Document RzX0nZgjowRQdVMwOOgK7vYB
FILE NAME: DuPont (DUP)
DATE: 1952
DOC#: DUP163
DOCUMENT DESCRIPTION: Journal Article - Cancerogenic Effect of Synthetic Films - Translated from German
Z. N a tu rfo rs c h 7 b ,n o .6: 353-6 (1952)
j . L. B r i l l , Film T ech n ical Li rary -6
TRANSLATION
CANCERQGENIC EFFECT OF SYNTHETIC TIMS. Hermann D ru ck rey and S i e t r i c h Schmaen
1. In conformance w ith Oppenheimer i t has been determ ined th a t
film s from rgnrted c e llu lo s e in ra ts .
are
cancerogenic
when im p lan ted
2. Crushed g lass wool d id not produce any cancer in co n tro l S e
3. Films ex tra cte d w ith b o ilin g benzene and pure film s of reg en erated c e llu lo se produced w ithout any ad d itio n had the same can cero g en ic e f f e c t as th e com m ercial p r o d u c t.'
L. The o b serv ed c a n c e ro g e n ic e f f e c t o f th e film s i s comp ared ^w ith th e e f f e c t of p o ly m eric s i l i c a t e s which p ro -
^b a ffe c t o f asbestos causing cancer, of b ifu n c tio n a l m ethylene diam ides, ethyleneim ines, epoxides fh ar* ^1 as N-m ustard-gas compounds, and re la te d to the fa c t ' th a t fu n c tio n a lly im portant c e ll p ro tein s are crosslinked w ith the lin e a r m acrom olecules by re sid u a l valences (hydrogen bonds) and are changed in t h i s way.
5. The c an c ero g en ic a c t i v i t y o f polyam ide film s to be e x p e c te d a c c o rd in g to th e ab o v e, i s d e term in e d on r a t s .
-he .iHr. f
^ ^ a t i n g - P l a t a l e t s of the p la stic "bakelite" under t s * Tl*r n r T l; o b se rv e d t h e l o c a l fo rm a tio n o f sarcom as
k
**a ;*on "
xan,i,ned, w h e th e r a ls o o th e r p l a s t i c s have
-if t h f e r_ Pro d u c in 8 e f f e c t . We a l l b r i e f l y r e p o r t about th e r e s u l t s
of 281 i S s rim en tS b8gUn ln 1949 ' WhlCh W*r e ca^ r ie d out on a t o t a l
, ,, ? 8VSa l sma11 di3C3 o f
aia o f P fen n in g o f com-
f l i a o f re g e n e ra te d c e llu lo s e (h y d ro c e llu lo se / were im-
u? d 8 rJ j h $ k in r t h ab d o m in al c a v ity o f r a t s o f our in -
SDk* ^
in which s in c e 1937 never spontaneous
o b s8 rv d * A t o t a l o f 13 o f th e 50 r a t s which liv e d
monger th a n one year developed lo c a l sarcomas** (F ig . 1 -3 * ),
B efo re us Oppenheim er ( 2 ) , who a ls o o bserved sarcom as on
`J o ? . *2? in P^a ^ t a t i o n o f c e l l u l o s e f i l m s , o b ta in e d th e same r e
s u l t s . H is r e s u l t s , ab o u t which we o n ly le a rn e d about 2 y e a rs ago
agree w ith ours in a ll p o in ts.
6 '
DUP 11-41940
w ith i t r I n o ta x f e r " ? r ? diiCir`S 8 ff8 C t o f th e c e ll u lo s e f i l a proved
I r
cannot be r e l a t e d to c o n ta m in a tio n s o r a d d itio n s since
we fo u n a e x t r a c t s , which were p ro duced from th e film s witfj b o i l ' - -
e x t - l c t i d nw ith h b* c a n c e ro Snic e f f e c t i v e . Whereas film s p re v io u s ly
ii nS ittiiaa l maattieriiaall anndd n?thhe2r f?i?l mt gsa,t8 dwmccah? Cw8rere(Fmiga*n uZf)a>ctuthreed dar oaer tahs i sth e 7
?hu03t h r0 r 8 S8 n e r a ta d c e l i u i o s e w ith o u t any a d d itio n iF ig . 3)
f e K S f r 1"*
h*s its
- *
cavitia1a3 t?hS . i 5 ;
iHFirf/* r1}r* pT ?helurca,dta-. inin whose abdominal
a B a l i S. 5 t a i avW8r iP*nted, usu ally showed numerous
S jS h a ^ S u aS llv
1 ?t 8:
r 2
Pf
* ^
)* d 3).
S* On
p l4 ?8 wh#r8 d isse c tio n , the
tha P la te le ts p latelets
r , s t d f r * ly in th e abdom inal c a v ity an even a f t e r 15
a Sc t iv it yt ^ oyf thh e 0fil?m sunmehusnt b!de - g rAe actc.ordTinog etxoc itthe a ct ,antcheer Xi tn X r o L mtZc a t
s h o r t h*
c o n tact is s u f f ic ie n t, which is considerably ^
sh o rte r than th e la te n t period u n til th e appearance of the grow ths.
o b serv ed a ? f ! ? ? ,1S8 ** Which coam inuted f i l a s had been f e d , we
s s r T ip H S :
inro
wjn t f l - i t e 3 t s in which we im p la n te d crushed g la s s wool
in to th e abdom inal c a v ity o f 12 r a t s , p ro duced no Sow tH ThS
m e c h X i l a l ^ f r t a t n g S e S . ? r i " # Ilta l 83cP8ri8nC 8S t h c h r o n ic a l,
canceroaenie
8 not cancaro g e n ic . Thus, th e
o f th e f i ? 8 ff e c t of th e f i l " 3 must be r e la te d to th e su ista n c e
are9 iliinnks oMd T- nttJo i a * m i ic.e llSa r 0bhoSnid5 Cbyl 8 rsec o n d avrya lavnal?t8m cceh afinoar c eosf cwe lhlousloo s e o rie n ta tio n v a rie s and is not defined. tX f i ^ X e l f X a e r
K X * . Ut f ? h % * b0dy f UidS 13 a la o a t inc one e iv a b le ? 1 *At
f r ! . SUh*
*ha f l l a a ; on t h * o th e r h an d , lin k a g e fo r c e s a re
f o r exam ple, dyes may be s tr o n g ly bound. The f a c t
in flu o re s c e n t su b sta n c es cannot be washed from th e film s is
fi a" ? oXe
f#atU re f r hyd ro C 8 llu lo ae film s from
in s u i t a b l ^ S S * ^ ain u at8 8 th a t a i so lin e a r c e ll p ro te in s , which
tthn ee
s w Xo lle n
ff iil lm
s
u
r
f
a
c
e
,C
m 8ay
i
b"
te 0
v
ee
rfyf
i
fci
ri
me nl
y t
l
yb oucnl od
s
e b
v
c
tohne t
a
ct w ith linear
a n t ^ t h e t ^ ^ t h - t 0** ayn t jj8 t l c r e s i n s , f o r example by hydrogen bonds
ee ffffee cc tteedd . 1 A lso s*p?l?it.ti?n*g cao5f$f 8or 5fuain divgiednuearla tmioonleocfu ltehse ocf etlhl se issyn-
DUP 1M 1941
- d-
th e tic su b stan ces lin k e d to a c s l l p ro te in from th e su rfa ce seems ^e in "clo n nae:c!t?io n" ewr >ithu ni .t .0 i th e a = 'iv e 3Ur- ace would s im u lta n e o u s ly
Numerous o b s e r v a tio n s made r e c e n tly speak in fa v o r of such a mecnanism. E a rle (4) found on tis s u e c u ltu re s which were
c u ltiv a te d or. h y d r o c e llu lo s e f il m s , in v i t r o a "sp o n tan e o u s" can cellatio n o. norm al c e l l s which was proved by r e tr a n s p la n tin g th e
o
f
anl f ? } S ' ia s " e
A ciordlnj
Jf^in g o
ofoSSSI??*1" , 2 i n ? . o u ra . " k e li v e i t p o s s ib le t h a t t h . o b serv ea
film |r a t i n al3 in th lS caa oust be attp ib u ted to the sy nthetic
...
