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EP-4735924-A1 - COATED OPTICAL ARTICLES DEMONSTRATING ANTI-FOGGING PROPERTIES AND METHODS OF PROVIDING AN OPTICAL ARTICLE WITH ANTI-FOGGING PROPERTIES

EP4735924A1EP 4735924 A1EP4735924 A1EP 4735924A1EP-4735924-A1

Abstract

Coated optical articles demonstrating anti-fogging properties are provided. The coated articles comprise: (1) an optical substrate; and (2) a coating layer applied as a topmost layer over a surface of the substrate. The coating layer is formed from a treatment composition comprising: (A) a polymer comprising carboxylic acid groups, pyrrolidone groups and alkoxysilane groups; (B) an alkoxysilane comprising an amino functional group, an ammonium functional group, an epoxy functional group, or ethylenic unsaturation; and (C) polyvinyl pyrrolidone.

Inventors

  • GUO, QUNHUI
  • HORNER, ELIZABETH AMELIA
  • WU, FANGHUI
  • ESTOK, Robin Nichole

Assignees

  • PPG Industries Ohio Inc.

Dates

Publication Date
20260506
Application Date
20240627

Claims (20)

  1. 1 . A coated optical article comprising: (1) an optical substrate; and (2) a coating layer applied as a topmost layer over a surface of the substrate, wherein the coating layer is formed from a treatment composition comprising: (A) a polymer comprising carboxylic acid groups, pyrrolidone groups and alkoxysilane groups; (B) an alkoxysilane comprising an amino functional group, an ammonium functional group, an epoxy functional group, or ethylenic unsaturation; and (C) polyvinyl pyrrolidone.
  2. 2. The coated optical article of claim 1 , wherein the substrate (1 ) comprises glass, polymethylmethacrylate, polycarbonate, polyethylene terephthalate (PET), polyurethane, polyurea-urethane, polythiourethane, polyamide, episulfide, cellulose triacetate (TAC), cyclic olefin polymer (COP), cyclic olefin copolymer (COC) and/or poly (allyl diglycol carbonate).
  3. 3. The coated optical article of claim 1 or claim 2, wherein the substrate has two opposing surfaces.
  4. 4. The coated optical article of claim 3, wherein the coating layer (2) is applied over one surface of the substrate.
  5. 5. The coated optical article of claim 3 or 4, wherein the coating layer (2) is applied over both opposing surfaces of the substrate.
  6. 6. The coated optical article of any of claims 1 to 5, wherein the polymer (A) is prepared from a mixture of vinyl monomers comprising: (i) a (meth)acrylic acid monomer, (ii) a (meth)acrylate functional alkoxysilane, and (iii) a pyrrolidone functional vinyl monomer.
  7. 7. The coated optical article of claim 6, wherein the polymer (A) is prepared from a mixture comprising 1 to 20 percent by weight (meth)acrylic acid, 10 to 70 percent by weight (meth)acrylate functional alkoxysilane, and 1 to 30 percent by weight pyrrolidone functional vinyl monomer, based on the total weight of monomers used to prepare the polymer (A).
  8. 8. The coated optical article of claim 6 or 7, wherein the (meth)acrylate functional alkoxysilane comprises 3- methacryloxypropyltri alkoxysilane.
  9. 9. The coated optical article of any of claims 6 to 8, wherein the pyrrolidone functional vinyl monomer comprises N-vinylpyrrolidone.
  10. 10. The coated optical article of any of claims 1 to 9, wherein the polymer (A) has a weight average molecular weight of 10,000 to 35,000, or 10,000 to 30,000, or 10,000 to 25,000, or 10,000 to 20,000, or 10,000 to 16,000, or 10,000 to 15,000, or 12,000 to 35,000, or 12,000 to 30,000, or 12,000 to 25,000, or 12,000 to 20,000, or 12,000 to 16,000, or 12,000 to 15,000Da, measured by GPC using polystyrene calibration standards.
  11. 1 1 . The coated optical article of any of claims 1 to 10, wherein the alkoxysilane (B) comprises 3-methacryloxypropyltrialkoxysilane, 3- glycidoxypropyltrialkoxysilane, dimethyloctadecyl[3- (trialkoxysilyl)propyl]ammonium chloride, 3-aminopropyltrialkoxysilane, N(beta- aminoethyl) gamma-aminopropyltrialkoxy-silane, 3-(2- aminoethylamino)propyltrialkoxysilane and/or 3-[2-(2- aminoethylamino)ethylamino]propyl-trialkoxysilane.
  12. 12. The coated optical article of claim 1 1 wherein the alkoxysilane (B) comprises 3-glycidoxypropyltrimethoxysilane and/or 3- glycidoxypropyltriethoxysilane.
  13. 13. The coated optical article of any of claims 1 to 12, wherein the polymer (A) is present in the treatment composition in an amount of 0.03 to 89.9 percent by weight, or 0.03 to 75 percent by weight, or 0.03 to 60 percent by weight, or 0.05 to 89.9 percent by weight, or 0.05 to 75 percent by weight, or 0.05 to 60 percent by weight, or 0.06 to 89.9 percent by weight, or 0.06 to 75 percent by weight, or 0.06 to 60 percent by weight; the alkoxysilane (B) is present in the treatment composition in an amount of 0.1 to 50 percent by weight, or 0.3 to 50 percent by weight, or 0.5 to 50 percent by weight, and the polyvinyl pyrrolidone (C) is present in the treatment composition in an amount of 10 to 99.5 percent by weight, or 10 to 99 percent by weight, or 35 to 99.5 percent by weight, or 35 to 99 percent by weight, or 40 to 99.5 percent by weight, or 40 to 99 percent by weight, based on the total weight of the polymer (A), the polysiloxane (B), and the polyvinyl pyrrolidone (C).
  14. 14. The coated optical article of any of claims 1 to 13, wherein the treatment composition further comprises (D) a tetraalkoxysilane.
  15. 15. The coated optical article of claim 14, wherein the tetraalkoxysilane (D) is present in the treatment composition in an amount of 0.1 to 15 percent by weight, or 0.1 to 10 percent by weight, or 0.1 to 5 percent by weight, based on the total weight of the polymer (A), the polysiloxane (B), and the polyvinyl pyrrolidone (C).
  16. 16. The coated optical article of claim 1 1 , wherein the tetraalkoxysilane (D) comprises tetramethoxysilane and/or tetraethoxysilane.
  17. 17. The coated optical article of any of claims 1 to 16, wherein the coating layer is applied indirectly over a surface of the substrate on top of an intervening layer, and wherein the intervening layer comprises a primer layer, a tinted layer, a photochromic layer and/or a hardcoat layer interposed between the substrate and the coating layer.
  18. 18. The coated optical article of claim 17, wherein the intervening layer on the surface of the substrate comprises a hardcoat layer, which in turn comprises a siloxane.
  19. 19. The coated optical article of any of claims 1 to 18, wherein the coating layer (2) demonstrates an initial water contact angle of less than 50°, or less than 30°, or less than 25°, measured via a sessile drop measurement technique using an optical goniometer/tensiometer.
  20. 20. The coated optical article of any of claims 1 to 19, wherein the coating layer (2) demonstrates a dry film thickness of 150 nm to 4000 nm.

