# US 12,006,416 B2 · Volatile or semi-volatile natural antioxidants sourced from a comestible byproduct

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- Number: US 12,006,416 B2
- Document ID: US12006416B2
- Status: Granted
- Kind: B2
- Application number: 17/252,011
- Filed: 2019-06-19
- Published: 2021-08-26
- Granted: 2024-06-11
- Earliest claimed: 2018-06-20
- Assignees: Kellogg Company
- Applicants: Kellogg Company
- Inventors: Ziyi Linghu; John David Pinkston
- Web page: https://patentgrep.com/patent/US12006416B2

## CPC

- C08K 5/13: Phenols; Phenolates
- A23B 2/733: Compounds of undetermined constitution obtained from animals or plants
- A23B 2/746: with singly-bound oxygen
- A23B 9/26: Organic compounds; Microorganisms; Enzymes
- A23L 5/21: {by heating without chemical treatment, e.g. steam treatment, cooking}
- A23L 29/03: {Organic compounds}
- B65D 65/40: Applications of laminates for particular packaging purposes {(B65D1/0215, B65D1/28, B65D3/22, B65D5/0281, B65D5/563, B65D9/30, B65D29/02, B65D31/02, B65D75/26, B65D77/2024, B65D81/1275, B65D81/3811, B65D81/3823, B65D81/3834, B65D81/3846, B65D81/3858, B65D81/3874, B65D81/3886, B65D81/3897 take precedence; laminates per se or laminated packages characterised by the composition or)}
- B65D 81/28: Applications of food preservatives, fungicides, pesticides or animal repellants
- C07C 41/09: by dehydration of compounds containing hydroxy groups
- C07C 41/40: by change of physical state, e.g. by crystallisation
- C07C 41/42: by distillation
- C07C 43/23: containing hydroxy or O-metal groups
- C09K 15/08: containing a phenol or quinone moiety
- A23L 5/15: {using wave energy, irradiation, electrical means or magnetic fields, e.g. oven cooking or roasting using radiant dry heat}
- A23L 5/17: {in a gaseous atmosphere with forced air or gas circulation, in vacuum or under pressure}
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A23V 2200/02: Antioxidant
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- A23B: PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- B65D: CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

A method of obtaining a volatile or semi-volatile natural antioxidant by toasting a comestible byproduct, natural antioxidants obtained by toasting the comestible byproduct, and packaging films incorporating such natural antioxidants are described herein.

## Claims

### Claim 1

A method of obtaining a volatile or semi-volatile natural antioxidant from a comestible byproduct, the method comprising:
providing a comestible byproduct including a source of phenolic acid or polyphenolic compounds and optionally grinding the comestible byproduct;
toasting the comestible byproduct or optionally ground comestible byproduct for a time and at a temperature effective to volatilize and thermally convert the phenolic acid or polyphenolic compounds of the comestible byproduct or the optionally ground comestible byproduct into volatilized compounds including one or more substituted phenolic compounds; and
recovering the volatilized compounds including the one or more substituted phenolic compounds for use as the volatile or semi-volatile natural antioxidant.

### Claim 2 (depends on 1)

The method of claim 1, wherein the comestible byproduct is selected from canola meal, wheat bran, pomace, straw, coffee fruit, green coffee bean, roasted coffee beans, roast and ground coffee, spent coffee grounds, and combinations thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein the toasting includes dry heating at atmospheric pressure for about 10 minutes to about 20 minutes at about 165° C. to about 250° C., optionally under an inert gas purge.

### Claim 4 (depends on 1)

The method of claim 1, wherein the recovering includes cold trapping of the volatilized compounds.

### Claim 5 (depends on 1)

The method of claim 1, further comprising incorporating the recovered volatilized compounding including the one or more substituted phenolic compounds into a polymer substrate for use as packaging material.

### Claim 6 (depends on 5)

The method of claim 5, wherein the polymer substrate is selected form polyethylene, low density polyethylene (LDPE), linear low density polyethylene (LLDPE), ethylene-vinyl acetate (EVA), polypropylene, polylactic acid (PLA), polybutylene, and mixtures thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein the one or more substituted phenolic compounds include a methoxy phenol compound, a 4,6-substituted 2-methoxy phenol, derivatives thereof and mixtures thereof.

### Claim 8 (depends on 7)

The method of claim 7, wherein the 4,6-substitutions are each independently selected from hydrogen, a methoxy group, a methyl group, a vinyl group, and combinations thereof.

### Claim 9 (depends on 1)

The method of claim 1, wherein the volatile or semi-volatile natural antioxidant has a vapor pressure from about 0.0005 mm to about 0.5 mm of Hg at about 25° C.