the following examples describe preparation of comparative reaction products ( crp ) for ( a ) germall ® 115 ( 1 : 1 . 5 ); at low caustic levels ; and ( b ) at high caustic levels ; and ( c ) germall ® ii ( 1 : 4 ), low caustic and ( d ) high caustic ; and invention reaction products ( irp ) germall ® iii ( 1 : 3 ), ( a ) laboratory and ( b ) commercial runs , with only enough caustic to neutralize the formic acid present in the formalin solution . [ 0013 ] ( 1 : 1 . 5 ) allantoin 15 . 8 g ( 0 . 1 mole ) formalin ( 37 %) 12 . 2 g ( 0 . 15 mole ) water 28 . 5 ml the above mixture was refluxed for one hour to form a clear solution . [ 0015 ] ( 1 : 1 . 5 ) allantoin 600 g ( 3 . 8 mole ) formalin ( 37 %) 450 g ( 5 . 5 mole ) sodium hydroxide 123 g refluxed for one hour to form a clear solution . concentrated acetic acid was added to adjust the ph to 4 . 0 . removed water to give a white powder . [ 0017 ] ( 1 : 4 ) allantoin 1053 g ( 6 . 66 mole ) formalin ( 37 %) 2160 g ( 26 . 64 mole ) the white suspension was heated to 85 ° c . and held for an additional hour ; upon cooling a clear solution was obtained . removed water under reduced pressure to give a white powder . [ 0019 ] ( 1 : 4 ) allantoin 158 . 1 g ( 1 . 0 mole ) formalin ( 37 %) 324 . 2 g ( 3 . 99 mole ) sodium hydroxide 10 % 32 . 0 g ( 0 . 08 mole ) refluxed at 85 ° c . for one hour . the clear colorless solution obtained was dried under reduced pressure to give solid white powder residue . a . niger c . albican atcc 9642 test solutions attc1023 ( for 3 days ) 0 . 3 % germall ® 115 + + ( exs . a / b ) 0 . 3 % germall ® — — ii ( exs . c / d ) [ 0023 ] ( 1 : 3 ) allantoin 1616 g ( 10 . 23 mole ) formalin lm *( 37 %) 2488 g ( 30 . 68 mole ) sodium hydroxide 50 % 24 g mixed and heated at 60 ° c . for 3 hours to give a clear solution . the ph of the product was adjusted to 7 . 2 with the sodium hydroxide solution to neutralize formic acid in formalin ® and the solution was spray dried to give a free - flowing , white powder . [ 0026 ] ( 1 : 3 ) allantoin . wet cake 2095 lbs ( 10 . 23 mole ) formalin lm ( 37 %) 2488 lbs ( 30 . 68 mole ) sodium hydroxide 50 % 23 . 6 lbs ph 6 . 5 - 7 . 0 reaction temp 40 - 60 ° c . the resultant mixture then was further reacted at 85 ° c . for 3 hours to give a clear solution at ph 7 . 2 . the solution was spray dried to remove water and other volatile by - products to give a free - flowing , white powder . a study was conducted to determine the level of methylene diol in the reaction products versus the number of equivalents of formaldehyde added during formation . these results are based on quantitative 13c - nmr analysis and summarized in table 1 below . [ 0029 ] table 2 bioactivity of germall ® compounds invention exs . preservative organism static cidal irp - germall ® staph aureus 300 ppm 1250 ppm iii ( 1 : 3 ) e . coli 300 ppm 1250 ppm p . aeruginosa 300 ppm 600 ppm b . cepacia 150 ppm 300 ppm c . albicans & gt ; 5000 ppm — a . niger 2500 ppm 2500 ppm crp - germall ® staph aureus 300 ppm 1250 ppm ii ( 1 : 4 ) e . coli 600 ppm 1250 ppm p . aeruginosa 600 ppm 1250 ppm b . cepacia 150 ppm 600 ppm c . albicans 5000 ppm & gt ; 5000 ppm a . niger 2500 ppm 2500 ppm crp - germall ® staph aureus 1250 ppm 2500 ppm 115 ( 1 : 1 . 5 ) e . coli 1250 ppm 2500 ppm p . aeruginosa 1250 ppm 2500 ppm b . cepacia 600 ppm 1250 ppm c . albicans & gt ; 5000 ppm a . niger 5000 ppm 5000 ppm the purpose of this test procedure is to screen experimental compounds for anti - microbial activity . the measurement of the lowest effective concentration of an anti - microbial or anti - microbial blend is important for recommending use concentrations . the mic test is an in vitro tube dilution procedure used to identify effective concentrations of anti - microbials . in this test , the experimental compound is diluted by serial concentrations into nutrient culture media . test organisms are then inoculated into the anti - microbial solutions . if the experimental compound is effective , there is no growth observed in the test dilution tubes and they are clear . if the experimental compound is not effective , the test dilution tubes are cloudy , indicating growth . this test will determine static as well as cidal activity concentrations . 4 . media : trypticase soy broth ( bbl 11043 ) and aoac letheen broth ( bbl 10914 ) 5 . test organisms : staphylococcus aureus atcc 6538 , escherichia coli atcc 8739 , pseudomonas aeruginosa atcc 9027 , burkholderia cepacia atcc 25416 , candida albicans atcc 10231 , and aspergillus niger atcc 16404 . 1 . antimicrobial stock solutions are prepared at predetermined concentrations ( i . e ., 10 % through 0 . 07 %) depending on the test material . serial doubling dilutions are made as follows . each culture tube contains 5 mis of trypticase soy broth . five mis of the stock solution are added to the first tube and vortexed . 5 mis are then removed and placed into the second tube , ( and so on , until the last tube ). at the final test concentration , 5 mis of the broth / antimicrobial mixture is decanted out . 