Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
1999-08-31
2002-03-05
O'Sullivan, Peter (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S059000, C564S060000, C564S061000, C564S278000, C528S049000, C528S053000, C528S054000, C528S059000, C528S060000, C528S062000, C528S064000, C528S065000
Reexamination Certificate
active
06353135
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an aliphatic or alicyclic ketimine and to its corresponding polyamine which are usable in coatings, composites, or adhesives.
BACKGROUND OF THE INVENTION
Polyamines has found widescale application in the preparation of composites, such as nylons and other polyamides or heterocycles such as imides, oxazoles, or thiazoles. The usefulness of the polyamines. however, is sometimes impacted by their reactivity. To slow and to control their reaction, we have discoverd that the amine functionalities can be blocked with ketones to form novel ketimines. The ketimines might be used as latent moisture cure resins in epoxy coatings or in two-part polyurethane systems where the ketimine evolves to the polyamine and reacts with an isocyanate or reacts directly with the isocyanate, as described in Dr. D. Wicks et al., “The Direct Reaction Between Ketimines and Aliphatic Isocyanates,” Water-Borne & Higher-Solids and Powder Coatings Symposium, Feb. 24-26, 1993, which we incorporate by reference.
SUMMARY OF THE INVENTION
The ketimine of the present invention is one component of a novel class of tetraketimines or polyamines useful as latent moisture cure resins or components in composites. The preferred tetraketimine is typically aliphatic and of reasonably high molecular weight to provide toughness with relatively high crosslinking but without brittleness. The tetraketimine is generally made by condensing a diisocyanate with a triamine having two, blocked primary amines and one free secondary amine. A preferred tetraketimine has the formula:
wherein Et is ethyl, Me is methyl, and R is a residue of a diisocyanate, and, preferably, an aliphatic or alicyclic hydrocarbon.
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patent: 4009307 (1977-02-01), Erikson et al.
patent: 5739194 (1998-04-01), Natesh et al.
patent: 6008410 (1999-12-01), Olli
patent: 26 30 013 (1978-01-01), None
patent: 2630013 (1978-12-01), None
Wicks, et al., “The Direct Reaction Between Ketimines and Aliphatic Isocyanates,” Water-Borne & Higher Solids and Powder Coatings Symp. Feb., 1993.
Hill, et al., “High Solids Coatings Based on a Novel Triisocyanate,” Waterborne, Higher Solids and Powder Coatings Symp., Feb. 1995 pp. 200-210.
Hammar John C.
O'Sullivan Peter
The Boeing Company
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