Ultraviolet radiation absorbing polymers

• US 9,469,725 B2
• Filed: 03/13/2013
• Issued: 10/18/2016
• Est. Priority Date: 06/28/2012
• Status: Active Grant

• Current Assignee: Johnson & Johnson Consumer Inc. (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Consumer Inc. (Johnson & Johnson)
• Inventors: Levins, Christopher G., Nathan, Aruna, Daly, Susan
• Primary Examiner(s): Song, Jianfeng
• Application Number:
  US13/799,193
• Publication Number:
  US 20140004060A1
• Time in Patent Office: 1,315 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/57 Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
• CPC Class Codes: A61K 8/85 Polyesters
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: C08G 63/54 the acids or hydroxy compounds containing carbocyclic rings
• CPC Class Codes: C08G 63/6856 Dicarboxylic acids and dihydroxy compounds

Abstract

The present invention includes an ultraviolet radiation absorbing polymer composition that includes polymers containing a UV-chromophore, as described in the specification and as claimed the reaction product of a monoglyceride and a poly-acid monomer containing a UV-chromophore.

Claims

1. An ultraviolet radiation absorbing polymer composition comprising the reaction product of a monoglyceride and a poly-acid monomer containing a UV-chromophore selected from the group consisting of triazoles;

dibenzoylmethanes;

4-aminobenzoic acid and alkane esters thereof;

anthranilic acid and alkane esters thereof;

salicylic acid and alkane esters thereof;

hydroxycinnamic acid and alkane esters thereof;

dihydroxy, dicarboxy, or hydroxycarboxybenzophenones and alkane ester or acid halide derivatives thereof;

dihydroxy, dicarboxy, or hydroxycarboxychalcones and alkane ester or acid halide derivatives thereof;

dihydroxy, dicarboxy, or hydroxycarboxycoumarins and alkane ester or acid halide derivatives thereof;

benzimidazole derivatives;

benzoxazole derivatives;

3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl);

6-octyl-2-(4-(4,6-di([1,1′

-biphenyl]-4-yl)-1,3,5-triazin-2-yl)-3-hydroxyphenoxy)propanoate and trioctyl 2,2′

,2″

-(((1,3,5-triazine-2,4,6-triyl)tris(3-hydroxybenzene-4,1-diyl))tris(oxy))tripropanoate.

2. The composition of claim 1, wherein the monoglyceride is selected from the group consisting of glycerol monostearate, glycerol monopalmitate, glycerol monomyristate, glycerol monocaprate, glycerol monodecanoate, glycerol monolaurate, glycerol monolinoleate, and glycerol monooleate.

3. The composition of claim 1, comprising the reaction product of said monoglyceride, said poly-acid monomer containing said UV-chromophore and a poly-ol selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, bis-2-hydroxyethyl ether, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, linear poly(ethylene glycol), branched poly(ethylene glycol), linear poly(propylene glycol), branched poly(propylene glycol), linear poly(ethylene-co-propylene glycol)s and branched poly(ethylene-co-propylene glycol)s glycols, polyglycerols, polyglycerol esters, glycerol, monosaccharide, disaccharides, polysaccharides, and linear polysiloxanes end-functionalized with carbinol groups.

4. The composition of claim 1, wherein the polymer composition is a reaction product of said monoglyceride, said poly-acid monomer containing said UV-chromophore and a poly-acid selected from the group consisting of natural multifunctional carboxylic acid, hydroxy acid and unsaturated acid;

wherein the natural multifunctional carboxylic acid is selected from the group consisting of succinic, glutaric, adipic, pimelic, suberic, and sebacic acids;

wherein the hydroxy acid is selected from the group consisting of diglycolic, malic, tartaric and citric acids;

wherein the unsaturated acid is selected from the group consisting of fumaric acid and maleic acid.

5. The composition of claim 1, wherein the ultraviolet radiation absorbing polymer composition has a weight average molecular weight from about 500 to about 50,000.

11. The composition of claim 1 wherein the monoglyceride is a C₁₂-C₁₈ monoglyceride.

6. An ultraviolet radiation absorbing polymer composition comprising a polymer comprising a repeat unit

7. The ultraviolet radiation absorbing polymer composition of claim 6, comprising a polymer having the structure

8. The ultraviolet radiation absorbing polymer composition of claim 6, wherein n is a number such that the ultraviolet radiation absorbing polymer composition has a weight average molecular weight from about 500 to about 50,000.

9. A composition comprising a cosmetically acceptable topical carrier and an ultraviolet radiation absorbing polymer composition that comprises the reaction product of a monoglyceride and a poly-acid monomer containing a UV-chromophore selected from the group consisting of triazoles;

dibenzoylmethanes;

4-aminobenzoic acid and alkane esters thereof;

anthranilic acid and alkane esters thereof;

salicylic acid and alkane esters thereof;

hydroxycinnamic acid and alkane esters thereof;

dihydroxy, dicarboxy, or hydroxycarboxybenzophenones and alkane ester or acid halide derivatives thereof;

dihydroxy, dicarboxy, or hydroxycarboxychalcones and alkane ester or acid halide derivatives thereof;

dihydroxy, dicarboxy, or hydroxycarboxycoumarins and alkane ester or acid halide derivatives thereof;

benzimidazole derivatives;

benzoxazole derivatives;

3-(3-(2H-benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl);

6-octyl-2-(4-(4,6-di([1,1′

-biphenyl]-4-yl)-1,3,5-triazin-2-yl)-3-hydroxyphenoxy)propanoate and trioctyl 2,2′

,2″

-(((1,3,5-triazine-2,4,6-triyl)tris(3-hydroxybenzene-4,1-diyl))tris(oxy))tripropanoate.

12. The composition of claim 9 wherein the monoglyceride is a C₁₂-C₁₈ monoglyceride.

10. A composition comprising a cosmetically acceptable topical carrier and an ultraviolet radiation absorbing polymer composition comprising a polymer comprising a repeat unit: