IP Library Granted Patent US 7,405,246
Granted Patent B2
US 7,405,246 · App. 11/165,092 · Granted Jul 29, 2008

Cure system, adhesive system, electronic device

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Quick Facts
Patent No.
US 7,405,246
App. No.
11/165,092
Granted
Jul 29, 2008
Kind
B2
Abstract

A cure system including a compatiblized and passivated refectory solid dispersed within a low temperature liquid curing agent is provided. An adhesive system including the cure system is provided, and an associated method. A device including the cured adhesive system is provided.

Claims (31)

1. A cure system, comprising:

a curing agent that is a low temperature liquid; and

a finely divided refractory solid, wherein the solid has an active termination site density that is less than about 5 per square nanometer and, wherein the solid is non-reactive relative to the curing agent.

2. The cure system as defined in claim 1 , wherein the solid is compatibilized and passivated.

3. The cure system as defined in claim 2 , wherein the curing agent comprises an anhydride.

4. The cure system as defined in claim 3 , wherein the anhydride comprises one or more aromatic carboxylic acid anhydride, aliphatic carboxylic acid anhydride, cycloaliphatic carboxylic acid anhydride, or siloxane dianhydride.

5. The cure system as defined in claim 3 , wherein the anhydride comprises one or more of benzoic anhydride; phthalic anhydride; hexahydro phthalic anhydride; methyl-hexahydro phthalic anhydride (MHHPA); 4-nitrophthalic anhydride; naphthalene tetracarboxylic acid dianhydride; naphthalic anhydride; tetrahydro phthalic anhydride; cyclohexane dicarboxylic anhydride; butanoic anhydride; dodecenyl succinic anhydride; 2,2-dimethyl glutaric anhydride; ethanoic anhydride; glutaric anhydride; hexafluoro glutaric acid anhydride; itaconic anhydride; tetrapropenylsuccinic anhydride; maleic anhydride; 2-methyl glutaric anhydride; 2-methyl propionic anhydride 1,2-cyclohexane dicarboxylic anhydride; octadecyl succinic anhydride; 2-octenyl succinic anhydride; n-octenyl succinic anhydride; 2-phenylglutaric anhydride; propionic acid anhydride; 3,3-tetramethylene glutaric anhydride; or derivatives thereof.

6. The cure system as defined in claim 1 , wherein the curing agent is a liquid at a temperature in a range of less that about 100 degrees Celsius.

7. The cure system as defined in claim 6 , wherein the curing agent is a liquid at a temperature in a range of less that about 50 degrees Celsius.

8. The cure system as defined in claim 7 , wherein the curing agent is a liquid at a temperature in a range of from about 25 degrees Celsius to about 35 degrees Celsius.

9. The cure system as defined in claim 1 , wherein the refractory solid comprises silica.

10. The cure system as defined in claim 9 , wherein the silica comprises silica particles.

11. The cure system as defined in claim 10 , wherein the silica particles have an average particle size that is nano-scale.

12. The cure system as defined in claim 11 , wherein the silica particles have an average particle size in a range of less than about 100 nanometers.

13. The cure system as defined in claim 1 , further comprising a catalyst or an accelerator.

14. The cure system as defined in claim 1 , further comprising one or more of pigment, reactive diluent, defoamer, flow modifier, flexibilizer, or flame retardant.

15. The cure system as defined in claim 1 , further comprising an adhesion promoter.

16. The cure system as defined in claim 1 , wherein the solid comprises one or both of alumina or boron nitride.

17. The cure system as defined in claim 1 , wherein the solid is present in an amount in a range of greater than about 30 weight percent based on the total weight of the composition.

18. The cure system as defined in claim 17 , wherein the solid is present in an amount in a range of from about 30 weight percent to about 70 weight percent based on the total weight of the composition.

19. An adhesive system comprising the cure system as defined in claim 1 , and further comprising a curable resin.

20. The adhesive system as defined in claim 19 , wherein the curable resin comprises one or more epoxy or oxirane moiety.

21. The adhesive system as defined in claim 20 , wherein the epoxy comprises one or more aliphatic epoxy resin, cycloaliphatic epoxy resin, or aromatic epoxy resin.

22. The adhesive system as defined in claim 19 , wherein the curable resin is present relative the cure system in a stoichiometric ratio in a range of about 1:1.

23. The adhesive system as defined in claim 19 , wherein the curable resin comprises a filler prior to mixing with the cure system.

24. A cured polymer layer comprising the adhesive system as defined in claim 19 .

25. An electronic device, comprising: a substrate; a chip secured to the substrate; and a cured polymer layer as defined in claim 24 disposed between the chip and the substrate.

26. A solvent-free adhesive system for use in an electronic device, comprising:

a curable resin comprising a first portion of refractory solid; and

a cure system operable to cure the resin, the cure system comprising a curing agent and a second portion of refractory solid, wherein the refractory solid is present in an amount greater than about 30 percent by weight relative to the total weight of the adhesive system and wherein the first and second portion of refractory solids each have an active termination site density that is less than about 5 per square nanometer.

27. The adhesive system as defined in claim 26 , wherein a mixture of the resin and the curing agent has a viscosity at about room temperature that is sufficiently low to enable application of the mixture to a substrate surface and to use as a no-flow underfill.

Assignments (27)
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
RELEASE OF SECURITY INTEREST Recorded Dec 24, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054883/0855 →
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
Reel/Frame 054387/0001 →
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →
SECURITY AGREEMENT Recorded Jul 1, 2009
From: MOMENTIVE PERFORMANCE MATERIALS, INC.; JUNIPER BOND HOLDINGS I LLC; JUNIPER BOND HOLDINGS II LLC; JUNIPER BOND HOLDINGS III LLC; JUNIPER BOND HOLDINGS IV LLC; MOMENTIVE PERFORMANCE MATERIALS CHINA SPV INC.; MOMENTIVE PERFORMANCE MATERIALS QUARTZ, INC.; MOMENTIVE PERFORMANCE MATERIALS SOUTH AMERICA INC.; MOMENTIVE PERFORMANCE MATERIALS USA INC.; MOMENTIVE PERFORMANCE MATERIALS WORLDWIDE INC.; MPM SILICONES, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL TRUSTEE
Reel/Frame 022902/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2007
From: GENERAL ELECTRIC COMPANY
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 019958/0749 →
SECURITY AGREEMENT Recorded Jul 3, 2007
From: MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 019511/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2005
From: RUBINSZTAJN, SLAWOMIR
To: GENERAL ELECTRIC COMPANY
Reel/Frame 016724/0726 →