Devices using silicone pressure sensitive adhesives containing organic wax

• US RE36,754 E
• Filed: 06/06/1996
• Issued: 06/27/2000
• Est. Priority Date: 07/22/1991
• Status: Expired due to Term

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Noel, Ross Alan
• Primary Examiner(s): VIGUSHIN, JOHN B
• Application Number:
  US08/653,637
• Time in Patent Office: 1,482 Days
• Field of Search: 424/448, 424/449, 524/277, 524/487, 525/478
• US Class Current: 424/449
• CPC Class Codes: A61K 9/7069 obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
• CPC Class Codes: A61K 9/7084 Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
• CPC Class Codes: A61L 15/34 Oils, fats, waxes or natural resins A61L15/225 takes precedence
• CPC Class Codes: A61L 15/58 Adhesives
• CPC Class Codes: C08L 91/06 Waxes
• CPC Class Codes: C09J 183/02 Polysilicates
• CPC Class Codes: C09J 183/04 Polysiloxanes

Abstract

Hot-melt silicone pressure sensitive adhesive compositions containing organic waxes, methods of using the compositions and devices made using the compositions are disclosed. The hot-melt silicone pressure sensitive adhesive compositions include a mixture of (i) a silicate resin, (ii) a silicone fluid, and (iii) an organic wax having a melting point of between 30° C. and 150° C. The organic wax decreases dynamic viscosity of the adhesive at temperatures equal to or below about 200° C.

Claims

1. A matrix transdermal drug delivery device for a bioactive agent, comprising:

(a) a backing substrate;

(b) an adhesive matrix atop at least portions of said backing substrate, said adhesive matrix formed of a non-flammable, hot-melt, silicone pressure sensitive adhesive composition having tackiness and adhesiveness containing (i) between about 30 and about 70 percent by weight of a benzene-soluble resinous copolymer containing silicon-bonded hydroxyl radicals and consisting essentially of triorganosiloxy units of the formula R₃ SiO_1/2 and tetra functional siloxy units of the formula SiO_4/2 in a ratio of about 0.6 to 0.9 triorganosiloxy units for each tetra functional siloxy unit present in the copolymer, wherein each R is a monovalent organic radical independently selected from the group consisting of hydrocarbon radicals of from 1 to 6 inclusive carbon atoms;

(ii) between about 22 and about 60 percent by weight of a polydimethylsiloxane fluid; and

(iii) between about 1.0 and about 25 percent by weight of an organic wax, all weight percents being based on total composition weight, said wax having a melting point of between about 30°

C. and about 150°

C., and said organic wax decreasing the dynamic viscosity of the resultant hot-melt silicone pressure sensitive adhesive at temperatures ranging up to about 200°

C., and said silicone pressure sensitive adhesive composition including ingredients selected from the group consisting of drugs, excipients, co-solvents, enhancers, and mixtures thereof where the silicone pressure sensitive adhesive composition is compatible with said drugs, excipients, co-solvents and enhancers wherein the silicone pressure sensitive adhesive composition has a tack value between about 50 and 800 g/cm² measured using a probe tack tester at a speed of 0.5 cm/second with a 0.5 second dwell time; and

(c) a release liner contacted on the adhesive matrix.

3. The matrix transdermal drug delivery device for a bioactive agent of claim 1, wherein the organic wax is selected from the group consisting of naturally occurring waxes including carnauba, candelilla, beeswax, paraffin, ozokerite, ceresine waxes, and mixtures thereof.

4. The matrix transdermal drug delivery device for a bioactive agent of claim 1, wherein the organic wax is present in an amount between about 5 percent and about 20 percent by weight based on total adhesive composition weight.

5. The matrix transdermal drug delivery device for a bioactive agent of claim 1, wherein the silicone pressure sensitive adhesive containing the organic wax has a dynamic viscosity of less than or equal to 800 poise at a temperature of about 200°

C.

9. The matrix transdermal drug delivery device of claim 1, wherein the silicone pressure sensitive adhesive composition has an adhesion value between about 100 and 2000 gm/cm determined by first adhering tape having the silicone pressure sensitive adhesive composition thereon to stainless steel using a 4 pound roller and, subsequently, stripping the tape from the stainless steel while pulling at a rate of 12 inches/minute at an angle of 180°

using a tensile testing machine.

