Anti-fog coating composition, process, and article

• US 20040247892A1
• Filed: 07/08/2004
• Published: 12/09/2004
• Est. Priority Date: 01/31/2002
• Status: Abandoned Application

• Current Assignee: SABIC Global Technologies BV (Government of Saudi Arabia)
• Original Assignee: SABIC Global Technologies BV (Government of Saudi Arabia)
• Inventors: Chen, Mao
• Application Number:
  US10/887,065
• Publication Number:
  US 20040247892A1
• Time in Patent Office: Days
• US Class Current: 428/429
• CPC Class Codes: C03C 17/30 with silicon-containing compounds
• CPC Class Codes: C03C 17/322 Polyurethanes or polyisocyanates
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/3893 containing silicon
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/6692 with compounds of group C08G18/34
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 2290/00 Compositions for creating anti-fogging
• CPC Class Codes: C08G 65/30 Post-polymerisation treatment, e.g. recovery, purification, drying
• CPC Class Codes: C08J 2475/00 Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
• CPC Class Codes: C08J 2483/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/044 Forming conductive coatings; Forming coatings having anti-static properties
• CPC Class Codes: C08J 7/054 Forming anti-misting or drip-proofing coatings
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: Y10T 428/25 Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
• CPC Class Codes: Y10T 428/266 : of base or substrate
• CPC Class Codes: Y10T 428/31551 : Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31612 : As silicone, silane or siloxane
• CPC Class Codes: Y10T 428/31663 : As siloxane, silicone or silane

Abstract

An anti-fog coating composition comprises a silicone polymer or oligomer, a water dispersible polyurethane polymer or oligomer, and water. A process for forming an anti-fog film comprises applying the anti-fog coating composition to a substrate and coalescing the silicone and polyurethane compounds to form the film. In another embodiment, the process for forming the anti-fog film comprises applying the components of the anti-fog coating composition to a substrate and crosslinking the components to form the anti-fog film. The components generally include a polyol, an isocyanate, a catalyst, and a silicone polymer or oligomer.

Claims

1. A process for forming an anti-fog film on a substrate comprising

applying an aqueous coating composition to the substrate, wherein the aqueous coating composition comprises a silicone compound free from a sulfonic acid group, a water dispersible polyurethane compound, and water;

and

coalescing the silicone compound and polyurethane compound to form a film on the substrate wherein the silicone compound is organosiloxane of the formula;

M_a M′

_bD_cD′

_dT_eT′

_fQ_g,

wherein the subscripts a, c, d, e, f, and g are zero or a positive integer, subject to the limitation that the sum of the subscripts b, d, and f is one or greater;

M has the formula;

R¹₃ SiO_1/2, wherein each R¹ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms;

M′

has the formula;

R²_3-h R³_h SiO_1/2, wherein each R² and R³ are independently monovalent hydrocarbon radicals having from one to forty carbon atoms, and the subscript h is 1, 2, or 3;

D has the formula;

R⁴₂ SiO_2/2, wherein each R⁴ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms;

D′

has the formula;

R⁵_2-iR⁶_iSiO_2/2, wherein each of R⁵ and R⁶ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms, and the subscript i is 1 or 2;

T has the formula;

R⁷SiO3/2, wherein each R⁷ is a monovalent hydrocarbon radical having from one to forty carbon atoms;

T′

has the formula;

R⁸SiO_3/2, wherein R⁸ is a monovalent hydrocarbon radical having from one to forty carbon atoms; and

Q has the formula;

SiO_4/2;

or an ionic or nonionic siloxane alkoxylate of the formula;

wherein each of R^9-17 are independently a monovalent hydrocarbon radical, R¹⁸ is of the general formula;

R¹⁹-Z-(C_mH_(2m-1)R²⁰O)_j(C_nH_2nO)_kR²¹, m and n are integers greater than or equal to 0;

j and k are integers greater than or equal to 0, subject to the proviso that the sum of j+k is greater than or equal to 1;

