Patented Aug. 27, 1929. 1,725,797

. UNITED STATES PATENT OFFICE. w MORTIMER. T. HARVEY, OF EAST ORANGE, NEW JERSEY, ASSIGNOR. To THE HARVEL CORPORATION, A CORPORATION OF NEw JERSEY. CASHEw-NUT-SHELL or L CONDENSER PRODUCT AND PROCESS FOR MAKING SAME. No Drawing. Application filed June 15, 1928. Serial No. 285,787. The present invention relates to materials classified as an acid oxidizing agent. Here and processes for making them, in which inafter the catalytic materials above men cashew nut shell liquid is employed. The in tioned will be referred to as driers, because 55 vention relates more particularly to mate they are employed to initiate or aid in drying 5 rials and processes involving the use of of the cashewnut shell liquid or products cashew nut shell liquid and an aldehyde made therewith, or in producing the drying with or without the use there with of a drying characteristic in cashew nut shell liquid. In oil or oils, such as linseed oil or tung oil, fish preparing products of this invention for use 60 oil or other equivalent oils, and in each case in the practical arts commercial cashew nut 10 with or without a drying agent or accelerator shell liquid is used, and this is secured as a or catalyst. w by-product of the cashew nut kernel, the It is an object of the invention to produce shell being burned or charred over an open from cashew nut shell liquid and other mate fire so that it can be removed by hand from 65 rials, products for coatings, impregnations, the kernel, the shell liquid being caught as it l3 paints, varnishes, molded compositions, for drips or flows from the opened shell. use in the paint industry, in electrical insula In the practice of this invention the alde tion, in molded articles and for use in the art hydes suitable are formaldehyde, paraform, generally. - acetaldehyde, paraldehyde, benzaldehyde, 70 It is another object of the invention to pro furfuraldehyde and other well known com. 20 vide a liquid coating material which will dry pounds comprising the aldehyde group of at normal temperatures within a few hours. atoms. The preferred aldehyde is formalde Other objects and advantages of the inven hyde and this can be used in its various forms, tion will appear from the following specifica namely; in the gaseous form; in solution in 5 tion in which the processes, methods, steps Water, the commercial forty per cent solution 25 and materials of the invention are fully de in water being suitable; and in the polymer scribed, and the invention also consists in ized form called metaformaldehyde or para the various methods and materials set forth form. The formaldehyde gas can be passed. in the appended claims. through a body of the cashew nut shell liq- 80 Primarily the method of the invention com uid; the water solution thereof can be mixed 30 prises bringing cashewnutshell liquid and an with the cashew nut shell liquid; and the aldehyde, preferably formaldehyde, together metaformaldehyde can be mixed with the to produce reaction products and materials cashew nut shell liquid. In the use of the having characteristics and properties herein different aldehydes and of different forms of 85 after set forth. a given aldehyde the reaction with the cashew 35 According to the invention the cashew nut nut shell liquid can take place at different shell liquid and formaldehyde can be reacted temperatures ranging from normal tempera with each other under different conditions of tures upwardly to points as high as 600° to temperature and pressure, and in each case 700° C. or more. When water solution of 90 with or without the influence of other mate formaldehyde is used, for some purposes the 40 rials such as driers or catalysts. Examples reaction is carried on at about 125° to 135° of the catalysts suitable for this purpose are C. but the reaction can be brought about at acid gums such, for example, as manganese temperatures above or below. The fact that resinate, rosin, and the like; acids, for exam formaldehyde passes as a gas from its water 95 ple, nitric acid, hydrochloric acid; alkali, for solution at about 95°C. is, in some cases, an 45 example, ammonia, lime, soda, baria, and so influencing factor in determining the tem on; oxygen containing metal compounds perature at which the reaction is brought other than those included in the above exam about, and in some cases the reaction is car ples, for example, copper oleate, copper car ried under a reflux condenser to return vapor- 100 bonate, copper ammonium sulphate, copper ized formaldehyde by means of condensed 50 ammonium hydroxide and so on; also metals water vapor which catches the formaldehyde such as copper, nickel and so on; and