Diisocyanates having urea groups, a process for their preparation and their use in the production of polyurethanes

Claim 2

A diisocyanate containing urea groups, which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: ##STR16## wherein m represents a number of from 0 to 3 which may be whole or fractional (on statistical average), R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkythio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom.

Claim 3

A diisocyanate as claimed in claim 1 wherein m is zero.

Claim 4

A diisocyanate as claimed in claim 2 which is liquid at room temperature.

Claim 5

A mixture which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C. comprising: (A) 5 to 50% by weight based on the mixture of a diisocyanate containing urea groups, which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: ##STR17## wherein m represents a number of from 0 to 3 which may be whole or fractional (on statistical average), R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atoms and the sulfur atom; and (B) an isocyanate prepolymer, which is liquid at room temperature or which can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: D--OCO--NH--A--NCO).sub.n wherein n has the value of a whole or fractional number, on statistical average, of from 2 to 4, A represents a residue as is obtained by the removal of the isocyanate groups from an organic diisocyanate, and D represents a residue of the type obtained by the removal of the hydroxyl groups from an n-functional polyhydroxyl compound within the molecular weight range of from 500 to 8,000 or by removal of the hydroxyl groups from a mixture of such polyhydroxyl compounds.

Claim 6

A mixture which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C. comprising: (A) 5 to 50% by weight based on the mixture of a diisocyanate containing urea groups, which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: ##STR17## wherein m represents a number of from 0 to 3 which may be whole or fractional (on statistical average), R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atoms and the sulfur atom; and (B) an isocyanate prepolymer, which is liquid at room temperature or which can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: D--OCO--NH--A--NCO).sub.n wherein n has the value of a whole or fractional number, on statistical average, of from 2 to 4, A represents a residue as is obtained by the removal of the isocyanate groups from an organic diisocyanate, and D represents a residue of the type obtained by the removal of the hydroxyl groups from an n-functional polyhydroxyl compound within the molecular weight range of from 500 to 8,000 or by removal of the hydroxyl groups from a mixture of such polyhydroxyl compounds.

Claim 7

A mixture as claimed in claim 4 wherein said diisocyanate is in the form of a solution in said prepolymer.

Claim 8

A mixture as claimed in claim 4 wherein m represents zero, n represents 2, and A represents an aliphatic hydrocarbon group having from 6 to 12 carbon atoms with at least 6 carbon atoms situated between the 2 nitrogen atoms, a cycloaliphatic hydrocarbon group having from 4 to 15 carbon atoms, a xylylene group or a group corresponding to the formula: ##STR18## wherein R 1 ' represents hydrogen, and R 2 ' represents a polymethylene group having from 2 to 6 carbon atoms or a 1,4-phenylene group.

Claim 9

A mixture as claimed in claim 6, wherein said diisocyanate is in the form of a solution in said prepolymer.

Claim 10

A process for the preparation of a diisocyanate containing urea groups which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C. comprising reacting: (A) a diisocyanate corresponding to the formula: ##STR19## wherein R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom; with (B) from 0.4 to 0.8 mol of water per mol of said diisocyanate or with a corresponding quantity of a compound which splits off water.

Claim 11

A process for the preparation of a diisocyanate containing urea groups which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C. comprising reacting: (A) a diisocyanate corresponding to the formula: ##STR19## wherein R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom; with (B) from 0.4 to 0.8 mol of water per mol of said diisocyanate or with a corresponding quantity of a compound which splits off water.

Claim 12

A process for the preparation of a mixture of a diisocyanate containing urea groups in an isocyanate prepolymer said mixture being a liquid at room temperature or liquefiable by heating to a temperature of not more than 80° C. comprising reacting: (A) a diisocyanate corresponding to the formula: ##STR20## wherein R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom; with (B) from 0.4 to 0.8 mol of water per mol of said diisocyanate or with a corresponding quantity of a compound which splits off water; and (C) from 50 to 95% by weight, based on the total mixture, of an isocyanate prepolymer which is liquid at room temperature or which can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: D--OCO--NH--A--NCO).sub.n wherein n has the value of a whole or fractional number, on statistical average, of from 2 to 4, A represents a residue as is obtained by the removal of the isocyanate groups from an organic diisocyanate, and D represents a residue of the type obtained by the removal of the hydroxyl groups from an n-functional polyhydroxyl compound within the molecular weight range of from 500 to 8,000 or by removal of the hydroxyl groups from a mixture of such polyhydroxyl compounds.

