IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`In re application of: R. Singh, et ai.
`
`Examiner: I. Zemei
`
`Application No;
`
`10/837,525 (Conf. 1983)
`
`Group Art Unit: 1711
`
`Filed:
`
`April 29, 2004
`
`Docket No.: H00(33965CIP-4510
`
`Titie: COMPOSITIONS CONTAINING FLUORINE SUBSTITUTED OLEFINS
`
`Commissioner for Patents
`
`Alexandria, VA 22313-1450
`
`RULE 132 DECLARATION OF DR. GEORGE RUSCH
`
`I, Dr. George Rusch, declare and state that:
`
`i.
`
`I am the Director of Toxicoiogy and Risk Assessment at Honeywell International inc.
`
`(“Honeywell”).
`
`I hold a Phi). degree in Chemistry from Adelphi University, in
`
`Garden City, NY. I have been employed by Honeywell andfor its predecessor in
`
`interest, the assignee of the application, since about August, 1980 holding various
`
`positions, including my current position as Director of Toxicoiogy and Risk
`Assessment.
`
`2.
`
`Toxicoiogicai testing of HFO—l225zc (1,1,3,3,3—pentafluoropropene)
`
`F30
`
`F
`
`H>j<F-"
`
`HFO—1225zc
`
`is described in the US. Department of Commerce, National Technical Information
`
`Service publication entitled “Support: Letter from Dupont Haskell Lab to US EPA
`
`Regarding Results of Bacterial Reverse Mutation Assay Conducted with i—Propene,
`
`1,1,3,3,3,—Peritafluoro-, dated 04/17/00” (Exhibit “A”). The toxicity tests were conducted
`
`by standard methods known to those of ordinary skill in the art. In particniar. the
`
`methods involve determining the LC5[} or median iethal concentration required -to kill half
`
`Page 1 01.20
`
`Arkema Exhibit 1142
`
`Page 1 of 20
`
`Arkema Exhibit 1142
`
`

`
`Application No. 10/837,525
`
`Attorney Docket No. H0003965CIP-4510
`Page 2 of 4
`
`the members of a tested population. The protocol used for this LC50 study consisted of a
`
`series of separate 4-hour exposures of groups of rats to the test compound. The animals
`
`are observed for mortality that may occur during the exposure or within the 14 day post-
`
`exposure observation period. Results of this test are reported in Table l below.
`
`Parameter
`
`I-IFO l225zc
`
`Table l
`
`Concentration (ppm)
`
`Initial Population Size (rats)
`
`}’opuEation Deaths during Exposure
`
`2,000
`
`30
`
`0
`
`
`
`
`
`i
`
`
`
`
`
`6
`
`4
`
`Less than
`2,(}{)(}*
`
`Popniation Deaths after Exposure
`
`Population Survival
`
`LC:-,0 (ppm)
`
`
`
`*At 2000 ppm, more than half (6/10) of the rats died.
`
`3.
`
`I have tested and/or supervised the toxicologicai testing of }~$O—l225ye (l,2,3,3,3—
`
`pentatlaoropropene)
`
`F3C>...<t-l
`
`F‘
`
`F
`
`HFO»I225ye .
`
`The I-E0 l’.Z25ye testing done under my supervision used substantially the same methods
`
`used to produce the results described in connection with the published testing of HFO-l225zc
`
`described above, except that a greater initial population was used in testing 1E*‘O~«E?.25zc.
`
`Honeywell uses srnali population sizes in toxicity testing where possible to minimize the use
`
`of animals in its testing programs. Results of the HFO~i225ye testing that we did, and which
`
`we believe to be reliable and representative of results comparable to the test results reported
`
`in Exhibit A, are reported in Tables 2 and 3 below.
`
`Page 2 of 20
`
`Page 2 of 20
`
`