the vapor and carries it back. And recourse can nitric acid or the manganese resinate can be be had to other and various expedients well 2 1,725,797 known in the practice of the science of chem material depends on the history of its treat istry and physics to adapt the particular ment and on the ingredients and proportions processes used to the nature of the various al thereof and also on the temperature at which dehydes and aldehyde compounds employed drying is carried on. The prepared mate in the practice of this invention. rials which have been made at normal or room 70 The paraform or metaformaldehyde is sol temperature require longer for drying but uble in cashew nut shell liquid in both the some of those prepared with the use of heat solid form and in the melted or liquid form, will dry at room temperature in twenty-four and can be used therewith for purposes for hours, and at about 100° C. in from one-half which formaldehyde is used. The paraform to two hours. Examples of time and tem 75 will react with cashew nut shell liquid at perature for drying will be given hereinafter normal or room temperature but the time of with detailed description of the making of reaction can be decreased by heating, for ex illustrative examples of the invention. ample, at about 90° C. to 120°C, and at It is to be understood in this description 5 other temperatures above and below this of the invention that while commercial ca 80 range. The time of heating is suited to the shewnut shell liquid is cited, said liquid se particular application to which the material cured in other ways than those described to be prepared is to be put. can be used such for example as by opening Below is a tabulation of relations and con the shell mechanically and then removing the 20. ditions showing generally, but not limiting, shell liquid, because the commercial liquid 85 the manner in which cashew nut shell liquid has essential characteristics which are and water solutions of formaldehyde can be neither lost nor received during the removal brought together; and the other forms of by charring the shell. For example, the formaldehyde, the gaseous form and the par commercial liquid, like the liquid from me 25 aform as well as the other aldehydes can be chanically opened shells, will stand for years 90 used generally in the same manner. In the eX d to the air without drying or forming following table cashew nut shell liquid is a I. referred to as cashew liquid. It is to be further noted that the incorpora (1) Raw cashew liquid and formaldehyde tion of formaldehyde in cashew nutshell 30 at normal temperature. , coatings, molded compositions, and so on, 95 S.) Cooked cashew liquid and formalde the chemical resistance electrical insulation hy e at normal temperature. characteristics are bettered very much even (3) Raw cashew liquid, formaldehyde and when very small quantities are used. For drier at normal temperature. - example, four milkraft paper impregnated 35 (4) Cooked cashew liquid, formaldehyde and coated with cashew nut shell liquid var 00 and drier at normal temperature. nish of a given kind to five to six mil total (5). Raw cashew liquid and formaldehyde, thickness has a puncture test of fifteen hun heated. dred volts per mill thickness of the varnished (6) Cooked cashew liquid and formalde- 9 aper, whereas in a similar varnished paper 40 hyde, heated. in which a like cashew nut shell liqui W8 05 (7). Raw cashew liquid and formaldehyde nish has incorporated therewith formalde heated, and drier added. hyde in amount eight-tenths of one per cent (8) Raw cashew liquid, formaldehyde and the puncture test is raised to eighteen hun drier, heated. - dred volts per mil. 45 (9) Cooked cashew liquid, formaldehyde, Likewise, the resistance to, solubility in il) heated and drier added. acids, alkalis, alcohol, benzol, gasoline and (10) Cooked cashew liquid, formalde 9ther materials and chemicals is appreciably hyde, and drier, heated. increased by the incorporation of formalde. Other variations in the method steps can hyde in the cashew nut shell varnish, or other 50 be used to suit conditions and requirements. preparation. Vanoline, herein referred to, 5 The driers can be those hereinabove cited, is a petroleum distillate taken off between and the time and temperatures of “cooking” gasoline and kerosene, the term is a common and “heating can be varied; for example, t)trade name.e - - - the “cooking' can be at 450° F. for two hours, ... In making molded compositions the cashew or the cashew liquid can be raised to 600° F. nut shell liquid preparations can be used in 20 and then immediately permitted to cool. the liquid form, or in jelly or