Methods for stabilizing ingredients within cosmetics, personal care and household products

• US 20050244349A1
• Filed: 04/27/2005
• Published: 11/03/2005
• Est. Priority Date: 04/28/2004
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Puccetti, Germain, Chaudhuri, Ratan, Lascu, Zoia, Marchio, Francois
• Granted Patent: US 7,150,876 B2
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 2800/52 Stabilizers
• CPC Class Codes: A61K 8/37 Esters of carboxylic acids
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61Q 1/04 for lips
• CPC Class Codes: A61Q 1/06 Lipsticks
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 17/02 containing insect repellants
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/04 for chemically tanning the skin topical sun or radiation screening or tanning preparations A61Q17/04
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 3/02 Nail coatings
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/06 Preparations for styling the hair, e.g. by temporary shaping or colouring
• CPC Class Codes: A61Q 5/065 Preparations for temporary colouring the hair, e.g. direct dyes
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C11D 3/0084 Antioxidants; Free-radical scavengers
• CPC Class Codes: C11D 3/2093 Esters; Carbonates
• CPC Class Codes: C11D 3/26 containing nitrogen C11D3/162, C11D3/164, C11D3/166, C11D3/168 take precedence
• CPC Class Codes: C11D 3/32 : Amides; Substituted amides
• CPC Class Codes: C11D 3/40 : Dyes ; Pigments
• CPC Class Codes: C11D 3/50 : Perfumes
• CPC Class Codes: C11D 7/266 : Esters or carbonates
• CPC Class Codes: C11D 7/3254 : Esters or carbonates thereof
• CPC Class Codes: C11D 7/3263 : Amides or imides

Abstract

The present invention relates to methods and compositions for using photostabilizer compounds for stabilizing formulation ingredients, like flavors, fragrances, colors, antioxidants, polymers, within cosmetics, personal care and household products, against degradation from sun light, heat and air oxidation resulting in improvement in storage stability, viscosity, and maintenance of color of the formulated products.

Claims

1. A method of stabilizing at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

said method comprising combining at least one compound of formulae ii, ii′

and/or i″

with said at least one photosensitive poly-unsaturated and/or aromatic compound in a ratio within a range of 10;

1 to 1;

2 based on total weight percent of the one or more compounds of formulae ii, ii′ and

/or i″

to the total weight percent of the one or more photosensitive poly-unsaturated and/or aromatic compounds,

wherein

each R_ii is independently linear or branched C₁ to C₈ alkyl;

R_ii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN;

X is O, NH or N-alkyl;

R_ii2 is linear or branched C₁ to C₂₀ alkyl;

R_ii3 is linear or branched C₁ to C₂₀ alkyl;

each R_ii4 is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN;

R<sub>ii′

2</sub> is linear or branched C₁ to C₃₀ alkyl;

R<sub>ii′

3</sub> is linear or branched C₁ to C₂₀ alkyl;

each R<sub>ii′

4</sub> is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen;

R<sub>ii′

6</sub> is linear or branched C₁-C₈ alkyl;

each R_i″

is independently linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy;

or one R_i″

is H and the other R_i″

is linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy,

R<sub>i″

1</sub> is COCH₃, CO₂R<sub>i″

5</sub>, CONH₂, CONH(R<sub>i″

6</sub>)₂, CN, COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>), or the quaternized salt form of the formula COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>)⁺Y⁻

,

n is an integer of 1 to 5,

Y⁻

is an anion,

R<sub>i″

2</sub>, R<sub>i″

3</sub> and R<sub>i″

4</sub> are independently linear or branched C₁ to C₂₀alkyl; and

R<sub>i″

5</sub> and R<sub>i″

6</sub> are independently hydrogen or linear or branched C₁-C₂₀ alkyl.

2. A method according to claim 1, wherein the ratio of the one or more compound (s) of formulae ii, ii′

and/or i″

to the one or more photosensitive poly-unsaturated and/or aromatic compound(s) is 5;

1 to 1;

1.

