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

Patent metadata

Field	Value
Publication number	US-2018002583-A1
Application number	US-201615545133-A
Country	US
Kind code	A1
Filing date	Feb 5, 2016
Priority date	Feb 9, 2015
Publication date	Jan 4, 2018
Grant date	—

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

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 -0- 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 or 1;

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 -0- 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 or 1;

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 method 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 . The visco-elastic polymer film of claim 13 , wherein the multi-phase pressure sensitive adhesive is used in a transdermal drug delivery system, a pressure sensitive adhesive film, film former or a medical device attachment.

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 can be tuned by selectively controlling the phase arrangement of th

Assignees

• Dow Corning

Inventors

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

Classifications

• C09J183/10 Primary

  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 title

• A61K31/565

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

• A61K9/7023

  Transdermal patches and similar drug-containing composite devices, e.g. cataplasms (galenical aspects of iontophoretic devices A61K9/0009; microneedle arrays A61K9/0021; buccal patches A61K9/006) · CPC title

• C08G77/442

  containing vinyl polymer sequences · CPC title

• C09J155/005

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