gum form. The The “heating” of the mixture of cashew liq jellies and gums are secured by heating the uid and formaldehvde, with or without other preparation for greater periods or at higher ingredients, can be at 190° to 250° F. for temperatures than are the liquid preparation two hours, for example. But since the reac and/or by using greater percentages of 25 60 tion will take place comparatively slowly at formaldehyde. room temperature it will be apparent that One general method of the invention com the time and temperature of heating can be prises eating commercial cashew nut shell varied to suit conditions and requirements, liquid up to a temperature of about 600°F. 65 The length of time of drying of the prepared and then cooling or permitting it to cool and 30 1,725,797 3 mixing formaldehyde therewith to produce nut shell liquid the product is fluent; but a product which is a modification of the when about 4% or more is used instead of cashew nut shell liquid. The heat can be about 2% or less the product is heavy and carried higher than 610°F., for example, as gummy. For making liquid material such as high as 850 F., and the heating can also be for vanishes and paints, electrical coil im at lower temperatures than 6000 F. The pregnating liquids, and the like, the about formaldehyde is added to the heat treated 0.2% to 2% formaldehyde is used. The cashew nut shell liquid, preferably at tem gummy material is suitable for making heavy peratures below the boiling point of water impregnations and molded compositions. 10 because asis well-known formaldehyde leaves Driers or accelerators can be used in this 75 the Water in which it is applied, at a tempera example of the invention and are useful there. ture below 100° C., that is, at about 95°C., in to hasten drying or setting thereof. Some the common commercial form of formalde of the driers and accelerators useful for this hyde being a 40% solution in water. In the purpose are for example, copper oleate, lead 5 preparation of this general example of the oxide, preferably as litharge, manganese material of the invention of the heat treated resinate, zinc oxide, and others above cited. cashew nut shell liquid is supplied with a The drier can be added at any time before, Solvent vehicle such as varnoline - or other during, or after the heat treatment of the Well-known solvent vehicles to adapt said liq cashew nut shell liquid and in one method 20 uid to be applied as a coating and the form under this general example of the invention 85 aldehyde is added after the addition of the the drier is added after the heat treatment vehicle because then it can be thoroughly and while the temperature is being brought and completely intermixed in the cashew nut down from upper heat treating temperature. shell liquid than when the latter is in the In this particular method the liquid after 25 uncut stage. The formaldehyde can be in being brought up to 600° to 610°F. is dropped 90 termixed with the cut cashew nut shell liq to 550 to 450° F., at which temperature it uid at room temperature after which the tem is held for about one hour, after which the perature is raised to produce or facilitate a drier is added and the temperature is then reaction between the treated cashew nut shell dropped further and solvent and formalde 30 liquid. The formaldehyde can also be added hyde added. to the heat treated cashewnutshell liquid as More specific example of the process of the it cools and before it has reached room tem invention is given helow, in the sequence of perature, the solvent, when it is added be its steps, but various modifications can be fore the formaldehyde, being also added be made in the steps and in the order of their 35 fore the liquid reaches room temperature. performance in the process: 00 As stated before, the temperature at the time About 4 parts, by weight, of raw cashew the formaldehyde is added is preferably, be nut shell liquid are heated to about 600° to low the boiling point of water and below the 610 F. and the heating is discontinued so temperature at which the formaldehyde that the liquid after reaching this tempera leaves its water solvent. After the formalde ture will start cooling. With quantities of 40 hyde is added to the heat treated cashew nut about fifty to one hundred gallons the tem shell liquid and stirred thereinto, the mix perature can be brought to about 580° and ture is brought up to a temperature about the heating discontinued whereupon the tem 280° to 300°F. or other suitable tempera perature will go as high as between 600 to tures depending on the solvent used, and so 610° F. and then begin to cool. At the upper 10 45 on, to drive