Contact lens and process for producing same

Patent metadata

Field	Value
Publication number	US-10221273-B2
Application number	US-201515314720-A
Country	US
Kind code	B2
Filing date	May 29, 2015
Priority date	Jun 3, 2014
Publication date	Mar 5, 2019
Grant date	Mar 5, 2019

Abstract

A contact lens is provided as hydrate of a copolymer of at least three components including (I) both terminal-polymerizable silicone oligomer exhibiting viscosity of at least 200 mPa·s at room temperature, (II) a hydrophilic monomer component having ethylenically unsaturated group, and (III) a hydrophobic monomer component having molecular weight of at most 700, wherein the lens exhibits an elastic-modulus ratio determined as ratio of a rupture elastic modulus to an initial elastic modulus in range of 0.8-1.2. The contact lens is transparent and by combination of high oxygen permeability and balance between softness and mechanical properties. The lens is produced through a process including steps of stirring material-liquid including at least three components of the above-mentioned (I), (II) and (III) under stirring power of 5-10000 W/m3 per unit volume of the material-liquid for at least 10 minutes, and injecting stirred material-liquid into a lens mold to polymerize material-liquid.

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 exhibiting a viscosity of at least 200 mPa·s at room temperature, (II) a hydrophilic monomer component having an ethylenically unsaturated group, and (III) a hydrophobic monomer component having a molecular weight of at most 700 g/mol, wherein the contact lens exhibits an initial elastic modulus of 0.1-0.5 N/mm 2 and an elastic-modulus ratio determined as a ratio of a rupture elastic modulus to the initial elastic modulus in a range of 0.8-1.2, and
the contact lens has been produced through a process, comprising: stirring a material liquid comprising said at least three 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 mold to polymerize the material liquid.

2. The contact lens according to claim 1 , exhibiting a rupture modulus of 0.1-0.5 N/mm 2 , and an initial modulus of 0.1-0.5 N/mm 2 .

3. The contact lens according to claim 1 , exhibiting 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).

4. 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 —U 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 S 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′, 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 (I-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 1 and R 2 are the same as denoted above), or a linear 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).

5. 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.

6. 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.

7. The contact lens according to claim 1 , wherein said copolymer is a polymerization product of a monomer mixture containing 0.05-1 wt. part of a crosslinking agent in addition to 100 wt. parts of said components (I)-(III).

8. The contact lens according to claim 1 , comprising: a copolymer forming 1-40 volume % of a hydrophobic region (A) which principally comprises a polymer of the component (I), 0.1-20 volume % of an intermediate region (B) which comprises a copolymer of the components (II) and (III) but does not solvate with any methanol/water mixture solvent, and 40-98.9 volume % of a hydrophilic region (C) which comprises a copolymer of the components (II) and (III).

9. 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 mold to polymerize the material liquid.

10. The process according to claim 9 , wherein said stirring is performed by means of a flat paddle blade.

11. The process according to claim 9 , wherein said material liquid has a viscosity of 0.01-0.40 Pa·s.

12. The process according to claim 9 , wherein said stirring provides a stirring energy of 5-20000 kJ/m 3 to a unit volu

Assignees

• Menicon Co Ltd

Inventors

• Ito Eri
• Yamamoto Katsuhiro

Classifications

• G02B1/043

  Contact lenses · CPC title

• C08F283/12 Primary

  on to polysiloxanes · CPC title

• B29K2083/00

  Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title

• B29D11/00134

  Curing of the contact lens material · CPC title