Process for preparing 1-cyano-3H-dibenz[f,ij]isoquinoline-2,7-diones and their use as toners for polyesters
AssigneeEastman Chemical Company
InventorsKim S. Chamberlin, Wayne P. Pruett, Max A. Weaver, Samuel D. Hilbert, Donna R. Quillen, Preston K. Salyer
Life of this patent
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Abstract
Provided is an improved process for the synthesis of 1-cyano-3H-dibenz[f,ij] isoquinoline-2,7-dione compounds, and process exhibiting improvements in quality of products, safety, fewer environmental concerns and economics when compared to presently known processes. The compounds are useful as colorants for polyesters, and selected compounds and when combined with small quantities of certain red colorants are particularly efficacious as blue toners for polyesters.
Claims14
A method for imparting improved whiteness to a polyester normally appearing yellow, which comprises admixing a blue toner compound of the formula ##STR17## wherein R is hydrogen, cycloalkyl, allyl, alkyl, aralkyl, alkoxyalkyl or cycloalkylalkylene;
- R.sub.2 is hydrogen, alkyl, aryl, alkoxy, arylalkoxy, alkylthio, arylthio, carbalkoxy, carbaralkoxy, carboxy, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkylarylsulfamoyl, cycloalkylsulfamoyl, arylsulfamoyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, alkylarylcarbamoyl, cycloalkylcarbamoyl, arylcarbamoyl, 2-pyrrolidono, acylamido or N-alkylacylamido;
- and
- n is an integer of 1 to 5;
- wherein one or more of said alkyl, alkoxy, aryl, aryloxy, alkylthio, arylthio or aralkyl groups contain one or more reactive groups selected from the group consisting of carboxy, carbalkoxy, carbaryloxy, N-alkylcarbamoyloxy, carbamoyloxy, acyloxy, chlorocarbonyl, hydroxyl, cycloalkylcarbonyloxy, N-arylcarbamoyloxy and N,N-dialkylcarbamoyloxy, wherein said alkyl and aryl groups may further contain one or more alkoxy, acyloxy, halo, cyano, hydroxy, and arylamido groups;
- in a concentration of about 1 to about 10 parts per million, along with one or more red compounds selected from the group consisting of ##STR18## wherein R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl substituted with hydroxy;
- R.sub.6 is C.sub.2 -C.sub.6 -alkylene;
- R.sub.7 is C.sub.1 -C.sub.4 -alkyl;
- R.sub.8 is selected from hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.9 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- and R.sub.10 is hydrogen or carb-C.sub.1 -C.sub.4 -alkoxy;
- in a concentration of about 0.1 to 3 parts per million.
A method for imparting improved whiteness to a polyester normally appearing yellow, which comprises copolymerizing in said polyester a blue toner compound of the formula ##STR20## wherein R is hydrogen, cycloalkyl, allyl, alkyl, aralkyl, alkoxyalkyl or cycloalkylalkylene;
- R.sub.2 is hydrogen, alkyl, aryl, alkoxy, arylalkoxy, alkylthio, arylthio, carbalkoxy, carbaralkoxy, carboxy, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkylarylsulfamoyl, cycloalkylsulfamoyl, arylsulfamoyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, alkylarylcarbamoyl, cycloalkylcarbamoyl, arylcarbamoyl, 2-pyrrolidono, acylamido or N-alkylacylamido;
- and
- n is an integer of 1 to 5;
- wherein one or more of said alkyl, alkoxy, aryl, aryloxy, alkylthio, arylthio or aralkyl groups optionally contain one or more reactive groups selected from the group consisting of carboxy, carbalkoxy, carbaryloxy, N-alkylcarbamoyloxy, carbamoyloxy, acyloxy, chlorocarbonyl, hydroxyl, cycloalkylcarbonyloxy, N-arylcarbamoyloxy and N,N-dialkylcarbamoyloxy, wherein said alkyl and aryl groups may further contain one or more alkoxy, acyloxy, halo, cyano, hydroxy, and arylamido groups;
- in a concentration of about 1 to about 10 parts per million, along with one or more red compounds selected from the group consisting of ##STR21## wherein R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl substituted with hydroxy;
- R.sub.6 is C.sub.2 -C.sub.6 -alkylene;
- R.sub.7 is C.sub.1 -C.sub.4 -alkyl;
- R.sub.8 is selected from hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.9 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- and R.sub.10 is hydrogen or carb-C.sub.1 -C.sub.4 -alkoxy;
- in a concentration of about 0.1 to 3 parts per million.
A polyester composition having admixed or copolymerized therein a blue toner compound of the formula ##STR23## wherein R is hydrogen, cycloalkyl, allyl, alkyl, aralkyl, alkoxyalkyl or cycloalkylalkylene;
- R.sub.2 is hydrogen, alkyl, aryl, alkoxy, arylalkoxy, alkylthio, arylthio, carbalkoxy, carbaralkoxy, carboxy, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl, alkylarylsulfamoyl, cycloalkylsulfamoyl, arylsulfamoyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, alkylarylcarbamoyl, cycloalkylcarbamoyl, arylcarbamoyl, 2-pyrrolidono, acylamido or N-alkylacylamido;
- and
- n is an integer of 1 to 5;
- wherein one or more of said alkyl, alkoxy, aryl, aryloxy, alkylthio, arylthio or aralkyl groups optionally contain one or more reactive groups selected from the group consisting of carboxy, carbalkoxy, carbaryloxy, N-alkylcarbamoyloxy, carbamoyloxy, acyloxy, chlorocarbonyl, hydroxyl, cycloalkylcarbonyloxy, N-arylcarbamoyloxy and N,N-dialkylcarbamoyloxy, wherein said alkyl and aryl groups may further contain one or more alkoxy, acyloxy, halo, cyano, hydroxy, and arylamido groups;
- in a concentration of about 1 to about 10 parts per million, along with one or more red compounds selected from the group consisting of ##STR24## wherein R.sub.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl substituted with hydroxy;
- R.sub.6 is C.sub.2 -C.sub.6 -alkylene;
- R.sub.7 is C.sub.1 -C.sub.4 -alkyl;
- R.sub.8 is selected from hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- R.sub.9 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
- and R.sub.10 is hydrogen or carb-C.sub.1 -C.sub.4 -alkoxy;
- in a concentration of about 0.1 to 3 parts per million.
Dependencies are inferred from the claim text.