Multi-phase silicone acrylic hybrid visco-elastic compositions and methods of making same

Patent metadata

Field	Value
Publication number	US-10316228-B2
Application number	US-201615545133-A
Country	US
Kind code	B2
Filing date	Feb 5, 2016
Priority date	Feb 9, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

A multi-phase silicone acrylic hybrid visco-elastic composition prepared by polymerizing an ethylenically unsaturated monomer and a silicon-containing pressure sensitive adhesive composition comprising acrylate or methacrylate functionality in a first solvent in the presence of an initiator, removing the first solvent, and adding a second solvent to form the multi-phase silicone acrylic hybrid visco-elastic composition. Alternatively, a multi-phase silicone acrylic hybrid visco-elastic composition prepared by polymerizing an ethylenically unsaturated monomer and a silicon-containing pressure sensitive adhesive composition comprising acrylate or methacrylate functionality in a first solvent in the presence of an initiator, adding a processing solvent having a higher boiling point than the first solvent, applying heat to selectively remove a majority of the first solvent, removing the processing solvent, and adding a second solvent to form the multi-phase silicone acrylic hybrid visco-elastic composition. The phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic compositions is selectively controlled by selection of the second solvent.

First claim

What is claimed is:

1. A method of making a multi-phase silicone acrylic hybrid visco-elastic composition comprising the steps of:
(i) providing a silicon-containing pressure sensitive adhesive composition comprising acrylate or methacrylate functionality and the condensation reaction product of:
a silicone resin,
a silicone polymer, and
a silicon-containing capping agent which provides said acrylate or methacrylate functionality, wherein said silicon-containing capping agent is of the general formula XYR′ b SiZ 3-b , wherein
X is a monovalent radical of the general formula AE—
where E is —O— or —NH— and A is an acryl group or a methacryl group,
Y is a divalent alkylene radical having from 1 to 6 carbon atoms,
R′ is a methyl or a phenyl radical,
Z is a monovalent hydrolyzable organic radical or a halogen, and
b is 1, or 2;

wherein the silicone resin and silicone polymer are reacted to form a pressure sensitive adhesive, wherein the silicon-containing capping agent is introduced prior to, during, or after the silicone resin and silicone polymer are reacted, and wherein:
the silicon-containing capping agent reacts with the pressure sensitive adhesive after the silicone resin and silicone polymer have been condensation reacted to form the pressure sensitive adhesive; or
the silicon-containing capping agent reacts in-situ with the silicone resin and silicone polymer;

(ii) polymerizing an ethylenically unsaturated monomer and the silicon-containing pressure sensitive adhesive composition of step (i) in a first solvent in the presence of an initiator at a temperature of from 50° C. to 100° C. to form a silicone acrylic hybrid composition;
(iii) removing the first solvent; and
(iv) adding a second solvent to form the multi-phase silicone acrylic hybrid visco-elastic composition, wherein the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition is selectively controlled by selection of the second solvent.

2. A method of making a multi-phase silicone acrylic hybrid visco-elastic composition comprising the steps of:
(i) providing a silicon-containing pressure sensitive adhesive composition comprising acrylate or methacrylate functionality and the condensation reaction product of:
a silicone resin,
a silicone polymer, and
a silicon-containing capping agent which provides said acrylate or methacrylate functionality, wherein said silicon-containing capping agent is of the general formula XYR′ b SiZ 3-b , wherein
X is a monovalent radical of the general formula AE—
where E is —O— or —NH— and A is an acryl group or a methacryl group,
Y is a divalent alkylene radical having from 1 to 6 carbon atoms,
R′ is a methyl or a phenyl radical,
Z is a monovalent hydrolyzable organic radical or a halogen, and
b is 0, 1 or 2;

wherein the silicone resin and silicone polymer are reacted to form a pressure sensitive adhesive, wherein the silicon-containing capping agent is introduced prior to, during, or after the silicone resin and silicone polymer are reacted, and wherein:
the silicon-containing capping agent reacts with the pressure sensitive adhesive after the silicone resin and silicone polymer have been condensation reacted to form the pressure sensitive adhesive; or
the silicon-containing capping agent reacts in-situ with the silicone resin and silicone polymer;

