IP Library Granted Patent US 12,227,531
Granted Patent B2
US 12,227,531 · App. 17/989,131 · Granted Feb 18, 2025

Silylated organomodified compounds

Inventors: Cheng Diao (White Plains, NY); Monjit Phukan (West Harrison, NY); Neal Patel (Nyack, NY)
Assignee: Momentive Performance Materials Inc.
C07F7/1804C08G18/289C08G77/388
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Quick Facts
Patent No.
US 12,227,531
App. No.
17/989,131
Granted
Feb 18, 2025
Kind
B2
Abstract

There is provided herein a silylated organo-modified compound which comprises: at least one moiety having the formula (A): wherein the subscript a is 1 or 2, each D is independently NH or O, each of X, Y and Z are independently an unsubstituted or substituted C or N, the dashed lines between X, Y, and Z indicate an optional double bond between either X and Y or Y and Z, with the proviso that when any of X, Y, or Z is a substituted N atom, such substituted N atom does not participate in a double bond, and each Q is independently O or S; and, at least two moieties having the formula (B):

Claims (29)

1. A silylated organo-modified compound, having the formula:

wherein L is a divalent linear or branched alkylene group of from 1 to about 20 carbon atoms and R 1 is a straight chain alkyl of from 1 to about 4 carbon atoms.

2. A silylated organo-modified compound, having the formula:

wherein each R 1 and R 5 are independently a straight chain alkyl of from 1 to about 4 carbon atoms and the subscript n is an integer of from 1 to about 1,000.

3. A silylated organo-modified compound, having the formula:

wherein each R 1 and R 5 are independently a straight chain alkyl of from 1 to about 4 carbon atoms, and optionally wherein one or more R 5 moieties are H, and the subscript n is an integer of from 1 to about 1,000.

4. A silylated organo-modified compound having the formula:

wherein each R 1 is independently a straight chain alkyl of from 1 to about 4 carbon atoms and each L is independently a linear, branched or cyclic alkylene of from 1 to about 8 carbon atoms.

5. A silylated organo-modified compound having the formula:

wherein each R 1 is independently a straight chain alkyl of from 1 to about 4 carbon atoms and each L is independently a linear or branched alkylene of from 1 to about 60 carbon atoms.

6. A process of making the silylated organo-modified compound of claim 1 , the process comprising:

reacting an isocyanato organosilane with at least one of 2,4-diamino-6-hydroxypyrimidine or 2,4,5-triamino-6-hydroxypyrimidine.

7. A process of making the silylated organo-modified compound of claim 1 , the process comprising:

reacting a diisocyanato molecule with at least one of 2,4-diamino-6-hydroxypyrimidine or 2,4,5-triamino-6-hydroxypyrimidine, wherein the diisocyanato molecule is added in molar excess, and reacting the resultant product with amine-functionalized silane to produce the silyated organo-modified compound.

8. A process of making the silylated organo-modified compound of claim 1 , the process comprising reacting isophorone diisocyanate and 2,4-diamino-6-hydroxypyrimidine, wherein the 2,4-diamino-6-hydroxypyrimidine is added in a molar excess amount, and reacting the resultant product with an isocyanato organosilane to produce the silylated organo-modified compound.

9. The process of claim 6 , wherein the isocyanato organosilane is of the general formula:

wherein L is a divalent linear or branched alkylene group of from 1 to about 20 carbon atoms and R 1 is a straight chain alkyl of from 1 to about 4 carbon atoms.

10. The process of claim 6 , further comprising reacting the isocyanato organosilane and the 2,4-diamino-6-hydroxypyrimidine in about a molar equivalent amount, and wherein the resulting product is reacted with triphenylmethane-4,4′,4″-triisocyanate in about molar ratio of about 3:1 to produce the silylated organo-modified compound.

