Wettable silicone hydrogel contact lenses

Patent metadata

Field	Value
Publication number	US-11513257-B2
Application number	US-202017122109-A
Country	US
Kind code	B2
Filing date	Dec 15, 2020
Priority date	Dec 16, 2019
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The invention relates to an ophthalmic product which comprises a sealed and autoclave-sterilized lens package including (1) a post-autoclave packaging solution containing a polymeric surfactant having an HLB value of from about 11 to about 16 and a Mn of from about 800 to about 20,000 Daltons and (2) a readily-usable silicone hydrogel (SiHy) contact lens immersed in the packaging solution. The readily-usable SiHy contact lens comprises the polymeric surfactant thereon providing an excellent wettability to the readily-usable SiHy contact lens directly out of the lens package, and also the leachable polymeric surfactant which is physically distributed in the polymer matrix of the SiHy contact lens and can be released to the eye of a patient for at least 7 days of daily wear and to replenish the lens surface-bound polymeric surfactant to provide sustainable wettabilities to the contact lens and the eye.

First claim

What is claimed is:

1. An ophthalmic product, comprising a sealed and autoclave-sterilized package which include a post-autoclave packaging solution and a readily-usable silicone hydrogel contact lens immersed therein,
wherein the post-autoclave packaging solution is a buffered saline having a pH of from about 6.0 to about 8.0 and includes a polymeric surfactant which comprises at least one hydrophilic poly(oxyethylene) segment and at least one hydrophobic poly(oxybutylene) segment and has an HLB value of from about 11 to about 16 and a number average molecular weight of from about 800 to about 20,000 Daltons, wherein the readily-usable silicone hydrogel contact lens is obtained by placing, sealing and autoclaving a pre-formed silicone hydrogel contact lens in a pre-autoclave packaging solution including the polymeric surfactant in a package, wherein the pre-formed silicone hydrogel contact lens is free of any coating thereon, wherein the readily-usable silicone hydrogel contact lens comprises the polymeric surfactant physically distributed in the polymer matrix of the readily-usable silicone hydrogel contact lens as evidenced by having a capability of releasing the polymeric surfactant in an amount of at least 0.2 μg/lens/24 hours as measured in an aqueous extraction process consisting of 7 cycles of simulated 1-day-wearing extraction, wherein the capacity of releasing the polymeric surfactant is the amount of the polymeric surfactant released per lens over 24 hours into an extraction medium which has been used in the last cycle of the 7 cycles of the simulated 1-day-wearing extraction, wherein the readily-usable silicone hydrogel contact lens further has a first static water contact angle, WCA OOP , of about 75° or less as measured directly out of the sealed package by sessile drop method, a second static water contact angle, WCA 7_S1DW , of about 85° or less as measured by sessile drop method immediately after being subjected to the 7 cycles of the simulated 1-day-wearing extraction, an oxygen permeability of at least 50 barrers, an elastic modulus of from about 0.2 MPa to about 1.5 MPa, and an equilibrium water content of from about 38% to about 80% by weight.

2. The ophthalmic product of claim 1 , wherein the readily-usable silicone hydrogel contact lens has a capability of releasing the polymeric surfactant in an amount of at least 0.4 μg/lens/24 hours as measured in the aqueous extraction process consisting of the 7 cycles of the simulated 1-day-wearing extraction.

3. The ophthalmic product of claim 1 , wherein the polymeric surfactant is a di-block copolymer designated as PEO-PBO or a tri-block copolymer designated as PEO-PBO-PEO or PBO-PEO-PBO, in which PEO represents poly(oxyethylene) segment and PBO represents poly(oxybutylene) segment.

4. The ophthalmic product of claim 1 , wherein the polymeric surfactant is a di-block copolymer of formula (S1)
RO-(EO) m (BO) n —H  (S1)

wherein: R is selected from the group consisting of hydrogen, methyl, ethyl, propyl and butyl; EO is ethyleneoxide —C 2 H 4 O—; BO is butyleneoxide —C 4 H 8 O—; m is an integer having an average value of 10 to 250; and n is an integer having an average value of 5 to 125, provided that the value of m/n is from about 2:1 to about 10:1.

5. The ophthalmic product of claim 1 , wherein the polymeric surfactant is a di-block copolymer of formula (S2)

wherein R is selected from the group consisting of hydrogen, methyl, ethyl, propyl and butyl; m is an integer having an average value of 10 to 250; and n is an integer having an average value of 5 to 125, provided that the value of m/n is from about 2:1 to about 10:1.

