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Unpolymerized, Unsaturated Polyester ‘ Resin

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Unpolymerized, Unsaturated Polyester ‘ Resin Nov. 3, 1970 F, FEKETE ET AL 3,538,188 POLYESTER RESIN COMPOSITION HAVING A THICKENING AGENT THEREYIN Filed Aug. 7, 1967 UNSATURATED AT LEASTI% MgO OR Mg(OH)2 POLYESTER RESIN PLUS AT LEAST O.l% Li‘Cl OR‘ LiBr OR LiNO3 THICKENER CHEMICALLY THICKENED UNPOLYMERIZED, UNSATURATED POLYESTER ‘ RESIN INVENTORS FRANK FEKETE 4’; BY MELVIN E. BAl/M 1 3,538,188 United States Patent 0‘ ice Patented Nov. 3, 1970 1 2 eventual viscosity buildaup; however, one of its draw 3,538,188 backs is that the initial thickening rapidly builds up the POLYESTER RESIN COMPOSITION HAVING A viscosity which reduces the pot-life of the resin. Another THICKENING AGENT THEREIN dif?culty encountered is the slow overall build-up of the Frank Fekete and Melvin E. Baum, Monroeville, Pa., as signors to Koppers Company, Inc., a corporation of viscosity of the resin. Resins modi?ed to rapidly cure to Delaware a B-stage have a tendency to continue to cure or harden Filed Aug. 7, 1967, Ser. No. 658,826 beyond the B-stage within a short period of time. Int. Cl. C08f 21/02 US. Cl. 260-865 8 Claims SUMMARY OF THE INVENTION 10 Quite surprisingly, we have discovered a system for chemically thickening polyester resins which comprise the ABSTRACT OF THE DISCLOSURE addition of a mixture of inorganic salts which inhibits The viscosity of unsaturated polyester resins formed viscosty build-up for about 24-48 hours and thereafter by dissolving the condensation polymers of unsaturated causes a rapid high viscosity buildup. The invention thus dicarboxylic acids and dihydric alcohols in ethylenically 15 allows the pot-life of the resin to be extended yet pro unsaturated copolymerizable monomers may be increased vides a rapid high viscosity build-up after the initial inhi by adding a mixture of inorganic lithium and magnesium bition of viscosity increase. After eight days, the viscosity salts to the unsaturated polyester resin. A mixture of mag of the polyester resins thickened in accordance with the nesium oxide and lithium chloride, yields particularly invention increases over 200 times the viscosity attained outstanding results. These salts initially inhibit the viscos 20 in the initial 24 hours. ity build-up during the ?rst 24 hours which lengthens the In accordance with the invention, an unsaturated poly pot-life. Unsaturated polyester resins having thickening ester resin composition which increases in viscosity after agents therein are useful in precoating of glass ?ber mats. formation of the composition comprises: (a) an unsatu rated polyester formed by condensing at least one dicar boxylic acid containing a,?-ethylenic unsaturation, and a BACKGROUND OF THE INVENTION dihydric alcohol; (b) an a,B-ethylenically unsaturated co polymerizable monomer; and (c) a thickening agent that Cured unsaturated polyester resins which have been will increase the viscosity of the composition after a reinforced by ?brous materials such as glass ?ber mats or spaced period of time, the thickening agent consisting es the like have excellent physical strength characteristics. sentially of a combination of inorganic magnesium and However, the formation of shaped objects with such ma lithium salts. The preferred inorganic magnesium salts are terials has presented problems because the ?bers initially oxides and hydroxides of magnesium, while the preferred immersed within the uncured liquid resin tend to rise to inorganic lithium salts are the halides and the oxides of the surface causing the object, after curing of the resin, nitrogen. to have irregularities in the surface. To avoid this problem, preforms have been made by DETAILED DESCRIPTION spraying glass ?bers onto screens similar in shape to the As previously described, in accordance with the inven ?nal desired product. Air is sucked through the screen tion, an unsaturated polyester resin may be thickened by to hold the ?bers in place. A binder is then sprayed over the addition of a combination of magnesium and lithium the ?bers and cured to hold the ?bers together in the de salts which initially inhibit viscosity buildup (thus giving sired form. The form is then placed into a mold and the a longer pot life) and then rapidly increasing the viscosity unsaturated polyester resin is poured into the mold and of the resin. cured therein. The resin must be viscous enough to adhere Unsaturated polyester resins are well known in the art to the form, yet not so viscous as to prevent proper wet (see, for example, US. Pat. 2,255,313, issued to Carleton ting of the ?bers. 45 Ellis)' The unsaturated polyester is a condensation poly~ To overcome the foregoing cumbersome and critical mer formed by polyesterifying dicarboxylic acids with process, it has been proposed to coat the glass ?bers with dihydric alcohols. To form the polyesters approximately the uncured unsaturated polyester resin liquid to thor equal-molar proportions of the dicarboxylic acids and oughly wet the ?ber. The liquid resin is then thickened dihydric alcohols