Abietic acid derivatives

Expandable PS Thermoplastic urethane Abietic acid derivatives Polyester fiber Chlorinated polyether resins Butadiene-acrylonitrile copolymers Melamine resin Polyurethane filament Cast epoxy Nylon-6... 

When the additive consisted of an Aroclor (a chlorinated biphenyl or terphenyl), a poly(styrene glycol), or an abietic acid derivative, the tensile moduli of the films increased as the concentration of additive was increased to about 30%. In two films (from the bisphenol I and bisphenol A polymers), the modulus increased as the concentration of a chlorinated terphenyl increased even to 40%. Instead of becoming more flexible, as would be expected, the films became stiffen Most of these additives, incidentally, were viscous or very viscous oils. The effect of two Aroclors on the tensile moduli is shown in Figure 1. 

The reaction can be effected at low temperature or at the boiling point of the amine. Methylamine or a lower homolog, ethylenediamine,58 or an alkyl-aniline56 is usually used. They often act simultaneously as proton donors, but in other cases ammonium salts must be added after termination of the reaction. In reductions of abietic acid derivatives it was shown that reaction of lithium in ethylamine is milder than in presence of tert-pentyl alcohol.59 A review of these reactions is given by Birch and Smith.60... 

The tricyclic diterpene carboxylic acid, abietic acid, is widely distributed (see Chap. 8.1) and commonly available commercially. Fisher implicated it in a case of allergic contact dermatitis because it is the major constituent of violinist s resin (58). It is also found in colophony and pine resins, on which Karlberg et al. (92) performed a dermatological study. Wahlberg (182) studied dermatitis caused by abietic acid and colophony. Abietic acid derivatives are also common, so some derivatives (161) of it have also been studied, notably dihydroabietyl alcohol (49). A white powder from the bark of Betula sp. causes skin eruptions in mill workers... 

Composition. Rosin is primarily a complex mixture of monocarboxyUc acids of alkylated hydrophenanthrene nuclei. These constituents, known as resin acids, represent about 90% of rosin. The resin acids are subdivided into two types, based on their skeletal stmcture. The abietic-type acids contain an isopropyl group pendent from the carbon numbered 13. The pimaric-type acids have a methyl and vinyl group pendent from the same carbon atom. Figure 1 shows the stmcture of typical resin acids abietic acid, C2QH2QO2 (1) is predominant. The remaining 10% of commercial rosin consists of neutral materials that are either hydrocarbons or saponifiable esters. These materials are derived from resin acids by decarboxylation or esterification. 

Rosin and tall oil-based tackifiers are derived from feedstock, which is typically obtained by extraction and distillation of the materials from shredded tree stumps or wood chips. A typical structure of one of the different products obtained through this process is this abietic acid structure shown in Fig. 14 as a representative of the rosin acid family. 

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. 

We focused our attention on Tall oil, a by-product of the paper industry, whenever this is prepared according to the KRAFT process. Said material consists of a mixture of highly unsaturated fatty acids (many of which with conjugated diene systems) and terpene derived rosin acids. The rosin acids have the molecular formula C20H30O2 and thus belong to the diterpenes (pimaric and abietic acids). Tall Oil has an iodine number equal to approximately 170 gl2/100 g. 

Besides taxodione and taxodone, these synthetic approaches have been conveniently modified to synthesize other related derivatives such as ferruginols, sugiols, and royleanones.51-52,56-57,60-62 In addition, the enantiomeric-selective synthesis of (+ )-taxodione 1 has been reported using (—)-abietic acid as the starting material63 or with a chiral ligand in the polyene cyclization process.64... 

Amber deriving from the extinct species Pinus succinifera is known as Baltic amber or succinite and consists of dimers of abietic acids and copolymers of communol and communic acid. Amber is less soluble than the other resins, but partially soluble in hot oil, so it has been used as an ingredient in varnish. 

There are several materials that make up this category, including wood-derived tall oil rosins and pine stump extracts sold under the well known VinsoH trade mark. They consist of complicated mixtures containing greater or lesser amounts of abietic acid (Fig 3.2) together with pimaric acid, and phenolic compounds such as phlobaphenes. 

Abietic Acid, Diazido Derivative, (Ns)aCl9HaT COOH — not found in Beil or CA through 1956... 

Abietic acid and derivatives 1 A2-A4 abietic acid 1 A2—A3 abietic acid, diazide derivs 1 A3 abietic acid, organic derivs 1 A3 abietic, azido derivs 1 A3 dinitroabietic acid 1 A3 polynitro derivs of abietic acid 1 A3 trinitroabietic acid 1 A3... 

Abietic acid, organic derivs 1 A3 Abietic, azido derivs 1 A3 Ability to propagate detonation (test) 1 VII Ablation 1 A4... 

Nitration of abietic acid was reported in 1904 [66]. Johansson [67] was the first to describe a crystalline nitro-derivative which he considered to be dinitro-abietic acid of the formula CI9H27(N02)2C00H, m.p. 178-184°C (see also [68]). Later reports by Dubourg [69], Goldblatt et al. [70] described the nitration in nitric acid (d = 1.42) in presence of acetic add to form dinitroabietic add C,8H2j(N02)2C00H of m.p. 171°C (yield 33%). 

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