IP Library Granted Patent US 9,376,614
Granted Patent B2
US 9,376,614 · App. 13/878,531 · Granted Jun 28, 2016

Optically active epoxy

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Quick Facts
Patent No.
US 9,376,614
App. No.
13/878,531
Granted
Jun 28, 2016
Kind
B2
Abstract

An optically active composition is described. The composition may include a copolymer of two or more polyepoxides covalently linked by a fused arene.

Claims (61)

1. A compound comprising a formula:

wherein:

B is a polyepoxide; and

Ar is a compound of formula:

wherein:

Ar 1 is a fused arene having 10 to 100 carbon atoms.

2. The compound of claim 1 , wherein B comprises bisphenol A epoxy, bisphenol F epoxy, naphthalene epoxy, diphenylfluorene epoxy, triglycidyl aminophenol epoxy, triglycidyl aminocresol epoxy, tetraglycidyl diaminodiphenylmethane epoxy, tetraglycidyl m-xylylene amine epoxy, N,N-diaminocresol epoxy, phenol novolac epoxy, cresol novolac epoxy, biphenyl epoxy, dicyclopentadiene epoxy, or combinations thereof.

3. The compound of claim 1 , wherein Ar 1 comprises acenaphthene, acenaphthylene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, chrysene, dibenz(a,h)anthracene, fluoranthene, fluorene, indeno(1,2,3-cd)pyrene, perylene, phenanthrene, pyrene, or combinations thereof.

4. The compound of claim 1 , wherein the compound fluoresces at a wavelength of about 300 nm to about 700 nm when excited by light of wavelength of about 10 nm to about 400 nm.

5. A composition comprising a copolymer of two or more polyepoxides covalently linked by a compound of formula:

wherein:

Ar 1 is fused arene having 10 to 100 carbon atoms.

6. The composition of claim 5 , wherein the polyepoxides comprise bisphenol A epoxy, bisphenol F epoxy, naphthalene epoxy, diphenylfluorene-epoxy, triglycidyl aminophenol epoxy, triglycidyl aminocresol epoxy, tetraglycidyl diaminodiphenylmethane epoxy, tetraglycidyl m-xylylene amine epoxy, N,N-diaminocresol epoxy, phenol novolac epoxy, cresol novolac epoxy, biphenyl epoxy, dicyclopentadiene epoxy, and combinations thereof.

7. The composition of claim 5 , wherein the fused arene comprises acenaphthene, acenaphthylene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi] perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, chrysene, dibenz(a,h)anthracene, fluoranthene, fluorene, indeno(1,2,3-cd)pyrene, perylene, phenanthrene, pyrene, or combinations thereof.

8. The composition of claim 5 , wherein the copolymer comprises a formula:

wherein:

B is a polyepoxide; and

Ar is a compound of formula:

wherein:

Ar 1 is fused arene having 10 to 100 carbon atoms.

9. The composition of claim 5 , further comprising one or more fillers, fibers, surfactants, organic binders, polymeric binders, crosslinking agents, coupling agents, aramid fibres, lubricants, mold release agents, pentaerythritol tetrastearate, nucleating agents, anti-static agents, conductive blacks, carbon fibers, carbon nanotubes, organic antistatic agents, polyalkylene ethers, alkylsulfonates, polyamide-containing polymers, catalysts, colorants, inks, dyes, antioxidants, stabilizers, plasticizers, impact agents, flame retardants, or combinations thereof.

10. The composition of claim 5 , wherein the composition fluoresces at a wavelength of about 300 nm to about 700 nm when excited by light of a wavelength of about 10 nm to about 400 nm.

11. An article of manufacture comprising a copolymer of two or more polyepoxides covalently linked by a compound of formula:

wherein:

Ar 1 is a fused arene having 10 to 100 carbon atoms.

