# US 2022/0033570 A1 · Curing agent composition for an epoxy resin compound, epoxy resin compound and multi-component epoxy resin system

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- Number: US 2022/0033570 A1
- Document ID: US20220033570A1
- Status: Published application
- Kind: A1
- Application number: 17/276,939
- Filed: 2019-09-09
- Published: 2022-02-03
- Earliest claimed: 2018-09-19
- Assignees: Hilti Aktiengesellschaft
- Applicants: Hilti Aktiengesellschaft
- Inventors: Nicole Behrens
- Web page: https://patentgrep.com/patent/US20220033570A1

## CPC

- C08G 59/5033: {aromatic}
- C08G 59/245: {aromatic}
- C08G 59/4014: {Nitrogen containing compounds}
- C08G 59/56: together with other curing agents
- C08G 59/68: characterised by the catalysts used
- C09K 8/44: containing organic binders only
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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.

## Claims

### Claim at position 1

1: 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.

### Claim at position 2 (depends on 1)

2: The curing agent composition according to claim 1, wherein R3 and R5 each represent H.

### Claim at position 3 (depends on 1)

3: The curing agent composition according to claim 1, wherein Z is selected from the group consisting of a direct bond, —C(R8)(R9)—, —C(R8)(aryl)-, —C(O)—, —S—, —O—, —S(O)—, —S(O)2—, a divalent heterocycle and —[C(R8)(R9)]m-arylene-[C(R10)(R11)]n—, where m and n are each independently between 0 and 5.

### Claim at position 4 (depends on 1)

4: The curing agent composition (B) according to claim 1, wherein R3 and R5 each represent H, and wherein Z is selected from a direct bond or —C(R8)(R9)—, where R8 and R9 are each independently selected from H or C1-C4 alkyl groups, or together form a lactone group.

### Claim at position 5 (depends on 1)

5: The curing agent composition according to claim 1, wherein the benzoxazine-amine adduct can be obtained by reacting a benzoxazine with an amine from the group of aliphatic and/or araliphatic amines, diamines, polyamines and mixtures thereof,
wherein the benzoxazine has one of the following structures:

### Claim at position 6 (depends on 1)

6: The curing agent composition according to claim 1, wherein the amine reactive to epoxy groups is selected from the group consisting of 2,2,4- or 2,4,4-trimethyl-1,6-diaminohexane and mixtures thereof, 3-aminomethyl-3,5,5-trimethylcyclohexane (IPDA), 1,3-bis(aminomethyl)-cyclohexane (1,3-BAC), 1,4-bis(aminomethyl)-cyclohexane (1,4-BAC), 2-methyl-1,5-pentanediamine (DYTEK A), (3(4),8(9)bis(aminomethyl)dicyclo[5.2.1.02,6]decane and isomer mixtures thereof (TCD-diamine), aminomethyltricyclo[5.2.1.02.6]decane and isomer mixtures thereof (TCD-amine), 1,6-hexamethylene diamine, diethylene triamine (DETA), triethylene tetramine (TETA), tetraethylene pentamine (TEPA), pentaethylene hexamine (PEHA), 1,3-benzenedimethanamine (mXDA), 1,4-benzenedimethanamine (pXDA), N,N′-dimethyl-1,3-benzenedimethanamine, and mixtures of two or more thereof.

### Claim at position 7 (depends on 6)

7: The curing agent composition according to claim 6, wherein the amine reactive to epoxy groups is selected from the group consisting of 3-aminomethyl-3,5,5-trimethylcyclohexane (IPDA), 2-methyl-1,5-pentanediamine (DYTEK A), 1,3-benzenedimethanamine (mXDA), 1,3-bis(aminomethyl)-cyclohexane (1,3-BAC) and mixtures thereof.

### Claim at position 8 (depends on 1)

8: The curing agent composition according to claim 1, wherein the at least one salt (S) is selected from the group consisting of nitrate (NO3−), iodide (I−), triflate (CF3SO3−) and mixtures thereof.

### Claim at position 9 (depends on 1)

9: The curing agent composition according to claim 1, wherein the at least one salt (S) is contained in the curing agent composition in an amount of from 0.1 to 15 wt. %, based on the total weight of the curing agent composition.

### Claim at position 10 (depends on 1)

10: An epoxy resin compound, comprising:
at least one curable epoxy resin; and
a curing agent composition according to claim 1.

### Claim at position 11 (depends on 10)

11: The epoxy resin compound according to claim 10, wherein the epoxy resin compound is a multi-component epoxy resin compound.

### Claim at position 12

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.

### Claim at position 13 (depends on 12)

13: The multi-component epoxy resin system according to claim 12, wherein the salt (S) is contained in the curing agent component.

### Claim at position 14 (depends on 10)

14: A method for the chemical fastening of a construction element in boreholes, the method comprising:
chemical fastening of the construction element with an epoxy resin compound according to claim 10.

### Claim at position 15

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.

### Claim at position 16 (depends on 12)

16: A method for the chemical fastening of a construction element in boreholes, the method comprising:
chemical fastening of the construction element with a multi-component epoxy resin system according to claim 12.

### Claim at position 17 (depends on 10)

17: A cured compound obtained by curing the epoxy resin compound according to claim 10.