# US 2019/0169425 A1 · Monolayer carbon dioxide barrier pet bottles

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- Number: US 2019/0169425 A1
- Document ID: US20190169425A1
- Status: Published application
- Kind: A1
- Application number: 16/025,232
- Filed: 2018-07-02
- Published: 2019-06-06
- Earliest claimed: 2011-09-12
- Assignees: Plastipak Packaging, Inc.
- Applicants: Plastipak Packaging, Inc.
- Inventors: Girish N. Deshpande
- Web page: https://patentgrep.com/patent/US20190169425A1

## CPC

- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C08K 5/1545: Six-membered rings
- C08K 5/3437: condensed with carbocyclic rings
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## 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

### Claim 1

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 Rl to R8 are each independently chosen from:
i) hydrogen;
ii) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl;
iii) C2-C12 substituted or unsubstituted linear, branched, or cyclic alkenyl;
iv) C2-C12 substituted or unsubstituted linear or branched alkynyl;
v) C6 or C10 substituted or unsubstituted aryl;
vi) C1-C9 substituted or unsubstituted heterocyclic;
vii) C1-C11 substituted or unsubstituted heteroaryl;
viii) —[C(R10a)(R10b)]yOR11;
wherein R11 is chosen from:
a) —H;
b) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl or C1-C12 substituted or unsubstituted linear, branched, or cyclic haloalkyl;
c) C6 or C10 substituted or unsubstituted aryl or C7-C20 alkylenearyl;
d) C1-C9 substituted or unsubstituted heterocyclic; and
e) C1-C11 substituted or unsubstituted heteroaryl;
ix) —[C(R10a)(R10b)]yN(R12a)(R12b);
wherein R12a and R12b are each independently chosen from:
a) —H;
b) —OR13;
R13 is hydrogen or C1-C4 linear alkyl;
c) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl;
d) C6 or C10 substituted or unsubstituted aryl;
e) C1-C9 substituted or unsubstituted heterocyclic;
f) C1-C11 substituted or unsubstituted heteroaryl; and
g) R12a and R12b 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(R10a)(R10b)]yC(O)R14;
wherein R14 is chosen from:
a) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl;
b) —OR15;
wherein R15 is hydrogen, substituted or unsubstituted C1-C4 linear alkyl, C6 or C10 substituted or unsubstituted aryl, Cl-C9 substituted or unsubstituted heterocyclic, C1-C11 substituted or unsubstituted heteroaryl; and
c) —N(R16a)(R16b);
wherein R16a and R16b are each independently hydrogen, C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; C6 or C10 substituted or unsubstituted aryl; C1-C9 substituted or unsubstituted heterocyclic; C1-C11 substituted or unsubstituted heteroaryl; or R16a and R16b 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(R10a)(R10b)]yOC(O)R17;
wherein R17 is chosen from:
a) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R18a)(R18b);
R18a and R18b are each independently hydrogen, C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; C6 or C10 substituted or unsubstituted aryl; C1-C9 substituted or unsubstituted heterocyclic; C1-C11 substituted or unsubstituted heteroaryl; or R18a and R18b 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(R10a)(R10b)]yNR19C(O)R20;
wherein R18 is chosen from:
a) —H; and
b) C1-C4 substituted or unsubstituted linear, branched, or cyclic alkyl;
wherein R20 is chosen from:
a) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R21a)(R21b);
R21a and R21b are each independently hydrogen, C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; C6 or C10 substituted or unsubstituted aryl; C1-C9 substituted or unsubstituted heterocyclic; C1-C11 substituted or unsubstituted heteroaryl; or R21a and R21b 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(R10a)(R10b)]yCN;
xiv) —[C(R10a)(R10b)]yNO2;
xv) —[C(R10a)(R10b)]ySO2R22;
R22 is hydrogen, hydroxyl, substituted or unsubstituted C1-C4 linear or branched alkyl; substituted or unsubstituted C6, C10, or C14 aryl; C7-C15 alkylenearyl; C1-C9 substituted or unsubstituted heterocyclic; or C1-C11 substituted or unsubstituted heteroaryl; and
xvi) halogen;
xvii) —[C(R10a)(R10b)]y(CHj′Xk′)hCHjXk; 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;
R10a and R10b are each independently hydrogen or C1-C4 alkyl; and
the index y is from 0 to 5;
R1 and R8 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.

