Ophthalmic lens

Patent metadata

Field	Value
Publication number	US-9657131-B2
Application number	US-201615177781-A
Country	US
Kind code	B2
Filing date	Jun 9, 2016
Priority date	Dec 16, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

An ophthalmic lens which gives excellent wearing comfort required for its use as a contact lens, and which has sufficiently high flexibility and an adequate degree of deformation recovery property required for its use as an intraocular lens. The ophthalmic lens is formed of a polymer having a young's modulus of 0.3-1.0 MPa and a stress relaxation rate of 10-20%.

First claim

The invention claimed is:

1. An ophthalmic lens formed of a polymer having a young's modulus of 0.3-1.0MPa and a stress relaxation rate of 10-20%, where the polymer is obtained from a polymerizable composition including a polysiloxane-based macromonomer having at least one polymerizable group and a polysiloxane chain having a siloxane unit as a repeating unit, wherein
the polysiloxane-based macromonomer has:
a polyoxyethylene chain having an oxyethylene group as a repeating unit, wherein a number of repetition of the oxyethylene group is “a”, and “a” is an integer not smaller than two, and
a polyoxyalkylene chain having an oxyalkylene group other than the oxyethylene group as a repeating unit, wherein a number of repetition of the oxyalkylene group is “b”, and “b” is an integer not smaller than two; and

the polysiloxane-based macromonomer has a value β calculated according to the following formula (B) being held within a range from 0.5 to 5.0:
β= n/ (“ a”+“b ”)  (B)

where
n represents a total number of Si atoms in a molecule of the polysiloxane-based macromonomer; wherein

the at least one polymerizable group is bonded to the polysiloxane chain constituting a main chain of a molecule of the polysiloxane-based macromonomer, through at least one urethane bond.

2. The ophthalmic lens according to claim 1 , wherein a value αcalculated according to the following formula (A) is held within a range from 0.02 to 0.10:
α= E/r   (A)

wherein E represents the young's modulus (MPa) of the polymer of the ophthalmic lens, and r represents the stress relaxation rate (%) of the polymer.

3. The ophthalmic lens according to claim 1 , wherein an HLB value of the polysiloxane-based macromonomer calculated according to the following formula (C) is held within a range from 0.7 to 6.0:
[HLB value]= W E /5  (C)

wherein W E represents a weight fraction (wt %) of the oxyethylene group in the molecule of the polysiloxane-based macromonomer.

4. The ophthalmic lens according to claim l wherein the number “a” of repetition of the oxyethylene group is within a range from 4 to 15.

5. The ophthalmic lens according to claim 1 , wherein the polyoxyalkylene chain is a polyoxypropylene chain having an oxypropylene group as a constituent unit.

6. The ophthalmic lens according to claim 5 , wherein a number of repetition of the oxypropylene group is within a range from 5 to 16.

7. The ophthalmic lens according to claim 1 , wherein the polysiloxane chain, the polyoxyethylene chain and the polyoxyalkylene chain constitute a main chain of the molecule of the polysiloxane-based macromonomer.

8. The ophthalmic lens according to claim 1 , wherein the polysiloxane-based macromonomer is represented by the following general formula (I):
A 1 -Z 1 —U 1 —Z 2 —Z 3 —(—S 1 —U 2 —) n —S 2 —Z 4 —Z 5 —U 3 —Z 6 -A 2   (I)

where
n is 0 or an integer within the range from 1 to 10;
A 1 is a group represented by a general formula (II):
Y 21 —R 21 —  (II)

where
Y 21 represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group, independently of each other, and
R 21 represents a direct bond or a linear or branched alkylene group having 2 to 6 carbon atoms, independently of each other;

A 2 is a group represented by a general formula (III):
—R 22 —Y 22   (III)

where
Y 22 represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group, independently of each other, and
R 22 represents a direct bond or a linear or branched alkylene group having 2 to 6 carbon atoms, independently of each other;

each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 represents a direct bond or a polyoxyalkylene chain having an oxyalkylene group as a repeating unit, independently of one another, wherein at least one of Z 1 to Z 6 is the polyoxyethylene chain in which the number of repetition of the oxyethylene group is two or more, and at least one of Z 1 to Z 6 which is not the polyoxyethylene chain is the polyoxyalkylene chain having the oxyalkylene group other than the oxyethylene group as the repeating unit;
U 1 is a group represented by a general formula (IV):
-E 21 -X 21 —  (IV)

and includes the urethane bond in the molecular chain of the polysiloxane-based macromonomer, where in the general formula (IV)
X 21 represents an oxygen atom, and
E 21 represents
a —NHCO— group, wherein E 21 forms the urethane bond with X 21 , or
a divalent group derived from a diisocyanate selected from a group consisting of saturated aliphatic diisocyanates, unsaturated aliphatic diisocyanates, alicyclic diisocyanates and aromatic diisocyanates, wherein E 21 forms the urethane bond with each of Z 1 and X 21 ;

U 2 is a group represented by a general formula (VI):
—R 41 —X 41 -E 41 -X 42 —R 42 —  (VI)

and includes the urethane bond in the molecular chain of the polysiloxane-based macromonomer, where the general formula (VI)
each of R 41 and R 42 represents a linear or branched alkylene group having 2 to 6 carbon atoms, independently of each other, and
each of X 41 and X 42 represents an oxygen atom or an alkylene glycol group, independently of each other, and E 41 represents a divalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic diisocyanates, unsaturated aliphatic diisocyanates, alicyclic diisocyanates and aromatic diisocyanates, wherein E 41 forms the urethane bond with each of X 41 and X 42 ;
U 3 is a group represented by a general formula (VII):
—X 22 -E 22 -  (VII)

and includes the urethane bond in the molecular chain of the polysiloxane-based macromonomer, where in the general formula (VII)
X 22 represents an oxygen atom, and
E 22 represents
the —NHCO — group, wherein E 22 forms the urethane bond with X 22 , or
a divalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic diisocyanates, unsaturated aliphatic diisocyanates, alicyclic diisocyanates and aromatic diisocyanates, wherein E 22 forms the urethane bond with each of Z 5 and X 22 ; and

each of S 1 and S 2 , which are independent of each other, is a group represented by a general formula (V):

where
each of R 31 and R 38 represents a linear or branched alkylene group having 2 to 6 carbon atoms, independently of each other, and
each of R 32 , R 33 , R 34 , R 35 , R 36 and R 37 represents an alkyl group having 1 to 6 carbon atom(s), a fluorine-substituted alkyl group or a phenyl group, independently of one another,
K is an integer within a range from 1 to 1500, and
L is 0 or an integer within a range from 1 to 1500, wherein a sum of K and L:
K+L

is an integer within the range from 1 to 1500.

9. The ophthalmic lens according to claim 1 , wherein the polysiloxane-based macromonomer is represented by one of the following general formulas (VIII), (IX) and (XIII):

where
R 51 represents a hydrogen atom or a methyl group,
a is an integer not smaller than two,
b is an integer not smaller than two,
n is an integer within a range from 1 to 1500, and
each of R 52 and R 53 is a hydrogen atom or a methyl group, wherein
if R 53 is a methyl group then R 52 is a hydrogen atom, and
if R 53 is a hydrogen atom then R 52 is a methyl group;

where
a′ is an integer not smaller than two,
b′ is an integer not smaller than two,
n′ is an integ

Assignees

• Menicon Co Ltd

Inventors

• Satake Kohsuke

Classifications

• C08L101/14

  the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08F290/068

  Polysiloxanes · CPC title

• C08G77/46

  containing polyether sequences · CPC title

• C08G18/61 Primary

  Polysiloxanes · CPC title