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1. (WO2017040024) STABILIZED POLYMERIC NANOCAPSULES, DISPERSIONS COMPRISING THE NANOCAPSULES, AND METHODS FOR THE TREATMENT OF BACTERIAL BIOFILMS
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CLAIMS

1. A nanocapsule comprising,

a liquid hydrophobic core comprising an essential oil; and

a shell encapsulating the core, the shell comprising a copolymer comprising repeating units of Formula (I) and (II)


wherein R4 and R5 are independently at each occurrence a C^ alkyl group and R6 and R7 are independently at each occurrence hydrogen or a Ci_6 alkyl group;

L1 is independently at each occurrence a divalent group that is (-CH2-)Z, wherein z is an integer from 1 to 10, a divalent a C1-20 alkylene oxide group, or a divalent poly(Ci-6 alkylene oxide) group;

R1 is independently at each occurrence hydrogen, a C1-12 alkylene group, or a -C(=0)-0-(Ci-6 alkyl) group;

y is 2 or 3;

p is 0 or 1 ; and

R2 is independently at each occurrence a C1-12 alkylene group, a C6-2o arylene group, a Ci-20 alkylene oxide group, a poly(Ci_6 alkylene oxide) group, or a zwitterionic group.

2. The nanocapsule of claim 1, wherein the copolymer further comprises repeating units of Formula (III)

wherein

X is independently at each occurrence -0-, -S-, -CH2-, -(CR4R5)-, or

wherein R4 and R5 are independently at each occurrence a C^ alkyl group and R6 and R7 are independently at each occurrence hydrogen or a Ci_6 alkyl group;

L2 is independently at each occurrence a divalent group that is (-CH2-)Z, wherein z is an integer from 1 to 10, a divalent a C1-20 alkylene oxide group, or a divalent poly(Ci-6 alkylene oxide) group;

R3 is independently at each occurrence hydrogen, a C1-12 alkylene group, or a -C(=0)-0-(Ci-6 alkyl) group;

a is 2 or 3; and

b is 0 or 1.

3. The nanocapsule of claim 1, wherein the copolymer further comprises repeating units of Formula (IV).

4. The nanocapsule of claim 1, wherein the copolymer further comprises repeating units of Formula (V)


wherein X is independently at each occurrence -0-, -S-, -CH2-, -(CR4R5)-, or


wherein R and R are independently at each occurrence a C^ alkyl group and R6 and R are independently at each occurrence hydrogen or a Ci_6 alkyl group;

R2 is independently at each occurrence a C1-12 alkylene group, a C6-2o arylene group, a Ci-20 alkylene oxide group, a poly(Ci_6 alkylene oxide) group, or a zwitterionic group; and

L3 is a divalent group that is (-CH2-)Z, wherein z is an integer from 1 to 10.

5. The nanocapsule of claim 1, wherein the core further comprises a hydrophobic anhydride-containing polymer in an amount of 0.01 to 15 weight percent, based on the weight of the core, wherein the hydrophobic anhydride-containing polymer comprising repeating units of Formula (VI)


wherein R is independently at each occurrence a hydrogen, a C1-20 alkyl group or a C6-2o aryl group.

6. The nanocapsule of claim 5, wherein at least a portion of the shell is crosslinked with the anhydride-containing polymer.

7. The nanocapsule of claim 1, wherein the essential oil is selected from the group consisting of peppermint oil, oregano oil, thymol, menthol, methyl salicylate, eucalyptol, carvacrol, camphor, anethole, carvone, eugenol, isoeugenol, limonene, osimen, n-decyl alcohol, citronel, a-salpineol, methyl acetate, citronellyl acetate, methyl eugenol, cineol, linalool, ethyl linalaol, safrola vanillin, spearmint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, laurel oil, cedar leaf oil, clove oil, cilantro oil, coriander oil, or a combination thereof.

8. The nanocapsule of claim 2, wherein the copolymer comprises

5 to 50 mole percent repeating units of Formula (I);

10 to 50 mole percent repeating units of Formula (II); and

25 to 45 mole percent repeating units of Formula (III);

wherein mole percent of each component is based on the total moles of the copolymer.

9. The nanocapsule of claim 1, wherein

X is -0-;

L1 is propylene;

R1 is hydrogen;

y is 3;

p is 1; and

R2 is a Ci-20 alkylene oxide group.

The nanocapsule of claim 1, wherein R2 is a group having the structure


wherein

n is 1, 2, 3, or 4; and

R10 is hydrogen, methyl, or a C

11. The nanocapsule of claim 2, wherein

R3 is hydrogen;

L2 is propylene;

a is 3; and

b is 1.

12. The nanocapsule of claim 1, wherein the copolymer has a number average molecular weight of 3,000 to 100,000 Daltons.

13. The nanocapsule of claim 1, comprising

90 to 99.9 weight percent of the core; and

0.1 to 10 weight percent of the shell;

wherein weight percent is based on the total weight of the nanocapsule.

14. The nanocapsule of claim 1, wherein the nanocapsule comprises

1 to 10 weight percent, based on the weight of the nanocapsule, of the core comprising carvacrol oil; and

90 to 99 weight percent, based on the weight of the nanocapsule, of the shell comprising the copolymer, wherein

each occurrence of X is -0-;

each occurrence of L1 is propylene;

each occurrence of R1 is hydrogen;

each occurrence of y is 3;

each occurrence of p is 1;

each occurrence of R2 is a group having the structure


wherein n is 4; and

the nanocapsule has a diameter of 1 to 100 nanometers.

15. The nanocapsule of claim 2, wherein the nanocapsule comprises

1 to 10 weight percent, based on the weight of the nanocapsule, of the core comprising

85 to 99.99 weight percent, based on the weight of the core, of carvacrol oil; and

0.01 to 15 weight percent, based on the weight of the core, of the hydrophobic anhydride containing polymer comprising repeating units of Formula (VI)


wherein m is an integer from 1 to 16; and

90 to 99 weight percent, based on the weight of the nanocapsule, of the shell comprising the copolymer, wherein

each occurrence of X is -0-;

each occurrence of L1 and L2 are propylene;

each occurrence of R1 is hydrogen;

each occurrence of y is 3;

each occurrence of p is 1;

each occurrence of R2 is a group having the structure


wherein n is 4;

each occurrence of R3 is hydrogen;

each occurrence of a is 3;

each occurrence of b is 1;

the nanocapsule has a diameter of 1 to 100 nanometers; and

wherein at least a portion of the shell is crosslinked with the anhydride- containing polymer.

16. A dispersion comprising a plurality of nanocapsules according to claim 1.

17. The dispersion of claim 16, wherein the nanocapsules are dispersed in an aqueous solution.

18. A method of treating a bacterial biofilm, the method comprising,

contacting the dispersion of claim 16 with a bacterial biofilm.

19. The method of claim 18, wherein the bacterial biofilm comprises Escherichia coli, Pseudomonas bacteria, Staphylococcal bacteria, Enterobacteriaceae bacteria, Streptococcus bacteria, Haemophilus influenzae, Leptospira interrogans, Legionella bacteria, or a combination thereof.