Pentachlorophenyl acrylate

Pentachlorophenyl acrylate, (1), was terpolymerized with methyl methacrylate (MMA) and n-butyl acrylate (nBA) (Scheme III) to give a latex containing 537 solids and a pll of 4.7 which was adjusted to 6.8 by adding aqueous NaOH. The latex was stable up to pH =10. A small aliquot vzas coagulated and the resulting polymer purified. Its intrinsic viscosity was 3.1 /g and analysis indicated 2 mole percent (1), 587 CIA and 40" nBA. Similar terpolyner latices were prepared from acrylates (2) and (3) (Scheme III). Another terpolymer latex made from (3), vinyl acetate, and 2-ethylhexyl acrylate contained 547 solids. Tliese latices and their compositions are summarized in the Table 1 and a sample experimental procedure is given in the experimental section. 

Table II. Minimum Inhibitory Concentrations of Pentachlorophenyl Acrylate, (1), and its Homopolymer Toward Micro-ogranlsms Using an Agar Dilution Method. (- means no growth + means growth).

In order to determine the reactivity of pentachlorophenyl acrylate, 8, in radical initiated copolymerizations, its relative reactivity ratios were obtained with vinyl acetate (M2), ri=1.44 and r2=0.04 using 31 copolymerization experiments, and with ethyl acrylate (M2), ri=0.21 and r2=0.88 using 20 experiments.The composition conversion data was computer-fitted to the integrated form of the copolymer equation using the nonlinear least-squares method of Tidwell and Mortimer,which had been adapted to a computerized format earlier. 

In this work,glass transition temperatures were studied as a function of copolymer composition. Poly(pentachlorophenyl acrylate) exhibited the high Tg value of 143°. Table 5 summarizes these Tg values versus Mj/M2 content of both vinyl acetate and ethyl acrylate copolymers.The Tg values for copolymers with higher mole fractions of 8 depended on their thermal history. Tg increases after heating above Tg the first time. For example a vinyl acetate copolymer (mole fraction of 8 = 0.67) exhibited Tg values of 77°, 99°, and 103°C in three successive heating cycles. 

Table 5-Glass Transition Temperatures For Pentachlorophenyl Acrylate (Mi) Copolymers With Vinyl Acetate or Ethyl Acrylate...

Attempts to make acrylic latlces containing o-benzyl-p-chlorophenyl acrylate, 17, using the same techniques employed for the systems In Table 6, failed. It was found that no 17 was Incorporated Into the polymer of these latlces. Similar attempts to make terpolymer latlces with vinyl pentachlorophenyl ether, 25 or vinyl 3,4 5-trlbromosallcylanlllde ether, 28 (with MMA and nBA) failed. These fungicidal vinyl ethers were not.Incorporated Into the resulting latex polymers. However, vinyl o-benzyl-p-chlorophenyl ether, 17, was successfully terpolymerized In latex form (see latex 12, Table 6). Formulations for latlces 1-3 and 5-14 are given In Table 7. 

The question of whether or not a polymer-anchored biocide can be active against microorganism growth was first tested by comparing the minimum inhibitory concentrations (MIC) of pentachlorophenol, its acrylate, 8, and the homopolymer of pentachlorophenyl acrylate 8. An agar dilution method was used. To a sterilized agar, a solution of the compound to be tested was added in the appropriate amount to make final concentrations of 1000, 500, 250, 100, 50, and 10 ppm. Following inoculation, the... 

Starting from nucleic acid bases, the carboxyethyl derivatives of the nucleic acid bases were prepared by a Michael type addition reaction of ethyl acrylate followed by hydrolysis. The carboxyethyl derivatives of nucleic acid bases were reacted with ( )-a-amino T-butyrolactone hydrobromide to give v-hutyrolactone derivatives of nucleic acid bases. For the coupling reactions, pentachlorophenyl ester derivatives were used with imidazole as a catalyst.22... 

B. Chemical Bonding with Polymerization. Two examples of this type are pesticide-isocyanate adducts with PVA and pentachlorophenyl acrylate with vinyl acetate (or ethyl acrylate). 

The other example, a polymer-bound fungicide, is found in the copolymerization of pentachlorophenyl acrylate with vinyl acetate and ethyl acrylate. This pentachlorophenol-based product could have use as an anti-fouling agent in marine coatings. In this case it was necessary to copolymerize with ethyl acrylate. The homopolymer was found to be too hydrophobic to allow decomposition of the polymer and allow release of the active agent in sufficiently high concentrations to have the appropriate biocide effect. 

Poly[ 1 -04-efliyl-N-( 1.4,7,10,13-penta-oxacyclopentadecyl)carbamoyl)ethylene] Poly(pentachlorophenyl acrylate) Poly(4-10,15,20-triphenylporphorin-21H,23H-5-ylphenyl... 

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