the foregoing discussion illustrates various exemplary embodiments of the application and barrier properties of sealing compounds and closure elements of the present invention . the following examples and data further exemplify the present invention . [ 0065 ] fig1 shows a capped bottle where the organic permeant concentration ( c 2 ) outside the bottle is greater than the concentration ( c 1 ) inside the bottle . when this case exists , the permeant ( s ) outside impact the liner material , sorb or dissolve into the liner material and then diffuse under a concentration gradient through the liner material or sealing element and finally release from the liner surface inside the bottle . the driving force for permeation is given as a partial pressure ( p 2 to p 1 ) difference of the permeant ( s ) across the sealing portion of the liner . the permeant concentration gradient shown above can be simulated experimentally in the laboratory making it possible to measure barrier improvement of cyclodextrin - containing sealing compounds and closure elements . the following procedures were used to measure improved closure material barrier to organoleptic permeants , such as , aliphatic aldehydes , unsaturated aldehydes and ketones and trichloroanisole . permeation across a barrier can be explained where the membrane at time zero ( t 0 ) is initially free from permeant vapor . the penetrant pressure p 2 at the upstream face of the membrane is increased giving a concentration in the surface layer c 2 ( see fig2 ). diffusion is a measure of how quickly permeants move in a membrane across the concentration gradient and the time it takes to reach steady state . the downstream pressure , p 1 , while measurable , is negligible at small times relative to the upstream pressure p 2 . the amount of vapor permeating the thermoplastic barrier increases linearly with time once steady state has been reached . at large times , the upstream pressure p 2 will equal the downstream pressure p 1 . the permeation test method used to evaluate organic barrier involves experimental techniques to measure organic molecule transport through a closure material test disc , using a static concentration gradient . the schematic assembly of the permeation cell is shown in fig2 . a monolayer disc of the closure material and various organic test permeants were used to evaluate barrier performance . high - resolution gas chromatography was used to qualitatively and quantitatively measure the cumulative downstream penetrant concentration p 1 at a specified time . the invention shows cyclodextrin dispersed into a closure material then formed into a disc reduces organic vapor transport , compared to the same material without cyclodextrin , both measured in static test cells ( fig2 ) and quantitated as a reduction in mass flux . monolayer discs and test permeants ( i . e ., aldehydes and ketones ) were initially evaluated to create a permeation profile . the time when p 2 = p 1 is determined for each closure material . the midpoint of the steady state profile or time t 1 / 2 is established for each closure material without cyclodextrin . an example closed - volume static permeation profile illustrating p 2 = p 1 and t 1 / 2 is provided in fig3 . three - closure materials ( svelon ® 855 a sealing compound for crown corks , polyliner ® 461 - 3 a sealing compound for plastic closures and oxylon ® cs25 a high - barrier sealing compound for crown corks ), all manufactured by ds - chemie , bremen , germany , were prepared and tested by the following preparation and analytical methods . table 1 provides time t 1 / 2 for each test closure material . closure materials were compounded with triacetyl gamma cyclodextrin ( ta - γ - cd ) using a laboratory scale batch mixer . triacetyl gamma cyclodextrin was dry blend mixed with the resin prior to compounding on a weight to weight basis of 0 . 30 % and 0 . 4 % triacetyl gamma cyclodextrin . the triacetyl gamma cyclodextrin was manufactured by wacker biochem corporation , adrian , mich . a brabender fusion bowl or batch mixer was used to compound the closure materials . the fusion bowl consists of two counter rotating roller blades in a number eight - shaped bowl . control closure material ( no cd ) and closure material + cd material was run using the procedure described below . the fusion bowl temperature was set at 125 ° c . with the rpm of the blades set at 60 , 40 grams of resin was dropped into the bowl . all the material is fed into the bowl over a 30 - second period . after another 6 . 