2 . the test organisms are prepared as with any organism inoculum ( mlm 100 - 3 , mlm 100 - 4 , and mlm 100 - 5 ). a saline suspension of each organism is prepared . the bacterial organisms and the yeast are a standardized at a concentration of 1 × 10 6 cfu / ml . the mold inoculum is approximately 1 × 10 5 cfu / ml . 3 . inoculate each culture tube with 0 . 10 mls of organism inoculum and vortex . 4 . incubate bacterial tubes for 24 hours at 35 ° c . incubate yeast or mold tubes for 48 hours at 25 ° c . read for growth ; turbid tubes for bacteria and yeast ; mold clearly visible tubes . this is the minimum inhibitory concentration ( static activity ). 5 . after the tubes are read , transfer all “ clear ” tubes and the first cloudy ( growth ) tube into letheen broth containing neutralizers . incubate the letheen broth tubes for 48 hours at the bacterial or fungal incubation temperatures . read for growth ; turbid tubes for bacteria and yeast ; mold clearly visible in mold tubes . this is the cidal activity concentration . the cidal activity of an anti - microbial can be rapidly screened by means of a mic test before further evaluation tests , such as longer preservative efficacy tests , are performed . this test is a tube serial dilution procedure limited only by the water solubility of the material . where anti - microbial materials are slightly insoluble , leaving the tsb broth turbid , a procedure modification can be made . tubes are incubated for 24 hours ( bacteria ) or 48 hours ( fungi ) but instead of transfer to letheen broth , the tsb tubes are streaked onto letheen agar . the agar plates are then incubated appropriately and then read for absence or presence of growth . depending on the degree of insolubility , a measure of cidal activity may be the only parameter measured . anti - microbial neutralization is important in this screening test . letheen broth or agar contains neutralizers but if these do not neutralize the anti - microbial adequately , others can be added . these are to be determined prior to testing . aseptic technique is important in any microbiological procedure . all functional operations are performed under the laminar flow hood with use of sterile pipettes , tubes and media to eliminate cross - contamination . surface sanitizers ( i . e ., alcohol ) are used on the work surface before and after each operation . ample time is allowed for recirculation of air within the sterile chamber of the hood . the bioactivity data show particular effectiveness against the organism cepacia b . ( cidal = 300 ppm vs . 600 ppm and 1250 ppm for germall ® ii and germall ® 115 , respectively ). however , if desired , even broader spectrum antibacterial activity can be achieved by combination products with the invention composition whose formulations are given below . [ 0053 ] combination blends ( by weight ) ( 1 ) germall ® iii 20 - 30 % mp - methyl paraben 8 - 12 % pp - propyl paraben 2 - 4 % pg - propylene glycol q . s . 100 ( 2 ) germall ® iii 40 - 45 % ipbc - iodopropynyl butyl carbamate 0 . 5 - 5 % pg - propylene glycol qs 100 ( 3 ) germall ® iii 98 . 5 - 99 . 5 % ipbc - iodopropynyl butyl carbamate 0 . 5 - 1 . 5 % ( powder ) a typical cosmetic emulsion was prepared for microbiological challenge testing and predetermined admixtures of a methylol compound and ipbc were added at various use levels . the emulsion thus prepared had the following composition : nonionic emulsion ( unpreserved control ) phase ingredient % wt . a water 69 . 80 a carbomer 10 . 00 b octyl palmitate 5 . 00 b cetearyl alcohol and ceteareth - 20 2 . 00 b glyceryl stearate and laureth - 23 2 . 50 b mineral oil 5 . 00 c triethanolamine ( 99 %) 0 . 20 d preservative 0 . 00 e hydrolyzed collagen 0 . 50 e water 5 . 00 total 100 . 00 standard screening emulsions % wt . phase a stearic acid 5 . 00 mineral oil 2 . 50 cetyl alcohol 1 . 00 lareth - 5 and ceteth - 5 and 0 . 50 oleth - 5 and steareth - 5 glycerol monostearate and 1 . 50 polyoxyethylene stearate phase b deionized water 88 . 0 triethanolamine 99 % 1 . 00 citric acid 30 % aqueous solution 0 . 60 preservative admixture qs to prepare the emulsion , phases a and b were heated separately to 75 °- 80 ° c . phase a then was added to phase b with mixing . the mixture then was cooled to 55 ″- 60 ° c . at this point the desired amount of the preservative admixture was added and the product was cooled to 50 ° c . while stirring . the citric acid solution then was added to adjust the ph and the mixture was stirred until a temperature of 30 ° c . was reached . the challenge tests were carried out using the following microorganisms : sa , ecoli , psa , pc , an and can , in this manner . 