Contact lens and process for preparation thereof

• US 4,632,968 A
• Filed: 09/03/1985
• Issued: 12/30/1986
• Est. Priority Date: 01/11/1984
• Status: Expired due to Term

• Current Assignee: Toray Industries Incorporated
• Original Assignee: Toray Industries Incorporated
• Inventors: Yokota, Mitsuru, Goshima, Tsutomu, Fujioka, Shuji
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/776,203
• Time in Patent Office: 483 Days
• Field of Search: 351/160 R, 351/160 H, 264/1.1, 526/279, 528/32, 528/26
• US Class Current: 526/279
• CPC Class Codes: B29D 11/00076 enabling passage of fluids, e.g. oxygen, tears, between the area under the lens and the lens exterior
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/615 containing carboxylic acid groups
• CPC Class Codes: C08G 18/671 Unsaturated compounds having only one group containing active hydrogen takes precedence on groups C08G18/675 - C08G18/69
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/771 oxygen
• CPC Class Codes: C08G 18/8158 with unsaturated compounds having only one group containing active hydrogen
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

Abstract

An oxygen-permeable contact lens consisting essentially of a polymer having an organic polysiloxane skeleton and a three-dimensional crosslinked structure, and a process for the preparation thereof. The polymer comprises structural units comprising (A) a residue of a trifunctional isocyanate, (B) a residue of at least one compound selected from the group consisting of unsaturated carboxylic acids, monoalkyl esters of unsaturated dicarboxylic acid, monoalkyl and dialkyl esters of unsaturated tricarboxylic acids, hydroxyalkyl esters of unsaturated carboxylic acids, acrylamide, methacrylamide, vinyl ethers, and styrene derivatives having an active hydrogen atom, (C) a polydimethylsiloxane residue modified with an active hydrogen-containing functional group, and (D) a residue of at least one compound selected from the group consisting of alkyl esters of acrylic acid, alkyl esters of methacrylic acid, fluorine-containing acrylates, fluorine-containing methacrylates, acrylates and methacrylates having an alicyclic hydrocarbon group, aryl acrylates and methacrylates, halogen-containing aryl acrylates and methacrylates, styrene, styrene derivatives, alkyl esters of unsaturated carboxylic acids.

Claims

1. An oxygen-permeable contact lens consisting essentially of a polymer having an organic polysiloxane skeleton and a three-dimensional crosslinked structure, said polymer comprising structural units comprising (A) a residue represented by the following formula:

##STR14## wherein R₁ and R₂ each stand for an organic residue, (B) a residue connected to residue (A) comprising at least one compound selected from the group consisting of unsaturated carboxylic acids, monoalkyl esters of unsaturated dicarboxylic acids, monoalkyl and dialkyl esters of unsaturated tricarboxylic acids, hydroxyalkyl esters of unsaturated carboxylic acids, acrylamide, methacrylamide, vinyl ethers, and styrene derivatives having an active hydrogen atom, (C) a polydimethylsiloxane residue connected to residue (A) modified with an active hydrogen-containing functional group, which is represented by the following general formula;

##STR15## wherein l and m stand for an integer of 0 to 200, n is an integer of 1 to 200, and R₄ stands for ##STR16##

3. A contact lens as set forth in claim 1, having an oxygen permeability of at least 5×

10^-10 ml·

cm/cm² ·

sec·

cmHg.

4. A contact lens as set forth in claim 1, wherein the component (A) is a residue of a β

-isocyanato-alkyl ester of 2,6-diisocyanato-caproic acid or 1,6,11-undecane triisocyanate.

6. A process according to claim 4, wherein a crosslinking agent which is a monomer having at least two polymerizable double bonds in the molecule is added.

7. A process according to claim 4, wherein the mixing ratio of the components (A), (B) and (C) is such that the ratio of the number of isocyanate groups in the component (A)/the number of active hydrogen-containing functional groups in the component (B)/the number of active hydrogen-containing functional groups in the component (C) is in the range of from 3/2/1 to 3/1/2.

8. A process according to claim 4, wherein the number of active hydrogen-containing functional groups in the component (B) is at least 2/6 of the sum of the number of isocyanate groups in the component (A), the number of active hydrogen-containing functional groups in the component (B) and the number of active hydrogen-containing functional groups in the component (C).

9. A process according to claim 4, wherein the contact lens is obtained by grinding and polishing.

2. in which p is an integer of 1 to 30, q and r stand for an integer of 0 to 30, s is an integer of 1 to 25 and t is an integer of 0 to 30,

copolymerized with (D) a residue of at least one compound selected from the group consisting of alkyl esters of acrylic acid, alkyl esters of methacrylic acid, fluorine-containing acrylates, fluorine-containing methacrylates, acrylates and methacrylates having an alicylic hydrocarbon group, aryl acrylates and methacrylates, halogen-containing aryl acrylates and methacrylates, styrene, styrene derivatives, dialkyl esters of unsaturated dicarboxylic acids and trialkyl esters of tricarboxylic acids wherein unit (A) connects an organic polysiloxane skeleton to a skeleton consisting of the residue of unit (D) through unit (B).

5. A process for the preparation of a contact lens, which comprises addition reacting (A) 1 to 40% by weight of a trifunctional isocyanate represented by the following formula:

##STR17## wherein R₁ and R₂ each stand for an organic residue, (B) 1 to 40% by weight of a monomer having a polymerizable double bond and an active hydrogen atom, (C) 20 to 80% by weight of a polydimethylsiloxane modified with an active hydrogen-containing functional group, which is represented by the following general formula;

##STR18## wherein l an m stand for an integer of 0 to 200, n is an integer of 1 to 200, and R₄ '"'"' stands for ##STR19## in which p is an integer of 1 to 30, q and r stand for an integer of 0 to 30, s is an integer of 1 to 25 and t is an integer of 0 to 30;

and (D) 20 to 80% by weight of a hydrophobic monomer having a polymerizable double bond and having no active hydrogen atom;

wherein components (A), (B), and (C) undergo an addition reaction and components (B) and (D) undergo a vinyl polymerization; and

forming a contact lens from the reaction product.