Contact lens and process for producing same

Patent metadata

Field	Value
Publication number	US-10183452-B2
Application number	US-201515314677-A
Country	US
Kind code	B2
Filing date	May 29, 2015
Priority date	Jun 3, 2014
Publication date	Jan 22, 2019
Grant date	Jan 22, 2019

Abstract

A contact lens is provided as a hydrate of a copolymer of at least three components including (I) a both terminal-polymerizable silicone oligomer component that forms a hydrophobic region (A) in the copolymer, (II) a hydrophilic component that forms a hydrophilic region (C) in the copolymer, and (III) a hydrophobic monomer component having a molecular weight of at most 700 that forms the hydrophilic region (C) together with the component (II) and also contributes to form an intermediate region (B) which does not solvate with a hydrophilic solvent between the hydrophobic region (A) and hydrophilic region (C), wherein the intermediate region (B) shows a volume rate of 5 to 40% with respect to the region (A) in the copolymer, and the contact lens is transparent and free from bubbles therein.

First claim

The invention claimed is:

1. A contact lens, comprising: a hydrate of a copolymer of at least three components including (I) a both terminal-polymerizable silicone oligomer component that forms a hydrophobic region (A) in the copolymer, (II) a hydrophilic monomer component that forms a hydrophilic region (C) in the copolymer, and (III) a hydrophobic monomer component having a molecular weight of at most 700 g/mol that forms the hydrophilic region (C) together with the component (II) and also contributes to formation of an intermediate region (B) which does not solvate with any methanol/water mixture solvent between the hydrophobic region (A) and the hydrophilic region (C), wherein said intermediate region (B) shows a volume rate of 5 to 40% with respect to the region (A) in the copolymer, and the contact lens is free from turbidity and bubbles therein by observation with eyes and exhibits an initial modulus of 0.1-0.5 N/mm 2 .

2. The contact lens according to claim 1 , comprising a hydrate of the copolymer which comprises 1 to 40% of the region (A), 0.1 to 20% of the region (B) and 40 to 98.9% of the region (C), respectively on a volume basis.

3. The contact lens according to claim 1 , wherein said both terminal-polymerizable silicone oligomer component (I) is a both terminal-polymerizable macro-monomer having a siloxane structure denoted by a general formula (I-1) or a general formula (I-2) as shown below, and shows a viscosity of at least 200 mPa-s at room temperature:
general formula (I-1):
A 1 -(U 1 —S 1 —) n Y 2 —S 2 —U 3 -A 2   (I-1),

[wherein A 1 and A 2 each independently denote an active unsaturated group which has an active unsaturated polymerizable terminal group, an alkylene group of 1-20 carbon atoms, or an alkylene glycol group of 1-20 carbon atoms,
U 1 denotes a diurethane unit which forms a urethane bond, a diurea unit which forms a urea bond, a diamide unit which forms an amide bond, or a diester unit which forms an ester bond, respectively, together with A 1 and S 1 or S 1 and S 1 , neighboring on both sides thereof,
U 2 denotes a diurethane unit which forms a urethane bond, a diurea unit which forms a urea bond, a diamide unit which forms an amide bond, or a diester unit which forms an ester bond, respectively, together with A 1 and S 2 or S 1 and 5 2 , neighboring on both sides thereof,
U 3 denotes a diurethane unit which forms a urethane bond, a diurea unit which forms a urea bond, a diamide unit which forms an amide bond, or a diester unit which forms an ester bond, respectively, together with S 2 and A 2 , neighboring on both sides thereof,
S 1 and S 2 each independently denote a group represented by:

(wherein R 1 and R 2 each independently denote an alkylene group of 1-20 carbon atoms, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each independently denote a linear, branched or cyclic alkyl group of 1-20 carbon atoms capable of being substituted by a fluorine atom, a group represented by a formula: A 3 -U 4 —R 1 —O—R 2 — (wherein A 3 denotes a terminal-polymerizable active unsaturated group, a terminal-polymerizable active unsaturated group having an alkylene group of 1-20 carbon atoms, or a terminal-polymerizable active unsaturated group having an alkylene glycol group of 1-20 carbon atoms, U 4 denotes a diurethane unit which forms a urethane bond, a diurea unit which forms a urea bond, a diamide unit which forms an amide bond, or a diester unit which forms an ester bond, respectively together with A 3 and R 1 , and R 1 and R 2 are the same as denoted above), or a linear or cyclic hydrocarbon group having at least one substituent selected from hydroxyl group and oxyalkylene group,
x denotes an integer of 1-1500, y denotes o or an integer of 0-1499, z denotes 0 or an integer of 1-1499, and x+y+z makes an integer of 1-1500),
n denotes 0 or an integer of 1-10];
B 1 —S 3 —B 1   General formula (1-2):

