CA2654809A1 - Polyketal compounds, synthesis, and applications - Google Patents
Polyketal compounds, synthesis, and applications Download PDFInfo
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- CA2654809A1 CA2654809A1 CA002654809A CA2654809A CA2654809A1 CA 2654809 A1 CA2654809 A1 CA 2654809A1 CA 002654809 A CA002654809 A CA 002654809A CA 2654809 A CA2654809 A CA 2654809A CA 2654809 A1 CA2654809 A1 CA 2654809A1
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Abstract
The invention relates to polyketal compounds. The compounds are synthesized by the selective ketalization of oxocarboxylic acids, e.g. keto acids and semialdehydes, and esters thereof with tetrols and higher polyols that products two or more cyclic ketal ester moieties per molecule, wherein the cyclic ketal moieties are situated in a bis-, tris-, or polyketal conformation. The invention further relates to applications of these compounds and subsequent reactions thereof.
Claims (30)
1. A polyketal having structure I:
wherein .alpha. is an integer of at least 1;
R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
R2, R3, R4, R5, and R6 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R7 is a covalent bond, methylene, ethylene, hydroxymethylene, oxygen, or -CH2-O-CH2- and R7 is the same or different for each occurrence;
R8 and R9 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contains one or more heteroatoms;
a is 0 or an integer of 1 to 12; and b is 0 or 1, wherein b = 0 indicates a five membered ring, and b = 1 indicates a 6 membered ring, and b is the same or different for each occurrence.
wherein .alpha. is an integer of at least 1;
R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
R2, R3, R4, R5, and R6 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R7 is a covalent bond, methylene, ethylene, hydroxymethylene, oxygen, or -CH2-O-CH2- and R7 is the same or different for each occurrence;
R8 and R9 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contains one or more heteroatoms;
a is 0 or an integer of 1 to 12; and b is 0 or 1, wherein b = 0 indicates a five membered ring, and b = 1 indicates a 6 membered ring, and b is the same or different for each occurrence.
2. A formulation comprising one or more polyketals having structure I.
3. An article comprising the formulation of claim 2.
4. A bisketal having structure II:
wherein:
R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2 and R3 are the same or different for each occurrence;
R4 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms;
and R4 is the same or different for each occurrence; and a is 0 or an integer of 1 to 12.
wherein:
R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2 and R3 are the same or different for each occurrence;
R4 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms;
and R4 is the same or different for each occurrence; and a is 0 or an integer of 1 to 12.
5. A formulation comprising one or more bisketals of structure II.
6. An article comprising the formulation of claim 5.
7. A polymeric composition comprising one or more repeat units comprising structure III:
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence;
R2, R3, R4, R5, and R6 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R7 is a covalent bond, methylene, ethylene, hydroxymethylene, oxygen, or -CH2-O-CH2- and R7 is the same or different for each occurrence;
R8 and R9 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contains one or more heteroatoms;
a is 0 or an integer of 1 to 12;
b is 0 or 1, wherein b = 0 indicates a five membered ring, b = 1 indicates a 6 membered ring, and b is the same or different for each occurrence;
.alpha. is an integer of at least 1; and .beta. is an integer of at least 1.
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence;
R2, R3, R4, R5, and R6 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R7 is a covalent bond, methylene, ethylene, hydroxymethylene, oxygen, or -CH2-O-CH2- and R7 is the same or different for each occurrence;
R8 and R9 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contains one or more heteroatoms;
a is 0 or an integer of 1 to 12;
b is 0 or 1, wherein b = 0 indicates a five membered ring, b = 1 indicates a 6 membered ring, and b is the same or different for each occurrence;
.alpha. is an integer of at least 1; and .beta. is an integer of at least 1.
8. A formulation comprising one or more polymeric compositions of structure III.
9. An article comprising the formulation of claim 8.
10. A polymeric composition comprising one or more repeat units comprising structure IV:
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2 and R3 are the same or different for each occurrence;
R4 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms;
and R4 is the same or different for each occurrence;
a is 0 or an integer of 1 to 12; and .beta. is an integer of at least 1.
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2 and R3 are the same or different for each occurrence;
R4 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms;
and R4 is the same or different for each occurrence;
a is 0 or an integer of 1 to 12; and .beta. is an integer of at least 1.
11. A formulation comprising one or more polymeric compositions of structure IV.
12. An article comprising the formulation of claim 11.
13. A polyketal having structure V:
wherein R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R4 and R5 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contain one or more heteroatoms;
a is 0 or an integer of 1 to 12 and a is the same or different for each occurrence;
b is 0 or 1 wherein b = 0 indicates a five membered ring, b = 1 indicates a 6 membered ring, and b may be the same or different for each occurrence; and .alpha. is an integer of at least 1.
wherein R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R4 and R5 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contain one or more heteroatoms;
a is 0 or an integer of 1 to 12 and a is the same or different for each occurrence;
b is 0 or 1 wherein b = 0 indicates a five membered ring, b = 1 indicates a 6 membered ring, and b may be the same or different for each occurrence; and .alpha. is an integer of at least 1.