2. A reservoir transdermal drug delivery device, comprising:

(a) a backing substrate;

(b) a reservoir attached to at least portions of the backing substrate, said reservoir containing compositions selected from the group consisting of drugs, excipients, co-solvents, enhancers, and mixtures thereof;

(c) a non-flammable hot-melt silicone pressure sensitive adhesive composition having tackiness and adhesiveness containing (i) between about 30 and about 70 percent by weight of a benzene-soluble resinous copolymer containing silicon-bonded hydroxyl radicals and consisting essentially of triorganosiloxy units of the formula R₃ SiO_1/2 and tetra functional siloxy units of the formula SiO_4/2 in a ratio of about 0.6 to 0.9 triorganosiloxy units for each tetra functional siloxy unit present in the copolymer, wherein each R is a monovalent organic radical independently selected from the group consisting of hydrocarbon radicals of from 1 to 6 inclusive carbon atoms;

(ii) between about 22 and about 60 percent by weight polydimethylsiloxane fluid; and

(iii) between about 1.0 and about 25 percent by weight of an organic wax, all weight percents being based on total composition weight, said wax having a melting point of between about 30°

C. and about 150°

C., and said wax decreasing dynamic viscosity of the hot-melt silicone pressure sensitive adhesive at temperatures ranging up to about 200°

C., wherein the silicone pressure sensitive adhesive composition has a tack value between about 50 and 800 g/cm² measured using a probe tack tester at a speed of 0.5 cm/second with a 0.5 second dwell time, coated on top of the reservoir and portions of the backing substrate not covered by the reservoir; and

(d) a release liner attached to the silicone pressure sensitive adhesive.

6. The reservoir transdermal drug delivery device of claim 2, wherein the organic wax is selected from the group consisting of naturally occurring waxes including carnauba, candelilla, beeswax, paraffin, ozokerite, ceresine waxes, and mixtures thereof.

7. The reservoir transdermal drug delivery device of claim 2, wherein the organic wax is present in an amount between about 5 percent and about 20 percent by weight based on total adhesive composition weight.

8. The reservoir transdermal drug delivery device of claim 2, wherein the silicone pressure sensitive adhesive containing the organic wax has a dynamic viscosity of less than or equal to 800 poise at a temperature of about 200°

C.

10. The reservoir transdermal drug delivery device of claim 2, wherein the silicone pressure sensitive adhesive composition has an adhesion value between about 100 and 2000 gm/cm determined by first adhering tape having the silicone pressure sensitive adhesive composition thereon to stainless steel using a 4 pound roller and, subsequently, stripping the tape from the stainless steel while pulling at a rate of 12 inches/minute at an angle of 180°

using a tensile testing machine. .Iadd.

11. A matrix transdermal drug delivery device for a bioactive agent, comprising:

(a) a backing substrate;

(b) an adhesive matrix atop at least portions of said backing substrate, said adhesive matrix formed of a non-flammable, hot-melt, silicone pressure sensitive adhesive composition having tackiness and adhesiveness containing (i) between about 30 and about 70 percent by weight of a cohydrolysis product of a trialkyl hydrolyzable silane and an alkyl silicate, wherein the cohydrolysis product contains a plurality of silicon-bonded hydroxy groups, (ii) between about 22 and about 60 percent by weight of a polydimethylsiloxane fluid; and

(iii) between about 1.0 and about 25 percent by weight of an organic wax, all weight percents being based on total composition weight, said wax having a melting point of between about 30°

C. and about 150°

C., and said organic wax decreasing the dynamic viscosity of the resultant hot-melt silicone pressure sensitive adhesive at temperatures ranging up to about 200°

C., and said silicone pressure sensitive adhesive composition including ingredients selected from the group consisting of drugs, excipients, co-solvents, enhancers, and mixtures thereof, wherein the silicone pressure sensitive adhesive composition is compatible with said drugs, excipients, co-solvents and enhancers, and the silicone pressure sensitive adhesive composition has a tack value between about 50 and 800 g/cm² measured using a probe tack tester at a sped of 0.5 cm/second with a 0.5 second dwell time; and

(c) a pressure sensitive adhesive release liner contacting the adhesive matrix. .Iaddend..Iadd.12. The matrix transdermal drug delivery device for a bioreactive agent of claim 11, wherein the organic wax is selected from the group consisting of naturally occurring waxes including carnauba, candelilla, beeswax, paraffin, ozokerite, ceresine, and mixtures thereof.

