# US 4,393,185 A · Thermally polymerizable mixtures and processes for the thermally-initiated polymerization of cationically polymerizable compounds

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- Number: US 4,393,185 A
- Document ID: US4393185A
- Status: Granted
- Kind: A
- Application number: 06/380,801
- Filed: 1982-05-21
- Granted: 1983-07-12
- Earliest claimed: 1981-06-02
- Assignees: Ciba-Geigy Corporation
- Inventors: Godwin Berner; Rudolf Kirchmayr
- Web page: https://patentgrep.com/patent/US4393185A

## CPC

- C08K 5/3462: Six-membered rings
- C08G 59/68: characterised by the catalysts used
- C08K 5/3432: Six-membered rings
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Cationically polymerizable compounds, in particular epoxy compounds, can be polymerized by heating in the presence of a catalyst and a co-catalyst. The catalyst employed is a quaternary ammonium salt of an aromatic-heterocyclic compound which contains 1 or 2 N-atoms, and a complex halide anion, e.g. PF.sub.6.sup..crclbar.. The co-catalyst employed is a diaryl ethane derivative, preferably benzpinacol, a silyl oligomer thereof, an organic per compound or a quinone.

## Claims

### Claim 1

A thermally polymerisable mixture which comprises
(A) one or more cationally polymerisable compounds,
(B) a quaternary ammonium salt of an aromatic-heterocyclic compound which contains 1 or 2 N-atoms, and of a complex halide anion selected from the series consisting of BF.sub.4.sup..crclbar., PF.sub.6.sup..crclbar., SbF.sub.6.sup..crclbar., SbF.sub.5 (OH).sup..crclbar. or AsF.sub.6.sup..crclbar.,
(C) a thermal radical former selected from one of the following classes
(C.sub.1) diaryl ethane derivatives of the formula I ##STR12## wherein Ar is phenyl, naphthyl or phenyl which is substituted by C.sub.1 -C.sub.4 alkyl or chlorine, R.sup.1 is OH, C.sub.1 -C.sub.4 alkoxy, --O--CO--R.sup.3 or --Osi(R.sup.4)(R.sup.5)(R.sup.6), wherein R.sup.3 is C.sub.1 -C.sub.8 alkyl or phenyl, and each of R.sup.4, R.sup.5 and R.sup.6 independently of the other is C.sub.1 -C.sub.4 alkyl or phenyl, and R.sup.2 is C.sub.1 -C.sub.4 alkyl, cyclohexyl or Ar,
(C.sub.2) an oligomeric compound of the Formula II ##STR13## wherein m is 2 to 20, (C.sub.3) an organic peroxide compound or
(C.sub.4) a quinone, and
(D) optionally further additives.

### Claim 2 (depends on 1)

A mixture according to claim 1, which contains, as component (B), a compound of the formula III, IV or V ##STR14## wherein R.sup.9 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.15 alkoxyalkyl or benzoylmethyl, each of R.sup.10, R.sup.11, R.sup.13 and R.sup.14 independently of the other is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, or R.sup.10 and R.sup.11 or R.sup.11 or R.sup.12 or R.sup.12 and R.sup.13 or R.sup.13 and R.sup.14, together with the two carbon atoms to which they are attached, are a fused benzo, naphtho, pyridino or quinolino radical, and X is BF.sub.4, PF.sub.6, SbF.sub.5 (OH) or AsF.sub.6.

### Claim 3 (depends on 1)

A mixture according to claim 1 which contains, as compoment (A), one or more epoxy compounds.

### Claim 4 (depends on 1)

A mixture according to claim 1, which contains, as component (C), an organic peroxide compound of the formula R--O--O--R', wherein R is alkyl, cycloalkyl, aralkyl, alkanoyl or aroyl, and R' is hydrogen, alkyl, cycloalkyl, aralkyl, alkanoyl or aroyl.

### Claim 5 (depends on 1)

A process for the thermal polymerisation of cationically polymerisable compounds or mixtures of compounds by heating in the presence of a catalyst and a co-catalyst, which process comprises using as catalyst a quaternary ammonium salt of an aromatic-heterocyclic compound which contains 1 or 2 N-atoms, and a complex halide anion selected from the group consisting of BF.sub.4.sup..crclbar., PF.sub.6.sup..crclbar., SbF.sub.6.sup..crclbar., SbF.sub.5 (OH).sup..crclbar. or AsF.sub.6.sup..crclbar., and, as co-catalyst, a thermal radical former according to component (C) of claim 1.