Process for producing polyurethane resins and sheet materials

A water-insoluble, water-nondispersible and solvent-soluble polyurethane resin having a quaternary nitrogen atom content of 0.05-0.23% by weight and having improved physical properties and improved dyeability, which has been obtained by reacting an organic diisocyanate (A) with active hydrogen atom-containing compounds comprising a macromolecular polyol (B) and a low-molecular weight polyfunctional compound (C), wherein (1) a part of the active hydrogen atom-containing compounds is at least one quaternary nitrogen atom-containing polyol (D) selected from the group consisting of low-molecular weight polyols, polyether polyols and polyester polyols having at least one quaternary nitrogen atom, (2) 40-100 equivalent % of (C) is a low-molecular weight polyfunctional compound (E) having no nitrogen atom other than the functional group, and (3) the equivalent ratio of the NCO groups of (A) to active hydrogen atom-containing groups of the active hydrogen atom-containing compounds in total is 1:0.9-1.1.

A process for producing sheet material comprising applying to a substrate a solution of water-insoluble, water-nondispersible polyurethane resin having a quaternary nitrogen atom content of 0.05-0.23% by weight, obtained by reacting an organic diisocyanate (A) with active hydrogen atom-containing compounds comprising a macromolecular diol (B.sub.1) and a low-molecular weight bifunctional compound (C.sub.1), wherein (1) a part of the active hydrogen atom-containing compounds is at least one quaternary nitrogen atom-containing diol (D.sub.1) selected from the group consisting of low-molecular weight diols, polyether diols and polyester diols having at least one quaternary nitrogen atome, (2) 40-100 equivalent % of (C.sub.1) is a low-molecular weight bifunctional compound (E.sub.1) having no nitrogen atom other than the functional group, and (3) the equivalent ratio of the NCO groups of (A) to active hydrogen atom-containing groups of the active hydrogen atom-containing compounds in total is 1:0.9-1.1.

A sheet material having improved physical properties and improved dyeabilities which comprises a layer formed by applying to a substrate a solution of a water-insoluble, water-nondispersable polyurethane resin having a quaternary nitrogen atom content of 0.05-0.23% by weight, obtained by reacting an organic diisocyanate (A) with active hydrogen atom-containing compounds comprising a macromolecular polyol (B) and a low-molecular weight polyfunctional compound (C), wherein (1) part of the active hydrogen atom-containing compounds is at least one quaternary nitrogen atom-containing polyol (D) selected from the group consisting of low-molecular weight polyols, polyether polyols and polyester polyols having at least one quaternary nitrogen atom, (2) 40-100 equivalent % of (C) is a low molecular weight polyfunctional compound (E) having no nitrogen atom other than the functional group, and (3) the equivalent ratio of NCO group of (A) to active hydrogen atom-containing group of the active hydrogen atom-containing compounds in total is 1:0.9-1.1, and immersing said substrate coated with said solution in a coagulating bath containing a liquid which is compatible with the solvent and is a non-solvent for the polyurethane resin.

A polyurethane composition, which comprises a solution in a solvent of a water-insoluble, water-nondispersible polyurethane resin having a quaternary nitrogen atom content of 0.05-0.23% by weight and having improved physical properties and improved dyeability, which has been obtained by reacting an organic diisocyanate (A) with active hydrogen atom-containing compounds comprising a macromolecular polyol (B) and a low-molecular weight polyfunctional compound (C), wherein (1) a part of the active hydrogen atom-containing compounds is at least one quaternary nitrogen atom-containing polyol (D) selected from the group consisting of low-molecular weight polyols, polyether polyols and polyester polyols having at least one quaternary nitrogen atom, (2) 40-100 equivalent % of (C) is a low-molecular weight polyfunctional compound (E) having no nitrogen atom other than in the functional group, and (3) the equivalent ratio of the NCO groups of (A) to the active hydrogen atom-containing groups of the active hydrogen atom-containing compounds in total is 1:0.9-1.1.