Naphthalene-containing polymers and methods of making the same

Patent metadata

Field	Value
Publication number	US-10364322-B2
Application number	US-201815879840-A
Country	US
Kind code	B2
Filing date	Jan 25, 2018
Priority date	Jan 25, 2017
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

The present disclosure relates to a dimer that includes a first hydroxyl-functionalized naphthalene group and a second hydroxyl-functionalized naphthalene group, where the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group. The present disclosure also relates to a polymer synthesized using the dimer, as well as methods for synthesizing both the dimer and the polymer.

First claim

What is claimed is:

1. A dimer comprising:
a first hydroxyl-functionalized naphthalene group; and
a second hydroxyl-functionalized naphthalene group, wherein:
the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group.

2. The dimer of claim 1 , wherein the bridging group comprises an aliphatic group.

3. The dimer of claim 1 , wherein the dimer has a structure selected from the group consisting of

and wherein R is the bridging group.

4. The dimer of claim 3 , wherein the structure is selected from the group consisting of

5. The dimer of claim 3 , wherein the structure is selected from the group consisting of

6. A polymer comprising:
a dimer comprising:
a first hydroxyl-functionalized naphthalene group; and
a second hydroxyl-functionalized naphthalene group, wherein:
the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group, wherein:

the polymer contains between 2 and 1500 units of the dimer, and
the bridging group comprises an aliphatic group.

7. The polymer of claim 6 , wherein the polymer has a structure selected from the group consisting of

wherein R is the bridging group and n is the number of units of the dimer.

8. The polymer of claim 7 , wherein the structure is selected from the group consisting of

9. The polymer of claim 8 , wherein the structure is selected from the groups consisting of

10. The polymer of claim 7 , wherein the polymer is endcapped with at least one of a hydroxyl group, a halogen, an amine, or an oxygenated aromatic.

11. The polymer of claim 6 , wherein the polymer has a structure selected from the group consisting of

wherein n is the number of units of the dimer.

12. The polymer of claim 6 , further comprising a weight averaged molecular weight, M W , between 3 kDa and 400 kDa.

13. The polymer of claim 6 , further comprising a degradation temperature between 150° C. and 500° C.

14. The polymer of claim 6 , further comprising a glass transition temperature, T g , between 50° C. and 200° C.

15. A method comprising:
reacting a precursor molecule with a first bridging molecule to form a dimer, wherein:
the precursor molecule comprises a hydroxyl-functionalized naphthalene, and
the first bridging molecule comprises at least one of a ketone, an aldehyde, or a halogenated aliphatic molecule.

16. The method of claim 15 , wherein the second bridging molecule comprises at least one of a carbonate or a phosgene.

17. The method of claim 15 , wherein:
the first bridging molecule has the structure

R 1 comprises a first aliphatic group, and
R 2 comprises a second aliphatic group.

18. The method of claim 15 , further comprising:
polymerizing the dimer with a second bridging molecule to produce a polymer, wherein:
the second bridging molecule has the structure

and
X comprises at least one of a hydroxyl group, a halogen, an amine, or an oxygenated aromatic.

19. The method of claim 16 , wherein the precursor molecule comprises at least one of a naphthol, methyl naphthalene, an ethyl naphthalene, a dimethyl naphthalene, a methyl naphthol, or a dimethyl naphthol.

20. A method for producing a dimer, the method comprising:
reacting 2-naphthol with Br 2 to produce 6-bromonaphthalen-2-ol;
reacting the 6-bromonaphthalen-2-ol to produce 2-bromo-6-methoxynaphthalene;
reacting the 2-bromo-6-methoxynaphthalene with magnesium to produce 6-methoxynaphthalene, 2-MgBr;
reacting the 6-methoxynaphthalene, 2-MgBr with 2,3-dibromobutane to produce 2,2′-(1,2-dimethyl-1,2-ethanediyl)di-(6-methoxynaphthalene); and
reacting the 2,2′-(1,2-dimethyl-1,2-ethanediyl)di-(6-methoxynaphthalene) to produce the dimer comprising 6,6′-(butane-2,3,-diyl)di(naphthalen-2-ol).

Assignees

• Alliance Sustainable Energy

Inventors

• Nimlos Mark R
• Wilson Andrew Nolan
• Mukarakate Calvin
• Price Mariel Jene

Classifications

• C07C39/14

  with at least one hydroxy group on a condensed ring system containing two rings · CPC title

• C08H6/00

  Macromolecular compounds derived from lignin, e.g. tannins, humic acids · CPC title

• C08L97/02

  Lignocellulosic material, e.g. wood, straw or bagasse {(manufacture of articles made from lignocellulosic material by dry processes B27N)} · CPC title

• C08G65/34 Primary

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C08G64/04 Primary

  Aromatic polycarbonates · CPC title