Coating composition

Abstract

Disclosed is a composition comprising a first component comprising an isocyanate, a second component comprising a first polyol comprising phosphorus, a second polyol comprising sulfur, or a combination of the first polyol and the second polyol; and a filler in an amount of at least 40% by weight based on the total weight of the composition. A substrate comprising a coating deposited from the composition and a method of coating a substrate are also disclosed.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Application No. 63 / 365,906, filed on June 6, 2022, and U.S. Provisional Application No. 63 / 486,521, filed on February 23, 2023, both of which are titled “Coating Compositions,” which are incorporated herein by reference in their entireties. Technical Field

[0003] The present disclosure relates to flame retardant compositions and flame retardant materials formed therefrom. Background Art

[0004] Potants and gaskets are known to be used in battery assemblies to minimize movement and provide stability to the battery cells. Summary of the invention

[0005] The present disclosure relates to a composition comprising: a first component, the first component comprising an isocyanate; a second component, the second component comprising a first polyol including phosphorus, a second polyol including sulfur, or a combination of the first polyol and the second polyol; and a filler, the filler being present in an amount of at least 40 weight percent based on the total weight of the composition.

[0006] Also disclosed is a method of coating a substrate, the method comprising contacting a portion of a surface of the substrate with any of the compositions disclosed herein.

[0007] Also disclosed is a method of forming an article comprising extruding any of the compositions disclosed herein.

[0008] Also disclosed is a substrate comprising a coating formed on a surface of the substrate from any of the compositions disclosed herein.

[0009] Also disclosed is a battery module comprising a battery cell and one of the compositions disclosed herein in an at least partially cured state positioned adjacent a surface of the battery cell.

[0010] Also disclosed is a battery comprising a battery cell and a coating formed from any of the compositions disclosed herein.

[0011] Also disclosed is a vehicle comprising any of the batteries disclosed herein.

[0012] Also disclosed is the use of any of the compositions disclosed herein for preparing a coating having a flame retardancy of V-0 or V-1 as measured according to the UL-94 standard and a thermal conductivity of at least 0.4 W / mK as measured using a TCi thermal conductivity analyzer from C-Therm Technologies Ltd using a modified transient plane source method in accordance with ASTM D7984.

[0013] Also disclosed is the use of a coating formed from any of the compositions disclosed herein for providing a substrate with a flame retardant performance of V-0 or V-1 as measured according to the UL-94 standard and a thermal conductivity of at least 0.4 W / mK as measured using a TCi thermal conductivity analyzer from C-Therm Technologies, Inc. using a modified transient plane source method conforming to ASTM D7984.

[0014] Also disclosed is a polyol comprising structure (I):

[0015]

[0016] Where R 1 and R 2 Each of (i.e., the substituents of structure (I)) comprises a (cyclo)alkyl, aryl, aromatic, polymer structure (including polyester or polyether), or can together form a (cyclo)alkyl, aryl or aromatic structure, and wherein R 1 and R 2 Can be the same or different. As used herein, throughout this disclosure, "(cyclo)alkyl" refers to both alkyl and cycloalkyl. As used herein, throughout this disclosure, when any R group in the R group "together can form a (cyclo)alkyl, aryl and / or aromatic group", it means that any two adjacent R groups are connected to form a cyclic portion.

[0017] Also disclosed is a polyol comprising structure (II):

[0018]

[0019] Where R 3 and R 4 (i.e., the substituents of structure (II)) contain (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 3 and R 4 Can be the same or different.

[0020] Also disclosed is a polyol comprising structure (III):

[0021]

[0022] Where R 5 , R 6 , R 7 and R 8 (i.e., the substituents of structure (III)) contain hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 5 , R 6 , R 7 and R 8 Can be the same or different.

[0023] Also disclosed is a polyol comprising structure (IV):

[0024]

[0025] Where R 9 , R 10 , R 11 and R 12 (i.e., the substituents of structure (IV)) contain hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 9 , R 10 , R 11 and R 12 Can be the same or different. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 is a schematic diagram of a top view of a cylindrical battery cell.

[0027] Figure 2 is a schematic diagram of an exploded isometric view of an array of prismatic battery cells.

[0028] Figure 3 is a schematic diagram of a front view of an array of pouch-shaped battery cells.

[0029] Figure 4 is a schematic diagram of an isometric view of a cylindrical battery cell positioned in a battery module.

[0030] Figure 5 is a schematic diagram of an exploded perspective view of a battery pack including a plurality of battery cells.

[0031] 6 is a schematic diagram of isometric views of (A) a battery cell, (B) a battery module, and (C) a battery pack.

[0032] Figure 7is a schematic diagram of a perspective view of a battery pack.

[0033] Figure 8 is a schematic diagram of the battery cell to battery pack configuration.

[0034] Fig. 9 is a schematic diagram of an isometric cutaway view of a battery cell to chassis battery assembly. DETAILED DESCRIPTION

[0035] For the purpose of this detailed description, it should be understood that the present disclosure may take alternative variations and step sequences except where explicitly stated otherwise. In addition, except in any operating examples or where otherwise indicated, in all cases, all numerals expressing the quantity of components used in the present specification and claims should be understood to be modified by the term "about". Therefore, unless otherwise indicated, the numerical parameters set forth in the following specification and the appended claims are approximate values ​​that can be changed according to the desired properties to be obtained by the present disclosure. At least, and not attempting to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be interpreted according to the number of reported significant figures and by applying common rounding techniques.

[0036] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the disclosure are approximations, the numerical values ​​set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements.

[0037] Furthermore, it should be understood that any numerical range recited herein is intended to include all subranges subsumed therein. For example, a range of "1 to 10" is intended to include all subranges between (and including) the recited minimum value of 1 and the recited maximum value of 10, i.e., having a minimum value equal to or greater than 1 and a maximum value equal to or less than 10.

[0038] As used herein, "including", "containing" and similar terms are understood to be synonymous with "comprising" in the context of this application, and are therefore open-ended and do not exclude the presence of additional undescribed or unrecited elements, materials, ingredients, or method steps. As used herein, "consisting of" is understood to exclude the presence of any unspecified elements, ingredients, or method steps in the context of this application. As used herein, "consisting substantially of" is understood to include the specified elements, materials, ingredients, or method steps "as well as elements, materials, ingredients, or method steps that do not materially affect the basic and novel characteristics of the described content" in the context of this application. As used herein, open-ended terms include closed terms, such as consisting substantially of and consisting of.

[0039] In this application, unless specifically stated otherwise, the use of the singular includes the plural and the plural encompasses the singular. For example, although reference is made herein to "an" isocyanate and "an" polyol, combinations of these components (ie, a plurality of these components) may be used.

[0040] Additionally, in this application, the use of "or" means "and / or" unless explicitly stated otherwise, even though "and / or" may be explicitly used in some cases.

[0041] As used herein, the terms "on," "onto," "applied on," "applied onto," "formed on," "deposited on," "deposited onto," "injected on," "injected onto," and the like mean formed, covered, deposited, or provided on a substrate surface but not necessarily in contact with the substrate surface. For example, a composition "applied to" a substrate surface does not preclude the presence of one or more other intermediate coatings of the same or different composition located between the composition and the substrate surface.

[0042] As used herein, "composition" or "coating composition" refers to a solution, mixture or dispersion capable of producing a coating on a portion of a substrate. As used herein, "coating" includes films, layers, and the like.

[0043] As used herein, the term "two-component" or "2K" refers to a composition that cures when mixed without activation from an external energy source, such as under ambient or mild heat conditions. Typically, ambient conditions range from 10°C to 32°C and 20% to 80% relative humidity, and mild heat conditions range from 32°C to 40°C. It will be understood by those skilled in the art that the two components of the composition are stored separately from each other and mixed when the composition is about to be applied. As described below, the two-component composition can be optionally heated or baked.

[0044] As used herein, the term "cure" or "curing" means that the components forming the composition interact or react to form a coating, as evidenced by an increase in viscosity measured after mixing the first component with the second component. Unless otherwise indicated, the viscosities disclosed herein can be measured under ambient conditions according to a Brookfield viscometer (Model DV-I, RV-7 spindle).

[0045] The term "curable" as used, for example, in connection with a coating composition means that the composition is capable of being cured under ambient or mild heat conditions.

[0046] As used herein, "Mw" refers to the weight average molecular weight, such as the theoretical value determined by gel permeation chromatography using a Waters 2695 separation module with a Waters 410 differential refractometer (RI detector) and polystyrene standards, with tetrahydrofuran (THF) used as the flow rate at 1 ml min -1 The eluate was mixed with two PL gel C columns for separation.

[0047] As used herein, "polymer" refers to oligomers, homopolymers, and copolymers.

[0048] As used herein, "small molecule" refers to a molecule that has a Mw of less than 1200 g / mol and is not a polymer (ie, is not composed of repeating monomer units).

[0049] As used herein, the term "reactive diluent" refers to a molecule or compound having a low vapor pressure, such as 2 mm Hg or less at 25°C as determined by differential scanning calorimetry according to ASTM E1782 and used to reduce the viscosity of the resin but having at least one functional group capable of reacting with a functional group on a molecule or compound in the composition.

[0050] As used herein, the term "plasticizer" refers to a molecule or compound that has no functional groups capable of reacting with functional groups on molecules or compounds in the composition and is added to the composition to reduce viscosity, lower the glass transition temperature (Tg) and impart flexibility.

[0051] As used herein, the term "promoter" means a substance that increases the rate of a chemical reaction or decreases the activation energy of a chemical reaction compared to the same reaction in the absence of the promoter. A promoter can be a "catalyst," i.e., does not undergo any permanent chemical change itself, or can be reactive, i.e., capable of chemical reaction and includes any level of reaction from partial reaction of the reactants to complete reaction.

[0052] As used herein, unless otherwise stated, the term "substantially free" means that the specific material is not intentionally added to the mixture or composition, respectively, and is present only in the form of trace impurities of less than 5% by weight, respectively, based on the total weight of the mixture or composition. As used herein, unless otherwise stated, the term "substantially free" means that the specific material is present only in an amount of less than 2% by weight, respectively, based on the total weight of the mixture or composition. As used herein, unless otherwise stated, the term "completely free" means that the mixture or composition does not contain the specific material, respectively, that is, the mixture or composition includes 0% by weight of such material.

[0053] Disclosed herein is a composition comprising, consisting essentially of, or consisting of a first component comprising an isocyanate; a second component comprising a first polyol comprising phosphorus, a second polyol comprising sulfur, or a combination of the first polyol and the second polyol; and a filler, the filler being present in an amount of at least 40 weight percent based on the total weight of the composition.

[0054] Isocyanate

[0055] The first component may comprise, consist essentially of, or consist of an isocyanate. The isocyanate may be monomeric or polymeric and may contain one or more isocyanate functional groups (-N=C=O).

[0056] Suitable monomeric isocyanate-containing compounds include p-tolyl isocyanate, hexyl isocyanate, phenyl isocyanate, arylethyl isocyanate, methacryloyloxyethyl isocyanate, and 3-(triethoxysilyl)propyl isocyanate.

[0057] Suitable isocyanate-containing compounds that can be used in the compositions described herein can include polyisocyanates. For example, the polyisocyanate can include C2-C 20 Linear, branched, cyclic, aliphatic and / or aromatic polyisocyanates.

[0058] Aliphatic polyisocyanates may include (i) alkylene isocyanates, such as trimethylene diisocyanate; tetramethylene diisocyanates, such as 1,4-tetramethylene diisocyanate; pentamethylene diisocyanates, such as 1,5-pentamethylene diisocyanate and 2-methyl-1,5-pentamethylene diisocyanate; hexamethylene diisocyanate ("HDI"), which may be Demodur XP 2617 (Covestro), such as 1,6-hexamethylene diisocyanate and 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate, or mixtures thereof; heptamethylene diisocyanates, such as 1,7-heptamethylene diisocyanate; propylene diisocyanates, such as 1,2-propylene diisocyanate; butylene diisocyanates, such as 1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate and 1,4-butylene diisocyanate; ethylene diisocyanate; decamethylene diisocyanates, such as 1,10-decamethylene diisocyanate; ethylene diisocyanate; and butylene diisocyanate. The aliphatic polyisocyanate may also include (ii) cycloalkylene isocyanates, such as: cyclopentane diisocyanate, such as 1,3-cyclopentane diisocyanate; cyclohexane diisocyanate, such as 1,4-cyclohexane diisocyanate, 1,2-cyclohexane diisocyanate, isophorone diisocyanate ("IPDI"), methylene bis(4-cyclohexyl isocyanate) ("HMDI"); and mixed aralkyl diisocyanates, such as tetramethylxylylene diisocyanate, such as meta-tetramethylxylylene diisocyanate ("m-tetramethylxylylene diisocyanate"). Commercially available from Allnex SA). Dimers, trimers, oligomers and polymers of the above polyisocyanates may also be used as the cyclotrimer of 1,6 hexamethylene diisocyanate (also known as the isocyanate trimer of HDI, commercially available as Desmoder N3300 (Covestro)).

