Hydrophilic gel materials and methods of making

Patent metadata

Field	Value
Publication number	US-10618266-B2
Application number	US-201414514429-A
Country	US
Kind code	B2
Filing date	Oct 15, 2014
Priority date	Dec 12, 2007
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

The present disclosure describes articles, such as medical articles, containing a substrate having disposed thereon a hydrophilic gel material (e.g., a shaped hydrophilic gel material or a coating of a hydrophilic gel material) and methods for making such articles. Methods are provided for making hydrophilic gel materials from a precursor composition that contains a polar solvent and a polymerizable material that is miscible with the polar solvent.

First claim

What is claimed is:

1. A method of making an article comprising a substrate and a hydrophilic gel material adhered thereto, the method comprising:
providing a precursor composition comprising:
(a) at least 10 weight percent polar solvent based on a total weight of the precursor composition, wherein the polar solvent comprises water; and
(b) polymerizable material capable of free-radical polymerization and having an average number of ethylenically unsaturated groups per molecule of polymerizable material equal to at least 1.2 relative to total polymerizable material, wherein the polymerizable material is miscible with the polar solvent and wherein the polymerizable material comprises a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl groups and having at least 5 alkylene oxide units;
wherein the precursor composition comprises no greater than 90 weight percent polymerizable material based on the total weight of the precursor composition

providing a mold having at least two separate wells;
adding the precursor composition to the mold, the precursor composition being positioned in at least a portion of at least two separate wells;
providing a substrate and positioning the substrate to at least partially contact the precursor composition; and
exposing the precursor composition within the wells to radiation to at least partially polymerize the polymerizable material and to form a first swollen shaped hydrophilic gel material adhered to the substrate.

2. A method of making an article comprising a substrate and a hydrophilic gel material adhered thereto, the method comprising:
providing a precursor composition comprising:
(a) at least 10 weight percent polar solvent based on a total weight of the precursor composition, wherein the polar solvent comprises water; and
(b) polymerizable material capable of free-radical polymerization and having an average number of ethylenically unsaturated groups per molecule of polymerizable material equal to at least 1.2 relative to total polymerizable material, wherein the polymerizable material is miscible with the polar solvent and wherein the polymerizable material comprises a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl groups and having at least 5 alkylene oxide units;
wherein the precursor composition comprises no greater than 90 weight percent polymerizable material based on the total weight of the precursor composition;

providing a mold having a substrate in contact therewith in a manner to form at least two separate wells;
adding the precursor composition to the mold, the precursor composition being positioned in at least a portion of at least two separate wells; and
exposing the precursor composition within the wells to radiation to at least partially polymerize the polymerizable material and to form a first swollen shaped hydrophilic gel material adhered to the substrate.

3. A method of making an article comprising a substrate and a hydrophilic gel material adhered thereto, the method comprising:
providing a precursor composition comprising:
(a) at least 10 weight percent polar solvent based on a total weight of the precursor composition; and
(b) polymerizable material capable of free-radical polymerization and having an average number of ethylenically unsaturated groups per molecule of polymerizable material equal to at least 1.2 relative to total polymerizable material, wherein the polymerizable material is miscible with the polar solvent and forms a single phase with the polar solvent and comprises a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl groups and having at least 5 alkylene oxide units and the poly(alkylene oxide (meth)acrylate) having a weight average molecular weight less than 2,000 g/mole;
wherein the precursor composition comprises no greater than 90 weight percent polymerizable material based on the total weight of the precursor composition;

coating the precursor composition on at least a portion of at least one surface of a substrate; and
exposing the precursor composition to radiation to at least partially polymerize the polymerizable material to provide a coating of first swollen hydrophilic gel material adhered to the substrate.

4. The method of claim 3 , wherein the precursor composition comprises:
(a) greater than 10 weight percent polar solvent based on a total weight of the precursor composition; and
(b) less than 90 weight percent polymerizable material based on the total weight of the precursor composition, the polymerizable material being miscible in the polar solvent and comprising:
i) a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl functional groups and having at least 5 alkylene oxide units; and
ii) 0 to less than 20 weight percent anionic monomer based on a total weight of polymerizable material in the precursor composition, wherein the anionic monomer comprises an ethylenically unsaturated group in addition to an acidic group, a salt of the acidic group, or a mixture thereof.

5. The method of claim 3 , wherein:
coating the precursor composition comprises using a non-contact deposition technique; and
exposing the precursor composition to radiation to at least partially polymerize the polymerizable material to provide a coating of first swollen hydrophilic gel material on a substrate comprises forming a discontinuous coating of first swollen hydrophilic gel material on at least a portion of at least one surface of a substrate.

6. The method of claim 5 , wherein the non-contact deposition comprises inkjet printing.

7. The method of claim 5 , wherein the non-contact deposition comprises spray atomization deposition.

8. The method of claim 3 , wherein the precursor composition further comprises an active agent.

9. A method of making an article comprising a substrate and a hydrophilic gel material adhered thereto, the method comprising:
providing a precursor composition comprising:
(a) at least 10 weight percent polar solvent based on a total weight of the precursor composition, wherein the polar solvent comprises water; and
(b) polymerizable material capable of free-radical polymerization and having an average number of ethylenically unsaturated groups per molecule of polymerizable material equal to at least 1.2 relative to total polymerizable material, wherein the polymerizable material is miscible with the polar solvent, wherein the polymerizable material comprises a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acryloyl groups and having at least 5 alkylene oxide units;
wherein the precurser composition comprises no greater than 90 weight percent polymerizable material based on the total weight of the precursor composition;

coating the precursor composition on at least a portion of at least one surface of a substrate; and
exposing the precursor composition to radiation to at least partially polymerize the polymerizable material to provide a coating of first swollen hydrophilic gel material adhered to the substrate.

10. A method of making an article comprising a substrate and a hydrophilic gel material adhered thereto, the method comprising:
providing a precursor composition comprising:
(a) at least 10 weight percent polar solvent based on a total weight of the precursor composition; and
(b) polymerizable material capable of free-radical polymerization and having an average number of ethylenically unsaturated groups per molecule of polymerizable material equal to at least 1.2 relative to total polymerizable material, wherein the polymerizable material is miscible with the polar solvent, and wherein the polymerizable material comprises:
i) a poly(alkylene oxide (meth)acrylate) having at least 2 (meth)acr

Assignees

• 3M Innovative Properties Co

Inventors

• Wright Robin E
• Krampe Stephen E
• Walter Richard L
• Ylitalo Caroline M
• Eibner William A
• Tokie Jeffrey H
• Scholz Matthew T

Classifications

• C08F299/00

  Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers · CPC title

• B32B2038/0076

  Curing, vulcanising, cross-linking · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title

• C09J133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F290/062

  Polyethers · CPC title