# US 2015/0148480 A1 · Optical material and articles formed therefrom

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- Number: US 2015/0148480 A1
- Document ID: US20150148480A1
- Status: Published application
- Kind: A1
- Application number: 14/404,870
- Filed: 2013-05-31
- Published: 2015-05-28
- Earliest claimed: 2012-06-01
- Assignees: Biofarmix Inc.
- Applicants: Biofarmix Inc.
- Inventors: Matthew McBrayer Ellison; Bernard Miles Malofsky; Adam Gregg Malofsky; Tanmoy Dey; Jeffrey M. Sullivan
- Web page: https://patentgrep.com/patent/US20150148480A1

## CPC

- C08G 63/00: Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule (polyester-amides C08G69/44; polyester-imides C08G73/16)
- C07C 69/38: Malonic acid esters
- C07C 69/708: Ethers
- C08F 18/14: Esters of polycarboxylic acids
- C08F 222/10: Esters
- C09J 5/00: Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J 167/00: Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09J177/12; based on polyester-imides C09J179/08); Adhesives based on derivatives of such polymers
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- G02B 6/255: Splicing of light guides, e.g. by fusion or bonding
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## 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

### Claim at position 1

1-28. (canceled)

### Claim 29

An 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′, R1 and R2, or R3 and R4 are independently selected from the group consisting of C1-C15 alkyl, C2-C15 alkenyl, halo-(C1-C15 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C15 alkyl), aryl-(C1-C15 alkyl), heteroaryl or heteroaryl-(C1-C15 alkyl), or alkoxy-(C1-C15 alkyl), each of which may be optionally substituted by C1-C15 alkyl, halo-(C1-C15 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C15 alkyl), aryl, aryl-(C1-C15 alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester; or
wherein, in the selected formula, R and R′, R1 and R2, or R3 and R4 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 C1-C15 alkyl, halo-(C1-C15 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C15 alkyl), aryl, aryl-(C1-C15 alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 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 (180 nm to 360 nm), the visible region (380 nm to 720 nm), the near infrared region (750 nm to 2,500 nm), the infrared region (2,500 nm to 10,000 nm), the far infrared region (10,000 nm or more) and the terahertz region (about 0.1 to 10 THz).

### Claim 30 (depends on 29)

The optical material according to claim 29, 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.

### Claim 31 (depends on 29)

The optical material according to claim 29 comprises a glass transition temperature (Tg) between −30° C. and 100° C.

### Claim 32 (depends on 29)

The optical material according to claim 29 exhibits a high solvent resistance.

### Claim 33 (depends on 29)

The optical material according to claim 29 comprises a decomposition temperature of about 200° C. or more.

### Claim 34 (depends on 29)

The optical material according to claim 29, wherein the selected formula is:
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 (180 to 360 nm) or the visible spectral region (380 to 720 nm).

### Claim 35 (depends on 29)

An optical component comprising the optical material according to claim 29.

### Claim 36 (depends on 35)

The optical component of claim 35 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.

### Claim 37 (depends on 36)

The optical component according to claim 36, 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.

### Claim 38

An optical material comprising:
a polymerizable material comprising a formula selected from:
wherein, in the selected formula, R and R′, R1 and R2, R3 and R4, and R5 and R6 are independently selected from the group consisting of C1-C5 alkyl, C2-C15 alkenyl, halo-(C1-C5 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C5 alkyl), aryl-(C1-C5 alkyl), heteroaryl or heteroaryl-(C1-C5 alkyl), or alkoxy-(C is alkyl), each of which may be optionally substituted by C1-C5 alkyl, halo-(C1-C5 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl- (C1-C5 alkyl), aryl, aryl-(C1-C5 alkyl), heteroaryl, C1-C5 alkoxy, C1-C5 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester; or
wherein, in the selected formula, R and R′, R1 and R2, or R3 and R4 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 C1-C5 alkyl, halo-(C1-C5 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C5 alkyl), aryl, aryl-(C1-C5 alkyl), heteroaryl, C1-C15 alkoxy, C1-C5 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester; or
wherein, in the selected formula, -[A]- represents —(CRARB)n—, —(CRARB)n—O(C═O)—(CH2)1-15—(C═O)O—(CRARB)n—, —(CH2)n-[CY]-(CH2), a polybutadienyl linking group, a polyethylene glycol linking group, a polyether linking group, a polyurethane linking group, an epoxy linking group, a polyacrylic linking group, or a polycarbonate linking group;
wherein each instance of RA or RB is independently H, C1-C15 alkyl, C2-C15 alkenyl, or a moiety represented by the formula:
wherein -L- is a linking group selected from the group consisting of alkylene, alkenylene, haloalkylene, cycloalkylene, cycloalkylene, heterocyclylene, heterocyclyl alkylene, aryl-alkylene, heteroarylene or heteroaryl-(alkylene), or alkoxy-(alkylene), each of which may be optionally branched and each of which may be optionally substituted by alkyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl- (alkyl), aryl, aryl-(alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, ester, each of which can be optionally branched;
R3 is independently selected from the group defined in R6 above; and
R4 is alkyl, alkenyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl alkyl), aryl-(alkyl), heteroaryl or heteroaryl- (alkyl), or alkoxy-(alkyl), each of which may be optionally branched and each of which can be optionally substituted by alkyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl-(alkyl), aryl, aryl-(alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, ester, each of which may be optionally branched;
-[CY]- represents an alkyl, alkenyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl alkyl), aryl-(alkyl), heteroaryl or heteroaryl-(alkyl), or alkoxy - (alkyl) group
n is an integer from 1 to 25;
m is an integer from 1 to 25;
each instance of Q represents —O— or a direct bond; and
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 curing.

### Claim 39 (depends on 38)

The polymerizable optical material according to claim 38, wherein the optical material is an optical adhesive.

### Claim 40 (depends on 39)

A method for bonding a first substrate and a second substrate of an optical component using the optical adhesive according to claim 39, the method comprising polymerizing the optical adhesive to form a bond between the first substrate and the second substrate.

### Claim 41 (depends on 40)

The method according to claim 40, wherein polymerizing the optical adhesive occurs at ambient temperature.

### Claim 42 (depends on 40)

The method according to claim 40, wherein the first substrate and the second substrate comprise optical fibers.

### Claim 43 (depends on 39)

An optical device comprising a first optical fiber, a second optical fiber and the optical adhesive according to claim 39 disposed between ends of the first optical fiber and the second optical fiber, such that an optical signal can pass from the first optical fiber to the second optical fiber therethrough without substantial signal loss after polymerization of the optical adhesive.

### Claim 44 (depends on 38)

A method of repairing an optical fiber comprising:
pre-placing ends of optical fibers requiring repair into a supported arrangement with the optical material according to claim 38 between the ends of the optical fibers; and
polymerizing the optical material to form a splice having optical characteristics substantially corresponding to those of the optical fibers.

### Claim 45 (depends on 44)

The method according to claim 44, wherein the optical fibers comprise circumferentially disposed cladding, and wherein the ends of the optical fiber repaired retain the cladding during the polymerizing of the optical material.

### Claim 46 (depends on 29)

An optical composite article comprising at least first and second optical materials according to claim 29, wherein the first optical material comprises reinforcing or filler members and the second optical material comprises a binder or polymeric matrix.

### Claim 47 (depends on 29)

An optical fiber comprising the optical material according to claim 29.

### Claim 48 (depends on 47)

The optical fiber according to claim 47 is a single-mode fiber or a multi-mode fiber.