Water-soluble UV-absorbing compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-10472319-B2
Application number	US-201916401193-A
Country	US
Kind code	B2
Filing date	May 2, 2019
Priority date	Dec 2, 2015
Publication date	Nov 12, 2019
Grant date	Nov 12, 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. A water-soluble, actinically-crosslinkable polyvinyl alcohol prepolymer, comprising:
repeating units of vinyl alcohol
repeating crosslinking units of formula (VI); and

repeating UV-absorbing units of formula (VII)

in which:
R 11 is hydrogen or C 1 -C 6 alkyl;
R 12 is an ethylenically unsaturated group of

in which q1 and q2 independently of each another are zero or one, and R 16 and R 17 independently of one another are a C 2 -C 8 alkylene divalent radical, R 18 is C 2 -C 8 alkenyl;
R 13 can be hydrogen or a C 1 -C 6 alkyl group;
R 14 is a C 1 -C 6 alkylene divalent radical;
R 15 is a monovalent radical of any one of formula (VIII)-(XII)

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;
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

X1 is O or NR o ;
one of R 19 and R 20 is H or a second hydrophilic group which is

while the other of R 19 and R 20 is a divalent radical of

2. The prepolymer of claim 1 , having a weight average molecular weight of at least about 2,000 Daltons, and comprising from about 1% to about 25% by mole of the repeating units of formula (VI).

3. The prepolymer of claim 1 , wherein R 14 is methylene divalent radical, R 11 is hydrogen or C 1 -C 4 alkyl, R 13 is hydrogen, and R 12 is a radical of

in which q2 is zero, R 18 is vinyl (*—CH═CH 2 ) or 1-methylethenyl (*—C(CH 3 )═CH 2 ).

4. The prepolymer of claim 3 , wherein R 15 is a monovalent radical of formula (VIII).

5. The prepolymer of claim 3 , wherein R 15 is a monovalent radical of formula (IX).

6. The prepolymer of claim 3 , wherein R 15 is a monovalent radical of formula (X).

7. The prepolymer of claim 3 , wherein R 15 is a monovalent radical of formula (XI).

8. The prepolymer of claim 3 , wherein R 15 is a monovalent radical of formula (XII).

9. A hydrogel contact lens comprising a crosslinked polymeric material which is a crosslinking and polymerizing product of at least one water-soluble actinically-crosslinkable polyvinyl alcohol prepolymer of claim 1 in the presence or absence of a vinylic monomer and/or a vinylic crosslinking agent, wherein the hydrogel contact lens has: an UVB transmittance of about 10% or less between 280 and 315 nanometers; a UVA transmittance of about 30% or less between 315 and 380 nanometers; optionally a Violet transmittance of about 60% or less between 380 nm and 440 nm; and a water content of from about 15% to about 80% when being fully hydrated.

10. The hydrogel contact lens of claim 9 , wherein R 15 is a monovalent radical of formula (VIII), R 14 is methylene divalent radical, R 11 is hydrogen or C 1 -C 4 alkyl, R 13 is hydrogen, R 12 is a radical of

in which q2 is zero, R 18 is vinyl (*—CH═CH 2 ) or 1-methylethenyl (*—C(CH 3 )═CH 2 ).

11. The hydrogel contact lens of claim 9 , wherein R 15 is a monovalent radical of formula (IX), R 14 is methylene divalent radical, R 11 is hydrogen or C 1 -C 4 alkyl, R 13 is hydrogen, R 12 is a radical of

in which q2 is zero, R 18 is vinyl (*—CH═CH 2 ) or 1-methylethenyl (*—C(CH 3 )═CH 2 ).

12. The hydrogel contact lens of claim 9 , wherein R 15 is a monovalent radical of formula (X), R 14 is methylene divalent radical, R 11 is hydrogen or C 1 -C 4 alkyl, R 13 is hydrogen, R 12 is a radical of

in which q2 is zero, R 18 is vinyl (*—CH═CH 2 ) or 1-methylethenyl (*—C(CH 3 )═CH 2 ).

13. The hydrogel contact lens of claim 9 , wherein R 15 is a monovalent radical of formula (XI), R 14 is methylene divalent radical, R 11 is hydrogen or C 1 -C 4 alkyl, R 13 is hydrogen, R 12 is a radical of

in which q2 is zero, R 18 is vinyl (*—CH═CH 2 ) or 1-methylethenyl (*—C(CH 3 )═CH 2 ).

14. The hydrogel contact lens of claim 9 , wherein R 15 is a monovalent radical of formula (XII), R 14 is methylene divalent radical, R 11 is hydrogen or C 1 -C 4 alkyl, R 13 is hydrogen, R 12 is a radical of

in which q2 is zero, R 18 is vinyl (*—CH═CH 2 ) or 1-methylethenyl (*—C(CH 3 )═CH 2 ).

Assignees

• Novartis Ag

Inventors

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

Classifications

• 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

• G02C7/108

  Colouring materials · CPC title

• C07C225/10

  with doubly-bound oxygen atoms bound to carbon atoms not being part of rings · CPC title

• B29D11/00038 Primary

  Production of contact lenses · CPC title