Document karZz3rX1Z1d7z5YB82RjDD8B

E. I. DU PONT DE NEMOURS & COMPANY PIGMENTS DEPARTMENT 256 VANDERPOOL STREET NEWARK, NEW JERSEY Copy Ho. * a :a ./- ^-dr~ x o i NEWARK PLANT PIGMENT COLOR RESEARCH REPORT FIML REPOS,? latprevomant of Flow of Lithol and "Duol* Rods Period Covered: buy 22, 1945 *0 Saptesabor 5* 1945 FILE: 222*11 l DATE: November 26, 1945 NJ3699 ^p, / / Soria! 8, 201-45-80 Copy Ho. Oepy to* #1 - Suaerieal File 2 * KesearoL Office (222,11) 3 - Ubnqr File (222.11) 4*- Imperial Chemical Industries* Ltd, n 77 * S. 8 Dawson* Newark- i-u-i * ~ HEWA8K PLAM pmmm c o l o r r e s e a r c h r e p o r t Final Report Title* Xn^roremsnt of Flow of Lithol and `Duel* Beds Period Covered* 5*22-45 to 9*5*45 DAIS ISSUED* ft DUP050150779 In B-44@4, at report vats made of as evaluation of 0*8* Patents 2.|jgBt 520*6 issued to 8herwin-mMaiB* is duns 1544, These cover improveaents Is ink properties of azo pigments and are of special interest is eosneetioa with ' the manufacture of hithol Rede characterized by superior flew* 3s the patents, considerable esphasis .is gives to the use of a resin* waleie anhydride eesdsBcaiioa preduet and the effectiveness of this compound is promoting flew is Lithol hods wets confirmed by the worts covered is the report* la view of tho isprovemenis in Ink properties, resulting from ths adduot, it was deoiled to investigate the use of maleic sold or other organic adds separately fro the rosin, both being is the fora of the sodium salts* Snob a X ess | it is beleivsd, weald set infringe os tho pajMKstft* X It was also proposed to attempt to matoti tfisi of eat stasdard Lithols and *BueW*! with the added property of flow by introducing the reads adduet into our own fwmlas and to figure approximate easts* Wee of naloie aeid in tho fora of its soditaa salt is conjunction with rosin bat sot eembised as is the Sbcrwln-^illiaffia patent example* was sot successful in presuming flow is Litfcol or ""Duel*1 Red inks* It was neesssary to prpare the adduct separately i order to obtain any advantage in ink properties* This wee found to bo the ease both is the type of formula described is the patents asd is oar RT-4&4-D formula* 4 number of organic acids other then maleie were also found to bo without effect when employed in a similar maimer* Modification of the RT-463-B formula by replacing the K Wood Rosin added after development with the rosin-malei anhydride adduet roaalted is products possessing exaellant flow* However, in depth of masetose, finish and etrosgth they resesbled a 0BuolM type rather then a Lithol Hod* Because of the greater solubility of its barium salt, it was necessary to increase the amount of the adduct to equal tho yield of timer obtained with wood rosin* Substitution of the rosin-maleic anhydride combination for the wood rosin used in the development of the toner resulted in weak'unturned* products* By further modification of the RT-463-Q formula* namely by increasing tho amount of Veod Rosin in the development stag# and by addition of rosin adduet after the development it was possible to approximate the depth and strength of WV283-D with definite superiority in flow* 4 product closer tlnotorially and also subtly cheaper was obtained by substituting the RT-283-B alkaline coupling for tho aeid typo employed in the modification of RT-463-D described above* 4s in RT-463-R* it was not possible to replace the rosin in the regular Rf-283-D formula with the rosin-maleie anhydride compound. Complete substi tution resultedin weak undeveloped products while partial (|K*) replacement had DUP050150780 $ only a slight effect on tinctorlel properties tut also gave very little improvement in flee* Flow wee imparted to R1-364-D by replacing the bl&nc fixe and barium resinate added after development by roein-aaleie anhydride condensation produet* In the ease of the calcium tonere, RT-425-8, HT-432-D, and KT-464-D, it was not possible to obtain an improvement in flow without adveree offset on strength* In view of the patent situation in respect to the use of the rosin adduet and the anticipated higher eost ecapered to weed resin, work on tide investi gation wan dieeontinued* It is estimated that ingredients eests for the barium tcnw,e#B283*"Sid RT364-D, in which the rosin-maleic anhydride compound was effective, would be increased by $2*11 and #1*32 respectively per ISO pounds of product* < is indicated above the RT-463-B formula was particularly adopted to treatment since the second addition of resin (about 40$ of the total amount) is made chiefly for the purpose w#id$lfciett end can be replaced by equivalent weights of ether ingredients* The lack of any effect on flew when maleic acid end rosin, as sodium salts, were added separately at this point is due in part to the solubility of the