US2019169425A1PendingUtilityA1
Monolayer carbon dioxide barrier pet bottles
Est. expirySep 12, 2031(~5.1 yrs left)· nominal 20-yr term from priority
Inventors:Girish Nilkanth Deshpande
C08K 5/3437C08L 67/02C08K 5/1545B32B 27/18C08L 65/00
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Claims
Abstract
Disclosed herein are articles comprising polymer compositions that can provide a barrier to carbon dioxide diffusion. The disclosed polymer compositions can be utilized in packaging to retard or prevent the diffusion of carbon dioxide out of a carbonated liquid, inter alia, a carbonated soft drink. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Claims
exact text as granted — not AI-modified1 . A polymer composition, comprising:
a) a base polymer; and b) from about 0.1% to about 10% by weight of a compound having the formula:
wherein R l to R 8 are each independently chosen from:
i) hydrogen;
ii) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl;
iii) C 2 -C 12 substituted or unsubstituted linear, branched, or cyclic alkenyl;
iv) C 2 -C 12 substituted or unsubstituted linear or branched alkynyl;
v) C 6 or C 10 substituted or unsubstituted aryl;
vi) C 1 -C 9 substituted or unsubstituted heterocyclic;
vii) C 1 -C 11 substituted or unsubstituted heteroaryl;
viii) —[C(R 10a )(R 10b )] y OR 11 ;
wherein R 11 is chosen from:
a) —H;
b) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl or C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic haloalkyl;
c) C 6 or C 10 substituted or unsubstituted aryl or C 7 -C 20 alkylenearyl;
d) C 1 -C 9 substituted or unsubstituted heterocyclic; and
e) C 1 -C 11 substituted or unsubstituted heteroaryl;
ix) —[C(R 10a )(R 10b )] y N(R 12a )(R 12b );
wherein R 12a and R 12b are each independently chosen from:
a) —H;
b) —OR 13 ;
R 13 is hydrogen or C 1 -C4 linear alkyl;
c) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl;
d) C 6 or C 10 substituted or unsubstituted aryl;
e) C 1 -C 9 substituted or unsubstituted heterocyclic;
f) C 1 -C 11 substituted or unsubstituted heteroaryl; and
g) R 12a and R 12b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
x) —[C(R 10a )(R 10b )] y C(O)R 14 ;
wherein R 14 is chosen from:
a) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl;
b) —OR 15 ;
wherein R 15 is hydrogen, substituted or unsubstituted C 1 -C 4 linear alkyl, C 6 or C 10 substituted or unsubstituted aryl, C l -C 9 substituted or unsubstituted heterocyclic, C 1 -C 11 substituted or unsubstituted heteroaryl; and
c) —N(R 16a )(R 16b );
wherein R 16a and R 16b are each independently hydrogen, C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; C 6 or C 10 substituted or unsubstituted aryl; C 1 -C 9 substituted or unsubstituted heterocyclic; C 1 -C 11 substituted or unsubstituted heteroaryl; or R 16a and R 16b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
xi) —[C(R 10a )(R 10b )] y OC(O)R 17 ;
wherein R 17 is chosen from:
a) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R 18a )(R 18b );
R 18a and R 18b are each independently hydrogen, C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; C 6 or C 10 substituted or unsubstituted aryl; C 1 -C 9 substituted or unsubstituted heterocyclic; C 1 -C 11 substituted or unsubstituted heteroaryl; or R 18a and R 18b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
xii) —[C(R 10a )(R 10b )] y NR 19 C(O)R 20 ;
wherein R 18 is chosen from:
a) —H; and
b) C 1 -C 4 substituted or unsubstituted linear, branched, or cyclic alkyl;
wherein R 20 is chosen from:
a) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R 21a )(R 21b );
R 21a and R 21b are each independently hydrogen, C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; C 6 or C 10 substituted or unsubstituted aryl; C 1 -C 9 substituted or unsubstituted heterocyclic; C 1 -C 11 substituted or unsubstituted heteroaryl; or R 21a and R 21b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
xiii) —[C(R 10a )(R 10b )] y CN;
xiv) —[C(R 10a )(R 10b )] y NO 2 ;
xv) —[C(R 10a )(R 10b )] y SO 2 R 22 ;
R 22 is hydrogen, hydroxyl, substituted or unsubstituted C 1 -C 4 linear or branched alkyl; substituted or unsubstituted C 6 , C 10 , or C 14 aryl; C 7 -C 15 alkylenearyl; C 1 -C 9 substituted or unsubstituted heterocyclic; or C 1 -C 11 substituted or unsubstituted heteroaryl; and
xvi) halogen;
xvii) —[C(R 10a )(R 10b )] y (CH j′ X k′ ) h CH j X k ; wherein X is halogen, the index j is an integer from 0 to 2, the index k is an integer from 1 to 3, j+k=3; the index j′ is an integer from 0 to 2, the index k′ is and integer from 0 to 2, j′+k′=2; the index h is from 0 to 5;
R 10a and R 10b are each independently hydrogen or C 1 -C 4 alkyl; and
the index y is from 0 to 5;
R 1 and R 8 can be taken together to from a 5 to 7 member ring containing from 3 to 7 carbon atoms and from 0 to 2 heteroatoms chosen from oxygen, sulfur, or nitrogen, wherein one or more of the carbon atoms can be substituted, unsubstituted, or a carbonyl unit.
