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IB&W) PROTECTED BY MINNESOTA TOBACCO LITIGATION" I~ROTECTIVE ORDER .! -252- PAPER 13 . NICOTINE ADDITION TO $1~OKE FROM FILTERS C.C. Greig BAT (UK&E) Limited Abstract Filters are conventionally regarded as a means of controlling delivery.by removal of smoke components, but have..th~.dr~wbac~_. of parallel (though not equal) removal of tar and nicotine. This paper will describe some experiments in which nicotine is added or bonded to filter materials, from which it can be released into smoke when this contacts the filter. Thus another means of manipulating nicotine delivery and tar:nicotine ratios is available beyond blend and cigarette design manipulations. 5700509139 CONFIDENTIAL MATERIAL PROTECTED BY ORDER OF THE CHANCERY COURT, JACKSON COUNTY, MS,

IB&W) PROTECTED BY MINNESOTA TOBACCO LITIGATION PROTECTIVE ORDER INTRODUCTION It iS becoming increasingly less acceptable to smoke in public, with increasing numbers and severity of bans on smoking in public places. In ~elation to the amount Of tobacco burnt to give sufficient mainstream smoke to :he smoker in an acceptable time', cigarettes are inefficient and produce butts, ash and sidestream smoke, all of which indicators of cigarette usage an~ contribute to social pressure. Slide ! shows the amounts of tobacco used in these various processes. There has long been a feeling that a non-smoke device able to deliver nicotine unobtrusively would be an acceptable alternative product. The first patents are ancient but recently the Advanced Tobacco Products Corporation in the USA have test marketed a series of products under the name FAVOR. .Slide 2 shows initial press comments and photographs.of these. The FAVOR Product -.FAVOR has been examined in detail-at BATUKE R&D Centre in Southampton in late IgB5 and early 1986. It was found to be an improvement on earlier designs made to prior ATP patents, in that less nicotine was contained per 'stick', and various physical details are recorded on Slide 3. Analysis of deliveries, as in Slide 4, showed low and erraticamounts of nicotine delivered. In relation to a UK low tar cigarette, it was thought unlikely, that the amount of nicotine deliQered by a conventional 3Sml pCff would be sufficient for user satisfaction after some hours of deprivation. Small scale panel tests.with expert smokers confirmed this, with only FAVOR Menthol proving at all acceptable. Problems with nicotine oxidation/degradation have been documented, possibly these having connected with taste descriptions of 'pepperinnss'. The accidentallighting of FAVOR was mimiced in the laboratory, concluding that large increases in nicotine delivery were unlikely but that a fire could perhaps be caused by burning polymer ~ebris. Solid state NMR (Slide 5) has now been used to investigate the constituents of the FAVOR source element and " the outer tube. Other materials are conventional. FAVOR as a Filter Element It was realised tha~ the FAVOR source element might be used as a means of fortifying nicotine in smoke if smoke acted as an eluant. The FAVOR source element was taped to a tobacco rod in the filter position, and the resultant device smoked Conventionally on a smoking machine. A puff-by-puff analysis showed prefential transfer of nicotine in the first few puffs, as demonstrated in Slide 6. Expressing these .data another way, Slide 7, demonstrates a falling nicotine transfer as. puff number increases similarly.to that seen in investigations of FAVOR itself when air alone is used as an eluant. 5'703509'70 T T CONFIDENTIAL MATERIAL PROTECTED BY ORDER OF THE CHANCERY COURT, JACKSON COUNTY, MS, IN RE TORACCf) LITIGATION. CASE No. 94-1429

IB&W) PROTECTED BY MINNESOTA TOBACCO LITIGATION PROTECTIVE ORDER Z Z Z -254- PAPER Demonstration of this ability to add nicotine to smoke has aroused considerable interest. Two immediate possible applications occur. One is to produce, for research and market test purposes, a variable tar/nicotine product without resource to the blend modifications which tO date have made this so difficult. Secondly, the drive towards lower blend costs is tending to reduce the use of high taste (and thus high nicotine and high price) tobaccos. If smoke nicotine could be increased by filter addition satisfactioh might be maintained. Modification of Paoer Filter Since the industry uses in the main cellulose acetate filters,'~ experiments with these and polypropylene were conducted to see if fortification would occur. Broadly similar transfer efficiences to th~ FAVOR plug source element.were found. It was however realised that nicotine degradation and migration would occur. The idea then arose of modifying paper filters to bond nicotine ionically and in~nobilise it against migration prior to smoking yet release it during smoking. Paper filters have the advantage that they are available to the indsutry and no new processing technology is required. It was thought that oxidation of the - CHzOH side chain to COOH and binding .of the base, nicotine, to this site would be feasible without grossly disrupting the fibre structure and leading to handling problems (Slide. B). Experiments using nitrogen dioxide as oxidant, and 13C solid state NMR as an analytical tool, showed that approximately 30% of the CH20H .... > COOH conversion could be attained in 60 hours (Slide g). This material remained intact but had somewhat lower strength than the starting material. Binding of nicotine to this is s~rongly pH dependent ($1.ide 10) and only lOW contents of nicotine are attained (,2% w/w). It is thought that moving to a more ~id- active site may be advantageou~ and experiments on cellulose phosphate and the related carboxylmethyl cellulose are in progress. "Arising from this work, two patents covering: (a) nicotine transfer from non-functionalised polymers, and (b) nicotine transfer from ionically bound nicotine on ox~dised cellulose have been filed. Work to support these is proceeding. ' 570~5:0SV1 CONFIDENTIAL MATERIAL PROTECTED BY ORDEI~ OF THE CHANCERY COURT, JACKSON COUNTY, MS,

