Polyurethane cured with an aromatic monosulfide diamine

Claim 2

A CURED POLYURETHANE PREPARED BY REACTING 4,4''DIAMINODIPHENYLSULFIDE WITH (A) A MIXTURE OF AN ORGANIC POLYISOCYANATE HAVING AN ISOCYANATE FUNCTIONALITY OF 2 TO 3 WITH A POLYMERIC POLYOL HAVING A HYDROXYL FUNCTIONALITY OF 2 TO 3 AND A MOLECULAR WEIGHT IN THE RANGE OF ABOUT 500 TO ABOUT 6000, WHERE THE RATIO OF ISOCYANATO GROUPS OF SAID POLYISOCYANATE TO HYDROXYL GROUPS OF SAID POLYMERIC POLYOL IS IN THE RANGE OF ABOUT 1.3/1 TO ABOUT 5/1 OR (B) THE REACTION PRODUCT OF SAID POLYISOCYANATE AND SAID POLYMERIC POLYYOL.

Claim 3

The cured polyurethane of claim 1 prepared by reacting 4,4''-diaminodiphenylsulfide at a temperature in the range of about 20*C to about 150*C with an isocyanate-terminated prepolymer prepared by the method which comprises reacting a polyisocyanate, having an isocyanate functionality of 2 to 3, selected from the group consisting of polyester polyols, polyether polyols and hydroxyl terminated unsaturated polymeric polyols, where the ratio of isocyanato groups to hydroxyl groups of the polyol is in the range of about 1.3/1 to about 5/1, where the ratio of amino groups of the 4,4''-diaminodiphenyl sulfide to excess isocyanato groups over said hydroxyl groups is in the range of about 0.5/1 to about 1.1/1, and where said hydroxyl terminated unsaturated polymeric polyol has a molecular weight of about 2000 to about 4000 and a corresponding hydroxyl number of about 50 to about 25 and is selected from unsaturated polymers of the type prepared by polymerizing a mixture of unsaturated monomers comprising about 70 to about 100 percent conjugated diene selected from 1,3-butadiene and isoprene and up to about 30 percent styrene.

Claim 4

The cured polyurethane of claim 2 where the 4,4''-diaminodiphenylsulfide is reacted at a temperature in the range of about 20*C to about 100*C with an isocyanate-terminated prepolymer prepared by reacting a polyisocyanate with a polymeric polyol having a molecular weight in the range of about 800 to about 5000, where the ratio of isocyanato groups to hydroxyl groups of the polyol is in the range of about 1.5/1 to about 3/1, and where the ratio of amino groups of the 4,4''-diaminodiphenyl sulfide to excess isocyanato groups over said hydroxyl groups is in the range of about 0.8/1 to about 1/1.

Claim 5

The cured polyurethane according to claim 2 where said polyisocyanate has an isocyanate functionality of about 2.3 to about 2.7.

Claim 6

The cured polyurethane according to claim 3 where the said polyisocyanate is selected from toluene diisocyanate, n-phenylene diisocyanate, 4-chloro-1,3-phenylene diisocyanate, 4,4''-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1, 10-decamethylene diisocyanate, 1,4-cyclohexylene diisocyanate, 4, 4''-methylene bis(cyclohexylisocyanate), 3,3''-dimethyl-4,4 -diphenyl methane diisocyanate and 1,5-tetrahydronaphthalene diisocyanate.

Claim 7

The cured polyurethane according to claim 3 where said polyester polyols are the condensation products of low molecular weight polyols selected from ethylene glycol, propylene glycol, butylene glycol, pentylene glycol and decamethylene glycol with an organic dicarboxilic acid selected from succinic acid, glutaric acid, adipic acid, phthalic acid, terephthalic acid, isophthalic acid, suberic acid, sebacic acid, pimelic acid and azelaic acid.

Claim 8

The cured polyurethane according to claim 3 where said polyester polyols are caprolactone polyesters derived by reacting a caprolactone selected from epsilon -caprolactone, Zeta caprolactone, and eta caprolactone with a glycol having 4 to 6 carbon atoms.

Claim 9

The cured polyurethane according to claim 3 where the polyether polyols are selected from those prepared by polymerizing or copolymerizing alkylene oxides selected from ethylene oxide, propylene oxide and butylene oxide and by polymerizing or copolymerizing low molecular weight glycols, and further by the reaction of at least one alkylene oxide selected from ethylene oxide, propylene oxide and butylene oxide with a polycarboxylic acid.

Claim 10

The cured polyurethane according to claim 8 where the polyether polyol is polytetramethylene ether glycol.

Claim 11

The cured polyurethane according to claim 3 which contains about 1 to about 15 weight percent of an epoxy resin, and at least sufficient amount of said resin to give an excess of epoxide groups relative to the total amount of amino groups of the monosulfide diamine curative over said excess isocyanato groups, where said epoxy resin is derived from epichlorhydrin and 2,2-bis(4-hydroxyphenyl) propane with an epoxide equivalency of about 150 to about 220.