Crosslinkable hydrophilic materials from reactive oligomers having pendent photoinitiator groups

• US 7,276,247 B2
• Filed: 04/11/2006
• Issued: 10/02/2007
• Est. Priority Date: 03/01/2004
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Gaddam, Babu N., Heilmann, Steven M., Lewandowski, Kevin M., Wendland, Michael S., Fansler, Duane D.
• Primary Examiner(s): Berman; Susan W.
• Application Number:
  US11/279,368
• Publication Number:
  US 20060165999A1
• Time in Patent Office: 539 Days
• Field of Search: 424/445, 424/447, 424/448, 522/121
• US Class Current: 424/445
• CPC Class Codes: A61L 15/26 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/60 Liquid-swellable gel-forming materials, e.g. super-absorbents
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]

Abstract

The present invention provides crosslinkable compositions useful in the preparation of hydrophilic gels, and are prepared from oligomers having pendent hydrophilic, poly(alkylene oxide) groups, pendent photoinitiator groups, and optionally polymerizable functional groups, and crosslinked by polyfunctional poly(alkylene oxides).

Claims

1. An absorbent dressing comprising a crosslinked hydrophilic gel absorbent layer comprising:

a) a first component oligomer comprising a plurality of polymerized monomer units having pendent hydrophilic poly(alkylene oxide) groups, and pendent photoinitiator groups; and

b) a hydrophilic poly(alkylene oxide) crosslinking agent of the formula;

Z-Q-CH(R¹)—

CH₂—

O—

(CH(R¹)—

CH₂—

O)_m—

CH(R¹) —

CH₂-Q-Z, wherein Z is a polymerizable ethylenically unsaturated moiety, R¹ is a H or a C₁ to C₄ alkyl group, and m is from 20 to 500, and Q is a divalent linking group selected from —

O—

, —

NR¹—

, —

CO₂— and

—

CONR¹—

.

2. The absorbent dressing of claim 1 wherein said oligomer has a degree of polymerization of less than 300, prior to crosslinking.

3. The absorbent dressing of claim 1, wherein said crosslinking agent is a poly(ethylene oxide)(co)polymer.

4. The absorbent dressing of claim 1, wherein said crosslinking agent is a poly(ethylene oxide-co-propylene oxide) copolymer.

5. The absorbent dressing of claim 1 wherein said first component oligomer comprises:

a) from 20 to 99 parts by weight of polymerized monomer units having pendent, hydrophilic poly(alkylene oxide) groups, and

b) from 0.1 to 25 parts by weight of polymerized monomer units derived from of an ethylenically-unsaturated monomer having a pendent photoinitiator group;

c) from 0 to 25 parts by weight of polymerized monomer units derived from of an ethylenically-unsaturated monomer having a pendent polymerizable group; and

d) from 0 to 30 parts by weight of polymerized monomer units derived from acrylic acid esters, preferably of non-tertiary alkyl alcohols containing 1-14 carbon atoms; and

c) from 0 to 40 parts by weight of at least one other monomer.

6. The absorbent dressing of claim 5, wherein the composition comprises both polymerization monomer units derived from of an ethylenically-unsaturated monomer having a pendent photoinitiator group;

and polymerized monomer units derived from of an ethylenically-unsaturated monomer having a pendent polymerizable group, and the total of such monomer units is 0.1 to 25 parts by weight.

7. The absorbent dressing of claim 5 wherein said first component oligomer comprises a plurality of polymerized monomer units having pendent photoinitiator groups, wherein said pendent photoinitiator groups are of formula:

8. The absorbent dressing of claim 1 wherein the amount of said crosslinking agent is sufficient to provide more than two crosslinks per first component oligomer chant upon crosslinking.

9. The absorbent dressing of claim 1 which comprises:

a) from 50 to 99.9 parts by weight of said first component oligomer, and

b) from 0.1 to 50 parts by weight of said crosslinking agent, wherein the crosslinked composition can absorb at least 50 wt. % water.

10. The absorbent dressing of claim 1, wherein said crosslinked hydrophilic gel absorbent has an average molecular weight between crosslinks of at least 1000.

11. The absorbent dressing of claim 1, wherein said Z of said crosslinking agent is selected from

12. The absorbent dressing of claim 1 comprising:

a permeable facing layer,

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

said hydrophilic gel absorbent layer disposed between the backing and facing layer.

13. The absorbent dressing of claim 12 having a layer of pressure sensitive adhesive on at least a portion of the front surface of the layer.

14. The absorbent dressing of claim 1 wherein the gel layer further comprises a pharmacologically active agent.

15. The absorbent dressing of claim 1 wherein gel layer further comprises a hydrocolloid.

16. The absorbent dressing of claim 1, wherein the gel layer further comprises a patterned surface.

17. The absorbent dressing of claim 1, wherein said absorbent layer is transparent upon swelling.