# US 5,352,831 A · Oligomeric cyanoguanidines

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- Number: US 5,352,831 A
- Document ID: US5352831A
- Status: Granted
- Kind: A
- Application number: 07/914,158
- Filed: 1992-07-14
- Granted: 1994-10-04
- Earliest claimed: 1987-09-02
- Assignees: Ciba-Geigy Corporation
- Inventors: Peter Flury; Martin Roth; Sameer H. Eldin
- Web page: https://patentgrep.com/patent/US5352831A

## CPC

- C07C 279/28: having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
- C08G 18/025: {the polymeric products containing carbodiimide groups}
- C08G 59/4021: {Ureas; Thioureas; Guanidines; Dicyandiamides}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Oligomeric cyanoguanidines of formula I ##STR1## wherein, for example, R.sup.1 and R.sup.2 are each phenyl, R is 1,4-phenylene and n is an integer from 1 to 20, are suitable latent hardeners for epoxy resins. They are readily soluble in solvents suitable for the application of epoxy resins, and the cured products obtained therewith have a high glass transition temperature.

## Claims

### Claim 1

An oligomeric cyanoguanidine of formula I ##STR13## wherein R is a divalent C.sub.2 -C.sub.20 aliphatic hydrocarbyl, mono- or polynuclear C.sub.5 -C.sub.20 cycloaliphatic, C.sub.6 -C.sub.20 aromatic radical; or
R is a divalent radical of furan, pyran, pyridine, pyrrole, imidazole or thiophene; or
R is a group of formula II ##STR14## wherein T is methylene, isopropylidene, CO, O, S or SO.sub.2 ;
R.sup.1 and R.sup.2 are each independently of the other C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.2 aralkyl or a monovalent radical of furan, pyran, pyridine, pyrrole, imidazole or thiophene; and,
n is an integer from 1 to 20,
which radicals R, R.sup.1 and R.sup.2 are unsubstituted or are substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, halogen, R.sup.3 OCO or R.sup.3 COO, where R.sup.3 is phenyl or C.sub.1 -C.sub.4 alkyl,
with the proviso that 1,6-hexane-bis(3-cyano-2-isobutylguanidine) is excluded.

### Claim 2 (depends on 1)

A cyanoguanidine according to claim 1, wherein n is an integer from 1 to 10.

### Claim 3 (depends on 1)

A cyanoguanidine according to claim 1, wherein R is an aliphatic radical of 2 to 10 carbon atoms, a cycloaliphatic radical of 5 or 6 carbon atoms or an aromatic radical of 6 to 10 carbon atoms, or is a group of formula II, wherein T is methylene or isopropylidene.

### Claim 4 (depends on 1)

A cyanoguanidine according to claim 1, wherein R.sup.1 and R.sup.2 are each independently of the other C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.6 -C.sub.10 aryl or benzyl.

### Claim 5 (depends on 1)

A cyanoguanidine according to claim 1, wherein R is phenylene, methylphenylene, the radical ##STR15## or a group of formula II, wherein T is methylene, and R.sup.1 and R.sup.2 are each independently of the other phenyl, tolyl, methoxyphenyl, naphthyl or cyclohexyl.

### Claim 6 (depends on 1)

A cyanoguanidine according to claim 1, wherein R, R.sup.1 and R.sup.2 are C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.12 aralkyl radicals.

### Claim 7 (depends on 1)

A cyanoguanidine according to claim 1, wherein R is methylphenylene or a group of formula II, in which T is methylene, and R.sup.1 and R.sup.2 are each phenyl.

### Claim 8 (depends on 1)

A mixture of cyanoguanidines obtainable by heating a mixture containing a monoisocyanate R.sup.1 --NCO and/or R.sup.2 --NCO and a diisocyanate OCN--R--NCO, in the prescence of a catalyst, to give a carbodiimide or formula III* ##STR16## wherein R.sup.1, R.sup.2 and R are as defined in claim 1 and n* is 0 or an integer from 1 to 20, and subsequently reacting said carbodiimide of formula III* with cyanamide.