High refractive index monomers for optical applications

• US 7,297,810 B2
• Filed: 12/30/2004
• Issued: 11/20/2007
• Est. Priority Date: 12/30/2004
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Goenner, Emily S., Kolb, Brant U., Noyola, Joan M., Mader, Roger A., Walker, Christopher B. Jr., Wang, Sharon
• Primary Examiner(s): Lipman; Bernard
• Application Number:
  US11/026,674
• Publication Number:
  US 20060147703A1
• Time in Patent Office: 1,055 Days
• Field of Search: 560/221
• US Class Current: 560/221
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07C 69/653 Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
• CPC Class Codes: G02B 1/10 Optical coatings produced by application to, or surface treatment of, optical elements G02B1/08 takes precedence
• CPC Class Codes: G02B 1/111 using layers comprising organic materials
• CPC Class Codes: G02B 1/14 Protective coatings, e.g. hard coatings
• CPC Class Codes: Y10T 428/256 Heavy metal or aluminum or compound thereof
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers

Abstract

The present invention includes optical coatings containing ultraviolet curable monomers employing a bromine substituted fluorene structure. The fluorene backbone of the monomers of the present invention may also be functionalized with one or more polymerizable or reactive functionalities, and most readily at the 9 position. Compositions of the present invention include the reactive bromosubstituted fluorenes combined with inorganic nanoparticles, particularly nanoparticles with reactive surface modifiers exhibiting polymerizable functionality. Reactive high index nanoparticles such as surface modified zirconia are contemplated.

Claims

1. A bromo-substituted fluorene monomer defined by either one of the following formulae:

2. The monomer of claim 1 selected from the group consisting of acrylic acid 3-[9-(3-acryloyloxy-propyl)-2,3,7-tribromo-9H-fluoren-9-yl]-propyl ester, acrylic acid 3-{9-[3-acyloyloxy-propoxy)-propyl]-2,3,7-tribromo-9H-fluoren-9-yl}-propyl ester, 3-[9-(3-acryloyloxy-propyl)-2,7-dibromo-9H-fluoren-9-yl]-propyl ester, and 2-[9-(2-acryloyloxy-ethyl)-2,7-dibromo-9H-fluoren-9-yl]-ethyl ester.

3. A polymerizable composition comprising a bromo-substituted fluorene monomer defined by either one of the following formulae:

4. The composition of claim 3 wherein said bromo substituted fluorene monomer is selected from the group consisting of acrylic acid 3-[9-(3-acryloyloxy-propyl)-2,3,7-tribromo-9H-fluoren-9-yl]-propyl ester, acrylic acid 3-{9-[3-acyloyloxy-propoxy)-propyl]-2,3,7-tribromo-9H-fluoren-9-yl}-propyl ester, 3-[9-(3-acryloyloxy-propyl)-2,7-dibromo-9H-fluoren-9-yl]-propyl ester, and 2-[9-(2-acryloyloxy-ethyl)-2,7-dibromo-9H-fluoren-9-yl]-ethyl ester.