WO2024144922A2 - Compositions durcissables - Google Patents

Compositions durcissables Download PDF

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Publication number
WO2024144922A2
WO2024144922A2 PCT/US2023/078147 US2023078147W WO2024144922A2 WO 2024144922 A2 WO2024144922 A2 WO 2024144922A2 US 2023078147 W US2023078147 W US 2023078147W WO 2024144922 A2 WO2024144922 A2 WO 2024144922A2
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WIPO (PCT)
Prior art keywords
composition
containing compound
weight
percent
component
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PCT/US2023/078147
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English (en)
Inventor
Joseph Peter KRILEY
JR. Marvin Michael POLLUM
David Joseph FORTMAN
Raymond Arel QUIROZ
Zachary Phillip THOMPSON
Calum Hugh Munro
Steven E. Bowles
Original Assignee
Ppg Industries Ohio, Inc.
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Application filed by Ppg Industries Ohio, Inc. filed Critical Ppg Industries Ohio, Inc.
Publication of WO2024144922A2 publication Critical patent/WO2024144922A2/fr

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  • FIG.1 is a schematic of a top-down view of cylindrical battery cells.
  • FIG.2 is a schematic of an exploded isometric view of an array of prismatic battery cells.
  • FIG.9 is a schematic of an isometric cut-out view of a cell to chassis battery assembly.
  • FIG.10 is a bar graph showing lap shear strength of compositions at room temperature, 71oC, and 150oC.
  • FIG.11 is a bar graph showing lap shear strength of compositions tested by 2K, Film, and 2K repaired.
  • FIG.12 is a plot of dynamic mechanical analysis of Composition X, displaying the reflow onset temperature of the composition. DETAILED DESCRIPTION [0023]
  • the disclosure may assume alternative variations and step sequences, except where expressly specified to the contrary.
  • a “conjugated diene” means an organic molecule containing two double bonds separated by a single bond. The double bonds are typically among carbon atoms, but the double bonds may comprise heteroatoms, such as nitrogen, oxygen, or sulfur.
  • a “dienophile” means a compound that reacts with the conjugated diene in a cycloaddition reaction, such as an alkene, alkyne, or other compound comprising a functional group comprising at least one double bond or triple bond.
  • a “Michael addition reaction” means a reaction between an electrophile and a nucleophile, wherein the nucleophile undergoes conjugate addition to a double bond of a conjugated system.
  • a “liquid” means a material having a viscosity less than 100,000 Pa*s at 25°C as measured by parallel plate rheology with a plate diameter of 25 mm, a gap of 0.5 mm, and a shear rate of 1 s -1 .
  • a “solid” means a material having a viscosity of at least 100,000 Pa*s at 25°C as measured by parallel plate rheology with a plate diameter of 25 mm, a gap of 0.5 mm, and a shear rate of 1 s -1 .
  • a “curable composition” refers to a composition, e.g., a solution, mixture, or a dispersion, that is capable of curing to form a coating.
  • a “sealant composition” refers to a curable composition, e.g., a solution, mixture, or a dispersion that, when cured, has the ability to resist atmospheric conditions such as temperature and moisture gradients and particulate matter, such as moisture and temperature, and block the transmission of materials, such as particulates, water, fuel, and other liquids and gasses.
  • an “adhesive composition” refers to a curable composition that, when cured, forms an adhesive or a structural adhesive.
  • an “adhesive” refers to a cured coating that produces a load- bearing joint, such as a load-bearing joint having a lap shear strength of at least 0.5 MPa and less than 5 MPa, as determined according to ASTM D1002-10 using an Instron 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.
  • ambient conditions generally refer to room temperature (e.g., 23oC) and humidity conditions or temperature and humidity conditions that are typically found in the area in which the composition is applied to a substrate, e.g., at 10oC to 40oC and 5% to 80% relative humidity, while slightly thermal conditions are temperatures that are slightly above ambient temperature, such as greater than 40oC to 60oC.
  • slightly thermal conditions are temperatures that are slightly above ambient temperature, such as greater than 40oC to 60oC.
  • the term “two-component” or “2K” refers to a composition in which a portion of the reactive components readily associate to form an interaction or react to form a bond (physically or chemically), i.e., cure, without activation from an external energy source, such as at ambient or slightly thermal conditions, when mixed.
  • the two components of the composition may be stored separately from each other and mixed just prior to application of the composition.
  • the components may be premixed and frozen and stored (“pre-mixed frozen” or “PMF” as described below).
  • PMF pre-mixed frozen
  • the components cure upon thawing.
  • Two-component compositions may optionally be heated or baked, as described below.
