Quinone diimmonium salts and their use to cure epoxies
AssigneeEpolin, Inc.
InventorMurray S. Cohen
Life of this patent
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Abstract
The invention relates to divalent immonium salts which are near infrared dyes of the formula (I). (R.sub.2 NAr).sub.2 --N.sup.+ .dbd.Ar'.dbd.N.sup.+ R.sub.2 +2X.sup.-(I) wherein: R.dbd.C.sub.1 to C.sub.6 alkyl; Ar=divalent phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups; Ar'=quinoidal phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups; and X=an anion of a strong acid. A double charged dye cation having an SbF.sub.6 anion associated with the dye can act both a near IR dye and an epoxy curative.
Claims6
The invention provides a near IR dye of the formula I:
- (R.sub.2 NAr).sub.2 --N.sup.+ .dbd.Ar'.dbd.N.sup.+ R.sub.2 +2X.sup.-(I)
- wherein:
- R=C.sub.1 to C.sub.6 alkyl;
- Ar=divalent phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups;
- Ar'=quinoidal phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups;
- and
- X=an anion of a strong acid.
A method of preparing a compound of the formula I:
- (R.sub.2 NAr).sub.2 --N.sup.+ .dbd.Ar'.dbd.N.sup.+ R.sub.2 +2X.sup.-(I)
- which comprises double oxidizing a compound of the formula II:
- (R.sub.2 NAr).sub.2 --N--Ar'--NR.sub.2 (II)
- wherein:
- R=C1-C.sub.6 alkyl;
- Ar=divalent phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups;
- Ar'=quinoidal phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups;
- and
- X=is an anion of a strong acid;
- wherein the oxidizing is conducted in the presence of an oxidant selected from the group consisting of silver salts and copper salts and a component having an anion of a strong acid.
A near IR dye compound of the formula IV:
- (R.sub.2 NAr).sub.3 N.sup.+ +PF.sub.6.sup.- (IV)
- wherein:
- R=C.sub.1 -C.sub.6 alkyl;
- Ar=divalent phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups.
Dependencies are inferred from the claim text.