Fluoropolymer coating compositions with multifunctional fluoroalkyl crosslinkers for anti-reflective polymer films

• US 7,351,471 B2
• Filed: 12/30/2004
• Issued: 04/01/2008
• Est. Priority Date: 12/06/2000
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Klun, Thomas P., Schultz, William J., Jing, Naiyong, Qiu, Zai-Ming, Fukushi, Tatsuo, Cao, Chuntao, Walker, Christopher B. Jr., Tatge, Timothy J.
• Primary Examiner(s): Mullis; Jeffrey
• Application Number:
  US11/026,754
• Publication Number:
  US 20050182199A1
• Time in Patent Office: 1,188 Days
• Field of Search: 525/326.3, 525/326.4, 428/339
• US Class Current: 428/339
• CPC Class Codes: G02B 1/111 using layers comprising organic materials
• CPC Class Codes: Y10T 428/269 including synthetic resin or polymer layer or component

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 and a fluoroalkyl containing multi-olefinic crosslinker. In another aspect of the invention, the composition further includes surface modified inorganic nanoparticles.

Claims

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

a fluoropolymer selected from the group consisting of a Br-containing fluoroelastomer, an I-containing fluoroelastomer, a CN-containing fluoroelastomers, and mixtures thereof, wherein the fluoropolymer is formed from TFE, HFP, VDF, and at least one halogen-containing cure site monomer, halogen-containing chain transfer agent, or CN-containing cure site monomer; and

a fluoroalkyl-containing perfluoropolyether multi-acrylate crosslinker; and

a plurality of surface modified inorganic nanoparticles.

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

3. The composition of claim 1, wherein said crosslinker comprises at least one monovalent C1 to C8 fluoroalkyl moiety.

4. The composition of claim 1, wherein said crosslinker comprises at least one monovalent C1 to C8 fluoroalkylene moiety.

5. The composition of claim 1 further comprising a compatibilizer selected from the group consisting of a fluoroalkyl-substituted monoacrylate, a fluoroalkyl-substituted multiacrylate, a fluoroalkylene-substituted monoacrylate and a fluoroalkylene-substituted multi-acrylate.

6. The composition of claim 5, wherein said compatibilizer is selected from the group consisting of C₄F₉SO₂N(CH₃)CH₂CH₂OC(O)CH═

CH₂, C₄F₉SO₂N(CH₂CH₂OC(O)CH═

CH₂)_2, and C₄F₉SO₂N(CH₃)CH₂CH₂OC(O)C(CH₃)═

CH₂.

7. The composition of claim 5, wherein said compatibilizer comprises a thiol or a polythiol compatibilizer.

8. The composition of claim 7, wherein said thiol or polythiol compatibilizer is selected from the group consisting of C₄F₉SO₂N(CH₃)CH₂CH₂OC(O)CH₂SH, C₄F₉SO₂N(CH₃)CH₂CH₂OC(O)CH₂CH₂SH, C₄F₉SO₂N(CH₃)CH₂CH₂SH, and C₄F₉SO₂N(CH₃)CH(OC(O)CH₂SH)CH₂OC(O)CH₂SH.

9. The composition of claim 1, wherein said crosslinker has the chemical formula:

R_fpeQ(X)_n,

wherein R_fpe is a residue of a monovalent HFPO moiety;

wherein Q is a connecting group selected from the group consisting of an alkylene group, an arylene group, an arylene-alkylene group, and an alkylene-arylene group, optionally containing heteroatoms;

wherein X is a free-radically reactive group selected from the group consisting of a meth(acryl) reactive group, an allyl reactive group, and a vinyl reactive group; and

wherein n is 2 to 3.

10. The composition of claim 9, wherein Q is selected from the group consisting of —

(CH₂)_m—

;

—

CH₂O(CH₂)₃—

; and

—

C(O)NRCH₂CH₂—

, where R is an H or lower alkyl of 1 to 4 carbon atoms and m is 1 to 6.

11. An antireflection film having a layer of the composition of claim 1 having a refractive index of less than 1.5, said antireflection film further comprising a high refractive index layer, having a refractive index of greater than 1.5, coupled to said layer of said low refractive index material.

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

17. The composition of claim 1 wherein when applied as layer to a substrate forms a coating layer having a refractive index of less than about 1.5.

18. The composition of claim 1 wherein when applied as layer to a substrate forms a coating layer having a refractive index of less than about 1.45.

19. The composition of claim 1 wherein when applied as layer to a substrate forms a coating layer having a refractive index of less than about 1.42.

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

i) a fluoropolymer selected from the group consisting of a Br-containing fluoroelastomer, an I-containing fluoroelastomer, a CN-containing fluoroelastomers, and mixtures thereof, wherein the fluoropolymer is formed from TFE, HFP, VDF, and at least one halogen-containing cure site monomer, halogen-containing chain transfer agent, or CN-containing cure site monomer;

ii) a fluoroalkyl-containing multi-olefinic crosslinker; and

iii) a plurality of surface modified nanoparticles.

14. A method for forming an optically transmissive, stain and ink repellent, durable optical display comprising:

providing an optical display having an optical substrate;

forming a low refractive index polymer composition comprising

a fluoropolymer selected from the group consisting of a Br-containing fluoroelastomer,

an I-containing fluoroelastomer, a CN-containing fluoroelastomers, and mixtures thereof,

wherein the fluoropolymer is formed from TFE, HFP, VDF, and at least one halogen-containing cure site monomer, halogen-containing chain transfer agent, or CN-containing cure site monomer;

a fluoroalkyl-containing perfluoropolyether multi-acrylate crosslinker; and

a plurality of surface modified nanoparticles;

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

curing said layer to form a cured film.

15. The method of claim 14, wherein providing an optical display comprises provided an optical display having a hard coat layer applied to an optical substrate.

16. The method of claim 14, wherein forming a low refractive index polymer composition comprises reactively coupling the fluoropolymer and the crossliniker.