[0059] The aromatic polyisocyanate may include (i) arylene isocyanates such as: phenylene diisocyanates, such as m-phenylene diisocyanate, p-phenylene diisocyanate and chlorophenylene 2,4-diisocyanate; naphthalene diisocyanates, such as 1,5-naphthalene diisocyanate and 1,4-naphthalene diisocyanate. Aromatic polyisocyanates may also include (ii) aralkylene isocyanates, such as: methylene interrupted aromatic diisocyanates, such as 4,4'-diphenylmethane diisocyanate ("MDI"), and alkylated analogs, such as 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate and polymeric methylene diphenyl diisocyanate; toluene diisocyanates ("TDI"), such as 2,4-tolylene or 2,6-tolylene diisocyanate or mixtures thereof, xylene diisocyanate; and 4,4-toluidine diisocyanate; xylene diisocyanate; o-dianisidine diisocyanate; xylylene diisocyanate; and other alkylated phenylene diisocyanates.

[0060] Polyisocyanates may also include triisocyanates such as triphenylmethane-4,4',4"-triisocyanate, 1,3,5-triisocyanatobenzene and 2,4,6-triisocyanatotoluene; tetraisocyanates such as 4,4'-diphenyldimethylmethane-2,2',5,5'-tetraisocyanate; and polymeric polyisocyanates such as tolylene diisocyanate dimer and trimer.

[0061] In addition to isocyanate functional groups, isocyanate-containing compounds can also have at least one functional group, such as siloxane functional groups, epoxy functional groups and / or acrylic functional groups. Isocyanate-containing compounds can be substantially free of, or substantially free of, or completely free of functional groups other than isocyanate functional groups. As used herein, when used in the absence of siloxane functional groups, the term "substantially free of" means based on the total weight of isocyanate-containing compounds, and the isocyanate-containing compounds contain less than 122 parts per million (ppm) of siloxane. As used herein, when used in the absence of epoxy functional groups, the term "substantially free of" means based on the total weight of isocyanate-containing compounds, and the isocyanate-containing compounds contain less than 44ppm of epoxides. As used herein, when used in the absence of acrylic functional groups, the term "substantially free of" means based on the total weight of isocyanate-containing compounds, and the isocyanate-containing compounds contain less than 71ppm of acrylates. As used herein, the term "completely free" when used with respect to the absence of functional groups other than isocyanate functional groups means that such functional groups are present in the composition only in an amount of less than 1 part per billion (ppb) based on the total weight of the composition, or such functional groups are below the detection limit of commonly used analytical techniques.

[0062] The first component may include at least 15 wt %, such as at least 30 wt %, of isocyanate, based on the total weight of the first component. The first component may include no more than 100 wt %, such as no more than 70 wt %, of isocyanate, based on the total weight of the first component. The first component may include from 15 wt % to 100 wt %, such as from 30 wt % to 70 wt %, of isocyanate, based on the total weight of the first component.

[0063] The first component of the composition can also include an isocyanate functional prepolymer. The isocyanate functional prepolymer can be the reaction product of any of the isocyanates disclosed herein and any of the polyols described herein, wherein the polyol has at least two hydroxyl functional groups. As used herein, "isocyanate functional prepolymer" refers to the reaction product of a polyisocyanate and a polyol. The isocyanate functional prepolymer has at least one free isocyanate functional group (NCO). The free isocyanate functional group can be terminal and / or can be located on a side chain. Combinations of isocyanate functional prepolymers can be used.

[0064] The Mw of the isocyanate functional prepolymer may be at least 300 g / mol, such as at least 600 g / mol, such as at least 1,000 g / mol, such as at least 3,000 g / mol, and the weight average molecular weight may be no more than 30,000 g / mol, such as no more than 20,000 g / mol, such as no more than 15,000 g / mol, such as no more than 10,000 g / mol. The Mw of the isocyanate functional prepolymer may be from 300 g / mol to 30,000 g / mol, such as from 600 g / mol to 20,000 g / mol, such as from 1,000 g / mol to 15,000 g / mol, such as from 3,000 g / mol to 10,000 g / mol.

[0065] The isocyanate equivalent weight of the isocyanate functional prepolymer may be at least 150, such as at least 300, such as at least 500, such as at least 1,500, and the isocyanate equivalent weight may be no more than 15,000, such as no more than 10,000, such as no more than 7,500, such as no more than 5,000. The isocyanate equivalent weight of the isocyanate functional prepolymer may be from 150 to 15,000, such as from 300 to 10,000, such as from 500 to 7,500, such as from 1,500 to 5,000.

[0066] The first component may include an isocyanate functional prepolymer, which may be present in the first component of the composition in an amount of at least 5 wt %, such as at least 30 wt %, based on the total weight of the first component. The first component may include an amount of no more than 100 wt %, such as no more than 70 wt %, based on the total weight of the first component. The first component may include an amount of 5 wt % to 100 wt %, such as 30 wt % to 70 wt %, based on the total weight of the first component.

[0067] Polyols

[0068] The second component may comprise or consist substantially of or consist of a polyol. The polyol may include diols, triols, tetraols and higher functional polyols, i.e. compounds containing five or more hydroxyls per molecule. The polyol may be linear, branched, cyclic, aliphatic and / or aromatic. The polyol may be a small molecule or a polymer. The polyol may optionally be a liquid. Combinations of such polyols may also be used.

[0069] Any of the polyols described below can be modified to include phosphorus, sulfur, or a combination thereof. For example, the polyol can be modified to include a phosphate, a phosphonate, a sulfide, a disulfide, a polysulfide, a sulfone, a thiol, a thioester, or a combination thereof.

[0070] Non-limiting examples of suitable polyols include, but are not limited to, polyether polyols, polyester polyols, polycaprolactone polyols, polycarbonate polyols, polyurethane polyols, polyvinyl alcohol, hydroxy-functional acrylate-containing polymers, hydroxy-functional methacrylate-containing polymers, allyl alcohol-containing polymers, hydroxy-functional polybutadiene, and mixtures thereof.

[0071] Polyol can be based on the polyether chain produced by ethylene glycol, propylene glycol, butylene glycol, hexylene glycol etc. and its mixture. Polyol can also be based on the polyester chain produced by the ring-opening polymerization of caprolactone (hereinafter referred to as polyol based on polycaprolactone). Suitable polyol can also include polyether polyol, polyurethane polyol, polyurea polyol, acrylic polyol, polyester polyol, polybutadiene polyol, hydrogenated polybutadiene polyol, polycarbonate polyol, polysiloxane polyol and its combination. Polyamine corresponding to polyol can also be used.

[0072] The polyol may comprise a polycaprolactone-based polyol. The polycaprolactone-based polyol may comprise a diol, a triol or a tetraol terminated with a primary hydroxyl group. Commercially available polycaprolactone-based polyols include those sold under the trade name Capa TMThose polyols are sold, for example, as Capa 2054, Capa 2077A, Capa 2085, Capa 2205, Capa 3031, Capa 3050, Capa 3091 and Capa 4101.

[0073] The polyol may comprise a polytetrahydrofuran-based polyol. The polytetrahydrofuran-based polyol may comprise a diol, a triol or a tetrols terminated with primary hydroxyl groups. Commercially available polytetrahydrofuran-based polyols include those available from Invista under the trade name Polyols based on polytetrahydrofuran are sold as PTMEG 250 and PTMEG 650, these are blends of linear diols in which the hydroxyl groups are separated by repeating tetramethylene ether groups.

[0074] Alternatively, the styrene-based polymer available from Cognis Corporation under the trade name and Polyols sold based on dimer diol or bio-based polyols such as castor oil.

[0075] In addition, the polyol may comprise a bio-based polyol produced from renewable raw materials. The bio-based polyol may comprise a diol, a triol or a tetraol terminated with a primary hydroxyl group. Commercially available bio-based polyols include castor oil-based polyols, soybean oil-based polyols, cashew oil-based polyols, palm oil-based polyols and dimer acid-based polyols. Suitable examples include Agrol 4.0 (available from BioBased Technologies), Elevance DC18 TM Polyols and Priplast TM Polyols.

[0076] The hydroxide functionality of the polyol may be at least 1, such as greater than 1, such as at least 2, such as at least 3. The hydroxide functionality of the polyol may be from 1 to 10, such as from 2 to 8. As used herein, the term "hydroxide functionality" means the number of hydroxyl functional groups on a hydroxyl-containing molecule.

[0077] As discussed above, any of the polyols disclosed herein can be modified to include phosphorus or sulfur, or both.

[0078] The weight average molecular weight of the polyol modified to include phosphorus can be at least 150 g / mol, such as at least 2,000 g / mol, as determined by gel permeation chromatography using polystyrene standards, and the weight average molecular weight can be no more than 8,000 g / mol, such as no more than 6,000 g / mol, as determined by gel permeation chromatography using polystyrene standards. The weight average molecular weight of the polyol modified to include phosphorus can be from 150 g / mol to 8,000 g / mol, such as from 2,000 g / mol to 6,000 g / mol, as determined by gel permeation chromatography using polystyrene standards.

[0079] In an example, the phosphorus-containing polyol may comprise structure (I):

[0080]

[0081] Where R 1 and R 2 (i.e., the substituents of structure (I)) contain hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 1 and R 2 Can be the same or different.

[0082] Suitable examples of phosphorus-containing polyols shown in structure (I) include structures (IA), (IB) and (IC):

[0083]

[0084] The phosphonate shown in structure (I) may be the reaction product of ε-caprolactone or lactide and a phosphonate polyol.

[0085]

[0086] (Reaction Schemes (IA), (IB), (IC)).

[0087] In an example, the phosphorus-containing polyol may comprise structure (II):

[0088]

[0089] Where R 3 and R 4 (i.e., the substituents of structure (II)) contain (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 3 and R 4 Can be the same or different.

[0090] Suitable examples of phosphorus-containing polyols shown in structure (II) include structure (IIA):

[0091]

[0092] The phosphonate shown in structure (II) can be the reaction product of a reaction product of a phosphonate, an anhydride, and an epoxide. For example, the phosphonate shown in structure (II) can be the reaction product of a phosphonate monool, an anhydride, and a diepoxide.

[0093]

[0094] The second component may include a polyol modified to include phosphorus, and the amount of the polyol (if present) is at least 1 wt %, such as at least 30 wt %, based on the total weight of the second component. The second component may include a polyol modified to include phosphorus, and the amount of the polyol (if present) is not more than 100 wt %, such as not more than 70 wt %, based on the total weight of the second component. The second component may include a polyol modified to include phosphorus, and the amount of the polyol (if present) is from 1 wt % to 100 wt %, such as from 30 wt % to 70 wt %, based on the total weight of the second component.

[0095] The sulfur-containing polyol may comprise structure (III) and / or structure (IV):

[0096]

[0097] Where R 5 , R 6 , R 7 and R 8 (i.e., the substituents of structure (III)) contain hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 5 , R 6 , R 7 and R 8 may be the same or different; and wherein R 9 , R 10 , R 11 and R 12 (i.e., the substituents of structure (IV)) contain hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structures (including polyesters or polyethers), or can together form (cyclo)alkyl, aryl or aromatic structures, and wherein R 9 , R 10 , R 11 and R 12 Can be the same or different.

[0098] Suitable examples of the sulfur-containing polyols shown in structure (III) include structure (IIIA):

[0099]

[0100] Where n=10-12.

