# US 4,393,180 A · Curing agents for epoxide resins and compositions containing them

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- Number: US 4,393,180 A
- Document ID: US4393180A
- Status: Granted
- Kind: A
- Application number: 06/390,468
- Filed: 1982-06-21
- Granted: 1983-07-12
- Earliest claimed: 1981-06-30
- Assignees: Ciba-Geigy Corporation
- Inventors: Christopher M. Andrews
- Web page: https://patentgrep.com/patent/US4393180A

## CPC

- C08G 59/4284: {together with other curing agents}
- C07F 7/10: containing nitrogen {having a Si-N linkage}
- C08G 59/4085: {silicon containing compounds}
- C08G 59/62: Alcohols or phenols
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Curable compositions contain an epoxide resin and, as curing agent, a mixture of (a) a silamine of the general formula ##STR1## wherein either m represents 1, in which case R.sup.1 represents the divalent residue of an aromatic, aliphatic, araliphatic, or cycloaliphatic diprimary amine after removal of two primary amino groups, and n represents zero or an integer of from 1 to 10, or m represents 2, in which case R.sup.1 represents the trivalent residue of an aliphatic triprimary amine after removal of the three primary amino groups, and n represents zero, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6, which may be the same or different, represent alkyl or aryl groups, and (b) a substantially anhydrous organic acid or a phenol. These compositions are stable for prolonged periods in the absence of water, but cure rapidly at room temperature or at elevated temperatures in the presence of water, which may be as water vapor or liquid water.

## Claims

### Claim 1

Compositions for curing epoxide resins and activated by water, said compositions comprising
(a) a silamine of the formula ##STR8## where either m represents 1, in which case R.sup.1 represents the divalent residue of an aromatic, aliphatic, araliphatic, or cycloaliphatic diprimary amine after removal of the two primary amino groups and n represents zero or an integer of from 1 to 10, or m represents 2, in which case R.sup.1 represents the trivalent residue of an aliphatic triprimary amine after removal of the three primary amino groups and n represents zero, and
R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6, which may be the same or different, each represent an alkyl group of 1 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms, and
(b) as accelerator, a substantially anhydrous organic acid or a substantially anhydrous phenol.

### Claim 2 (depends on 1)

The compositions of claim 1, wherein R.sup.1 represents a group having from 2 to 20 carbon atoms.

### Claim 3 (depends on 1)

The compositions of claim 1, wherein R.sup.1 represents an ethylene, hexamethylene, trimethylhexamethylene, xylylene, cyclohexylene, substituted cyclohexylene of formula ##STR9## bis(phenylene)methane, bis(phenylene) sulfone, 2,2-bis(phenylene)-propane, or phenylene group.

### Claim 4 (depends on 1)

The compositions of claim 1 in which R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 each represent methyl, ethyl, n-propyl, phenyl, or phenyl substituted by one or more alkyl groups of 1 to 4 carbon atoms or by one or more halogen atoms.

### Claim 5 (depends on 1)

The compositions of claim 1 in which component (b) is acetic, phthalic, methanesulfonic, salicylic, maleic, 2,2-dichloropropionic, adipic, trimellitic, or cyanoacetic acid or, where such acid is di- or polybasic, a partial ester of the acid.

### Claim 6 (depends on 1)

The compositions of claim 1 in which component (b) is phenol itself, an alkylated phenol, a halogenated phenol, resorcinol, bisphenol F, or bisphenol A.

### Claim 7 (depends on 1)

The compositions of claim 1 which further contain
(c) an epoxide resin.

### Claim 8 (depends on 7)

The compositions of claim 7 in which the weight ratio of the said acid or phenol to the epoxide resin is within the range 0.5-20:100.

### Claim 9 (depends on 7)

The compositions of claim 7 which contain sufficient of the silamine to supply from 0.7 to 1.4 amino-hydrogen equivalents, calculated after removal of substantially all the silyl groups, per 1,2-epoxide equivalent of the epoxide resin.

### Claim 10 (depends on 7)

A process for curing an epoxide resin which comprises exposing the compositions of claim 7 to liquid water or water vapour at ambient or elevated temperature.