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That Woulukuuta THATWOULUKUUTA US009920146B2 (12 ) United States Patent ( 10 ) Patent No. : US 9 ,920 , 146 B2 Nacharaju et al. ( 45 ) Date of Patent: Mar. 20 , 2018 ( 54 ) METHODS OF TREATMENT TO IMPROVE ( 52 ) U . S . CI. THE QUALITY OF ALCOHOLIC ??? .. C08F 126 / 10 ( 2013 . 01 ) ; C08F 222 / 10 BEVERAGES USING VINYL ( 2013 . 01 ) ; C08F 222 / 18 (2013 . 01 ) ; C12H LACTAM - DERIVED POLYMER -HYDROGEN 1 /0424 ( 2013. 01 ) PEROXIDE COMPLEXES 8 ) Field of Classification Search CPC .. C08F 126 / 10 ; C08F 222 / 10 ; C08F 222/ 18 ; (71 ) Applicant : ISP Investments LLC , Wilmington , DE C12H 1 /0424 (US ) See application file for complete search history . (72 ) Inventors : Krishnamurthy Nacharaju , Hilliard , (56 ) References Cited OH (US ) ; Giovanni Nicola Onnembo , Wayne, NJ (US ) ; Mustafa Rehmanji , U . S . PATENT DOCUMENTS Riverdale , NJ (US ) ; Andrew Mola , 3 ,480 ,557 A 11/ 1969 Shiraeff Highland Lakes , NJ (US ) ; Bala 3 , 933 , 766 A 1 / 1976 Hofmann et al . Balasanmugam , Wayne , NJ (US ) ; 4 ,594 ,250 A * 6 / 1986 Lautenschlaeger .. A23C 7 /043 Joycelyn Yapchulay, Jersey City , NJ 426 /257 5 , 008 , 093 A 4 / 1991 Merianos (US ) 5 ,744 , 183 A * 4 / 1998 Ellsworth .. C12H 1 /0424 426 / 330 . 4 (73 ) Assignee : ISP Investments LLC , Wilmington , DE 6 , 239 , 206 B1 * 5 / 2001 Fussnegger . .. .. .. .. B01D 15 / 00 (US ) 426 / 271 2008/ 0113071 A15 /2008 Cohen ( * ) Notice : Subject to any disclaimer , the term of this patent is extended or adjusted under 35 OTHER PUBLICATIONS U . S . C . 154 (b ) by 0 days . International Search Report , PCT/ US2015 /031943 published on ( 21 ) Appl . No .: 15 /313 , 278 Nov . 26 , 2015 . (22 ) PCT Filed : May 21, 2015 * cited by examiner ( 86 ) PCT No. : PCT/ US2015 / 031943 Primary Examiner — Anthony Weier $ 371 ( c )( 1) , ( 74) Attorney , Agent, or Firm — William J . Davis ( 2 ) Date : Nov. 22 , 2016 (57 ) ABSTRACT (87 ) PCT Pub . No .: WO2015 /179622 Provided is a method of treatment of an alcoholic beverage , particularly beer or wine, for removing ingredient ( s ) causing PCT Pub. Date : Nov. 26 , 2015 undesirable sulfury and / or fatty flavor ( s ) , by contacting the beverage with a composition having a polymer -hydrogen (65 ) Prior Publication Data peroxide complex , wherein the polymer is derived from at US 2017/ 0190813 A1 Jul. 6 , 2017 least one N - vinyl lactam monomer, and wherein the hydro gen peroxide is present in an amount from about 1 % by weight to about 50 % by weight of the complex . Provided Related U . S . Application Data further is a method of treatment of an alcoholic beverage to (60 ) Provisional application No .62 /002 , 391 , filed on May remove at least ( a ) at least one ingredient causing at least one 23 , 2014 . undesirable sulfury and / or fatty flavor, and ( b ) at least one ingredient causing colloidal haze , including contacting the (51 ) Int. Ci. beverage with a composition described herein . Provided C08F 126 / 10 ( 2006 . 01 ) furthermore is an alcoholic beverage obtained by themethod C08F 222 / 10 ( 2006 .01 ) ( s ) of treatment described herein . C08F 222 / 18 ( 2006 . 01) C12H 1 / 056 ( 2006 .01 ) 10 Claims, 2 Drawing Sheets U . S . Patent Mar. 20 , 2018 Sheet 1 of 2 US 9 ,920 , 146 B2 Figure 1 Morten Meilgaard ' s Beer Flavor Wheel ISOVALERIOBUTYRICS DIACETYE KRANCID SMOKYKLOSBAKELITE CARBOLICCHEOROPHENOLLERS, LE ISODOFORMA MATCHTRIKING HUSKYCORN IGRITSWORTY PRES PHENOLICA, STRAW- LIKE ONIONECOOKED | FRESHLYCUT GRASS BIGRAN BEANYALMONDI E GRANS PORN PAPERSLEATHERY WALNUTCOCONUT ?? WOODY 3 PINEY . HOP OIL KLERE Seethe . ASNOHO DRY-HOP AN SEMSL KETTLE-HOP FLORAL MED HEMSELF BERMITAME VENA: PERFUMYGERANIOL FLORALSED,FRUITY ,ECOAGRANT ESONKINE |2- PHENYLETHANOIACETALDEHYDERIO STRAWBERRY SOLVENTA:KERA JOH097431 TOWNIORSKOFDENGANIST SUBSTUSREEMASPERO. RASPBERRYPEARBLACK CURRANI MOUTHCOATINGALE MELONY E LEARNINGNONOSATALCOHOURS NEREZONOS WNWNWAPPLE ETHYLACETATE INIESYOND, Shallo ISOAMYL|ACETATELAQUER LIKESCAN-LINERS PLASTICS D ETHYLHEXANOATES VINOSSPICY MUTHI ONIMIVS 5570 U . S . Patent Mar. 20 , 2018 Sheet 2 of 2 US 9 ,920 , 146 B2 Figure 2 PeroxydoneTM complexes containing a mixture of 1 : 1 and 1 : 2 ratios of hydrogen peroxide to N - vinyl pyrrolidone DOOI OHOOL H202 PVP 1 : 1 [ 23 . 45 % H202 ] 0 0 E0"H "H 03. - CH2 - CH2 H202 PVP 1 : 2 [ 131 . 