Cardanol-based curing agent for epoxy resin compositions

Abstract

The present invention relates to new compounds based on cardanol useful as curing agents, compositions comprising the new compounds, the manufacture of such compounds and such compositions, and the use of these compositions, in particular in potting processes of electrical and electronic components and devices.

Description

[0001] This invention relates to novel cashew nut phenol-based compounds that can be used as curing agents, compositions containing the novel compounds, the manufacture of such compounds and compositions, and the use of such compositions, particularly in the potting process of electrical and electronic components and devices. Background of the Invention

[0003] Polyamides possess several excellent properties, such as good processability, mechanical properties, heat resistance, rigidity, abrasion resistance, and chemical resistance. Due to these unique properties, polyamides are widely used as component materials in various automotive, electrical, and electronics industries (see, for example, US2012 / 0177937 A1). Polyamides are prepared from various carboxylic acids. Terephthalic acid and trimellitic acid are contained in benzene rings with carboxylate groups at the 1 and 4 positions, and at the 1, 2, and 4 positions, respectively (see, for example, WO2012 / 082727A1). Generally, polyamides are prepared from raw materials derived from petroleum-reactive diacids and their diamines (see, for example, US2012 / 0165466A1, US8,822,629B2, US6846868B2, and Journal of Applied Polymer Science, Vol. 68, Issue 2, pp. 305-314,

[1998] , Wiley Periodicals, Inc.). Alternatively, polyamides can be prepared from biomass by microbial synthesis under controlled conditions in a fermenter, as described in WO2012 / 082727A1.

[0004] Synthetic methods for bio-based polyamides are available in several publications, such as unsaturated polyamides prepared from bio-based Z-octadecano-9-enediic acid (Macromolecular Chemistry and Physics, Vol. 209, Issue 1, pp. 64-74,

[2008] , John Wiley & Sons, Ltd.). Bio-based polyamides have also been prepared from castor oil (European Polymer Journal, Vol. 59, pp. 69-77,

[2014] , Elsevier Ltd.). Polyamides prepared from bio-based cashew nut shells are reported in the Progress in Organic Coatings, Vol. 104, pp. 250–262,

[2017] , Elsevier BV.

[0005] In light of this, more attention is being paid to thermosetting materials derived from renewable resources, particularly epoxy thermosetting resins. Until now, only bio-based aromatic acids or anhydrides have been used as epoxy curing agents, and only a few bio-based diamines have been industrially available, but most of them are weakly soluble in most solvents or produce harmful byproducts. Phenalkamine, prepared by the Mannich reaction, is known as the best bio-based curing agent for epoxy resins. Phenalkamine is prepared from cashew nut shell liquid (CNSL), an inedible byproduct of the CNSL industry. It is indeed a promising source of abundantly available aromatic renewables (European Journal of Lipid Science and Technology, Vol. 117, pp. 178-189,

[2015] , WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim). According to US6229054B1, CNSL derivatives have numerous industrial uses in, for example, epoxy curing agents, phenolic resins, surfactants, and demulsifiers.

[0006] Phenolic amines are prepared by the Mannich reaction, which involves reacting cashew nut kernel extract (containing extracts derived from cashew nut shell liquid), aldehydes (such as formaldehyde), and polyamines (US6262148 B1 and Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 52, pp. 472-480,

[2014] , Wiley Periodicals, Inc.). Phenolic amines still have some drawbacks, such as the very dark color and instability of the cured epoxy materials. Therefore, the use of phenolic amines in epoxy resins is very limited (RSC Advances, Vol. 6, pp. 105744-105754,

[2016] , Royal Society of Chemistry).

[0007] Balguade et al. (disclosed in Progress in Organic Coatings, 2016) disclosed the reaction of the hydrocarbon chain of cashew nut shell with maleic anhydride and the use of the resulting product as a curing agent.

[0008] Given the uncertainty of the oil market and the limited availability of petroleum products for future uses, it is ideal to have amide-containing polymers or resins that can be derived from raw materials that can be prepared from renewable resources.

[0009] The novel compounds of this invention solve the aforementioned problems. In fact, they allow for the preparation of amide-containing polymers that can be prepared from naturally available raw materials that are not petroleum derivatives.

[0010] Furthermore, this new compound can be included in the in-situ synthesis of amide-modified phenolic amines and amide-modified polyether-modified phenolic amines.

[0011] Compositions containing the compounds of this invention cure rapidly and produce stable materials.

