weight ratio of component (i) to component (ii) is from 1:20 to 4:1, and wherein the aromatic polyester polyol is a liquid at 25°C and contains a hydroxy number ranging from about 30 to about 600.

2. 10. The method of claim 1, wherein the aromatic polyester polyol compound has a viscosity ranging from about 200 to about 150,000 centipoise at 25[deg.]C.

3. 10. The method of claim 1, wherein the acid number of the aromatic polyester polyol compound ranges from about 0.1 mg KOH per gram to about 10 mg KOH per gram.

4. 10. The method of claim 1, wherein the method comprises reacting components (i), (ii), (iii) and (iv) in a single-pot synthesis.

5. 10. The method of claim 1, wherein the reaction does not occur in the presence of a solvent.

6. 1. An aromatic polyester polyol compound containing imide moieties, wherein the aromatic polyester polyol is a reaction product of a reactive mixture comprising the following components (i) through (vi): (i) Structure (1), Structure (2), or a combination thereof Structure (1): 【Transformation 3】 Structure (2): 【Chemistry 4】 wherein X is a cyclic anhydride moiety, OH or COOH, which is attached to the structure directly or through R, R is a direct bond or an aromatic ring, an aliphatic ring, or an aliphatic chain group, each containing from 1 to 12 carbon atoms, with or without alkyl branching, and with or without heteroatoms, including O, N, S, etc., and n is an integer from 0 to 1. wherein component (i) is present in the reactive mixture in an amount of from 3% to 20% by weight; (ii) a phthalic acid-based compound, wherein component (ii) is present in the reactive mixture in an amount of 2% to 40% by weight; (iii) Structure (3) Structure (3): NH 2 -R-X wherein X is —NH, —OH, or —COOH, and R is an aromatic ring, an aliphatic ring, or an aliphatic chain group, each containing from 1 to 12 carbon atoms, with or without alkyl branching, and with or without heteroatoms, including O, N, S, or combinations thereof. wherein component (iii) is present in said reactive mixture in an amount of 1% to 15% by weight; (iv) an aliphatic diol compound, wherein component (iv) is present in the reactive mixture in an amount of 40% to 70% by weight; (v) optionally, a high functionality low molecular weight polyether polyol compound having 3 or more active hydrogen atoms per molecule and a molecular weight of up to 1000 Daltons; (vi) optionally, a hydrophobic compound having one or more substantially non-polar organic moieties;

7. 7. The aromatic polyester polyol compound of claim 6, wherein the viscosity of the aromatic polyester polyol compound ranges from about 200 to about 150,000 centipoise at 25°C.

8. 7. The aromatic polyester polyol of claim 6, wherein the acid number of the aromatic polyester polyol compound ranges from about 0.1 mg KOH per gram to about 10 mg KOH per gram. ol compounds.

9. 7. The aromatic polyester polyol compound of claim 6, prepared by reacting components (i), (ii), (iii), and (iv) in a single-pot synthesis process.

10. 7. The aromatic polyester polyol compound of claim 6, wherein the reaction does not occur in the presence of a solvent.

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