of the water carried thereby, temperature, that is about 600 F., one part, care being taken to prevent excessive evapora by weight, of raw linseed oil is added to tion or volatilization of the formaldehyde the cashew nut shell liquid and intermixed from the mixture. The rate of reaction of therewith. The cooling mixture is permitted formaldehyde with the treated cashew nut to drop to between 550° and 450°F. and then 5 50 shell liquid is rapid enough to prevent loss held there for about one hour, for example, of excessive amounts of the formaldehyde by again applying heat, and at the end when the temperature is raised to drive of of this period driers are added about equal water, and to permit a single heating with parts each of litharge and magnanese resin: continuous rising temperature to suffice both ate, together totaling about 2% in weight of 20 55 for accelerating the reaction and for driving the mixture of cashew nut shell liquid and off water. w linseed oil. The preparation is then cooledor The resulting product of the heat treated permitted to cool to about 300 F. at which cashew nut shell liquid and formaldehyde temperature an equal amount of varnoline or varies in consistency from a comparatively other solvent is added as a vehicle. The 60 fluent liquid to a viscous mass depending upon preparation is then permitted to cool to room the proportion of formaldehyde to the treated temperature, as by letting stand over-night, after which 1% by volume of a 40% water cashewnut shell liquid. When about 2% by solution of formaldehyde is added and mixed volume of a 40% water solution of formalde 130 65 hyde is mixed with the heat treated cashew in. The mixture is then heated up to 280° 4. 1,725,797 F. to react the formaldehyde with the prepa 20% of the volume of cashew nut shell liquid ration and drive off water. The prepara used, then raise to about 190° F., preferably tion is then cooled or permitted to cool and under a reflux condenser, and hold for about then is ready for use. one to two hours, then removing reflux con 5 In this example there are about 50% solids denser if used, raise to 240° F. to drive off in the varnish solution, and the proportion of water and any excess formaldehyde. Add formaldehyde is approximately 0.5% of the another equal volume of varnoline and permit cashew nut shell liquid or 1% of the total. to cool. The product is a liquid varnish If the amount of formaldehyde used is which will dry under above stated conditions 10 doubled, then the reaction product of the and time. cashew nut shell liquid and formaldehyde is In a variation of this last example, the pre immediately formed as a jelly. heating of the cashew nut shell liquid to 450° A further characteristic of these reactions F. can be omitted and the product will dry is that the character of the solvent and the at room temperature in less than ten hours. “degree of solution' affect, to some extent, In the above method and if other methods 80 the rate or ease of reaction of the cashew nut of the invention, the linseed oil can be omitted shell liquid and formaldehyde. There is and straight cashew nut shell liquid used, some indication that there is a loose relation 'or tung oil, chinawood or japan wood oil, between the solvent and the cashew nut shell fish oil, castor oil or other drying oils can liquid because when large proportions of a be used. Also, instead of using raw oil, given solvent, varnoline, is used then larger boiled or jellied or blown linseed or tung or proportions of formaldehyde are needed to fish oil can be used; also the cashew nut shell get a given product with given changing liquid can be pretreated with heat before time and temperature characteristics etc.; and being brought up to the high temperature 2 likewise, when a solvent is used in which the herein cited. Further the drying oil or oils, 90 cashew nut shell liquid is more easily soluble whatever used, can be added before or after such as naptha instead of varnoline, a greater the cashew nut shell liquid is brought up. percentage of formaldehyde is needed to get to the high temperature, or it can be added a given product. This means, for example, in lots at different times during the process. O that with increased proportions of varnoline An explanation of the process in this regard 95 or when using naptha instead of varnoline, may be that cashew nut shell liquid is heated greater proportions of formaldehyde must to the cited high temperatures in order to be used to get a jelly. It is to be noted that modify it to suit it to reaction with small when no solvent at all is used for the cashew Quantities of formaldehyde to produce an nut shell liquid