3. A method according to claim 1, wherein only one photosensitive poly-unsaturated and/or aromatic compound is stabilized and the ratio of the one or more compound(s) of formulae ii, ii′

and/or i″

to the one photosensitive poly-unsaturated and/or aromatic compound is 10;

1 to 1;

1 and the one photosensitive poly-unsaturated and/or aromatic compound is a color compound, an antioxidant, a fragrance compound or a flavor compound.

4. A method according to claim 1, wherein the at least one compound of formulae ii, ii′

and/or i″

is at least one compound of formulae iii, iii′

, iv and/or iv′

wherein

R_iii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN,

R_iii2 is linear or branched C₁ to C₂₀ alkyl,

R_iv1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN,

R_iv2 is linear or branched C₁ to C₂₀ alkyl,

R<sub>iii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN,

R<sub>iii′

2</sub> is linear or branched C₁ to C₃₀ alkyl,

R<sub>iii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen,

R<sub>iv′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN,

R<sub>iv′

2</sub> is linear or branched C₁ to C₃₀ alkyl, and

R<sub>iv′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen,

wherein R_ii3, R_ii4, R<sub>ii′

3</sub>, and R<sub>ii′

4</sub> are defined as in claim 1.

5. A method according to claim 1, wherein R_ii2, R_ii′

2, R_ii3 and R<sub>ii′

3</sub> are each a linear or branched C₁ to C₈ alkyl.

6. A method according to claim 1, wherein the compound of formulae ii, ii′

and/or i″

is

ethyl-alpha-cyano-3,5-dimethoxy-4-hydroxy cinnamate,

ethyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy cinnamate,

iso-propyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy cinnamate,

iso-amyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy cinnamate,

2-ethylhexyl-alpha-acetyl-3,5-dimethoxy-4-hydroxy cinnamate,

diethyl-3,5-dimethoxy-4-hydroxy benzylidene malonate,

di-(2-ethylhexyl)-3,5-dimethoxy-4-hydroxy benzylidene malonate,

diisoamyl-3,5-dimethoxy-4-hydroxy benzylidene malonate,

didodecyl-3,5-dimethoxy-4-hydroxy benzylidene malonate,

dipalmitoyl-3,5-dimethoxy-4-hydroxy benzylidene malonate,

di-isopropyl-3,5-dimethoxy-4-hydroxy benzylidene malonate,

ethyl-alpha-cyano-3-methoxy-4-hydroxy cinnamate,

ethyl-alpha-acetyl-3-methoxy-4-hydroxy cinnamate,

iso-propyl-alpha-acetyl-3-methoxy-4-hydroxy cinnamate,

iso-amyl-alpha-acetyl-3-methoxy-4-hydroxy cinnamate,

2-ethylhexyl-alpha-acetyl-3-methoxy-4-hydroxy cinnamate,

diethyl-3-methoxy-4-hydroxy benzylidene malonate,

di-(2-ethylhexyl)-3-methoxy-4-hydroxy benzylidene malonate,

diisoamyl-3-methoxy-4-hydroxy benzylidene malonate,

didodecyl-3-methoxy-4-hydroxy benzylidene malonate,

dipalmitoyl-3-methoxy-4-hydroxy benzylidene malonate,

di-isopropyl-3-methoxy-4-hydroxy benzylidene malonate,

7. A method according to claim 1, wherein the compound of formulae ii, ii′

and/or i″

is

Di-2-ethylhexyl 3,5 dimethoxy 4 hydroxy benzylidene malonate,

Isoamyl alpha acetyl-3,5 dimethoxy 4 hydroxy benzylidene malonate, or

Bis-N[3′

-(N,N dimethylamino)propyl]-3,5-dimethoxy-4 hydroxybenzylidene malonamide bis ethyl sulfate.

8. A method according to claim 1, wherein the one or more photosensitive compound(s) is protected from both visible light and UV.

9. A method according to claim 1, wherein the one or more photosensitive compound(s) is protected from visible light only or from substantially visible light only.