12. The article of manufacture of claim 11 , wherein the polyepoxides comprise bisphenol A epoxy, bisphenol F epoxy, naphthalene epoxy, diphenylfluorene epoxy, triglycidyl aminophenol epoxy, triglycidyl aminocresol epoxy, tetraglycidyl diaminodiphenylmethane epoxy, tetraglycidyl m-xylylene amine epoxy, N,N-diaminocresol epoxy, phenol novolac epoxy, cresol novolac epoxy, biphenyl epoxy, dicyclopentadiene epoxy, or combinations thereof.

13. The article of manufacture of claim 11 , wherein Ar 1 comprises acenaphthene, acenaphthylene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, chrysene, dibenz(a,h)anthracene, fluoranthene, fluorene, indeno(1,2,3-cd)pyrene, perylene, phenanthrene, pyrene, and combinations thereof.

14. The article of manufacture of claim 11 , wherein the copolymer comprises a formula:

wherein:

B is a polyepoxide; and

Ar is a compound of formula:

wherein:

Ar 1 is fused arene having 10 to 100 carbon atoms.

15. The article of manufacture of claim 11 , wherein the article fluoresces at a wavelength of about 300 nm to about 700 nm when excited by light of wavelength 10 nm to 400 nm.

16. The article of manufacture of claim 11 , wherein the copolymer comprises a detectable fluorescent tag.

17. A method for preparing an optically active epoxy, the method comprising:

providing at least one functionalized fused arene of formula:

wherein:

Ar 2 is a compound of formula:

wherein:

Ar 1 is a fused arene having 10 to 100 carbon atoms;

X and X′ are each independently comprise a functional group; and

contacting the functionalized fused arene with a polyepoxide under conditions that allow the functionalized fused arene to react with the polyepoxide to produce an optically active epoxy.

18. The method of claim 17 , further comprising contacting the optically active epoxy with one or more crosslinking agents, one or more curing agents, or combinations thereof under conditions that allow the one or more crosslinking agent, one or more curing agents, or combinations thereof to become incorporated into the optically active epoxy.

19. The method of claim 17 , further comprising contacting the optically active epoxy with one or more additional additives under conditions that allow the one or more additional additives to become incorporated into the optically active epoxy.

20. The method of claim 17 , wherein Ar 1 comprises acenaphthene, acenaphthylene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, chrysene, dibenz(a,h)anthracene, fluoranthene, fluorene, indeno(1,2,3-cd)pyrene, perylene, phenanthrene, pyrene, or combinations thereof.

21. The method of claim 17 , wherein X comprises ester, ketone, ether, hydroxyl, carboxylic acid, amine, amino, phenol, aniline, or benzoic acid.

22. The method of claim 17 , wherein X′ comprises ester, ketone, ether, hydroxyl, carboxylic acid, amine, amino, phenol, aniline, or benzoic acid.

23. The method of claim 17 , wherein the optically active epoxy comprises a formula:

wherein:

B is a polyepoxide; and

Ar is a compound of formula:

wherein:

Ar 1 is fused arene having 10 to 100 carbon atoms.

24. A method for identifying a component of a device, the method comprising:

providing a device having an optically active component including a copolymer of two or more polyepoxides covalently linked by a compound of formula:

wherein:

Ar 1 is a fused arene having 10 to 100 carbon atoms;

irradiating the device with ultraviolet (UV) light having a wavelength of from about 10 to about 400 nm; and

identifying the component of the device by determining a fluorescence wavelength emitted by the component, wherein the fluorescence wavelength is from about 300 nm to about 700.

25. The method of claim 24 , wherein identifying comprises correlating the fluorescence wavelength with a know fluorescence wavelength corresponding to a property of the component, wherein the property is selected from the group consisting of a type of the component, a material associated with the component, a warning regarding the component, a component manufacturer, a manufacturing date of the component, and a serial number of the component.

Assignments (3)
RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019 AT REEL 048373 FRAME 0217 Recorded Sep 22, 2025
From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 072936/0464 →
RELEASE OF SECURITY INTEREST Recorded Nov 29, 2023
From: CRESTLINE DIRECT FINANCE, L.P.
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 065712/0585 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →