Foaming properties of rosin soap and their comparison with those of fatty acid soaps

Summary The foam production of soaps made from rosin, modified rosins, and rosin acids were evaluated. The foam production of rosin soaps was compared with soaps made from the individual fatty acids. There was no difference in the foaming properties of soaps made from longleaf and slash pine rosin. Oxidation of the unstable rosin acids in rosin caused the foaming properties of the rosin soap to become more nearly proportional to the concentration. The more hydrogen present in the rosin acid molecule the greater were the foaming properties of the rosin soap. At temperatures between 200° C. and 275° C., the lower the temperature employed for producing pyroabietic acid catalytically, the greater were the foaming properties of the pyroabietic acid soap. There was a difference in the foaming properties of commercial stabilized rosins. In foaming properties the soaps made from rosins, modified rosins, and rosin acids were more like sodium laurate than the other individual fatty acid soaps tested. The author wishes to express his indebtedness to to Dr. G. S. Jamieson and W. G. Rose of the Agricultural Chemical Research Division for the pure lauric, myristic, palmitic and stearic acid used in this study.     

Detergent action of rosin soaps and fatty acid — Rosin soaps

Summary A method for evaluating the detergent action of soaps has been described and applied to a series of soap solutions. The detergent action of rosin soaps, the effect of compounds present in soap or used with soap on the detergent action of a rosin soap, and the effect of rosin soap on the detergent action of tallow soap have been tested. The effect of temperature on the detergent action of some of the detergent solutions has also been determined. The results of these detergent tests on rosin, fatty acid and fatty acid-rosin soaps indicated the following: (1) Rosin soaps made from different gum rosins, produced from longleaf and slash pine gums, have equal detergent action; (2) The presence of soaps of oxidized rosin acids has no effect on detergent action of the rosin soap; (3) The detergent action of soaps made from pyroabietic acid, abietic acid and hydrogenated rosin parallels their ability to lower the surface tension of water and the amount of hydrogen present in the rosin acids; (4) The addition of builders that increase the alkalinity of the rosin soap solution improves the detergent action of the solution; (5) The blending of rosin soap with tallow soap improves the detergent action of the tallow soap in solutions having a soap concentration of 0.25 percent or more; (6) Temperature affects the detergent action of rosin and coconut oil soaps more than tallow soap.     

The germicidal activity of rosin soap and fatty acid-rosin soap as indicated by hand-washing experiments

Summary and Conclusions Price’s procedure as slightly modified (4) was used for studying the germicidal action of cleaning agents on the hands and showed that rosin soap and a commercial soap containing rosin were more active germicidally on the bacteria normally found on human skin than the usual commercial fatty acid soaps free from rosin soap. The experiments indicate that the lather of a 10-percent coconut oil soap solution and of a 10-percent coconut oil-rosin soap solution are germicidally active against the organisms removed. However, three 2-minute washes with these soap solutions had little effect on the bacteria not removed from the hands. The use of a 10-percent rosin soap solution in the same manner had a marked germicidal effect against both the organisms removed and those remaining. The lather of a commercial soap containing rosin soap was shown to be germicidally active, but three 2-minute washes had only a slight effect on the resident flora. However, the regular use of this soap daily for one week led to substantial reduction of both the transient and resident flora of the hands. The evidence of germicidal activity of rosin soaps and soaps containing rosin, both with regard to these hand-washing experiments and the “in vitro” (7) experiments, indicates that wider consideration might well be given this type of soap where germicidal activity is of importance. L. S. Stuart was employed in the Industrial-Farm Products Research Division when this work was done.     

Surface tension of rosin soap solutions

Summary The surface tension of soap solutions made from rosins and rosin acids has been measured and the surface tension of fatty acid soap solutions and fatty acidresin soap solutions have been measured and compared.     

Solubility of calcium soaps of gum rosin,rosin acids and fatty acids

Summary The solubility of calcium soaps of rosin acids and fatty acids have been determined and compared. The solubility of calcium soaps of rosin acids (d-pimaric, dihydroabietic, and l-abietic acids) present in gum rosin was found to be greater than that of the calcium soaps of the following saturated fatty acids: lauric, myristic, palmitic, and stearic acids. The calcium oleate was much more soluble than the calcium stearate. As the amount of hydrogen in the rosin acid molecule is increased, l-abietic to dihydroabietic to tetrahydroabietic acid, the solubility of the calcium soap is decreased. The author wishes to express his indebtedness to Dr. G. S. Jamieson and W. G. Rose of the Agricultural Chemical Research Division for the pure lauric, myristic, palmitic and stearic acid used in this study.     

