IP Library Granted Patent US 9,758,701
Granted Patent B2
US 9,758,701 · App. 15/285,680 · Granted Sep 12, 2017

Release modifier composition

Inventors: Roy Melvin Griswold (Ballston Spa, NY); Melania Lapinski (Mechanicville, NY)
Assignee: Momentive Performance Materials Inc.
C09J7/0228C08L83/04C09D5/00C09D7/125C09D7/1233C09D183/04C09D183/14C08G77/12C08G77/20C09J2483/005Y10T428/2839
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Quick Facts
Patent No.
US 9,758,701
App. No.
15/285,680
Granted
Sep 12, 2017
Kind
B2
Abstract

There is described a release composition including a polyorganosiloxane polymer and a release modifier. The release modifier includes comprising an alkenyl silsesquioxane an organo functional siloxane of the formula MD x M, wherein M represents R 3 SiO 1/2 , D represents R 2 SiO 2/2 , wherein R is alkyl or alkenyl of 1 to 40 carbon atoms, or hydrogen wherein the organo functional siloxane has a viscosity of from about 5 centipoises to about 80 centipoises and x is from about 5 to about 80, and an optionally a reactive diluent. The release composition includes at least one siloxane cross-linking agent, an inhibitor; and a hydrosilation catalyst.

Claims (33)

1. A release modifier comprising:

i) an alkenyl functional silicone resin represented by structures chosen from M x M Vi y Q or M x D Vi z Q where the sum of x and y range from 0.6 to 1.2, z is 0.05 to 0.25, M represents R 6 3 SiO 1/2 , M Vi represents R 3-p R 1 p SiO 1/2 , D Vi represents R 6 ViSiO 2/2 , Q represents SiO 4/2 , R is selected from the group consisting of one to forty carbon monovalent hydrocarbon radicals, R 1 is selected from the group consisting of two to forty carbon atom olefinic monovalent hydrocarbon radicals, p ranges from 1 to 3, R 6 is alkyl of 1 to 40 carbon atoms,

ii) one or more organo functional siloxanes of the formula MD x M, wherein M represents R 5 3 SiO 1/2 , D represents R 5 2 SiO 2/2 , wherein R 5 is alkyl or alkenyl of 1 to 40 carbon atoms, or hydrogen wherein the organofunctional siloxane has a viscosity of from about 5 centipoise to about 80 centipoise and wherein x is from about 5 to about 80; and

a reactive diluent selected from the group consisting of: α-olefins and vinyl ethers.

2. The release modifier according to claim 1 , wherein z is 0.10 to 0.20.

3. The release modifier of claim 1 , wherein R 5 is an alkyl or alkenyl of 1 to 40 carbon atoms.

4. The release modifier of claim 1 , wherein R 5 is hydrogen.

5. The release modifier according to claim 1 , wherein the organofunctional siloxane is a blend of at least one organofunctional siloxane, wherein R 5 is alkyl or alkenyl of 1 to 40 carbon atoms and at least one organofunctional siloxane, wherein R 5 is hydrogen.

6. The release modifier according to claim 1 , wherein the organo functional siloxane has a viscosity of from about 5 centipoises to about 50 centipoises.

7. The release modifier according to claim 1 , wherein the reactive diluent is an α-olefin selected from the group consisting of 1-octadecene, 1-dodecene, 1-tetradecene, 1-hexandecene, and vinyl cyclohexane.

8. The release modifier according to claim 1 , wherein the reactive diluent is vinyl ether selected from the group consisting of dodecyl vinyl ether, ethyl hexyl vinyl ether, cyclohexyl vinyl ether, butanediol mono and divinyl ether, and diethylene glycol vinyl ether.

9. A release composition comprising the release modifier of claim 1 and a polyorganosiloxane polymer.

10. The release composition of claim 9 , wherein the polyorganosiloxane polymer is represented by:

M vi a T b D c M d

where M vi =R 3-p R 1 p SiO 1/2 , where R is selected from the group consisting of one to forty carbon monovalent hydrocarbon radicals, R 1 is selected from the group consisting of two to forty carbon atom olefinic monovalent hydrocarbon radicals, p ranges from 1 to 3; T=R 2 SiO 3/2 , where R 2 is selected from the group consisting of R and R 1 ; D=R 3 R 4 SiO 2/2 , where R 3 and R 4 are each independently selected from the group consisting of R and R 1 ; and M=R 3 SiO 1/2 , where each R is independently selected, and the subscript a has a value ranging from about 2 to about 5, the subscript b has a value ranging from 0 to 5, c is an integer ranging from about 50 to about 1,000 and d has a value ranging from 0 to 0.5.

11. The release composition of claim 9 , wherein the polyorganosiloxane polymer comprises from about 10 weight percent to about 90 weight percent of the release composition.

12. The release composition of claim 9 , further comprising one or more optional components chosen from one or more reactive diluents, one or more siloxane cross-linking agents, one or more inhibitors, or one or more hydrosilation catalysts.

13. The release composition of claim 12 , wherein the siloxane cross-linking agent comprises SiH-containing polyorganosiloxanes.

14. The release composition according to claim 12 , wherein the siloxane cross-linking agent comprises a substantially linear hydrogen siloxane selected from the group of consisting of:

MD e D′ f M

MD′ f M

MD e D′ f M′

M′D e D′ f M′, and

MD e M′

where M is R 3 SiO 1/2 ,

M′ is H g R 3-g SiO 1/2 ,

D is RRSiO 2/2 where each R is independently selected, and

D′ is RHSiO 2/2 ,

where R is as previously defined, the subscripts e and f may be zero or positive wherein the sum of e and f ranges from about 10 to about 100 subject to the limitation that the sum of f and g is two or greater.

15. The release composition according to claim 12 , wherein the inhibitor is selected from the group consisting of: ethylenically unsaturated amides, aromatically unsaturated amides, acetylenic compounds, ethylenically unsaturated isocyanates, olefinic siloxanes, unsaturated hydrocarbon diesters unsaturated hydrocarbon monoesters of unsaturated acids, conjugated ene-ynes, hydroperoxides, ketones, sulfoxides, amines, phosphines, phosphites, nitrites, and diaziridines.

16. The release composition of claim 12 , wherein the hydrosilation catalyst is metal selected from the group consisting of: nickel, palladium, platinum, rhodium, iridium, ruthenium and osmium.

17. A multi-layered product comprising: (a) a release sheet comprising (i) a carrier and a release film and (ii) an adhesive sheet comprising a carrier and an adhesive film, wherein said release film is formed of the composition of claim 9 , and wherein said release film is in contact with the adhesive film.

18. A substrate, comprising the composition according to claim 9 , disposed on a surface of the substrate and cured.

Assignments (10)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 6, 2016
From: GRISWOLD, ROY MELVIN; LAPINSKI, MELANIA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 039952/0543 →
Continuity (2)
Division 14287606 · May 27, 2014
Related Publication 20170022395A1 · Jan 26, 2017