Silicone pressure sensitive adhesive containing alkylmethylsiloxane wax and related methods and devices

• US 5,300,299 A
• Filed: 07/22/1991
• Issued: 04/05/1994
• Est. Priority Date: 07/22/1991
• Status: Expired due to Term

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Sweet, Randall P., Ulman, Katherine L., Durfee, Loren D.
• Primary Examiner(s): Page, Thurman K.
• Assistant Examiner(s): LEVY, NEIL S
• Application Number:
  US07/733,573
• Time in Patent Office: 988 Days
• Field of Search: 424/448, 424/449, 424/447, 424/443, 524/267
• US Class Current: 424/448
• 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: A61L 15/34 Oils, fats, waxes or natural resins A61L15/225 takes precedence
• CPC Class Codes: A61L 15/585 Mixtures of macromolecular compounds
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09J 183/04 Polysiloxanes
• CPC Class Codes: C09J 183/10 Block or graft copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09J151/08, C09J153/00
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer
• CPC Class Codes: Y10T 428/31652 Of asbestos
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Hot-melt silicone pressure sensitive adhesive compositions containing alkylmethylsiloxane 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 alkylmethylsiloxane wax having a melting point of between 30° C. and 70° C. The alkylmethylsiloxane wax decreases dynamic viscosity of the adhesive at temperatures ranging from about 50° C. to about 200° C.

Claims

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

(a) a backing substrate;

(b) a matrix atop at least portions of said backing substrate, said matrix containing a hot-melt, silicone pressure sensitive adhesive composition containing a mixture of (i) a silicate resin, (ii) a silicone fluid, and (iii) an alkylmethylsiloxane wax which decreases dynamic viscosity of the adhesive composition at temperatures ranging from 50°

C. to about 200°

C. and said adhesive including compositions selected from the group consisting of drugs, excipients, co-solvents, enhancers, and mixtures thereof where the adhesive is compatible with said drugs, excipients and co-solvents and enhancers, said hot-melt, silicone pressure sensitive adhesive being disposed within said matrix; and

(c) a release liner contacted on the matrix.

2. The matrix transdermal drug delivery device of claim 1, wherein the drugs include drugs selected from the group consisting of cardiovascular agents, antiarrhythmic agents, antianginal agents, antibiotics, antifungals, antimicrobials, antihypertensives, analgesics, local anesthetics, contraceptives, hormonal supplements, anti-smoking agents, appetite suppressants, hypnotics, anxiolytics, and mixtures thereof.

3. The matrix transdermal drug delivery device of claim 1, wherein the matrix is between about 1 and about 15 mils thick.

4. The matrix transdermal drug delivery device of claim 1, wherein the co-solvents and excipients are selected from the group consisting of fatty acid esters, polyols, surfactants, terpenes, glycerol esters, polyethylene glycol esters, amides, sulfoxides, lactams, nonionic surfactants, sorbitan esters, and mixtures thereof.

12. The matrix transdermal drug delivery device of claim 1, wherein the alkylmethylsiloxane wax is selected from the group consisting of waxes having the following formulations:

space="preserve" listing-type="equation">(RMeSiO).sub.x

wherein R is C_n H_1n+1, Me is CH₃, 14≦

n≦

28, and X is an integer from 4 to 6;

space="preserve" listing-type="equation">RMe.sub.2 SiOSiMe.sub.2 R

wherein Me is CH₃, R is C_n H_2n+1, and n≧

18;

space="preserve" listing-type="equation">RMe.sub.2 SiOSiMe.sub.3

wherein Me is CH₃, R is C_n H_2n+1, and n≧

24;

space="preserve" listing-type="equation">RMeSi(OSiMe.sub.3).sub.2

wherein Me is CH₃, R is C_n H_2n+1, and n≧

24;

space="preserve" listing-type="equation">Me.sub.3 SiO(RMeSiO).sub.x (R'"'"'MeSiO).sub.y SiMe.sub.3

wherein Me is CH₃, R is C_n H_2n+1, and n≧

18, R'"'"' is H or C_n H_2n+1 and n≧

1, when R'"'"' is H or CH₃ then the ratio of X;

Y is greater than 1;

3;

space="preserve" listing-type="equation">RSiO.sub.3/2

wherein R is C_n H_2n+1, and n≧

1;

and mixtures thereof.

13. The matrix transdermal drug delivery device of claim 1, wherein the alkylmethylsiloxane wax is present in an amount between about 1.0 and about 25.0 percent by weight based on total adhesive composition weight.

14. The matrix transdermal drug delivery device of claim 1, wherein the alkylmethylsiloxane wax is present in an amount between about 5 percent and about 15 percent by weight based on total adhesive composition weight.

