UV-absorbing vinylic monomers and uses thereof

A hydrogel contact lens, comprising a crosslinked polymeric material which comprises repeating units of a UV-absorbing vinylic monomer of any one of formula (I) to (VII),

• in which:
• RO is H or CH3;
• R1, R2 and R2′ independent of one other are H, CH3, CCl3, CF3, Cl, Br, OH, OCH3, or NR′R″ in which R′ and R″ independent of each other are H or C1-C4 alkyl;
• R1′ independent of each other are H, CH3, CCl3, CF3, Cl, Br, OH, OCH3, SO3H, SO3Na, or NR′R″ in which R′ and R″ independent of each other are H or C1-C4 alkyl;
• R3 and R4 independent of each other are H or a first hydrophilic group which is *—CH2—(OC2H4)n1—OCH3, *—CH2—(OC2H4)n1—OH,
• provided that at least one of R3 and R4 is the first hydrophilic group;
• R5 is H, *—COOH, *—CONH—C2H4—(OC2H4)n1—OCH3 or —CONH—C2H4—(oC2H4)n1—OH;
• one of R6 and R7 is H or a second hydrophilic group which is *—CH2—(O2H4)n1—OCH3,*—CH2—(OC2H4)n1—OH,
• while the other of R6 and R7 is
• R8 is CH3, C2H5,
• R9′ is H, SO3Na,
• R10 is methyl or ethyl;
• L1 is a direct bond or a linkage of
• L2 is a linkage of *—CH2—*,*—C2H4—*,*—C3H6—*, *—C3H6—S—C2H4—*, *—C3H6—S—C3H6—* or
• Y1, Y2, and Y3 independent of one another are a C2-C4 alkylene divalent radical;
• Q1, Q2, and Q3 independent of one another are a (meth)acryloylamido or (meth)acryloyloxy group;
• m1 is zero or 1, provided that if m1 is zero, then Q2 is a (meth)acryloylamido group;
• and
• n1 is an integer of 2 to 20,
• wherein the hydrogel contact lens has:
• an UVB transmittance (designated as UVB % T) of about 10% or less between 280 and 315 nanometers;
• an UVA transmittance (designated as UVA % T) of about 30% or less between 315 and 380 nanometers;
• optionally a Violet transmittance (designated as Violet % T) 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.

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

• (1) obtaining a lens formulation comprising
• (a) from about 0.1% to about 4% by weight of a UV-absorbing vinylic monomer of any one of formula (I) to (VII),
• in which:
• R0 is H or CH3;
• R1, R2 and R2′ independent of one other are H, CH3, CCl3, CF3, Cl, Br, OH, OCH3, or NR′R″ in which R′ and R″ independent of each other are H or C1-C4 alkyl;
• R1′ independent of each other are H, CH3, CCl3, CF3, Cl, Br, OH, OCH3, SO3H, SO3Na, or NR′R″ in which R′ and R″ independent of each other are H or C1-C4 alkyl;
• R3 and R4 independent of each other are H or a first hydrophilic group which is *—CH2—(OC2H4)n1—OCH3, *—CH2—(OC2H4)n1—OH,
• provided that at least one of R3 and R4 is the first hydrophilic group;
• R5 is H, *—COOH, *—CONH—C2H4—(OC2H4)n1—OCH3 or —CONH—C2H4—(OC2H4)n1—OH;
• one of R6 and R7 is H or a second hydrophilic group which is *—CH2—
• while the other of R6 and R7 is
• R8 is CH3, C2H5,
• R9′ is H, SO3Na,
• R10 is methyl or ethyl;
• L1 is a direct bond or a linkage of
• L2 is a linkage of *—CH2—*, *—C2H4—*, *—C3H6—*, *—C3H6—S—C2H4—*, *—C3H6—S—C3H6—* or
• Y1, Y2, and Y3 independent of one another are a C2-C4 alkylene divalent radical;
• Q1, Q2, and Q3 independent of one another are a (meth)acryloylamido or (meth)acryloyloxy group;
• m1 is zero or 1, provided that if m1 is zero, then Q2 is a (meth)acryloylamido group;
• and
• n1 is an integer of 2 to 20,
• (b) from about 0.1% to about 2.0% by weight of at least one free-radical initiator, and
• (c) at least one polymerizable components selected from the group consisting of a hydrophilic vinylic monomer, a water-soluble silicone-free prepolymer, a silicone-containing prepolymer, a non-silicone hydrophobic vinylic monomer, a siloxane-containing vinylic monomer, a siloxane-containing vinylic macromer, a vinylic crosslinking agent, and combinations thereof;
• (2) introducing the lens formulation into a mold for making a soft contact lens, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces;
• and
• (3) curing thermally or actinically the lens formulation in the mold to form the UV-absorbing contact lens, wherein the formed UV-absorbing contact lens is characterized by having a UVB % T of about 10% or less between 280 and 315 nanometers and a UVA % T of about 30% or less between 315 and 380 nanometers and and optionally a Violet % T of about 60% or less between 380 nm and 440 nm.