A s im ila r e f f e c tiv e mechanism must be assumed f o r th e
p ro d !?C8 " s i l i c o s i s " ( 5 ) . Monomeric and amorphous 3 i l i c a * 83 d not produce any s i l i c o s i s , w hereas c r y s ta ll in e
in
t h ? e i a s t m and tb e mope so , th e h ig h e r th e o r ie n ta tio n
The c h a rS d e sig n ( "L ad u n g sm u ster") o f th e
s u rp ris in g ly ag rees w ith th a t in co llag en . Also in
I t r h l' ? - 3wassumed as p ro b a b le t h a t c e l l p r o te in s a re bound a t th e su rfa ce by lin e a r polym eric s i l i c a t e m olecules and th a t
th e a g g re g a te s form ed may s p l i t o f f , th e a c ti v e s u rfa c e b ein g
?l tfyv 1noffr ?thee nseurar^fa8cde la y` e r sIn o f q uma retazn ptiamr et ic lteh se wr ealsa pt irvoevel yd g(6ooad). s o l u b i l -
solut^an v3 l l i c i c acid i n , th e body f lu id s in i t s e l f speaks for a s o lu tio n , .h e q u a rtz p a r t i c l e s may p a ss from c e l l to c e l l and
change th e l a t t e r , w ith o u t lo s in g t h e i r a c t i v i t y (W. G iese,
n h ^ a ^ ? r d ir *f1t J a e g e r (5)). The " s i l i c o s i s " - p r o d u c i n g e f f e c t pharm acdogically agrees w ith the cancer-producing e ffect in th at
ooSnllyv d^ encadi e- sreVa 2f tre3rlb Ieex paonsdu rae r. e M n ii* * te d in man and cause d e a th ,' o fte n
?n a3b stos, which lik e w ise i s in so lu b le in th e body and o f b a a t in oen 43 w e ll as e x p e rim e n ta lly in an im als p ro per f5ir^8rCan?8r' T fiud anoth8r example f o r th e can cero g en ic a c tiv ity of polym eric substai ces of lin e a r macromolecules.
A ccording t o most r e c e n t e x am in atio n s, th e same e f f e c tiv e mechanism has become p ro b ab le a ls o fo r fo u r o th e r c la s s e s of sub s ta n c e s , whicn have a " ra d io o im e tic " e f f e c t on c e l l s , and which are
X1Cv.a ? wel1 aa m uta8 n ic and c a n c e ro g e n ic , i . e . m ethylene ^ ? . d5 th y le n e im in e , ep o x id e and th e n itro g e n -m u s ta rd -g a s compounds which may be cnanged in v iv o in to e th y le n e im in e s or ep o x id es (T able :
Some s u b s ta n c e s o f t h i s kind were u sed in Germany f o r a ^o r f in is h in g t e x t i l e s . They produced permanent
changes in c ellu lo se or p ro te in fib e rs , i .e . due to the fa c t th a t tney are bound by re s id u a l valences alongside th e fib e rs or produce
ro as lin k a g e s With th e se su b sta n c es, in v itr o a lso changes are observed in n u c le ic a c id s ( 9 ) . When t&ey a c t on d iv id in g c e l l s , tn e y produce obvious a b n o rm a litie s on chromosomes (10) which c o rreepond to those a f te r ra d ia tio n e ffe c t ("radiooim etric e ffe c t" ).
DUP 1141942
Table 1. M ethylene amide:
C ancerogenic su b stan ces (according to Henary (14
hoh2c m r nh : h2oh
Ethyleneim ine:
H2 ^ ^ ch2
NR Epoxide:
0 N -m ustard-gas compounds:
^ ch2 ch2 c i ^C H 2 CH2C1
VHpC - CH2
/\ R CH2 CH2C1
/ ch2 . CH2C1 \ c^ h2
. ,, ,, . j .,, B ifu n c tio n a l m o lecu les, i . e . th e b is-o eth y len e-am id es, bisepoxides, b is-e th y le n eim in es and b i s - ( c h lo ro e th y l)-a lk y l-am in e s (11)
sp ecially cancerogenic e ffe c t. In v itro , these substances probably give ra d ic a ls , in any case, they re a d ily fora lin e a r poly-
,, . . The c y to to x ic , m utagenic and obviously stro n g cancero genic e ffe c t of th is kind of substances is re la te d to the fa c t th a t th e monomers in th e body form l i n e a r p o ly m ers, which th e n , as in
v itr o has been obeerved w ith c e llu lo s e , p ro te in s and n u cleic acids
a re c ro ss-lin k e d or a re lo n g itu d in a lly bound w ith fu n c tio n a lly im portant p ro te in s o r n u c le o p ro te in s o f th e c e ll , which po ssess
d u p lic a tin g " p r o p e r tie s , and in t h i s way i r r e v e r s ib ly change or Diock them (1 1 ;. That such p o ly m e riz a tio n s can a c tu a lly ta k e p lace m th e body, i . e . a lso such which in v itr o only take p lace w ith
y ?t a * w*a r# c # n t^7 p ro v ed by th e example o f th e a c r y l i c amide * b a s ic s u b s ta n c e f o r im p o rta n t p l a s t i c s . So f a r a c r y lic
am ide h as n o t been examined a s t o i t s c a n c e ro g e n ic e f f e c t . The sim p le st cancerogenic su b stan ce from t h i s s e r ie s is th e b u tad ien ediepoxide (13) ( I ) .
