Solutions of amines in functional and non-functional resins

Abstract

This disclosure provides a potential curing accelerator and a composition containing such a potential curing accelerator together with a substance to be cured (e.g., an epoxy resin). The potential curing accelerator comprises an amine and an encapsulant system having at least one additional excipient selected from functional and / or non-functional components. Methods for production and use are further provided.

Description

Technical Field

[0001] Background Compositions containing epoxy resins and curing agents (hardeners) have been known for decades. Many curing agents react with epoxy resins at room temperature and thus must be mixed immediately before use. Others, known as latent hardeners, are stable when mixed with epoxy resins at ambient temperature and provide curing only when heated to elevated temperatures. Some compounds also act as accelerators for latent curing agents, dicyandiamide (DICY) or acid anhydrides, and provide curing of epoxy resins at elevated temperatures. There is a need for latent epoxy curing agents or accelerators that exhibit long-term storage stability at ambient temperature and cure rapidly above 100 °C.

[0002] U.S. Patents 3,519,576 and 3,520,905 describe the use of salts of monomeric polyvalent phenols containing polyamines as latent curing agents for epoxy resins. These compositions rapidly cure the resin at ambient temperature. U.S. Patents 4,701,378 and 4,713,432 describe the use of polymeric phenols and polyamine salts to accelerate epoxy curing induced by dicyandiamide (DICY), a commonly used latent curing agent. U.S. Patent 4,866,133 describes the use of solid solutions of polymeric polyvalent phenols and polyamines for curing epoxy resins. The polyamines used contain at least two amine groups, at least one of which is a primary amine. These curing agents are used to cure liquid epoxy resins at a concentration of at least 10% by weight relative to the epoxy resin. U.S. Patent No. 4,689,390 describes the preparation of potential curing agents by reacting diamines having tertiary amine groups and primary or secondary amino groups with polyepoxy compounds and phenolic resins or phenolic compounds. A solution of tertiary polyamines in polyphenolic resins made from bisphenol A diglycidyl ether and polyamino secondary amines is described as a potential epoxy curing agent in U.S. Patent Application No. 13 / 075403. U.S. Patent No. 7,910,667 describes a polyphenolic resin solution of a polyurea derivative of a tertiary polyamine used as a potential epoxy curing agent. U.S. Patent No. 9,546,243 describes a polyphenolic resin solution of a specific class of amines used as a sole potential epoxy curing agent and DICY accelerator. Finally, U.S. Patent No. 9,000,120 reports a thermally activatable DICY accelerator consisting of a tertiary amine and a novolac resin.

[0003] There remains a need for lower-cost and more efficient latent epoxy curing agents. Furthermore, from an energy-saving perspective, there is a prominent need for latent epoxy curing agents and accelerators that can cure epoxy resins at lower temperatures without sacrificing the storage stability of epoxy formulations. The methods and curing agents described above have several drawbacks, including high usage levels, low curing temperatures and poor storage stability, or the fact that precursor amines are obtained through multi-step processes, such as addition with polyepoxides. This specification describes a new class of latent epoxy curing agents that solve most of the problems inherent in these current curing systems and reduce the curing temperature without impairing the latent properties of one-component epoxy resin compositions.

[0004] overview Accordingly, this specification provides epoxy curing agents and related compositions that enable lower curing temperatures without impairing the latent properties of epoxy resin compositions.

[0005] The inventors have found that by using a solution containing a specific class of amines and a polymer resin encapsulating a polymer resin in combination with one or more monomer or polymer compounds, each of which may be functionalized with acidic substituents that can interact with tertiary amines (e.g., OH, COOH, SO3OH, PO(OH)3, and PO(OH)2), it is possible to obtain an epoxy curing agent with improved storage stability, a lower curing temperature, and a lower usage level (less than 10% by weight relative to the epoxy compound). Non-functional compounds or non-functional polymers do not have these functional groups and do not interact with tertiary amines.

[0006] In a first aspect, the disclosure relates to a potential curing accelerator composition [Composition 1] comprising: Amines, and A mounting system comprising additional excipients selected from functional components (e.g., compounds or polymers functionalized by carboxy and / or hydroxyl groups) and / or non-functional components.