10. A method as in claim 1, wherein said one or more photosensitive poly-unsaturated and/or aromatic compound(s) is combined with at least one compound of formula ii, ii′

and/or i″

within a cosmetic composition, personal care product or household product, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of about 0.001 to 10.0 wt %, based on the total weight of the cosmetic composition, personal care product or household product.

11. A method as in claim 1, wherein said one or more photosensitive poly-unsaturated and/or aromatic compound(s) is combined with at least one compound of formula ii, ii′

and/or i″

within a cosmetic composition, personal care product or household product, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of about 0.01 to 4.0 wt %, based on the total weight of the cosmetic composition, personal care product or household product.

12. A method as in claim 1, wherein said one or more photosensitive poly-unsaturated and/or aromatic compound(s) is combined with at least one compound of formula ii, ii′

and/or i″

within a cosmetic composition, personal care product or household product, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of about 0.01 to 1.0 wt %, based on the total weight of the cosmetic composition, personal care product or household product.

13. A method as in claim 10, wherein the cosmetic composition, personal care product or household product is within a container for retail sale when the combination is formed.

14. A method as in claim 10, comprising the additional step of transferring the combination of at least one photosensitive poly-unsaturated and/or aromatic compound and at least one compound of formula ii, ii′

and/or i″

to a cosmetic composition, personal care product or household product within a container for retail sale, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of 0.001 to 10.0 wt %, based on the total weight of the cosmetic composition, personal care product or household product.

15. A method as in claim 10, comprising the additional step of transferring the combination of at least one photosensitive poly-unsaturated and/or aromatic compound and at least one compound of formula ii, ii′

and/or i″

to a cosmetic composition, personal care product or household product within a container for retail sale, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of 0.01 to 4.0 wt %, based on the total weight of the cosmetic composition, personal care product or household product.

16. A method according to claim 1, wherein the photosensitive compound is a carotenoid, tocopherol, guaiazulene, vanillin or menthylanthranillate.

17. A method as in claim 1, wherein the photosensitive poly-unsaturated color compound is a carotenoid, Ubiquinone or Azulene.

18. A method as in claim 17, wherein the Azulene photosensitive poly-unsaturated color compound is azulene, guaiazulene, or guaiol.

19. A method as in claim 17, wherein the carotenoid photosensitive poly-unsaturated color compound is Lycopene, Zeaxanthine, Cantaxanthine, α

-, β

- γ

- &

δ

-Carotenes, Astacin, Astaxanthin, Chrysanthemaxanthin, Torularhodin, Violaxanthin, Capsanthin or Capsorubin.

20. A method as in claim 17, wherein the Ubiquinone photosensitive poly-unsaturated color compound is photo-sensitive Coenzyme Q_n in which n=1-12.

21. A method as in claim 1, wherein the photosensitive poly-unsaturated color compound is a photosensitive dye or organic pigment.

22. A method as in claim 21, wherein the photosensitive organic pigment is a curcuminoid.

23. A method as in claim 21, wherein the curcuminoid is curcumin, Cassumunin A, Cassumunin B, demethoxycurcumin or bisdemethoxycurcumin.

24. A method according to claim 1, wherein said photosensitive poly-unsaturated compound is a fragrance that is combined with at least one compound of formula ii, ii′

and/or i″

, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of about 0.001 to 10.0 wt %, based on the total weight of the resultant composition, and wherein the fragrance is

25. A method according to claim 1, wherein said photosensitive poly-unsaturated compound is a flavor that is combined with at least one compound of formula ii, ii′

and/or i″

, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of 0.001-10 wt %, based on the total weight of the resultant composition, and wherein the flavor is

26. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 1.

27. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 5.

28. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 10.

29. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 11.

30. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 12.

31. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 19.

32. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof,

wherein said photosensitive poly-unsaturated and/or aromatic compound is stabilized by the method of claim 21.

33. A product which is a cosmetic composition, personal care product or household product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is a fragrance compound,

wherein said fragrance compound is stabilized by the method of claim 24.

