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Patent Searching and Data


Title:
SELECTIVELY WETTABLE AND OXYGEN-PERMEABLE LENSES
Document Type and Number:
WIPO Patent Application WO/2020/112030
Kind Code:
A4
Abstract:
A contact lens includes a body, having the plurality of monomers including at least some silicone monomer units including at least one zwitterionic distributed throughout the body. The contact lens includes a front surface and a back surface, where the silicone monomer including at least one zwitterionic group can be present in a greater concentration nearest the front surface than the back surface or a point therebetween. The contact lens can be formed by casting a polymer mixture containing the silicone monomer including at least one zwitterionic group.

Inventors:
NEWMAN STEPHEN D (SG)
WATANABE TASUKU (SG)
Application Number:
PCT/SG2019/050592
Publication Date:
July 23, 2020
Filing Date:
November 30, 2019
Export Citation:
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Assignee:
MENICON SINGAPORE PTE LTD (SG)
International Classes:
C08F30/08; G02C7/04
Attorney, Agent or Firm:
INFINITUS LAW CORPORATION (SG)
Download PDF:
Claims:
AMENDED CLAIMS

received by the International Bureau on 25 May 2020 (25.05.2020)

1. A composition comprising:

at least one silicon containing monomer;

wherein the silicon containing monomer includes at least one zwitterionic group; wherein the composition includes an acrylate or methacrylate salt; and wherein the composition is 0.1-9 wt% silicone.

2. The composition according to claim 1, wherein the silicon containing monomer has a single zwitterionic group.

3. The composition according to claim 1 or 2, wherein the zwitterionic group comprises one of a phosphorylcholine, alkyl carbobetaine, alkylamide carbobetaine, alkyl sulfobetaine, alkylhydroxy sulfobetaine, alkylamide sulfobetaine, alkylamidehydroxy sulfobetaine and thereof.

4. The composition according to any one of claims 1 to 3, wherein the relaxation rate of the composition is less than 5.5%.

5. The composition according to claim 4, wherein the relaxation rate is less than 4.0%.

6. The composition according to any one of claims 1-3, wherein the dynamic friction of the composition comprises less than 50 mN.

7. The composition according to claim 6, wherein the dynamic friction comprises less than 40 mN.

38

8. The composition according to any one of claims 1-7, wherein the silicon containing monomer comprises isomers conforming to formulae (la) to (Ic):

(la) (lb) (Ic)

wherein:

R1 is a group containing a polymerizable moiety comprising, but not limited to, methacryloyl, acryloyl, styryl, or allyl;

R2 is a group containing a Cl -Cl 5 alkenyl group terminated in a silicone moiety of structure (II), where R4 is either -CH3 or -[-Si(CH3)2-0-]n-Si(CH3)3 where n=0-50;

R3 is a zwitterionic group, including, but not limited to phosphorylcholine, betaine, sulfobetaine, or amphoacetate.

9. The composition according to claim 8, wherein the composition includes between 0 and 10 wt% of a non-silicone monomer containing phosphorylcholine.

10. An ophthalmic lens, comprising:

a body including:

a hydrogel polymer formed from a composition including a plurality of monomers, the plurality of monomers including a silicon containing monomer including at least one zwitterionic group distributed throughout the body; a front surface configured to face away from a wearer;

a back surface configured to contact an eye of the wearer; and

a greater amount of silicon containing monomer including at least one zwitterionic group at the front surface than at a point in the body between the front surface and the back surface.

11. The ophthalmic lens of claim 10, wherein:

a total silicone ratio of the hydrogel polymer is 0.1-9 wt%; and

the hydrogel polymer further comprises a methacrylate salt.

12. The ophthalmic lens of claim 10 or 11, wherein the relaxation rate is less than 5.5%.

13. The ophthalmic lens of claim 10 or 11, wherein the dynamic friction comprises less than 50 mN.

14. The ophthalmic lens of claim 10 or 11, wherein:

the silicon containing monomer including at least one zwitterionic group comprises one of SiGMA-PC or SiMA-PC; and

the hydrogel polymer further comprises sodium methacrylate.

15. The ophthalmic lens of claim 14, wherein the plurality of monomers comprises one or more of glyceryl methacrylate, (hydroxyethyl)methacrylate, 2-(4-Benzoyl-3- hydroxyphenoxy)ethyl acrylate, ethylene glycol dimethacrylate, benzoin methyl ether, or a combination of any of the foregoing.

16. The ophthalmic lens of claim 15, wherein the SiGMA-PC monomer is about 0.5 to about 15 weight percent (wt%) of the hydrogel polymer, glyceryl methacrylate is about 10 wt% to about 50 wt% of the hydrogel polymer, and the 2-hydroxyethyl methacrylate is about 20 wt% to about 80 wt% of the hydrogel polymer.

17. The ophthalmic lens of claim 14, wherein:

the body has a larger concentration of SiGMA-PC or SiMA-PC at the front surface than at the back surface;

the lens includes an oxygen transmissibility value (Dk/thickness) greater than 20; and

the lens exhibits a Young’s modulus of about 0.1 MPa to about 0.5 MPa.

18. A method of making a contact lens, comprising:

applying a liquid lens material into a mold; and

curing the liquid lens material in the mold;

wherein the liquid lens material includes a plurality of monomers, the plurality of monomers including at least some 3,5,8,13-tetraoxa-4-phospha-12,14-disilapentadecan- 1-aminium, 4-hydroxy-N,N,N, 12,14, 14-hexamethy l-6-[[(2-methyl- l-oxo-2-propen-l- yl)oxy]methyl]-12-[(trimethylsilyl)oxy]-, inner salt, 4-oxide (“SiGMA-PC”) monomer units.

19. The method of claim 18, wherein the mold comprises a spin-cast mold; and

curing the liquid material comprises spinning the liquid lens material while at least partially curing the liquid lens material.

20. The method of claim 18, wherein the mold comprises a cast mold.