[0007] In some embodiments, composition 1 is defined as follows: 1.1 Composition 1, wherein the amine is a tertiary amine. 1.2 Amines, (a) alkyl-substituted or aryl-substituted tertiary amines (e.g., monotertiary amines) (b) Tertiary amines having more than two peralkylated nitrogen atoms (c) Tertiary amines having more than two nitrogen permethylated atoms (d) N,N-dimethyl polyamine having at least one primary amine and one secondary amine (e) Crosslinked or condensed bicyclic diamines, and / or (f) Composition 1 or 1.1, selected from at least one of alkyl, aryl, alkylaryl, alkyl ether, alkylamino, or imidazoles which may be substituted with at least one halogen (e.g., alkylamino-substituted imidazole, 2-alkyl-substituted or 2-aryl-substituted imidazole, e.g., 2-methylimidazole). 1.3 Any of the aforementioned compositions, wherein the amine comprises one or more of the following: 3,3',3”-imino-tris-(N,N-dimethylpropylamine), 1,8-diazabicyclo(5.4.0)undeca-7-ene (DBU), triethylenediamine (TEDA), 1-(3-aminopropyl)imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, [(dimethylamino)methyl]phenol, bis-[(dimethylamino)methyl]phenol and tris-(dimethylaminomethyl)phenol (e.g., 2,4,6-tris-(dimethylaminomethyl)phenol), [(dimethylamino)methyl]phenol, and mixtures of bis- and tris-(dimethylamino)methyl substituted phenols. 1.4 Any of the above compositions, wherein the amine is an N,N-dimethyl polyamine having at least one primary and one secondary amine. 1.5 Any of the aforementioned compositions, wherein the amine is selected from [(dimethylamino)methyl]phenol, bis-[(dimethylamino)methyl]phenol and tris-(dimethylaminomethyl)phenol (e.g., 2,4,6-tris-(dimethylaminomethyl)phenol) and combinations thereof. 1.6 Any of the aforementioned compositions, wherein the amine comprises or consists of bis-[(dimethylamino)methyl]phenol and tris-(dimethylaminomethyl)phenol (e.g., 2,4,6-tris-(dimethylaminomethyl)phenol) and combinations thereof. 1.7 Any of the aforementioned compositions, wherein the amine comprises a mixture of bis- and tris-[(dimethylamino)methyl]phenol. 1.8 Any of the aforementioned compositions, wherein the amine is present in an amount of about 10% to about 75% by weight, about 10% to about 60% by weight, about 20% to about 60% by weight, about 30% to about 60% by weight, about 30% to about 50% by weight, or about 40% to about 50% by weight (for example, preferably about 10% to about 60%) based on the total weight of the composition. 1.9 Any of the aforementioned compositions, wherein the additional excipient is a functional compound containing one or more carboxyl groups and / or hydroxyl groups, and comprises (a) an acrylic resin, (b) a polyether resin, (c) a polybutadiene resin, (d) a polyamide resin, and optionally (e) one or more monomeric carboxylic acids, sulfonic acids, phosphonic acids, phosphoric acids, or boric acids. 1.10 Any of the aforementioned compositions, wherein the additional excipient is present in an amount of about 10% to about 75% by weight, about 10% to about 60% by weight, about 20% to about 60% by weight, about 30% to about 60% by weight, or about 40% to about 60% by weight (for example, preferably about 20% to about 60%) based on the total weight of the composition. 1.11 Any of the aforementioned compositions, comprising or consisting of an additional excipient, which is present in an amount of about 10% to about 75% by weight, about 10% to about 60% by weight, about 20% to about 60% by weight, about 30% to about 60% by weight, or about 40% to about 60% by weight (for example, preferably about 20% to about 60%) based on the total weight of the composition, a functional compound. 1.12 Any of the aforementioned compositions, wherein the additional excipient is a monomeric carboxylic acid, a sulfonic acid, a phosphonic acid, a phosphoric acid, or a boric acid. 1.13 Any of the above compositions, wherein the additional excipient comprises or consists of a monomeric carboxylic acid. 1.14 Any of the aforementioned compositions, wherein the additional excipient comprises or consists of a monomer sulfonic acid. 1.15 Any of the aforementioned compositions, wherein the additional excipient comprises or consists of a monomer phosphonic acid. 1.16 Any of the above compositions, wherein the additional excipient comprises or consists of a monomer phosphate. 1.17 Any of the aforementioned compositions, wherein the additional excipient comprises or consists of monomeric boric acid. 1.18 Any of the above compositions, wherein the additional excipient is an acrylic resin or comprises an acrylic resin. 1.19 The acrylic resin has the following structure: [ka] In the formula, R1 is H or C 1-3 Selected independently of alkyl, R2 is H or C 1-8 The aforementioned composition, wherein the alkyl group may be substituted with an -OH group. 1.20 The acrylic resin has the following structure: [ka] In the formula, R1 is selected independently of H or CH3. R2 is H or C 1-8The aforementioned composition, wherein the alkyl group may be substituted with an -OH group. 1.21 Any of the above compositions, wherein the acrylic resin is formed by free radical polymerization of acrylic monomers and vinyl monomers together with unsaturated monomers containing hydroxyl or carboxyl groups. 1.22 Any of the above compositions, wherein the acrylic resin is formed by free radical polymerization of an acrylic monomer containing a hydroxyl group, a carboxyl group, and / or an ester group. 1.23 Any of the above compositions, wherein the acrylic resin is formed by free radical polymerization of an acrylic monomer containing a carboxyl group. 1.24 Any of the above compositions, wherein the acrylic resin is formed by free radical polymerization of an acrylic monomer containing an ester group. 1.25 Any of the above compositions, wherein the acrylic resin is formed by the free radical polymerization of an acrylic monomer containing a hydroxyl group. 1.26 Any of the above compositions, wherein the acrylic resin has an acid value of approximately 50 to approximately 120 mg / KOH, approximately 60 to approximately 100 mg / KOH, or approximately 70 to approximately 90 mg / KOH (for example, approximately 70 mg / KOH). 1.27 Any of the above compositions, wherein the additional excipient comprises or consists of a polyether resin. 1.28 Any of the above compositions, wherein the additional excipient is polyalkylene glycol. 1.29 The aforementioned composition, wherein the polyalkylene glycol has a molecular weight of approximately 1,000D to approximately 100,000D. 1.30 The aforementioned composition, wherein the polyalkylene glycol has a molecular weight of approximately 1,500D to approximately 35,000D. 1.31 The aforementioned composition, wherein the polyalkylene glycol has a molecular weight of approximately 1,500D to approximately 10,000D. 1.32 Any of the above compositions, wherein the additional excipient comprises or consists of a polybutadiene resin. 1.33 The composition described above, wherein the polybutadiene resin is carboxylated polybutadiene. 1.34 The composition described above, wherein the carboxylated polybutadiene has a polybutadiene backbone microstructure composed of a combination of vinyl 1,2 bonds, trans 1,4 bonds, and cis 1,4 bonds. 1.35 Any of the compositions 1.33 - 1.34, wherein the carboxylated polybutadiene has an average molecular weight of about 500D to about 10,000D. 1.36 Any of the compositions 1.33 - 1.35, wherein the carboxylated polybutadiene has a molecular weight of about 1,000D to about 7,000D. 1.37 Any of the compositions 1.33 - 1.36, wherein the carboxylated polybutadiene has a molecular structure composed of 70 - 90% cis double bonds, 10 - 30% trans double bonds, and 0 - 3% vinyl double bonds. 1.38 Any of the compositions 1.33 - 1.37, wherein the carboxylated polybutadiene is a maleic anhydride adduct of cis - 1,4 - polybutadiene (e.g., low molecular weight cis - 1,4 - polybutadiene) that may have succinic anhydride pendant groups randomly distributed in the polymer chain. 1.39 Any of the above - mentioned compositions, wherein the additional excipient comprises or consists of a polyamide resin. 1.40 The composition described above, wherein the polyamide resin is nylon (e.g., nylon - 6, nylon 6 - 6, a copolymer of nylon - 6 and nylon 6 - 6, nylon - 9, nylon - 10, nylon - 11, nylon - 12, nylon 6 - 10), aromatic polyamide, elastomeric polyamide, and mixtures thereof. 1.41 Any of the compositions 1.39 - 1.40, wherein the polyamide resin is an acid - functional thermoplastic polyamide. 1.42 Any of the above - mentioned compositions, wherein the additional excipient is a non - functional component that is a polymer compound selected from acrylates, polybutadiene, polyamides, ketone - aldehyde condensation resins, polyimides, styrene - butadiene resins, copolymers of olefins, and combinations thereof. 1.43 Any of the aforementioned compositions, wherein the additional excipient comprises or consists of a non-functional compound present in an amount of about 10 wt% to about 75 wt%, about 10 wt% to about 60 wt%, about 10 wt% to about 50 wt%, about 10 wt% to about 40 wt%, about 10 wt% to about 30 wt%, or about 10 wt% to about 20 wt% (e.g., preferably about 10 wt% to about 30 wt%) based on the total weight of the composition. 1.44 Any of the aforementioned compositions, wherein the weight ratio of the amine to the encapsulation system is about 1:0.3 to about 1:10, or about 1:0.3 to about 1:2, or about 1:0.5 to about 1:1.5, or about 1:0.8, or about 1:1.1, or about 1:1.4. 1.45 Any of the aforementioned compositions, wherein the composition is prepared by dissolving the amine in an encapsulating agent system comprising an additional excipient. 1.46 Any of the aforementioned compositions, which is combined with an epoxy resin to form a curable epoxy system. 1.47 Composition 1.46, wherein the curable epoxy system has an onset temperature of about 130 °C to about 151 °C. 1.48 Composition 1.46 or 1.47, wherein the curable epoxy system has an onset temperature of about 133 °C to about 146 °C. 1.49 Any of Compositions 1.46 to 1.48, wherein the curable epoxy system has a viscosity of about 20,000 cP to about 45,000 cP. 1.50 Any of Compositions 1.46 to 1.49, wherein the curable epoxy system does not gel after 4 weeks under accelerated degradation conditions (i.e., storage at 40 °C for 4 weeks). 1.51 Any of Compositions 1.46 to 1.50, wherein the curable epoxy system provides a lap shear strength of about 500 psi to 1700 psi. 1.52 Any of Compositions 1.46 to 1.51, wherein the additional excipient is an acrylic resin and the curable epoxy system provides a lap shear strength of about 800 psi to about 1500 psi. 1.53 Any of Compositions 1.46 to 1.52, wherein the curable epoxy system provides an adhesion strength of about 50 pli to 130 pli as determined by a T-peel test. 1.54 Any of compositions 1.46 to 1.53, wherein the additional excipient component of the potential curing accelerator composition is an acrylic resin, and the curable epoxy system yields an adhesive strength of approximately 50 pli to 130 pli, as determined by a T-type peel test. 1.55 Any of the aforementioned compositions, wherein the composition is in liquid or solid powder form. 1.56 Any of the above compositions, wherein the composition is in the form of an aqueous solution. 1.57 Any of the above compositions further comprising one or more wetting agents, fillers, defoamers, and rheological modifiers. 1.58 Any of the above compositions, wherein the composition is a potential curing agent for epoxy resins (e.g., a sole potential curing agent).