Description

COATED OPTICAL ARTICLES DEMONSTRATING ANTI-FOGGING PROPERTIES AND METHODS OF PROVIDING AN OPTICAL ARTICLE WITH ANTI-FOGGING PROPERTIES FIELD OF THE DISCLOSURE [0001] The present disclosure relates to coated optical articles such as eyeglass lenses, comprising substrates coated with a coating layer that exhibits anti-fogging properties. BACKGROUND [0002] When a person wears optical articles such as eyeglasses or face goggles, lens fogging often occurs in high humidity or high temperature conditions, or at interfacial boundaries where there is a significant temperature or humidity difference, such as when wearing swimming goggles in a pool, or along a bottom edge of a lens when a person is also wearing a face mask. Antifogging coatings have been developed to reduce the fogging. [0003] Several different types of hydrophilic anti-fog coatings for optical articles are known. However, these coatings often have issues with effectiveness or durability. Optical articles with currently available anti-fog coatings often become saturated with moisture, making them uncomfortable or affecting the wearer’s vision. Certain coatings may be scratched easily, which results in decreased durability, reduced vision, or unacceptable appearance. [0004] It would be desirable to provide an alternative optical article with antifogging properties while mitigating or avoiding at least some of the drawbacks of the prior art. SUMMARY [0005] Coated optical articles demonstrating anti-fogging properties are provided. The coated articles comprise: (1 ) an optical substrate; and (2) a coating layer applied as a topmost layer over a surface of the substrate. The coating layer is formed from a treatment composition comprising: (A) a polymer comprising carboxylic acid groups, pyrrolidone groups and alkoxysilane groups; (B) an alkoxysilane comprising an amino functional group, an ammonium functional group, an epoxy functional group, or ethylenic unsaturation; and (C) polyvinyl pyrrolidone. [0006] Also provided are methods of providing an optical article with antifogging properties, the method comprising: applying a coating layer as a topmost layer over a surface of an optical substrate, wherein the coating layer is formed from the treatment composition described above. DETAILED DESCRIPTION [0007] Other than in any operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions and so forth used in the specification and claims are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties to be obtained. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. [0008] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the disclosure are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contain certain errors necessarily resulting from the standard deviation found in their respective testing measurements. [0009] Also, it should be understood that any numerical range recited herein is intended to include all sub-ranges subsumed therein. For example, a range of “1 to 10” is intended to include all sub-ranges between (and including) the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10. [0010] As used in this specification and the appended claims, the articles "a," "an," and "the" include plural referents; i. e., are understood to mean “at least one”, unless expressly and unequivocally limited to one referent. [0011 ] The various examples of the coated optical article as presented herein are each understood to be non-limiting with respect to the scope of the disclosure. [0012] As used in the following description and claims, the following terms have the meanings indicated below: [0013] The term “reactive” refers to a functional group such as an alkoxysilane or silanol group, capable of undergoing a chemical reaction with itself and/or other functional groups spontaneously or upon the application of heat or in the presence of a catalyst or by any other means known to those skilled in the art. [0014] The term "optical quality", as used for example in connection with polymeric materials, e.g., a "resin of optical quality" or "organic polymeric material of optical quality" means that the indicated material, e.g., a polymeric material, resin, or resin composition, is or forms a substrate, layer, film or coati