IP Library Granted Patent US 10,407,528
Granted Patent B2
US 10,407,528 · App. 15/925,042 · Granted Sep 10, 2019

UV-absorbing polymers and formulations thereof

Inventors: Krishnamurthy Nacharaju (Hilliard, OH); Osama M. Musa (Bedminster, NJ); Michael A. Tallon (Aberdeen, NJ)
Assignee: ISP INVESTMENTS LLC
C08F265/02A61K8/8164A61K9/0014A61K47/32A61Q5/06A61Q17/04A61Q19/00C08F255/08C08F255/10C08F257/02C08F261/06A61K2800/10
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Quick Facts
Patent No.
US 10,407,528
App. No.
15/925,042
Granted
Sep 10, 2019
Kind
B2
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.

Claims (37)

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

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: HERCULES LLC; ISP INVESTMENTS LLC
Reel/Frame 051561/0676 →
SUPPLEMENTAL SECURITY AGREEMENT Recorded May 24, 2019
From: HERCULES LLC; ISP INVESTMENTS LLC
To: THE BANK OF NOVA SCOTIA
Reel/Frame 049286/0434 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2018
From: NACHARAJU, KRISHNAMURTHY; MUSA, OSAMA M.; TALLON, MICHAEL A.
To: ISP INVESTMENTS INC.
Reel/Frame 045275/0891 →
CHANGE OF NAME - CONVERSION TO LLP Recorded Mar 19, 2018
From: ISP INVESTMENTS INC.
To: ISP INVESTMENTS LLC
Reel/Frame 045640/0013 →
Continuity (4)
Division 15400271 · Jan 6, 2017
Continuation 14769388
Provisional Application 61789582 · Mar 15, 2013
Related Publication 20180208695A1 · Jul 26, 2018