`
`Application No. 10/837,525
`
`Attorney Docket No. H0003965CIF-4510
`Page 3 of 4
`
`Table 2
`
`
`
`
`Concentration (ppm)
`
`§00,0001250,000*
`
` Initial Population Size (rats)
`3 per group
`
`0,0
`
`0/0
`3 per group
`
`250,000
`
`
`
`*Two separate exposures were conducted. The first was at 100,000 ppm and the second at
`
`250,000 pprra. Both were four (4) hours in duration.
`
`4.
`
`The results in Table 2 illustrate that Hi-“‘O—i225ye is far less toxic than I~[FO—l225zc.
`
`In particuiar, this information evidences that HFO-l225ye has a toxicity, as measured by
`
`LC50, at least approximately 125 times less than HFO—1225zc.
`
`5.
`
`In addition to the testing above, I supervised toxicological testing of I-I.FO-l22Sye using
`
`mice as the test population as mice are believed in many cases to be more sensitive than rats
`
`to toxins. The results of the tests using mice were generally consistent with those conducted
`
`using rats. The mice tests qualitatively indicate tE1atHFO—i225ye is substantially less toxic
`
`than HFO—1225zc. The results of these tests are "reported in Table 3 below.
`
`Tabie 3
`
`
`
`
`
`Concentration (ppm)
`
`1995309
`
`250.000
`
`Erritiai Population Size (mice)
`
`Population Deaths during
`Exposure
`
`Population Deaths after
`Exposure
`
`Population Survival
`
`3
`
`1
`
`2
`
`3
`
`0
`
`2
`
`l
`
`Greater than
`Greater than 300,000 and less
`
`
`3-C50 (PPFTF)
`1 ()0, 000
`than 250,000
`
`
`
`
`
`
`
`
`
`Page 3 of 20
`
`
`
`
`Population Deaths during Exposure
`
`Population Deaths after Exposure
`Popuiation Survival
`
`
`
`R
`
`Page 3 of 20
`
`

`
`Application No. 19/837,525
`
`Attorney Docket No. H€)00396SCIP-4510
`Page 4 of 4
`
`6.
`
`I hereby declare that all statements made herein of my knowledge are true and that all
`
`statements made on information and belief are believed to be true and further that the
`
`statements were made with the knowledge that willful false statements and the like so made
`
`are punishable by fine or imprisonment, or both, under {$1001 of Title 18 of the United States
`
`Code and that such willful false statements may jeopardize the validity of the application or
`
`any patem issued thereon.
`
` ¥
`
`(l./‘:2
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`asI\l'3\§l0NEY\VELl..\P:.llcnl§\Al_l.lD\§72f1vW-5'3 lISA\D:::fI:\P26~i4(i-HUSA-Decizaraslilieux-4,xl:>c
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`Date
`
`Page 4 of 20
`
`Page 4 of 20
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`

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`One Source. One Search. One Solution.
`
`‘ SUPPORT: LETTER FROM DUPONT HASKELL LAB TO
`USEPA REGARDING RESULTS OF BACTERIAL
`REVERSE MUTATION ASSAY CONDUCTED WITH
`1-PROPENE, 1,1,3,3,3-PENTAFLUORO-, DATED
`04/17/00
`
`17 APR
`
`
`
`U.S. Department of Commerce
`National Technical Information Service
`
`Page 5 of 20
`
`Page 5 of 20
`
`

`
`coomc FORMS FOR sac INDEXING
`
`Microfiche No.
`
`0TS0573989
`
`BE!‘-{Q-0100-M638
`
`nmw. SUBMISSION: LETTER mom nurom HASICELL tans -to usem
`nsaAnnmo'1u=.suLrs.or Acursmmumon 1-ox1&:m"s-nmvm nwrs
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`wrm 1-morass, 1.1.33.3-PENTAFLUOR0-. om,-:9 oxmioo
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`’
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`l-PROPENE.I.v1.3,3,3-PAEN1'AFLUORO-
`
`Page 6 of 20
`
`Page 6 of 20
`
`