[0012] Furthermore, compared to polyamide curing agents, the cost of this curing agent system can be reduced by developing low-cost phenolic amines.

[0013] Materials derived from curing compositions exhibit excellent thermal shock resistance, good chemical resistance, and very low water absorption. They also demonstrate superior mechanical properties compared to existing polyamide systems. Invention Details

[0015] The present invention relates to compounds comprising substituted cashew nut shells, wherein the hydrocarbon chain of the cashew nut shell is substituted with at least one group having at least one amino functional group having an active hydrogen atom linked to an amine group and at least one amide group; and the aromatic ring of the cashew nut shell is substituted with at least one group having at least one amino functional group having an active hydrogen atom linked to an amine group.

[0016] In another preferred embodiment of the compound of the present invention, the group having at least one active hydrogen atom attached to an amine group comprises a secondary amine.

[0017] In another preferred embodiment of the compound of the present invention, each of the groups comprising at least one active hydrogen atom linked to an amine group further comprises a group selected from alkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl groups. More preferably, the compound of the present invention further comprises a group selected from alkyl and heterocycloalkyl groups.

[0018] In a preferred embodiment of the compound of the present invention, the group having at least one active hydrogen linked to an amine group further comprises at least one ether group.

[0019] In a preferred embodiment of the compound of the present invention, the group further comprising at least one ether group comprises a polyether segment.

[0020] The present invention further relates to curable compositions comprising any of the compounds of the present invention and an amine-reactive resin.

[0021] The amine-reactive resin of the curable composition can also react with –OH groups.

[0022] Preferably, the amine-active resin is an epoxy resin. More preferably, the epoxy resin has an average of at least one epoxy group per molecule, and more preferably at least one glycidyl group per molecule.

[0023] In another embodiment, the present invention relates to the use of compositions comprising amine-reactive resins cured with the compounds of the present invention. Epoxy resins are preferred. More preferably, the epoxy resin has an average of at least one epoxy group per molecule, and more preferably at least one glycidyl group per molecule.

[0024] In a preferred embodiment, any compound of the present invention may be used in any curable composition comprising an amine-reactive resin in the embodiment described herein.

[0025] More preferably, epoxy resins are those having 1.8 epoxy groups per molecule.

[0026] Commercially available epoxy resins are suitable for curing with the compounds of the present invention. Preferably, the commercially available epoxy resins suitable for the present invention are based on bisphenol A, bisphenol F, or mixtures thereof.

[0027] In another embodiment, the present invention relates to the use of compositions comprising the compounds of the present invention in potting electrical and electronic components or devices.

[0028] In another embodiment, the present invention relates to the use of the compounds of the invention in the composition in potting electrical and electronic components or devices.

[0029] In another embodiment, the present invention relates to a method for preparing the compounds of the present invention.

[0030] In another embodiment, the present invention relates to a method for preparing any of the compounds of the present invention, comprising the steps of:

[0031] a) React cashew phenol with maleic anhydride in the presence of a catalyst;

[0032] b) React the reaction product of step a) with at least one compound having at least one primary or secondary amine group in the presence of formaldehyde and a catalyst.

[0033] In a preferred embodiment, the primary or secondary amine further comprises an ether group, preferably a polyether segment.

[0034] In a preferred embodiment, the primary or secondary amine further comprising an ether group is a polyetheramine.

[0035] In another preferred embodiment, the primary and / or secondary amine groups further comprise groups selected from alkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl groups.

[0036] In a further preferred embodiment, the catalyst in step a) comprises a metal complex. Preferably, the metal is selected from transition metals, and more preferably, the transition metal complex is a solution of transition metal complexes. More preferably, the transition metal is cobalt or manganese. Most preferably, the catalyst is cobalt naphthenate.

[0037] In another preferred embodiment, the catalyst in step b) is an acid compound, preferably oxalic acid.

[0038] In another embodiment, the present invention relates to a method for preparing articles or materials, comprising the steps of:

[0039] a. Mixing an epoxy resin having an average of at least one epoxy group per molecule, preferably at least one glycidyl group per molecule, with a curing agent according to any one of claims 1-5.

[0040] b. Allow the mixture from step a to solidify.

[0041] In another embodiment, the present invention relates to an article of manufacture obtained by a method comprising the steps of:

[0042] a. Mixing an epoxy resin having an average of at least one epoxy group per molecule, preferably at least one glycidyl group per molecule, with a curing agent according to any one of claims 1-5.