12. Iaddend..Iadd.13. The matrix transdermal drug delivery device for a bioactive agent of claim 11, wherein the organic wax is present in an amount between about 5 percent and about 20 percent by weight based on total adhesive composition weight. .Iaddend..Iadd.14. The matrix transdermal drug delivery device for a bioactive agent of claim 11, wherein the silicone pressure sensitive adhesive containing the organic wax has a dynamic viscosity of less than or equal to 800 poise at a temperature of about 200°

C. .Iaddend..Iadd.15. The matrix transdermal drug delivery device of claim 11, wherein the silicone pressure sensitive adhesive composition has an adhesion value between about 100 and 2000 gm/cm determined by first adhering tape having the silicone pressure sensitive adhesive composition thereon to stainless steel using a 4 pound roller and, subsequently, stripping the tape from the stainless steel while pulling at a rate of 12 inches/minute at an angle of 180°

using a tensile testing machine. .Iaddend..Iadd.16. A reservoir transdermal drug delivery device for a bioactive agent, comprising;

(a) a backing substrate;

(b) a reservoir attached to at least portions of said backing substrate, said reservoir containing compositions selected from the group consisting of drugs, excipients, co-solvents, enhancers, and mixtures thereof;

(c) a non-flammable hot-melt, silicone pressure sensitive adhesive composition having tackiness and adhesiveness coated on top of the reservoir and portions of the backing substrate not covered by the reservoir, the silicone pressure sensitive adhesive containing (i) between about 30 and about 70 percent by weight of a cohydrolysis product of a trialkyl hydrolyzable silane and an alkyl silicate, wherein the cohydrolysis product contains a plurality of silicone-bonded hydroxy groups, (ii) between about 22 and about 60 percent by weight of a polydimethylsiloxane fluid; and

(iii) between about 1.0 and about 25 percent by weight of an organic wax, all weight percents being based on total composition weight, said wax having a melting point of between about 30°

C. and about 150°

C., and said organic wax decreasing the dynamic viscosity of the resultant hot-melt silicone pressure sensitive adhesive at temperature ranging up to about 200°

C., wherein the silicone pressure sensitive adhesive composition has a tack value between about 50 and 800 g/cm² measured using a probe tack tester at a speed of 0.5 cm/second with a 0.5 second dwell time; and

(c) a pressure sensitive adhesive release liner attached to the silicone pressure sensitive adhesive. .Iaddend..Iadd.17. The reservoir transdermal drug delivery device for a bioactive agent of claim 16, wherein the organic wax is selected from the group consisting of naturally occurring waxes including carnauba, candelilla, beeswax, paraffin, ozokerite, ceresine, and mixtures thereof. .Iaddend..Iadd.18. The reservoir transdermal drug delivery device for a bioactive agent of claim 16, wherein the organic wax is present in an amount between about 5 percent and about 20 percent by weight based on total adhesive composition weight. .Iaddend..Iadd.19. The reservoir transdermal drug delivery device for a bioactive agent of claim 16, wherein the silicone pressure sensitive adhesive containing the organic wax has a dynamic viscosity of less than or equal to 800 poise at a temperature of about 200°

C.

13. Iaddend..Iadd.20. The reservoir transdermal drug delivery device of claim 16, wherein the silicone pressure sensitive adhesive composition has an adhesion value between about 100 and 2000 gm/cm determined by first adhering tape having the silicone pressure sensitive adhesive composition thereon to stainless steel using a 4 pound roller and, subsequently, stripping the tape from the stainless steel while pulling at a rate of 12 inches/minute at an angle of 180°

using a tensile testing machine. .Iaddend.