are used. To provide unsaturation without actually curing the resin by chemical or physical within the polyester, at least a portion of the dicarboxylic means. The physical means include: (1) driving off a acids contain u,[3-ethylenic unsaturation. Examples of such volatile solvent in which a viscous polyester resin has been unsaturated dicarboxylic acids include maleic and fumaric dissolved, or (2) using a heated viscous polyester resin acids. The remainder of the dicarboxylic acids are usually and then cooling the coated ?bers after application. The either saturated normal aliphatics such as adipic acid, suc chemical means include: (1) the addition of a thickening cinic acid, or the like, or aromatic diacids such as phthalic agent such as MgO to the polyester resin, or (2) the par acid, isophthalic acid or the like. tial copolymerization or curing of the resin to a gelled Illustrative of the dihydric alcohols are ethylene glycol, or B-stage. propylene glycol, 1,2-butanediol, 1,3-butanediol, 1.4-bu However, such systems each have certain economic tandiol, diethylene glycol, polyproylene glycol, 2,2’~di drawbacks. The solvent system, of course, results in loss 60 methyl-1,3-propanediol, 1,4-cyclohexane dimethanol and of the solvent plus disposal of the fumes. Heating viscous adducts or reaction products of alkylene oxides and 2,2’ polyesters to reduce their viscosity is costly and cumber bis(4~hydroxy phenylene) propane (Bisphenol A). some. Chemically thickening the polyester resin such as The dicarboxylic acid and dihydric alcohols are reacted by the addition of MgO or Mg(OH)2 as shown in US together in approximately equimolar proportions to form Pat. 2,568,331, issued to Vincent Frilette results in an 65 a polyester. The average molecular weight of the polymer 8,588,188 is most conveniently measured with respect to the acid invention by the use of MgO alone would result in a end groups. A gram of the polyester is titrated with KOH system having too high an initial viscosity for practical and the number of milligrams of KOH necessary to neu use. tralize the gram of polyester is called the acid number In accordance with the invention, a mixture of mag of the polyester. Acid numbers below 100 usually signify nesium and lithium inorganic salts are added to the un polyesters having su?icient molecular weight to possess saturated polyester resin before application of the resin good physical properties. Therefore, the unsaturated poly to a substrate or ?ber mat or the like. The salts may esters useful in the invention are those possessing a be added before, during or after the addition of the per molecular weight indicated by an acid number below 100. oxide catalysts commonly used in such systems. After formation, the unsaturated polyester is usually 10 The amount of the inorganic salts and the ratios there“ dissolved in an ethylenically unsaturated monomer such between may vary somewhat depending upon the amount as styrene or vinyl toluene. The unsaturated polyester resin of viscosity build-up desired. It has been found, however, (polyester and monomer) is then cured by initiating a that the magnesium salt must be used in a minimum free radical polymerization between the ethylenically un amount of 1.0% by weight of the polyester resin and the saturated monomer and the unsaturated polyester at the lithium salt must be used in a minimum amount of at u,?-ethylenic double bonds in the polyester. This copolym least 0.1% by weight of the polyester resin. While larger erization may be initiated by UV light or radiation, but amounts of either salt may be used, it has been found is more commonly initiated by addition of a peroxide that amounts in excess of 2.0% magnesium salts or 1.0% catalyst followed by heating. The polyester resin copolym lithium salts are unnecessary to achieve the rapid and erizes to form a cross-linked thermoset resin. 20 high viscosity chemical thickening of the invention. Illustrative of the copolymerizable ethylenically unsat The preferred magnesium salts are magnesium oxide urated monomers are styrene, a-methylstyrene, chloro and magnesium hydroxide, while the preferred lithium styrene, vinyl toluene, divinyl benzene and the like. salts are the halides and the oxides of nitrogen, (i.e., Examples of peroxide catalysts commonly used to lithium ?uoride, lithium chloride, lithium bromide, lith initiate the copolymerization include benzoyl peroxide, 25 ium iodide, lithium nitrate, and lithium nitrite). Especial methylethyl ketone peroxide, cumene hydroperoxide, and ly preferred salts are magnesium oxide and lithium chlo the like. ride. Other inorganic salts of these metals also be used Other free radical generating catalysts may also be used such as lithium sulfate, lithium hydroxide, lithium acetate, as, for example: 2,2'-azobisisobutyronitrile. lithium nitrate and lithium phosphate. However, the re~ In accordance with the invention, the viscosity of the sults obtained with these salts are not as outstanding as polyester resin is increased before the ?nal curing of the the results obtained using the preferred salts.
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