2 . A composition according to claim 1 , wherein the substitutions are each independently chosen from:
i) C 1 -C 12 linear, branched, or cyclic alkyl, alkenyl, and alkynyl; ii) C 1 -C 12 linear, branched, or cyclic alkoxy, alkenyloxy, and alkynyloxy; iii) C 1 -C 12 linear, branched, or cyclic haloalkyl, haloalkenyl, and haloalkynyl; iv) C 6 or C 10 aryl; v) C 6 or C 10 alkylenearyl; vi) C 1 -C 9 heterocyclic rings; vii) C 1 -C 9 heteroaryl rings; viii) —(CR 102a R 102b ) z OR 101 ; ix) —(CR 102a R 102b ) z C(O)R 101 ; x) —(CR 102a R 102b ) z C(O)OR 101 ; xi) —(CR 102a R 102b ) z C(O)N(R 101 ) 2 ; xii) —(CR 102a R 102b ) z N(R101) 2 ; xiii) halogen; xiv) —(CR 102a R 102b ) z CN; xv) —(CR 102a R 102b ) z NO 2 ; xvi) —CH j X k ; wherein X is halogen, the index j is an integer from 0 to 2, j+k=3; for example, xvii) —(CR 102a R 102b ) z SR 101 ; xviii) —(CR 102a R 102b ) z SO 2 R 101 and xix) —(CR 102a R 102b ) z SO 3 R 101 ; wherein each R 101 is independently hydrogen, substituted or unsubstituted C 1 -C 6 linear, branched, or cyclic alkyl, phenyl, benzyl, heterocyclic, or heteroaryl; or two R 101 units can be taken together to form a ring comprising 3-7 atoms; R 102a and R 102b are each independently hydrogen or C 1 -C 4 linear or branched alkyl; the index z is from 0 to 4.
3 . The composition according to claim 1 , wherein R 2 to R 7 are each hydrogen.
4 . The composition according to claim 1 , wherein R 1 and R 8 can be taken together to from 6 member ring containing from 4 to 5 carbon atoms and 1 or 2 heteroatoms chosen from oxygen, sulfur, or nitrogen, wherein one or more of the carbon atoms is a carbonyl unit.
5 . The composition according to claim 1 , wherein the compound is chosen from:
i) benzo[d]isochromen-1(3H)-one having the formula:
ii) 1H-henzo[d]isoquinoline-1,3(2H)-dione having the formula:
and
iii) 2,3-dihydro-1H-benzo[de]isoquinolin-1-one having the formula:
6 . The composition according to claim 1 , wherein the compound is benzo[de]-isochromene-1,3-dione having the formula:
7 . The composition according to claim 1 , wherein the compound has the formula:
R 1 and R 8 are each independently:
i) hydrogen; or
ii) —C(O)R 14 ;
wherein R 14 is —OR 15 or —N(R 16a )(R 16b ); R 15 is hydrogen or methyl; R 16a and R 16b are each independently hydrogen or methyl.
8 . The composition according to claim 1 , wherein the compound is naphthalene-1,8-dicarobxamide having the formula:
9 . The composition according to claim 1 , wherein the oxygen scavenger is an N-allylic amine or N-benzylic amide.