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`INITIALINITIAL
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`Page 7 of 20
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`_ Document PtocessingCenter(740‘l)
`Attention: 8(e) Coordinator
`-
`. Office 'ofPdllution-Preve.'tuionandToxics
`. U. S. Enviromnentnl Protection Agency
`40! M-Street sw
`Washington.DC 20460_
`_
`_
`.
`_
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`
`Dear8(c) Coordinator.
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`'
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`O
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`‘~'.-';- 4,
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`l-Ptopenc. l.l,3§3..3-pcntafluoroi
`'
`CAg $27-7 .
`
`to‘ infonu you of the results of an acute inhalation toxicity‘ study conducted '
`' This letter
`_
`ahove'refer'eno,ed_test material.
`*-_.‘.2'- ' - ‘
`" __
`in ms with
`'- . ‘..-’
`"2 -
`r.“",-'-_:'.'-.'
`"._-"'_.___...';".';;_‘
`Four groups‘of5 male and 5 fem.Ile__8-week’ old C;lI':_CD_°{SD)lG§ BR‘rnts',gv'e_re_-c:‘tp.os'::'d f
`- nose‘-only,to gas aunospheres of the test material for _a. single. 4§hour petiqd. .
`‘
`'
`'
`Concentrations tested included 500. 2000, 3300. a_nd_ 4500.‘ pm_. Rats were
`_ ' ' Trot;
`clinical signs-of toxicity immediately following
`aidfiuririg a'14-day‘reooV.e1y'-
`period. ‘In addition. approximately I day prior to
`(baseline) ehd ap‘proxirn_ately. ‘
`l'hour'and 24 hours after exposure, each rat wu systematically oh‘serve§'for
`_
`behavioral anotmliesinanopen field.
`_
`_'
`-'
`7
`1 -'
`
`-
`
`_
`
`'
`
`-
`
`'
`
`Cage:s_idc exsttnjnation of rats fr_oztI the 500 ppm concentration group revealed no clinical
`signs of toxicity ttnmed"iately fol|o'v'wit'tg' exposure‘_ or dining the recovery period. Death
`“d.-P!?81Z¢$5iV¢lY-9°Y°'P€=“n3°€l.$i8“S9“°Xi9i!Y-“¢='?9bS¢fi'°¢iI3@iS:f*9!i‘
`tire.
`remaining-Iydups, and these signs included lethargy. tremors,
`prosuation. ‘abnotinal gait. splayed limbs. and spasms. All clinical signs ottioxiéiiy were
`re\¢er§i_blg_in
`ta_ls from all_groups,
`‘
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`Page 8 of 20
`
`Page 8 of 20
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`

`
`IA.--04
`
`‘For neurobehuviomi endpoints in open field. all rats had scores within normal
`parameters on’ the day prior to exposure. ‘Approximately l hr :tft'er'é'xpc'stire, nits in the
`500 ppm group generally appeared to be normal except that 5/10 rats exhibited paipebral
`closure in the open field. One day after exposure. ZIIO of the 500 ppm rats had low
`arousal.
`'l'hese'signs appeared to he transieru and are sometimes identified in control rats
`in other studies. The lack of a concurrent control group. involving the same’ confinement
`characteristics of the nose-only exposure system. precludes a definitive neurobdraviqral
`no-observable-adverse-effect level for this concentration. Signs identified I hr after
`exposure in the 2000 ppm group included abnormal posture. slow righting reflex. poor
`coordination of movement. abnormal gait. and palpebml closure in the open field. These ~
`signs were also present l day later. but appeared to be more severe. Mortality occurred
`3-5 days after exposure for 6/10 of the rats in the 2000 ppm group. In general. the rats‘
`that died exhibited more severe behavioral effects. Some of the rats that survived until
`the scheduled sacrifice. however, also exhibited some behavioral effects, but to a lesser
`extent. Both the incidence of mortality (M0 at 33(1) ppm and 9/10 at 4500 ppm) and
`severity of the behavioral symptoms were greater in the 3300 and 4500 pptngroups than
`at 2W0 ppm.
`.
`
`‘
`
`Under these experimental conditions, the findings described above appear to be
`reportable. baed upon EPA guidance regarding the reportability of such data under
`TSCA Section 8(e) criteria.
`'
`'
`
`A
`
`V
`
`C .
`‘3’5<‘c-;._‘._
`‘
`
`A
`
`e
`A. Michael Kaplan. Ph.D.
`Direaor-Regulatory Affairs
`
`AMKlIRB:clp
`(302)366-5260
`
`Page 9 of 20
`
`Page 9 of 20
`
`

