Rosin salts

Studies of the metal-exchange process of P.R.49 (Na) to P.R.49 1 (Ba) [1] revealed that the process, apart from the temperature, is not only influenced by the crystal structure and the concentration of the barium ions but also by the amount of rosin soap. Colophony-based rosin which is assumed to act as a surfactant, is converted during the laking process into colorless insoluble rosinate salts. These salts are incorporated in the pigment til up to 30% by weight without a loss of tinctorial strength. Very often the color strength is even increased, accompanied by a color shift to more bluish reds. 

Table VI lists the relationship between the sample preparation and the amount of hydrocarbon (Cj) on the surface. Obviously, those samples with internal sizing added have an elevated hydrocarbon content. It is this hydrocarbon, in the form of rosin and rosin salts, that imparts the low surface energy and resistance to water penetration to the paper. In other cases, the hydrocarbon is probably in the form of lignin remaining from the pulping operation or adventitious carbon simply from the handling of the sample.

Table VI also shows the relationship between the amount of hydrocarbon in the form of percent Ct and the relative fuse grade. The number of samples in Table VI is reduced from previous tables since many of the papers, because of their properties, were unable to withstand the abrasive fuse grade testing. For example, the sample with high levels of filler separated rather easily and pulled fibers from the surface, invalidating the test procedure. Even without these samples, however, a clear relationship between the amount of hydrocarbon on the surface, either in the form of rosin and rosin salts or lignin, is clearly related to the adhesion of the toner polymers to the paper surface. A least square fit of these data has a (relatively low) correlation coefficient of 0.85, and a slope of -0.8. Although the relationship may not be a linear one, it is clearly reasonable to presume that higher quantities of hydrocarbon on the surface of paper do prevent adequate adhesion of toner. This result corresponds with the previous work done by Borch(16) and also with results presented elsewhere in this symposium volume.

Elastomeric ionomers have also been developed from ethylene-propylene-diene ternary copolymers known as EPDM rubbers. The diene is commonly ethylidene norbomene. Du Pont made carboxylated ionomers by free-radical grafting of maleic anhydride (0.5—5%) onto the diene moiety of the polymer and neutralized the product with rosin salt. The ethylidene norbomene can also be sulfonated, thus ... 

Synonyms Potassium rosin salt Potassium soap of rosin... 

Potassium rosin salt. See Potassium rosinate Potassium saccharin CAS 10332-51-1... 

Rosin salts of polyvalent metals, e.g., Ca, Zn, Pb, and Mn, have been used as driers for paint and varnish and in printing inks. Six million pounds of rosin salts were produced in 1980, mostly from tall oil rosin the and Na-i-resinates have been used in emulsion paints. 

CAS 61790-50-9 61790-51-0 EINECS/ELINCS 263-144-5 Synonyms Potassium rosin salt Potassium soap of rosin Ionic Nature Anionic... 

When heated with small amounts of iodine, rosins, taU. oil, and other wood products are converted to more stable forms (135,136). Iodine has been used with some tin salts as a catalyst in the hydrogenation of coal (qv) and its distillation products (137,138), and has been recommended as a catalyst for the production of drying oils (qv) from unsaturated animal fats (139,140). 

Tall oil rosin is a by-product of paper manufacturing. Raw wood chips are digested under heat and pressure with a mixture of sodium hydroxide and sodium sulfide. Soluble sodium salts of lignin, rosin, and fatty acids are formed, which are removed from the wood pulp as a dark solution. The soaps of the rosin and fatty acids float to the top of the mixture, where they are skimmed off and treated with sulfuric acid to free the rosin and fatty acids. This mixture, known as cmde tall oil (CTO), is refined further to remove color and odor bodies fractional distillation separates the tall oil rosin acids from the fatty acids (see Tall oil). 

