Document N2eOrM4eZdoNx1p2x3V9qV8RR

....... ......... ' ...... | Sorlal to. M-W-mS 04ff lo* / \ JACSSCf pmwmm o h o u p tssMiaa mp q m * < >K Ttfcla i- Batallisoa Pigg&mta- fzm ata*oxym|iifc&olo' aoia K~SS02, JtoUind'** B(M> mmslUmflm I ' g^611 Pe2*aaifeosailiiia * (auasd <%J3awr ldbtlNMi9' PmritaS Ctemtdt -3O"40 to i- Flic:- 222*2 SUM* S-t-48 N42145 Serial Ho* KH-47-47 Copy So. / Copy tot #1 - Humorleal File8 Research file (222,2) 3 Library Pile (888*8) 4 Dr* J, I* Booge, Wilmington 5 Br* W. F. Spengeaan, Sewark 6 Mr* A* Siegel/ Mr* A,A*Brlz*olara,H*k, ? Br* D* B. Killian* Jaokaon Lab** filn* 8 Mr* A* D* Sol dinger* " 8 Mr* J, M* Tinker, ft a 18 y, M* Tinker, 11 18 Impe rial Ob*18* b industries Ltd* 15 14 Extra Oopy JACKSOH LABORATORY I LIMITS GROUP RESEARCH REPORT Title t Metallized Pigments fron Beta-oxy-naphtholc acid K-2502, Aniline * BOH, Miekel Complex K-2511* Paranitroaniline -* BOH* Hiokel (and other amines) Period Coveredt September 50, 1848 September 88,104? Charge* SUBMITTED BY* Cl-236 * * DATE SUBMITTED* 12-11-47 APPROVED BY} '//v/fy DATE ISSUED} 2-9-48 j. DUP050066706 anoiettia> Pigments of excellent lightfastneas hew been obtained at Jackson Laboratory by forming & complex metallic salt of diasotlsed arylamines coupled to beta-oxymaphtbolo acid* 8,8* 2,396,328 <Dtt Pont) covers the preparation of metallic complexes, the first component of which are amines devoid of OE, GGOH, and 3%H groups# The products are red, maroon and brown, the former being Handily somewhat dull compared to the simple metal salts. The nickel com* plexes are usually of better intensity than other metals, euch as copper or cobalt# It was planned to prepare samples of the most promising of the nickel compounds for evaluation and outdoor exposure. mimjmsmmmm* The following samples have been prepared and sent to Hewark for testing# Final results on these products will be available in Exposure Reports and the other Paint Laboratory memoranda referred to below * This pigment is a light brown with a tint of reddish hue considerably duller than the average organic red, Lightfastness of tho sample both in full shads and in sine oxide extension was e xcellent by Fade-O-Meter test# The only modification of the original Jackson Laboratory formula was in heating the seupled dye to 60*0 before isolat* ing, which improved filtration rate and appeared to give increased depth and strength# For complete results refer to Point Laboratory Memo #144 and Exposure Series #7118# A sample of the nickel salt containing 1/8 atom of Hi per mole of dye was also prepared# This is much more intense in m&cstene than the metallic complex but is definitely inferior in ll#itfastness# Seme Interest in the metal salts of this combination has been observed, eg Harmon*s Topes Red (the da salt)- and Calee** Bed Lake R, and' a number of similar' derivatives haw been evaluated at Hewark* - Outdoor durability of KH-103 is being determined# See Exposure Series '7184, , ..... 