Water-soluble UV-absorbing compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-10322993-B2
Application number	US-201615352132-A
Country	US
Kind code	B2
Filing date	Nov 15, 2016
Priority date	Dec 2, 2015
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

Described herein are dimethyl acetal-containing UV-absorbing compounds and their uses in preparing UV-absorbing polyvinyl alcohol prepolymers suitable for producing UV-absorbing contact lenses capable of blocking ultra-violet (“UV”) radiation and optionally (but preferably) violet radiation with wavelengths from 380 nm to 440 nm, thereby protecting eyes to some extent from damages caused by UV radiation and potentially from violet radiation. This invention also provides a UV-absorbing polyvinyl alcohol prepolymer.

First claim

What is claimed is:

1. An acetal-containing, UV-absorbing compound of any one of formula (I) to (V)

in which:
R a is CH 3 or C 2 H 5 ;
R o is H or CH 3 ;
R 1 , R 2 and R 2 ′ independent of one other are H, CH 3 , CCl 3 , CF 3 , Cl, Br, NR′R″ in which R′ and R″ independent of each other are H or C 1 -C 4 alkyl, OH, or OCH 3 ;
R 1 ′ independent of each other are H, CH 3 , CCl 3 , CF 3 , Cl, Br, NR′R″ in which R′ and R″ independent of each other are H or C 1 -C 4 alkyl, OH, OCH 3 , SO 3 H, or SO 3 − Na + ;
R 3 and R 4 independent of each other are H or a first hydrophilic group which is

provided that at least one of R 3 and R 4 is the first hydrophilic group;
r1 is an integer of 1 to 8;
n1 is an integer of 2 to 20;
R 5 is H, *—COOH, *CONH—C 2 H 4 (OC 2 H 4 ) n1 —OCH 3 , or —CONH—C 2 H 4 —(OC 2 H 4 ) n1 —OH; one of R 6 and R 7 is H or a second hydrophilic group which is

while the other of R 6 and R 7 is

R 8 is CH 3 , C 2 H 5 ,

R 9 is SO 3 Na,

R 9 ′ is H, SO 3 Na,

R 10 is methyl or ethyl;
L1 is a linkage of

L2 is a linkage of

L3 is a linkage of

and
X1 is O or NR o .

2. The acetal-containing, UV-absorbing compound of claim 1 , being defined by formula (I).

3. The acetal-containing, UV-absorbing compound of claim 1 , being defined by formula (II).

4. The acetal-containing, UV-absorbing compound of claim 1 , being defined by formula (III).

5. The acetal-containing, UV-absorbing compound of claim 1 , being defined by formula (IV).

6. The acetal-containing, UV-absorbing compound of claim 1 , being defined by formula (V).

7. The acetal-containing, UV-absorbing compound of claim 2 , wherein the acetal-containing, UV-absorbing compound is further defined by

in which R a is methyl or ethyl, R 1 and R2 independent of each other are H, CH 3 , CCl 3 , CF 3 , Cl, Br, NR′R″, OH, or OCH 3 , in which R′ and R″ independent of each other are H, methyl or ethyl.

8. The acetal-containing, UV-absorbing compound of claim 3 , wherein the acetal-containing, UV-absorbing compound is further defined by

in which: R a is methyl or ethyl; R 1 and R 2 independent of each other are CH 3 , CCl 3 , CF 3 , Cl, Br, NR′R″, OH, or OCH 3 ; R′ and R″ independent of each other are H, methyl or ethyl; R 3 and R 4 independent of each other are

R 10 is methyl or ethyl.

9. The acetal-containing, UV-absorbing compound of claim 4 , wherein the acetal-containing, UV-absorbing compound is further defined by

in which: R a is methyl or ethyl; R 1 and R2 independent of each other are CH 3 , CCl 3 , CF 3 , Cl, Br, NR′R″ OH, or OCH 3 ; in which R′ and R″ independent of each other are H or C 1 -C 4 alkyl; R 8 is CH 3 , C 2 H 5 ,

R10 is methyl or ethyl; and r1 is an integer of 3 to 6.

10. The acetal-containing, UV-absorbing compound of claim 5 , wherein the acetal-containing, UV-absorbing compound is further defined by

in which R a is methyl or ethyl; R o is H or CH 3 ; R 1 and R 2 independent of each other are H, CH 3 , CCl 3 , CF 3 , Cl, Br, NR′R″ in which R′ and R″ independent of each other are H or C 1 -C 4 alkyl, OH, or OCH 3 .

11. The acetal-containing, UV-absorbing compound of claim 6 , wherein the acetal-containing, UV-absorbing compound is further defined by

in which R a is methyl or ethyl, r1 is an integer of 3 to 6, and Z═CH 3 or COOH.

Assignees

• Novartis Ag

Inventors

• Chang Frank
• Desousa Ryan
• Holland Troy Vernon
• Laredo Walter R

Classifications

• G02B1/043

  Contact lenses · CPC title

• C08F116/06

  Polyvinyl alcohol {; Vinyl alcohol} · CPC title

• C07C225/22 Primary

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• G02C7/049

  Contact lenses having special fitting or structural features achieved by special materials or material structures · CPC title

• B29D11/00038 Primary

  Production of contact lenses · CPC title