[0043] b. Allow the mixture from step a to solidify.

[0044] In another embodiment, the present invention relates to a material obtained by a method comprising the steps of:

[0045] a. Mixing an epoxy resin having an average of at least one glycidyl group per molecule with a curing agent according to any one of claims 1-5,

[0046] b. Allow the mixture from step a to solidify.

[0047] Preferred compounds having primary and / or secondary amine groups for use in the methods of the present invention are aliphatic amines, alicyclic amines, heterocyclic amines, and aromatic amines.

[0048] Therefore, a compound containing at least one primary or secondary amine may further contain a group selected from alkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl groups.

[0049] Preferably, the compound containing at least one primary or secondary amine is selected from N-aminoethylpiperazine; diethylenetriamine; triethylenetetramine (TETA); tetraethylenepentamine; 2-methylpentamethylenediamine; 1,3-pentanediamine; trimethylhexamethylenediamine; polyamide; polyamide amines and combinations thereof; trimethylolpropane tri[poly(propylene glycol), amine-terminated] ether; 2-(1-piperazinyl)ethylamine; 3-aminomethyl-3,5,5-trimethylcyclohexylamine; 3,6,9,12-tetraazatetradecane-1,14-diamine; tetraethylenepentamine and triethylenetetramine; 3,6-diazoctanethylenediamine; 3,6,9 - Triaza-undemethylenediamine, 1,3-bis(aminomethyl)benzene, 1,3-bis(aminomethyl)cyclohexane, 5-diethyltoluene-2,4-diamine and 3,5-diethyltoluene-2,6-diamine (a mixture of two isomers), 2,2′-(ethylenedioxy)bis(ethylamine), 1,6-diamino-2,2,4(2,4,4)-trimethylhexane, N'-(3-aminopropyl)-N,N-dimethylpropane-1,3-diamine, 4,4′-diaminodicyclohexylmethane, 1,2-cyclohexanediamine and mixtures thereof.

[0050] Preferred compounds having at least a primary or secondary amine group and further comprising at least one ether group are polyetheramines. Preferably, the polyetheramines of the present invention comprise at least one ethylenediamine oxide segment, ethylenetriamine oxide segment, or polyethylene oxide diamine segment. Preferably, the polyetheramines of the present invention comprise at least one propylene oxide segment, ethylene oxide segment, or a mixture thereof.

[0051] Preferred polyetheramines used in this invention are commercially available under the trademark JEFFAMINE from Huntsman Corporation, Houston, Texas, such as JEFFAMINE D-230, JEFFAMINE D-400, JEFFAMINE D-2000, JEFFAMINE T-403, JEFFAMINE ED-600, JEFFAMINE ED-900, JEFFAMINE ED-2001, JEFFAMINE D-148, JEFFAMINE XTJ-509, JEFFAMINE T-3000, JEFFAMINE T-5000, and combinations thereof. The preferred polyetheramine of this invention is JEFFAMINE. ® D-230.

[0052] The curable compositions of this invention may further comprise inorganic and / or organic fillers. Suitable inorganic fillers include barium sulfate, silica, alumina, calcium oxide, magnesium oxide, sodium oxide, potassium oxide, iron oxide, titanium oxide, other oxides, or mixtures thereof. Other suitable fillers include silica gel, calcium silicates, calcium nitrate, calcium phosphate, calcium molybdate, calcium carbonate, calcium hydroxide, pyrolytic silica, clays such as bentonite, aluminum trihydrates, magnesium dihydrates, glass microspheres, hollow glass microspheres, polymer microspheres, and hollow polymer microspheres. Organic fillers such as aromatic polyamide fibers and polyolefin fibers such as polyethylene fibers can be used in the curable compositions.

[0053] The curable composition may contain any suitable amount of filler. It may contain 0.01-50% by weight of filler based on the total weight of the curable composition.

[0054] The compounds of the present invention can be used to cure compositions containing amine-reactive resins (preferably epoxy resins), more preferably epoxy resins having an average of at least one glycidyl group per molecule.

[0055] The present invention further relates to a method for preparing the compounds of the present invention. The method comprises the steps of reacting cashew phenol and / or bisphenol with at least one compound having at least one primary or secondary amine group and a compound having at least one primary or secondary amine group and further comprising an ether group in the presence of formaldehyde and a catalyst.

[0056] The present invention further relates to a method for preparing articles or materials, comprising the steps of: mixing an amine-reactive resin, preferably an epoxy resin, with the compound of the present invention, and curing the mixture.

