IP Library Granted Patent US 9,175,198
Granted Patent B2
US 9,175,198 · App. 14/137,074 · Granted Nov 3, 2015

Process for the preparation of a silicone pressure-sensitive adhesive

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Quick Facts
Patent No.
US 9,175,198
App. No.
14/137,074
Granted
Nov 3, 2015
Kind
B2
Abstract

Silicone pressure sensitive adhesive (PSA) compositions and methods for their preparation are provided. In one embodiment, PSAs are formed from a silicone polymer mixture by condensation polymerization of low viscosity polyorganosiloxanes in inert solvents and/or silicone fluids, and optionally adding a silicone resin (MQ) during polymerization. The silicone polymer mixture formed may also be mixed with a silicone resin (MQ) and bodying catalyst, and bodying is allowed to continue until the desired reaction product is formed.

Claims (35)

1. A method of obtaining a silicone pressure-sensitive adhesive composition comprising the sequential steps of:

(I) forming a polymer mixture comprising:

(A) forming a silicone polymer by condensation polymerization of at least one polyorganosiloxane in the presence of at least one hydrocarbon solvent or silicone fluid,

wherein the at least one polyorganosiloxane has an average solution viscosity of from about 1 mm 2 /s to about 200 mm 2 /s at 25° C. and at least one hydroxyl group capable of undergoing condensation polymerization,

wherein polymerization is facilitated by addition of at least one condensation catalyst and occurs at a temperature of from about 30° C. to about 110° C., wherein the silicone polymer formed has a solution viscosity of from about 10,000 mm 2 /s to about 5,000,000 mm 2 /s at 25° C. and has a molecular weight greater than 1,000,000 g/mol and wherein the polymer mixture includes the silicone polymer;

(B) optionally, including a silicone resin that has at least one hydroxyl group capable of undergoing condensation polymerization and that is soluble in at least one hydrocarbon solvent or silicone fluid,

wherein the resin has a hydroxyl group content of from about 0.5% to about 2.5% (by weight based on resin solids content),

wherein the resin comprises R 3 SiO 1/2 units and SiO 4/2 units in a molar ratio of from about 0.6 to about 1.5 (R 3 SiO 1/2 units: SiO 4/2 units),

wherein R is independently selected from a monovalent hydrocarbon or a halohydrocarbon radical having from 1 to 20 carbon atoms, an alkenyl radical, or a hydroxyl radical and wherein the polymer mixture optionally includes the silicone resin; and

(C) optionally, including a neutralizing agent, wherein the neutralizing agent is added in an amount sufficient to neutralize the condensation catalyst and wherein the polymer mixture optionally includes the neutralizing agent;

(II) mixing with the polymer mixture of (I), at least one bodying catalyst and a silicone resin that has at least one hydroxyl group capable of undergoing bodying; and then allowing a bodying reaction to occur at a temperature of from about 40° C. to about 145° C. to form the silicone pressure-sensitive adhesive composition,

wherein the resin is soluble in at least one hydrocarbon solvent or silicone fluid,

wherein the resin has a hydroxyl group content of from about 0.5% to about 2.5% (by weight based on resin solids content),

wherein the silicone resin comprises R 3 SiO 1/2 units and SiO 4/2 units in a molar ratio of from about 0.6 to about 1.5 (R 3 SiO 1/2 units: SiO 4/2 units), and

wherein R is independently selected from a monovalent hydrocarbon or a halohydrocarbon radical having from 1 to 20 carbon atoms, an alkenyl radical, or a hydroxyl radical; and

(III) optionally, adding to the silicone pressure-sensitive adhesive composition of (II) from about 0.5% to about 3.5% (by weight) of an organic peroxide.

2. A method according to claim 1 , wherein the polyorganosiloxane is generally characterized by the formula

R 1 O[R 2 R 3 SiO] x H

wherein R 1 is independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, tert-butyl, perfluorobutylethyl, phenyl ethyl, chloropropyl, fluoropropyl, vinyl, and phenyl and R 2 and R 3 are each independently selected from methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, tert-butyl, perfluorobutylethyl, phenyl ethyl, chloropropyl, fluoropropyl, vinyl, and phenyl; and wherein x is an integer with a value of at least 2.

3. A method according to claim 2 , wherein the polyorganosiloxane is polydimethylsiloxane.

4. A method according to claim 1 , wherein the polyorganosiloxane has a solution viscosity of from about 10 mm 2 /s to about 100 mm 2 /s at 25° C.

5. A method according to claim 1 , wherein the at least one hydrocarbon solvent or silicone fluid is selected from xylene, heptane, benzene, toluene, naptha, mineral spirits, polydimethylsiloxane, isododecane, hexane, and decane.

6. A method according to claim 1 , wherein the condensation catalyst is selected from [PCl 3 ═N—PCl 2 ═N—PCl 3 ] + PCl 6 − .

7. A method according to claim 1 , wherein the silicone polymer has an average viscosity of from about 80,000 mm 2 /s to about 750,000 mm 2 /s at 25° C.

8. A method according to claim 7 , wherein the pressure-sensitive adhesive has from about 20% to about 60% (by weight) of a silicone polymer.

9. A method according to claim 1 , wherein the silicone resin of step (I)(B) undergoes condensation polymerization with the silicone polymer prior to addition of the neutralizing agent.

10. A method according to claim 9 , wherein the silicone resin of step (I)(B) is the same as the silicone resin of step (II).

11. A method according to claim 9 , wherein the silicone resin of step (I)(B) is different from the silicone resin of step (II).

12. A method according to claim 1 , wherein the pressure-sensitive adhesive has from about 40% to about 80% (by weight) of silicone resins.

13. A method according to claim 1 , wherein the organic peroxide of step (III) is selected from benzoyl peroxide and dichlorobenzoyl peroxide.

14. A method according to claim 1 , wherein the pressure-sensitive adhesive has less than 0.1 wt % octamethylcyclotetrasiloxanes or decamethylcyclopentasiloxanes.

15. A method according to claim 1 , wherein the silicone polymer of step (I)(A) comprises branched polyorganosiloxanes.

16. A method according to claim 15 , wherein forming the silicone polymer of step (I)(A) comprises forming the silicone polymer by condensation polymerization in the presence of trialkoxyphenylsilanes, tetraalkoxysilanes, or combinations thereof.

17. A method according to claim 16 , wherein forming the silicone polymer of step (I)(A) comprises forming the silicone polymer by condensation polymerization in the presence of trimethoxyphenylsilane, tetraethoxysilane, or combinations thereof.

18. A method according to claim 1 , wherein the silicone polymer is present in an amount of 50% by weight in solvent.

Assignments (6)
CHANGE OF NAME Recorded Feb 27, 2018
From: DOW CORNING CORPORATION
To: DOW SILICONES CORPORATION
Reel/Frame 045460/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: EKELAND, ROBERT ALAN
To: DOW CORNING CORPORATION
Reel/Frame 036230/0806 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: CRAY, STEPHEN EDWARD
To: DOW CORNING LTD.
Reel/Frame 036230/0837 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: DAVIO, DELPHINE; STAMMER, ANDREAS
To: DOW CORNING EUROPE SA
Reel/Frame 036230/0865 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: DOW CORNING EUROPE SA
To: DOW CORNING CORPORATION
Reel/Frame 036230/0876 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: DOW CORNING LTD.
To: DOW CORNING CORPORATION
Reel/Frame 036230/0983 →