V CH2 - CH
/ \ CH - CH2
DUP 1M l 943
- 5-
shooww ad-3j--ana cnesc eo/i c jf. yT ^t or S7V.5 iA' i Tbeitw e*ecnt i vt h; e " at"om* c.aanaholfn t hn.fs e s e r i e s b rid g e r in g s , which c o rre sp o n d to th o s e betw een th e Pn u rin **31nS pyrim idine n u c le i in n u c le ic a c id s ( U K t a w t h S k Snr
so, also substances w ith d ev iatin g distances are s t i l '
'i v n r - r i a p S S i U - M o 'f o ^ ^ i r 6" " 0"
E w J d fTM
S g S K ^ j i M ? fS S t-"L S ? I S S 2 i 1y s s i S ^ z l i r ?Xi ~ e T l nS . ? S L *
f ^ e 'r L I d ^ i v U raira'
example th e ir lin e a r d ista n c e from each o th e r in th e polym ers.
. . Hendry and c o lla b o ra to rs d isc u ss such an e ffe c tiv a
. " Anes, which d e fin e t h e i r cancerogenic a c tiv ity in
tZhZ eCi rt ws ubosst tMa n?tiiJyi ?i t?/" ii . ee .t h t!hh Pe irr0 pcaarpt ia2b?iil?i tfy8dyt o#^be w"hdicihr e c*ttlivp"S labesorb
p o r t L t ^ ? r oh=i i : S S ? ,, ` f i h ' rS <l` ) v Such v ie w p o in ts r a t i b^ S
th . S i
P ^foacology, because the esse n tial functionaries -
"5Spli^itiS|"aprSpS?lyfb0V" l U tnS U n " r "" crotolscule^with""
g y ^ S e li^ S iS 'S E S s h t M r * M
to i t s cancerogenic e ffe c t, i .e . e-caprolactam f il m s ( I I ) . '
H H- He
He
X a ^ V ' " X c / X a ^ C\ i / V C\ c /
H 0
Hj H2 H2 H H2
S tru ctu re of e-caprolactam polym er.
Planted im tV iiS " ^ ^ !
f j r a f * A n t ^ i o vs ^
aSnaT v eEry mLa liEg n aSn t 1s. a*rc1o"m- as, whichf w ere d'i'st r"i biui tne di r iorvaeir r ton ep ^e inlfi-iep^l e
o01fd ?c Se lilluS lioo 8s ee aff iillmi isi i afAndd4 saeJe`ms Ttio b! ef f aecvet n cgo rrreeastpeorn dthsa ne ntthiar et l yonteo. t h a t
i-har 1-w. Handry (11) r e p o r t s in a supplem ent to h is l a s t a r t i c l e i i n i ? i \ capror -atfayleneiffline i 111) c lo se ly re la te d to t h ? e - '
P0**" *' *s s tr o n g ly c a n c e ro g e n ic . O r ie n ta tio n e x p e r i-
f I b r i c ^ i 5 fr?! 0?n e! gMa ti^v5e aisio%f at ,rX, tai ilt!hwo'u ghicthh ea s oOb srelorvn .a tinoynlontimaen dw^aesr l o n
i i B? , t S V f 1" ?* f f " * f , b r i d i f f . r o n ly in t h . i r C ap ro y l-eth v len eim in ec^ " ic4 ^ ^ from t h . corresponding film s, it
2 HC
/
H2 h 2
w. H-
DUP 1 M 1 9 4 4
- 6-
must be assumed as p o s s ib le th a t a lso th e m echanical in jury of th e
=e l l 3 by th e sh&rp edge o f th e f ilm p la y s a p a r t in i t s c a r 'e r o z e r ' -
e f f e c t and p o s s ib ly I n i t i a t e s i t . By i t s . 1 T , however t b f
5
c h ro n ic a l m e ch a n ic al i r r i t a t i o n c an n o t p ro d u ce c an c e r as was proved ag ain by th e n e g a tiv e r e s u l t s from our c o n tro l te s t s in wna.ch c ru sh ed g l a s s wool had been im p la n te d . T h e re fo re th
th S ta n i a }'
tb e
be th e e s s e n tia l f a c to r . Thus
th e mechanism o f t h i s c a n c e ro g e n ic e f f e c t o f l i n e a r polym ers may '
t0 t ^i a t t d i n f e c t i o n w ith R ous-sarcom a v ir u s which
mayebe3exam lned3 e x p e r im e n ta ily . C 8l~3 ( 1 8 ) `
-- < 4 P-blem s
oolvBa^ ,
he p re se n t fin d in g s , i t must be requested th a t
polym eric s y n th e tic su b stan ces must be used as p la s tic masses
th _rou*h e x a m in a tio n in endurance t e s t s on
hoe1^utsieHd 'ffro, Tr htrhh ?i sl a Sp ut ircpso swe .hicil 32,8 found t o be can c e ro g en ic must no t
.