[0008] In a second embodiment, this disclosure is, Potential curing accelerator compositions (i.e., Composition 1, and subsequent compositions), and This relates to a curable epoxy system [System 1] containing epoxy resin.

[0009] In some embodiments, System 1 is defined as follows. 1.1 System 1, wherein the potential curing accelerator composition is composition 1 and any of the following. 1.2 System 1 or 1.1, where the epoxy is a glycidyl ether, a polyhydric phenol, or an alicyclic epoxide (including diepoxides of alicyclic esters of dicarboxylic acids). 1.3 Epoxy is a polymer defined by the following formula: [ka] In the formula, m is an integer and R is a divalent hydrocarbon radical of divalent phenol, one of the aforementioned systems. 1.4 The system is one of the aforementioned systems having an onset temperature of approximately 130°C to approximately 151°C. 1.5 The system is one of the aforementioned systems having an onset temperature of approximately 133°C to approximately 146°C. 1.6 The system is one of the aforementioned systems having a viscosity of approximately 20,000 cP to approximately 45,000 cP. 1.7 Any of the aforementioned systems that does not gel after 4 weeks under accelerated degradation conditions (i.e., 4 weeks of storage at 40°C). One of the aforementioned systems, where the 1.8 system provides a lap shear strength of approximately 500 psi to 1700 psi. 1.9 Any of the aforementioned systems, wherein the additional excipient in the potential accelerator composition is an acrylic resin, and the system yields a lap shear strength of about 800 psi to about 1500 psi. 1.10 is one of the aforementioned systems that provides an adhesive strength of approximately 50 pli to 130 pli, as determined by a T-type peel test. 1.11 Any of the aforementioned systems, wherein the additional excipient in the potential accelerator composition is an acrylic resin, and the system yields an adhesive strength of about 50 pli to 130 pli, as determined by a T-type peel test. 1.12 Any of the above systems further comprising one or more wetting agents, fillers, defoamers, and rheological modifiers. 1.13 Any of the above systems, wherein the potential accelerator composition is a potential curing agent for epoxy resins (e.g., the sole potential curing agent). 1.14 Any of the aforementioned systems, further including DICY.

[0010] In a third aspect, this disclosure is: Amine and, The present invention relates to a method for curing a substance by the use of a potential curing accelerator composition comprising an encapsulant system containing additional excipients selected from functional and / or non-functional components, The method includes the steps of combining a substance with a potential curing accelerator composition and heating the resulting mixture.

[0011] In some embodiments, Method 1 is defined as follows: 1.1 Method 1, where the substance is epoxy resin. 1.2 Method 1 or 1.1, wherein the potential curing accelerator composition is composition 1 and subsequent compositions. 1.3 Any of the methods described above, which involves heating a mixture containing a substance with a potential curing accelerator to a temperature of about 130°C to about 151°C. 1.4 Any of the methods described above, which involves heating a mixture containing a substance that includes a potential curing accelerator to a temperature of about 133°C to about 146°C. 1.5 Any of the methods described above, wherein the potential curing accelerator composition is formed by blending an amine and a mounting agent system under a nitrogen atmosphere and heating to a temperature of 130°C to 180°C. 1.6 Any of the above methods, wherein the composition is a potential curing agent for epoxy resins (e.g., a sole potential curing agent). 1.7 Any of the methods described above, wherein the composition is used as an accelerator for curing agents such as DICY or as an acid anhydride for epoxy resins. 1.8 Any of the methods described above, in which the composition is used as a potential curing accelerator for structural adhesives and composites, electrical potting and encapsulation, reinforcement and / or damping, in-situ curing pipes, impact adhesives, filament winding, transfer molding powder, prepregs containing solid or liquid epoxy, sheet molding compounds, coatings for concrete, wood, metal and the like, resin transfer molding, and / or battery pack adhesives.

[0012] This disclosure further provides potential curing accelerator compositions for use in methods for curing materials, for example, for use in Method 1 and any of the subsequent methods.

[0013] This disclosure further provides the use of a potential curing accelerator composition in the manufacture of a curable formulation, including a substance and a potential curing accelerator composition, for use in Method 1 and any of the subsequent methods.

[0014] Modes for carrying out the invention This disclosure provides potential curing accelerators, as well as compositions containing such potential curing accelerators together with a substance to be cured (e.g., epoxy resin). Methods for manufacturing and using these agents are further provided.