`
`CERTIFICATE or AUTHENTICITY
`
`THIS Isfocefifllflmnuunuudmnacuuppouhgmmbuflanllcggum meant.
`and complain nptoduwom 0! an ucardn or 0.8. Envlronmcnual Pnlulnn Acnncy
`
`_ document: at dclvlrod In on ugu!_u eouru cl business to: mlctollmlng.
`
`3; 05
`
`Page 10 of 20
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`Page 10 of 20
`
`

`
`IA 0 1
`
`CODING FORMS FOR SRC INDEXING
`
`Microfiche No.
`
`OTSOS73989
`
`8EHQ-0200-14638
`
`02/22/00
`
`Submitting Organization
`E 1 DUPONTDENEMOURS .3; co
`
`A SUPPORT: LETTER FROM DUPONT HASKELL LAB TO USEPA INFORMING OF
`ADDTNL RESLTS OE ATOX INHALATION & RAT BONE MARROW
`
`MICRONUCLEUS ASSAY W/I.l.3.3.3-PENTAFLUOROPROPENE, DATED 02/2]/00
`
`Chemical Category
`
`1-PROPENE. l.l.3.3,3-PENTAFLUORO-
`
`Page 11 of 20
`
`Page 11 of 20
`
`

`
`
`
`SUPPORTSUPPORT
`
`Page 12 of 20
`
`

`
`.§rEH¢-o:.oo- ‘FM 3?
`
`Dufnnl Haskell Laboratory
`to: Toxtologv and Indusuul Medicine
`Elliot! itoao. P.0. no: so
`Newark. DE lsrt-M050
`
`RECEl‘\’ED‘
`oer: cane
`
`zatafie 22 at-‘.:l= 1:5
`DllPunt Haskell Ltlb0l‘;ll0l'_\'
`
`
`
`=Z|lid6a{mi0002
`
`
`
`Ol3i‘i.i.ddO03/ll333U
`
`
`
`.
`
`‘
`
`;.
`echo-ea-14333
`
`February 21. 2000
`
`Via Federal Express
`
`Document Processing center (7407)
`Attention: 8(e) Coordinator
`Ollice oi Pollmion Prevention and Toxic:
`
`U.'S. Environmental Protection Agency
`
`401 Mstreet SW
`Washington. DC 20460
`
`Dear 8(e) Coordinator:
`
`.
`
`1-Fropene, 1.1 ,3.3.3-pentatluoro-
`_
`Q E S ! an 211
`
`_
`
`This letter is to irrlorm you at additional results lrom an acute inhalation toxicity study conducted
`in rats and previously reported to you in our letter of January 21, 2000 and the results ot a rat
`bone marrow micronucieus assay by inhalation.
`
`Acute Inhalation Toxicity Study
`
`Four groups or 5 male and 5 remale B-week old Crl:CD"(SD)lGS BR rats were exposed nose-
`only to gas atmospheres oi the test material tor a single. 4-hour period. Concentrations tested
`included 500. 2000. 3300: and 4500 ppm. Rats underwent a 14-day recovery period tollowing
`exposure. The lung. liver, and kidneys trom rats in the 500 and 2000 ppm groups were euanfned
`microscopically. An uneaoosed control group oi rats was not used tor comparative purposes.
`
`Compound-related microscopic lmdngs were present in the kidneys 0! male and ternaie rats
`exposed to 500 or 2000 ppm oi the test compound.
`In all 2000 ppm rats found dead within 5
`days lollowing the exposure. kidney lesions were characterized by severe acute necrosis of renal
`tubules. Kidney dtanges in all 500 and 2000 ppm rats that survived the 14-day observation
`period primarily consisted ol regeneration oi renal tubules. The extent or tubular regeneration
`was dose related and tended to be more prominent in male rats compared to lemoles.
`
`Other microscopic linuings that may be rented to compound exposure include the iollowingz
`
`- Acute necrosis and intlammation in the lungs of 1 female rat exposed to 2000 ppm
`-
`Pulmonary hemorrhage in 2 males exposed to 2000 ppm and 1 temale exposed to 500 ppm
`-
`.inflammaIi0rI'a-'Id Iransitionai eel hwerplasia or the renal pelvis in 1 remote exposed to 2000
`PM
`.
`Pertportal latty change in the liver at 1 male and 1 temale exposed to 2000 ppm ,
`
`-
`
`In addition to these findings. microscopic changes suggestive of hypertrophy were present in the
`livers of 500 ppm male rats. However. comparison with a study control group would be necessary to
`definitively diagnose this change.
`
`' 8
`
`588888 142
`
`min Pun!
`in-i-nrv.iI!J
`
`l.l.evvuourn Murreursuutstarr:
`«
`
`Page 13 of 20
`
`Page 13 of 20
`
`

