Process for producing naphthalimide diester fluorescent dyes and compositions thereof
AssigneeSpectronics Corporation
InventorDaniel Scott Tyson
Life of this patent
Estimating the term…
Abstract
Provided are processes for producing fluorescent naphthalimide diesters of Formula (I), useful as fluorescent tracer dyes for fluid system leak detection, wherein each of R1 and R2 is, independently of the other, a saturated, linear hydrocarbon chain having from 2 to 10 carbon atoms; and each of Z1 and Z2 is, independently of the other, a fatty acid moiety having a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds. Also provided are compositions of the aforesaid diesters of Formula (I).
Claims27
A process for preparing a naphthalimide diester of Formula (I) or mixture thereof,
- wherein
- each of R1 and R2 is, independently of the other, a saturated, linear hydrocarbon chain having from 2 to 10 carbon atoms;
- each of Z1 and Z2 is, independently of the other, a fatty acid moiety having a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds;
- the process comprising:
- reacting a naphthalimide diol of Formula (II) or mixture thereof
- wherein
- each of R1 and R2 is, independently of the other, a saturated, linear hydrocarbon chain having from 2 to 10 carbon atoms;
- with an ester of Formula (III) or mixture thereof
- wherein
- R is selected from saturated or unsaturated, linear or branched, hydrocarbon chain having from 1 to 8 carbon atoms and from 0 to 2 double bonds, and phenyl optionally substituted with from 1 to 3 saturated or unsaturated, linear or branched, hydrocarbon chains having from 1 to 6 carbon atoms and from 0 to 2 double bonds;
- and
- R3 is a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds,
- to provide a compound of Formula (I) or mixture thereof.
A process for preparing a naphthalimide diester of Formula (I) or mixture thereof,
- wherein
- each of R1 and R2 is, independently of the other, a saturated, linear hydrocarbon chain having from 2 to 10 carbon atoms;
- each of Z1 and Z2 is, independently of the other, a fatty acid moiety having a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds;
- the process comprising:
- (a) reacting a fatty acid having the formula (IV) or mixture thereof
- wherein R3 is a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds,
- with a molar excess of naphthalimide diol of Formula (II) with respect to said fatty acid,
- wherein
- each of R1 and R2 is, independently of the other, a saturated, linear hydrocarbon chain having from 2 to 10 carbon atoms;
- until substantially all of the fatty acid of formula (IV) has been reacted to form a naphthalimide diester of Formula (I);
- and
- (b) reacting unreacted naphthalimide diol with an ester of Formula (III) or mixture thereof
- wherein
- R is selected from saturated or unsaturated, linear or branched, hydrocarbon chain having from 1 to 8 carbon atoms and from 0 to 2 double bonds, and phenyl optionally substituted with from 1 to 3 saturated or unsaturated, linear or branched, hydrocarbon chains having from 1 to 6 carbon atoms and from 0 to 2 double bonds;
- and
- R3 is a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds,
- to form additional compound of Formula (I) or mixture thereof.
A composition comprising a naphthalimide diester of Formula (I) or mixture thereof,
- wherein
- each of R1 and R2 is, independently of the other, a saturated, linear hydrocarbon chain having from 2 to 10 carbon atoms;
- and
- each of Z1 and Z2 is, independently of the other, a fatty acid moiety having a saturated or unsaturated, linear or branched, hydrocarbon chain having from 8 to 24 carbon atoms, and from 0 to 4 double bonds;
- the composition having an acid value according to ASTM D664-11ae1 of about 2 mg/g KOH or less.
Dependencies are inferred from the claim text.