Document 4a3omZEX5nMzBK7pZB1gYvmZa

E. I. DU PONT DE NEMOURS & COMPANY KREBS PIGMENTS DEPARTMENT 256 VANDERPOOL STREET NEWARK. NEW JERSEY Serial No. KN-49-6 Copy No. X Numberical, File -Library Title: Period Covered; Charge: NEWARK PLANT PIGMENT COLOR RESEARCH REPORT Final Report REACTIVITY OF RT-551-D, LABORATORY 90% 5-Nitro-2 -Amino-Anisole -* "NaphthaniltM ASD 10$ 5-Nitro-2-Amino-Ani30le BON, Manganese FEBRUARY 1946 to JUNE 1948 A-IC-40 FILE: 221 DATE: 11-9-49 N42190 Swift* Ho, KH-49-6 Copy So* Copy 9os #1 - Huaerloal File , 8 - Reeearok Office (221) S * Ubrow File (801) 4 * t* ChmlupakS. - Fit* Fils 5 - W. F. Spengoman S * 0, B. Killian HffFjjfflK' BLAST PIGISEBT COLOR RESEARCH REPORT Final Report n%10| REACTIVITY OF RT*651*D# LABORATORY 90g 5-Hltro-2-Aisino-Anisole "Haphthimll* ASP 10% S^Hitro-S-Amino-Anisole * BOH* Manganese Period Covered: FEBRUARY 194# to JCHE 194S P.huygft j 4*10*40 Misra Hi A* D, RILLS APPROVED &?f h at e timmim t*m*m 11-9-49 DUP050067151 ZSgBOBPOTIOVl BS-SSl-D(A), K-2292 ($-nltro-2*aaia0-anlaole l^aphthImil,, ASD) it ft durable automotive maroon for use in alkyd systems but lift* severs reactivity and thixotropy upon aging in the can. A study tat undertaken in the laboratory to eliminate, it possible, these imdesirable rheological properties* During the eoorse of tht work aeveral distinct lines were developed, which will* of necessity, have to be reported separately* m this report the several dovelopfr stents rill bo correlated and the general results summarized, there were too lines of thought concerning the approach and both were considered simultaneously, these core variations In the coupling per se (variable study) and a study of the effect of possible impurities such as "LithosOl" Acid BOV, ortho toluidlne, the aoda salt of BOV and V-ASD, idle coupling of S-nltro-2-salno* an1sole * BOP, nifcroaamlne salt and decomposed dless* 1. the adding of the aforementioned possible impurities to Hf-S81-D(A) in 1$ amounts insulted In two leads* One vas the use of Smltro-2-mino-anla ole ** BOB, Manganese and the other de composed diaso* Decomposed di&so gave results equivalent to the BOB aenganeso product but because of the unstable nature of these decomposition products the work on the BOB coupling material (B*6?1D) was stressed* . Warn this latter material was blended u|thR|^81-B(|yn a 10/00 ratio, the reactivity in alkyds was grei . lad to tho dovdopsent of H!T-5S1-D{ D) which ia a blend of BO parts of h t -888-D(b ) (originally RT*551-Dli| }and 10 parts of fffn#0) and is practically non-reactive in 0E*2488* Other amounts of ili BOB, Ha additive, from $ to B$, were used but tbs 10$ snots tho greatest effect without detracting iron tho durability* complete laboratory, seml-raxks and plant developments are in KV-49-6, K8-49-I, and KB-49-10. 2* Modifying the coupling procedure of tho S-nifcro-Bamino-anisole -* VASD by tho usual variables did not reduce the reactivitydMant ilftll* HoweAveAr,mavltkptfrModAu#ct lighStOer/tratvitmfeaoMtonwrially vamc&M 'usas WtHwihftPn^Vija vnnowtpvs* grweens*^njwsrws -aw ss^swwrn . ^n**eawnw ^rvw wpwesaww gyvw* gyneesaSinS' .msnvn. mm ooded K*2411* Vhe work laraffiii to this fcrania will kb: covered: separately in KV-49-11* 3* Various materials, such as natal oxides and and other pigments nado from BOV and laked with manganese, to BT-S51-D(I) but with no significant results* 4* She procedure of eo*eoupllng the BOV and SASD fol" lowed by lakiag with manganese was attempted rad in story case As reactivity was inoreassd* DUP050067152 ftFt*.' And Blent bStOheS RS-588-D tmi 'SBFWW WCea WPSW^WPWe WWffS'^^wae OfbP ^pw ^Bf Ww V aw Rf-SVl-B were evaluated in the laboratory and the resulting nixes Imre