IP Library Granted Patent US 7,915,330
Granted Patent B2
US 7,915,330 · App. 12/205,546 · Granted Mar 29, 2011

Photostabilizing silicone fluids

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Quick Facts
Patent No.
US 7,915,330
App. No.
12/205,546
Granted
Mar 29, 2011
Kind
B2
Abstract

A silicone fluid comprising a chromophore-substituted polyorganosiloxane having a formula (2): wherein x is an integer in the range of 60 to 2000; y is an integer in the range of 5 to 100; a ratio x:y is in a range of about 10:1 to about 20:1; and X is a photostabilizing chromophore.

Claims (33)

1. A method of photostabilizing a photodegradable UV-absorbing compound or polymer comprising

adding a photostabilizing amount of a silicone fluid to the photodegradable compound or polymer,

wherein the silicone fluid has a formula (2):

wherein x is an integer in the range of 60 to 150; y is an integer in the range of 6 to 30; a ratio x:y is in a range of about 10:1 to about 20:1; and X is a photostabilizing chromophore of formula (3):

wherein k and l equal zero or one of k and l equals 1 and the other is zero; R is an alkoxide; R′ is an organic linker; m is an integer in a range of zero to about ten; and n is an integer in a range from two to about twenty.

2. A method of photostabilizing a photodegradable UV-absorbing compound or polymer comprising

adding a photostabilizing amount of a silicone fluid to the photodegradable compound or polymer, wherein the silicone fluid comprises a photostabilizing-chromophore-substituted linear, random copolymer of formula IV:

wherein the random copolymer comprises end caps (E), multiple mer(A) units, and multiple mer(B) units; wherein the end caps (E) are independently selected from the group consisting of —Si(CH 3 ) 3 and —Si(CH 3 ) 2 (X); the mer(A) units are —OSi(CH 2 ) 2 —; the mer(B) units are —OSi(CH 2 )(X)—; a ratio of the number of units of mer(A):mer(B) is at least 10:1, a sum of the number of mer(A) units and mer(B) units is in the range of 80 to 300; and X is a photostabilizing chromophore of a formula (6):

wherein R is selected from the croup consisting of methoxy and ethoxy; R′ is an organic linker; k and l equal zero or one of k and l equals 1 and the other is zero; m is an integer in a range of zero to about ten; and n is an integer in a range of 2 to about 20.

3. The method of claim 2 , wherein the sum of the number of units of mer(A) and mer(B) is in the range of 80 to 150.

4. The method of claim 3 , wherein the sum of the number of units of mer(A) and mer(B) is in the range of 80 to 120.

5. The method of claim 2 , wherein m is equal to one and the organic linker is selected from the group consisting of CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH(CH 3 )CH 2 , CH 2 C(CH 3 ) 2 CH 2 , CH 2 OCH 2 , CH 2 CH 2 OCH 2 CH 2 , and mixtures thereof.

6. The method of claim 5 , wherein the organic linker is CH 2 C(CH 3 ) 2 CH 2 .

7. The method of claim 2 , wherein the photodegradable compound comprises a dibenzoylmethane derivative.

8. The method of claim 7 , wherein said dibenzoylmethane derivative is selected from the group consisting of 2-methyldibenzoylmethane; 4-methyldibenzoylmethane; 4-isopropyldibenzoylmethane; 4-tert-butyldibenzoylmethane; 2,4-dimethyldibenzoylmethane; 2,5-dimethyldibenzoylmethane; 4,4′-diisopropyldibenzoylmethane; 4,4′-dimethoxydibenzoylmethane; 4-tert-butyl-4′-methoxydibenzoylmethane; 2-methyl-5-isopropyl-4′-methoxydibenzoylmethane; 2-methyl-5-tert-butyl-4′-methoxydibenzoylmethane; 2,4-dimethyl-4′-methoxydibenzoylmethane; 2,6-dimethyl-4-tert-butyl-4′-methoxydibenzoylmethane, and combinations thereof.

9. The method of claim 2 wherein the photodegradable compound comprises a photoactive compound selected from the group consisting of p-aminobenzoic acid and salts and derivatives thereof; anthranilate and derivatives thereof; salicylate and derivatives thereof; cinnamic acid and derivatives thereof; dihydroxycinnamic acid and derivatives thereof; camphor and salts and derivatives thereof; trihydroxycinnamic acid and derivatives thereof; dibenzalacetone naphtholsulfonate and salts and derivatives thereof; benzalacetophenone naphtholsulfonate and salts and derivatives thereof; dihydroxy-naphthoic acid and salts thereof; naphthalene dicarboxylic acids, derivatives, dimers, oligimers, polymers, and salts and combinations thereof; o-hydroxydiphenyldisulfonate and salts and derivatives thereof; p-hydroxydiphenyldisulfonate and salts and derivatives thereof; coumarin and derivatives thereof; diazole derivatives; quinine derivatives and salts thereof; quinoline derivatives; hydroxy-substituted benzophenone derivatives; methoxy-substituted benzophenone derivatives; uric acid derivatives; vilouric acid derivatives; tannic acid and derivatives thereof; hydroquinone; benzophenone derivatives; 1,3,5-triazine derivatives, phenyldibenzimidazole tetrasulfonate and salts and derivatives thereof; terephthalylidene dicamphor sulfonic acid and salts and derivatives thereof; methylene bis-benzotriazolyl tetramethylbutylphenol and salts and derivatives thereof; bis-ethylhexyloxyphenol methoxyphenyl triazine and salts and derivatives thereof; diethylamino hydroxybenzoyl hexyl benzoate and salts and derivatives thereof; and combinations thereof.