34. A product which is a cosmetic product which contains at least one photosensitive poly-unsaturated and/or aromatic compound which is a flavor compound,

wherein said flavor compound is stabilized by the method of claim 25.

35. A product of claim 26, which is a household product that is a cleaning composition, detergent, dishwashing liquid or powder, glass or furniture cleaning and/or polishing composition, or floor cleaning and/or polishing composition.

36. A product of claim 30, which is a cosmetic composition, which contains a flavor compound.

37. A product of claim 26, wherein the photosensitive poly-unsaturated and/or aromatic compound is an organic pigment which is a curcuminoid selected from curcumin, Cassumunin A, Cassumunin B, demethoxycurcumin or bisdemethoxycurcumin.

38. A product of claim 25, wherein the photosensitive poly-unsaturated and/or aromatic compound is a carotenoid, tocopherol, guaiazulene, vanillin, menthylanthranillate, ubiquinone, azulene, guaiazulene, or guaiol.

39. A method as in claim 16, wherein the tocopherols are either natural or synthetic or a combination thereof.

40. A method as in claim 39, wherein the tocopherols are a mixture of α

, β

, γ and

δ

lipid—

soluble tocopherols and α

, β

, γ and

δ

lipid-soluble tocotrienols.

41. A method as in claim 39, wherein the tocopherols are a mixture of synthetic DL tocopherols and their acetates.

45. A method according to claim 1, wherein X is N—

C_1-8 Alkyl.

46. A method according to claim 1, wherein X is N-Me.

42. A method for stabilizing photosensitive polymeric thickening agent in a cosmetic composition, personal care product or household product comprising processing at least one compound of formulae ii, ii′

and/or i″ and

said polymeric thickening agent into said cosmetic composition, personal care product or household product in a ratio within a range of 10;

1 to 1;

2 based on total weight percent of the one or more compounds of formulae ii, ii′ and

/or i″

to the total weight percent of the polymeric thickening agent,

wherein

each R_ii is independently linear or branched C₁ to C₈ alkyl;

R_ii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN;

X is O, NH or N-alkyl;

R_ii2 is linear or branched C₁ to C₂₀ alkyl;

R_ii3 is linear or branched C₁ to C₂₀ alkyl;

each R_ii4 is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN;

R<sub>ii′

2</sub> is linear or branched C₁ to C₃₀ alkyl;

R<sub>ii′

3</sub> is linear or branched C₁ to C₂₀ alkyl;

each R<sub>ii′

4</sub> is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen;

R<sub>ii′

6</sub> is linear or branched C₁-C₈ alkyl;

each R_i″

is independently linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy;

or one R_i″

is H and the other R_i″

is linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy,

R<sub>i″

1</sub> is COCH₃, CO₂R<sub>i″

5</sub>, CONH₂, CONH(R<sub>i″

6</sub>)₂, CN, COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>), or the quaternized salt form of the formula COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>)⁺Y⁻

,

n is an integer of 1 to 5,

Y⁻

is an anion,

R<sub>i″

2</sub>, R<sub>i″

3</sub> and R<sub>i″

4</sub> are independently linear or branched C₁ to C₂₀ alkyl; and

R<sub>i″

5</sub> and R<sub>i″

6</sub> are independently hydrogen or linear or branched C₁-C₂₀ alkyl.

43. A method according to claim 42, wherein the polymeric thickening agent is a carbomer, acrylate/acrylonitrile copolymer, xanthan gum or a combinations thereof.

44. A method according to claim 42, wherein the ratio of the one or more compound (s) of formulae ii, ii′

and/or i″

to the polymeric thickening agent is 5;

1 to 1;

1.

47. A method according to claim 42, wherein X is N—

C_1-8 Alkyl.

