Patent GB-1083991-A (GB)
Title: Organo silicon compounds
IPC: C09K23/54
Filed: 1964-08-26
Abstract: The invention comprises tertiary aminosilanes of the formula <FORM:1083991/C3/1> and tertiary aminosiloxanes of the formula <FORM:1083991/C3/2> together with the corresponding amine oxides and quaternary ammonium salts, where R is a hydrocarbon, hydroxy-terminated polyalkyleneoxy, alkenyloxy-terminated polyalkyleneoxy, hydroxyalkyl or aminoalkyl group, or a divalent group which together with the nitrogen atom forms a heterocyclic ring, a is 0-2, x is at least one, R1 and R11 are alkylene groups of at least two carbon atoms, R111 is a hydrocarbon group free of aliphatic unsaturation, Z is a hydrocarbonoxy group and b is 0-2. The aminosiloxanes may be homopolymers or copolymers with other siloxanes which may contain alkylene groups. The aminosilanes and siloxanes are prepared by reacting a hydrosilicon compound with an alkenyl ether of a tertiary hydroxyalkylamine in the presence of a Pt catalyst, e.g. chloroplatinic acid, Pt/charcoal or Pt/g -Al2O3. The reaction may be conducted in an inert atmosphere.  The amine oxides are prepared by oxidizing the amines, e.g. with aqueous H2O2 or an anhydrous oxidizing agent such as ozone, peracetic acid or perbenzoic acid.  Quatenary amine salts are prepared by reacting the amine with a hydrocarbyl halide, a dihydrocarbyl sulphate, a hydrogen halide, a monohydrocarboxylic acid or a hydrocarbyl ester of a haloalkanoic acid, e.g.methyl or benzyl chloride. Metal co-ordination compounds are produced from the amines by reaction with a transition metal halide, hydroxide, nitrate, salt of carboxylic acid, sulphate or phosphate, e.g. FeCl3. 6H2O, CoCl2.6H2O or CuCl2.2H2O.  In Example (I), the allyl ether of N,N-dimethylethanolamine, Me2NCH2CH2OCH2CH=CH2 is added to a hydrosiloxane of average formula Me3SiO(Me2SiO)8.5(MeHSiO)3.5SiMe3 in the presence of chloroplatinic acid to give a siloxane of average formula <FORM:1083991/C3/3> which is reacted with MeCl to give the quaternary ammonium salt. The amines are useful corrosion inhibitors for metals which come into contact with aqueous liquids.  The salts are useful as emulsifying agents for water-dimethylsiloxane oil mixture and water-paraffin oil mixtures, and for increasing the dispersibility of inorganic fillers and pigments in liquids such as latex paints. Those salts which are waxes are useful in metal polishes.  The co-ordination compounds are useful as emulsifying agents for water-oil mixtures and as mould release agents. The amine, oxides, salts and co-ordination compounds are useful as sizes for organic textile and glass fibres.  Those which are gums are useful in producing elastomers, and those which are resins are useful as protective coatings for metals.ALSO:N,N - Dimethylethanol amine Me2NCH2 CH2OH is treated with ethylene oxide in the presence of sodium ethoxide to give Me2N (CH2CHO)15CH2CH2OH.  The sodium salt of this reacts with allyl chloride to give Me2N(CH2 CH2O)16CH2CH=CH2 (see Example XIII).ALSO:A size for textile fibres, e.g. cotton comprises compounds of the formula <FORM:1083991/D1-D2/1> or the corresponding amine oxides or quaternary ammonium salts where R is a hydrocarbon, hydroxy-terminated polyalkyleneoxy, alkenyloxy-terminated polyalkyleneoxy, hydroxyalkyl or aminoalkyl group, or a divalent group which together with the nitrogen atom for a heterocyclic ring, a is 0-2, x is at least 1, R\sv and R\yF are alkylene groups of at least two carbon atoms, R\yG is a hydrocarbon group free of aliphatic unsaturation, Z is a hydrocarbonoxy group, b is 0-2.  The aminosiloxanes may be homopolymers or copolymers with other siloxanes which may contain alkylene groups.  See Example 14.ALSO:An emulsifying agent for water-paraffin oil mixtures comprise a quaternary ammonium salt of a compound of the formula:- <FORM:1083991/B1-B2/1> where R is a hydrocarbon, hydroxy-terminated polyalkyleneoxy alkenyloxy-terminated polyalkyleneoxy, hydroxyalkyl or aminoalkyl group, or a divalent group which together with the nitrogen atom for a heterocyclic ring, a is 0 - 2, x is at least 1, R\sv and R\yF are alkylene groups of at least two carbon atoms, R\yF lene groups of at least two carbon atoms, R\yG is a hydrocarbon group free of aliphatic unsaturation, Z is a hydrocarbonoxy group, b is 0-2.  The aminosiloxanes may be homopolymers or copolymers with other siloxanes which may contain alkylene groups see Example 9.