Patent GB-946021-A (GB)
Title: Furan derivatives and antimicrobial compositions containing furan derivatives
IPC: D06M16/00
Filed: 1960-01-18
Abstract: The invention relates to compounds of the general formula: <FORM:0946021/C2/1> in which R, R1 and R11 are alkyl radicals, aryl radicals or heterocyclic radicals, and may be the same as or different from one another, but are not all methyl.  In examples stannous chloride dihydrate was added to hydroxymethyl furfural in propionic anhydride to yield hydroxymethyl furfural tripropionate.ALSO:Paints are rendered antimicrobial by incorporating a furan compound of a formula: <FORM:0946021/C3/1> where R is CH3, CH3CH2-, <FORM:0946021/C3/2> , <FORM:0946021/C3/3> CH3CH2CH(C2H5) CHCH2-, CH2=C (CH2)8-, COOH(CH2)4-, COOH(CH2)x-, MOOC(CH2)x-; z being an alkyl group having up to 8 carbon atoms; <FORM:0946021/C3/4> <FORM:0946021/C3/5> where R is CH3-, C2H5-, CH2=CH-CH2-; <FORM:0946021/C3/6> <FORM:0946021/C3/7> <FORM:0946021/C3/8> where R is (CH2)8, CH2CH2, CH=CH,(CH2)4, or (C6H4)-; <FORM:0946021/C3/9> where R is CH3-, CH3CH2-, C3H7-, and R1 is COOH(CH2)xCO-, and MOOC(CH2)xCO-; <FORM:0946021/C3/100> and R1 may be the same as or dissimilar from R; Z being 1-8 alkyl group <FORM:0946021/C3/111> <FORM:0946021/C3/122> where R is COOH(CH2)xCO-, or MOOC(CH2)x CO-; x in all the above compounds is an integer of 2 or greater and M is zinc, copper, cobalt, sodium, or calcium; <FORM:0946021/C3/133> where R, R1, and R11 are lower alkyl particularly methyl or ethyl groups, and may be the same as or different from each other; <FORM:0946021/C3/144> where X is halogen such as chlorine or bromine <FORM:0946021/C3/155> where X is a halogen; <FORM:0946021/C3/166> where R is methyl, ethyl, or alkyl. In an example a naval ship paint comprises titanium dioxide, zinc oxide, lamp black, extender, plaskon, mineral spirits, a vinyl chloride/vinyl acetate copolymer, xylene and driers.  In another example a naval ship paint comprises lecithin, extender, titanium dioxide, methocel, fungicide, anti-foam, hexylene and diethylene glycol, and acrylonitrile-vinylidene chloride.ALSO:A paraffin wax composition having antimicrobial properties comprises 2-90% of methoxymethylfurfural.  Soaps are rendered antimicrobial by incorporating therein a furan compound of the formula <FORM:0946021/C3/1> Z being an alkyl group having up to 8 carbon atoms. <FORM:0946021/C3/2> <FORM:0946021/C3/3> where R is CH3-, C2H5-, CH2=CH-CH2-; <FORM:0946021/C3/4> <FORM:0946021/C3/5> <FORM:0946021/C3/6> where R is (CH2)8, CH2CH2, CH=CH, (CH2)4, or (C6H4)-; <FORM:0946021/C3/7> where R is CH3-, CH3CH2-, C3H7-, and R1 is COOH(CH2)xCO-, and Z being 1-8 alkyl group MOOC(CH2)xCO-; <FORM:0946021/C3/8> and R1 may be the same as or dissimilar from R; <FORM:0946021/C3/9> <FORM:0946021/C3/100> where R is COOH(CH2)xCO-, or MOOC (CH2)xCO-; x in all the above compounds is an integer of 2 or greater and M is zinc, copper, cobalt, sodium or calcium; <FORM:0946021/C3/111> where R, R1 and R11 are lower alkyl, particularly methyl or ethyl groups, and may be the same as or different from each other; <FORM:0946021/C3/122> where X is a halogen such as chlorine or bromine; <FORM:0946021/C3/133> where X is a halogen; <FORM:0946021/C3/144> where R is methyl, ethyl, or alkyl.ALSO:An antimicrobial composition comprises a dispersion in a carrier medium of a furan compound of the formula: <FORM:0946021/A5-A6/1> wherein R is CH3, CH3CH2-, <FORM:0946021/A5-A6/2> , <FORM:0946021/A5-A6/3> CH3CH2CH(C2H5)CHCH2-, CH2 = CH(CH2)8-, COOH(CH2)4-, COOH(CH2)x-, MOOC(CH2)x-; Z being an alkyl group having up to 8 carbon atoms; <FORM:0946021/A5-A6/4> <FORM:0946021/A5-A6/5> where R is CH3-, C2H5-, CH2 = CH-CH2-; <FORM:0946021/A5-A6/6> ; <FORM:0946021/A5-A6/7> ; <FORM:0946021/A5-A6/8> wherein R is (CH2)8, CH2CH2, CH = CH, (CH2)4, or (C6H4)-; <FORM:0946021/A5-A6/9> where R is CH3-, CH3CH2-, C3H7-, and R1 is COOH(CH2)xCO-, and MOOC(CH2)xCO-; <FORM:0946021/A5-A6/100> and R1 may be the same or dissimilar from R; Z being 1-8 alkyl group; <FORM:0946021/A5-A6/111> ; <FORM:0946021/A5-A6/122> where R is COOH(CH2)xCO-, or MOOC (CH2)xCO-; x in all the above compounds is an integer of 2 or greater and M is zinc, copper, cobalt, sodium or calcium; <FORM:0946021/A5-A6/133> where R, R1 and R11 are lower alkyl particularly methyl or ethyl groups, and may be the same as or different from each other; <FORM:0946021/A5-A6/144> where X is a halogen such as chlorine or bromine <FORM:0946021/A5-A6/155> where X is a halogen; <FORM:0946021/A5-A6/166> where R is methyl, ethyl, or alkyl.  