(ii) polymerizing an ethylenically unsaturated monomer and the silicon-containing pressure sensitive adhesive composition of step (i) in a first solvent in the presence of an initiator at a temperature of from 50° C. to 100° C. to form a silicone acrylic hybrid composition;

(iii) adding a processing solvent, wherein the processing solvent has a higher boiling point than the first solvent, and
(iv) applying heat at a temperature of from 70° C. to 150° C. such that a majority of the first solvent is selectively removed;
(v) removing the processing solvent; and
(vi) adding a second solvent to form the multi-phase silicone acrylic hybrid visco-elastic composition, wherein the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition is selectively controlled by selection of the second solvent.

3. The method of claim 1 or claim 2 , further including the step of blending the silicone acrylic hybrid composition from step (ii) with a non-hybrid pressure sensitive adhesive composition prior to step (iii), wherein the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition is selectively controlled by the blending step.

4. The method of claim 1 , further including the step of blending the multi-phase silicone acrylic hybrid visco-elastic composition with a non-hybrid pressure sensitive adhesive composition after step (iv), wherein the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition is selectively controlled by the blending step.

5. The method of claim 2 , further including the step of blending the multi-phase silicone acrylic hybrid visco-elastic composition with a non-hybrid pressure sensitive adhesive composition after step (vi), wherein the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition is selectively controlled by the blending step.

6. The method of claim 1 or claim 2 , wherein the resulting multi-phase silicone acrylic hybrid visco-elastic composition contains a continuous, silicone external phase and a discontinuous, acrylic internal phase as selectively controlled by selection of the second solvent.

7. The method of claim 1 or claim 2 , wherein the resulting multi-phase silicone acrylic hybrid visco-elastic composition contains a continuous, acrylic external phase and a discontinuous, silicone internal phase as selectively controlled by selection of the second solvent.

8. The method of claim 1 or claim 2 , wherein the second solvent is selected from a volatile silicone, an aliphatic solvent, an aromatic solvent, a ketone, an ester, a halogenated solvent, a mineral spirit, and combinations thereof.

9. The method of claim 1 or claim 2 , wherein where the second solvent is heptane, the multi-phase silicone acrylic hybrid visco-elastic composition contains a silicone external phase.

10. The method of claim 1 or claim 2 , wherein where the second solvent is ethyl acetate, the multi-phase silicone acrylic hybrid visco-elastic composition contains an acrylate external phase.

11. A multi-phase silicone acrylic hybrid visco-elastic composition formed by the method of claim 1 or 2 .

12. A multi-phase silicone acrylic hybrid visco-elastic composition formed by the methods of claim 1 or 2 , wherein the ratio of silicone to acrylate is from 5 to 95 parts silicone to 95 to 5 parts acrylate to selectively control the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition.

13. A visco-elastic polymer film formed by a method of applying the multi-phase silicone acrylic hybrid visco-elastic composition formed by the methods of claim 1 or 2 to a substrate and subsequently removing the second solvent.

14. A transdermal drug delivery system comprising the visco-elastic polymer film of claim 13 .

15. A transdermal drug delivery system comprising at least one active and the multi-phase silicone acrylic hybrid visco-elastic composition formed by the method of claim 1 or 2 , wherein release of an active from the transdermal drug delivery system is capable of being tuned by selectively controlling the phase arrangement of the multi-phase silicone acrylic hybrid visco-elastic composition.

16. The visco-elastic polymer film of

Assignees

• Dow Silicones Corp

Inventors

• Evans Chana Wilson
• Huber Robert O
• Nartker Linda S
• Schalau Ii Gerald K
• Thomas Xavier
• Toth Simon

Classifications

• C09J155/005

  Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond · CPC title

• C09J183/04

  Polysiloxanes · CPC title

• C08F290/068

  Polysiloxanes · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• A61K31/565

  not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol · CPC title