IP Library Patent Application 15148654
Patent Application
App. No. 15/148,654

ANTIFOG COATING COMPOSITION

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Patent No.
US None
App. No.
15/148,654
Abstract

A curable composition includes (i) an acrylic functional silicone material; (ii) an acrylic functional organic material; (iii) an acrylic functional urethane material; and optionally (iv) metal oxide particles. Upon curing, the compositions provide a coating that may exhibit good optical clarity, adhesion to various plastics, and good antifog performance.

Claims (38)

1 . A curable coating composition comprising:

(i) at least one acrylic functional silicone material;

(ii) at least one acrylic functional organic material; and

(iii) at least one acrylic functional urethane material.

2 . The curable composition of claim 1 , wherein the acrylic functional silicone material (i) is chosen from a silicone polyether acrylate, a silicone dimethacrylate, a silicone acrylamide, or a combination of two or more thereof.

3 . The curable composition of claim 1 , wherein the acrylic functional silicone material (i) is chosen from a compound of the formula:

wherein R 1 and R 2 are independently chosen from a C1-C10 alkyl group, a C6-30 aryl group or R 4 ; wherein each occurrence of R 3 is independently chosen from a C1-C10 alkyl group or a C6-C30 aryl group; wherein each occurrence of R 4 is independently a linear or a branched alkylene chain of 1 to 10 carbon atoms optionally substituted with at least one heteroatom chosen from O, N or S; wherein each occurrence of R 5 is independently chosen from hydrogen or a C1-C6 alkyl group; R 10 is polyether unit; m is an integer ≧0; n is an integer from 1 to 100, and p is an integer from 0 to 100.

4 . The curable composition of claim 1 , wherein the acrylic functional silicone material (i) is present in an amount of from about 2 wt. % to about 60 wt. % based on the weight of a dry film formed from the composition.

5 . The curable composition of claim 1 , wherein the acrylic functional organic material (ii) is chosen from a compound of the formula:

wherein

R 6 is independently selected from the group consisting of: O; H; a linear alkyl group containing from 1 to 5 carbon atoms; a linear alkyl group containing from 1 to 5 carbon atoms substituted with a hydroxy or an alkoxy group; an aromatic group; a hydroxy group; an alkoxy group containing from 1 to 3 carbon atoms; a methacrylate; and an acrylate group; wherein a is 0 or 1;

R 7 is independently chosen from H or CH 3 ;

R 8 is independently selected from the group consisting of H, an alkyl group having from 1 to 6 carbon atoms, a hydroxy group, an alkoxy group having from 1 to 3 carbon atoms, a methacrylate group, and an acrylate group;

A is independently selected from the group consisting of O, a substituted or unsubstituted linear alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted divalent aromatic group having from 6 to 20 carbon atoms, an alkylene oxide, and a substituted or unsubstituted divalent heterocyclic group having from 5 to 20 carbon atoms;

A′ is independently selected from H, a substituted or unsubstituted linear alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted divalent aromatic group having from 6 to 20 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having from 5 to 20 carbon atoms, a methacrylate group, and an acrylate group;

B is independently selected from O, an NH moiety, a substituted or unsubstituted linear alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted divalent aromatic group having from 6 to 20 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having from 5 to 20 carbon atoms, and a bisphenol A unit; wherein e is an integer from 0 to 1;

D is independently selected from null, direct bond, a substituted or unsubstituted linear alkyl group having from 1 to 20 carbon atoms, isopropanol, epoxy ring opened unit, a substituted or unsubstituted divalent aromatic group having from 6 to 20 carbon atoms, a substituted or unsubstituted divalent heterocyclic group having from 5 to 20 carbon atoms; and

y is an integer from 1 to 50 and x is an integer from 0 to 50.

