UV/visible-absorbing vinylic monomers and uses thereof

• US 10,268,053 B2
• Filed: 02/16/2017
• Issued: 04/23/2019
• Est. Priority Date: 02/22/2016
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Holland, Troy Vernon, Chang, Frank, Laredo, Walter R., Jiang, Xuwei, DeSousa, Ryan
• Primary Examiner(s): Pepitone, Michael F
• Application Number:
  US15/434,098
• Publication Number:
  US 20170242274A1
• Time in Patent Office: 796 Days
• CPC Class Codes: C07C 225/22 having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 233/33 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 237/32 having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
• CPC Class Codes: C07C 237/34 having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures
• CPC Class Codes: G02C 7/108 Colouring materials

Abstract

Described herein are UV-absorbing vinylic monomers and their uses in preparing UV-absorbing contact lenses capable of blocking ultra-violet (“UV”) radiation and 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.

Claims

1. A UV-absorbing vinylic monomer, being selected from the group consisting of:

2. A contact lens comprising a crosslinked material which comprises monomeric units of a UV-absorbing vinylic monomer selected from the group consisting of:

3. The contact lens of claim 2, wherein the contact lens is a hydrogel contact lens.

4. The contact lens of claim 2, wherein the contact lens is a silicone hydrogel contact lens.

5. The contact lens of claim 2, wherein the 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;

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% by weight (at room temperature, about 22°

C. to 28°

C.) when being fully hydrated.

6. A method for producing UV-absorbing contact lenses, comprising the steps of:

(1) obtaining a lens formulation comprising

(a) a UV-absorbing vinylic monomer selected from the group consisting of

7. The method of claim 6, wherein the free-radical initiator is a thermal initiator, wherein the step of curing is carried out thermally.

8. The method of claim 6, wherein the free-radical initiator is a photoinitiator, wherein the step of curing is carried out by irradiation with a light having a wavelength within the range from 380 nm to 500 nm.

9. The method of claim 8, wherein the mold is a reusable mold, wherein the step of curing is carried out under a spatial limitation of radiation.