IP Library Patent Application 16042127
Patent Application
App. No. 16/042,127

CRACK RESISTANT COATING COMPOSITION AND METHOD OF MAKING THEREOF

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Quick Facts
Patent No.
US None
App. No.
16/042,127
Filed
Jul 23, 2018
Art Unit
1787
USPC
428/447
Abstract

Provided is a coating composition comprising (a) a component A of the formula (R 1 ) d Si(OR 2 ) 4−d , wherein R 1 is a C1-C3 monovalent hydrocarbon, R 2 is an R 1 or a hydrogen radical and d is 0, 1 or 2; (b) a component B selected from the group consisting of (R 3 ) a Si(OR 4 ) 4−a (Formula 1) and/or (R 5 O) m (R 6 ) n Si(R 9 ) x (R 10 ) y Si(R 11 ) z Si(R) o (OR 7 ) p (Formula 2); (c) metal oxide particles; (d) UV absorber; (e) a catalyst; and (f) a solvent. The coating composition may provide a coating exhibiting good optical properties as well as durability, abrasion resistance, and/or crack resistance.

Claims (87)

1 . A composition comprising:

Component A of the formula (R 1 ) d Si(OR 2 ) 4−d , wherein R 1 is a C 1 -C 3 monovalent hydrocarbon, R 2 is a C 1 -C 3 monovalent hydrocarbon or a hydrogen radical and d is 0, 1, or 2, and

Component B, is selected from the group consisting of Formula 1, Formula 2, or a combination thereof:

(R 3 ) a Si(OR 4 ) 4−a   Formula 1

(R 5 O) m (R 6 ) n Si(R 9 ) x (R 10 ) y (R 11 ) z Si(R 8 ) s (OR 7 ) p   Formula 2

wherein R 3 is chosen from a C 5 -C 20 linear or branched alkyl radical, a C 5 -C 20 fluoroalkyl, a mixture of hydrocarbon and fluorocarbon chain, C 5 -C 20 linear or branched hydrocarbon chain containing thioester group, C 6 -C 24 saturated or unsaturated linear or cyclic hydrocarbon chain containing amino group or urea group, R 4 is C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical; a is 0, 1, 2, to 3;

R 5 and R 7 are independently chosen from a C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical;

R 6 and R 8 are independently selected from a C 1 to C 3 monovalent hydrocarbon radical or a hydrogen radical; m and p are 1 to 3; n and s are 1 to 3 such that m+n is 3, and s+p is 3;

R 9 is chosen from a C 1 -C 24 divalent hydrocarbon radical;

R 10 and R 11 are independently chosen from C 1 to C 24 monovalent hydrocarbon radical;

x is 1 to 20, y is 0 to 20, and z is 0 to 20;

metal oxide particles;

UV absorber;

a catalyst; and

a solvent.

2 . The composition of claim 1 , wherein the component B is present in an amount of about 1 weight percent to about 60 weight percent based on the total weight of the component A and the component B.

3 . The composition of claim 1 , wherein R 3 of component B is chosen from pentyl, hexyl, heptyl, octyl, nonyl decyl, dodecyl, 3,3,3-triflurorpentyl, 3,3,3-triflurorhexyl, 3,3,3-trifluroheptyl, 3,3,3-triflurooctly, perfluoropentyl, pefluorohexyl, pefluoroheptyl, or perfluorohexyl.

4 . The composition of claim 1 , wherein R 4 is chosen from methyl or ethyl.

5 . The composition of claim 1 , wherein component B is chosen from a silane of Formula 2 having the formula 2a:

(R 5 O) m (R 6 ) n Si—Z—Si(R 8 ) s (OR) p   2a

where Z is a C 1 -C 24 bivalent hydrocarbon radical.

6 . The composition of claim 5 , wherein the bivalent hydrocarbon radical Z is of the formula —R 21 —R 23 —R 22 — where R 21 and R 22 are independently C 1 -C 6 bivalent hydrocarbon groups, and R 23 is a C 5 -C 10 bivalent cyclic group, which may be saturated, unsaturated, or aromatic.

7 . The composition of claim 1 , wherein component A is methyltrimethoxy silane.

8 . The composition of claim 1 , wherein the metal oxide particles are present in an amount of from about 0.1 weight percent to about 50 weight percent based on the weight of the composition.

9 . The composition of claim 1 , wherein the metal oxide particles are chosen from silica, zirconia, titania, alumina, ceria, tin oxide, zinc oxide, antimony oxide, or a combination of two or more thereof.

10 . The composition of claim 1 , wherein the metal oxide particles have an average particle size of from about 1 nm to about 250 nm.

11 . The composition of claim 1 further comprising additives selected from an antioxidant, a thermal stabilizer, an adhesion promoter, filler, UV absorber, surfactant or a combination of two or more thereof.

12 . The composition of claim 1 , wherein the solvent is chosen from an aliphatic alcohol, a glycol ether, a cycloaliphatic alcohol, an aliphatic ester, a cycloaliphatic ester, an aliphatic hydrocarbon, a cycloaliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated aliphatic compound, a halogenated cycloaliphatic compound, a halogenated aromatic compound, an aliphatic ether, a cycloaliphatic ether, an amide solvents, a sulfoxide solvent, or a combination of two or more thereof.

13 . The composition of claim 1 , wherein the catalyst is at least one member selected from the group consisting of tetra-n-butylammonium acetate, tetra-n-butylammonium formate, tetra-n-butylammonium benzoate, tetra-n-butylammonium-2-ethylhexanoate, tetra-n-butylammonium-p-ethylbenzoate, tetra-n-butylammonium propionate and TBD-acetate (acetate of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)).

14 . A coating forming composition comprising the composition of claim 1 , wherein the coating forming composition is applied to a substrate, said substrate selected from an acrylic polymer, a polyamide, a polyimide, an acrylonitrile-containing polymer, a polyvinyl halide, a polyolefin, a polycarbonate, or a copolycarbonate, a metal, a glass, or a combination of two or more thereof.

15 . An article comprising a substrate and a coating composition covering at least a portion of said substrate, the coating composition comprising

Component A of the formula (R 1 ) d Si(OR 2 ) 4−d , wherein R 1 is a C 1 -C 3 monovalent hydrocarbon, R 2 is a C 1 -C 3 monovalent hydrocarbon or a hydrogen radical and d is 0, 1, or 2, and

Component B is selected from the group consisting of at least one of formula 1 or 2:

(R 3 ) a Si(OR 4 ) 4−a   Formula 1

(R 5 O) m (R 6 ) n Si(R 9 ) x (R 10 ) y (R 11 ) z Si(R 8 ) s (OR 7 ) p   Formula 2

wherein R 3 is chosen from a C 5 -C 20 linear or branched alkyl radical, a C 5 -C 20 fluoroalkyl, a mixture of hydrocarbon and fluorocarbon chain, C 5 -C 20 linear or branched hydrocarbon chain containing thioester group, C 6 -C 24 saturated or unsaturated linear or cyclic hydrocarbon chain containing amino group or urea group, R 4 is C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical; a is 0, 1 to 3;

R 5 and R 7 are independently chosen from a C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical;

R 6 and R 8 are independently selected from a C 1 to C 3 monovalent hydrocarbon radical or a hydrogen radical; m and p are 1 to 3; n and s are 1 to 3 such that m+n is 3, and s+p is 3;

R 9 is chosen from a C1-C24 divalent hydrocarbon radical;

R 10 and R 11 are independently chosen from C 1 to C 24 monovalent hydrocarbon radical;

x is 1 to 20, y is 0 to 20, and z is 0 to 20;

metal oxide particles;

UV absorber;

a catalyst; and

a solvent.

wherein the coating composition when cured has a critical strain of about 1 to 10 as measured at 3-10 micron coating thickness.

16 . The article of claim 15 , wherein component B is present in an amount of from about 1 weight percent to about 60 weight based on the total weight of the component A and the component B.

17 . The article of claim 15 , wherein R 3 is chosen from pentyl, hexyl, heptyl, octyl, nonyl decyl, dodecyl, 3,3,3-triflurorpentyl, 3,3,3-triflurorhexyl, 3,3,3-trifluroheptyl, 3,3,3-triflurooctyl, perfluoropentyl, pefluorohexyl, pefluoroheptyl, or perfluorohexyl.

18 . The article of claim 15 , wherein the R 4 is chosen from methyl or ethyl.

19 . The article of claim 15 , wherein the component A is methyltrimethoxy silane.

20 . The article of claim 15 , wherein the metal oxide particles are present in an amount of from about 0.1 weight percent to about 50 weight percent based on the weight of the composition.

21 . The article of claim 15 , wherein the metal oxide particles chosen from silica, zirconia, titania, alumina, ceria, tin oxide, zinc oxide, antimony oxide or a combination of two or more thereof.

22 . The article of claim 15 , wherein the metal oxide particles have an average particle size of from about 1 nm to about 250 nm.