50 g aliquots of the test emulsion containing various amounts of the preservative admixture were inoculated with approximately 10 7 - 10 8 of the challenge organisms . the test samples then were stirred to disperse the challenge inoculum . the samples were incubated and assayed at 48 hours , 7 , 14 , 21 and 28 days . the assays were performed on 1 g of the test sample by serially diluting 10 1 to 10 6 of the original concentration . the plating medium for bacteria was letheen agar and for fungi it was low ph mycophil agar with tween 20 . each plated sample was incubated for 48 hours at 37 ° c . for bacteria , 5 days at 25 ° c . for mold , and 3 days at 25 ° c . for fungi . after incubation , readings of the number of colonies per milliliter ( cfu / ml ) were made . at 21 days the test product was reinoculated with half of the original inoculum . the data is presented in tables 3 - 11 below . [ 0064 ] table 3 comparison of activity of germall iii to germall ii and 115 ( screening emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days germall ii 1000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 160 , 000 78 , 000 63 , 000 260 , 000 210 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 1000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 160 , 000 380 , 000 380 , 000 810 , 000 640 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall 115 2000 ppm sa 3000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 490 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 230 , 000 2 , 000 , 000 650 , 000 1 , 500 , 000 1 , 200 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 2000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 150 9 , 600 48 , 900 490 , 000 210 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 2000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 6000 195 , 000 460 , 000 690 , 000 1 , 070 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved 0 sa 2 , 100 , 000 57 , 000 90 & lt ; 10 68 , 000 ec 37 , 000 96 , 000 96 , 000 43 , 000 790 , 000 psa 70 4600 500 10 , 100 170 , 000 bc 2 , 100 , 000 860 , 000 1 , 520 , 000 3 , 520 , 000 & gt ; 10 e6 can 1 , 100 , 000 168 , 000 67 , 000 270 , 000 460 , 000 an 700 , 000 56 , 000 44 , 000 190 , 000 320 , 000 [ 0065 ] table 4 comparison of activity of germall iii to germall ii and 115 ( nonionic emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days germall iii 2000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 820 , 000 1 , 680 , 000 1 , 350 , 000 700 , 000 & gt ; 1e6 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 2000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 320 , 000 720 , 000 650 , 000 730 , 000 & gt ; 1e6 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall 115 2000 ppm sa 1 , 500 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 52 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & gt ; 1e6 & gt ; 1e6 & gt ; 1e6 700 , 000 & gt ; 1e6 an & lt ; 10 20 390 370 & gt ; 1e4 germall iii 4000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 24 , 000 & gt ; 1e6 & gt ; 1e6 730 , 000 & gt ; 1e6 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 4000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 50 10 , 000 620 , 000 460 , 000 & gt ; 1e6 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall 115 4000 ppm sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 1 , 500 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 1 , 060 , 000 1 , 000 , 000 & gt ; 1e6 & gt ; 1e6 & gt ; 1e6 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved 0 sa & gt ; 1e6 6 , 300 & gt ; 1e4 & lt ; 10 & gt ; 1e4 ec & gt ; 1e6 900 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 20 , 000 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 500 , 000 510 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0066 ] table 5 comparison of activity of germall iii to germall ii and 115 ( screening emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days germall iii 250 ppm sa 69 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 11 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc 200 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 430 , 000 120 , 000 70 , 000 150 , 000 850 , 000 an 100 , 000 200 70 40 1 , 300 germall ii 250 ppm sa 55 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 5500 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 290 , 000 170 , 000 71 , 000 46 , 000 680 , 000 an 50 , 000 & lt ; 10 & lt ; 10 & lt ; 10 100 germall 115 250 ppm sa 117 , 000 30 & lt ; 10 & lt ; 10 1 , 500 ec 40 , 000 20 & lt ; 10 & lt ; 10 3600 psa & lt ; 10 320 & gt ; 1e4 & gt ; 1e6 & gt ; 1e6 bc 11 , 000 & gt ; 1e6 & gt ; 1e6 & gt ; 1e6 & gt ; 1e6 can 1 , 090 , 000 270 , 000 1 , 120 , 000 770 , 000 & gt ; 1e6 an 90 , 000 20 , 000 20 , 000 29 , 000 300 , 000 germall iii 500 ppm sa 38 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 18 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 100 , 000 210 , 000 310 , 000 270 , 000 & gt ; 1e6 an 9000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 500 ppm sa 17 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 610 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 170 , 000 100 , 000 90 , 000 320 , 000 930 , 000 an 40 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall 115 500 ppm sa 140 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec 24 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 290 , 000 760 , 000 790 , 000 1 , 210 , 000 & gt ; 1e6 an 130 , 000 1 , 000 40 290 80 , 000 unpreserved 0 sa & gt ; 1e6 34 , 000 6 , 800 20 & gt ; 1e4 ec 18 , 000 4 , 900 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 50 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can 970 , 000 270 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 150 , 000 280 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0067 ] table 6 comparison of activity of germall plus and germall iii / ipbc ( screening emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days germall plus sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 1980 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 20 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 1980 sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 20 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 100 germall iii 1960 sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 40 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved sa 580 , 000 3200 180 & lt ; 10 & gt ; 1e4 ec 5 , 200 70 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 18 , 000 40 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can & gt ; 1e6 200 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 210 , 000 270 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0068 ] table 7 comparison of activity of liquid germall plus and germall iii / ipbc - liq ( screening emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days liqgermplus sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 790 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 8 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liqgermplus sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 1580 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 20 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 100 germall iii 790 sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liquid psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 26 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 1580 sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 20 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liquid psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved 0 sa 580 , 000 3200 180 & lt ; 10 & gt ; 1e4 ec 5200 70 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 18 , 000 40 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can & gt ; 1e6 200 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 210 , 000 270 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0069 ] table 8 comparison of activity of germall plus and germall iii / ipbc ( screening emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days germall plus sa 42 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 495 ec 40 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 5 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 48 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an 100 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall plus sa 300 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 990 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 495 sa 46 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 5 ec 25 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 11 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 990 sa 24 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 10 ec 1 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa 19 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & gt ; 1e6 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 2 , 500 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 490 sa 23 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 10 ec 900 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa 18 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & gt ; 1e6 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 2800 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 980 sa 2 , 700 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 20 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved 0 sa & gt ; 1e6 54 , 000 4 , 400 20 & gt ; 1e4 ec 80 , 000 67 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 2 , 000 4200 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can 990 , 000 320 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 380 , 000 170 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0070 ] table 9 comparison of activity of liquid germall plus and germall 111 / 0 . 5 % or 0 . 8 % ipbc ( screening emulsion ) organ - preservative conc . ism 48 hrs 7 days 14 days 21 days 28 days liqgermplus sa 110 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 195 ec 2 , 600 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 2 . 