Patent GB-1122445-A (GB)
Title: Halogenated diurethanes
IPC: D06M16/00
Filed: 1966-03-01
Abstract: Novel di-urethanes of formula Ar-OOC-HN-R-NH-COO-Ar where R represents an alkylene radical having 2 to 18 carbon atoms, which may be interrupted by O, S, SO, SO2 or by an N-alkyl group containing up to 8 carbon atoms; or a divalent aromatic or araliphatic radical; and Ar represents a tri- or tetra-halogenophenyl radical; which have biocidal properties, may be incorporated in a plasticized polyvinylchloride paste.ALSO:Novel diurethanes of formula ArOOC-NH-R-NH-COOAr, where R represents an alkylene radical having 2-18 carbon atoms which may be interrupted by O, S, SO, SO2 or an N-alkyl group containing up to 8 carbon atoms; or a divalent aromatic or araliphatic radical; and Ar represents a tri- or tetra-halogenophenyl radical, are prepared by reacting a compound of formula X-R-X with approximately 2 mols. of a compound of formula Ar-Y, where X and Y represent residues capable of forming the bridge -OCONH- by condensation or addition, and, if the starting material used is a hypohalogenated compound of formula Ar-Y, further halogenating the di-urethane obtained to the desired degree.ALSO:A halogenated di-urethane of formula Ar OOC-NH-R-NH-COO Ar where R represents an alkylene radical containing 2 to 18 carbon atoms which may be interrupted by O, S, SO, SOz or by an N-alkyl group containing up to 8 carbon atoms; or a divalent aromatic or aliphatic radical, and Ar represents a tri- or tetrahalogenophenyl radical, is used, e.g. mixed with: a biocide or pesticide, an adhesive, a surface-active agent such as a soap, water, a liquid solvent, an inert solid or gaseous diluent, for disinfecting seeds.ALSO:Di-urethanes of formula:-  Ar-OOC-HN-R-NH-COO-Ar where R is an alkylene radical containing 2-18 carbon atoms which may be interrupted by O, S, SO, SO2 or an N-alkyl group containing up to 8 carbon atoms; or a divalent aromatic or araliphatic radical, and Ar represents a tri- or tetra-halogenophenyl radical, may be used as preservatives in the cellulose and paper industries, e.g. for preventing slime formation in paper making machines caused by micro-organisms.ALSO:Disinfectant compositions having activity against harmful micro-organisms, which may be used in plant protection, timber protection, for protecting fibrous materials (including textiles), preserving agricultural produce, as disinfectants for preserving a wide variety of technical products such as textile auxiliaries and adjuvants, glues, binding agents, paints, thickeners, colour and printing pastes and similar preparations based on organic or inorganic dyestuffs or pigments, as washing or cleansing agents and as pharmaceutical and cosmetic agents, contain as active ingredient at least one di-urethane of formula ArOOC-HN-R-NH-COOAr where R represents an alkylene radical containing 2-18 carbon atoms which may be interrupted by O, S, SO, SO2 or by an N-alkyl group containing up to 8 carbon atoms; or a divalent aromatic or araliphatic residue, and Ar represents a tri- or tetra-halogenophenyl radical, together with at least one other ingredient such as a solvent, a solid, liquid or gaseous diluent, an adhesive, an emulsifier, a dispersant, a wetting agent or another pesticide.  In washing and cleansing compositions the di-urethanes may be combined with surface-active agents such as alkylaryl sulphonates, condensation products of fatty acids with methyltaurine, hydroxyethanesulphonates or proteins, primary alkyl sulphonates, anionic, non-ionic or cationic compounds, industrial detergents such as a condensed phosphate, or an organic lyophilic polymer capable of increasing the dirt-carrying capacity of the washing liquor, e.g. an alkali metal salt of carboxymethylcellulose.  Other biocides with which the di-urethanes may be combined include 3,4-dichlorobenzyl alcohol, ammonium compounds, e.g. 3,5-diisobutylphenoxyethoxyethyl dimethyl benzyl ammonium chloride, cetyl pyridinium chloride, cetyl trimethylammonium bromide, halogenated dihydroxydiphenylmethanes, tetramethylthiuram disulphide, 2,2-thio-bis-(4,6-dichlorophenol) and organic compounds that contain the thiotrichloromethyl group, 2-nitro-2-furfuryl iodide, salicylanilides, dichloro-, dibromo- and tribromo salicylanilides, dichlorocyanuric acid tetrachlorosalicylanilides, aliphatic thiuran sulphides and hexachlorophen.  Compositions may also contain anti-oxidants, light filters, optical brighteners, softeners and perfumes. Formulations include soaps in tablet, semi-solid or liquid form, pastes, powders, emulsions, suspensions, solutions in organic solvents, sprays, granulates, tablets, pencils, capsules ointments, skin and shaving creams, mouthwashes, dental preparations, shampoos and other preparations for the care of the hair.  The di-urethanes may also be incorporated in synthetic materials, these synthetics having sterile properties may be used for a wide variety of objects for daily use.