then jelly is formed immedi usable product, and the drying oils are added 00 ately with even very small proportions of to further modify the cashew nut shell liquid formaldehyde. Also when proportionately as regards body, texture, finish and so on. It highly diluted solutions of the cashew nut is to be noted in the particular example of shell liquid in varnoline or other solvent are linseed oil cashew shell liquid varnish above ...) used then the less the difference in results given that the raw linseed oil when added when the amount of solvent is varied. Also, to the cashew shell liquid at the upper tem the greater the amount of heating of the peratures serves to cool the latter liquid down cashew nut shell liquid before or after the Or at least to absorb some of the heat there formaldehyde is added, the less formalde from. hyde is needed to get a jelly. In modifications of the particular example O Conversely, when raw cashew nut shell above given, and in other cases, the formalde liquid is used comparatively great propor hyde can be added to the preparation before tions of formaldehyde can be used without it has reached room temperature on cooling getting a jelly also with the higher propor from the high temperatures, but in any case 50 tions of formaldehyde the lower the tem control of the effective amount added is at perature needed for drying a liquid varnish, tained and loss of formaldehyde by evapora for example. tion is prevented by adding the formalde As an example of the difference in charac hyde below the temperature of volatiliza ter between the raw cashew nut shell liquid tion thereof from its water solution, which and the same liquid heated to 600°F., the temperature is about 95° C. for 40% solution 20 following is given, the product being a var of formaldehyde in water or common com nish which will dry in air at room tempera mercial formaldehyde. ture in from five to eight hours. Heat one As an example of a process and product volume of commercial cashew nut shell liquid of the invention where no heat is applied 60 to 450° F. and add 2.5 to 5% manganese during the preparation, the following is resinate which dissolves therein and then given: About 25 parts by volume of cashew permit to cool to about 300° F. and add an nut shell liquid and about 10 parts of a 40% equal volume of varnoline. Then cool to water solution of formaldehyde, and about about 140° F. and add a 40% water solution five parts of concentrated hydrochloric acid of formaldehyde, in volume about 10% to are mixed together in about 50 parts of gaso 2 1,725,797 5 line or other suitable solvent and the mixture shell liquid equal parts by weight of these is let stand for about forty-eight hours at materials are mixed together (the phenol room temperature. During this time a re being commercial crystals, and the formalde action occurs which produces a small amount hyde being a 40% solution in water) and of water and a product soluble in the gasoline heated to about 330° F. and allowed to cool. and two layers are formed, one a top gaso The resulting product cut with a vehicle, 70 line layer which carries the dissolved reac varnoline, for example, when applied as a tion product and the other a water layer coating to paper and varied at 250° F. gave which carries unreacted acid and to the bot a hardened somewhat flexible film. 0 tom of which settles reaction products which In another example, to equal parts of 75 are not soluble in the gasoline. As the re cashew nut above described, about 3% of a action continues the gasoline, solution layer 28% ammonia solution was added and the thickens in consistency until the reaction mixture brought up to 330 F. and allowed agents have substantially all reacted. The to cool. The product was hard and brittle, 5 gasoline solution is then separated from the could be powdered and was fusible, but on 80 water and is preferably washed to remove heating for about one-half to three-quarters traces of acid. The solution of reaction prod of an hour become infusible. This material uct in gasoline made in this manner will dry is suitable among other purposes, for mak in from three to five minutes at a tempera ing molded compositions and impregnations. 