5 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 240 , 000 120 & lt ; 10 & lt ; 10 & gt ; 1e4 an 230 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liqgermplus sa 2 , 800 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall ii 390 ec 1100 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 5 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 11 , 000 & lt ; 10 & lt ; 10 & lt ; 10 20 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 100 germall iii 195 sa 260 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 2 . 5 ec 4 , 300 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liquid psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 150 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & gt ; 1e4 an 200 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 390 sa 170 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 5 ec 2 , 500 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liquid psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 50 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & gt ; 1e4 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 195 sa 70 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 4 ec 1400 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liquid psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 41 , 000 & lt ; 10 & lt ; 10 & lt ; 10 40 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germall iii 390 sa 76 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ipbc 8 ec 3 , 400 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 liquid psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 14 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved 0 sa & gt ; 1e6 54 , 000 4 , 400 20 & gt ; 1e4 ec 80 , 000 67 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 2 , 000 4200 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can 990 , 000 320 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 380 , 000 170 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0071 ] table 10 comparison of activity of germaben ii and germaben iii ( screening emulsion ) use organ - preservative level ism 8 hrs 7 days 14 days 21 days 28 days germaben ii 0 . 30 % sa 480 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 20 , 000 100 2 , 600 380 , 000 380 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germaben ii 0 . 75 % sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 100 germaben iii 0 . 30 % sa 7 , 000 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 14 , 000 120 & gt ; 1e4 470 , 000 190 , 000 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germaben iii 0 . 75 % sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 5 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 unpreserved 0 sa & gt ; 1e6 46 , 000 & gt ; 1e4 60 & gt ; 1e4 ec & gt ; 1e6 170 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 psa 690 24000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 bc & gt ; 1e6 & gt ; 1e6 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 can 440 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 an 87 , 000 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 & gt ; 1e4 [ 0072 ] table 11 comparison of activity of germaben iie and germaben iiie ( screening emulsion ) use organ - preservative level ism 48 hrs 7 days 14 days 21 days 28 days germaben iie 0 . 30 % sa 580 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 1 , 600 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germaben iie 0 . 75 % sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germaben iiie 0 . 30 % sa 270 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can 4 , 000 & lt ; 10 & lt ; 10 & lt ; 10 90 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 germaben iiie 0 . 75 % sa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 ec & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 psa & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 bc & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 can & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 an & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 & lt ; 10 the 28 day challenge results reported in tables 3 - 11 above demonstrate the effectiveness of the preservative composition of the invention in a use emulsion composition against a wide range of bacteria and fungi organisms . while the invention has been described with particular reference to certain embodiments thereof , it will be understood that changes and modifications may be made which are within the skill of the art . accordingly , it is intended to be bound only by the following claims , in which :
this invention relates to a reaction product of allantoin and formaldehyde made in a molar ratio of about 1 : 2 . 75 - 1 : 3 . 25 , preferably 1 : 3 , respectively , preferably under controlled ph and temperature conditions , which product contains free formaldehyde , and methylene diol of about 580 - 1385 ppm , preferably at a ph of 7 . 2 , with advantageous long - lasting , anti - microbial properties , particularly against the organism b . cepacia , and in combination products with parabens and iodopropynyl butyl carbamate .