### Claim 2 (depends on 1)

A composition according to claim 1, wherein the substitutions are each independently chosen from:
i) C1-C12 linear, branched, or cyclic alkyl, alkenyl, and alkynyl;
ii) C1-C12 linear, branched, or cyclic alkoxy, alkenyloxy, and alkynyloxy;
iii) C1-C12 linear, branched, or cyclic haloalkyl, haloalkenyl, and haloalkynyl;
iv) C6 or C10 aryl;
v) C6 or C10 alkylenearyl;
vi) C1-C9 heterocyclic rings;
vii) C1-C9 heteroaryl rings;
viii) —(CR102aR102b)zOR101;
ix) —(CR102aR102b)zC(O)R101;
x) —(CR102aR102b)zC(O)OR101;
xi) —(CR102aR102b)zC(O)N(R101)2;
xii) —(CR102aR102b)zN(R101)2;
xiii) halogen;
xiv) —(CR102aR102b)zCN;
xv) —(CR102aR102b)zNO2;
xvi) —CHjXk; wherein X is halogen, the index j is an integer from 0 to 2, j+k=3; for example,
xvii) —(CR102aR102b)zSR101;
xviii) —(CR102aR102b)zSO2R101 and
xix) —(CR102aR102b)zSO3R101;
wherein each R101 is independently hydrogen, substituted or unsubstituted C1-C6 linear, branched, or cyclic alkyl, phenyl, benzyl, heterocyclic, or heteroaryl; or two R101 units can be taken together to form a ring comprising 3-7 atoms; R102a and R102b are each independently hydrogen or C1-C4 linear or branched alkyl; the index z is from 0 to 4.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein R2 to R7 are each hydrogen.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein R1 and R8 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.

### Claim 5 (depends on 1)

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:

### Claim 6 (depends on 1)

The composition according to claim 1, wherein the compound is benzo[de]-isochromene-1,3-dione having the formula:

### Claim 7 (depends on 1)

The composition according to claim 1, wherein the compound has the formula:
R1 and R8 are each independently:
i) hydrogen; or
ii) —C(O)R14;
wherein R14 is —OR15 or —N(R16a)(R16b); R15 is hydrogen or methyl; R16a and R16b are each independently hydrogen or methyl.

### Claim 8 (depends on 1)

The composition according to claim 1, wherein the compound is naphthalene-1,8-dicarobxamide having the formula:

### Claim 9 (depends on 1)

The composition according to claim 1, wherein the oxygen scavenger is an N-allylic amine or N-benzylic amide.

### Claim 10 (depends on 1)

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

### Claim 11

(canceled)

### Claim 12

(canceled)

### Claim 13

(canceled)

### Claim 14

(canceled)

### Claim 15

(canceled)

### Claim 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 Rl to R8 are each independently chosen from:
i) hydrogen;
ii) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl;
iii) C2-C12 substituted or unsubstituted linear, branched, or cyclic alkenyl;
iv) C2-C12 substituted or unsubstituted linear or branched alkynyl;
v) C6 or C10 substituted or unsubstituted aryl;
vi) C1-C9 substituted or unsubstituted heterocyclic;
vii) C1-C11 substituted or unsubstituted heteroaryl;
viii) —[C(R10a)(R10b)]yOR11;
wherein R11 is chosen from:
a) —H;
b) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl or C1-C12 substituted or unsubstituted linear, branched, or cyclic haloalkyl;
c) C6 or C10 substituted or unsubstituted aryl or C7-C20 alkylenearyl;
d) C1-C9 substituted or unsubstituted heterocyclic; and
e) C1-C11 substituted or unsubstituted heteroaryl;
ix) —[C(R10a)(R10b)]yN(R12a)(R12b);
wherein R12a and R12b are each independently chosen from:
a) —H;
b) —OR13;
R13 is hydrogen or C1-C4 linear alkyl;
c) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl;
d) C6 or C10 substituted or unsubstituted aryl;
e) C1-C9 substituted or unsubstituted heterocyclic;
f) C1-C11 substituted or unsubstituted heteroaryl; and
g) R12a and R12b 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(R10a)(R10b)]yC(O)R14;
wherein R14 is chosen from:
a) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl;
b) —OR15;
wherein R15 is hydrogen, substituted or unsubstituted C1-C4 linear alkyl, C6 or C10 substituted or unsubstituted aryl, Cl-C9 substituted or unsubstituted heterocyclic, C1-C11 substituted or unsubstituted heteroaryl; and
c) —N(R16a)(R16b);
wherein R16a and R16b are each independently hydrogen, C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; C6 or C10 substituted or unsubstituted aryl; C1-C9 substituted or unsubstituted heterocyclic; C1-C11 substituted or unsubstituted heteroaryl; or R16a and R16b 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(R10a)(R10b)]yOC(O)R17;
wherein R17 is chosen from:
a) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R18a)(R18b);
R18a and R18b are each independently hydrogen, C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; C6 or C10 substituted or unsubstituted aryl; C1-C9 substituted or unsubstituted heterocyclic; C1-C11 substituted or unsubstituted heteroaryl; or R18a and R18b 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(R10a)(R10b)]yNR19C(O)R20;
wherein R18 is chosen from:
a) —H; and
b) C1-C4 substituted or unsubstituted linear, branched, or cyclic alkyl;
wherein R20 is chosen from:
a) C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; and
b) —N(R21a)(R21b);
R21a and R21b are each independently hydrogen, C1-C12 substituted or unsubstituted linear, branched, or cyclic alkyl; C6 or C10 substituted or unsubstituted aryl; C1-C9 substituted or unsubstituted heterocyclic; C1-C11 substituted or unsubstituted heteroaryl; or R21a and R21b 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(R10a)(R10b)]yCN;
xiv) —[C(R10a)(R10b)]yNO2;
xv) —[C(R10a)(R10b)]ySO2R22;
R22 is hydrogen, hydroxyl, substituted or unsubstituted C1-C4 linear or branched alkyl; substituted or unsubstituted C6, C10, or C14 aryl; C7-C15 alkylenearyl; C1-C9 substituted or unsubstituted heterocyclic; or C1-C11 substituted or unsubstituted heteroaryl; and
xvi) halogen;
xvii) —[C(R10a)(R10b)]y(CHj′Xk′)hCHjXk; 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;
R10a and R10b are each independently hydrogen or C1-C4 alkyl; and
the index y is from 0 to 5;
R1 and R8 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.

