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Photochromic polydiorganosiloxane vinylic crosslinkers

a polydiorganosiloxane vinylic crosslinker and photochromic technology, applied in the field of photochromic polydiorganosiloxane vinylic crosslinkers, can solve the problems of limited compatibility between known polymerizable photochromic compounds and polymerizable components, limited compatibility, and still susceptible to hydrolysis

Pending Publication Date: 2021-09-16
ALCON INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a photochromic polysiloxane vinoylic crosslinker that is useful in making soft contact lenses. The crosslinker comprises a polydiorganosiloxane segment and two terminal ethylenically-unsaturated groups. The technical effect of this invention is the ability to create soft contact lenses that change color when exposed to light, providing a more comfortable and customizable lens for ophthalmic applications.

Problems solved by technology

However, known polymerizable photochromic compounds have limited compatibility with the polymerizable components, in particular, polymerizable hydrophilic components, in a lens formulation for making silicone hydrogel contact lenses, due to their very bulky and hydrophobic structures.
Such a limited compatibility poses a great challenge in formulating a lens formulation for making optically-clear and photochromic silicone hydrogel contact lenses.
Furthermore, although known polymerizable photochromic compounds are chemically incorporated into the polymer matrix of a silicone hydrogel contact lens, they are still susceptible to hydrolysis, especially when they are located in hydrophilic microscopic regions containing water in a silicone hydrogel contact lens.
Slow hydrolysis could slowly reduce the photochromic capability / property of the silicone hydrogel contact lenses.

Method used

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  • Photochromic polydiorganosiloxane vinylic crosslinkers

Examples

Experimental program
Comparison scheme
Effect test

example 1

Oxygen Permeability Measurements

[0296]Unless specified, the oxygen transmissibility (Dk / t), the intrinsic (or edge-corrected) oxygen permeability (Dki or Dkc) of a lens and a lens material are determined according to procedures described in ISO 18369-4.

Equilibrium Water Content

[0297]The equilibrium water content (EWC) of contact lenses are determined as follows.

[0298]Amount of water (expressed as percent by weight) present in a hydrated hydrogel contact lens, which is fully equilibrated in saline solution, is determined at room temperature. Quickly stack the lenses, and transfer the lens stack to the aluminum pan on the analytical balance after blotting lens in a cloth. The number of lenses for each sample pan is typically five (5). Record the pan plus hydrated weight of the lenses. Cover the pan with aluminum foil. Place pans in a laboratory oven at 100±2° C. to dry for 16-18 hours. Remove pan plus lenses from the oven and cool in a desiccator for at least 30 minutes. Remove a sing...

example 2

[0302]A polydiorganosiloxane vinylic crosslinker having pendant reactive functional groups (e.g., primary amino groups) is prepared according to the procedures shown in Scheme 1

Synthesis of the Precursor

[0303]275.9 g of octamethylcyclotetrasiloxane (M.W. 296.62), 12.0 g of 1,3,5,7-tetramethylcyclotetrasiloxane (M.W. 240.51), 15.3 g of 1,3-bis(3-methacryloxypropyl) tetramethyldisiloxane (M.W. 386.63), and 0.9 g of trifluoromethanesulfonic acid (M.W. 150.08) are weighed into a 500 mL round bottom flask. After the reaction is run at 35° C. for 24 h, 170 mL of 0.5% sodium hydrogen carbonate is added. The collected organic portion is further extracted five times with de-ionized water (170 mL per cycle). Anhydrous MgSO4 is added to the collected organic solution, followed by ˜350 mL of additional CHCl3, and the solution is then stirred overnight. After filtration, the solvent is removed via Rotovap, followed by high vacuum. 102 g of final product (the precursor) is obtained.

Hydrosilylatio...

example 3

[0305]A photochromic polydiorganosiloxane vinylic crosslinker is prepared according to the procedures shown in Scheme 2.

[0306]4.87 g of polydiorganosiloxane vinylic crosslinker with pendant aminopropyl groups (1 eq amine), 2.33 g of 3,3-bis(4-methoxyphenyl)-6,11-dimethyl-13-(2-hydroxycarbonylethyl)carboxyethoxy-13-phenyl-3H,13H-indeno [2′,3′:3,4]naphtho[1,2-b]pyran (5 eq), 0.96 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), 0.76 of N,N-dimethylaminopyridine (DMAP), 50 mL of dichloromethane (DCM) are added into a 500 mL round bottom flask.

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Abstract

The invention provides a class of photochromic polydiorganosiloxane vinylic crosslinkers. Each of the photochromic polydiorganosiloxane vinylic crosslinkers of the invention comprise (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and photochromic siloxane unit having one methyl substituent and one organic substituent having a photochromic moiety that capable of undergoing a reversible color change upon exposure to UV-irradiation or high-energy-violet light; (2) two terminal ethylenically-unsaturated groups. The invention also provides a soft photochromic contact lens, especially a photochromic silicone hydrogel contact lens, which comprises a crosslinked polymeric material comprising repeating units of at least one of such a class of photochromic polydiorganosiloxane vinylic crosslinkers. The invention further provides a method of producing a photochromic contact lens from a polymerizable composition comprising at least one of such a class of photochromic polydiorganosiloxane vinylic crosslinkers.

Description

[0001]This application claims the benefits under 35 USC § 119 (e) of U.S. provisional application No. 62 / 987,925 filed 11 Mar. 2020, incorporated by references in their entireties.[0002]The present invention relates to photochromic polydiorganosiloxane vinylic crosslinkers each having one or more photochromic siloxane units having one methyl substituent and one organic substituent having one photochromic group capable of undergoing a reversible color change upon exposure to UV-irradiation or high-energy-violet light (HEVL) and their uses in making photochromic ophthalmic devices, in particular, photochromic silicone hydrogel contact lenses.BACKGROUND OF THE INVENTION[0003]Conventionally, UV-absorbing compounds have been incorporated into contact lenses to make UV-absorbing contact lenses to protect eyes from UV-radiations. Recently, there have been proposed various photochromic contact lenses for protecting eyes from UV-radiations (see, e.g., U.S. Pat. Nos. 4,681,412, 6,017,121, 6,1...

Claims

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Application Information

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IPC IPC(8): C08F283/12G02B1/04C08G77/06C08G77/442C08L83/12C09K9/02
CPCC08F283/124G02B1/043C08G77/06C08G77/442C09K2211/1088C09K9/02G02B2207/109C08L2312/06C08L83/12C08G77/20C08G77/14C08G77/388C08L83/06C08L83/08G02C7/04G02C7/102C08K5/0041C08L83/04C08G2210/00
Inventor CHANG, YUANGE, JUNHAOZHANG, STEVE YUNLANG, WEIHONG
Owner ALCON INC