Supplement by th e c o rresp o n d en t: R ecently Oppenheimer and
t ^ a t ?rS
r e p o r te d about f u r t h e r f in d in g s w ith p l a s t i c s on
r a ts and m ice. Genuine cellophane film s produced in about 36# of
the cases sarcomas film s p rev io u sly e x tracted with alcohol even
. * t he ther hand, th e a lc o h o l e x t r a c t was i n e f f e c t i v e , c o n tro l t e s t s , in which g la ss p la t e l e t s or co tto n were im planted
V in v l r h ? f t^ f % ? ? nC 8r* Th8Se r e s u lts are in conformance w ith o u rs. r id 8 f i l a s we re ab o u t as e f f e c t i v e a s c ello p h a n e f il m s ,
. lB e f i l a s , on th e o th e r h an d , d i s t i n c t l y w eaker (1 3 # ), as had to be expected according to th e conceptions developed about tne im portance of groups capable of binding bridges fo r the a c tiv ity .
N o tes.
* Fif- 1-3, see Table ( ille g ib le ) .
. i t u h i s t l f i c a l d ia g n o s is we a re g r a t e f u l to P ro f. H. Ham-
p e r l . M arburg, and D r. W. A ltm ann, F r e ib u r g .
1 . F. C. T u rn e r, J . n a t . C ancer I n s t . 2 , 81 (1 9 4 1 ).
2
The work was made p o s s ib le by th e D eutsche F o rschungsgem einschaft. a . S. Oppenheimer T. E. Oppenheimer and A, ? . S to u t, T ran sa ct.
J J VX7^0) e P h y a ic ia n a 1943, 343; P ro c . S oc. exp. B io i. Med: 87, 3 . G. Sandor 2 . an g ev . Chem. 42, 1108 (1 9 3 7 ). 4 . K. K. S a n fo rd W. R. E a r le , E. S h e lto n , E . L. S c h i l l i n g . E. M.
351^*1950)^*
and
ec^
C an c e rln st. 11,
5 R Jagsr, E o l l o i d - z . 119, 165 (1 9 5 0 ). R eport on S ilik o se -T a g u n g in
M unster, O ctober 19, 1949. "C o llo id al chemical view points in th e d u s t-lu n g re s e a rc h " in J o e tte n -G a e rtn e r: The d u st-lu n g d e se a se s. D arm stadt, 1950. " Staublungenforschung und Gewerbe h y g ie n e " , com piled by K. W. J o e t t e n , B u n d e s a r b e its b la tt 1951, no.
DUP 1M l 945
- 7-
6 . R. J a e g e r, R e c ip ro c a l a c tio n s betw een q u a rtz and o rz a n 's m
L e c tu re Bochum 1951, p u b lis h e d in : B e itra e g e S ilik o te f o r a c h * .
No. 1 5. Bochum 1952.
.
'
.6 a* R itc h ie , N at0ucrecu ?(LT*oMnddonV) N16, 296, 5|3?s^ 7(*19?5*2)B. * Dempster and P. d'.
7 . H. W. W edler, D ts c h . med. W schr. 6 9 , 575 (1 9 4 3 ). 8 M. Nordmann and A. S o rg e, 2. K re b sfo rs c h g . 51. 168 (1941);
W. C. Hueper " O c c u p a tio n a l and e n v iro n m e n ta l c an c e r" P u b l.
H ealth Rep. 1948. 209.
