Gel material

Patent metadata

Field	Value
Publication number	US-12037422-B2
Application number	US-201917270973-A
Country	US
Kind code	B2
Filing date	Aug 27, 2019
Priority date	Aug 28, 2018
Publication date	Jul 16, 2024
Grant date	Jul 16, 2024

Abstract

Disclosed is a gel material having a high water content and excellent mechanical properties. The gel material includes repeating units derived from the following monomers (A) and (B): (A) an anionic monomer containing a polymerizable carbon-carbon multiple bond and an aromatic ring, and (B) a cationic monomer containing a polymerizable carbon-carbon multiple bond and an aromatic ring. The gel material has a water content of 20% by mass to 95% by mass, a tensile elastic modulus of 9 MPa to 1000 MPa, and a tensile elongation at break of 50% to 5000%.

First claim

The invention claimed is:

1. A gel material comprising repeating units derived from the following monomers (A) and (B):
(A) an anionic monomer containing a polymerizable carbon-carbon multiple bond and an aromatic ring; and
(B) a cationic monomer containing a polymerizable carbon-carbon multiple bond and an aromatic ring;
the gel material having
a water content of 20% by mass to 95% by mass,
a tensile elastic modulus of 9 MPa to 1000 MPa, and
a tensile elongation at break of 200% to 5000%,
wherein the lower limit of the total molar concentration of monomer components in the monomer composition (Cm; unit, mol/L) is 2.0 and
wherein the ratio (mol/mol) between the repeating units derived from the monomer (A) and the repeating units derived from the monomer (B) is within the range of 35/65 to 75/25.

2. The gel material according to claim 1 , which is heat-moldable at a temperature within the range of 60° C. to 250° C.

3. The gel material according to claim 1 , comprising a copolymer containing repeating units derived from the monomers (A) and (B).

4. The gel material according to claim 1 , wherein the (A) is an anionic monomer represented by the following Formula (1):

wherein
X 1 represents a group selected from the group consisting of (meth)acryloyl and vinyl;
Z 1 represents a group selected from the group consisting of sulfo and carboxy, or a salt thereof;
L 1 and L 2 each independently represent a direct bond, or C 1 -C 10 alkylene;
Y 1 represents a direct bond, or a group selected from the group consisting of O, S, and N—R 2 ;
Y 2 represents a direct bond, or a group selected from the group consisting of O, S, N—R 3 , OCO, and N—R 4 CO;
R 1 represents a group selected from the group consisting of C 1 -C 10 alkyl, phenyl, halogeno, and hydroxy;
R 2 to R 4 each independently represent hydrogen, or a group selected from the group consisting of C 1 -C 10 alkyl and phenyl; and
m represents an integer of 0 to 4.

5. The gel material according to claim 4 , wherein
the L 1 and L 2 are each independently a direct bond or C 1 -C 5 alkylene;
the Y 1 and Y 2 are direct bonds; and
the R 1 is C 1 -C 5 alkyl.

6. The gel material according to claim 1 , wherein the (B) is a cationic monomer represented by the following Formula (2):

wherein
X 3 represents a group selected from the group consisting of (meth)acryloyl and vinyl;
Z 3 represents amino or a salt thereof;
L 3 and L 4 each independently represent a direct bond, or C 1 -C 10 alkylene;
Y 3 represents a direct bond, or a group selected from the group consisting of O, S, and N—R 6 ;
Y 4 represents a direct bond, or a group selected from the group consisting of O, S, N—R 7 , OCO, and N—R 8 CO;
R 5 represents a group selected from the group consisting of C 1 -C 10 alkyl, phenyl, halogeno, and hydroxy;
R 6 to R 8 each independently represent hydrogen, or a group selected from the group consisting of C 1 -C 10 alkyl and phenyl; and
n represents an integer of 0 to 4.

7. The gel material according to claim 6 , wherein
the Z 3 is a quaternary ammonium salt;
the L 3 and L 4 are each independently a direct bond or C 1 -C 5 alkylene;
the Y 3 and Y 4 are direct bonds; and
the R 5 is C 1 -C 5 alkyl.

8. The gel material according to claim 1 , wherein the (A) is an anionic monomer selected from the group consisting of benzyl (meth)acrylate-based anionic monomers, benzyl (meth)acrylamide-based anionic monomers, phenyl (meth)acrylate-based anionic monomers, phenyl (meth)acrylamide-based anionic monomers, and styrene-based anionic monomers.

9. The gel material according to claim 1 , wherein the (B) is a cationic monomer selected from the group consisting of benzyl (meth)acrylate-based cationic monomers, benzyl (meth)acrylamide-based cationic monomers, phenyl (meth)acrylate-based cationic monomers, phenyl (meth)acrylamide-based cationic monomers, and styrene-based cationic monomers.

10. The gel material according to claim 1 , wherein the (A) is styrenesulfonic acid or a salt thereof.

11. The gel material according to claim 1 , wherein the (B) is dialkylaminoalkyl styrene or a salt thereof.

12. The gel material according to claim 11 , wherein the (B) is (vinylbenzyl)trimethylammonium chloride.

13. The gel material according to claim 1 , which is optically transparent.

14. A medical gel material comprising the gel material according to claim 1 .

15. An ophthalmic gel material comprising the medical gel material according to claim 14 .

16. An ophthalmic lens gel material comprising the ophthalmic gel material according to claim 15 .

17. A medical device comprising the medical gel material according to claim 14 .

18. The medical device according to claim 17 , which is an ophthalmic lens.

Assignees

• Univ Hokkaido Nat Univ Corp
• Toray Industries

Inventors

• Gong Jian Ping
• Kurokawa Takayuki
• Guo Honglei
• Matsuda Takahiro
• Yo Chengtao

Classifications

• G02B1/041

  Lenses · CPC title

• C08J3/075

  Macromolecular gels · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title

• A61L27/52

  Hydrogels or hydrocolloids · CPC title

• A61L27/16

  obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title