Patent GB-834308-A (GB)
Title: Oxazoline and oxazine derivatives, polymers, copolymers thereof and method of preparation
IPC: C07D265/08
Filed: 1957-05-07
Abstract: The invention comprises compounds of formula <FORM:0834308/IV (b)/1> in which R1 and R2, when taken individually are alkyl radicals, one being methyl and the other containing from one to eight carbon atoms, or when taken together form a divalent saturated aliphatic hydrocarbon group containing 4-9 carbon atoms, which, together with the carbon atom to which R1 and R2 are attached, form a five- or six-membered carbocycle; n is 1 or 2; and m is 1 or 2.  They may be prepared by various methods from amino compounds having the formula HO-(CH2)nC(R1)(R2)NH2.  In one method these amino compounds are reacted with lower alkyl esters of acrylic and methacrylic acid of formula CH2 = C(Cm-1H2m-1)COOR3 in which R3 is an alkyl radical having from one to eight carbon atoms, in the presence of a polymerization inhibitor and of a metal alkoxide of formula M(OR4)x in which M is aluminium, titanium, gallium or zirconium, x has the same value as the valency of M and R4 is an alkyl radical preferably containing not more than 5 carbon atoms.  In another method an excess of the amino compound defined above is heated with an acryloyl or methacryloyl halide of formula CH2 = C(Cm-1H2m-1)COX, in which X is chlorine or bromine to give an amide of formula CH2 = C(Cm-1H2m-1)-CONH-C(R1) (R2)(CH2)nOH, this amide is then heated with a minor proportion of a strong mineral acid and a polymerization inhibitor to give the required compounds.  In a third method the amino compound defined above is heated with acrylic or methacrylic acid in the presence of a polymerization inhibitor to give the desired compounds.  The products, of which a large number of examples are given, are useful for incorporation in fungicides (see Group VI), for treatment of paper and cloth fabrics for protection from mould and fungi (see Group VIII), as floxation agents (see Group II) and also in the production of polymers (see Group IV (a)).ALSO:The invention comprises polymers and copolymers of compounds of the formula <FORM:0834308/IV (a)/1> in which R1 and R2, when taken individually, are alkyl radicals, one being methyl and the other having from 1 to 8 carbon atoms, or, when taken together, form a divalent saturated aliphatic hydrocarbon group containing 4-9 carbon atoms which together with the carbon atom to which R1 and R2 are both bonded form a 5- or 6-membered ring, n is 1 or 2 and m is 1 or 2. The monomers may be polymerized with the aid of a free-radical catalyst such as one or more azodiisobutyramide, dimethyl-, diethyl- or dibutylazodiisobutyrate, azobis- (a ,g -dimethylvaleronitrile), azobis - (a  - methylbutyronitrile), azobis - (a  - methylvaleronitrile), and dimethyl or diethylazobix - methyl valerate.  Polymerization may be effected in bulk, solution or in emulsion.  Copolymers are prepared from the new monomers with other vinylidine compounds which are polymerizable with free radical catalysts.  The above-methioned catalysts are suitable or the copolymerization may be carried out in dispersion with the aid of a redox system used in conjunction with one or more peroxide catalysts, e.g. benzoyl peroxide, acetyl peroxide, caproyl peroxide, butyl perbenzoate and butyl hydroperoxide.  Suitable compounds for copolymerization include acrylic and methacrylic acids and their esters, amides, salts, nitriles, and styrene, and their homologues and analogues.  When two or more free radical polymerizable vinylidene groups occur, as in divinyl benzene, ethylene di-acrylate or methacrylate, trivinylbenzene, bis-(vinyloxyethyl)-urea or vinyloxyethyl acrylate or methacrylate, insoluble copolymers result. Copolymerization may be effected in bulk, solution, emulsion or suspension.  The polymers and copolymers formed may be used in coating compositions.  The polymers upon copolymerization with polyvinylidene monomers can be lightly cross-linked to give a resin having ion-exchange capacity.ALSO:Compounds of formula: <FORM:0834308/II/1> in which R1 and R2 taken individually are alkyl radicals, one being methyl and the other containing from 1 to 8 carbon atoms, of R1 and R2 when taken together form a divalent saturated aliphatic hydrocarbon group containing from 4 to 9 carbon atoms which together with the carbon atom on to which R1 and R2 are bonded form a five- or six-membered ring, n is 1 or 2 and m is 1 or 2, are stated to be useful for the classification of ores and when dissolved in water are effective flotation agents.ALSO:Fungicidal compositions comprise as active ingredients compounds of formula <FORM:0834308/VI/1> in which R1 and R2 are alkyl radicals, one being methyl and the other containing from 1 to 8 carbon atoms, or R1 and R2 when taken together form a saturated aliphatic hydrocarbon group which together with the carbon atom to which R1 and R2 are both bonded form a five- or six-membered ring, and n and m are 1 or 2. The compositions may be formulated into sprays or dusts or dissolved in an organic solvent miscible with water the resulting solution being extended with water to give a solution.  An emulsifiable concentrate may be prepared by dissolving one of the active agents in an organic solvent, e.g. naphtha or xylene, and adding an emulsifier such as alkylphenoxypolyethoxyethanols, methylene bis diamylphenoxypolyethoxyethanols, and oleic acid-polyglycerol condensates.  Wet-table powders may be prepared by taking up the active agent in a finely divided solid, such as clay, and incorporating a dispersing agent, such as the sodium salt of condensed naphthalene-formaldehyde sulphonates, and a wetting agent such as one of the above emulsifiers or sodium dodecyl sulphate or octyl-phenoxyethoxyethoxyethyl sulphonate.