6 . The curable composition of claim 1 , wherein the acrylic functional organic material (ii) is chosen from a poly(ethyleneoxy)methacrylate, a poly(ethyleneoxy)acrylate, a poly(ethyleneoxy)monomethylether acrylate, a poly(ethyleneoxy)monomethylether methacrylate, a pentaerythritol triacrylate, a glycerol dimethacrylate, a glycerol diacrylate, a bisphenol-A-glycerol tetraacrylate, a bisphenol-A-glycerol diacrylate, a bisphenol-A-ethyleneoxy diacrylate, or a combination of two or more thereof.

7 . The curable composition of claim 1 , wherein the acrylic functional organic material (ii) is chosen from Isooctyl Acrylate; 2-2(Ethoxyethoxy)ethyl Acrylate; Isodecyl Acrylate; Isodecyl Methacrylate; Lauryl Acrylate; Lauryl Methacrylate; Isodecyl Acrylate; Propoxylated Neopentyl Glycol Diacrylate; Alkoxylated Difunctional Acrylate Ester; Glycidyl Methacrylate; Propoxylated Neopentyl Glycol Diacrylate; Alkoxylated Difunctional Acrylate Ester; Tridecyl Methacrylate; Tridecyl Acrylate; Caprolactone Acrylate; Tripropylene Glycol Diacrylate; Stearyl Methacrylate; Tris (2-Hydroxy Ethyl) isocyanurate Triacrylate; 1,3-Butylene Glycol Dimethacrylate; 1,3-Butylene Glycol Diacrylate; Neopentyl Glycol Diacrylate; Neopentyl Glycol Dimethacrylate; Ethylene Glycol Dimethacrylate; Alkoxylated Aliphatic Diacrylate Ester; 1,4-Butanediol Diacrylate; 1,4-Butanediol Dimethacrylate; C14-C15 Acrylate Terminated Monomer; Tetrahydrofurfuryl Methacrylate; Hexanediol Diacrylate; 1,6-Hexanediol Dimethacrylate; 1,6-Hexanediol Diacrylate; Tetrahydrofurfuryl Acrylate; Hexanediol Dimethacrylate; Propoxylated Trimethylolpropane Triacrylate; Cyclohexyl Acrylate; Highly Propoxylated Glyceryl Triacrylate; Tetrahydrofurfuryl Acrylate; Cyclohexyl Methacrylate; Triethylene Glycol Dimethacrylate; C14-C15 Methacrylate Terminated Monomer; Tetraethylene Glycol Dimethacrylate; Propoxylated 3 Trimethylolpropane Triacrylate; Diethylene Glycol Diacrylate; Polyethylene Glycol Dimethacrylate; Propoxylated Glyceryl Triacrylate; Triethylene Glycol Diacrylate; Diethylene Glycol Dimethacrylate; Highly Propoxylated Glyceryl Triacrylate; Tetraethylene Glycol Diacrylate; Caprolactone Acrylate; Polyethylene Glycol (200) Diacrylate; Polyethylene Glycol (400) Dimethacrylate; Di-trimethylolpropane Tetraacrylate; Polyethylene Glycol (600) Dimethacrylate; Polyethylene Glycol (400) Diacrylate; Polyethylene Glycol (600) Dimethacrylate; Polyethylene Glycol (600) Diacrylate; Ethoxylated Trimethylolpropane Triacrylate; Ethoxylated 3 Trimethyolopropane Triacrylate; Ethoxylated 6 Trimethylolpropane Triacrylate; Ethoxylated 9 Trimethylolpropane Triacrylate; Ethoxylated 15 Trimethylolpropane Triacrylate; Alkoxylate d Trifunctional Acrylate Ester; Ethoxylated Trimethylolpropane Triacrylate; Ethoxylated 20 Trimethylolpropane Triacrylate; Trimethylolpropane Trimethacrylate; Ethoxylated Trimethylolpropane Triacrylate; Ethoxylated Pentaerythritol Triacrylate; Isobornyl Acrylate; Trimethylolpropane Triacrylate; Trifunctional Methacrylate Ester; Trifunctional Methacrylate Ester; Trifunctional Methacrylate Ester; Isobornyl Acrylate; Isobornyl Methacrylate; Isobornyl Methacrylate; Di-Trimethylolpropane Tetraacrylate; Pentaerythritol Triacrylate; Aliphatic Urethane Acrylate; Low Viscosity Aliphatic Diacrylate; Pentaerythritol Tetraacrylate; Dipentaerythritol Pentaacrylate; Low Viscosity Aliphatic Triacrylate Oligomer; Dimethacrylate Aliphatic Urethane Acrylate; Ethoxylated Nonylphenol Acrylate; Phenoxyethyl Methacrylate; 2-Phenoxyethyl Methacrylate; Ethoxylated 10 Bisphenol A Diacrylate; Phenoxyethyl Acrylate; 2-Phenoxyethyl Acrylate; Ethoxylated 6 Bisphenol A Dimethacrylate; Ethoxylated 4 Bisphenol A Dimethacrylate; Ethoxylated 4 Bisphenol A Diacrylate; Ethoxylated Bisphenol A Dimethacrylate; Ethoxylated 2 Bisphenol A Dimethacrylate; Ethoxylated Bisphenol A Diacrylate, or a combination of two or more thereof.

