IP Library Granted Patent US 8,217,107
Granted Patent B2
US 8,217,107 · App. 11/728,904 · Granted Jul 10, 2012

Rapid deep-section cure silicone compositions

Assignee: Momentive Performance Materials Inc.
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Quick Facts
Patent No.
US 8,217,107
App. No.
11/728,904
Granted
Jul 10, 2012
Kind
B2
Abstract

The present invention relates to room-temperature curable silicone compositions possessing rapid deep-section cure. The silicone sealant compositions of the present invention find application in insulating glass units as elements of windows, skylights, doors and related products.

Claims (44)

1. A curable sealant composition comprising:

a) at least one silanol-terminated diorganopolysiloxane;

b) at least one crosslinker for the silanol-terminated diorganopolysiloxane(s) selected from the group consisting of cross-linkers possessing the general formula:

(R 7 O)(R 8 O)(R 9 O)(R 10 O)Si

where R 7 , R 8 , R 9 and R 10 are independently chosen monovalent C 1 to C 60 hydrocarbon radicals and methyltrimethoxysilane;

c) at least one catalyst for the crosslinking reaction;

d) a rapid deep-section curing amount of zinc oxide having an average particle size of from about 50 nm to about 70 nm and possessing a surface area of from about 5 to 30 m 2 /gram;

e) at least one additional component selected from the group consisting of alkyl-terminated diorganopolysiloxane, filler, UV stabilizer, antioxidant, adhesion promoter, cure accelerator, thixotropic agent, plasticizer, moisture scavenger, pigment, dye, surfactant, solvent and biocide; and,

wherein the composition when cured achieves a level of deep-section cure in 24 hours which is at least 7 percent greater and a level of cure in 48 hours which is at least 10 percent greater than an equivalent composition cured over the same period in the absence of zinc oxide.

2. The curable sealant composition of claim 1 wherein the diorganopolysiloxane polymer, component (a), is a silanol terminated diorganopolysiloxane having the formula:

M a D b D′ c

wherein a=2, b is equal to or greater than 1, c is zero or a positive integer;

M=(HO) 3-x-y R 1 x R 2 y SiO 1/2 ;

wherein x=0, 1 or 2 and y is either 0 or 1, with the proviso that x+y is less than or equal to 2, R 1 and R 2 are monovalent C1 to C60 hydrocarbon radicals;

D=R 3 R 4 SiO 1/2 ;

wherein R 3 and R 4 are monovalent C1 to C60 hydrocarbon radicals; and

D′=R 5 R 6 SiO 2/2 ;

wherein R 5 and R 6 are independently chosen monovalent C1 to C60 hydrocarbon radicals.

3. The curable sealant composition of claim 1 wherein the crosslinker, component (b), is at least one selected from the group consisting of tetra-N-propylsilicate, and tetraethylortho silicate.

4. The curable sealant composition of claim 1 wherein the catalyst, component (c), is a tin catalyst.

5. The curable sealant composition of claim 4 wherein the tin catalyst is at least one selected from the group consisting of dibutyltindilaurate, dibutyltindiacetate, dibutyltindimethoxide, tinoctoate, isobutyltintriceroate, dibutyltinoxide, solubilized dibutyl tin oxide, dibutyltin bis-diisooctylphthalate, bis-tripropoxysilyl dioctyltin, dibutyltin bis-acetylacetone, silylated dibutyltin dioxide, carbomethoxyphenyl tin tris-uberate, isobutyltin triceroate, dimethyltin dibutyrate, dimethyltin di-neodecanoate, triethyltin tartarate, dibutyltin dibenzoate, tin oleate, tin naphthenate, butyltintri-2-ethylhexylhexoate, tinbutyrate, and diorganotin bis β-diketonates.

6. The curable sealant composition of claim 1 wherein the catalyst, component (c), is a titanium compound.

7. The curable sealant composition of claim 6 wherein the titantium compound is at least one selected from the group consisting of Di(isopropoxide) Titanium bis(ethylacetoacetate), Di(isobutoxide) Titanium bis(ethylacetoacetato), Di(n-butoxide) Titanium bis(ethylacetoacetato), 1,3-propanedioxytitanium bis(ethylacetoacetate), Titanium (triethanolaminato)isopropoxide, Bis(triethanolamino) titanium di(methyl diglycolate), Titanium diisopropoxide (bis-2,4-pentanedionate), Titanium ethoxide isopropoxide bis-(2,4-pentanedionate), Titanium bis-(2,4-pentanedionate) (2-EHA), tetra n-butyl titanate, and tetra-isopropyl titanate.

8. The curable sealant composition of claim 7 wherein the titanium compound is Di(isopropoxide) Titanium bis(ethylacetoacetate).

