Compositions for controlled release of volatile compounds

Patent metadata

Field	Value
Publication number	US-11013249-B2
Application number	US-201716301365-A
Country	US
Kind code	B2
Filing date	May 12, 2017
Priority date	May 13, 2016
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

It is provided a composition for controlled-release of volatile compounds comprising at least one poly(ethylene glycol) (PEG) polymer and one or more volatile compounds, the composition used for preserving food when incorporated in a food packaging. The volatile compounds are antimicrobial compounds such as allyl isothiocyanate (AITC), diacetyl, cinnamaldehyde, thymol, carvacrol and a combination thereof. The composition can comprise a blend of two or more PEG polymers of different molecular weights and/or a mixture of poly(lactic acid) (PLA) and poly(ethylene oxide) (PEO).

First claim

What is claimed is:

1. A composition for controlled-release of volatile compounds to preserve food, comprising:
two polymers and at least one antimicrobial volatile compound comprising an antimicrobial volatile impregnated material, the antimicrobial volatile impregnated material comprised of a melt blended sheeting of two polyethylene glycol (PEG) polymers, one of the PEG polymers having a high molecular weight of at least PEG 10k and another of the PEG polymers having a low molecular weight of at PEG 400 or lower or the antimicrobial volatile impregnated material comprised of insoluble electrospun nonwoven fibers wherein the two or more polymers comprise polyethylene oxide (PEO) and polylactic acid (PLA).

2. The composition of claim 1 , wherein the two PEG polymers have a molecular mass from about 100 Da to about 50,000 Da.

3. The composition of claim 2 , wherein the two PEG polymers comprise PEG400 and PEG10K in a ratio by weight of PEG400 and PEG10K from about 1:4 to about 4:1.

4. The composition of claim 1 , wherein the at least one volatile compound comprises diacetyl and allyl isothiocyanate (AITC) up to 10% (w/w) based on weight of the PEG polymers.

5. The composition of claim 1 , wherein the at least one volatile compound comprise about 0.05% (w/w) to about 5% (w/w) based on weight of the PEG polymers.

6. The composition of claim 1 , wherein the antimicrobial compound is selected from the group consisting of allyl isothiocyanate (AITC), diacetyl, cinnamaldehyde, thymol, or carvacrol or a combination thereof.

7. The composition of claim 6 , wherein the antimicrobial compound is selected from the group consisting of allyl isothiocyanate (AITC) or diacetyl or a combination thereof.

8. The composition of claim 7 , wherein the antimicrobial compound comprises a mixture of diacetyl and AITC in a weight ratio of between 9:1.

9. The composition of claim 1 , wherein the antimicrobial compound comprises a mixture of diacetyl, AITC and cinnamaldehyde in a ratio of 1:4:60, respectively.

10. The composition of claim 1 , wherein the two or more polymers comprise the electrospun fibers to form a carrier, the at least one volatile compound dispersed in the carrier.

11. The composition of claim 1 , wherein the mixture of PLA and PEO is in a ratio of 7:3.

12. The composition of claim 1 , wherein the electrospun nonwovens fibers are prepared from electrospinning a solution containing the PEO and a cellulose derivative.

13. The composition of claim 12 , wherein the cellulose derivative comprises one of ethylcellulose (EC) or cellulose acetate (CA).

14. The composition of claim 1 , wherein the composition is provided in packaging material for a food product.

15. The composition of claim 3 , wherein a crystallinity of PEG10K is greater than 96%.

16. The composition of claim 11 , wherein a mixture of 9% PLA and 3% PEO in Tetrahydrofuran (THF) at a weight ratio of 7:3 results in a depression of PLA melting point of at least 30 degrees C. as cinnamaldehyde is increased to 42% w/w.

17. The composition of claim 16 , wherein when the cinnamaldehyde loading is increased from a 0 to 42% level, a blue shift for the absorbance at approximately 1082 cm −1 is present due to C—O—C vibration as detected by Fourier transform infrared spectroscopy, by 5 to 10 cm −1 .

18. The composition of claim 16 , wherein when cinnamaldehyde loading is increased from a 0 to 42% level, a blue shift for the absorbance at approximately 1749 cm −1 is present due to C═O vibration as detected by Fourier transform infrared spectroscopy, by 5 to 10 cm −1 .

19. The composition of claim 13 , wherein polymer solutions for electrospinning are comprised of 10% w/w EC at 46-48% ethoxy content, 1% w/w PEO300, and thymol at 1, 3 or 5% w/w dissolved in 80% v/v aqueous ethanol.

20. The composition of claim 19 , wherein when thymol loading increased from 5% level, a red shift for the absorbance is present at approximately 1242 cm −1 due to C—O vibration of thymol as detected by Fourier transform infrared spectroscopy, by 5 to 10 cm −1 .

21. The composition of claim 13 , wherein polymer solutions for electrospinning are comprised of 10% w/w CA at 40% acetyl content, 1 w/w PEO100 or PEO300, and carvacrol at 1, 5 or 10% w/w dissolved in acetic acid:acetone at a ratio of 1:0, 3:1 or 1:1 v/v blend solvent.

22. The composition of claim 21 , wherein an addition of carvacrol would not result in any shift in Fourier transformed infrared spectra for the two or more polymers and carvacrol.

Assignees

• Univ Guelph

Inventors

• Lim Loong-Tak
• Wang Wenjing
• Huang Wenyu

Classifications

• A23B2/767

  Organic compounds containing sulfur · CPC title

• A23B2/746

  with singly-bound oxygen · CPC title

• A23B2/729

  Organic compounds; Microorganisms; Enzymes · CPC title

• A23B2/75

  with doubly-bound oxygen · CPC title

• A23B2/7295 Primary

  Antibiotics · CPC title