Patented July 30, 1946 2,404,896 UNITED STATES PATENT office POLISHING COMPOSITIONS David Aelony, Dayton, Ohio, assignor to Monsanto Chemical Company, a corporation of Delaware No Drawing. Application December 31, 1942, Seriai No. 470,873 8 Claims. (C. 106-8) 1. 2 The present invention relates to new synthetic is a soft, sticky wax whose value lies in good sol and to compositions containing the same. vent retention and in its plasticizing effect on the I have found that higher N-acyl derivatives of hard waxes. Paraffin is useful as a diluent for mono-aminobiphenyl having the general for. Waxes and as a retainer, but in itself it na: possesses no shining properties. No commercial polish is made up of a single wax because at present there is no wax available in which there are combined all the desirable wherein R is an aliphatic radical of properties of the individual waxes. Carnauba, from 7 to 35 carbon atoms, are highly valuable 10 wax is particularly desirable because it gives a as wax. Substitutes in polishing compositions. Of film which is harder and more brilliant than that particular interest are those N-acyl derivatives of the other commercially available waxes. How of mono-aminobiphenyl in which the acyl radical ever, it is by far the most expensive. Also, car contains, 12 or more carbon atoms, for example, nauba wax in common with most natural prod N-hexacoSoyl-p-aminobiphenyl, N-hexacosoyl-o- s ucts exhibits considerable variations in composi aminobiphenyl, N-hexacosoyl-m-aminobiphenyi, tion, which variations are regarded as trouble N-stearoyl-p-aminobiphenyl, N-stearoyl-O-ami some by progressive manufacturers. Since waxes nobiphenyl, N-stearoyl-m-aminobiphenyl, etc. used in polishes are generally employed in col Solid Or liquid Waxing and polishing composi loidal form, the physical properties of the polishes tions which contain compounds having the gen 20 necessarily vary with changes in the composition eral formula given above are characterized by of the ingredients. Hence, a synthetic product of their ability to confer a hard, brilliant, substan Constant composition but having the desirable tially water-proof coating to materials to which properties of the natural Wax Would be preferable they are applied. The higher N-acyl mono-ami to the natural products. nobiphenyls may be employed alone in form of I have found that with respect to hardness and Solutions or dispersions Or, if desired, with other gloss of film the present higher N-acyl derivatives Substances suitable for the superficial treatment of mono-aminobiphenyl are excellent substitutes of the material which is to be coated, as for ex for . Moreover, being synthetic ample with other waxy substances of natural or products prepared from readily available domestic synthetic origin, oils, , coloring materials, 30 materials, i. e., biphenyl, nitric acid and higher emulsifying agents, etc. The products thus ob fatty acids, their use in polishing compositions tained may be advantageously employed for the assures both constancy of product and avail Waterproofing and polishing of materials of all ability. The higher N-acyl derivatives of mono kinds, such as leather, wood, linoleum, etc. Com aminobiphenyls are especially desirable as con positions containing the present amides in con 35 stituents of the gel type of shoe polishes, the sub junction with paraffin and are admir stitution of the mono-amides for carnauba wax ably suited as shoe polishes. Wery desirable floor in this type of polish yielding products which waxes are prepared by incorporating a higher possess the following characteristics: (a) ability N-acyl-mono-aminobiphenyl with a minor pro to give a smooth, hard, shiny surface, (b) a suff portion of other waxy substances together with 40 ciently high softening temperature so that morpholine and water. polishes do not liquefy in hot summer weather, The function of waxes in polishing compositions (c) lack of blooming (crystallization on the Sur-, is to form a continuous, lustrous film which is face) and (d) lack of hysteresis (release of a hard, pliable and substantially water-resistant. part of the solvent by the gel). The film should not smear easily, but when it does 45 The higher N-acyl derivative of the mono-ami become smeared, it should buff readily to the nobiphenyls which are employed in the present Original shiny surface. invention may be readily obtained in good yields The most commonly used waxes are carnauba, by the reaction of ortho, para-, or meta-amino candelilla, and paraffin. Carnauba is bipheny with higher fatty acids possessing from a somewhat crystalline, hard, shiny Wax which 8 to 36 carbon atoms or with technically available possesses poor solvent retention. Candelilla is a mixtures of such fatty acids. Instead of the medium hard wax. It has good solvent retention fatty acids there may be employed the corre and serves as a good plasticizer for carnauba; sponding acyl halides or acid anhydrides. Ad however, it yields a smeary shine if present in mirably suited are the higher N-acyl derivatives more than i:1 ratio with carnauba. BeeSWax 55 of ortho-aminobiphenyl which are described in

