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United States Patent \ .J Patented Oct 2,907,738 United States Patent \ .j Patented Oct. 3, 1959 1 2 dibasic acids would also give polymerization in which the natural resin acid ester becomes an intimate part ‘ 2,907,738 of the ?nal polymer chemical composition. Such esteri ‘MIXED RESIN ACID ESTERS OF 4,4-BIS(47 ?cation reactions involving the phenolic hydroxyl groups HYDROXYARYL) PENTANOIC ACID 01 would conveniently be carried out by heating with a mix ture of the dibasic acid and acetic anhydride. Sylvan 0. Greenlee, Racine, Wis., assignor to The hydroxyaryl—substituted aliphatic acids contem~ S. C. Johnson & Son, Inc., Racine, Wis. plated for use in preparing the desired resinous poly No Drawing. Application June 30,1955 hydric phenols have two hydroxyphenyl groups attached ‘ Serial No.‘ 519,279’ 10 to a single carbon atom. The preparation of these sub~ stituted acids may be most conveniently carried out by 9 Claims. (Cl. 260-24)‘ condensing a keto-acid with the desired phenol. Expe rience in the preparation of bisphenols and related com pounds indicates that the carbonyl group of the keto This invention relates to new compositions which are 15 acid must be located next to a terminal carbon atom in ‘mixed esters of‘polyhydric alcohols, natural resin,acids, order to obtain satisfactory yields. A terminal carbon and hydroxyaryl-substituted aliphatic acids. atom as used herein refers to primary carbon atoms An object of this invention is to produce new com other ‘than the carboxyl carbon atom of the keto-acid. positions from natural resin acids, polyhydric alcohols Prior applications, Serial Nos. 464,607 and 489,300, and hydroxyaryl-substituted aliphatic acids which are 20 ?led October 25, 1954, and February 18, 1955, respec~ valuable as intermediates in the production of other more tively, disclose a number of illustrative compounds suit complex compositions. able for use as the hydroxyaryl-substituted acid, and Another object of this invention is to produce new methods of preparing'the same. These materials, which compositions of the hereinbefore described ‘character are referred to for convenience as Diphenolic Acid, or which are valuable in the manufacture of more complex 25 DPA a trademark of S. C. Johnson & Son, Inc., com~ reaction products having unusually good chemical resist- , prise the condensation products of levulinic acid and ance, hardness, gloss, etc. phenol, substituted phenols or mixtures thereof. It is These and other objects and advantages ‘are attained to be understood that the phenolic nuclei of the ,Diphe ' by the present invention,‘ various novel features of which nolic Acid may be substituted with any groups which will become more fully apparent from the following 30 will not interfere with the esteri?cation reactions. For description, with particular‘reference to speci?c exam example, the nuclei may be alkylated as disclosed in ples which are to be considered as illustrative only. Serial No. 489,300 or they may be halogenated. The The compositions of this invention, being esters of Diphenolic Acid derived from 1 mol of levulinic acid polyhydric alcohols and mixtures of natural resin acids and 2 mols of phenol is particularly advantageous in and hydroxyaryl-substituted aliphatic acids, are relatively that it may be readily prepared to a high degree of high molecular weight resinous polyhydric phenols. The purity, whereas the use of substituted phenols, such as number of phenolic groups per molecule. are dependent the alkylated products, usually results in. mixed compo on the number of alcoholic hydroxyl groups present in sitions which are less readily puri?ed. On the other the polyhydric alcohol esteri?ed, as well as on the hand, there are cases Where the Diphenolic Acid derived amounts and proportions of natural resin acid and from alkylated phenols are more desirable than those hydroxyaryl-substituted aliphatic acid used in the prep derived from the nonalkylated product on the basis that aration of the esteri?ed product. the alkyl groups tend to give better organic solvent solu The mixed esters of this invention combine ‘within bility, ‘?exibility, and better water resistance. the same chemical molecule natural resin acid esters and The natural resin acids which may be used with these a phenolic residue, the natural resin acid ester portion 45 hydroxyaryl-substituted acids in the co-esteri?cation of being similar to the natural resin acid portion present the polyhydric alcohols are illustrated by the commercial in the so-called ester gums which are natural resin acid grades of rosin and other natural-occurring acid resins, esters of polyhydric alcohols. This property renders the such as the kauri, copal, damar, and Congo gums. compositions of this invention particularly valuable in Typical commercial grades