An epoxy resin adhesive including at least one epoxy resin in the resin component, at least one adduct AD including primary amino groups which is free-flowing at room temperature and is formed from (i) at least one polyepoxide and (ii) at least one amine of the formula (I) and optionally further amines, and additionally at least one accelerator B having at least one dimethylamino group in the hardener component, and a total of at least 50% by weight of at least one inorganic filler. The epoxy resin adhesive has low odor and good processibility, rapidly builds up strength at room temperature and under cold conditions and, after curing, has high strengths, especially particularly high compressive strengths, and high bonding forces to substrates such as steel, carbon fiber composites (CRP) and concrete.

An epoxy resin adhesive including at least one epoxy resin in the resin component, at least one adduct AD including primary amino groups which is free-flowing at room temperature and is formed from (i) at least one polyepoxide and (ii) at least one amine of the formula (I) and optionally further amines, and additionally at least one accelerator B having at least one dimethylamino group in the hardener component, and a total of at least 50% by weight of at least one inorganic filler. The epoxy resin adhesive has low odor and good processibility, rapidly builds up strength at room temperature and under cold conditions and, after curing, has high strengths, especially particularly high compressive strengths, and high bonding forces to substrates such as steel, carbon fiber composites (CRP) and concrete.

A curing agent composition comprising anhydride and approximately equimolar amount of tertiary amine or imidazole and carboxylic acid, the amine being 1-piperidinylethanol (N-hydroxyethyl-piperidine, NHEP) represented by the structure below or an imidazole represented by the structure below:

##STR00001##

where R.sub.1=H, a C1-C20 straight chain or branched alkyl, or a monocyclic aryl; R.sub.2=a C1-C20 straight chain or branched alkyl, or a monocyclic aryl. The carboxylic acid is represented by RCOOH; R=a C1-C20 straight chain or branched alkyl, or a monocyclic aryl. The composition comprises a lower ratio of epoxy resin to anhydride (1:0.4-0.6) than typically used (1:0.8-1.1). In addition, it uses a higher loading of the hindered latent tertiary amine or the imidazole in combination with the carboxylic acid (wt % ratio of combined amine and carboxylic acid to anhydride 10%). With this composition a full cure can be achieved in less than 2 hr at a significantly lower temperature (100 C.).

A curing agent composition comprising anhydride and approximately equimolar amount of tertiary amine or imidazole and carboxylic acid, the amine being 1-piperidinylethanol (N-hydroxyethyl-piperidine, NHEP) represented by the structure below or an imidazole represented by the structure below:

##STR00001##

where R.sub.1=H, a C1-C20 straight chain or branched alkyl, or a monocyclic aryl; R.sub.2=a C1-C20 straight chain or branched alkyl, or a monocyclic aryl. The carboxylic acid is represented by RCOOH; R=a C1-C20 straight chain or branched alkyl, or a monocyclic aryl. The composition comprises a lower ratio of epoxy resin to anhydride (1:0.4-0.6) than typically used (1:0.8-1.1). In addition, it uses a higher loading of the hindered latent tertiary amine or the imidazole in combination with the carboxylic acid (wt % ratio of combined amine and carboxylic acid to anhydride 10%). With this composition a full cure can be achieved in less than 2 hr at a significantly lower temperature (100 C.).

The invention relates to the use of an epoxy resin composition, containing at least one reaction product from the reaction of at least one amine of formula (I) with at least one carbonyl compound of formula (II) and hydrogen, as a cold curing primer or adhesive. Primers or adhesives of this type cure rapidly and trouble-free at ambient temperature, even at cold temperatures such as 10 or 5 C., suffer remarkably little yellowing and are free from toxic phenol compounds such as phenol, tert-butylphenol or nonylphenol. The primer has a particularly low viscosity and is particularly suitable for priming porous mineral substrates.

The invention relates to the use of an epoxy resin composition, containing at least one reaction product from the reaction of at least one amine of formula (I) with at least one carbonyl compound of formula (II) and hydrogen, as a cold curing primer or adhesive. Primers or adhesives of this type cure rapidly and trouble-free at ambient temperature, even at cold temperatures such as 10 or 5 C., suffer remarkably little yellowing and are free from toxic phenol compounds such as phenol, tert-butylphenol or nonylphenol. The primer has a particularly low viscosity and is particularly suitable for priming porous mineral substrates.

A task is to provide a method for producing a polycyclic aromatic aminophenol compound through a reduced number of steps at a low cost with high safety. The method for producing a polycyclic aromatic aminophenol compound includes the step of reacting a compound represented by the general formula (1) below and an aromatic amino compound with each other: ##STR00001##
Wherein n represents an integer of 1 to 8, Ar represents a benzene ring optionally having a substituent, or a naphthalene ring optionally having a substituent, each of R.sup.1 and R.sup.2 independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, or an aromatic group optionally having a substituent, and R.sup.3 represents a hydroxyl group, a methoxy group, or a halogen atom.

A task is to provide a method for producing a polycyclic aromatic aminophenol compound through a reduced number of steps at a low cost with high safety. The method for producing a polycyclic aromatic aminophenol compound includes the step of reacting a compound represented by the general formula (1) below and an aromatic amino compound with each other: ##STR00001##
Wherein n represents an integer of 1 to 8, Ar represents a benzene ring optionally having a substituent, or a naphthalene ring optionally having a substituent, each of R.sup.1 and R.sup.2 independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, or an aromatic group optionally having a substituent, and R.sup.3 represents a hydroxyl group, a methoxy group, or a halogen atom.

Provided is a curable resin composition for obtaining a cured product that can satisfy both high heat resistance and high adhesiveness to metal, a cured product thereof, and methods of producing the curable resin composition and the cured product, and a semiconductor device using the cured product as a sealant. A curable resin composition containing (A) a multifunctional benzoxazine compound having two or more benzoxazine rings, (B) a multifunctional epoxy compound having at least one norbornane structure and at least two epoxy groups, (C) a curing agent, (D) a triazole-based compound, and optionally (E) a curing accelerator and (F) an inorganic filler, a cured product thereof, and methods of producing the curable resin composition and the cured product. A semiconductor device in which a semiconductor element is disposed in a cured product obtained by curing a curable resin composition containing components (A) to (D), and optionally components (E) and (F).

The present disclosure provides a curing agent comprising a polyetheramine, a tertiary amine and an alkanolamine. The curing agent may be combined with an epoxy resin to form a curable composition which is capable of being applied to a substrate and cured to form a cured article.