Cured adhesive compositions and method of making

1. A multiple-part curable composition comprising:

a) a part A comprising an oxalamido-containing compound having a molecular weight of at least 250 grams/mole and having at least two oxalamido groups of formula —NR 2 —(CO)—(CO)—OR 1 ,

wherein

R 1 is a hydrocarbyl; and

R 2 is hydrogen or hydrocarbyl; and

b) a part B comprising a derivatized polyethylene imine comprising a reaction product of a polyethylene imine with a glycidyl ether, the derivatized polyethylene imine comprising monomeric units of Formula (VI)

wherein

R 3 is an alkyl having at least 4 carbon atoms, an aryl, an aralkyl, or an alkaryl; and

each asterisk (*) is an attachment site to another monomeric unit of the derivatized polyethylene imine.

2. The multiple-part curable composition of claim 1 , wherein the oxalamido-containing compound is a compound of Formula (II)

R 1 O—(CO)—(CO)—[NR 2 —R 4 —NR 2 —(CO)—(CO)] q —OR 1   (II)

wherein

R 1 is a hydrocarbyl;

R 2 is hydrogen, or a hydrocarbyl; and

R 4 is a hydrocarbylene; and

q is an integer in a range of 1 to 10.

3. The multiple-part curable composition of claim 2 , wherein R 4 is an alkylene, alkenylene, arylene, or a combination thereof.

4. The multiple-part curable composition of claim 1 ,

wherein

R 1 is alkyl, aryl, aralkyl, or alkaryl; and

R 2 is hydrogen, alkyl, aryl, aralkyl, or alkaryl.

5. The multiple-part curable composition of claim 1 , wherein the derivatized polyethylene imine further comprises monomeric units of Formula (V) and/or of Formula (VII)

wherein

R 3 is an alkyl having at least 4 carbon atoms; and

each asterisk (*) is an attachment site to another monomeric unit of the derivatized polyethylene imine.

6. The multiple-part curable composition of claim 1 , wherein 10 to 25 mole percent of the monomeric units in the derivatized polyethylene imine are of Formula (VI) and/or Formula (VII)

based on total moles of monomeric units in the derivatized polyethylene imine,

wherein

R 3 is an alkyl having at least 4 carbon atoms; and

each asterisk (*) is an attachment site to another monomeric unit of the derivatized polyethylene imine.

7. The multiple-part curable composition of claim 1 , wherein part A and/or part B further comprises a carboxylic acid having at least 4 carbon atoms.

8. The multiple-part curable composition of claim 7 , wherein the carboxylic acid is a fatty acid.

9. The multiple-part curable composition of claim 7 , wherein the carboxylic acid is in part A and in an amount of 0.01 to 10 weight percent based on a total weight of part A.

10. The multiple-part curable composition of claim 1 , wherein part A has a first viscosity (V1) and part B has a second viscosity (V2) and wherein the second viscosity (V2) is in a range of 0.1(V1) to 10(V1).

11. The multiple-part curable composition of claim 1 , wherein the molar ratio of primary amino groups in the derivatized polyethyleneimine of part B to oxalamido-containing compound in part A is in a range of 0.75 to 3.5.

12. A cured composition comprising a cured reaction product of a multiple-part curable composition of claim 1 , wherein the cured composition is an adhesive.

13. The cured composition of claim 12 , wherein the adhesive has a percent elongation at break that is in a range of 20 to 80 percent using ASTM method D882-2018 and/or has a closure strength of at least 2 Newtons using ASTM method F2458-05.

14. The cured composition of claim 12 , wherein the adhesive is a tissue adhesive.

15. The cured composition of claim 12 , wherein the adhesive is a wound closure adhesive.

16. A method of providing a cured composition, the method comprising:

a) preparing or obtaining a part A composition comprising an oxalamido-containing compound having a molecular weight of at least 250 grams/mole and having at least two oxalamido groups of formula —NR 2 —(CO)—(CO)—OR 1 ,

wherein

R 1 is a hydrocarbyl; and

R 2 is hydrogen or hydrocarbyl; and

b) preparing or obtaining a part B composition comprising a derivatized polyethylene imine comprising a reaction product of a polyethylene imine with a glycidyl ether, the derivatized polyethylene imine having monomeric units of Formula (VI)

wherein

R 3 is an alkyl having at least 4 carbon atoms, an aryl, an aralkyl, or an alkaryl; and

each asterisk (*) is an attachment site to another monomeric unit of the derivatized polyethylene imine;

c) combining part A with part B to form a reaction mixture; and

d) curing the reaction mixture to form a cured composition that is an adhesive.

17. The method of claim 16 , wherein combining part A with part B comprises placing part A and part B in separate syringes, dispensing part A and part B from the separate syringes, and combining part A with part B in a mixing chamber to form the reaction mixture.

18. The method of claim 17 , further comprising discharging the reaction mixture from the mixing chamber prior to curing the reaction mixture.

19. The method of claim 18 , wherein discharging comprises applying the reaction mixture to a tissue surface.

20. The method of claim 18 , wherein discharging comprises applying the reaction mixture to an open wound to close the wound.