2,404,896 3 4. the copending application of Earl W. Gluesen kamp, Serial Number 435,835, filed March 23, Eacample 3 1942. A wax gel shoe polish is prepared by the foll While I am aware that the higher N-acyl de lowing formula: rivatives of para-diaminobiphenyl, i.e., benzidine 5 Per cent have been previously suggested for use as Wax p-Stearamidobiphenyl ------11 substitutes in French Patent Number 842,725 to N-Stearoyl-alpha-naphthylamine ------8 I. G. Farbenindustrie, the use of such benzidine Paraffin ------6 derivatives for this purpose has never attained BeeSWax ------2 commercial application in that the melting points O Turpentine ------73 thereof, usually being in the neighborhood of The polish obtained is of as hard a consistency 2000 C., are too high to permit ready incorpora as that obtained from the carnauba wax for tion of the same into polishing compositions. In mula given in Example 1. Upon application to the industry, waxes are blended into such com leather and subsequent buffing it gives a glossy positions by melting the same in steam-heated 5 kettles, the temperature of which, accordingly, film which does not smear. does not exceed 150° C. Moreover, the Eacample 4 which are employed, for example, mineral Spirits, turpentine or , boil at temperatures which A wax gel shoe poish is prepared by the foll are substantially below the melting point of the 20 lowing formula: benzidine derivatives, hence incorporation of the Per cent same into such solvents often involves consider p-Stearamidobiphenyl ------8 able solvent loss. On the other hand, the melt Hydrogenated castor oil ------13 ing points of the N-acyl derivatives of the mono Paraffin ------6 aminobiphenyls, approximating that of the use 95 Turpentine ------73 ful natural waxes, entail no change in Operating The polish obtained has the consistency of that procedures of the polish-manufacturing indus obtained from the carnauba wax formula of tries. The mono-acyl derivatives of benzidine, Example 1. The p-stearamidobiphenyl formula which have also been suggested are undesirable, of the present example yields a polish which particularly because of discoloration due to oxi 30 dation of the free amino group. Such discolora when applied to leather and subsequent buffing tion would render the product unusable in neutral gives a smooth, glossy, hard film that does not or light colored polishes. Moreover, the mono Sea. derivative would be toxic. Eacample 5 The present invention is illustrated, but not 35 A paste polish is prepared by employing the limited, by the following examples: following formula: Eacample 1 w Per cent, A typical wax gel shoe polish formula, exclu p-Stearamidobiphenyl ------8 sive of coloring matter, may be made in accord Hydrogenated castor oil------8 ance with the following formula, the figures being 40 Farafin Wax ------8 expressed in percent by weight: Mineral Spirits ------76 Per cent, The composition obtained may be employed with Carnauba. Wax ------8 advantage for polishing wooden floors. The paste Candelilla Wax ------8 45 is of good consistency and yields upon applica BeeSWax ------2 tion to porous materials, and subsequent buffing, Paraffin ------6 a Smooth, hard, glossy Surface which is substan Turpentine ------76 tially unaffected by water at Ordinary or mod The substitution of either ortho- or para erately increased temperatures. stearamidobiphenyl for the carnauba wax in the 50 Eacample 6 above formula results in a polish which yields a film that is equal in gloss and hardness to that A solution type of floor or furniture polish was obtained from the carnauba-containing material. prepared by using the following formula: When formulating these and the following shoe Per cent, polish compositions it is customary to melt the 55 O-Stearamidobiphenyl ------2 waxes, add the