Physical-chemical properties of tall-oil soap solutions

Summary Acid-refined tall-oil was separated into resin acid and fatty acids of approximately 94% purity, made into soaps, and compared with those made from oleic acid and rosin. Tall-oil resin-acid soap and rosin soap are roughly comparable in dispersing power and lowering of surface tension and interfacial tension. The tall-oil fatty-acid soap shows some points of inferiority to sodium oleate, as might reasonably be expected because of its greater unsaturation. Presented at 113th meeting of the American Chemical Society, Chicago, Ill., April 14–23, 1948.     

Comparative value of fatty acids and resin acids of tall oil in soaps

Summary A study has been made of the detergency and foaming power of soaps made from a typical acid-refined American tall oil. Sodium soap of tall oil, straight tall oil fatty-acid soap, and straight tall oil resin-acid soap were evaluated. The effect of fatty acid-resin acid ratio was determined by using mixtures of those soaps. Sodium rosinate, sodium oleate, and mixtures of these soaps were used as comparison standards. Curves plotted show wash-test data and foaming values as functions of the ratio of fatty soap to resin soap. The data indicate in terms of detergency: a) tall oil soap has a higher value than sodium rosinate; b) sodium oleate is better than tall oil fatty-acid soap, but the latter is approximately equivalent to soaps from various unsaturated vegetable oils; c) both tall oil resin-acid soap and rosin soap have low detergency on cotton; d) the detergency of most mixtures of tall oil fatty-acid and resin-acid soaps at lower concentrations is greater than would be predicted from the individual soaps, indicating a synergistic effect. As a rough approximation, tall oil soap without unsaponifiables is equivalent to a corresponding mixture of sodium oleate and sodium rosinate. The presence of unsaponifiables lowers both detergency and foaming. Tall oil soap is somewhat less sensitive to hard water than sodium oleate. Significant differences between detergencies of soaps, and especially between soap mixtures, are obscured when launderometer tests are run at moderate soap concentrations. These differences are readily detected at lower concentrations. Presented at 113th meeting of the American Chemical Society, Chicago, Ill., April 14–23, 1948.     

9,10,12,13-四羟基硬脂酸钠在低温硬质水及中性pH条件下的特异性能

以天然亚油酸为原料,经氧化水解制备得到9,10,12,13-四羟基硬脂酸(THSA),采用FTIR、ESI-MS和1HNMR表征了THSA的结构。测定了THSA的钠皂9,10,12,13-四羟基硬脂酸钠(STHS)的克拉夫特点、钙离子稳定性、钙皂分散剂消耗量、表面张力、临界胶束浓度和泡沫性能,并与对照物亚油酸、油酸及硬脂酸的钠皂进行比较。结果表明,STHS具有其他脂肪酸钠皂不具备的优秀钙皂分散性能和钙离子稳定性,并在低温和中性条件下显示出更好的水溶性。STHS不仅克服了普通脂肪酸钠皂不耐硬水和中性条件下溶解性差两大共同缺陷,也克服了饱和脂肪酸钠皂低温溶解性差以及不饱和脂肪酸钠皂易氧化酸败的缺点,因此,STHS具有在中性皂、低温皂和抗硬水皂配方中用作新皂基表面活性剂的潜质。     

Studies in soap crystallization processes. Part III. Acid soap crystallization in the segregation of tall oil fatty acids

Tall oil fatty acids have been fractionated into 80–90% oleic acid, and 60–80% linoleic acid fractions, by precipitation of the oleic acid as acid soap from polar solvents. Sodium and potassium acid soaps are equally effective, but ammonium acid soaps require lower operating temperatures. The choice of solvent is not critical as regards degree of separation, but technically attractive filtration rates have been obtained only with methanol and acetone. Acidulation gives colorless oleic acid of very low rosin acid and unsaponifiable content, but with 5–10% of conjugated linoleic acid.     

Rosin/acid oil-based liquid soap

Soapstock was converted into a liquid soap from its acid oil and formulated with varying amounts of rosin. The characteristics of the acid oil and rosin were experimentally estimated. Liquid soaps were characterized by density, pH, total fatty matter, free caustic alkali, critical micelle concentration, foaming capacity, wetting power, and washing performance. The foaming results indicated that the liquid soap is best used as an ingredient in a washing-machine detergent. The dark aspect of a formulation with 10% rosin precluded higher substitution.     