[0101] The sulfide shown in structure (III) can be the reaction product of a thiol-functional compound and an epoxy-functional compound such as a monoepoxide or a diepoxide.

[0102]

[0103] The sulfide shown in structure (IV) can be the reaction product of a thiol-functional compound and an epoxy-functional compound such as a monoepoxide or a diepoxide.

[0104]

[0105] The second component may include a polyol modified to include sulfur, and the amount of the polyol (if present) is at least 1 wt %, such as at least 30 wt %, based on the total weight of the second component. The second component may include a polyol modified to include sulfur, and the amount of the polyol (if present) does not exceed 100 wt %, such as does not exceed 70 wt %, based on the total weight of the second component. The second component may include a polyol modified to include sulfur, and the amount of the polyol (if present) is from 1 wt % to 100 wt %, such as from 30 wt % to 70 wt %, based on the total weight of the second component.

[0106] The second component may include a polyol modified to include phosphorus and a polyol modified to include sulfur, the total amount of the two polyols being at least 1 wt %, such as at least 30 wt %, based on the total weight of the second component. The second component may include a polyol modified to include phosphorus and a polyol modified to include sulfur, the total amount of the two polyols not exceeding 100 wt %, such as not exceeding 70 wt %, based on the total weight of the second component. The second component may include a polyol modified to include phosphorus and a polyol modified to include sulfur, the total amount of the two polyols being from 1 wt % to 100 wt %, such as from 30 wt % to 70 wt %, based on the total weight of the second component.

[0107] The composition may also optionally further comprise a polyol other than a phosphorus-containing polyol and a sulfur-containing polyol. That is, the composition may further comprise a polyol (such as a third polyol) comprising any of the polyols described above but not modified to contain phosphorus and / or sulfur. As used herein with respect to polyols, reference to "first", "second", "third", etc. is only for convenience and does not refer to the order of addition to the composition, etc.

[0108] The second component may include such a polyol: the amount of the polyol (if present) is at least 1 wt %, such as at least 30 wt %, based on the total weight of the second component. The second component may include such a polyol: the amount of the polyol (if present) is not more than 99 wt %, such as not more than 70 wt %, based on the total weight of the second component. The second component may include such a polyol: the amount of the polyol is from 1 wt % to 99 wt %, such as from 30 wt % to 70 wt %, based on the total weight of the second component.

[0109] filler

[0110] The composition disclosed herein may also include a filler. The filler may include a thermally conductive electrically insulating filler (referred to herein as a "TC / EI filler" and described in more detail below) and / or a thermally conductive electrically conductive filler (referred to herein as a "TC / EC filler" and described in more detail below) and / or a non-thermally conductive electrically insulating filler (referred to herein as a "NTC / EI" filler material). TC / EI, TC / EC and / or NTC / EI fillers (collectively referred to as "fillers") may be present in the first component, the second component and / or the third component. TC / EI, TC / EC and / or NTC / EI fillers may include organic or inorganic materials and may include particles of a single type of filler material or may include particles of two or more types of TC / EI fillers and / or two or more types of TC / EC fillers and / or two or more types of NTC / EI fillers. That is, the filler may include a first TC / EI filler and may further include at least a second (i.e., second, third, fourth, etc.) TC / EI filler in addition to the first TC / EI filler. Likewise, the filler may comprise a first TC / EC filler and may further comprise at least a second (i.e., second, third, fourth, etc.) TC / EC filler in addition to the first TC / EC filler. Optionally, the filler may comprise a first NTC / EI filler and may further comprise at least a second (i.e., second, third, fourth, etc.) NTC / EI filler in addition to the first NTC / EI filler. References to "first," "second," etc., as used herein with respect to types of fillers, are for convenience only and do not refer to the order of addition to the composition, etc.

[0111] Optionally, any of the fillers may include a surface coating. The surface coating may include a silane, an amino-silane and / or a multidentate polymer.

[0112] The reported average particle size of the filler in at least one dimension can be at least 0.01 μm, such as at least 2 μm, such as at least 10 μm, as reported by the manufacturer, and the reported average particle size in at least one dimension can be no more than 500 μm, such as no more than 400 μm, such as no more than 300 μm, such as no more than 100 μm, as reported by the manufacturer. The reported average particle size of the filler in at least one dimension can be 0.01 μm to 500 μm, such as 0.1 μm to 400 μm, such as 2 μm to 300 μm, such as 10 μm to 100 μm, as reported by the manufacturer. The particle size can be measured by methods known to those skilled in the art, such as using a scanning electron microscope (SEM), such as Quanta 250FEG SEM or equivalent instruments. For example, the powder can be dispersed on a carbon ribbon fragment attached to an aluminum rod and coated with Au / Pd for 20 seconds. The samples can then be analyzed in a SEM under high vacuum (accelerating voltage 10 kV and spot size 3.0), measuring 30 particles from three different areas to provide an average particle size for each sample. Those skilled in the art will recognize that there can be variations in this procedure that retain the basic elements of microscopic imaging and average representative size.

[0113] The thermally conductive filler may include particles and agglomerates thereof, each of the particles having, for example, a plate-like, spherical or needle-like shape. As used herein, "plate-like" refers to a two-dimensional material having a substantially flat surface and a thickness in one direction less than 25% of the largest dimension.

[0114] The thermal conductivity of the thermally conductive filler (i.e., TC / EI and / or TC / EC filler) may be at least 5 W / m·K (measured according to ASTM D7984) at 25° C., such as at least 18 W / m·K, such as at least 55 W / m·K, and the thermal conductivity may be no more than 3,000 W / m·K, such as no more than 1,400 W / m·K, such as no more than 450 W / m·K at 25° C. The thermal conductivity of the thermally conductive filler may be 5 W / m·K to 3,000 W / m·K (measured according to ASTM D7984) at 25° C., such as 18 W / m·K to 1,400 W / m·K, such as 55 W / m·K to 450 W / m·K.

[0115] Optionally, the composition may further comprise a non-thermally conductive filler. The thermal conductivity of the non-thermally conductive filler may be less than 5 W / m·K at 25°C (measured according to ASTM D7984), such as no more than 3 W / m·K, such as no more than 1 W / mK, such as no more than 0.1 W / mK, such as no more than 0.05 W / mK, such as 0.02 W / m·K at 25°C to 5 W / m·K at 25°C. The thermal conductivity may be measured as described above.

[0116] The filler may be electrically insulating. The electrically insulating filler may have a volume resistivity of at least 1 Ω·m (measured according to ASTM D257), such as at least 10 Ω·m, such as at least 100 Ω·m.

[0117] The filler may be electrically conductive. The volume resistivity of the electrically conductive filler may be less than 1 Ω·m (measured according to ASTM D257), such as less than 0.1 Ω·m.

[0118] Suitable TC / EI fillers include: boron nitride (e.g., available as CarboTherm from Saint-Gobain, CoolFlow and PolarTherm from Momentive, and hexagonal boron nitride powder available from Panadyne), silicon nitride or aluminum nitride (e.g., available as aluminum nitride powder available from Micron Metals Inc. and Toyalnite from Toyal); metal oxides such as boehmite, pseudoboehmite, alumina (e.g., available as Microgrit from Microgrit); Abrasives), commercially available as Nabalox from Nabaltec, as Aeroxide from Evonik, and as Alodur from Imerys), magnesium oxide, beryllium oxide, silicon dioxide, titanium oxide, zinc oxide, nickel oxide, copper oxide, or tin oxide; metal hydroxides, such as aluminum trihydrate, aluminum hydroxide, or magnesium hydroxide; arsenides, such as boron arsenide; carbides, such as silicon carbide; minerals, such as agate and corundum; ceramics, such as ceramic microspheres (for example, commercially available from Zeeospheres Ceramics or 3M); silicon carbide; and diamond. These fillers can also be surface-modified, such as PYROKISUMA 5301K available from Kyowa Chemical Industry Co., Ltd. These thermally conductive fillers can be used alone or in combination of two or more.

[0119] Suitable TC / EC fillers include: metals such as silver, zinc, copper, gold or metal-coated hollow particles; carbon compounds such as graphite (such as Timrex commercially available from Ingres or ThermoCarb commercially available from Asbury Carbons), carbon black (e.g., Vulcan commercially available from Cabot Corporation), carbon fibers (e.g., milled non-carbon fibers commercially available from Zoltek), graphene and graphene carbon particles (e.g., xGnP graphene nanoplatelets commercially available from XG Sciences and / or graphene particles such as described below); carbonyl iron; copper (e.g., spherical powder commercially available from Sigma Aldrich); zinc (e.g., Ultrapure commercially available from Purity Zinc Metals and Ultrapure commercially available from US Zinc Corporation); Zinc) obtained by XL and XLP) etc. "Graphene carbon particles" include carbon particles with a structure of one or more layers of single-atom-thick planar sheets of sp2-bonded carbon atoms, and the carbon atoms are closely packed in a honeycomb lattice. The average number of stacked layers can be less than 100, for example, less than 50. The average number of stacked layers can be 30 or less, such as 20 or less, such as 10 or less, such as 5 or less. Graphene carbon particles can be substantially flat, however, at least a portion of the planar sheet can be substantially curved, curled, wrinkled or buckled. Particles generally do not have a spherical or equiaxed morphology. Suitable graphene carbon particles are described in U.S. Publication No. 2012 / 0129980,

[0059] -

[0065] , and the cited portion of the U.S. Publication is incorporated herein by reference. Other suitable graphene carbon particles are described in U.S. Pat. No. 9,562,175 at 6:6 to 9:52, the cited portion of which is incorporated herein by reference. As used herein, the term "substantially flat" means a plane; a "bent" or "curled" material deviates from a plane by having a non-zero curvature; and a "wrinkled" or "buckled" means that at least a portion of the region is thicker than a sheet, such that a plane is folded in half or folded upon itself.

[0120] Suitable NTC / EI fillers include, but are not limited to, mica, wollastonite, calcium carbonate, glass microspheres, clay, or combinations thereof.

[0121] As used herein, the term "mica" generally refers to sheet silicate (layered silicate) minerals. Mica may include muscovite. Muscovite includes a mineral having the formula KAl2(AlSi3O 10(F,OH)2 or (KF)2(Al2O3)3(SiO2)6(H2O). Exemplary non-limiting commercially available muscovite includes DakotaPURE available from Pacer Minerals. TM Products for sale, such as DakotaPURE TM 700、DakotaPURE TM 1500、DakotaPURE TM 2400、DakotaPURE TM 3000、DakotaPURE TM 3500 and DakotaPURE TM 4000. Wollastonite comprises calcium inosilicate minerals (CaSiO3) that may contain small amounts of iron, aluminum, magnesium, manganese, titanium and / or potassium. The BET surface area of ​​wollastonite may be 1.5 to 2.1 m 2 / g, such as 1.8m 2 / g, and the median particle size may be 6 to 10 microns, such as 8 microns. Non-limiting examples of commercially available wollastonite include NYAD 400 available from NYCO Minerals, Inc.

[0122] Calcium carbonate (CaCO3) may comprise precipitated calcium carbonate or ground calcium carbonate. The calcium carbonate may or may not be surface treated, such as with stearic acid. Non-limiting examples of commercially available precipitated calcium carbonate include calcium carbonate available from Specialty Minerals, and Albacar and available from Solvay SPT. Non-limiting examples of commercially available ground calcium carbonate include Duramite available from Ingol Ceramics TM and available from Specialty Minerals

[0123] Useful clay minerals include nonionic platy fillers such as talc, pyrophyllite, chlorite, vermiculite, or combinations thereof.

[0124] The glass microspheres may be hollow borosilicate glass.Non-limiting examples of commercially available glass microspheres include 3M Glass Bubbles VS, K Series, and S Series available from 3M Company.

[0125] As discussed above, fillers can be present in the first component, the second component, and / or the third component or higher components. Based on the total weight of the composition disclosed herein, the composition can include an amount of at least 40% by weight, such as at least 55% by weight of filler. The composition disclosed herein can include an amount of no more than 75% by weight, such as no more than 90% by weight of filler. Based on the total weight of the composition disclosed herein, the composition can include an amount of 40% to 90% by weight, such as 55% to 75% by weight of filler.

