Ketal amide compounds, methods of making, and applications
Disclosed herein are ketal amide compounds. The ketal amide compounds are synthesized by the reaction of ketal acids or ketal esters with amine functional compounds. Also disclosed are methodologies useful to make the ketal amide compounds. Also disclosed herein are formulations and articles containing the ketal amide compounds.
1. A compound comprising one or more fragments having structure V:
wherein
α is an integer of at least 1;
β is an integer of at least 1;
each X is independently O or NR 2 —;
each R 1 is independently a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl group, optionally comprising one or more heteroatoms; each R 2 is independently hydrogen or an alkyl group having between 1 and 6 carbon atoms, or a portion of a piperazine moiety wherein X is NR 2 ;
each R 3 , R 4 , R 5 , R 6 , and R 7 is independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl group, optionally comprising one or more hetero atoms;
each R 8 is independently a covalent bond, methylene, ethylene, or hydroxymethylene;
R 9 and R 10 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally comprises one or more heteroatoms;
each a is independently 0 or an integer of 1 to 12; and
each b is independently 0 or 1, wherein b=0 indicates a five membered ring:
and b=1 indicates a 6 membered ring:
2. A compound comprising one or more fragments having structure V′:
wherein
β is an integer of at least 1;
each X is O;
each a is independently 0 or an integer of 1 to 12;
each R 1 is independently a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl group, optionally comprising one or more heteroatoms;
each R 2 is independently hydrogen or an alkyl group having between 1 and 6 carbon atoms, or a portion of a piperazine moiety wherein X is NR 2 ; and
each R 3 , R 4 , and R 5 is independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl group, optionally comprising one or more heteroatoms.
3. The compound of claim 1 , wherein a is 0, 1 or 2.
4. The compound of claim 1 , wherein a is 2 and all R 3 and R 4 are hydrogen.
5. The compound of claim 4 , wherein R1 is 1,2-cyclohexyl, —(CH 2 ) 3 —, or —(CH 2 ) 6 —.
6. The compound of claim 1 , wherein β is 1.
7. The compound of claim 1 , wherein β is between about 2 and about 500.
8. A formulation comprising the compound of claim 1 .
9. An article comprising the compound of claim 1 .
10. The article of claim 9 , wherein the article is transparent.
11. A film comprising the compound of claim 1 .
12. An injection-molded product comprising the compound of claim 1 .
13. An extrusion coated product comprising the compound of claim 1 .
14. A fiber comprising the compound of claim 1 .
15. A foam comprising the compound of claim 1 .
16. A thermoformed product comprising the compound of claim 1 .
17. An extruded profile or sheet comprising the compound of claim 1 .
18. A coating comprising the compound of claim 1 .
19. The coating of claim 18 , wherein the coating is a paint, adhesive, or glue.
20. A polymer blend comprising the compound of claim 1 and an aromatic/aliphatic polyester, a biodegradable polyester, a polystyrene, a copolymer of polystyrene, a polyurethane, a polycarbonate, a polyamide, or a polyolefin.
21. A polymer blend comprising the compound of claim 1 and a starch, cellulose, chitosan, alginate, natural rubber, or natural fiber.
22. A polymer alloy comprising the compound of claim 1 and a polyamide polymer or a polyamide copolymer.
23. The compound of claim 2 , wherein a is 0, 1 or 2.
24. The compound of claim 2 , wherein all R 2 and R 3 are hydrogen.
25. The compound of claim 24 , wherein R 1 is 1,2-cyclohexyl, —(CH 2 ) 3 —, or —(CH 2 ) 6 —.
26. The compound of claim 2 , wherein β is 1.
27. The compound of claim 2 , wherein 0 is between about 2 and about 500.
28. A formulation comprising the compound of claim 2 .
29. An article comprising the compound of claim 2 .
30. The article of claim 29 , wherein the article is transparent.
31. A film comprising the compound of claim 3 .
32. An injection-molded product comprising the compound of claim 2 .
33. An extrusion coated product comprising the compound of claim 2 .
34. A fiber comprising the compound of claim 2 .
35. A foam comprising the compound of claim 2 .
36. A thermoformed product comprising the compound of claim 2 .
37. An extruded profile or sheet comprising the compound of claim 2 .
38. A coating comprising the compound of claim 2 .
39. The coating of claim 38 , wherein the coating is a paint, adhesive, or glue.
40. A polymer blend comprising the compound of claim 2 and an aromatic/aliphatic polyester, a biodegradable polyester, a polystyrene, a copolymer of polystyrene, a polyurethane, a polycarbonate, a polyamide, or a polyolefin.
41. A polymer blend comprising the compound of claim 2 and a starch, cellulose, chitosan, alginate, natural rubber, or natural fiber.
42. A polymer alloy comprising the compound of claim 2 and a polyamide polymer or a polyamide copolymer.