Methods of layer by layer self-assembly of polyelectrolyte comprising light absorbing or stabilizing compound and articles

• US 9,902,869 B2
• Filed: 04/14/2014
• Issued: 02/27/2018
• Est. Priority Date: 05/31/2013
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Schmidt, Daniel J., Buckanin, Richard S., Hebrink, Timothy J., Miller, James R.
• Primary Examiner(s): Bernshteyn, Michael M
• Application Number:
  US14/782,125
• Publication Number:
  US 20160068703A1
• Time in Patent Office: 1,415 Days
• Field of Search: 428522
• CPC Class Codes: B05D 5/061 Special surface effect
• CPC Class Codes: B05D 5/063 Reflective effect B05D5/067 takes precedence
• CPC Class Codes: B05D 7/04 to surfaces of films or sheets producing layered products by applying coatings of pasty or pulverulent plastics B29C41/00
• CPC Class Codes: B05D 7/56 Three layers or more
• CPC Class Codes: C03C 17/42 at least one coating of an organic material and at least one non-metal coating
• CPC Class Codes: C03C 2217/48 having a specific function
• CPC Class Codes: C03C 2217/74 UV-absorbing coatings
• CPC Class Codes: C03C 2217/78 Coatings specially designed to be durable, e.g. scratch-resistant
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 220/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08F 220/60 containing nitrogen in addition to the carbonamido nitrogen
• CPC Class Codes: C08F 226/04 Diallylamine
• CPC Class Codes: C08K 2003/2241 Titanium dioxide
• CPC Class Codes: C08K 3/22 of metals
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09D 139/00 Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 5/00 Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced electrically insulating plastics, resins or waxes H01B3/30; Filling pastes

Abstract

Methods of protecting a substrate from light-induced degradation are described. The methods comprise providing a substrate and disposing onto the substrate a plurality of layers deposited by layer-by-layer self-assembly. At least a portion of the layers comprise an organic light absorbing compound, an organic light stabilizing compound, or a combination thereof dispersed within a polyelectrolyte. Also described are articles comprising a substrate and a plurality of layers deposited by layer-by-layer self-assembly wherein at least a portion of the layers comprise an organic light absorbing compound, an organic light stabilizing compound, or a combination thereof dispersed within a polyelectrolyte. Random copolymers suitable for use in the method and articles are also described.

Claims

1. A method of protecting a substrate from light-induced degradation comprising:

providing a substrate comprising an organic polymeric material;

disposing onto the substrate a plurality of layers deposited by layer-by-layer self-assembly wherein at least a portion of the layers comprise a polyelectrolyte copolymer of an ionic monomer and a copolymerizable organic light absorbing compound, copolymerizable organic light stabilizing compound, or a combination thereof;

and wherein the organic light stabilizing compound or the organic light absorbing compound comprises a group selected from the group consisting of a hindered amine, benzotriazole, benzophenone, triazine, and mixtures thereof.

4. The method of claim 1 wherein the substrate is light-transmissive to visible light.

5. The method of claim 1 wherein the substrate is an inorganic material further comprising a coating comprising an organic polymeric material, the coating disposed between the substrate and plurality of layers deposited by layer-by-layer self-assembly.

6. The method of claim 1 wherein the copolymerizable organic light absorbing or light stabilizing compound comprises a (meth)acryl or vinyl group.

7. The method of claim 1 wherein the ionic monomer comprises a (meth)acryl or vinyl ether group and an ionic group.

8. The method of claim 1 wherein the polyelectrolyte copolymer is a grafted copolymer or a random copolymer.

9. The method of claim 1 wherein the organic light absorbing compound reduces the transmission of ultraviolet light.

10. The method of claim 1 wherein the plurality of layers deposited by layer-by-layer self-assembly further provide a durable top coat or a reduction in surface reflections at 550 nm to less than 2%.

11. The method of claim 1 wherein the substrate is selected from the group consisting of woven or nonwoven fabric, an optical film, architectural film, greenhouse film, window film, protection film, fenestration product, solar light tube film, traffic signage film, commercial graphics film, a solar photovoltaic front-sheet film, and solar power concentrating mirror.