8* iSaiO PrOfltt^v X0 ft IIUULa maroon with a bluish red tint of fair intensity. Qi* nrasent smmalea Jackson Laboratory offering but DUP050066707 Whieh were of equal Intensity compared to the letter were poorer in fait resistance and Improvement in lightfastness was obtained only by Increasing the heating period from three to eighteen hows with resulting loss of masstone .quality# other details in Bspesure series vii* Although sewswhat deeper in masstone than the aniline salt, this pi nt is"much duller in tint and poorer in lightfastness* A sample being tested for outdoor durability* see Exposure Series Tbs produst obtained with this 'first component was deBoer end more Intense than the fEA counterpart, but was Inferior in light* fastness* There is evidence that the Hi salt was obtained with only partial metallization. Ho sample was prepared far outdoor exposure. The metallised complex is a light brows similar to the aniline derivative* The nickel salt Is mush .mors intense but poorer in li#xtfastness* irthir'-appeared to have any advantage oyer the corresponding product .made from aniline and samples were not prepared for outdoor evaluation* Difficulty was encountered in controlling the process tm this combination. Although the pigment is more intense In mass-tomeew-a bluer in that than the somespending enllifiS complex, it was decided not to do further work until the merits of the latter had been determined* This product is characterized by its deep mad relatively intense masston, MetsL lization does not appear to be collets and llghtfastnsss is consequently .not as good as desired* However, outdoor tests are being mads {Exposure Series #712i)* DUP050066708 Xh all oases, difficulty vac encountered in obtaining con* distent results possibly due to the complex structure of the products In stitch the metal Is presumably combined both as a simple salt with the earboxy group and in coordinate linkage with the .esc gronps In ' the following manner * A limited process study was made particularly in the ease of the paranitroanillne derivative. With this diaso component, coupling to BOH was best carried cut in buffered acid medium. Sodid* carbonate or bicarbonate alkalinity gave lighter, yellower products with poorer lightfastness. Use of HaOE may be possible if excess alkali is neutralized after coaling# The coupled dye was isolated and roslurried since a weaker product with poorer lightfastness was obtained In the one Instance in which a straight thru procedure was tried. Metallization was carried cut with m excess of ammonia by heating at 90c for 3 hours or longer* The FHA * BOH, Hi complex was improved in lightfaatness by an 18 hour .development period but maastone color was duller* With sodium acetate as buffer or cold acceptor formation of the complex did not appear to he complete. The other diaso components * aniline, etc. were coupled with soda ash as alkali* Ho other significant changes were made in the formula for coupling and metallizing the products from tholr amines. .For additional information on this type of pliant refer to Jilt*43*434 * Fast-to-Light Red Pigment ytH*43*443 * Fast-to-Light Maroon Pigment Copies of K-S502 and K-2511, which are representative procedures are attached. DUP050066709 . mf&us * Safer to Notebooks 1B3S, 1256 and 1260, Aniline - Beta oxy naphthoic acid SB 1256, lapis, 7, 11, 1$ m 1266, Bxpts. 5, 16, 25 fans nitre aniline - Beta oxy naphthoio mold MS 1235. Expts. 56.' 60 NmB 1256, 1260, Expfcs* Ixpte, 6, 2, 810, , 14, 11, 20, 16, 26, 22 46, 59, 56 Bara ohlo? ortho nitre aniline Beta oxy naphthoic acid Ml 1259, Sxpts. 