[0057] Another object of the present invention is an article or material prepared by a method comprising the steps of: mixing an amine-reactive resin with a compound of the present invention, and curing the mixture.

[0058] The invention will be explained in more detail by way of the following non-limiting embodiments.

[0059] Example

[0060] The phenolic amine of the present invention is synthesized using a synthetic procedure similar to that given in US6262148 B1 and Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 52, pp. 472-480,

[2014] , Wiley Periodicals, Inc.

[0061] The reaction of cashew phenol with maleic anhydride is similar to that of Balguade et al. (disclosed in Progress in Organic Coatings, 2016).

[0062] Example 1

[0063] Preparation of intermediate 1 obtained using cashew nut shellac and maleic anhydride

[0064] The following components are placed in a three-liter reaction flask:

[0065] 1600.00g cashew phenol

[0066] 392.24g maleic anhydride

[0067] 10g of 5-10% cobalt naphthenate solid solution as a catalyst

[0068] In a 3-liter reaction flask equipped with a water-cooled reflux condenser, 1600 g of cashew nut shell powder and 392.24 g of maleic anhydride were added with stirring. 10 g of cobalt naphthenate was then added to the mixture with stirring. The mixture was slowly heated to 190 °C with continuous stirring for 2.5 hours.

[0069] Example 2.1

[0070] Cashew nut shell-based polyamides were prepared using intermediate 1 and TETA (triethylenetetramine).

[0071] The following components are placed in a one-liter reaction flask:

[0072] 228g Hydrolyzed Maleic Acid Cashew Phenol

[0073] 130g TETA (Triethylenetetramine)

[0074] 43g DETA (Diethylenetriamine)

[0075] 100g SOFA (Soybean Fatty Acids)

[0076] 0.2g oxalic acid (catalyst)

[0077] In a 1-liter reaction flask equipped with a water-cooled reflux condenser, 228 g of hydrolyzed maleic acid-modified cashew phenol, 130 g of TETA, 43 g of DETA, and 100 g of SOFA were added with stirring. 0.2 g of oxalic acid was then added with stirring. The mixture was slowly heated to 210 °C with continuous stirring for 2.5 hours. At this temperature, a clear mixture was obtained, indicating that the reaction had been completed. Residual water present in the mixture was removed by applying a vacuum of 650 mm / Hg to the system for 1 hour.

[0078] Example 2.2

[0079] Cashew phenol-based polyamides were prepared using intermediate 1 and TEPA (tetraethylenepentamine).

[0080] The following components are placed in a 1-liter reaction flask:

[0081] 228g Hydrolyzed Maleic Acid Cashew Phenol

[0082] 145g TEPA (Tetraethylenepentamine)

[0083] 43g DETA (Diethylenetriamine)

[0084] 100g SOFA (Soybean Fatty Acids)

[0085] 0.2g oxalic acid (catalyst)

[0086] The same procedure described above is used to synthesize cashew phenol-based polyamides using hydrolyzed maleic acid cashew phenol and TEPA (tetraethylenepentamine).

[0087] Example 2.3

[0088] Cashew nut phenol-based polyamides were prepared using intermediate 1 and AEP (aminoethylpiperazine).

[0089] The following components are placed in a 1-liter reaction flask:

[0090] 228g Hydrolyzed Maleic Acid Cashew Phenol

[0091] 147g AEP (Aminoethylpiperazine)

[0092] 43g DETA (Diethylenetriamine)

[0093] 100g SOFA (Soybean Fatty Acids)

[0094] 0.2g oxalic acid (catalyst)

[0095] The same procedure described above is used to synthesize cashew phenol-based polyamides using hydrolyzed maleic acidified cashew phenol and AEP (aminoethyl piperazine).

[0096] Example 3.1

[0097] Curing agents based on polyamide-phenolic amines were prepared using intermediate 1, TETA (triethylenetetramine), and oligooxymethylene.

[0098] The following components were added to a 1-liter reaction flask to prepare a polyamide-phenolic amine-based curing agent using TETA:

[0099] 180g Hydrolyzed Maleic Acid Cashew Phenol

[0100] 5g paraformaldehyde

[0101] 102g TETA (Triethylenetetramine)

[0102] 35g DETA (Diethylenetriamine)

[0103] 78g SOFA (Soybean Fatty Acids)

[0104] 0.2g oxalic acid (catalyst)

[0105] All the above additives were loaded into a 1-liter reaction flask equipped with a water-cooled reflux condenser under continuous stirring and slowly heated to 180°C for 2.5 hours with continuous stirring. After the reaction was complete, residual water in the mixture was removed by applying a vacuum of 650 mm / Hg to the system for 1 hour.

