Low refractive index fluoropolymer coating compositions for use in antireflective polymer films

• US 7,323,514 B2
• Filed: 12/30/2004
• Issued: 01/29/2008
• Est. Priority Date: 12/30/2004
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Tatge, Timothy J., Klun, Thomas P., Schultz, William J., Jing, Naiyong, Qiu, Zai-Ming, Fukushi, Tatsuo, Cao, Chuntao, Coggio, William D., Walker, Christopher B. Jr.
• Primary Examiner(s): Lipman; Bernard
• Application Number:
  US11/026,640
• Publication Number:
  US 20060147723A1
• Time in Patent Office: 1,125 Days
• Field of Search: 525/102, 525/254, 525/276
• US Class Current: 525/102
• CPC Class Codes: G02B 1/111 using layers comprising organic materials
• CPC Class Codes: Y10T 428/24942 including components having same physical characteristic in differing degree
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

An economic, optically transmissive, stain and ink repellent, durable low refractive index fluoropolymer composition for use in an antireflection film or coupled to an optical display. In one aspect of the invention, the composition is formed from the reaction product of a fluoropolymer or reactive fluoropolymer, an amino silane ester coupling agent or ester equivalent, a multi-olefinic crosslinker, and optional surface modified inorganic particles or sol gel precursors.

Claims

1. A coatable low refractive index composition for use in an antireflection coating of an optical display component, the composition comprising the reaction product of:

a reactive fluoropolymer;

at least one amino organosilane ester coupling agent or its ester equivalent; and

a multi-olefinic crosslinker.

2. The composition of claim 1, wherein said multi-olefinic crosslinker comprises a multi-acrylate crosslinker.

3. The composition of claim 1 wherein said reactive fluoropolymer comprises a crystalline reactive fluoropolymer.

4. The composition of claim 1, wherein said reactive fluoropolymer comprises an amorphous reactive fluoropolymer.

5. The composition of claim 4, wherein said amorphous reactive fluoropolymer is selected from the group consisting of a Cl-containing fluoroelastomer, a Br-containing fluoroelastomer, an I-containing fluoroelastomer, a nitrile-containing fluoroelastomer, a carbonyl-containing fluoroelastomer, an ester-containing fluoroelastomer and a C═

C containing fluoroelastomer.

6. The composition of claim 1, wherein said one amino organosilane ester coupling agent or its ester equivalent is selected from the group consisting of 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, (aminoethylaminomethyl)phenethyltrimethoxysilane, (aminoethylaminomethyl)phenethyltriethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 4-aminobutyltrimethoxysilane, 4-aminobutyltriethoxysilane, 3 -aminopropylmethyldiethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyldimethylmethoxysilane, 3-aminopropyldimethylethoxysilane, 2,2-dimethoxy-1-aza-2-silacyclopentane-1-ethanamine, 2,2-diethoxy-1-aza-2-silacyclopentane-1-ethanamine, 2,2-diethoxy-1-aza-2-silacyclopentane, 2,2-dimethoxy-1-aza-2-silacyclopentane, 4-aminophenyltrimethoxy silane, and 3-phenylaminopropyltrimethoxy silane.

7. The composition of claim 2, wherein said multi-acrylate crosslinker comprises a fluorinated multi-acrylate crosslinker.

8. The composition of claim 7, wherein said fluorinated multi-acrylate crosslinker comprises a perfluoropolyether multi-acrylate crosslinker.

9. The composition of claim 8, wherein said perfluoropolyether multi-acrylate crosslinker comprises an HFPO-multiacrylate crosslinker.

10. The composition of claim 2, wherein said multi-acrylate crosslinker is selected from the group consisting of PETA and TMPTA.

11. The composition of claim 2, further comprising a monoacrylate.

12. The composition of claim 11, wherein said monoacrylate comprises a fluorinated monoacrylate.

13. The composition of claim 12, wherein said fluorinated monoacrylate comprises a perfluoropolyether monoacrylate.

14. The composition of claim 13, wherein said perfluoropolyether monoacrylate comprises an HFPO-monoacrylate.

15. The composition of claim 1 further comprising a plurality of surface modified inorganic nanoparticles.

16. The composition of claim 15, where in the surface modified particles comprises a mixture of reactive functionality such as acryl, methacryl and/or vinyl groups and non-reactive groups such as trimethylsilyl, and high alkyl and fluoroalkyl silyl groups.

17. The composition of claim 1, wherein said composition further comprises a sol gel precursor selected from the group consisting of a tetraalkoxysilane, a trialkoxysilane, and mixtures thereof.

18. The composition of claim 17, wherein said tetraalkoxysilane is selected from the group consisting of tetraethoxysilane and vinyl triethoxysilane.

19. An antireflection film having a layer of said low refractive index material of claim 1, said antireflection film further comprising a high refractive index layer coupled to said layer of said low refractive index material.

20. An antireflection film having a layer of said low refractive index composition of claim 1, said antireflection film further comprising a zirconium-containing high refractive index layer coupled to said layer of said low refractive index composition.

21. An optical device comprising a layer of said low refractive index composition formed according to claim 1.

22. A method for forming an optically transmissive, stain and ink repellent, durable optical display for use on an article, the method comprising:

providing an optical display having an optical substrate;

forming a low refractive index polymer composition comprising the reaction product of a reactive fluoropolymer, an amino silane ester coupling agent or ester equivalent, and a multi-olefinic crosslinker;

applying a layer of said low refractive index polymer composition to said optical substrate; and

curing said layer to form a cured film.

23. The method of claim 22, wherein providing an optical display comprises providing an optical display having a hard coat layer applied to an optical substrate.

24. The method of claim 22, wherein forming a low refractive index polymer composition comprises:

reactively coupling a fluoropolymer and at least one amino organosilane ester coupling agent or its ester equivalent to form an aminosilane modified fluoropolymer; and

introducing a multi-olefinic crosslinker to said aminosilane modified fluoropolymer.

25. A coatable low refractive index composition for use in an antireflection coating of an optical display component, the composition comprising the reaction product of:

a fluoropolymer;

at least one amino organosilane ester coupling agent or its ester equivalent;

a multi-olefinic crosslinker; and

a plurality of surface modified nanoparticles.

26. An antireflection film having a layer of said low refractive index composition of claim 25, said antireflection film further comprising a zirconium-containing high refractive index layer coupled to said layer of said low refractive index composition.

27. A coatable low refractive index composition for use in an antireflection coating of an optical display component, the composition comprising the reaction product of:

a fluoropolymer;

at least one amino organosilane ester coupling agent or its ester equivalent;

a multi-olefinic crosslinker; and

a sol gel precursor selected from the group consisting of a tetraalkoxysilane, a trialkoxysilane, and mixtures thereof.

28. An antireflection film having a layer of said low refractive index composition of claim 27, said antireflection film further comprising a zirconium-containing high refractive index layer coupled to said layer of said low refractive index composition.