23 . The article of claim 15 , wherein the substrate is chosen from an acrylic polymer, a polyamide, a polyimide, an acrylonitrile-styrene copolymer, a styrene-acrylonitrile-butadiene terpolymer, a polyvinyl halide, a polyethylene, a polycarbonate, a copolycarbonate, a metal, a glass, or a combination of two or more thereof.

24 . The article of claim 15 , wherein the coating composition is cured.

25 . The article of claim 25 comprising optionally a primer coating disposed between the coating composition and the substrate.

26 . A process for forming a coating composition comprising providing:

(i) Component A of the formula (R 1 ) d Si(OR 2 ) 4−d , wherein R 1 is a C 1 -C 3 monovalent hydrocarbon, R 2 is a C 1 -C 3 monovalent hydrocarbon or a hydrogen radical and d is 0, 1, or 2, and

(ii) Component B, is selected from the group consisting of Formula 1, Formula 2, or a combination thereof:

(R 3 ) a Si(OR 4 ) 4−a   Formula 1

(R 5 O) m (R 6 ) n Si(R 9 ) x (R 10 ) y (R 11 ) z Si(R 8 ) s (OR 7 ) p   Formula 2

wherein R 3 is chosen from a C 5 -C 20 linear or branched alkyl radical, a C 5 -C 20 fluoroalkyl, a mixture of hydrocarbon and fluorocarbon chain, C 5 -C 20 linear or branched hydrocarbon chain containing thioester group, C 6 -C 24 saturated or unsaturated linear or cyclic hydrocarbon chain containing amino group or urea group, R 4 is C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical; a is 0, 1, 2, to 3;

R 5 and R 7 are independently chosen from a C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical;

R 6 and R 8 are independently selected from a C 1 to C 3 monovalent hydrocarbon radical or a hydrogen radical; m and p are 1 to 3; n and s are 1 to 3 such that m+n is 3, and s+p is 3;

R 9 is chosen from a C 1 -C 24 divalent hydrocarbon radical;

R 10 and R 11 are independently chosen from C 1 to C 24 monovalent hydrocarbon radical;

x is 1 to 20, y is 0 to 20, and z is 0 to 20;

(iii) metal oxide particles;

(iv) UV absorber;

(v) a catalyst; and

(vi) a solvent; and mixing (i)-(vi) to form a composition.

27 . A method for forming a coated article comprising applying a coating composition to a surface of a substrate of an article, wherein the coating composition comprises:

Component A of the formula (R 1 ) d Si(OR 2 ) 4−d , wherein R 1 is a C 1 -C 3 monovalent hydrocarbon, R 2 is a C 1 -C 3 monovalent hydrocarbon or a hydrogen radical and d is 0, 1, or 2, and

Component B, is selected from the group consisting of Formula 1, Formula 2, or a combination thereof:

(R 3 ) a Si(OR 4 ) 4−a   Formula 1

(R 5 O) m (R 6 ) n Si(R 9 ) x (R 10 ) y (R 11 ) z Si(R 8 ) s (OR 7 ) p   Formula 2

wherein R 3 is chosen from a C 5 -C 20 linear or branched alkyl radical, a C 5 -C 20 fluoroalkyl, a mixture of hydrocarbon and fluorocarbon chain, C 5 -C 20 linear or branched hydrocarbon chain containing thioester group, C 6 -C 24 saturated or unsaturated linear or cyclic hydrocarbon chain containing amino group or urea group, R 4 is C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical; a is 0, 1, 2, to 3;

R 5 and R 7 are independently chosen from a C 1 -C 20 monovalent hydrocarbon radical or a hydrogen radical;

R 6 and R 8 are independently selected from a C 1 to C 3 monovalent hydrocarbon radical or a hydrogen radical; m and p are 1 to 3; n and s are 1 to 3 such that m+n is 3, and s+p is 3;

R 9 is chosen from a C 1 -C 24 divalent hydrocarbon radical;

R 10 and R 11 are independently chosen from C 1 to C 24 monovalent hydrocarbon radical;

x is 1 to 20, y is 0 to 20, and z is 0 to 20;

metal oxide particles;

UV absorber;

a catalyst; and

a solvent.

28 . The method of claim 27 , wherein the coating composition is applied by a coating deposition method selected from spray, dip, flow, spin.

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 →
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 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2018
From: SAMANTARA, LAXMI; DAVID, JENNIFER LYNN; HAYES, ROBERT; MURUGESAN, KARTHIKEYAN
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 047394/0127 →