IP Library Granted Patent US 11,466,126
Granted Patent B2
US 11,466,126 · App. 17/132,350 · Granted Oct 11, 2022

Condensation curable composition comprising siloxane-imide base polymer

Inventors: Subrata Mandal (Bangalore, IN); Tetsuo Fujimoto (Gunma, JP); Debanga B. Konwar (Bangalore, IN)
Assignee: Momentive Performance Materials Inc.
C08G77/455C08G77/08C08G77/16C08G77/70C08G77/80C08K3/22C08K5/5419C08G2150/00C08G2170/00C08K2003/2272
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Quick Facts
Patent No.
US 11,466,126
App. No.
17/132,350
Granted
Oct 11, 2022
Kind
B2
Abstract

A condensation curable silicone adhesive composition comprising a siloxane-imide base polymer, condensation curable organopolysiloxane crosslinker, a condensation catalyst and an additive is shown and described herein. The composition is curable at relatively room temperatures and shows good heat stability.

Claims (29)

1. A condensation curable composition comprising: (a) a silicone-imide base polymer; (b) a crosslinker; (c) a condensation cure catalyst; and (d) optionally, an additive, wherein the silicone-imide polymer (a) is selected from a compound of the formula (I):

wherein R 1 is chosen from a C5-C20 aryl or a polycyclic aryl group comprising two or more C5-C20 aryl groups, where R 1 is optionally unsubstituted or substituted with a C1-C6 alkyl, a halogen, a haloalkyl, a hydroxy, and/or a C1-C5 alkoxy groups;

C 1 can be chosen from C1 to C5 alkyl, a C5-C20 aryl, a C7-C16 arylalkyl, or a C7-C16 alkylaryl;

R 2 , R 3 , and R 4 may be same or different from one another, and are selected from a C1-C3 alkyl or phenyl;

R 5 may be same or different and can be chosen from C1-C30 alkyl, a C1-C30 alkoxy group, a C1-C30 acetoxy group, or a C1-C30 ketoxime group;

m is an integer between 1 and 30; and

n is an integer between 1 and 200.

2. The curable silicone composition of claim 1 , wherein R 1 is selected from benzene, naphthalene, benzophenone, biphenyl, a biphenyl alkane, biphenylether, isopropylidinediphenylphenoxy, biphenyl sulfone, biphenyl sulfide, norbornyl and hexafluoromethylbiphenyl.

3. The curable composition of claim 1 , wherein R 1 is benzene.

4. The curable composition of claim 1 , comprising the silicone-imide base polymer (a) in an amount of from about 40 weight % to about 95 weight % based on the total parts by weight of the curable silicone composition.

5. The curable composition of claim 1 , wherein the silicone-imide base polymer (a) is present in an amount of from about 50 weight % to about 91 weight % based on the total parts by weight of the curable silicone composition.

6. The curable silicone composition of claim 1 , wherein the crosslinker (b) is selected from an alkoxysilane, an alkoxysilicate, an alkoxysiloxane, an oximosilane, an oximosiloxane, an enoxysilane, an enoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkarylaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, or a combination of two or more thereof.

7. The curable composition of claim 6 , wherein the crosslinker (b) is selected from tetraethylorthosilicate (TEOS), methyltrimethoxysilane (MTMS), or a combination thereof.

8. The curable composition of claim 1 , comprising the crosslinker (b) in an amount of from about 0.5 parts to about 50 parts based on the total parts by weight of the curable silicone composition.

9. The curable composition of claim 1 , comprising the crosslinker (b) in an amount of from about 5 parts to about 10 parts based on the total parts by weight of the curable silicone composition.

10. The curable silicone composition of claim 1 , wherein the catalyst (c) is selected from (i) a metal or organometal catalyst comprising a metal selected from Ca, Ce, Bi, Fe, Mo, Mn, Pb, Ti, V, Zn, Sn, and Y, or (ii) a non-tin catalyst comprising a carboxylic acid component, an amino containing silane, and optionally an amino containing siloxane component.

11. The curable silicone composition of claim 10 , wherein the organometal catalyst is dibutyltin dilaurate.

12. The curable composition of claim 1 , comprising the catalyst (c) in an amount of from about 0.01 parts to about 5 parts based on the total parts by weight of the curable silicone composition.

13. The curable silicone composition of claim 1 , wherein the additive (d) is selected from a filler, a pigment, a lubricant, a viscosity modifier, an antioxidant, a photostabilizer, a heat stabilizer, a flame retardant, an inhibitor, an adhesion promoter, or a combination of two or more thereof.

14. The curable composition of claim 13 , wherein the additive (d) is a filler selected from SiO 2 , TiO 2 , MgO, ZnO, CaCO 3 , CeO 2 , Fe 2 O 3 , SiC, Clay Material, Graphene Oxide, Boron Oxide, BN, Carbon Nano Tube, Zirconium Oxide, Fly Ash, Zr(OEt) 4 , Ti(OEt) 4 , a powder form of any Polyimide, Polybenzimidazole, Polyamideimide, Poly BPA Sulfone, Siloxane-Polyimide, Siloxane-Benzimidazole, Siloxane-Polysulfones, a combination of two or more thereof.

15. The curable composition of claim 14 , wherein the filler is Fe 2 O 3 .

16. The curable composition of claim 14 , comprising the filler in an amount of from about 0 parts to about 50 parts by weight based on the total weight of the curable composition.

17. The curable composition of claim 14 , comprising the filler in an amount of from about 10 parts to about 40 parts by weight based on the total weight of the curable silicone composition.

18. A cured silicone-imide material formed from the composition of claim 1 .

19. The cured silicone-imide material of claim 18 having a thermal degradation of 400° C. to 600° C. as measured by thermogravimetric analysis.

20. The cured material of claim 18 , wherein the cured silicone-imide material is employed on or as part of an article in an aerospace device, an electronic device, an electronic component, an automobile, insulation, a coating, or a solvent resistant membranes.

21. An article comprising a substrate, wherein the silicone-imide composition of claim 1 is coated or adhered on a surface of the substrate.

22. The article of claim 21 , wherein the substrate comprises a material selected from a plastic material, a ceramic, a glass, a rubber material, a filled metal, a metal alloy, a metallized plastic, a coated or painted metal, or a combination of two or more thereof.

23. The article of claim 21 , wherein the substrate material is selected from an acrylic polymer, a polyester, a polyamide, a polyimide, an acrylonitrile-styrene copolymer, a styrene-acrylonitrile-butadiene terpolymer, polyvinyl chloride, polyethylene, polycarbonate, a copolycarbonate, or a combination of two or more thereof.

Assignments (5)
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 →
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 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2021
From: MANDAL, SUBRATA; FUJIMOTO, TETSUO; KONWAR, DEBANGA B.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 055047/0987 →
Continuity (1)
Related Publication 20220195125A1 · Jun 23, 2022