`
`A 04
`
`Rat Bone Marrow Mlcronucieus Assay by Inhalation
`
`Two groups (low and intermediate concentrations) ot 5 male 8-week old Cri:CD"(SD)lGS BR rats
`and 1 group (high concentration) oi 16 male 8-week old CrI:CD"(sD)lG$ E3 rats were erposed
`nose-only to gas atmospheres of the test material tor a single. 6-hour period. concentrations
`were targeted at 300, 600, and 1200 ppm. A concurrent control group or to male rats ol the
`same age was exposed nose-only to ab’ only.
`
`Groups or 5 rats at the 0. 300. and 600 ppm concentrations were sacriliced 24 hours post
`exposure and evaluated tor micronucieated poiychromallc erythrocytes (MNPCEs). The lirst 10
`or 16 animals tram the 1200 ppm group were also sampled 24 hours (5 rats) and 48 hours (5
`rats) alter treatment and evaluated for micronuctei. The remaining 6 rats from this group were
`sacrificed without evaluation.
`in addition. a group of 5 vehicle control rats was sacrtlicod 48 hours
`post exposure and evaluated tor MNPCES.
`
`A statistically significant increase in the trequency ol MNPCEs was observed it rats exposed to
`1200 ppm and sampled 24 hours after treatment. Rats at the highest concentration that were
`sampled 48 hours post exposure did not show a statistically signiiicant elevation in MNPCE
`scores; however. 2 out or 5 rats did respond comparably to positive control rats.
`
`The MNPCE counts tor the 2 lower concentrations were not significantly elevated over the vehicle
`controls: however 2 out oi 5 aninais in each group did respond comparably to positive control
`rats.
`in addition. the Jonckheere test for trends lrom the 0 to the 1200 ppm groups was
`statistically significant at a level or alpha . one
`
`Under these experimental conditions. the ilndings described above appear to be reportable,
`based upon EPA guidance regarding the reportabitity ol such data under TSCA Section 8(e)
`criteria.
`.
`
`Sincerely.
`
`A. Michael Kaplan, Pb.
`Director - Regulatory Affairs
`
`AMI-<lJRB:cp
`(302)368-5260
`
`Page 14 of 20
`
`Page 14 of 20
`
`

`
`CERTIFICATE or AUTHENTICITY
`
`1HlS IS TO CERTIFY mu lho mlctalmagu nppuring on this mluofléjo In uacu-do
`and complain llploducflons of mo (laid: of U.3. Envltonmunul Protection Agency
`
`_ documents no ulmrad In In! nguju cautu cl buulnou lor mlcmmmlna.
`
`My
`
`.30
`
`(Month)
`
`(0-1)
`
`(Y-I0
`
`Page 15 of 20
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`Page 15 of 20
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`

