Patent GB-815159-A (GB)
Title: Organotitanium compounds
IPC: C07F7/00
Filed: 1956-04-24
Abstract: Fuel oil compositions, coating compositions and pigment dispersions, comprise kerosene or mineral spirits containing monomeric or polymeric b -aminoalkyl acyl titanates in which the Ti is quadrivalent, the monomeric form contains Ti covalently bonded to 1 to 3 mols. of b -aminoalkoxy groupings, 0.2 to 2 mols. of acyloxy groupings and 0 to 2.8 mols. of C2-18 alkoxy groupings per gram atom of titanium and the polymeric form contains from 1 to 2.8 Ti-O-Ti bonds per titanium atom, 1 to 2.8 mols. of covalently bonded b -aminoalkoxy grouping per gram atom of titanium and 0.2 to 2 mols. of covalently bonded acyloxy groupings per gram atom of titanium, any remaining covalencies being satisfied by C2-18 alkoxy groupings, said acyloxy grouping being a C2-20 grouping derived from a saturated or unsaturated aliphatic or aromatic monocarboxylic acid which may bear unreactive halogen substituents and said b -aminoalkoxy grouping being derived from a b -aminoalcohol of the formula: HO-CHR11-CH2-NR111R1111 where R11 is H or a C1-5 aliphatic hydrocarbon grouping and R111 and R1111 are H, C1-20 aliphatic hydrocarbon groupings, C2-9 aminoalkyl groupings or C2-5 hydroxyalkyl groupings.  A solution of a b -aminoethylethanolamine oleoyl titanate in xylene is brushed on to a ceramic body to give a thin water-repellent film thereon after evaporation of the solvent. Specification 755,728 is referred to.ALSO:Polymeric b -aminoalkyl acyl titanates in which the Ti is quadrivalent and which contain from 1 to 2.8 Ti-O-Ti bonds per titanium atom, 1 to 2.8 mols. of covalently bonded b -aminoalkoxy groupings per gram atom of titanium and 0.2 to 2 mols. of covalently bonded acyloxy groupings per gram atom of titanium, any remaining covalencies being satisfied by C2-18 alkoxy groupings, said acyloxy grouping being a C2-20 grouping derived from a saturated or unsaturated aliphatic or aromatic monocarboxylic acid which may bear unreactive halogen substituents and said b -aminoalkoxy grouping being derived from a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111, where R11 is H or a C1-5 aliphatic hydrocarbon grouping and R111 and R1111 are H, C1-20 aliphatic hydrocarbon groupings, C2-9 aminoalkyl groupings or C2-5 hydroxyalkyl groupings, are prepared by acylating a condensed C2-18 alkyl titanate with from 0.2 to 2 mols. of an acid R1.COOH, where R1 is a C2-20 saturated or unsaturated aliphatic or aromatic radical, for each gram atom of titanium present and reacting the condensed alkoxy titanium acylate product with from 1 to 2.8 mols. of a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111 per gram atom of titanium present.  In an example, slightly aqueous butanol is added with stirring to a butanol solution of butyl titanate to produce a solution of condensed butyl titanate, which is acylated with stearic acid and the resulting condensed stearoyl butyl titanate is reacted with triethanolamine to give a condensed triethanolamine stearoyl titanate.  Uses.-The above products may be added to fuel oils or to aqueous systems to give colloidal dispersions suitable for imparting water-repellancy to fabrics.  Specification 755,728 is referred to.ALSO:The invention comprises monomeric and polymeric b -aminoalkyl acyl titanates in which the Ti is quadrivalent, the monomeric form contains Ti covalently bonded to 1 to 3 mols. of b -aminoalkoxy groups, 0.2 to 2 mols. of acyloxy groupings and 0 to 2.8 mols. of C2-18 alkoxy groupings per gram atom of titanium and the polymeric form contains from 1 to 2.8 Ti-O-Ti bonds per titanium atom, 1 to 2.8 mols. of covalently bonded b -aminoalkoxy groupings per gram atom of titanium and 0.2 to 2 mols. of covalently bonded acyloxy groupings per gram atom of titanium, any remaining covalencies being satisfied by C2-18 alkoxy groupings, said acyloxy grouping being a C2-20 grouping derived from a saturated or unsaturated aliphatic or aromatic monocarboxylic acid and said b -aminoalkoxy grouping being derived from a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111 where R11 is H or a C1-5 aliphatic hydrocarbon grouping and R111 and R1111 are H,C1-20 aliphatic hydrocarbon groupings, C2-9 aminoalkyl groupings or C2-5 hydroxyalkyl groupings.  The compounds are prepared by reacting an alkyl titanate of the formula Ti(OR)4, where R is a C2-18 alkyl group, or the corresponding condensed alkyl titanate, with an appropriate amount of an acid R1.COOH, where R1 is a C2-20 saturated or unsaturated aliphatic or aromatic radical, to form an alkoxy titanium acylate of the formula (RO)4-nTi(OCOR1)n, where n is from 0.2 to 2, or the corresponding condensed alkoxy titanium acylate, and reacting the products respectively with from 1 to 3 or from 1 to 2.8 mols. per gram atom of titanium of a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111 The acid employed for acylation may contain non-reactive halogen atoms but is preferably a C12-18 saturated fatty acid.  In the examples isopropyl titanate is acylated with stearic acid and the stearoyl isopropyl titanate is reacted with triethanolamine or triisopropanolamine to give a triethanolamine or triisopropanolamine stearoyl titanate; isopropyl titanate is acylated with lauric acid and the lauroyl isopropyl titanate is reacted with monoethanolamine to give a monoethanolamine lauryl titanate; butyl titanate is acylated with oleic acid and the oleoyl butyl titanate is reacted with b -aminoethylethanolamine to give a b -aminoethylethanolamine oleoyl titanate; 2-ethylbutyl titanate is acylated with pelargonic acid and the pelargonoyl 2-ethylbutyl titanate is reacted with diisopropanolamine to give a diisopropanolamine pelargonoyl titanate; butyl titanate is acylated with acetic acid and the acetyl butyl titanate is reacted with N-ethyldiethanolamine to give an N-ethyldiethanolamine acetyl titanate; isopropyl titanate is acylated with benzoic or para-chlorobenzoic acid and the benzoyl or para-chlorobenzoyl isopropyl titanate is reacted with triethanolamine to give a triethanolamine benzoyl or para-chlorobenzoyl titanate; slightly aqueous butanol is added with stirring to a butanol solution of butyl titanate to produce a solution of condensed butyl titanate, which is acylated with stearic acid and the condensed stearoyl butyl titanate is reacted with triethanolamine to give a condensed triethanolamine stearoyl titanate.  Specification 755,728 is referred to.