10. The method of claim 1 , wherein the ratio x:y is about 10:1.

11. The method of claim 1 , wherein x is an integer in the range of 60 to about 100.

12. The method of claim 11 , wherein x is about 60.

13. The method of claim 11 , wherein x is about 80.

14. The method of claim 11 , wherein x is about 100.

15. The method of claim 1 , wherein m is equal to one and the organic linker is selected from the group consisting of CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH(CH 3 )CH 2 , CH 2 C(CH 3 ) 2 CH 2 , CH 2 OCH 2 , CH 2 CH 2 OCH 2 CH 2 , and mixtures thereof.

16. The method of claim 15 , wherein the organic linker is CH 2 C(CH 3 ) 2 CH 2 .

17. The method of claim 1 , wherein the photodegradable UV-absorbing compound comprises a dibenzoylmethane derivative.

18. The method of claim 17 , wherein said dibenzoylmethane derivative is selected from the group consisting of 2-methyldibenzoylmethane; 4-methyldibenzoylmethane; 4-isopropyldibenzoylmethane; 4-tert-butyldibenzoylmethane; 2,4-dimethyldibenzoylmethane; 2,5-dimethyldibenzoylmethane; 4,4′-diisopropyldibenzoylmethane; 4,4′-dimethoxydibenzoylmethane; 4-tert-butyl-4′-methoxydibenzoylmethane; 2-methyl-5-isopropyl-4′-methoxydibenzoylmethane; 2-methyl-5-tert-butyl-4′-methoxydibenzoylmethane; 2,4-dimethyl-4′-methoxydibenzoylmethane; 2,6-dimethyl-4-tert-butyl-4′-methoxydibenzoylmethane, and combinations thereof.

19. The method of claim 1 , wherein the photodegradable UV-absorbing compound comprises a photoactive compound selected from the group consisting of p-aminobenzoic acid and salts and derivatives thereof; anthranilate and derivatives thereof; salicylate and derivatives thereof; cinnamic acid and derivatives thereof; dihydroxycinnamic acid and derivatives thereof; camphor and salts and derivatives thereof; trihydroxycinnamic acid and derivatives thereof; dibenzalacetone naphtholsulfonate and salts and derivatives thereof; benzalacetophenone naphtholsulfonate and salts and derivatives thereof; dihydroxy-naphthoic acid and salts thereof; naphthalene dicarboxylic acids, derivatives, dimers, oligimers, polymers, and salts and combinations thereof; o-hydroxydiphenyldisulfonate and salts and derivatives thereof; p-hydroxydiphenyldisulfonate and salts and derivatives thereof; coumarin and derivatives thereof; diazole derivatives; quinine derivatives and salts thereof; quinoline derivatives; hydroxy-substituted benzophenone derivatives; methoxy-substituted benzophenone derivatives; uric acid derivatives; vilouric acid derivatives; tannic acid and derivatives thereof; hydroquinone; benzophenone derivatives; 1,3,5-triazine derivatives, phenyldibenzimidazole tetrasulfonate and salts and derivatives thereof; terephthalylidene dicamphor sulfonic acid and salts and derivatives thereof; methylene bis-benzotriazolyl tetramethylbutylphenol and salts and derivatives thereof; bis-ethylhexyloxyphenol methoxyphenyl triazine and salts and derivatives thereof; diethylamino hydroxybenzoyl hexyl benzoate and salts and derivatives thereof; and combinations thereof.

20. A method of photostabilizing a photodegradable UV-absorbing compound or polymer comprising

adding a photostabilizing amount of a silicone fluid to the photodegradable compound or polymer,

wherein the silicone fluid has a formula (2):

wherein x is about 100; a ratio x:y is in a range of about 10:1 to about 15:1; and X is a photostabilizing chromophore of formula (3):

wherein k and l equal zero or one of k and l equals 1 and the other is zero; R is a methoxyl or an ethoxy group; R′ is an organic linker selected from the group consisting of CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH(CH 3 )CH 2 , CH 2 C(CH 3 ) 2 CH 2 , CH 2 OCH 2 , CH 2 CH 2 OCH 2 CH 2 , and mixtures thereof; m is an integer in a range of zero to about ten; and n is an integer in a range from two to about twenty.

21. The method of claim 1 , further including the step of adding a second photostabilizer to the photodegradable UV-absorbing compound or polymer.

22. The method of claim 21 , wherein the second photostabilizer is octocrylene to provide photostabilizing synergism.

Assignments (7)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2013
From: BONDA, CRAIG A.; PAVLOVIC, ANNA; O'LENICK, ANTHONY J., JR.
To: HALLSTAR INNOVATIONS CORP.
Reel/Frame 030381/0650 →
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 →