### Claim 17 (depends on 16)

A article according to claim 16, wherein the substitutions are each independently chosen from:
i) C1-C12 linear, branched, or cyclic alkyl, alkenyl, and alkynyl;
ii) C1-C12 linear, branched, or cyclic alkoxy, alkenyloxy, and alkynyloxy;
iii) C1-C12 linear, branched, or cyclic haloalkyl, haloalkenyl, and haloalkynyl;
iv) C6 or C10 aryl;
v) C6 or C10 alkylenearyl;
vi) C1-C9 heterocyclic rings;
vii) C1-C9 heteroaryl rings;
viii) —(CR102aR102b)zOR101;
ix) —(CR102aR102b)zC(O)R101;
x) —(CR102aR102b)zC(O)OR101;
xi) —(CR102aR102b)zC(O)N(R101)2;
xii) —(CR102aR102b)zN(R101)2;
xiii) halogen;
xiv) —(CR102aR102b)zCN;
xv) —(CR102aR102b)zNO2;
xvi) —CHjXk; wherein X is halogen, the index j is an integer from 0 to 2, j+k=3; for example,
xvii) —(CR102aR102b)zSR101;
xviii) —(CR102aR102b)zSO2R101 and
xix) —(CR102aR102b)zSO3R101;
wherein each R101 is independently hydrogen, substituted or unsubstituted C1-C6 linear, branched, or cyclic alkyl, phenyl, benzyl, heterocyclic, or heteroaryl; or two R101 units can be taken together to form a ring comprising 3-7 atoms; R102a and R102b are each independently hydrogen or C1-C4 linear or branched alkyl; the index z is from 0 to 4.

### Claim 18 (depends on 16)

The article according to claim 16, wherein R2 to R7 are each hydrogen.

### Claim 19 (depends on 16)

The article according to claim 16, wherein R1 and R8 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.

### Claim 20 (depends on 16)

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:

### Claim 21 (depends on 16)

The article according to claim 16, wherein the compound is benzo[de]-isochromene-1,3-dione having the formula:

### Claim 22 (depends on 16)

The article according to claim 16, wherein the compound has the formula:
R1 and R8 are each independently:
i) hydrogen; or
ii) —C(O)R14;
wherein R14 is —OR15 or —N(R16a)(R16b); R15 is hydrogen or methyl; R16a and R16b are each independently hydrogen or methyl.

### Claim 23 (depends on 16)

The article according to claim 16, wherein the compound is naphthalene-1,8-dicarobxamide having the formula:

### Claim 24 (depends on 16)

The article according to claim 16, wherein the oxygen scavenger is an N-allylic amide or N-benzylic amide.

### Claim 25 (depends on 16)

The article according to claim 16, wherein the base polymer comprises a polyester.

### Claim 26

(canceled)