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Chapter 17. the Dissolution of the Matrix and Its Ingredients

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Chapter 17. the Dissolution of the Matrix and Its Ingredients CHAPTER 17 The Dissolution of the Matrix and Its Ingredients Although the matrix is at least as important as paints because of their tendency to react with the toxic, the properties which make certain pigments (1, 8). Yet this very acidity and the matrix ingredients useful for the formulation of resultant solubility in sea water is the principal antifouling paints have often not been recognized. reason for the satisfactory performance of anti- As shown in the previous chapter, some paints fouling paints containing such ingredients. depend l!pon the solubility of a matrix ingredient to maintain an adequate steady-state leaching rate THE COMPOSITION OF ROSIN AND of the toxic. The slowly dissolving matrix eventu- ITS DERIVATIVES ally exposes toxic particles which .lie deep within The use of rosin as a constituent of antifouling the paint film, thus permitting them to dissolve paints was patented in 1867 (3), and since that and exert their toxic effect on the fouling organ- time, because of its availability and cheapness, isms. Thus the toxic and the matrix dissolve its use has been constantly expanded. Its only simultaneously, resulting in a gradual decrease serious competitor has been shellac, another in thickness of the film. Since the toxics commonly acidic resin from natural sources. But shellac used dissolve more rapidly than the matrix ingredi- suffers from the drawback that it must be '.im- ents, the rate of solution of the latter controls ported into the United States, a fact that led the the rate of solution of the entire film. This chapter Navy in 1926 to discontinue its use (1). The summarizes the current knowledge concerning reason for the effectiveness of rosin was not known the factors affecting the rate at which certain until 1943, when investigations at the Mare Island matrix ingredients dissolve in sea water. Navy Yard and the Woods Hole Oceanographic For convenience, the factors controllng the Institution simultaneously showed that its virtue solution of matrix materials may be divided into depended upon its solubility (5, 9). two classes: those arising from the nature of the Rosin is obtained from the exudation of pine dissolving medium employed, and those inherent and fir trees, the greater portion of the world's in the matrix film itself. In the first group of supply coming from Pinus palustris (the longleaf factors we must consider the chemical composition pine) and Pinus carribea. The fresh gum, or of the dissolving solution, such as its alkalinity oleoresin, is subjected to steam distilation to and the nature of the salts it contains. The second remove the low-boiling volatile fraction known as group of factors includes the chemical composition turpentine. The residual material, crude rosin, is a of the matrix film, the proportion and nature of dark amorphous solid at room temperature. It is acidic and neutral materials, the number of composed of about 90 per cent of acidic materials, phases present, and such physical properties as called resin acids, and about 10 per cent of neutral smoothness and hardness. In addition, the time materials that are apparently non-volatile sesqui- elapsed between the mixing of the paint and its and diterpenes. The resin acids all have the em- application, the conditions under which the mix- pirical formula C2oHao02, and consist of a mixture ture was prepared, and the age of the paint film of substances the nature of which is not yet itself on the panel or ship bottom may influence entirely clear (6). The acids are known to comprise the solution rate. a mixture of the acid-stable d-pimaric acid and a Many acidic resins are soluble in sea water. Their series of acids (levopimaric acid, the sapinic acids, dissolution requires the formation of soluble etc.) which are all converted by boiling with alkaline salts, and they are not, consequently, mineral acid into abietic acid, a substance that soluble in neutral or acid aqueous solutions. Such represents a relatively stable stage in a series of resins are rendered insoluble if the free acid group complex changes. The formulas of three of these of the molecule is neutralized by esterification or compounds are given on the next page (6). by the formation of an insoluble salt or soap. Methods have been developed for the determi- Paint technologists have commented on the nation of both d-pimaric acid (11) and levopimaric acidic nature of natural resins and have suggested acid (7) in resin acid mixtures. In the original modifying them to overcome this "diffculty," or oleoresin from which rosin is prepared, it has been have even stated that they cannot be used in found that the acid fraction contains 38 per cent 302 