Chemical and physical characteristics of soap made from distilled fatty acids of palm oil and palm kernel oil

Manufacture of soaps from distilled fatty acids of palm oil (PO) and palm kernel oil (PK) is a well-established technology in Malaysia. Data on quality and characteristics of various blends of PO/PK fatty acid-based (palm-based) soaps made in Malaysia are not available, however. In view of this, the study described in this paper was undertaken. Eleven blends of palm-based bar soaps were made, and their properties were evaluated. There was an increase in the acid value of blended raw materials with increasing amounts of PK fatty acids. The iodine value and titer (°C) of blended raw materials, however, bear an inverse relationship with the amount of PK fatty acids. As expected, the hardness of the soap bars from the various blends increased with increasing PK fatty acid. Total fatty matter ranged from 76–85%, free caustic content was 0.1%, and sodium chloride content was 0.3–0.4%. Characteristics of soap blends made for this study were comparable with those from other countries. Quality of the soap obtained was comparable to those produced commercially.     

Saponification of Emulsified Triglyceride Oil in Presence of Rosin and Fatty Acid Soaps

Saponification of triglyceride oil emulsified in alkaline aqueous solution is found to proceed faster in presence of soaps from rosin acids than with soaps from fatty acids. The results are discussed in relation to differences in phase properties between the two types of soaps and applications in alkaline pulping.     

Properties of soaps derived from distilled palm stearin and palm kernel fatty acids

Soaps made from blends of distilled palm stearin (PS) and palm (PK) kernel fatty acids were evaluated for total fatty matter, sodium chloride content, moisture content, hardness, Hunter whiteness, foamability, iodine value, titer value, and acid value. Data showed that these soaps had properties similar to palm-based soaps made from distilled palm oil and palm kernel fatty acids. The soaps showed good whiteness (greater than 80%) and foamability. Total fatty matter ranged from 10–18%, sodium chloride content was 0.5%, and free caustic was 0.1% except for blend 8 containing 10 PS:90 PK, which had a free caustic of 0.03%. Initial penetration value, a reflection of soap hardness, ranged from 32–126 mm, with an average value of 54 mm. This value is within the range of the best blends of palm-based soaps (50–63 mm). There was no obvious trend observed. Penetration value, however was found to stabilize after a month of storage with an average value of 19.4 mm. Soap with this hardness value is relatively hard and therefore should be blended with a small amount of soft oils.     

C-21 dicarboxylic acids in soap and detergent applications

A unique polycarboxylic acid, 5(6)-carboxy-4-hexyl-2-cyclohexene-1-octanoic acid, has been available commercially for over 15 years. A new high-purity (>97%), light-color version of the C-21 dicarboxylic acid has been developed recently. Soaps of the C-21 dicarboxylic acid can be used as hydrotropes to increase the solubility of nonionic surfactants in aqueous solutions containing builders and/or anionic surfactants. Since these soaps are anionic fatty acid derivatives, they reduce the surface tensions of formulations, thus improving detergency. The nontoxic and biodegradable nature of this dicarboxylic acid makes it an attractive formulation component. This paper outlines application evaluations of the soaps prepared from the C-21 dicarboxylic acids. These evaluations demonstrate how the soaps interact with nonionic surfactants or pine oil to provide clear formulations, how they wet cotton skeins in neutral to highly alkaline solutions, and how they inhibit gel formation when preparing high-solids fatty acid soap solutions. Furthermore, the preparation and characterization of the soaps of the C-21 dicarboxylic acid products are discussed. Mass-balance equations describe the preparation of aqueous soap solutions at any given concentration. Characterization of the resulting soap solutions includes acid number, pH, color, color stability, foam stability, surface tension as a function of concentration, and hard-water compatibility.     

Current future fat-based raw materials for soap manufacture

The traditional use of coconut and palm oils for soap manufacture can be expected to continue indefinately. Certain oils of the oleic/ linoleic acid group are too unsaturated to yield soaps of the desired degree of hardness and stability. They may be hydrogenated to form suitable hard soap fats; a quantity of these oils is used regularly in the preparation of soft soaps and in blends with harder fats. The chief animal fat used in soapmaking is tallow. Other fats and oils less frequently used include babassu, palm kernel and olive oil. The ratio of tallow/coconut oil used for the manufacture of toilet soaps ranges from 85:15 to 75:25. A correlation of soap properties with the ratio of 95:5 to 75:25 of tallow and coconut oil demonstrates that properties such as cracking, swelling and hardness are not as sensitive to the changes in the blend ratios as are erosion characteristics, slushing and lather. Present production of Russian and Eastern European soap is from huge quantities of straight-chain, odd- and even-numbered, carbon saturated synthetic fatty acids (SFA). Future fat-based raw materials might include certain fractionated fatty acids, methyl ester intermediates, acidulated sunflower and/or safflower soapstocks. Jojoba wax might be a surprising new raw material.     

