Document dYMKJVRjkrBBVGgp6Oxn3peQ9

E. I. DU PONT DE NEMOURS & COMPANY KREBS PIGMENTS DEPARTMENT 256 VANDERPOOL STREET NEWARK, NEW JERSEY Serial No. KK-45-X3 Copy No. i Numerical Pile j 1? OPY NEWARK PLANT PIGMENT COLOR RESEARCH REPORT Floal Report PTHSA--y BH PRIOR ART SEARCH Period Covered: JASHJAKX 1$ 1$45 - FEBRUARY 28* 1945 ' DATE: 150 3/14/45 NJQeaa N37975 Serial So. KN-45-13 Copy Ho 1 Copy tot #1 - Numerical File 2 - Research Office (150) 3 - Library File (150) 4 - Imperial Chemical Industries. Ltd. 5 ? - D. U Pawson/E.R.Allen - Hewark, 8 - Extra 9#" 10 - fl (I 1 -vt- NEWARK PLANT PIGMENT COLOR RESEARCH REPORT Final Report PTMSA -----* BN PRIOR ART SEARCH JANUARY 1, 1945 - FEBRUARY 28, 1945. SUBMITTED BYi D. B. Killian APPROVED BY: H. Cooper DATE SUBMITTED* 2/28/45 DATE ISSUED* 3/14/45 DU P050149993 mmasassuk The various Isomeric toluidine sulfonic acids have been known for many years. A number of azo combinations derived from these amines have been in commerce for the fast half century or longer. Perhaps the best known of these are Orange R (I.C.jpl6l), o-toluidine-p-sulfonie acid coupled to beta naphthol and Lithol Rublne (Z.O.fldS)t para-toluidin meta sulfonic acid coupled to beta-oxy-naphtholc acid. Recently a process has been developed at Newark for pre paration of a red pigment based on the azo dye derived from p-toluidlne-a-sulfonic acid and beta-naphthol (PTNSA--7 BN), tlnctorially similar to the well known Lake Red C colors. The usual aso coupling procedures (e.g* the methods used for prepara tion of Lithol Reds, such as RI-364-D or RT-283-D) applied to this combination invariably result in orgnge pigments similar tinotortally to the well known Persian Orange (sulfanllic acid --^beta-naphthol). Until reeentlyf the PTMSA------^ BN combinations had been considered at Hewark to be Inherently orange in shade* Since PTMSA Is one of the cheapest first components available for aso pigment preparation, and since the new PTMSA --^ BH color appears to have Ink properties very close to those of the Lake Red C pigments, this product is of definite interest as a relatively cheap red in the price range of Lithol Rads. The specific combina tion of most value is the barium pigment, rosinated or unroslnated. A prior art search has been made In the general and patent literature covering the PTMSA --> BH azo combination from the years 1880-1943, inclusive. 1. Schultz, Farbstoff - Tabellsn, 7th Ed. 2. Society of Dyers & Colourists Colour Index, F.M.Rows, 1st Ed. 1924 3. Belistin - Prager - Jacobsen, Organische Chemie, 4th Ed. (through 1920). ,, System Nos. 2120, 2153, 2202 4. frledlander, Fortschritte der Teerfarben Fabrlkation, 1877-1940 o-amlno sulfonsaure p-amido azo toluol sulfonsaure p-toluidine sulfonsaure (o, and m) beta naphthol 5. Chemisches Zentrallblat (a) Sachs Register * 1897-1939 amino toluol sulfonsaure Toluol sulfonsaure azo naphthol Farblacke (b) Formula Indexes* 1922-1939 C7H9O3K VwW DUP050149994 V fw ;> y>', -2- 6* Chemical Abstracts, 1907-1943 4-amino toluene-3-sulfonic acid l-methyl~4-amino~benzene-3-3ulfonic acid 4-amlm-l-mathyl-benzem-3-8ulfonlc acid 4-aethyl-anlllne-2-sulfonic acid l-aralno-4-methyl-benzene-2-3ulfonic acid para -toluidine -mate *eulfonlc acid bata naphthol 7* Hewark Patent Folders 631 631.131(a) 631.131(aa) 631*131(01) 631.13KCA) 641 641.0 641.00 641.02 641.1 641.10 641.122 651.4 653.14 3. Jackson Laboratory Patent Referencess p-toluidine-3-sulfonic acid. 4-amino-toluene-3-sulfonic acid Ho disclosure of the PTMSA --^ BH azo combination has been found. s u mmar y as p gmmamL 1. The azo combination derived from dlazotlzed paratoluidine-meta-sulfonie acid (4-amlno-toluene-3-sulfonio acid) coupled with beta-naphthol has not been disclosed In the literature. 2. A process has been developed at Newark for the preparation of the barium pigment of PTMSA --* BH as a red color similar tinctortally to Lake Red C pigments. This new pigment Is of Interest as a relatively cheap red In the cost range of Llthol reds, and better than the latter In ink properties* 3. To the best of our knowledge, no PTMSA ^ BH pigment has ever been marketed in this country. 4, The PTMSA--"9 BH combination appears patentable as a new form of matter, and also the process for preparation of its pre cipitated alkaline, alkaline earth, and heavy metal pigments. DUP050149995