The carboxyl group reacts with metal oxides, hydroxides, or salts to form rosin soaps or salts (resinates). The soaps of alkah metals, such as sodium and potassium, are usehil in paper sizing and as emulsifiers in mbber polymerization. 

The most commonly used emulsifiers are sodium, potassium, or ammonium salts of oleic acid, stearic acid, or rosin acids, or disproportionate rosin acids, either singly or in mixture. An aLkylsulfate or aLkylarenesulfonate can also be used or be present as a stabilizer. A useful stabilizer of this class is the condensation product of formaldehyde with the sodium salt of P-naphthalenesulfonic acid. AH these primary emulsifiers and stabilizers are anionic and on adsorption they confer a negative charge to the polymer particles. Latices stabilized with cationic or nonionic surfactants have been developed for special apphcations. Despite the high concentration of emulsifiers in most synthetic latices, only a small proportion is present in the aqueous phase nearly all of it is adsorbed on the polymer particles. 

Ethoxylation of alkyl amine ethoxylates is an economical route to obtain the variety of properties required by numerous and sometimes smaH-volume industrial uses of cationic surfactants. Commercial amine ethoxylates shown in Tables 27 and 28 are derived from linear alkyl amines, ahphatic /-alkyl amines, and rosin (dehydroabietyl) amines. Despite the variety of chemical stmctures, the amine ethoxylates tend to have similar properties. In general, they are yellow or amber Hquids or yellowish low melting soHds. Specific gravity at room temperature ranges from 0.9 to 1.15, and they are soluble in acidic media. Higher ethoxylation promotes solubiUty in neutral and alkaline media. The lower ethoxylates form insoluble salts with fatty acids and other anionic surfactants. Salts of higher ethoxylates are soluble, however. Oil solubiUty decreases with increasing ethylene oxide content but many ethoxylates with a fairly even hydrophilic—hydrophobic balance show appreciable oil solubiUty and are used as solutes in the oil phase. 

Black Liquor Soap Acidulation. Only two-thirds of a typical black Hquor soap consists of the sodium salts of fatty acids and resin acids (rosin). These acids are layered in a Hquid crystal fashion. In between these layers is black Hquor at the concentration of the soap skimmer, with various impurities, such as sodium carbonate, sodium sulfide, sodium sulfate, sodium hydroxide, sodium Hgnate, and calcium salts. This makes up the remaining one-third of the soap. Cmde tall oil is generated by acidifying the black Hquor soap with 30% sulfuric acid to a pH of 3. This is usually done in a vessel at 95°C with 20—30 minutes of vigorous agitation. Caution should be taken to scmb the hydrogen sulfide from the exhaust gas. 

Latex Types. Latexes are differentiated both by the nature of the coUoidal system and by the type of polymer present. Nearly aU of the coUoidal systems are similar to those used in the manufacture of dry types. That is, they are anionic and contain either a sodium or potassium salt of a rosin acid or derivative. In addition, they may also contain a strong acid soap to provide additional stabUity. Those having polymer soUds around 60% contain a very finely tuned soap system to avoid excessive emulsion viscosity during polymeri2ation (162—164). Du Pont also offers a carboxylated nonionic latex stabili2ed with poly(vinyl alcohol). This latex type is especiaUy resistant to flocculation by electrolytes, heat, and mechanical shear, surviving conditions which would easUy flocculate ionic latexes. The differences between anionic and nonionic latexes are outlined in Table 11. 

The most important single reactions produced in the carboxyl functionality of the resin acids are salt formation, Diels-Alder additions, and esterification. Other reactions, such as disproportionation and polymerization, are less important. For some specific applications, rosins are subjected to a combination of these reactions. 

Salt formation. The resin acids have a low acid strength. The pa s (ionization constants) values of resin acids are difficult to obtain, and values of 6.4 and 5.7 have been reported [23] for abietic and dehydroabietic acids, respectively. Resin acids form salts with sodium and aluminium. These salts can be used in detergents because of micelle formation at low concentrations. Other metal salts (resinates) of magnesium, barium, calcium, lead, zinc and cobalt are used in inks and adhesive formulations. These resinates are prepared by precipitation (addition of the heavy metal salt to a solution of sodium resinate) or fusion (rosin is fused with the heavy metal compound). 

