Curing with complexes of selected diamines and alkali metal salts

Claim 2

A PROCESS FOR CURING AN AMINO CURABLE POLYMER OR PREPOLYMER WHICH COMPRISES CURING SAID POLYMER WITH A CURING AGENT CONSISTING ESSENTIALLY OF (A) A SOURCE OF ACTIVE HYDROGEN HAVING ONE OR MORE ZEREWITINOFF ACTIVE HYDROGENS AND AN IONIZATION CONSTANT SUCH THAT ITS PKA IS GREATER THAN 6.0, AND (B) A COMPLEX OF 4,4''-METHYLENE DIANILINE AND A SALT, THE SALT BEING SELECTED FROM THE GROUP CONSISTING OF SODIUM CHLORIDE, SODIUM BROMIDE, SODIUM IODIDE, SODIUM NITRITE, LITHIUM CHLORIDE, LITHIUM BROMIDE, LITHIUM IODIDE, LITHIUM NITRITE AND SODIUM CYANIDE, OR A COMPLEX OF RACEMIC 2,3-DI(4-AMINOPHENYL)BUTANE WITH A SALT, SAID SALT BEING SELECTED FROM THE GROUP CONSISTING OF SODIUM CHLORIDE, SODIUM BROMIDE, SODIUM IODIDE, POTASSIUM CHLORIDE, POTASSIUM BROMIDE, POTASSIUM IODIDE, RUBIDIUM CHLORIDE, RUBIDIUM BROMIDE, RUBIDIUM IODIDE, CESIUM CHLORIDE, CESIUM BROMIDE AND CESIUM IODIDE; THE RATIO OF SAID DIANILINE OR SAID BUTANE TO SAID SALT IN SAID COMPLEX BEING 3 MOLES TO 1 MOLE.

Claim 3

A process for curing an amine-curable polymer or prepolymer which consists essentially of curing said polymer or prepolymer with (a) an active hydrogen source having one or more Zerewitinoff active hydrogens and an ionization constant such that its pKa is greater than 6.0, and (b) a complex of 4,4''-methylene dianiline and a salt, selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole.

Claim 4

A process for curing an amine-curable polymer or prepolymer which consists essentially of curing said polymer or prepolymer with (a) an active hydrogen source having one or more Zerewitinoff active hydrogens and an ionization constant such that its pKa is greater than 6.0, and (b) a complex of 4,4''-methylene dianiline and a salt, selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole.

Claim 5

The process of claim 2 wherein said prepolymer or polymer is a urethane containing free isocyanato groups.

Claim 6

The process of claim 3 wherein said curing takes place at ambient temperature and a plastic gum is formed.

Claim 7

The process of claim 3 wherein said complex is derived from 4,4''-methylene dianiline and sodium Chloride.

Claim 8

The process of claim 3 wherein said complex is derived from 4,4''-methylene dianiline and lithium chloride.

Claim 9

The process of claim 3 wherein said curing takes place at a temperature of about 0* to 195* C.

Claim 10

The process of claim 3 wherein said source of active hydrogen is selected from the group consisting of alcohols, polyols, phenols and primary and secondary aromatic amines.

Claim 11

The process of claim 3 wherein said source of active hydrogen is a polyfunctional alcohol.

Claim 12

The process of claim 3 wherein said source of active hydrgen is 1,4-butanediol.

Claim 13

The process of claim 3 wherein said source of active hydrogen is glycerol.

Claim 14

The process of claim 1 wherein the complex and source of hydrogen are maintained in a dispersion of an inert liquid which is subsequently commingled with the amine-curable polymer or prepolymer.

Claim 15

The process of claim 12 wherein said inert liquid is di(2-ethylhexyl)phthalate.

Claim 16

The product of claim 1.

Claim 17

The product of claim 2.

Claim 18

The product of claim 3.

Claim 19

The product of claim 9.

Claim 20

The product of claim 10.

Claim 21

The product of claim 11.

Claim 22

The product of claim 4.