  • the term “hot melt composition” refers to a curable composition comprising two co-reactive components.
  • a hot melt composition cures to form a solid (i.e., a hot melt) at temperatures less than 30oC, flows when heated to a hot melt composition, and, upon cooling, returns to a solid-state hot melt.
  • the composition begins to cure when the components of the composition are mixed resulting in the reaction of the reactive functional groups of the components of the composition.
  • the curable composition may also be subjected to curing conditions such that a substantially complete cure is attained and wherein further curing results in no significant further improvement in the coating properties such as, for example, increased lap shear performance.
  • Mn refers to the number average molecular weight as determined by Gel Permeation Chromatography using Waters 2695 separation module with a Waters 410 differential refractometer (RI detector), polystyrene standards, using tetrahydrofuran (THF) used as the eluent at a flow rate of 1 ml min -1 and two PL Gel Mixed C columns for separation.
  • the “thiol equivalent weight” is the total weight of the thiol- containing component divided by the molar equivalents of thiol functionality. The value may be determined theoretically by dividing the theoretical molecular weight of the thiol-containing component by the theoretical molar equivalents of thiol functional groups, or may be determined experimentally, for example, by titrating a sample with alcoholic silver nitrate using pyridine as a solvent and THF, isopropyl alcohol, acetone, glycol ethers, or hydrocarbons as co-solvents.
  • the “amine equivalent weight” is the total weight of the amine- containing component divided by the molar equivalents of amine functionality. The value may be determined theoretically by dividing the theoretical molecular weight of the amine-containing component by the theoretical molar equivalents of amine functional groups or may be determined experimentally by a variety of titration methods, for example, ASTM D2073 or ASTM D2896.
  • the “furan equivalent weight” is the total weight of the furan- containing component divided by the molar equivalents of furan functionality. The value may be determined theoretically by dividing the theoretical molecular weight of the furan-containing component by the theoretical molar equivalents of furan functional groups.
  • the “maleimide equivalent weight” is the total weight of the maleimide-containing component divided by the molar equivalents of maleimide functionality. The value may be determined theoretically by dividing the theoretical molecular weight of the maleimide-containing component by the theoretical molar equivalents of maleimide functional groups.
  • the term “accelerator” means a substance that increases the rate or decreases the activation energy of a chemical reaction in comparison to the same reaction in the absence of the accelerator.
  • An accelerator may be either a “catalyst,” that is, without itself undergoing any permanent chemical change, or may be reactive, that is, capable of chemical reactions and includes any level of reaction from partial to complete reaction of a reactant.
  • the term “substantially free” means that a particular material is not purposefully added to a mixture or composition, respectively, and is present only as an impurity in a trace amount of less than 5 percent by weight based on a total weight of the mixture or composition, respectively.
  • the term “essentially free” means that a particular material is not purposefully added to a mixture or composition and is present only as an impurity in a trace amount of less than 2 percent by weight based on a total weight of the mixture or composition, respectively.
  • the present disclosure is directed to a composition comprising, or consisting essentially of, or consisting of, a first component and a second component.
  • the first component may comprise, consist essentially of, or consist of, a thiol-containing compound, an amine- containing compound, or a combination thereof, and a furan-containing compound.
  • the second component may comprise, consist essentially of, or consist of, a maleimide-containing compound comprising one maleimide group.
  • the first component and/or the second component may be liquid.
  • thiol-containing compound means a compound comprising a thiol functional group and having a general structure: (VI) wherein R10 may comprise an alkyl, a (cyclo)alkyl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane).
  • R10 may comprise an alkyl, a (cyclo)alkyl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane).
  • suitable thiol-containing compounds include monfunctional thiols or polythiols.
  • the polythiol compound may comprise a dithiol, trithiol, tetrathiol, pentathiol, hexathiol or higher functional polythiol compound.
  • polythiol compounds may comprise dipentaerythritol hexakis-3-mercaptopropionate (commercially available as THIOCURE® DiPETMP from BRUNO BOCK Chemische Fabrik GmbH & Co. KG). Combinations of polythiol molecules or compounds, such as those disclosed herein, may also be used.
  • the polythiol molecule or compound may comprise a mercaptan terminated polysulfide.
  • Suitable commercially available mercaptan terminated polysulfides include those sold under the trade name THIOPLAST® GTM fromNouryon, including, but not limited to, G 10, G 112, G 131, G 1, G 12, G 21, G 22, G 44 and G 4.
  • the polythiol molecule or compound may comprise a mercaptan terminated polyether.
