Soft, high oxygen permeability ophthalmic lens

• US 5,196,458 A
• Filed: 10/15/1991
• Issued: 03/23/1993
• Est. Priority Date: 10/15/1991
• Status: Expired due to Term

• Current Assignee: Johnson & Johnson Vision Products, Inc.
• Original Assignee: Johnson & Johnson Vision Products, Inc.
• Inventors: Nunez, Ivan M., Molock, Frank, Ford, James D.
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): MERRIAM, ANDREW EDWIN
• Application Number:
  US07/777,767
• Time in Patent Office: 525 Days
• Field of Search: 351/160 H, 526/238.23, 523/106, 536/18.3
• US Class Current: 523/106
• CPC Class Codes: C08G 18/4883 containing cyclic groups having at least one oxygen atom in the ring
• CPC Class Codes: C08G 18/8158 with unsaturated compounds having only one group containing active hydrogen
• CPC Class Codes: C08L 75/00 Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A low water contact lens material having high O₂ permeability, a lower water content and reduced polymer matrix size provides adequate O₂ to the cornea, but does not wick water away from the eye nor allow protein or other tear components to penetrate and deposit in the lens. Such a lens is made by polymerizing and crosslinking a prepolymer which contains a cyclic polyol with polyalkylether segments containing curable segments. The cyclic polyols consist of alkoxylated glucose or sucrose which are then reacted with an isocyanate to produce an ultraviolet curable prepolymer. The prepolymer is then placed in a mold and polymerized by exposure to ultraviolet light. The free hydroxyl groups of the material react with a highly hydrophilic reagent to form covalent bonds thus making the surface of the material more wettable.

Claims

1. A soft ophthalmic lens adapted for placement over the cornea or in the eye made from a polymer having repeating units of:

##STR12## where;

R₁ is one of the group consisting of N-aliphatic and branched aliphatic chains having between 1 and 7 carbon atoms,

R₂ =either of the group consisting of CH₃ and H, ##STR13## R₄ =either of the group consisting of O and NH, R₅ =either of the group consisting of H and R₃,

space="preserve" listing-type="equation">a≦

75 for R.sub.2 =CH.sub.3, a≦

225 for R.sub.2 =H

and

space="preserve" listing-type="equation">≦

w+x+y+z≦

50

2. A soft ophthalmic lens adapted for placement over the cornea or in the eye made from a polymer having repeating units of:

##STR14## where;

R₂ =either of the group consisting of CH₃ and H, ##STR15## R₄ =either of the group consisting of O and NH, R₅ =either of the group consisting of H and R₃,

space="preserve" listing-type="equation">a≦

75 R.sub.2 =CH.sub.3, a≦

225 for R.sub.2 =H

and

space="preserve" listing-type="equation">≦

m+p+q+r+s+t+u+v+≦

50

3. A method of making the prepolymer:

##STR16## where;

R₁ is one of the group consisting of N-aliphatic and branched aliphatic chains having between 1 and 7 carbon atoms,

R₂ =either of the group consisting of CH₃ and H,

R₄ =either of the group consisting of O and NH, ##STR17## R₇ =either of the group consisting of H and R₆,

space="preserve" listing-type="equation">a≦

75 for R.sub.2 =CH.sub.3, a≦

225 for R.sub.2 =H

and

space="preserve" listing-type="equation">≦

w+x+y+z≦

50

comprising the steps of;

reacting the high molecular weight, uv curable isocyanate;

##STR18## with the alkoxylated glucose;

##STR19## in the ration from about 1 to 4 molecules of said isocyanate to 1 molecule of said alkoxylated glucose.

5. The method of claim 3 or 4 wherein said high molecular weight, uv curable isocyanate is formed by reacting the intermediate polymer:

##STR24## with a benzo-di isocyanate.

6. The method of claim 5 wherein said intermediate polymer is formed by reacting isocyanoethyl methacrylate:

##STR25## with either of (propoxylated or polypropylene) glycol and the corresponding amine terminated polyglycol;

space="preserve" listing-type="equation">HR.sub.4 (CH.sub.2 CHR.sub.2 O) CH.sub.2 CH.sub.2 R.sub.4 --H

7. The method of claim 3 or 4 wherein said high molecular weight, uv curable isocyanate si formed by reacting hydroxymethylmethacrylate:

##STR26## with toluenediisocyanate;

##STR27## to form;

##STR28## which is then reacted with the intermediate polymer;

##STR29##

8. The method of claim 3 or 4 wherein said high molecular weight, uv curable isocyanate is formed by reacting hydroxymethylmethacrylate:

##STR30## with isophorone diisocyanate;

##STR31## to form;

##STR32## which is then reacted with the intermediate polymer;

##STR33##

9. The method of claim 3 or claim 4 wherein said method is for making a soft ophthalmic lens for placement on the cornea or in the eye, further comprising the additional steps of:

mixing said prepolymer with a diluent,

placing said prepolymer/diluent mixture into a lens mold, at least one surface of said mold containing a non-zero optical power,

polymerizing said prepolymer into a contact lens by impinging said mixture with energy sufficient to cause polymerization,

removing the polymerized lens from said mold, and

hydrating the lens by displacing the diluent with water.

4. A method of making the prepolymer:

##STR20## where;

R₂ =either of the group consisting of CH₃ and H, ##STR21## R₄ =either the group consisting of O and NH, R₇ =either of the group consisting of H and R₆,

space="preserve" listing-type="equation">a≦

75 for R.sub.5 =CH.sub.3, ≦

225 for R.sub.5 =H

and

space="preserve" listing-type="equation">≦

m+p+q+r+s+t+u+v≦

50

comprising the step of;

reacting the high molecular weight, uv curable isocyanate;

##STR22## with the alkoxylated sucrose;

##STR23## in the ratio of from about 1 to 8 molecules of said isocyanate to 1 molecule of said alkoxylated sucrose.

10. The prepolymer:

##STR34## where;

R₁ is one of the group consisting of N-aliphatic and branched aliphatic chains having between 1 and 7 carbon atoms.

R₂ =either of the group consisting of CH₃ and H, ##STR35## R₄ =either the group consisting of O and NH, R₇ =either of the group consisting of H and R₆,

space="preserve" listing-type="equation">a≦

75 for R.sub.2 =CH.sub.3, ≦

225 for R.sub.2 =H

and

space="preserve" listing-type="equation">≦

w+x+y+z+≦

50

11. The prepolymer:

##STR36## where;

R₂ =either of the group consisting of CH₃ and H, ##STR37## R₄ =either the group consisting of O and NH, R₇ =either of the group consisting of H and R₆,

space="preserve" listing-type="equation">a≦

75 for R.sub.5 =CH.sub.3, ≦

225 for R.sub.5 =H

and

space="preserve" listing-type="equation">≦

m+p+q+r+s+t+u+v≦

50