Patent GB-895431-A (GB)
Title: New oxazole compounds and process for their manufacture
IPC: C11D3/48
Filed: 1959-05-25
Abstract: Ultra-violet light screening agents and bactericidal or fungical agents comprise oxazole compounds in which the two vicinal carbon atoms of the oxazole ring are members of a substituted or unsubstituted benzene ring and the other carbon atom of the ring is bound to a carbon atom of a pyridine ring, e.g. of general formula, <FORM:0895431/III/1> or <FORM:0895431/III/2> where X represents a hydrogen atom, a methyl group or a phenyl residue, X1 a hydrogen or chlorine atom, or an alkyl group containing up to 4 carbon atoms or a phenyl residue, and X2 and X3 each represent a hydrogen or chlorine atom (see Group IV(a)) The compounds may be incorporated in hydrophobic oily, fatty or wax-like substances such as soaps; salts of sulphonate detergents, e.g. salts of substituted benzimidazoles substituted by a higher alkyl residue at the 2-carbon atom, salts of monocarboxylic acid esters of 4-sulphophthalic acid with higher fatty alcohols, or salts of fatty acid sulphonates, alkyl-aryl sulphonic acids or condensation products of higher fatty acids with aliphatic oxy- or amino-sulphonic acids; non-ionic detergents, e.g. polyglycol ethers from ethylene oxide and higher fatty alcohols, alkyl-phenols or fatty amines; together with optional additives such as alkali metal carbonates, phosphates, pyrophosphates, polyphosphates, metaphosphates, silicates, perborates or percarbonates, and insecticides, bactericides, dyestuffs and optical bleaching agents. The mixtures are prepared by conventional mixing or grinding and are in the form of powder, flakes, pieces, shavings or pastes.  Examples describe the preparation of a dispersion of a compound derived from 1-amino-2-hydroxy-5-methyl benzene and isonicotinic acid with sodium lauryl sulphate, sodium dodecyl-benzenesulphonate, sodium tripolyphosphate and sodium sulphate and a coating composition of polyvinyl chloride, dioctyl phthalate, methyl ethyl ketone, toluene and copper phthalocyanine tetramethoxy-propylsulphamide, and the compound derived from 1-amino-2-hydroxy benzene and nicotinic acid applied to tin foil, and protected by a second film of the same composition without the dyestuff, to yield a film of good light fastness.ALSO:Ultra-violet light screening and bactericidal or fungicidal agents comprise oxazole compounds in which the two vicinal carbon atoms of the oxazole ring are members of a substituted or unsubstituted benzene ring and the other carbon atom of the ring is bound to a carbon atom of a pyridine ring, e.g. compounds of the general formula <FORM:0895431/IV (a)/1> <FORM:0895431/IV (a)/2> where X represents a hydrogen atom, a methyl group or a phenyl residue, X1 a hydrogen or chlorine atom or an alkyl group containing up to 4 carbon atoms or a phenyl residue, and X2 and X3 each represent a hydrogen or chlorine atom (see Group IV(b)).  The compounds may be incorporated in a substratum as a protection therefor, or to protect substances in the substratum, or used as a "filter-layer".  Cellulose materials, which may be natural, such as cotton, hemp, flax, linen, jute or ramie, or synthetic, such as regenerated cellulose, and polymeric materials, such as polyacrylonitrile or polyamides, and other natural or synthetic resins or rubbers are protected.  Examples describe the use of the compound derived from 1-amino-2-hydroxy -5-methyl benzene and isonicotinic acid in the treatment of a cotton calico fabric to render it resistant to Chaetomium globosum, and the addition of the compound to a cellulose acetate spinning solution. The lightscreening of a composition of polvinyl chloride, a stabilizer, dioctyl phthalate, methyl ethyl ketone, toluene, and copper phthalocyanine tetramethoxypropyl-sulphamide, with a compound derived from 1-amino 2-hydroxy-benzene and nicotinic acid, which composition is applied as a film and covered by a second film of the composition without the dyestuff, is also described.ALSO:The invention comprises oxazole compounds in which the two vicinal carbon atoms of the oxazole ring are members of a substituted or unsubstituted benzene ring, and the carbon atom between the nitrogen and oxygen atoms of the oxazole ring is bound to a carbon atom of a pyridine ring, e.g. of general formula <FORM:0895431/IV (b)/1> <FORM:0895431/IV (b)/2> where X represents a hydrogen atom, a methyl group, or a phenyl residue, X1 a hydrogen or chlorine atom, or an alkyl group containing up to 4 carbon atoms or a phenyl residue, and X2 and X3 each represent a hydrogen or chlorine atom, and in formula II the pyridine ring is bound by the 3- or 4-position to the oxazole ring.  