of rosin, for example, have the manufacture‘ of complex products such as coating 50 and molding compositions, where the natural resin acid acid values of, around 150-175. Acid values as used esters are desirable for the purpose of contributing hard herein are de?ned as the number of milligrams of KOH ness and gloss to the ?nished product. The phenolic required to neutralized the acid present in a one-gram residues present in the compositions and introduced by sample. Typical damar gums have acid values ranging the hydroxyaryl-substituted aliphatic acids contribute‘ re~ 55 from 18 to 60. Kauri gums have acid values of from active phenolic hydroxyl groups which for the most part 60-80, while copal gums have acid values in the range do not enter into the esteri?cation reaction used in the of 105-130. The essential composition or" all these preparation of the mixed ‘esters of this invention. These natural-occurring resin acids are cyclic terpenic type functional groups permit further reaction between the acids of which abietic acid is fairly typical. mixed esters of this invention and such materials as 60 The polyhydric alcohols may be the nonresinous type aldehydes, epoxides, and carboxylic acids to yield addi~ or the resinous type. These polyhydric alcohols, be tional complex products. Reaction with aldehydes, cause of their polyfunctionality, will esterify with natural either in' the presence or absence of other compounds resin acids and hydroxyaryl-substituted acids to give a capable of polymerization with aldehydes, gives com resinous phenolic product. Illustrative of the nonresin positions which are valuable constituents of protective 65 ous type polyhydric alcohols are such materials as ethyl coatings and‘ molding resins. Similarly, the phenolic ene glycol, polyethylene glycols, propylene glycol, poly hydroxyl groups of the phenolic residues‘ may be reacted propylene glycols, 1,3-butane diol, 2,5-pentane diol, with polyepoxide compositions to give highly polymer 1,6-hexane diol, neopentyl glycol, glycerol, erythritol, ized products containing within the same molecule the pentaerythritol, polypentaerythritols, sorbitol, mannitol, natural resin acid ester‘residues. Esteri?cation‘ of the 70 alpha methyl, glucoside, polyallyl alcohols, diethanol phenolic hydroxyl groups of the phenolic residue with amine, triethanolamine, and tetramethylol cyclohexanolZ 2,907,738 'i' 3 4 The resinous polyhydfie alcohols Which may be used Esteri?eation of either the nonresinous or resinous in the preparation of the subject esters may be illustrated polyhydric alcohols with Diphenolic Acid and natural by Such materials as the l'esinells Ieaetion Products of resin acids is conveniently carried out by direct heating bisttlehvdroxyphenyl)isopropylidene With ethylene ch10‘ at temperatures of from 190—275° C. under conditions Tohydr’iil . 61‘ glycerol mo?eehlofohydrin- The reaction 5 where the water produced during condensation is continu ef the ‘Same. dihydrie Phenol with ‘epichlorohydfln or ously removed as it is formed. In the case where ep g'll’eei'ol 'die'hlofohydfin gives resinous polyhydric a100- oxide groups of, for example, a resinous composition of H015 which ‘are Polymeric polyhydric alcohols and Which the Epon resin type produced by Shell Chemical Corpo in some cases. in‘ addition to the alcholic hydroxyl groups. ration are partially esteri?ed only to the, extent of one 'eollt'ai‘n ePOXide groups- (The epoxidereenwinihg PYOd- 10 carboxyl group reacting with one epoxide group, lower nets are 'well illustrated by the commercially availa le temperatures may be used and no water is formed since Epon resins marketed by Shell Chemical Corporation) the reaction of the carboxyl group with the epoxide The preparation of these resinous polyhydric alcohols are group is that of direct addition with the formation of an described in US. Patents 2,456,408, 2,503,726, 2,615,008, ester-linkage and a free hydroxyl group. Since the Di '2,6'68,805, 2,668,807 and 2693,315- 15 phenolic Acid ‘and the polyhydric alcohols have boiling ‘ Other resinous polyhydri'c'alwhols which may be em- points which are in all cases above 190° C., the Water ployedwmay be illustrated by those which are prepared mayberemoved by permitting ittoyolatilize during es~ ‘by’ the'reaction of phenol-formaldehyde‘condensates with teriiication, Rgmoval of thelwam-vmayp also-be fad“ ‘chlorohydrins. For example, analkylphenol may be Con- tated by continuously bubblin'gthrou‘gh the reaction mix ‘dells'ed With formaldehyde, followed by treatment of 8m 20 ture during esteri?cation a stream of inert gas, such as alkaline solution of this intermediate methylol derivative carbon dioxideor nitrogen, It is also sometimes conven ‘With ‘3 ‘chlerohydrln, Such as glycerol'mollqehlorohydfini lent to. facilitate
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