IP Library Granted Patent US 10,047,192
Granted Patent B2
US 10,047,192 · App. 14/404,870 · Granted Aug 14, 2018

Optical material and articles formed therefrom

Inventors: Matthew McBrayer Ellison (Mason, OH); Bernard Miles Malofsky (Bloomfield, CT); Adam Gregg Malofsky (Loveland, OH); Tanmoy Dey (Willington, CT); Jeffrey M. Sullivan (Goshen, OH)
Assignee: Sirrus, Inc.
C08G63/00C07C69/38C07C69/708C08F18/14C08F222/10C09J5/00C09J167/00G02B1/04G02B6/255
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Quick Facts
Patent No.
US 10,047,192
App. No.
14/404,870
Granted
Aug 14, 2018
Kind
B2
Abstract

Optical materials including polymerizable compositions and oligomeric and polymeric material formed therefrom. The oligomer or polymer material include structural repeat units. The optical material has low or substantially no absorbance of wavelengths in at least one of the spectral regions of interest. Optical components include adhesives, waveguides, spherical or non-spherical optical lenses, architectural articles, automotive components, laminated structures and composites.

Claims (24)

1. An optical component comprising an optical material, the optical material comprising:

an oligomer or polymer material comprising structural repeating units represented by any of the formulas selected from:

wherein the oligomer or polymer material is formed by curing a polymerizable composition;

wherein, in the selected formula, R and R′, R 1 and R 2 , or R 3 and R 4 are independently selected from the group consisting of C 1 -C 15 alkyl, C 2 -C 15 alkenyl, halo-(C 1 -C 15 alkyl), C 3 -C 6 cycloalkyl, halo-(C 3 -C 6 cycloalkyl), heterocyclyl, heterocyclyl-(C 1 -C 15 alkyl), aryl-(C 1 -C 15 alkyl), heteroaryl, heteroaryl-(C 1 -C 15 alkyl), and alkoxy —(C 1 -C 15 alkyl), each of which may be optionally substituted by C 1 -C 15 alkyl, halo-(C 1 -C 15 alkyl), C 3 -C 6 cycloalkyl, halo-(C 3 -C 6 cycloalkyl), heterocyclyl, heterocyclyl-(C 1 -C 15 alkyl), aryl, aryl-(C 1 -C 15 alkyl), heteroaryl, C 1 -C 15 alkoxy, C 1 -C 15 alkylthio, hydroxyl, nitro, azido, cyan, acyloxy, carboxy, or ester; or

wherein, in the selected formula, R and R′, R 1 and R 2 , or R 3 and R 4 are taken together with the atoms to which they are bound to form a 5-7 membered heterocyclic ring which may be optionally substituted by C 1 -C 15 alkyl, halo-(C 1 -C 15 alkyl), C 3 -C 6 cycloalkyl, halo-(C 3 -C 6 cycloalkyl), heterocyclyl, heterocyclyl-(C 1 -C 15 alkyl), aryl, aryl-(C 1 -C 15 alkyl), heteroaryl, C 1 -C 15 alkoxy, C 1 -C 15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester; and

wherein the optical material has a low absorbance, or substantially no absorbance, of wavelengths in one or more of the spectral regions including the vacuum ultraviolet region below 200 nm, the ultraviolet region between 180 nm to 360 nm, the visible region between 380 nm to 720 nm, the near infrared region between 750 nm to 2,500 nm, the infrared region between 2,500 nm to 10,000 nm, the far infrared region greater than 10,000 nm and the terahertz region between about 0.1 THz and 10 THz.

2. The optical component according to claim 1 , wherein the polymerizable composition has a refractive index between 1.40 and 1.50 when measured at 25° C. in a liquid state, prior to polymerization.

3. The optical component according to claim 1 , wherein the optical material comprises a glass transition temperature (T g ) between −30° C. and 100° C.

4. The optical component according to claim 1 , wherein the optical material exhibits a high solvent resistance.

5. The optical component according to claim 1 , wherein the optical material comprises a decomposition temperature of about 200° C. or more.

6. The optical component according to claim 1 , wherein structure repeating unit has the formula:

and

wherein R and R′ are independently ethyl or methyl groups; and

wherein the optical material has low absorbance, or substantially no absorbance, of wavelengths in the ultraviolet spectral region between 180 nm to 360 nm or the visible spectral region between 380 nm to 720 nm.

7. The optical component of claim 1 , which includes one or more of:

an optical waveguide for transmitting electromagnetic radiation selected from the group consisting of infrared, ultraviolet, and visible radiation;

a spherical or non-spherical optical lens;

a substantially transparent architectural article;

an automotive component; and

one or more layers of a laminated structure, wherein at least one layer of the laminated structure comprises the optical material.

8. The optical component according to claim 7 , wherein the automotive component is one or more of a headlight lens, a fog light lens, a turn indicator lens, a brake light lens, an illumination cover, or an illumination accessory.

9. An optical composite article comprising at least first and second optical materials according to claim 1 , wherein the first optical material comprises reinforcing or filler members and the second optical material comprises a binder or polymeric matrix.

10. An optical fiber comprising the optical material according to claim 1 .

11. The optical fiber according to claim 10 is a single-mode fiber or a multi-mode fiber.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2021
From: SIRRUS, INC.
To: NIPPON SHOKUBAI CO., LTD.
Reel/Frame 057725/0797 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2017
From: PACIFIC WESTERN BANK, AS SUCCESSOR IN INTEREST BY MERGER TO SQUARE 1 BANK
To: SIRRUS, INC.
Reel/Frame 041799/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2017
From: MALOFSKY, BERNARD M.
To: SIRRUS, INC.
Reel/Frame 041150/0218 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2017
From: DEY, TANMOY
To: SIRRUS, INC.
Reel/Frame 041150/0333 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2017
From: ELLISON, MATTHEW MCBRAYER
To: SIRRUS, INC.
Reel/Frame 041097/0838 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2015
From: MALOFSKY, ADAM GREGG
To: SIRRUS, INC.
Reel/Frame 035974/0215 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2015
From: SULLIVAN, JEFFREY M.
To: SIRRUS, INC.
Reel/Frame 035974/0419 →
SECURITY INTEREST Recorded Feb 13, 2015
From: SIRRUS, INC.
To: SQUARE 1 BANK
Reel/Frame 034962/0874 →
Continuity (3)
Provisional Application 61693626 · Aug 27, 2012
Provisional Application 61654586 · Jun 1, 2012
Related Publication 20150148480A1 · May 28, 2015