WO2012055027A1

WO2012055027A1 - Coating composition comprising surfactant-containing organosilicon and functionalized silane and methods of making thereof

Info

Publication number: WO2012055027A1
Application number: PCT/CA2011/001195
Authority: WO
Inventors: Naiheng Song; Grzegorz Czeremuszkin; Guillermo Mendoza-Suarez; Mohamed Latreche
Original assignee: Revision Military S.A.R.L.
Priority date: 2010-10-29
Filing date: 2011-10-26
Publication date: 2012-05-03

Abstract

The present disclosure relates to a coating composition comprising at least one of surfactant-containing organosilicon having an ionic and/or neutral character, one or more epoxy functionalized silane, one or more multifunctional acid, and a solvent or a mixture thereof. The present disclosure further relates to methods of applying the coating composition as defined above and articles comprising cured composition as defined above.

Description

COATING COMPOSITION COMPRISING SURFACTANT-CONTAINING

ORGANOSILICON AND FUNCTIONALIZED SILANE AND METHODS OF MAKING

THEREOF

FIELD OF THE DISCLOSURE

The present invention relates to novel coating compositions comprising surfactant-containing organosilicons and functionalized silanes, methods of applying same and articles comprising cured composition as defined herein.

BACKGROUND OF THE DISCLOSURE

Condensation of moisture on cool surfaces with a temperature lower than the dew-point of the air is commonly known as fog. Depending on the nature of the surface, the condensates may form droplets or spread as a thin film. For transparent articles, such behaviour has significant effect on their applications. For example, due to scattering of light by the condensed water droplet, optically clear articles such as protective eyewear (goggles, face shields, visors, etc.), ophthalmic lenses, automobile windshields, windows, and the like may lose their see-through characteristic, which in some cases results in dangerous situations. To prevent the formation of water droplets or 'fogging', anti-fog coatings that improve the hydrophilicity of the article are desirable.

Most of the known coatings having hydrophilic properties react slowly with water condensation and exhibit initial fogging upon contact with high humidity. Other known coatings may use reactive components resulting in a short pot life. Delayed fogging may also be observed with coatings exhibiting relatively poor water and solvent resistance.

Most of the known hydrophilic coatings also have poor abrasion resistance, which limits their practical applications in fields such as protective eyewear and transparent armour.

SUMMARY

In one aspect of the disclosure, there is provided a coating composition comprising

- at least one of surfactant-containing organosilicon having an ionic and/or neutral character;

- one or more epoxy functionalized silane;

- one or more multifunctional acid; and

- a solvent or a mixture thereof. In another aspect of the disclosure, there is provided a method for coating at least one surface of an article comprising:

- applying a coating composition as defined herein on at least said one surface, and

- curing said composition.

In yet another aspect of the disclosure, there is provided an article having on a surface thereof a coating obtainable by curing a composition as defined herein.

In a further aspect of the disclosure, there is provided a method of providing an article with an anti-fog surface comprising:

- applying a coating composition as defined herein to the surface of said article, and

- curing said composition.

In another aspect of the disclosure, there is provided a method of providing an article with an anti-fog and abrasion resistant surface comprising:

- curing said composition.

DESCRIPTION OF THE EMBODIMENTS

In accordance with one embodiment, the disclosure provides a coating composition comprising

- at least one surfactant-containing organosilicon having an ionic and/or neutral character;

- one or more epoxy functionalized silane;

- one or more multifunctional acid; and

- a solvent or a mixture thereof.

In accordance with another embodiment, the disclosure provides a coating composition comprising

- one or more epoxy functionalized silane;

- one or more multifunctional acid;

- a solvent or a mixture thereof;

- optionally one or more tetrafunctional silane; and

- optionally one or more multifunctional disilane. In accordance with another embodiment, there is provided a coating composition as defined herein, wherein the at least one surfactant-containing organosilicon is a neutral surfactant- containing organosilicon.

In accordance with a further embodiment, there is provided a coating composition as defined herein, wherein the at least one surfactant-containing organosilicons are a cationic and a neutral surfactant-containing organosilicons.

In another embodiment, there is provided a coating composition as defined herein, wherein the at least one surfactant-containing organosilicon are an anionic and a neutral surfactant-containing organosilicons.

In accordance with another embodiment, there is provided a coating composition as defined herein, wherein the at least one surfactant-containing organosilicon are a cationic and an anionic surfactant-containing organosilicons.

In accordance with a further embodiment, there is provided a coating composition as defined herein, wherein the at least one surfactant-containing organosilicon are a cationic, an anionic and a neutral surfactant-containing organosilicons.

In another embodiment, the surfactant-containing organosilicon is represented by Formula I

(R'L)_n (R²0)_4-n Si I

wherein

when said surfactant-containing organosilicon is neutral then R¹ is a neutral residue having surfactant properties, and L is a bond between R¹ and Si;

when said surfactant-containing organosilicon is ionic then R¹ is an ionic surfactant, and L is either associated with R¹ by ionic interactions and comprises a counterion residue to said ionic surfactant, or L is an organic linkage covalently bonding R¹ to Si;

R² is H or Cl -20 alkyl; and

n is an integer of 1 to 3.

In accordance with one embodiment, said surfactant-containing organosilicon is cationic and is represented by Formula I as defined herein, wherein R¹ is a quaternary ammonium surfactant compound. In accordance with one embodiment, said surfactant-containing organosilicon is cationic and is represented by Formula I as defined herein, wherein R^l is a quaternary ammonium surfactant comprising at least one saturated or unsaturated linear or branched chain of 8 or more carbon atoms; preferably 8 to 20 carbon atoms; wherein said chain is optionally substituted.

In accordance with one embodiment, said surfactant-containing organosilicon is cationic and is represented by Formula I as defined herein, wherein R¹ is a quaternary ammonium surfactant selected from tetraalkyl ammonium, alkyl pyridinium, and benzyl trialkyl ammonium wherein at least one of said alkyl is a saturated or unsaturated linear or branched chain of 8 or more carbon atoms; preferably 8 to 20 carbon atoms; wherein said chain is optionally substituted.

In accordance with another embodiment, said surfactant-containing organosilicon is cationic and is represented by Formula I as defined herein, wherein R¹ is ricinoleamidopropyl dimethyl ethylammonium, stearamidopropyl dimethylethanolammonium, octadecyl dimethyl ethanol ammonium, cetyl trimethylammonium (hexadecyl trimethyl ammonium), cetylpyridinium, benzalkonium, benzethonium, or dimethyldioctadecylammonium.

