Gel materials, medical articles, and methods

• US 20060039982A1
• Filed: 10/21/2005
• Published: 02/23/2006
• Est. Priority Date: 04/12/2002
• Status: Abandoned Application

• 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
• Application Number:
  US11/255,396
• Publication Number:
  US 20060039982A1
• Time in Patent Office: Days
• 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 homopolymer or copolymer of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average 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.

2. The medical article of claim 1 wherein the gel material comprises a homopolymer of the multifunctional poly(alkylene oxide) macromonomer.

3. The medical article of claim 1 wherein the multifunctional macromonomer is a difunctional macromonomer 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 CH₃, R³ is an aromatic group, aliphatic group, alicylic group, or combinations thereof, W is an alkylene or alkylene oxide group, and r=2-10.

4. The medical article of claim 1 wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer.

5. The medical article of claim 4 wherein the multifunctional macromonomer is a difunctional macromonomer 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 CH₃, R³ is an aromatic group, aliphatic group, alicylic group, or combinations thereof, W is an alkylene or alkylene oxide group, and r=2-10.

6. The medical article of claim 5 wherein R¹ is methyl, the mole ratio of m:

n is about 1;

3, and X and Y are each independently

wherein R² is CH₃.

7. The medical article of claim 5 wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer and a monofunctional poly(alkylene oxide) monomer.

8. The medical article of claim 5 wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer and a polar monomer.

9. The medical article of claim 5 comprising a copolymer of the multifunctional macromonomer, a polar monomer, a monofunctional poly(alkylene oxide) monomer, and a hydrophobic monomer.

10. The medical article of claim 1 wherein the multifunctional macromonomer is difunctional.

11. The medical article of claim 10 wherein the multifunctional macromonomer is linear.

12. A medical article comprising a gel material comprising a homopolymer or copolymer prepared from monomers comprising:

about 5 wt-% to 100 wt-% of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric 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;

0 wt-% to about 80 wt-% of a monofunctional poly(alkylene oxide) monomer; and

0 wt-% to about 40 wt-% of a polar monomer.

13. The medical article of claim 12 which is a wound dressing or wound packing.

14. The medical article of claim 12 wherein the gel material is transparent and absorbent.

15. A multifunctional macromonomer comprising a copolymeric random alkylene oxide moiety 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, R¹ is a (C1-C4)alkyl group, and X and Y are independently selected from the group consisting of

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.

19. A polymer prepared from the macromonomer of claim 15.

16. A multifunctional macromonomer comprising 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;

and wherein the macromonomer comprises two or more end groups selected from the group consisting of

and mixtures thereof, 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.

20. A polymer prepared from the macromonomer of claim 16.

17. A multifunctional macromonomer having a molecular weight of at least about 2000, wherein the multifunctional macromonomer comprises a copolymeric random alkylene oxide moiety 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, R¹ is a (C1-C4)alkyl group, and X and Y are independently selected from the group consisting of

wherein R² is H or Me and r=2-10.

21. A polymer prepared from the macromonomer of claim 17.

18. A multifunctional macromonomer having a molecular weight of at least about 2000, wherein the multifunctional 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;

and wherein the macromonomer comprises two or more end groups selected from the group consisting of

and mixtures thereof, wherein R² is H or Me and r=2-10.

22. A polymer prepared from the macromonomer of claim 18.

23. A syrup polymer mixture comprising a partially polymerized homopolymer or copolymer prepared from monomers comprising:

about 0.1 wt-% to 100 wt-% of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric alkylene random 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;

0 wt-% to about 80 wt-% of a monofunctional poly(alkylene oxide) monomer;

0 wt-% to about 40 wt-% of a polar monomer; and

0 wt-% to about 20 wt-% of a hydrophobic monomer.

24. A method of making a gel, the method comprising

forming a syrup polymer mixture comprising a partially polymerized homopolymer or copolymer prepared from monomers comprising:

about 0.1 wt-% to 100 wt-% of a multifunctional poly(alkylene oxide) free-radically polymerizable macromonomer having a weight average molecular weight of at least about 2000, wherein the multifunctional poly(alkylene oxide) macromonomer comprises a copolymeric alkylene random 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;

0 wt-% to about 80 wt-% of a monofunctional poly(alkylene oxide) monomer;

0 wt-% to about 40 wt-% of a polar monomer; and

0 wt-% to about 20 wt-% of a hydrophobic monomer; and

forming a gel from the syrup polymer mixture.

25. The method of claim 24 wherein the syrup polymer mixture comprises a photo initiator.

26. The method of claim 25 wherein the step of forming a gel from the syrup polymer mixture comprises applying radiation.

27. The method of claim 24 wherein the step of forming a gel from the syrup polymer mixture comprises applying thermal energy.

28. The method of claim 25 wherein the step of forming a gel from the syrup polymer mixture comprises applying ultraviolet radiation and thermal energy sequentially.