[wherein B 1 denotes a terminal-polymerizable active unsaturated unit having a urethane bond, a urea bond, an amide bond, or an ester bond,
S 3 denotes a group represented by:

(wherein R 1 and R 2 each independently denote an alkylene group of 1-20 carbon atoms, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 each independently denote a linear, branched or cyclic alkyl group of 1-20 carbon atoms 1-20 capable of being substituted by a fluorine atom, a group represented by a formula: A 3 -U 4 —R 1 —O—R 2 — (wherein A 3 denotes a terminal-polymerizable active unsaturated unit, a terminal-polymerizable active unsaturated unit having an alkylene group of 1-20 carbon atoms, or a terminal-polymerizable active unsaturated unit having an alkylene glycol group of 1-20 carbon atoms, U 4 denotes a diurethane unit which forms a urethane bond, a diurea unit which forms a urea bond, a diamide unit which forms an amide bond, or a diester unit which forms an ester bond, respectively together with A 3 and R 1 , and R 2 are the same as denoted above), or a linear or cyclic hydrocarbon group having at least one substituent selected from hydroxyl group and oxyalkylene group,
x denotes an integer of 1-1500, y denotes 0 or an integer of 1-1499, z denotes 0 or an integer of 1-1499, and x+y+z makes an integer of 1-1500).

4. The contact lens according to claim 1 , wherein said hydrophilic monomer component (II) is a hydrophilic monomer selected from the group consisting of 1-alkyl-3-methylene-2-pyrroridones, N-substituted acrylamides, N-vinyl lactams, hydroxyalkyl (meth)acrylates, (alkyl)amino-alkyl (meth)acrylates, alkylene glycol mono-(meth)acrylates, and (meth)acrylic acid.

5. The contact lens according to claim 1 , wherein said hydrophobic monomer component (III) having a molecular weight of at most 700 is selected from the group consisting of silicone-containing alkyl (meth)acrylates, alkyl (meth)acrylates, and fluorine-containing alkyl (meth)acrylates.

6. The contact lens according to claim 1 , wherein said copolymer is a polymerization product of a monomer mixture including 1-40 wt. % of the component (I), 10-60 wt. % of the component (II) and 10-45 wt. % of component (III) (the above wt. % values being based on total amount of the components (I)-(III)), and also 0.05-1 wt. part of a crosslinking agent in addition to 100 wt. parts in total of said components (I)-(III).

7. The contact lens according to claim 6 , wherein said copolymer is a polymerization product of a monomer mixture including 2-35 wt. % of the component (I), 20-50 wt. % of the component (II) and 15-40 wt. % of component (III) (the above wt. % values being based on total amount of the components (I)-(III)), and also 0.1-0.8 wt. part of a crosslinking agent in addition to 100 wt. parts in total of said components (I)-(III).

8. The contact lens according to claim 6 , exhibiting an oxygen permeability coefficient Dk of at least 87×10 −11 (cm 2 /sec)·(mL O 2 /mL×mmHg).

9. The contact lens according to claim 1 , exhibiting a rupture modulus of 0.1-0.5 N/mm 2 , a stress relaxation coefficient of 8 to 25%, and an oxygen permeability coefficient Dk of at least 56×10 −11 (cm 2 /sec)·(mL O 2 /mL×mmHg).

10. A process for producing a contact lens according to claim 1 , comprising: stirring a material liquid comprising at least three components of said components (I), (II) and (III) under a stirring power of 5-10000 W/m 3 per unit volume of the material liquid for at least 10 minutes, and then injecting the stirred material liquid into a lens mo

Assignees

• Menicon Co Ltd

Inventors

• Ito Eri
• Yamamoto Katsuhiro

Classifications

• B29D11/00038

  Production of contact lenses · CPC title

• B29D11/00067 Primary

  Hydrating contact lenses · CPC title

• C08F220/10

  Esters · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• C08F290/068 Primary

  Polysiloxanes · CPC title