[0015] Amine The potential curing accelerator of this disclosure comprises at least one amine compound. The class of amines used in this composition is: (a) alkyl-substituted or aryl-substituted tertiary amines (e.g., monotertiary amines) (b) Tertiary amines having more than two peralkylated nitrogen atoms (c) Tertiary amines having more than two nitrogen permethylated atoms (d) N,N-dimethyl polyamine having at least one primary amine and one secondary amine (e) Crosslinked or condensed bicyclic diamines, and (f) comprising an imidazole which may be substituted with alkyl, aryl, alkylaryl, alkyl ether, alkylamino, or at least one halogen (e.g., alkylamino-substituted imidazole, 2-alkyl-substituted or 2-aryl-substituted imidazole, e.g., 2-methylimidazole).

[0016] Non-limiting examples of amines that may be used in the disclosed compositions include 3,3',3”-iminotris(N,N-dimethylpropylamine), 1,8-diazabicyclo(5.4.0)undeca-7-ene (DBU), triethylenediamine (TEDA), 1-(3-aminopropyl)imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, [(dimethylamino)methyl]phenol, bis[(dimethylamino)methyl]phenol, and 2,4,6-tris(dimethylaminomethyl)phenol. Further examples of amines include monosubstituted phenol compounds, e.g., [(dimethylamino)methyl]phenol (marketed by Evonik Corporation as Ancamine 1110), and mixtures of bis- and tris-dimethylaminomethyl substituted phenols (marketed by Evonik Corporation as Ancamine K54). Evonik Corporation is part of this disclosure. Other commercially available tertiary amines from the Corporation include pentamethyldiethylenetriamine, bis(2-dimethylaminoethyl) ether, trimethylaminopropoxyethanol, bisdimethylaminopropylamine, dimethylaminopropylamine (DMAPA), and trisdimethylaminopropylamine.

[0017] The amine may be present in the potential curing accelerator composition in an amount of about 10% to about 75% by weight based on the total weight of the composition. In further embodiments, the amine may be present in an amount of about 10% to about 75% by weight, about 10% to about 60% by weight, about 20% to about 60% by weight, about 30% to about 60% by weight, about 30% to about 50% by weight, or about 40% to about 50% by weight (for example, preferably about 10% to about 60%) based on the total weight of the composition.

[0018] Additional excipients In various embodiments, the encapsulation systems of the present disclosure further include additional excipients, which may be functional or non-functional monomer or polymer compounds. Exemplary excipients are provided below. In various embodiments, the additional excipients may be present in an amount of about 1% to about 75% by weight based on the total weight of the composition. In further embodiments, the additional excipients may be present in an amount of about 10% to about 75% by weight, about 10% to about 60% by weight, about 20% to about 60% by weight, about 30% to about 60% by weight, or about 40% to about 60% by weight (for example, preferably about 20% to about 60%) based on the total weight of the composition. If one or more additional excipients are present, this concentration may refer to the total amount of the additional excipients or to individual additional excipients.

[0019] functional compound The functional compounds described herein include a variety of chemical substances, such as phenols, alkyl or aryl-substituted carboxylic acids, sulfonic acids, phosphoric acids, phosphonic acids, and boric acids.

[0020] Representative phenolic compounds that can be used include phenols or substituted phenols (substituents include alkyl, aryl ether, amino groups, or halogen atoms), such as p-tert-butylphenol, p-sec-butylphenol, o-tert-butylphenol, o-sec-butylphenol, p-tert-amylphenol, p-tert-octylphenol, p-nonylphenol, p-cumylphenol, p-dodecylphenol, styrylphenol, 2,6-di-tert-butylphenol, 2,4-di-tert-butylphenol, di-sec-butylphenol, 2,4-di-tert-amylphenol, 2,4-di-cumylphenol, o-cumyloctylphenol, α-naphthol, β-naphthol, bis-phenol A, bis-phenol F, bis-phenol TMC, and mixtures thereof, comprising at least one member selected from this group.

[0021] Representative carboxylic acids that may be used include at least one member selected from the group consisting of acetic acid, propanoic acid, hexanoic acid, 2-ethylhexanoic acid, decanoic acid, stearic acid, benzoic acid, salicylic acid, tall oil fatty acids (TOFAs), dimer acids, and mixtures thereof.

[0022] It is intended that a variety of other acidic functional compounds may be used in the compositions of this disclosure. Non-limiting examples of such compounds include sulfonic acids, such as p-toluenesulfonic acid, methanesulfonic acid, dodecylbenzenesulfonic acid, trifluoromethanesulfonic acid, phosphonic acid, phosphoric acid, and boric acid. Functional polymer compounds include a variety of chemical substances, such as acrylics, polyethers, polybutadienes, polyamides, and combinations thereof.

[0023] As used herein, the terms “functional” or “functionalized” refer to compounds or polymers that contain, or are modified to contain, one or both, a carboxyl group and / or a hydroxyl group.

[0024] Acrylic resin The acrylic polymers useful in this disclosure can be prepared by free radical polymerization of an unsaturated monomer having a hydroxyl group or a carboxyl group with acrylic and vinyl monomers. Useful acrylic resins include those having hydroxyl functional groups with a hydroxyl value of greater than 1 to 200 and carboxyl functional groups with an acid value of greater than 1 to 300. The preferred softening point of the acrylic polymer is about 50°C to 200°C.

[0025] Useful functional monomers are selected from acrylic acid, methacrylic acid, crotonic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, and hydroxypropyl methacrylate. Other acrylic monomers can be selected from the group consisting of esters of α,β-ethylenically unsaturated carboxylic acids having 3 to 8 carbon atoms. Preferred acrylic monomers have the following structure: [ka] It has, In the formula, R1 is H or C 1-3 Selected independently of alkyl, R2 is H or C 1-8 It is an alkyl group, and the alkyl group may be substituted with an -OH group.

[0026] Examples of acrylic monomers useful in the compositions of this disclosure include ethyl acrylate, butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, and lauryl methacrylate.

[0027] In various embodiments, acrylic polymers may optionally contain ethylenically monounsaturated vinyl comonomers distinct from functional monomers and acrylic monomers. Examples of potentially useful ethylenically unsaturated vinyl comonomers include styrene, propylene, vinyltoluene, dimethylstyrene, α-methylstyrene, and vinyl acetate. Acrylic compounds may be liquids, solids, or solutions in organic solvents.

[0028] Copolymers can be prepared in any known manner, preferably by free radical polymerization in bulk, solution, emulsion, or suspension. Preferably, the reaction is carried out in the presence of a free radical initiator, such as an azo compound, e.g., benzoyl peroxide, tert-butyl peroxide, decanoyl peroxide, or azobisisobutyronitrile. Such initiators may be present in an amount ranging from 0.1 to about 5% by weight of the total monomers.

