The United States of America As Represented by the United States

USA As Represented by Secretary of the Navy

The United States of America As Represented by the Department of Energy

The United States of America

Peter R Hammond

James F Feeman

Ronald A Henry

John A Trias

George F Field

Erhard J Schimitschek

Aaron N Fletcher

Ronald L Atkins

Richard Swart Hughes

Nicholas Bottka

Theodore G Pavlopoulos

George Field

James F Freeman

Erhard J Schimitischek

Novel water soluble dyes of the formula I are provided ##STR1## wherein R.sup.1 and R.sup.4 are alkyl of 1 to 4 carbon atoms or hydrogen; or R.sup.1 -R.sup.2 or R.sup.2 -R.sup.4 form part of aliphatic heterocyclic rings; R.sup.2 is hydrogen or joined with R.sup.1 or R.sup.4 as described above; R.sup.3 is --(CH.sub.2).sub.m --SO.sub.3.sup.-, where m is 1 to 6;

Water soluble laser dyes

Methods for the efficient preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline include a first method in which the acylation of m-aminophenol obtains a lactam which is reduced to give the desired quinoline and a second method in which tetrahydroquinoline is nitrated and hydrogenated and then hydrolyzed to obtain the desire quinoline. 7-hydroxy-1,2,3,4-tetrahydroquinoline is used in the efficient synthesis of four lasing dyes of the rhodamine class.

Method for preparation of 7-hydroxy-1,2,3,4-tetrahydroquinoline from

A novel method for the synthesis of 6-hydroxyindolines and new fluorescent dyes produced therefrom, which dyes are ring-constrained indoline-based rhodamine class dyes. These dyes have absorption and emission spectra which make them particularly useful in certain dye laser applications.

Preparation of 6-hydroxyindolines and their use for preparation of novel

New oxazine compounds useful as dye laser media in solution, are superiior to prior art materials. The oxazine dyes useful when pumped by the 578.2 nm copper line to operate in the 700-800 nm range are described by formula I ##STR1##

Oxazine laser dyes

A novel class of dye is disclosed which is particularly efficient and stable for dye laser applications, lasing between 540 and 570 nm.

Fluorinated laser dyes

Novel fluorinated laser dyes

A dye of the DCM family, [2-methyl-6-[2-(1,2,3,4-tetrahydro-1-methyl-6-quinolinyl)ethenyl]-4H-pyran -4-ylidene]-propanedinitrile, dissolved in 2-phenoxyethanol, is non-mutagenic, stable and efficient, particularly in a pumped continuous wave laser system.

Dye system for dye laser applications

Method of preparing novel fluorinated laser dyes

A novel class of dye is disclosed which is particularly efficient and stable for dye layer applications, lasing between 540 and 570 nm.

Methods are provided for making certain m-aminophenols using a sulfonation/alkali fusion procedure. The aminophenols are key intermediates in the synthesis of dyes, particularly efficient, stable dyes for laser application. Preparations of some rhodamine and phenoxazone dyes from the m-aminophenols are described.

Preparation of certain m-aminophenols and the use thereof for

Compounds having the formula: ##STR1## wherein X is selected from the group consisting of NH and O, R is selected from the group consisting of H, CH.sub.3 and phenyl, R' is selected from the group consisting of OCH.sub.3, CF.sub.3 CH.sub.3 and H and R' is selected from the group consisting of H, CH.sub.3 and CH.sub.2 CO.sub.2 C.sub.2 H.sub.5. The compounds are stable, efficient laser dyes.

Substituted -6,7,8,9-tetrahydro-pyrido- and 2H-pyrano

2-Keto-6,7,8,9-tetrahydro-2H-pyrano(3,2-g)-quinoline and 2-keto-9-methyl-,8,9-tetrahydro-2H-pyrano(3,2-g)-quinoline, compounds useful as laser dyes, are prepared from 7-hydroxy-1,2,3,4-tetrahydroquinoline.

[3,2-g] Pyranoquinoline derivatives

A dye laser comprising a laser dye solution of a compound having the general structure: ##STR1## wherein at least one of the 5, 6 and 8 ring positions is occupied by a nitrogen atom in lieu of the corresponding CR group and X is OH, alkoxy, or amino including amino substituted by at least one of the following: alkyl, aryl, acyl, aracyl, a group which taken together with the nitrogen atom of the amino group forms a heterocyclic ring, or part of one or two 5 or 6 membered aliphatic heterocyclic rings attached to ring A at positions 6 or 8 or both depending on where the N in ring A is located. R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.8 are hydrogen or other groups as defined below. The compounds lase in the blue-green to near ultraviolet region.

Azacoumarin dye lasers

A dye laser comprising a laser dye solution of a compound having the general structure: ##STR1## wherein at least one of the 5, 6 and 8 ring positions is occupied by a nitrogen atom in lieu of the corresponding CR group and X is OH, alkoxy, or amino including amino substituted by at least one of the following: alkyl, aryl, acyl, aracyl, a group which taken together with the nitrogen atom of the amino group forms a heterocyclic ring, or part of one or two 5 or 6 membered aliphatic heterocyclic rings attached to ring A at positions 6 or 8 or both depending on where the N in ring A is located. R.sub.1, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.8 are hydrogen or other groups as defined below. The compounds lase in the blue to near ultraviolet region.

Azaquinolone dye lasers

Methods for preparing ##STR1## wherein n is 3 or 4 and R is H, CH.sub.3 or C.sub.2 H.sub.5. The methods involve forming ##STR2## by reacting p-terphenyl or quaterphenyl with acetic acid and fuming nitric acid, forming ##STR3## by refluxing the dinitro derivative with stannous chloride, hydorchloric acid and acetic acid and forming the dialkylamino derivative by refluxing the diamino derivatives with a suitable trialkyl phosphate. Also, ##STR4## derivatives may be prepared by refluxing the diamino derivatives with sodium nitrite and hydrochloric acid to form ##STR5## AND REACTING THIS INTERMEDIATE WITH A MIXTURE OF ACETIC ACID AND EITHER WATER OR ALCOHOL. The compounds are useful as lasing dyes.

Growing community of inventors

Livermore, CA, United States of America

Peter R Hammond