[0126] Accelerator

[0127] The disclosed composition may optionally include a promoter. The promoter may be an amine-based catalyst. For example, the promoter may be guanidine, substituted guanidine, substituted urea, melamine resin, guanamine derivative, cyclic tertiary amine, aromatic amine, acid-blocked amine or a combination thereof. It should be understood that, as used herein, "guanidine" refers to guanidine and its derivatives.

[0128] Useful promoters include, for example, trimethylamine; tributylamine; N,N-bis(N,N-dimethyl-2-aminoethyl)methylamine; N,N-dimethylcyclohexylamine; N-methylmorpholine; N-ethylmorpholine; piperidine; piperazine; pyrrolidine; homopiperazine; 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine; 1,4,5,6-tetrahydropyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,5 ,7-triazabicyclo[4.4.0]dec-5-ene; 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene; 1,5-diazabicyclo[4.3.0]non-5-ene; 6-(dibutylamino)-1,8-diazabicyclo(5,4,0)undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; 7-azabicyclo[2.2.1]heptane; N,N-dimethylaniline; 4,5-dihydro-1H-imidazole; and guanidine-based catalysts such as guanidine, methylguanidine, dimethylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, methylisobiguanide, dimethylisobiguanide, tetramethylisobiguanide, hexamethylisobiguanide, heptamethylisobiguanide, phenylguanidine, diphenylguanidine, butylbiguanide, 1-o-tolylbiguanide, 1-phenylbiguanide, 1-methyl-3-nitroguanidine, 1,8-bis(tetramethylguanidino)-naphthalene and N,N,N',N'-tetramethyl-N"-[4-morpholino(phenylimino)methyl]guanidine. Examples of substituted guanidines are methylguanidine, dimethylguanidine, trimethylguanidine, tetramethylguanidine, methylisobiguanide, dimethylisobiguanide, tetramethylisobiguanide, hexamethylisobiguanide, heptamethylisobiguanide and in particular cyanoguanidine (dicyandiamide, available, for example, from AlzChem Representatives of suitable guanamine derivatives which may be mentioned are alkylated benzoguanamine resins, benzoguanamine resins or methoxymethylethoxymethylbenzoguanamine.

[0129] The promoter may comprise azoles, diazoles, triazoles, higher functional azoles and combinations thereof. Suitable alkaloid compounds include pyrrolidine, tropane, pyrrolizidine, piperidine, quinolizidine, indolizidine, pyridine, isoquinoline, oxazole, isoxazole, thiazole, quinazoline, acridine, quinoline, indole, imidazole, purine, phenylethylamine, muscarine, benzylamine, derivatives of these alkaloid compounds or combinations thereof.

[0130] For example, guanidine may comprise compounds, moieties and / or residues having the following general structure (V):

[0131]

[0132] Wherein each of R1, R2, R3, R4 and R5 (i.e., the substituents of structure (V)) comprises hydrogen, (cyclo)alkyl, aryl, aromatic, organometallic, polymer structure, or can form a cycloalkyl, aryl or aromatic structure together, and wherein R1, R2, R3, R4 and R5 can be the same or different. When any R group in the R group "can form a (cyclo)alkyl, aryl and / or aromatic group together", it means that any two adjacent R groups are connected to form a cyclic portion, such as the ring in structures (VI)-(IX) below.

[0133] It should be understood that the double bond between the carbon atom and the nitrogen atom depicted in Structure (V) can be located between the carbon atom and another nitrogen atom of Structure (V). Therefore, depending on where the double bond is located within the structure, various substituents of Structure (V) can be attached to different nitrogen atoms.

[0134] The guanidine may comprise a cyclic guanidine, such as a guanidine of structure (V), wherein two or more R groups of structure (V) together form one or more rings. In other words, the cyclic guanidine may comprise > 1 ring. For example, the cyclic guanidine can be a monocyclic guanidine (1 ring), as depicted in structures (VI) and (VII) below, or a bicyclic or polycyclic guanidine ( > 2 rings), as depicted below in structures (VIII) and (IX).

[0135]

[0136]

[0137] Each substituent R1-R7 of structure (VI) and / or (VII) may comprise hydrogen, (cyclo)alkyl, aryl, aromatic, organometallic, polymer structure, or may form together a cycloalkyl, aryl or aromatic structure, and wherein R1-R7 may be the same or different. Similarly, each substituent R1-R9 of structure (VIII) and (IX) may be hydrogen, alkyl, aryl, aromatic, organometallic, polymer structure, or may form together a cycloalkyl, aryl or aromatic structure, and wherein R1-R9 may be the same or different. In addition, in some examples of structure (VI) and / or (VII), certain combinations of R1-R7 may be part of the same ring structure. For example, R1 and R7 of structure (VI) may form part of a monocyclic structure. In addition, it should be understood that any combination of substituents (R1-R7 of structure (VI) and / or (VII) and R1-R9 of structure (VIII) and / or (IX)) may be selected, as long as the substituents do not substantially interfere with the catalytic activity of the cyclic guanidine.

[0138] Each ring in a cyclic guanidine may contain > 5 members. For example, a cyclic guanidine can contain a 5-membered ring, a 6-membered ring, and / or a 7-membered ring. As used herein, the term "member" refers to an atom located in a ring structure. Thus, a 5-membered ring will have 5 atoms in the ring structure ("n" and / or "m" = 1 in Structures (VI)-(IX)), a 6-membered ring will have 6 atoms in the ring structure ("n" and / or "m" = 2 in Structures (VI)-(IX)), and a 7-membered ring will have 7 atoms in the ring structure ("n" and / or "m" = 3 in Structures (VI)-(IX)). It should be understood that if a cyclic guanidine contains > If the cyclic guanidine comprises two rings (e.g., structures (VIII) and (IX)), the number of members in each ring of the cyclic guanidine can be the same or different. For example, one ring can be a 5-membered ring and the other ring can be a 6-membered ring. > 3 rings, then, except for the combinations recited in the preceding sentence, the number of members in the first ring of the cyclic guanidine may be different from the number of members in any other ring of the cyclic guanidine.

[0139] It is also understood that the nitrogen atoms of structures (VI)-(IX) may further have additional atoms attached thereto. In addition, the cyclic guanidine may be substituted or unsubstituted. For example, as used herein in conjunction with cyclic guanidines, the term "substituted" refers to cyclic guanidines in which R5, R6 and / or R7 of structures (VI) and / or (VII) and / or R9 of structures (VIII) and / or (IX) are not hydrogen. As used herein in conjunction with cyclic guanidines, the term "unsubstituted" refers to cyclic guanidines in which R1-R7 of structures (VI) and / or (VII) and / or R1-R9 of structures (VIII) and / or (IX) are hydrogen.

[0140] The cyclic guanidine may comprise a bicyclic guanidine, and the bicyclic guanidine may comprise 1,5,7-triazabicyclo[4.4.0]dec-5-ene ("TBD" or "BCG").

[0141] As measured by dynamic light scattering, the guanidine particles have a D98 particle size of less than or equal to 40 μm, such as a D98 particle size of 20 μm, such as a D98 particle size of 15 μm. Instruments for measuring D98 include LS13 320 laser diffraction particle size analyzer (available from Beckman Coulter) or similar instruments.

[0142] In other examples, the promoter may include an amidoamine or polyamide catalyst, such as those available from Air Products. One of the products; amines (such as DY9577 boron complex, ARDUR HT 973 and ARDUR 1167 available from Huntsman Advanced Materials Americas); dihydrazide or dicyandiamide adducts and complexes, such as those available from Ajinomoto Fine Techno Company One of the products; 3,4-dichlorophenyl-N,N-dimethylurea (also known as Diuron) available from AlzChem, or may contain an acid-blocked amine, such as Niax* catalyst available from Momentive Performance Materials Inc., or a combination thereof.

[0143] Based on the total weight of the composition disclosed herein, the composition may include at least 0.01% by weight, such as at least 0.1% by weight of the accelerator (if present). Based on the total weight of the composition disclosed herein, the composition may include no more than 2% by weight, such as no more than 1% by weight of the accelerator (if present). Based on the total weight of the composition disclosed herein, the composition may include from 0.01% to 2% by weight, such as from 0.1% to 1% by weight of the accelerator (if present).

[0144] Synergist

[0145] The disclosed composition may optionally further comprise a synergist for improving the flame retardant efficiency of the first polyol and / or the second polyol. The synergist may be present in the first component, the second component and / or the third or higher component. Suitable examples of this type of synergist include antimony trioxide, antimony pentoxide, sodium antimonate, titanium oxide, zinc oxide, nanoclay, zinc borate, aerogel or a combination thereof. As used herein, the term "synergist" refers to an agent that interacts with another agent and produces an enhanced effect compared to the effect produced by a separate synergist or other agents.

[0146] Based on the total weight of the composition disclosed herein, the composition may include an amount of at least 0.1 wt%, such as at least 1 wt%, of a synergist (if present). Based on the total weight of the composition disclosed herein, the composition may include an amount of no more than 10 wt%, such as no more than 8 wt%, of a synergist (if present). Based on the total weight of the composition disclosed herein, the composition may include an amount of 0.1 wt% to 10 wt%, such as 1 wt% to 8 wt%, of a synergist (if present).

[0147] additive

[0148] The composition may optionally include at least one additive. The additive may be present in the first component, the second component and / or the third or higher component. As used herein, "additive" refers to a dispersant, a rheology modifier, a coupling agent, silicon dioxide, an active life extender, a tackifier, a thermoplastic polymer, a UV stabilizer, a colorant, a coloring agent, a plasticizer, an antioxidant, a pigment, a silane or a combination thereof.

[0149] As used herein, "coupling agent" refers to a compound that provides a chemical bond between two different materials, such as an inorganic material and an organic material. Suitable examples include, but are not limited to, organosilanes, titanates, such as isopropoxy tris(ethylaminoethylamino) titanate, zirconates, 1,2 diketones, nitrogen heterocyclic compounds, cobalt compounds, and combinations thereof.

[0150] As used herein, a "pot life extender" is a chemical that allows the components to mix together while extending the cure time. Suitable examples include mercaptans, acetylacetone, 3,5-dimethylpyrazole, and combinations thereof.

[0151] Dispersants suitable for use in the composition include fatty acids, phosphates, polyurethanes, polyamines, polyacrylates, polyalkoxylates, sulfonates, polyethers and polyesters or any combination thereof. Non-limiting examples of commercially available dispersants include ANTI-TERRA-U100, DISPERBYK-102, DISPERBYK-103, DISPERBYK-111, DISPERBYK-171, DISPERBYK-2151, DISPERBYK-2059, DISPERBYK-2000, DISPERBYK-2117 and DISPERBYK-2118 available from BYK Company; and SOLSPERSE 24000SC, SOLSPERSE 16000 and SOLSPERSE 8000 hyperdispersants available from The Lubrizol Corporation. As used herein, the term "dispersant" refers to a substance that may be added to the composition to enhance separation of the particles by wetting the thermally conductive filler particles and breaking up agglomerates.

[0152] Useful rheology modifiers that can be used include polyamides, amide waxes, polyether phosphates, oxidized polyolefins, castor waxes, and organoclays. Commercially available thixotropes that can be used in the present disclosure include Disparlon 6500 available from King Industries, Garamite 1958 available from BYK, Bentone SD2 available from Elementis, and ST and Crayvallac SLX available from Palmer Holland.

[0153] The reactive diluent can be a monomer, a small molecule or a polymer and can be monofunctional, difunctional or multifunctional. The reactive diluent can be an adhesion promoter or a surfactant. Suitable examples of reactive diluents include propylene carbonate, oxazolidine, aldimine, ketimines and combinations thereof.

[0154] For example, the boiling point of the reactive diluent at 1 atm may be greater than 100°C, such as greater than 130°C, such as greater than 150°C, and for example, the boiling point of the reactive diluent at 1 atm may be less than 425°C, such as less than 390°C, such as less than 360°C. The reactive diluent may reduce the viscosity of the mixture. According to the present disclosure, the viscosity of the reactive diluent at 298°K and 1 atm according to ASTM D789 may be 1 mPa·s to 4,000 mPa·s, for example, 1 mPa·s to 3,000 mPa·s, 1 mPa·s to 2,000 mPa·s, 1 mPa·s to 1,000 mPa·s, 1 mPa·s to 100 mPa·s, or 2 mPa·s to 30 mPa·s.