[0029] In various embodiments, commercially available acrylic resins used in the compositions of this disclosure include ISOCRYL C-78 (sold by Estron Chemical Inc.), ISOCRYL H-89 (sold by Estron Chemical Inc.), and JONCRYL 67 (sold by BASF).

[0030] Polyether resin A preferred polyether resin used in the compositions of this disclosure is polyalkylene glycol. Polyalkylene glycol may have a molecular weight of 1,000 to 100,000 D [Daltons], preferably 1,500 to 35,000 D, and particularly preferably 1,500 to 10,000 D. A particularly preferred polyalkylene glycol is polyethylene glycol. Furthermore, polypropylene glycol, polytetrahydrofuran, or polybutylene glycol are also suitable, and these are obtained from 2-ethyloxirane or 2,3-dimethyloxirane. Other suitable polyethers are random or block copolymers of polyalkylene glycols obtained from ethylene oxide, propylene oxide, and butylene oxide, such as polyethylene glycol-polypropylene glycol block copolymer. The block copolymer may be of type AB or ABA.

[0031] More preferable polyalkylene glycols include those alkylated at one or both terminal OH groups. Suitable alkyl radicals include branched or linear C 1-22 Alkyl radical, preferably C 1-18 Alkyl radicals, such as methyl, ethyl, n-butyl, isobutyl, pentyl, hexyl, octyl, nonyl, decyl, dodecyl, tridecyl, or octadecyl radicals.

[0032] Preferred polyalkylene glycols also include those that are acid-capped at one or both terminal OH groups. An example of such a preferred polyalkylene glycol is a phosphonic acid-terminated polyether. Another example of a preferred polyalkylene glycol is a polyoxyethylene chain grafted onto a polycarboxylate-type skeleton.

[0033] The method for producing polyether copolymers according to this disclosure is generally known in the prior art. Preparation is preferably carried out by free radical polymerization in solution, in a non-aqueous organic solvent, or in a non-aqueous / aqueous mixed solvent. Suitable preparation processes are described, for example, in International Publication Nos. 2007 / 051743 and International Publication Nos. 2009 / 013202, and the disclosure relating to the preparation processes is incorporated herein by reference in whole.

[0034] Polybutadiene resin Examples of polybutadiene-based polyol resins used in the compositions of this disclosure include homopolymers, such as 1,2-polybutadiene polyol and 1,4-polybutadiene polyol; copolymers, such as poly(pentadiene butadiene) polyol, poly(butadiene styrene) polyol and poly(butadiene acrylonitrile) polyol; and hydrogenated polybutadiene-based polyol resins obtained by hydrogenating these polyol resins. These polybutadiene-based polyol resins are commercially available, for example, from Idemitsu Kosan Co., Ltd. as Poly bd R-15HT (hydroxyl value = 102.7 mg KOH / mg, Mw1200) and Poly bd R-45HT (hydroxyl value = 46.6 mg KOH / mg, Mw2800). Furthermore, due to the advantages of this disclosure, the hydroxyl value of the polybutadiene-based polyol resin is preferably 40 to 330 mg KOH / g, more preferably 40 to 110 mg KOH / g. The polybutadiene-based polyol preferably has a weight-average molecular weight (GPC) of 50 to 3,000, more preferably 800 to 1,500.

[0035] Other polybutadiene resins suitable for use in the compositions of this disclosure include carboxylated polybutadiene, which may be in the form of a liquid polymer having a polybutadiene skeletal microstructure consisting of a combination of vinyl 1,2, trans 1,4, and cis 1,4 bonds, and is transparent at room temperature. The vinyl 1,2 bonds are preferably 30% by weight or less. The cis 1,4 bonds are preferably 40% by weight or more. If the cis 1,4 bonds are less than 40% by weight, it may lead to a decrease in the adhesion of the resulting composition and is therefore undesirable.

[0036] The carboxylated polybutadiene component can be obtained by reacting a carboxyl group-introduced compound with liquid polybutadiene. The 1,3-butadiene and carboxyl group-introduced compound constituting the liquid polybutadiene are preferably used in proportions of 80-98% by mass (1,3-butadiene) and 2-20% by mass (carboxyl group-introduced compound), respectively.

[0037] The liquid polybutadiene used in the reaction preferably has a number-average molecular weight of 500 to 10,000, more preferably 1,000 to 7,000. A broad molecular weight distribution is desirable for the liquid polybutadiene. More preferably, the liquid polybutadiene has an iodine value of 30 to 500 g of iodine per 100 g of material, as determined according to DIN 53241. Preferably, the liquid polybutadiene has a molecular structure consisting of 70 to 90% cis double bonds, 10 to 30% trans double bonds, and 0 to 3% vinyl double bonds.

[0038] Examples of carboxyl group-introduced compounds that can be used include ethylene-based unsaturated dicarboxyl compounds, such as ethylene-based unsaturated dicarboxylic acids, and their anhydrides or monoesters. Specific examples of compounds include maleic acid, fumaric acid, itaconic acid, 3,6-tetrahydrophthalic acid, itaconic anhydride, 1,2-dimethylmaleic anhydride, monomethyl maleic acid, or monoethyl maleic acid. Of these, maleic anhydride is preferred due to its safety, economy, and reactivity (polybutadiene maleate is preferred).

[0039] Methods for producing polybutadiene / maleic anhydride adducts are generally known in the prior art.

[0040] Maleic acid liquid polybutadiene has an acid value of preferably 50 to 120 mg KOH / g, more preferably 70 to 90 mg KOH / g, as measured according to DIN ISO 3682. If the acid value is less than 50 mg KOH / g, the adhesiveness of the resulting composition will decrease, but if the acid value exceeds 120 mg KOH / g, it will lead to an increase in the viscosity of the resulting composition, reducing its workability.

[0041] The maleic acid ratio of maleic acid-coated liquid polybutadiene needs to be considered along with viscosity, but is preferably 6-20%, more preferably 6-15%, and even more preferably 7-10%.

[0042] The viscosity of liquid polybutadiene with maleic acid, as determined by DIN 53214 (at 20°C), is preferably 3 to 16 Pa·s, more preferably 5 to 13 Pa·s, and even more preferably 6 to 9 Pa·s.

[0043] Furthermore, the maleic acid-coated liquid polybutadiene contains 30% or less vinyl double bonds. Liquid polybutadiene with cis double bonds within the above range tends to have higher flexibility and a higher maleic acid ratio (i.e., acid value) compared to liquid polybutadiene with cis double bonds at a lower percentage than the above lower limit. As a result, the composition has high adhesion and sufficient polarity, making it possible to produce a more flexible composition and to easily adjust the flexibility of the composition of this disclosure. Moreover, the resulting composition has improved decorative properties.

