IP Library Granted Patent US 8,728,345
Granted Patent B2
US 8,728,345 · App. 13/329,430 · Granted May 20, 2014

Epoxy-containing polysiloxane oligomer compositions, process for making same and uses thereof

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Quick Facts
Patent No.
US 8,728,345
App. No.
13/329,430
Granted
May 20, 2014
Kind
B2
Abstract

The present invention relates to stable, zero or low VOC epoxy-containing polysiloxane oligomer compositions that provide for a high degree of chemical resistance to compositions containing organic resins, while at the same time, maintaining or improving the flexibility of these organic resin-containing compositions, to processes for preparing epoxy-containing polysiloxane oligomer compositions, and to uses in coatings, sealants, adhesives, and composites containing the same.

Claims (20)

1. An epoxy-containing polysiloxane oligomer composition comprising,

(i) from 5 to 65 mole percent of a polysiloxane of the Formula (I):

(ii) from 10 to 55 mole percent of a polysiloxane of the Formula (II):

(iii) from 5 to 45 mole percent of a polysiloxane of the Formula (III):

(iv) from 1 to 20 mole percent of a polysiloxane of the Formula (IV):

(v) from 0.1 to 20 mole percent of a polysiloxane of the Formula (V):

wherein each occurrence of R 1 is —CH 2 CH 2 CH 2 — and the mole percent of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v).

2. The epoxy-containing polysiloxane oligomer composition of claim 1 , wherein component (i) is from 9 to 30 mole percent, component (ii) is from 30 to 50 mole percent; component (iii) is from 20 to 40 mole percent; component (iv) is from 5 to 18 mole percent; component (v) is from 2 to 8 mole percent, wherein the mole percent of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v).

3. The epoxy-containing polysiloxane oligomer composition of claim 2 , wherein component (i) is from 10 to 20 mole percent, component (ii) is from 35 to 48 mole percent; component (iii) is from 25 to 35 mole percent; component (iv) is from 7 to 15 mole percent; and component (v) is from 3 to 6 mole percent, wherein the mole percent of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v).

4. The epoxy-containing polysiloxane oligomer composition of claim 1 wherein the polysiloxane oligomer composition has a viscosity of from 50 centistokes to 250 centistokes at 20° C. in accordance with ASTM method D-1545.

5. The epoxy-containing polysiloxane oligomer composition of claim 1 wherein the polysiloxane oligomer composition has a number average molecular weight of from 500 grams per mole to 700 grams per mole.

6. The epoxy-containing polysiloxane oligomer composition of claim 1 wherein the polysiloxane oligomer composition has less than 1 weight percent releasable alcohol, based upon the sum of the weights for components (i), (ii), (iii), (iv) and (v).

7. The epoxy-containing polysiloxane oligomer composition of claim 1 further comprising a stabilizing agent having the Formula (VII):

R 4 (OR 5 ) p   (VII)

wherein:

R 4 is a boron atom, a HP(═O)(−) 2 group, a P(═O)(−) 3 group, a R 6 C(═O)(−) group a polyvalent hydrocarbon group containing from 3 to 20 carbon atoms;

each R 5 is independently a hydrogen, a R 6 C(═O)(−) group, or a hydrocarbon containing from 1 to 6 carbon atoms;

each R 6 is independently a monovalent hydrocarbon containing from 1 to 5 carbon atoms; and

p is an integer of from 1 to 6.

8. The polysiloxane composition of claim 7 wherein the stabilizing agent is selected from the group consisting of boric acid, phosphoric acid, phosphorus acid, acetic acid, acetic acid anhydride, glycerol, 2-methyl-1,3-propanediol, 1-methoxy-2,3-propanediol, 1,2-hexanediol, and 2,3-dimethyl-2,3-butanediol.

Assignments (22)
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 PATENT RIGHTS Recorded May 4, 2023
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063548/0383 →
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 →
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 →
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 - 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
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 →