Patent GB-942547-A (GB)
Title: Hydroxy-terminated polyether-based urethanes and coating compositions containing same
Inventor: DAMUSIS ADOLFAS
IPC: C08G18/48
Filed: 1960-03-18
Abstract: Hydroxy terminated urethanes of the general formula: <FORM:0942547/C2/1> where R is hydrogen or methyl, y is zero or one, Q is the same in both occurencies and is the radical of a branched polyether polyol in which a hydroxyl hydrogen has been removed, said branched polyether polyol containing three or four hydroxyl groups per molecule, and being an alkylene oxide addition product (b) of a polyhydric aliphatic alcohol containing up to eight carbon atoms inclusive and containing three or four hydroxy groups per molecule, or an alkylene-oxide addition product (d) of a polyol containing at least one tertiary nitrogen atom, are made by reacting about one molar proportion of arylene diisocyanate with about two molar proportions of a polyether polyol (b) or (d). Specified polyether polyols (b) are compounds of the general formula: <FORM:0942547/C2/2> where R1 with attached oxygen atoms represents a polyhydric aliphatic alcohol radical, n is 1, 2 or 3 and x and z are zero or one. Specified polyols (d) are of the formula: <FORM:0942547/C2/3> where Z is an alkylene radical containing from 2 to 6 carbon atoms inclusive, n is 1, 2 or 3 and x is zero, or of the formula: <FORM:0942547/C2/4> where n is 1, 2 or 3 and x is zero or one.  The examples describe the preparation of hydroxy terminated urethanes from: (1) a polyoxypropylene derivative of trimethylol propane and toluylene diisocyanate; (2) a monoethylene oxide addition product of a polyoxypropylene derivative of trimethylol propane and phenylene diisocyanate; (3) a propylene oxide-pentaerythritol addition product and diphenyl methane -4:4diisocyanate; (4) a propyleneoxide-pentaerythritol addition product and toluylene diisocyanate; (5) toluylene diisocyanate and a hexanetriol-propylene oxide addidtion product; (6) toluylene diisocyanate and a polyoxypropylene derivative of triisopropanolamine; (7) toluylene diisocyanate and a polyoxypropylene derivative of N:N:N1:N1-tetrakis(2-hydroxypropyl)ethylene diamine; (8) toluylene diisocyanate and an addition product of propylene oxide and N:N:N1:N1-tetrakis (2-hydroxypropyl) ethylene diamine; (9) toluylene diisocyanate and an addition product of ethylene oxide and propylene oxide with N:N:N1:N1-tetrakis (2-hydroxypropyl) ethylene diamine; (10) toluylene diisocyanate and a propylene oxide-triisopropanolamine reaction product and (11) toluylene diisocyanate and a polyoxypropylene derivative of triisopropanolamine. The preparations are all effected in the presence of 2-ethoxyethyl acetate and xylene.ALSO:Hydroxy terminated urethanes of the general formula: <FORM:0942547/C3/1> where R is hydrogen or methyl, y is zero or one, Q is the same in both occurencies and is the radical of a branched polyether polyol in which a hydroxyl hydrogen has been removed, said branched polyether polyol containing three or four hydroxyl groups per molecule, and being an alkylene oxide addition product (b) of a polyhydric aliphatic alcohol containing up to eight carbon atoms inclusive and containing three or four hydroxy groups per molecule, or an alkylene-oxide addition product (d) of a polyol containing at least one tertiary nitrogen atom, are made by reacting about one molar proportion of arylene diisocyanate with about two molar proportions of a polyether polyol (b) or (d). Specified polyether polyols (b) are compounds of the general formula: <FORM:0942547/C3/2> where R1 with attached oxygen atoms represents a polyhydric aliphatic alcohol radical, n is 1, 2 or 3 and x and z are zero or one. Specified polyols (d) are of the formula: <FORM:0942547/C3/3> where Z is an alkylene radical containing from 2 to 6 carbon atoms inclusive, n is 1, 2 or 3 and x is zero, or of the formula: <FORM:0942547/C3/4> where n is 1, 2 or 3 and x is zero or one. The examples describe the preparation of hydroxy terminated urethanes from: (1) a polyoxypropylene derivative of trimethylol propane and toluylene diisocyanate; (2) a monoethylene oxide addition product of a polyoxypropylene derivative of trimethylol propane and phenylene diisocyanate; (3) a propylene oxide-pentaerythritol additional product and diphenyl methane-4:41-diisocyanate; (4) a propylene oxide-pentaerythritol addition product and toluylene diisocyanate; (6) toluylene diisocyanate and a polyoxypropylene derivative of triisopropanolamine; (7) toluylene diisocyanate and a polyoxy-propylene derivative of N:N:N1:N1-tetrakis (2-hydroxypropyl) ethylene diamone; (8) toluylene diisocyanate and an addition product of propylene oxide and N:N:N1:N1-tetrakis (2-hydroxypropyl) ethylene diamine; (9) toluylene diisocyanate and an addition product of ethylene oxide and propylene oxide with N:N:N1:N1-tetrakis (2-hydroxypropyl) ethylene diamine; (10) toluylene diisocyanate and a propylene oxide-triisopropanolamine reaction product and (11) toluylene diisocyanate and a polyoxypropylene derivative of triiso propanolamine. The preparations are effected in the presence of 2-ethoxyethyl acetate and xylene and the products admixed with (a) an isocyanate terminated reaction product of toluylene diisocyanate with a propylene oxide addition product of trimethylol propane or (b) an isocyanate terminated reaction product of polypropylene glycol, to form two-component urethane coating compositions.