5 minutes of processing , the screw speed was reduced to zero and the molten resin is removed and collected on aluminum foil . the bowl and the roller blades were thoroughly cleaned before starting the next run . closure material disc preparation . several grams of compounded closure material were placed into an atlas lab - mixing molder . the mold was heated to 175 ° c ., the resin mixed to a molten state , and then the resin was injected into the heated ( 85 ° c .) mold . the dimensions of the mold cavity are 1 . 75 - cm × 4 . 45 - cm × 0 . 10 - cm thick . a 1 . 27 - cm diameter punch is used to cut two discs from the molded part for static permeation testing . organic vapor permeation . the permeation method involves experimental techniques to measure organic molecule transport through a polymer packaging structure , using a static concentration gradient . high - resolution gas chromatography ( hrgc ) operated with a flame ionization detector ( fid ) or with electron capture detection ( ecd ) is used to measure the cumulative downstream penetrant concentration at time t 1 / 2 . apparatus . disc samples (˜ 1 , 000 μm thick × 1 . 27 cm diameter and weighing approximately 125 mg ) were tested in a closed - volume vapor permeation device ( refer to fig2 ). the experimental aluminum measurement cell has two compartments ( i . e ., cells ) separated by a molded disc of closure material under study ( effective disc area = 1 . 3 cm 2 ) and capped at both ends using teflon ® faced butyl rubber septa and aluminum crimp - tops . the test disc is placed into the upper cell ; the cell is assembled using an o - ring to firmly seal the test disc and screws to pull upper and lower cells together . next , the upper cell is capped with a teflon ® faced butyl rubber septa and aluminum crimp - top . two permeation standards are prepared . the first permeant standard contains octanal , nonanal , trans - 2 - nonenal and 1 - octen - 3 - one , and the second permeation standard contains 2 , 4 , 6 - trichloroanisole . all of the permeants are dispersed in a deionized water / surfactant mixture . the permeant water / surfactant mixture is injected into the lower cell providing a concentration p 2 at t 0 shown in tables 2 to 6 . individual permeant concentrations p 2 in the lower cell are expressed in parts per million μl / l ( vol ./ vol .) using gas law conversion . then the lower cell is immediately capped with teflon ® faced butyl rubber septa and aluminum crimp - top . aldehydes and ketone . this method involves experimental techniques designed to simultaneously measure the flux of co - permeants across the closure material test disc . the test methodology simulates accelerated shelf - life testing conditions by using an elevated cell storage temperature of 50 ° c . hrgc operated with a fid was used to measure the change in the cumulative penetrant concentration at time t 1 / 2 in the upstream cell . at time t 1 / 2 , a sample was collected by solid phase microextraction ( spme ) from the upper cell and analyzed by hrgc / fid . individual permeant concentrations were determined from calibration standards and measured in nl / l or parts per billion ( vol ./ vol .) using gas laws . [ 0085 ] table 3 concentration of co - permeants measured by static permeation using headspace hrgc / fid in a control polyliner ® disc and polyliner ® discs with 0 . 40 % triacetyl gamma cyclodextrin - permeation cell temperature maintained at 50 ° c . conc . p 2 at concentration − p 1 time = 0 at time = 6 hours all samples control 0 . 40 % ta - γ - cd permeant μ / l nl / l nl / l octanal 98 370 360 nonanal 91 43 30 trans - 2 - nonenal 89 29 21 1 - octen - 3 - one 103 92 83 total 381 534 494 test cells were prepared and analyzed in triplicate . tables 2 and 3 contain four permeants , the concentration p 2 of each of the permeants in the lower cell at t = 0 , and the concentration p 1 of each of the permeants in the upper cell at time t 1 / 2 or 6 - hours in the control and the triacetyl gamma cyclodextrin ( ta - γ - cd ) samples . trichloroanisole . hrgc operated with an ecd was used to measure the change in the cumulative trichloroanisole concentration at time t 1 / 2 in the upstream cell . at time t 1 / 2 , a sample was collected by solid phase microextraction ( spme ) from the upper cell and analyzed by hrgc / ecd . the trichloroanisole concentration is determined from calibration standards and measured in pl / l or parts per trillion ( vol ./ vol .) using gas laws . test cells are prepared and analyzed in triplicate . table 4 to 6 contain the concentration p 2 of tca in the lower cell at t = 0 , and the concentration p 1 of tca in the upper cell at time t 1 / 2 in the control and the triacetyl gamma cyclodextrin ( ta - γ - cd ) samples . [ 0088 ] table 5 concentration of trichloroanisole measured by static permeation using headspace hrgc / ecd in a control polyliner ® disc and polyliner ® discs with 0 . 