Determination of hexachlorophene content of soaps using ferric chloride reagent

Summary Hexachlorophene is determined in soap by measuring the color produced by reaction with ferric chloride in alcohol solution with controlled conditions of time and temperature. The precision is within ±5% of the hexachlorophene content at the 1/2% level or above. As a criterion, any soap that will give a finely dispersed barium soap and that does not form a precipitate with ferric chloride under the conditions of the method give good results. This includes all milled bar soaps. The effect of phenolic perfume ingredients on the result is negligible. Five per cent abietic acid in the fatty acid composition has no effect on the result. The method is slightly modified for use with liquid potassium soaps.     

Methyl glucoside fatty acid diesters

Summary and Conclusion Procedures are described for the preparation of methyl glucoside diesters by direct esterification, using a ratio of one mole of methyl glucoside with two moles of fatty acids. Rate studies indicated that lead or stannous soaps are more effective catalysts than the sodium soaps for speeding up tis esterification. With equal molar quantities of methyl glucoside and fatty acid, the lead and the sodium soap catalysts give products containing predominantly diester and half the methyl glucoside remaining unreacted. Under the same conditions stannous soap catalysis gives high yields of monoesters containing only very small percentages of unreacted methyl glucoside. From the standpoint of speed of reaction, color of the final produets, ease of removal of catalyst from the ester products, and catalyst cost, litharge is the preferred cytalyst for the preparation of methyl glucoside diesters. Properties of various methyl glucoside fatty acid diesters, prepared on a laboratory scale, are given. Du Noüy surface-tension measurements indicate that small quantities of the methyl glucoside dilaurate, dicaprate, or dioleate are quite effective in lowering the surface tension of water.     

Thermal analysis and calorimetry of some fatty acid sodium soaps

Transition temperatures and enthalpies and some phase diagrams of pure odd and even sodium soaps have been determined by means of dif-ferential thermal analysis and scanning calorim-etry. Branched sodium soaps have been added for comparison. No essential difference has been found between the number, type, and enthalpy of the transitions of the neighboring odd and even soaps. The total enthalpy and entropy of transition are consider-ably lower than those of the corresponding par-affins and fatty acids. The entropy of the subneat-neat and perhaps of the neat isotropic transition has an alternating character, which suggests a different methyl end-group packing for even and odd soap. These two facts suggest that the melted soap is still in an organized state. Presented at the AOCS Meeting, New Orleans, May 1967.     

表面活性剂复配体系的分析

介绍了一种使用经典的分析技术定量测定液体皂、皂胶、洗衣皂及香皂中存在的皂类、脂肪酸、非离子表面活性剂及除肥皂以外的阴离子表面活性剂和两性表面活性剂混合物的分析方法。这种方法克服了分析混合表面活性剂系统时常常会碰到的问题。     

Tall oil fatty acids

About 1949, with the advent of effective fractional distillation, the tall oil industry came of age, and tall oil fatty acids (TOFA), generally any product containing 90% or more fatty acids and 10% or less of rosin, have grown in annual volume ever since, until they amount to 398.8 million pounds annual production in the U.S. in 1978. Crude tall oil is a byproduct of the Kraft process for producing wood pulp from pine wood. Crude tall oil is about 50% fatty acids and 40% rosin acids, the remainder unsaps and residues; actually, a national average recovery of about 1–2% of tall oil is obtained from wood. On a pulp basis, each ton of pulp affords 140–220 pounds black liquor soaps, which yields 70–110 pounds crude tall oil, yielding 30–50 pounds of TOFA. Separative and upgrading technology involves: (a) recovery of the tall oil; (b) acid refining; (c) fractionation of tall oil; and occasionally (d) conversion to derivatives. TOFA of good quality and color of Gardner 2 corresponds to above 97% fatty acids with the composition of 1.6% palmitic & stearic acid, 49.3% oleic acid, 45.1% linoleic acid, 1.1% miscellaneous acids, 1.2% rosin acids, and 1.7% unsaponifiables.