8 . The curable composition of claim 1 , wherein the acrylic functional organic material (ii) is present in an amount of from about 1 wt. % to about 80 wt. % based on the weight of a dry film formed from the composition.

9 . The curable composition of claim 1 , wherein the acrylic functional urethane (iii) comprises two or more acrylate functional groups.

10 . The curable composition of claim 1 , wherein the acrylic functional urethane (iii) is chosen from an aliphatic polyester urethane acrylate, an aliphatic polyether urethane acrylate, an acrylated polyurethane dispersion, or a combination thereof.

11 . The curable composition of claim 1 , wherein the acrylic functional urethane (iii) is present in an amount of from about 5 wt. % to about 98 wt. % based on the weight of a dry film formed from the composition.

12 . The curable composition of claim 1 further comprising metal oxide particles (iv) chosen from silica oxide particles, aluminum oxide particles, cerium oxide, titanium oxide, zinc oxide particles, tin oxide particles, or a combination of two or more thereof.

13 . The curable composition of claim 1 , wherein the metal oxide particles (iv) are functionalized with a silane and siloxane.

14 . The curable composition of claim 1 , wherein the metal oxide particles (iv) are present in an amount of from about 0.1 to about 40 wt. % based on the weight of a dry film formed from the composition.

15 . The curable composition of claim 1 further comprising a photoinitiator, thermal initiator, surface active agent, cure promoters and mixtures thereof.

16 . The curable composition of claim 1 further comprising at least one surfactant chosen from an ionic surfactant, a non-ionic surfactant, or a combination thereof.

17 . An article comprising a substrate, wherein at least a portion of a surface of the substrate comprises a coating formed the curable composition of claim 1 .

18 . The article of claim 17 , wherein the substrate is chosen from an acrylic polymer, a polyamide, a polyacrylate, a polyimide, an acrylonitrile-styrene copolymer, a styrene-acrylonitrile-butadiene terpolymer, a polyvinyl chloride, a polyethylene, a polycarbonate, or a combination thereof.

19 . The article of claim 17 , wherein the substrate comprises a polycarbonate.

20 . The article of claim 17 , wherein the coating has a transmittance of coating of at least 85%.

21 . The article of claim 17 , wherein the coating after curing has a transmittance of coating of at least 89%.

22 . The article of claim 17 , wherein the article is an automobile headlight, a windshield, eyeglasses, goggles, a mirror, a storage container, a window, or a camera lens.

23 . A method of forming an article coated with an antifog coating comprising:

applying the curable composition of claim 1 to a surface of a substrate; and

exposing the curable composition to actinic or electron beam radiation to cure the coating.

Assignments (6)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
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 →
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 Sep 26, 2018
From: SAMANTARA, LAXMI; HAEUSELER, ANDREAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 046971/0332 →