IP Library Granted Patent US 10,640,732
Granted Patent B2
US 10,640,732 · App. 15/116,437 · Granted May 5, 2020

Lens solution, contact lens, and production method therefor

Inventors: Kazuhiro Iso (Minato-ku, JP); Satoshi Hyugaji (Minato-ku, JP)
Assignees: JSR CORPORATION; JSR Life Sciences Corporation
C11D3/0078C11D3/378C11D3/3765C11D3/3773C11D3/3784G02B1/043G02C7/049A61F2/16G02C7/04G02C2202/16
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,640,732
App. No.
15/116,437
Granted
May 5, 2020
Kind
B2
Abstract

Provided is a lens solution which has excellent lipid detergency, exhibits high hydrophilization performance, and exhibits an excellent lipid adhesion preventive effect and an excellent lubricity-imparting effect when the solution is used to coat a lens. Disclosed is a lens solution containing a polymer having 2.5% to 95% by mass of the following repeating unit (A) and 2.5% to 95% by mass of the following repeating unit (B): (A) a hydrophilic repeating unit; and (B) a repeating unit having a polyoxyalkylene group in a side chain and having the end of the side chain formed from an alkyl group having 5 to 30 carbon atoms, an alkanoyl group having 5 to 30 carbon atoms, or an aryl group.

Claims (86)

1. A solution comprising a polymer having 2.5% to 95% by mass of the following repeating unit (A) and 2.5% to 95% by mass of the following repeating unit (B):

(A) a hydrophilic repeating unit; and

(B) a repeating unit having a polyoxyalkylene group in a side chain and having the end of the side chain formed from an alkyl group having 5 to 30 carbon atoms, an alkanoyl group having 5 to 30 carbon atoms, or an aryl group,

wherein the repeating unit (A) comprises a repeating unit (A-3) represented by the following formula (4) and a betaine-containing repeating unit (A-6) represented by the following formula (7):

in which in formula (4),

R 12 represents a hydrogen atom or a methyl group; and

R 13 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a hydroxyalkyl group,

in which in formula (7),

Y represents —(C═O)O − , —(O═S═O)O − , —O(O═S═O)O − , —(S═O)O − , —O(S═O)O − , —OP(═O)(OR 24 )O − , —OP(═O)(R 24 )O − , —P(═O)(OR 24 )O − , or —P(═O)(R 24 )O − , wherein R 24 represents an alkyl group having 1 to 3 carbon atoms;

R 19 represents a hydrogen atom or a methyl group;

R 20 and R 21 each independently represent a divalent organic group having 1 to 10 carbon atoms; and

R 22 and R 23 each independently represent a hydrocarbon group having 1 to 10 carbon atoms.

2. The solution according to claim 1 , wherein the repeating unit (B) is represented by the following formula (10):

in which in formula (10),

R 32 represent an alkylene group having 2 to 4 carbon atoms;

R 33 represents an alkyl group having 5 to 30 carbon atoms, an alkanoyl group having 5 to 30 carbon atoms, or an aryl group;

R 34 represents a hydrogen atom or a methyl group;

R 35 represents —O—, **—(C═O)—O—, **—(C═O)—NR 36 —, **—NR 36 —(C═O)—, wherein R 36 represents a hydrogen atom or an organic group having 1 to 10 carbon atoms; and the symbol ** represents the position at which the moiety is bonded to the carbon atom to which R 34 in formula (10) is bonded, or a phenylene group; and

m represents 2 to 100 as an average value.

3. The solution according to claim 1 , wherein the polymer further comprises 40% by mass or less of a repeating unit (C), the repeating unit (C) being one or more selected from the group consisting of a repeating unit represented by the following formula (11), and a repeating unit having a group represented by the following formula (12) at the end of a side chain:

in which in formula (11),

R 37 represent a hydrogen atom or a methyl group;

R 38 represents —O—, ***—(C═O)—O—, ***—(C═O)—NR 40 —, ***—NR 40 —(C═O)—, wherein R 40 represents a hydrogen atom or an organic group having 1 to 10 carbon atoms; and the symbol *** represents the position at which the moiety is bonded to the carbon atom to which R 37 in formula (11) is bonded, or a phenylene group; and

R 39 represents a hydrocarbon group having 4 to 30 carbon atoms,

in which in formula (12),

R 41 represents a divalent organic group having 1 to 10 carbon atoms;

R 42 and R 43 each independently represent an organic group having 1 to 10 carbon atoms;

R 44 , R 45 and R 46 each independently represent —OSi(R 49 ) 3 , wherein R 49 's each independently represent a hydrogen atom or an organic group having 1 to 8 carbon atoms, or an organic group having 1 to 10 carbon atoms; and

r represents 0 to 200 as an average value.