In accordance with a further embodiment, the surfactant-containing organosilicon is ionic and represented by Formula I as defined herein, wherein L is an organic linkage between the Si and a counterion that is positively or negatively charged to balance the charge(s) of the cationic or anionic surfactant.

In a further embodiment, in any of the embodiments provided with regard to Formula I, L is of general formula Cl -6alkylene-X-C l -6alkylene-N⁺(lower alkyl)₃ wherein X is O, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH; said lower alkyl is linear or branched chain of 1 -3 carbon atoms; preferably a methyl or ethyl.

In a further embodiment, in any of the embodiments provided with regard to Formula I, L is Cl- 3alkylene-X-Cl -2alkylene-N⁺(lower alkyl)₃, wherein X is O, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH, said lower alkyl is linear or branched chain of 1-3 carbon atoms. In a further embodiment, in any of the embodiments provided with regard to Formula I, L is Cl- 3alkylene-NH(CO)0-C l -2alkylene-N⁺(lower alkyl)₃, wherein said lower alkyl is methyl or ethyl.

In a further embodiment, in any of the embodiments provided with regard to Formula I, L is of general formula C l-6alkylene-X-Cl-6alkylene-Y^~ wherein X is O, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH, and Y is -OS0₂0\ -S0₂0\ -C0₂ ^", or -OP(0 )₂.

In a further embodiment, in any of the embodiments provided with regard to Formula I, L is of general formula Cl -6alkylene-X-Cl-6alkylene, wherein X is O, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH.

In another embodiment, the surfactant-containing organosilicon is represented by Formula la

(R²0)₃ Si (LR¹) la

wherein R is CI -3 alkyl; and LR is as defined herein.

In another embodiment, the surfactant-containing organosilicon is represented by Formula lb

lb

wherein the quaternary ammonium has a counterion residue.

In another embodiment, the surfactant-containing organosilicon is represented by Formula Ic

Ic

In another embodiment, the surfactant-containing organosilicon is represented by one of Formula (R²0)₃Si-(C,.₆)alkylene-X-(Ci.₆)alkylene-N⁺(lower alkyl)₃ O₃S-aryl-alkyl Id

(R²0)₃Si-(Ci.3)alkylene-X-(C,.₃)alkylene-N⁺(lower alkyl)₃ O₃S-phenyl-alkyl Ie

(EtO)₃Si-propylene-X-ethylene-N⁺(lower alkyl)₃ O₃S-phenyl-alkyl If

(EtO)₃Si-propylene-NH(CO)0-ethylene-N⁺(lower alkyl)₃ ^"0₃S-phenyl-alkyl Ig

In another embodiment, the surfactant-containing organosilicon has the formula

wherein said alkyl in "alkyl-phenyl-S0₃ ^"" and "alkyl-aryl-S0₃ ^"" is an alkyl of 8-14 carbon atoms; said aryl being preferably having 6 carbon atoms.

In accordance with a further embodiment, the surfactant-containing organosilicon is neutral and represented by Formula I as defined herein, wherein R¹ is of general formula alkyl-0(lower alkyloxy)_n- alkylphenyl-0(lower alkyloxy)_n- or alkyl(CO)0(lower alkyloxy)_n-. Said alkyl is a saturated or unsaturated linear or branched chain of 8 or more carbon atoms; preferably 8 to 20 carbon atoms; wherein said chain is optionally substituted, said lower alkyl is ethyl or propyl and n is 1 to 25.

In accordance with a further embodiment, the surfactant-containing organosilicon is neutral and represented by Formula I as defined herein, wherein R¹ is of general formula alkyl-0(2- propyloxy)_n- alkylphenyl-0(2-propyloxy)_n- or alkyl(CO)0-(2-propyloxy)_n- Said alkyl is a saturated or unsaturated linear or branched chain of 8 or more carbon atoms; preferably 8 to 20 carbon atoms; wherein said chain is optionally substituted, and n is 1 to 25.

In accordance with a further embodiment, the surfactant-containing organosilicon is neutral and represented by Formula I as defined herein, wherein R¹ is of general formula alkyl-O- (ethyloxy)n-, alkylphenyl-0(ethyloxy)_n- or alkyl(CO)0-( ethyloxy)_n- . Said alkyl is a saturated or unsaturated linear or branched chain of 8 or more carbon atoms; preferably 8 to 20 carbon atoms; wherein said chain is optionally substituted, and n is 1 to 25. In accordance with a further embodiment, the surfactant-containing organosilicon is neutral and represented by Formula I as defined herein, wherein R¹ is C 10-20alkyl-(ethyloxy)i_25- or C 10- 20alkyl(CO)O -(ethyloxy),.₂₅-.

In accordance with a further embodiment, the neutral surfactant-containing organosilicon represented by Formula I as defined herein, wherein R¹ is polyoxyethylene lauryl ether or polyoxyethylene monooleate.

In another embodiment, the neutral surfactant-containing organosilicon is represented by one of Formula:

(R²0)₃Si-(C,_-6)alkylene-X-(ethyloxy)n-(CO)C₈-₂oalkyl Ii

(R²0)₃Si-(Ci.₃)alkylene-X-(ethyloxy)n-(CO)Cio_-2oalkyl Ij

(EtO)₃Si-propylene-X-(ethyloxy)n-(CO)Ci₀.₂₀alkyl Ik

wherein n is 1 to 25

(EtO)₃Si-propylene-NH(CO)0-(ethyloxy)_n -γ-oleate II

wherein n is 10 to 15

In a further embodiment, in any of the embodiments provided with regard to Formula I, la, lb, Id, le, Ii and Ij as defined herein R² is H or CI -5 alkyl; H or CI -2 alkyl; H, methyl or ethyl, H or ethyl, methyl or ethyl; or preferably ethyl.

In a further embodiment, in any of the embodiments provided with regard to Formula I, regarding the substituent on the Si atom, as defined herein n is preferably 1.

