deterrent to birds flying toward those surfaces. [US20070190343A1]. 2-Hydroxy-4-(3-Triethoxysilylpropyl)diphenylketone (SIH6200.0). Compound A. Si H. OEt.
UV Active Silanes: The Synthesis and Application as Bird-deterrent Glass Coatings Joel Zazyczny, Youlin Pan and Barry Arkles Research and Development, Gelest Inc. 11 East Steel Road, Morrisville, PA 19067, USA Background
Synthesis Glass Surface Treatment: A 10% solution of compound B is prepared in ethanol, IPA, acetone
1hr treatment(no IPA rinse)
4
1hr treatment(IPA rinse)
3.5
1hr treatment(no IPA rinse) 4hr treatment(IPA rinse) 4hr treatment(no IPA rinse) 12hr treatment(IPA rinse)
Wavelength(nm)
The white–throated sparrow is the most frequent collision victim in New York City.
Target Compounds 2-Hydroxy-4-(3-Triethoxysilylpropyl)diphenylketone (SIH6200.0) Compound A Si H +
O
OH
O
EtO
Me Si H +
O
Pt Catalyst
Absorbance
450
437
424
411
398
385
372
359
346
333
320
3 2.5
Absorbance (AU)YK-1
2
Absorbance (AU)YK-3
1.5
Absorbance (AU)YK-4
Absorbance (AU)YK-2
Absorbance (AU)YK-5
1
Absorbance (AU)YK-6
0.5
410
399
388
377
366
355
344
333
322
311
300
289
278
267
256
245
234
223
212
190
Adhesion promoter: SIB1817.0 UV active silane: SIH6200.0 Solvent: Acetone
201
0 Wav e le ngth(nm)
UV Microscopy (Transimitted) at 320 nm
2. Samples YK-1: 1% SIH6200.0 YK-2: 1% SIH6200.0 YK-3: 0.5% SIH6200.0 YK-4: 1% SID4352.0 YK-5: 0.5% SID4352.0 YK-6: untreated borosilicate glass slides
YK-1 YK-6
YK-2
YK-3
YK-4
YK-5
UV Microscopy (Transimitted) at 365 nm
Si
YK-1 YK-6
O
Me EtO
Si OEt
O
O
Lab and field experiments to understand the effectiveness of the treated windows and glass panels in homes, commercial buildings and sports stadiums are currently under investigation.
Conclusion § Two hydroxy diphenylketone-containing organosilanes were synthesized and purified. § The UV-absorbing and antireflective organosilanes coatings for transparent or translucent coatings were formulated.
O
OEt
2-Hydroxy-4-(3-Methyldiethoxysilylpropyl)diphenylketone (SIH6198.0) OH O OH Compound B OEt
3.5
OEt
Pt Catalyst
OEt
EtO
4
Coating Formation
Many attempts to address the problem of bird collision have been reported, these include placing objects, or netting on or in front of window glass panels. Our approach to resolving this issue is the development of UV active silanes/UV-absorbing coatings, and applying such coatings to windows or glass exterior-face surfaces. The treated windows or glass panels will provide sufficient optical absorption to make their surfaces visible to birds and act as a deterrent to birds flying toward those surfaces. [US20070190343A1]
EtO
307
UV active silane- UV spectroscopy
Approach
OH
Wavelength(nm)
4.5
1. Formulation of UV active coating Main resin: SIB1660.0 Catalyst: SND2950
OEt
294
12hr treatment(no IPA rinse)
281
450
437
424
411
398
385
372
359
346
333
320
307
294
281
0
268
0
255
0.5
242
0.5
229
1
216
1
203
1hr treated(IPA rinse)
2 1.5
268
2 1.5
3 2.5
255
12hr treatment(no IPA rinse)
242
12hr treatment(IPA rinse)
229
3 2.5
216
4hr treatment(IPA rinse)
Absorbance
4hr treatment(no IPA rinse)
203
4 3.5
190
4.5
respectively, along with water and acetic acid. Water in the amount of 1.5 mol is added to the solution. The solution is aged twenty minutes to allow partial hydrolysis of the ethoxy groups. The solution is then applied to at least a part of the transparent or translucent exterior surface, i.e. commercial building window, in the form of an aerosol spray or a resin. Dipodal silane,1,2SIH6200 Bis(triethoxysilyl)ethane in IPA treated glass slides- effect of (SIB1817.0) rinsing the treatedwas mixed with compound SIH6200+SIB1817 in IPA treated glass slideeffect of to the B to(5/1) improve bonding strength surface before curing rinsing the treated surface before curing glass surface. A UV analysis of those glass slides is 4.5 depicted as follows:
190
Hydrosilylation of the uvinol with methyldiethoxysilane, or triethoxysilane in the presence of Pt-catalyst under mild conditions results in the formation of compound A and B in 60 to 80% yield. Purification can be achieved with wiped film distillation. The structures of both compounds have been confirmed by conventional analytical methods including FTIR, and 1HNMR. The purity of compound A and B has been determined by HPLC.
Absorbance
Ornithologists estimate that up to one billion birds are killed each year in the United States by collision with windows and glass panels in homes, commercial buildings and sports stadiums. The collisions are primarily due to the transparent and reflective nature of glass. In the case of transparent glass, birds see an open path, and in the reflective glass, birds see images that appear as a mirror showing familiar escape routes, and thus, fly unaware into the window or other glass panels to their demise.
YK-2
YK-3
YK-4
YK-5
Wavelength from 300nm to 400nm is visible to birds but transparent to humans. UV spectroscopy confirmed the absorbance of UV light from the UV active silane coated surface compared to the untreated glass slide. In addition, UV microscopy presents dark images at UV wavelengths from the UV active silane treated surface relative to the transparent image on untreated glass slide (YK-6).
§ The coating resin was applied to glass substrates by dipping or in the form of aerosol spray. § Abating bird-strikes on glass can be achieved with a non-reflective UV opaque coating based on new siliceous resins.
