IP Library Granted Patent US 9,725,675
Granted Patent B2
US 9,725,675 · App. 13/347,498 · Granted Aug 8, 2017

Lipid-soluble formulations containing mixtures of antioxidants

Inventors: Clifford Adams (Antwerp, BE); Stefaan Van Dyck (Brasschaat, BE); Aimee Teunckens (Meerhout, BE); Tom Verleyen (Wilrijk, BE)
Assignee: KEMIN INDUSTRIES, INC.
C11B5/0092A23L3/3463A23L3/3472C09K15/08
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Quick Facts
Patent No.
US 9,725,675
App. No.
13/347,498
Granted
Aug 8, 2017
Kind
B2
Abstract

A substantially oil- and fat-free single phase, homogenous antioxidant formulation that is readily dispersible in lipid matrices at ambient temperature by gentle stirring. The formulation includes a phenolic antioxidant compound, a liquid carrier, preferably a metal chelator, an emulsifier, and a polarity modifier. In preferred embodiment, a combination of lipid-soluble and water-soluble antioxidant compounds is included to provide an improved antioxidant effect.

Claims (26)

1. A method of protecting oils and fats from oxidation, comprising the steps of:

(a) formulating a homogenous single phase product substantially free of oils or fats comprising:

i. a phenolic antioxidant composition having:

A. at least one water-soluble antioxidant; and

B. at least one lipid-soluble antioxidant selected from the group consisting of butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), ethoxyquin, gallic acid and esters of gallic acid, flavones, phenolic di- and tri-terpenes, phenolic extracts of sage, phenolic extracts of rosemary, and phenolic extracts of thyme;

ii. a liquid polar carrier selected from the group consisting of monopropylene glycol, polyethylene glycol, and glycerol;

iii. an emulsifier; and

iv. a polarity modifier;

(b) adding the homogenous single phase product to the oil or fat; and

(c) dissolving both the water-soluble and lipid-soluble antioxidants into the oil or fat by mixing.

2. A method as defined in claim 1 , wherein the emulsifier is selected from the group consisting of acylglycerides, di-acylglycerides, phospholipids, and lysophospholipids.

3. A method as defined in claim 1 , wherein the polarity modifier is selected from the group consisting of short chain fatty acids.

4. A method as defined in claim 3 , wherein the short chain fatty acid is selected from the group consisting of propionic acid, butyric acid and acetic acid.

5. A method as defined in claim 1 , further comprising a metal chelator.

6. A method as defined in claim 5 , wherein the metal chelator comprises organic acids.

7. A method as defined in claim 6 , wherein the organic acid is selected from the group consisting of ascorbic acid and citric acid.

8. The method of claim 1 , wherein the method is carried out at ambient temperature.

9. The method of claim 1 , wherein the antioxidant components are present in an amount between about 10 and about 30 weight percent of the homogenous product.

10. The method of claim 1 , further comprising adding about 5% citric acid, and wherein the liquid polar carrier is between 25-30% monopropylene glycol, the polarity modifier is between 15-25% propionic acid and the emulsifier is between 25-30% monoglycerides.

11. The method of claim 1 , further comprising adding about 5% citric acid, and wherein the lipid-soluble antioxidant is about 7% gallic acid, 10% propyl gallate, and 3% octyl gallate, the liquid polar carrier is about 27.5% monopropylene glycol, the polarity modifier is about 19% propionic acid, the emulsifier is about 26.5% monoglycerides, and about 2% phospholipids.

12. The method of claim 1 , further comprising adding about 5% citric acid, and wherein the lipid-soluble antioxidant is about 7% gallic acid, 10% propyl gallate, and 2% octyl gallate, the liquid polar carrier is about 27% monopropylene glycol, the polarity modifier is about 20% propionic acid, and the emulsifier is about 29% monoglycerides.

13. A product made according to the method of claim 1 , further comprising adding about 5% citric acid, and wherein the lipid-soluble antioxidant is about 17% propyl gallate and 2% octyl gallate, the liquid polar carrier is about 27% monopropylene glycol, the polarity modifier is about 20% propionic acid, and the emulsifier is about 29% monoglycerides.

14. The method of claim 1 , further comprising adding about 5% citric acid, and wherein the lipid-soluble antioxidant is about 7% gallic acid and 10% propyl gallate, 27% the liquid polar carrier is about monopropylene glycol, the polarity modifier is about 20% propionic acid, and the emulsifier is about 29% monoglycerides.

15. The method of claim 1 , further comprising adding about 5% citric acid, and wherein the lipid-soluble antioxidant is about 7% gallic acid, 10% propyl gallate, and 3% octyl gallate, the liquid polar carrier is about 30% monopropylene glycol, the polarity modifier is about 19% propionic acid, and the emulsifier is about 26% monoglycerides.

16. The method of claim 1 , further comprising adding about 5% citric acid, and wherein the lipid-soluble antioxidant is about 7% gallic acid 12% propyl gallate, and 5% BHA, the liquid polar carrier is about 27% monopropylene glycol, the polarity modifier is about 20% propionic acid, and the emulsifier is about 29% monoglycerides.

17. The method of claim 1 , wherein the dissolving of the water-soluble and lipid-soluble antioxidants into the oil or fat is performed at room temperature.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Jul 6, 2026
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: KEMIN FOODS, L.C.; KEMIN HOLDINGS, L.C.; KEMIN INDUSTRIES, INC.
Reel/Frame 075184/0555 →
IP SUPPLEMENT (PATENTS) Recorded Sep 4, 2012
From: KEMIN FOODS, L.C.; KEMIN INDUSTRIES, INC.; KEMIN HOLDINGS, L.C.
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 028896/0885 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2012
From: ADAMS, CLIFFORD; VAN DYCK, STEFAAN M.O.; TEUNCKENS, AIMEE; VERLEYEN, TOM
To: KEMIN INDUSTRIES, INC.
Reel/Frame 028186/0005 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2012
From: ZORICH, CRIS
To: KEMIN INDUSTRIES, INC.
Reel/Frame 027926/0927 →
Continuity (2)
Continuation 10407285 · Apr 4, 2003
Related Publication 20120215016A1 · Aug 23, 2012