barium maleate formed in the color* Although used in much greater than equiv alent amounts, no precipitation as its Barium salt eeeurfcd probably because of the high temperature and relatively high dilution of the strike volume* The lew yields obtained in separate preparation of barium maleate confirmed this supposition* Similarly, the solubility of other organic adds as their barium salts is sufficient to prevent precipitation* Among these tried were adipic, citric, /tartaric, and bensele acids. A slight improvement in ink body wee effected by precipitation of hansels acid as its aluminum salt which is such lees soluble* However, the improvement is net considered sufficient to be of interest especially in view of the eost of the treatment* The following derivatives of bonsoic aoid were else tried without successsalicylic, anthranilie, o-ehler benzoic, p-isopropyl-benzoic, and e-bcaeoyl* benzoic acids* In addition to these, oxalic, stearic, and linseed oil fatty acids were tried without effect on flew* The solubility of the barium salt of the rosin-maleic anhydride condensation product is also greater than the corresponding resin salt, seeessitatiag an increass of about JfO$ in the amount of adduct used when substituted in the RT-4&3-B formula.Ilth this amount yield was equal to that obtained with resin > and flew was definitely improved* DUP050150781 3- other eeadonaatioa flow wars Petros (jk i*> rssia-sediw polysaifibft stators* . but net found to b* ueefal in preswiing asfeydridt) frisol SOiUsMii oil-seleis anhydride rosins ana also a lit of Isiprni'iKwnt in flaw which can b# obtained by us* of tbs " ' a^duet is of tb* order of 20 yala&s (1 point" 0*1 iaeb) fists mm. r#plarijf mm oa rubout ink* prepared in #X brans- taraisb bat warn also i&sskad a* tbs standard type flaw plat using flew-ws# Sfessrirsd in tbe case of the litfcole and .... r . .... aig thaeddust for nsaia in nan darkeri strong!? and loon ^diMiy then that standard*' ^ Inorwiilwg tits g YiM ln ft* tiis dowl^swn* iff dii# typiSal tteX* was efcfaihed* ' Oenparsd to 8^*283** this .w* more Intents bat in asaaeioaa and dsfiattsi? ysllsw bind* fids diffsrwaoe mi retaead to a considerable metsnt % fallowing 'tbs 8Y-383-B alkaline type nailing, press&are* da stated in tbs esXslsw lith&is an# ^Basle? 4*4 not to tr^itnest as did tbs barium tenors* la tbs eat* of Rt-464-0 and lidd incraasa la flow was*"mw * effected twes*r after*pw** *ws tmrwewa^^wtmn^esewwnTMt* withw aps * thew****wr bat tt-'waa fteesspuited by a i|p> last in treating strength,, tbs ts^fsosat la not seasidsrsd sf psmeiieal interest. MM&4> suffered a lose iii strength without eerreipoiiding inersaas in flaw* Preparation of tba retin-iaaXele anhydride condensation .prodast was- in powdered fora* Is lbs present went tbs otoicfalcaaetrie niu, st eggsmslmtoty 3 parts of rosin and 1 part of saleie anhydride was used* However, in tbs ewaapla of tbs patent a ratio of 6*8*1 is employed* ifea 'ssattsp&i&il seals tbs fasten could probably be tests is a mutiisb kettle. In* grsdisat cost f tbs coopouiHl is calculated to bs $0*10 with a possible total staking east of be*2# tests of than with lap* 548-35- &$-283*b Ss^* 548-4)C RY-364- in wbisb ibis resin is used weald tborsfers bo 25*84 2343 3300 28*78 flew 17 0 13 0 DUP050150782 - 4- 6** Jfotoboak 54d 4 list of experimeate made- is tabulated bl| r *-443-b 548-14 n \i it 29 19 K-2103. to 2*2043* to ebook standard K-2043# toia*nl44e aafepiride ffifiaiifil Ik *maAm& fif yftkii 2-204$ typo {<md Ifaristioa in final pit of formula Use of maleia oa^ritlfo rod* anhydride* naphthenic eeid and sodium sulphate # U 2# at 31 33 34 38 37 548-20 30 32 35 Cittit* taftefttc* beuaolc acids used in after treataoa* linseed fatty aside* trine! @0 * * * * Barleatimta of banstie wwin ** ** See of thdr metallic salto to precipitate roaia adduct* Alee fstesw* cwiftitifr* itiff* fftffffftfr acids Increase in nn*m* *y bowtote ooid Increase in amount of ftires Styrene* laden and ethylene isaleie anhydride resin. Also roain- eodiua polypulfit mixture* RT-283-S 2*9595# ftfeleie adfcydrid roaia adduct end sodium molest ro* placing X Wood Roaia laereaa K toed Roaia in 170. formula to mtcb Rt-283-B Continuation of 548-40 170 formula modified by uae of alkaline coupling ana Buola 548-3 41 39 40 42 23 25 RT-4&WD Haleie anhydride-rosin aad maleic anhydride iwphtheaic acid addaoto replacing para soap end naphthenic sold* RT-464- addition of M*A* rosin addaet to strews Rf-464*0 RW-425-&* Substitute roaia oddaot fear K-Weed Roaia Rf-364-B. Substitute rosin adduet far blane-fixe sad barium roeiaata Rf-432-S* Substitute roaia oddaot for 1 Wood Roaia# Also add ia after treatment# U.S. 2,350*520 example* Separate additii of sodium molests end sodium rooiaato Reeheefc 548-2$ DUP050150783