Gel materials, medical articles, and methods

• US 7,005,143 B2
• Filed: 04/12/2002
• Issued: 02/28/2006
• Est. Priority Date: 04/12/2002
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Gaddam, Babu N., Abuelyaman, Ahmed S., Kavanagh, Maureen A., Lewandowski, Kevin M., Seiler, Peter M., Burton, Scott A., Stickels, Steven C., Fansler, Duane, Hattam, Paul
• Primary Examiner(s): Zalukaeva, Tatyana
• Application Number:
  US10/121,518
• Publication Number:
  US 20030203011A1
• Time in Patent Office: 1,418 Days
• Field of Search: 424/487, 424/78.17, 525/329.5
• US Class Current: 424/487
• CPC Class Codes: A61K 6/90 Compositions for taking dental impressions
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: C08F 290/062 Polyethers
• CPC Class Codes: C08F 290/142 Polyethers

Abstract

A gel material and medical articles including such material, wherein the transparent gel material includes a polymerized poly(alkylene oxide) macromonomer that, prior to polymerization, is free-radically polymerizable, multifunctional (preferably difunctional), and has an average molecular weight of at least about 2000.

Claims

1. A medical article comprising a gel material comprising a copolymer of a difunctional poly(alkylene oxide) macromonomer, a polar monomer, a monofunctional poly(alkylene oxide) monomer, and a hydrophobic monomer, wherein the hydrophobic monomer is alpha-methylstyrene;

and

wherein the difunctional macromonomer has a weight average molecular weight of at least about 2000, and is of the formula;

XO—

(—

CH(R¹)—

CH₂—

O—

)_m . . . (—

CH₂—

CH₂—

O—

)_n—

Y

 

wherein;

the mole ratio of m;

n is within a range of about 1;

9 to about 9;

1; and

R¹ is a (C1–

C4) alkyl group; and

X and Y are each independently selected from the group consisting of

 

wherein R² is H or CH_3, R³ is an aromatic group, aliphatic group, alicylic group, or combinations thereof, W is an alkylene or alkylene oxide group, and r =2–

10.

2. The medical article of claim 1 which is selected from the group consisting of a wound dressing, a wound packing, an adhesive, an adhesion preventing material, a blood purification absorbent, a base material for releasing a pharmacologic agent, a dental molding, a dental impression, a dental restorative, a dental coating, a dental composite, a dental sealant, and combinations thereof.

3. The medical article of claim 1 wherein the gel material is absorbent.

4. The medical article of claim 1 wherein R¹ is methyl, the mole ratio of m:

n is about 1;

3, and X and Y are each independently

wherein R² CH₃.

5. The medical article of claim 1 wherein the monofunctional poly(alkylene oxide) monomer is of the formula:

H₂C═

C(R²)—

C(O)-Q-(—

CH(R¹)—

CH₂—

O—

)_x . . . (—

CH₂—

CH—

O—

)_y-Z

wherein the mole ratio of x;

y is within a range of 0 to 1;

R²═

H or CH₃R¹ is a (C1–

C4)alkyl group;

Z is H or a (C1–

C4)alkyl group, an aryl group, a (C1–

C4)alkaryl group, or an ar(C1–

C4alkyl group; and

Q is —

O—

, —

(H)N—

C(CH₃)₂—

C(O)—

O—

, —

O—

CH₂CH₂—

N(H)—

C(O)—

O—

, or

wherein R² is H or CH₃, R³ is an aromatic group, aliphatic group, alicylic group, or combinations thereof, and W is an alkylene or alkylene oxide group.

6. The medical article of claim 1 wherein the polar monomer is selected from the group consisting of 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl(meth)acrylate, 3-hydroxypropyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate, N-vinyl caprolactam, N-vinyl acetamide, N-vinyl pyrrolidone, acrylamide, mono- or di-N-alkyl substituted acrylamide, (meth)acrylic acid, itaconic acid, beta-carboxyethyl acrylate, glycerol methacrylate, [2(meth)(acryloyloxy)ethyl]trimethylammonium chloride, [2-(meth)(acryloyloxy)ethyl]trimethylammonium methyl sulfate, and combinations thereof.

7. The medical article of claim 1 wherein the hydrophobic monomer is a (meth)acrylic acid ester.

8. The medical article or claim 7 wherein the (meth)acrylic acid ester is selected from the group consisting of lauryl acrylate, 2ethylhexyl acrylate, isooctyl acrylate, and combinations thereof.

9. The medical article of claim 1 wherein the gel material is substantially acid free.

10. The medical article or claim 1 wherein the gel material further comprises hydrocolloid particles.

11. A medical article of claim 10 wherein the hydrocolloid particles comprise carboxymethyl cellulose particles.

12. The medical article of claim 1 wherein the gel material is transparent when dry or swollen with an aqueous solution.

13. The medical article of claim 1 further comprising a pharmacologically active agent.

14. The medical article of claim 2 which is a wound dressing or wound packing.

15. The medical article of claim 2 which is a dental impression material.

19. The medical article of claim 1 further comprising:

a film on which the gel material is disposed; and

a perforated film.

20. The medical article of claim 1 further comprising:

a permeable facing layer having a layer of pressure sensitive adhesive on at least a portion of the front surface of the facing layer;

a backing layer bonded to said facing layer at the periphery; and

the gel material disposed between the backing and facing layers.

21. The medical article of claim 20 wherein the backing layer is permeable to moisture vapor.

22. The medical article of claim 20 further comprising a release liner secured to the adhesive layer.

23. The medical article of claim 20 wherein the backing layer and facing layer are transparent.

24. The medical article of claim 20 wherein said adhesive is selected from acrylic adhesives.

25. A method of maintaining a moist wound healing environment, the method comprising applying the gel material of claim 1.

16. A medical article comprising a transparent gel material comprising a copolymer prepared from monomers comprising:

a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight avenge molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric random alkylene oxide moiety of the formula;

—

(—

CH(R¹)—

CH₂—

O—

)_m . . . (—

CH₂—

CH₂—

O—

)_n—

 

wherein the mole ratio of m;

n is within a range of about 1;

9 to about 9;

1; and

R¹ is a (C1–

C4)alkyl group;

a monofunctional poly(alkylene oxide) monomer; and

a polar monomer.

17. The medical article of claim 16 which is a wound dressing or wound packing.

18. The medical article of claim 16 wherein the gel material is transparent and absorbent.