10 . The composition according to claim 1 , wherein the base polymer comprises a polyester or a polypropylene.
11 . (canceled)
12 . (canceled)
13 . (canceled)
14 . (canceled)
15 . (canceled)
16 . An article of manufacture, comprising:
a) a base polymer; b) from about 0.1% to about 10% by weight of a compound having the formula:
wherein R l to R 8 are each independently chosen from:
i) hydrogen;
ii) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl;
iii) C 2 -C 12 substituted or unsubstituted linear, branched, or cyclic alkenyl;
iv) C 2 -C 12 substituted or unsubstituted linear or branched alkynyl;
v) C 6 or C 10 substituted or unsubstituted aryl;
vi) C 1 -C 9 substituted or unsubstituted heterocyclic;
vii) C 1 -C 11 substituted or unsubstituted heteroaryl;
viii) —[C(R 10a )(R 10b )] y OR 11 ;
wherein R 11 is chosen from:
a) —H;
b) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl or C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic haloalkyl;
c) C 6 or C 10 substituted or unsubstituted aryl or C 7 -C 20 alkylenearyl;
d) C 1 -C 9 substituted or unsubstituted heterocyclic; and
e) C 1 -C 11 substituted or unsubstituted heteroaryl;
ix) —[C(R 10a )(R 10b )] y N(R 12a )(R 12b );
wherein R 12a and R 12b are each independently chosen from:
a) —H;
b) —OR 13 ;
R 13 is hydrogen or C 1 -C4 linear alkyl;
c) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl;
d) C 6 or C 10 substituted or unsubstituted aryl;
e) C 1 -C 9 substituted or unsubstituted heterocyclic;
f) C 1 -C 11 substituted or unsubstituted heteroaryl; and
g) R 12a and R 12b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
x) —[C(R 10a )(R 10b )] y C(O)R 14 ;
wherein R 14 is chosen from:
a) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl;
b) —OR 15 ;
wherein R 15 is hydrogen, substituted or unsubstituted C 1 -C 4 linear alkyl, C 6 or C 10 substituted or unsubstituted aryl, C l -C 9 substituted or unsubstituted heterocyclic, C 1 -C 11 substituted or unsubstituted heteroaryl; and
c) —N(R 16a )(R 16b );
wherein R 16a and R 16b are each independently hydrogen, C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; C 6 or C 10 substituted or unsubstituted aryl; C 1 -C 9 substituted or unsubstituted heterocyclic; C 1 -C 11 substituted or unsubstituted heteroaryl; or R 16a and R 16b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
xi) —[C(R 10a )(R 10b )] y OC(O)R 17 ;
wherein R 17 is chosen from:
a) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R 18a )(R 18b );
R 18a and R 18b are each independently hydrogen, C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; C 6 or C 10 substituted or unsubstituted aryl; C 1 -C 9 substituted or unsubstituted heterocyclic; C 1 -C 11 substituted or unsubstituted heteroaryl; or R 18a and R 18b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
xii) —[C(R 10a )(R 10b )] y NR 19 C(O)R 20 ;
wherein R 18 is chosen from:
a) —H; and
b) C 1 -C 4 substituted or unsubstituted linear, branched, or cyclic alkyl;
wherein R 20 is chosen from:
a) C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R 21a )(R 21b );
R 21a and R 21b are each independently hydrogen, C 1 -C 12 substituted or unsubstituted linear, branched, or cyclic alkyl; C 6 or C 10 substituted or unsubstituted aryl; C 1 -C 9 substituted or unsubstituted heterocyclic; C 1 -C 11 substituted or unsubstituted heteroaryl; or R 21a and R 21b can be taken together to form a substituted or unsubstituted ring having from 3 to 10 carbon atoms and from 0 to 3 heteroatoms chosen from oxygen, nitrogen, and sulfur;
xiii) —[C(R 10a )(R 10b )] y CN;
xiv) —[C(R 10a )(R 10b )] y NO 2 ;
xv) —[C(R 10a )(R 10b )] y SO 2 R 22 ;
R 22 is hydrogen, hydroxyl, substituted or unsubstituted C 1 -C 4 linear or branched alkyl; substituted or unsubstituted C 6 , C 10 , or C 14 aryl; C 7 -C 15 alkylenearyl; C 1 -C 9 substituted or unsubstituted heterocyclic; or C 1 -C 11 substituted or unsubstituted heteroaryl; and
xvi) halogen;
xvii) —[C(R 10a )(R 10b )] y (CH j′ X k′ ) h CH j X k ; wherein X is halogen, the index j is an integer from 0 to 2, the index k is an integer from 1 to 3, j+k=3; the index j′ is an integer from 0 to 2, the index k′ is and integer from 0 to 2, j′+k′=2; the index h is from 0 to 5;
R 10a and R 10b are each independently hydrogen or C 1 -C 4 alkyl; and
the index y is from 0 to 5;
R 1 and R 8 can be taken together to from a 5 to 7 member ring containing from 3 to 7 carbon atoms and from 0 to 2 heteroatoms chosen from oxygen, sulfur, or nitrogen, wherein one or more of the carbon atoms can be substituted, unsubstituted, or a carbonyl unit.
