Silicone hydrogel contact lenses and method for manufacturing the same

Patent metadata

Field	Value
Publication number	US-11198751-B2
Application number	US-202016999036-A
Country	US
Kind code	B2
Filing date	Aug 20, 2020
Priority date	May 25, 2017
Publication date	Dec 14, 2021
Grant date	Dec 14, 2021

Abstract

The present invention provides a water-soluble silicone macromer. The water-soluble silicone macromer has a general formula: E−(M 1 ) x −(M 2 ) y , wherein M 1 is a repeating unit which is derived from a silicone containing monomer, M 2 is a repeating unit which is derived from a first hydrophilic monomer, and E is an ethylenically unsaturated group. The amount of M 1 is in a range of 30-60 wt % based on the total weight of the water-soluble silicone macromer, and the amount of M 2 is in a range of 40-70 wt % based on the total weight of the water-soluble silicone macromer. A silicone hydrogel composition containing the water-soluble silicone macromer and a silicone hydrogel lens made of the silicone hydrogel composition are also provided herein.

First claim

What is claimed is:

1. A silicone hydrogel contact lens made by crosslinking and curing a silicone hydrogel composition, wherein the silicone hydrogel composition comprises:
a water-soluble silicone macromer in the amount of 50-80 wt % based on the total weight of the silicone hydrogel composition, wherein the water-soluble silicone macromer has a structure presented by formula (1) below:
E−(M 1 ) x −(M 2 ) y   formula (1);

wherein M 1 is a repeating unit comprises

or a combination thereof, wherein formula (8) and formula (9) has a number-averaged molecular weight of less than 1500, p is an integer of 0-4, q is 0 or 1, k is an integer of 4-20, and R 2 is C1-C10 alkyl group;
M 2 is a repeating unit comprises

of molecular weight less than 1000, or a combination thereof, wherein a is an integer of 1-21, and a weight ratio of (M 1 ) x to (M 2 ) y is from 30:70 to 50:50;
E is a terminal group comprises

wherein a symbol “*” in formula (20)-(23) indicates a position to be linked to M 1 ;
x is an integer of 1-20;
y is an integer of 1-20;
a number-average molecular weight (Mn) of the water-soluble silicone macromer ranges from 2000 to 5000; and
an aqueous solution composed of 0.5 wt % of the water-soluble silicone macromer and water has a light transmittance of greater than 20% at a wavelength of 450 nm;
a hydrophilic monomer in the amount of 19-50 wt % based on the total weight of the silicone hydrogel composition;
a crosslinker in the amount of 0.1-1.5 wt % based on the total weight of the silicone hydrogel composition;
an initiator in the amount of 0.1-1 wt % based on the total weight of the silicone hydrogel composition; and
an organic solvent.

2. The silicone hydrogel contact lens of claim 1 , wherein the silicone hydrogel contact lens has a water content of 52-72% and an oxygen permeability of 50-75 DK.

3. A silicone hydrogel contact lens, which is made of a water-soluble silicone macromer of claim 1 using a photo curing process, and after the photo curing process, the silicone hydrogel contact lens is free of extraction using organic solvent.

4. A method for manufacturing silicone hydrogel contact lenses, comprising:
providing the silicone hydrogel composition of claim 1 ;
crosslinking and a curing the silicone hydrogel composition to form a silicone hydrogel contact lens; and
extracting an uncured portion of the water-soluble silicone macromer in the silicone hydrogel contact lens using a liquid comprising water to remove the uncured portion of the water-soluble silicone macromer.

5. The method of claim 4 , wherein the liquid comprising water further comprises a surfactant having a hydrophilic-lipophilic balance between 13 and 17.

Assignees

• Pegavision Corp

Inventors

• Lai Yu-Chin
• Kuan Ting-Chun
• Kung Hsiang-Ho
• Yeh Min-Tzung
• Yang Ching-Wen
• Hsu Tsung-Kao

Classifications

• C08F2/38

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C08F290/068

  Polysiloxanes · CPC title

• C08F230/08

  containing silicon · CPC title

• C08F290/046 Primary

  Polymers of unsaturated carboxylic acids or derivatives thereof · CPC title

• C08G18/8116

  esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group · CPC title