IP Library Granted Patent US 7,446,136
Granted Patent B2
US 7,446,136 · App. 11/165,093 · Granted Nov 4, 2008

Method for producing cure system, adhesive system, and electronic device

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Quick Facts
Patent No.
US 7,446,136
App. No.
11/165,093
Granted
Nov 4, 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 (30)

1. A method of producing a cure system, comprising:

mixing 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 refractory solid is non-reactive with the curing agent.

2. The method as defined in claim 1 , wherein the refractory solid is compatiblized and passivated.

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

4. The method 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 method 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-phenyiglutaric anhydride; propionic acid anhydride; 3,3-tetramethylene glutaric anhydride; or derivatives thereof.

6. The method 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 method 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 method 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 method as defined in claim 1 , wherein the refractory solid comprises silica.

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

11. The method as defined in claim 9 , wherein the silica particles have an average particle size that is nano-scale.

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

13. The method as defined in claim 1 , further comprising admixing a catalyst or an accelerator into the mixture of curing agent and solid.

14. The method as defined in claim 1 , further comprising admixing one or more of pigment, reactive diluent, suspension agent, defoamer, flow modifier, flexibilizer, or flame retardant into the mixture of curing agent and solid.

15. The method as defined in claim 1 , further comprising admixing an adhesion promoter into the mixture of curing agent and solid.

16. The method as defined in claim 2 , wherein the refractory solid comprises one or both of alumina or boron nitride.

17. The method as defined in claim 1 , wherein the refractory 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.

18. A cure system produced by the method as defined in claim 1 .

19. An adhesive system comprising a curable resin and the cure system as defined in claim 18 .

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 19 , wherein the adhesive system has a viscosity at about room temperature that is sufficiently low to enable application of the adhesive system to a substrate surface and to be used as a no-flow underfill.

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

23. A method, comprising: dispersing a compatibilized and passivated refractory solid into a mixture or solution of a low temperature liquid curing agent and a low boiling solvent, wherein the solvent is free of hydroxyl-groups and the curing agent does not react with the solid and wherein the solid has an active termination site density that is less than about 5 per square nanometer; and removing the solvent from the mixture or solution to form a solvent-free liquid dispersion of curing agent and refractory solid.

24. The method as defined in claim 23 , further comprising mixing the dispersion with a curable resin to form an adhesive system.

25. The method as defined in claim 24 , further comprising applying a portion of the adhesive system to a substrate and contacting the portion with an electronic component, and curing the adhesive system to secure the chip to the substrate.

26. A system, comprising:

means for securing a chip to a substrate;

means for curing the securing means and wherein the securing means is the cured polymer layer of claim 22 ; and

means for matching the coefficient of thermal expansion of the securing means to one or both of the chip or substrate, wherein the matching means is dispersed in the curing means.

Assignments (23)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
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 →
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 →
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 →
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 →
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 049194/0085 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
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 034113/0331 →
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 →
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 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 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 019958/0746 →
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 016693/0155 →