[0155] Useful colorants or tints may include phthalocyanine blue.

[0156] The composition may optionally include at least one plasticizer. Examples of plasticizers include: diisononyl phthalate (Jayflex available from Exxon Mobil); TM DINP), diisodecyl phthalate (Jayflex available from ExxonMobil TM DIDP) and alkyl benzyl phthalate (Santicizer 278 available from Valtris); benzoate-based plasticizers such as dipropylene glycol dibenzoate (available from Emerald Performance Materials ); and other plasticizers, including terephthalate-based dioctyl terephthalate (DEHT available from Eastman Chemical Company), alkyl sulfonates of phenol (Mesamoll available from Borchers), and diisononyl 1,2-cyclohexanedicarboxylate (HexamollDINCH available from BASF). Other plasticizers may include hydrogenated terphenyl isophthalate, quaterphenyl and higher benzenes or polyphenyls, phthalates, chlorinated paraffins, modified polyphenyls, naphthalenesulfonates, trimellitates, adipates, sebacates, maleates, sulfonamides, organic phosphates, polybutenes, and combinations of any of the foregoing. These plasticizers may be polymers such as polyacrylates.

[0157] Based on the total weight of the composition disclosed herein, the composition may include a total amount of up to 10% by weight, such as at least 0.01% by weight, such as at least 2% by weight of additives (if present). Based on the total weight of the composition disclosed herein, the composition may include a total amount of no more than 10% by weight, such as no more than 7% by weight of additives (if present). Based on the total weight of the composition disclosed herein, the composition may include a total amount of 0.01% to 10% by weight, such as 2% to 7% by weight of additives (if present).

[0158] Compositions, systems and methods

[0159] The 2K composition disclosed herein may include, or may consist essentially of, or may consist essentially of: a first component comprising, or consisting essentially of, an isocyanate; a second component comprising, or consisting essentially of, a first polyol comprising phosphorus, a second polyol comprising sulfur, or a combination of the first polyol and the second polyol, or consisting essentially of, or consisting of; and a filler in an amount of at least 40 weight percent based on the total weight of the composition. The filler may be present in the first component and / or the second component. Optionally, the second component may further include an accelerator and / or a third polyol in addition to the first polyol and the second polyol. Optionally, any of the synergists and / or additives described above may be present in the first component and / or the second component.

[0160] The 3K (or higher component) composition disclosed herein may include, or may consist essentially of, or may consist of: a first component comprising, or consisting essentially of, or consisting of an isocyanate; a second component comprising, or consisting essentially of, or consisting of, a first polyol comprising phosphorus, a second polyol comprising sulfur, or a combination of the first polyol and the second polyol; and a filler in an amount of at least 40% by weight based on the total weight of the composition; and a third component or higher. The filler may be present in the first component, the second component, and / or the third or higher component. Optionally, the second component and / or the third component or higher may further include an accelerator, a synergist, and / or a third polyol in addition to the first polyol and the second polyol.

[0161] The compositions disclosed herein may include isocyanate in an amount such that the equivalent ratio of isocyanate groups to hydroxyl groups is at least 0.8: 1, such as at least 1: 1. The compositions disclosed herein may include isocyanate in an amount such that the equivalent ratio of isocyanate groups to hydroxyl groups is no more than 2: 1, such as no more than 1.5: 1. The compositions disclosed herein may include isocyanate in an amount such that the equivalent ratio of isocyanate groups to hydroxyl groups is from 0.8: 1 to 2: 1, such as from 1: 1 to 1.5: 1.

[0162] The viscosity of the second component of the composition disclosed herein may be no more than 96,000 Cp, such as no more than 90,000 Cp, such as no more than 80,000 Cp, such as no more than 70,000 Cp, such as no more than 60,000 Cp, such as no more than 50,000 Cp, such as no more than 40,000 Cp, such as no more than 30,000 Cp, such as no more than 25,000 Cp, such as no more than 20,000 Cp, such as no more than 15,000 Cp, such as no more than 10,000 Cp, such as no more than 5,000 Cp, such as no more than 4,000 Cp, such as no more than 3,000 Cp, such as no more than 2,000 Cp, such as no more than 1,000 Cp, as measured under ambient conditions using a Brookfield viscometer (Model DV-I, RV-7 spindle).

[0163] The viscosity of the composition disclosed herein may be at least 1,000 Cp, such as at least 10,000 Cp, as measured at ambient conditions according to a Brookfield viscometer (Model DV-I, RV-7 spindle), and the viscosity may not exceed 500,000 Cp, such as not more than 250,000 Cp, as measured at ambient conditions according to a Brookfield viscometer (Model DV-I, RV-7 spindle). The viscosity of the composition disclosed herein may be from 1,000 Cp to 500,000 Cp, such as from 10,000 Cp to 250,000 Cp, as measured at ambient conditions according to a Brookfield viscometer (Model DV-I, RV-7 spindle).

[0164] The compositions disclosed herein may be substantially free, or substantially free, or completely free of halogens.

[0165] Based on the total weight of the composition disclosed herein, the composition may include at least 2.5 wt %, such as at least 10 wt % of the first component. Based on the total weight of the composition disclosed herein, the composition may include no more than 50 wt %, such as no more than 30 wt % of the first component. Based on the total weight of the composition disclosed herein, the composition may include 2.5 wt % to 50 wt %, such as 10 wt % to 30 wt % of the first component.

[0166] Based on the total weight of the composition disclosed herein, the composition may include at least 50% by weight, such as at least 65% by weight of the second component. Based on the total weight of the composition disclosed herein, the composition may include no more than 97.5% by weight, such as no more than 80% by weight of the second component. Based on the total weight of the composition disclosed herein, the composition may include 50% to 97.5% by weight, such as 65% to 80% by weight of the second component.

[0167] Also disclosed herein is a method for preparing one of the compositions disclosed above. The method may optionally include mixing an isocyanate with any of the optional ingredients that may be included in the first component to form a first component containing a mixture. For example, an isocyanate may be mixed with a thermally conductive filler and / or an additive to form a first component. A polyol may optionally be mixed with a thermally conductive filler and / or an additive to form a second component. The first component and the second component and optionally a third or higher component may be mixed to form one of the compositions disclosed above. Such mixing may be carried out at a temperature below 50°C, such as 0°C to 50°C, such as 15°C to 35°C, such as at ambient temperature.

[0168] The above-mentioned compositions can be applied individually or as part of a system that can be deposited on a plurality of different substrates in a variety of different ways. Thus, disclosed herein are methods for treating substrates, comprising, or consisting substantially of, or consisting of: contacting at least a portion of the surface of the substrate with one of the compositions described herein above. That is, the composition can be applied to the surface of the substrate in any number of different ways, non-limiting examples of which include brushes, rollers, films, pellets, trowels, scrapers, dippers, spray guns, and applicator guns for forming a coating on at least a portion of the substrate surface.

[0169] After being applied to the substrate, the composition can be cured. For example, the composition can be allowed to solidify at room temperature or under a slight heat condition, and continue any desired time period (for example, 5 minutes to 1 hour) sufficient to solidify the composition on the substrate. The composition can be solidified under ambient conditions or under a slight heat condition to form a coating on the substrate surface. The coating can include, for example, a sealant, an adhesive, a gap filler, a potting agent, an encapsulant such as a solid, a gel or a foam and / or a liner, such as a preformed liner, a prefabricated liner or a liner formed in situ.

[0170] The system may comprise multiple coatings that are the same or different.The coating is typically formed when a composition deposited onto at least a portion of a substrate surface is cured by methods known to those of ordinary skill in the art, such as under ambient conditions.

[0171] A method for forming a bond between two substrates for various potential applications is also disclosed, wherein the bond between the substrates provides a specific mechanical property associated with lap shear strength. The method may include or consist of or consist of the following: applying the composition described above to a first substrate; contacting the second substrate with the composition so that the composition is positioned between the first substrate and the second substrate; and curing the composition under ambient conditions or microthermal conditions. For example, the composition may be applied to one or both substrate materials in the bonded substrate material to form an adhesive bond therebetween, and the substrates may be aligned, and pressure and / or spacers may be added to control the bond thickness. The composition may be applied to a clean or uncleaned (i.e., including oily or oiled) substrate surface.

[0172] As mentioned above, the compositions of the present disclosure can also form sealants on substrates or substrate surfaces. The sealant composition can be applied to substrate surfaces, and the substrate surface includes a vehicle body or a car frame or an aircraft component as a non-limiting example. The sealant formed by the composition disclosed herein provides enough acoustic damping, tensile strength and tensile elongation. The sealant composition can be applied to cleaned or uncleaned (that is, including oily or oiled) substrate surfaces. The sealant composition can also be applied to substrates that have been pre-treated, coated with an electrodepositable coating, coated with other layers such as primers, undercoats or topcoats. The coating composition is intended to be dried or cured under ambient conditions after being applied to the substrate, or the substrate coated with the coating composition can be optionally subsequently baked in an oven to cure the coating composition.

[0173] The composition can be injected or otherwise placed in a die casting machine or mold and cured under ambient conditions or by exposure to an external energy source, for example by heating to a temperature of less than 180°C, such as less than 130°C, such as less than 90°C, to form a part or component and optionally can be machined into a specific configuration.

[0174] 3-D Printing

[0175] The compositions of the present disclosure may be applied or deposited using any suitable method, including the methods described above. Alternatively, the composition may be cast, extruded, molded, or machined to form a part or component in a cured state.

[0176] The compositions disclosed herein can be used in any suitable additive manufacturing technology, such as three-dimensional (3D) printing, extrusion, spraying, and binder jetting.Additive manufacturing refers to the process of producing a part or component by building up the part or component layer by layer, such as one layer at a time.

[0177] The present disclosure also relates to the use of additive manufacturing processes (such as 3D printing) to produce structural articles, such as acoustic damping pads as a non-limiting example. 3D printing refers to a computerized process, which optionally includes artificial intelligence modulation, by which materials are printed or deposited in successive layers to produce 3D parts or components, such as acoustic damping pads in battery assemblies as a non-limiting example. 3D parts or components can be produced by depositing successive parts or layers on a substrate of any spatial configuration and then depositing additional parts or layers on the underlying deposited parts or layers and / or adjacent to previously deposited parts or layers to produce 3D printed parts or components.

[0178] It will be appreciated that the configuration of the 3D printing process, including the selection of suitable deposition equipment, depends on a variety of factors, such as the deposition volume, the viscosity of the composition, and the complexity of the component being manufactured. Any suitable mixing, delivery, and 3D printing equipment known to those skilled in the art may be used. The composition may be printed or deposited in droplets or extrudates of any size and / or shape and in any pattern to produce a 3D structure.

[0179] The compositions disclosed herein can be applied or deposited by any suitable 3D printing method known to those skilled in the art. The first component and the second component of the 2K composition can be mixed and then deposited, or the first component and the second component can be deposited separately (such as simultaneously and / or sequentially).

[0180] The first component and the second component can be premixed, i.e., mixed together, before application and then deposited. When the material is deposited, the mixture can react or be thermosetting; the deposited reaction mixture can at least partially react after deposition and can also react with previously deposited portions of the article and / or subsequently deposited portions, such as underlying layers or overlying layers of the article.

[0181] In a non-limiting example, the first component and the two components can be released from their respective storage containers and pushed (e.g., pumped) through a conduit (e.g., a hose) into a mixer (e.g., a static or dynamic mixer), where the composition can be mixed for a sufficient time to homogenize the composition, where the composition can then be released through an outlet. The outlet can be a deposition device, such as a print head, and / or the material can leave the mixing unit and be pushed through a conduit (e.g., a hose) to the print head, such as by a pump. The print head can optionally be mounted on a 3D rotating robot to allow the 3D printing composition to be delivered to any substrate in any spatial configuration, and / or the substrate can be manipulated in any spatial configuration during the 3D printing process.

[0182] Alternatively, the first component and the second component can be deposited independently from different print heads. The first component can be deposited by one print head and the second component can be deposited by a second print head. The first component and the second component can be deposited in any pattern so that the first component and the second component comprising any deposited layer can react together or with underlying and / or overlying layers to produce a 3D printed part or component.

