UV-absorbing polymers and formulations thereof

Patent metadata

Field	Value
Publication number	US-10407528-B2
Application number	US-201815925042-A
Country	US
Kind code	B2
Filing date	Mar 19, 2018
Priority date	Mar 15, 2013
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

UV-absorbing polymers are provided that have at least one anhydride repeating unit that is covalently attached to at least one UV-absorbing moiety selected from the group consisting of functionalized dibenzoylmethanes, benzophenone sulfonamides, triphenyl triazines, and combinations thereof. Also provided are formulations comprising the UV-absorbing polymers.

First claim

What is claimed is:

1. A polymer comprising: a first repeating unit selected from the group consisting of:

and combinations thereof, wherein
each X is independently selected from the group consisting of O, NR 1 , and combinations thereof;
each R 1 and R 2 is independently selected from the group consisting of hydrogen, halogen, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms;
each R 3 is independently selected from the group consisting of hydrogen, U, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms;
each M is independently selected from the group consisting of alkali metal ion, alkaline earth metal ion, ammonium ion, and combinations thereof;
each U has a structure independently selected from the group consisting of:

and combinations thereof, wherein each R 12 , R 13 , R 15 , R 16 , R 22 , R 24 , R 25 , R 32 , R 34 and R 35 is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms, and combinations thereof;
each Y is independently selected from the group consisting of O, NR 1 , S, and combinations thereof;
each Q is independently selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; and
each (wavy bond) indicates the point of attachment for each said U.

2. The polymer according to claim 1 wherein said first repeating unit is selected from the group consisting of:

and combinations thereof, wherein each Z is a residue of a monomer independently selected from the group consisting of functionalized and unfunctionalized alpha-olefins, maleimides, maleamic acids, maleic anhydride, 4-vinyl-1,2,3-triazoles, 5-vinyl-1,2,3-triazoles, (meth)acrylamides, (meth)acrylates, vinyls, allyls, α,□β-olefinically unsaturated carboxylic nitriles, styrenes, vinyl ethers, vinyl esters, vinyl acetates, vinyl amides, vinyl alcohols, vinyl carbonates, vinyl carbamates, vinyl thiocarbamates, vinyl ureas, vinyl halides, vinyl imidazoles, vinyl lactams, vinyl pyridines, vinyl silanes, vinyl siloxanes, vinyl sulfones, allyl ethers, and combinations thereof, and wherein said X, Y, Q, R 1 , R 2 , R 3 , M, U, R 12 , R 13 , R 15 , R 16 , R 22 , R 24 , R 25 , R 32 , R 34 and R 35 retain their definitions according to claim 1 .

3. The polymer according to claim 2 wherein said vinyl ether is selected from the group consisting of: methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, octyl vinyl ether, ethyl hexyl vinyl ether, decyl vinyl ether, dodecyl vinyl ether, tetradecyl vinyl ether, octadecyl vinyl ether, and combinations thereof.

4. The polymer according to claim 2 wherein said alpha-olefin is selected from the group consisting of: isobutylene, octadecene, and combinations thereof.

5. The polymer according to claim 1 wherein each said U has an independently selected structure:

wherein each (wavy bond) indicates the point of attachment for said U.

6. The polymer according to claim 2 having a structure selected from the group consisting of:

wherein b, c, d, e, and f are mole fractions such that sum of said mole fractions for each said polymer equals to 1.0.

7. A polymer comprising: a first repeating unit selected from the group consisting of:

and combinations thereof, wherein
each X is independently selected from the group consisting of O, NR 1 , and combinations thereof;
each R 1 and R 2 is independently selected from the group consisting of hydrogen, halogen, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms;
R 3 is selected from the group consisting of hydrogen, U, and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms;
M is selected from the group consisting of alkali metal ion, alkaline earth metal ion, and ammonium ion;
each U has an independently selected structure:

and combinations thereof, wherein each R 12 , R 13 , R 15 , and R 16 is independently selected from the group consisting of hydrogen, halogen, amino, alkyl amino, hydroxyl, alkoxyl, sulfonyl, carboxyl, functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms, and combinations thereof;
each R 5 is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms;
each R 6 and R 7 is independently selected from the group consisting of functionalized and unfunctionalized hydrocarbyl optionally having one or more heteroatoms;
each Q is independently selected from the group consisting of functionalized and unfunctionalized hydrocarbylene optionally having one or more heteroatoms; and
each (wavy bond) indicates the point of attachment for each said U.

8. The polymer according to claim 7 wherein said first repeating unit is selected from the group consisting of:

and combinations thereof, wherein each Z is a residue of a monomer independently selected from the group consisting of functionalized and unfunctionalized alpha-olefins, maleimides, maleamic acids, maleic anhydride, 4-vinyl-1,2,3-triazoles, 5-vinyl-1,2,3-triazoles, (meth)acrylamides, (meth)acrylates, vinyls, allyls, α,□β-olefinically unsaturated carboxylic nitriles, styrenes, vinyl ethers, vinyl esters, vinyl acetates, vinyl amides, vinyl alcohols, vinyl carbonates, vinyl carbamates, vinyl thiocarbamates, vinyl ureas, vinyl halides, vinyl imidazoles, vinyl lactams, vinyl pyridines, vinyl silanes, vinyl siloxanes, vinyl sulfones, allyl ethers, and combinations thereof, and wherein said X, Q, R 1 , R 2 , R 3 , M, U, R 12 , R 13 , R 15 , R 16 , R 5 , R 6 , and R 7 retain their definitions according to claim 7 .

9. The polymer according to claim 8 wherein said vinyl ether is selected from the group consisting of: methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, octyl vinyl ether, ethyl hexyl vinyl ether, decyl vinyl ether, dodecyl vinyl ether, tetradecyl vinyl ether, octadecyl vinyl ether, and combinations thereof.

10. The polymer according to claim 8 wherein said alpha-olefin is selected from the group consisting of: isobutylene, octadecene, and combinations thereof.

11. The polymer according to claim 7 wherein each said U is independently selected from the group consisting of:

and combinations thereof, wherein eac

Assignees

• Isp Investments Llc

Inventors

• Nacharaju Krishnamurthy
• Musa Osama M
• Tallon Michael A

Classifications

• A61Q17/04

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

• A61K2800/10

  General cosmetic use · CPC title

• C08F265/02 Primary

  on to polymers of acids, salts or anhydrides · CPC title

• C08F8/32

  by reaction with amines · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title