  • Commercially available mercaptan terminated polyether include POLYTHIOL QE-340M available from Toray Fine Chemicals Co., Ltd.
  • the thiol-containing compound may comprise a thiol equivalent weight of at least 45 g/eq, such as at least 75 g/eq, such as at least 100 g/eq.
  • the thiol-containing compound may comprise a thiol equivalent weight of no more than 2,000 g/eq, such as no more than 500 g/eq, such as no more than 250 g/eq.
  • the thiol-containing compound may comprise a thiol equivalent weight of 45 g/eq to 2,000 g/eq, such as 75 g/eq to 500 g/eq, such as 100 g/eq to 250 g/eq.
  • the first component may comprise an amine-containing compound.
  • the amine-containing compound may comprise an amine equivalent weight of 17 g/eq to 10,000 g/eq, such as 25 g/eq to 5,000 g/eq, such as 40 g/eq to 5,000 g/eq, such as 25 g/eq to 1,000 g/eq, such as 40 g/eq to 1,000 g/eq.
  • the first component may comprise a furan-containing compound.
  • Furfuryl alcohol may also be reacted with compounds comprising carboxylic acid or anhydride functional groups to generate furan-containing compounds further comprising ester linkages.
  • Furan- containing compounds further comprising additional reactive functional groups may also be used to generate polyfunctional furan-containing compounds.
  • Suitable furan-containing compounds include reaction products of furfuryl amine with compounds containing isocyanate, epoxy, acrylate, methacrylate, aldehyde, or other amine-reactive functional groups.
  • Further suitable furan-containing compounds include reaction products of furfuryl mercaptan with isocyanate, epoxy, acrylate, methacrylate, maleimide, alkene, or other thiol-reactive functional groups.
  • urethane linkage means a bond formed between two molecules forming the linkage RNHCOOR, wherein R may comprise an alkyl, an alkylene, a (cyclo)alkyl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane).
  • urea linkage means a bond formed between two molecules forming the linkage RNHCONRR, wherein R may comprise an alkyl, an alkylene, a (cyclo)alkyl, an aromatic, or a polymeric structure (including a polyester, a polyurethane, a polyether, an acrylic, or a siloxane).
  • the furan-containing compound may comprise a furan equivalent weight of at least 65 g/eq, such as at least 150 g/eq, such as at least 250 g/eq.
  • the furan-containing compound may comprise a furan equivalent weight of no more than 2,000 g/eq, such as no more than 1,000 g/eq, such as no more than 500 g/eq.
  • the furan-containing compound may comprise a furan equivalent weight of 65 g/eq to 2,000 g/eq, such as 150 g/eq to 1,000 g/eq, such as 250 g/eq to 500 g/eq.
  • the second component may comprise, consist essentially of, or consist of a maleimide-containing compound.
  • the maleimide-containing compound may comprise a maleimide equivalent weight of at least 95 g/eq, such as at least 200 g/eq, such as at least 250 g/eq.
  • the maleimide- containing compound may comprise a maleimide equivalent weight of no more than 5,000 g/eq, such as no more than 2,000 g/eq, such as no more than 1,000 g/eq.
  • the maleimide-containing compound may comprise a maleimide equivalent weight of 95 g/eq to 5,000 g/eq, such as 200 g/eq to 2,000 g/eq, such as 250 g/eq to 1,000 g/eq.
  • the first component may comprise the thiol-containing compound and/or the amine-containing compound and the furan-containing compound in a molar ratio of at least 50:1, such as at least 10:1, such as at least 3:1, such as at least 3:8.
  • the first component may comprise the thiol-containing compound and/or the amine-containing compound and the furan-containing compound in a molar ratio of no more than 1:50, such as no more than 1:10, such as no more than 1:3, such as no more than 1:1.
  • polyepoxides include polyglycidyl ethers of polyhydric alcohols, polyglycidyl esters of polycarboxylic acids, polyepoxides that are derived from the epoxidation of an olefinically unsaturated alicyclic compound, polyepoxides that are derived from the epoxidation of an olefinically unsaturated nonaromatic cyclic compound, polyepoxides containing oxyalkylene groups in the epoxy molecule, and epoxy novolac resins.
  • the anhydride may comprise hexahydrophthalic anhydride and its derivatives (e.g., methyl hexahydrophthalic anhydride); phthalic anhydride and its derivatives (e.g., methyl phthalic anhydride); maleic anhydride; succinic anhydride; trimelletic anhydride; pyromelletic dianhydride (PMDA); 3,3′,4,4′- oxydiphthalic dianhydride (ODPA); 3,3′,4,4′-benzophenone tetracarboxylic dianhydride (BTDA); and 4,4′-diphthalic (hexafluoroisopropylidene) anhydride (6FDA).