17 . A article according to claim 16 , wherein the substitutions are each independently chosen from:
i) C 1 -C 12 linear, branched, or cyclic alkyl, alkenyl, and alkynyl; ii) C 1 -C 12 linear, branched, or cyclic alkoxy, alkenyloxy, and alkynyloxy; iii) C 1 -C 12 linear, branched, or cyclic haloalkyl, haloalkenyl, and haloalkynyl; iv) C 6 or C 10 aryl; v) C 6 or C 10 alkylenearyl; vi) C 1 -C 9 heterocyclic rings; vii) C 1 -C 9 heteroaryl rings; viii) —(CR 102a R 102b ) z OR 101 ; ix) —(CR 102a R 102b ) z C(O)R 101 ; x) —(CR 102a R 102b ) z C(O)OR 101 ; xi) —(CR 102a R 102b ) z C(O)N(R 101 ) 2 ; xii) —(CR 102a R 102b ) z N(R101) 2 ; xiii) halogen; xiv) —(CR 102a R 102b ) z CN; xv) —(CR 102a R 102b ) z NO 2 ; xvi) —CH j X k ; wherein X is halogen, the index j is an integer from 0 to 2, j+k=3; for example, xvii) —(CR 102a R 102b ) z SR 101 ; xviii) —(CR 102a R 102b ) z SO 2 R 101 and xix) —(CR 102a R 102b ) z SO 3 R 101 ; wherein each R 101 is independently hydrogen, substituted or unsubstituted C 1 -C 6 linear, branched, or cyclic alkyl, phenyl, benzyl, heterocyclic, or heteroaryl; or two R 101 units can be taken together to form a ring comprising 3-7 atoms; R 102a and R 102b are each independently hydrogen or C 1 -C 4 linear or branched alkyl; the index z is from 0 to 4.
18 . The article according to claim 16 , wherein R 2 to R 7 are each hydrogen.
19 . The article according to claim 16 , wherein R 1 and R 8 can be taken together to from 6 member ring containing from 4 to 5 carbon atoms and 1 or 2 heteroatoms chosen from oxygen, sulfur, or nitrogen, wherein one or more of the carbon atoms is a carbonyl unit.
20 . The article according to claim 16 , wherein the compound is chosen from:
i) benzo[d]isochromen-1(3H)-one having the formula:
ii) 1H-henzo[d]isoquinoline-1,3(2H)-dione having the formula:
and
iii) 2,3-dihydro-1H-benzo[de]isoquinolin-1-one having the formula:
21 . The article according to claim 16 , wherein the compound is benzo[de]-isochromene-1,3-dione having the formula:
22 . The article according to claim 16 , wherein the compound has the formula:
R 1 and R 8 are each independently:
i) hydrogen; or
ii) —C(O)R 14 ;
wherein R 14 is —OR 15 or —N(R 16a )(R 16b ); R 15 is hydrogen or methyl; R 16a and R 16b are each independently hydrogen or methyl.
23 . The article according to claim 16 , wherein the compound is naphthalene-1,8-dicarobxamide having the formula:
24 . The article according to claim 16 , wherein the oxygen scavenger is an N-allylic amide or N-benzylic amide.
25 . The article according to claim 16 , wherein the base polymer comprises a polyester.
26 . (canceled)Join the waitlist — get patent alerts
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