[0183] The methods provided by the present disclosure include printing the composition on the manufactured part. The methods provided by the present disclosure include directly printing the part.

[0184] The method provided by the present disclosure can be used to manufacture the component. The entire component can be formed from one of the compositions disclosed herein, one or more parts of the component can be formed from one of the compositions disclosed herein, one or more different parts of the component can be formed using the compositions disclosed herein, and / or one or more surfaces of the component can be formed from the compositions provided by the present disclosure. In addition, the internal area of ​​the component can be formed from the compositions provided by the present disclosure.

[0185] Coatings and molded parts and their uses

[0186] Disclosed herein are coatings and molded parts which surprisingly have flame retardancy in the cured state of V-0 or V-1 as measured according to the UL-94 standard and thermal conductivity of at least 0.4 W / mK as measured with a TCi thermal conductivity analyzer from C-Therm Technologies, Inc. using a modified transient plane source method in accordance with ASTM D7984.

[0187] Also disclosed is a battery having a flame retardancy of V-0 or V-1 and a thermal conductivity of at least 0.4 W / mK, wherein the flame retardancy is measured according to the UL-94 standard and the thermal conductivity is measured using a TCi thermal conductivity analyzer from C-Therm Technology Co., Ltd. using a modified transient plane source method that complies with ASTM D7984.

[0188] Such coatings and / or molded articles can be formed from the compositions disclosed herein.

[0189] The compositions disclosed herein can be used to form coatings and the like and to provide a coating to a substrate, wherein the coating has a flame retardancy of V-0 or V-1 as measured according to the UL-94 standard and a thermal conductivity of at least 0.4 W / mK as measured using a TCi thermal conductivity analyzer from C-Therm Technologies, Inc. using a modified transient plane source method in accordance with ASTM D7984.

[0190] Substrate

[0191] The compositions described herein can be coated or deposited on any substrate or surface, or otherwise contacted with any substrate or surface, such as but not limited to metals or metal alloys, polymeric materials, such as plastics, including filled and unfilled thermoplastic or thermosetting materials, and / or composite materials. Other suitable substrates include, but are not limited to, glass or natural materials such as wood. The substrate can include two or more of any different materials in any combination, such as but not limited to two different metals, or metals and metal alloys, or metals and metal alloys and one or more composite materials.

[0192] Suitable substrates can include but are not limited to flexible and rigid metal substrates, such as ferrous metals, aluminum, aluminum alloys, magnesium, titanium, copper and other metal and alloy substrates. Ferrous metal substrates can include, for example, iron, steel and its alloys. The non-limiting examples of useful steel materials include cold-rolled steel, nickel-plated cold-rolled steel, galvanized (zinc-coated) steel, electrogalvanized steel, stainless steel, acid-leached steel, such as zinc-iron alloys such as GALVANNEAL and combinations thereof. Aluminum alloys, such as 1XXX, 2XXX, 3XXX, 4XXX, 5XXX, 6XXX, 7XXX or 8XXX series of aluminum alloys and coated aluminum alloys and cast aluminum alloys, such as A356, 1XX.X, 2XX.X, 3XX.X, 4XX.X, 5XX.X, 6XX.X, 7XX.X or 8XX.X series of coated aluminum alloys and cast aluminum alloys can also be used as substrates. The substrate may also comprise, for example, magnesium, such as magnesium alloys of the AZ31B, AZ91C, AM60B or EV31A series, titanium and / or titanium alloys, such as titanium alloys of grades 1-36, including H-grade variants, copper and copper alloys or other non-ferrous metals, and alloys of these materials. The substrate may comprise composite materials, such as plastics, glass fibers and / or carbon fiber composites.

[0193] It should also be understood that the substrate may comprise a bare substrate, or the substrate may be at least partially pretreated or precoated with one or more layers. Suitable pretreatment solutions may include, but are not limited to, zinc phosphate pretreatment solutions, such as those described in U.S. Pat. Nos. 4,793,867 and 5,588,989, or zirconium-containing pretreatment solutions, such as those described in U.S. Pat. Nos. 7,749,368 and 8,673,091.

[0194] The substrate can be in any form, such as but not limited to a sheet, foil, laminated foil, liner, prefabricated component, assembly or article. The composition comprising the materials disclosed herein can be used to coat a substrate, such as by depositing, applying the composition onto a substrate surface, or contacting the composition with a substrate surface. The cured composition can be used in any form, such as but not limited to a coating, sealant, adhesive, potting agent or encapsulant, such as a solid, gel or foam, liner, such as an in-situ formed liner or a discrete prefabricated or preformed liner.

[0195] In an example, the substrate can be a multi-metal article. As used herein, the term "multi-metal article" refers to (1) an article having at least one surface comprising a first metal and at least one surface comprising a second metal different from the first metal, (2) a first article having at least one surface comprising a first metal and a second article having at least one surface comprising a second metal different from the first metal, or (3) both (1) and (2).

[0196] The compositions disclosed herein are not limited and can be particularly suitable for various industrial or transportation applications, including automotive applications, commercial transportation applications, rail locomotives, marine applications and / or aerospace applications. Suitable substrates for use in the present disclosure include substrates used in assemblies of vehicle bodies (such as, but not limited to, doors, body panels, trunk lids, top panels, hoods, tops and / or longitudinal beams, rivets, landing gear components and / or skins used on aircraft), vehicle frames, vehicle parts, motorcycles, wheels, and industrial structures and assemblies. As used herein, "vehicles" or variations thereof include, but are not limited to, civilian vehicles, light and heavy commercial vehicles, civilian and military aircraft and / or land vehicles, such as automobiles, motorcycles and / or trucks. The compositions disclosed herein can also be suitable for various industrial applications, including electrical appliances, personal electronic devices, circuit boards, etc., or combinations thereof.

[0197] Figures 1 to 9 Non-limiting examples of battery assembly components and configurations are presented, as well as non-limiting applications or uses of the compositions disclosed herein in such battery assemblies. Figures 1 to 9 Specific examples of battery cell shapes and battery cell arrangements are shown, but the battery cells can be arranged in any configuration known to those skilled in the art. In addition, the cured composition can be used to form gaskets, adhesives, coatings, potting agents, etc. to provide thermal protection between battery cells, within battery modules, and / or within battery packs. These materials can be used on any surface or in any space within such battery assemblies. For example, the compositions disclosed herein can also be used in battery assemblies, including but not limited to battery cells to modules ( Figure 3 , 4 , 6B), module to battery pack ( Figure 6C, 7 ), battery cell to battery pack ( Figure 8 ) and battery unit to chassis battery assembly ( Fig. 9 ). Such battery assemblies may be used for, but are not limited to, any of the above applications.

[0198] A battery assembly can be any combination of one or more battery cells, interconnects that provide conductivity between the battery cells, and auxiliary components, such as control electronics and components that ensure the structural, mechanical, and environmental requirements required for a particular battery operation, in a non-limiting example (for example, but not limited to, battery cell interconnects such as wires, battery pack housings including trays and covers, module housings, module frames and frame plates, module brackets, cooling and heating components including cooling plates, cooling fins and cooling tubes, electrical bus bars, battery management systems, battery thermal management systems, chargers, inverters, and converters).

[0199] The battery cell 10 is generally a single unit energy storage container that can be connected in series or in parallel. The battery cell can be any suitable size or shape known to those skilled in the art, such as but not limited to cylindrical ( Figure 1 , 4 and 9), prismatic ( Figure 2 , 5 -8) and / or bag-shaped ( Figure 3 ). The battery cell 10 is enclosed to provide the desired mechanical protection and environmental isolation for the battery cell. For example, cylindrical and prismatic battery cells may be enclosed in metal cans, boxes and covers, while pouch-shaped battery cells may be enclosed in multi-layer laminated foils. The battery terminal 1 connects the electrode inside the battery cell to the circuit outside the battery cell, one of which is the positive terminal and the other is the negative terminal. Figure 4 As shown, the battery cells 10 may be connected in series or in parallel with other battery cells 10 via interconnector wires 5 to enable current to flow between the battery cells 10 .

[0200] like Figure 3 , 4 , 5, 6B, 6C and 7, the battery cells 10 can be arranged in a module 100 including a plurality of battery cells 10 connected in series or in parallel. The module 100 may include at least a portion of the housing of the arranged battery cells 10. Auxiliary components such as those mentioned above may be included. Spaces of any size may be located between the plurality of battery cells, auxiliary components, substrates and / or any inner surface of the module wall or other housing 120.

[0201] Figure 1A top view of a cylindrical battery cell 10 with a terminal 1 is shown. As shown, the battery cells are arranged in rows with cooling tubes 3 or dielectric and thermal insulation paper (insulating paper) 4 between the rows. As shown, materials, such as adhesives 6 and / or potting agents 7, optionally formed from the compositions disclosed herein, can be positioned between the battery cells 10, the cooling tubes 3, and / or the insulating paper 4.

[0202] Figure 2 An exploded isometric view of an array of prismatic battery cells 10 is shown. As shown, each prismatic battery cell 10 can include a top 11, a bottom, and walls 13 positioned between the top and the bottom and each having a surface. As shown, a material formed from a composition disclosed herein, such as a gasket 8, can be positioned between the surfaces of the battery cell walls 13 of adjacent battery cells 10.

[0203] Figure 3 A cutaway front view of an array of pouch-shaped battery cells 10 in a module 100 is shown. Module walls 120 may partially surround the battery cells 10. As shown, a gasket 8 formed of a composition disclosed herein may be positioned between surfaces of the battery cells 10.

[0204] Figure 4 An isometric view of a cylindrical battery cell 10 in a battery module 100 is shown. Each battery cell may include a top 11, a bottom 12, and a wall 13 positioned between the top and the bottom and each having a surface. The top 11 and the bottom 12 may be oppositely charged terminals, one of which is a positive terminal 1 and the other is a negative terminal (not shown). The battery cells may be connected at their terminals by interconnectors, such as wires 5, etc., so that current can flow between electrochemical battery cells. The module 100 or the module wall 120 may form a space having a volume. The battery cell 10 may be positioned in the space to consume a portion of the volume. A material formed by a composition disclosed herein, such as a potting agent 7, may be positioned, and a material formed by a coating composition disclosed herein may be positioned in the space to consume at least a portion of the volume, so that the material is adjacent to the surface of the battery cell wall 13 and / or the inner surface of at least one wall of the wall 120 of the module 100.

[0205] Figure 5An exploded perspective view of a battery module 100 is shown, which includes one or more arrays of battery cells 10, cooling fins 230, and / or cooling plates 240. Materials formed from the compositions disclosed herein, such as gaskets 8, can be positioned between the battery cells 10. Additional gaskets 8 can be positioned between the battery cells 10, cooling fins 230, and / or cooling plates 240. Additional materials formed from the compositions disclosed herein, such as gaskets 8, or optionally, such as adhesives and / or potting agents, can be positioned between the battery cell arrays and the inner surface of the wall 120. Other gaskets 8 can be positioned adjacent to the outer surface of the wall 120.

[0206] FIG. 6 shows a battery cell 10 ( Fig. 6A ) to the battery module 100( Figure 6B ) to battery pack 200( Figure 6C ) isometric view of a battery assembly. The battery module 100 includes a plurality of battery cells 10 , and the battery pack 200 includes a plurality of battery modules 100 .

[0207] Figure 7 A perspective view of a cutout of a battery pack 200 is shown. The battery pack includes a plurality of battery modules 100 and battery cells 10 located within each module 100. The base of the battery pack 200 includes a cooling plate 240. A material such as an adhesive 9 formed from a composition disclosed herein can be positioned between the cooling plate 240 and the inner surface of the wall of the battery pack 200. A material such as a gasket 8 formed from a composition disclosed herein can be positioned between the battery cells 10 within the module 100.

[0208] Figure 8 An isometric view of the battery cell 10 to pack battery 200 assembly is shown. The battery cells 10 are arranged within the pack 200 (rather than in separate modules).

[0209] In other cases, the battery cell may be disposed on or in an article, such as, but not limited to, Fig. 9 The battery cell to chassis battery assembly is shown, wherein one or more battery cells are used to construct a battery assembly without prior assembly of the battery cells into modules and / or packs. Fig. 9 There is shown an isometric cutaway view of a battery cell to chassis battery assembly 300. The battery cells 10 are arranged on a substrate that includes a chassis 55 and is supported by the vehicle frame 45 and is located below the vehicle interior floor 35.