48. A method according to claim 42, wherein X is N-Me.

49. A cosmetic composition, personal care product or household product containing a compound of formula ii, ii′

and/or i″

within, wherein the at least one compound of formula ii, ii′ and

/or i″

is used in an amount of about 0.001 to 10.0 wt %, based on the total weight of the cosmetic composition, personal care product or household product

wherein

each R_ii is independently linear or branched C₁ to C₈ alkyl;

R_ii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN;

X is N-alkyl;

R_ii2 is linear or branched C₁ to C₂₀ alkyl;

R_ii3 is linear or branched C₁ to C₂₀ alkyl;

each R_ii4 is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN;

R<sub>ii′

2</sub> is linear or branched C₁ to C₃₀ alkyl;

R<sub>ii′

3</sub> is linear or branched C₁ to C₂₀ alkyl;

each R<sub>ii′

4</sub> is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen;

R<sub>ii′

6</sub> is linear or branched C₁-C₈ alkyl;

each R_i″

is independently linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy;

or one R_i″

is H and the other R_i″

is linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy,

R<sub>i″

1</sub> is COCH₃, CO₂R<sub>i″

5</sub>, CONH₂, CONH(R<sub>i″

6</sub>)₂, CN, COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>), or the quaternized salt form of the formula COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>)⁺Y⁻

,

n is an integer of 1 to 5,

Y⁻

is an anion,

R<sub>i″

2</sub>, R<sub>i″

3</sub> and R<sub>i″

4</sub> are independently linear or branched C₁ to C₂₀ alkyl; and

R<sub>i″

5</sub> and R<sub>i″

6</sub> are independently hydrogen or linear or branched C₁-C₂₀ alkyl.

50. A composition according to claim 49, wherein X is N—

C_1-4 Alkyl.

51. A composition according to claim 49, wherein X is N-Me.

52. A composition according to claim 49, further containing at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof.

53. A composition consisting essentially of

one or more photosensitive poly-unsaturated and/or aromatic compound which are either one or more color compounds, one or more antioxidants, one or more fragrance compounds, one or more flavor compounds or a combination thereof, and

one or more compounds of formulae ii, ii′

and/or i″

,

wherein

each R_ii is independently linear or branched C₁ to C₈ alkyl;

R_ii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN;

X is O, NH or N-alkyl;

R_ii2 is linear or branched C₁ to C₂₀ alkyl;

R_ii3 is linear or branched C₁ to C₂₀ alkyl;

each R_ii4 is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN;

R<sub>ii′

2</sub> is linear or branched C₁ to C₃₀ alkyl;

R<sub>ii′

3</sub> is linear or branched C₁ to C₂₀ alkyl;

each R<sub>ii′

4</sub> is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen;

R<sub>ii′

6</sub> is linear or branched C₁-C₈ alkyl;

each R_i″

is independently linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy;

or one R_i″

is H and the other R_i″

is linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy,

R<sub>i″

1</sub> is COCH₃, CO₂R<sub>i″

5</sub>, CONH₂, CONH(R<sub>i″

6</sub>)₂, CN, COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>), or the quaternized salt form of the formula COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>)⁺Y⁻

,

n is an integer of 1 to 5,

Y⁻

is an anion,

R<sub>i″

2</sub>, R<sub>i″

3</sub> and R<sub>i″

4</sub> are independently linear or branched C₁ to C₂₀ alkyl; and

R<sub>i″

5</sub> and R<sub>i″

6</sub> are independently hydrogen or linear or branched C₁-C₂₀ alkyl.

54. A composition according to claim 53, wherein the ratio of the total weight percent of the one or more compounds of formulae ii, ii′

and/or i″

to the total weight percent of the at least one photosensitive poly-unsaturated and/or aromatic compound which is either a color compound, antioxidant, a fragrance compound, a flavor compound or a combination thereof, is within a range of 10;

1 to 1;

2.