Claim 23

A composition of matter consisting essentially of a partially cured, compression-moldable plastic gum prepared by mixing an amine-curable prepolymer or polymer with a curing agent and partially curing said polymer or prepolymer; said curing agent consisting essentially of (a) a source of active hydrogen having one or more Zerewitinoff active hydrogens and an ionization constant such that its pKa is greater than 6.0, and (b) a complex of 4,4''-methylene dianiline and a salt, the salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, or a complex of racemic 2,3-di (4-aminophenyl) butane with a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide, the ratio of said dianiline or said butane to said salt in said complex being 3 moles to 1 mole.

Claim 24

A composition of matter consisting essentially of a partially cured, compression-moldable plastic gum prepared by mixing an amine-curable prepolymer or polymer with a curing agent and partially curing said polymer or prepolymer; said curing agent consisting essentially of (a) a source of active hydrogen having one or more Zerewitinoff active hydrogens and an ionization constant such that its pKa is greater than 6.0, and (b) a complex of 4,4''-methylene dianiline and a salt, the salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, or a complex of racemic 2,3-di (4-aminophenyl) butane with a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide, the ratio of said dianiline or said butane to said salt in said complex being 3 moles to 1 mole.

Claim 25

The composition of claim 21 wherein the polymer being cured is an isocyanate-terminated polyurethane, the source of active hydrogen is 1,4-butanediol, and the complex is a complex of 4,4''-methylene dianiline and sodium chloride.

Claim 26

As a new composition of matter, a dispersion of (1) a complex of 4,4''-methylene dianiline and a salt, the salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, or a complex of racemic 2,3-di(4-amino-phenyl)butane with a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide, the ratio of said dianiline or said butane to said salt in said complex being 3 moles to 1 moles, in (2) a liquid selected from the group consisting of a poly(alkylene ether)glycol, a poly-(alkylene ether) polyol, and a hydroxyl-terminated polyester of a polyhydroxyl alcohol and a polycarboxylic acid.

Claim 27

As a new composition of matter, a dispersion of (1) a complex of 4,4''-methylene dianiline and a salt, the salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, or a complex of racemic 2,3-di(4-amino-phenyl)butane with a salt, said salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, potassium chloride, potassium bromide, potassium iodide, rubidium chloride, rubidium bromide, rubidium iodide, cesium chloride, cesium bromide and cesium iodide, the ratio of said dianiline or said butane to said salt in said complex being 3 moles to 1 moles, in (2) a liquid selected from the group consisting of a poly(alkylene ether)glycol, a poly-(alkylene ether) polyol, and a hydroxyl-terminated polyester of a polyhydroxyl alcohol and a polycarboxylic acid.

Claim 28

The dispersion of claim 23 which additionally contains an inert liquid carrier.

Claim 29

The dispersion of claim 24 wherein said liquid carrier is dioctylphthalate.

Claim 30

The dispersion of claim 23 wherein said liquid (2) has an equivalent weight of 200-2000.

Claim 31

The dispersion of claim 23 wherein said complex 1) is a complex of 4,4''-methylene dianiline and sodium chloRide and said liquid (2) is poly(tetramethylene ether)glycol.

Claim 32

In a process of curing an amine-curable polymer or prepolymer with a complex of 4,4''-methylene dianiline and a salt, the salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the improvement comprising employing said complex in the form of a dispersion in a liquid selected from the group consisting of a poly(alkylene ether)glycol, a poly(alkylene ether)polyol, and a hydroxyl-terminated polyester of a polyhydroxyl alcohol and a polycarboxylic acid.

Claim 33

In a process of curing an amine-curable polymer or prepolymer with a complex of 4,4''-methylene dianiline and a salt, the salt being selected from the group consisting of sodium chloride, sodium bromide, sodium iodide, sodium nitrite, lithium chloride, lithium bromide, lithium iodide, lithium nitrite and sodium cyanide, the ratio of said dianiline to said salt in said complex being 3 moles to 1 mole, the improvement comprising employing said complex in the form of a dispersion in a liquid selected from the group consisting of a poly(alkylene ether)glycol, a poly(alkylene ether)polyol, and a hydroxyl-terminated polyester of a polyhydroxyl alcohol and a polycarboxylic acid.

Claim 34

The process of claim 28 wherein said polymer or prepolymer is an isocyanato-terminated polyurethane.

Claim 35

The process of claim 29 wherein said complex is a complex of 4,4''-methylene dianiline and sodium chloride, and said liquid is poly(tetramethylene ether)glycol.