12. The method of claim 11 wherein the optical film is a multilayer film selected from the group consisting of an ultraviolet reflector, a blue-reflector, a visible reflector, an infrared reflector, or a combination thereof.

13. The method of claim 12 wherein the plurality of layers deposited by layer-by-layer self-assembly comprise alternating stacks of low refractive index bi-layers and high refractive index bi-layers that increase the total reflectivity of the multilayer optical film.

14. The method of claim 1 wherein the polyelectrolyte copolymer is provided in an aqueous solvent.

2. A method of protecting a substrate from light-induced degradation comprising:

providing a substrate;

disposing onto the substrate a plurality of alternating layers of a polyelectrolyte and inorganic oxide nanoparticles deposited by layer-by-layer self-assembly wherein at least a portion of the layers comprise a polyelectrolyte copolymer of an ionic monomer and a copolymerizable organic light absorbing compound, copolymerizable organic light stabilizing compound, or a combination thereof; and

wherein the organic light stabilizing compound or the organic light absorbing compound comprises a group selected from the group consisting of a hindered amine, benzotriazole, benzophenone, triazine, and mixtures thereof.

3. The method of claim 2 wherein the substrate consists of an inorganic material or an organic material.

15. An article comprising

a substrate comprising an organic polymeric material;

a plurality of layers deposited by layer-by-layer self-assembly disposed on the substrate, wherein at least a portion of the layers comprise a polyelectrolyte copolymer of an ionic monomer and a copolymerizable organic light absorbing compound, copolymerizable organic light stabilizing compound, or a combination thereof; and

wherein the organic light stabilizing compound or the organic light absorbing compound comprises a group selected from the group consisting of a hindered amine, benzotriazole, benzophenone, triazine, and mixtures thereof.

17. The article of claim 15 wherein the substrate consists of an inorganic material or an organic material.

18. The article of claim 15 wherein the substrate comprises an organic polymeric material.

19. The article of claim 15 wherein the substrate is light-transmissive to visible light.

20. The article of claim 15 wherein the substrate is an inorganic material further comprising a coating comprising an organic polymeric material, the coating disposed between the substrate and plurality of layers deposited by layer-by-layer self-assembly.

21. The article of claim 15 wherein the copolymerizable organic light absorbing or light stabilizing compound comprises a (meth)acryl or vinyl group.

22. The article of claim 15 wherein the ionic monomer comprises a (meth)acryl or vinyl ether group and an ionic group.

23. The article of claim 15 wherein the polyelectrolyte copolymer is a grafted copolymer or a random copolymer.

24. The article of claim 15 wherein the organic light absorbing compound reduces the transmission of ultraviolet light.

25. The article of claim 15 wherein the plurality of layers deposited by layer-by-layer self-assembly further provide a durable top coat or a reduction in surface reflections at 550 nm to less than 2%.

26. The article of claim 15 wherein the substrate is selected from the group consisting of woven or nonwoven fabric, an optical film, architectural film, greenhouse film, window film, protection film, fenestration product, solar light tube film, traffic signage film, commercial graphics film, a solar photovoltaic front-sheet film, and solar power concentrating mirror.

27. The article of claim 15 wherein the optical film is a multilayer film selected from the group consisting of an ultraviolet reflector, a blue-reflector, a visible reflector, an infared reflector, or a combination thereof.

28. The article of claim 15 wherein the plurality of layers deposited by layer-by-layer self-assembly comprise alternating stacks of low refractive index bi-layers and high refractive index bi-layers that increase the total reflectivity of the multilayer optical film.

16. An article comprising

a substrate;

a plurality of alternating layers of a polyelectrolyte and inorganic oxide nanoparticles deposited by layer-by-layer self-assembly disposed on the substrate wherein at least a portion of the layers comprise a polyelectrolyte copolymer of an ionic monomer and a copolymerizable organic light absorbing compound, copolymerizable organic light stabilizing compound, or a combination thereof; and

wherein the organic light stabilizing compound or the organic light absorbing compound comprises a group selected from the group consisting of a hindered amine, benzotriazole, benzophenone, triazine, and mixtures thereof.