Compositions and Methods of Using Polyamidopolyamines and Non-Polymeric Amidoamines

1 . A composition comprising a polyamidopolyamine produced by the reaction of a polybasic acid and primary polyamine, which is linear, cyclic, branched or cross-linked, said polyamidopolyamine having a molecular weight of about 500 to about 100,000 and having one or more repeating pendant amino groups

2 . The composition according to claim 1 , further comprising one or more of:

(a) a polyamidopolyamine that comprises an imide group;

(b) unreacted polyamine;

(c) multiple different polyamidopolyamines,

(d) multiple different polyamidopolyamines having an imide group, multiple different unreacted polyamines, or any combination thereof.

3 . The composition according to claim 1 , wherein said polyamidopolyamine is of the Formula I, Formula II, Formula III, Formula IV, or Formula V.

4 . The composition according to claim 1 , wherein said polyamidopolyamine is of the

(a) Formula A:

wherein:

each polybasic acid is a dimer acid;

each primary polyamine is independently a diamine, a triamine, or a tetraamine or an amine comprising 5 or more free amino groups;

a and a′ are independently 1 or 2;

b is 0, 1 or 2; and

r is a number between 2 to about 10, including both endpoints of the range; or

(b) Formula A′:

wherein a is 1, 2, 3, or 4, and said reaction has a 1:1 molar ratio of polyamine to dimer acid; or

(c) Formula B:

wherein:

each polybasic acid is a trimer acid;

each primary polyamine is independently a diamine, a triamine, or a tetraamine or an amine comprising 5 or more free amino groups;

a, c, d and e are independently 1 or 2;

b is 0, 1 or 2; and

r is a number between 3 to about 10, including both endpoints of the range; or

(d) Formula C:

wherein:

each polybasic acid is a tetrabasic acid;

each primary polyamine is independently a diamine, a triamine, or a tetraamine or an amine comprising 5 or more free amino groups;

a, c, d, and e are independently 1 or 2;

b is 0, 1 or 2; and

r is a number between 4 to 10, including both endpoints of the range.

5 . The composition according to claim 1 , further comprising (i) an organic hydroxyl containing diluent; or (ii) water as a diluent; or (iii) a water-soluble acid to increase the solubility of the polyamidopolyamine and non-polymeric amidoamine in water

6 . (canceled)

7 . The composition according to claim 1 , which is characterized by one of more of:

(a) low-foaming, non-foaming, or defoaming properties;

(b) antimicrobial or bioresistant properties;

(c) lubricating properties;

(d) a cloud point of about 25° C. to about 82° C., or of about 77° F. to about 180° F., in water;

(e) a pH of about 8 to about 11:

(f) water-soluble; and

(g) water dispersible.

8 . A method for preparing a composition of claim 1 comprising condensing:

(a) a polyamine comprising a primary amino group, and a C 3 to C 16 polybasic acid or derivative thereof, optionally in the presence of an organic hydroxyl-containing diluent; or

(b) a polyamine comprising three primary amino groups, and a C 3 to C 16 polybasic acid or derivative thereof, optionally in the presence of an organic hydroxyl-containing diluent; or

(c) two polyamines comprising three amino groups and a C 3 to C 16 polybasic acid or derivative thereof; or

(d) a polyamine comprising three amino groups and two C 3 to C 16 polybasic acids or derivative thereof; or

(e) a polyamine comprising three amino groups, a polyamine comprising two amino groups, and a C 3 to C 16 polybasic acid or derivative thereof.

9 . A method for preparing a composition comprising a polyamidopolyamine, wherein said method comprises:

(a) reacting a polybasic acid with a polyamine and an optional hydroxyl-containing solvent to produce a first polyamidopolyamine as a reaction product;

(b) reacting the product (a) with the same or different a polybasic acid and an optional hydroxyl-containing solvent to produce another polyamidopolyamine as a subsequent reaction product;

(c) performing additional sequential condensation reactions by reacting the polyamidopolyamine reaction product of each preceding condensation reaction with the same or different polybasic acid and an optional hydroxyl-containing solvent, and

(d) terminating the reaction sequence when the composition demonstrates a desired characteristic selected from anti-foaming, defoaming, lubricity, bioresistance, antimicrobial activity or any combination thereof.