[0210] Any battery assembly may further include a thermal management system (not shown) including an air or fluid circuit, which may be liquid-based (e.g., ethylene glycol solution) or direct refrigerant-based. Flame retardant materials may be adjacent to any of these components of the battery assembly.

[0211] The following examples illustrate the disclosure, which, however, should not be considered to limit the disclosure to its details. Unless otherwise indicated, all parts and percentages in the following examples and throughout the specification are by weight.

[0212] Examples

[0213] The following Synthesis Examples A and B provide descriptions of the synthesis of phosphorus-containing polyols and sulfur-containing polyols, respectively, used to prepare the compositions of Examples 5-9 described in further detail herein.

[0214] Synthesis Example

[0215] Example A - Modification of Phosphonates with Lactide

[0216] The secondary hydroxyl functional phosphonate was prepared from the following charge:

[0217] Table 1. Ingredients used to prepare phosphorus containing polyols

[0218]

[0219] 1 Diethyl bis(2-hydroxyethyl)aminomethylphosphonate is commercially available from ICP-IP America Inc. 2 Vercet lactide M3002 is meso-lactide and is commercially available from NatureWorks.

[0220] 3 Butylstannoic acid is commercially available from Arkema Inc.

[0221] Charge 1 is added into a 500mL 4-necked flask equipped with a motor-driven stainless steel stirring blade, a water-cooled condenser, a nitrogen blanket and a heating jacket with a thermometer connected by a temperature feedback control device. The reaction mixture is heated to 135°C. The reaction mixture is maintained at 135°C until the IR spectrum using Thermo Scientific Nicolet iS5 FT-IR shows the absence of characteristic lactide bands (936cm -1 ) until the reaction product was poured off at 80°C. The Mw of this secondary hydroxyl functional phosphonate was 979 as determined by gel permeation chromatography using a Waters 2695 Separation Module, a Waters 410 Differential Refractometer (RI detector) and polystyrene standards. -1Tetrahydrofuran (THF) was used as the eluent at a flow rate of 1.5 wt % and two PL gel mixed C columns were used for separation.

[0222] Example B - Synthesis of Sulfur-Containing Polyols

[0223] Sulfur-containing polyols were prepared from the following charges:

[0224] Table 2. Ingredients used to prepare sulfur-containing polyols

[0225]

[0226] 1 PETMP is pentaerythritol tetrakis(3-mercaptopropionate) and is commercially available from Bruno Bock. 2 DBU is 1,8-diazabicyclo[5.4.0]undec-7-ene and is commercially available from Air Products & Chemicals.

[0227] 3 Epodil 748 is commercially available from Evonik Industries.

[0228] Charge 1 was added to a 500 mL 4-necked flask equipped with a motor-driven stainless steel stirring blade, a water-cooled condenser, a nitrogen blanket, and a heating jacket with a thermometer connected by a temperature feedback control device. Charge 2 was added dropwise to the reaction mixture at room temperature over 60 minutes. After addition, the reaction mixture was slowly heated to 80° C. The reaction mixture was maintained at 80° C. until the EEW exceeded 10,000 by titration (glacial acetic acid containing 0.1 N perchloric acid). The reaction product was poured out at 40° C. The Mw of the hydroxy-functional sulfur-containing resin was 2316, as described in Example A above.

[0229] Example 1

[0230] The materials used to prepare the compositions of Examples 1 to 9 are listed in Table 3.

[0231] Table 3. Ingredients used to prepare the compositions of Examples 1 to 9

[0232]

[0233]

[0234] Table 4. Sample Preparation - Examples 1 to 9

[0235]

[0236]

[0237] *“Not measurable” means not measurable under the test conditions and using the test parameters utilized in these Examples.

[0238] All samples were prepared using a Speedmixer DAC 600FVZ (commercially available from FlackTeck Inc.) according to the following procedure. The polyol, dispersant, catalyst (with or without liquid flame retardant) were mixed together at 2350 revolutions per minute ("rpm") at ambient temperature for about 1 minute, and then fillers (both thermally conductive and non-thermally conductive) were added to the mixture at 2350 rpm for 1 minute. The mixture was then mixed with isocyanate at 2350 for another 1 minute. Afterwards, the mixture was transferred to an aluminum weighing pan (Fisherbrand, catalog number 08-732-101) and a laboratory-made Teflon mold for mechanical and flame retardant testing, and allowed to cure at ambient temperature for one week. The cured samples were removed from the aluminum weighing pan and Teflon mold for thermal conductivity, mechanical and flame retardant testing.

[0239] Thermal conductivity test. The thermal conductivity of the cured samples was tested using a TCi thermal conductivity analyzer from C-Therm Technology Co., Ltd. using a modified transient plane source (MTPS) method (compliant with ASTM D7984). The sample size was at least 20 mm by 20 mm with a thickness of 5 mm. A load of 500 g was added to the top of the sample to ensure that the sample was in full contact with the flat probe.

[0240] Pot life / viscosity measurement. Pot life is defined as the time required for the formulation to reach a viscosity of 100,000 cPs. Viscosity rise is measured using a Brookfield viscometer (DV-I, RV-7 spindle). The formulation is poured into a 40 mL vial. The vial is fixed and the viscometer spindle is lowered into the solidified formulation. The viscometer is connected to a data recording A / D device and software from which a viscosity curve is generated.

[0241] The data shown in Table 3 show that compared with the composition not including the intumescent flame retardant, the conventional intumescent flame retardant has a significant effect on viscosity (Comparative Example 2 is relative to Comparative Example 1, and the viscosity is 96,100Cp relative to 23,400Cp, respectively). The data also show that the viscosity of the composition caused by the inclusion of liquid phosphorus-containing polyol (Veriquel R100, Experimental Example 3) is significantly lower than that of Examples 1 and 2, and the coating has good flame retardancy and good thermal conductivity. When a higher loading level of thermally conductive filler (Nabalox 625-31) is added (Experimental Examples 4 and 9), the formed coating has excellent flame retardancy and thermal conductivity, although the viscosity cannot be measured due to the high filler loading. Compositions comprising synthetic phosphorus-containing polyols (Experimental Example 5), synthetic sulfur-containing polyols (Experimental Example 6) or both (Experimental Examples 7 and 8) have good viscosity and produce coating compositions with flame retardancy and / or thermal conductivity.

[0242] Although specific features of the present disclosure have been described above for purposes of illustration, it will be apparent to those skilled in the art that many changes may be made in the details of the coating compositions, coatings, and methods disclosed herein without departing from the scope of the appended claims.

Claims

1. A composition comprising: a first component, the first component comprising an isocyanate; a second component comprising a first polyol comprising phosphorus, a second polyol comprising sulfur, or a combination of the first polyol and the second polyol; and Filler, the amount of filler is at least 40% by weight based on the total weight of the composition.

2. The composition of claim 1, wherein the isocyanate comprises an aromatic isocyanate, an aliphatic isocyanate, an isocyanate prepolymer, or a combination thereof.

3. The composition of claim 1 or claim 2, wherein the isocyanate comprises 4,4'-diphenylenemethane diisocyanate (MDI), toluene diisocyanate (TDI), methylene bis(4-cyclohexyl isocyanate) (HMDI), isophorone diisocyanate (IPDI), or a combination thereof.

4. A composition according to any one of the preceding claims, wherein the first component comprises the isocyanate in an amount of at least 15 wt %, such as at least 30 wt %, such as not more than 100 wt %, such as not more than 70 wt %, such as from 15 wt % to 100 wt %, such as from 30 wt % to 70 wt %, based on the total weight of the first component.

5. The composition according to any one of claims 2 to 4, wherein the isocyanate prepolymer has a Mw of at least 300 g / mol, such as at least 600 g / mol, such as at least 1,000 g / mol, such as at least 3,000 g / mol, such as no more than 30,000 g / mol, such as no more than 20,000 g / mol, such as no more than 15,000 g / mol, such as no more than 10,000 g / mol, such as from 300 g / mol to 30,000 g / mol, such as from 600 g / mol to 20,000 g / mol. / mol, such as 1,000 g / mol to 15,000 g / mol, such as 3,000 g / mol to 10,000 g / mol, and / or the isocyanate equivalent weight of the isocyanate prepolymer is at least 150, such as at least 300, such as at least 500, such as at least 1,500, such as not more than 15,000, such as not more than 10,000, such as not more than 7,500, such as not more than 5,000, such as 150 to 15,000, such as 300 to 10,000, such as 500 to 7,500, such as 1,500 to 5,000.

6. The composition according to any one of claims 2 to 5, wherein the first component comprises the isocyanate prepolymer in an amount of at least 5 wt %, such as at least 30 wt %, such as not more than 100 wt %, such as not more than 70 wt %, such as from 5 wt % to 100 wt %, such as from 30 wt % to 70 wt %, based on the total weight of the first component.

7. The composition according to any one of the preceding claims, wherein the isocyanate comprises, in addition to the isocyanate functional group, at least one functional group, such as a siloxane functional group, an epoxy functional group and / or an acrylic functional group.

8. The composition of any one of claims 1 to 6, wherein the isocyanate is substantially free, or essentially free, or completely free of functional groups other than the isocyanate functional groups.

9. A composition according to any one of the preceding claims, wherein the second component comprises a total amount of at least 1 wt %, such as at least 30 wt %, such as not more than 100 wt %, such as not more than 70 wt %, such as from 1 wt % to 100 wt %, such as from 30 wt % to 70 wt % of the first polyol and / or the second polyol, based on the total weight of the second component.

10. The composition of any one of the preceding claims, further comprising a third polyol in addition to the first polyol and the second polyol.

11. The composition of claim 10, wherein the second component comprises the third polyol in an amount of at least 1 wt%, such as at least 30 wt%, such as no more than 99 wt%, such as no more than 70 wt%, such as from 1 wt% to 99 wt%, such as from 30 wt% to 70 wt%, based on the total weight of the second component.

12. The composition of any one of the preceding claims, wherein the first polyol, the second polyol, and / or the third polyol comprises a polyether polyol, a polyester polyol, a polycaprolactone polyol, a polycarbonate polyol, a polyurethane polyol, a polyvinyl alcohol, a polymer comprising a hydroxy-functional acrylate, a polymer comprising a hydroxy-functional methacrylate, a polymer comprising an alcohol, a hydroxy-functional polybutadiene, or a combination thereof.

13. The composition of any one of the preceding claims, wherein the first polyol and / or the second polyol has a weight average molecular weight of at least 150 g / mol, such as at least 2,000 g / mol, such as no more than 8,000 g / mol, such as no more than 6,000 g / mol, such as from 150 g / mol to 8,000 g / mol, such as from 2,000 g / mol to 6,000 g / mol, as determined by gel permeation chromatography using polystyrene standards.

14. The composition of any one of the preceding claims, wherein the first polyol, the second polyol and / or the third polyol have a hydroxide functionality of at least 1, such as greater than 1, such as at least 2, such as at least 3, such as from 1 to 10, such as from 2 to 8.

15. The composition of any one of the preceding claims, wherein the first polyol further comprises sulfur and / or the second polyol further comprises a phosphate ester.

16. The composition of any one of the preceding claims, wherein the first polyol, the second polyol, and / or the third polyol comprises a liquid.

17. The composition of any one of the preceding claims, wherein the first polyol comprises a phosphate ester and / or a phosphonate ester.

18. The composition of any one of the preceding claims, wherein the first polyol comprises the reaction product of ε-caprolactone or lactide and a phosphonate polyol.

19. The composition of any one of the preceding claims, wherein the first polyol comprises structure (I): Where R 1 and R 2 Each of the above comprises a (cyclo)alkyl, aryl, aromatic, polymer structure, or can form a (cyclo)alkyl, aryl or aromatic structure together, and wherein R 1 and R 2 Can be the same or different.

20. The composition according to any one of the preceding claims, wherein the first polyol comprises and / or 21. The composition of any one of claims 1 to 17, wherein the first polyol comprises the reaction product of a phosphonate, an anhydride, and an epoxide.