The composition may be prepared as dispersions e.g. emulsions of the compounds in solutions in aqueous media or in organic monomeric or polymeric alcohols, such as ethyl or butyl alcohol, propylene glycol, sorbitol, and polyoxyglycols; chlorinated solvents or aromatics as benzene and xylene; mineral spirits, oils such as neatsfoot, and soybean oil; or waxes such as carnauba wax, and also dispersed in an inert carrier.  There may also be added to the composition stearic acid, anhydrous lanolin, glycol stearate, sorbitol solution, isopropyl palmitate.ALSO:Leather and textile materials are rendered antimicrobial by incorporating a furan compound of a formula <FORM:0946021/D1-D2/1> where R is CH3, CH3CH2-, <FORM:0946021/D1-D2/2> , <FORM:0946021/D1-D2/3> CH3CH2CH(C2H5) CHCH2-, CH2=CH(CH2)8-, COOH(CH2)4-, COOH(CH2)x-MOOC(CH2)x-; z being an alkyl group having up to 8 carbon atoms; <FORM:0946021/D1-D2/4> <FORM:0946021/D1-D2/5> where R is CH3-, C2H5-, CH2=CH-CH2-; <FORM:0946021/D1-D2/6> ; <FORM:0946021/D1-D2/7> ; <FORM:0946021/D1-D2/8> where R is (CH2)8, CH2CH2, CH=CH, (CH2)4, or (C6H4)-; <FORM:0946021/D1-D2/9> where R is CH3-, CH3CH2-, C3H7-, and R1 is COOH(CH2)xCO-, and MOOC(CH2)xCO-; <FORM:0946021/D1-D2/100> and R1 may be the same as or dissimilar from R; Z being 1-8 alkyl group <FORM:0946021/D1-D2/111> ; <FORM:0946021/D1-D2/122> where R is COOH(CH2)xCO-, or MOOC(CH2)xCO-; x in all the above compounds is an integer of 2 or greater and M is zinc, copper, cobalt, sodium, or calcium; <FORM:0946021/D1-D2/133> where R, R1 and R11 are lower alkyl particularly methyl or ethyl groups, and may be the same as or different from each other; <FORM:0946021/D1-D2/144> where X is halogen such as chlorine or bromine <FORM:0946021/D1-D2/155> where X is a halogen; <FORM:0946021/D1-D2/166> where R is methyl, ethyl, or alkyl.  In an example a naval ship paint comprises titanium dioxide, zinc oxide, lamp black, extender, plaskon, mineral spirits, a vinyl chloride/vinyl acetate copolymer, xylene and driers.  In another example a naval ship paint comprises lecithin, extender, titanium dioxide, methocel, fungicide, anti-foam, hexylene and diethylene glycol, and acrylonitrile-vinylidene chloride.ALSO:Microbial spoilage in food e.g. ground beef, poultry, pancake syrup, orange juice and bread is reduced by incorporating therein a furan compound of the formula <FORM:0946021/A1-A3/1> where R is <FORM:0946021/A1-A3/2> <FORM:0946021/A1-A3/3> Z being an alkyl group having up to 8 carbon atoms; <FORM:0946021/A1-A3/4> <FORM:0946021/A1-A3/5> where R is CH3-, C2H5-, CH2=CH-CH2-; <FORM:0946021/A1-A3/6> <FORM:0946021/A1-A3/7> <FORM:0946021/A1-A3/8> where R is (CH2)8; CH2CH2, CH=CH, (CH2)4, or (C6H4)-; <FORM:0946021/A1-A3/9> where R is CH3-, CH3 CH2-, C3H7-, and R1 is COOH(CH2)xCO-, and MOOC(CH2)xCO-; <FORM:0946021/A1-A3/100> and R1 may be the same as or dissimilar from R; Z being 1-8 alkyl group. <FORM:0946021/A1-A3/111> <FORM:0946021/A1-A3/122> where R is COOH(CH2)xCO-, or MOOC (CH2)xCO-; x in all the above compounds is an integer of 2 or greater and M is zinc, copper, cobalt, sodium, or calcium; <FORM:0946021/A1-A3/133> where R, R1, and R11 are lower alkyl groups, particularly methyl or ethyl, and may be the the same as or different from each other; <FORM:0946021/A1-A3/144> where X is a halogen such as chlorine or bromine; <FORM:0946021/A1-A3/155> where X is a halogen; <FORM:0946021/A1-A3/166> where R is methyl, ethyl, or alkyl.