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Phenalkamine epoxy curing agents and epoxy resin compositions containing the same

a technology of epoxy resin and curing agent, which is applied in the direction of adhesive types, coatings, organic chemistry, etc., can solve the problem of not being able to easily control the molecular weight distribution of these products, and achieve the effects of high gloss and clarity, low viscosity, and faster amine-epoxy reaction ra

Active Publication Date: 2021-11-18
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]The present disclosure discloses a new structural class of phenalkamines, curing agent compositions comprising such phenalkamines, methods of making such phenalkamines, and methods of making such compositions. These phenalkamines and curing-agent compositions may be used to cure, harden, and / or crosslink an epoxy resin. This invention solves problems associated with phenalkamines and curing agents comprising phenalkamines by providing curing agents which are of low viscosity (<3000 cP at 25° C.) which can be used neat or dissolved in a minimum amount (<20 wt %) of an organic solvent or diluent to effect cure of epoxy resins. In addition, this inventive phenalkamine curing agent can provide dry cure of epoxy coatings at ambient temperature (25° C.) in <8 h or at 5° C. in <16 h.
[0012]Articles of manufacture produced from amine-epoxy compositions disclosed herein include, but are not limited to, adhesives, coatings, primers, sealants, curing compounds, construction products, flooring products, and composite products. Further, such coatings, primers, sealants, or curing compounds may be applied to metal or cementitious substrates. The mix of curing agent and epoxy resin often requires no “ripening time” for obtaining contact products with high gloss and clarity. Ripening time or incubation time or induction time is defined as the time between mixing epoxy resin with amine and applying the product onto the target substrate. It could also be defined as the time required for the mix to become clear. Furthermore, the novel phenalkamine compositions also provide faster amine-epoxy reaction rate, and relatively low viscosity. These unique properties provide the advantages of lower tendency to carbamate, shorter time for coatings to dry, and reduced or eliminated amount of solvent needed.

Problems solved by technology

In general, it is not possible to easily control the molecular weight distribution of these products and hence they are usually viscous liquids.

Method used

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  • Phenalkamine epoxy curing agents and epoxy resin compositions containing the same
  • Phenalkamine epoxy curing agents and epoxy resin compositions containing the same
  • Phenalkamine epoxy curing agents and epoxy resin compositions containing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

of the Phenalkamine of Triaminononane with Molar Ratio of Cardanol:Triaminononane:Formaldehyde (1:1:1)

[0053]A 3-neck 1 L round bottom flask equipped with N2 inlet, addition funnel and temperature probe was charged with cardanol (298 g, 1.0 mole) and triaminononane (TAN) (173.3 g, 1.0 mole). The mixture was heated to 80° C. A 37% solution of formaldehyde (81 g, 37 wt. %, 30 g, 1.0 mole) was added to maintain a reaction temperature of 80-90° C. After the addition the mixture was kept at 90-95° C. for 1 h. Water was distilled at 120° C. and the product was obtained as a light brown liquid.

example 2

of the Phenalkamine of Triaminononane with Molar Ratio of Cardanol:Triaminononane:Formaldehyde (1:1.3:1.3)

[0054]A 3-neck 1 L round bottom flask equipped with N2 inlet, addition funnel and temperature probe was charged with cardanol (298 g, 1.0 mole) and TAN (225.29 g, 1.30 mole). The mixture was heated to 80° C. A 37% solution of formaldehyde (105.40 g, 37 wt. %, 39 g, 1.3 mole) was added to maintain a reaction temperature of 80-90° C. After the addition the mixture was kept at 90-95° C. for 1 h. Water was distilled at 120° C. and the product was obtained as a light brown liquid.

examples 1a-3b

[0055]Curing agent mixtures were prepared by mixing the components given in the above examples. with the epoxy component of standard bisphenol-A based epoxy resin of (Epon 828, DER 331 type), EEW 190, unless specified otherwise. The formulations used are defined in Table 1. They were then mixed employing a stoichiometric level of 1:1 (amine:epoxy equivalents). The curing agents were tested neat and at 80% solids in a combination of xylene:n-butanol (3:1 by weight). Comparative Example (3) is a commercially available Phenalkamine Curing Agent Derived from Ethylenediamine [EDA] and was Used as a Reference.

TABLE 1Clear Coat Formulation Screening - TAN PhenalkaminesEx 1AEx2AEx3AEx 1BEx2BEx 3BPropertySolvent freeSolvent basedLiquid BADGE Epoxyg100100100100100100resin (EEW190)Curing agentg49——49——[Ex 1] (AHEW92)Curing agentg—51——51—[Ex 2] (AHEW97)Commercial [EDA]g——65.6——65.6phenalkamine[Ex 3] (AHEW125)Xylene / n-butanolg—0012.312.716.4(3:1 by wt)Total solids%10010010092.392.290.9Total mixg...

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Abstract

The present invention relates to a new structural class of phenalkamines, curing agent compositions comprising the phenalkamines, their use, as well as and methods of producing such phenalkamines and compositions. The phenalkamines of the present invention can be prepared by reacting cardanol with an aldehyde compound and triaminononane. These curing-agent compositions may be used to cure, harden, and / or crosslink an epoxy resin. The curing-agent compositions of this invention are of low viscosity and can be used neat or dissolved in a minimum amount of an organic solvent or diluent to effect cure of epoxy resins.

Description

BACKGROUND OF THE INVENTION[0001]The Mannich reaction is based on the reaction of an aldehyde, generally formaldehyde, a phenolic compound and an amine. Various forms of phenolic compounds, amines and aldehydes have been utilized in this reaction. The Mannich base products are particularly suitable for curing epoxy resins.[0002]Phenalkamine curing agents are a class of Mannich bases obtained by reacting cardanol, an extract of cashew nutshell liquid, an aldehyde compound, such as formaldehyde, and an amine. Generally, they are produced from the reaction of one molar equivalent of cardanol with one to two molar equivalent of an aliphatic polyethylene polyamine and one to two molar equivalent of formaldehyde at 80-100° C. Sometimes aromatic polyamines have also been used for this reaction. The commercially available phenalkamines NC 541 and NC 540 available from Cardolite Inc. use ethylenediamine and diethylenetriamine as the amine sources. The Sunmide 1151 phenalkamine available from...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G59/50C08G59/32C09D163/00C09J163/00C07C215/50C07C213/00
CPCC08G59/5033C08G59/3218C07C213/00C09J163/00C07C215/50C09D163/00C08G59/4014C08G59/504C07C215/46C07C213/02C08G59/621C08G59/56C08G59/245C08G59/223
Inventor LAL, GAURI SANKARCOOK, MICHAELVEDAGE, GAMINI ANANDAROUMPELAKIS, EMMANOUIL
Owner EVONIK OPERATIONS GMBH
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