Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1993-05-12
1994-12-06
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
556419, 556424, 528 28, 528 41, 428412, 428447, 428469, 10628716, 525105, C07F 710, C08G 7700, C08F 800, B32B 2736
Patent
active
053712617
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
It is known to use sol-gel hydrolyzation/condensation procedures with a reaction mixture comprising one or more metal alkoxide(s) and a trialkoxysilane-functionalized organic reagent to form organic/inorganic hybrid materials having interesting properties. Some recent publications which are representative of work in this area include: Huang, H. et al., Macromolecules. 1987 20(6), 1322; Huang, H. et al., ACS Symposium Series, 1987, 360, 354; and Huang, H. et al., Polym. Bull., 1987, 18, 455. There is interest in expanding the area of known organic/inorganic hybrid systems to novel combinations.
Certain disclosures also exist in the art regarding alkoxysilane-functionalized aliphatic polyamine compounds:
U.S. Pat. No. 3,847,860 shows compounds in which the amino groups are not fully functionalized with alkoxysilane groups for use in relatively minor amount (0.02%-3%) in a cold setting or thermosetting adhesive.
U.S. Pat. No. 4,448,694 also shows compounds in which less than all the amino groups are functionalized with alkoxysilane moieties. These compounds are described for use as chelants for metals after being immobilized on an inorganic solid.
U.S. Pat. No. 4,791,214 and British Patent No. 1,458,533 show "hybrid" compounds containing an alkoxysilane-functionalized amine group and either a glycidyl group or an N-substituted amino group. These compounds are used as bonding agents or adhesion promoters in resin compositions or organic adhesives.
SUMMARY OF THE INVENTION
The present invention is directed to a novel class of fully alkoxysilane-functionalized aliphatic polyamine compounds that are useful, for example, as the predominant reagent in the aforementioned type of sol-gel reactible compositions as sources of the organic moieties (or domains) in organic/inorganic hybrid materials.
This class of reagent can be cured, without the additional presence of a metal alkoxide, such as a tetralkylsilicate or zirconium alkoxide, to form hybrid organic/inorganic materials generally analogous to the previously described materials reported in the Huang et al. publications described before.
DESCRIPTION OF THE DRAWINGS
The Drawings enclosed herewith as part of the present invention illustrate certain embodiments of the invention wherein:
FIG. 1 is a graphical representation of the wear resistance for a 30% zirconium isopropoxide-70% triethoxysilane-capped diethylenetriamine (DETA) material when cured at 145.degree. C. and when such a cured material is allowed to remain in water for forty-eight hours at 60.degree. C. then dried and tested;
FIG. 2 is a plot of the wear of a series of compositions, such as tested in FIG. 1, on polycarbonate resin showing the effect of different curing temperatures for the coating; and
FIG. 3 is a plot of the effect of triethoxysilane functionality for a coating derived from a series of alkoxy silane-functionalized aliphatic polyamine compounds.
DETAILED DESCRIPTION OF THE INVENTION
As used herein the term "fully alkoxysilane-functionalized" is intended to connote that the number of alkoxysilane moieties and reacted amine moieties in the functionalized product are substantially equal. In other words, substantially all the amine groups (--NH or --NH.sub.2, if terminal) have been functionalized with alkoxysilane groups. The term "aliphatic" as used herein is intended to cover moieties which include alkylene groups (CH.sub.2), and, in the case of the diamine compound shown in Example 8, below, the group >C.dbd.O.
The aliphatic polyamine compounds which are appropriately functionalized by means of the present invention may have the formula: preferred compound has m and n both equal to 2 and is a triamine. Another aliphatic polyamine compound useful in accordance with the present invention has the formula:
The foregoing type of compounds are functionalized by reaction with a compound having an amine-reactive group ("A") at one end (such as an isocyanate group) and an alkoxysilane group at the other. In the case of trialkoxysilane-containing compounds, w
REFERENCES:
patent: 3856756 (1974-12-01), Wagner et al.
patent: 3940370 (1976-02-01), DiSalvo
patent: 4448694 (1984-05-01), Plueddemann
patent: 4719262 (1988-01-01), Plueddemann
patent: 4746366 (1988-05-01), Philipp et al.
Wang Bing
Wilkes Garth L.
Fennelly Richard P.
Morris Louis A.
Shaver Paul F.
Virginia Tech Intellectual Properties Inc.
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