Alkenone-based formulations for topical applications

Patent metadata

Field	Value
Publication number	US-2018296451-A1
Application number	US-201615776401-A
Country	US
Kind code	A1
Filing date	Nov 16, 2016
Priority date	Nov 16, 2015
Publication date	Oct 18, 2018
Grant date	—

Abstract

The use of long-chain alkenones to impart desired characteristics in personal care compositions for topical applications is described. The preparation of mixtures long-chain alkenones and synthetic derivatives thereof is presented. Examples of compositions include abrasive soaps, with alkenones serving as natural exfoliating agents. Alkenones and their derivatives can serve as emollients, occlusive agents, encapsulating agents, stabilizing agents, binding agents, thickening agents, surfactants, and anti-microbials.

First claim

1 . A personal care composition, comprising:
a compound of Formula (I):

wherein
R 1 is methyl or ethyl; and
R 2 is a C 30-45 alkenyl having at least one trans double carbon-carbon bond, or R 2 is a C 30-45 alkyl;
provided that the compound of Formula (I) is not

2 . The personal care composition of claim 1 , further comprising a synthetic agent selected from synthetic solubilizing agents, synthetic emulsifying agents, synthetic humectants, synthetic emollients, synthetic occlusive agents, synthetic surfactants, synthetic preservatives, synthetic binding agents, synthetic thickeners, synthetic solvents, synthetic fragrances, and any combination thereof.

3 . The personal care composition of claim 1 , further comprising a naturally occurring agent selected from natural emollients, natural occlusive agents, natural emulsifying agents, natural anti-oxidants, natural colorants, natural fragrances, and any combination thereof.

4 . The personal care composition of claim 1 , wherein R 2 is a C 35-45 alkenyl having at least one trans double carbon-carbon bond.

5 . (canceled)

6 . The personal care composition of claim 1 , wherein R 2 has 2 to 4 trans double carbon-carbon bonds.

7 . (canceled)

8 . The personal care composition of claim 1 , wherein the compound of Formula (I) is selected from the group consisting of:

wherein R 1 is methyl or ethyl, and R 2-C34 is C 34 alkenyl having 2 or 3 trans double carbon-carbon bonds;

wherein R 1 is methyl or ethyl, and R 2-C35 is C 35 alkenyl having 2 or 3 trans double carbon-carbon bonds;

wherein R 1 is methyl or ethyl, and R 2-C36 is C 36 alkenyl having 2 or 3 trans double carbon-carbon bonds;

wherein R 1 is methyl or ethyl, and R 2-C37 is C 37 alkenyl having 1, 2, 3, or 4 trans double carbon-carbon bonds;

wherein R 1 is methyl or ethyl, and R 2-C38 is C 38 alkenyl having 1, 2, 3, or 4 trans double carbon-carbon bonds; and

wherein R 1 is methyl or ethyl and R 2-C39 is C 39 alkenyl having 1, 2, 3, or 4 trans double carbon-carbon bonds.

9 . The personal care composition of claim 1 , wherein R 2 has two or more trans double carbon-carbon bonds, and at least two of the trans double carbon-carbon bonds are spaced from one another by 5 carbon atoms.

10 . (canceled)

11 . The personal care composition of claim 1 , wherein the composition is in the form of a topical formulation.

12 . The personal care composition of claim 1 , wherein the composition is selected from the group consisting of a skin-care composition, a hair-care composition, and a cosmetic composition.

13 - 15 . (canceled)

16 . The personal care composition of claim 1 , wherein the compound of formula (I) is present from 1-50% w/w of the total composition.

17 . The composition of claim 1 , wherein the compound of formula (I) is derived from algae selected from the group consisting of Isochrysis, Emiliania huxleyi , and Gephyrocapsa oceanica.

18 . The composition of claim 1 , wherein the composition does not include any petroleum-based waxes or oils, plant-based fats, animal-based fats, or any combination thereof.