Claim 13

A process for the preparation of a mixture of a diisocyanate containing urea groups in an isocyanate prepolymer said mixture being a liquid at room temperature or liquefiable by heating to a temperature of not more than 80° C. comprising reacting: (A) a diisocyanate corresponding to the formula: ##STR20## wherein R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom; with (B) from 0.4 to 0.8 mol of water per mol of said diisocyanate or with a corresponding quantity of a compound which splits off water; and (C) from 50 to 95% by weight, based on the total mixture, of an isocyanate prepolymer which is liquid at room temperature or which can be liquefied by heating to a temperature of not more than 80° C., corresponding to the formula: D--OCO--NH--A--NCO).sub.n wherein n has the value of a whole or fractional number, on statistical average, of from 2 to 4, A represents a residue as is obtained by the removal of the isocyanate groups from an organic diisocyanate, and D represents a residue of the type obtained by the removal of the hydroxyl groups from an n-functional polyhydroxyl compound within the molecular weight range of from 500 to 8,000 or by removal of the hydroxyl groups from a mixture of such polyhydroxyl compounds.

Claim 14

A process as claimed in claim 9 wherein n represents 2 and A represents an aliphatic hydrocarbon group having from 6 to 12 carbon atoms with at least 6 carbon atoms situated between the 2 nitrogen atoms, a cycloaliphatic hydrocarbon group having from 4 to 15 carbon atoms, a xylylene group or a group corresponding to the formula: ##STR21## wherein R 1 ' represents hydrogen and R 2 ' represents a polymethylene group having from 2 to 6 carbon atoms or a 1,4-phenylene group.

Claim 15

A process as claimed in claim 9 wherein components (A) and (B) are first reacted and then added to component (C).

Claim 16

A process as claimed in claim 9 wherein components (A) and (C) are first added together and then reacted with component (B).

Claim 17

A process as claimed in claim 11 wherein n represents 2 and A represents an aliphatic hydrocarbon group having from 6 to 12 carbon atoms with at least 6 carbon atoms situated between the 2 nitrogen atoms, a cycloaliphatic hydrocarbon group having from 4 to 15 carbon atoms, a xylylene group or a group corresponding to the formula: ##STR22## wherein R 1 ' represents hydrogen and R 2 ' represents a polymethylene group having from 2 to 6 carbon atoms or a 1,4-phenylene group.

Claim 18

A process as claimed in claim 12 wherein n represents 2 and A represents an aliphatic hydrocarbon group having from 6 to 12 carbon atoms with at least 6 carbon atoms situated between the 2 nitrogen atoms, a cycloaliphatic hydrocarbon group having from 4 to 15 carbon atoms, a xylylene group or a group corresponding to the formula: ##STR23## wherein R 1 ' represents hydrogen and R 2 ' represents a polymethylene group having from 2 to 6 carbon atoms or a 1,4-phenylene group.

Claim 19

A process for the preparation of polyurethanes comprising reacting an organic isocyanate with a compound containing isocyanate-reactive hydrogen atoms wherein said organic isocyanate comprises a diisocyanate containing urea groups, which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C. corresponding to the formula: ##STR24## wherein m represents a number of from 0 to 3 which may be whole or fractional (on statistical average), R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom.

Claim 20

A process for the preparation of polyurethanes comprising reacting an organic isocyanate with a compound containing isocyanate-reactive hydrogen atoms wherein said organic isocyanate comprises a diisocyanate containing urea groups, which is liquid at room temperature or can be liquefied by heating to a temperature of not more than 80° C. corresponding to the formula: ##STR24## wherein m represents a number of from 0 to 3 which may be whole or fractional (on statistical average), R 1 represents hydrogen, an alkyl group having from 1 to 4 carbon atoms or an alkylthio group having from 1 to 4 carbon atoms, and R 2 represents a phenylene group, optionally substituted by alkyl groups having from 1 to 4 carbon atoms or by an alkylthio group having from 1 to 4 carbon atoms, or represents a linear or branched chain aliphatic hydrocarbon group having from 2 to 12 carbon atoms, with at least 2 carbon atoms being situated between the nitrogen atom and the sulfur atom.

Claim 21

A process as claimed in claim 15 wherein m represents zero.

Claim 22

A process for the preparation of polyurethanes comprising reacting a compound containing isocyanate-reactive hydrogen atoms with a mixture as claimed in claim 4.