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or~ mo CONI;II)ENTIAL MINNESOTA 'I'OBACC() I~I'I'I(.;ATION ------- r SMOKES WITI-IOUT FIRE Restrictions on cigarette smoking .are becoming more widespread in all advan- ced countries. Help for the addicted is on the way this year from San Antonio, Texas, home of AdVanced Tobacco Products. producer o[ the soon-to-be marketed, world's first smokeless cigarette - Favor• The ersatz Cigarette is no joke. Test marketing has begun and it goes on sale in San Antonio ~n Sep'tember. Manui'accuring and sales abroad will b~ by licence and ATP is c.rrently, talking to prospective licencees in Japan and Britain. Favor' was the inspiration.o[ a three-pack-a-day smoker and met data processing magnate, J. P. Ray. He began research into nicotine in 1978 and [ound thac considerable pleasure ~ould be.had [rom sucking the end of a tube' stuffedwith nicotine-soaked cellulose.wadding. No tobacco in the product means - initially at/east - no government health warning, no tar or carbon monoxide (because there is no burriing) and bes~ all no governme.nc taxes. • "i"" ' Disgui,sed to look like the smoker's friend, Favors are entrepreneur (compute~, oil, cable television) reckons that manufactured on conventional though specially modified even a tiny share of the $160 billion world cigarette market cigarette:making machinery. With manufacturing' costs is wortha considerable fortune: less than 3 per cent o[ the estimated at 16 cents a pack and each pack selling [or just market should give the ~l~mpan'y $600 million-a-year over a dollar, the men. behind Favor stand to make a serious ' revenues.' Of course getting thac market share, Will require amount,ot" money i[ the little brutes take off. a Ioc 0.[ advertising, buc chert again Favor, no~ being a real ~e chairman. Gerald R..Mazur' a millionaire cigarette, isn't subject to restrictions on advertising. (~Ugu!~;id ,(q ~u!,(doD 3o3 pm3~lOSpuv, uo~l~lWI o33~3qo~L mosouu!H u! BA:~I~I ~(q p~anpoJd lu~tuoocI Jo ,~doD) Ak~l~I £fi p~3npoad :NOI,LVgLLI~I H~IOOIAI

CON 1;1 I)ENTIA L M I N N I,;,N O'I'A TO I|A CC() I ATI GATION I FAVOR ADVANCED TOBACCO PRODUCTS CORR SAN ANTONIO, U.S.A. M,,~RI<ET TEST VERSIONS-1985 CORK WHITE 84mm NICOTINE CONTENTS REGULAR ~ 10-11 mg LIGHTS ~_ 6- 7 mg MENTHOL ~ 5- 6 mg Z÷: 6-7 mg MENTHOL) TOTAL WT.. ... 1285 mg TIPPING .... 40 mg SOURCE ELEMENT 160 mg SOURCE ELEMENT -. POLYPROPYLENE ? - OPEN CELLED FOAM .TYPE STRUCTURE ? -:I~ENSITY __~ 400 m9/cc - P. DROP ~ .. lOcmwg REGULAR, 7.5 LIGHTS + MENTHOL (sjj!lu]~;id £q :~u!fidoD aoj popoloS pro; uo!1~8!1!"I o33~3qoj, t;io,~oUU!lN u! A~f~t ~(q poonpoJd iuou~OO(l jo/{doD) A~[/{~i poonpoJd :NOIJ,VDI.LI'-I HHOOIAI

IB&W PROTECTED BY MI.NNESO'I'A TOBACCO LITIGATION PROTECTIVE OR.DER 1- SLIDE . PAPER 13 " " 1_ • , 570350975 CONFIDENTIAL MATERIAL PROTECTED BY. ORDER OF THE CHANCERY COURT, JACKSON ~OUNTY, MS,

(B&W) PROTECTED BY MINNESOTA TOBACCO LITIGATION PROTECTIVE ORDER FAVOR .. CONSTRUCTION MATERIALS . SOLID STATE C13 NMR Z ..... SOURCE" EEEMENT OUTER ~'UBE CONFIDENTIAL MATERIAL PROTECTED BY ORDER OF THE CHANCERY COURT, JACKSON COUNTY, MS,

I B&W} PROTECTED BY 5IINNESOTA TOBACCO LITIGATION PROTECTIVE ORDER 260 PAPER 13 SLIDE 6 FAVOR as a nicotine adding filter NlC (mg/puff) 10 mm 0.3 0.2 0.1 + FAVOR ~,. 1 2 3 4 5 .6 PUFF NUMBER 570350977 © o CONFIDENTIAL MATERIAL PROTECTED BY ORDER OF THE CHANCERY COURT, JACKSON CQUNTY, MS,

.I PROTECTED BY MINNESOTA TOBACCO LITIGATION PROTECTIVE O'RD~R SLIDE 7 140 i00 5O %NICOTINE FAVOR ADDED TO SMOKE I ~ | 1 4 5 .6 7 PUFF .NUMBER 570350S78.. CONFIDENTIAL MATERIAL PROTECTED BY ORDER OF THE CHANCERY COURT, JACKSON COUNTY, MS,