[0106] Example 3.2

[0107] Curing agents based on polyamide-phenolic amines were prepared using intermediate 1, TEPA (tetraethylenepentamine), and oligooxymethylene.

[0108] The following components were added to a 1-liter reaction flask to prepare a polyamide-phenolic amine-based curing agent using TEPA:

[0109] 180g Hydrolyzed Maleic Acid Cashew Phenol

[0110] 5g oligooxymethylene

[0111] 119g TEPA (Tetraethylenepentamine)

[0112] 35g DETA (Diethylenetriamine)

[0113] 78g SOFA (Soybean Fatty Acids)

[0114] 0.2g oxalic acid (catalyst)

[0115] The same procedure described above is used to synthesize polyamide-phenolic amines using TETA.

[0116] Example 3.3

[0117] Curing agents based on polyamide-phenolic amines were prepared using intermediate 1, AEP (aminoethyl piperazine), and oligooxymethylene.

[0118] The following components were added to a 1-liter reaction flask to prepare a polyamide-phenolic amine-based curing agent using AEP:

[0119] 180g Hydrolyzed Maleic Acid Cashew Phenol

[0120] 5g oligooxymethylene

[0121] 112g AEP (Aminoethylpiperazine)

[0122] 35g DETA (Diethylenetriamine)

[0123] 78g SOFA (Soybean Fatty Acids)

[0124] 0.2g oxalic acid (catalyst)

[0125] The same procedure described above is used to synthesize polyamide-phenolic amine via AEP.

[0126] Example 4.1

[0127] Polyetheramine-modified polyamides were prepared using cashew phenol-based polyamides prepared by TETA, oligooxymethylene, and polyetheramine. Amine-phenolic amine

[0128] The following components were added to a 1-liter reaction flask to prepare a curing agent based on polyetheramine-modified polyamide-phenolic amine:

[0129] 250g of cashew phenol-based polyamide prepared by TETA

[0130] 11.60g oligooxymethylene

[0131] 125g Jeffamine D 230 polyetheramine

[0132] 0.2g oxalic acid (catalyst)

[0133] All the above additives were loaded into a 3-liter reaction flask equipped with a water-cooled reflux condenser under continuous stirring and slowly heated to 120°C for 2.5 hours. After the reaction was complete, residual water in the mixture was removed by applying a vacuum of 650 mm / Hg to the system for 1 hour.

[0134] Example 4.2

[0135] Polyetheramine-modified polyamides were prepared using cashew phenol-based polyamides prepared from TEPA, oligooxymethylene, and polyetheramine. Amine-phenolic amine

[0136] The following components were added to a 1-liter reaction flask to prepare a curing agent based on polyetheramine-modified polyamide-phenolic amine:

[0137] 250g of cashew phenol-based polyamide prepared from TEPA

[0138] 11.60g oligooxymethylene

[0139] 125g of polyetheramine Jeffamine D 230

[0140] 0.2g oxalic acid (catalyst)

[0141] The same procedure described above is used to synthesize polyetheramine-modified polyamide-phenolic amine prepared from cashew phenol-based polyamides, oligooxyformaldehyde, and polyetheramines prepared from TEPA.

[0142] Example 4.3

[0143] Polyetheramine-modified polyamides were prepared using cashew phenol-based polyamides, oligooxymethylene, and polyetheramines prepared by AEP. Amine-phenolic amine

[0144] The following components were added to a 1-liter reaction flask to prepare a curing agent based on polyetheramine-modified polyamide-phenolic amine:

[0145] 250g of cashew phenol-based polyamide prepared by AEP

[0146] 11.60g oligooxymethylene

[0147] 125g of polyetheramine Jeffamine D 230

[0148] 0.2g oxalic acid (catalyst)

[0149] The same procedure described above is used to synthesize polyetheramine-modified polyamide-phenolic amine prepared from cashew phenol-based polyamides, oligooxyformaldehyde, and polyetheramines prepared by AEP.