In accordance with another embodiment, the epoxy functionalized silane is represented by Formula II

R¹⁰ _mR^u ₁(R¹ O)_4-m.,Si II

wherein

R¹⁰ is independently an epoxy-containing Cl-20alkyl;

R^{1 1} is Cl-20alkyl;

R¹² is independently H or Cl-20alkyl;

m is an integer of 1 to 3; and

1 is an integer of 0 to 2, provided that m + 1 < 3 wherein each alkyl is independently saturated or unsaturated, linear or branched; optionally substituted chain and said alkyl chain is optionally interrupted by an oxygen.

In accordance with another embodiment, R¹⁰ is epoxy-containing Cl-lOalkyl. In accordance with another embodiment R¹⁰ is epoxy-Cl-5alkyleneoxy-C l -5 alkyl. In accordance with another embodiment R¹⁰ is glycidoxy-Cl -5alkylene. In accordance with another embodiment R¹⁰ is glycidoxy-propylene.

In a further embodiment, in any of the embodiments provided with regard to Formula II as defined herein R^{1 1} is CI -5 alkyl; or CI -2 alkyl.

In a further embodiment, in any of the embodiments provided with regard to Formula II as defined herein R^{1 1} is methyl, ethyl or a combination thereof.

In a further embodiment, in any of the embodiments provided with regard to Formula II as defined herein R is H or CI -5 alkyl; H or CI -2 alkyl; H, methyl or ethyl; H or ethyl; methyl, ethyl or a combination thereof.

In a further embodiment, in any of the embodiments provided with regard to Formula II as defined herein, preferably m is 1 and 1 is 0.

In accordance with another embodiment, the epoxy functionalized silane is represented by Formula Ila

R^I0(R^I2O)₃Si Ila

wherein R¹⁰ and R¹² are as defined above. Preferably, R¹⁰ is glycidoxy-Cl-5alkylene or more preferably glycidoxy-propylene and R¹² is methyl, ethyl or a combination thereof and more preferably methyl.

In accordance with yet another embodiment, the epoxy functionalized silane is selected from glycidoxymethyltrimethoxysilane, 3-glycidoxypropyltrihydroxysilane,

3 -glycidoxypropyldimethylhydroxsilane, 3 -glycidoxylpropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropyldimethylmethoxysilane,

3-glycidoxypropyltributoxysilane, 2,3-epoxypropyltrimethoxysilane, and

3,4- epoxybutyltrimethoxysilane.

In accordance with another embodiment, there is provided a coating as defined herein further comprising a tetrafunctional silane, multifunctional disilane(s) or siloxane oligomers or polymers.

In accordance with yet another embodiment, the tetrafunctional silane is represented by

Formula III

Si(OR²⁰)₄ III

wherein

R²⁰ is independently H or Cl-20alkyl.

In a further embodiment, R is H or CI -5 alkyl; CI -5 alkyl; H or CI -2 alkyl; H, methyl or ethyl; H or ethyl; methyl; or ethyl or a combination thereof.

In accordance with an embodiment, the tetrafunctional silane selected from tetramethyl orthosilicate, tetraethyl orthosilicate, tetrapropyl orthosilicate, tetraisopropyl orthosilicate, tetraisobutyl orthosilicate, tetraisobutyl orthosilicate, tetrakis(methoxyethoxyethoxy)silane, trimethoxyethoxysilane, and triethoxymethoxysilane.

In accordance with an embodiment, there is provided a coating composition as defined herein further comprising a multifunctional disilane represented by Formula IV

(R³⁰O)_3-o(R³¹)oSiBSi(R³²)p(OR³³)3.p IV

wherein

R³⁰ and R³³ are independently H or Cl-20alkyl;

R³¹ and R³² are independently Cl -20alkyl;

B is divalent hydrophilic bridge having 1 to 500 carbon atoms; and

o and p are independently an integer of 0 to 2.

In accordance with another embodiment, R³⁰ and R³³ are independently Cl -5akyl or CI -2 alkyl. In accordance with another embodiment, R and R³³ are independently methyl, ethyl or a combination thereof.

In accordance with another embodiment, in any of the embodiments provided with regard to Formula IV as defined herein, R³¹ and R³² are independently Cl -5akyl or C I -2 alkyl.

In accordance with another embodiment, in any of the embodiments provided with regard to Formula IV as defined herein, R³¹ and R³² are independently methyl, ethyl or a combination thereof.

In accordance with another embodiment, in any of the embodiments provided with regard to Formula IV as defined herein, B is a poly(ethylene glycol) segment of molecular weight 100 - 4,000.

In accordance with another embodiment, in any of the embodiments provided with regard to Formula IV as defined herein, B is Cl-6alkylene-X-(ethyloxy)_n-X-Cl-6alkylene, wherein X is O, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH and n is 2 to 100 repeat units. Preferably, B is C3alkylene-NH(CO)0-(ethyloxy)_n-(CO)NH- C3alkylene, and n is 4 to 30.

In accordance with another embodiment, in any of the embodiments provided with regard to Formula IV as defined herein, o and p are 0.

In accordance with an embodiment, the multifunctional disilane is represented by Formula IVa

(R³⁰O)₃SiBSi(OR³³)₃ IVa

wherein R³⁰ and R³³ are independently Cl-20alkyl;

B is a poly(ethylene glycol) segment of molecular weight 100 - 4,000.

In accordance with an embodiment, the multifunctional disilane is represented by Formula IVa (R³⁰O)₃SiBSi(OR³³)₃ IVa

wherein R³⁰ and R³³ are independently Cl-20alkyl;

B is C3alkylene-NH(CO)0-(ethyloxy)_n-(CO)NH-C3alkylene. The term "surfactant" used with reference to ionic or neutral surfactant-containing organosilicon refers to chemical species that contain both hydrophilic and hydrophobic segments and act as surface active agents for lowering the surface tension and increasing the wettability of the coating and increasing the spreadability of water droplets on the coating surface.

An "ionic surfactant-containing organosilicons" can be a cationic surfactant-containing organosilicon or an anionic surfactant-containing organosilicon.

An "ionic surfactant" can also be a cationic surfactant or an anionic surfactant.

"Cationic surfactant" refers to moieties having hydrophobic tail and positively charged (hydrophilic) head, independently of the counter ion. The hydrophobic tail may be, for example, substituted or unsubstituted Cl-20alkyl or C6-30aryl group. The positively charged head may be, for example, quaternary ammonium cations. Examples of cationic surfactant include, but are not limited to, ricinoleamidopropyl dimethyl ethylammonium ethosulfate, stearamidopropyl dimethylethanolammonium methasulfate, and octadecyl dimethyl ethanol ammonium chloride.

