Proteinoid emulsions and methods for preparation and use thereof

• US 6,051,258 A
• Filed: 06/07/1995
• Issued: 04/18/2000
• Est. Priority Date: 06/07/1995
• Status: Expired due to Term

• Current Assignee: NOVO Nordisk North America Operations A/S
• Original Assignee: Emisphere Technologies, Inc. (Novo Nordisk A/S)
• Inventors: Kantor, Martin L.
• Primary Examiner(s): Harrison, Robert H.
• Application Number:
  US08/475,885
• Time in Patent Office: 1,777 Days
• Field of Search: 424/491, 424/489, 424/499, 514/937, 514/975, 514/2, 514/773, 516/DIG. 4, 516/DIG. 6, 530/317, 530/345, 530/350, 530/370, 530/378
• US Class Current: 424/491
• CPC Class Codes: A61K 47/183 Amino acids, e.g. glycine, EDTA or aspartame
• CPC Class Codes: A61K 47/20 containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
• CPC Class Codes: A61K 47/42 Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein oligopeptides having up to five amino acids A61K47/183; polyamino acids A61K47/34
• CPC Class Codes: A61K 9/107 Emulsions ; Emulsion preconcentrates; Micelles composition of emulsions A61K47/00

Abstract

The present invention provides emulsions, and a method for preparing emulsions, comprising (A) an aqueous phase, (B) an non-aqueous phase, and (C) (i) a proteinoid emulsifier, (ii) a modified hydrolyzed vegetable protein emulsifier wherein said modified hydrolyzed vegetable protein is modified with an amine reactive modifying agent, (iii) an acylated non-α-amino acid emulsifier, (iv) an acylated poly amino acid emulsifier, (v) an acylated peptide emulsifier, (vi) a sulfonated non-α-amino acid emulsifier, (vii) a sulfonated poly amino acid emulsifier, (viii) a sulfonated peptide emulsifier, or (ix) any combination of any of (i), (ii), (iii), (iv), (v), (vi), (vii), and (viii). The proteinoids, modified hydrolyzed vegetable proteins, modified non-α-amino acids, modified poly amino acids, and modified peptides used in the present invention provide emulsions having improved stability against degradation and/or decomposition.

Claims

1. An emulsion comprising

(A) an aqueous phase;

(B) an non-aqueous phase; and

(C) (i) a mixed amino acid proteinoid emulsifier;

(ii) a modified hydrolyzed vegetable protein emulsifier wherein said modified hydrolyzed vegetable protein is modified with an amine reactive modifying agent;

(iii) an acylated non-α

-amino acid emulsifier;

(iv) an acylated poly amino acid emulsifier;

(v) an acylated peptide emulsifier;

(vi) a sulfonated non-α

-amino acid emulsifier;

(vii) a sulfonated poly amino acid emulsifier;

(viii) a sulfonated peptide emulsifier;

or

(ix) any combination of (i), (ii), (iii), (iv), (v), (vi), (vii) and (viii).

2. The emulsion of claim 1, wherein said non-aqueous phase comprises an oil.

3. The emulsion of claim 2, wherein said emulsion is selected from the group consisting of an oil-in-water emulsion and a water-in-oil emulsion.

4. The emulsion of claim 2, wherein said non-aqueous phase comprises soy oil.

5. The emulsion of claim 1, wherein said non-aqueous phase comprises a composition comprising at least one vinyl monomer.

6. The emulsion of claim 5, wherein said vinyl monomer is selected from the group consisting of vinyl acetate, butyl acrylate, methyl methacrylate, and a mixture of any of the foregoing.

7. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier is a linear proteinoid of mixed amino acids.

8. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier comprises a condensation polymer of mixed amino acids.

9. The emulsion of claim 8, wherein said mixed amino acid proteinoid emulsifier comprises a thermal condensation polymer of mixed amino acids.

10. The emulsion of claim 8, wherein said mixed amino acid proteinoid emulsifier comprises a directed condensation polymer of mixed amino acids.

11. The emulsion of claim 8, wherein said mixed amino acid proteinoid emulsifier comprises a random condensation polymer of mixed amino acids.

12. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier comprises a diketopiperazine.

13. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier has a molecular weight ranging from about 250 to about 2400.

14. The emulsion of claim 13, wherein said mixed amino acid proteinoid emulsifier has a molecular weight ranging from about 250 to about 400.

15. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier comprises from about 2 to about 20 amino acids.

16. The emulsion of claim 15, wherein said mixed amino acid proteinoid emulsifier has from about 2 to about 8 amino acids.

17. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier comprises an acid-soluble proteinoid.

18. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier comprises a base-soluble proteinoid.

19. The emulsion of claim 7, wherein said mixed amino acid proteinoid emulsifier is selected from the group consisting of Glu-Asp-2Arg-Phe, Glu-Asp-Tyr-Phe-0.5Orn, and Glu-Asp-0.4Lys-Phe.

20. The emulsion of claim 1, wherein said modified hydrolyzed vegetable protein emulsifier comprises acid hydrolyzed soybean protein.

21. The emulsion of claim 1, wherein said amine reactive modifying group is selected from the group consisting of a benzene sulfonyl group, a benzoyl group, a phthaloyl group, a tetrahydrophthaloyl group, and a cyclohexanoyl group.

22. The emulsion of claim 1, wherein said acylated non-α

-amino acid is N-cyclohexanoyl-6-aminohexanoic acid.

23. The emulsion of claim 1, comprising from about 1 to about 15 percent by weight of emulsifier, based on 100 parts by weight of said emulsion.

24. The emulsion of claim 23, comprising from about 4 to about 8 percent by weight of emulsifier, based on the 100 parts by weight of said emulsion.

25. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier is a branched proteinoid of mixed amino acids.

26. The emulsion of claim 1, wherein said mixed amino acid proteinoid emulsifier is a cyclic proteinoid of mixed amino acids.