6. The ophthalmic product of claim 5 , wherein the readily-usable silicone hydrogel contact lens comprises at least about 40 μg/lens of the polymeric surfactant.

7. The ophthalmic product of claim 5 , wherein the pre-autoclave packaging solution further comprises from about 0.1% to about 2% by weight of a hydrophilic polymer having a number average molecular weight of at least 100,000 Daltons.

8. The ophthalmic product of claim 1 , wherein the pre-autoclave packaging solution further comprises from about 0.1% to about 2% by weight of a hydrophilic polymer having a number average molecular weight of at least 100,000 Daltons.

9. The ophthalmic product of claim 8 , wherein the hydrophilic polymer is a polyvinylpyrrolidone or a copolymer of N-vinylpyrrolidone and at least one amino-containing vinylic monomer, wherein the amino-containing vinylic monomer is selected from the group consisting of alkylaminoalkylmethacrylate having 8-15 carbon atoms, alkylaminoalkylacrylate having 7-15 carbon atoms, dialkylaminoalkylmethacrylate having 8-20 carbon atoms, dialkylaminoalkylacrylate having 7-20 carbon atoms, and N-vinylalkylamide having 3-10 carbon atoms.

10. The ophthalmic product of claim 9 , wherein the pre-formed silicone hydrogel contact lens is an inherently wettable silicone hydrogel contact lens.

11. The ophthalmic product of claim 9 , wherein the pre-formed silicone hydrogel contact lens is composed of a silicone hydrogel material comprising (1) repeating units of at least one silicone-containing vinylic monomer and/or repeating units of at least one polysiloxane vinylic crosslinker, and (2) repeating units of at least one hydrophilic vinylic monomer, wherein said at least one silicone-containing vinylic monomer is selected from the group consisting of a vinylic monomer having a bis(trialkylsilyloxy)alkylsilyl group, a vinylic monomer having a tris(trialkylsilyloxy)silyl group, a polysiloxane vinylic monomer, 3-methacryloxy propylpentamethyldisiloxane, t-butyldimethyl-siloxyethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, and trimethylsilylmethyl vinyl carbonate, and combinations thereof.

12. The ophthalmic product of claim 11 , wherein the silicone hydrogel material comprises repeating units of at least one polysiloxane vinylic crosslinker, wherein said at least one polysiloxane vinylic crosslinker comprises a vinylic crosslinker of formula (I)

in which:
υ1 is an integer of from 30 to 500 and ω1 is an integer of from 1 to 75, provided that ω1/υ1 is from about 0.035 to about 0.15;
X 01 is O or NR N in which R N is hydrogen or C 1 -C 10 -alkyl;
R o is hydrogen or methyl;
R I1 and R I2 independently of each other are a substituted or unsubstituted C 1 -C 10 alkylene divalent radical or a divalent radical of —R I4 —O—R I5 — in which R I4 and R I5 independently of each other are a substituted or unsubstituted C 1 -C 10 alkylene divalent radical;
R I3 is a monovalent radical of any one of formula (Ia) to (Ie)

p1 is zero or 1; m1 is an integer of 2 to 4; m2 is an integer of 1 to 5; m3 is an integer of 3 to 6; m4 is an integer of 2 to 5;
R I6 is hydrogen or methyl;
R I7 is a C 2 -C 6 hydrocarbon radical having (m2+1) valencies;
R I8 is a C 2 -C 6 hydrocarbon radical having (m4+1) valencies;
R I9 is ethyl or hydroxymethyl;
R I10 is methyl or hydromethyl;
R I11 is hydroxyl or methoxy;
X I1 is a sulfur linkage of —S— or a teriary amino linkage of —NR I12 — in which R I12 is C 1 -C 1 alkyl, hydroxyethyl, hydroxypropyl, or 2,3-dihydroxypropyl; and
X I2 is an amide linkage of

Assignees

• Alcon Inc

Inventors

• Zheng Ying
• Chiou Jang-Shing
• Dou Jinbo
• Chang Yuan
• Ge Junhao
• Zhang Steve Yun
• Yao Li
• Sentell Karen Belinda
• Hong Ye

Classifications

• C08L39/06

  Homopolymers or copolymers of N-vinyl-pyrrolidones · CPC title

• B29D11/00067 Primary

  Hydrating contact lenses · CPC title

• B29K2059/00

  Use of polyacetals {, e.g. POM, i.e. polyoxymethylene or derivatives thereof}, as moulding material · CPC title

• G02C7/04

  Contact lenses for the eyes (disinfection or sterilisation of contact lenses A61L12/00) · CPC title

• B29K2105/0061

  Gel or sol · CPC title