[0150] Example 5

[0151] Using cashew phenol-based polyamide / polyamide-phenolic amine / polyether amine modified polyamide-phenolic amine with epoxy resin Preparation of cured materials with grease

[0152] The diglycidyl ether of bisphenol A epoxy resin was mixed with each of the above Examples 2.1, 2.2, 2.3, 3.1, 3.2, 3.3, 4.1, 4.2, and 4.3. The mixture was degassed at 650 mm / Hg for 15 minutes, and then poured into a suitable container at room temperature for 3 hours to form a thermosetting resin.

[0153] All thermosetting resins (i.e. cured materials) obtained in Example 5 were subjected to 10 thermal cycling tests at (-40 / 100°C) for 1 hour each.

[0154] Comparison of physical properties between the newly developed system and curing agents based on standard polyamides

[0155]

[0156] method

[0157] The performance summarized in Table 2 above was measured using the following methods.

[0158] Viscosity was measured at 25°C using a BROOKFIELD viscometer, spindle number 27, at a shear rate of 10 rpm [expressed as cP].

[0159] The amine value, expressed in mg KOH / g, is measured using the following method:

[0160] Reagent: --Glacial acetic acid

[0161] 0.1N standardized perchloric acid in glacial acetic acid

[0162] Crystal violet indicator solution (1.0 g crystal violet dissolved in 100 ml glacial acetic acid)

[0163] Equipment: --Idometric flask - 250ml capacity

[0164] Glass graduated cylinder - 50ml capacity

[0165] Burette - 25ml capacity (minimum 0.1ml)

[0166] Precision balance

[0167] Procedure: 1. Accurately weigh 0.3-0.5g of the sample into a clean and dry iodine flask.

[0168] 2. If necessary, slowly dissolve in about 50 ml of glacial acetic acid and cool to room temperature.

[0169] 3. Titrate with crystal violet indicator solution relative to standardized perchloric acid until the color changes from purple to green.

[0170] 4. Mark the reading. (R ml)

[0171] calculate:

[0172]

[0173] N = Equivalent concentration of perchloric acid

[0174] R = the number of ml of perchloric acid required.

[0175] The gelation time was measured at temperature using a gelation timer (TECHNE instrument) and expressed in minutes (resin to hardener mixing ratio: 65:35).

[0176] The glass transition temperature (Tg / °C) was measured in air (25°C to 600°C) using a Metter Toledo at a rate of 10°C / min.

[0177] Hardness (Shore D) was measured at 25°C using a DUROMETER from HIROMETER.

[0178] Thermal shock cycling was performed using a CM Envirosystem, model Kinetic 25 B2, at -40 / 100°C. The number of thermal cycles performed during each period was [number missing] for a duration of 1 hour at -40 / 100°C.

Claims

1. Compounds containing substituted cashew phenols, in: The hydrocarbon chain of cashew phenol is replaced by at least one group having at least one amino functional group having an active hydrogen linked to an amine group and at least one amide group. Furthermore, the aromatic ring of cashew phenol is substituted by at least one group having at least one amino functional group having an active hydrogen linked to an amine group.

2. The compound of claim 1, wherein the amino functional group having an active hydrogen bonded to an amine group comprises a secondary amine.

3. The compound of claim 2, wherein each of the amino functional groups having an active hydrogen bonded to an amine group further comprises a group selected from alkyl, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl groups.

4. The compound according to any one of claims 1-3, wherein at least one amino functional group further comprises at least one ether group.

5. The compound of claim 4, wherein the group further comprising at least one ether group comprises a polyether segment.

6. A curable composition comprising a compound according to any one of claims 1-5 and an amine-reactive resin.

7. The curable composition according to claim 6, wherein the amine reactive resin is an epoxy resin.

8. Use of the compound according to any one of claims 1-5 for curing compositions comprising amine reactive resins.

9. The use according to claim 8, wherein the amine reactive resin is an epoxy resin.

10. Use of the curable composition according to claim 6 or 7 for potting electrical and electronic components or devices.

11. A method for preparing a compound according to any one of claims 1-5, comprising the steps of: a. React cashew phenol with maleic anhydride in the presence of a catalyst; b. React the reaction product of step a) with at least one compound having at least one primary or secondary amine group in the presence of formaldehyde and a catalyst.

12. The method of claim 11, wherein the primary or secondary amine further comprises an ether group.

13. The method of claim 12, wherein the primary or secondary amine further comprising an ether group is a polyether amine.

14. A method for preparing an article or material, comprising the steps of: a. Mixing an amine-reactive resin with a compound according to any one of claims 1-5; b. Allow the mixture from step a. to solidify.

15. The article obtained by the method according to claim 14.

16. The material obtained by the method according to claim 14.

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