55. A composition according to claim 53, containing one or more fragrance compounds.

56. A method of stabilizing an oil and/or wax, said method comprising combining at least one compound of formulae ii, ii′

and/or i″

with said oil and/or wax,

wherein the ratio of the total weight percent of the one or more compounds of formulae ii, ii′ and

/or i″

to the total weight percent of the oil and/or wax, is within a range of 10;

1 to 1;

2.

wherein

each R_ii is independently linear or branched C₁ to C₈ alkyl;

R_ii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN;

X is O, NH or N-alkyl;

R_ii2 is linear or branched C₁ to C₂₀ alkyl;

R_ii3 is linear or branched C₁ to C₂₀ alkyl;

each R_ii4 is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN;

R<sub>ii′

2</sub> is linear or branched C₁ to C₃₀ alkyl;

R<sub>ii′

3</sub> is linear or branched C₁ to C₂₀ alkyl;

each R<sub>ii′

4</sub> is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen;

R<sub>ii′

6</sub> is linear or branched C₁-C₈ alkyl;

each R_i″

is independently linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy;

or one R_i″

is H and the other R_i″

is linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy,

R<sub>i″

1</sub> is COCH₃, CO₂R<sub>i″

5</sub>, CONH₂, CONH(R<sub>i″

6</sub>)₂, CN, COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>), or the quaternized salt form of the formula COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>)⁺Y⁻

,

n is an integer of 1 to 5,

Y⁻

is an anion,

R<sub>i″

2</sub>, R<sub>i″

3</sub> and R<sub>i″

4</sub> are independently linear or branched C₁ to C₂₀ alkyl; and

R<sub>i″

5</sub> and R<sub>i″

6</sub> are independently hydrogen or linear or branched C₁-C₂₀ alkyl.

57. A method of stabilizing a vitamin, said method comprising combining at least one compound of formulae ii, ii′

and/or i″

with said oil and/or wax,

wherein the ratio of the total weight percent of the one or more compounds of formulae ii, ii′ and

/or i″

to the total weight percent of the vitamin, is within a range of 10;

1 to 1;

2.

wherein

each R_ii is independently linear or branched C₁ to C₈ alkyl;

R_ii1 is —

C(O)CH₃, —

CO₂R_ii3, —

C(O)NH₂, —

C(O)N(R_ii4)₂, or —

CN;

X is O, NH or N-alkyl;

R_ii2 is linear or branched C₁ to C₂₀ alkyl;

R_ii3 is linear or branched C₁ to C₂₀ alkyl;

each R_ii4 is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

1</sub> is —

C(O)CH₃, —

CO₂R<sub>ii′

3</sub>, —

C(O)NH₂, —

C(O)N(R<sub>ii′

4</sub>)₂, or —

CN;

R<sub>ii′

2</sub> is linear or branched C₁ to C₃₀ alkyl;

R<sub>ii′

3</sub> is linear or branched C₁ to C₂₀ alkyl;

each R<sub>ii′

4</sub> is independently hydrogen or linear or branched C₁ to C₈ alkyl;

R<sub>ii′

5</sub> is linear or branched C₁-C₈ alkyl or hydrogen;

R<sub>ii′

6</sub> is linear or branched C₁-C₈ alkyl;

each R_i″

is independently linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy;

or one R_i″

is H and the other R_i″

is linear or branched C₁ to C₈ alkyl, or linear or branched C₁ to C₈ alkoxy,

R<sub>i″

1</sub> is COCH₃, CO₂R<sub>i″

5</sub>, CONH₂, CONH(R<sub>i″

6</sub>)₂, CN, COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>), or the quaternized salt form of the formula COX(CH₂)n-N—

(R<sub>i″

2</sub>)(R<sub>i″

4</sub>)(R<sub>i″

3</sub>)⁺Y⁻

,

n is an integer of 1 to 5,

Y⁻

is an anion,

R<sub>i″

2</sub>, R<sub>i″

3</sub> and R<sub>i″

4</sub> are independently linear or branched C₁ to C₂₀ alkyl; and

R<sub>i″

5</sub> and R<sub>i″

6</sub> are independently hydrogen or linear or branched C₁-C₂₀ alkyl.

58. A method according to claim 57, wherein the vitamin is Vitamin E, C or K or a derivative thereof.