Z is —

O—

, —

S—

, —

CO—

, —

NH—

, or —

NH₂—

;

R¹⁹ is a divalent hyrdocarbylene radical, R²⁰ and R²¹ are independently hydrogen, alkyl, hydroxyalkyl, amino, amido, amineoxide, cyano, isocyano, aryl, arylene, carboxy, alkoxy, halogen, haloalkyl, haloalkoxy, sulfo, sulfamo, phosphono, salts thereof, combinations comprising at least one of the foregoing, and the like; and

wherein x and y are integers greater than or equal to 0, subject to the proviso that x+y is greater than or equal to 1.

2. The process according to claim 1, further comprising heating the substrate to a temperature of about 20°

C. to about 150°

C.

3. The process according to claim 1, wherein the substrate comprises a polyester, a cellulose ester, a polycarbonate, a polystyrene, a polyvinyl acetate, a polyolefin, and combinations comprising at least one of the foregoing.

4. The process according to claim 1, wherein the aqueous coating composition further comprises a co-solvent selected from the group consisting of N-methyl pyrrolidone, glycol ether, isopropanol, and combinations comprising at least one of the foregoing co-solvents.

5. The process according to claim 1, wherein the silicone compound is chemically bound to the polyurethane compound.

6. The process according to claim 1, wherein the co-solvent is about 5 to about 10 weight percent of the coating composition.

7. The process according to claim 1, wherein the silicone is a polydimethylsiloxane selected from poly[dimethylsiloxane-co-methyl(3-hydroxypropyl)siloxane]graft-poly(ethylene glycol) methyl ether, poly[dimethylsiloxane-co-[3-[2-(2-hydroxyethoxy)ethoxy]propyl]methylsiloxane, poly[dimethylsiloxane-co-(3-aminopropyl)methylsiloxane], poly[dimethylsiloxane-co-methyl(3-hydroxypropyl)siloxane]-graft poly(ethylene/propylene glycol) methyl ether, poly[dimethylsiloxane-co-methyl(3-hydroxypropyl)siloxane]-graft-tetrakis(1,2-butylene glycol), poly(dimethylsiloxane-co-alkylmethylsiloxane), poly[dimethylsiloxane-co-methyl(stearoyloxyalkyl)siloxane], poly[dimethylsiloxane-co-methyl(3-hydroxypropyl)siloxane]-graft-poly(ethylene/propylene glycol), poly[dimethylsiloxane-co-methyl(3-hydroxypropyl)siloxane]-graft-poly(ethylene glycol) [3-(trimethylammonio)propyl chloride, poly[dimethylsiloxane-co-methyl(3-hydroxypropyl)siloxane]graft-poly(ethylene glycol) 3-aminopropyl ether, poly[dimethylsiloxane-co-methyl(3,3,3-trifluoropropyl)siloxane], poly(dimethylsiloxane bis[[3-[(2-aminoethyl)amino]propyl]dimethoxysilyl] ether, and poly(dimethylsiloxane) ethoxylate/propoxylated.

8. A process for forming an anti-fog film, the process comprising:

applying a coating composition to a substrate, wherein the coating composition comprises a silicone compound free from a sulfonic acid functional group, an isocyanate, a polyol and a catalyst; and

crosslinking the coating composition to form the anti-fog film, wherein the crosslinking comprises heating the substrate to a temperature and for a time effective to form the film.