28 % H202 ] US 9 ,920 , 146 B2 METHODS OF TREATMENT TO IMPROVE method most likely to minimize the formation of volatile THE QUALITY OF ALCOHOLIC sulfur compounds. Though strain -dependent , lager yeasts BEVERAGES USING VINYL generally produce a much larger variety of sulfur com LACTAM - DERIVED POLYMER -HYDROGEN pounds during fermentation than ale yeasts ; sulfury flavors PEROXIDE COMPLEXES are therefore one way of distinguishing between lagers and ales . Not all sulfury flavors are formed during the normal BACKGROUND brewing process , they can also result from bacterial con tamination or poor handling . These antagonists transform Field of the Invention sulfur compounds that otherwise are not flavor -active ( such The invention relates to methods of treatment of alcoholic 10 as the sulfur- containing amino acids methionine and cyste beverages to improve the quality thereof by contacting the ine ) into undesirable off flavors such as hydrogen sulfide and beverage with compositions comprising vinyl lactam -de - mercaptans. rived polymers that exist in the form of molecular com - Sulfury flavors are caused due to the presence of one or plexes with hydrogen peroxide . Particularly , the invention more sulfur - containing ingredients . One of the most impor relates to methods of treatment of alcoholic beverages to 15 tant sources of sulfur in beer is the sulfate ion . Sulfate ions remove one or more ingredients causing one or more unde - are derived from sulfuric acid or sulfate salts and consist of sirable sulfury and / or fatty flavors. The invention further a sulfur atom covalently bonded to four oxygen atoms. In relates to methods of treatment of alcoholic beverages to nature , they are often found in combination with positively remove one or more ingredients causing one or more unde charged calcium and magnesium ions (which hydrate to sirable sulfury and / or fatty flavors and as well as one or more 20 form gypsum and Epsom salts , respectively ) . ingredients causing colloidal haze . The sulfite ion is derived from salts of sulfurous acid and Description of Related Art consists of a sulfur atom bonded to three oxygen atoms. Alcoholic beverages include fermented beverages and Sulfites and bisulfites are both strong reducing agents , distilled beverages . Non - limiting examples of fermented capable of accepting oxygen atoms from other compounds beverages include beer, cauim (made from cassava or 25 to form sulfur dioxide and water. Most of the sulfites in beer maize ) , chicha (made from cassava , maize root , grape , apple are bound to carbonyl compounds, which diminishes both or other fruits ) , cider (made from apple juice or other fruit their flavor activity and their reducing capacity . A very small juice ) , huangjiu (Chinese , made from rice , millet , or wheat amount will remain free and eventually form sulfur dioxide . using a special starter culture of yeast , mold , and bacteria ) , When present in high concentrations in beer ( typically icariine liquor , mead (made from honey ) , palm wine (made 30 greater than 20 ppm ) , sulfur dioxide gives the aroma of a from the sap of various palm trees ), pulque ( originally made struck match . by the natives ofMexico , made from the sap of the maguey Sulfidic flavors are produced by hydrogen sulfide, thiols plant ) , tiswin (made from corn or saguaro , a large cactus ) , ( or mercaptans ) , thioesters , and related compounds . All are and wine . A distilled beverage , spirit, or liquor is an alco undesirable in beer , and all become more offensive as their holic beverage containing ethanol that is produced by dis - 35 concentrations increase . Hydrogen sulfide ( H , S ) is probably tilling ethanol produced by means of fermenting grain , fruit , the best understood member of this group . It is a fermenta or vegetables. Vodka , gin , baijiu , tequila , rum , whisky , tion by - product with a low sensory threshold of only a few brandy , and soju are non - limiting examples of distilled ppb . It makes its presence known by imparting to beer the beverages . aroma and taste of rotten eggs. Beer is an alcoholic beverage produced by the sacchari - 40 Thiols , also known as mercaptans , are closely related to fication of starch and fermentation of the resulting sugar. hydrogen sulfide . The most relevant members of the thiol The preparation of beer is called brewing . family in brewing are methyl - , ethyl - , and butyl- mercaptans . More than 1 ,000 different flavor ingredients have been These compounds have aromas that may remind one of identified in beer , and more are being found as increasingly putrefied cabbage , garlic , onion , or egg. At very high con sensitive analytical methods are developed . Some of these 45 centrations they may be perceived as shrimplike" Piike .. flavors are derived from raw materials (malt , adjuncts , hops , Other sulfidic flavors attributed to mercaptans have garlic , and water ) , but the vast majority are formed by yeast during cabbage , or burnt rubber notes . Similar flavors are associ fermentation . Chemical and physical methods of analysis ated with diethyl sulfide , diethyl disulfide , and polysulfides . can provide a great deal of information about these ingre - These diethyl compounds are generally regarded as equiva dients
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