solvent, cool until a temperature Beeswax ------2 of about 43° C. to 50° C. is reached, after which the polish is poured into cans. Variations may, Faraffin ------2 of course, be made in the proportions of the war Mineral Spirits ------94 ious ingredients employed in order to obtain mod 60 A clear solution of the waxy substances is thus ifications as may be desirable. obtained which solution is eminently suitable as a dressing and polishing composition for articles Eacample 2 made of Wood, or other porous materials. A wax gel shoe polish is prepared employing Eacample 7 the following formula: 65 Per cent An emulsion type polish was prepared by em O-Stearamidobiphenyl ------6 ploying the following formula: Candelilla Wax ------14 Per cent Beeswax ------2 O-Stearamidobiphenyl ------Paraffin ------4 BeeSWax------1. Turpentine ------74. Faraffin ------2 The above formula gives a gel of good son Stearic acid------sistency. Upon application to leather and sub Morpholine ------0.25 sequent buffing there is obtained a highly lustrous, Water ------88.75 hard and pliant film which does not smear. 75 Melt the waxes including the fatty acid and the

2,404,896 5 6 stearamidobiphenyl by heating to a temperature 2. A polishing composition containing the foll just above the melting point of the mixture. Pour lowing in per cent by weight: into the water containing the morpholine, stirring Fer cent rapidly until a homogeneous emulsion is formed, O-Stearamidobiphenyl------6 then cool with gentle stirring until room tempera 5 Candelilla wax------4. ture is reached. The resulting product was a Beeswax------2 white, mobile emulsion which showed no tend Farafin ------4 ency to separate out upon prolonged standing. Turpentine------74 When applied to articles made of wood, or leather 3. A polishing composition containing the fol it gives a quick shiny film possessing resistance to 0 lowing materials in emulsified form: wear, abrasion and water which is equal to or superior to films obtained by the employment of O Per cent carnauba-containing polishes of the emulsion O-Stearamidobiphenyl------. type. Beeswar------1. I have referred specifically to N-acyl-Substi 15 Faraffin------2 tuted mono-aminobiphenyls in which the acyl Stearic acid------1 group is the stearoyl group, because at the pres orpholine ------0.25 ent time stearic acid is the most readily available Water------Balance of the fatty acids, but the employment of other 4. A polishing composition, free from cellulose high N-acyl, derivatives of the mono-aminobi 20 derivatives, and comprising natural waxes, N phenyls likewise results in the production of de Stearoyl aminobiphenyl and turpentine as a sol sirable liquid or solid polishing compositions. Went therefor. While I have illustrated the use of the higher 5. A wax-type polishing composition, free from N-acylated mono-aminobiphenyls in combination cellulose derivatives, and comprising a natural with other waxes as the hardness- and gloSS-in 25 Wax, , N-stearoyl aminobiphenyl, and parting constituent of wax-compositions, these mineral spirits as a solvent therefor. amides may likewise be used either alone, as such, 6. A polishing composition, free from cellulose or in form of Solutions or emulsions in various derivatives, and comprising N-stearoyl aminobi media in order to confer hard, pliant and gloSSy phenyl, candelilla wax, beeswax, paraffin and tur. films to surfaces upon which they are applied. 30 pentine as a solvent therefor. The present mono-amides are waxy Solids that 7. In the process of making polishing compo are insoluble in water and soluble in the Organic sitions comprising natural waxes, the improve solvents which are customarily employed in the ment comprising substituting for a part of the preparation of liquid type polishes. At the pres- . natural wax an N-acyl aminobiphenyl in which 35 the acyl group contains from 8 to 36 carbon ent time, however, from an economical standpoint atoms. the incorporation of the amides with the less ex 8. A polishing composition consisting principal pensive paraffin wax, hydrogenated castor oil, etc., ly of a mixture of natural and synthetic solid is recommended. Wax-like materials and a solvent therefor, said What I claim is: 40 Synthetic solid wax-like material being an N-acyl 1. A paste-type polishing composition free from aminobiphenyl wherein the acyl group contains cellulose derivatives comprising stearamidobi from 8 to 36 carbon atoms. phenyl, a wax and mineral Spirits. DAWD AELONY.