DISSOLUTION OF THE MATRIX AND ITS INGREDIENTS 303 CHa ÇOOH CHa COOH ""/ from rosin and low molecular weight alcohols, /"" /"" such as methyl and ethyl alcohols, are far softer XA I I I than rosin, while those formed from polyhydroxy VIV~I I CHa V""(~i iHa alcohols, such as glycol or diethylene glycol, are usually harder and more brittle than rosin. CHa \)( CRa /-CH It should be pointed out that these modified CH=CR2 I rosins are mixtures, as is the parent substance. CHa d-pimaric acid levopimaric acid In addition, the esterification is never complete, so that the product always contains some acid CRa COOH materiaL. The following compounds are typical V rosin esters. The trade name of the material used /"" /"" is given in each case. In these formulas RCOOH Vl~ CHa is used to represent the resin acid. I II I CHa ""/-CH Methyl Abietate (Abalyn) RCOOCHa This material is 92-94% i CHa neutral and is liquid at abietic acid room temperature. d-pimaric acid and 36 per cent levopimaric acid, Glycol diabietate (Flexalyn) the balance consisting entirely of those inter- RCOOCH2-CH200CR This material is 94.5% mediary acids that are convertible into abietic neutral and softens at acid. There is no evidence that any abietic acid 45-50° C. exists as such in oleoresin. In commercial rosin the Glyceryl triabietate (Ester Gum) isomerization process probably takes place to CH2-CH-CH2 This material is 94% some extent during the process of steam distila- I I I neutral, melts at about tion, and abietic acid may be present in amounts o 0 0 100°C., and is quite depending upon the extent'of the heat treatment. o 0 0 britte. Rosin is graded according to its color, and is C C C purified, generally by solvent extraction, for the R R R purpose of removing the color bodies present (10). Pentaerythritol esters of rosin (Pentalyn M) The resin acids of rosin contain two carbon- (HOCH2)aC CH200CR This material consists of carbon double bonds and one carboxyl group per a mixture of all four molecule. The former give rise to the characteristic (HOCH2)2C (CH200CRh possible rosin esters of instabilty of rosin, while the latter enables rosin HOCH2 C (CH200CR)a pentaerythritol, the higher molecular weight to be dissolved in alkali, though the acid itself is C (CH200CR)4 ester predominating. It quite insoluble in neutral or acid aqueous solutions. melts at 165° C., and is The resin acids dissolve in the form of the resinate 97.5% neutral. ion, which is formed by the attack of the hydroxyl The properties of rosin are also changed when the ion of the alkali: double bond.s of the resin acids are modified. The RCOOH + OH--+RCOO-+ H20. double bonds of abietic acid oxidize readily, as evi- The resinate ion wil stay in solution as long as denced by the fact that freshly prepared abietic there is no substance present that wil react with acid becomes quite yellow after a few days. This re- it to form an insoluble compound. In sea water action is represented as follows: the resin ate ion reacts to a certain extent with CHa COOH CRa COOR calciupi and magnesium ions to form the corre- ""/ sponding insoluble soaps. This reaction may also X take place on solid rosin surfaces, and in this way 01/n the rosin becomes at least partially covered with ""/1 ""/"'OH insoluble material, which effectively cuts down the díaVI. I L OH solution rate in sea water. ~~-F CH CRa / "" When the carboxyl group of a resin acid is CHa CHa esterified with a mono- or polyhydroxy alcohol, an Abietic Dihydroxy- alkali-insoluble ester is formed. The esters formed Acid abietic acid 304 MARINE FOULING AND ITS PREVENTION CRa COOH Methyl dihydroabietate (Rercolyn) ""/ CRa COOCRa /"" /""-0 R This material is 99% neu- 1""/1""),, 0 R I)\A I II tral and is liquid at room I i-OR Vl""/. "" CRa temperature. eRa ",/i-OR I I i CR CRaV-FR / "" CRa CRa CRa Tetrahydroxy- abietic acid Maleic anhydride adduct of glyceryl triabietate (Lewisol 33) CR2-CR-CR2 The first step of the oxidation is the more rapid RAI IRA IRA and attacks the more sensitive of the two double bonds. This oxidation increases the acidic proper- RA in this formula is: ties of the rosin, making it dissolve more rapidly in oI alkaline solutions. I Hydrogenation of the double bonds reduces the CRa C=O acid strength and decreases the solubilty of the ~/ This material product in alkali. Staybelite resin is rosin hydro- is 97.5% neu- genated by the addition of one and one-half moles 0('ì CR-CO tral; it softens Vi""/"-, CHa "" of hydrogen to each mole of abietic acid, and con- "- over the range sists of about equal proportions of dihydro- and dIal II tR o 152-1680 C. tetrahydroabietic acid: i /1 / V CRa CR-CO/ CRa COOR CRa COOH Maleic anhydride adduct of diethylene glycol mono- ""/ A V abietate (Neolyn 40) /"" ii CRa COOCR2-CR2-O-CR2-CR20R VIY TRa C/"" ""/ 101 TRa AA This material CRa "")-TR CRaV-TR vl~ CRa CR-CO "" is.
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