[0044] The viscosity of liquid polybutadiene with cis double bonds present in a proportion lower than the lower limit mentioned above increases rapidly with increasing maleic acid content, while the viscosity of liquid polybutadiene with cis double bonds within the above range shows only a slight increase. This low viscosity within the above range ensures high reactivity and improves workability. Furthermore, the resulting composition exhibits improved decorative properties.

[0045] Non-limiting examples of polybutadiene resins provided herein are maleic anhydride adducts of cis-1,4-polybutadiene (e.g., low molecular weight cis-1,4-polybutadiene), which may have succinic anhydride pendant groups randomly distributed in the polymer chain. Examples of such polybutadiene resins include POLYVEST OC 800S, POLYVEST OC 1200S, and POLYVEST MA-75, each manufactured by Evonik Industries.

[0046] Polyamide resin Polyamides are typically condensation copolymers formed by the reaction of dicarboxylic acids with diamines or by ring-opening of lactams. Various polyamides can be produced by adjusting the number of carbon atoms. The nomenclature used herein indicates first the number of carbon atoms in the diamine, and then the number of carbon atoms in the dicarboxylic acid. Thus, polyamide-6,6 has 6 carbon atoms from the diamine and 6 carbon atoms from the dicarboxylic acid, and polyamide-6,12 has 6 carbon atoms from the diamine and 12 carbon atoms from the dicarboxylic acid. Polyamide-6 is a homopolymer formed by ring-opening polymerization (i.e., ring-opening polymerization of caprolactam). Polyamides may also be nylon-9, nylon-12, nylon-11, nylon-4,6, nylon-6,10, or any of the polyamides listed herein.

[0047] Useful polyamide resins in the compositions of this disclosure include nylon-6, nylon 6-6, copolymers of nylon-6 and nylon 6-6, nylon-9, nylon-10, nylon-11, nylon-12, nylon 6-10, aromatic polyamides, elastomer polyamides, and mixtures thereof.

[0048] The conditions and COOH / NH2 ratio for preparing polyamide resins can be selected to obtain a final product with an acid value or amine value within the intended range. A polyamide resin is classified as acid-functional if its amine value is lower than its acid value (AV). A resin is classified as amine-functional if its acid value is lower than its amine value. Evonik's ANCATHERM 592 is an example of an acid-functional thermoplastic polyamide.

[0049] Non-functional polymer compounds Examples of non-functional polymer compounds useful in the compositions of this disclosure include copolymers of acrylates, polybutadienes, polyamides, ketone-aldehyde condensation resins, polyimides, styrene-butadiene resins, and other olefins, as well as combinations thereof.

[0050] Examples of non-functional resin compounds that may be used in accordance with this disclosure include compounds from Evonik's POLYVEST liquid polybutadiene product line, thermoplastic acrylic resins and MBS polymers from Dow's Paraloid product line, non-functional polyamides from Evonik's Vestamid product line, styrene-based block copolymers (SBCs) from Kraton produced from butadiene, styrene, and isoprene raw materials, and finally, ketone-aldehyde condensation resins, such as Evonik's TEGO Variplus AP, which may also be used in the compositions of this disclosure.

[0051] Curable epoxy resin Solutions and combinations of amines containing the other resins described above are used as curing agents for epoxy resins. Epoxy resins commercially available under trade names DER 383 or DER 333 (available from Dow) and EPON 826 or EPON 828 (available from Hexion Specialty Chemicals) are suitable for use with the potential curing accelerator compositions of this disclosure.

[0052] Other epoxy resins include, but are not limited to, bifunctional epoxy resins, such as bisphenol-A and bisphenol-F resins. When used herein, polyfunctional epoxy resins refer to compounds containing two or more 1,2-epoxy groups per molecule. This type of epoxide compound is well known to those skilled in the art and is incorporated herein by reference in Y. Tanaka, “Synthesis and Characteristics of Epoxides,” in CA May, ed. Epoxy Resins Chemistry and Technology (Marcel Dekker, 1988).

[0053] One class of epoxy resins suitable for use in this disclosure comprises glycidyl ethers of polyhydric phenols, including glycidyl ethers of dihydric phenols. Exemplary examples include, but are not limited to, glycidyl ethers such as resorcinol, hydroquinone, bis-(4-hydroxy-3,5-difluorophenyl)-methane, 1,1-bis-(4-hydroxyphenyl)-ethane, 2,2-bis-(4-hydroxy-3-methylphenyl)-propane, 2,2-bis-(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis-(4-hydroxyphenyl)-propane (commercially available as bisphenol A), bis-(4-hydroxyphenyl)-methane (commercially available as bisphenol-F, which may contain varying amounts of 2-hydroxyphenyl isomers), or any combination thereof. Furthermore, highly dihydric phenols having the following structures are also useful in this disclosure: [ka] In the formula, m is an integer, and R is a divalent hydrocarbon radical of a divalent phenol, such as the divalent phenol described above.

[0054] Materials according to this formula can be prepared by polymerizing a mixture of divalent phenol and epichlorohydrin, or by proceeding with a mixture of diglycidyl ether of divalent phenol and divalent phenol. In any given molecule, the value of m is an integer, but the material is always a mixture that can be characterized by an average value of m that is not necessarily an integer. Polymer materials having an average value of m from 0 to about 7 can be used in one embodiment of this disclosure. In other embodiments, the epoxy component may be a polyglycidylamine from one or more of 2,2'-methylenedianiline, m-xylenedianiline, hydantoin, and isocyanates.

[0055] The epoxy component may be an alicyclic epoxide. Examples of suitable alicyclic epoxides include diepoxides of alicyclic esters of dicarboxylic acids, e.g., bis(3,4-epoxycyclohexylmethyl) oxalate, bis(3,4-epoxycyclohexylmethyl) adipate, bis(3,4-epoxy-6-methylcyclohexylmethyl) adipate, vinylcyclohexene diepoxide; limonene diepoxide; bis(3,4-epoxycyclohexylmethyl) pimelate; dicyclopentadiene diepoxide; and other suitable alicyclic epoxides. Other suitable diepoxides of alicyclic esters of dicarboxylic acids are described, for example, in International Publication 2009 / 089145 A1, which is incorporated herein by reference.

[0056] Other alicyclic epoxides include 3,3-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, e.g., 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate; 3,3-epoxy-1-methylcyclohexylmethyl-3,4-epoxy-1-methylcyclohexanecarboxylate; 6-methyl-3,4-epoxycyclohexylmethylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate; and 3,4-epoxy-2-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate. Other suitable 3,4-epoxycyclohexylmenthyl-3,4-epoxycyclohexanecarboxylates are described, for example, in U.S. Patent No. 2,890,194, which is incorporated herein by reference. In other embodiments, the epoxy component may include polyol polyglycidyl ethers from polyethylene glycol, polypropylene glycol, or polytetrahydrofuran or a combination thereof.

