Monolayer carbon dioxide barrier PET bottles

Patent metadata

Field	Value
Publication number	US-10011714-B2
Application number	US-201213612064-A
Country	US
Kind code	B2
Filing date	Sep 12, 2012
Priority date	Sep 12, 2011
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

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.

First claim

What is claimed is:

1. A polymer composition, comprising:
a) a base polymer comprising a polyester or polypropylene; and
b) from about 0.1% to about 10% by weight of a compound having the formula:

wherein R 1 and R 8 are each independently chosen from:
ii) C 7 -C 12 linear, branched, or cyclic alkyl;
iii) C 2 -C 12 linear, branched, or cyclic alkenyl;
iv) C 2 -C 12 linear or branched alkynyl;
v) C 6 or C 10 aryl;
viii) —[C(R 10a )(R 10b )] y OR 11 ;
wherein R 11 is chosen from:
a) —H;
b) C 1 -C 12 linear, branched, or cyclic alkyl or C 1 -C 12 linear, branched, or cyclic haloalkyl; and
c) C 6 or C 10 aryl or C 7 -C 20 alkylenearyl;

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 -C 4 linear alkyl;

c) C 1 -C 12 linear, branched, or cyclic alkyl; and
d) C 6 or C 10 aryl; and
wherein when y is 0 R 12a and R 12b are not both a C 1 -C 12 linear, branched, or cyclic alkyl;

x) —[C(R 10a )(R 10b )] y C(O)R 14 ;
wherein R 14 is chosen from:
a) C 1 -C 12 linear, branched, or cyclic alkyl;
b) —OR 15 ;
wherein R 15 is hydrogen, C 1 -C 4 linear alkyl, or C 6 or C 10 aryl; and

c) —N(R 16a )(R 16b );
wherein R 16a and R 16b are each independently hydrogen, C 1 -C 12 linear, branched, or cyclic alkyl; or C 6 or C 10 aryl;

xi) —[C(R 10a )(R 10b )] y OC(O)R 17 ;
wherein R 17 is chosen from:
a) C 1 -C 12 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 linear, branched, or cyclic alkyl; or C 6 or C 10 aryl;

xii) —[C(R 10a )(R 10b )] y NR 19 C(O)R 20 ;
wherein R 19 is chosen from:
a) —H; and
b) C 1 -C 4 linear, branched, or cyclic alkyl;
wherein R 20 is chosen from:
a) C 1 -C 12 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 linear, branched, or cyclic alkyl; or C 6 or C 10 aryl;

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, C 1 -C 4 linear or branched alkyl; C 6 , C 10 , or C 14 aryl; or C 7 -C 15 alkylenearyl;

xvi) halogen; and
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; or
xviii) R 1 and R 8 together form a 6 membered ring containing from 4 to 6 carbon atoms and from 0 to 2 heteroatoms chosen from oxygen, sulfur, or nitrogen, wherein one or more of the carbon atoms can form a carbonyl unit; and
R 10a and R 10b are each independently hydrogen or C 1 -C 4 alkyl; and
the index y is from 0 to 5; and
wherein R 2 to R 7 are each hydrogen.

2. The composition according to claim 1 , wherein R 1 and R 8 are each independently chosen from:
i) C 7 -C 12 linear, branched, or cyclic alkyl, alkenyl, and alkynyl;
ii) C 1 -C 12 linear, branched, or cyclic alkoxy;
iii) C 1 -C 12 linear, haloalkyl;
iv) C 6 or C 10 aryl;
v) C 7 -C 20 alkylenearyl;
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(R 101 ) 2 , wherein when z is 0 then R 101 is not C 1 -C 6 linear, branched, or cyclic alkyl;
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;
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, C 1 -C 6 linear, branched, or cyclic alkyl, phenyl, or benzyl; 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 1 and R 8 together form a 6 membered 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 forms a carbonyl unit.

4. The composition according to claim 1 , wherein the compound is chosen from:
i) benzo[de]isochromen-1(3H)-one having the formula:

ii) 1H-benzo[de]isoquinoline-1,3(2H)-dione having the formula:

and
iii) 2,3-dihydro-1H-benzo[de]isoquinolin-1-one having the formula:

5. The composition according to claim 1 , further comprising from about 0.1% to about 10% by weight of an oxygen scavenger; wherein the oxygen scavenger is an N-allylic amine or N-benzylic amide.

6. The composition according to claim 1 , wherein the base polymer comprises a polyester.

7. The composition according to claim 6 , wherein the polyester base polymer comprises polyethylene terephthalate or a copolymer thereof.

8. The polymer composition of claim 1 , wherein the base polymer comprises polypropylene.

9. A preform comprising the composition according to any one of claims 1 , 2 , 3 , 4 and 5 - 8 .

10. An article of manufacture comprising the composition according to any one of claims 1 , 2 , 3 , 4 and 5 - 8 .

11. The article according to claim 10 , wherein the article is a monolayered article.

12. An article of manufacture, comprising:
a) a base polymer comprising a polyester or polypropylene;
b) from about 0.1% to about 10% by weight of a compound having the formula:

wherein R 1 and R 8 are each independently chosen from:
ii) C 7 -C 12 linear, branched, or cyclic alkyl;
iii) C 2 -C 12 linear, branched, or cyclic alkenyl;
iv) C 2 -C 12 linear or branched alkynyl;
v) C 6 or C 10 aryl;
viii) —[C(R 10a )(R 10b )] y OR 11 ;
wherein R 11 is chosen from:
a) —H;
b) C 1 -C 12 linear, branched, or cyclic alkyl or C 1 -C 12 linear, branched, or cyclic haloalkyl; and
c) C 6 or C 10 aryl or C 7 -C 20 alkylenearyl;

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 -C 4 linear alkyl;

c) C 1 -C 12 linear, branched, or cyclic alkyl; and
d) C 6 or C 10 aryl; and
wherein when y is 0, then R 12a and R 12b are not both a C 1 -C 12 linear, branched, or cyclic alkyl;

x) —[C(R 10a )(R 10b )] y C(O)R 14 ;
wherein R 14 is chosen from:
a) C 1 -C 12 linear, branched, or cyclic alkyl;
b) —OR 15 ;
wherein R 15 is hydrogen, C 1 -C 4 linear alkyl, or C 6 or C 10 aryl; and

c) —N(R 16a )(R 16b );
wherein R 16a and R 16b are each independently hydrogen, C 1 -C 12 linear, branched, or cyclic alkyl; or C 6 or C 10 aryl;

xi) —[C(R 10a )(R

Assignees

• Deshpande Girish N
• Plastipak Packaging Inc

Inventors

• Deshpande Girish N

Classifications

• C08K5/1545 Primary

  Six-membered rings · CPC title

• C08L67/02 Primary

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) · CPC title

• C08K5/3437

  condensed with carbocyclic rings · CPC title

• C08L65/00

  Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers · CPC title

• B32B27/18

  characterised by the use of special additives · CPC title