20 ture of about 104° C., that is the solvent will Cashew nut shell liquid formaldehyde 85 be driven off and the reaction product will products can be used with phenol formalde be set into a condition in which it is insoluble hyde condensation products to make prod in gasoline, benzene, benzol, naphtha, alco ucts which have the general characteristics hol, and other similar solvents, and also in of cashew nut shell liquid products and 25 soluble in dilute or concentrated acids or al phenol formaldehyde condensation products 90 kalis, and in which it will be unaffected by boiling water. and which have a degree of flexibility and In the above example of method, the water E.ormaldehyde not beforecondensation obtained products; with phenol and can be driven off by heating to about 100° C. drying oils, such as those above cited can be 30 or more and this heating will affect the reac used to increase pliability and give body and 95 tion product to produce further reaction so on to the final product. In this class of therein so that the drying time, when ap E. formaldehyde from the phenol plied, is reduced. g ormaldehyde condensation product can be In all of the examples described herein the utilized for reaction with the cashew nut 35 reaction product may be in colloidal suspen shell liquid with or without the adddition of 00 sion in tR. vehicle or in solution therein or other formaldehyde. partly in both these phases, and in the claims In all or most of the general and specific ex hereof solution is intended to cover whatever amples above given variation can be made to relation there is between the reaction product put the cashew nut shell liquid, formalde 40 and the vehicle. hyde, drier, and solvent (and drying oil The solvents above cited are generally all when used) all together at the same time to volatile solvents but non-volatile solvents get products suitable for particular purposes can be used, particularly when the material and uses. used for the solvent can be left in the prod A great advantage, among others, of the 45 uctor when it forms a part thereof as by some cashew nut shell liquid-formaldehyde prod 0. reaction. For example, cresol, phenol, or ucts of this invention, with or without dry resorcinol can be used as solvents to catch ing oil or oils, is that in drying a coagula the reaction product as it is formed to pre tion and hardening takes place uniformly vent the formation of the gummy reaction throughout the mass of the products. This 50 product when comparatively large per is of prime importance in the impregnation 15 centages of formaldehyde are used with the of electric coils with products of this inven cashew nut shell liquid. These products, tion because the impregnation will dry or set namely, phenol, cresol, resorcinol, etc., have uniformly throughout the body of the coils the same effect in blanketing or retarding the even though the inner parts have no exposure 55 rate of reaction between cashew nut shell to the air. The drying or setting reaction 120 liquid and formaldehyde as does the vola is in the nature of the catalytic and the re tile solvents as above pointed out. It is per sults seem to indicate that the products of tinent however that phenol, cresol, and resor the drying reaction formed at the surface cinol react with the cashew nut shell liquid influence the inner parts within infinitesmal 60 and formaldehyde to form distinctive prod periods of time to produce a uniform product 125 ucts and can be used even when minor quanti entirely through the mass. This is in con ties of dehyde are used and when trasting distinction from the nature of dry solvent per se can be omitted. - ing oils, such as linseed oil, tung oil and so on In one example of method and product and their products, in setting, in which class using phenol, formaldehyde and cashew nut of materials drying or setting takes place 30 6 1,725,797 slowly, beginning at the surface and absorb ing cashew nut shell oil and a material reac ing enormous quantities of oxygen, and in tive therewith together in the presence of a which films formed at the outer surfaces. solvent for a reaction product thereof, and hinder the passage of oxygen inwardly and removing any water or any insoluble mate retard the drying or setting of the inner por rial formed. 70 tions so that in cases where the mass is of a 11. The process which comprises bringing little extent, as in electrical coils, the inner cashew nut shell oil and a material reactive portions remain in the liquid state for long therewith together in the presence of a vola periods of time after the coils have been put tile solvent E. a reaction product thereof. O in use, in some cases for months and years, 12. The process which comprises bringing 75 even though heat has been applied in an ef cashew nutshell oil and a material reactive fort to aid setting or drying. In the use of therewith together in the presence of a vola the products of this invention the insulation tile solvent for a reaction product thereof, value and the binding and cementing of the and removing any water or any insoluble 15 coils together is secured immediately and material formed. 