"Anionic surfactant" refers to moieties having hydrophobic tail and negatively charged (hydrophilic) head, independently of the counter ion; The hydrophobic tail may be, for example, substituted or unsubstituted Cl-20alkyl or C6-30aryl group. The negatively charged head may be, for example, -OS0₂0^~, -S0₂0^", -C0₂ ^", -OP(0^")₂.

"Neutral surfactant" refers to moieties having hydrophobic tail and non-ionic hydrophilic head, connected to each other, for example by an ether or ester linker. The hydrophilic head is connected to the Si atom by a single bond or a linkage and provided that if the head has some ionizable functionalities, the non-ionic hydrophilic tail plays the critical role in its effect of increasing the wettability or spreadability to water. The hydrophobic tail may be, for example, substituted or unsubstituted Cl-20alkyl or C6-30aryl group. The non-ionic hydrophilic head may be, for example, poly(alkylene glycol) with 2 - 20 repeat units. In another embodiment, the non- ionic hydrophilic head may be, for example, poly(alkylene glycol) with 10 - 15 repeat units. In another embodiment, the non-ionic hydrophilic head may be, for example, poly(alkylene glycol) with 2 - 10 repeat units. The surfactants mentioned above may contain reactive functional group(s) that can react with functional group(s) on silanes to form part of the linkage L.

The counter ions of the cationic or anionic surfactants are not limited and can be any cations or anions that can bind tightly to the surfactants.

The coating composition may comprise the ionic or neutral surfactant-containing organosilicon of formula I in a molar concentration of 2 to 80% (including all surfactant-containing organosilicon) relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In another embodiment, the composition may comprise the ionic or neutral surfactant-containing organosilicon in a molar concentration of 5 to 50% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In yet another embodiment, the composition may comprise the ionic or neutral surfactant-containing organosilicon in a molar concentration of 5 to 40% or alternatively 10 to 40% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s).

The coating composition may comprise the epoxy functionalized silane of formula II in a molar concentration of 2 to 80% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In another embodiment, the composition may comprise the epoxy functionalized silane in a molar concentration of 10 to 60% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In yet another embodiment, the composition may comprise the epoxy functionalized silane in a molar concentration of 20 to 60% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s).

The coating composition may comprise the tetrafunctional silane in a molar concentration of 10 to 80% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In another embodiment, the composition may comprise the tetrafunctional silane in a molar concentration of 20 to 70% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In yet another embodiment, the composition may comprise the tetrafunctional silane in a molar concentration of 30 to 60% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s).

A "divalent hydrophilic bridge" is a moiety having a 1 to 500 carbon atoms optionally containing heteroatoms such as O, S, N or P and functional groups such as ether, ester, carbonate, carbamate, amide, imide, and the like. For example, the divalent hydrophilic bridge may be a poly(ethylene glycol) segment of molecular weight 100 - 4,000. Examples of divalent hydrophilic bridge include, but not limited to PEG-200, PEG-300, PEG-400, PEG- 1000, and PEG-2000.

Hydrolyzed or partially hydrolyzed multifunctional disilanes are also included.

The coating composition may comprise the multifunctional disilanes in a molar concentration of 10 to 80% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In another embodiment, the composition may comprise the multifunctional disilanes in a molar concentration of 20 to 70% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In yet another embodiment, the composition may comprise the multifunctional disilanes in a molar concentration of 30 to 60% relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s). In another embodiment, the composition may comprise the multifunctional disilanes in a molar concentration of 1 to 40%, preferably 1 to 20%, relative to the total amount of all components of the composition excluding both the multifunctional acid(s) and the solvent(s).

Siloxane polymers are the hydrolysis and condensation products of the above silanes or can be general siloxane polymers represented by the following formulae: R₂SiO; or -R₂Si-0-R₂Si-0- wherein R is hydrocarbon. Examples of siloxane polymers include, but are not limited to, polydimethylsiloxane and polydiphenylsiloxane.

In one embodiment, the composition as defined herein may further comprise a solvent or a mixture thereof. The solvent may be any solvent which does not interact detrimentally with the other components of the composition during mixing, under aging or during curing. Examples include organic solvents, water or mixtures thereof including aqueous solvent mixtures. Examples of solvents include alcohols, water or an aqueous-alcohol solvent mixture. Examples of alcohol solvent include, but not limited to, methanol, ethanol, propanol, isopropanol, pentanol, l-methoxy-2-propanol, tert-butanol, diacetone alcohol, etc. The organic solvent may also be an alkelene glycol ether such as ethylene glycol ether, propylene glycol ether and preferably ethylene glycol methyl ether or propylene glycol methyl ether. The amount of solvent or aqueous-solvent mixtures in the coating composition may be 10-95% by weight, preferably 40- 85% by weight.

As used herein "multifunctional acid" is an organic compound at least substituted with two carboxylic acid functional group which is represented by the following formula: HOOC-R- COOH, wherein R is alkyl, alkenyl, alkynyl or aryl on which functional groups may be attached. The multifunctional acid is compatible with the coating composition, capable of interacting with the hydrolysis and condensation products of the silanes as well as the epoxy functional group to provide a coating composition which, upon curing, produces a transparent and abrasion resistant coating. Examples of multifunctional acids include, but not limited to, fumaric acid, malic acid, aconitic acid (cis, trans), oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, o-phtalic acid, isophthlic acid, maleic acid, glutaconic acid, itaconic acid, 1 ,3,5- benzene tricarboxylic acid, and 1 ,3-cyclohexanedicarboxylic acid.

In one embodiment, the at least one surfactant-containing organosilicon is at least two of formula la.

In one embodiment, the at least one surfactant-containing organosilicon is at least one of formula lb or Ic and at least one of formula Id, Ie, If, Ig or Ih.

In one embodiment, at least one surfactant-containing organosilicon is at least one of formula lb or Ic and at least one of formula Ii, Ij, Ik or II.

In one embodiment, the at least one surfactant-containing organosilicon is at least one of formula lb or Ic; at least one of formula Id, Ie, If, Ig or Ih; and at least one formula Ii, Ij, Ik or II.

