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US 5,310,910 AGranted
Polycyclic diamines
AssigneeMinnesota Mining and Manufacturing Company
InventorsGary J. Drtina, Leif Christensen
Life of this patent
Estimating the term…
Abstract
Polycyclic diamines, incorporating a basic framework similar to [3.3.3]propellane, and derivatives of the basic polycyclic diamines and a process for preparing same are provided. The diamines are prepared by subjecting bispyridine compounds to electroreductive coupling in an acidic solution. The polycyclic diamines and derivatives thereof are useful as chain extenders, crosslinking agents and curatives in various polymer systems.
Claims6
Polycyclic diamines and derivatives thereof represented by Formula I:
- ##STR19## wherein R.sup.1 and R.sup.2 are independently selected from hydrogen, alkenyl or alkenylene containing 2 to 20 carbon atoms, alkyl or alkenylene containing 1 to 20 carbon atoms, aryl or arylene containing 5 to 12 ring atoms in which up to 5 of the ring atoms may be selected from S, Si, N, O, and P heteroatoms, cycloalkyl or cycloalkylene containing 3 to 12 ring atoms in which one or more ring atoms may be selected from S, Si, N, O, and P heteroatoms, and acyl, wherein acyl is ##STR20## wherein R.sup.4 is described as for R.sup.1 and R.sup.2, and further R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may include functional groups selected from the group consisting of aryl, amide, thioamide, ester, thioester, ketone (including oxo-carbons), thioketone, nitrile, nitro, sulfide, sulfoxide, sulfone, disulfide, tertiary amine, ether, urethane, dithiocarbamate, quaternary ammonium and phosphonium, halogen, silyl, and siloxy, wherein the functional groups requiring substituents are substituted with hydrogen.
Derviatives of the polycyclic diamines comprising compounds represented by Formula II:
- ##STR22## wherein R5 and R6 are independently selected from hydrogen, alkenyl or alkenylene containing 2 to 20 carbon atoms, alkyl or alkenylene containing 1 to 20 carbon atoms, aryl or arylene containing 5 to 12 ring atoms in which up to 5 of the ring atoms may be selected from S, Si, N, O, and P heteroatoms, cycloalkyl or cycloalkylene containing 3 to 12 ring atoms in which one or more ring atoms may be selected from S, Si, N, O, P heteroatoms, and acyl, wherein acyl is:
- ##STR23## wherein R.sup.4 is described as for R.sup.1 and R.sup.2, and further R.sup.1, R.sup.2, R.sup.3, and R.sup.4 may include functional groups selected from the group consisting of aryl, amide, thioamide, ester thioester, ketone (including oxo-carbons), thioketone, nitrile, nitro, sulfide, sulfoxide, sulfone, disulfide, tertiary amine, ether, urethane, dithiocarbamate, quaternary ammonium and phosphonium, halogen, silyl, and siloxy, wherein the functional groups requiring substituents are substituted with hydrogen and further, R.sup.5 and R.sup.6 taken together with the carbon atom to which they are joined, form a carbocyclic ring of 3 to 12 ring atoms, in addition to carbon, the ring atoms may be selected from S, Si, N, O and P heteroatoms.
Dependencies are inferred from the claim text.