15. The matrix transdermal drug delivery device of claim 1, wherein the silicone pressure sensitive adhesive containing the alkylmethylsiloxane wax has a dynamic viscosity less than or equal to 800 poise at a temperature equal to or below 200°

C.

16. The matrix transdermal drug delivery device of claim 1, wherein the hot-melt silicone pressure sensitive adhesive composition contains

(a) between about 30 and about 70 percent by weight silicate resin;

(b) between about 22 and about 60 percent by weight silicone fluid; and

(c) between about 1.0 and about 25 percent by weight based of an alkylmethylsiloxane wax,

all weight percents being based on total composition weight.

5. 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 hot-melt silicone pressure sensitive adhesive composition containing a mixture of (i) a silicate resin, (ii) a silicone fluid, and (iii) an alkylmethylsiloxane wax

which decreases dynamic viscosity of the adhesive composition at temperatures ranging from about 50°

C. to about 200°

C. 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 5, wherein the drugs include drugs selected from the group consisting of cardiovascular agents, antiarrhythmic agents, antianginal agents, antibiotics, antifungals, antimicrobials, antihypertensives, analgesics, local anesthetics, contraceptives, hormonal supplements, anti-smoking agents, appetite suppressants, hypnotics, anxiolytics, and mixtures thereof.

7. The reservoir transdermal drug delivery device of claim 5, wherein the co-solvents and excipients are selected from the group consisting of fatty acid esters, polyols, surfactants, terpenes, glycerol esters, polyethylene glycol esters, amides, sulfoxides, lactams, nonionic surfactants, sorbitan esters, and mixtures thereof.

8. The reservoir transdermal drug delivery device of claim 5, wherein the silicone pressure sensitive adhesive is between about 1 and about 15 mils thick.

9. The reservoir transdermal drug delivery device of claim 5, further comprising a rate controlling membrane, said rate controlling membrane being positioned over said reservoir and sealing the reservoir between the backing substrate and the rate controlling membrane.

10. The reservoir transdermal drug delivery device of claim 5, wherein the reservoir is a liquid reservoir.

11. The reservoir transdermal drug delivery device of claim 5, wherein the reservoir is a solid state reservoir.

17. The reservoir transdermal drug delivery device of claim 5, wherein the alkylmethylsiloxane wax is selected from the group consisting of waxes having the following formulations:

space="preserve" listing-type="equation">(RMeSiO).sub.x

wherein R is C_n H_2n+1, Me is CH₃, 14≦

n≦

28, and X is an integer from 4 to 6;

space="preserve" listing-type="equation">RMe.sub.2 SiOSiMe.sub.2 R

wherein Me is CH₃, R is C_n H_2n+1, and n≧

18;

space="preserve" listing-type="equation">RMe.sub.2 SiOSiMe.sub.3

wherein Me is CH₃, R is C_n H_2n+1, and n≧

24;

space="preserve" listing-type="equation">RMeSi(OSiMe.sub.3).sub.2

wherein Me is CH₃, R is C_n H_2n+1, and n≧

24;

space="preserve" listing-type="equation">Me.sub.3 SiO(RMeSiO).sub.x (R'"'"'MeSiO).sub.y SiMe.sub.3

wherein Me is CH₃, R is C_n H_2n+1, and n≧

18, R'"'"' is H or C_n H_2n+1 and n≧

1, when R'"'"' is H or CH₃ then the ratio of X;

Y is greater than 1;

3;

space="preserve" listing-type="equation">RSiO.sub.3/2

wherein R is C_n H_2n+1, and n≧

1;

and mixtures thereof.

18. The reservoir transdermal drug delivery device of claim 5, wherein the alkylmethylsiloxane wax is present in an amount between about 1.0 and about 25. 0 percent by weight based on total adhesive composition weight.

19. The reservoir transdermal drug delivery device of claim 5, wherein the alkylmethylsiloxane wax is present in an amount between about 5 percent and about 15 percent by weight based on total adhesive composition weight.

20. The reservoir transdermal drug delivery device of claim 5, wherein the silicone pressure sensitive adhesive containing the alkylmethylsiloxane wax has a dynamic viscosity less than or equal to 800 poise at a temperature equal to or below 200°

C.

21. The reservoir transdermal drug delivery device of claim 5, wherein the hot-melt silicone pressure sensitive adhesive composition contains

(a) between about 30 and about 70 percent by weight silicate resin;

(b) between about 22 and about 60 percent by weight silicone fluid; and

(c) between about 1.0 and about 25 percent by weight based of an alkylmethylsiloxane wax,

all weight percents being based on total composition weight.