IP Library › Granted Patent US 7,235,587

Granted Patent B2

US 7,235,587 · App. 10/883,507 · Granted Jun 26, 2007

Diesters containing two crylene or fluorene moieties, sunscreen compositions containing the same, and methods of photostabilizing a sunscreen compositions containing the same

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Patent No.: US 7,235,587
App. No.: 10/883,507
Granted: Jun 26, 2007
Kind: B2

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Abstract

Diesters that include one or more of a crylene and/or a fluorene moiety, and sunscreen compositions including a mixture of a photoactive compound and one or more of a diester that includes one or more of a crylene and/or a fluorene moiety are described herein. Also disclosed are methods for stabilizing a sunscreen composition, methods of stabilizing a dibenzoylmethane derivative, and methods for protecting human skin from ultraviolet radiation with one or more of a diester that includes one or more of a crylene and/or a fluorene moiety are described herein.

Claims (96)

1. A compound of formula (I):

wherein A and B are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 1 and R 3 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 2 is selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne; R 4 , R 5 , R 6 and R 7 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and a, b, c and d are each in the range of 0 to 4.

2. The compound of claim 1 , wherein R 1 and R 3 are selected from the group consisting of C 2 -C 15 alkyl.

3. The compound of claim 2 , wherein R 1 and R 3 are the same and are 3,3-dimethyl propane.

4. The compound of claim 1 , wherein R 2 is selected from the group consisting of C 2 -C 10 alkylene.

5. The compound of claim 4 , wherein R 2 is selected from the group consisting of (2E)but-2-ene and (2Z)but-2-ene.

6. The compound of claim 1 , wherein A and B are oxygen.

7. A compound of formula (II):

wherein C and D are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 8 and R 10 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 9 is selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne; R 11 , R 12 , R 13 and R 14 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and e, f, g and h are each in the range of 0 to 4.

8. The compound of claim 7 , wherein R 8 and R 10 are selected from the group consisting of C 2 -C 15 alkyl.

9. The compound of claim 8 , wherein R 8 and R 10 are the same and are 3,3-dimethyl propane.

10. The compound of claim 7 , wherein R 9 is selected from the group consisting of C 2 -C 10 alkylene.

11. The compound of claim 10 , wherein R 9 is selected from the group consisting of (2E)but-2-ene and (2Z)but-2-ene.

12. The compound of claim 7 , wherein C and D are oxygen.

13. A compound of formula (III):

wherein E and F are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 15 and R 17 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 16 is selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne; R 18 , R 19 , R 20 and R 21 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and i, j, k and l are each in the range of 0 to 4.

14. The compound of claim 13 , wherein R 8 and R 10 are selected from the group consisting of C 2 -C 15 alkyl.

15. The compound of claim 14 , wherein R 8 and R 10 are the same and are 3,3-dimethyl propane.

16. The compound of claim 13 , wherein R 9 is selected from the group consisting of C 2 -C 10 alkylene.

17. The compound of claim 16 , wherein R 9 is selected from the group consisting of (2E)but-2-ene and (2Z)but-2-ene.

18. The compound of claim 13 , wherein E and F are oxygen.

19. A sunscreen composition, comprising a mixture of a photoactive compound and a compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof:

wherein A, B, C, D, E and F are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 1 , R 3 , R 8 , R 10 , R 15 and R 17 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 2 , R 9 and R 16 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne; R 4 , R 5 , R 6 , R 7 , R 11 , R 12 , R 13 , R 14 , R 18 , R 19 , R 20 and R 21 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and a, b, c, d, e, f, g, h, i, j, k and l are each in the range of 0 to 4.

20. The composition of claim 19 , wherein R 1 , R 3 , R 8 , R 10 , R 15 and R 17 are selected from the group consisting of C 2 -C 15 alkyl.

21. The composition of claim 20 , wherein R 1 and R 3 are each 3,3-dimethylpropane.

22. The composition of claim 20 , wherein R 8 and R 10 are each 3,3-dimethylpropane.

23. The composition of claim 20 , wherein R 15 and R 17 are each 3,3-dimethylpropane.

24. The composition of claim 19 , wherein A, B, C, D, E and F are each oxygen.

25. The composition of claim 19 , further comprising a diester or polyester of naphthalene dicarboxylic acid selected from the group consisting of compounds of formulae (XX) and (XXI), and combinations thereof:

wherein R 93 and R 94 are the same or different and selected from the group consisting of C 1 -C 22 alkyl groups, diols having the structure HO—R 91 —OH and polyglycols having the structure HO—R 90 —(—O—R 91 —) γ —OH; wherein each R 90 and R 91 is the same or different and selected from the group consisting of C 1 -C 6 straight or branched chain alkyl groups; and wherein α and γ are each in a range of 1 to 100 and β is in a range of 0 to 100.

