Patent GB-995861-A (GB)
Title: Acryloxyalkyl-ketimines and -aldimines and derivatives thereof
IPC: C08F8/12
Filed: 1961-06-19
Abstract: The invention comprises compounds of the following formulae <FORM:0995861/C2/1> where R is H or CH3, A is C2-12 alkylene, R1 and R2 are each a C1-12 alkyl group or a cycloalkyl group, m is 4 or 5, and R3 is phenyl, halophenyl or a C1-4-alkoxyphenyl group; and their preparation by reaction under alkaline conditions between an acrylic or methacrylic ester and an appropriate iminoalkanol, e.g. in the presence of a tetraalkyl titanate or an alkali metal alkoxide.  A polymerization inhibitor is preferably present.  The starting iminoalkanols may be obtained from appropriate aminoalkanols and aldehydes or ketones. The compounds of the above formulae may be hydrolysed under acid conditions to produce the corresponding aminoalkyl ester salt.  The compounds of the invention, and the hydrolysed aminoalkyl ester salts, can be polymerized (see Division C3). Specifications 518,057 and 579,698 are referred to.ALSO:The invention comprises homopolymers and copolymers of the compounds of the formulae <FORM:0995861/C3/1> where R is H or CH3, A is C2- 12 alkylene, R1 and R2 are each a C1- 12 alkyl group or a cycloalkyl group, m is 4 or 5, and R3 is phenyl, halophenyl, or a C1- 4-alkoxyphenyl group (see Division C2), and copolymers of these with monoethylenically unsaturated monomers, e.g. with 0.5-99.5%, by weight of monomer mixture, of vinyl acetate, acrylonitrile, acrylamide, methacrylamide, styrene, vinyltoluene, vinylidene chloride, vinyl chloride, vinyl laurate, or a C1- 18 alkanol ester of acrylic or methacrylic acid.  Polymerization may be effected by bulk, solution, or aqueous emulsion techniques, using azo-catalysts such as azodiisobutyronitrile and dimethyl a ,a 1-azodiisobutyrate; suitable organic solvents are benzene, toluene, xylene, acetone, dioxan, dimethylformamide and acetonitrile.  An example also uses benzoyl peroxide as initiator. Acidic hydrolysis of the polymers produces corresponding amino - substituted polymers, which may also be prepared by polymerization of the aminoalkyl acrylates and methacrylates obtained by acidic hydrolysis of the imine monomers. The uses of the polymers referred to include the production of coatings, impregnants and adhesives for paper, textiles, leather, wood and metals, e.g. when mixed with polyepoxides, many suitable examples of which are given; and the polymers may be used as binders for pigments, as flocculating agents, and as lubricant additives. Reference is also made to copolymerization of a compound of the formulae given with glue.  Specifications 518,057 and 579,698 are referred to.ALSO:The invention comprises a lubricating oil having dissolved therein a copolymer of a compound of formula <FORM:0995861/C4-C5/1> or <FORM:0995861/C4-C5/2> with another monoethylenically unsaturated monomer; in these formulae R is H or CH3, A is C2- 12 alkylene, R1 and R2 are each a C1- 12 alkyl group or a cycloalkyl group, m is 4 or 5, and R3 is phenyl, halophenyl or a C1- 4-alkoxyphenyl group (see Division C3).  Reference is also made to the use as lubricating oil derivatives of polymers of the imines in which the imino groupings have been hydrolysed to -NH2. Specifications 518,057 and 579,698 are referred to.ALSO:Coatings and impregnants for paper, textiles, glass, leather, wood, and metals comprise a polymer of a compound of the formulae <FORM:0995861/B1-B2/1> or <FORM:0995861/B1-B2/2> where R is H or CH3, A is C2-12 alkylene, R1 and R2 are each a C1-12 alkyl group or a cycloalkyl group, m is 4 or 5, and R3 is phenyl, halophenyl or a C1-4-alkoxyphenyl group; or a corresponding polymer in which the imino grouping has been replaced by NH2; or copolymers or these with monoethylenically unsaturated compounds (see Division C3). Polyepoxides may also be present.  Examples prepare coatings from acetone and benzene solutions of the polymers.  Specifications 518,057 and 579,698 are referred to.ALSO:Polymers of compounds of the formulae <FORM:0995861/D1-D2/1> or <FORM:0995861/D1-D2/2> where R is H or CH3, R1 and R2 are each a C1-12 alkyl group or a cycloalkyl group, A is a C2-12 alkylene radical, m is 4 or 5, and R3 is phenyl, halophenyl or a C1-4 -alkoxyphenyl group, and their copolymers with vinyl acetate, acrylonitrile, acrylamide, methacrylamide, styrene, vinyltoluene, vinylidene chloride, vinyl chloride, vinyl laurate, or esters of acrylic or methacrylic acid, or corresponding polymers in which the imino grouping has been replaced by -NH2 (see Division C3) are of use (i) for the stabilization of wool fabrics against shrinkage on laundering; (ii) for the binding of fibres in non-woven fabrics; and (iii) as impregnants imparting wet-strength to paper. Specifications 518,057 and 579,698 are referred to.