40 % triacetyl gamma cyclodextrin - permeation cell temperature maintained at 50 ° c . conc . p 2 at concentration − p 1 time = 0 at time = 6 hours all samples control 0 . 40 % ta - γ - cd permeant μl / l pl / l pl / l 2 , 4 , 6 - 0 . 925 9 , 100 5 , 700 trichloro - anisole total 0 . 925 9 , 100 5 , 700 [ 0089 ] table 6 concentration of trichloroanisole measured by static permeation using headspace hrgc / ecd in a control oxylon ® disc and oxylon ® discs with 0 . 40 % triacetyl gamma cyclodextrin - permeation cell temperature maintained at 50 ° c . conc . p 2 at concentration − p 1 time = 0 at time = 16 hours all samples control 0 . 30 % ta - γ - cd permeant μl / l pl / l pl / l 2 , 4 , 6 - trichloro - 0 . 925 920 620 anisole total 0 . 925 920 620 test cells were prepared and analyzed in triplicate . tables 4 and 6 contain 2 , 4 , 6 - trichloroanisole permeant , the concentration p 2 of each of the permeants in the lower cell at t = 0 , and the concentration p 1 of each of the permeants in the upper cell at time t 1 / 2 ( 6 - hours for svelon and polyliner , and 16 - hours for oxylon ) in the controls and the triacetyl gamma cyclodextrin ( ta - γ - cd ) samples . the data in tables 2 to 6 show a low loading of cyclodextrin material having compatible pendant groups can provide excellent mass flux reduction in sealing compounds and liner materials . these data show that the closure elements or sealing elements according to the present invention provide excellent barrier properties and organic permeants reductions . the following procedures were used to measure the reduction or complexation of residual volatiles in closure materials . svelon ® 855 was compounded with triacetyl beta cyclodextrin using a laboratory scale batch mixer . triacetyl beta cyclodextrin ( moisture content & lt ; 2 , 000 ppm by weight ) was dry blend mixed with the resin prior to compounding on a weight to weight basis of 0 . 40 % triacetyl beta cyclodextrin . the cyclodextrin is dried at 105 ° c . for a minimum of 6 hours at 1 ″ hg vacuum . a brabender fusion bowl or batch mixer was used to compound the svelon ® 855 + cd . the fusion bowl consists of two counter rotating roller blades in a number eight - shaped bowl . a control svelon ® 855 ( no cd ) and the svelon ® 855 + cd material was run using the procedure described below . the fusion bowl temperature was set at 125 ° c . with the rpm of the blades set at 60 , 40 grams of resin is dropped into the bowl . all the material is fed into the bowl over a 30 - second period . after another 6 . 5 minutes of processing , the screw speed is reduced to zero and the molten resin is removed and collected on aluminum foil . the bowl and the roller blades are thoroughly cleaned before starting the next run . compounded svelon ® 855 material is milled into shavings having ˜ 20 um thickness for residual resin volatiles testing . residual resin volatiles . volatile compounds in the svelon ® 855 samples out - gas into the vial &# 39 ; s headspace during confinement . these volatiles are then purged from the vial &# 39 ; s headspace and the individual components subsequently identified and quantitated by dynamic headspace high - resolution gas chromatography / mass spectrometry ( dh hrgc / ms ). seventy - six ( 76 ) specific compounds quantitated in the dh hrgc / ms method are combined into ten broad chemical families ( i . e ., aliphatic alcohols , aliphatic aldehydes , aromatic aldehydes , unsaturated aldehydes , saturated ketones , alpha unsaturated ketones , aromatics , alkanes , alkenes and acetates ) typically associated with off - odor / flavor compounds . a 2 . 00 ± 0 . 