[0057] In addition to the components described above, potential curing accelerators may be used in the curable epoxy composition, which may further contain additives, such as wetting agents (e.g., silicones, fatty acid alcohols, ionic and nonionic surfactants), fillers (e.g., calcium carbonate, calcium oxide, talc, coal tar, carbon black, textile fibers, glass particles or fibers, aramid pulp, boron fibers, carbon fibers, silicate minerals, mica, powdered quartz, hydrated aluminum oxide, bentonite, wollastonite, kaolin, fumed silica, silica aerogel, or metal powders such as aluminum powder or iron powder), defoamers (e.g., nonionic surfactants, silicones, mineral oils), and rheology modifiers (e.g., fumed silica, bentonite clay, organic clay, precipitated calcium carbonate).

[0058] In various embodiments, the potential curing accelerator compositions of the present disclosure are first prepared by introducing the components into a two-piece glass reactor equipped with a mechanical stirrer, thermocouples, and reflux condenser under an N2 atmosphere. The reaction components are heated to 130-180°C for a set period of time, for example, 1 hour, and the hot solution is poured onto a Teflon block or aluminum sheet and cooled to room temperature. The resin can be added to the reactor undiluted as described above, or dissolved in a certain polar solvent, such as methanol. In the latter case, the resulting reaction mixture is refluxed for 2 hours to form a clear solution. The mixture is then cooled to room temperature and the solvent is removed by evaporation. The resulting product is further dried under vacuum.

[0059] Upon removal from the reactor, the final curing agent formulation may be liquid or solid. If solid, the material is ground into a fine powder using methods such as spray drying, ceramic bead grinding, jet grinding, or coffee grinding. The particle size of the powder may range from 1 to 100 microns. The powder is then kneaded into the epoxy resin and mixed using a speed mixer, Cowles blade mixer, or planetary mixer. If the final curing agent is liquid, it is kneaded directly into the resin using a similar mixing method. Optional additives, such as wetting agents, fillers, defoamers, and rheology modifiers, may be added as needed.

[0060] The curing agent of this composition can be used to cure epoxy resins, either as a standalone component or as an accelerator with DICY. In addition, it can be used as an accelerator for anhydride-cured epoxies, polymercaptan-cured epoxies, and other amine-cured epoxies.

[0061] Epoxy formulations containing the curing agent of this composition as a standalone curing agent or accelerator can be used in a variety of applications where epoxy systems are preferred. Applications of particular interest include, but are not limited to, structural adhesives and composites, electrical potting and encapsulation, compositions for reinforcement and / or damping, in-situ curing pipes, impact-resistant adhesives, filament winding, transfer molding powders, prepregs containing solid or liquid epoxy, sheet molding compounds, coatings for concrete, wood, metal, etc., resin transfer molding, and battery pack adhesives. [Examples]

[0062] Example 1: Preparation of amine solutions in acrylic resin: Add the amine to a two-piece glass reaction flask under an N2 atmosphere and heat to 130-180°C. Slowly add the non-phenolic resin while stirring. Once the addition is complete, hold the mixture at 130-180°C for another hour. Pour the molten solution onto a Teflon block or aluminum sheet and allow to cool to room temperature. Grind the solid product in a coffee grinder, then pulverize it to the appropriate size using a speed mixer with ceramic beads. Use this method to prepare the following amine solutions. (a) Formulation 1: Solution of 2,4,6-tris(dimethylaminomethyl)phenol (Ancamine K54) in acrylic resin Joncryl 67. Weight ratios of amine to acrylic resin of 100 / 140, 100 / 110, and 100 / 80 were prepared as follows. The first blend was prepared as described above using 110 g of 2,4,6-tris(dimethylaminomethyl)phenol and 154 g of acrylic resin. The second blend was prepared using 125 g of 2,4,6-tris(dimethylaminomethyl)phenol and 137.5 g of acrylic resin. The third blend was also prepared using 125 g of 2,4,6-tris(dimethylaminomethyl)phenol and 100 g of acrylic resin. The preparation of formulation 1 is summarized below. [Table 1] (b) Formulation 2: Solution of 2,4,6-tris(dimethylaminomethyl)phenol (Ancamine K54) in acrylic resin Joncryl 67 and Epomatt G-152. Weight ratios of amine to acrylic resin of 100 / 140, 100 / 110, and 100 / 80 were prepared as follows. The weight ratio of Joncryl 67 to Epomatt G-152 resin used in this example is 50 / 50. Prepared as described above using 110 g of 2,4,6-tris(dimethylaminomethyl)phenol and 77 g of each acrylic resin (Joncryl 67 and Epomatt G-152). The second blend was prepared using 125 g of 2,4,6-tris(dimethylaminomethyl)phenol and 68.75 g of each acrylic resin. Further preparations were made using 125 g of 2,4,6-tris(dimethylaminomethyl)phenol and 50 g of each acrylic resin. The preparation of formulation 2 is summarized below. [Table 2]

[0063] Example 2: Differential scanning calorimetry (DSC) of amine solutions in functional and non-functional polymer and monomer resins: DSC as a DICY accelerator A sample of the amine solution from Example 1 was mixed with dicyandiamide (DICY), fumed silica, and bisphenol A diglycidyl ether (mass ratio 2:6:2:100). The mixture was analyzed by DSC (TA instruments QA20, software V24.10 build 122) to determine the curing onset temperature, reaction heat (ΔH), and glass transition temperature (Tg). DSC was performed according to standard procedures using the software included with the DSC. The sample was heated from -25°C to 300°C at a heating rate of 10°C per minute. Undiluted 2,4,6-tris(dimethylaminomethyl)phenol was used as a reference accelerator. The results are shown in the table below. [Table 3]

[0064] Example 3: Latency of amine solutions in functional and non-functional polymer and monomer resins: A sample of the amine solution from Example 1 was mixed with dicyandiamide (DICY), fumed silica, and bisphenol A diglycidyl ether (mass ratio 2:6:2:100). The latency of the resulting epoxy compound was monitored using a 0.5 mL sample at 25°C with a Brookfield Cone and Plate viscometer (model HADV II+CP) equipped with a #52 spindle, as the viscosity change during degradation at 40°C. Storage stability was determined by visual observation, and the gelation time was determined. The results are shown in the table below. [Table 4]

[0065] Example 4: Adhesive properties The adhesive properties of a simple epoxy adhesive formulation containing the curing agent of Example 1 were measured by lap shear strength and T-peel technique. Lap shear strength measurements were performed at least 5 times in an Instron Model 1125 apparatus according to ASTM method D1876. The test material was applied to a 1-inch x 0.4-inch x 0.32-inch cold-rolled steel panel (ACT cold-rolled steel 01X04X032 B952 P60 DIW: unpolished). The material was applied to the 1 / 2-inch end of a coupon using 10 mil glass beads (1% based on the weight of the formulation). Another coupon was placed so as to overlap the 1 / 2-inch strip of the other coupon. The panel containing the test material was cured at a temperature of 130°C to 160°C for 15 to 30 minutes, and then cooled to room temperature before measurement.

