C - Chemistry – Metallurgy – 09 – B
Patent
C - Chemistry, Metallurgy
09
B
150/19, 530/15.1
C09B 29/36 (2006.01) C07D 275/04 (2006.01) G01N 31/22 (2006.01) G01N 33/52 (2006.01)
Patent
CA 1340759
The present invention involves a newly synthesized chromogenic thiol-indicating isobenzothiazolone derivative having the structure: (see formula I) In this. structure at least one of R1 and R2 is preferably nitro, arylazo, substituted arylazo, benzylideneamino or substituted benzylideneamino. When only one of R1 and R2 is so substituted, one of R1 and R2 may be hydrogen. The R3 substituent is preferably alkyl, carboxyalkyl, hydroxyalkyl, aminoalkyl, haloalkyl, aryl, carboxyaryl, hydroxyaryl, aminoaryl, heteroaryl, carboxyheteroaryl, hydroxyheteroaryl, aminoheteroaryl, hydroxy, alkoxy, or amino. Preferred species of the isobenzothiazol-3-one derivative of the present invention are seen which comprise R1 as nitro and R2 as hydrogen. Other preferred species include derivatives where R2 is hydrogen and R1 is the the arylazo, phenylazo, the substituted arylazo, 4-hydroxyphenylazo, 4-nitro-2-methylphenylazo, 2-hydroxy-1-napthylazo, 2-hydroxy-5-methylphenylazo, 2-hydroxy-4-methyl-5-nitro- phenylazo, 4-hydroxy-1-napthylazo, 4-hydroxy-3- methyl-1-napthylazo, 4-hydroxy-5-aza-1-napthylazo, 2-amino-1-napthylazo, 1-hydroxy-2-napthylazo, 1-hydroxy-2-(N-dimethylaminopropylcarbamoyl)-4- naphthylazo, 1-hydroxy-4-methoxy-2-naphthylazo, 2-hydroxy-3-carboxy-1-naphthylazo, 1-hydroxy-3,6- disulfo-2-naphthylazo, 2,3-dihydroxy-1-naphthylazo, and 2-hydroxy-3,5-dimethyl-1-phenylazo. In one particular embodiment R1 is the substituted benzylideneamino, 2,4-dinitrobenzylideneamino and R2 is hydrogen. Particularly preferred compounds of the present invention may have R3 which is alkyl, aryl, hydroxy, alkoxy, phenyl or amino. These, in turn, can be substituted with functional groups selected such that they provide the necessary reactivity and/or solubility properties. Some functional groups are chosen so that they will react with macromolecules, causing the indicator to be immobilized. A central utility of the compounds of the present invention involves their use in the detection of thiols. Thus, the present invention comprises a process for measuring the presence or appearance of thiols, particularly in an aqueous system. This process comprises contacting said aqueous system with a chromogenic thiol-indicating isobenzothiazolone derivative as described herein. Chromophoric changes due to thiol-mediated reduction of the isobenzothiazolone derivative then occur. Such changes can be in a solution or on an indicator surface in contact or having been in contact with the aqueous system. The chromophoric changes, due to a bathochromic shift in characteristic light absorption upon reduction of isobenzothiazolone derivative, are proportional to the amount or rate of appearance of thiols in the aqueous system.
601459
Albarella James P.
Garling David L.
Hatch Robert P.
Albarella James P.
Corporation Bayer
Garling David L.
Hatch Robert P.
Osler Hoskin & Harcourt Llp
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