11. The process of claim 6 , further comprising reacting the isocyanato organosilane with 2,4,5-triamino-6-hydroxypyrimidine in a molar ratio of about 2.8:1 to about 3.2:1.

12. A resin composition comprising the silylated organo-modified compound of claim 1 , and a resin selected from the group consisting of polyimide, colorless polyimide, polyetherimide, polyethylene terephthalate, glycol-modified polyethylene terephthalate, polybutylene terephthalate, and mixtures thereof.

13. A flexible copper clad laminate or a flexible display comprising the silylated organo-modified compound of claim 1 .

14. A resin composition comprising the silylated organo-modified compound of claim 2 , and a resin selected from the group consisting of polyimide, colorless polyimide, polyetherimide, polyethylene terephthalate, glycol-modified polyethylene terephthalate, polybutylene terephthalate, and mixtures thereof.

15. A flexible copper clad laminate or a flexible display comprising the silylated organo-modified compound of claim 2 .

16. A resin composition comprising the silylated organo-modified compound of claim 3 , and a resin selected from the group consisting of polyimide, colorless polyimide, polyetherimide, polyethylene terephthalate, glycol-modified polyethylene terephthalate, polybutylene terephthalate, and mixtures thereof.

17. A flexible copper clad laminate or a flexible display comprising the silylated organo-modified compound of claim 3 .

18. A resin composition comprising the silylated organo-modified compound of claim 4 , and a resin selected from the group consisting of polyimide, colorless polyimide, polyetherimide, polyethylene terephthalate, glycol-modified polyethylene terephthalate, polybutylene terephthalate, and mixtures thereof.

19. A flexible copper clad laminate or a flexible display comprising the silylated organo-modified compound of claim 4 .

20. A resin composition comprising the silylated organo-modified compound of claim 5 , and a resin selected from the group consisting of polyimide, colorless polyimide, polyetherimide, polyethylene terephthalate, glycol-modified polyethylene terephthalate, polybutylene terephthalate, and mixtures thereof.

21. A flexible copper clad laminate or a flexible display comprising the silylated organo-modified compound of claim 5 .

Assignments (4)
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 →
Continuity (2)
Provisional Application 63282790 · Nov 24, 2021
Related Publication 20230159571A1 · May 25, 2023
References Cited (13)
US 20040065227A1 · Breton et al. · 2004 [cited by applicant]
US 20060018856A1 · Bosman · 2006 [cited by examiner]
US 20190233592A1 · Yao et al. · 2019 [cited by applicant]
EP 3686232A1 · 2020 [cited by applicant]
FR 2961100A1 · 2011 [cited by applicant]
WO 2011080494A2 · 2011 [cited by applicant]
WO 2015133357A1 · 2015 [cited by applicant]
Kadhirvel (Journal of Chromatography A, 1424, 2015, 59-68). [cited by examiner]
International Search Report for International Application PCT/US2022/050200 dated Feb. 28, 2023. [cited by applicant]
Hirschberg et al, Supramolecular Polymers from Linear Telechelic Siloxanes with Quadruple-Hydrogen-Bonded Units, Scientific Article, Dec. 18, 1998, pp. 2696-2705, Macromolecules. [cited by applicant]
Zha et al, End Groups of Functionalized Siloxane Oligomers Direct Block-Copolymeric or Liquid-Crystalline Self-Assembly Behavior, Scientific Article, Mar. 1, 2016, pp. 5693-5698, Journal of the American Chemical Society. [cited by applicant]
Wipf et al, Synthesis of Chemoreversible Prodrugs of ara-C with Variable Time-Release Profiles. Biological Evaluation of Their Apoptotic Activity, Scientific Article, May 14, 1996, pp. 1585-1596, Pergamon. [cited by applicant]
Stefan Kairies et al., Novel Precursors for Inorganic-Organic Hybrid Materials, Published Jul. 26, 2005, 543-549, Wiley-VCH Verlag GmbH & Co. KGaA, Germany. [cited by applicant]