The compounds are prepared by heating and/or treating with an agent capable of splitting off water, an acyl compound derived from an o-amino-oxyaryl compound of the benzene series having a primary amine group and a pyridine carboxylic acid, or by heating an o-aminooxy compound of the benzene series containing a primary amino group with a pyridine carboxylic acid or a functional derivative, e.g. alkyl ester thereof.  The reaction may be carried out with or without a solvent, in the presence of boric or polyphosphoric acid. 1-amino-2-oxybenzenes and pyridine carboxylic acid starting materials are listed and examples describe the condensation of 1-amino-2-hydroxy-5-methylbenzene with nicotinic or isonicotinic acids, 1-amino-2-hydroxy-benzene, 1-amino-2-hydroxy-benzene, 1-amino-2 - hydroxy - 5 - phenylbenzene 1 - amino - 2 - hydroxy - 5 - chlorobenzene, 1 - amino - 2 - hydroxy - 3 : 5 : 6 - trichlorobenzene with nicotinic acid using polyphosphoric acid as solvent and condensing agent, in the absence of air.  The preparation of a quaternary ammonium compound by the reaction of p-chlorobenzyl chloride and dimethyl formamide on the product of the reaction of nicotinic acid and 1-amino-2-hydroxy-5-methyl benzene is also described.  The compounds are suitable for use as U.V. light screening agents for textiles, natural and synthetic, animal or vegetable fibrous materials, coatings, films, cosmetics and photography and also as bactericidal or fungicidal agents.ALSO:Ultra-violet light screening and bactericidal or fungicidal agents comprise oxazole compounds in which the two vicinal carbon atoms of the oxazole ring are members of a substituted or unsubstituted benzene ring and the other carbon atom of the ring is bound to a carbon atom of a pyridine ring, e.g. compounds of the general formula <FORM:0895431/IV (c)/1> where X represents a hydrogen atom, a methyl group or a phenyl residue, X1 a hydrogen or chlorine atom or an alkyl group containing up to 4 carbon atoms or a phenyl residue, and X2 and X3 each represent a hydrogen or chlorine atom (see Group IV(a)).  Textile materials such as wool, silk, cotton, hemp, flax, linen, jute, ramie or regenerated cellulose, dyed or undyed, are protected, and the compound may be incorporated in the substratum or in a filter layer in an amount in a range 0.01% to 10% of the material.  An example describes the treatment of a cotton calico fabric with ethanol solutions of compounds derived from 1 - amino - 2 - hydroxy - 5 - methyl-benzene or -5-phenyl-benzene and 1-amino-2-hydroxybenzene and nicotinic acid as protection against chaetomium globosum, and the treatment of a film of acetyl cellulose as protection against ultra-violet light.ALSO:Bactericidal or fungicidal agents suitable for use in the food industry comprise oxazole compounds in which the two vicinal carbon atoms of the oxazole ring are members of a substituted or unsubstituted benzene ring and the other carbon atom of the ring is bound to a carbon atom of a pyridine ring, e.g. of general formula <FORM:0895431/VI/1> where X represents a hydrogen atom, a methyl group, or a phenyl residue, X1 a hydrogen or chlorine atom, or an alkyl group containing up to 4 carbon atoms or a phenyl residue, and X2 and X3 each represent a hydrogen or chlorine atom (see Group IV (a)).  The compounds may be used in conjunction with detergents such as salts of sulphonated substituted benzimidazoles, monocarboxylic esters of 4-sulphophthalic acid with higher fatty alcohols, polyglycol ethers derived from ethylene oxide and higher fatty alcohols, alkyl-phenols or fatty amines, mixed with alkali metal carbonates, phosphates, pyrophosphates, polyphosphates, metaphosphates, silicates, perborates or percarbonates, and in an example, a mixture of sodium lauryl sulphate, sodium dodecyl-benzene sulphonate, sodium tripolyphosphate and sodium sulphate with compounds derived from 1-amino-2-hydroxy-5-methylbenzene with isonicotinic and nicotinic acids gives inhibitive or lethal effect on Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Trichophyton interdigitale and Endomyces albicans.