10, 12 MS 1235, Expta, 14, 46 Bara chior aniline MB 1256, Expta, 14, 46 Sara ehlor ortho toluldine MS 1260, Expta, 6 Seta Haphtl lamina MB 12 i, Sxpts* 9, 29 \ DUP050066710 fo .pggpaye B/tS/'fl Br?m> famt ifcsylfetl?e of (gt,tligg * BQ8) far ars&l>fcloR . 2*0 r- ?,,. m c? y Xelu I2&0^, A 3 K&p&ASv) '*' Ys I 40 t fOO I aoM '..c.tsr aat8lna<i 1b mi ! ! I l*a&& said 2 flforiyfclo saMi XOQft ' ' J 3182..1 | Bilr IQ^gO Mmitae to dlfteolyg 1 Go?;, to, 3?.af S 'J <':; Oi: ................ r ... I I Yfeasa add la 2-3 siitxt^m I:|^j nitrite* J .d5.&SX'?8&J! ^ j 5* *V3^ i 43 ! 400 ! i,ir ___.......J...,____J.. . iJBtlg.%$*$ ?.;&.wiwfcir*t . !'>y*vff>*,iaii;,,3l?r~ir35<^. llSI..lm& ! %&< CE> KX flliaat ~ . 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T<t` .; . 1>a` iy,-ft'vr.' fifta ; s. a in t '.''? xj .ft'ft'ft:, Tft ftftft ;3 * ;: ,, Ils Manas. ftvis.8 e.sft4 fa cMMaa rf Mar ac-ft-T-l ;fl f%; fafftift"; to tl:-;; ftdsisMI, ^ijCvoa; v :s a--'ij-rL:' 3. a tlto 3'%.? t^:ju,t' '<" Ik * ts ft -o'M'ftdglM ifft'a ).aaaa;::|a;:!4- ftcl'isa m& % a-;:<;i," ; ftctat .: %.% ftftft.sfis 80% in pX&s of % ,.% ?or ift. v|:` % ^Zsjibls wo; fasti 0:1 1% sostft. iMaiM fifsAgifts fftovfft .t.'i-', fift-V'. ;;.r %-'% if tfs A-fta Ivacftftftft c?t iMai'c;;;: % It;-;- 8;K%:U f %'s io tfcrt' f aa fttOft' :%** o itiXiar-ing to f;,l'-i>7:ftica ?,?< . M.-cfa bf. r7% %%!.<,< 'atif lA'fthst :%& %'. ;h ! of Ar,fcffi? wt 'g.:fefesa'.? ffca:a:;a of t-,ft s:k %.-.1 f onfs'ofj r;:%it`:u ol t% crii?as earMaatc s ro; ftftftMaicn > ? Msg Mft" fa X cM.;*- ftftOosMvaftfu f f.atra'lt 'Is 'U. -s' -:.:'vo' *: aft .. : at 4f<> ffi-al otrg* r::.jsi j>n X Xlft '"7 i"J. sf ,:;,'f;, ftftift 0 '; ftft f X %'ftfft, /(a ; K : aftf '.'XX 'fi %;ft,".':j.<.. fr t ?. aa M 3% ;" >, /a's,. f ifts- '} ,<i :.*f a;:;-; sxvv %Q7 t'".v .ft.;.ft*fta% s/ris: ft-, ft'CciaX''I fM i?' /-* 'f "~- ^ ^ .ft., t., rs-ia.ftXsfa"' 1 , DUP050066713 .Isrsssa toms? msarn BC10 K- 2$U DUP050066714 S/3-3/4t ifarotsa xei J?}*'*l3R?\rS0:4 l&eslwyry rergigsg ealc^ ,;jB I 3.2D-C: | ;lofux|.fe0l4 &<M 2?U DUP050066715 it* % iw&l'iz of pesmdLtr<waai'll'3M ** 80$ # rotated i chos&o&X sti'ucte'fc to &(&* It do ee&aMffS'abdj *? sad orA iai^sg dims ites lattoo appro .ciMtig -r, fsrrsoa ia &k&dsfe. JMSSilS iwiffomi tift we^lda proofoslu ros.&i3$r mio tfc pH drops Sx&oW il roeowondod rang* 4.2 * 45* la ss& mis# addition -of & wail wwt of s4a am % tawie. Id b&J&aoo of eisspommi'ii sJatHsid fea ?t ole#* Coupling m iito elk&iAm id (soils o&rbonet cUfcaH) gar liglitss* aad iwa&or preiuate* > $& oouploi d&r* i Of filtration ad ms&iug* to 140*? Iksfore fiXtorlag to iaprCv st iSfAljLIgaTiOg. IssoMtiosi of t!; snaplfes! tiff Ooforo cOarartiog-do tfc uiotol ws^lo* r%ltod la & streamer Kf latr^o jprodaat tfcoa 4xilration of t& ooaplod 0la2>rf Botto* Ii#ifegta*;ss luishledtos* blues? Xor &$ ofctaiijes! Xg? i of wsoai ttea witfe .todirat kcist ssfi eguotl oAeu - iO Slows* dWlt!SKt ^osstoi UBOd la fi^8 fWOfi fXt dotted ?* t& ^raparatiofe of a #.'%Xo for sraXuo&lon oiaoo Uest Xigjhtfaotaeeo mo obtain! nXtiTtho lflgox" p.yiod- If t!* sradwst proTos to bo of lutoraoi^ furtfeor gtudf of oonaltfoao -oo-xXO b jn&ox'tc&oR.c- " TisXa is ths owe^fi of tr ~pri&mta and 'sM.Xo it is raj^owartatlra Emjr not bo o^aaX to & 50a! yi34 * JSEssOO A. S. AfcEDUKBW f/S9/i DUP050066716