[0066] T-type delamination was measured at least five times in an Instron Model 1125 apparatus according to the ASTM method D1876 for lap shear strength. The test material was applied to a 1-inch x 4-inch x 0.32-inch cold-rolled steel panel (ACT cold-rolled steel 01X04X032 B952 P60 DIW: unpolished) that had been pre-bent at a right angle from the edge, leaving a 3 1 / 8-inch x 1-inch surface. The material was applied using 10 mil glass beads (1% based on the weight of the mixture). The test material was cured at a temperature of 130°C to 160°C for 15 to 30 minutes, and then cooled to room temperature before measurement. The results of the lap shear strength and T-type delamination measurements are shown in the table below. [Table 5]

[0067] While the present invention has been described with reference to specific aspects or embodiments, those skilled in the art will understand that various modifications can be made and elements can be replaced with equivalents without departing from the scope of the invention. Furthermore, many modifications can be made to adapt the teachings of the invention to specific situations or materials without departing from the essential scope of the invention. Thus, the invention is not limited to the specific aspects or embodiments disclosed as the best mode intended for carrying out the invention, and the invention is intended to include all embodiments that fall within the scope of the appended claims, including the use of aspects or embodiments of the invention individually or in combination with each other.

Claims

1. Amine and, An encapsulation system comprising additional excipients selected from functional and / or non-functional components, A potential curing accelerator composition containing the above.

2. The aforementioned amine, (a) Alkyl or aryl-substituted tertiary amines (e.g., monotertiary amines) (b) Tertiary amines having more than two peralkylated nitrogen atoms (c) Tertiary amines having more than two permethylated nitrogen atoms (d) N,N-dimethyl polyamine having at least one primary amine and one secondary amine (e) Crosslinked or condensed bicyclic diamines, and / or (f) The composition according to claim 1, selected from at least one of alkyl, aryl, alkylaryl, alkyl ether, alkylamino, or imidazole which may be substituted with at least one halogen (e.g., alkylamino-substituted imidazole, 2-alkyl or aryl-substituted imidazole, e.g., 2-methylimidazole).

3. The composition according to claim 1 or 2, wherein the amine comprises one or more of the following: 3,3',3"-imino-tris-(N,N-dimethylpropylamine), 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), triethylenediamine (TEDA), 1-(3-aminopropyl)imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, [(dimethylamino)methyl]phenol, bis-[(dimethylamino)methyl]phenol and tris-(dimethylaminomethyl)phenol (e.g., 2,4,6-tris-(dimethylaminomethyl)phenol), [(dimethylamino)methyl]phenol, and mixtures of bis- and tris-(dimethylamino)methyl substituted phenols.

4. The composition according to any one of claims 1 to 3, wherein the amine is selected from [(dimethylamino)methyl]phenol, bis-[(dimethylamino)methyl]phenol, and tris-(dimethylaminomethyl)phenol (e.g., 2,4,6-tris-(dimethylaminomethyl)phenol), and combinations thereof.

5. The composition according to any one of claims 1 to 4, wherein the additional excipient is a functional polymer compound, for example, a polymer compound containing one or more carboxyl groups and / or hydroxyl groups.

6. The composition according to any one of claims 1 to 5, wherein the additional excipient is selected from one or more of polyamide resins, polybutadiene resins, polyether resins, and acrylic resins.

7. The composition according to any one of claims 1 to 6, wherein the additional excipient is an acrylic resin.

8. The acrylic resin has the following structure: 【Chemistry 1】 In the formula, R １ However, H or C １－３ Selected independently of alkyl, R ２ However, H or C １－８ The composition according to claim 6 or 7, wherein the alkyl group is alkyl, and the alkyl group may be substituted with -OH.

9. The composition according to any one of claims 6 to 8, wherein the acrylic resin is formed by free radical polymerization of an acrylic monomer and a vinyl monomer with an unsaturated monomer containing a hydroxyl group or a carboxyl group.

10. The composition according to any one of claims 6 to 9, wherein the acrylic resin is formed by free radical polymerization of an acrylic monomer containing a hydroxyl group, a carboxyl group, and / or an ester group.

11. The composition according to any one of claims 1 to 10, wherein the additional excipient is a polybutadiene resin.

12. The composition according to any one of claims 1 to 11, wherein the additional excipient is a polyamide resin.

13. The composition according to any one of claims 1 to 12, wherein the weight ratio of the amine to the mounting agent system is about 1:0.3 to about 1:10, or about 1:0.3 to about 1:2, or about 1:0.5 to about 1:1.5, or about 1:0.8, or about 1:1.1, or about 1:1.

4.

14. The composition according to any one of claims 1 to 13, wherein a curable epoxy system is formed in combination with an epoxy resin, and the curable epoxy system does not gel after 4 weeks under accelerated degradation conditions (for example, storage at 40°C for 4 weeks).

15. The composition according to any one of claims 1 to 14, wherein the epoxy resin is combined with the composition to form a curable epoxy system, and the curable epoxy system provides a lap shear strength of at least 500 psi, for example, about 500 psi to 1700 psi.

16. Amine and, An encapsulation system comprising additional excipients selected from functional and / or non-functional components, A method for curing a substance by using a potential curing accelerator composition, comprising: A method comprising the steps of combining the substance with the potential curing accelerator composition and heating the resulting mixture.

17. The method according to claim 16, wherein the substance is an epoxy resin.

18. The method according to claim 16 or 17, wherein the composition is a latent curing agent for epoxy resins (e.g., a sole latent curing agent), or the composition is used as an accelerator for a curing agent for epoxy resins, such as DICY or an acid anhydride.

19. The method according to any one of claims 16 to 18, wherein the composition is used as a potential curing accelerator for structural adhesives and composites, electropotting and encapsulation, reinforcement and / or damping, in-situ curing pipes, impact adhesives, filament winding, transfer molding powder, prepregs containing solid or liquid epoxy, sheet molding compounds, coatings for concrete, wood, metal and the like, resin transfer molding, and / or EV battery pack adhesives.

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