submitted to the plant for blending Into RT-SSl-D* fho actual blending of the seal-worka end plant products la covered in KS-49-7 end BSB-49-9. nd; Tialnox* 'reduced the reactivity bet to dittoed ha odor m to be of no practical value* Considerable work on a variable study of Bf-S81-D{A) wee done but notblmg reduced the reactivity within the desired tinctorial rouge* In moat eases tho undeveloped products were superior In re* activity to tho developed but the ooler too light* fhe prosene# of B6S wot believed to be contributing to tho reactivity of ST-8X but aeveral attempts woro mods to dissolve purified *$apht!ianit* ASB at room temperature with the aid of wotting agents hut no change In roaotivity was recorded. Also a coupling was made in an alcohol medium to eliminate oonversion to BOH hut no advantage woo shown* Attempts were made to redueo the roaotivity of l$*hSX*0 by coupling with a deficiency of MSB, coating with sodium methyl sillcolate, treating presseake with toluene and treating slurrtea oeleium roeinato and maeneslum naUhthenate hut none imoroved the reactivity* Regarding the actual blending to prepare B!M&S1t D(B} all the semi-works mad "plant iota of E2^7X-D and Rf'-588*l> {gHBgMj were pre*blende.d in th laboratory and evaluated in alkyd (GE-24S8) for color end viscosity* As those blends constituted plant development of Rf-SSl-D, a separata report will sow this phase* ' B2-688-D* DUP050067153 8f*86d*l> 1* the present oode for the straight "Haphthanil" ooupllng fosaerly Rf-BSlHDfA) BT-871-D (A#S & 0) Rf-571*D always refers to the additive S-nitro-E-aalno-anlsole - BOH, 88gDN* Originally ooded K-2384. Hf**S81HD (BfC & D) - 90/10 blends with RT-SSS-D and R7Hm-D (AtB & C), i Evaluation* were wad# fy> the alkyd vehicle QB**$458 in the followlag proportion** 17 g. Ptwmt (18.5 g. R7-S8S-B 1.5 g R7-871-S) 78 1. m*84m 0 g. onion go Ground 48 hours* @0 g* GS-2488 0 g* Min 50 8*8 oo* K7*0 file experimental reference* for*** (1) the variables covered la detail la this report are** g.B. Preparation of samples believed to be lapuritles* Evaluation of 1197*5. Temperature of Coupling Study. Preparation of deconposed dlaso* Bse of additional oauatlo la coupling. Teauerature of oouulin* variable la K*9948. . Repeat evaluation of 1197*5. Reduction in ate HASD, HaHQOi & volume* Study met of wetting agent* with BASS* Bae purified HASD * Buponol WA* Study pH of coupling *| X-8S9S, , f amount' ofhydrolysi* ^ of RASP* '- >ing developed slurries with RC1. JfaQK & /, SigC{h Variation in temseratmMi of oouollms* Addition of various mangancc*B05 Toners. Ruboufc of Sf*8il*2> vs. Ramon*a Xf*2O0. A*dwditio*n "of M<* M to rl"{l*n acjf SSSh SS S S S S tS S .o ^.o ^c t DUP050067154 K*B* Eatp. Page 1245 a s a B a a 8 Addition of various natal oxides & hydroXldeS. 8 Preparation of large sample of K-8054* 84 Couple K-8898 with a defiolenoy of BASS* 88 Preparation of largo snsple of deconp.dlaso* 88 too of soditm nethyl ailooolate on K-22&2. 49 Bepeat of 1245-34* 8 Repeat of 1848*86 84 freatasmt of pressoake with toluene* 1264 M B W S Coupling in an aloohol nediuau 5 a a a 13 Sval* of exude t-BOg-iSSg-An* 88 Substitution of Bgf BOB* Mono Acid F & R salt for si BASH* 26 Rubout of 1197-22A 8 Bg# 38 Substitution of CacO* for HalOO* & use of ealolun rosinate and magnesium naphthenate. (2) All the work on this problem lnoludlng the dewelopnent of RT-571-D, K*2413 end tho blending of plant lota la covered in the following notebooks* 1197 1248 1264 1308 oomplete complete Bap. #3 Wsf KH*49*7 ~ Plant Blending of 27-831-0* SB-49-8 - KB-49-9 * KB-49-10- HB-49-11- Laboratory Development of K-2413* EB-40-18- Seal-Works bo b # DSH-49-9- Plant Blading of 27*881-D* DUP050067155