4. The solution according to claim 1 , wherein the polymer is a water-soluble polymer.

5. The solution according to claim 4 , formulated for cleaning or storage of a contact lens.

6. The solution according to claim 5 , comprising 0.001% to 10% by mass of the polymer.

7. The solution according to claim 1 formulated, for coating a contact lens.

8. A method for producing a surface-modified contact lens, comprising bringing the solution according to claim 1 into contact with at least a part of a contact lens surface.

9. A contact lens comprising, in at least a part of the surface, a polymer containing 2.5% to 95% by mass of the following repeating unit (A) and 2.5% to 95% by mass of the following repeating unit (B):

(A) a hydrophilic repeating unit; and

(B) a repeating unit having a polyoxyalkylene group in a side chain and having the end of the side chain formed from an alkyl group having 5 to 30 carbon atoms or an alkanoyl group having 5 to 30 carbon atoms,

wherein the repeating unit (A) comprises a repeating unit (A-3) represented by the following formula (4) and a betaine-containing repeating unit (A-6) represented by the following formula (7):

in which in formula (4),

R 12 represents a hydrogen atom or a methyl group; and

R 13 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a hydroxyalkyl group,

in which in formula (7),

Y represents —(C═O)O − , —(O═S═O)O − , —O(O═S═O)O − , —(S═O)O − , —O(S═O)O − , —OP(═O)(OR 24 )O − , —OP(═O)(R 24 )O − , —P(═O)(OR 24 )O − , or —P(═O)(R 24 )O − , wherein R 24 represents an alkyl group having 1 to 3 carbon atoms;

R 19 represents a hydrogen atom or a methyl group;

R 20 and R 21 each independently represent a divalent organic group having 1 to 10 carbon atoms; and

R 22 and R 23 each independently represent a hydrocarbon group having 1 to 10 carbon atoms.

10. The solution according to claim 1 , wherein a content of the repeating unit (A) is 30 to 95% by mass in the polymer, and a content of the repeating unit B is 2.5% to 70% by mass in the polymer.

11. The solution according to claim 1 , wherein a content of the repeating unit (A) is 40 to 95% by mass in the polymer, and a content of the repeating unit B is 2.5 to 60% by mass in the polymer,

and wherein

the repeating unit (A) is dimethylacrylamide/N-methacryloyloxyethyl-N,N-dimethylammonium-α-N-methylcarboxybetaine, and

the repeating unit (B) is lauroxypolyethylene glycol monomethacrylate.

12. A polymer comprising 2.5% to 95% by mass of the following repeating unit (A) and 2.5% to 95% by mass of the following repeating unit (B):

(A) a hydrophilic repeating unit; and

(B) a repeating unit having a polyoxyalkylene group in a side chain and having the end of the side chain formed from an alkyl group having 5 to 30 carbon atoms, an alkanoyl group having 5 to 30 carbon atoms, or an aryl group, wherein

the repeating unit (A) comprises a repeating unit (A-3) represented by the following formula (4) and a betaine-containing repeating unit (A-6) represented by the following formula (7):

in which in formula (4),

R 12 represents a hydrogen atom or a methyl group; and

R 13 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a hydroxyalkyl group,

in which in formula (7),

Y represents —(C═O)O − , —(O═S═O)O − , —O(O═S═O)O − , —(S═O)O − , —O(S═O)O − , —OP(═O)(OR 24 )O − , —OP(═O)(R 24 )O − , —P(═O)(OR 24 )O − , or —P(═O)(R 24 )O − , wherein R 24 represents an alkyl group having 1 to 3 carbon atoms;

R 19 represents a hydrogen atom or a methyl group;

R 20 and R 21 each independently represent a divalent organic group having 1 to 10 carbon atoms; and

R 22 and R 23 each independently represent a hydrocarbon group having 1 to 10 carbon atoms.