A mixture of 142.5 g of "Rosin Amine D" containing about 70% dehydroabietylamine and 30% dihydro and tetrahydroabietylamine, 47.0 g of ethylene dibromide, and 60.6 g of tri-ethylamine is dissolved in 350 cc of anhydrous xylene and refluxed for about 16 hours. Thereafter the triethylamine dibromide salt formed Is separated from the solution by filtering the cool reaction mixture and washing with ether. The solution is then concentrated under reduced pressure to dryness to remove the ether, xylene and excess triethylamines present. 

The viscous oil resin Is slurried twice with 250 cc portions of methanol to remove any unreacted primary amines. The oil residue after being washed with methanol is dissolved in ethyl alcohol and 75 cc of concentrated hydrochloric acid is added dropwise to the warm alcohol solution of the base. The dihydrochloride salts of the several hydroabietyl ethylenediamines precipitates immediately from solution. The salt is then separated by filtering and is washed twice with 100 cc portions of cooled ethyl alcohol. The dihydrochloride salts of the dehy-droabietyl, dihydroabietyl and tetrahydroabietyl ethylenediamine mixture have a melting point of about 292°C to 295°C. On subjecting the mixture to solubility analyses it Is found that the dehydroabietyl ethylenediamine is present in substantially the same proportion as is the dehydroabietylamine in the original "Rosin Amine D."... 

Most of the inhibitors in use are organic nitrogen compounds and these have been classified by Bregman as (a) aliphatic fatty acid derivatives, b) imidazolines, (c) quaternaries, (d) rosin derivatives (complex amine mixtures based on abietic acid) all of these will tend to have long-chain hydrocarbons, e.g. CigH, as part of the structure, (e) petroleum sulphonic acid salts of long-chain diamines (preferred to the diamines), (/) other salts of diamines and (g) fatty amides of aliphatic diamines. Actual compounds in use in classes (a) to d) include oleic and naphthenic acid salts of n-tallowpropylenediamine diamines RNH(CH2) NH2 in which R is a carbon chain of 8-22 atoms and x = 2-10 and reaction products of diamines with acids from the partial oxidation of liquid hydrocarbons. Attention has also been drawn to polyethoxylated compounds in which the water solubility can be controlled by the amount of ethylene oxide added to the molecule. 

Diazotization of the aminosulfonic acid and subsequent coupling onto the sodium salt of 2-hydroxy-3-naphthoic acid initially affords the monoazo compound in the form of its soluble sodium salt. Subsequent reaction with chlorides or sulfates of alkaline earth metals or with a manganese salt, frequently in the presence of a dispersion agent, or rosin or its derivatives, at elevated temperature yields the insoluble BONA pigment lake. 

Rosin, a brittle solid, mp 80 °C, is obtained from the gum of trees and tree stumps as a residue after steam distillation of the turpentine. It is made of 90% resin acids and 10% neutral matter. Resin acids are tricyclic monocarboxylic acids of formula C20H30O2. The common isomer is 1-abietic acid. About 38% of rosin is used as paper size (its sodium salt), in synthetic rubber as an emulsifier in polymerization (13%), in adhesives (12%), coatings (8%), and inks (8%). 

Equally important is the salt formation of solid bases with gaseous acids. An example has been cited above (30 31). This type of reaction is quite general. Strong and very weak bases react quantitatively and the gas-solid technique does not have problems with moisture. Amino acids such as L-phenylalanine, D-penicillamine (42), DL-penicillamine, L-cysteine, L-leucine, L-proline, DL-ty-rosine and others are quantitatively converted into their hydrohalides with... 

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