10 . The method according to claim 9 , further comprising at least one of

(e) further terminating additional free amino groups to amide acids or salts with cyclic anhydride to cap amino groups at a temperature below the condensation reaction temperature;

(f) adding an organic hydroxyl-containing diluent or solvent at the initiation of the reaction; or

(g) adding water or an organic hydroxyl-containing diluent or solvent at the end of the reaction to adjust viscosity of the composition.

11 . The method according to claim 8 , wherein the resulting composition comprises a polyamidopolyamine, which is a linear, cyclic, branched or cross-linked amide comprising multiple primary amine groups.

12 . The method according to claim 8 , wherein said polybasic acid comprises two C(O)OH groups or derivatives thereof.

13 . The method according to claim 9 , wherein said polyamines are different.

14 . The method according to claim 9 , further comprising:

(a) having a mole ratio of polybasic acid to polyamine is equal to or greater than about 1: (1×), wherein X is the number of C(O)OH groups in the polybasic acid; or

(b) having a mole ratio of the polybasic acid to the polyamine is about is about 1:1, with an optional organic hydroxyl-containing solvent.

15 . The method according to claim 8 , wherein said polyamine is:

(a) triaminononane or 4-aminomethyl-1,8-octanediamine;

(b) the formula:

wherein:

R 1 , R 3 and R 5 are independently H, methyl, ethyl, propyl or butyl;

R 2 , R 4 and R 6 are independently methyl, ethyl, propyl, or butyl; and

a, b and c are additively a number between 0 to about 90, including both endpoints of the range; or

(c) of the formula:

wherein s, t and u are additively a number between 3 to about 90, including both endpoints of the range; or

(d) the formula:

wherein:

R 1 , is H, methyl, ethyl, propyl or butyl;

R 2 , R 3 , and R 4 are, independently, methyl, ethyl, propyl, or butyl; and

e and f are additively a number between 0 to about 90, including both endpoints of the range; or

(e) the formula:

NH 2 CH(CH 3 )CH 2 —(O—CH 2 CF 2 ) g —(O—CH 2 CH(CH 3 )) h —(O—CH 2 CH(CH 3 ))—NH 2

wherein g and h are additively a number between 0 to about 90, including both endpoints of the range; or

(f) the formula:

wherein:

R 1 , R 3 , R 5 and R 7 are independently H, methyl, ethyl, propyl or butyl;

R 2 , R 4 , R 6 , and R 8 are independently is methyl, ethyl, propyl, or butyl; and

w, j, k and m are additively a number between 0 to about 90, including both endpoints of the range; or

(g) the formula:

wherein h, n, o and p are additively a number between 4 to about 90, including both endpoints of the range; or

(h) the formula:

wherein:

R 1 , R 3, and R 5 are independently H, methyl, ethyl, propyl or butyl;

R 2 , R 4, and R 6 are independently methyl, ethyl, propyl, or butyl; and

a′, b′ and c′ are additively a number between 0 to 90, including both endpoints of the range; or

(i) the formula:

wherein e′, f′ and g′ are additively a number between 3 to 90.

16 . A composition comprising a non-polymeric amidoamine, which is a linear or branched amide containing a primary amine group, said non-polymeric amidoamine having a molecular weight of about 290 to about 5000.

17 . The composition according to claim 16 , wherein said composition is produced by the reaction of a monobasic acid and a primary amine.

18 . The composition according to claim 16 , further comprising an amide comprising a diamide, a triamide or a tetraamide, or a mixture thereof.

19 . The composition according to claim 1 , further comprising a non-polymeric amidoamine, which is a linear or branched amide containing a primary amine group, said non-polymeric amidoamine having a molecular weight of about 290 to about 5000.

20 . The composition according to claim 19 , wherein said non-polymeric amidoamine is:

(a) of the Formula F:

wherein x, y, and z are, are additively a number between 3 to about 90, including both endpoints of the range; and R 1 is C 1 to C 11 alkyl or C 1 to C 11 substituted alkyl; or

(b) of the Formula G:

wherein x, y, and z are, additively a number between 3 to about 90, including both endpoints of the range; and R 1 , and R 2 are, independently, C 1 to C 11 alkyl or C 1 to C 11 substituted alkyl.

21 . A composition of claim 1 , produced by a condensation reaction wherein the reactants comprise an acid and a polyamine, wherein the acid is a polybasic acid, a monobasic acid, or both a polybasic acid and a monobasic acid, in the optional presence of an organic hydroxyl-containing diluent.