80 usually before the coils are put to use. 13. The process which consists in bringing Coatings, impregnations, molded composi formaldehyde and cashew nut shell oil to tions, and so on, prepared according to the ex gether in the presence of a petroleum solvent. ample processes described above have a high "14. The process which consists in bringing degree of resistance to acids, alkalis, and to formaldehyde and cashew nut shell oil to common solvents such as varnoline, gasoline, gether in the presence of a petroleum sol alcohol, benzine, and so on, and have high vent holding them together while a reaction dielectric strength. product is formed and dissolved in the solvent I claim:- - and then removing any water or any in 25 1. The process which comprises in bring soluble product formed. ing cashew nut shell liquid, formaldehyde, 15. The dissolved product in a solvent, and a drier together in a common solvent. which is a reaction product between cashew 2. The process which comprises in bring nut shell oil and formaldehyde when ing formaldehyde into contact with cashew brought together in said solvent. 30 nut shell liquid while the latter is in solu 16. The process which comprises bringing 95 tion in a solvent for the initial reaction prod together about 25 parts by volume of cashew uct of said materials. nut shell oil and about 10 parts of a 40% 3. The process which comprises in bring water solution of formaldehyde in about 50 ing formaldehyde into contact with cashew parts of a solvent for the initial reaction 35 nut shell liquid while the latter is in solution product of cashew nut shell oil and formalde 00 in a solvent for the initial reaction product hyde, and letting stand to effect a reaction of said materials, and then adding a drier. product soluble in the gasoline 4. The process which comprises in bring 17. The process which comprises bringing ing formaldehyde into contact with cashew together about 25 parts by volume of cashew 40 nut shell liquid while the latter is in solution nut shell oil, and about 10 parts of a 40% 105 water solution of formaldehyde in about 50 incashew a solvent nut shell of theliquid product and formaldehyde. of reaction of parts of a solvent for the initial reaction 5. The process which comprises bringing product of cashew nut shell oil and formalde cashew nut shell liquid and formaldehyde-to hyde, and letting stand to effect a reaction gether in a common solvent, and heating the product soluble in the gasoline, and then O cashew nut shell liquid at some stage to in separating out any water present. crease the rate of reaction of said shell 18. The method of making and holding in liquid. condition for applying a product which con 6. A solution of cashew nut shell liquid sists in the process which comprises bringing 50 and formaldehyde in a solvent for the initial together about 25 parts by volume of cashew 115 reaction product of said materials. nut shell oil, about 10 parts of a 40% water 7. A potentially reactive composition con solution of formaldehyde, and about 1 to 5 taining cashew nut shell liquid formalde parts of a drier in a solvent for the initial hyde and a solvent for the initial reaction reaction product of cashew nut shell oil and product of the first two mentioned materials. formaldehyde, and letting stand to effect a 120 8. A potentially reactive composition con reaction product soluble in the gasoline, sep taining cashew nut shell liquid, formalde arating out water, acid, or insoluble reaction hyde, a drier and a solvent for the initial product present. reaction product of the first three named 19. The method which comprises subject 125 materials. . . ing cashew nut shell liquid to the action of 9. The process which comprises bringing formaldehyde, in a solvent for a reaction cashew nut shell oil and a material reactive product of said materials. . . . therewith together in the presence of a sol 20. A composition of matter obtained by vent for a reaction product thereof. subjecting cashew nut shell liquid to the ac 65 10. The process which comprises bring tion of formaldehyde ln the presence of a 30 1,725,797 ...... 7 solvent for a reaction product of said mate- process step of reacting cashew nut shell rials. E. formaldehyde and a drier in a solvent 21. The process which comprises Enging for the reaction product of said materials, 10 cashew nutshell liquid, formaldehyde, an In testimony, that I claim the invention set 5 a drier together in the presence of a solvent forth above I have hereunto set my hand for a reaction product thereof. this 5th day of June, 1928. 22. The product which is made by the MORTIMER. T. HARVEY.