02 g sample is placed into a 22 - ml glass headspace vial . the vial is capped using a teflon faced septa and aluminum crimp - top . residual resin volatiles are desorbed from the sample into the headspace by heating the vial at 85 ° c . for 24 - hours . at the end of the time interval , the sample is removed from the controlled environment to a purge and trap sampler interfaced via ajet separator to the mass spectrometer . mass spectra from the sample total ion chromatograms are searched against an in - house reference spectra file of the seventy - six compounds . quantitation is carried out with two internal standards and two surrogate standards , all added prior to sample purge . the analytical results ( compounds are expressed in nanograms per gram of resin or parts per billion ) are provided in table 7 . when a commercial closure liner material ( svelon ® 855 ) is analyzed by gas chromatography for mobile migrant contaminants , it is shown to contain a very complex mixture of volatiles . over fifty individual compounds are detected chromatographically . these residual volatile materials are principally branched alkanes , alkenes and cycloalkanes to a smaller number of organoleptic compounds such as saturated and unsaturated aldehydes and substituted aromatic compounds . the largest chemical families represent by svelon ® 855 residual volatiles are aromatic ( ten individual compounds ) and alkanes ( three individual compounds ). saturated and unsaturated aldehydes and the saturated ketone families contained only a single compounds each . in all , sixteen of the seventy - six compounds were identified above the estimated quantitation level of the method — generally low parts per billion for most of the listed compounds . the organoleptic compounds of most interest in table 7 are the aldehydes ( acetaldehyde and acrolein ) and to a lesser extent styrene and alpha methylstyrene . acetaldehyde is the one of the larger analytes in the svelon ® 855 and generally associated with off - flavor in bland beverages such as mineral water . further acetaldehyde is a very mobile contaminant in the resin . the aromatic and alkane family compounds have significantly less odor and taste impact . the compound ( s ) and their off - odor / flavor impact is dependent on the specific beverage or container content . triacetyl beta cyclodextrin ( ta - β - cd ) shows the best reduction of svelon ® 855 residual resin volatiles . using dh hrgc / ms ( dynamic headspace high - resolution gas chromatography / mass spectrometry ) to measure residual volatiles , the total volatile compounds ( all sixteen compounds detected in the 76 compound list ) reduction is 38 % for an admix of 0 . 4 % ta - β - cd . specific organoleptic compounds ( e . g ., acetaldehyde and acrolein ) present in large amounts were greatly reduced by ta - β - cd . acetaldehyde and acrolein were reduced by 45 % and 69 % respectively . styrene and alpha methylstyrene were reduced 31 % and 30 % respectively . acetone , not considered an organoleptic compound , was reduced by 46 %. the more difficult resin volatiles to reduce are in the aromatic and alkane families ; smaller reductions of 29 % and 21 % were achieved for the combined compounds in the aromatic and alkane families , respectively . a closure composition was tested comprising low density polyethylene ( ldpe ). molded closure compositions were compounded with and without cyclodextrin materials [ maleic anhydride grafted alpha cyclodextrin copolymer ( ma graft α - cd ), triacetyl alpha cyclodextrin ( ta α - cd ) and alpha cyclodextrin ( α - cd )] and immersed in deionized water containing ozone inside glass bottles , which were sealed with aluminum faced metal screw cap closures . the bottles containing the closure compositions were stored at 40 ° c . for 7 days . at the end of the accelerated storage period , the aqueous contents were solvent extracted , concentrated and then analyzed . masterbatch materials . α - cd , triacetyl α - cd and α - cd grafted ldpe were individually compounded into masterbatches . the three masterbatches and closure liner composition ( polyliner 461 , ds - chemie , bremen , germany ) were compounded to provide an α - cd loading of 0 . 50 wt .-%. the final let down liner compositions with cd polyolefin masterbatch compositions were further prepared prior to accelerated ozonated water storage . the ethylene - maleic anhydride copolymer / ldpe was compounded with a stoichiometric weight loading of unmodified α - cd ( 2 . 78 wt -%) using a brabender platicorder mixing bowl forming the masterbatch . two masterbatch samples of ldpe resin were also compounded on a brabender plasticorder mixing bowl containing umnodified α - cd and ta α - cd ( 2 . 78 wt .-%). all resins were dried at 85 ° c . for 2 hours under vacuum (& lt ; 0 . 