13. The polymer according to claim 12 , wherein R 13 and R 14 in formula (4) each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

14. The polymer according to claim 12 , wherein R 20 and R 21 in formula (7) each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms.

15. The polymer according to claim 12 , wherein the repeating unit (B) is represented by the following formula (10):

in which in formula (10),

R 32 represent an alkylene group having 2 to 4 carbon atoms;

R 33 represents an alkyl group having 5 to 30 carbon atoms, an alkanoyl group having 5 to 30 carbon atoms, or an aryl group;

R 34 represents a hydrogen atom or a methyl group;

R 35 represents —O—, **—(C═O)—O—, **—(C═O)—NR 36 —, **—NR 36 —(C═O)—, wherein R 36 represents a hydrogen atom or an organic group having 1 to 10 carbon atoms; and the symbol ** represents the position at which the moiety is bonded to the carbon atom to which R 34 in formula (10) is bonded, or a phenylene group; and

m represents 2 to 100 as an average value.

16. The polymer according to claim 15 , wherein R 33 in formula (10) represents an alkyl group having 5 to 30 carbon atoms.

17. The polymer according to claim 15 , wherein R 35 in formula (10) represents **—(C═O)—O − , **—(C═O)—NR 36 —, **—NR 36 —(C═O)— or a phenylene group.

18. The polymer according to claim 12 , further comprising one or more of a repeating unit (C) selected from the group consisting of a repeating unit (C-1) represented by the following formula (11), and a repeating unit (C-2) having a group represented by the following formula (12) at the end of a side chain:

in which in formula (11),

R 37 represent a hydrogen atom or a methyl group;

R 38 represents —O—, ***—(C═O)—O—, ***—(C═O)—NR 40 —, ***—NR 40 —(C═O)—, wherein R 40 represents a hydrogen atom or an organic group having 1 to 10 carbon atoms; and the symbol *** represents the position at which the moiety is bonded to the carbon atom to which R 37 in formula (11) is bonded), or a phenylene group; and

R 39 represents a hydrocarbon group having 4 to 30 carbon atoms,

in which in formula (12),

R 41 represents a divalent organic group having 1 to 10 carbon atoms;

R 42 and R 43 each independently represent an organic group having 1 to 10 carbon atoms;

R 44 , R 45 and R 46 each independently represent —OSi(R 49 ) 3 , wherein R 49 's each independently represent a hydrogen atom or an organic group having 1 to 8 carbon atoms, or an organic group having 1 to 10 carbon atoms; and

r represents 0 to 200 as an average value.

19. The polymer according to claim 18 , wherein the repeating unit (C) is the repeating unit (C-1).

20. The polymer according to claim 18 , wherein a content of the repeating unit (C) is 0.1% by mass to 40% by mass.

Assignments (5)
CHANGE OF NAME Recorded Mar 25, 2026
From: JSR LIFE SCIENCES CORPORATION
To: MBL MATERIALS CO., LTD.
Reel/Frame 075228/0228 →
CHANGE OF ADDRESS Recorded Mar 25, 2026
From: MBL MATERIALS CO., LTD.
To: MBL MATERIALS CO., LTD.
Reel/Frame 075228/0238 →
CHANGE OF NAME Recorded Sep 22, 2025
From: JICC-02 CORPORATION
To: JSR CORPORATION
Reel/Frame 072326/0282 →
MERGER Recorded Sep 22, 2025
From: JSR CORPORATION
To: JICC-02 CORPORATION
Reel/Frame 072935/0152 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2016
From: ISO, KAZUHIRO; HYUGAJI, SATOSHI
To: JSR CORPORATION; JSR LIFE SCIENCES CORPORATION
Reel/Frame 039334/0381 →
Priority Claims (1)
JP 2014-021271 · Feb 6, 2014 · national
Continuity (1)
Related Publication 20170058237A1 · Mar 2, 2017