26. The composition of claim 19 , wherein said compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof is present in a range of about 0.1% to about 50% by weight of the total weight of the composition.

27. The composition of claim 26 , wherein said compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof is present in a range of about 0.1% to about 25% by weight of the total weight of the composition.

28. The composition of claim 27 , wherein said compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof is present in a range of about 0.1% to about 10% by weight of the total weight of the composition.

29. The composition of claim 19 , comprising a dibenzoylmethane derivative.

30. A method of photostabilizing a sunscreen composition comprising a photoactive compound, said method comprising the step of, adding to said sunscreen composition a photostabilizing amount of a compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof:

31. The method of claim 30 , wherein R 1 , R 3 , R 8 , R 10 , R 15 and R 17 are selected from the group consisting of C 2 -C 15 alkyl.

32. The method of claim 31 , wherein R 1 and R 3 are each 3,3-dimethylpropane.

33. The method of claim 31 , wherein R 8 and R 10 are each 3,3-dimethylpropane.

34. The method of claim 31 , wherein R 15 and R 17 are each 3,3-dimethylpropane.

35. The method of claim 30 , wherein A, B, C, D, E and F are each oxygen.

36. A method of photostabilizing a dibenzoylmethane derivative, said method comprising the step of, adding to said dibenzoylmethane derivative a photostabilizing amount of a compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof:

37. The method of claim 36 , wherein R 1 , R 3 , R 8 , R 10 , R 15 and R 17 are selected from the group consisting of C 2 -C 15 alkyl.

38. The method of claim 37 , wherein R 1 and R 3 are each 3,3-dimethylpropane.

39. The method of claim 37 , wherein R 8 and R 10 are each 3,3-dimethylpropane.

40. The method of claim 37 , wherein R 15 and R 17 are each 3,3-dimethylpropane.

41. The method of claim 36 , wherein A, B, C, D, E and F are each oxygen.

42. A method of protecting human skin from ultraviolet radiation comprising topically applying to said skin, in a cosmetically acceptable carrier, a compound selected from the group consisting of compounds of formula (I), compounds of formula (II), compounds of formula (III), and combinations thereof:

43. The method of claim 42 , wherein R 1 , R 3 , R 8 , R 10 , R 15 and R 17 are selected from the group consisting of C 2 -C 15 alkyl.

44. The method of claim 43 , wherein R 1 and R 3 are each 3,3-dimethylpropane.

45. The method of claim 43 , wherein R 8 and R 10 are each 3,3-dimethylpropane.

46. The method of claim 43 , wherein R 15 and R 17 are each 3,3-dimethylpropane.

47. The method of claim 42 , wherein A, B, C, D, E and F are each oxygen.

48. A compound of formula (IV):

wherein G and H are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 22 and R 23 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 24 , R 25 , R 26 and R 27 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and m, n, o and p are each in the range of 0 to 4.

49. The compound of claim 48 , wherein R 22 and R 23 are selected from the group consisting of C 2 -C 15 alkyl.

50. The compound of claim 49 , wherein R 22 and R 23 are the same and are 3,3-dimethyl propane.

51. The compound of claim 48 , wherein G and H are oxygen.

52. A compound of formula (V):

wherein I and J are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 28 and R 29 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 30 , R 31 , R 32 and R 33 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and q, r, s and t are each in the range of 0 to 4.

53. The compound of claim 52 , wherein R 28 and R 29 are selected from the group consisting of C 2 -C 15 alkyl.

54. The compound of claim 53 , wherein R 28 and R 29 are the same and are 3,3-dimethyl propane.

55. The compound of claim 52 , wherein I and J are oxygen.

56. A compound of formula (VI):

wherein K and L are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 34 and R 35 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 36 , R 37 , R 38 and R 39 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and u, v, w and x are each in the range of 0 to 4.

57. The compound of claim 56 , wherein R 34 and R 35 are selected from the group consisting of C 2 -C 15 alkyl.

58. The compound of claim 57 , wherein R 34 and R 35 are the same and are 3,3-dimethyl propane.

59. The compound of claim 56 , wherein K and L are oxygen.

60. A compound of formula (VII):

wherein M and N are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 40 and R 41 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 42 , R 43 , R 44 and R 45 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and y, z, a and b are each in the range of 0 to 4.