1 ″ of hg ) before use , while α - cd and ta - α - cd were dried at 105 ° c . for 30 minutes . the following masterbatch compositions were compounded . alpha cyclodextrin compounding in ethylene - maleic anhydride copolymer / ldpe ( ema / ldpe ) masterbatch . 1 . 11 gms of alpha cyclodextrin ( wacker biochem corp ) was compounded into 39 . 89 gms of ema / ldpe ( plexar px 175 ) and 1 . 11 gms of α - cd or ta α - cd ( wacker biochem corp ) was compounded in ldpe ( na 204 , equistar chemicals , l . p .) using a brabender plasticorder mixing bowl for 5 minutes at 130 ° c . and 80 rpm . closure test compositions . final test compositions of cd masterbatches and closure liner composition were made compounding the materials in a brabender plasticorder mixing bowl for 5 minutes at 130 ° c . and 80 rpm . the wt .-% test compositions are provide in table 8 . this material was then molded into sample coupons 4 . 45 cm × 1 . 59 cm × 0 . 10 cm with an atlas laboratory mixing molder set at 140 rpm , 150 ° c . for 2 minutes , with a mold temperature of 90 ° c . a laboratory system to generate ozone includes passing pure oxygen from a feed gas ( 5 . 5 liters / min ) into a corona discharge ozone generator producing high purity ozone . a continuous ozone monitor records the ozone generator output . ozone is absorbed into the water yielding a substantial level of dissolved ozone gas in a given volume of water ( approximately 800 ppb ozone ). the ozone containing water is suitable for use in testing sealing element materials . the test involves liner material test coupons exposed to water sterilized with 800 ppb ozone and stored in 500 ml glass bottles with 475 ml of ozonated di water , metal screw caps with aluminum - faced liners . a 4 . 45 cm × 1 . 59 cm × 0 . 10 cm in test coupon is wedged into the mouth of the bottle . triplicate bottles are stored on their sides for seven days at 40 ° c . following the storage period , the aqueous contents are extracted 3 times with 30 ml methylene chloride , the methylene chloride extracts are dried through sodium sulfate drying columns , and the volume reduced to 0 . 5 ml using kuderna - danish evaporator . the internal standard acenaphthene d - 10 was added to the reduced extracts . standards were prepared by spiking three levels of aldehyde ( 0 . 1 ppb , 0 . 25 ppb and 1 . 0 ppb ) into the same water used to fill the test sample bottles and then liquid extracted with dichloromethane and volume reduced to 0 . 5 ml . erucamide was spiked at 11 . 5 ppb in extracted in the same manner . the internal standard acenaphthene d - 10 was added to the reduced extracts . all mass spectrometer response factors were taken relative to an internal standard of acenaphtene d - 10 that was spiked into the final solvent extract . the solvent extracted and concentrated samples were analyzed by gas chromatography / mass spectrometry gc / ms using the conditions in table 9 . when exposed to ozone treated water , closure compositions containing ta α - cd and α - cd produced ppb and sub - ppb levels of c 6 to c 9 aldehydes , while the ma grafted ( α - cd showed concentrations less than the gc / ms method detection limit of 0 . 10 ppb . in all cases , the cyclodextrin containing closure compositions produced lower aldehyde migrants . in the ozonated water , a number of saturated and unsaturated amides where detected as migrants . in the control water sample , as well as the cyclodextrin containing samples , the principal unsaturated and saturated fatty acid amide migrants were c 18 , c 14 to c 16 unsaturated and saturated fatty acid amides were approximately 4 × less than c 18 , c 12 to c 14 unsaturated and saturated fatty acid amides were approximately 15 × less than c 18 and erucamide was a trace migrant at approximately 1 ppt . in all cases , the cyclodextrin containing closure compositions produced lower fatty acid amide migrants in the ozonated water . the obtained results are shown in table 10 . fatty acid amide lubricants provide internal and external lubrication to the liner composition . the rate of penetration of the lubricant into the polymer is governed by its solubility , which depends on the carbon length and unsaturation . the results clearly show the effectiveness of the three alpha cyclodextrin compositions for reducing oxidative decomposition products of the lubricant and transfer of amide lubricants from the liner surface into the ozone treated water . the cyclodextrin containing liner formulations did not adversely affect closure torque measurements .