Steady 3-isothiazolylone compsns.
A technology of isothiazolone and composition, applied in the field of improved stable 3-isothiazolone microbicides
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Embodiment 1
[0035] Prepare five samples of a 3:1 mixture of 5-chloro-2-methyl-3-isothiazolone ("CMI") and 2-methyl-3-isothiazolone ("MI") in deionized water, one Samples are used as controls, other samples are labeled A-D. The control contained only the 3-isothiazolone mixture and deionized water. Samples A-D contained a 3-isothiazolone mixture, deionized water, and 1,1'-azobis(N,N-dimethylformamide) as a stabilizer. In addition, Sample B also contained 2,2'-dithiobis(pyridine-N-oxide) as a second stabilizer. The levels of 3-isothiazolone and stabilizer in the Control and Samples A-D are reported in Table 1. The remainder of the material in each sample was deionized water.
[0036] An aliquot was taken from each sample for initial analysis. The samples were then placed in an oven at 55°C. Aliquots were removed after 2 and 4 weeks of storage and analyzed by HPLC for the amount of total 3-isothiazolone remaining. The results are reported in Table 1. Stabilizer A is 1,1'-azobis(N,N-di...
Embodiment 2
[0047] Six samples of a 3:1 mixture of CMI and MI in deionized water were prepared. Two samples were used as controls, the other samples were labeled E-H. The control contained only the 3-isothiazolone mixture and deionized water. Samples E-H contained a 3-isothiazolone mixture, deionized water, and azodicarbonamide as a stabilizer. The levels of 3-isothiazolone and stabilizer in the Control and Samples E-H are reported in Table 2. The remainder of the material in each sample was deionized water.
[0048] Due to its limited solubility in water, azodicarbonamide was placed in a water-permeable bag with a molecular weight cutoff of 3500. One bag was then placed in each of Samples E-H. An aliquot was taken from each sample for initial analysis. The samples were then placed in an oven at 55°C. Aliquots were removed after 1, 2 and 4 weeks of storage and analyzed by HPLC for the amount of total 3-isothiazolone remaining. The results are reported in Table 2.
[0049] Table 2:...
Embodiment 3
[0060] A solution labeled I of 0.27 g of a 3:1 mixture of CMI and MI was prepared as a sample in 14.6 g of deionized water. To this solution was added 0.2 g of 1,1'-(azobiscarbonyl)dipiperidine as a stabilizer. The samples were mixed, but the stabilizer was not completely dissolved. Undissolved stabilizer remains at the bottom of the vial. This sample was compared to a control containing only a 3:1 mixture of CMI and MI and deionized water. The contents of 3-isothiazolone and stabilizer in the samples and controls are reported in Table 3.
[0061] An aliquot was taken from each sample for initial analysis. The samples were then placed in an oven at 55°C. Aliquots were removed after 1 week of storage and analyzed by HPLC for the amount of total 3-isothiazolone remaining. The results are reported in Table 3.
[0062] Table 3: Percentage of remaining 3-isothiazolones
[0063] CMI+MI stabilizer
[0064] Sample Initial %wt (%wt) 1 week
[0065] Control 5.6 0 19
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