Патент USA US2106551код для вставки
Jan‘, 25, 1938} R. L. JENKINS 2,106,551 4-AMINODIPHENYL COMPOUNDS v Filed Jan. 24, 1955 I50 7 T _ \ / MOL RHTlO~l-'l \ -' 12o // HO 9 / E6 I00 / ‘ v 90 I?! m 80 \ / / V _ / FREEZING POINT DIAGRAM A-4~AM|N0 DIPHENYL E L“ \ ‘ (1. w \\ ’ 6 ~' ?-NAPHTHOL. 70 60/ 5o 0 A 10 Z0 50 40 5o 60 70 80 so WEIGHT PERCENT OF E) 100 vE» IINVENTOR RLJENKINS Y W 5”“ TORNEY‘ Patented Jan. 25, 1938 2,106,551 UNITED STATES PATENT OFFICE 2,106,551 4-AMINODIPHENYL COMPOUNDS Russell L. Jenkins, Anniston, Ala., assignor, by mesne assignments, to Monsanto Chemical Company, a corporation of Delaware Application January 24, 1935, Serial No. 3,265 2 Claims. (Cl. 260-1305) This invention comprises a molecular com stituent compounds thereof. This fact affords a ready means for removing from solution either one of the constituent compounds by the addition of a solution containing the requisite quantity of pound of 4-aminodiphenyl and beta-naphthol. One object of this invention is to provide a new compound of 4-aminodiphenyl and beta-naphthol 5 which is useful as an antioxidant or a constituent the other compound. thereof, or which may be used for disinfecting or preservative purposes and for other general chem _ ical purposes where the amino and phenolic grouping in complex form is desired. 10 Reference is made to the accompanying draw ing, the single ?gure of which illustrates the freez ing point of my new compound and also the ini tial freezing point (or hold point) of compositions addition of either an alkali or an acid to the complex. Accordingly, I may add an acid to the complex and thereby form the acid salt of the amine. If the acid so chosen forms an insoluble salt, I leach the acidi?ed mixture with an appro priate solvent to remove the other constituent. containing varying proportions of the complexes. 15 In the same manner I may add an alkaline solu In the drawing: Figure 1 shows the melting point range for the tion to the complex, form the naphtholate, and 15 then dissolve the naphtholate from the mixture. Having now particularly described my inven system: 4-aminodiphenyl, beta-naphthol, and indicates a molecular compound of the type NI-Iz tion and the manner of compounding the same, it (para)C12H9.C1oHaOH, having a melting point of will be apparent that it is susceptible to various 20 approximately 132° C. This compound is a crys changes and modi?cations without departing 20 talline body. This ?gure also illustrates the freezing points (or hold points) of compositions containing varying proportions of the compound from the spirit thereof, and I desir , cated at one end of the curve. The compound herein disclosed may be pre addition product being characterized by the fact pared by mixing together the constituent sub are less soluble in most solvents than the con v erefore, that it be not limited except as indicated by the prior art or as set out in the appended claims. What I claim is: 1. As a chemical compound the addition prod- 25 uct of 4-aminodiphenyl and beta naphthol, said together with one or the other of its constituent 25 substances. The presence of a eutectic is indi stances in the proportion indicated and melting 30 and then cooling the mixture. An alternative method is to effect the combination by mixing to gether solutions containing the constituent com pounds and thereby causing the compound to pre cipitate from solution. 35 I have observed that the compounds described The molecular compound may be broken up by forming a salt of one of the constituents by the that upon the addition of acid thereto 4-aminodi phenyl acid addition salt and beta naphthol are 30 _ liberated. 2. A method of preparing the addition prod uct of 4-aminodiphenyl and beta naphthol which comprises heating a mixture of said materials in the absence of solvents to melting temperature. 35 RUSSELL L. JENKINS.