IP Library Granted Patent US 11,104,814
Granted Patent B2
US 11,104,814 · App. 15/043,725 · Granted Aug 31, 2021

Primer formulations with improved photostability

Inventors: Raghuraman Govindan Karunakaran (Hosur, IN); Karthikeyan Murugesan (Bangalore, IN); Indumathi Ramakrishnan (Bangalore, IN); Robert Hayes (Mechanicville, NY)
Assignee: MOMENTIVE PERFORMANCE MATERIALS INC.
C09D7/62C09D5/002C09D5/02C09D5/32C09D133/12C08K9/06
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Quick Facts
Patent No.
US 11,104,814
App. No.
15/043,725
Granted
Aug 31, 2021
Kind
B2
Abstract

A primer composition comprising metal oxide particles modified with an alkyltrialkoxy silane; an organic polymer; and a solvent. The weight ratio of alkyltrialkoxy silane to metal particles is at least 0.9:1. The primer compositions produce films having excellent optical and adhesion characteristics.

Claims (33)

1. A primer composition comprising:

(a) cerium oxide particles, wherein the surface of the cerium oxide particles is modified with a silane such that the silane is applied directly to the cerium oxide particles surface and the silane is of the formula:

where R 1 , R 2 , R 3 , and R 4 are independently chosen from a C1-C10 alkyl;

(b) from about 45 wt. % to about 80 wt. % of an organic polymer based on the dry weight of a film formed from the composition, wherein the organic polymer is chosen from a homopolymer of an alkyl acrylate, a copolymer of an alkyl acrylate, a polycarbonate, a polyvinylpyrrolidone, a polyvinylbutyral, a poly(ethylene terephthalate), poly(butylene terephthalate), or a combination thereof; and

(c) a solvent

wherein the silane is present in an amount of about 10 wt. % to about 30 wt. % based on the dry weight of a film formed from the composition, and the weight ratio of silane to cerium oxide particles is 0.9:1 to 2:1.

2. The primer composition of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently chosen from a C1-C4 alkyl.

3. The primer composition of claim 1 , wherein the solvent is chosen from an alcohol, an acetone, a ketone, an ether, or a combination thereof.

4. The primer composition of claim 1 , wherein the organic polymer is chosen from a homopolymer of an alkyl acrylate, a copolymer of an alkyl acrylate, or a combination thereof.

5. The primer composition of claim 1 , wherein the organic polymer is polycarbonate.

6. The primer composition of claim 1 , wherein the organic polymer is chosen from a polyvinylpyrrolidone, a polyvinylbutyral, or a combination of two or more thereof.

7. The primer composition of claim 1 , wherein the cerium oxide particles have a particle size of about 1 nm to about 190 nm.

8. The primer composition of claim 1 , wherein the cerium oxide particles have a particle size of about 10 nm to about 100 nm.

9. A primer composition comprising:

(a) cerium oxide particles, wherein the surface of the cerium oxide particles, is modified with a silane such that the silane is applied directly to the cerium oxide particles surface and the silane is of the formula:

where R 1 , R 2 , R 3 , and R 4 are independently chosen from a C1-C10 alkyl;

(b) from about 45 wt. % to about 80 wt. % of an organic polymer based on the dry weight of a film formed from the composition, wherein the organic polymer is chosen from a homopolymer of an alkyl acrylate, a copolymer of an alkyl acrylate, a polycarbonate, a polyvinylpyrrolidone, a polyvinylbutyral, a poly(ethylene terephthalate), poly(butylene terephthalate), or a combination thereof; and

(c) a solvent

wherein the silane is present in an amount of about 10 wt. % to about 30 wt. % based on the dry weight of a film formed from the composition, and the weight ratio of silane to cerium oxide particles is 0.9:1 to 2:1, and the composition is free of an ionic surfactant.

10. A method of making a primer composition comprising:

combining (a) cerium oxide particles with (b) an organic polymer chosen from a homopolymer of an alkyl acrylate, a copolymer of an alkyl acrylate, a polycarbonate, a polyvinylpyrrolidone, a polyvinylbutyral, a poly(ethylene terephthalate), poly(butylene terephthalate), or a combination thereof and (c) a solvent, wherein the surface of the cerium oxide particles, is modified with a silane such that the silane is applied directly to the cerium oxide particles surface and the silane is of the formula:

where R1, R2, R3, and R4 are independently chosen from a C1-C10 alkyl, the organic polymer is present in an amount of from about 45 wt. % to about 80 wt. % based on the dry weight of a film formed from the composition, the silane is present in an amount of about 10 wt. % to about 30 wt. % based on the dry weight of a film formed from the composition, and the weight ratio of silane to cerium oxide particles is 0.9:1 to 2:1.

11. A substrate and a primer film disposed on at least a portion of a surface of the substrate, the primer film comprising:

(a) cerium oxide particles wherein the surface of the cerium oxide particles, is modified with a silane such that the silane is applied directly to the cerium oxide surface and the silane is of the formula:

where R 1 , R 2 , R 3 , and R 4 are independently chosen from a C1-C10 alkyl; and

(b) from about 45 wt. % to about 80 wt. % of an organic polymer based on the dry weight of the primer film, wherein the organic polymer is chosen from a homopolymer of an alkyl acrylate, a copolymer of an alkyl acrylate, a polycarbonate, a polyvinylpyrrolidone, a polyvinylbutyral, a poly(ethylene terephthalate), poly(butylene terephthalate), or a combination thereof;

wherein the silane is present in an amount of about 10 wt. % to about 30 wt. % based on the dry weight of the primer film, and the weight ratio of silane to cerium oxide particles is 0.9:1 to 2:1.

12. The substrate of claim 11 , wherein R 1 , R 2 , R 3 , and R 4 are independently chosen from a C1-C4 alkyl.

13. The substrate of claim 11 , wherein the organic polymer is chosen from homo and copolymers of alkyl acrylates, polycarbonate, polyvinylpyrrolidone, polyvinylbutyral, poly(ethylene terephthalate), poly(butyl ene terephthalate), or a combination thereof.

14. The substrate of claim 11 , wherein the primer film comprises (i) the cerium oxide particles in an amount of from about 10 wt. % to about 25 wt. %, and (ii) the silane in an amount of from about 10 wt. % to about 30 wt. %, the wt. % being based on the weight of the dry film, and wherein the weight ratio of silane to cerium oxide particles is 1:1.

15. The substrate of claim 11 , wherein the primer film comprises the cerium oxide particles in an amount of about 10 wt. % to about 20 wt. % and the silane in an amount of from about 10 wt. % to about 20 wt. %, the wt. % being based on the weight of the dry film.

16. The substrate of claim 11 , wherein the substrate is chosen from an acrylic polymer, a polyamide, a polyimide, an acrylonitrile-styrene copolymer, a styrene-acrylonitrile-butadiene terpolymer, a polyvinyl chloride, a polyolefin, a polycarbonate, a copolycarbonate, or a combination thereof.

17. The substrate of claim 11 comprising a silicone hardcoat overlying the primer film.

Assignments (10)
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 PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
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 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 21, 2017
From: KARUNAKARAN, RAGHURAMAN GOVINDAN; MURUGESAN, KARTHIKEYAN; RAMAKRISHNAN, INDUMATHI; HAYES, ROBERT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 041656/0452 →