  • hexahydrophthalic anhydride and its derivatives e.g., methyl hexahydrophthalic anhydride
  • phthalic anhydride and its derivatives e.g., methyl phthalic anhydride
  • maleic anhydride e.g.,
  • the diacid used to form the epoxy-adduct may comprise any suitable diacid known in the art.
  • the diacids may comprise phthalic acid and its derivatives (e.g., methyl phthalic acid), hexahydrophthalic acid and its derivatives (e.g., methyl hexahydrophthalic acid), maleic acid, succinic acid, adipic acid, and the like.
  • Suitable acrylate-functional compounds include trimethylolpropane triacrylate, tripropyleneglycol diacrylate, dipropylene glycol diacrylate, cyclohexanedimethanol diacrylate, hexanediol diacrylate, pentaerythritol tetraacrylate, di-trimethylolpropane triacrylate, neopentylglycol propoxylate diacrylate, ethoxylated trimethylolpropane triacrylate, urethane acrylate oligomer, propoxylated glyceryl triacrylate, and aliphatic tetrafunctional polyester acrylate oligomer.
  • Suitable acrylate-functional oligomers and polymers include those having an acrylic, polyester, polyether, epoxy, siloxane, melamine, or urethane chemical backbone.
  • Suitable acrylate functional oligomers and polymers include Miramer products commercially available from Miwon Specialty Chemical Co., Sartomer products commercially available from Arkema S.A., and Photomer products commercially available from IGM Resins.
  • the composition may comprise (a) the thiol-containing compound and/or the amine-containing compound and (b) the acrylate-functional compound in a molar ratio of at least 50:1, such as at least 25:1.
  • the composition may comprise (a) the thiol-containing compound and/or the amine-containing compound and (b) the acrylate-functional compound in a molar ratio of no more than 2:1, such as no more than 1.3:1.
  • the composition may comprise (a) the thiol- containing compound and/or the amine-containing compound and (b) the acrylate-functional compound in a molar ratio of 50:1 to 2:1, such as 25:1 to 1.3:1.
  • the components of the composition according to the present disclosure may be substantially free, essentially free, or completely free of disulfide linkages.
  • Such compounds include tris(2,3- dibromopropyl) phosphate (brominated tris) and chlorinated organophosphates such as tris(1,3- dichloro-2-propyl)phosphate (chlorinated tris or TDCPP) and tetrakis(2- chlorethyl)dichloroisopentyldiphosphate (V6).
  • Suitable examples of organic compounds include carboxylic acid, dicarboxylic acid, melamine, and organonitrogen compounds.
  • Other suitable flame retardants include ammonium polyphosphate and barium phosphate.
  • the accelerator may comprise a guanidine, a substituted guanidine, a substituted urea, a melamine resin, a guanamine derivative, a cyclic tertiary amine, an aromatic tertiary amine, or combinations thereof.
  • guanidine refers to guanidine and derivatives thereof.
  • the bond between the two substrates may be reformed by the method of bonding two substrates described herein above, heating the assembly above the reflow onset temperature of the composition, then cooling the assembly, as described herein above.
  • the present disclosure is also directed to a method of repairing an article, coating, or film formed from one of the compositions disclosed herein.
  • the present disclosure is further directed to a method of forming an article comprising extruding any of the compositions disclosed herein. The extruding may comprise three-dimensional printing.
  • Suitable substrates may include, but are not limited to, both flexible and rigid metal substrates such as ferrous metals, aluminum, aluminum alloys, magnesium, titanium, copper, and other metal and alloy substrates.
  • the ferrous metal substrates may include, for example, iron, steel, and alloys thereof.
  • useful steel materials include cold rolled steel, nickel plated cold rolled steel, galvanized (zinc coated) steel, electrogalvanized steel, stainless steel, pickled steel, zinc-iron alloy such as GALVANNEAL, and combinations thereof.
  • the substrate may be in any form, such as, without limitation, a sheet, a foil, a laminate foil, a pad, a fabricated part, a component, or an article.
  • Compositions comprising the materials disclosed herein may be used to coat a substrate, such as by depositing, applying or contacting the compositions on a substrate surface.
  • FIG.9 illustrates an isometric cut-out view of a cell to chassis battery assembly 300.
  • Cells 10 are arranged on a base comprising the undercarriage 55 and supported by the vehicle frame 45 and under the vehicle interior floor 35.
  • Any battery assembly may further comprise a thermal management system comprising air or fluid circuits which may be liquid based (for example glycol solutions) or direct refrigerant based.
