Derivatives of mono-(alkylene ureido alkyl) ureas, and bis-(alkylene ureido alkyl) ureas

Claim 2

A compound having the formula: ##STR83## where A 1 and A 5 are each independently H, Q 6 H or ##STR84## A 3 and A 4 are each independently H, Q 1 H or ##STR85## provided that at least one of A 1 , A 3 , A 4 and A 5 is a group having the moiety ##STR86## R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Q 1 is (R 5 -O) m where m is zero or an integer from 1 to about 100, and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms; Q 2 is ##STR87## where A 2 is H, ##STR88## where t is zero or an integer from 1 to 10; Q 3 is (O-R 6 ) n where n is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; Q 6 is (R 9 -O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m and n and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 and R 6 ; and Y is CH 2 or ##STR89##

Claim 3

A compound according to claim 1 wherein A 1 , A 3 , A 4 and A 5 are each independently H or ##STR90## provided that at least one of A 1 , A 3 , A 4 and A 5 is ##STR91##

Claim 4

A compound according to claim 2 wherein Q 2 is ##STR92##

Claim 5

A compound according to claim 2 wherein Y is CH 2 .

Claim 6

A compound according to claim 2 wherein Y is ##STR93##

Claim 7

A compound according to claim 2 wherein both R 1 and R 2 are ethylene.

Claim 8

A compound having the formula: ##STR94## where A is H, Q 4 H or ##STR95## A 1 is H, Q 6 H or ##STR96## A 3 is H, Q 1 H or ##STR97## A 6 is H, Q 8 H or ##STR98## provided that at least one of A, A 1 , A 3 or A 6 is a group having the moiety ##STR99## R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Q 1 is (R 5 -O) m where m is zero or an integer from 1 to about 100, and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms; Q 2 is ##STR100## where A 2 is H, ##STR101## where t is zero or an integer from 1 to 10; Q 3 is (O-R 6 ) n wherein n is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; Q 4 is (R 7 -O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m and n, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 or R 6 ; Q 5 is (O-R 8 ) q where q is zero or an integer from 1 to about 100 and may be the same as or different from m, n and p, and R 8 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 and R 7 ; and Q 6 is (R 9 -O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p and q, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 and R 8 ; and Q 7 is (O-R 10 ) s where s is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p, q and r, and R 10 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 , R 8 , and R 9 ; Q 8 is (R 11 -O) w where w is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p, q, r and s, and R 11 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms and may be the same as or different from R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 ; and Y is CH 2 or ##STR102##

Claim 9

A compound having the formula: ##STR94## where A is H, Q 4 H or ##STR95## A 1 is H, Q 6 H or ##STR96## A 3 is H, Q 1 H or ##STR97## A 6 is H, Q 8 H or ##STR98## provided that at least one of A, A 1 , A 3 or A 6 is a group having the moiety ##STR99## R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Q 1 is (R 5 -O) m where m is zero or an integer from 1 to about 100, and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms; Q 2 is ##STR100## where A 2 is H, ##STR101## where t is zero or an integer from 1 to 10; Q 3 is (O-R 6 ) n wherein n is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; Q 4 is (R 7 -O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m and n, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 or R 6 ; Q 5 is (O-R 8 ) q where q is zero or an integer from 1 to about 100 and may be the same as or different from m, n and p, and R 8 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 and R 7 ; and Q 6 is (R 9 -O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p and q, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 and R 8 ; and Q 7 is (O-R 10 ) s where s is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p, q and r, and R 10 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 , R 8 , and R 9 ; Q 8 is (R 11 -O) w where w is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p, q, r and s, and R 11 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms and may be the same as or different from R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 ; and Y is CH 2 or ##STR102##

Claim 10

A compound according to claim 7 wherein A, A 1 , and A 3 and A 6 are each independently H or ##STR103## provided that at least one of A, A 1 , A 3 and A 6 is ##STR104##

Claim 11

A compound according to claim 8 wherein Q 2 is ##STR105##

Claim 12

A compound according to claim 8 wherein Y is CH 2 .

Claim 13

A compound according to claim 8 wherein Y is ##STR106##

Claim 14

A compound according to claim 8 wherein both R 1 and R 2 are ethylene.

Claim 15

A composition of matter made by reacting (1) an unsaturated glycidyl ether or ester having the formula: ##STR107## where R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Y is CH 2 or ##STR108## and Q 3 is (O-R 6 ) n where n is zero or an integer from 1 to about 100 and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, with (2) an alkylene urea having the formula: ##STR109## where Z is ##STR110## where R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; Q 1 is (R 5 -O) m where m is zero or an integer from 1 to about 100 and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms; Q 4 is (R 7 -O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; Q 6 is (R 9 -O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m and p, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 and R 7 ; and Q 8 is (R 11 -O) w where w is zero or an integer from 1 to about 100 and may be the same as or different from m, p and r, and R 11 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms and may be the same as or different from R 5 , R 7 and R 9 ; and in a molar ratio of from about 0.5 to about 10 moles of unsaturated glycidyl ether or ester per mole of alkylene urea and at a temperature in the range of from about 50° C. to about 250° C.

Claim 16

A composition of matter made by reacting (1) an unsaturated glycidyl ether or ester having the formula: ##STR107## where R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Y is CH 2 or ##STR108## and Q 3 is (O-R 6 ) n where n is zero or an integer from 1 to about 100 and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, with (2) an alkylene urea having the formula: ##STR109## where Z is ##STR110## where R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; Q 1 is (R 5 -O) m where m is zero or an integer from 1 to about 100 and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms; Q 4 is (R 7 -O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; Q 6 is (R 9 -O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m and p, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 and R 7 ; and Q 8 is (R 11 -O) w where w is zero or an integer from 1 to about 100 and may be the same as or different from m, p and r, and R 11 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms and may be the same as or different from R 5 , R 7 and R 9 ; and in a molar ratio of from about 0.5 to about 10 moles of unsaturated glycidyl ether or ester per mole of alkylene urea and at a temperature in the range of from about 50° C. to about 250° C.

Claim 17

A composition of matter according to claim 13 wherein the unsaturated glycidyl ether or ester is an ether having the formula: ##STR111## where R 3 is H or CH 3 ; and R 4 is H or CH 3 .

Claim 18

A composition of matter according to claim 13 wherein the alkylene urea has the formula: ##STR112## where R 1 is alkylene having 2 to 3 carbon atoms; and R 2 is alkylene having 2 to about 10 carbon atoms.

Claim 19

A composition of matter according to claim 15 wherein the unsaturated glycidyl ether or ester is allyl glycidyl ether.

Claim 20

A composition of matter according to claim 13 wherein the alkylene urea has the formula: ##STR113## where R 1 is alkylene having 2 to 3 carbon atoms and R 2 is alkylene having 2 to about 10 carbon atoms.