# US 5,352,761 A · Naphthalene dicarboxylic acids and esters substituted with aroyl groups

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- Number: US 5,352,761 A
- Document ID: US5352761A
- Status: Granted
- Kind: A
- Application number: 08/160,766
- Filed: 1993-12-03
- Granted: 1994-10-04
- Earliest claimed: 1993-12-03
- Assignees: Eastman Chemical Company
- Inventors: Allan S. Jones; Charles E. Sumner, Jr.
- Web page: https://patentgrep.com/patent/US5352761A

## CPC

- C07D 307/92: Naphthofurans; Hydrogenated naphthofurans
- C07C 69/76: Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C08G 63/189: containing a naphthalene ring
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

This invention relates to naphthalene dicarboxylic acids or naphthalene dicarboxylic esters substituted with aroyl groups. More particularly, this invention relates to the following compounds: dialkyl 1-benzoyl-2,6-naphthalene dicarboxylate, 7-C1-C.sub.8 -alkoxycarbonyl-1-C1-Cs-alkoxy-l-aryl(1,3-H.sub.2 naphtho {1,2-c} furan-3-ones), and dialkyl 1-(2-naphthoyl)-2,6-naphthalene dicarboxylate. The compounds are useful in any polymer composition where dicarboxylic acids or dicarboxylic esters are used especially in poly(ethylene 2,6-naphthalene dicarboxylate) compositions where reduced fluorescence is desired.

## Claims

### Claim 1

A substituted 1,3-H.sub.2 naphtho{1,2-c}furan-3-one compound having the formula: ##STR5## wherein R is independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkoxy group; R.sup.4 is an aryl group; R.sup.5 is independently selected from the group consisting of hydrogen and halogen.

### Claim 2 (depends on 1)

The dimethyl 1-(2-naphthoyl)-2,6-naphthalene dicarboxylate according to claim 1 having the formula: ##STR6##

### Claim 3 (depends on 1)

The 7-MeOOC-1-MeO-1Ph-(1,3-H.sub.2 -naphtho{1,2-c}furan-3-one) according to claim 1 having the formula: ##STR7##

### Claim 4

A poly(ethylene 2,6-naphthalene dicarboxylate) composition with reduced fluorescence comprising repeat units from:
(a) a dicarboxylic acid component which comprises at least 85 mole percent of a dicarboxylic acid selected from the group consisting of naphthalene-2,6-dicarboxylic acid, and naphthalene-2,6-dicarboxylate ester;
(b) a diol component which comprises at least 85 mole percent of ethylene glycol; and
(c) 0.1 to 5 mole percent, based on 100 mole percent dicarboxylic acid and 100 mole percent diol, of one or more substituted 1,3-H.sub.2 naphtho{1,2-c}furan-3-one compounds having the formula: ##STR8## wherein R is independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cyclo alkyl and aryl; R.sup.3 is a C.sub.1 -C.sub.8 alkoxy group; R.sup.4 is an aryl group; R.sup.5 is independently selected from the group consisting of hydrogen and halogen.

### Claim 5 (depends on 8)

A poly(ethylene 2,6-naphthalene dicarboxylate) composition with reduced fluorescence according to claim 8 comprising repeat units from:
(a) a dicarboxylic acid component which comprises at least 85 mole percent of a dicarboxylic acid selected from the group consisting of naphthalene-2,6icarboxylic acid, and naphthalene-2,6icarboxylate ester;
(b) a diol component which comprises at least 85 mole percent of ethylene glycol; and
(c) 0.3 to 2.5 mole percent, based on 100 mole percent dicarboxylic acid and 100 mole percent diol, of one or more substituted 1,3-H.sub.2 naphtho[1,2-c]furan-3-one compounds having the formula: ##STR9## wherein R is independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cyclo alkyl and aryl; R.sup.3 is a C.sub.1 -C.sub.8 alkoxy group; R.sup.4 is an aryl group; R.sup.5 is independently selected from the group consisting of hydrogen and halogen.