US 2022/0033570 A1Published application

Curing agent composition for an epoxy resin compound, epoxy resin compound and multi-component epoxy resin system

AssigneeHilti Aktiengesellschaft

InventorNicole Behrens

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Abstract

A curing agent composition for an epoxy resin compound useful for the chemical fastening of construction elements, an epoxy resin compound, and a multi-component epoxy resin system are provided. Methods for the chemical fastening of construction elements in boreholes and the use of a salt (S) as an accelerator in an epoxy resin compound for chemical fastening are provided, the epoxy resin compound including a benzoxazine-amine adduct and an amine which is reactive to epoxy groups.

Claims17

Dependent claims

A curing agent composition (B), comprising:
a benzoxazine-amine adduct selected from the group consisting of substances according to formula Ia, substances according to formula Ib and mixtures thereof, having the following structures:
where R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroalkyl, alkoxy, hydroxyl, hydroxyalkyl, carboxyl, halo, haloalkyl, amino, aminoalkyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, sulfonic acid, alkylsulfonyl groups, and also from combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted;
where R6 and R7 each independently represent H or an amino, diamino or polyamino group selected from the group consisting of aliphatic, alicyclic, aromatic or araliphatic amine groups, and also combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted;
where Z is selected from the group consisting of a direct bond, —C(O)—, —S—, —O—, —S(O)—, —S(O)2—, —C(R8)(R9)—, —[C(R8)(R9)]m—C(R8)(R9)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(R8)(aryl)-[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S—[C(R10)(R11)]n—, —[C(R8)(R9)]m—O—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)2—[C(R10)(R11)]n—, a divalent heterocycle and —[C(R8)(R9)]m-arylene-[C(R10)(R11)]n—, where m and n are each independently between 0 and 10, where R8, R9, R10 and R11 each independently have the same meaning as the groups R1 to R5;
and
an amine which is reactive to epoxy groups and is selected from the group consisting of aliphatic, alicyclic, aromatic and araliphatic amines and which has on average per molecule at least two reactive hydrogen atoms bonded to a nitrogen atom,
wherein the curing agent composition comprises at least one salt (S) selected from the group consisting of salts of nitric acid, salts of nitrous acid, salts of halogens, salts of trifluoromethanesulfonic acid and combinations thereof.

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12:

A multi-component epoxy resin system, comprising:
an epoxy resin component (A), and
a curing agent component,
wherein the epoxy resin component (A) contains a curable epoxy resin, and the curing agent component comprises a benzoxazine-amine adduct and an amine which is reactive to epoxy groups,
wherein the benzoxazine-amine adduct is selected from the group consisting of substances according to formula Ia, substances according to formula Ib and mixtures thereof, having the following structures:
where R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroalkyl, alkoxy, hydroxyl, hydroxyalkyl, carboxyl, halo, haloalkyl, amino, aminoalkyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, sulfonic acid, alkylsulfonyl groups, and also from combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted:
where R6 and R7 each independently represent H or an amino, diamino or polyamino group selected from the group consisting of aliphatic, alicyclic, aromatic or araliphatic amine groups, and also combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted;
where Z is selected from the group consisting of a direct bond, —C(O)—, —S—, —O—, —S(O), —S(O)2—, —C(R8)(R9)—, —[C(R8)(R9)]m—C(R8)(R9)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(R8)(aryl)-[C(R10)(R11)]n, —[C(R8)(R9)]m—C(O)—[C(R10)(R11)]n, —[C(R8)(R9)]m—S—[C(R10)(R11)]n, —[C(R8)(R9)]m—O—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)2—[C(R10)(R11)]n—, a divalent heterocycle and —[C(R8)(R9)]m-arylene-[C(R10)(R11)]n—, where m and n are each independently between 0 and 10, where R8, R9, R10 and R11 each independently have the same meaning as the groups R1 to R5;
and the amine which is reactive to epoxy groups is selected from the group consisting of aliphatic, alicyclic, aromatic and araliphatic amines and has on average per molecule at least two reactive hydrogen atoms bonded to a nitrogen atom,
wherein a salt (S) selected from the group consisting of salts of nitric acid, salts of nitrous acid, salts of halogens, salts of trifluoromethanesulfonic acid and combinations thereof is contained in the epoxy resin component (A) and/or in the curing agent component.

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15:

A method, comprising:
accelerating an epoxy resin compound with at least one salt (S) selected from the group consisting of salts of nitric acid, salts of nitrous acid, salts of halogens, salts of trifluoromethanesulfonic acid and combinations thereof,
wherein the epoxy resin compound comprises a benzoxazine-amine adduct and an amine which is reactive to epoxy groups,
wherein the benzoxazine-amine adduct is selected from the group consisting of substances according to formula Ia, substances according to formula Ib and mixtures thereof, having the following structures:
where R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroalkyl, alkoxy, hydroxyl, hydroxyalkyl, carboxyl, halo, haloalkyl, amino, aminoalkyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, sulfonic acid or alkylsulfonyl groups, and also from combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted:
where R6 and R7 each independently represent H or an amino, diamino or polyamino group selected from the group consisting of aliphatic, alicyclic, aromatic or araliphatic amine groups, and also combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted;
where Z is selected from the group consisting of a direct bond, —C(O)—, —S—, —O—, —S(O), —S(O)2—, —C(R8)(R9)—, —[C(R8)(R9)]m—C(R8)(R9)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(R8)(aryl)-[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S—[C(R10)(R11)]n—, —[C(R8)(R9)]m—O—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)2—[C(R10)(R11)]n—, a divalent heterocycle and —[C(R8)(R9)]m-arylene-[C(R10)(R11)]n—, where m and n are each independently between 0 and 10, where R8, R9, R10 and R11 each independently have the same meaning as the groups R1 to R5, and wherein the amine which is reactive to epoxy groups is selected from the group consisting of aliphatic, alicyclic, aromatic and araliphatic amines and has on average per molecule at least two reactive hydrogen atoms bonded to a nitrogen atom.

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Abstract

A curing agent composition (B), comprising:
a benzoxazine-amine adduct selected from the group consisting of substances according to formula Ia, substances according to formula Ib and mixtures thereof, having the following structures:
where R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroalkyl, alkoxy, hydroxyl, hydroxyalkyl, carboxyl, halo, haloalkyl, amino, aminoalkyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyl, alkylcarbonyl, alkylsulfonylamino, aminosulfonyl, sulfonic acid, alkylsulfonyl groups, and also from combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted;
where R6 and R7 each independently represent H or an amino, diamino or polyamino group selected from the group consisting of aliphatic, alicyclic, aromatic or araliphatic amine groups, and also combinations of two or more of these groups, wherein the groups are each unsubstituted or optionally substituted;
where Z is selected from the group consisting of a direct bond, —C(O)—, —S—, —O—, —S(O)—, —S(O)2—, —C(R8)(R9)—, —[C(R8)(R9)]m—C(R8)(R9)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(R8)(aryl)-[C(R10)(R11)]n—, —[C(R8)(R9)]m—C(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S—[C(R10)(R11)]n—, —[C(R8)(R9)]m—O—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)—[C(R10)(R11)]n—, —[C(R8)(R9)]m—S(O)2—[C(R10)(R11)]n—, a divalent heterocycle and —[C(R8)(R9)]m-arylene-[C(R10)(R11)]n—, where m and n are each independently between 0 and 10, where R8, R9, R10 and R11 each independently have the same meaning as the groups R1 to R5;
and
an amine which is reactive to epoxy groups and is selected from the group consisting of aliphatic, alicyclic, aromatic and araliphatic amines and which has on average per molecule at least two reactive hydrogen atoms bonded to a nitrogen atom,
wherein the curing agent composition comprises at least one salt (S) selected from the group consisting of salts of nitric acid, salts of nitrous acid, salts of halogens, salts of trifluoromethanesulfonic acid and combinations thereof.

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