*
9.
BS;iochem. J . 2 ,* 3 0 8 1948. D- Jo rd " ,n d " F- Tay i ' .
10 R. J . G o ld a c re , A. L o v e le ss and W. C. J . R oas, N ature (London)
163. 667 1949.
*
4 1 . F. S. P h i l l i p s J . P h arm aco l, e x p . T h e ra p e u t, 99,281 1950. J . A.
Hendry, . . L. n o se and A. L. W alpole, B r i t . J , P&armacolT Chemotherapy 6 , 201 1951: J . A. H endry, F . L. R ose, A. L. Wal-
3 5 7 1 9 1 R* F * Homer S r i t * P h arm aco l. Chemotherapy 6, 235,
12. G. W ilke, N a tu rw is s . 388, 532 (1 9 5 1 ).
13. J . A. Henary and c o l l a b o r a t o r s , l o c . c i t . (1 1 ).
i* D ixon ,G* M* C h ris to p h e r and D. L. S a lle y , P aper Trade
ic u n 7 * f 55 (1948) 5 J * A* Hendry and c o l l a b o r a t o r s , l o c . c i t . (11),
15 n . D ruckrey, D. Schmaehl and P. D anneberg. N atu rw iss. 39 (1952)
being p rin te d .
'
'
16. Th. V ik k e r s ta f f "The p h y s ic a l c h e m istry o f dyeing" O liv e r it Boyd, London 1950.
17. H. S ta u d in g e r, "M akrom olekulare Chemie und B io lo g ie " Weof
Basel 1947.
'
18. D oerr, B le y e rt and Schm idt, 2. K rebsforschg. 36, 256 (1932). *Fig. 4, see Table P. 353a.
I** Bl,i^l M itte ilu n g and B. S. O ppenheim er, T. Oppenheimer and A. ? . S to u t , P r o c . Soc. ex p . B io l. Med. 79, 366 (1 9 5 2 ).
T rans1:
Technical Library K a r ita s M. B lu m s/ssc December 2 , 1954
DUP 1141946
- 76. RL.e cJtauereg eBr,ichRuemc i1p9ro51c,a l paucbtliios hnesd beintw: eeBne iqtruaaergtze oanidlikoorsgeafnoirsst
6 a . ^ j " h n g f " c i p ; 2Med. 4 . 2 6
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7 . H ^ W ^ W e d le r^ D ta c h S d . V icto r. 69 , 575
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8 . M. Nordmann and A. S o rg e, Z. K re b sfo rs c h g . 51, J W, C. Hueper " O c c u p a tio n a l and e n v iro n m e n ta l c an c e r , r
9. Da ThE S r e 7 2S r , M ?G illan d , D. 0 . Jo rd a n and H. F. W. Ta
10 R ^ j b S i d i r i 'A?0 L o T e llis and W. C. J . R oas, N ature (I*n
1 1. 1rF6.' 3k5, . 6"6Pp7hh ii1ll9li ii4po9ss. J . P h arm aco l, e x p . T h e ra p e u t. 99.281 150 H ^ y F. L 03; and A. L. W alpole, B r i t . J . P f i m c S T Chemot i e r an y 6 201 1951: J . A. H endry, F . L. R ose, A. L. p S i f l n f S ! F . ' H0 . r r i r i t . J. P h arm aco l. ch.mother.py 6,
12. ii r 1r J
N a tu rw ia s. 388, 532 (1 6 5 1 ). a Hendrv and c o l l a b o r a t o r s , l o c . c i t . IAj u . K* DiSon G. L. M. C h ris to p h e r and D. L. S a lle y , Paper
* j ! 127 455 ( l9 4 8 ) ; J . A. Hendry and c o lla b o r a t o r s , lo c .c * .
15. H. D ru ck rey , D. Schmaehi and P. D anneberg, N aturw xss. 39
16. T h ^ v f k k e r s t a f f , "The p h y s ic a l chem istry of dyeing" O live:
17. H ? ^ S ta u d in g e r, "M akrom olekulare Chemie and B io lo g ie " , Wep*
18. D o e rr, ^ B le y e rt and Schm idt, Z. K re b sfo rsch g . 36, 256 (193-
19.
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Technical Library K a r ita s M. B lum s/ssc December 2 , 1954
DUP I H