In one embodiment, the at least one surfactant-containing organosilicon is at least one of formula Id, Ie, If, Ig or Ih. In one embodiment, the at least one surfactant-containing organosilicon is at least one of li, Ij, Ik or II.

In one embodiment, the at least one surfactant-containing organosilicon is at least one of formula lb or Ic; at least one of formula Id, Ie, If, Ig or Ih; or at least one formula li, Ij, Ik or II; or a combination thereof.

In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula lb or Ic, or at least one of formula Id, Ie, If, Ig or Ih; or at least one of formula li, Ij, Ik or II; or a combination thereof ;

- one or more epoxy functionalized silane represented by Formula Ila;

- one or more multifunctional acid represented by the following formula: HOOC-R-COOH, wherein R is alkyl, alkenyl, alkynyl or aryl on which functional groups may be attached;

- a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III; and

- optionally one or more multifunctional disilane of formula IVa.

In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula lb or Ic and at least one of formula Id, Ie, If, Ig or Ih;

- one or more epoxy functionalized silane represented by Formula Ila;

- a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III.

In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula lb or Ic and at least one of formula li, Ij, Ik or II;

- one or more epoxy functionalized silane represented by Formula Ila;

- a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III. In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula lb or Ic and at least one of formula Ii, Ij, Ik or II;

- one or more epoxy functionalized silane represented by Formula Ila;

- a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III; and

- one or more multifunctional disilane of formula IVa.

In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula lb or Ic, at least one of formula Id, Ie, If, Ig or Ih; and at least one of formula Ii, Ij, Ik or II;

- one or more epoxy functionalized silane represented by Formula Ila;

- a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III; and

- one or more multifunctional disilane of formula IVa.

In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula Id, Ie, If, Ig or Ih;

- one or more epoxy functionalized silane represented by Formula Ila;

- a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III.

In one embodiment, the composition as defined herein may comprise

- at least one surfactant-containing organosilicon of formula Ii, Ij, Ik or II;

- one or more epoxy functionalized silane represented by Formula Ila;

- one or more multifunctional acid represented by the following formula: HOOC-R-COOH, wherein R is alkyl, alkenyl, alkynyl or aryl on which functional groups may be attached; - a solvent or a mixture thereof; and

- one or more tetrafunctional silane of formula III.

In one embodiment, the composition as defined herein may further comprise one or more additive.

The term "alkyl", unless otherwise defined, represents a saturated or unsaturated, linear or branched; optionally substituted chain. Preferably, the alkyl comprises 1-20 carbon atoms. Examples of "alkyl" groups include but are not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, terl-butyl, pentyl, isopentyl, neopentyl, te -pentyl, hexyl, isohexyl or neohexyl.

The term "alkoxy", unless otherwise defined, represents an alkyl moiety which is covalently bonded to the adjacent atom through an oxygen atom. Examples include but are not limited to methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, ieri-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, isohexyloxy, and neohexyloxy.

The term "aryl" represents a carbocyclic moiety containing at least one benzenoid-type ring (i.e., may be monocyclic or polycyclic). Examples include but are not limited to phenyl, tolyl, dimethylphenyl, aminophenyl, anilinyl, naphthyl, anthryl, phenanthryl, or biphenyl, or alkyl substituted thereof.

The coating composition of the present disclosure can be applied to the surface of an article by any conventional methods such as spray coating, dip coating, flow coating, spin coating, roll coating, brushing and the like. In one embodiment, the coating composition may be applied by flow coating.

Depending of the intended use, the coating composition may be applied on one or more surfaces, for example one or both sides of a substrate. If both sides are coated, the same or different compositions can be used.

The coating composition can be applied in any desirable thickness. In one embodiment, the coating composition can be applied to provide a thickness of the cured coating of from about 1 - about 50 μιη, with about 3 - about 25 μηι more preferred. The composition in accordance with the present disclosure, once cured, can provide anti-fog or abrasion-resistant properties or a combination thereof depending on the desired properties by adjusting the nature and proportion of the components in the composition.

The material comprised in articles susceptible of being coated with a composition as defined herein include, but are not limited to, plastics, glass, ceramics, metals, composites and combinations thereof. Non-limiting examples of plastics include CR39, polycarbonates, polyurethanes, polyamides, and polyesters. Non-limiting examples of glass include windows and optical elements. Non-limiting examples of ceramics include transparent armour. Non-limiting examples of metals include metallic mirrors.

In one embodiment, there is provided a method for coating at least one surface of an article comprising: applying a coating composition as defined herein on at least said one surface, and curing said composition.

In one embodiment, there is provided a method of providing an article with an anti-fog surface comprising: applying a coating composition as defined herein to the surface of said article, and curing said composition.

In one embodiment, there is provided a method of providing an article with an anti-fog and abrasion resistant surface comprising: applying a coating composition as defined herein to the surface of said article, and curing said composition.

The articles to which the coating composition can be applied are not especially limited and include optically clear articles such as protective eyewear (goggles, face shields, visors, etc.), ophthalmic lenses, automobile windshields, windows, and the like. If required by the nature of the article or surface to be coated, in practicing the present invention, the substrate can be treated with a primer or a surface modification method.

Preparation of the compositions of the disclosure

The composition of the present disclosure can be prepared according to the procedures denoted in the following Examples or modifications thereof using readily available starting materials, reagents, and conventional procedures or variations thereof well-known to a practitioner of ordinary skill in the art of synthetic polymer chemistry.

The following examples are provided to further illustrate details for the preparation and use of the composition of the present disclosure. They are not intended to be limitations on the scope of the instant invention in any way, and they should not be so construed. Furthermore, the compositions described in the following examples are not to be construed as forming the only genus that is considered as the contribution of the inventors to the art. Those skilled in the art will readily understand that known variations of the conditions and processes of the following preparative procedures can be used to prepare these compositions. All temperatures are in degrees Celsius unless noted otherwise.