9. The curable sealant composition of claim 1 wherein the adhesion promoter is selected from the group consisting of n-2-aminoethyl-3-aminopropyltrimethoxysilane, 1,3,5-tris(trimethoxysilylpropyl)isocyanurate, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, aminopropyltrimethoxysilane, bis-γ-trimethoxysilypropyl)amine, N-Phenyl-γ-aminopropyltrimethoxysilane, triaminofunctionaltrimethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropylmethyldiethoxysilane, methacryloxypropyltrimethoxysilane, methylaminopropyltrimethoxysilane, γ-glycidoxypropylethyldimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxyethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)propyltrimethoxysilane, β-(3,4-epoxycyclohexyl) ethylmethyldimethoxysilane, isocyanatopropyltriethoxysilane, isocyanatopropylmethyldimethoxysilane, β-cyanoethyltrimethoxysilane, γ-acryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, 4-amino-3,3,-dimethylbutyltrimethoxysilane, n-ethyl-3-trimethoxysilyl-2-methylpropanamine, and mixtures thereof.

10. The curable sealant composition of claim 1 wherein the optional filler is selected from the group consisting of clays, nano-clays, organo-clays, ground calcium carbonate, precipitated calcium carbonate, colloidal calcium carbonate, calcium carbonate treated with compounds stearate or stearic acid; fumed silica, precipitated silica, silica gels, hydrophobized silicas, hydrophilic silica gels, crushed quartz, ground quartz, alumina, aluminum hydroxide, titanium hydroxide, clay, kaolin, bentonite montmorillonite, diatomaceous earth, iron oxide, carbon black and graphite, talc, mica, and mixtures thereof.

11. The curable sealant composition of claim 1 comprising a non-ionic surfactant selected from the group consisting of polyethylene glycol, polypropylene glycol, ethoxylated castor oil, oleic acid ethoxylate, alkylphenol ethoxylates, copolymers of ethylene oxide and propylene oxide, and mixtures thereof in an amount ranging from about 0.1 weight percent to about 10 weight percent.

12. The curable sealant composition of claim 1 wherein the diorganopolysiloxane polymer, component (a), ranges from in amount from about 5 weight percent to about 95 weight percent of the total composition.

13. The curable sealant composition of claim 1 wherein the diorganopolysiloxane polymer, component (a), ranges from in amount from about 20 weight percent to about 85 weight percent of the total composition.

14. The curable sealant composition of claim 1 wherein the diorganopolysiloxane polymer, component (a), ranges from in amount from about 30 weight percent to about 60 weight percent of the total composition.

15. The curable sealant composition of claim 1 wherein the amount of the cross-linker, component (b), ranges in amount from about 0.1 weight percent to about 10 weight percent of the total composition.

16. The curable sealant composition of claim 1 wherein the amount of the cross-linker, component (b), ranges in amount from about 0.3 weight percent to about 5 weight percent of the total composition.

17. The curable sealant composition of claim 1 wherein the amount of the cross-linker, component (b), ranges in amount from about 0.5 weight percent to about 1.5 weight percent of the total composition.

18. The curable sealant composition of claim 1 wherein the total amount of catalyst, component (c), ranges in amount from about 0.001 weight percent to about 1 weight percent of the total composition.

19. The curable sealant composition of claim 1 wherein the total amount of catalyst, component (c), ranges in amount from about 0.003 weight percent to about 0.5 weight percent of the total composition.

20. The curable sealant composition of claim 1 wherein the total amount of catalyst, component (c), ranges in amount from about 0.005 weight percent to about 0.2 weight percent of the total composition.

21. The curable sealant composition of claim 1 wherein the amount of zinc oxide, component (d), ranges in amount from about 1 to about 60 weight percent of the total composition.

22. The curable sealant composition of claim 1 wherein the amount of zinc oxide, component (d), ranges in amount from about 2 to about 30 weight percent of the total composition.

23. The curable sealant composition of claim 1 wherein the amount of zinc oxide, component (d), ranges in amount from about 5 to about 20 weight percent of the total composition.

24. The curable sealant composition of claim 1 wherein the amount of filler, ranges in amount from 0 to about 90 weight percent of the total composition.

25. The curable sealant composition of claim 1 wherein the amount of adhesion promoter ranges in amount from about 0.5 weight percent to about 20 weight percent of the total composition.

26. The cured composition of claim 1 .

27. A cured sealant comprising the curable sealant composition of claim 1 .

28. The curable sealant composition of claim 1 wherein the rapid deep-section curing amount of zinc oxide is from about 10 weight percent to about 30 weight percent of the total weight of the composition.

Assignments (26)
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 10, 2020
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
Reel/Frame 054372/0391 →
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 →
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 →
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 - 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 →
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 →
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 034066/0662 →
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
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SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
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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 →
SECURITY AGREEMENT Recorded Jul 2, 2008
From: MOMENTIVE PERFORMANCE MATERIALS, INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
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ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2007
From: RAMAKRISHNAN, INDUMATHI; NESAKUMAR, EDWARD J.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 019166/0019 →
Continuity (1)
Related Publication 20080242763A1 · Oct 2, 2008