Patent GB-977212-A (GB)
Title: Improvements relating to polyurethanes
IPC: C08G18/66
Filed: 1962-06-22
Abstract: Halogenated polyurethanes are produced by a process which comprises reacting in any order (a) 2 to 3 molecular proportions of one or more ring-polyhalogenated toluene 2,4- or 2,6-di-isocyanates, in which the halogen is chlorine or bromine or both, (b) one molecular proportion of one or more polyether or polyester glycols of number-average molecular weight 750 to 3,500, and (c) one or more non-polymeric aliphatic dihydroxy compounds, being either cis-1, 4-dihydroxycyclohexane or a 2,2-di-substituted-1, 3-propanediol wherein the substituents are inert to isocyanate groups, with or without at least one organic compound of number average molecular weight 92 to 4,000 having 3 or more hydroxyl groups per molecule as the sole isocyanate reactable functionality; the total molecular proportion of hydroxyl groups in (c) being 75 to 100% of the difference between the total molecular proportions of isocyanate groups in (a) and of hydroxyl groups in (b) with the proviso that no more than 20% of the total molecular proportion of hydroxyl groups in (c) be supplied by organic compounds having 3 or more hydroxyl groups per molecule.  The polyether glycols used may be polyalkylene or polyalkylene-arylene ether or ether-thioether glycols. Starting materials for the preparation of polyether glycols are specified. Halogenated diisocyanates specified are 3, 5-dichlorotoluene-2, 4-di-isocyanate; 3, 5-dichlorotoluene-2, 6-diisocyanate; 3, 5, 6-trichlorotoluene-2, 4-diisocyanate; 3, 5-dibromotoluene-2, 4-di-isocyanate; 3, 5-dibromotoluene-2, 6-di-isocyanate; 3, 5, 6-tribromotoluene-2, 4-di-isocyanate; 3-bromo -5- chlorotoluene-2, 4-di-isocyanate; 5-bromo -3- chlorotoluene-2, 6-di-isocyanate; 6-bromo-3, 5-dichlorotoluene-2, 4-di-isocyanate; 3, 6-dichlorotoluene-2, 4-di-isocyanate and 5, 6-dichlorotoluene-2 4-di-isocyanate.  Substituted propanediols specified are 2, 2-dimethyl-1, 3-propanediol; 2-ethyl -2- methyl-1, 3-propanediol; 2-methyl -2-n-propyl-1, 3-propanediol; 2, 2-di-isobutyl-1, 3-propanediol; 2-allyloxymethyl-2-methyl-1, 3-propanediol; 2-methyl -2- (4-pentenyloxymethyl)-1, 3-propanediol; 2-allyloxyethyl -2- methyl-1, 3-propanediol; 2-methyl-2-(10-undecenyloxymethyl)-1, 3-propanediol and 2-(3-methallyloxymethyl) -2- methyl-1, 3-propanediol. Triols and polyols specified are polyether triols; polyester triols; glycerol; 1,2, 6-hexanetriol; 1, 1, 1-trimethylolpropane; 1, 1, 1-trimethylolethane; pentaerythritol; 3-(2-hydroxyethoxy)-1, 2-propanediol; mannitol; galactitol; talitol; iditol; allitol; gulitol; arobitol; ribitol; xylitol; erythritol; threitol; 1, 2, 5, 6-tetrahydroxyhexane; meso-inositol; sucrose; glucose; galactose; mannose; fructose; xylose; arabinose; dihydroxyacetone; glucose -a - methyl/glucoside; 1, 1, 1-tris(2-hydroxyethoxymethyl)ethane; and 1, 1, 1-tris(2-hydroxypropoxymethyl)propane. Catalysts such as triethylenediamine; stannous octoate; dibutyltin dilaurate; N-ethylmorpholine N-oxide and ferric acetylacetonate may also be present as may inert solvents such as methyl isobutyl ketone, ethyl acetate, toluene, xylene, hexane, trichloroethylene, tetrachloroethylene and tetrahydrofuran. The elastomeric products of the invention are useful in seals, gaskets, hose, shoe soles, shoe heels, solid tyres, protective covering sheet material, diaphragms, bellows, printing rolls, stoppers, shock absorbers and instrument and machinery mountings. Specifications 733,624 and 801,023 are referred to.