Anti-fogging property

In the examples hereinbelow, evaluation of anti-fog property was carried out using the following three methods: A) observation with bare eyes on whether fogging develops due to breathing moisture onto coated surface; B) exposure of the coated surface, which is kept at around 1 °C by applying cooling power at the back, to 100% relative humidity of ca. 35 °C for ca. 10 min. The anti-fog quality of the samples is assessed by measuring the intensity of a laser light scattered on the sample surface at four pre-selected angles (i.e., 1, 2, 4 and 8 degrees) from the direction of the incident beam. Simultaneously, the scattering pattern was observed on the translucent screen and it was recorded for documentation purposes. The exposed surface may be dried with blowing nitrogen and followed by another exposure to moisture. Three exposure-drying-exposure cycles were typically carried out; C) EN 168 test for resistance to fogging of oculars, where samples were conditioned in de-ionized water for ca. 1 h, dabbed dry, and then conditioned in air with 50% relative humidity for at least 12 h before the optical evaluation. The anti-fog property was classified as: 'fail' (fog develops during anti-fog test A or B); 'acceptable' (pass anti-fog tests A and B, but may show some non-uniformity of water condensation during the tests); 'good' (pass anti-fog tests A and B easily); and 'very good' (pass all anti-fog tests A, B and C).

Hardness property

The pencil hardness of the coating was estimated by scratching the surface with pencils with different hardness (6B - 9H). The specific hardness of a pencil that can cause permanent scratches on the surface is recorded as the pencil hardness of the coating. No standard was strictly followed due to the low thickness of the coating. It is known that the soft substrate could affect greatly the pencil hardness test (e.g., ASTM D3363-05) on very thin films. As references, the pencil hardness of Makrolon® polycarbonate (Bayer Inc.) was rated herein as "F" and cast PMMA (Vermont Plastics Specialties) as "6H".

Abrasion resistance property

Abrasion resistance of the coated samples was assessed by the sand falling method. The instrument and procedures according to EN 168 test for resistance to surface damage by fine particles were employed. 3.00 kg of sand (alumdun ceramic grit #46, Dawson Macdonald Co., Inc.) defined in Technical Purchase Description for the Canadian Forces was trickled onto the coated surface of a rotating sample and the reduced luminance factor (RLF) of the sample after the falling sand was determined using the method and instrument specified in EN 167 light diffusion test. Cast poly(methyl methacrylate) (PMMA, Vermont Plastics Specialties) plaques of 0.08" thick and 1.5"xl .5" in dimension were used as a reference.

Optical transparency and haze properties

The optical transparency and haze were measured using BYK haze-gard plus. The thickness of coating was measured using Filmetrics F40 (Filmetrics, Inc.).

Coating solution characterization

Solid content of the coating solution was measured using HB 43-S halogen moisture analyzer (Mettler-Toledo, Canada). Viscosity was measured with Merlin II viscometer (Rheosys LLC).

Preparation of materials

Choline linear alkylbenzene sulfonate solution in diacetone alcohol (solution A) Choline linear alkylbenzene sulfonate (linear alkylbenzene sulfonic acid was commercially available from Alfa Aesar) was prepared according to the method disclosed in U.S. Pat. No. 5,877,254. The obtained sulfonate (66.5 g) and dibutyltin dilaurate (DBTDL, 0.33 g, Alfa-Aesar) were dissolved in 66.5 g of dry diacetone alcohol (Sigma-Aldrich) and stored over molecular sieves (3 A, Union Carbide Corp. Linde Division).

2-(T iethoxysilylpropylcarbamyl)choline linear alkylbenzene sulfonate (TESCS) To solution A (23.4 g) at room temperature was added (3-isocyanatopropyl) triethoxy silane (TESI, 6.88 g, Sigma-Aldrich). The solution was stirred at room temperature for 72 h before use. 12-Triethoxysilylpropylcarbamyl ricinoleamidopropyl ethyldimonium ethosulfate (TESRS) A solution of ricinoleamidopropyl ethyldimonium ethosulfate (lipoquat R^tm, Lipo Chemicals, Inc.) in diacetone alcohol was prepared by dissolving 27.3 g of lipoquat R^tm and 0.14 g of DBTDL in 27.3 g of diacetone alcohol. The solution was stored over molecular sieves (3 A) overnight (solution B). To 21.0 g of solution B was added 5.0 g of TESI. The resulting solution was stirred at room temperature for 72 h before use. a-(Triethoxysilylpropylcarbamyl) poly (ethylene glycol) -γ-oleate (EGMSi) A solution of poly(ethylene glycol) monooleate (PEGMO, average Mw = 860, Sigma-Aldrich) in diacetone alcohol was prepared by dissolving 50.0 g of PEGMO and 0.12 g of DBTDL in 50.0 g of dry diacetone alcohol. The solution was stored over molecular sieves (3 A) overnight before use (solution C). To 20.0 g of solution C was added 2.9 g of TESI. The solution was stirred at room temperature overnight before use. a, o Bis(triethoxysilylpropylcarbamyl) poly(ethylene glycol) (EGTES-400) A solution of poly(ethylene glycol) (PEG-400, Mw « 400, Sigma-Aldrich) in diacetone alcohol was prepared by dissolving 50.0 g of PEG-400 and 0.1 1 g of DBTDL in 50.0 g of dry diacetone alcohol. The solution was stored over molecular sieves (3 A) overnight before use (solution D). To 20.0 g of solution D was added 12.3 g of TESI. The solution was stirred at room temperature overnight before use. a, CLhBis(triethoxysilylpropylcarbamyl) poly (ethylene glycol) (EGTES-1000) A solution of poly(ethylene glycol) (PEG- 1000, Mw « 1000, Sigma-Aldrich) in diacetone alcohol was prepared by dissolving 15.0 g of PEG- 1000 and 0.02 g of DBTDL in 20 g of dry diacetone alcohol. The solution was stored over molecular sieves (3 A) overnight before use (solution E). To solution E obtained above was added 7.4 g of TESI. The solution was stirred at room temperature overnight before use.

Coating application method

Various coating methods may be used to coat the composition onto a surface of a desired substrate, for example, spin-coating, dip-coating, doctor-blade coating, roller coating, spray coating, or flow coating. Prior to coating, the substrate can be treated with a primer or a surface modification method to improve adhesion of the composition to the substrate. In the following examples, the surface of the substrate were treated with a primer. All primers conventionally used for optically clear articles, such as protective eyewear (goggles, face shields, visors, etc.), ophthalmic lenses, automobile windshields, windows, and the like, may be used herein. Particularly, primers based on poly(meth)acrylic latex and polyurethane latex are preferred. Primer compositions can be deposited onto the surface(s) of the transparent PC substrate by typical coating methods, for example but not limited to dip-coating or flow coating, then air dried or thermally dried.

The substrate, for example a transparent polycarbonate (PC) plaque, should be thoroughly cleaned with aqueous detergent solution (for example, a solution of ca. 150 mL of neutral Sunlight™ detergent or alkaline Simple Green in 1000 mL of de-ionized water) by, for example, ultrasonication for 3 - 60 min, and rinsed with de-ionized water and dried before application of primer or the coating.

Preferably, the coated film is thermally treated for drying and curing to form a cross-linked polymeric network. Suitable drying temperatures are preferably at about 40 °C to about 100 °C, with 50 - 80 °C more preferred. The drying time is preferred to be about 5 - 60 min. Suitable temperatures for curing the coating composition are preferably at about 40 °C to about 150 °C, with 50 - 130 °C more preferred, and with 100 - 130 °C even more preferred. The duration of heating should be effective to form a mechanically stable and abrasion-resistant film and is preferably about 0.5 to 4 h. The temperatures and times are not intended to be limiting. It should be recognized by the skill in the art that the temperatures and times utilized will vary according to the actual situations, for example, the ratio of components, and the coating layer thickness, etc.

The thickness of the coating is preferably 1 - 50 μηι, with 3 - 25 μιη more preferred. Example 1

To 5.4 g of de-ionized water was added dropwise a mixture of 2.36 g of 3-glycidoxypropyl trimethoxy silane (GPTMS, Sigma-Aldrich), 2.5 g of TESCS, and 2.5 g of TESRS. The resulting mixture was magnetically stirred at room temperature for 1 h before a solution of 0.33 g of itaconic acid (ITA, Sigma-Aldrich) in 5.0 g of propylene glycol methyl ether (PM ether, Alfa- Aesar) was added in one shot. The solution was stirred at room temperature for 30 min, to which was added dropwise 6.0 g of tetraethoxysilane (TEOS, Sigma-Aldrich). The solution was stirred at room temperature overnight. The solution has a viscosity of 13.8 cp, and a solid content of 24.8%. The solution was applied to one of the primed surfaces of PC substrate by flow coating technique, then dried at 60 °C for 30 min and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The thickness of the film is about 7 - 9 μηι. The coated sample had a transparency of 91.2%, a haze of 0.3%, a pencil hardness of 6H, and a reduced luminance factor (RLF) of 3.9 cd.m^"2.lx^"' after falling sand (note: PMMA reference has a RLF of 30.4 cd.m^"2.lx^"'). The coating showed acceptable fog resistance when tested according to the methods described above.

Example 2

To 3.6 g of de-ionized water was added dropwise 2.4 g of GPTMS. The mixture was stirred for 30 min. A mixture solution of 3.2 g of TESRS and 2.8 g of TESCS was added dropwise. After the resulting mixture was stirred for 30 min, a solution of 0.33 g of IT A in 3.6 g of PM ether was added in one shot. The reaction solution was stirred at room temperature for another 30 min before 3.1 g of TEOS was slowly dropped in. The solution was stirred at room temperature overnight. The solution has a solid content of 30.5%. The solution was flow-coated onto primed PC substrate, dried at 60 °C for 30 min, and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The coated sample had a transparency of 91.1%, a haze of 0.25%, a pencil hardness of 5H, and a RLF of 2.37 cd.m^"2.lx^"' after falling sand [note: PMMA reference has a RLF of 21.67 cd.m^*2.lx^"']. The coating showed good fog resistance when tested according to the method described above.

Example 3

To 2.6 g of de-ionized water was added dropwise 2.4 g of GPTMS. The mixture was stirred for 30 min. A mixture solution of 4.9 g of EGMSi and 1.28 g of TESRS was added dropwise. After the resulting mixture was stirred for 30 min, a solution of 0.36 g of ITA in 2.4 g of PM ether was added in one shot. The reaction solution was stirred at room temperature for 30 min before 1.6 g of TEOS was slowly dropped in. The solution was stirred at room temperature overnight. The solution has a viscosity of 26.4 cp, a solid content of 34.7%. The solution was flow-coated onto primed PC substrate, dried at 60 °C for 30 min, and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The thickness of the films is ca. 8 - 10 μι^η. The coated sample had a transparency of 91.1%, a haze of 0.21%, a pencil hardness of 3H, and a RLF of 6.15 cd.rn llx^"1 after falling sand [note: PMMA reference has a RLF of 24.57 cd.m^"2.lx^"']. The coating showed very good fog resistance when tested according to the methods described above.

When the coating was applied onto primed glass slide, the same smooth and optically transparent films were obtained, which showed very good fog resistance when tested according to the methods described above.

Example 4

To 4.5 g of de-ionized water was added dropwise a mixture of 2.4 g of GPTMS, 2.0 g of TESRS, 4.0 g of EGMSi, and 3.5 g of EGTES-400. The mixture was stirred at room temperature for 1 h. To the solution was added a solution of 0.4 g of ITA in 4.5 g of PM ether in one shot. After the solution was stirred for 30 min, 2.0 g of TEOS was slowly dropped in. The solution was stirred at room temperature overnight. The solution has a solid content of 30.8%. The solution was flow-coated onto primed PC substrate, which was dried at 60 °C for 30 min and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The coated sample had a transparency of 91.1%, a haze of 0.21%, a pencil hardness of 6H, and a RLF of 2.2 cd.m^"2.lx^"' after falling sand [note: PMMA reference has a RLF of 25.4 cd.m^"2.lx^"']. The coating showed very good fog resistance when tested according to the method described above.

Example 5

To 8.0 g of de-ionized water was slowly added dropwise 3.0 g of EGTES-400 under stirring. The mixture was stirred for 30 min before a mixture of 2.0 g of TESRS, 2.0 g of TESCS, 2.0 g of EGMSi, and 2.4 g of GPTMS was slowly dropped in. The solution was then stirred for another 30 min before 0.4 g of itaconic acid in 8.0 g of PM ether was added in one shot. The resulting solution was stirred at room temperature for 30 min. 4.0 g of TEOS was slowly dropped into the solution, which was allowed to stir at room temperature overnight before use. The solution was flow-coated onto primed PC substrate, which was dried at 60 °C for 30 min and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The coated sample had a transparency of 89.8%, a haze of 0.44%, and a RLF of 1.34 cd.m^"2.lx^"' after falling sand [note: PMMA reference has a RLF of 10.0 cd.m^"2.lx^"']. The coating showed very good fog resistance when tested according to the methods described above. Example 6

To 3.6 g of de-ionized water was added dropwise 2.4 g of GPTMS. The mixture was stirred at room temperature for 30 min. To the solution was added dropwise 6.0 g of TESCS. The resulting mixture was stirred for 30 min before a solution of 0.33 g of ITA in 3.6 g of PM ether was added in one shot. The reaction solution was stirred at room temperature for another 30 min, followed by the addition of 3.1 g of TEOS in drops. The solution was stirred at room temperature overnight. The solution has a solid content of 32.2%. The solution was flow-coated onto primed PC substrate, which was dried at 60 °C for 30 min and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The coated sample had a transparency of 90.8%, a haze of 0.24%, pencil hardness of 6H, and a RLF of 4.4 cd.m^"2.lx^"' after falling sand [note: PMMA reference has a RLF of 20.4 cd.m^" .lx^" ]. The coating showed acceptable fog resistance when tested according to the methods described above.

Example 7

To 4.0 g of de-ionized water was added dropwise 2.4 g of GPTMS. The mixture was stirred at room temperature for 30 min. To the solution was added dropwise 6.0 g of EGMSi. The resulting mixture was stirred at room temperature for 30 min before a solution of 0.4 g of ITA in 4.0 g of PM ether was added in one shot. The reaction solution was stirred at room temperature for 30 min. To the solution was added dropwise 1.6 g of TEOS. The solution was stirred at room temperature overnight. The solution has a solid content of 27.6%. The solution was flow-coated onto primed PC substrate, which was dried at 60 °C for 30 min and cured at 120 °C for 2 h.

A very smooth and optically transparent film was obtained. The coated sample had a transparency of 91.2%, a haze of 0.21%, pencil hardness of 3H, and a RLF of 7.48 cd.m^~2.lx^"' after falling sand [note: PMMA reference has a RLF of 22.7 cd.m^"2.lx^"']. The coating showed good fog resistance when tested according to the methods described above.

All references cited herein are incorporated by reference.

Claims

Claims:

1. A coating composition comprising

- one or more epoxy functionalized silane;

- one or more multifunctional acid; and

- a solvent or a mixture thereof.

2. The coating composition of claim 1 , wherein the surfactant-containing organosilicon is represented by Formula I

wherein

R² is H or CI -20 alkyl; and

n is an integer of 1 to 3.

3. The coating composition of claim 1 or 2, wherein the epoxy functionalized silane is represented by Formula II

R¹⁰ _mRⁿ,(R¹²O)4._m-|Si II

wherein

R¹⁰ is independently an epoxy-containing Cl-20alkyl;

R^{1 1} is Cl -20alkyl;

R¹² is independently H or Cl-20alkyl;

m is an integer of 1 to 3; and

1 is an integer of 0 to 2, provided that m + 1 < 3

wherein each alkyl is independently saturated or unsaturated, linear or branched; optionally substituted chain and said alkyl chain is optionally interrupted by an oxygen.

4. The coating composition of any one of claims 1 to 3, wherein the surfactant-containing organosilicon is represented by Formula la (R²0)₃ Si (LR¹) la

wherein R² is CI -3 alkyl; and LR¹ is as defined in claim 2.

5. The coating composition of any one of claims 1 to 4, wherein the epoxy functionalized silane is represented by Formula Ila

R¹⁰(R¹²O)₃Si Ila.

wherein R¹⁰ and R¹² are as defined in claim 3.

6. The coating composition of any one of claims 1 to 5, further comprising a

tetrafunctional silane represented by Formula III

Si(OR²⁰)₄ III

wherein R²⁰ is independently H or Cl-20alkyl.

7. The coating composition of any one of claims 1 to 6, further comprising a

multifunctional disilane represented by Formula IV

(R³⁰O)_3-o(R ¹)_oSiBSi(R³²)_p(OR³³)₃._p IV

wherein

R³⁰ and R³³ are independently H or Cl -20alkyl;

R³¹ and R³² are independently Cl-20alkyl;

B is Cl -6alkylene-X-(ethyloxy)_n-X-Cl-6alkylene, wherein X is O, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH; and

o and p are independently an integer of 0 to 2.

8. The coating composition of claim 7, wherein the multifunctional disilane is represented by formula IVa

(R³⁰O)₃SiBSi(OR ³)₃ IVa.

9. The coating composition of claim 1 , comprising

- at least one surfactant-containing organosilicon of formula lb

or at least surfactant-containing organosilicon of formula Id

(R²0)₃Si-(C_1-6)alkylene-X-(Ci_₆)alkylene-N⁺(lower alkyl)₃ ^"O3S-ary.-a.kyl Id or at least one surfactant-containing organosilicon of formula Ii

(R²0)₃Si-(C, .₆)alkylene-X-(ethyloxy)_n-(CO)C₈.₂₀alkyl Ii

or a combination of said surfactant-containing organosilicon thereof, wherein R is as defined in claim 2 and X is 0, (CO), 0(CO)0, (CO)O, O(CO), NH(CO)0, 0(CO)NH, NH(CO), (CO)NH or NH(CO)NH;

- one or more epoxy functionalized silane represented by Formula Ila;

R¹⁰(R^,2O)₃Si Ila

wherein R¹⁰ and R¹² are as defined in claim 3

- a solvent or a mixture thereof;

- one or more tetrafunctional silane of formula III as defined in claim 6; and

- optionally one or more multifunctional disilane of formula IVa

(R³⁰O)₃SiBSi(OR³³)₃ IVa

30 33

wherein R , R^JJ and B are as defined in claim 7.

10. A method for coating at least one surface of an article comprising:

- applying a coating composition as defined in claim 1 on at least said one surface, and

- curing said composition.

1 1. A method of providing an article with an anti-fog surface comprising:

- applying a coating composition as defined in claim 1 to the surface of said article, and

- curing said composition.

12. A method of providing an article with an anti-fog and abrasion resistant surface comprising:

- curing said composition.

13. An article having on a surface thereof a coating obtainable by curing a composition as defined in claim 1.

14. The method of any one of claims 10-12 or the article of claim 13 wherein said article is an optically clear article.

15. The method of any one of claims 10- 12 or the article of claim 13 wherein said article is comprising plastics, glass, ceramics, metals, composites or a combination thereof.