  • composition of any of aspects 44 to 47 wherein the composition comprises (a) the thiol-containing compound and/or the amine-containing compound and (b) the acrylate-functional compound in a molar ratio of at least 50:1, such as at least 25:1, such as no more than 2:1, such as no more than 1.3:1, such as 50:1 to 2:1, such as 25:1 to 1.3:1.
  • the composition is formulated as a coating composition, an adhesive composition, a sealant, an encapsulated composition, a pottant, a foam, or a pad.
  • 50 The composition of any of the preceding aspects, further comprising an accelerator.
  • a method for forming a film comprising: casting the film comprising the composition of any of aspects 1 to 54.
  • 66 A method of forming a bond between two substrates comprising: applying the composition of any of aspects 1 to 54 to a first substrate; and contacting a second substrate to the coating composition such that the coating composition is located between the first substrate and the second substrate.
  • 67 The method of aspect 66, wherein a joint between the first substrate and the second substrate is at least partially broken prior to the contacting and wherein the contacting forms a repair joint.
  • 68. A method of forming an article comprising extruding or molding the composition of any of aspects 1 to 54.
  • 69 A method of forming a bond between two substrates comprising: applying the composition of any of aspects 1 to 54 to a first substrate; and contacting a second substrate to the coating composition such that the coating composition is located between the first substrate and the second substrate.
  • the composition comprises a lap shear strength of at least 4 MPa at failure, wherein the composition comprises a lap shear strength of at least 4 MPa at failure, wherein the lap shear displacement and the lap shear strength are measured according to ASTM D1002-10 using 4130 CRS substrate of 0.063 in. thickness, as measured by an INSTRON 5567 machine in tensile mode with a pull rate of 1.3 mm per minute.
  • the composition comprises a pottant, a pad, a foam, a coating, or combinations thereof.
  • a 3D-printed structural article comprising the composition of any of aspects 1 to 54.
  • Samples of Composition III were prepared by mixing the components in the manner and amounts as described in Table 3 above and applied using a metal spatula onto the zirconium treated steel. These specimens were then sandwiched together at the desired overlap and held together using small binder clips. Excess adhesive was removed from the joint using a metal spatula. These specimens were then allowed to cure at 70°C for approximately 12 hours.
  • Each of the baked lap joint specimens were tested using an INSTRON 5567 Machine in tensile mode with 25.4 mm of substrate in each grip and at a pull rate of 1.3 mm/minute in accordance with ASTM D1002-10. [0295] The lapshear test results of all these specimens can be found in Table 4 below.
  • compositions IV – VI in Tables 5 below were prepared by blending the components listed in their indicated amounts in a DAC cup and mixing for 4 minutes at 2350 RPM using a SpeedMixer®.
  • compositions IV – VI in Tables 5 above were then taken and blended with the components prescribed in Table 6 below for 2 minutes at 2350 RPM using a SpeedMixer®.
  • Test specimens were then prepared on 0.032” thick CRS from ACT, which were treated with Zircobond 4200 as described in the earlier example.
  • Test specimens were prepared in three different manners: 2K, Film, and 2K repaired.
  • the 2K specimen was prepared by mixing the components in the manner and amounts listed in Table 5, above, and applying to a piece of the zirconium treated steel. The two pieces were sandwiched together at the desired overlap and held together using small binder clips. The specimens were then allowed to cure at 70°C for approximately 12 hours.

Abstract

La présente invention concerne des compositions comprenant un premier composant comprenant un composé contenant un thiol, un composé contenant une amine, ou une combinaison de ceux-ci; et un composé contenant du furane; et un second composant comprenant un composé contenant du maléimide. La présente invention concerne également des substrats comprenant une surface revêtue de l'une quelconque des compositions de l'invention ou intégrée dans celle-ci. La présente invention concerne également des revêtements, des films et des articles structuraux imprimés en 3D formés à partir de l'une quelconque des compositions de l'invention. La présente invention concerne également des procédés de formation de revêtements comprenant le mélange de l'un quelconque des premiers et seconds composants de l'invention pour former la composition; et l'application de la composition sur une surface du substrat. La présente invention concerne également des procédés de formation d'un film comprenant le mélange de l'un quelconque des premiers et seconds composants selon l'invention pour former la composition; et la coulée du film.
PCT/US2023/078147 2022-12-29 2023-10-30 Compositions durcissables WO2024144922A2 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US63/477,568 2022-12-29

Publications (1)

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WO2024144922A2 true WO2024144922A2 (fr) 2024-07-04

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