Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-10-04
1998-05-19
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D207325
Patent
active
RE0358029
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a silane-type compound which can be used as a coupling agent, comprising a functional group capable of reacting in order to be incorporated in the chain of an electrically-conducting polymer, it being possible for the silane group, for its part, to be chemically bonded to an inorganic substrate, especially glass, in order to form an adherent coating of this polymer.
In accordance with a usage established in industry, "silane" here refers to a compound containing a group --Si(--OR.sup.1).sub.3, R.sup.1 being a monovalent radical and more particularly an alkyl radical.
The compound according to the invention has the formula ##STR1## which may be substituted in position 3 and/or 4, X and Y represent bivalent radicals, Z represents an at least bivalent radical, R and R.sup.1 represent monovalent radicals, (x+y) being equal to the valency of Z and z being between 0 and 2.
The invention is targeted in particular at a compound having the following formula: --sI(OR.sup.1).sub.3 ( II) represents a monovalent radical or a hydrogen atom, n is equal to 1 or 2 and p is equal to 2-n.
In a specific example of the compound according to the invention, R.sup.1, R.sup.2 and R.sup.3 respectively represent the C.sub.2 H.sub.5, CH.sub.2 and (CH.sub.2).sub.3 radicals, and n is equal to 2.
The invention is also targeted at a coupling agent having the following formula: --Si(--OR.sup.1).sub.3 !.sub.n (III).!. --Si(--OR.sup.1).sub.3 !.sub.n ( III) represents a monovalent radical or a hydrogen atom, n is equal to 1 or 2 and p is equal to 2-n.
Another subject of the invention is a process for the preparation of the compound defined above, in which two molecules containing mutually reactive groups are reacted together, one of these molecules additionally containing a pyrrolidyl group and the other containing a group --SiR.sub.z (OR.sup.1).sub.3-z.
Advantageously, the mutually reactive groups are an amine group and an epoxide group.
By way of example, the molecules used in the process according to the invention may be ##STR2## . V).
The molecule of the formula (IV) above may be obtained in particular by introducing pyrrole dropwise into an aqueous reaction mixture containing sodium hydroxide, tetrabutylammonium hydrogensulfate and epichlorohydrin, which is stirred vigorously and cooled so as not to exceed room temperature.
Alternatively, the molecules used may be, on the one hand, commercial silane containing an epoxide functional group: ##STR3## and, on the other hand, one of the following compounds:
The molecule of the formula (VII) is easily prepared according to the process described by Foulds in Anal. Chem., 60, 2473 (1988). The molecule of the formula (VIII) can likewise be obtained according to the process described in European Patent Application 338,989.
The invention is also targeted at the use of the compounds of formula (I) defined above for the production of an electrically-conducting coating which adheres to an inorganic substrate, for example made of glass or silica, by formation of covalent bonds between the silicon atoms of the compound and the surface of the substrate, and oxidation of the and of an additional pyrrole in order to form a polymer which includes the compound and to make this polymer conducting. This additional pyrrole may be pyrrole properly so called or a pyrrole which is substituted at one or both of the positions .beta. to the nitrogen atom.
In a more detailed way, the use according to the invention provides that the alkoxysilane groups of the compound (I) are hydrolyzed in a water/alcohol solution, that the substrate is immersed in the solution, that the treated substrate is then immersed in an aqueous ferric chloride solution and that the additional pyrrole is introduced therein while stirring vigorously.
In a variation of the use according to the invention, instead of reacting the preconstituted compound according to the invention with the substrate, a molecule containing the pyrrolidyl radical is reacted with the substrate which has been treated beforehand with a commercial
REFERENCES:
patent: 3346588 (1967-10-01), Ashby
patent: 5066748 (1991-11-01), Nagasubramanian et al.
Journal of the American Chemical Society, vol. 104, No. 7, Apr. 7, 1982, Gaston, Pa. US, pp. 2031-2034.
Chemistry Letters, No. 4, Apr. 1984, Tokyo, JP, pp. 509-512.
Ancelle Jacques
Andrieux Claude
Attias Andre
Audebert Pierre
Bloch Bertrand
Office National d'Etudes et de Recherches Aerospatiales
Powers Fiona T.
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