22. The composition of any one of claims 1 to 17 and 21, wherein the first polyol comprises structure (II): Where R 3 and R 4 Contains a (cyclo)alkyl, aryl, aromatic, polymer structure, or can form a (cyclo)alkyl, aryl or aromatic structure together, and wherein R 3 and R 4 Can be the same or different.

23. The composition of any one of claims 1 to 17, 21 and 22, wherein the first polyol comprises 24. The composition of any one of claims 1 to 16, wherein the second polyol comprises a sulfide, a disulfide, a polysulfide, a sulfone, a thiol, a thioester, or a combination thereof.

25. The composition of any one of claims 1 to 16 and 24, wherein the second polyol comprises the reaction product of a thiol-functional compound and an epoxy resin.

26. The composition of any one of claims 1 to 16, 24 and 25, wherein the second polyol comprises: Structure (III) Where R 5 , R 6 , R 7 and R 8 Contains hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structure, or can form (cyclo)alkyl, aryl or aromatic structure together, and wherein R 5 , R 6 , R 7 and R 8 may be the same or different; and / or Structure (IV): Where R 9 , R 10 , R 11 and R 12 Contains hydrogen, (cyclo)alkyl, aryl, aromatic, polymeric structure, or can form together a (cyclo)alkyl, aryl or aromatic structure, and wherein R 9 , R 10 , R 11 and R 12 Can be the same or different.

27. The composition of any one of claims 1 to 16 and 24 to 26, wherein the second polyol comprises structure (IIIA): Where n=10-12.

28. A composition according to any one of the preceding claims, comprising the filler in an amount of at least 55 wt%, such as not more than 90 wt%, such as not more than 75 wt%, such as from 40 wt% to 90 wt%, such as from 55 wt% to 75 wt%, based on the total weight of the composition.

29. The composition of any one of the preceding claims, wherein the filler comprises (i) a thermally conductive and electrically insulating filler, (ii) a thermally conductive and electrically conductive filler and / or (iii) a non-thermally conductive and electrically insulating filler, and / or wherein the filler comprises a surface coating.

30. The composition of any preceding claim, further comprising an enhancer, a synergist, an additive, or a combination thereof.

31. The composition of claim 30, wherein the composition comprises: (a) an accelerator in an amount of at least 0.01 wt %, such as at least 0.1 wt %, such as not more than 2 wt %, such as not more than 1 wt %, such as from 0.01 wt % to 2 wt %, such as from 0.1 wt % to 1 wt %, based on the total weight of the composition; (b) an amount of at least 0.01 wt %, such as at least 0.1 wt %, such as no more than 2 wt %, such as no more than 1 wt %, such as from 0.01 wt % to 2 wt %, such as from 0.1 wt % to 1 wt % of the synergist, based on the total weight of the composition; and / or (c) a total amount of up to 10 wt %, such as at least 0.01 wt %, such as at least 2 wt %, such as not more than 10 wt %, such as not more than 7 wt %, such as from 0.01 wt % to 10 wt %, such as from 2 wt % to 7 wt % of said additives, based on the total weight of the composition.

32. A composition according to claim 30 or claim 31, wherein the promoter comprises guanidine, a guanidine derivative, an imidazole, an acid-blocked amine, or a combination thereof, the synergist comprises antimony trioxide, titanium oxide, zinc oxide, nanoclay, zinc borate, aerogel, or a combination thereof and / or the additive comprises a dispersant, a rheology modifier, a coupling agent, silica, a promoter, a potlife extender, a tackifier, a thermoplastic polymer, a UV stabilizer, a colorant, a dye, a plasticizer, an antioxidant, a pigment, a silane, or a combination thereof.

33. The composition according to any one of the preceding claims, wherein the first component, the second component and / or the third component comprises the at least one filler, the synergist and / or the additive.

34. A composition according to any one of the preceding claims, wherein the second component and / or the third component comprises the accelerator.

35. A composition according to any one of the preceding claims, comprising the isocyanate and the polyol in an amount sufficient to provide an equivalent ratio of isocyanate groups to hydroxyl groups of at least 0.8:1, such as at least 1:1, such as no more than 2:1, such as no more than 1.5:1, such as from 0.8:1 to 2:1, such as from 1:1 to 1.5:

1.

36. A composition according to any of the preceding claims, comprising at least 2.5 wt %, such as at least 10 wt %, such as no more than 50 wt %, such as no more than 30 wt %, such as from 2.5 wt % to 50 wt %, such as from 10 wt % to 30 wt % of the first component, based on the total weight of the composition, and / or at least 50 wt %, such as at least 65 wt %, such as no more than 97.5 wt %, such as no more than 80 wt %, such as from 50 wt % to 97.5 wt %, such as from 65 wt % to 80 wt % of the second component, based on the total weight of the composition.

37. A composition according to any of the preceding claims, wherein the viscosity of the second component is no more than 96,000 Cp, such as no more than 90,000 Cp, such as no more than 80,000 Cp, such as no more than 70,000 Cp, such as no more than 60,000 Cp, such as no more than 50,000 Cp, such as no more than 40,000 Cp, such as no more than 30,000 Cp, such as no more than 25,000 Cp, such as no more than 20,000 Cp, such as no more than 15,000 Cp, such as no more than 10,000 Cp, such as no more than 5,000 Cp, such as no more than 4,000 Cp, such as no more than 3,000 Cp, such as no more than 2,000 Cp, such as no more than 1,000 Cp, the viscosity being measured at ambient conditions using a Brookfield viscometer (Model DV-I, RV-7 spindle).

38. A composition according to any of the preceding claims, wherein the viscosity of the composition measured within 1 minute of mixing the first component and the second component is at least 1,000 Cp, such as at least 10,000 Cp, such as no more than 500,000 Cp, such as no more than 250,000 Cp, such as 1,000 Cp to 500,000 Cp, such as 10,000 Cp to 250,000 Cp, the viscosity being measured according to a Brookfield viscometer (Model DV-I, RV-7 spindle) under ambient conditions.

39. The composition of any preceding claim, wherein the composition is substantially halogen-free.

40. A method of coating a substrate, the method comprising: A portion of the surface of the substrate is contacted with a composition according to any one of the preceding claims.

41. The method of claim 40, further comprising mixing the first component with the second component to form a composition according to any one of claims 1 to 39; and optionally heating the composition after the contacting.

42. The method of claim 40 or claim 41, further comprising contacting a surface of a second substrate with the composition such that the composition is located between the first substrate and the second substrate.

43. A method of forming an article, the method comprising extruding the composition of any one of claims 1 to 39.

44. The method of claim 43, wherein the extruding comprises three-dimensional printing.

45. An article formed by the method of claim 44 or claim 44.

46. ​​A substrate comprising a coating formed on a portion of a surface of the substrate from the composition according to any one of claims 1 to 39.

47. The substrate of claim 46, wherein the coating has a flame retardancy of V-0 or V-1 as measured according to UL-94 standard and a thermal conductivity of at least 0.4 W / mK as measured using a TCi thermal conductivity analyzer from C-Therm Technologies Ltd using a modified transient plane source method in accordance with ASTM D7984.

48. A substrate according to claim 45 or claim 47 coated according to the method of any one of claims 40 to 42.

49. The substrate of any one of claims 46 to 48, wherein the coating comprises a sealant, an adhesive, a gap filler, a pottant, an encapsulant such as a solid, gel or foam, and / or a gasket such as a preformed gasket, a prefabricated gasket or an in-situ formed gasket.

50. The substrate of any one of claims 46 to 49, wherein the substrate comprises an article, a part, or a combination thereof.

51. The substrate of claim 50, wherein the article comprises a vehicle, an appliance, a personal electronic device, a circuit board, a battery cell, a multi-metal substrate, or a combination thereof.

52. The substrate of claim 50, wherein the component comprises a vehicle component.

53. The substrate of claim 51 or claim 52, wherein the vehicle comprises a land vehicle or an aircraft.

54. A battery comprising a battery cell and a coating formed from the composition according to any one of claims 1 to 39.

55. The battery of claim 54, wherein the battery cells and the combination are housed in a module.

56. The battery of claim 54, wherein the battery and the combination are housed in a pack.

57. The battery of claim 54, wherein the modules are housed in packs.

58. The battery of claim 54 located adjacent to a vehicle chassis.

59. The battery of any one of claims 54 to 58, further comprising a battery component.

60. A battery according to any one of claims 54 to 59, wherein the coating has a flame retardancy of V-0 or V-1 and a thermal conductivity of at least 0.4 W / mK, the flame retardancy being measured according to the UL-94 standard, and the thermal conductivity being measured using a TCi thermal conductivity analyzer from C-Therm Technologies, Inc. using a modified transient plane source method in accordance with ASTM D7984.

61. The battery of any one of claims 54 to 60, wherein the coating comprises a sealant, an adhesive, a gap filler, a potting agent, an encapsulant such as a solid, gel or foam, and / or a gasket such as a preformed gasket, a prefabricated gasket or an in-situ formed gasket.

62. A vehicle comprising a battery according to any one of claims 54 to 61.

63. The vehicle of claim 62, wherein the vehicle comprises a land vehicle or an aircraft.

64. Use of a composition according to any one of claims 1 to 39 for preparing a coating having a flame retardancy of V-0 or V-1 and a thermal conductivity of at least 0.4 W / mK, the flame retardancy being measured according to the UL-94 standard, the thermal conductivity being measured using a TCi thermal conductivity analyzer from C-Therm Technologies Ltd. using a modified transient plane source method in accordance with ASTM D7984.

65. Use of a coating formed from a composition according to any one of claims 1 to 39 for providing to a substrate: flame retardancy of V-0 or V-1 as measured according to UL-94 standard and a thermal conductivity of at least 0.4 W / mK as measured using a TCi thermal conductivity analyzer from C-Therm Technologies, Inc. using a modified transient plane source method in accordance with ASTM D7984.

66. A polyol comprising structure (I): Where R 1 and R 2 Each of the above comprises a (cyclo)alkyl, aryl, aromatic, polymer structure, or can form a (cyclo)alkyl, aryl or aromatic structure together, and wherein R 1 and R 2 Can be the same or different.

67. The polyol of claim 66 comprising Structure (IA), Structure (IB) and / or Structure (IC): and / or 68. A polyol according to claim 66 or claim 67, wherein the polyol comprises the reaction product of ε-caprolactone or lactide and a phosphonate polyol.

69. The polyol of any one of claims 66 to 68, wherein the polyol comprises a reaction product formed according to Reaction Scheme (IA), Reaction Scheme (IB), and / or Reaction Scheme (IC):

70. A polyol comprising structure (II): Where R 3 and R 4 Contains a (cyclo)alkyl, aryl, aromatic, polymer structure, or can form a (cyclo)alkyl, aryl or aromatic structure together, and wherein R 3 and R 4 Can be the same or different.

71. The polyol of claim 70 comprising structure (IIA):

72. A polyol according to claim 70 or claim 71, wherein the polyol comprises the reaction product of a phosphonate, an anhydride and an epoxide.

73. The polyol of any one of claims 70 to 72, wherein the polyol comprises a reaction product formed according to reaction scheme (II):

74. A polyol comprising structure (III): Where R 5 , R 6 , R 7 and R 8 Contains hydrogen, (cyclo)alkyl, aryl, aromatic, polymer structure, or can form (cyclo)alkyl, aryl or aromatic structure together, and wherein R 5 , R 6 , R 7 and R 8 Can be the same or different.

75. The polyol of claim 74 comprising structure (IIIA): Where n=10-12.

76. A polyol according to claim 74 or claim 75, wherein the polyol comprises the reaction product of a thiol functional compound and an epoxy functional compound.

77. The polyol of any one of claims 74 to 76, wherein the polyol comprises a reaction product formed according to reaction scheme (III):

78. A polyol comprising structure (IV): Where R 9 , R 10 , R 11 and R 12 Contains hydrogen, (cyclo)alkyl, aryl, aromatic, polymeric structure, or can form together a (cyclo)alkyl, aryl or aromatic structure, and wherein R 9 , R 10 , R 11 and R 12 Can be the same or different.

79. The polyol of claim 78, wherein the polyol comprises the reaction product of a thiol-functional compound and an epoxy-functional compound.

80. The polyol of claim 78 or claim 79, wherein the polyol comprises a reaction product formed according to reaction scheme (IV):

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