61. The compound of claim 60 , wherein R 40 and R 41 are selected from the group consisting of C 2 -C 15 alkyl.

62. The compound of claim 61 , wherein R 40 and R 41 are the same and are 3,3-dimethyl propane.

63. The compound of claim 60 , wherein M and N are oxygen.

64. A sunscreen composition, comprising a mixture of a photoactive compound and a compound selected from the group consisting of compounds of formula (IV), compounds of formula (V), compounds of formula (VI), compounds of formula (VII), and combinations thereof:

wherein G, H, I, J, K, L, M and N are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 24 , R 25 , R 26 , R 27 , R 30 , R 31 , R 32 , R 33 , R 36 , R 37 , R 38 , R 39 , R 42 , R 43 , R 44 and R 45 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 2 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl, substituted heterocycloalkyl, hydroxyl, ester, carboxy, cyano, amino, amido, sulfur and halo; and m, n, o, p, q, r, s, t, u, v, w, x, y, z, a and b are each in the range of 0 to 4.

65. The composition of claim 64 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are selected from the group consisting of C 2 -C 15 alkyl.

66. The composition of claim 65 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are each 3,3-dimethylpropane.

67. The composition of claim 64 , wherein G, H, I, J, K, L, M and N are each oxygen.

68. The composition of claim 64 , comprising a dibenzoylmethane derivative.

69. A method of photostabilizing a sunscreen composition comprising a photoactive compound, said method comprising the step of, adding to said sunscreen composition a photostabilizing amount of a compound selected from the group consisting of compounds of formula (IV), compounds of formula (V), compounds of formula (VI), compounds of formula (VII), and combinations thereof:

70. The method of claim 69 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are selected from the group consisting of C 2 -C 15 alkyl.

71. The method of claim 70 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are each 3,3-dimethylpropane.

72. The method of claim 69 , wherein G, H, I, J, K, L, M and N are each oxygen.

73. A method of photostabilizing a dibenzoylmethane derivative, said method comprising the step of, adding to said dibenzoylmethane derivative a photostabilizing amount of a compound selected from the group consisting of compounds of formula (IV), compounds of formula (V), compounds of formula (VI), compounds of formula (VII), and combinations thereof:

74. The method of claim 73 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are selected from the group consisting of C 2 -C 15 alkyl.

75. The method of claim 74 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are each 3,3-dimethylpropane.

76. The method of claim 73 , wherein G, H, I, J, K, L, M and N are each oxygen.

77. A method of protecting human skin from ultraviolet radiation comprising topically applying to said skin, in a cosmetically acceptable carrier, a compound selected from the group consisting of compounds of formula (IV), compounds of formula (V), compounds of formula (VI), compounds of formula (VII), and combinations thereof:

78. The method of claim 77 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are selected from the group consisting of C 2 -C 15 alkyl.

79. The method of claim 77 , wherein R 22 , R 23 , R 28 , R 29 , R 34 , R 35 , R 40 and R 41 are each 3,3-dimethylpropane.

80. The method of claim 77 , wherein G, H, I, J, K, L, M and N are each oxygen.

Assignments (10)

THIRD AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 20, 2024

From: THE HALLSTAR COMPANY; HALLSTAR INNOVATIONS CORP.; HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY; UNIPLEX COMPANY

To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT

Reel/Frame 069747/0045 →

THIRD AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 3, 2023

From: THE HALLSTAR COMPANY; HALLSTAR INNOVATIONS CORP.; HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY; UNIPLEX COMPANY

To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT

Reel/Frame 065448/0262 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2018

From: HALLSTAR INNOVATIONS CORP.

To: HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY

Reel/Frame 046977/0359 →

SECOND AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 25, 2014

From: HALLSTAR INNOVATIONS CORP.

To: BANK OF AMERICA, N.A., AS AGENT

Reel/Frame 034468/0854 →

AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 21, 2012

From: HALLSTAR INNOVATIONS CORP.

To: BANK OF AMERICA, N.A., AS AGENT

Reel/Frame 027742/0917 →

SECURITY INTEREST Recorded Oct 16, 2008

From: HALLSTAR INNOVATIONS CORP.

To: LASALLE BANK NATIONAL ASSOCIATION, AS AGENT

Reel/Frame 021709/0286 →

INTELLECTUAL PROPERTY RELEASE Recorded Oct 14, 2008

From: LASALLE BANK NATIONAL ASSOCIATION, AS AGENT

To: HALLSTAR INNOVATIONS CORP.

Reel/Frame 021669/0701 →

CHANGE OF NAME Recorded May 14, 2007

From: CPH INNOVATIONS CORP.

To: HALLSTAR INNOVATIONS CORP.

Reel/Frame 019287/0001 →

SECURITY AGREEMENT Recorded Jan 25, 2006

From: CPH INNOVATIONS CORP.

To: LASALLE BANK NATIONAL ASSOCIATION, AS AGENT

Reel/Frame 017207/0546 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2005

From: BONDA, CRAIG A.; PAVLOVIC, ANNA

To: CPH INNOVATIONS CORPORATION

Reel/Frame 016300/0001 →