14. A formulation comprising one or more polyketals of structure V.
15. An article comprising the formulation of claim 14.
16. A polyketal having the structure VI:
wherein R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence; and .alpha. is 1 or 2.
wherein R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence; and .alpha. is 1 or 2.
17. A formulation comprising one or more compounds of structure VI.
18. An article comprising the formulation of claim 17.
19. A polymeric composition comprising one or more repeat units comprising structure VII:
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R4 and R5 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contain one or more heteroatoms;
a is 0 or an integer of 1 to 12 and a is the same or different for each occurrence;
b is 0 or 1 wherein b = 0 indicates a five membered ring, b = 1 indicates a 6 membered ring, and b may be the same or different for each occurrence;
.alpha. is an integer of at least 1; and .beta. is an integer of at least 1.
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence;
R2 and R3 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, or alkaryl; and optionally contains one or more heteroatoms; and R2, R3, R4, R5, and R6 is the same or different for each occurrence;
R4 and R5 are independently hydrogen, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or a polymeric moiety; and optionally contain one or more heteroatoms;
a is 0 or an integer of 1 to 12 and a is the same or different for each occurrence;
b is 0 or 1 wherein b = 0 indicates a five membered ring, b = 1 indicates a 6 membered ring, and b may be the same or different for each occurrence;
.alpha. is an integer of at least 1; and .beta. is an integer of at least 1.
20. A formulation comprising one or more polymeric compositions having structure VII.
21. An article comprising the formulation of claim 20.
22. A polymeric composition comprising one or more repeat units comprising structure VIII:
wherein R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
.alpha. is 1 or 2; and .beta. is an integer of at least 1.
wherein R1 is hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms;
and R1 is the same or different for each occurrence;
.alpha. is 1 or 2; and .beta. is an integer of at least 1.
23. A formulation comprising one or more polymeric compositions having structure VIII.
24. An article comprising the formulation of claim 23.
25. A bisketal having the structure IX:
wherein each R is independently hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms.
wherein each R is independently hydrogen, a metal cation, an organic cation, a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms.
26. A formulation comprising one or more bisketals having structure IX.
27. An article comprising the formulation of claim 26.
28. A polymeric composition comprising one or more repeat units comprising structure X:
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence, and .beta. is an integer of at least 1.
wherein R1 is a linear, branched, or cyclic alkyl, a linear, branched, or cyclic alkenyl, alkynyl, aryl, alkaryl, or an oligomeric or polymeric moiety; and optionally contains one or more heteroatoms; and R1 is the same or different for each occurrence, and .beta. is an integer of at least 1.
29. A formulation comprising one or more polymeric compositions having structure X.
30. An article comprising the formulation of claim 29.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2674778A CA2674778C (en) | 2007-10-09 | 2008-10-09 | Polyketal compounds, synthesis, and applications |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96062707P | 2007-10-09 | 2007-10-09 | |
| US96062807P | 2007-10-09 | 2007-10-09 | |
| US96062607P | 2007-10-09 | 2007-10-09 | |
| US60/960,628 | 2007-10-09 | ||
| US60/960,627 | 2007-10-09 | ||
| US60/960,626 | 2007-10-09 | ||
| US8440108P | 2008-07-29 | 2008-07-29 | |
| US61/084,401 | 2008-07-29 | ||
| PCT/US2008/079337 WO2009049041A2 (en) | 2007-10-09 | 2008-10-09 | Polyketal compounds, synthesis, and applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2674778A Division CA2674778C (en) | 2007-10-09 | 2008-10-09 | Polyketal compounds, synthesis, and applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2654809A1 true CA2654809A1 (en) | 2009-04-09 |
| CA2654809C CA2654809C (en) | 2011-03-29 |
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ID=40580767
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2654809A Expired - Fee Related CA2654809C (en) | 2007-10-09 | 2008-10-09 | Polyketal compounds, synthesis, and applications |
| CA2674778A Expired - Fee Related CA2674778C (en) | 2007-10-09 | 2008-10-09 | Polyketal compounds, synthesis, and applications |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2674778A Expired - Fee Related CA2674778C (en) | 2007-10-09 | 2008-10-09 | Polyketal compounds, synthesis, and applications |
Country Status (1)
| Country | Link |
|---|---|
| CA (2) | CA2654809C (en) |
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2008
- 2008-10-09 CA CA2654809A patent/CA2654809C/en not_active Expired - Fee Related
- 2008-10-09 CA CA2674778A patent/CA2674778C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2674778A1 (en) | 2009-04-09 |
| CA2674778C (en) | 2011-11-29 |
| CA2654809C (en) | 2011-03-29 |
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| EEER | Examination request | ||
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Effective date: 20161011 |