Stock material or miscellaneous articles – Coated or structually defined flake – particle – cell – strand,... – Particulate matter
Patent
1986-08-26
1988-07-12
Kittle, John E.
Stock material or miscellaneous articles
Coated or structually defined flake, particle, cell, strand,...
Particulate matter
428407, 428409, 428410, 428429, 55 67, 210656, 502401, 502407, B32B 516, B32B 1700, B01D 1508, B01S 2010
Patent
active
047569719
DESCRIPTION:
BRIEF SUMMARY
This invention concerns an organosilicon compound for imparting lipophilic properties to a hydrophilic surface, such as that of glass, quartz, oxidized silicon, metal-metal oxide or of a plastic containing OH-and/or NH-groups. By means of the invention the physicochemical characteristics, especially the adsorption characteristics of such a surface may be selectively modified and/or improved. According to one mode of the invention, the compound according to the invention may be polymerized, optionally using known silicon compounds, to form a silicon polymer, which may be applied by adsorption to a surface which advantageously has been pretreated according to the invention. Important fields of use of the compounds of this invention are in chromatography, both gas and liquid chromatography, especially gas chromatography, and in electronics.
It is known to treat surfaces of, e.g., glass, with organosilicon compounds or polymers in order to modify their hydrophilic characteristics, such as for chromatographic purposes, cf DE Nos. 834 002, 29 30 516, Advances in Chemistry Series, vol. 87 (1968), Bascom W. D. and GB No. 1,354,357. However, in these known methods, primarily aliphatic silanes have been used. In instances were aromatic silanes have been used, the phenyl substituent has either been unsubstituted or substituted with groups or atoms, notably halogen atoms, which do not provide the desired selectivity according to the invention. It is also known to form surface films containing more complicated substituted aromatic groups. However, rather than using the film-forming compound as such to make the film, the film is formed by building the desired molecule from smaller molecular moieties, starting from the substrate surface and proceeding therefrom in an outward direction by consecutively adding the required molecular moieties (Journal of American Chemical Society, vol. 102 (1980) no 12, p. 4029 to 4030).
It is an object of the invention to provide new organosubstituted silanes, containing as a substituent a phenyl group which is further substituted, so as to provide compounds by means of which the properties of the treated surface may be tailor-made in a highly selective manner. This object is achieved by selectively choosing such substituents on the phenyl group(s) in the silane, which are able to actively participate in intermolecular forces, such as in the formation of charge-transfer complexes.
The organo-substituated silane according to the invention is represented by the general formula ##STR4## wherein Z.sup.1 and Z.sup.2 each is independently chlorine, fluorine, bromine, alkoxy with not more than 6 carbon atoms, NH, --NH.sub.2, --NR.sub.2 ', wherein R' is alkyl with 1 to 3 carbon atoms, --SH, --CN, --N.sub.3 or hydrogen, and R.sup.1 is ##STR5## wherein each of the S-substituents, S.sub.1, S.sub.2, S.sub.3, S.sub.4 and S.sub.5 are independently selected from the group consisting of hydrogen, alkyl with 1 to 4 carbon atoms, methoxy, ethoxy, and cyano, provided that at least one of the S-substituents is other than hydrogen and when there is a methyl or methoxy S-substituent then (i) at least two of the S-substituents are other than hydrogen, (ii) two adjacent S-substituents form with the phenyl nucleus a naphtalene or anthracene group, or (iii) three adjacent S-substituents form together with the phenyl nucleus a pyrene group, and X is the group --(CH.sub.2).sub.n --, wherein n is 0 to 20, preferably 10 to 16 when n is not 0, i.e., X is a spacer group, the S-substituents, especially S.sub.3, can also be phenoxy and biphenyl, or one of the following groups ##STR6## and R.sup.2 is equal to Z.sup.1 or R.sup.1, or is lower alkyl, lower alkenyl, phenyl, or phenyl substituted with lower alkyl or lower alkoxy.
The term "lower" in connection with groups or compounds, means from 1 to 7 and, preferably from 1 to 4, carbon atoms.
Especially advantageous compounds according to the invention are obtained when R.sup.1 is one of the following groups ##STR7## which groups R.sup.1 are attached directly to the silicon a
REFERENCES:
patent: 2546330 (1951-03-01), Barry et al.
patent: 2556462 (1951-06-01), Barry et al.
patent: 2626270 (1953-01-01), Sommer
patent: 3312727 (1967-04-01), Merker
patent: 3651117 (1972-03-01), Bennett
patent: 3722181 (1973-03-01), Kirkland et al.
patent: 3853726 (1974-12-01), Valmehielm et al.
patent: 3899328 (1975-08-01), Limburg
patent: 4099981 (1978-07-01), Mui et al.
patent: 4164509 (1979-08-01), Laufer
patent: 4242227 (1980-12-01), Nestrick et al.
patent: 4363925 (1982-12-01), Acker et al.
patent: 4539061 (1985-09-01), Sagiv
"Steric Hindrance in Highly-Substituted Organosilicon Compounds, I, the Reaction of Aryllithium Compounds with Some Chlorosilanes, Ethoxysilanes, and Related Compounds," Henry Gilman and G. N. Russell Smart, Journal of Organic Chemistry, vol. 15, 1950, pp. 720-740.
"Covalent Attachment of Arenes to SNO.sub.2 -Semiconductor Electrodes," Marye Anne Fox, Frederick J. Nobs, and Tamara A. Voynick, Journal of the American Chemical Society, Jun. 4, 1980, pp. 4029-4036.
"The Wettability of Ethyl- and Vinyltriethoxysilane Films Formed at Organic Liquid Silica Interfaces," Willard D. Bascom, Advances in Chemistry Series, vol. 87, 1968, pp. 38-41.
Kinnunen Paavo K. J.
Kulo Arvo E.
Virtanen Jorma A.
Kittle John E.
KSV-Chemicals Oy
Rucker Susan S.
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