Ultraviolet radiation absorbing polymers

Patent metadata

Field	Value
Publication number	US-9469725-B2
Application number	US-201313799193-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Jun 28, 2012
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

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.

First claim

We claim:

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.

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

wherein X comprises 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, and R 1 is a saturated or unsaturated hydrocarbon moiety having a number of carbon atoms between 4 and 30.

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.

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

wherein X comprises 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.

11. The composition of claim 1 wherein the monoglyceride is a C 12 -C 18 monoglyceride.

12. The composition of claim 9 wherein the monoglyceride is a C 12 -C 18 monoglyceride.

Assignees

• Johnson & Johnson Consumer Inc

Inventors

• Levins Christopher G
• Nathan Aruna
• Daly Susan

Classifications

• C08G63/54

  the acids or hydroxy compounds containing carbocyclic rings · CPC title

• A61K2800/57

  Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances · CPC title

• C08G63/6856 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• A61Q17/04 Primary

  Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations · CPC title

• A61K8/85 Primary

  Polyesters · CPC title