9. The process according to claim 8, wherein the silicone compound is of the formula:

M_a M′

_bD_cD′

_dT_eT′

_fQ_g,

wherein the subscripts a, c, d, e, f, and g are zero or a positive integer, subject to the limitation that the sum of the subscripts b, d, and f is one or greater;

M has the formula;

R¹₃ SiO_1/2, wherein each R¹ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms;

M′

has the formula;

R²_3-h R³_h SiO_1/2, wherein each R² and R³ are independently monovalent hydrocarbon radicals having from one to forty carbon atoms, and the subscript h is 1, 2, or 3;

D has the formula;

R⁴₂ SiO_2/2, wherein each R⁴ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms;

D′

has the formula;

R⁵_2-iR⁶_iSiO_2/2, wherein each of R⁵ and R⁶ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms, and the subscript i is 1 or 2;

T has the formula;

R⁷SiO_3/2, wherein each R⁷ is a monovalent hydrocarbon radical having from one to forty carbon atoms;

T′

has the formula;

R⁸SiO_3/2, wherein R⁸ is a monovalent hydrocarbon radical having from one to forty carbon atoms; and

Q has the formula;

SiO_4/2.

10. The process according to claim 8, wherein the silicone compound is an ionic or nonionic siloxane alkoxylate of the formula:

11. The process according to claim 8, wherein crosslinking the coating composition to form the anti-fog film comprises heating the substrate to a temperature of about 20°

C. to about 150°

C.

12. The process according to claim 8, wherein the substrate comprises a polyester, a cellulose ester, a polycarbonate, a polystyrene, a polyvinyl acetate, a polyolefin, and combinations comprising at least one of the foregoing.

13. The process according to claim 8, wherein the polyol comprises a polycarbonate polyol.

14. The process according to claim 8, wherein the catalyst comprises a metal acetyl acetonate.

15. The process according to claim 8, wherein the catalyst is selected from bis(2,4-pentanedionate) nickel (II), diacetonitrilediacetylacetonato nickel, diphenylnitrilediacetylacetonato nickel, and bis(triphenylphosphine)diacetyl acetylacetonato nickel.

16. The process according to claim 8, wherein the coating composition further comprises a co-solvent.

17. A glass or plastic article having an anti-fogging surface comprising:

a glass or plastic substrate; and

an anti-fog coating disposed on at least one surface of the substrate, the anti-fog coating comprising a crosslinked film formed from a silicone, an isocyanate, a polyol and a catalyst.

18. The glass or plastic article of claim 17, wherein the silicone compound is of the formula:

M_a M′

_bD_cD′

_dT_eT′

_fQ_g,

wherein the subscripts a, c, d, e, f, and g are zero or a positive integer, subject to the limitation that the sum of the subscripts b, d, and f is one or greater;

M has the formula;

R¹₃ SiO_1/2, wherein each R¹ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms;

M′

has the formula;

R²_3-h R³_h SiO_1/2, wherein each R² and R³ are independently monovalent hydrocarbon radicals having from one to forty carbon atoms, and the subscript h is 1, 2, or 3;

D has the formula;

R⁴₂ SiO_2/2, wherein each R⁴ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms;

D′

has the formula;

R⁵_2-iR⁶_iSiO_2/2, wherein each of R⁵ and R⁶ is independently a monovalent hydrocarbon radical having from one to forty carbon atoms, and the subscript i is 1 or 2;

T has the formula;

R⁷SiO3/2, wherein each R⁷ is a monovalent hydrocarbon radical having from one to forty carbon atoms;

T′

has the formula;

R⁸SiO_3/2, wherein R⁸ is a monovalent hydrocarbon radical having from one to forty carbon atoms; and

Q has the formula;

SiO_4/2.

19. The glass or plastic article of claim 17, wherein the silicone compound is an ionic or nonionic siloxane alkoxylate of the formula:

20. The glass or plastic article of claim 17, wherein the polyol comprises a polycarbonate polyol.

21. The glass or plastic article of claim 17, wherein the catalyst comprises a metal acetyl acetonate.

22. The glass or plastic article of claim 17, wherein the catalyst is selected from bis(2,4-pentanedionate) nickel (II), diacetonitrilediacetylacetonato nickel, diphenylnitrilediacetylacetonato nickel, and bis(triphenylphosphine)diacetyl acetylacetonato nickel.