19 . (canceled)

20 . (canceled)

21 . A personal care composition, comprising:
at least one compound of Formula (II), Formula (III), or Formula (IV):

wherein
R 3 is selected from —OH, —O(CH 2 CH 2 ) n OSO 3 − , and —O(CH 2 )(CHOH)(CHOH),
wherein n is an integer of from 1 to 200, and

R 2 is a C 30-45 alkenyl having at least one trans double carbon-carbon bond, or R 2 is a C 30-45 alkyl;

wherein
R 1 is methyl or ethyl;
R 2 is a C 30-45 alkenyl having at least one trans double carbon-carbon bond, or R 2 is a C 30-45 alkyl;
R 4 , R 5 , and R 6 are each independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, and halo; and
R 7 is selected from H and —CO 2 − ;

wherein
R 1 is methyl or ethyl;
R 2 is a C 30-45 alkenyl having at least one trans double carbon-carbon bond, or R 2 is a C 30-45 alkyl;
R 8 is selected from —SO 3 − , PO 2 − OR 9 , and —CONHR 10 ,
wherein R 9 is —CH 2 CH 2 N + R 11 R 12 R 13 , wherein R 11 , R 12 , and R 13 are each independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, and halo, and
R 10 is —(CH 2 ) m SO 3 − , —(CH 2 ) m N + R 14 R 15 CH 2 CO 2 − , —(CH 2 ) m N + R 16 R 17 R 18 ,
wherein m is an integer of from 1 to 10; R 14 , R 15 , R 16 , R 17 , and R 18 are each independently selected from H, C 1-6 alkyl, C 1-6 haloalkyl, and halo.

22 . (canceled)

23 . The personal care composition of claim 21 , further comprising a synthetic agent selected from synthetic solubilizing agents, synthetic emulsifying agents, synthetic humectants, synthetic emollients, synthetic occlusive agents, synthetic surfactants, synthetic preservatives, synthetic binding agents, synthetic thickeners, synthetic solvents, synthetic fragrances, and any combination thereof.

24 . The personal care composition of claim 21 , further comprising a naturally occurring agent selected from natural emollients, natural occlusive agents, natural emulsifying agents, natural anti-oxidants, natural colorants, natural fragrances, and any combination thereof.

25 . The personal care composition of claim 21 , wherein in the compound of Formula (II), (III), or (IV), R 2 is independently a C 35-45 alkenyl having at least one trans double carbon-carbon bond.

26 - 28 . (canceled)

29 . The personal care composition of claim 21 , wherein in the compound of Formula (II), (III), or (IV), R 2 is independently selected from:
C 34 alkenyl having 2 or 3 trans double carbon-carbon bonds; C 35 alkenyl having 2 or 3 trans double carbon-carbon bonds; C 36 alkenyl having 2 or 3 trans double carbon-carbon bonds; C 37 alkenyl having 1, 2, 3, or 4 trans double carbon-carbon bonds; C 38 alkenyl having 1, 2, 3, or 4 trans double carbon-carbon bonds; and C 39 alkenyl having 1, 2, 3, or 4 trans double carbon-carbon bonds.

30 . The personal care composition of claim 21 , wherein R 2 has two or more trans double carbon-carbon bonds, and at least two of the trans double carbon-carbon bonds are separated

Assignees

• Oneil Gregory W
• Reddy Christopher M
• Western Washington Univ
• Woods Hole Oceanographic Inst

Inventors

• O'Neil Gregory W
• Reddy Christopher M

Classifications

• A61K2800/43

  Pigments; Dyes · CPC title

• A61K8/9761

  Cupressaceae [Cypress family], e.g. juniper or cypress · CPC title

• A61K8/55

  Phosphorus compounds · CPC title

• A61K2800/49

  Solubiliser, Solubilising system · CPC title

• A61K8/9771

  Ginkgophyta, e.g. Ginkgoaceae [Ginkgo family] · CPC title