CA2481765A1 - Gel materials, medical articles, and methods - Google Patents

Gel materials, medical articles, and methods Download PDF

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Publication number
CA2481765A1
CA2481765A1 CA002481765A CA2481765A CA2481765A1 CA 2481765 A1 CA2481765 A1 CA 2481765A1 CA 002481765 A CA002481765 A CA 002481765A CA 2481765 A CA2481765 A CA 2481765A CA 2481765 A1 CA2481765 A1 CA 2481765A1
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Canada
Prior art keywords
alkylene oxide
macromonomer
medical article
group
multifunctional
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Granted
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CA002481765A
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French (fr)
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CA2481765C (en
Inventor
Ahmed S. Abuelyaman
Scott A. Burton
Duane D. Fansler
Babu N. Gaddam
Paul Hattam
Maureen A. Kavanagh
Kevin M. Lewandowski
Peter M. Seiler
Steven C. Stickels
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3M Innovative Properties Co
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Individual
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/142—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/90—Compositions for taking dental impressions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G

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 a free-radically polymerizable, multifunctional (preferably difunctional), having a weight average molecular weight of at least 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.

Claims (53)

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 is a (C1-C4)alkyl group.
2. ~The medical article of claim 1 wherein the gel material is transparent.
3. ~The medical article of claim 1 wherein the gel material is absorbent.
4. ~The medical article of claim 1 wherein the gel material comprises a homopolymer of the multifunctional poly(alkylene oxide) macromonomer.
5. 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.
6. The medical article of claim 8 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 1 wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer.
8. The medical article of claim 7 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.
9. The medical article of claim 8 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.
10. The medical article of claim 8 wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer and a monofunctional poly(alkylene oxide) monomer.
11. The medical article of claim 10 wherein the monofunctional poly(alkylene oxide) monomer is of the formula:
H2C=C(R2)-C(O)-Q-(-CH(R1)-CH2-O-)x...(-CH2-CH2-O-)y-Z
wherein the mole ratio of x:y is within a range of 0 to 1; R2 = H or CH3; R1 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-C4)alkyl 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.
12. The medical article of claim 8 wherein the gel material comprises a copolymer of the multifunctional poly(alkylene oxide) macromonomer and a polar monomer.
13. The medical article of claim 12 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.
14. The medical article of claim 8 comprising a copolymer of the multifunctional macromonomer, a polar monomer, a monofunctional poly(alkylene oxide) monomer,, and a hydrophobic monomer.
15. The medical article of claim 14 wherein the hydrophobic monomer is a (meth)acrylic acid ester.
16. The medical article of claim 15 wherein the (meth)acrylic acid ester is selected from the group consisting of lauryl acrylate, 2-ethylhexyl acrylate, isooctyl acrylate, and combinations thereof.
17. The medical article of claim 14 wherein the hydrophobic monomer is alpha-methylstyrene.
18. The medical article of claim 1 wherein the multifunctional macromonomer is difunctional.
19. The medical article of claim 18 wherein the multifunctional macromonomer is linear.
20. The medical article of claim 1 wherein the gel material is substantially acid free.
21. The medical article of claim 1 wherein the gel material further comprises hydrocolloid particles.
22. The medical article of claim 21 wherein the hydrocolloid particles comprise carboxymethyl cellulose particles.
23. The medical article of claim 1 wherein the gel material is transparent when dry or swollen with an aqueous solution.
24. The medical article of claim 1 further comprising a pharmacologically active agent.
25. The medical article of claim 1 which is a wound dressing or wound packing.
26. The medical article of claim 1 which is a dental impression material.
27. A medical article comprising a gel material comprising a copolymer prepared from monomers comprising:
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 is a (C1-C4)alkyl group;
a monofunctional poly(alkylene oxide) monomer; and a polar monomer.
28. The medical article of claim 27 which is a wound dressing or wound packing.
29. The medical article of claim 27 wherein the gel material is transparent and absorbent.
30. 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 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.
31. The medical article of claim 30 which is a wound dressing or wound packing.
32. The medical article of claim 30 wherein the gel material is transparent and absorbent.
33. A medical article comprising:
a film;
a gel material comprising a polymerized 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 is a (C1-C4)alkyl group; and a perforated film.
34. A wound dressing 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 a gel material disposed between the backing and facing layers, wherein the gel material comprises a polymerized 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 is a (C1-C4)alkyl group.
35. The wound dressing of claim 34 wherein the backing layer is permeable to moisture vapor.
36. The wound dressing of claim 34 further comprising a release liner secured to the adhesive layer.
37. The wound dressing of claim 34 wherein the backing layer and facing layer are transparent.
38. The wound dressing of claim 34 wherein said adhesive is selected from acrylic adhesives.
39. A method of maintaining a moist wound healing environment, the method comprising applying a gel material comprising:
a polymerized 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 is a (C1-C4)alkyl group.
40. 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.
41. 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 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.
42. 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.
43. 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 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.
44. A polymer prepared from the macromonomer of claim 40.
45. A polymer prepared from the macromonomer of claim 41.
46. A polymer prepared from the macromonomer of claim 42.
47. A polymer prepared from the macromonomer of claim 43.
48. 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 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.
49. 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.
50. The method of claim 49 wherein the syrup polymer mixture comprises a photoinitiator.
51. The method of claim 50 wherein the step of forming a gel from the syrup polymer mixture comprises applying radiation.
52. The method of claim 49 wherein the step of forming a gel from the syrup polymer mixture comprises applying thermal energy.
53. The method of claim 50 wherein the step of forming a gel from the syrup polymer mixture comprises applying ultraviolet radiation and thermal energy sequentially.
CA2481765A 2002-04-12 2003-03-27 Gel materials, medical articles, and methods Expired - Fee Related CA2481765C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/121,518 US7005143B2 (en) 2002-04-12 2002-04-12 Gel materials, medical articles, and methods
US10/121,518 2002-04-12
PCT/US2003/009556 WO2003086493A1 (en) 2002-04-12 2003-03-27 Gel materials, medical articles, and methods

Publications (2)

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CA2481765A1 true CA2481765A1 (en) 2003-10-23
CA2481765C CA2481765C (en) 2011-09-13

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US (2) US7005143B2 (en)
EP (2) EP1494727B1 (en)
JP (1) JP4550428B2 (en)
KR (1) KR100982415B1 (en)
CN (1) CN1327908C (en)
AT (1) ATE381355T1 (en)
AU (1) AU2003228392A1 (en)
BR (1) BRPI0309109B8 (en)
CA (1) CA2481765C (en)
DE (1) DE60318189T2 (en)
ES (1) ES2297161T3 (en)
MX (1) MXPA04009963A (en)
WO (1) WO2003086493A1 (en)

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