Patent GB-1018114-A (GB)
Title: Organic silicon materials
Inventor: EMBLEM HAROLD GARTON
IPC: C07F7/18
Filed: 1962-05-14
Abstract: The invention comprises condensation products of aminoalkoxy silanes <FORM:1018114/C3/1> with a mono-oxirane compound; R1 is an alkylene or hydroxyalkylene group of 1-6 C atoms, R2 is H or an alkyl or hydroxyalkyl group of 1-6 C atoms, R3 is a phenyl or 1-5 carbon alkyl or alkenyl group, m is 0, 1, or 2, n is 1, 2, or 3, and n + m is 1, 2, or 3.  The oxirane compound is styrene oxide, or of formula <FORM:1018114/C3/2> where R7 and R8 are each hydrogen or alkyl, hydroxyalkyl or allyloxyalkyl groups, the whole not exceeding 6 C atoms.  At least 0.5 oxirane molecules are provided for each active amino hydrogen of the silane.  The reaction takes place when the mixture is heated, preferably in an inert atmosphere under pressure if necessary. The products are heat hardenable and may be used alone or in solution to provide heat-curable surface coatings, e.g. to metal surfaces.  When n, above, is 1, the products are water soluble, and may be used in aqueous solution for such coating.  Pigments (e.g. TiO2, Example 15) may be added to these solutions, giving a hard paint film on stoving. The compounds are used as hardeners for epoxy resins in amounts of 0.3-2.5 parts by weight per part of resin. Specified epoxy resins are a bisphenol A-epichlorhydrin condensate and dicyclopentadiene dioxide (Example 4).  The compounds of the invention may also be reacted with isocyanates, e.g. tolylene diisocyanate, hexamethylene diisocyanate, or phenyl isocyanate to give heat curable resins with isocyanate or hydroxy end groups. These can be cured alone or with other polyols or polyisocyanates. The end-groups, if hydroxy, may be reacted with simple isocyanates (e.g. phenyl isocyanate), or, if isocyanate, with hydroxy compounds (e.g. ethanol, phenol). The Examples 1-16 describe the reactions, mainly of 1,2-butylene oxide, with methyl tri(2-aminoethoxy) silane, methyl tri-(3-aminopropoxy) silane, dimethyl di-(2-aminoethoxy) silane, methyl ethoxy di-(2-aminoethoxy) silane, ethyl tri-(2-aminoethoxy) silane, methyl tri(N-methyl 2-aminoethoxy) silane, dimethyl di(N-methyl 2-aminoethoxy) silane, vinyl tri-(2aminoethoxy) silane, phenyl tri-(3-aminopropoxy) silane and phenyl ethoxy di-(2-aminoethoxy) silane.  1,2-propylene oxide, styrene oxide, or mixtures are used in Examples 2, 3, 8, 12, 14 and 16.  Examples 5-7 and 12-17 describe the use of the products in hardening epoxy resins, and Examples 18-22 their use in making isocyanate resins.  All these resins are characterized as coatings on glass.ALSO:Surfaces exemplified by glass or metal are coated with organosilicon materials which are then heat-cured.  The materials may be (I) products of the reaction between a monooxirane compound (e.g. styrene oxide or alkylene oxides, especially propylene or butylene oxide) and an aminoalkoxysilane containing alkyl, alkenyl or phenyl groups, also, or solutions of these (e.g. in water), to which pigments may be added (Example 15), or (II) mixtures of 0,3-2,5 parts of the products (I) with 1 part (by weight) of an epoxy resin, with or without added solvent, or (III) reaction products of materials (I) with mono- or di-isocyanates.  In Examples 1-4 and 15 the simple materials (I) are stoved on glass (metal in Example 15) at 140  DEG C.; in Examples 5-7 and 12-17 materials (II) are stoved at 140-220  DEG C.; in Examples 18-22 materials (III) in ethyl acetate are stoved at 90-140  DEG C., as films on glass in all cases.