`
`A01
`
`CODING FORMS FOR SRC INDEXING
`
`Microfiche No.
`
`OTS0573989
`
`SEHQ-0400-14638
`
`Submitting Otganiulion
`E I DUPONT DENEMOURS 8!. CO
`
`DUPONT HASKELL LAB
`
`SUPPORT: LETTER FROM DUPONT HASKELL LAB TO USEPA REGARDING
`
`RESULTS OF BACTERIAL REVERSE MUTATION ASSAY CONDUCTEDWITH
`
`I-PROPENE. l,1,3,3.3-PENTAFLUORO-. DATED 04/17/00
`
`1-PROPENE, 1,l,3,3,3-PENTAFLUOR0-
`
`Page 16 of 20
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`Page 16 of 20
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`

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`Page 17 of 20
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`

`
`E’ 3
`-
`'‘'_‘-'-~-----—--———-————.\
`
` DuPont Haskell Laboratory
`
`953914533
`
`April 17. zooo
`Viaf-'eder.tl Express
`
`DuPont Haskell tabntatory
`Ioricxieologv and Industrial Mmcine
`Ethan flood. M. So: 50
`Newark. DE ISIN-M50.
`
`5
`
`7
`
`Document Processing Center (7407)
`Attention: 8(e) Coordinator
`Office of Pollution Prevention and Toxic:
`U. 8. Environmental Protection Agency
`401 M Street sw
`
`Washington.DC204500001
`
`-.
`Dear 8(e) Coordinator.
`
`.
`
`_
`
`C°’.7la1n No GB
`
`]
`
`'-er’-5'1
`
`"’
`
`:-.'. <
`
`'
`
`1-Propene. 1. 1.3.3.3-pentafluorc»
` &___
`
`This letter is to inform you of the results of a bacteria! reverse mutation assay conducted
`with the above referenced test substance.
`
`The test substance was evaluated in the bacterial reverse mutation assay using
`Salmonella typht'nturt'um strains TA97a. TA98. TA 100. TAl535. and Escherichia coli
`strain WP2 uvrA (pKMl0l) in the presence and absence of an exogenous metabolic
`activation system (Aroclor 0-induced rat liver 89).
`
`Tester status were exposed to the test substance at actual mean concenuations of
`approximately 0.08. 0.14. 0.5. 1.1 and 4.8% in the presence and absence of 59.
`Preliminary testing at concentmtions of 15% or greater were cytotoxic to bacteria. Test
`substance-related toxicity. as evidenced by the reduction of the rnicrvocolorzy bakground
`lawn andlor as a concentration-related reduction in the mean number of tevertants per
`plate. was observed with S. ryphinturium strain TA97n in the presence and absence of the
`metabolic activation system at 1.1 and4.8‘ib. Evidence of mutagenicity was detected
`with tester strain TA98 without activation at 0.5% or greater. and with "l'Al53S with
`activation at 4.8%. Both strains exhibited concentration-related increases of the mean
`revennnts per plate compared to their concurrent negative controls. Under the conditions
`of this study. the test substance was concluded to be positive for the induction of
`rnritagenicity in the bacterial reverse mutation test.
`
`
`I rdniunblhuuuutmuan
`
`i
`" lfl
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`Page 18 of 20
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`Page 18 of 20
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`Under these experimental conditions and when viewed in light of the positive resultspf
`an in viva micronucleus assay previously reported to the agency (2/21/00). the findings
`described above appear to be reportable based upon EPA guidance n garding the
`reponability of such data under TSCA Section 8(c) criteria
`
`Sincerely.
`
`6?.
`
`A. Michael Kaplan, Ph.D.
`Director - Regulatory Affairs
`
`AMK/RV:clp
`(302) 366-5260
`
`(4
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`Page 19 of 20
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`Page 19 of 20
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`CERTIFICATE or AUTHENTICITY
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`and complain reproductions 0! Inc ucom at us. Envlronmonul Protccnun Aqua;
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`Page 20 of 20
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